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I looked down at my chest, and what he was doing to it. “You know what? What I love most about you fucking my tits is that your cock makes them look a lot bigger.”
He groaned a little, although I don’t know if it was the joke at his expense, or the pleasure at my expense. Well, it wasn’t really an expense. I was enjoying this.
“Mmm, yeah,” I teased, squeezing my breasts together more for him. “You love fucking my tomboy tits, don’t you?”
The tomboy reference never failed to get him more… interested. It’s not that they were uniquely tomboy tits, even if they did belong to a tomboy. But if my friend was made happy by me calling them that, then I’m not going to judge.
You might wonder how I got myself into this position. Well, if you want to be literal, I took off my shirt and laid back on his bed. But in a more general sense, it started several weeks back during another night out at the bar with our friends. This turned into a discussion of some drama involving other mutual friends from our group. Two of them were a couple, but one had gone down on a third friend after a… well, after a night like this. None of them were out this night, for obvious reasons. In fact, some of us had just found out via yet another mutual friend who actually did come out that night. Although they seemed confused about the issue, because they said oral sex wasn’t sex.
That started a whole debate, bordering on an argument, about what acts counted as sex. That led to a tangent about what sex actually meant. Then there was yet another tangent about whether something could be sex, and not cheating. Or not count as sex, but still count as cheating.
The only thing we agreed on was that we had no real agreement. There were too many variables, and everyone had a “but what if?” scenario to cloud the discussion.
I was sharing an Uber home with my friend by the time the night ended, even if the argument hadn’t been resolved. I only lived a block away from him, so it made sense for us to share a ride. We continued the debate, much more civilly than most of our friends had been doing. But I always got along with him best out of our friends. Our driver was a nice enough seeming, quiet-ish guy. I think they were amused by the discussion.
We’d actually been silent for a minute, when an idea came to me. I turned to my friend. “Hey, I was thinking about a boob job.”
He looked at me. “Well, if it’s what you want, but I think you’re fine with the ones you have.”
I was a little flustered, first for not making the best choice in words there, and secondly for the compliment. Personally, I thought mine were a little small, not that I obsessed over it too much.
“No, no.” I shook my head. “I meant boob sex. We didn’t talk about that tonight. We talked about pretty much every other even vaguely sexual act, but not that.”
“Hmm.” He looked thoughtful. “I guess we didn’t. We talked about some I hadn’t even heard of, but we didn’t talk about that.”
“So…” I said expectantly. “What’s your thoughts on boob sex?”
“Well,” he began slowly. “It seems less sexual than a lot of other stuff. I suppose the guy is getting something out of it, but I don’t see what the woman gets out of it. So I don’t know if I’d call it sex. Maybe cheating though.”
Something with how he said it stuck with me. “Wait, you’ve never fucked a girl’s tits before?”
He looked embarrassed. “Um, no. I guess I wouldn’t mind it. I’d probably like it. It just always struck me as unfair, though, because it’s not like a girl could fuck my tits.”
I laughed. “Unless you keep putting away those chicken wings like you did tonight.” Cue the mental image in my head of my friend, quite a few founds heavier, and some girl sitting on his stomach with her girlcock between his hairy boobs. Well, there was no forgetting that one.
He laughed too. He was nowhere near having fuckable tits, and he actually could pretty much eat whatever he wanted without it adding a single pound to him. “Does the girl actually get any fun out of it, though?”
I snorted. “You actually think I’ve done it? With tits like these?” I gestured at my breasts. Like I said, I always saw them as smaller than normal, although I guess part of me recognized that as just society placing a big value on big breasts. I grabbed them, squeezing them for emphasis. “Do these look at all fuckable to you?”
I wasn’t fishing for compliments. I was expecting an honest “no” from him. Instead, I got silence. Was he afraid of feeding my small hangup over my small breasts?
Or was he not saying anything because he actually thought they were fuckable? I could see him not knowing what to say if that was the case. It had been a weird conversation all night, but apparently he didn’t want to turn it into a different kind of weird.
