Two weeks ago Sam asked you if you would try this, Dean said he was for it if you were, and to be honest it sounded hot. You were a little nervous when you went shopping but the harness fit you like a glove, and well you always did like shopping for lingerie.
You guys were off a case and nothing on the horizon so now was as good a time as any. So you tapped Sam and led him down to get ready.
“Y/n stay, I....I’m going to need help.” Sam mumbled.
“Ok” you said calmly and closed the door behind you.
You opened the bag and pulled all the tissue paper out. Sam hadn't seen what you bought him yet, you went alone; but you had a hard time picking a color imagining each piece on him that was until you saw the black and cream lace.
Pulling the pieces out you watch Sam's face, the warring emotions embarrassment and excitement.
“Ok, strip, can’t help you get dressed in your new pretties if your still dressed” you said excitedly.
Sam started pulling layers off leaving them in a heap near the closet door til he was naked. You motioned him toward you, and picked up the black lace panties, they had a cream bow in the front and cream satin panels on each side. You knelt down in front of Sam and let you put the panties on him, you slid them up the miles of tanned legs over his hips, the material straining to cover his half hard cock. You stood picking up the black lace camisole, it has cream straps and cream accent lace down both sides. You helped Sam pull it down over his head, smoothing the fabric over his toned abs. There was more, cream thigh high stockings and some black heels. Kneeling back down in front of Sam he lifts one foot as you start unrolling the stocking up his leg, all the way to mid thigh where they end with a black lace band, repeating on the other side you then grab the heels, sliding each one on his feet in turn.
You stand taking it all in. Sam is gorgeous tanned, wrapped in lace height accentuated by thigh highs and 4 inch heels making him tower over you even more at 6’8”. You lead him out of “his room” it's more of a study since the three of you started sleeping together, but Dean is waiting in your room for you to bring Sam in. Holding his hand and walking ahead of him you head 4 rooms down and open the door, Dean is laying on the bed in just a pair of tight black boxer briefs and looks up as you come in keeping Sam just out of sight.
“Is he ready?” Dean asks eyes wide.
“He is, are you? Because I've seen him, I got to help dress him and wow.” you say filled with awe at the gorgeous man behind you.
Dean nods and you pull Sam in the room. You can hear that Dean stopped breathing, he’s taking in everything. You know what picture Sam makes and its stunning.
“wow, I mean Sammy damn, baby boy, you look amazing” Dean announces and Sam beams.
“Thank you De, but y/n picked it out and dressed me, I couldn't have done it alone” Sam responds quietly.
“Speaking of y/n, you are wearing too many clothes.” Dean points out.
Now is the time that you were really nervous about, you bought coordinating lingerie for yourself, same colors different items. You pulled your top over your head to reveal a cream push-up bra covered in black lace, then pulled your yoga pants off, revealing a pair of cream satin panties, with black lace overlay and see through black lace back. You dropped your clothes in a pile next to you. And looked up, sure that you had blown it because both boys were silent.
Dean's mouth is hanging open, and Sam looks like he can’t believe what he's seeing.
“I, I'm sorry I shouldn't have, I'll just go. We can do this another time. You don't need me.” you stammer bending to pick up your clothes.
Sam reaches toward you, “ Y/n, wait, you look amazing, can, can I touch you”
You nod, Sam reaches out to stroke the lace on your bra down to your panties. Then cups a hand around your hip and pulls you towards him. Leaning down to capture your mouth in a kiss. You stretch up on your toes so he doesn’t have to bend so far deepening the kiss, when you hear a camera shutter click. Both you and Sam turn to look, and the camera clicks again.
“Guys you look so hot together” Dean explains.
“Wanna get this show on the road Sammy?” you ask.
“Oh yea, baby girl, so ready, De move your ass” Sam says excitedly.
Dean gets up and stands behind you while you both watch Sam climb on the bed.
“De, will you help me?” you ask.
Dean nods and opens the drawer on the nightstand, pulling out the lube, dildo and harness.
“You going to leave the underwear on or take them off?” Dean and asks you.
“What do you think, is it going to be hard for you if I leave them on? You ask, needing Dean's opinion.
“Take ‘em off, y/n” Sam says from his place on the bed. Dean grunts in agreement.
You slip your panties off, and Drawn walks over with the harness and helps you step in and buckles and cinches it up, the straps between your legs holding you open and framing your ass. You watch Sam's eyes dilate as you slide the 7” dildo into place and lock it in.
“You still on board?” you check in.
“Oh yea, can hardly wait for you to be in me” Sam all but moans.
Before you climb on the bed you pull Sam's heels off and drop them next to the bed. Then you tap his hip to get him to turn over, shoving a pillow under his hips.
“Wait, y/n before you get on the bed, Sammy suck her dick” Dean says.
You step up near Sam's head and take hold of your cock and slide it into Sam's mouth; watching him work around it you hear the shutter click. You grab Sam's hair in one hand keeping it out of his face and leaning back as you start to fuck his face, you hear the shutter click in rapid succession, then a groan. You look up and Dean is standing a few feet away eyes blown, flush down his chest. You pull out of Sam's mouth with a slick pop and climb up on the bed between his stocking clad thighs.
Once you're settled you slide his panties down just under the curve of his ass, still covering his hard cock. You set the lube next to your calf and then grab both globes of Sam's ass you spread him to get a good look, and before either he or Dean can guess what your going to do you lean down and lick a wet stripe over Sam's hole, causing him to moan and Dean to gasp. You wink at Dean and get a better grip on Sam and go to work, licking the flat of your tongue over his hole until you felt him relax then started probing in, loosening him up and getting him ready.
