Hi readers, I’m a long time reader of this subreddit myself, but first time I decided to try and share a story myself. This is a story from my college days, up in the Midwest a-ways. I was about 23 at the time (I’m 30 now), studying heavily for a Computer Science degree. So I spent a lot of time coding, at coffee shops, on campus, and even out at the bars. There were a few choice places in this decently sized college town, for a young man to quietly enjoy a beer during long coding sessions. I made myself a little home at one of these bars, frequenting it often, getting to know the bartenders, who would have my favorite smoke and drink available when I walked in, especially during the winter months. It was a great place to be, I met a lot of good friends there, and on a couple lucky occasions, I got lucky enough to meet a girl here and take her home.
So to start, a brief description of me; Hispanic, about 5′ 9″, lean but in good shape, broad shoulders for my height. Very caramel skin, which stood out in the Midwest. Long, dark and curly hair, which is probably my best physical attribute when it comes to attracting ladies. I’ve had numerous a woman compliment me on my locks. Even had a girl draw me at the bar randomly one time, no lie. So I’m under the impression I’m no slouch when it comes to looks, even though I’m not the most muscular of physical specimens. But genetics was kind to me and I’ve got size where it counts. 6″ cock, average when it comes to length, but girthy. Enough so that that, too, has been commented on in a good way.
And apparently enough of a draw for my first ever FWB. She was incredibly sexy. Older than me by a few years, a bit taller, dark complexion (I later found out she had a healthy dose of Native American heritage) full, luscious lips, and wonderful curves. Her breasts where C cups if memory serves, not enormous but nothing to scoff at. But her ass was incredible, full and squeeze-able, but not fat in the slightest. She’d always wear these dresses that accentuated her figure, and when we were seeing each other I couldn’t get enough of seeing her in them. The first time I met her she was in one.
I was at the bar working. I may have put away my laptop for a bit but I most likely had a notebook out, jotting ideas and brainstorming methods or techniques I would use in my next bit of coding. It was a Saturday afternoon, nice and bright, I believe early winter just as the cold was starting to set in. She came up to the bar after me, sat next to me but with one bar stool in between us. She ordered her drink and relaxed, the bar was still quite empty at this time, just a few regulars milling about. I noticed her immediately when she sat down, giving her a quick once over and recognizing her beauty, but I was fairly focused and just continued to work, not thinking much. But I really must have caught her attention. She kept shooting me sideways glances, subtle at first but then increasingly obvious, turning her head and looking at me as if to draw my attention. Part of me was still focused and part of me was interested but wasn’t sure if I was reading the signals right.
She finally says something to me, along the lines of asking me what I was working on. It honestly surprised me, and I had been so absorbed in what I was doing, I had no good reply ready. So it ended up being fairly short responses, just kind of matter-of-factly stating that I was a coder, was working on a project for school, blah blah blah… I either bored her or offended her initially, because she quickly gave up and went out for a smoke. It was at this point that it hit me, the young horny part of my brain finally awaking from its nap and telling me to go talk to this lady.
So I went outside and bummed a smoke off of her and inquired a bit about her and her day. She immediately perked up, and I could tell this was a good chemistry. We didn’t talk for long, but long enough to learn that she was bar hopping that afternoon and invited me to meet her at a specific bar after I finished up my work. I told her I’d be more than happy to, and upon receiving her name – We’ll call her K – I went back inside to finish my work as quickly as I could to join this lady, and she closed out her tab and headed out.
I screwed up this part. I finished my work and darted over to the bar she had mentioned, it’s a college town with a small downtown, so everything was in walking distance. But I was too late. She must have already left this specific bar and hopped over with her friends to another one. I had missed my shot. I teetered around downtown for a few more minutes, stopping in at a couple more bars to see if I would randomly run into her again, but to no avail. I had missed my chance, or so I thought.
That night, name in hand, I hopped on Facebook and found her in my local groups and sent her a message. I was again lucky, she recognized me immediately and we struck up a quick FB conversation. The conversation quickly escalated to heavy flirting, which escalated to us sexting over Facebook that very night, and her telling me that she had had an orgasm from our chat. This was definitely going very well very quickly, and things didn’t stop there.
