[FM] The story of how I (28m), almost impregnated my best friend (25f) during grad school

This is the true story of how before marrying my wife, I managed to get into some serious trouble with one of our close friends. Or alternatively, you could call it “The true story of how I had to choose between two fantastic women from Thailand.” Everything you are about to read is true with minimal embellishment. It all happened around 2013. I (28M) was in graduate school in a professional field, living in a converted greek frat house, now just a co-operative house with no greek affiliation. It was on campus but technically it’s own thing. There were about 25 students living in the house, all in close quarters but with our own private rooms. Everything else was communal. Needless to say, lots of close friends were made, and it was hard to avoid running into each other. Fair warning, this story involves cheating. It was the last time it ever happened and it was a learning experience.

My now wife, Stacy, and I were in the same class, and had been dating for 1-2 years. We had an on-again-off-again style relationship, and things were rocky at points. We were in a difficult graduate school program, with intense work schedules and lots of studying. We were “official” in that everyone that knew us knew we were an item, but at that time we were not fully committed to getting married and spending the rest of our lives together or anything. We were open to the possibility, but it wasn’t written yet. We knew that we had a lot of work to get done and you never know whats going to happen. So we were “a couple” and that was that. She was, and is, an awesome girl. 3 years my junior, full blooded thai, five foot zero, and about 110 pounds. Her ass was beautiful and much more substantial than you’d expect given her frame. Solid C cup breasts. Perfectly proportional, with some cushion. She had a no nonsense bob haircut and was a total nerd, but super hot in her nerdiness. She was a salt-of-the-earth kind of girl, into gardening and chickens. She was also kind of a work-a-holic and studied a lot more than me. She came from a conservative immigrant family, and she frequently made weekend trips back home to see them. One thing in particular that made our relationship difficult, was that she wanted to wait for marriage before anything sexual. She wasn’t even into kissing, without knowing it was going to lead to marriage. So we were in this long, drawn out courtship without a clear end game. Were we going to get married? Who knows. I knew I was really into her, and it felt right, but I wasn’t sure if I could stand a long sexless courtship lasting 4-5 years+. I was so horny and always wanting to sleep in the same bed as her, but most of the time it just didn’t happen because it would be too tempting. So we kept to our own separate rooms. During the day, we were inseparable. We did everything together.

Our mutual friend, Brenda, lived only a few feet away in another bedroom upstairs. She was the same age, also from Thailand, twenty five years old, about 110 pounds, 5’8″, with long flowing thin black hair, and a lanky slight frame–not much cushion but super hot just the same. Definitely petite. Her personality was a little different than my girlfriend’s. She was a city girl, pretty much down for anything “urban” and she was a lot more “cosmopolitan” than my girlfriend, but it was sort of a facade. Deep down she was also a huge nerd. She had some daddy issues and came from a broken, non-traditional family, another major difference from my girlfriend.

Now, I can tell you that we were all friends. We would go out for dinner together, attend holiday parties, sometimes just the three of us, but there were many other friends in the group as well. It was all platonic fun. The closest I ever got to Brenda on a private basis is, we would study together, or maybe watch a TV show together, sitting next to each other on the communal couch. The problem was that there was a sexual tension between us. Not overt, and pretty easy to ignore for the most part. But the major issue was that I was chronically sex starved, due to the arrangement with my girlfriend where we wouldn’t do anything sexual at all. There was always internet porn to satiate my desires, but I wanted to just sleep next to a beautiful woman so badly. I mostly just quietly kept chugging along, relieving myself in the privacy of my own room whenever the need arose. But it wasn’t the most fulfilling thing ever.

