Izzy here, with my fanfic, “Branching Out,” a Fitzsimmons pegging fig. Adult-rated, obviously. Marvel owns them.

Branching Out

By Izzy

Leo Fitz was starting to get really good at sex. Or at least, he was getting really good at sex with Jemma Simmons, and it wasn’t like he was interested in engaging in any other kind of sex.

He’d never had that much sex in his life, mostly because just about every time he’d tried it, he gotten so swamped with anxieties about what the person he was trying to do it with thought about him, and how they might react to him, and if he could give them what they wanted, that it had been kind of hard to enjoy it. He’d watched Jemma sleep around, and in the early years, before had it occurred to him to be jealous, he’d mainly wondered how she managed it without ever worrying about those things.

The first minute or so in Bucharest, he had managed to not be plagued by such thoughts. But then had come the moment he’d found himself staring at Jemma’s newly bared chest, there’d been several thoughts floating through his mind about what he should do next, but something in his head had been afraid to grab a course of action and take it, when he hadn’t known which course of action she wanted him to take or what would happen if he took the wrong one.

He’d been frozen with terror for a very long twenty seconds, before she’d realized what was going on. Then she’d said to him very gently, “It’s all right, Fitz. We’re experimenting here; we can’t expect everything to go perfectly. Just put your hands on my breasts, see if you like it, because I think I will.”

She’d kept up the instructing for a while, so things had gone better after that. Instructions he could do.

He thought his developing cunnilingus-on-Jemma skills were the thing he was proudest of. Especially since it was now five minutes since he’d managed to put Jemma in a full-out post-orgasmic daze and she was still in it, still clinging loosely to him the way she’d done during the ten seconds after she’d come it had taken to get him off with her hands, like he was a teddy bear. They ought to clean up and go to sleep, but it was relatively early in the evening.

Also, when she finally came out of it, Jemma looked at him in that way she got sometimes, so he asked, “Want to talk about something?”

“Well,” she said, “I’d give you some praise, but you have to promise me you won’t get too embarrassed.”

“Can’t promise that, sorry.” He tended to feel uncomfortably squirmy inside when she praised him during sex, even when they were in the middle of vaginal intercourse and he ought to be too distracted for embarrassment. Being praised when he wasn’t doing anything but laying there would definitely be too much. Besides, he could tell there was something else she wanted to talk about.

Sure enough, she then said, “Actually, there is something else I’d been meaning to talk to you about. Have you ever been penetrated? Anally, I mean.”

“Twice,” Fitz said, confused. “I’ve, uh, never penetrated anyone else anally, though.” He hoped she didn’t want to be his first there. He didn’t see the point in that anyway; she had a perfectly well-functioning vagina.

But she was still grinning, asking, “And did you like it?”

“Well, yeah. Kind of.” The act itself had been good; he had a prostrate that responded very well to stimulation. But all the same, even when he at least had been spared the need to know what to do, it had been a bit much, to be so overwhelmed and vulnerable to men he’d known, and on one of those occasions worked with, but had never been at all close with. The worst part had been the moments just afterwards, where he’d felt sore and used and judged for every action he’d taken and reaction he’d had.

He thought she’d guessed as much, when she said, “If it was me doing it, then?”

“That would be better,” said Fitz without hesitation, because it absolutely would be. “But, uh…you, uh, don’t have…”

“Fitz!” She was laughing, though kindly. “Fitz, you are not telling me you’ve never heard of a strap-on!”

Fitz had, in fact, possessed vague knowledge that such objects existed, but, “I, uh, don’t know that much about them.”

“Maybe you should see one, then,” she said, and scooted over to the nightstand on the bed, and opened the bottom drawer. Fitz took in the sight of what she pulled out, the weird silicon penis and the belt and harness with the rather absurd colours. “I’ve only ever used this on other girls, though. You’d really be the more experienced of us here, if we did this.”

“You want to?” he asked. It seemed to be a strange thing for her to want to do, when putting a piece of silicon into his anus wasn’t going to be giving her any sensations.

