“How would you feel about bringing someone else into our play?”
Will sat upright, intrigued by her suggestion. “Yeah? Like who?” His mind went to the new blonde intern with long legs he’d run into on the 13th floor. Or maybe the young redhead with the large chest on the 4th.
Diane looked up at him. “Cary.”
“Carrie who? Is she new here?”
“Cary as in our Cary. Cary Agos.”
Her eyebrow crooked. “What? Did you think it’d be the blonde intern? Or maybe the brunette with the perfect ass on 7?”
He looked up at her and thought, “how… oh. I forgot about her…”
“I’ve seen you interact. Plus I know your type. And,” she started before leaning forward, “I’ve been looking too.”
Will’s jaw dropped. “You… what? Really?”
“Well, your birthday is coming up. I wouldn’t want to ruin any surprise, though.”
His mind whirled. “Would she really?”
“But back to my question. Cary.” She looked at him matter-of-factly and waited for his response.
“Oh. Wait… why?”
“I overheard him talking and he reminded me of you when we first started playing. I thought it’d be fun.”
“What would… I mean, would he, and I…?”
Diane let out a hearty laugh. “No, Pet. You wouldn’t have to do anything except be my toy to show him the ropes. Help me break him in. Unless it’s something you two decide you’re willing to try.”
He looked at her, almost incredulous.
“For my benefit, solely, you understand.” Diane sat back in her chair, placed one hand on her breast, and closed her eyes as she began thinking through the possibilities. “You both will be strapped to my bed, hard as granite as I take turns pleasuring myself on you two. He bites your nipple as I fuck you.” Her hips began grinding into the chair.
Diane sighed as her hips rocked gently against her seat. “You groan knowing full well we’ve got miles to go before you can think of that sweet release. I climb off of you and mount his face as I stroke him, tell you to try to convince me to touch you again. But his mouth is so fucking talented,” she kept on, with a quiet whimper, her hand gripping her breast harder than before.
He nodded but Will’s face flushed, a contrasting and disgusting thought crossing his mind.
She looked up at him, noticing how quiet he’d become all of a sudden. It only took her a second before she realized the problem. “Don’t be jealous, Pet. You will always be my number one. I just thought it might be something fun to do. I haven’t broken in a newbie in quite a while. Remember?”
Diane raised her foot to his lap and slowly started massaging him, delighting tremendously in the fact that he was already half hard.
“Mm. I do.” Will’s body began to melt into his chair as he finally let himself enjoy this.
“You can show him how well trained you are and just how much you like getting me off. Isn’t that right?”
“Oh god yes, Siren.”
She laughed a deep throaty laugh. “We’ll talk with him tomorrow. Right now,” she removed her foot from his lap and placed it back on the floor, “you’re going to bend me over in the bathroom and fuck me. Lock the door and meet me in there.”
Diane rose and watched as he panted, rising from his seat to lock her office door.
She walked into the bathroom and slid down her wet panties and leaving her skirt in place before bending over and watching for him in the mirror.
Moments later Will walked in and pressed his hips and hands against her ass.
“May I, Siren?” He locked eyes with her in the mirror, begging for her to say yes.
Will unbuckled his belt, slipped down his trousers and underwear before falling to his knees.
Diane watched, wondering what he was planning on doing as he sank to the floor.
He bunched her skirt up around her hips and groaned when he found her wet, without panties, in front of him. Will inhaled deeply and put his lips up to hers, before asking permission against them, “may I?”
She put her hand on his head and tugged his hair into her. “Yes!”
Will dove in deep, sparing a long session for another time. He slid his hands around to the front of her thighs and held on tight. Diane was already almost dripping wet and he knew how easy it’d be to get her off. His tongue slid between her lips and up to her ass.
She yelped at the change in sensations and grinned at the pleasure he was giving her. “Yes,” she panted.
He flicked her clit, hard and fast as her thighs tensed. She was getting close.
Will groaned, pulling away and standing as quickly as he could.
Diane whimpered, her eyes flashing open in anger. But before the words could come to her lips, Will slammed himself into her.
“Christ!” She barked.
Will gripped her hips as he continued to drill her hard and fast for several minutes, continuously watching her face in the mirror.
“Please cum, Siren.”
She locked eyes with him in the mirror. Her internal muscles clenched as she got closer and closer to her climax.
“Please?” He begged, knowing full well how close he was getting.
Diane gripped the sink, pushing back into him.
He fucked her harder, giving her everything he had.
“You’ve got me so hard.”
She nodded, biting down on her lower lip.
“I need to make you cum. Please?” Will’s fingers dug deeper into her hips as he tried desperately to hold back.
Diane’s eyes slammed shut as she came hard. Her face contorted as her body froze, briefly, before spasming on him. She pushed back into him, barely eking out, “go.”
That simple command was his permission for release. He let himself go deep within her, pushing deeper with each thrust.
Her body slowed its movements while she gasped for air, shockwaves hitting her.
Will wrapped an arm around her midsection and pulled her closer to him. Diane opened her eyes and met his in the mirror.
She smiled as she looked at his lips. “Kiss me.”
He smiled as his hands moved to her hips. Diane pulled away slowly, letting him slip out of her. Will groaned, still quite sensitive, as Diane grabbed a few tissues and turned around, cleaning him off gently before embracing him fully, his semi-hardness pressed between the two of them.
She wrapped her arms around his neck and pulled him in for a kiss. “You know me well.”
He grinned. “What? Did you think I was going to leave my Siren high and dry?” He chuckled, “so to speak.” He kissed her deeply, once more. “You own my cock.”
“And I know better. You have me very well trained.”
Diane smiled as she ran her tongue long his bottom lip before nipping at his upper lip. “That I do.”
“Cary, meet me in my office at 7?” Diane asked as she walked past his desk.
“Oh. Sure,” he replied with a flirty smile.
She smiled back and walked over to Will’s office, knocking quietly so as not to startle him. He’d been working hard on an intense case lately so she’d found him to be slightly jumpy. “Hey.”
“Hmm? Oh. Hey Diane.”
“So I was thinking about talking to Cary tonight. I plan to talk to him one on one at first and then maybe have you come in, maybe around 730. Would that work for you?”
The corner of his mouth ticked upwards and he let out a grateful sigh. “Sure. I’m exhausted but damn I could use the release.”
“Oh Pet, we’re not actually going to play with him tonight. I just want to talk with him and level set expectations.”
Will tried to hide his disappointment.
She mocked his sad face, frowning in response. “I know. I’m a horrible no-good, meanie aren’t I?”
“No, Siren,” he replied knowing full well she had both of their best interests in mind.
Diane walked over to his desk and leaned over next to him as though she were reading something on his computer over his shoulder. “Keep it up and I won’t make you my personal bourbon flavored lollipop this evening,” she warned, quietly and oh so sexily.
Will swallowed hard. “Yes, Siren.”
“Good!” She smacked the desk, jolting him back to reality, as she rose to leave. “730?”
Cary knocked on Diane’s door and waited to for an invitation to come in. “Diane?”
“Oh. Hi Cary. Come have a seat.” Diane gestured to the seat next to her couch as she rose and walked over to sit next to him.
He took the proffered seat and unbuttoned his coat as he did.
“I’ve noticed you flirting with me.”
“No. It’s okay.”
He relaxed a little. “Really?”
She smiled, warmly. “Actually, I overheard you talking with some interns the other day and it reminded me of Will several years ago.”
“Okay…?” He replied skeptically.
“And I’d like to share something with you but it cannot leave this room. Understood?”
“Actually, I’d like you to sign this. It’s just to ensure what we discuss stays among the three of us.”
“You, me, and Will.”
Cary reviewed the short document in front of him and after attempting to scrutinize the eight word statement, “This conversation stays among the three of us,” and noting where both Will and Diane had already signed below, he asked for a pen.
Diane handed him one.
“Why do I feel like I’m signing my life away?”
She chuckled. “You’re not. I just can’t have this conversation getting around to anyone. And what kind of lawyer would I be if I didn’t present you with something like this?”
Cary signed the paper and handed both the pen and it back to Diane.
Diane took it from him and smiled as she walked over and set it on her desk.
“A few years ago, Will and I began a sexual relationship. It started as one of convenience and then one thing lead to another…”
Cary tried his best to hold his jaw in place as she continued.
“And he began submitting to me.”
“He became my Pet.” She paused to judge his reaction. When he didn’t automatically recoil or flee the room, she decided it was safe to continue. “My plaything. And I thought you’d be fun to train.”
“Yes. How to fulfill my needs, sexually and otherwise.”
“Oh. Like… How?”
Diane grinned. “Have you seen Fifty Shades of Grey?”
His eyes grew large. “Well, I…” he stammered, “a girl I was seeing at the time... she…”
She chuckled. “No need to be ashamed. Well, other than the whole execution of that atrocity. Honestly, it’s an abusive relationship and just because he has money people think it’s okay. ‘Mommy porn’ my ass. No sub should be…” Diane stopped and looked over at Cary, eyes still wide.
“Sorry. It’s a bit of a sore spot with me. And I’m the one who brought it up.” She sighed with a chuckle before regrouping. “Okay, it’s sort of like that, only completely different. It’s consensual and I’m not going to pull some bullshit and show up in public and possess you and act like I own you. Ugh. Honestly…”
Diane stopped again and tried to hold back her blush. “Sorry.”
She walked over to him and sat in a chair across from him, leaning in to place a hand on his knee. “Of course, I’ll own you in the bedroom.” Diane arched an eyebrow and smiled. “If you choose to participate.”
“I know. It’s a lot. So you don’t have to give me an answer tonight.”
“I’ve asked Will to come in shortly in case you had any questions.”
“Do you have to be here for them?”
Diane smiled inwardly, knowing that answer showed his interest had peaked.
“I’d prefer to be. But I can sit in the back and just listen. I wouldn’t be here to intimidate. All right?” She moved her hand on his knee, reassuringly. “I just want to make sure we’re all on the same page.”
Cary nodded again.
“Hey. This isn’t meant to be scary. I think you’ll find it quite liberating.” She paused to watch his face, offering, “but I’ll fully understand if you’re not interested.”
“Oh, I’m interested,” he replied quickly, without thinking.
She smiled. “Good. So am I.”
“So,” he started, still somewhat uncertain. “Would I… Would Will…?”
“No,” Will interjected.
Both Diane and Cary looked up at the interruption.
“That was my first question too.” Will shut the door behind him before walking over to her desk and moving her spare next to them. “It’d be solely for Diane’s pleasure, unless you and I discussed something privately and came to a consensus.” He smiled and looked over at her.
She shook her head with a smile. “Such a good Pet.” Diane moved her hand from Cary’s knee and placed it on Will’s cheek, tapping it affectionately.
Will smiled. “What kinds of questions do you have for me?”
“I… I don’t know where to begin. I’m assuming I can come back after I’ve had time to think about all of this?”
“Absolutely,” they replied in tandem.
All three sat quietly for a few moments, Will shifting slightly.
Cary broke the silence. “You enjoy this?” He asked Will.
“I do. It’s quite a release to let someone else take the reins, especially when things get stressful around here.”
Diane nodded. “That’s why it works for us. You may find it to be enjoyable for another reason entirely. And that’s okay.”
He relaxed in his chair, slouching slightly and crossing his hands in his lap. “Could I…”
“Could you what, Dimples?”
