Failed anal adventures with Ava [MF]

When I was in college I studied abroad in Asia.

It was an incredible experience, and I recommend it to everyone who has the opportunity. But my time there was made truly special by my first real girlfriend: Ava.

Ava was the language partner of a friend of mine. For those who don’t know, this means a local in your city who wants to learn your language, and you want to learn theirs, so you informally hang out together. I met her at dinner with friends, and we hit it off. She had long silky black hair, a perfect slender frame, nice curled lips, pretty brown eyes, and a cute butt. She was also a year older than me, at 21 (I’ve always liked older women). After a few more times hanging out with friends, I asked her to take a walk with me around our university at night, and I kissed her beneath the pines trees in the warm night air.

We became pretty inseparable after that, dating officially, spending large amounts of time together, and just generally basking in the happiness of young summer love.

One problem we had, however, was sex.

Ava’s relatively conservative culture expected young women to remain virgins until marriage, and Ava took those expectations very seriously. Thankfully, that didn’t stop us from exploring in other ways, and one of my earliest and best memories is Ava wearing one of my black button-down shirts and nothing else, my face buried between her legs, and her grabbing my hair and screaming in pleasurable agony.

She loved my tongue, and I loved her throat; but we both wanted more.

I, being the genius that I am, suggested anal sex. “That way you’re still a virgin!” I explained. Her skeptical frown suggested she felt otherwise. But we were both young, and in love, and really fucking horny. So after talking about it more, she finally caved. “Ok, let’s try it this weekend,” she said.

The next day I went and got condoms and lube. When the weekend came, I also bought her a half-dozen roses. And some booze. Vital, vital booze.

We drank our plum wine, and began kissing in my bed. I took her clothes off, and she got me down to my underwear. “Turn over,” I said, and she nervously flipped onto her stomach. I rubbed her cute butt for a bit, both because I loved it and to calm her down; then I got the lube and squirted some on her butt and some on my middle finger. I rubbed both around her aperture, and slowly slid my finger it.

Now, it could be that her asshole was just really tight (possible), or this Asian lube was crap (probable), or that my technique was flawed (almost certainly); but almost immediately Ava started grimacing and groaning, saying it burned and didn’t feel good at all. That was enough for me to feel so bad I lost my erection. I slid my finger out, laid down next to her, and made out with her until we fell asleep. At this point, we both agreed that our mutual desire to preserve the peaceful integrity of her butt was more important than our mutual desire for me to stick my cock in it.

We tried again a few times, with both of us initiating it at different points; but it was always the same. Her ass would burn from my finger or the lube or both, and she would just be in too much pain. At one point she said “just stick your dick in,” so I grabbed a condom and lubed up; but I only got the head in when she started saying “no no no no.” (Ava, if you’re reading this, you were a goddamn trooper.)

But soon the summer was ending, and I was getting ready to go home. We were both very sad to leave each other, but agreed long distance at this age wouldn’t work, and we’d enjoy the time we’d had together and part as friends. That sadness, however, turned into some really hot making out and oral. One of our last nights together, we were getting hot and heavy under the covers, already naked. I was rubbing her pussy and she was moaning, when all of the sudden she grabs my hand to stop me. She gets out from under the covers, walks around to the edge of the bed, gets on her knees, and bends over.

“I want to have anal sex before you leave, Acrobatsaresexyhot.”

Well fuck me. I nearly jump out of bed, racing to the bathroom to grab the condoms and lube. She’s so horny already, I think, that this just might work. I lube her asshole. I squirt some on my dick, and place him at the entrance to her back door. I slowly push in. This time, I make it in past the head. I leave my dick there for a minute, letting her get used to it. And it…it seems like it’s working. She’s rubbing her clit a little, and seems to be ok! My dick is in her ass!

Now, to all the ladies out there who tried and failed to take it up the butt for their partners, I’d just like to apologize. Most of us mean well, we really do. We like your butts so much, we want to express that profound affection in every possible way. We just…get a little carried away sometimes.

I was so elated that it was finally working, we were finally having sex. So I thrust the rest of my cock into her ass until my balls were touching her pussy.

This, dear reader, was the downfall of a young and stupid man. If I had just let Mr. Happy rest contented halfway in Ava’s ass, and slowly pumped in and out, we would’ve made love for the first time that night. As it was, she screamed in pain, immediately started crying, and ran to the bathroom. After about 5 minutes, she came out with puffy eyes. I felt like her asshole probably felt.

She said “it’s just not gonna work,” and hugged me; and I hugged her back, and we cuddled all night. And two days later, I left, forever.

Source: reddit.com/r/gonewildstories/comments/6w2p6j/failed_anal_adventures_with_ava_mf