“I know it might seem a little odd of me,” she said, and she sounded embarrassed. “But, well, I think it would be hot. I mean, I kind of fantasized about it while masturbating once, before we got together, and I know reality isn’t like fantasy, but I still think I’d like it more than enough, as long as you would enjoy it. In fact, if it makes you feel really good, then I really want to do it.”

She’d already mastered plenty of ways to make him feel really good, of course. But that was just like Jemma, Fitz thought, to want to find all the ways to do it.

He thought about it. It was weird to think about being penetrated by that thing, which looked even sillier than Fitz might admit a real penis did. But when he could get himself to stop dwelling on that detail, he thought about what it would feel like to be stretched open and filled, to be fucked, thrusts hitting his prostrate, without worry, because the only person there to judge him would be Jemma. He thought about having her above him, her face bearing that intense look if always got when she was riding him or working on him with her hands or similar. It sure sounded like it would get her aroused; he thought about the grunts she might let out, how she might hold him in place the way the first bloke who had fucked him had done, just pin him down and take.

“I…I think I might like that,” he finally said. His voice was slightly hoarse, and his cock was even twitching, though he wasn’t up to full arousal at the moment.

“Good,” she said, and kissed him. “Maybe not immediately, though. How long has it been for you?”

“About five years.”

“Oh, yes,” she said. “We should definitely take a night to just loosen you up first.”


The next day was long and wearying, and the next night they weren’t up for anything except talking about it a little more. Jemma ended up explaining to him what rimming was, shocked that he hadn’t already known. “I thought gay blokes all loved that,” she said. “I mean, I’ve gotten that impression, and that it creates very intense sensations. None of the blokes you’ve slept with ever brought it up with you?” Well, there had only ever been four of them. Once she had explained it to him, and told him that yes, she really did want to put her tongue in that part of him, Fitz found he was game enough to let her, though.

Although all in all, when the night after that, she ended up getting called in for a brief conference with the new director after dinner, Fitz took the time to shower, glad Jemma’s new high rank compared with them sharing a room meant they also had a bathroom to themselves. He washed his entire body, but paid special attention to his anus, even digging a soapy finger in, trying to get himself as clean there as possible. It also gave him a chance to note his own reactions to being penetrated. He’d been already, of course, but he’d been too anxious during the fingers part to really pay much attention. The cavity was tight; five years was a long time. But he found the feeling of being pierced and clenching around his finger to be oddly pleasant, even though he made no attempt to seek out his prostrate.

Jemma came in to find him sitting in bed naked, combing his curls out. He had the bedclothes covering anything indecent, but when she stopped and looked him over, he saw her eyes darken, as she stared at him like he was good enough to eat. It was still something Fitz was not used to, thinking of himself as something to be desired, but he couldn’t say he minded being thought of like that, at least if it was by Jemma. “The things I have been thinking about doing to you while I’ve been walking back here,” she breathed, and Fitz felt the first tug of a potential erection.

That business escalated when she walked right over to the bed with every cell in her body visibly screaming Intent, shedding her clothes as she did so. He’d have figured she’d want to use the toilet or have a glass of water first, but apparently not.

Fitz was being kissed, not aggressively, but firmly, deeply, hot enough for him to feel the heat in his toes, even as Jemma pulled the blankets back to expose his entire lower body to the cold air. He was hardening rapidly by the time they broke apart, and he thought he heard a tiny chuckle as Jemma bent her head down and saw it. But she took her trip down slowly, stopping to make tiny kitten licks to his nipples which made his breath hitch, suck hickeys in his sides, just above his hips, nuzzle around his groin without quite getting to it. She’d done this before performing fellatio on him, and he knew she was working herself up with it as well as him.

It couldn’t but make him just a little nervous, since unlike in the usual case, he had no idea just what Jemma was going to do when she got down there. It didn’t help matters that she herself paused when she did, as if considering strategy. Or maybe thinking she should get her lube. He knew there was a bottle in the drawer where they kept the condoms, although they two of them had never needed it. Then she started by flicking her fingers up and down his cock, which was a good distraction, then running those of one hand more firmly as she twisted herself around and reached out with the other, until she was able to get the drawer open and the lube out.