Both Cary and Will looked up at her.
“Just something I’m trying out.”
He sighed. “Could I watch once? To see how it goes?”
Diane looked over to Will. “What do you say?”
Will smiled and readjusted his position once again. “I believe you mentioned something about a ‘personal bourbon flavored lollipop’?”
She purred, “I did. William, lock the door. Dimples? Accompany me to my restroom?”
Diane rose and reached for Cary’s hand.
He took it and followed her in to the bathroom.
“Stand in the corner, hands clasped behind your back.”
Cary looked at her, slightly uncertain.
“Did you think you were getting a free show? That’s not how it works Dimples. You can look but you can’t touch.” Her eyes darted to his groin, where she noted a bit of a bulge growing. She leaned in close, her lips almost touching his, “anything.”
Diane placed her hand on his cheek. “Go on. As I said.”
Cary did as he was instructed and awaited what was to come.
Will walked in to the room and grinned. “May I enter, Siren?”
She turned to face him. “You may.”
“Siren?” Cary asked.
“Yes.” Diane replied.
“It’s what I call her.” Will walked into the small space and placed a small tumbler of amber liquid on the sink.
“Is that what I’m to call you, too?”
Diane smiled. “No. Get creative and I’ll let you know if it’s permissible.”
“Now, Pet,” she started, turning to face Will. “Tell me the last instruction I gave you, this evening.”
“I was to touch myself, thinking of my favorite memory of you, of us, but not to let myself cum.”
“That’s correct, Pet.”
“Are you comfortable with letting Dimples see what you have to offer?”
Will looked up at Cary and let out a deep breath, “yes. If it pleases you, Siren.”
She grinned. “It does.”
Diane turned to look at Cary. “Once he takes himself out, I ask that you stay in this room until all is complete. Is that acceptable?”
She leaned forward and placed a gentle kiss on his lips, patting his cheek. “We’ll see if that works.” Diane looked him in the eyes, “thank you. If you get uncomfortable, just close your eyes.”
Cary nodded in understanding and let himself watch as Diane turned to face Will.
“Tell me what you were remembering as you stroked yourself for me.”
Diane moved closer to him, grasping the glass in one hand, cupping his cheek in the other.
Will closed his eyes and recounted an encounter in public. “We’d just won the Thorpe case and we’d gone out for a few drinks. That drunk was hitting on you but I stepped in. He pissed me off because he insulted you.”
She chuckled. “From what I recall, he called your prowess into question.”
He grinned, shaking his head. “No.”
Diane touched the liquid to her lips, dipping her tongue in slightly. It stung but only long enough for her to flick Will’s lips with her tongue. “No?”
Almost instinctually, he bit down on his lower lip to get a taste. “No. He insulted your age.”
“Did he?” Diane reached down and slowly unzipped his zipper and breathed on his lips.
“Yes,” he sighed. “But I made sure he left you alone.”
“Then what?” Diane reached in and pulled his hard cock out.
Will sighed at the first touch. “Then… Then I…” He smiled, “we discussed baseball.”
Diane laughed. “Cal Ripken?”
He thrust his hips forward into her hand. “My favorite. Player.”
She pumped him harder. “Continue.”
“I rubbed your clit through your red silk panties, pulling an incredible climax from you. No one was the wiser.”
“I remember. Anything else?”
“You took off your panties and put them in my pocket that night. Then stuffed them in my mouth later, as you rode me on my couch.”
Cary groaned, audibly.
Diane grinned and licked her lips and released Will, who, in turn, opened his eyes to find out why. She walked over to Cary and took ahold of his chin. “Look at me,” she whispered.
He did, struggling to keep his breathing in control.
“You like what you’re hearing?”
“I’m going to need verbal confirmation.”
“Yes. Yes, Mistress.”
Diane smiled. “Pet? You may stroke yourself as you continue on.” She turned to look at him, “assuming you’re not finished?”
“No Siren.” Will took ahold of his cock and stroked himself slowly.
“Dimples,” Diane started. She kissed him gently. Cary groaned at the first touch of her lips. “Are you enjoying what you’re seeing?”
“And what about what you’re feeling?”
“God yes. Mistress.”
“Does it make you want to touch yourself?”
“Mm. I bet it does. Will you?”
Cary looked at her and blinked deliberately. “Can… I mean… Am I allowed?”
Diane chuckled. “Not now. I want to be the one to make you cum. You want that, don’t you? To please me?” She asked, her voice rising in timbre as she bit down on his lower lip.
“Oh god yes.”
She looked him straight in the eyes, “continue, Will.” Diane leaned in close, her mouth next to his ear, “would you like me to touch you?”
He whimpered. “Yes, please.”
“Good to know.” She flicked his earlobe with her tongue before turning and facing Will. “I said continue, Pet.”
Cary shuddered as he released the painful breath he didn’t realize he was holding.
“Yes, Siren. After I got you off, you returned the favor. I was so fucking hard but you stroked me with impeccable skill.”
Diane walked over to him and, setting the tumbler on the floor, placed her hand on Will’s, taking it from his cock. Will took her hand and helped her to the floor in front of him. He began stroking himself again as she settled on her knees.
She took a deep breath, taking in the scent of his cock. Diane licked her lips once before wrapping her lips around his head, flicking her tongue over his wet slit.
Will’s hips jerked backwards as he let himself go. “Ah!”
“Keep going,” she remarked as she pulled back, taking ahold of the tumbler. Diane took a healthy drink from the glass, swallowing a small portion of the liquid before trailing it over his length. It dribbled onto his balls and the front of his navy blue trousers.
“Oh god. I… I came in my pants. So fucking hard.”
She sucked him deep and hard.
Cary watched and panted, trying not to cum in his pants. He hadn’t known to wear dark pants this morning. It’d be difficult to conceal a wet spot in his grey slacks.
Diane set the glass on the floor next to her as she continued to suckle him.
“Then we… we went back to… Oh god! Yes! Um, to my… my place. God! Oh fuck, Diane.”
She sucked hard and pulled back, looking at him waiting for acknowledgement of his mistake.
Will bit down on his lower lip, finally recognizing his misstep.
Diane slapped his cock, hard, secretly delighting in watching it bounce side to side.
“Oh! I’m sorry!” He panted. “Mistr… Siren. Please forgive me Siren?”
“Uh… We… We went back to my place. You climbed on top of me and fucked me until I got hard. God I loved that.”
Diane watched as Will continued to recount that night.
“Please what, Pet?” She asked, quietly.
“Please. I’m close.”
She grasped his cock and slowly began stroking him again. “Keep going. How did that night end?”
“You pinned my hands over my head and I made you cum. Hard. All over my cock.”
Diane shifted, leaning forward and taking him in her mouth once more. “Mmhmm.”
She sucked him harder and faster as she grasped his balls, placing her thumb on his taint, pushing in and up.
“I can’t…” he whimpered, pathetically.
“Mm mm,” she negated.
Will’s brow furrowed as he concentrated on waiting for her okay.
“You… God! You… I woke up a few hours… hours later. Fuck! Your mouth wrapped around me. Hard. Deeper. You…”
Will’s thoughts disintegrated, becoming more and more disjointed.
Diane deep throated him and dug her nails into his thigh, nodding deliberately.
He fell forward, bracing himself against the wall as he released himself into her throat. She took all he had to give, swallowing everything, rocking her head side to side, unrelenting.
“Christ!” He gasped as his knees shook almost violently.
Diane pulled back from him slowly as she continued to swirl her tongue around the entirety of his length.
His hips jerked backwards. “Ah!”
She released him from her mouth, licking the last few pearl drops from his head as they became visible.
Will’s body slumped forward as he swallowed hard. But his release only lasted a few moments before he remembered where he was and what he was doing. He stood and offered a hand.
Diane placed the glass on her sink and took his hand, rising soon after.
She placed a gentle kiss on his lips and stepped back. “You’re released. You came close there, William.”
He sighed. “I know. I’m sorry.”
Diane reached for then handed him a tissue, which he took so he could clean himself up before tucking himself in and pulling up his zipper.
She turned around and looked at Cary. “Is that something you’d enjoy?”
“God yes,” he gasped.
“You do realize I have yet to cum.”
“I do,” he replied, sobering as he realized he didn’t fully understand their arrangement.
“I don’t always. Don’t worry,” she started as she stepped closer, placing her hand back on his cheek as she reached behind her for the glass. Will recognized her movements and quickly placed it in her hands. Diane moved the glass to her lips and swallowed what was left. “My needs have been met for this evening. But that doesn’t mean I’m foregoing an orgasm. I am, however, a fair Domme. I promised Will a reward for this evening.”
Cary’s eyes darted to Will, who confirmed what she was saying with a slight nod of his head.
Her hand moved from his cheek to the back of his head, pulling him into her mouth. Diane’s lips all but pressed into his, “may I kiss you?”
All he could do was nod.
She smiled and kissed him. Diane sucked on his top lip and bit down as she pulled back from him. “You won’t cum until I say so, will you?”
Cary shook his head.
Diane took a step back and released him. “You may go gentlemen.”
Will locked eyes with Cary and nodded slowly.
He opened the door and walked out, holding it open for Cary to walk behind him.
Cary looked at Diane and after readjusting himself somewhat awkwardly, he followed.
Will’s eyes met Diane’s. He nodded once and shut the door behind them
She turned and stretched before looking at herself in the mirror, touching up her lipstick, grinning. “This is going to be fun.”
Two days later, Cary walked into the office, slowly, deliberately.
“Yeah, I pulled a muscle at the gym,” he offered to Diane’s secretary. “Is she in?”
“She is. I hope you feel better soon. Let me know if I can do anything to help you.”
Cary shook his head as he walked into Diane’s office, “if you only knew.”
He knocked and slowly entered her office, sitting on the chair across her desk. “May I?”
Diane smiled. “Of course. How are you?”
He groaned. “Been better, actually…”
She chuckled. “Do you have plans this evening?”
“I was planning on playing racquetball but I don’t know how well I’d do.”
“I thought we could have a drink. And I might be able to relieve some of your tension.”
He groaned and readjusted his seat. “The three of us?”
“I was thinking just the two of us but if you’d prefer company, I could ask Will to join us.”
Cary smiled. “Do you think I’m ready to be alone with you?”
“You’ve gotta start somewhere,” she purred. “What do you call what we’re doing right now?”
“That’s right. One on one.”
“Would Will be okay with it?”
She smiled. “I don’t need his approval nor are we mutually exclusive. However, we do have a certain level of respect for one another and we’ve already discussed this. He’s okay with us going out and getting to know one another. Admittedly, she’s not fully sold on me having someone to play with other than him but we want each other to be happy. And it’s not like I’m trying to replace him.”
“Are you trying to convince me or yourself?”
“Let’s just say he and I had an interesting conversation earlier today. But everything is settled. So. Drinks around 7?
“Sure.” Cary rose, gingerly, and walked towards his desk. “It’s going to be a long day.”
“You’ll survive,” she chuckled. “My office at 7.”
The day passed slowly, for Cary anyway, and a few minutes before the hour, Cary packed up for the night and grabbed his coat, folding it over his arms in front of him. He walked to her office and leaned against the doorframe. “Drinks, Miss Lockhart?”
She took off her glasses and smiled. “Yes. That sounds perfect. I know I quiet restaurant down the street from my home. Would that work for you?”
“Okay.” Cary smiled and reached for her coat. “Ready to go?”
