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English
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Published:
2025-03-28
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1/1
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Linda and Teddy

Summary:

Since moving in with his favorite couple and their kids, Teddy has had sex plenty of times with Bob and Linda together. This is his first time having sex with just Linda, and he's a little nervous.

Notes:

This story contains brief references to Teddy being verbally abused in his previous relationship. There are a couple points where I reference Teddy's ex-wife shaming his body in a transphobic way. It's not gratuitous and can easily be skimmed over. Still, consider that a content warning if you decide to read this one.

Work Text:

Since Teddy had moved in with his favorite family, he hadn’t had very much alone time, which was just how he liked it. All the years he’d spent living alone in his old apartment after he and Denise split up had given him enough loneliness for a lifetime. Still, an afternoon to himself here and there at this point in his life was just fine, especially with the inundation of love and, well, noise he’d had from his partners and their kids for the past months he’d spent living with them.

Like today. The kids were at school, and Bob and Linda were downstairs in the restaurant for another few hours.

Teddy sank deeper into the couch, still smelling like sweat from the half-day of work he’d returned home from a little while ago. He wasn’t hungry yet, having eaten the lunch Bob had packed for him that morning, so instead of making his way downstairs for an afternoon burger he’d decided he was okay waiting to eat until dinner.

Teddy pulled his phone out, idly flipping his thumb through his various apps. Without really thinking about it, he opened up a file with backups of some of his favorite… videos that he’d downloaded over the years. Oops.

He looked at the time again. It would be another hour and a half, at least, before the kids were home from school, and honestly they usually stopped by the restaurant before they came upstairs anyway. And Bob and Linda were probably hard at work, not planning on coming up until their workday was over.

It wasn’t as if Teddy wasn’t having enough sex or anything. Sharing a bed with Bob and Linda every night, he’d had more sex these past few months than he’d had in his whole life. But that didn’t mean he didn’t still like paying attention to himself too.

His thumb moved over the folder of videos, scrolling for a bit, before finally he settled on a familiar thumbnail of two women standing near a bale of hay in an old barn. One of them, the older one, had on overalls and a hat, thick glasses perched on her nose. The younger one had pigtails and a tied-up shirt with denim shorts. They each had tattoos that made them look a little more city-like than the characters they were portraying, but Teddy liked that in a way, being reminded it was actors, real people, who made this stuff.

He clicked on the video, and it began to play. The plot was simple, like the best porn plots were. The woman in overalls had caught the woman in pigtails masturbating in the barn when she should have been doing her work. Apparently this was not the first time this had happened, so the woman in overalls decided she would no longer be lenient. Soon, her friend found herself bent over the hay bale being whipped with a thick leather strap. The older woman said she didn’t like having to punish someone this way, but soon a gleam took over her bespectacled eyes that made it obvious that wasn’t the case. After a few minutes of hard whipping with the strap, her fingers found her way between her friend’s legs, working to finish the activity that had gotten her friend in trouble in the first place.

The whole video was only about ten minutes long, but it usually did the trick. Still, as Teddy’s hand worked its way into his pants and started to rub, he found something strange happening. Where he was usually able to immerse himself in whatever—or whoever—he was watching when he did this, he found himself unable to right now. This time he was thinking more about Bob and Linda than the women in the video. Bob’s belt. Linda with her hair in pigtails. Bob’s stern voice and Linda’s rapid breathing.

Teddy grunted, wet enough now that he was able to slip two fingers inside himself. If images of Bob and Linda invading his conscious when he was watching porn was what was going to get him off, then so be it.

The video was coming to an end, and Teddy nearly was too, when he heard the knob turn on the door to the apartment, downstairs.

“Oh, no!” He yanked his hand out of his pants. His hand that had a very distinct smell and stickiness between two fingers. “Uh—”

Having to decide between buttoning his pants back up and quickly muting the video, he went for muting the video. Unfortunately, he pressed the wrong button and the volume shot way up instead of down, wet sounds and loud gasping practically echoing against the walls of the apartment.

“Ahhh!” Teddy exclaimed just as Linda was coming up the stairs.

His fingers scrambled across his phone, getting some of that stickiness on the screen while he was at it. He finally managed to silence the video, but not before Linda had made her way to the couch, leaning over Teddy’s shoulder and peering at the scene playing silently on the old, cracked screen.

