Trying Anal Sex With Christina

It was a Friday night in May 2012. I was on Yahoo Messenger and Christina messaged me.

“Why don’t you come over? I haven’t seen you for a few weeks,” Christina said.

“I’ll get a shower and head over,” I replied.

“I need to get ready too,” Christina replied.

I asked, “What do you need to do?”

“I need to shower and shave my pussy for you,” Christina replied.

“Go ahead and shower but please don’t shave, I want to see you unshaven,” I said.

After my shower, I drove to Christina’s place. She had a nice guest house in Northridge. I called her when I had parked. She came outside in a bathrobe and let me in.

We’d been seeing each other for almost two years at this point. We were comfortable with one another. We hugged for a moment and then I went to one side of her bed. I took all of my clothes and lay down. Christina came up to the other side of the bed and removed her bathrobe. All she had on underneath was a very small purple thong. It was see-through on the front and just a string around the sides and in the back.

“Do you like it? I just got it,” Christina said.

I replied, “You know I love it.”

I could see Christina’s bush through the front of it. Sometimes she was completely shaven, other times she was natural. I didn’t mind either way but many times I preferred natural. So many girls shaved their pussies, it got old after a while.

Christina lay down next to me. She was to my left, I put my arm around her and started caressing her ass cheeks. We began slowly kissing each other. Our mouths were closed at first but soon they were open. Our tongues were exploring each other’s mouths.

“I love coming over here,” I said.

Christina replied, “I love our visits. Where should we start tonight?”

“Why don’t you take your panties off and sit on my face?” I replied.

Christina slid the panties off. She got up next to my head and straddled my face. I was looking up at her pussy and tits. We had tried the sixty-nine position before but it was more fun to do one at a time for us. I started kissing and licking her pussy. She was already very wet; her pussy hair was grinding into my nose. Christina would ride my face, I’d usually work on the clit. But then I’d work my head back and lick her pussy and asshole too.

Christina was moaning with pleasure. When I could tell she was cumming I went back to just licking her clit. She seemed to have the best orgasm from that.

When Christina had finished she unmounted my face and went right to my cock. She was sucking it very aggressively tonight. She was working on the head of my cock and stroking the shaft with her right hand. I had to stop her twice because I almost came.

“I really need to destress tonight, I’ve had a rough week at work,” Christina said.

I was already laying down so she went right into the cowgirl position. She was riding me hard tonight. Sometimes she would stop and let me thrust up into her. Then I’d grab her hips and we’d coordinate our rhythm. We went at it for a good ten minutes and finally, she came hard.

Then she turned around and went into reverse cowgirl. I love the view from this position. She was gripping my legs tight and riding me hard.

After about ten more minutes she moved forward into the doggy position.

“Your turn, fuck me hard,” Christina said.

I got behind her and slid my cock right back into her wet pussy. I was pumping her hard, she was also moving her hips back into my cock. Then she reached back and started playing with her clit. She’d also reach back and tickle my balls with her nails.


Christina always had long nails and they were always painted nicely.

There were several times I had to stop myself from cumming. I was good at it now. If I held it back too many times it could be hard to finish.

We stopped, and Christina turned around and lay down on her back. She put her legs in the air. I slid my cock back into her. She wrapped her legs around me as I fucked her slowly and deeply. She started cumming again.

“Let’s cum at the same time,” she said.

She started cumming again. She had a nice long orgasm where I was pounding her the whole time. But I had stopped myself too many times, it wasn’t happening for me.

Finally, I had to take a break. We had been fucking for forty minutes. My cock was still hard though. Christina reached into a drawer and pulled out a bottle of lube. She put it all over my cock and started giving me an aggressive handjob.

“I have an idea. Can we try anal tonight?” I asked.

“I’d love that. Can you lube me?” Christina said.

Christina got in the doggy position and put her ass in the air.

“Use a lot, I haven’t done this lately,” Christina said. I squirted some lube around her asshole and started working it in with my fingers. She was moaning from that already. I was pushing two fingers deep in her ass and putting more lube there as I fingered her.

Finally, I was pretty sure that she was ready. I squirted some lube on my cock and made sure it was completely ready. Then I moved up behind Christina and put the head of my cock on her asshole. I gently pushed the head in. She pushed back against me and my cock went into her ass deeper. Her ass was so tight, I was going to have no trouble cumming soon.

“Are you ok?” I asked her.

“It feels great. Fuck me slowly though, ok?” Christina replied.

It was a slow and tight grind. The sight of my cock going in and out of her asshole was so hot. She had shown me a pic of her getting fucked in the ass with one of her other lovers. I wanted to take a picture but I was too into what we were doing. Christina reached back and started rubbing her clit. After about five minutes I started to cum.

“Cum in my ass!” Christina said.

“I’m going to shoot it on your pussy,” I replied.

I pulled my cock out of Christina and started jerking it tightly with my right hand. Finally, I started shooting cum on her pussy, getting it all into her full bush. I came between her ass cheeks too and on the back of her legs. It was a glorious mess and it was dripping down on her comforter.

I put my left hand on Christina’s ass for a few seconds. I was a bit light-headed after fucking for so long.

“Don’t move,” I said to Christina.

I went to her bathroom and got a hand towel. I returned and cleaned her up. I wiped my cum off of the back of her legs. Then I cleaned her ass, there was a lot of cum and lube there. Lastly, I cleaned up her beautiful unshaven pussy and bush.

“We finally did anal. I loved it but next time I want you to cum in my ass,” Christina said.

The next day I got a message on Yahoo Messenger from Christina.

“Thanks for coming over. That was so much fun, can we do it again soon?” Christina asked.

I replied, “Sooner for sure. Your ass is so tight, I can’t get the thought of it out of my mind.”

“We really should have done that much sooner. Let’s add it to our routine,” she replied.