“Sure.” Diane rose, turned off her PC monitor and walked towards the door, getting into her coat. She shut off the light to her office and, after grabbing her purse, walked to the elevator. He pushed the button; they waited until the doors opened and walked in. “Follow me in your car?”
“You don’t have to be so nervous. If anything happens, it happens. If not, no pressure.” She looked down at his crotch and chuckled. “So to speak.”
He laughed, a bit nervously. “Yeah, sorry about that.”
“I should apologize to you.” Diane closed the distance between the two of them, “it can’t be easy walking around with a hard on all day.” She placed a hand on his chest and moved her lips close to his.
He sighed with a slight laugh, looking down at his offending appendage. “It is.”
“I know. And you shall be rewarded. Handsomely.” She trailed her hand down his chest, stopping just before she reached his cock.
Cary sighed as the doors opened and Diane walked out towards her car. “O’Leary’s.”
“She’s killing me,” he thought. He walked behind her and watched the way her ass moved as she walked. It was perfect. How had he never noticed her before? “God! And the way she smiles. Her lips…”
Diane got to her car, and Cary watched as she licked her lips subconsciously.
“I am so fucked,” he mumbled.
“If you play your cards right. See you at that bar.”
She got into her car and drove off.
Cary shook his head and followed behind.
Several minutes later, they arrived at the bar. Cary parked close by and jogged to open the door for her.
“Thank you.” She smiled. He shut the door behind her and put his arm around her waist as they walked in to the little restaurant.
The couple was escorted to a small table in the corner and, after divesting themselves of their coats, took a seat and ordered two scotches, on the rocks. When they arrived, the couple toasted.
Cary drank all of the liquid and grimaced as the heat hit his throat.
Diane giggled. “Take it easy.”
“Sorry. Scotch isn’t really my thing. I’m more of a beer guy, to be honest.”
“Then get one. It’s not like you need to impress me.” Diane waved over the waitress and Cary ordered what he really wanted. She asked for another scotch and an order of bruschetta for them to share.
The couple talked and as the alcohol disappeared the tension eased.
“So how did you get into this?”
“Well, it just sort of happened. I’ve always been domineering in the bedroom so, one thing lead to another… I did a lot of reading and,” she laughed as she remembered, “and then, believe it or not, Colin Sweeney waltzed into our firm.”
“You’re kidding! How…?”
“It’s not what you think, I swear!” She laughed, reaching across the table and taking ahold of his hand. “In doing research for his defense, I met some interesting people. I learned a lot about them and, conversely, about myself. I met ‘Mistress Lola,’ and I recognized a lot of myself in her. And vice versa. Turns out, by day, she’s a CEO of a paper manufacturing plant, just outside of Chicago.”
Cary sat and listened, completely enthralled.
“So we struck up a friendship of sorts, if you will. We still meet for coffee once a month or so, just to talk about work and politics and men.” She smiled and winked before taking another drink.
Diane leaned back in her seat and kicked off one of her heels before trailing up his leg and coming to rest on his groin. She smiled, somewhat surprised at how hard he already was.
He sighed as her foot made contact with him, his eyes closing to let himself focus on this feeling.
“Look at me.”
Cary’s eyes opened. He swallowed hard as he looked at her.
Diane’s toes played with him, rubbing his balls through his pants, her big toe moving up to his zipper and tugged on it.
His breathing hitched in his throat. “Please.”
She let out a low, throaty chuckle as she moved her foot down his thigh. “You think you’re going to get off that easily, Mister Agos?”
“No. It’s just been a while. And I’ve been hard all day.”
“I know. So I’ll go easy on you tonight.” Diane stepped down into her shoe and slid it back up to his cock, pressing down harder than she had before. “How about we get out of here?”
Cary nodded. “Yeah.”
They got the check and several minutes later, Cary followed her to her home, just down the street.
He parked in her guest space and followed her inside.
Their coats came off and before he knew it, Diane had Cary pinned against her front door with her body. “Do you want to please me?”
He swallowed hard again and nodded.
Diane’s hand trailed down his chest, this time coming to rest on his cock. She gave him a firm squeeze. “I’m going to need a verbal confirmation.” She squeezed him a little harder. “I asked you if you wanted to please me.”
Cary groaned. “Fuck. Yes. Yes, Mistress.”
With her free hand, she moved it up into his hair and tugged, exposing his neck. Diane licked up and bit down on his earlobe. “You understand you’re not to cum until I give you permission, correct?”
She moved his head back in front of her and kissed him. Her lips covered his, her tongue pushing through them. Cary responded in kind, his tongue sparring with hers even more skillfully than she’d anticipated.
Diane continued kissing him while she moved both hands to his shoulders, pulling back to push him down in front of her. “On your knees.”
He did as instructed and waited for his next order.
She turned and walked toward what appeared to be her kitchen. “Come.”
Cary began to rise to his feet but, as though she could see him, ordered, “crawl to me.”
Diane walked into her living room and sat in the middle of her couch, watching as her prey followed eagerly behind her. He stopped at her feet and looked up, awaiting further instruction.
“You’re a quick learner. I like that.”
She rose and quickly removed her skirt and hose, letting them fall to her feet, sitting once more.
“Take your pants and shorts off and position yourself between my thighs.”
Cary took his pants and blushed slightly when Diane noticed he was wearing bikini briefs and not shorts.
“You’re full of surprises, aren’t you?”
“Yes Mistress,” he mumbled.
“It’s nothing to be ashamed of, Dimples. I quite enjoy your choice of undergarments. Take your shirt and tie off as well, then come to me.”
Cary removed the rest of his clothing before moving between her legs and looked up at her.
Diane parted her legs and reached forward, taking ahold of his head as she pulled him in close to her, close enough for him to smell her musk.
“Tongue out. You’ll do as I guide you. Nothing more unless instructed. Understood?”
“Yes, Mistress.” He stuck out his tongue, eagerly anticipating her next move.
“Hands on my thighs, don’t move them.” She threaded her fingers in his hair and pulled him even closer, close enough for his tongue to trace the outline of her lips outside of her blue silk panties. Diane moved him up and down as she watched his fingers dig deeper into her flesh.
“Please?” He begged against her.
“Please may I taste you?”
She tilted his head back and looked at him. “Do you think you’ve earned it?”
“I… I haven’t cum since Tuesday morning. It hurts.”
“It sounds like a personal problem, Mister Agos.”
“I need to make you cum. Your scent is driving me crazy.”
She smiled. “And that’s all?”
He bit down on his lower lip, “I… I have an oral fixation. I really fucking need this,” he panted.
Diane grinned. Apparently he’d said the magic words. She reached down and pulled her panties to the side before pulling him into her. “Show me.”
Cary’s fingers dug into her thighs as he smiled before diving in. He groaned at the first taste of her; it was even better than he could have imagined.
His tongue found her clit almost immediately, causing Diane’s hips to buck against his face.
He licked up and down her slit, nibbled and tugged on her lips with his teeth, slid his tongue into her wetness as he fucked her with it. His hands never moved from their location on her legs, but there sure as hell would be light bruises in the morning. And for once, she couldn’t have cared less.
He really did have an oral fixation and good god was she grateful she’d found out this way. Cary flicked her clit with the tip of his tongue before pulling back and blowing a steady stream of cool air into her.
Diane shivered. “Oh god.”
His tongue circled her clit before he latched on, sucking harder and deeper, humming into her with satisfaction. He shook his head side to side as his five o’clock shadow scraped her thighs.
“Good boy. Don’t stop.”
He pushed into her harder, following her body deeper into the couch before her hips bucked back against him.
“Do you want… oh fuck. Want to make me cum?”
“Mm!” Cary’s jaw pressed into her as he continued going down on her. Without even thinking, his hips began to rock back and forth in anticipation.
Diane reached down to move one of his hands from her thigh up to her breast. Cary growled into her as soon as he realized what he was doing, his fingers kneaded her.
Her thighs clasped around his head as she rode his face. She’d cut off his air supply but he didn’t even notice. All he wanted, in this moment, was to get her off.
“Yes!” She screamed as she came against his face.
Cary’s head moved with her, not to be deterred by her movements.
Her hips relaxed as she panted, jerking a few times as her climax slowly left her. Cary inhaled desperately but refused to let her go.
“Okay. Okay okay okay…”
But he didn’t relent.
“Fuck. I said enough!”
Cary sat back on his feet and gasped for air, smiling as he licked his lips.
“Holy shit. You’re… you’re like a fucking pit bull. You just don’t let go.”
“I told you I have an oral fix.”
“You did,” she panted.
Diane sat up and as she rose, looked down at Cary. “My, my. You’ve made a mess haven’t you?”
Cary looked down and few drips of precum he’d left on the floor in front of him. “Oh.”
“Lick it up and leave it on your tongue. I’m going to go to my bedroom to retrieve something. I expect you to be on the couch, ready for me when I return.”
She steadied herself, her knees still a bit wobbly as she waited for Cary to do as instructed.
Cary licked up his mess and grimaced at the taste before standing then sitting on the couch.
Diane walked into her bedroom, returning quickly wearing nothing but her favorite black heels, with a condom in one hand.
He smiled, feeling relief at what she came back with. His mind raced with all kinds of possibilities.
She tore it open with her teeth and stroked him a few times before slowly sliding the prophylactic down over him. Diane straddled him and placed him at her wet entrance. “Show me your tongue.”
Cary did as he was told, showing off the small bit of cum he still had in his mouth.
“Good Puppy.” Diane kissed him, taking it out of his mouth and swallowing it as she slowly sank down on his cock.
Once she’d taken him within her, fully, she sat back and sighed. “Jesus Christ you’re thick.”
“And you’re so fucking tight.”
Diane blushed before she remembered where she was and what she was doing. This wasn’t the time to be demure, even if it was the first time she was sleeping with him.
She reached for his hands and pinned them above his head as she slowly began riding him.
“Oh fuck. Does that feel good?”
“God yes, Mistress.”
“Mm. Yes, it does.” She gasped when Cary flexed his internal muscles. Diane rocked her hips around his, “do that again.”
He did and she shivered.
She leaned forward and thrust her chest into his face, riding him harder. “Again.”
Cary did as he was told but felt him getting too close for comfort.
“Not yet.” She bounced on him and delighted as she watched his face contort, his fingers flexing in her grip, in frustration.
“Oh god. Please?” He begged.
“No. You’re to make me cum again. Then and only then are you allowed a release.”
He pushed back into her, not quite knowing how he’d manage but that he’d do is damnedest to try.
“I need to make you cum.”
“Yes, you do,” she groaned. “More.”
“Your pussy is so hot and tight. It feels so good on my fat cock.”
She gasped. “Yes!”
“Cum for me? Please? I’ve been a good little Puppy.”
“Oh fuck!” She screamed as she fell forward. Her hands released his as she grasped the couch behind him, using it as leverage to ride him harder. His hands moved to her hips, tugging and pulling her body against his.
Diane came, finally letting Cary follow.
His toes curled as he, too, screamed. Pain and pleasure and the release of days of sexual frustration washed over his face.
“Mm!” She cooed, kissing his jawline.
Cary’s body jerked a few times as the last ripples of his orgasm hit him.
“That wasn’t so bad, was it?”
He sighed, “I almost didn’t make it.”
She ran her fingers though his hair as she flexed her internal muscles. “We’ll work on that.”