Then she said, “I know you know what teabagging is, because Harvey explained it to everyone back when the Tea Party were foolish enough to call themselves Teabaggers.”

“Yeah, I remember that,” Fitz managed. On some nights, he supposed, the suggestion she might do that might have unnerved him. But on a night where he expected her fingers and tongue to be in his butt…well, his testicles were right near his cock anyway. It wasn’t that much of a move.

So he made no protest when she said, “Much as I dislike the notion of having anything in common with the Tea Party,” and nudged his hips up slightly to get easier access to his balls. Fitz tried to think what her mouth might feel like around them. She’d played with them with her hands plenty, but he suspected this might feel a bit different.

Except she didn’t take them in her mouth right away. Instead there was her nose nudging them and sending tremors up his spine, and then there was her tongue, flicking over them lightly, then firmly, then wrapping itself around them, and… ”Ohhh…” Fitz had known all those organs were sensitive, but this was like some delicate electric shock, charges released through his body anew with every stroke of Jemma’s tongue. Some of most indecent sounds Fitz had ever heard were coming out of his own mouth; he couldn’t hear his arms flailing against the sheets; he couldn’t keep still, exquisite, agonizing pleasure rocking his body on the bed.

When Jemma’s tongue retreated, Fitz had a fleeting moment to catch his breath. Then she was taking his balls into her mouth, and he groaned loudly with the sensation of her sucking on them, steady and relentless. She’d subjected his cock to this more than enough times for Fitz to know she could do this for ages, until he was out of his head and begging for mercy. He dug his feet into the mattress as best he could and tried to hold on.

He was trying to get enough concentration together to get one of his own hands on his cock, because he was going to die if somebody didn’t touch that soon, when she reached back, and he felt lubricated fingers slide between the cheeks of his arse. A moment later her mouth was off of his balls, and she was gently nudging his legs up further even as she parted the cheeks to expose his rectum. Fitz gasped against the overwhelming feeling of vulnerability, okay only because it was Jemma he was vulnerable to. He couldn’t breathe at all for a moment when he first felt the warm, wet swipe of her tongue.

Initially it didn’t cause much in the way of physical sensation. At least nothing Fitz could pay much attention to when all he could think was She’s actually doing this, she’s actually licking my arsehole. Then she nudged her nose in, and her tongue poked into his anus.

Fitz was still breathing, but he had no idea how. He wasn’t even sure what it was about the softness and dampness of her tongue that drove him this crazy. He might have even thought it absurd, if he’d been capable of thinking anything at that moment besides goodpleasemore.

And he was getting more, because Jemma was following tongue with fingers even as she kept the first in there, prying him open still further, more of that thing slithering into him, taking him with the most delicious invasion he could ever imagine. Being fucked hadn’t felt like this, like parts of himself he rarely thought about were being explored for Jemma to know, for her to find every last drop of pleasure they could give him.

Fitz was just thinking there couldn’t be any more for her to find when her finger got just a little further in, and, oh, there it was, as he outright yelled at the pressure right on his prostrate. He thought her heard her chuckle against his hole, the vibrations of it sizzled up and down his spine, even before she jabbed her finger in again, and then one of Fitz’s hands somehow found his cock, and a single grab finished him; hot semen spilled itself over his shaking body, the pleasure ripping through him so strong he thought he might black out.

“Oh, God, Fitz.” Jemma’s voice was desperate as she clambered to her knees, and when Fitz could get his arms to move again he helped her straddle his face. She was so wet his chin was soaked even before he got his mouth onto her clit, and the noises she made were wild. It didn’t take long at all.

“That was fun,” said Jemma, as she slid down to kiss him, “but I didn’t really get you that open. I think we’re going to need another night.”


One week and three more nights later, the two of them showered together. Standing behind her, Fitz happily ran his hands down her back, until they stroked the cheeks of her arse. He’d long since learned she liked that, and now it got a little sigh of pleasure out of her. He seriously wondered for the first time what it would be like to go more inward.

