First Anal sex with Alice

 So my first girlfriend in college was sexually inexperienced when I first met her, but she – and I – were very adventurous, and tried many new things. Including anal. When we started dating, I thought Alice was by far the most beautiful girlfriend I’ve ever had, and she still is to this day.  She had long, thick, dark black hair. She had lovely brown eyes, and an amazing smile. While certainly not overweight by any means, she just wasn’t that skinny. I think the term used now is curvy. 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,  by far the largest breasts of any girlfriend I’d had to that point, with large, dark areola and sensitive nipples that always seemed to be budding out.  She also had a very luxurious patch of dark pubic hair that drove me wild.  I love women with a full bush. When we started getting physical, she made it clear she was going to remain a virgin until she married.  That didn’t stop us from fully naked and experimenting with oral sex, but neither of us was experienced at that time to fully satisfy each other.  So we began to masturbate together. She had an unusual technique to get off: Laying on her side, and she flexed her muscles around her pussy and thighs. 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. After a year of dating, we discovered a new, fun way to get off. She would lay on her stomach and thrust her ass up in the air. I usually drizzled a little lube on her ass and slip my cock between them. I would start thrusting up and down, as if my cock was in a pussy. As I thrust up and down along her beautiful, plump ass, she did her muscle flexing thing. The first time we did this, I was so turned on I came within a few minutes. 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, we were both exceptionally horny, and by the time I came, she had squeezed her way through two delicious cums. Ten minutes later, I was getting hard, and started thrusting between her lovely cheeks.  Because I already came once, it was taking me longer than usual to get there. She got a little impatient, turned her head around, and looked at me. “Do you want to, you know…try anal sex?” she asked me. “Um…yeah!” I said. She handed me the bottle of  lube. “You’ll need to use a lot of that,” she told me. My cock had never been so hard in my life.  I stroked my cock to make sure it was fully covered in lube. Alice got on her knees, the settled her head and shoulders onto her pillow on the bed.  “Put some lube on my hand.”  I gave the bottle a squeeze and watched her rub it between her glorious cheeks. “Spread your knees some.” I told her. She did, and there was her rosebud, waiting for me to penetrate it. 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 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. All the way 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 my cock almost all the way out of her, leaving only the head.  Then I pushed back in.  She was so tight! It felt exquisite. Every inch of my cock was being squeezed by her. I pulled back out, and thrust in again. I could feel my imminent cum and knew it wouldn’t be long. 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 cum inside 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 if it hurt. “No, it’s…not bad. It’s just…uncomfortable. It feels really full.” She let out a breath and said, “That was so hot. I’m so turned on.” I watched her do her leg squeezing thing, and it wasn’t long before she came.   My cock was still in her, and I felt a new sensation of her muscles tightening and and releasing as she quickly pusher herself over the edge for a third time My hard-on slowly went down, and I slipped it out of her. “Wow….”I said. “That was incredible. Thank you.”  She turned and sat up, and we exchanged lingering wet kiss. 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 uncomfortable for her. I was terrified of hurting her, so I pulled out and went back to thrusting between her asscheeks method.  Still, those few times I was lucky enough to penetrate her ass all the way in, the exquisite feelings along my cock made me cum pretty quickly.  I think she was glad it didn’t take me very long. Three months later she let me try her pussy. After that, our relationship gradually cooled down, and we broke up before she left the country to study abroad the next school year. But I’ll never forget the first time Alice and I tried anal sex.