Will hadn’t been too happy with the addition of Cary to their play but considering he and Diane were not exclusive, there shouldn’t have been any reason for him to be upset.
“I am not jealous,” he told himself while working out one morning. “No. I’m not the jealous type. She told me…” He ran on the treadmill harder to work out his frustration for a few minutes. His heart rate increased and after a few minutes of intense running, he stopped.
Panting, he rested his head on his arm. “Fuck me. I’m jealous.”
This did not make him feel any better about this situation. There’s no way in hell he’d be able to admit to Diane that he wanted their OT3 back down to an OTP. He couldn’t even begin to imagine how he’d be humiliated both in and out of bed.
Once in the shower, Will resolved to get out and meet someone new. Or, at the very least, go home with someone who wasn’t Diane. She might not think anything of it but his ego could use the stroking right now.
That night, Will went to a bar down the street from his home to see about meeting someone, to see if anything would come of it.
He met Tiffani, Joie, Anna, and Amber. And while all of the girls he met were young and had a large chest, no one was really doing it for him. So, he continued to drink. The night dwindled on and the girls had all paired off with someone else, which only left him more depressed.
That’s when he met Stacey. Stacey was a grad student, studying learned behavior in geriatric patients in nursing homes. She’d needed a night out and decided that even if her friends had left early, she wasn’t going to get in before midnight. She had earned that much.
Stacey saw Will nursing a tumbler of brown liquid and thought, “I’ve had enough tequila. I’m going to go say hi.” He seemed to be interested in the hockey game so that gave her an in.
“Hi. I’m Stacey.”
“Will,” he replied with a nod of his head, still watching the game on the TV in front of him.
“You like hockey?”
He looked over to her and gave a polite smile. “Yeah.”
Stacey took a seat next to him. “I know a little about hockey. You know Jack Gelineau?”
Will’s ears perked up. “Yeah? He was a goaltender for the Blackhawks from 53 to 54.”
“He was my grandpa.”
“Really?” Will turned to face her, giving her his full attention.
She giggled. “No. That’s just my pickup line in bars. Of course he was!” She pulled out her phone and went to her Facebook page, pulling up a picture of her as a kid with him at Christmas.
“Yep! So are you a ‘Hawks fan?”
They talked for a while before the lights came up for last call. The two exchanged numbers and decided to meet again for dinner over the weekend.
As Will walked to his car, he felt pretty good about himself, meeting someone and it wasn’t just about sex. That night had gone better than expected.
The next morning, he walked around the office with a smugness he hadn’t shown in quite some time.
“Well hello Mister Gardner,” Diane greeted.
“Miss Lockhart,” he nodded with his cup of coffee.
“Have a good night.”
“Wouldn’t you like to know?”
She smiled at him before dropping her voice low, “really?”
“Not yet. But yeah.”
“Good for you.”
“How’s things on your end?”
“Training is going well.”
He smiled, “I’d expect nothing less.”
She smiled back and returned to her office.
The next few days passed, texting with Stacey as often as he was available, and they decided to meet on Thursday night close to his office.
They met and talked and realized they had enough in common to keep this up. Sure she was young but Will was young at heart so keeping up shouldn’t be an issue. Plus, she wasn’t looking for long term commitment, just someone to have fun with. This woman was speaking his language!
After their second date, Will suggested they go back to his place for a drink, with the hint that something more would be welcome. She readily accepted and before he knew it, she was curled up on his couch next to him, making out with him.
Will pulled her on top of him to straddle his lap. She wrapped her arms around his shoulders as his hands made their way to her hips. He kneaded her as his hands made their way to her ass. She rocked her hips into him and whimpered in encouragement.
Stacey ran her hand down his chest and came to rest on his cock. She massaged him before climbing off and settling next to him, reaching down to undo his zipper. Stacey pulled him out of his pants and greedily began sucking him, taking all of him down her throat. She massaged his balls and stroked him as her tongue circled his head.
Will sighed as he looked down on the woman giving him head. Stacey loved doing this looked up at him and continued.
But something wasn’t working. Will couldn’t get fully hard.
She tried for several minutes, pulling out every trick she knew, everything she’d heard of or seen done before but it just wasn’t happening.
He put his hand on her shoulder and sighed in defeat. “I don’t think this is going to happen.”
Stacey sat back on her heels and tried not to show the hurt she felt.
“It’s not you. I swear. Maybe I had too much to drink.”
She nodded not really believing him but trying to be understanding, regardless.
“How about we try again next week? Tuesday?”
“I have a presentation on Tuesday. What about Wednesday?”
“In court all day. No idea when I’ll be done.”
“Yeah. Let’s shoot for Thursday.” He placed his hand on her thigh and smoothed it from side to side. “I’m sorry.”
“It happens, right? Um, I’m gonna go. ‘Kay?”
“You don’t have to. You can tell me more about your study of old people.”
She laughed as she stood. “Nah, I think I’ll call it a night.”
He rose and tucked himself back in to his pants. “Text me when you get home so I know you’re safe?”
“Yes mom,” she joked.
Stacey turned to kiss him good night, adding an extra twirl of her tongue before pulling back and looking at him in the eyes. “Nothing?”
He sighed. “Sorry. I promise it’s not you.”
“Okay. Good night.”
She walked back to her car and was able to hold in the tears until she closed the door. Stacey put the key in the ignition and as soon as the radio started, so did her tears. After a moment of sobbing, she reminded herself, “it’s not me. It’s him.” She put the car in gear and drove back to her apartment.
Will walked into his bedroom and started to get ready for bed. He caught sight of himself in the mirror. “What the fuck? This has never happened before.” Looking down at his offending appendage, he asked, “what’s the deal?”
He went to bed but didn’t sleep much. Again, this had never happened to him before so his mind raced with possibilities. He knew he hadn’t had too much to drink, it’s just that whiskey dick is always an easy out. Work was stressful, sure, but nothing beyond what he was really used to. Family had been quiet so there was nothing there that could have been on his mind. He had a smart, gorgeous girl who was into sports, sucking his dick, and for the life of him, he couldn’t figure out why his body didn’t respond like it was supposed to.
Will tried to fall asleep throughout the night when it hit him. “I’m such a shit! I didn’t even offer…” Now, on top of not being able to get it up, he realized he didn’t even offer to do for her. The one thing that never failed to turn him on he’d completely forgotten about.
The next morning, he got up, exercised, showered, and made his way to work, looking like he felt- tired and disheveled.
“Good morning Will,” a voice interjected from the direction of his door.
“You look like hell. Everything all right?”
“Oh, uh, yeah. Just had a rough night.”
“Just wanted to say good morning. I’ll come by later, after you’ve woken up a bit. Please tell me you don’t have clients this morning.”
Will looked at his computer, “first interaction is at ten, over the phone. I’m good.”
Diane turned to leave and as she did, the pen she’d been twirling between her fingers, slipped from her hand. She bent over to pick it up and went back on her way to the conference room.
Will felt a twinge in his pants. “What…?” He stared at her ass as she walked away and felt himself continue to stiffen. “Holy s…”
He grabbed his phone, sending a quick text. “Thinking of you. Looking forward to Thursday night.”
Suddenly, he felt a hell of a lot better. Whatever had stopped him last night was clearly in the past so when he got back a smiley face from Stacey, he replied back with a “sorry again” followed quickly by a flirty/kissy emoji then got back to work.
“Whatever the hell that was is in the past. Thank god,” he mumbled out loud.
Diane came by after lunch and knocked on Will’s door. “Hey. How’s it going?”
He smiled. “Much better thank you.”
“Good. Got a minute?”
“Sure. What’s up?”
She walked into his office and shut the door behind her. “I was thinking of having some playtime with the three of us, probably next weekend. What do you say?”
“I can do Saturday if that works.”
“I’m sure that’ll be fine. I’ll run it by the puppy to see if he’s available.”
“Sounds good. Anything I can or need to do?”
“I’m not certain yet but I’ll let you know before next weekend.” She rose to leave and as her hand hit the door, she remarked, “don’t let this go to your head and it’s nothing against him, but I’ve missed our time together.”
He smiled back. “Yeah. Me too.”
“All right, well, I’ll catch you later.”
Diane walked back to her office and, once again, Will caught himself staring at her posterior.
“I’d love to take a bite out of that. I wonder how bad she’d punish me...” His mind wandered as he kept staring. He sat back in his seat and chuckled to himself. “It’d be worth it!”
Will went home later that night and just to prove it was a fluke, watched porn and quickly rose to the occasion. He decided he’d been through enough and let himself have the release he should have gotten the night before. It didn’t take long to get himself off.
He slept quite well that night.
Will and Stacey texted and talked on the phone, however briefly, daily. By the time Thursday came around, Will was ready to see her. He tried not to be too worried that the fluke would happen again, mostly because he’d been able to get it up since that night.
They skipped the pleasantries and went straight to her place. Will pinned Stacey to the wall, kissing her and pressing his body against hers. They made it to Stacey’s bedroom, clothes being flung from their bodies left and right. By the time they got to her bed, they were both nude.
Before Stacey could make a move, Will climbed on the bed next to her and moved between her thighs. His training springing to mind, before he placed his mouth on her, Will looked up and asked, “may I?”
Stacey giggled as he kissed between her thighs, getting closer and closer to where she needed him before letting out an, “oh god yes!”
He slid his tongue along her slit and teased before finding her clit. Will breathed in her scent and went to work, making himself comfortable between her legs.
Stacey placed her hand on his head and ran her fingers through his hair, tugging each time he hit a favorable spot. He continued pleasuring her, knowing he had the stamina to bring her to orgasm at least once. And he did. His head moved up and down with her hips as she came against his mouth.
Not satisfied with one, Will slowly slid in a single finger and began fucking her with it.
“More?” She laughed.
“Mmhmm.” Will didn’t let go with his mouth to answer and slowly slid in a second finger. She yelped when he moved them around and shuddered when he hit her g-spot.
He kept at it until she came again and damn near climbed the wall trying to get away from his mouth. “Okayokayokayokay stopstopstopstopstop!”
He chuckled into her thigh as he made his way back up her body.
Stacey struggled to catch her breath, panting as Will curled up next to her. He took her hand in his and kissed her palm, waiting for her to come down from her high.
Her breathing slowed. Will nuzzled her neck, “hey.”
She smiled. “Hey.”
“Oh yeah. Who knew you could do that?”
He chuckled and silently thanked Diane and all of her coaching.
“I’m…” she started. “Yeah. Wow.”
He laughed into her neck and kissed her shoulder.
A few moments later, Stacey opened her eyes and propped herself up on her elbow. “Most guys my age don’t do that. Why?”
Will was somewhat caught off guard but gave her question serious thought. “Honestly, I don’t know. They’re missing out, if you ask me.”
She laughed and leaned forward to kiss him. “Ooh. I like the taste!”
“Me too.” He made a show of licking his lips.
“So…” she started again, “how about…” she looked down and saw that he was already half hard, so she continued on. “How about we keep going?”
Stacey’s hand made its way down his stomach and straight to his cock. She began stroking him, commenting on how big he already was, about how good it was going to feel to get fucked by him, anything she could think of to stroke his ego and try to get him harder.
Will groaned. “How about you come show me?” He rolled onto his back and pulled her on top of him.
Stacey climbed on top and positioned him at her entrance. She leaned forward and kissed him, rubbing her wetness over him before sitting up. “Oh! Condom!”