I laughed again, a little playfully. “So you do think they’re fuckable?” I squeezed them again, with a little more emphasis. Then I squeezed them together suggestively.
Now he really looked embarrassed. “Like I said earlier, I think your… chest is fine as it is, and… um… definitely capable of boob sex.”
Maybe it was the alcohol from earlier that night, although my tolerance was high, and this ride was taking forever. Or maybe I was just in a rare mood that night. But still cupping my breasts through my shirt, I leaned into him a little, before asking. “But do you want to fuck my boobs?”
He looked startled, and the car swerved a bit. I glanced at the driver, who suddenly had his eyes intently on the road. I had forgotten about him.
“Not here,” I clarified. “But we’re almost to your place. We could both just get off there, and then… well, me and my boobs could get you off.”
He looked… confused? But intrigued. Contrigued, maybe? I know it’s not a word, but it was the only way to describe him right now. “Why are you offering?” He asked.
I shrugged. “Well, we’re both boob sex virgins. We’re also in agreement that as far as sexual stuff goes, it’s fairly minimal. So why shouldn’t we do it? I do kind of want to see if a guy can fuck my tits properly. Neither of us are seeing anyone, so the ‘is it cheating?’ thing isn’t relevant.”
That’s when the car pulled up in front of his place. I told the driver I’d just get off here, but paid and tipped him for the entire route. He’d definitely been entertained during the ride.
So there my friend and I were, standing outside his place. We went inside, because it’s not like he was going to make me stand out there or walk home on my own. It’s not like he was afraid of my breasts. Maybe of me at times, but my breasts never scared anyone.
I think he thought I was bluffing until we got inside. But I immediately pulled off my shirt. I’ve never been fond of bras, so he was staring right at them. Then I pushed him back so that he sat heavily on the couch. I unzipped his pants, struggled with the position for a bit, and then… well, what do you know? My breasts really are fuckable. It turned out this really wasn’t a great position for this kind of thing, but we made it work.
He warned me before he was going to cum, otherwise I might have taken a headshot from his load. Instead, I graciously allowed him to cum all over my breasts. It seemed like the right thing to do, and honestly, I hadn’t thought this out all that well. I didn’t have some tissues for him to cum into or anything like that. I could either let him make a mess someplace in his living room, or on my face, or someplace that would take this deeper into sex territory, like if I let him cum in my mouth. Or I could let him splash it all over my breasts, which is what he did after I reassured him it was okay.
Then I had to reassure him afterward, because apparently guys think differently when the blood is back in their big head. But I laughed and told him it was okay. I cleaned off in his bathroom, then left before things could get awkward, walking the last block back to my place. Well, we walked together, even though I’d probably end up protecting him if something happened. But it was nice of him, and we said goodbye before he walked back.
Somehow, it became a regular thing. He obviously liked it, and I… well, I didn’t mind it, other than having to clean up after. I think I liked the idea that my tits were definitely fuckable, and also that someone would enjoy doing that so much. It became a regular thing after our get-togethers with friends, or any time we were sharing a ride. Or if I needed to go to his place for some reason. Like, say, to let him fuck my tits, disguised as “hey, let’s watch the game.” We weren’t quite just friends anymore. Technically, we were friends with benefits. Honestly, though, I kind of preferred the term “bosom buddies”.
And that brings us to tonight. Going out with our friends was less of a thing now, given that two of those three friends in the maybe cheating scandal I mentioned earlier had run off together, and the other one just wasn’t going out anymore. Whatever. My friend and I would make our own fun. More and more, that took the form of him fucking my tits, like he was doing now.
He really didn’t have a small cock, any more than my tits were actually as small as my insecurities said they were. I just liked to kid him about having a small penis, because that was the kind of friendship we had. I guess we also have the kind of friendship now where him sliding his cock in between my breasts is also a thing. But it makes sense, because it turns out his cock and my breasts fit perfectly together. And with my squeezing them around his cock, they do look a lot bigger.
