My First Anal Experience

I would like to tell you about the first time my old girlfriend and I had anal sex… We hadn’t been going out for very long and it was still in the beginning glow of sex all the time. Our day had been good and we were on number 3 sex session for the day. This was still in the time of the do it and do it all and do it right now at the beginning of a relationship. She was great in bed regardless but that added the extra spice.

The first time that day was after we woke up in the morning and I went down on her to get ride of my morning breath. Naturally she returned the favor by engulfing my cock in her mouth, she couldn’t deep throat me, but she still gave very good head. She was always ready to suck my dick and loved doing it. She would lick all around the head, very gently. One of my favorite things to do was walk in on her in the bathroom and whip my dick out and have her suck me when she was on the toilet. She wouldn’t complain, she would just smile and then lick and suck me for a minute or two to tease me and then finish her business and we would go on with what we were doing. If you were wondering I have a moderately sized dick, about 7 1/2 inches long, and quite thick, it was as thick as her wrist, now that I think about it. The first time we ever did actually have sex, the first time I put it in her, she grunted kind of oddly. We were doing it missionary and she had of course already seen me and played with it a good bit, sucked on it etcetera but apparently it didn’t really strike home until I was deep in her pussy. I pulled back and stopped moving to ask her

“Honey, what’s wrong? Are you all right?” She looked back up at me with this lustful expression as she said,

“No, I’m okay, it’s just that you’re much bigger than I am used too.” Talk about an ego building moment!

“Do you want to stop, does it hurt?” I asked.

“No! Don’t stop, it feels fuckin’ great!” she exclaimed. And too prove her point, she pulled my hips back down into her again. But I digress.

She always tasted oh so sweet. I had shaved her pussy about 3 days ago, it was the first time for her, and we both really liked it. She said that there was better sensation, and I liked it because I didn’t have any hair in my mouth, and wow did it look awesome. Her name was Irene and man what a lady. She didn’t have really big boobs or a great ass, but it was a nice ass, and good firm small titties. This is a true story, not a fantasy. But she had wonderfully sensitive nipples and would gasp and moan every time I would suck on them or play with them. Sorry, back to the story. As I was licking on her clit, and she was sucking my dick, I could tell she was getting close to cumming, she was starting to move her hips around in a circular motion, and she was moaning around my dick also she was pushing up with her pussy into my mouth, especially when I would lick her clit with the underside of my tongue, the smoother side so to speak. To make her cum just a little sooner and a little better, I put two fingers inside her pussy and started to rub around the top wall towards my chin, I could feel her g-spot after a moment or two of searching. It was an awkward position for my arm, but the way she moaned made it was totally worth it… She started almost humming on my cock as she got closer and closer to cumming with my dick in her mouth. Quicker than I thought, she came, spitting out my cock and pulling my head down on her pussy. She had a very nice little orgasm from that manipulation of her pussy and pushed me over on my side, off of her. Then she turned over, got on all fours, and made here decision very clear.

“Fuck me.” She moaned in a soft voice.

I could still see the ripples on her thighs as she continued to have small contractions from her orgasm. Quickly I got a squirt of Wet, (a wonderful lubricant if you need some!) rubbing it all over my very hard dick and then smeared the rest on and in her already wet pussy. I moved in behind her and aimed as best I could without being able to see very well at her little slice of heaven. Of course, I missed, and hit right between her pussy and backdoor, pushing down to the right spot she pushed back as she felt me on her opening. In I went and both of us stared to grunt and moan and strain as we fucked faster and faster. I first I was just holding her hips, and then pulling on her hips, then unable to get enough leverage I moved one hand to her shoulders and then both to pull her back even faster and harder onto my cock. “Faster, more, more, harder! Yes, here I cum,” she cried, I could feel her pussy pulsating around me and soon I exploded deep inside her.