With that, she crawled off of him and reached into her night stand to find one. Will reached down to begin stroking himself, not entirely understanding why he wasn’t hard. This girl had perfect boobs and a killer ass.
Once she found one, she tore it open. “Wanna see a party trick?”
Will chuckled. “What kinds of parties are you going to?”
She giggled and put the condom in her mouth then proceeded to get between his legs and attempt to put it on his cock. Stacey grasped him and started stroking him again while looking up into his eyes, smiling through hers.
Finally, he was hard enough for her to put the condom on him. She did then promptly climbed on top. “You ready for me?”
“Oh yeah,” he grinned.
Stacey slid him against her slit and slowly lowered herself on him, bouncing slowly as she took the entirety of him within her.
“Oh shit,” Will thought. This wasn’t an “oh shit” of pleasure. It was an “oh shit I’m starting to go soft.”
His eyes slammed shut. He thought maybe if he could continue to focus on the feeling of what was happening that maybe he could stay hard.
“Oh Jesus. This is not happening. Um… uh…” He struggled to find something to fixate on to keep going long enough to where he could fake an orgasm and get the hell out of there.
His face twisted before Stacey fell forward, pressing her chest against his and kissed him.
“What do… Oh god!” He kissed her back and thrusted upwards trying to hold on to what little he had.
And then it dawned on him. “Diane.”
Just like that, he saw her bent over in front of him, picking up her pen. He admired the way her skirt clung to her body, how good her cleavage looked, when she let just enough show so as to stay tasteful. This was working! He remembered how wet she gets for him and how incredible she feels when he first gets to sink himself into her.
He pushed back into Stacey, harder, with renewed vigor.
She squealed with delight before moving her head next to his, to whisper dirty things to him.
“Cum for me,” he begged.
“I… oh shit.”
She rocked on him, grinding her clit into his hip.
“God,” he croaked. In his mind, Diane was bouncing on top of him, whispering nasty things in his ear as he worked to pleasure her.
His eyes remained closed tightly as one hand moved to her clit. He rubbed her furiously and felt her begin to contract around him.
“Yes,” he grunted.
“I’m cumming!” She eked out just before climaxing.
Will let himself go, finally getting his release.
She stilled on him before falling off to the side, apologizing when he groaned.
“It’s okay. I just wasn’t ready yet.”
“I’m sorry!” She rolled over and kissed his chest and sighed as they both worked to catch their breath.
Several minutes passed before Stacey asked, “who is she?”
“Diane,” he replied without even thinking. His eyes flew open to look at her. “How…”
“It’s okay. The last time I asked a guy that, her name was Steve.”
Will laughed. “I’m really sorry. I honestly had no idea I was so hung up on her.” He moved her hand to his mouth and placed a kiss on it. “Damn.”
“It’s all right. I’m not kicking you out but give me a call if you get over it. Cuz that was the best head I’ve ever gotten. She’s lucky.”
He laughed again, this time louder. “I am sorry.”
“Stop apologizing!” Stacey moved her hand from his and playfully slapped his chest. “Do you want to talk about it?”
They sat in quiet, enjoying the silence.
“I should probably go,” he offered as he sat up.
Will went to find his pants, dressing as he found his clothing. “By the way. Your party trick is fantastic.”
Stacey sat up and beamed. “Yeah? I practiced on a lot of cucumbers.”
“Cucumbers?” Will came back into the room and looked at her while buttoning his shirt.
“Yeah. They’re easier than bananas. Bananas have that sharp edge and they just tore the rubbers. Plus cucumbers taste better on the outside.”
“I’m sure they do.”
“The only trick is trying to find ones small enough that fit in my mouth!”
“Well nicely done.”
Stacey got up and threw on an oversized sweatshirt then walked Will to the door. “Don’t forget what I said. Seriously. A mouth like that is a rarity.”
He leaned forward and placed a kiss on her lips. “I will. Thanks for being so… awesome.”
She chuckled. “’Awesome’? Is that the best you can do?”
Will smiled. “Amazing? Spectacular? Wonderful?”
Stacey smirked, “keep going.”
As Monday morning rolled around, Will walked into his office earlier than usual, coffee in hand, still making eye contact with no one. Even though his date had been on Thursday night, he still was rather embarrassed by it all. No one knew about it, obviously, but for some strange reason he figured people could tell just by looking at him. No eye contact was safest.
He took off his coat and sat down at his desk. He looked up across the hall and saw his partner was already in, too. “Of course,” he sighed.
Diane noticed he was in early and decided to go say good morning. “Good morning Will.”
He sighed. “Morning.”
“You okay? Have a rough weekend?”
Will gestured to the chair across from him, “got a minute?”
She walked in and shut the door behind her, then set her cup of coffee on his desk. Diane cleared some space on the corner and sat up on it, wrapping her hands around her mug. “What’s up, Pet?”
He chuckled. “Uh.”
“Something got you down?”
“You have no idea,” he snickered sadly to himself.
“Better,” he mumbled. “Listen. I have a problem and I want to talk to you about it but you can’t laugh. You can’t or it’ll just… it’ll be bad.”
She set her coffee down and took ahold of his hand. “Are you okay?”
“Yeah, I’m fine. It’s just… I’ve been… Damn.”
Diane sat in silence and waited for her friend to open up to her.
He looked up at her and sighed. “I’ve had a difficult time getting hard lately.”
She blinked deliberately a few times as she took in this information. “You’re telling me this because…?”
“Because I’ve only been able to get hard when I think of you.”
Her heart sank. She was quiet as she took in this information for several moments, before replying quietly, “you’re incredibly sweet. You know that?”
“I am not!”
“It’s not an insult, Pet. I’m genuinely touched.”
“Stacey was nice about it. She sends her thanks for the oral tricks by the way.” Will looked to his feet, still deeply embarrassed.
Diane laughed aloud. “She’s very welcome.” She kicked off one of her heels and placed her foot in his lap. “How are you feeling now?” Her foot trailed along his inseam until she hit his cock.
He jumped and looked up at her.
“You seem to be doing better, from what I can tell.”
He groaned. “I’ve missed this.”
“Tell me, Pet. Did you cum?”
“Well, yes. But only after imagining you were on top of me.”
“Thank you. But that’s not what I asked you.”
“Good.” Her foot rubbed him harder. “You know we’re not exclusive, right?”
“I know.” Will glanced at her thighs and noticed she was wearing thigh highs, not stockings, which only served to make him harder.
“That’s not to say you need to find another Siren.”
“No. I only have one Siren,” he sighed.
“That’s right. You know, Pet, my heart is full right now. What do you say we run to the bathroom on the next floor up and you show me how much you’ve missed me?”
“Yeah?” His expression brightened.
“Yeah.” She hopped off his desk, looked behind her quickly then took off her panties, stuffing them in his pocket. She winked then put her shoe back on. “Meet me upstairs in the men’s room.” She raised an eyebrow and added, “now.”
Will rose, adjusted his semi and sprinted up the stairs.
Diane walked back into her office, emptied her coffee mug, and took the elevator up a floor. She walked into the men’s room and found Will standing, hands clasped behind him, a grin on his face.
With one finger, she beckoned him to her, with the other hand, she locked the door behind her.
Will walked to her and pressed her against the wall, his body not yet touching hers. His hands were placed on either side above her head as he awaited instructions.
“Pants off. And kiss me.”
He complied and fumbled with his slacks while his other hand stayed in place on the door.
They made out for as long as it took for his pants and shorts to hit the floor.
Diane reached down and grabbed his erection in her hands and slowly started pumping him. She pulled her head back to ask, “tell me William. Were you careful?”
“Yes Siren. We used protection.”
She bit her lower lip. “Good Pet. I don’t have any on me this morning and I really need a good fuck.”
“Puppy not doing it for you?” He replied, with a smug grin on his face.
“Cute. We haven’t had time to engage in any playtime lately, hence this weekend. Plus…” she paused, “I’ve missed you.”
Will groaned in anticipation and inhaled deeply. God he loved the way she smelled.
She continued to stroke him as she continued on. “Lucky for you, William, I wore thigh highs today. No need to fumble with hose.”
“Thank you, Siren. May I touch you.”
“I think you’d better.”
Will leaned down and reached under her skirt to slip his fingers into her easily. “Fuck you’re wet.”
“Mm.” She let him finger her for a few moments before stopping him. “Lick your fingers for me.”
He pulled out his hand and did as he was instructed. Before going to replace them, however, he looked at her, asking for his next move.
“You’re going to push me against this door and fuck me. Hard.” She flicked his upper lip with her tongue and looked into his eyes.
He hesitated. It wasn’t usually this easy.
“It’s early and we need to get back to work,” she replied, seemingly reading his mind. “I need to cum. You need to cum. What do you say?”
He grinned before lifting her and pinning her to the door with his body. Will reached down between them and easily slid himself into her.
She gasped at the welcomed intrusion, smiling almost immediately. He began sliding in and out of her, slowly, but quickly realizing they didn’t really have time to linger. So, in making up for lost time, Will slid a hand between them to rub her clit.
Diane groaned as her head hit the door behind her.
Will pushed into her harder and faster, his thumb working just as hard as his hips.
“Will!” She gasped. “So… good.”
He grinned as he kissed her again, still slamming himself into her.
“More,” she begged.
Will placed his lips to hers and playfully admonished, “shh. Don’t wanna get caught.”
She placed a hand on his cheek as she kissed him again.
“You want this? Hmm?”
“Yeah,” she nodded.
“Tell me. Tell me how bad you’ve missed me.”
“Will. Oh god I’ve missed this. Oh fuck me.”
“Yeah?” He drilled her harder. “More.”
“Your cock belongs to me.”
“Yeah,” he grunted.
“Mine.” They kissed again. “Make me cum.”
He could feel she was close and, so was he.
“Cum for me, please? I need it,” he begged
“Yeah,” she sighed.
Her body hit the door harder and harder as they both got closer and closer to climax.
“Diane,” he groaned.
Her eyes slammed shut as the first wave of pleasure hit her. “Shit!”
Will pushed himself into her and held himself deep, rocking his hips against hers, removing his hand from between them to hold her other hip.
As soon as he felt her pulse from within, he was gone. They’d stopped the role playing mid-fuck but he learned to hold back until she came, regardless of the situation. It was just a good idea.
He grunted as he pushed himself into her harder, sporadically, as shocks hit them both.
She began to relax before he did, one last wave making her shiver.
Will held her against the door for a few moments longer.
“Ready?” She asked before kissing him once more.
He nodded and slowly backed off, letting her down gently. They gave each other a deep, meaningful kiss before parting ways. Will reached into his pocket to hand her the panties she stuffed in earlier. Diane waved him off then walked into an empty stall to clean herself, flushing the evidence of their encounter before walking back and straightening his tie and wiping traces of her lipstick from his mouth.
“Buy me a cup of coffee?”
“I just gave you an orgasm,” he replied. “Now you want coffee.” He winked as he unlocked the door.
“No. I gave you an orgasm. Never forget that. Coffee is just a bonus.”
They walked to the elevator and waited for the car to get them.
“If we’re seen together, no one will think much of it.”
“Except you’re glowing, Diane.”
“It happens when I’m satisfied.”
He grinned. “I know.”
“Let’s set some ground rules.”