“Whatcha watching there, Teddy?” she asked, a curious look in her eyes.

“Oh, you know—” Teddy gestured vaguely and paused the video, accidentally stilling it on a very conspicuous close-up of two fingers inserted inside a pink, hairy vulva. “Shoot.”

“Woah,” Linda said, leaning in further, a faint coffee smell on her breath.

Teddy winced, thinking of the time Denise had found some of his magazines in their garage and called him disgusting.

But all Linda said, in a breathy tone that sounded almost impressed, was, “She can really take it, huh?”

Teddy chuckled nervously. “Yeah.”

“What website is this?” Linda asked.

“Oh, uh, I have this one,” Teddy said. “I bought it and downloaded it, I mean. I don’t really remember from where.”

He winced again, worried it was embarrassing and pathetic to buy porn when there was so much free stuff out there. And more embarrassing to watch it when when he had two people to have sex with in real life now.

But again, Linda surprised him. She was always surprising him. It was one of his favorite things about her.

“That’s cool,” she said. “Knowing what you like enough to, you know, buy it.”

“I—I guess,” Teddy said, closing out of the video and looking up at Linda sheepishly.

“Oh!” Linda exclaimed suddenly, her voice loud enough that Teddy jumped a little. “Were you not finished? Am I being rude?”

“No,” Teddy said in a rush. “I mean, you’re not being rude. I’m the one jacking off on your couch.”

“Our couch,” Linda said emphatically as she stood up straight and looked at him. “Aw, our couch.”

The two of them looked at each other, and Teddy was sure that, despite the awkwardness of the situation, his own face mirrored the sappy expression currently on Linda’s. It really was nice, being a part of a family, even if family sometimes walked in at awkward times.

“You know,” Linda said slyly after about a minute of amiable silence, “if you weren’t done yet when I came up the stairs, I could help you out a little bit. I probably have about twenty minutes of break before I need to go back. I actually came up just to have a snack, but I can get a little distracted.”

Some of the flashes in Teddy’s mind he’d had of Bob and Linda returned, and he felt himself twitch, wanting. Then, that old sense of nervousness, of what Denise might say to him if she was here, rose in his stomach again.

“Geez, Linda, I don’t know—”

Linda tilted her head, her lips pursing. “You don’t want to? I mean, that’s okay. You just usually want to, that’s all. But if you don’t, I’ll—”

“I do want to,” Teddy hurried to say, worried he’d offended her. “Trust me. It’s just—well, it’s still light out. And we usually do it in the dark, like after the kids are asleep. Plus the two of us have never, you know, without Bob around and usually it’s mostly Bob doing stuff to the two of us. So I just wasn’t sure if you’d like—”

“Aw, Teddy, are you shy?” Linda asked, sitting next to him on the couch and putting her hand on his thigh. “Because you don’t need to be, even if it is pretty cute. Anyway, the only reason we usually do it after the kids are asleep is because that’s when we have time. Maybe I want to look at you in the light. And I love it when it’s the two of us and Bobby, but maybe it sounds kind of nice to have you all to myself. You two have done plenty of stuff on your own, you know. And Bobby and me too, I mean obviously. So I want you and me to have some… special alone time if you want it too.”

Teddy wasn’t used to being wanted. So often these days, he had to remind himself, with varying degrees of force, that Bob and Linda did both want him. Those old voices in his head were so hard to kill.

“Okay,” he said. “I’m, uh, kind of sweaty from work though. I was replacing a part on somebody’s sink in an apartment with no fan or air conditioning or anything, and I—”

“Yeah?” Linda interrupted, tilting her head and looking intrigued.

“Yeah.”

“I don’t know if I can just take your word for it. Show me how sweaty you are.” Linda scooted even closer than she already was, so her body was between Teddy’s ankles where he still sat, sideways on the old couch.

“Oh, uh—” Somehow, Teddy had thought they might go to the bedroom at least, but Linda didn’t look like she wanted to take the time for that. So, Teddy’s shaking hands found his waistband and he tugged his pants, then his underwear, off and tossed them in a heap on the floor. “Here. I’m, ah, this sweaty.”

