Producer’s note: This story was originally published here.
This is a true story that basically spans an entire decade. Obviously all personal details have been changed.
I went to high school in a small town. My junior year a girl moved to the town from several states away; her name was Amy. As it turns out, Amy lived only about a mile from me, but neither of us knew that at the time.
Amy and I had several classes together, but I wasn’t attracted to her at all initially. She was quite tall for a girl (5’10” or so) and, while she was skinny, she was also sort of bulky, if that makes any sense. She just didn’t appear very feminine. She had this short hair cut that I didn’t find appealing. Her face was also not classically pretty. Her body seemed about average.
She started talking to me a lot and honestly I found her annoying. It didn’t occur to me that she was hitting on me until she became way more forward about it. At this point probably half a year had passed since I first met her. When I realized she liked me, I tried to avoid her even more, because I didn’t have the same feelings towards her. This is when I realized she lived so close to me, which I was pissed about because it meant she started asking if she could come over since I was practically within walking distance.
Eventually I decided to just let her come over, and we jumped on the trampoline in my parents’ yard. Something about her was different this day. She was way more attractive than she’d ever been previously. It was a little cold out and she was wearing this pink sweater that looked really good on her. Her thick black hair had grown out over the year and I realized she was actually pretty. I also noticed for the first time that she had huge DD boobs. She always dressed modestly and they just weren’t very detectable until this moment.
From that point on I saw her differently. I started becomingly increasingly attracted to her. We ended up dating for about 1.5 years. To compress this part of the story, which isn’t all that interesting, our relationship was not that great. We did have sex, but neither of us was any good at it. I did love her tits though. She got them pierced at one point with rings, which was super hot. The problem is that she was not very stable mentally. This caused enough problems that it prevented us from ever having a decent sex life. I learned that she had a troubled home life, her parents were divorced, her dad was a bit creepy and a drunk, and she had all these astoundingly irrational quirks that troubled me more than charmed me. She’d come from a very poor family, and I’d come from an upper middle class family; to be honest I struggled to relate to some degree. It was a foreign notion to me that she had to get a fast food job in high school, distracting her from her schoolwork, just so she could get a new shirt or pair of shoes that she desperately needed. I realize this reflects poorly on me, and that’s fine — I had a sheltered life growing up and at this point in time had not yet moved out of my parents’ home.
Combine all this with the transition to college and we broke up somewhat nastily.
In fact, to say it was nasty would be an understatement. The precipitating event was when I turned her down for sex one night. She’d been out at a club and came back at around 4am. I woke up to banging on the door; it was a mutual friend with Amy more or less draped over her shoulder. Amy was too drunk to walk. We laid her on the bed next to me, and she was on the verge of passing out. The mutual friend left and I prepared to go back to sleep. Amy woke up just enough to put the moves on me though. It was clear she was very horny, but it was also clear she was way too drunk to consent. I didn’t want to even play in that ballgame at all so I politely explained that she was too drunk and we could have sex in the morning. I didn’t think she’d even be able to remember.
I thought she understood and things were fine, but holy hell was I wrong. All hell broke loose the next day. It was as if her entire universe collapsed on her. I don’t think she’d ever been turned down for sex in her life, and she was totally incapable of coping. It didn’t matter to her that my reason was that I didn’t want to ambiguously fucking rape her when she could barely talk and form sentences and couldn’t walk. She told literally the entire floor that we lived on that I refused to have sex with her and she spread a rumor that I was gay, which evidently people believed. This pissed me off on multiple levels, one of which was simply… why the hell is being gay still viewed as an insult anyway? Jesus Christ, have we made no progress?
Anyway, I never had many friends on that floor anyway and she ensured I never would, as my effort at not fucking her when she was too drunk to consent had caused me to be ostracized by that particular social group. The school I was at sucked academically too, and I ended up transferring a few semesters later to a top-ranked school in a different state. She ended up transferring too — to the other side of the country.
That, I thought, was where the saga with Amy ended. I was glad to be rid of her.
Fast forward many years. I’ve graduated top of my class and have become pretty successful in life. Amy got married and had three kids. I had dated but ultimately stayed single and childfree at this time. Over the years she’d occasionally sent me messages on Facebook giving me updates on her life, but I didn’t care and often didn’t even respond.
One day she apologized. I guess it took her 5+ years of reflection on the event to realize that she might have overreacted just a bit. I was hesitant to accept her apology, but I decided that forgiveness is the best antidote to your own suffering. After this, I was willing to chat with her more. We chatted on and off for about a month. We were still living in opposite areas of the country.
At one point, she made the claim that she was always “crazier” than me when we were dating. Keep in mind our chats had been 100% PG and platonic up to this point. I wasn’t sure what “crazy” meant in this context, and given that she was married with kids I didn’t want to push it. But she’d struck my interest so using my most masterful and delicate language, I massaged the topic for a while as we periodically found each other online until she admitted of her own volition that “crazy” meant “sexually crazy”.
I contested her claim, saying that I was just inexperienced and we had a lot of other baggage in that relationship that distracted both of us from the sex life. She seemed open to admitting that this might be true, and this led to a discussion of exactly how “crazy” each of us was and is. This was the ice-breaker we needed. It didn’t just break the wall; it shattered it.
We both realized that we were way more sexually compatible than we ever previously thought. Our relationship had been so shitty that we never realized we both had so many of the same kinks. Our sex had always been vanilla and gentle. But I like much rougher sex, and I didn’t think she did at the time. I told her as much, and she couldn’t do anything except laugh — her biggest turn on, it turns out, is just being relentlessly pounded from behind while having her hair pulled.
