Unfortunately, this story didn’t happen to me — I was way too shy and reserved during the first two years in college. This is a story told to me by one of my close friends at the time, and I’m retelling it here (through his perspective to make things easier). He told me this story as it was happening through several updates, which I’ve chained together here. It used to be a major player in my spank bank but I guess it got pushed out by other things over the years and I sort of forgot about it. The memory recently came flooding back to me, and I figured I’d share it. Obviously I’ve taken a little bit of artistic liberty with some of the more subtle details, but my friend was a pretty vivid storyteller and I think this is pretty close to accurate.
***
The dorm where I lived in college was co-ed (well, all the dorms there were). Pairs of rooms shared a bathroom to form a suite; suites were same-sex, but two neighboring suites might be co-ed. Floors usually had a fairly even mix of males and females, with shared common spaces but no communal bathrooms or anything. It wasn’t uncommon for neighbors to hook up, be fuck buddies, or try dating. It was inevitable, then, that some people would get reputations as the year went on — “easy” girls, guys who “will fuck anything”, etc.
One of the girls who got a reputation was Jenn. She was pretty average looking — medium height, not quite “petite” but definitely on the skinnier side, with long, curly, brown hair framing a cute face. Definitely attractive, but not in a way that people talked about. Her one above-average feature was her chest. I remember someone saying once that they were DD’s, but that was probably just speculation. Anyway, she had a pretty great rack. They weren’t huge in a way that makes you wonder how she contained them, but they were definitely sizable, and looked even bigger on her smallish frame. Most of the time she wore clothes that sort of covered them up, but occasionally she’d wear something more revealing. Her reputation was as an easier girl to hook up with, but as I would soon learn, it was much more specific than that.
A few of us were hanging out in someone’s dorm room one time and started getting pretty drunk (a fairly normal occurrence). As we often did, we started talking about some of the girls on our floor and Jenn came up. When she did, another guy said he had slept with her, too. After the Eskimo brother jokes subsided, the first guy said that she was the first girl he’d ever tittyfucked. The other guy said that he tittyfucked her, too, and they recalled how talented she was at it (apparently it takes a little bit of skill on the woman’s part to make it a good experience). The conversation moved on to other girls, and Jenn didn’t come up again.
A week or two later I was at another kickback in another dorm room, but this time with close to 10 people crammed inside. Everyone was drinking and smoking, and after a while we were all pretty intoxicated. As things started calming down, I ended up standing in a corner next to Jenn. She seemed a bit uncomfortable — I think the person she was talking to unexpectedly left to talk to someone else, leaving her alone — so I started making small talk. She seemed relieved for a break in the awkwardness and we started chatting. We warmed up to each other and the conversation moved from small talk to a little deeper conversation. It helped that we were both buzzed. I said something about how Jack (the guy who’s room we were in) usually organized pretty good parties, and she admitted that she almost didn’t come because she was afraid of running in to a certain guy there. I jokingly asked if he was a one night stand that she was afraid to see in public, to which she chuckled to herself and said, “Kind of.” At that point I was curious so I started fishing a little more.
Jenn admitted to me that she’d had quite a few one night stands, and that normally she didn’t mind bumping in to people again, but that this guy got really attached and started borderline stalking her. With the help of some guy friends she finally got the message through to him that she wasn’t interested, but she was still a little uncomfortable about the whole thing. As she’s telling me this story, my one track mind was still stuck on the way she casually and unabashedly admitted that she’d had “quite a few one night stands.” I tried to steer the conversation back in that direction and said something to the effect of, “It’s good that you aren’t weird about having a lot of one night stands — you should be proud of your sexuality!” It was super cringe-worthy and almost certainly wouldn’t have worked under normal circumstances, but the booze played in my favor this time. “Thanks, I know!” she said. “Some people try to give me shit about it, but honestly I just really like helping people do something they’ve always wanted to do.” That last part struck me as weird. “Wait, what do you mean?” I asked. Her facial expression changed, and I could tell that she was wishing she hadn’t said that. She started to blush a little, but I made sure to act super nonjudgmental and prodded. After a while she opened up a little bit.
“I had a boyfriend my senior year in high school who was really into… fucking my tits.”
“Tittyfucking?” I blurted out, probably a little too loudly.
She laughed and replied, “I mean, I always thought that word sounded stupid. But yeah. He’s how I learned how to do it. And honestly, since I didn’t now any different, I just assumed it was a normal part of sex. I guess I never really stopped to think about what flat chested girls do.”
“Yeah, I mean, most girls can’t. I’ve never been with a girl who could,” I said, just trying to be honest and reciprocate some of her vulnerability. She gave me a weird look for just a second, then continued.
“Well, the first time I had sex in college, I just got in position and started doing it without really thinking about it. He got super excited all of the sudden, which I didn’t really understand at the time. Again, it was a normal part of sex for me. He ended up… finishing like that.” She looked a little embarrassed at herself that she had just talked to me about a guy cumming on her tits.
“It must have been his first time,” I said, trying to keep the conversation feeling natural.
“Yeah, probably. I was talking with some girlfriends later and they were talking about how their boyfriends always want to do it, but they either aren’t well enough endowed or just don’t enjoy it that much. I decided to do a little experiment and tried it with the next couple guys I slept with, paying attention to their reactions. Almost all of them were the same — they were super in to it, like some animalistic part of them had been unlocked. I love seeing how happy it makes them, and then later, they’re always super thankful about it. It makes me feel really good.”