Diane sat behind her desk, hands crossed in front of her, with both Will and Cary sitting across from her. It was the end of a slower than usual day so they all had the availability to sit and talk.
“First: As I’ve stated before, I don’t think we’ll need it but the safe word is ‘pineapple’. Understood?”
Cary nodded as Will confirmed, “yes Siren.”
“I’m going to need a verbal confirmation from you, Puppy.”
“Good. Second: My pleasure comes first. Always. Second, as always, no one cums without my say so. Agreed?”
“Now, on to better things. Do you know what a ‘cuckold’ is?”
“Sure. Adultery,” Will answered
“Well, yes. But in our context,” she gestured amongst the three of them. “Do you?”
They both paused.
“Actually I don’t think I do.”
“How about you, Cary?”
He nodded in agreement.
Will stopped and considered where this conversation started. “Wait. What does this have to do with adultery?”
“It’s not adultery, Pet.” She walked over to him and placed a hand on his cheek. “Look it up. ‘Cuckold and Kink’.”
Will took out his phone and typed in her phrasing and hit “Search.”
He clicked the first link and read, his eyes going wide. “Oh,” he looked up at Diane, whose eyebrow was arched. “Me?”
“I haven’t quite decided. Although I’m not certain I could be as cruel as to not finish one of my boys off.” She thought for a moment and replied with a smile, “I guess you could say I’m a softie.”
Cary found a sense of comfort in her last statement, whereas Will was left uneasy, knowing full well what she’s capable of. Still, he tried to remind himself that she’d always taken care of him and she was his Siren for a reason.
“I’d like to meet up Friday evening at my place. Until then, what’s my rule, William?”
He looked down at his feet, “no orgasms.”
“No orgasms,” she repeated almost immediately after him. “That’s right. And you know what comes next.”
Will got to his feet and looked straight ahead, clasping his hands behind his back. Cary looked between Diane and Will before rising, looking forward, and doing the same with his hands.
Diane walked to the two of them and placed her hands on each of their groins, kneading gently. She sighed as she felt them begin to harden for her. “My boys.”
Cary grunted at her touch.
“Yes, Siren.” Will replied before swallowing hard.
“Whose cocks are these?”
Both replied at the same time.
She cooed. “Exactly. Have you two discussed touching of each other?”
The two men whose minds were elsewhere shook their heads “no.”
“That’s fine. Just curious. Besides, I didn’t plan on letting you near one another just yet anyway. And you’re both okay with the proximity to one another while nude, for my benefit, correct? Pet?”
She continued to massage them through their pants as she thanked god she wasn’t a man so that she could get incredibly turned on by watching them squirm without betraying her arousal to either.
Diane released Cary and placed that hand on Will’s chest before leaning in close to his ear and whispering, “would you like to make me cum?” Her hot breath on his neck sent shivers up his spine.
“Ye… yes. Mistress.”
“Mm,” she chuckled quietly, “I’ll bet.”
“And what about you, Puppy? Would you like to see Pet make me cum?”
“Um, no, Siren.”
“No?” She stopped and walked over to him to look him straight in the eye, dumbfounded by his response.
“I’d rather be the one to give you pleasure, Siren,” he answered before she could ask.
“Oh Puppy,” she purred as she placed both hands on his chest and slowly trailed them lower. “That’s not what I asked, you was it?”
“Well thank you, Cary. You’ve just made my decision for me. You will be my cuckold.”
Will sighed in relief as quietly as he could. He could have sworn he’d be her choice as he was the stronger, more experienced sub of her two playthings.
Cary closed his eyes and berated himself, realizing he didn’t answer the question asked and, as a lawyer, he should know better.
Diane placed her hand on his crotch and, looking at Cary, stated, “Will this doesn’t mean you’re off the hook.”
“In fact I’ll need to get a little creative.”
“Yes Siren,” he replied somewhat sadly.
She chuckled and looked over at him. Diane placed a hand on his cheek and asked, “have I ever been cruel to you without cause?”
“Then why would I start now?”
Will thought about all of their experiences together and he realized through everything they’ve been through, everything they’ve done, she’s always been fair and just and has never given him reason to worry. Despite this, every time she spoke of getting creative, his stomach sank.
“Now. As a night cap of sorts, I’ll send you off with a taste.” Diane unzipped her slacks and slid a hand into her panties, moaning half for show, half in pleasure and coating her fingers in her essence then taking them back out again.
“William?” She looked over at him before continuing. “Seeing as you’re the more experienced of the two, you decide. Do you go first or do you get to choose the finger to taste?”
He thought on it for a moment before replying, “finger. I want the middle one.”
Diane laughed as she folded the longer of her two digits to her palm and moved her extended finger to Cary’s lips. “Care for a taste?”
Cary licked her finger clean, sucking greedily which only served to pull memories of his mouth on her. Diane suppressed a groan as she pulled back and walked over to Will, offering her whole hand.
He licked up her palm then gently took her middle finger in his mouth, making love to it with her tongue as he sucked her clean. Will loved the way Diane tasted and did anything he could to get as much of her wetness in his mouth for as long as he could.
She pulled her hand back and took a step back, zipping up her slacks. “Such greedy boys. Save it for Friday night.”
Diane walked back to her desk and sat down to focus on wrapping up for the night. “You can last two days, can’t you?”
Both Will and Cary readjusted themselves, trying not to look at one another and keep their focus on Diane.
She sat back in her chair and took her glasses from her desk, placing them between her lips, toying with them with her tongue to torture her boys even further. “You can touch, but you can’t cum. Just thinking of how hard you’re going to make me cum gets me so turned on.” She whimpered in affectation. “Mm. Both of my boys getting me off is almost too much to stand.”
Diane continued on as she unbuttoned the top two buttons on her blouse. She leaned forward so as to show some cleavage. “Thinking about it gets me wet.”
Will and Cary had already both begun to lean forward in anticipation.
“Now. We’re done here.” She put her glasses on and went back to work. “You can show yourselves out.”
The two men bumped into each other as they turned to walk out of her office.
Diane laughed to herself, pleasantly surprised she could have such an effect on them as she continued pretending she didn’t see their gaffe.
“I don’t know about you but I’m going home to take a cold shower,” Cary started as he walked out of her office.
“I found running helps,” Will offered.
The next morning, Cary found he had awoken with a severe case of blue balls. Will was in only marginally better shape, running an extra two miles on the treadmill.
Both knew that if they could get through today and tomorrow, that tomorrow night would be well worth the wait.
Cary walked into Will’s office around lunch time. “Got a minute?”
“Sure. What’s up?”
He shut the door behind him and took a seat across from Will. “Well, I was wondering if you wanted to talk about the touching thing, with Diane?”
“Oh. Not here. Drinks tonight?”
“Sure. I should wrap up around 6. Does that work for you?”
Will looked at his calendar then back up at Cary. “I think can do 630. Meet me across the street?”
“Sounds good.” Cary rose to leave but stopped himself. “Should I be worried? About what’s going to happen tomorrow night?”
The older of the two chuckled. “No. Diane’s always been fair. She’ll push your limits but she’s always respected boundaries. Just make sure you talk to her before during and after and you should be fine.”
“How are you holding up, by the way?”
Cary turned to look at him as he opened the door to leave. “A little blue?”
Will let out a hearty laugh. “Me too.”
The two of them met for drinks at the bar in the lobby of the hotel across the street.
Cary took a sip of his drink and sat back in his chair. Looking squarely at Will, he started, “so how do you feel about touching?”
“Honestly? I really haven’t given it much thought. I’m not really into men.”
“Makes sense. I think I’d be comfortable with you touching my arm or leg but I’m not really sure about more than that.”
They looked at each other and Cary blushed, slightly.
“Don’t worry about it. It’s good you’re open,” Will encouraged. “And that’s why we’re here, right? To talk about this.” He, too, took a sip from his drink and waited to see what kind of response he’d get.
“Thanks. This is just really new to me.”
“I mean, maybe it’s the booze but I’ve fooled around with men before. In college. It wasn’t awful. I just prefer women.”
“Makes sense. I never did. Well, I mean, I sword fought after games in high school but that was kid stuff.”
The two of them chuckled as they began to feel a bit more at ease with one another.
“How do you feel about touching?”
“I think,” Will started, “ that I’m okay with arms and legs, too.”
They sat in silence for a few moments before Will continued. “What if we had a safe word for each other? Like if we feel like we’re crossing a line while we’re with her?”
“That makes sense. What do you think?”
“What about…” he thought for a moment. “Cinnamon?”
“Keeping in line with the food theme. Cinnamon it is!” Cary raised his glass and toasted Will.
“Now that that’s out of the way, can I ask more about this arrangement?”
“Sure. I’ll let you know if I’m not comfortable with something.”
“So… how long have you been doing this? How’d you get started? Have you always been her ‘Pet’?”
Will laughed. “Off and on for a few years. It’s never been serious so we date others if the situation presents itself.
“It started at a bar, of all places. We were celebrating a big win and fooled around.” He stopped and took a sip of his drink. “Of course, this stays just between us.”
“We went back to my place and one thing led to another and here we are. She took control that night and it just sort of evolved. She’s really blossomed since then. And I like the fact that I can let go and not have to think about things for a while. I trust her implicitly.”
“As far as me ‘always being her Pet,’ that just kind of happened as it evolved.”
“I did top her once though.”
“Really?” His eyes widened at the potential of story time.
“Yes. Once, in public. It was a nice change of pace but I definitely prefer her taking the lead.”
“In public? Really?”
“Yep. But that’s all you’ll get out of me, unfortunately.”
“That’s fair. You think I could…?”
“Not for me to say, “ he interrupted. “That’s a conversation you need to have with her. Just be prepared for the answer, though.”
“What does that mean?”
“It means she may not give you the answer you’re looking for, whatever that may be.”
“Don’t get discouraged. I’d never topped someone before her. Most of what I know came from her. Always look for ways to learn. Diane is a brilliant teacher. Just something I’ve learned.”
“Think we should tell Diane we talked?”
“Absolutely. And about ‘Cinnamon.’”
“Isn’t that our thing?”
“Yes. But we want her as in the loop as much as possible. What if I eek it out and you don’t hear me? One thing about a good top is to always have your sub’s best interests in mind. That way she can relay the message to make sure we’re all taken care of.”
“That does make a lot of sense.”
“I told you, she’s a brilliant teacher. Diane and I have learned a lot from one another. You know she’s got a friend who’s a Domme?”
“Yeah, she told me.”
“Yeah. I haven’t met her but Diane has mentioned her a couple of times.”
“Yeah. Very cool.”
“It is.” Will finished his spirit and set his glass on the table in front of him. “So you think you’re ready for tomorrow night?”
“Yeah, I think so. I’m definitely ready for the release.”
“Ha. Tell me about it. Just be grateful, deep down, she’s got a big heart and would never let us go without. We might have to wait and work for it but she’s always made sure I was taken care of, if need be or if a lesson needed to be taught.”
“That’s good.” The younger man finished his drink and set it on the table. “Wait, what?”
“There have been times I’ve done for her without thinking about her doing for me. You know, like any normal, healthy relationship?”
“Oh. You scared me for a moment.”
“What about the lesson?”
“Well, she decided to see how well I was paying attention and I fell for it. So it was me and my right hand until I worked to fix it.” He took ahold of his glass and sipped what little water had come from the ice and bourbon. Will thought back on that night and remembered just how close to breaking he’d been. “I deserved it.”