Later that day… at about 12 or so, we had been watching tv and just relaxing on the couch for a while. Neither of us was wearing very much at all and she was leaning up against me. This was some great cuddle time and after not too much longer it started to have an effect on my second head. Up it rose, like a submarine periscope. I wasn’t really doing anything about it other than enjoying my hand on her tit as we sat there, but soon she noticed my member at attention. I was in sweats so it was pretty noticeable I guess, she reached down to the waistband and pushed it back behind my balls. Gently she leaned over and licked the head, slowly while looking sideways up at me. It was so erotic, she even did the porn star hair flip so that I could watch as she bobbed up and down on my cock. Licking and sucking gently, using her lips a lot, and going even farther down to suck my balls occasionally. After she had really got my dick nice and wet she stood up and took her shorts and t-shirt off.

“I wanna try a position that I saw in porno movie one time.” She had the most devilish grin.

“Sure, what do we need to do?” I asked, very interested as you can imagine. Porno positions?? What’s next with her?

“Okay, I am going to lie on the floor with my legs in the air and my back against the couch, I want you to put your cock in me from above, while I have my legs out to the sides.”

Having said that, she promptly moved into that position. It took some doing, and a little acrobatics to get into this contortion, I think its called the “pile driver” and it seemed okay, but neither of us liked it too much. It hurt a little to have my dick pointing straight down and she said that all the blood had rushed to her head, so she wasn’t getting as much sensation out of it. We even tried turning around so that I was facing towards her butt, and doing it that way, it was easier to get into that position, and a little easier on my cock, but didn’t do too much for her or I. After about 5 more minutes of that we stopped. I sat back on the couch, and she got up to sit in my lap with me now back where I belonged inside her tight puss. I could also suck on her tits from this position and was quite able to get both nipples in my mouth at the same time. She felt so nice and it was much less energetic and painful. But still very friendly, fairly quickly she rode me to a great orgasm for both of us. Have you ever had a simultaneous orgasm? When you can just feel her contracting and pulsating around you, sometimes you can feel her juices just flowing out and around your cock, as you feel like you’re about to blow the top of her head off from your own eruption? Its one of the best feelings in the world.

But the reason that I started this story was to tell you about the first time I ever had anal sex. After our lunchtime fun, I had gone to run some errands and do some things at my house. She had had to go out and about as well and we agreed to meet at her place at about 8:00 that night to go out and have a good time with some friends. Well when I got to her apartment, she was there, but in a foul mood. I don’t remember exactly why, maybe it was traffic; maybe she just couldn’t get her errands done. Either way, after I was there for a little while, I noticed that she was being really bitchy. Never one to be yelled at for nothing, and still horny from earlier that day, I tried to talk with her for a while about what was wrong. To listen, not to fix a problem, just too listen. That seemed to take some of the wind out of her sails. Maybe a better way to say that is that it seemed to help her to be able to just vent about it. Then I just decided that I didn’t want to wait until after dinner and some time out to get laid again. She was also getting dressed at the time and was only wearing a bra and thong. That might have had something to do with turning me on. I love a good thong, where you know its disappeared into the crack of her ass, and you can just barely see it in between her cheeks as she walked around the room. I moved in for the kill.

As I started to approach Irene, I had stopped talking with her. She looked over her shoulder at my silent approach and smiled slightly, and moved farther down her closet from me. Not much, but I knew and why and so did she. The farther I moved forward, the farther down the wall/closet she moved. It was a full wall 3-door closet. Mostly full too. As she got to the end, she turned and put her finger up in my face.

“Doug!” she exclaimed. But she also had this devilish smile on her face at the time.

“Yeah? What? You tell me to stop I will. Just say NO, but until then I am going to get you naked and the fuck the hell out of you, maybe it will put you in a better mood. Telling me No is the only way I will stop.” I said. I was actually getting kind of irritated at her for the way she had been acting. On the other hand if she was willing to put out, well it would make her feel better and me too. As I grabbed her arms and pulled her close, she struggled just a bit, but only playfully. I had given her the out, if she said no, I was really going to stop. I pulled her too me and started to nibble on her neck, slowly moving up to her ear, nipping the lobe and gently biting the skin. Not hard, but softly. I held her arms down on her sides, so she couldn’t reach all the way around me as I reached behind her for her bra clasp. After that was undone and I was holding her tight too me, I reached down to her ass and pulled her tight against my thighs. She is 5’4” I am 5’ 11” and about 70 lbs heavier than her at 195 or so. It wasn’t so much of a contest of strength, just of wriggling until her bra was gone. By this point she was starting to kiss me back and run her hands up my back and to pull me closer to her.