We talked for a few more nights, obviously attracted to one another, and I inquired as to how we could hang out one night. She had ended up at a dance club near downtown the night in question. We had traded numbers already, and she let me know that once she was done dancing that she would call me, and if I liked to I could pick her up and take her back to my place. I couldn’t believe that things were going down this way. I, who had been pretty damn shy around women at the time, had actually scored a date from a random encounter. I was excited and hardly containing my anticipation for the phone call. Lo and behold, she calls around 10pm or so, we chat for a bit, and she lets me know where she’ll be to pick her up out front. I hop in my little car and jet over as quickly as I can, already hard from the thought of what could happen this evening.
I pull up to the building and there she is. It’s hard to make out details this late at night but I know it’s her, and she pokes her head in the passenger side door before hopping with me and away we go, back towards the apartment. We are flirting heavily in the car the whole way home, hands on each other’s legs, coy smiles and laughter back and forth. It was not just a hot date, it was genuinely fun times.
We arrived at my small apartment complex. I was living garden-level in a one-bedroom at the time, and I lead her down the short flight of stairs and into my apartment. It was sparsely decorated at the time, I had a TV on a footlocker and a couch in the living room, and then in the bedroom nothing fancy at all. Just a mattress on the floor and computer desk in the corner, like a true college student. But she didn’t seem to mind at all. We both sat/knelled/fell down on my bed and began to make out almost right away. I’ll never forget her lips, so full and plump, the kind of lips you die to see go down on you. Incidentally, she did not give me a blowjob that night, but they were sexy all the same. She began to feel my arousal through my jeans, gripping at the girth through layers of fabric. My own hands began to explore her body, feeling her up from her tummy to her wonderful round tits, covered in a tank top and sweater, the latter of which quickly came off. I love a woman in a tank top, something about it barely restraining a pair of perky tits, exposing a lot of skin topside, which is incredibly sexy to me. I reveled in the sight and feel of her chest, and I think she appreciated the attention I was giving to her breasts.
But she was quickly ready for escalation. She laid herself down on my mattress, and slid her panties off from underneath her long dress, not taking the dress off. I began to kiss her legs, starting at her ankles and very slowly working my way down further and further. I took my time, kissing, licking and sucking almost every square inch of her tan, toned legs. I could hear her breathing begin to quicken in anticipation. I myself could feel my heart pounding out of my chest. My slow and steady approach to her nether regions was arousing me greatly, I could feel that I was completely hard underneath my jeans, so hard it was straining to be released. I wanted so badly to just rip my clothes off and plunge my thickness into her, but I knew I had to take it easy. My lips reached her pelvis, mere centimeters away from landing on her lower lips. I didn’t want any of this time to end, so I took my time and kissed every spot of skin around her beautiful, shaved pussy. This drove her crazy, and she writhed at my teasing, fondling her breasts in both hands, pinching her nipples through the thin fabric of her top, biting her lip, moaning; Every indication of how turned on she was, was there. It pleased me greatly to have this sexy MILF goddess in full throes of pleasure under my mouth.
I finally ceased the teasing and placed my mouth over her pussy. My tongue ran a full stroke up from the opening of her pussy to her clit. Her light groaning erupted into a full-fledged moan, and thus began my oral session on her. I would run my tongue up and down her slit, running swirls around her clit when I reached the top, and sliding it in as far as it would go into her when I reached the bottom, tasting all of her. The “oh my god”s that escaped her lips over and over kept me going, focusing on the clit at times, taking each of her pussy lips in turn into my mouth and sucking on them, running my tongue along them. When I played with her clit her back would arch, hands squeezing her tits tightly, and I was wondering if she was cumming right then and there. She was vocal, not saying words but not holding in the flood of moans and groans and ‘yes’s. She’d grab my hair with her hands and press down on my head, driving my mouth onto her now soaking wet pussy even more, encouraging me to speed up my tongue flicks, or the occasional ‘right there’ when I hit a good spot inside her. Knowing that I was giving her this much pleasure was a real treat, I could tell I was doing a good job and to have her writhing under my tongue was a turn on in and of itself.