“So you played with her and went without. Interesting.”
“Again, if I’d payed better attention to my lover’s needs, yes I used ‘lover’ and not Siren because that’s important but you know that, then I would have caught on and fixed it sooner than I did. That was a hell of a night.”
“Yeah. She’s taught me a lot,” he reflected. “And don’t piss her off. She gets creative when she’s pissed off,” he added with a knowing laugh.
“Sounds like it.”
“I’ve got stories for days. But I’m out of bourbon. Another or are you done?”
“I think I’m done for the night. Gotta be well rested for Friday night.”
“That we do. Let’s get the check.”
Diane left work around three on Friday, telling her assistant she had an appointment to deal with but that she’d be checking email periodically throughout the day and definitely through the weekend. She had a smile on her face all day as she worked.
Will and Cary stopped by her office in the morning talk of their previous evening’s discussions and conclusions, all of which Diane was happy to hear of. She hadn’t had anything in mind wherein the two would come in contact with one another but now that she knew they’d spoken and set limits, it made her happy. Happy to see them getting along, happy to see their willingness to work together for her benefit, happy to get more creative with her evening’s and futures’ plans.
Cary left first, with Will not far behind, both mutually deciding it’d be in their best interests to go home and shower and shave before heading to Diane’s place. They’d learned, each in their own ways, that she wasn’t really a fan of pubic hair. So, Will passed along this bit of wisdom to Cary, who’d always preferred to be somewhat groomed, regardless.
After their discussion on Wednesday night, instead of heading home, Cary decided to get waxed as a sort of surprise for Friday night’s encounter. What he hadn’t counted on, obviously, was the fact that his skin would be irritated for more than 24 hours. Luckily for him, though, by this time, it had been almost 48 so when the irritation had almost completely gone by the end of Friday, he started feeling much better about his decision.
Will went home, showered, shaved, groomed, and stopped at his favorite local liquor store for a new bottle of bourbon. He wasn’t certain which but had at least narrowed his decision down to a brand name. He stopped in the store, giving himself enough time to decide and still get to her apartment to get things started.
Meanwhile, at home, Diane laid out her myriad of toys, new and old, accessories, and changed into her favorite dark purple bustier, lacy black underwear, and covered it with her silk robe. She placed her pair of black heels next to the door for when her company began to arrive. Diane took her time getting ready, looking forward to this evening’s activities with her boys.
She’d never gotten to play with more than one man at a time before so that, on top of the fact that she adored them both, made her a little giddy. Diane considered a shot of something stiff to help take the edge off but she’d always maintained staying completely sober before playtime. There was little room for mistakes and she’d never forgive herself if there was an accident.
Will arrived first, twelve minutes before they were scheduled to start. He got to her door, looked at his watch, and hoped that it wouldn’t be too early to go in.
When the bell rang, she looked at the clock and knew who it’d be. She slipped on her shoes and smiled.
“William. Early as always. Come in.”
“Thanks. I brought a spirit for after. I’ve never had it but read good things.”
“Thank you!” She leaned forward to take the bottle from him and placed a sweet kiss on his cheek. Diane pulled back and looked at him, “tonight is okay with you, right? I can modify plans if it’s not.”
The butterflies in Will’s stomach jumped at the offer. “This is fine. I haven’t gotten to please my Siren in a while, so I’m actually looking forward to it.” He placed a kiss on her cheek then turned to take off his coat, doing his best to shake off any nerves.
She walked into the kitchen to look at the bottle of bourbon and smiled. It happened to be one of her favorite brands.
“I was thinking,” Will started as he entered the kitchen behind her. “I’ve never been in a Devil’s Threesome before. Have you?”
“Hm. I hadn’t thought about that. No, it’ll be a first for me, too.”
Diane opened the bottle of bourbon to smell the spirit.
“I haven’t had this one. Have you?”
“Oh yes.” She popped the stopper and licked the cork, placing it back in the bottle, not realizing what she’d done to Will. “It’s one of my very favorites. Thank you. We’ll have some later.”
“You’re killing me, Diane.”
“Licking the cork. You’re killing me.”
Diane looked down at the bottle and only then had she realized what he was talking about. She grinned and placed a hand on his chest, “sorry about that, Pet. I couldn’t help myself.”
Before he could reply, the doorbell rang.
“Excuse me.” Diane walked to the door and let in the younger of the two men. “Welcome. You can leave your shoes by the door.” She leaned in to give him a kiss on the cheek. “Are you okay with this? We can change things if you’re not,” she reassured him, quietly.
“No, this is going to be great. I’ve been looking forward to it. To you.”
“Perfect. You can go ahead and leave your coat. Will and I were in the kitchen talking. Care to join us?”
He hung up his coat, took off his shoes, and followed her into the kitchen. Will shook his hand then caught sight of the bottle on the counter.
“I’ve read great things about Jefferson’s. I’m not much of a bourbon drinker, though.”
“I remember. There are other spirits for afterwards.”
“No. Our faculties need to be sharp. Sorry if you were counting on getting rid of some of the pre-fun jitters.” She winked and smiled at him.
“Oh, that’s fine. And that makes sense. Guess I’ve still got a lot to learn.”
“All in time, Puppy.” She patted him on the chest.
“Are my boys ready?”
Diane leaned forward and kissed Will, his hands snaking around her hips, fingers gripping the delicate silk, as he kissed her back. Slowly, she pulled away, placing one smaller kiss on his lips before moving to Cary.
“Are you okay with kissing me after I kissed him?”
“In this instance, it’s Diane asking. I don’t want any awkwardness if something like this were to happen again. It’s a boundaries discussion that we should have had before. I’m sorry about that.”
“Oh,” he looked at her slightly relieved. “Yeah, it’s fine Diane.”
“Good.” She leaned in and kissed him, placing her hands on his shoulders and slowly running them down his chest. Cary wasn’t entirely sure what to do with his hands, so they rested gently on her hips.
She stood back and admired both men. “Now. Go to my bedroom and disrobe, placing your clothing on the loveseat. Will, when looking at it, you’ll be on the right side of the bed, Cary, the left. Leave enough room between the two of you for me to sit with my legs crossed. I expect you to be hard and ready with your hands at your sides when I enter. You have three minutes.”
Diane’s eyebrows rose before she whispered. “Go.”
Will walked out first, his hands working his belt. Cary followed close behind, he unzipping his pants.
The two disrobed and, facing opposite directions, stroked themselves to ensure they were hard, as instructed. However, given her tone of voice, her smell, her taste, and every little bit that just transpired, they were ready.
Each took their respective places on the bed, both still fluffing themselves quietly as they listened for the click of her heels.
Not a full minute passed before Cary put his hand on Will’s. “I think I hear her.”
Both stopped and placed their hands at their sides as instructed.
Diane walked in the dimly lit room, her robe around her shoulders, her sash loose around her hips, and leaned against the doorway. “Look at me.”
At first, they were uncertain where their gazes should lie so when she instructed them, they were only too happy to oblige.
“This is my favorite teddy,” she started as she let her robe fall to the floor. Diane walked over to her chest of drawers to look at what she’d laid out beforehand. First, she grabbed her bottle of lube and Will’s plug.
“Knees up, Pet.”
Will complied, moving his feet close to his body, spreading his legs as he did. He knew what was coming and actually sort of looked forward to it. They hadn’t played with it in a while but he never forgot the incredible orgasm he had when he came untouched.
Diane inspected his grooming job and patted him on the thigh. “Nicely done, Pet.” She lubed up his toy and slowly worked it in his ass.
“Oh god,” he groaned.
She smiled as she pumped it within him a few times.
“Thank you, Siren.” Will’s cock throbbed with the need to be touched.
“Puppy? Are you adverse to a toy in your ass?” She asked as she watched what she was doing to Will.
“Good. Because I have a gift for you, too.”
Diane walked back over to her chest of drawers and cut open the packaging of a similar plug, but in maroon. “You’re a Harvard boy, right? I got you one in your school’s color. Knees up.” She moved next to him, on the other side of the bed and lubed up a finger before positioning it at his entrance.
Cary didn’t grimace when her finger slid into him. He grinned, her finger penetrated him easily. She slid in another and massaged his P-spot, making his hips jerk hard.
Diane grinned. “Are you ready for the toy?”
“Yes Mistress,” he panted.
“Ooh. Very good.”
As her finger slid out, Diane stopped, suddenly struck by something. “Puppy? Did you… get waxed?”
“Oh my. How incredibly smooth.” She trailed her hand down over his hips, tugging on his balls gently. “William? You’re to do the same the next time we play. Understood?”
“Yes, Siren,” he bit out, trying to withhold his simmering anger.
“Perfect. Now, take a deep breath and let it out for me, Puppy.”
Cary did as instructed and as soon as he’d finished, Diane slipped the toy into him and slowly fucked him with it. She delighted when his cock twitched and the first drop of precum hit his stomach. He groaned happily.
“Mm.” She cooed as she felt herself getting painfully wet.
“Have you ever cum untouched, Puppy?”
He thought about it, trying to refocus on her question rather than what she was doing to his body. “No. I don’t think so, Mistress.”
“My Pet did. For me.” She looked over at Will. “Do you remember, Pet?”
“Yes, Siren. Quite well.” His cock twitched as he remembered that night.
Diane continued working Cary’s ass. “How does that feel?” She asked quietly, her voice low and smooth.
“So good,” Cary replied, panting, wishing he could touch himself.
“Perfect. Hold it in place.”
Cary whimpered at the loss of movement.
Diane rose and stood at the end of her bed. “My boys,” she admired. “Stroke yourselves slowly. Puppy, tell me why you deserve to fuck me tonight.”
Cary’s hand went to his swollen cock, quickly and gratefully, before sliding up and down his girth, slowly, as instructed. “I’ve been a good Puppy, learning a lot. Mm,” he groaned as he realized how badly he’d needed this. “I want to make you cum over and over. It’s been entirely too long since I’ve been able to do that for you.” His hand squeezed a bit harder as he continued. “And truth be told, Mistress, I’d love to fuck you with my mouth. You taste incredible and I’d be lucky to be given the honor.”
“Close,” Will thought to himself somewhat smugly.
“Very good Puppy,” she verbalized, while screaming “sweet Jesus I wish I could ride that pretty face,” on the inside. “Pet? You’re next.”
“I, too, need to make you cum tonight. I want to get you off with my mouth and my fingers and my cock. Anything.” He paused as the thoughts of making her cum sent jolts of pleasure to his cock. Will’s voice dipped lower, quieter, as he continued on. “This is your body and cock to do with what you please. I’m willing to show your Puppy how it’s done.”
Cary looked over to Will with a confused, “what the fuck?” glance.
Diane laughed, having made up her mind whom she was going to ride. “A little healthy rivalry. I like it.” Will had his own way with his mouth that seemed to work for her.
The younger of the two men turned his head back to look at Diane, brow still somewhat furrowed, but glad the jab wasn’t meant as anything personal. Apparently he really did still have a lot to learn.
She walked to Will’s side of the bed then began to run her crimson nails up his thighs and watched as he stroked himself. Will’s eyes watched her face, almost begging her to look up at him, for that connection he’d missed. Diane pushed his hand to the side and slid her thumbnail along the underside of his cock, slowly enough to elicit a chill from him. She grinned as she watched him shake.