One weekend my girlfriend Stacy went home to visit her parents. This was pretty common as she didn’t get to see them a whole lot. It was a 2 hour drive away. She usually spent the whole weekend there and I got lonely when she was gone. It was a quiet weekend in our frat house, and Brenda was home. I was home. Maybe a few other people. A lot of the lights were turned out downstairs. I knew that I would be hanging out with Brenda. In fact, it wouldn’t have been a surprise to Stacy either. She knew we were all friends. She even knew I was attracted to Brenda and we had several conversations about it, that were along the lines of “I understand its hard for you being a guy and not being able to have sex…” I couldn’t really tell if there was a sub-textual “permission” in there, or not. I never really asked, but the implication was there. Whether I was imagining it or not, well, I’m not sure if I’ll ever know. Anyway, that night, I knocked on Brenda’s door and found her light to be on, and she was wide awake even though it was getting late, around 10:30pm or so.

“Watcha doing?” I asked.

“Oh nothing just studying” she sighed, obviously done and needing something else to do to wind down at the end of a long day.

“How about a beer?” I knew she’d say yes, since that’s what we all did to unwind.

“Sure!”

So we grabbed a few bottles from downstairs and headed back up to her room. I got out my guitar and played some tunes. We made small talk. At some point during the evening, the topic came around to sex. She knew I wasn’t getting any. Well it turns out neither was she. She was a bit of a chronic under-achiever with the opposite sex. Despite being classically sexy, of Thai origin, and in really good shape, she could never close the deal with men. She came off as kind of a weird combination of innocent, yet crazy, which always seemed to put men off. But me knowing her really well, I could see past that, to the basically good natured, chill woman she was.

We were getting a bit tipsy and I ventured into uncharted territory.

“What would you think about sleeping in the same bed tonight, platonically?” I asked, half jokingly, with a wisecrack smile on my face.

“Yea right” she scoffed. “Come on! You’re practically engaged.”

“Right. But with none of the benefits. I’ve been alone every night for years. I won’t lie it sucks.”

She softened and felt genuinely bad for me. “Awww”. She gave me a platonic intentioned hug, but it felt like a little more than that. She was dressed in pajamas and a robe, very mom attire. But her arms were uncovered, and her skin felt warm and inviting.

I steeled myself–“Come on! We can do this. Everyone is gone this weekend. It’s cold and dark outside. Why not? Let’s just see what happens. Worst case scenario we just keep each other warm and get a good nights sleep. It’s not like we have to have sex.”

Outwardly she wasn’t buying it, but inwardly I’m sure she was thinking about it. I wasn’t the only one battling a long string of lonely nights. A few more minutes of playful banter and one more beer, and the decision was made. She would stay over in my room tonight, and we would have a platonic sleepover. I think there was this sense between both of us that we had to see this through and figure out what was going on.

Later on, we literally got into my bed together with our shirts off and laid next to each other. We talked about how nice it felt to lay next to someone. She was nervous and not sure where this was going. I wasn’t trying to cheat on my girlfriend either. I literally just wanted some company and some skin to skin contact for my mental sanity, and that’s exactly what we gave each other that night. I have a memory of leaning up on my elbow looking at her perfect tiny breasts before turning off the light. Nothing else happened. We woke up the next morning honestly surprised that nothing terrible had happened. It felt like we were really good friends, maybe bordering on brother/sister love. We went about our day and I looked forward to my girlfriend coming home.

That was as deep as things got for a while. Actually a long while. At the time, we were 2 years into our 4 year program. The next year and a half went by quickly and we all continued to be good friends. Stacy never found out about that night, and we didn’t think much of it either. In fact we almost forgot about it. That is, until just before we were all set to graduate.

Once again, Stacy was out of town for a few days. Still no sex but our relationship was progressing. We were going to move in together after completing our program. Things were getting serious, but we were so busy that we didn’t have time to contemplate marriage yet. We were very happy with our relationship where it was, and neither of us were looking for other partners. She was set on marriage and kids. I was nervous, because I wasn’t completely sure that was what I wanted yet.

Brenda had since moved out of the frat house and gotten her own apartment. Most people just waited until they graduated, but a few decided to move out earlier for their own sanity and privacy. It was an extremely rainy night and I had just finished a long week of school. I texted Brenda.

“What are you up to?”

