I met Anna at the beginning of my sophomore year of college. She was pretty: long, brown hair, tattoos up and down both arms, glasses. She had a perfectly thin layer of fat that, along with her broad hips, gave her a luscious ass. She seemed nice, at least at first. She liked film, literature, and art; in other words, your standard liberal arts girl. But in terms of attitude, she was a suburban white soccer mom interrogating an H&M manager about a pair of yoga pants that don’t stretch enough. She did not like me and nor I her. She would constantly criticize me, and she talked incessantly. I tried to get away, but at the beginning of that year, she started dating my best friend, Mark. I fully sympathize with Mark for dating her, and I commend him for sticking with the relationship for as long as he did. She made him fucking miserable.
I would like to say that Anna’s personality spoiled her looks for me, and that I hated her so much that the thought of even touching her repulsed me. In reality, the only thing that kept the thought of undressing her in the middle of a crowded party and fucking her on the floor was that my best friend was dating her. She was, truly and honestly, very hot.
Mark and Anna date for around a year, then comes a disastrous break up. It actually happened while they were staying with Anna’s parents two states away for Thanksgiving, and Mark ended up hitchhiking all the way back to school, but that’s another story.
After the break-up, Anna confirmed what everyone had known all along: that she was deeply, deeply horny. In the span of the next year, she dated and dumped four guys and fucked many more. Rumor spread that she had regular threesomes with her female roommate and whichever guy was attached to her at the moment. Dudes were throwing themselves at her.
I am on the sidelines for this spectacle. Anna and I began to get on better terms around this time now that we weren’t constantly in contact a la her dating Mark. Sexual tension rose here and there, when she wasn’t otherwise involved, but I knew in my soul that banging her was a bad idea. It would ruin my relationship with Mark, who was still recovering from the breakup (knowing his ex was getting around didn’t help). And it didn’t really seem like any guy who fucked her really came out ahead. If you caught a feel, she didn’t. If you didn’t, she did. Nobody won.
This was my thinking throughout junior and senior years. Just stay away. But, as it happened, the two of us ended up sharing a very small class in the last semester of my senior year. Neither of us really knew anyone else, so naturally we would do homework and group projects together. I began spending around an evening a week at her apartment, often lying on her bed as we worked out complex Latin grammar exercises together. She started inviting me to parties she would throw at her place. Often, if I stayed late enough at these parties, she would start drunkenly holding onto me, not letting ago until I’d left to go back home. To be clear, I had no romantic feelings or intentions. We were friends.
But feeling her body against mine at a crowded party, having her sit on my lap and feeling her ass – her whole body – through the thin fabric of her dress pressed against me, it was making me majorly blueballed. She had an active finsta with nudes that became my lifeline. Toward the end of the year, we couldn’t have an afternoon study session where I didn’t think of seeing her completely naked and fucking her.
It’s graduation. Amidst all of the celebration, I host a party for close friends at my apartment. Mark is there, and after both of us are six or seven drinks deep, we are talking outside alone. He asks me the dreaded question.
“Did you fuck Anna?”
This had been a growing tension in our relationship for months, ever since Anna and I had started spending more time together. Clearly, people had seen us at parties behaving like more than just friends. I told him the truth.
“Mark, hand to god, I swear I haven’t hooked up with Anna. I would not do that to you. I know we’ve been touchy-feely, and I’m sorry for that, but you have my word it hasn’t gone beyond that.”
“Dude, listen, I don’t care. Even if you had – maybe I would be a little pissed – but honestly I stopped having feelings for her months ago.”
I could tell he was genuine. I was drunk, and he was leaving the next day, so I knew I wouldn’t have the chance again.
“Mark, can I fuck Anna? Before I leave?”
Mark burst out into laughter, almost crying. “Yes, dude, you have my blessing.”
——
I had never really “decided” to have sex with someone before. I had definitely hit on girls at parties, but every hookup I’d ever had ultimately just kind of ‘happened,’ without me really planning beforehand. So when I decided to fuck Anna, I wasn’t really sure how to go about it. Do I just ask her? Do I ask to hang out and see where things go? Anna was staying in our college town for the summer, since she still had a year to go, and I was hanging around for two weeks until I moved away. I had time – but I didn’t want to leave without having fucked her.
Much like her ass had on so many occasions, the opportunity fell onto my lap. She texts me the next day about helping her move some furniture to her new apartment, just down the street from her original one. Of course I agree.