I could have gone on for an hour like that, I was enjoying myself immensely, but she had other plans in mind. “Hurry up and fuck me.” Those where the magic words that lifted me up from between her legs. I was ready to go; I had been rock hard for at least an hour, since the moment she called earlier that night. I stood up next to the bed, and quickly undid the button restraining my cock in my pants. I slid my pants and underwear down in one fell swoop, and my cock stood at attention. I have a slight upward curve to mine, which I’ve heard is good because it rubs against certain spots in certain positions, but I have no way to verify that myself. All I know is that she stared at it greedily, hungrily, as I walked over to my nightstand to pull out a condom. She took it in her hand as I undid the wrapper, took the tip into her mouth briefly as I fiddled with the rubber, which was a huge tease because those lips were oh so perfect for blowjobs, but I was not to receive one that night. She was too horny and ready to fuck. And as I rolled the rubber on to my cock and made myself ready for what was to come; so did she. Without a work she let me know how she wanted it. She turned her ass to me and got on all fours, pulling her dress up to fully expose that wonderful ass, and the tattoo at the small of her back. Doggy style is my favorite position, and I had never fucked a woman with a tramp stamp before, so seeing it was actually a turn on. This woman knew what she wanted, and made this one of the best “fuck-her-from-behind” experiences I have ever had.
With her dress up and ass open for me, I quickly got on my knees behind her and angled my swollen cock up to her entrance. She was so wet from earlier that I slid in with no problem, and she grunted in pleasure when my entire cock had filled her canal up, pressing against her walls. The feel of her ass against my hips drove me crazy, and I wasted no time on building a rhythm, the sound of flesh on flesh ringing out in my small apartment bedroom. The slap-slap was accompanied by the ‘oh-yes’ from her mouth, as with each deep thrust she expressed her pleasure. I had my hands on her hips, pulling her into me as I drove my hips forward, my cock like a piston into her. I was fucking this chick hard, my abs tight from the exercise, pounding as fast and hard as I could maintain at a steady pace. She wasn’t vocalizing words at this point, only guttural moans and even the occasional cute squeak betraying the amount of pleasure she was feeling to me. I loved every second of it. I spread her ass cheeks with my hands at one point, to get a view of her tight little asshole while I fucked her. I always fantasized about getting into that ass, but we never breached that topic, and I still wonder about it to this day.
But for now, her pussy was wonderful, and I was nearing my own climax. At the time, I hadn’t realized that I had made her cum a couple times, the condom dulls some of the feeling you get. But I was feeling it coming on. I am quiet in bed, I don’t make a lot of noises or say a lot, so my signal that I was getting close was to shift position a bit, scooting forward and driving my cock into her from more of an upward angle. I was really riding her at this point, and I leaned over to kiss and bite her in the middle of her shoulder blades, which caused her to moan in ecstasy and throw her head back. I grabbed her hair with one hand and worked up to my conclusion. As I came I pulled her hair and took one last deep plunge into her ravaged pussy, and she yelled out in delight as I held my cock in her as deep as it would go, my cock spasms in the condom. I could feel her clench around my cock as I came, almost like she was massaged every last drop of cum out of my dick with her pussy. I must have filled that condom up with how much I came, and I stayed like that, mounted on her, until the last wave of orgasm washed over me, and my cock finally began to ease up and soften. I slid out of her and lay next to her on the bed, and she snuggled in close and we made out while basking in the glow.
That was only the first of our nights together, we became FWB and I would head over to her place and spend the night, fucking at night and in the morning. We saw each other for a few months, but it ended when I graduated and left the state. I tried to hook back up with her on one of my visits back to my alma mater, but I don’t think she had any interest at that time. But she remains one of the best lays I ever had, and my only real FWB situation. I hope ya’ll enjoyed the story, I had the itch to put some of my experiences to pen and paper, metaphorically, and if this gets positive reception I can definitely add more in future.
Happy Reading!
EDIT: I messed up the title and some bad spelling/grammatical errors, had to repost
Source: reddit.com/r/gonewildstories/comments/6vzwk2/my_collegeera_fwb_and_first_milf