Again, Diane stepped to the end of the bed and beckoned her first toy. “Pet? Come.”
Will rose to walk to her, not entirely certain what she had in mind.
“Stand behind me and press your body against mine.
He did as instructed, groaning as he felt his cock press into her ass. It was almost painful but Diane, somehow seeming to know already, reached back and pulled it up to rest between the two of them.
Cary released himself from his hand and walked over to her, stopping at her side. She took a step to face him, Will’s body still molded against hers, then proceeded.
“On all fours, Puppy.”
Again, Cary did as he was told. Diane reached down and pulled down her panties, pressing her ass into Will even more, pulling a painful groan from him. They fell to the floor before Diane placed her foot on Cary’s back. She pushed him down a little so as to be more comfortable.
“Watch how he fucks me. If I were a cruel Mistress, I’d tell you the only way you’re going to get to taste me this evening is by licking my cum off of his cock. But my guess is you two haven’t discussed that so I’m going to leave it as is.”
“Yes Mistress,” he replied. Cary probably wouldn’t have had much of a problem with sucking her off of Will but like she’d stated, they hadn’t really talked with each other any more than just touching so as far as he thought anyone was concerned, and as much as he really wanted it, cleaning Diane off of Will was off limits.
Diane reached behind her and grasped Will’s hard cock, pumped him twice, then positioned him at her wet entrance. She pushed back on him and sighed once he was fully inside her. “Fuck me Pet.”
Will placed his hands on her hips and began to slide himself within her. She grinned as he moved faster.
Cary panted in frustration at her feet as he watched Will fuck her. He licked at his lips, doing everything in his power not to lunge forward and take her in his mouth. The smell of her arousal alone was enough to make him salivate but watching, so close yet so far, this was torture.
Will moved one of his hands to the front of Diane’s body to begin rubbing her clit. Diane moaned in pleasure, clearly pleased by his initiative.
“Do you know what would please me, Pet?”
“No, my Siren,” Will grunted as he tried to keep up the pace.
She let out a low, cool laugh. “It’d please me to have him on my clit while you slip into me. Would you be adverse to that?”
Diane placed her hand on his and stood straight. “Stop.”
Will froze. He’d never heard her tell him to stop what they were doing before. He’d wondered if something was wrong. It’d have to be to stop mid fuck, right?
“I mean it. He may touch your cock as you slide into me. This conversation should have come before playtime started as I fear either of you may feel guilty about saying no. William?”
He held himself within her, not entirely certain how to respond. Personally, he wasn’t really into men but the idea of getting laid and his dick licked at the same time wasn’t necessarily a turn off. He’d enjoyed it in the past with two girls. And from what he’d heard, Cary was quite talented with his mouth. Besides, Cary wouldn’t do it on purpose, right? Then there was the prospect of being able to do this for Diane, for his Siren that truly turned him on.
“I… I think it’s okay.”
“Really?” Cary piped up. “I’ll try to stay in place. But I can get carried away.”
Diane’s heart swelled. She knew they were doing this for her. “If at any point this becomes uncomfortable I need my boys to promise safe words will be spoken.”
“Good.” Diane straightened, removing her heeled foot from Cary’s back. Will slipped out of her before she walked over to the edge of the bed. She leaned forward and placed her hands on the bed in front of her.
“It’s time to make me cum,” she ordered as she widened her stance.
Will walked over to her and aligned himself behind her, waiting for Cary to take his place.
Cary crawled over to her, after all, he was a quick study, and placed his hands on her thighs as he sat on his calves.
“Pet, you are to count to thirty before you may slide into me. Puppy, proceed.”
He leaned forward and tried to count to thirty so as to ensure he got a little teasing in before he had to stay in place. Cary licked up her slit and back down before quickly flicking her clit with the tip of his tongue.
Will placed his hand on her hips and smiled, knowing he was seconds closer to getting to feel her again. With his free hand, he slid it slowly down her spine as he made his way to her other hip.
Diane shivered. Her Domme façade was slowly slipping but with the promise of this much pleasure and this unique experience, she really could not have cared less.
“27… 28… 29… 30.” That served as the only warning before Will impaled himself in her. He pushed into her hard, her body moving forward with force. “Fuck you’re wet, Diane.”
She nodded. Cary latched on to her clit sucking harder, his hands digging into her thighs. She’d probably have bruises in the shapes of fingers there in the morning but no one would see.
Diane’s body began to shake as her first orgasm slammed into her body. Will reached forward and wrapped a hand around her lower abdomen, holding her as she came on his cock.
Cary released her from his mouth to give her a brief respite, and let his tongue explore. It ventured over her lips and, eventually down to where she and Will were joined.
Will began pumping himself again and closed his eyes as he felt her body begin come down from this climax.
Cary pressed his tongue harder, massaging Will’s cock through her thin skin. He groaned in pleasure. This felt incredible and he could not have cared less who was giving him his pleasure.
“Keep going,” Will begged.
Diane pushed back into him while Cary let his tongue trail further down on to Will’s cock and over his balls.
“Wait,” Will groaned. “Cinnamon.”
Cary pulled back almost immediately and moved his tongue back to Diane’s clit and began to refocus his oral assault on her.
Diane groaned in pleasure when he did, grateful his attention had returned to her. She moved a hand down to his head and held him in place.
Will resumed his pace within her. It didn’t seem to dawn on him that his balls, that were just being serviced by Cary, were now bouncing off of the younger man’s cheek.
All energies refocused on Diane. Her fingers flexed and tugged at Cary’s hair as she felt her next orgasm begin to build. She pushed back and down, finding the perfect rhythm.
“Ahh,” she groaned. “I’m gonna cum.”
“Come on,” Will grunted.
Cary sucked on her clit harder as his way of begging her to cum for him.
Her fingers tugged hard as she came again, this time her body pitching forward on to the bed. Cary reached up and spanked her clit as she was now out of reach of his talented mouth.
Diane’s body jerked. “Oh god,” she screamed.
Moments later she pushed herself back up and stood, her body fully pressed against Will’s. “Cary…” she panted. “Cary. Stand up here with me?”
Cary rose and stood in front of her, not sure what she needed but he knew he’d give it to her.
Diane reached forward and pulled him to her. She reached down and slowly stroked him, kissing him greedily.
Will moved his hand from her tummy to her hip then took a step back to slowly start fucking her again.
She whimpered into Cary’s mouth as her hand moved faster, gripped him tighter. Diane released him from her mouth and asked, against his full lips, “are you ready to cum for me?”
“Lay on the bed so I can suck on you, head on the pillow.”
He did as he was told and positioned himself on the edge of the bed.
Diane reached back to thread her fingers through Will’s hair. “And you? Are you ready to cum for me?”
He grinned. “Only if you’re finished with me.”
“I’m never finished with you.”
Will kissed her shoulder as his hand slowly moved up and down her side.
She giggled. “I mean for now. I don’t know how much more I can give.”
Both men smiled at this fact, knowing they were responsible for her pleasure, even their playtime had shifted from Domme/sub, to that of a Devil’s Threesome.
“We can play again later,” she promised. “It’s time.”
She leaned forward and placed one hand on Cary’s balls and the other on his cock. Her tongue swirled around the head as she took more of him into her mouth. Diane pushed back on Will as her focus shifted from her pleasure to theirs.
Cary placed his hand on the back of her shoulder instead of where he usually placed his hand when he got head but was by no means complaining. He knew it wouldn’t take much before Diane got him off. It’d been a few days and she really was incredible with her mouth.
Diane clenched her PC muscles as she continued to push back on Will who, in turn, gripped her hips hard enough to leave his own set of bruises. It wouldn’t take much for him, either. He’d been inside her for a while and knowing she was satiated, he was ready.
She sucked Cary harder and deep throated him, which only made his hips buck forward. As soon as she placed her thumb on the toy still dutifully held in place, and pushed Cary growled, “oh fuck!” His fingers dug into her back as the first wave of an intense climax hit him.
Diane pulled up just long enough to suck in a quick breath before deep throating him once more. She swallowed everything he had to give.
Will stilled within her, half because he knew it’d be cruel to continue, but also because, selfishly, he wanted to ensure the same attention was paid to his orgasm.
She wiggled the toy a bit as her tongue continued her assault on him.
Cary’s hips bucked once more as Diane slowly pulled off of him, her fist replacing her mouth. She gasped for air as her eyes watered. Diane cleaned him off and let Cary’s cock fall to his stomach.
Diane rested her forehead on his abdomen as she reached behind her to focus her attention on Will. “Your turn,” she panted.
Will slid himself within her at a quickening pace, she tugged at his balls each time he closed in. “Cum for me, Will.”
As his name slipped from her lips, Will slammed himself into her. She contracted her internal muscles and Will came. She massaged him with both her hands and from the inside. He groaned as his climax slowed to a halt.
“Oh my god.”
Diane rose to press her back against his body, both panting. She grabbed his hand and placed it on her clit. “I’m almost there,” she gasped. “Please?”
Will moved his free hand over her bodice, down to her clit, as he tried to refocus his attention. He tried to stay as hard as he could for her but god only knew how long it’d last. He was spent.
His hand moved over her clit faster.
Cary’s eyes flew open at the sound of her pleasure. “Cum for me Diane. Cum for us.”
“Yes, cum for us,” Will suggested.
Diane pitched forward as Will’s hand moved faster, pulling a final orgasm from her. She came hard, quickly pushing Will out of her. Her body shook as Will tried to hold on to her.
A final twitch signaled she really did have no more to give. Cary scooted over to allow for both of them to get into the bed, too, which they did.
Diane laid in the middle of them, on her back, her hands resting on each of their chests.
The three of them lay there, quietly for several minutes, both men neither really wanting to be the first to break the spell.
“Wow,” Diane stated. “That was… wow.”
Both Will and Cary laughed.
Diane’s eyes opened. “I’m sorry I didn’t stay in the right mindset. I’ve just never had two men to play with before. I hope you’re not disappointed.” Her head moved side to side to check for displeasure on their faces.
“That was amazing.”
“Are you kidding?”
She smiled. “I’m glad. Anyone up for a drink? I think there’s something in the kitchen calling my name. And before you ask, Cary, I’ve a six pack in the fridge so you wouldn’t be left out.”
He smiled, too. “Thanks. You’re such a caring Mistress.”
“You bet your ass I am. And don’t think I won’t forget that when we’re one on one again.”
“I count on it.” Cary leaned over and placed a kiss on her shoulder before rolling off the bed to grab his pants.
Diane followed suit and looked over to Will to ask if he was ready to join but found him asleep. She chuckled as she reached for her panties and then for her robe. She put both on and walked behind Cary to the kitchen.
“You can take that out, you know,” she told him, pointing to the toy still held in place.
“Thank you. But if it’s all the same, I’d like to keep it in place for a while longer.”
Diane got two glasses, sure Will would join them shortly, then took a bottle from her fridge. She popped the top and handed it to Cary then reached for her bottle of bourbon. Even though it was her norm, she went without ice; this spirit was too good to dilute. And given how incredible she was feeling, there was no need to ruin that, too. Diane poured two healthy fingers of bourbon and took her glass in hand. As she was about to toast with Cary, Will walked in.
“Starting without me?”
“Hello Sleeping Beauty,” Diane teased. She handed him her glass then poured one for herself. Again, she hoisted the glass she was holding.
“To us. And to one hell of a night.”
“To one hell of a night,” they echoed.