“Oh nothing just tired from a long week.”

“Want to go grab a drink?”

“Sure. Where’s STACY? :)”

“At her parents.”

“Ah, sure. Okay fine let’s go.” She was always up for hanging out.

So off we went to this trendy little bar in downtown. This was to be just a meetup for drinks. I had no intentions of following her back to her new apartment even though that is in fact what happened. She started the evening with a lemoncello and I had a nice IPA. She was dressed in a cute dress that was form fitting. It was a little formal, but that’s sort of how she dressed. Always with the designer shoes and fancy clothes. Even with casual friends.

We hadn’t really hung out in a while so we did some catching up, small talk, etc. She had a few failed attempts at online dating. I updated her on my relationship with Stacy–how I was feeling apprehensive about going out into the real world of adults. Having to get my own place to live, and the prospect of sharing that place with my girlfriend, who wanted to be my wife. It was all very overwhelming. She knew how I felt. She wasn’t ready to settle down yet. Not even close. We each had 2-3 drinks and stopped there as we had to get home still. Although it turns out her apartment was just down the street from the bar.

“Want to come see my new apartment? It’s awesome!”

“Umm, yea sure. Actually that would be good since I think I need a couple hours and a few glasses of water before I can drive.”

And so we walked back to her apartment. On our way there, I kept on admiring her petite figure. Her shoes had high heels, and they kept on making her trip up on the sidewalk. She wasn’t drunk enough to be tripping over things–it was the shoes. Little black shoes with heels. She was such a lovable dork. I loved her like my own sister. She was the friend I needed.

Once in her 3rd floor apartment, a few glasses of water turned into a few more glasses of wine. She ended up wanting to take a shower, but she said I could hang out and play her acoustic guitar that never gets played.

“Play me some sweet music! I’ll leave the door open so I can hear it!”

My stomach tied itself in a knot. The thought of her peeling off those formal clothes and letting them drop to the floor gave me an instant hard on. I knew I would eventually move in with my girlfriend and probably marry her. And I wasn’t looking to change that. But this was literally the last opportunity I would ever have to do something spontaneous, or at least it felt like it was. And so right after that, I did something very, very dumb.

I got up and peaked into the half open door leading to her steamy bathroom.

“What happened to the music??” She asked, genuinely concerned. I’m a pretty good guitar player and she was trying to learn as well.

“Oh my coordination is bad right now, I can’t play. It probably sounds like crap”

“What? NO way man. You are really good.” This conversation is happening between her in the shower and me in her hallway halfway looking through her bathroom door. I see a foggy outline of her frame behind the shower door, moving in shadows, creamy pale skin colored shadows.

“Aww you’re too nice” I said absent mindedly. Somehow those few drinks were really having an effect. What I did next was something I would never normally do. I took my clothes off and tossed them in the hallway and then went into the bathroom and shut the door.

“Hello?” She wasn’t done showering yet. I think it had only been 2 minutes since she got in.

“Hey Brenda?”

“Yea?”

“What happens next can never leave this apartment.”

“What are you talking about silly?” She had no idea I was naked, or in the bathroom.

Emboldened, I quickly opened the shower door and got in the shower with her. She was so shocked she didn’t know how to react. She was frozen. She had a bar of soap in her hand and she dropped it. It was a tub/shower with a mottled glass door. Space for two but not much more. She was facing me. The overhead lights were very bright which was not flattering for either of us. Our imperfections were on full display.

“Umm, here.” I bent over and picked up the soap. It was yellow and smelled like a candle. I extended it towards her, an offering, an apology maybe. The water streamed over us. She had the tiniest little boobs, but so perfect. She was instinctively crossing her legs, but there was a bit of black hair showing at the top of her triangle. I had a massive hard on and I couldn’t hide it.

“Oh no…no…no….what about Stacy…” she uttered, and I shushed her with an upright finger to my lips, reaching out with my other hand and touching her shoulder lightly, brushing my fingers along her collar bone to the base of her neck. I looked her in the eyes and said,

“I want you so badly right now”. She had no answer to that. Her nipples were rock hard. Tiny nipples, dark colored, with those little dots around them. I wanted to suck on them so badly.

