First Ass

Linda and I met about a month ago at a friends party, we had both been drinking, but weren’t really drunk and we just hit it off right away. We left the party around 2am and she ended up going back to my place where we had some of the hottest sex I’d had in a long time. I usually don’t pick up girls at parties, and wasn’t really looking for one that night, but hey, if it happens, it happens! Anyway she was really good looking dressed, and even better without clothes.

It turned out it had been a while since either one of us had had sex, so it quickly turned from hot necking into a sexual frenzy. We kissed, sucked, sucked and fucked almost every part of each other we could. That started it, and we’ve been going out together and having sex every chance we get since.

A couple of nights ago, we were lying on the bed, after a few hours of really hot sex, and Linda asked me if there was anything “special” that I’d like to do that we hadn’t done yet. Well, the only thing we hadn’t done was anal sex, in fact I’d never done it. I told her and she got a funny look in her eye, and said that she’d never done it either, but had always thought about it. I got up and pulled out a porn flick that I had in the bedroom, and fired up the VCR. It was a hot one, with lot’s of anal action that I’d watched many a time, wondering what it would be like to put my cock up someone’s ass.

It didn’t take long for the action to start, with a girl getting her ass fingered while the guy ate her out. Soon she was getting stuffed with a fair size cock while she played with herself. We could both see the ring of her asshole stretching as it took his cock in and then closing as he all but pulled it out on each stroke. Meanwhile, Linda was slowly stroking my cock, while I fingered her and alternated between kissing her lips and her sensitive nipples. By the time the movie was over, we were both as hot as we could get without cumming. I asked her if she wanted to try it and she said “Yes, but with one condition. If you want to fuck me up the ass, you’ve got to let me do your ass first”.

Now I’d thought about fucking a girls ass for a long time, but I hadn’t really considered having anything up mine. But after thinking about it for a few seconds, I figured that fair was fair so I agreed. I was all for doing it right then, but Linda said she wasn’t quite ready and wanted to wait until the next night for our “anal initiation”. We were both horny as hell again though, so she climbed up on top of me and rode me like one of those bull riders you see on TV. It didn’t take long before we both came, loud and long.

Throughout the next day, I kept thinking about what was to come, excited yet nervous. Each time I did, my cock would stiffen in anticipation, so I had to be careful not to daydream too much or someone around the office would surely notice me walking around with a bulge in my pants! I don’t think that it had ever taken so long for 5 o’clock to get there.

When I got home, Linda was waiting for me, wearing a sheer gown that she’d worn a couple of times before, with a couple of drinks sitting on the bar. After we’d finished them, she led me toward the bathroom, saying she wanted us to both be clean for each other. By this time I was already hard, and watching her undress me while she kissed and touched my skin as it was exposed made me stiffen even more. Finally, she slipped off her gown and turned on the shower. We were constantly kissing and fondling as we soaped and washed each other. She jumped a bit as my finger slipped over her anal pucker, but didn’t pull away as the very tip of my finger worked it’s way into her ass. Just as I was wondering what it felt like, I felt her soapy finger running down my crack, and across my asshole.

When she touched it, it almost felt like an electric shock and my cock twitched. It felt even better when the tip of her finger slipped into my ass, just as mine was in hers. I’d never had anything up my ass before, not even my finger, and now I was wondering why I waited so long, because it felt great. As we kissed and fingered each other’s ass, she said she was ready for more. So we got out of the shower, dried off and went to the bedroom. The lights were dimmed, but I could see a bunch of things laid out on the night table. Suddenly I was nervous again, and almost as if she knew, Linda turned and kissed me saying, “don’t worry, I wouldn’t hurt you, any more than you would hurt me.”

Linda told me to lay on my back near the edge of the bed with my legs slightly spread, and my knees pulled up. She knelt on the floor in front of me, and began stroking my now throbbing cock, planting light kisses on my thighs and hips. Soon those kisses moved to the head of my cock, which soon disappeared into the hot wetness of her mouth. After a minute or so of this, I could feel her fingers tracing patterns around my ass, with each stroke of her tongue, they got closer and closer to my back door. Just as I was reaching the point where cumming was inevitable, she stopped and told me to roll over and kneel on the bed just like the girl in the video had.

As I knelt there, I felt very exposed, feeling for the first time, how a woman must feel before being entered by a man. I looked back as she picked up a tube of lube and put some on her finger. As she applied it to my asshole, I could feel her finger working it’s way into me, just as it had in the shower. Soon she had it buried all the way up my ass and began moving it in and out, like a thin cock. Just as I was starting to get used to the feeling, she added a second finger to the first and leant forward and told me to let her know if it hurt at all and she would quit. It did hurt a bit at first, but it felt so good that there was no way I was going to tell her to quit!