“Jemma,” he said, “not that I want to do this, necessarily, but I’m curious. Have *you* ever been penetrated anally?”

“Never with a cock,” answered Jemma readily. “Beatrice and I experimented with fingers, though. And…”

She drifted off, and Fitz knew what that meant. “Will?” All her other lovers the two of them could now discuss freely without any pain on Fitz’s part. He even thought he’d get there with Will, sooner or later. Even now, he could keep his voice steady as he said, “Well, that makes sense, I suppose, since you two didn’t have access to birth control.”

“We didn’t have access to proper lubricant either, though. Even my body wasn’t producing much. Honestly, I don’t know if I could’ve managed vaginal intercourse even had we been willing to risk it. So we didn’t go beyond anal fingering either. Maybe if I’d been there longer…” Then she seemed to realize this was a bit much to be talking about Will to him right now, and said, “We should probably finish quick; I think the water is about to get cold.” At least there was more of it, now that they were no longer trying to keep everyone in the world from noticing the Playground’s existence. Jemma had been at Hydra during the worst months of utility rationing, but they both knew they were lucky they could now shower both before and after sex.

The strap-on was placed on the bed, still in the towel Jemma had wrapped it in after she had very thoroughly cleaned it earlier that day. Fitz unmade the bed and lay back on the sheets. At first he thought Jemma actually donning that thing would be too nerve-wracking to watch, but even at this point, all he could think when looking at her with it on was how ridiculous those colours were.

The look on her face, however, when she took in the sight of him naked on the bed, was another matter. The heat flushed Fitz’s face, then the rest of him, as she said, “Lube.”

They’d obtained a new bottle earlier in the week, still unopened now. When Jemma struggled with the cap, Fitz reached out, and she handed it over. It was a tight cap; it took him half a minute to finally get it to give way. That helped center him, and the feeling remained even as he handed the bottle back, bent his knees up, and rocked back just enough to expose his arse to the air.

He watched as Jemma took the scene in, then shook her head. “This isn’t the way to start this,” she declared. It was weird to see her uncertain in bed like this; that was usually his job. She replaced the cap on the bottle and moved up to kiss him.

One good thing about that was that it helped Fitz lose track of time to some extent. Not entirely, unfortunately. Occasionally during the following minutes the thought of how long they’d been kissing and whether they should move on battered at his head. But then he’d focus back on Jemma’s mouth on his, her hands on his chest and back, his holding her to him, and he wouldn’t think.

She took one hand off him when she moved to kiss around his neck, his shoulders. She had to take the other one off when she got the bottle reopened, but she even continued to kiss around his chest for half a minute or so after that. By the time she withdrew, Fitz had his center again, and also was hard, and because he’d kept the lower half of his body in position, it was easy for her, then, to move an arm down, and poke the first lubricated finger in.

Fitz had now at one point during the past week had four of her fingers in his ass at once, albeit briefly. They were much smaller than those of the two guys who’d opened him before. One should have been nothing. But it made him too aware of what was coming. He focused on holding still, and breathing in and out, in and out. Jemma had a second finger in, and the stretch was more pleasant than not. “Scissoring…” he heard her murmur to herself, before she took the action. He was very aware of her eyes down there, looking at him as she stretched him out. For the first time, though, that felt just a little thrilling, having that feeling of absolute trust in her.

Three fingers hurt, of course; there was no avoiding that. It wasn’t that bad, though. Fitz found himself stroking his cock, keeping mostly hard while distracting himself from the pain. Also distracting was the sound of Jemma’s breathing; it was definitely getting quicker. That sent Fitz trying to spread his legs just a little wider. He wanted her to have him like this now, honestly. A lot. And it wasn’t really like he’d ever not wanted it for himself, even if that desire hadn’t often been at the forefront.

When Jemma withdrew Fitz even hissed in anticipation, ready to welcome what came next. But when Jemma pulled herself up into position, she cried out, “Oh!” and stopped.

Fitz had to push himself up on his elbows, but then he saw she was looking at his cock. He’d stopped stroking near the end, and was still half-hard, but the pain had taken its toll.