Looking her right in the eye, “Get naked and on the bed, right now!” I growled softly in her ear. She looked at me, smiled and quickly backed away from me, pulled off her thong and got on the bed, lying on her side to watch as I undressed. That took about 45 seconds at the most, and I quickly got on the bed with her. But not exactly like she was expecting. I kneeled on the bed and as I moved towards her, I moved right too her head, my cock was stiff as could be and standing at its normal 65 degree angle. I moved right too her face and pushed it into her mouth. She smiled around my cock as she started to suck and lick at the head. She wasn’t moving really deep on it as she was licking, but it still felt like a warm bath, as she breathed out and on my dick. I was really enjoying her lips and suction as she slowly continued the blowjob. Playing with her tits as she sucked me was quite nice as well, but I really wanted to fuck her and fuck her now. Besides it was more about making her feel good and not me at this point. So after letting go of her head I shifted my body around so that I could get at licking her sweet pussy. She moved to her back and kept up her good work on the head of my cock. After about 10 more minutes of eating her pussy and another orgasm, I decided that it was time to fuck what I was eating. So I sat up, pulled my dick out of her mouth, along with her murmured protest, and moved in between her legs. As I slipped the head up and down her slit to tease her, she started to pout and tried to pull me inside by grabbing my hips.

“Ha! Not a chance babe” I smirked down at her

Slowly I teased her pussy for about 30 seconds or so, moving up and down, pushing hard on her clit, rubbing back and forth, all the way down to her ass and pushing a little on that and then back up, I even pushed along her clit and almost up to her belly button… She really liked that and it tickled me as well. Finally though I wanted to be in her tight heat and slipped in her. She closed her eyes as I slowly pushed all the way into the very bottom. I could feel the string from her diaphragm and so could she. We looked into each other’s eyes as I started to piston my hips up and down. She was moaning and thrashing on the bed very soon after that and reached up to run her nails across my lower back. Unfortunately she had really sharp nails. I probably still have scars to prove it. On the other hand it got me even deeper inside of her, which was what she wanted. I wasn’t about to complain other than about the red nearly bleeding streaks in the skin of my back.

It was at this point that I realized I really wanted her to be on top. She usually didn’t like that, said she felt fat in that position. It’s a silly complaint, especially when I am as deep inside her as I can get at the time, I certainly didn’t feel she was fat, and she didn’t look that way to me, even more important, I have less stimulation if she’s on top and can last almost indefinitely from that position. Ah well. On the other hand, I didn’t give her a choice. I simply pulled her left leg in tight to me and rolled that way. It squishes her leg for moment, but that’s about it. Like I said, I didn’t give her the choice and as she was on top, I pulled her down so I could kiss her and suck her nipples and I started to fuck up into her pussy. Reaching around I started to finger her asshole, it was always one of my big fantasies to do a girl in the ass, and little did I suspect! As I reached, and started to finger gently around her asshole, I started to gently tease her pucker, ever outside, but mainly to just let her know of what I was thinking about and test out her reaction. The reaction was good, she gasped straight in my ear as I put in my middle finger to the second knuckle and started to wiggle it around inside her butt. God it felt soooo good in there,

There we were on the bed, doing it with her on top and she suddenly pressed down on my cock sat up straight, put her hands on my chest and looked down into my eyes.

“I wanna switch to doggy style on the floor next to the bed.”

Now I am a gentleman and always willing to please a lady, so I let go of her hips and she got off of me. It was at this point that I told her to “assume the position” it was our favorite position, and that was the code words for doing it doggy. I scooted up behind her and slipped into her wonderfully tight pussy. Like I said it was the 3rd time that day, so I was able to last quite a while, even in though doggy gives me the most stimulation. I started to really pound into her pussy from behind. Holding tightly on to her hips so that she couldn’t get too far forward and I certainly didn’t want to slip out. We were both so sweaty at this point it probably would have been dangerous. Besides, I already knew that she loved to have her hips held tightly as we did it doggy style, she said it felt even better than normal that way. Its her hips, who am I too argue??