“But, this is so wrong. I mean, you’re like a brother to me! I have to pee!”

Right then, almost as if on cue, the shower water ran cold, and we both sort of freaked out a little. The reality of the situation set in. What in the hell did we think we were doing?

She shut off the water and we both got out and dried off. She turned on the heating lamp above and the whole bathroom got darker and cast in this red glow. It also got very warm very quickly. We were standing in the bathroom trying to stay on the same bath mat, toweling ourselves off, occasionally bumping body parts and feeling skin on skin. We were slightly tipsy and neither of us knew what was going to happen next. The shower running cold had been a sort of temporary reprieve from the intensity of the moment, but now that we were under the warming lamp and drying off, it seemed like nothing could stop what was going to happen in the next hour. It was inevitable.

I grabbed her towel from her playfully revealing her naked body from head to toe and she laughed and played at stealing mine. We may have been physiologically in our mid to late twenties, but in that moment psychologically we might as well have been in our mid teens. I threatened to snap her with my towel and she cowered in the corner, laughing and grinning widely. I walked over and as she stood up, I pushed her against the inside of the bathroom door and kissed her on the lips. She didn’t stop me, and for the first time she wasn’t holding her legs locked together in the triangle death grip. Her pussy was outlined in soft, straight black hair. Totally natural. When I kissed her, I felt the tip of my circumcised dick brush slight across that hair, which sent a searing, sharp sensation right into my core. She wasn’t ready just yet. Then she disentangled herself from me, opening the door.

“I have to get dressed. And YOU have to settle down mister.” Still with the playfulness.

We stumbled out of the bathroom and into her bedroom. She went to her walk in closet and grabbed a pair of white cotton panties, with a flower print from her drawer. She awkwardly pulled them on facing away from me as I watched. With each passing minute our desire grew, despite her feeble attempt to stop it by putting on a pair of the most “little girl” panties she had in her collection. She turned around to face me and then slumped down to the ground in her closet beneath her oddly formal wardrobe. Whatever fight we had left was now gone.

I scooted up to her, both of us sitting on the floor facing each other. We were very close now. In fact my dick was so close to her that I swear it was resting ever so slightly on the outside of her panties. I reached out and very lightly touched her nipples. I put my finger in my mouth to wet it, then back to her nipple again, just like a feather. It seems that this was the tipping point….we got up and tripped over dirty piles of clothes to get into her queen size bed in a dimly lit bedroom. It was un-made.

She laid down on her back, eyes closed. I was on my hands and knees in front of her, laying kiss after kiss all over her little feminine breasts and tummy, which was flat and sexy. Her belly button was an inny and I licked the inside of it as I ran my hands all over her body. She was no longer verbal, though she did still have those little girl panties on. Finally I got down on my stomach and put my lips right up against her panties. Only a thin layer of flower print fabric separated her womanhood from my mouth. She smelled so wet and humid, the panties offering only a theoretical barrier. I could tell she was wet. I pressed in a little, and it was literally squishy. The panties suddenly seemed irrelevant. I reached up and slipped them up over her legs. She protested a bit but it was only a formality given her soft moaning. As they came off, it was like a wave of heat and humidity came out from underneath. I returned to my original position, lips hovering just outside of her soaking pussy, just taking it all in. I pushed ever so slightly forward with my lips, still closed, and made contact with her fine black hairs (she was totally natural, remember) overlying her swollen labia. Instantly I felt her juices which were barely contained within her soft lips. There were drops of female cum leaking down her slit and collecting at the bottom. Her pussy was absolutely fucking soaking. I don’t think I’d ever seen or felt a pussy this wet, in all my life before that, and after. She was so turned on and had been for the last hour, it felt like a vindication of some sort, that yes, in fact, she was incredibly ready for me. Whatever barriers existed in the physical world, they didn’t exist within her, at all. You could have shoved absolutely anything into her at that point, it wouldn’t have mattered. There was enough gooey cum there to swallow anything. And it only made my throbbing dick that much harder, and my building orgasm seem that much more inevitable.

