(M)y (f)irst time anal with Allison | 2016

So my first girlfriend in college was sexually inexperienced when I first met her, but she – and I – were sexually adventurous, and tried many new things. Including anal.

Appearance-wise, Allison was far different from the last two girlfriends I’d had in high school. She had long, thick, dark black hair. She had lovely brown eyes, and an amazing smile. She was my height, and while certainly not overweight by any means, she just wasn’t that skinny. I think the term used now is curvy. And she definitely had the curves. She bought her first thong underwear when we dated, it made her generous ass look fantastic. Her breasts were 36C, she had by far the largest breasts of any girlfriend, I went crazy for them. She also had a very luxurious patch of dark pubic hair. (This was back in the day when a completely shaved pussy wasn’t all the rage, and women looked like women).

I never actually penetrated her pussy until three years into our relationship. It started with other masturbating together on her bed. She had an unusual technique to get off: She’d lay on her side, and flexed her muscles around her pussy, doing something like exercising kegels. She explained it to me, but I never quite understood. All I knew is that it didn’t take her long, and it was incredibly sexy to watch her get off. I’d be stroking my cock, and she’d watch me, and I guess that got her going too.

A year into college, we each had our own single dorm rooms, and plenty of privacy to try out all sorts of sexual kinks. She still wouldn’t let me penetrate her, but we found lots of fun things to do with our bodies. Suffice to say, it was exciting times.

We discovered a new, fun way to get off. She would more or less lay on her stomach, and thrust her ass up in the air. I would slip my cock between her lovely ass cheeks, and kinda push them together around my cock. I would start thrusting up and down, as if my cock was in a pussy. Soon, we found it worked better if I used lube—sometimes we used hand lotion, or Vaseline, and once in a while, when one of us was brave enough, we’d go to a pharmacy and buy a bottle of KY (yeah, we were that naive back then). I had been masturbating a lot with Vaseline at the time, so it felt pretty natural.

As I thrust up and down along her asscrack, she do her muscle flexing thing. The first time we did this, it was so exciting for me that I came pretty quickly. After a while, it got to the point where I could last long enough for her to cum twice, and then I’d spray my jizz all over her lower back.

One night, for some reason it took me longer than usual to get off. She had actually worked her way through three delicious cums. I think she got a little impatient, but then she turned her head around and looked at me.

“Do you want to, you know…try anal sex?” she asked me.

“Um…yeah!” I said. Now, I’d had pretty normal sex with my high school girlfriends, usually the basic missionary, preceded by some oral and maybe a bit of hand work. Allison and I had tried a lot of neat stuff, including getting off outside, in the laundry room, the library, and a movie theatre. Several times we snuck into the women’s bathroom late at night and play around in the shower. We’d often do oral. We even experimented around with pee games. Toys. Handcuffs. Yeah.

Anal sex, however, was my own personal holy grail. This was during the early days of the internet, so I’d heard of a lot, and asked my girlfriends if they’d like to try it. I was only rejected, that I thought I’d never get the chance. As such, I never brought it up with Allison. And here she was the one suggesting it!

Almost at the same time, we reached for the Vaseline. “You’ll need to use a lot of that,” she told me. I had read up on it on the internet, and knew as much. I could feel my cock harden more than it ever had as I sloped it up with my hand. It was positively dripping with lube and precum.

Allison must’ve read up on the act as well. She got on her knees, the settled her head and shoulders onto her pillow on the bed.

“Spread your knees some.” I told her. She did, and there was her rosebud, waiting for me to penetrate it. I paused to take in the glorious sight. She wiggled her hips suggestively, impatient for me to begin. With my hand, I placed the head of my cock at her entrance. I knew I should go slow, but all of me wanted to thrust into her. I held it there, at the entrance, for several seconds, and then, made a small push— “Aaaahhhh,” she hissed. No! I didn’t want this to be painful for her. I pulled back. She looked back at me, grimaced, but yet still looking expectant. “It’s okay, try it again.”

So I did. I must have got about half of the head of my cock in her when she gasped again. Felling me back out, she told me, “No, it’s okay, keep going.” She gasped again as I got my entire cockhead in. I paused again, to savor the feelings. This was by far way tighter than any pussy my cock had previously been in.

Now it was time for business. “You okay?” I asked her.

“Yeah,” she grunted. “Keep going.”

I slowly thrust the rest of my cock in her, making it all the way in less than ten seconds. It felt exquisite. Every inch of my cock was being squeezed by her.

Suddenly, she did something with her muscles. It felt like she was tightening her grip at the base of my cock, and then the sensation of pressure rode all the way up along my member. And that was enough for me. I came, and I came hard. I had not expected it, and the breath was taken out of me as I felt my cock spray it’s cum all over inside of her. Holy crap! This was probably one of the most incredible orgasms I’ve had in my life. “Did you just cum?” She asked me. I was too breathless to answer, but she looked behind her and saw me nod. “Shit, that didn’t take you long, did it” I shook my head.

“Don’t pull it out yet,” she instructed me. She was still grimacing, and I was worried she was in pain. I asked her. “No, it’s…not bad. It’s just…uncomfortable. It feels really full.”

In time, my hard-on went down, and I slipped it out of her. “Wow….”I said. “That was incredible. Thank you.” She turned and sat up, and me, still on my knees, leaned in to kiss her. She kissed me back, and we shared a lingering wet kiss, full with tongue. Then she quickly scampered up and away from the bed, pleading a call of nature.

So that was our first time. We tried it several times afterward. Sometimes it worked, but sometimes it was just too painful for her. Still, those few times I was lucky to make it all the way in, the exquisite feelings along my cock made me cum pretty quickly. It was probably another three months after that first time we had anal sex that she let me try her pussy. And from there, the relationship gradually deteriorated, and we were over when she left the country the next school year.

But I’ll never forget how kinky we got.