As my sphincter got used to the fingers stretching it, she began moving them in and out, fucking my ass with them. Again, once I had fully adjusted to two fingers, I felt a third begin it’s entry. I wasn’t sure if I could take all three, but she took it slow and easy, and soon my ass was stuffed with her fingers. The feeling was incredible, and I could hardly wait to reciprocate with her. She tried four fingers but could only get them in part way without it hurting more than the pleasure it was giving me, so she pulled out, leaving me with a throbbing cock and a well lubed ass. I didn’t look back, as I wanted whatever was going to happen next to be a surprise – and surprise it was. I felt the end of something pressing up against my ass, and as it slowly entered me, I realized it was the dildo that I had given her the week before.

Thinking of the size and shape of it, I wondered how much of it I could take, and just as quickly realized I was going to find out. Just as slowly as she had with her fingers, she worked the dildo into my ass, going in a bit farther with each stroke. It felt much softer than her fingers had, and I relaxed and let her fuck me with it. Soon I realized that it wasn’t going in any more and looked back to see only a couple of inches of that 10″ dildo remaining visible. As the speed of her thrusts increased, so did my pleasure, soon she was fucking my ass just as hard as I usually fucked her when we made love – and it felt great! Suddenly she changed tactics, pulling it all the way out and then putting just the head in. I could feel my sphincter expand and contract with each stroke.

This felt even better and I could feel an orgasm building in me. I told her I was going to cum soon, so she lay on her back and slid her head under me so she could suck my cock while she ran the dildo in and out of my ass. The combination of dildo and mouth were too much and I started cumming. Now I usually have a fairly hard orgasm, but this one was unbelievable. I must have shot 15 or 20 times, filling her mouth with my hot fluid, some of it running down the sides of her face. It wasn’t the first time I’d cum in her mouth, and she has always said she liked the taste and feeling as she swallowed it.

As she pulled the dildo out of my ass, she rolled me over and lay on top of me, leaning over to kiss me. As my tongue entered her mouth, I could taste the salty traces of my cum. I was totally surprised though when her tongue slid past mine and I realized she hadn’t swallowed all my cum as she allowed what was left to slip into my mouth. At first I was kind of grossed out, but quickly found the taste not at all unappealing and swallowed it myself as my tongue searched out any remaining cum inside.

As we lay there kissing and fondling each other, she told me how much she had enjoyed it, and that she was ready for me to take her anal cherry too. I had her lie on her back on the bed, and lay on top of her. I started kissing her mouth, and licked up the few strings of cum that had run down her face. As I worked my way down to her nipples, I was fondling her sopping wet pussy. When I had her nipples as hard as my cock had been, I moved on again, leaving a wet trail of kisses down her stomach to her pussy. I have always enjoyed eating out a woman, and Linda was no exception.

She always kept the hair trimmed from around her lips, so I had total access to her hot, wet slit. It was my turn to tease now, as I ran my tongue around her pussy – getting close to but never quite touching her hardened clit. I slipped a couple of fingers into her slit, working them in and out until she was hunching her pussy into my face. Next I started teasing her clit with the tip of my tongue, and then stopping to blow cool air on it. After a few minutes of this, I started licking and sucking her clit, just as she had done to my cock earlier. It wasn’t long before I could tell she was getting ready to cum, so I stopped and told her to kneel on the bed, exposing her asshole and pussy to me. I looked down at her, and just knowing that I would soon have my cock buried in her virgin ass caused my it to quiver and grow. I continued licking her slit, slowly but surely working my fingers down and over her asshole.

Finally I stopped and picked up the lube. As I spread it over her puckered hole with my finger, she continued to push back against me, forcing it into her. Linda’s ass accepted the first finger easily. As I watched it slide in and out, I was remembering how good her fingers had felt in my ass not too long ago. My fingers were considerably larger than hers, and her ass was smaller, so I had a little more trouble getting two fingers into her, and when I tried three, she told me to stop for a bit. She took the lube and spread more on my fingers and her ass and told me to just hold my hand there and she would do the work. The extra lube did the trick and soon I had three fingers buried all the way up her ass. She was rubbing her clit and moaning as she thrust herself on and off my fingers. I knew she couldn’t take all four up her ass, although one night she’d taken my whole hand up to the knuckles in her pussy, so I pulled my fingers out and greased up my cock.

As I placed the head of my cock against her butt hole, I leant forward and kissed her neck. She turned her face to mine and we kissed as my cock made it’s way into her ass for the first time. The feeling was incredible! I took it very slowly at first so I didn’t hurt her, but soon she was pushing back against me for more. Inch by inch it went in, until all 8 inches was buried in her ass. It was so tight it felt like a cord had been wound around my cock. As we increased our thrusts against each other, Linda grabbed the dildo she’d used on me and pulled the condom off of it. She was so wet that it slid easily into her pussy. I actually feel it against my cock as she slid it in and out. We both knew we were too hot for it to last much longer. Suddenly, her whole body tightened as she came, and she began thrusting wildly back against my cock. The tightness and the thrusting were too much and I began to cum as well, shooting my hot cum deep into her ass.

It was certainly a night of firsts – but we both agreed that it wouldn’t be the last!