Aside from the obvious issues of trying to sexually please strangers, I was getting really turned on by our conversation. Despite the whiskey dick, I had a semi that was making a bit of a bulge in my pants. I tried shifting to cover it up, but that only drew her attention to it. She gave me that same, weird look from earlier when I said I’d never tittyfucked anyone. Then she turned her head away, surely trying to cover up the fact that she’d just caught me adjusting my junk, and saw a friend of her’s who had walked in while we were talking. They did that typical, college white girl “Hey girl!” and started talking. I went back to drinking with my friends, and Jenn and I didn’t talk for the rest of the night.
The next weekend, my roommate and I went to yet another kickback in yet another dorm room (gotta love college). I saw Jenn and decided to say hi. She hugged me and seemed happy to see me. I flirted with her over the next hour or so, and she was flirting back. I was feeling pretty good about myself. At one point we were alone in another corner again, talking about something (I don’t remember what), her laughing at my jokes, me trying to make subtle physical contact, and eventually us making out. She was a really passionate kisser, and I actually started to get a little self-conscious about the fact that we were making out so intensely in front of so many people. I looked around the room until I saw my roommate, confirming that he was still here and, consequently, not in our room. I looked at Jenn and asked her if she wanted to go to my room. She looked me in the eyes and gave me a devilish smile, then said, “Yes.”
Fortunately, my room was just a short walk down the hall. Once inside, she was all over me. I’d never been jumped like that before. We were making out while shedding clothes, and we hadn’t even made it to my bed yet. I was down to my socks by the time we got there, and she was wearing just her bra. She watched me as she took it off, clearly wanting to see my reaction. And for good cause — they were outstanding. Big without being saggy — not quite perky, but not with that droop that tends to plague large breasts (ah, the benefits of being 19). She giggled and started kissing me again, and we fell in to my bed. I was giving special attention to her tits, rubbing them and repeatedly moving my tongue and lips down to play with her nipples. She was grabbing and stroking my cock, which was rock hard already. I’ve always enjoyed going down on girls, so I made my way down between her legs and started eating her pussy. She was very vocal, and I kept looking up because I loved watching her tits heave with her heavy breathing. She seemed like she was getting close to cumming, but then she pulled me back up to kiss her. Breaking the kiss, she gave me another one of her devilish smiles and then, pointing toward the mess of clothes and such on the floor, said, “Hand me my clutch.”
She pulled out a small tube of KY and seductively squeezed some out on to her tits. I was already pretty sure that I was going to get to tittyfuck Jenn, but that act removed any doubts. She made show of rubbing it in to her tits until they were glistening. Then she got off the bed and got in to this sort of semi-squatting position against the side of it. It’s hard to describe, but it basically resulted in her being higher than if she were kneeling, but lower than standing. Basically, her tits were at perfect dick level. This girl clearly was not lying about her experience.
I stepped forward and she grabbed me around the waist, positioning me just so. When my dick was nestled between her tits to her liking she let go of me and squeezed them together. I was enveloped in warmth. I started to thrust and was surprised by how it felt. Not like I had imagined, but still so good. I’m a big visual guy and I think the picture of the whole thing was half the fun. This attractive girl with tits that were just big enough, smiling at me while I fucked them. She didn’t hide the fact that she really enjoyed it — she definitely liked seeing other people get as excited as I was. Soon I was thrusting out of control — it felt so good, she looked so good, everything was really coming together. I knew I was close and, as is habit, told her I was getting there. She moaned and once again flashed her devilish grin. In what must have been an extension of her liking to please people, she said, “You want to cum on my face, don’t you?”
That was pretty much it for me. Several things happened at once. I groaned, “Fuck yeah,” or something equally unintelligible; she let go of her tits and pulled her hair back; I started stroking my cock (I’m not one of those guys who can cum hands free); she dropped from her semi-squatting position to a sitting position so that her face was just below my dick; and finally, she looked up at me with that pretty face and that mischievous expression. I told her I was cumming and she closed her eyes. I was rocked by an extremely powerful orgasm, and I watched my first shot of cum hit the side of her nose and run down her cheek. I shot another rope on her other cheek, and another across her lips. She felt the shot on her lips and opened her mouth, sticking her tongue out just a little bit. I shot a final strand on to her tongue and looked down to see cum dripping on to her tits, mixing with the lube. I stepped back, spent and out of breath. She smiled, looked at me, and said, “That was really hot.” I laughed and said, “You’re telling me!”
After that I was fortunate enough to become one of Jenn’s friends with benefits (turns out she had more than a couple). Living on the same floor was a huge plus. Some times we would fuck, some times we would go down on each other (she turned out to be really in to 69), but there was always at least some amount of tittyfucking. Over the summer I saw on Facebook that she got a boyfriend, and I moved in to an apartment just off campus the next fall. We didn’t keep in touch, but I’ll never forget that year in the dorms with Jenn.
Source: reddit.com/r/gonewildstories/comments/5h9i37/some_women_just_want_to_watch_the_world_tittyfuck
Been way too long since this sub a good tittyfucking story! Thank you!
Loved it. Good story.