Her husband, apparently, was horrible at sex. She’d been fantasizing for years about being fucked hard and deep. Our chats got her so turned on that she had to stay up late at night, often until 3AM, just so she could get some privacy and furiously masturbate.
It wasn’t long before she started sending me nudes. And holy shit her tits were huge. They’d continued to grow since high school, and they were now in DDD territory. Our chats got her so wet that she started masturbating daily to the fantasy of meeting up.
Months passed until she had an opportunity to buy a plane ticket and come visit me. I still don’t know exactly how she explained it to her husband, but she managed to pull it off. When she landed, she texted me that her pussy had been soaked in anticipation the entire time she’d been on the plane. She was coming on a Friday evening and was going to head back on Sunday, so we had a weekend to ourselves at my place.
She took Uber directly to my apartment. When she arrived, I went out to greet her and walked her back to my unit. The initial greeting was, of course, awkward. There’s no way it couldn’t be: two people who haven’t seen each other in nearly a decade, whose last parting was on less than good terms, who are both dying to fuck each other, and for her it would constitute cheating. We tried making smalltalk but it wasn’t working all that well.
She was wearing a short skirt with a tank top. Her huge tits were basically bursting out, and her legs were perfectly shaved. Just seeing that got me hard because I knew it meant she’d just shaved or waxed her pussy too. She was looking hot as fuck, and her thick black wavy hair rolled down and adorned her shoulders beautifully.
Each step towards my apartment brought us closer to the hard, explosive fuck that we’d both wanted since we first started dating so many years ago. When we got in, we couldn’t be held back. Immediately after closing the door I pinned her against the wall and started making out with her. She was so turned on that even just kissing her made her moan. I pulled her tank top down to expose her huge tits. She had no bra on. I left the shoulder straps on so it sort of propped her tits up. She’d also re-pierced her nipples, so they were incredibly sensitive. I grabbed both her tits and sucked on her nipples; I think she almost came just from that as she got weak at the knees. I reached down and up into her skirt to feel her pussy through her panties; she was literally dripping wet, like her legs were soaked. She let out a muffled “fuck”, but she was too turned on to really speak in complete sentences.
I turned her around, bent her over a bit against the wall, and pulled down her skirt. She was wearing a thong, and I immediately grabbed her nice, super pale ass cheeks. (I didn’t mention it above, but Amy is white and pale as fuck.) “Fuck me hard,” she begged. I wasted no time. I pulled down my pants, quickly put on a condom that I’d already laid out in preparation, and right before insertion I realized that this is possibly the hardest my cock had ever been. It felt literally like a rock, like it was going to explode. I slipped the thong to the side, teased her pussy a bit with the head of my cock, and then slipped it in all the way. Now I’m not huge down there, but I’m a solid 7 inches or so and reasonably thick. I’m big enough that I have to be careful. So I was slow at first until I had my cock deep inside her, and she just let out this incredible “FUCKKK…”. I hadn’t even started fucking her really and her pussy juices were pouring out. I’ve never had someone respond so enthusiastically to sex; I guess this is what many months of anticipation will do.
I immediately started pounding her, because I knew she wanted it and could take it. Juices were freely seeping out of her pussy and my whole groin area was getting wet. Every thrust was accompanied by this sloshing sound. Within a minute I heard her say, “Fuck I’m cumming, oh fuck, oh god, I’m fucking cumming.” She came extremely hard on my dick, then turned around, got on her knees, ripped the condom off, and basically shoved my cock down her throat. I had no idea she could deep throat, but she basically swallowed my entire throbbing cock.
I grabbed her hair and started gently face fucking her. She loved it. This is something I never would’ve done in high school. So I started fucking her face a bit harder, and she started rubbing her clit. She seemed to be on the verge of cumming again just from this when she got up, ran to the couch, laid back, and spread her legs and pussy. I grabbed another condom and put it on. This position and angle let me pound her relentlessly hard, and her sopping wet pussy seeped juices all over the couch. I can’t count how many “fuck”s she let out during this.
Eventually I was ready to explode. I pulled out, ripped off the condom, and completely covered her tits and stomach in cum. We laid back on the couch a bit in bliss, marveling at what had just happened, at how much sexual chemistry we had and yet it had taken us so long to discover it. We talked a bit about random things while she lay there covered in cum. About 15 minutes later I was getting hard again. We started making out again. I realized I was rock hard, so I jumped up, grabbed a condom, and started pounding her right away, no build-up this time. “FUCK yes,” she said when I pounded her with no warning. This was the first time I’d fucked someone who was already drenched in my cum, and she seemed to love it. She started running her hands all over her tits, rubbing the cum in all over herself as her pussy became drenched in juices yet again. Within a minute or two I heard, “fuck, fuck, fuck, oh shit, I’m cumming again. FUCK.” She absolutely cursed like a sailor during sex. She arched her head back in bliss as her pussy came again all over my cock, and I saw all my cum glistening on her pierced tits as they were sort of propped up in the air in this moment.
It wasn’t long until I was ready to explode again, so I pulled out, ripped off the condom, and came a second time all over her tits. She rubbed her hands through it and then sucked the rest off my cock.
That was the beginning of my weekend with Amy. This was the first (and only) time I’d basically had sex with someone twice in a row. For the remainder of the weekend, we basically hung out in the apartment, naked or half-naked the whole time, fucking hard in a variety of positions, occasionally leaving to walk to a nearby cafe for food. If there’s any interest, I might write a second post about some of the other sex we had that weekend.