I come over around 11. It’s a hot, late May day. She’s wearing a miniskirt and a loose t-shirt with no bra. It’s really only a couple pieces of furniture, but with the temperature, we’re sweaty and exhausted by the time we’re done. Sitting alone in her new apartment, we plop down on the couch.
“Hey, want some water?” She asks.
“Sure.” As she gets up, the back of her skirt flies up and I see, for a split second, her glorious ass and the blue thong that barely contains it. A moment later, our hands touch as she passes me the cold glass. We chat for a while, and there’s a little silence.
“I can’t believe you’re leaving in a couple weeks,” she says, “I’m gonna miss you.” She rests her head on my shoulder.
At this point, I couldn’t give less than a fuck. I put my arm around her. She wraps her arms around me. I can feel her tits, small but significant, pressing against my stomach.
“Are your surprised?” I ask.
“About what?”
“That we never hooked up?”
She looks up at me, smiling and incredulous.
“I never thought you wanted to.”
“Oh boy, I have wanted to for months.”
“Really?”
“Absolutely.”
“Was it Mark?”
“Yeah, but we talked. There’re no issues there.”
She smiles, blushing. A silence.
“So,” I ask, “what do you wanna do?”
“Um, well-“ I kiss her before she can finish. It’s one of those electric kisses that is alive with all the tension that led up to it. We kiss again, and then again, and soon she is sitting on my lap as we make out. I can feel her heavy ass through the thin fabric of her miniskirt. My arms are around her waist; hers, around my neck. She is grinding her hips into mine. I am lifting the back of her skirt and feeling her magnificent ass.
“I’m so glad this is happening,” she says as I kiss her neck.
“Me too, “ I say.
We keep kissing, her on top of me, running her hands through my hair. I lift up her shirt and toss it to the floor. Her tits, the tits I’d been fantasizing about for years, were in front of me. I bury my face into them, kiss her perfectly round nipples, marveling at how soft they are. Southerly, I am rock hard. She is grinding my dick against her panties. She is unbuttoning my shirt. As soon as the last button is free, I push her off me, so that she stands in front of me. I pull her skirt down to her ankles. Next, her blue thong. I kiss her perfect, shaved pussy, gliding my tongue across her clit. I turn her around so her ass, that otherworldly ass, faces me, and give it a firm smack.
She turns around and lowers to her knees. My pants come off, then my underwear. She takes my dick in her hand expertly, slowly and firmly. I
l’ll never forget the feeling of gliding into her mouth, how deep she could take me, the way she would lick down my shaft and softly kiss my balls. I was in the fucking zone.
“Here, stand up.” She complies. I pull her towards me.
“Do I need a condom?” I ask.
“No, just please don’t cum in me.”
“Okay, I won’t.”
She lowers down onto me, audibly gasping as I go inside her. I’m not huge, but the way she almost shook as she said “Oh my god, you’re so big,” made be believe, in that moment, that I was a goddamn pornstar. She rode me up and down, up and down as we both moaned, her perfect ass slapping against my thighs and her tits jumping in my face. After a few minutes, I pushed her off.”
“Here, get on your hands and knees.” Again, she complied, and I fucked her doggy on her couch as her moans echoed around the empty apartment along with the sound of me clapping her ass. It was the best sex I’ve ever had.
“I’m gonna cum,” I said finally.
“Um, okay, just cum on–“
“Can I cum on your face?” I heard myself say.
“Oh, uh, sure.”
I pulled out of her and directed her to her knees, on the floor. I put my dick in her mouth. As she jacked me off, I could feel every ounce of frustration I’d ever felt toward her building up. Every memory of indignation pulsed through me as I pushed my dick deeper into her mouth until she almost choked.
“Is that okay?” I asked, as tears streamed down her face.
“Yes,’ she said, smiling.
I grew closer and close to cuming. She looked up at me, smiling and expectant, until finally I bust the fattest load I’ve ever mustered onto her beautiful face. She is truly covered. My cum is dripping off her chin onto her chest.
We cleaned up and hung out for a little longer. In the two weeks before I left, we had sex a few more times, and each time was just as fantastic. That was about a year ago. She has a new boyfriend now, and we don’t talk much anymore, but I have fond memories of the last few weeks we spent together.
Source: reddit.com/r/gonewildstories/comments/d0bgtr/i_fucked_my_best_friends_ex_who_i_hated_with
can we get some screenshots of her finsta?