“Hey,” I said impulsively. “Do you want to try something different tonight? I could make an exception and let you cum on my face.”
He looked down at my face, then really looked, as if wondering what it would look like plastered with his cum. I could tell he was on board with the idea. Of course, as aroused as he was, it would be hard for him to say no.
“Or,” I continued casually. “You could go down on me. It’s not that this isn’t entertaining, but I’m ready for some fun of my own, I think.”
I had meant after he came himself, but he pivoted from fucking my tits pretty quickly to helping me pull down my jeans. I think he was looking forward to making me cum for a change. When the panties came off, that was his first time seeing me naked.
As he moved his head between my legs, he looked up at me. “You’re sure? This is a bit more sexual than what we had been doing. At least according to our discussion that night.”
I laughed. “It’s still pretty tame in my book, especially for two friends that have absolutely no other romantic complications in their life.”
I looked down at him slyly. “Besides… don’t you want to know what my tomboy pussy tastes like?”
I can’t imagine that it tastes much different than regular pussy. But sometimes you slap a fancy label on something and people go wild over it. Once he actually got to work, he sure seemed to like it, and I liked what he was doing to it. Unlike having my tits fucked, having my pussy eaten wasn’t something new for me. It had been a while, although I don’t remember it being as good as this was. I think part of it was that my friend was very intent on paying me back for all the orgasms I gave him recently.
With a cry of pleasure and the arching of my back, he lowered his debt by one. It felt good to cum. I’d toyed with the idea of masturbating after our previous get-togethers, but had resisted the urge. This one was long overdue. But he didn’t stop with just one. He’d learned what I’d liked on his first attempt, and seemed to make it his mission to be even better the second time around. That didn’t mean making me cum faster, although he could have. It meant making me cum even harder and louder. This time I grabbed onto his head tightly, calling out much louder this time.
As I came down from that second orgasm, he lifted his head to look up at me. “Are you ready for more?”
I looked down at him fondly, still coming down from the experience. “Yes, much more.” I looked him carefully in the eyes. “I want you to fuck me.”
That caught him off-guard. There’d been some relatively rapid escalation here. “Are you sure? Isn’t that crossing some kind of line?”
I laughed, stroking his head fondly. “If it isn’t, then it wouldn’t be nearly as fun. Besides, I want to try something where we can both cum.” I smiled mischievously. “At least, if you think that little cock can make me cum as much as your big mouth.”
He smiled back, slowly moving up my body. “Little cock, eh? I’ll show you what my ‘little’ cock can do.”
I kissed him gently as he moved into place on top of me. “That’s what I’m counting on.”
It definitely didn’t feel little when he slowly took me. He also most definitely knew what to do with it, especially now that he had something more than my tits to work with.
It felt a little wrong, but not because of what we were doing. It felt wrong because we hadn’t done it sooner. We were a good fit for each other, like his cock was for at least two different parts of my body. Other than the delayed timing, everything else felt right.
I came again. I was too worked up still, while he had time to recover since being between my breasts. But I was pretty sure I had another orgasm in me, and I was saving that for when he came.
“No more cumming on my chest,” I told him as we worked towards the grand finale. “This time, you’ll be cumming inside of me.” I paused, then corrected myself. “My tomboy pussy.”
He looked down at me intently. “I’d happily cum in your pussy, even if you wore pink dresses and ribbons in your hair.”
I sighed. “Oh, that’s so sweet…” Then I came. It was a little earlier than I planned, but it was okay. He was right there with me, his orgasm synchronized with mine, and not even caring about what adjectives were in front of my pussy as long as his cum was inside of it.
Since he seemed less hung up on the tomboy part, I was a little more girly with him afterward as we cuddled. I mean, not too much. I didn’t want to spoil him or misrepresent myself. But I’m allowed some softer, tender times with my long-time best friend and… well, how long we’d been lovers depends on how broad your definition of sex is. The important thing is that we were lovers now, and somehow the idea of doing this kind of stuff with him for… well, forever, I guess, didn’t sound like such a bad deal for either of us.