Performing oral sex on her at this point seemed a little pointless. There was no way she could become any more ready to get penetrated. I love giving oral, but its a lot more fun when you can start from scratch. She was so ready for my manhood that anything else just seemed like a waste of time.

I got up into missionary position and placed the head of my dick just outside her lips near her clit. I was going to take this one slowly. I reached down and guided her hand to my balls and told her to hang on lightly which she did.

“Are you sure about this……” she breathed, obviously far away in a world of anticipation.

I rubbed myself up and down across her sensitive clit, but only after picking up some of her cum near the bottom of her slit to lubricate with. With all of that cum, mixed with my pre-cum, my dick slid perfectly across her clit, and I remained there, playing with her for at least a full 2 minutes. Every time I slid past it, she let out a little whimper which communicated that she had completely given in.

Just when she couldn’t take it anymore and seemed to be approaching orgasm, I stopped, taking her right to the edge but then denying anything further until I was inside her. I re-positioned her on the bed to my liking, her head straight back on the bed with no pillow. I reached around with both of my hands to cup both sides of her ass, with the tips of my fingers right around that area between the pussy and ass. I massaged that area, getting her muscles ready to take me. She was moaning more and louder. My penis, covered in her sticky girl cum, had no trouble sliding in. But she was still incredibly tight, almost virginal. I could tell she hadn’t had sex in a long time. Her vaginal muscles contracted tightly around me. I could feel the individual ridges on my dick, doing what they were made to do. They seemed to grab and hold on. She reached around my back and clasped her hands, and her legs went instinctively up in the air.

I went slowly in and out, very intentionally at first, taking note of every sensation, every ridge of muscle gripping my manhood, every squirt and squeek as her juices flowed all around me and out around the base of my dick. It was the most perfect pussy I’d ever felt. And I couldn’t help but stretch my chin up to admire her petite breasts. And as I took those first few strokes in and out, I put my mouth over her right nipple and sucked on it, eliciting some fairly deep moans of pleasure from her. With every moment that passed, her sounds got deeper and deeper, which made her seem more and more animalistic, more biological. Her closet full of weird clothes seemed miles away even though it was only across the room. Right now there were just two naked souls, doing what humans do.

I quickened my pace, being careful not to go to fast, since my orgasm which had been building for hours, no days, no weeks, now, was fast approaching uncontrollable territory. But I wanted her to have an explosive orgasm and I knew that I could do it with just my dick alone. I slowly but surely increased pace every few moments, burying my dick deeper inside her with each stroke, and leaving it buried a little longer each time. I could feel the tip of my dick squishing in against her cervix and the end of her pussy each time. There was a particular spot that each time the head of my penis went past, she seemed to let out this really primordial moan. That was the spot. I adjusted my strokes so that I always went past that spot, then started to go faster.

I still had my hands down around her ass, but to change things up I brought my hands up behind her head and gathered her long fine black hair in my fist and pulled it tight behind her head, pulling her head slightly back in the process. This seemed to really push her deeper into the experience, but I couldn’t keep my hands away from her ass. It was so little, that it was easy to grab and play with. So there my hands returned. I used my middle fingers on either side to gather some juices from her pussy, and then I used that to go back and forth between her ass (not asshole, I don’t do that) and pussy, massaging that area right between with her own juices, loosening her up to take my cum which I knew was coming, and couldn’t be stopped. Miraculously, our orgasms seemed to be coming along at exactly the same pace. I knew it. I was slamming into her quite hard now, and she was so wet it made no difference. I swear her juices were splashing off her pussy hairs everytime I penetrated her. The sheets were wet right underneath her pussy. I slowed my pace a bit so we could think for a few seconds before the orgasms came.