He held his breath, waiting for Linda to look grossed out or something. When Teddy had first told Denise he was thinking about going on testosterone, the first thing she’d told him was how disgusting testosterone would make “it” look, when it grew. The second thing she’d told him was that he would shrivel up all dry and ugly inside, and the dry part had been true at first, although that wasn’t anything the topical cream his doctor prescribed couldn’t fix. Still, those words stayed with Teddy—he knew a lot of women felt the same way Denise did about guys like him.

And even aside from all that, Teddy knew he wasn’t exactly conventionally attractive because of how heavy he was, all the extra skin around the part Linda would need to get to.

And God, Linda was so hot compared to him.

Linda bit her lip. “It looks like some of that isn’t sweat,” she said, moving her finger in close and tracing a line between Teddy’s legs.

With how worked up Teddy already was from the video he’d been watching and the thoughts he’d been having earlier, all it took was Linda’s light touch to make him shiver. “Oh, geez, Lin. That feels good.”

“Yeah?” Linda traced another line, this time pressing in with her finger a little bit harder. “You want me to do what was happening in your little video, Teddy?”

“Yes,” Teddy said, spreading his legs wider. “Please.”

“Ooh, somebody’s eager,” Linda laughed.

With that, she moved her index finger inside of Teddy, pressing it in deep before swirling it in a little circle.

“Ahh,” Teddy breathed.

Linda, he noticed then, looked a little nervous too, and he wondered if this was her first time doing this to anyone with similar parts to what she had.

She looked at him, looking at her. “Is that good?” she asked.

Somehow, the fact that Linda seemed a little insecure helped Teddy feel more comfortable.

“Yeah,” he said. “You could even put in another finger if you want. You won’t hurt me.”

Linda grinned. “You don’t have to tell me twice.”

With that, she pulled out her index finger and inserted it again, this time with her middle finger added into the mix as well. With her thumb, she began to circle Teddy’s little dick, adding just the right amount of pressure and not seeming like she thought Teddy was gross at all. The look in her eyes as she gazed down at Teddy was almost one of hunger.

Teddy groaned and tilted his head back, staring at the slightly stained ceiling above them. Linda breathed a happy sigh and Teddy closed his eyes, content to let her do her thing.

And damn, her thing was good. About half of Teddy wanted this to go on forever, while the other half of him was just desperate to cum already. Seeming to pick up on that, Linda took her fingers out and pressed them in harder and deeper than ever, adding her ring finger—not on the hand with her wedding ring on it, thankfully.

Teddy gasped, his breath shaking and his legs starting to shake too. Linda continued to rub her thumb, gently, gently, then with increased pressure.

“Mmph,” Teddy whimpered.

“Gorgeous,” Linda murmured, and Teddy didn’t last long after that.

Within minutes, he was coming apart in Linda’s hand, soaking her fingers and practically convulsing against her as he rode the wave of intense euphoria she’d just given him.

As boisterous as the two of them could get, especially when they were together, they were quiet for a few minutes after that. Slowly, Linda withdrew her fingers from Teddy, leaving a sweet ache where they’d been before. Teddy opened his eyes and slowly raised his head to look at her. She was about as sweaty as he was now, which made sense. She’d really worked on him.

“I should probably get back downstairs before Bobby starts wondering where I am,” Linda said. “And wash my hands first, I guess. You can come down and visit us, or you can take a nap. You look tired. And I guess I’m to thank for that—hah!”

“Oh, man,” Teddy said, a realization dawning on him. When Linda looked worried, he explained, “You didn’t get to have your snack.”

“What are you talking about? I’ve got a snack right here.” Linda put her fingers in her mouth, sucked and then took them out. “Salty. I’ll probably grab some crackers before I had down too. I’ve got enough time for that. And put your pants back on. We should probably flip the couch cushions over. The kids’ll be home soon.”

The shift back into mom mode made Teddy smile, and he obediently moved to grab his pants and underwear from the floor as Linda went into the kitchen to wash her hands and probably her forearms too, and grab her crackers. As Teddy, dressed again, made his way to the bathroom, the ache between his legs making way for a strong urge to go, he had a huge grin on his face, practically unable to believe that this was his life now. But it was. And it was, well, as Linda had said. Gorgeous.