That was when she really threw me for a loop, we were going at it hammer and tongs, and she knew that I was a curious about putting my cock in her ass from prior conversations, aside from just having my finger in there. She looked back after she had come like two more times and I was starting to get close… and said

“Doug do you want to fuck my ass?” Such wonderful words!

“Oh god! Honey do you mean it?!?” I gasped back to her, my eyes very wide. She grinned and nodded.

Now remember that this was my first time… and I pretty much fucked it up. I pulled out, got up grabbed the bottle of Wet and put some on my cock and her ass, some in her ass as well. She jumped when I put it on, and so did I. Dang that stuff was cold!!! I might have been too rough with putting some in her ass as well, know that I think about it. So after getting the lube on both of us, and without any of the better preparation that I would do these days, you know, fingers, toys, possibly my tongue, or my tongue on her clit as I played with her pussy and put a toy or fingers into her ass, but oh no, not me, I put the head to her ass and pushed too hard. She yelped and jumped forward to get off my cock then she looked back and said, “Hold still so that I can get used to your cock up my ass!” What a wonderful thing to say! I can still see her face as she pushed back on to my throbbingly hard cock. “Line it up again, and I will do the work.” Of course I readily complied with that command!

She slowly pushed back on to me, it felt like my whole body was on fire as my cock entered her ass, I swear it was about 150 degrees in the room at that point, even though it was snowing out at the time. So gently, slowly, lovingly she pushed more than the head into herself. It was at this point that my cock twitched and she jumped again. It wasn’t on purpose, but the reaction to how good it felt almost made me cum. When I twitched later on after I was all the way in, just let out a soft cry and moaned, “yes, do it again!” And then she pressed even farther back until I was all the way in to the hilt, buried in her colon.

Have you ever felt a woman’s ass-cheeks pressed against your groin when you are as deep as you can get inside her ass? I was in heaven! Holy shit it was great! I can still feel her hips and everything pressed back to me. I could even lightly feel my balls pressed against her pussy and her fingers manipulating away on her clit, I leaned forward and played with her nice little titties, she was so close to orgasm at that point that she went over the top with the extra stimulation of my tongue in her ear, and my hands on her boobs, along with playing with her clit and my dick up her ass. I can still imagine her as I look down from behind her and can feel the contractions in her ass and pussy as she came really nice and hard. Even more so as I lay on her back playing with her boobs.

After she was more used to me, she said to start fucking her ass, which I did, a bit too hard and then as I was really getting into it she tightened up, a lot, and not in a good way.

Unfortunately I didn’t realize this at first, and was getting really close my self. I was pulling hard on her hips and had gotten back up off of her back as I fucked into her ass at high normal pussy speeds. Like when you’re both close and really want to come hard and fast. It was my fault for not noticing, she groaned and then cried out in a very different tone of voice and she had to reach back to stop me, she pushed on my lower stomach to stop me from still pummeling her asshole. As she did I understood that there was a problem.

She grimaced a bit and said, “I tightened up and to hold still for a while so that I can calm down and relax.”

“Is that normal?”

“No but it happens,” she replied I asked, I was in a state of aroused and frozen shock, I didn’t want to hurt her at all of course, and here I had gone and hurt her anyway. I don’t know when exactly she tightened up as I was too caught up in the moment, but there were probably three full strokes that I did before I knew that there was a problem. I felt terrible about that and still do. We waited about a minute or so and then after she felt better she told me to hold still and she put her head down and started moving her hips on my cock. I was back in heaven. I could feel the tightening and loosening as her sphincter worked to eject me from her tunnel, it wasn’t having any luck, but it felt so damn good. Then she reached down to her pussy again and after tickling my balls she pressed two fingers inside herself and up against the back wall of her pussy. I could feel her fingers right against the bottom of my cock, but inside her pussy and through the walls of flesh, she was so amazing! Suddenly I couldn’t take it any more and grabbed her hips and pushed as hard as I could up her ass and she leaned back against me. We could both feel this molten blast coming out of my cock up into her rectum, I usually have a pretty good load but that one was out of this world. She came right at about the same time, God it was wonderful! She usually wasn’t very loud, but that time she made the most wonderful sounds. And they were loud sounds! Things like “fuck my ass faster, a little harder, oooh more more, right there, Yes YES!