You'd been working a way at him when Sam started thrusting back on your tongue and moaning like a pornstar. You hear a click, followed by another closer than another further away. Dean's apparently going to take pictures the whole time. You grab the lube and slick your fingers and start with one working it in next to your tongue, when he starts to loosen enough for you to thrust in and out easy you add a second and twist and scissor them, opening him up to take a third. Then you hook your fingers and pull at his rim making sure you have him all stretched out. Hitting his prostate every now and then to keep him squirming in pleasure, Sam's cock is soaking his panties with precome, and rocking back into your fingers you remove them causing Sam to whine and slick your cock.
He stops whining as you line up, sliding your knees under his hips and sliding in, in one smooth thrust. Burying your cock in Sam, your hips flush with his ass. You pause giving Sam a moment to adjust, when you feel his hips circle you pull back and thrust back in.
“Right there, y/n” Sam moans.
You keep your angle and thrust in to Sam with a steady but hard thrust. Your hands on his hips pulling him back to you as you thrust forward.
“You going to make him come, baby girl? You think he can come on your cock?” Dean taunts.
“He's going to come on my cock or not at all” you growl back. Causing Sam to moan.
You thrust harder, and faster working Sam up, making sure to hit his prostate every thrust in.
“Please, y/n, please let me come, need to come” Sam begs.
“You gonna come on my cock Sammy, just on my cock, gonna ruin those pretty panties I bought you” you answer.
“If you say, yes wanna ruin my panties and come on your cock” Sam pants.
“Then come” you demand. Sam comes all his muscles locking up and flooding his panties with come, you thrust steady working him through his orgasm. You stop, and give Sam a moment to catch his breath before you pull out.
You pull Sam's panties down his legs to his knees then help him turn over, and pull the pillow from under his hips. You remove the soiled panties and lean down to lick the come off his stomach and softening cock, gently. You can hear the shutter click, so you turn to face dean while you finish cleaning off Sam and hear the shutter click a few more times. Once Sam is cleaned up you lean over him and kiss your way up to his mouth, both of you getting carried away in the kiss, not paying attention to Dean.
“Baby girl, you are so wet, it's running down your thighs. Do you want to be taken care of now?” Dean asks running a hand over your hip.
“Please De, will you fuck me?” you beg.
“Aw, all you had to do was ask nicely” Dean responded.
You sat up from Sam and unhooked the dildo from the front of the harness and set it on the nightstand. You moved Sam's legs so you were straddling his hips, and Dean moved in behind you, pressing you forward so your chest was pressed against Sam's.
Dean lined up and slid in, burying himself in you. Your moan half pain half pleasure, was swallowed by Sam who started kissing you again and touching wherever he can reach. Dean sets up an almost brutal pace, thrusting in and bottoming out against your cervix on every thrust. Giving you the best kind of pleasure pain. You feel your orgasm building, and Dean keeps thrusting hard and steady as you tip over the edge, moaning into Sam's mouth.
You can feel Sam hardening again against your stomach, and you keep coming spasming over and over on Dean's cock, causing him to come with a surprised grunt, filling you with his come. Your leaning on Sam's chest as Dean pulls out and watches his come start to drop out of you, pushing it back in with his fingers.
Sam rolls his hips to slide his hard cock against your wet slit. You sit up and reach behind you to slide Sam's cock into you, through Dean's mess. Sam groans as you stink down and he bottoms out.
“That's so hot, you gonna fuck my come into her?” Dean asks Sam.
“Oh yea De, gonna make her an even sloppier mess” Sam groans back. Thrusting up into you.
Dean is captivated watching Sam fuck up into you, he reaches out and slides a finger into you next to Sam's cock. Causing you both to moan and grind together. So he adds a second and as you stretch a third, and fucks you with his fingers next to Sam; you toss your head back and moan more. Both Sam and Dean have to clamp a hand to the base of their cocks to stop them from coming.
Dean slicks his cock with a bit of lube, and pushes in next to Sam. All three of you moan, you from the stretch and the boys from the tight fit. Dean bottoms out next to Sam, both of them grinding their cocks into you, causing you to spasm with pleasure pain.
“You're so tight, I'm not going to last” moans Dean.
“De, you feel good, in her with me, need to come” begs Sam.
They both start to thrust into you, steady but not hard. Causing you to groan in frustration, “not going to break, fuck me like you mean it”.
Sam and Dean pick up their pace, both entering you at the same time and bottoming out before they pull back, they get about five hard thrusts in before you start coming, and squeezing them, one orgasm after another as they fuck you hard and fast chasing their own end.
“y/n so good. I'm gonna come” growls Dean, as he starts pumping you full of come again, the feeling of Dean's come triggers Sam to start to fill you up. Both thrusting slowly through the aftershocks.
Sam goes to pull out but Dean stops him and grabs his phone and hits record.
“Y/n let us in her at the same time,” he starts to pull out and so does Sam, “Look at all that come, she took three loads” Dean says with a bit of awe in his voice, recording himself pushing the come back in with his fingers, til you tremble with over sensitivity and turning the phone off. When Dean goes to get some water, you help Sam remove his camisole, and roll down his stockings, then he helps unhook your bra and harness.
You lie tangled together, paging through the pictures on Dean's phone until he comes back. You all drink some water and cuddle together to sleep. As you drift off you hear Sam whisper, “thank you for that, I love you”