Of course. The previous nights, she hadn’t gotten much chance to look at his cock, only pulled her head up after the burn had faded and he’d either gotten hard again or come. She’d probably never gone beyond one or two fingers with Beatrice or Will; she’d had no idea.

“It’s fine,” he told her. “This happened the other two times too. You go beyond a couple of fingers and it hurts at first. Trust me, it’s worth the pain.”

“You mean you were in pain, and those two bastards told you to just put up with it?! Oh God, Fitz, why didn’t you…what have I…”

“You’ve done nothing wrong!” Fitz nearly shouted, because he sure as Hell wasn’t letting her think that. “Honestly, that went a lot better than it did with the two blokes. And I really do think this is just what happens. Maybe not if a someone’s fucked a lot, but I don’t really know. The anus isn’t self-lubricating, remember, and it doesn’t stretch as easily as a vagina does, and even that hurts, sometimes, especially if it hasn’t been penetrated before.”

By now he’d completed deflated, but at least she was nodding. She looked down further, at her strap-on, already lubricated. “So you mean this…going in…”

“Yes,” said Fitz. “But believe me, Jemma, I want you to do it.”

She moved to get in position, fumbling with the silicon as she placed it at the orifice. “You seemed to be fine with four of my fingers,” she still pointed out.

Might be a good idea to continue to talk. “Remember you had my testicles in your mouth at the time, and that was distracting…” The last word dissolved into a grunt as she pushed in, and yeah, that did hurt, and more than three fingers. But Fitz had been prepared for this, for how much bigger it was. The temperature was different, since it wasn’t self-heating, but Jemma had warmed it enough with her hands. And despite the pain, he couldn’t say he entirely disliked how he was feeling at the moment.

“Sorry I’m not more flexible,” said Jemma, with a weak smile, and that was good to see. “That would be an interesting experiment, if I was, though, but maybe…” As she pushed in further, she reached down and stroked his balls.

“Too much,” Fitz groaned. “But one the blokes stroked my cock, and that felt good.” It felt good when Jemma did it too, using her other hand to brace them on the bed as she bottomed out. Fitz felt full and tight and like his arse was on fire. Also like he might like it if she moved. “Keep going.”

“Pain’s starting to fade,” he was able to report as she pulled out and back in. “It’s starting to feel good now.” Warmer now, with his body heat, and he liked the feeling of it more than he remembered. Maybe that was because he wasn’t anxious about the way Jemma was looking at him. She was started to relax now, to murmur, “If I remember correctly your prostrate should be about…”

She hit it, and Fitz had honestly been unprepared for how hard the sensation would hit him, like being knocked across a room. “That’s very good,” he gasped. “Do that again, pl-” He hadn’t needed to ask; she hit it again, gasping a little as she did so. “Yeah, just keep doing that forev-”

She built up a rhythm quickly, thrusting into him again and again, losing all worry, it seemed, as he grew fully hard again in her hands and his moans filled the air, almost drowning out her breathing. Almost, but not quite, and as Fitz’s eyes rolled into the back of his head with each thrust she made into him, even as the rest of the world fell away he held onto that sound, to Jemma panting and even moaning a little herself, to her skin pressed against his where he legs twitched on either side of her, and where both her hands too were on his skin, one still stroking his cock, the other on his hip.

“Fitz…” She breathed his name as if in awe, and Fitz had to force himself to look, had to see her as she was doing this to him. The look on her face was adoring, possessive, hungry, demanding, and happy all at once, and even when another hard thrust snapped his eyes shut again he could still see it. “You…” she whispered, and he eagerly pushed back. God, he wished she could feel that, feel what he felt when he sank his cock into her like this. But from the noises she made, she definitely still liked it, liked seeing him take it on a visceral level, liked seeing his body writhe on the bed under her hands, all sweat-covered limbs which she could send flying every which way with every move of her hips.

“Jemma, gonna…” he managed, and the sound she made was shockingly desperate as the hand on his cock started moving fast, the way she knew would finish him. She rammed into him one last time and Fitz came apart completely, the pleasure overwhelming, his limbs practically melting with it. She kept on moving through it, the way he usually did when she came first during intercourse, sending further spasms up and down his spine, until finally he was done and left panting on the bed, wondering if he’d ever be able to move again.