“You can’t……..you can’t…..” she moaned.

A few more thrusts, slowly. Some more silence. Deeper moaning. My grip on her ass took on a new dimension, I was squeezing hard now. I shortened my strokes to focus on her g-spot and made them much quicker. I didn’t remove my dick nearly as far, keeping it basically buried to the hilt, only moving back and forth about half an inch each stroke. Her legs were flailing around in the air but then she locked them around the small of my back. I wasn’t getting out now.

She opened her eyes for the first time, and her mouth started to open. Her face twisted into this distorted caricature of a normal human face, and I watched as her orgasm ramped up. She took in a few rapid deep breaths, which I matched with my dick in her pussy. She arched her back and her heels dug into my back simultaneously, locking our pelvis’ together in synchronous motion as I uncontrollably pounded her vagina, having absolutely no idea what was going to happen afterwards.

“oh my god….” I said……

“…..just…..just……okay…oh my god….oh my god…..cum…..cum….please”

And then, my dick and balls lit up sending shockwaves radiating outwards up my spine, all my muscles contracted at once and I fired what seemed like the biggest load of cum of my entire life deep into the very back of her pussy. From where my dick was shoved up against her cervix, I’m fairly certain I shot the cum directly into her uterus.

As my cum pumped into her, her vagina grabbed my dick so tight and held on for dear life. Her legs didn’t let go either, locking my dick into her pussy for the full duration, until the last contraction subsided. And as my cum streamed into her, waves of pleasure rippled through her entire body, shaking her to the core. Her peak subsided but her muscles still held my dick inside her, so I couldn’t really roll over, but merely collapse on her chest, dick still throbbing within her.

As I regained my conscious awareness, some mixed feelings danced across my mind. “What have I done? Did I just get my best friend pregnant and destroy my relationship with my girlfriend?” But we both were so exhausted and still under the spell of ecstasy that I pushed those thoughts away for tomorrow. Then, I just rested, and smelled the sweet scent radiating up off her chest. As I pulled out of her, I noticed nothing came out. That cum went straight in, no doubt about it.

The next five minutes were bizarrely normal. We got up, drank some water. We shared a look or two. I got dressed and went home. I honestly had no idea what was going to happen the next day. I was a little terrified, but a good nights rest does wonders. I woke up the next morning to a text from Brenda.

“I’m on birth control, don’t worry about it!”

“Oh, thank god.” I replied.

“Let’s never mention, or do that again” she said.

“Yea, probably a good idea.”

Later on, we caught up in person and deconstructed what happened. Obviously, we were both sexually starved. What we did was very, very wrong, but perfectly explainable. Combine hard school work, lots of stress, and my girlfriend insisting on a long sexless courtship, along with some some honest attraction, albeit slightly of the brother/sister kind, and it was inevitable. Wrong, but inevitable. And ironically, that experience might have been what caused me to eventually marry Stacy. Brenda insisted that I marry her, and stay true to her. She told me that I was in for a lifetime of that kind of sex if I could stay true. Brenda was truly a great friend. She easily could have ghosted me or something (because we no longer lived in the same building), but she didn’t.

And so I did marry Stacy a few years later. At the end of the day, she was more my type. More marriage/mom material. More shared interests. We were never the urban/cosmo type of people. I simply got along better with Stacy and had more to do. She also had the better ass and boobs, for sure. She has no idea this ever happened. We have a happy marriage and two children, and we do have amazing sex, although not as frequent after the kids. I lost touch with Brenda, although she still lives in our state. Her phone number is still in my phone and I could text her any time, but I never have. Maybe some day we’ll all have a reunion. In the meantime, my wife Stacy, and only Stacy, gets to have the earth-shaking vaginal orgasms.

Still, that night with Brenda was easily, without a doubt, the most mind blowing incredible sex I’d ever had, and I’ll never forget it.

Source: reddit.com/r/gonewildstories/comments/jcr0nv/fm_the_story_of_how_i_28m_almost_impregnated_my