There was an ache and a burn when she pulled out, but Fitz couldn’t focus on them, not after he got his eyes open to see her struggling with the harness in her haste to get it off. He managed to get enough motor control back to hold out his hands just as it fell free. Jemma didn’t have the patience to get all the way to his mouth, just grabbed one and brought it to crotch, and the rest was muscle memory for Fitz by now. She lasted just long enough to bend down and kiss him, then groaned her release into his mouth.

“You all right?” she whispered into his neck, after they had spent a little time catching their breath. “I mean, I absolutely loved that, but…”

“I might hope to do most of my tasks in the lab tomorrow standing up, but it was worth it,” said Fitz. “That was true the last two times too, except it was even more worth it this time.”

Jemma didn’t respond to that, maybe not sure how to. “I want you to do it again,” he added. “In a few weeks or so. Honestly, Jemma, that was incredible by the end.”

“That’s good, then,” she managed, then lifted herself up and kissed him. “I’ll get the strap-on cleaned, and then we can shower.” She kissed him and stumbled off the bed, though she was walking fine by the time she disappeared into the bathroom.

Fitz rested a little bit longer, listening to the water running and her tsks contentedly. When she came back in and put the contraption away, he pushed himself up, grabbing the bottle of lube and handing it to her to put away too. “Maybe amend that few weeks to a couple of months,” he said, but at least everything besides his arse felt more or less normal again.

“Better watch it,” she said, in a teasing tone it was relieving. “By then we might just figure out how to wire these things to feed me sensations, same as we did for Coulson’s arm. I might just want to do this a little more often then.”

She’d probably meant it jokingly, but Fitz found himself thinking out loud, “That might be doable, actually. I’m pretty sure we’d have to work on it on our own time, of course…”

“Well, if we succeeded, the sales could probably fund S.H.I.E.L.D.’s entire budget. The government might be much less wary of us, then.” That sent them both giggling, and she let him lean on her as they headed for the shower.

“Might be trickier, too, with the bodies parts involved,” she said as she turned the water on. “The most logical thing would be to connect the sensations to the clitoris somehow…”

“We’d have to be careful,” said Fitz. “Don’t want to risk any damage to that.” That might actually stop them, he supposed, but he was really starting to like this idea.

They’d still only been half-meaning it, but under the spray, Jemma asked, “Would that interest you, though? That kind of challenge?”

It being a challenge was another point in its favor, perhaps. “Jemma,” he said, putting a hand on her shoulder, “If being inside me feels half as good as being inside of you does, I’d love to help you experience that.”

She just smiled and kissed him, then. Just a little bit, before she went for the soap.

After half a minute or so of them washing in silence, she continued, “I wonder how different it feels, though. Penetrating the anus, as compared to penetrating the vagina.”

“If we could find someone who’s done both and is willing to talk to us…” Fitz supposed Mack probably had, though he’d be way too embarrassed to talk about it with him.

“Or you could penetrate me anally. That might be the best way to determine it, actually. We could have vaginal intercourse one night and anal intercourse the next, so you can compare them when they’re both fresh in your memory. Plus it would not only be the same pair of people, but you’d be a similar state of health for both experiences, we can make sure the room’s the same temperature both times, if we wash the bedclothes before both we can see to it they’re in the same state…”

This one, Fitz thought, they definitely were going to do, as Jemma continue to list up the variables they could try to control out loud even as she worked on scrubbing his back. He found the idea of penetrating her anally not as intimidating as he would have before this. Obviously it would be a bit more difficult, since she was smaller, but he was confident she’d know her limits when it came to pain, and he’d make damn well sure he didn’t actually hurt her any. He supposed she might or might not be able to get the kind of enjoyment out of it he had, but if she didn’t, they simply wouldn’t do it again. It was worth a shot.

It was as she’d said back in Bucharest, they were experimenting. Fitz could do that with her, he was good with that. Especially after this recent experiment had been such a resounding success.