Written By: Gentle Virgin

I remember I had always been terrified at the thought of anal sex. However, deep down, I will admit to always having a huge curiosity about it. It scared me, but still... My first time had always been something we had talked about. He liked it a lot. Loved it in fact, probably. I wanted to, but at the same time, I couldn't imagine something that sized being shoved up my ass. So there I was, wanting to but scared. We actually hadn't talked about it for awhile. So the whole thing took me completely by surprise.

I had always envisioned a great deal of pain. I had my ideas about anal sex from, ok, from reading about prisoners. That was my whole mental picture. But at the same time, so many people I know just raved about it. He had always said, if the doer was considerate, there didn't have to be any pain involved. I wanted to believe, especially since I had a girlfriend that swore her best orgasms came from anal.

I remember I was getting ready to go to work. Leisurely wandering aroundthe house with coffee and a cigarette, watching the news and waking up slowly. He appeared in the doorway to the living room. That in and of itself was a notable occasion. He was never functional in the morning, he just staggered into the shower, put his clothes on, and played zombie out to the car. So I was a little surprised to be greeting a wide-awake and relatively cheerful boyfriend.

He sat down next to me, took a drag off my cigarette, and a sip of mycoffee. "Who are you, and what have you done with Steve?" was about the best I could manage from this coherent morning person that was sitting on the couch with me.

"I just felt like being awake this morning."

Taking my cigarette back, I turned my attention from the television to him. I remember I wasn't fully dressed yet, I had on stockings, shoes, and a skirt but from the waist up, I was still naked. He grabbed the cigarette out of my hand and set it down in the ashtray. Before I could gripe or grab my smoke, I was in his arms, getting my neck nuzzled. Deciding this was more pleasant than the little bit of bitching I had planned, I relaxed and enjoyed it. Leaning me back against the couch, he began kissing and sucking at my breasts.

I started getting a little frisky myself and began stroking and licking his body wherever I could reach. Always a big fan of morning sex, it didn't take me long to be completely ready for him. As his mouth was still involved with my tits, I could feel his hands all over my body. My skirt was up around my waist in no time. I kept reaching over to pull down his pajama bottoms, but he kept moving my hands away. I shifted my ass on the couch and had my legs around his waist.

"Please Steve, fuck me now or I will end up late for work."

Instead of answering me, he put his thumb right on top of my clit and started rocking it back against my pelvic bone just the way I loved it. He watched my expression for a moment, and then finally spoke.

"Oh, not to worry. I AM going to fuck you. But not right now."

I didn't like that answer a bit. I frowned and was opening my mouth to disagree with him When he stopped me with a finger on my lips. Still rocking my clit with his other hand, he was silent for a moment longer. I was getting ready to cum, I was so close I could feel my pelvic muscles tightening that last time, and then he stopped.

"Now go get dressed for work. I don't want you to be late. Just consider this an appetizer."

I got up off the couch and headed into the bedroom, thoroughly pissed off. As I was putting on my bra, and throwing my shirt on, I heard him approach the door of the bedroom on his way into the bathroom. As he passed the door, he said "and by the way, don't even THINK about having an orgasm until you get home from work." There I was, completely
denied and not liking it a bit. I was starting to think about "to hell with it" and doing just that before I left for work. But I decided to hold off a bit and see what he had in mind.

I put it all out of my mind, well as best as I could, considering I was still turned on and so wanting to get laid. I finished dressing,
finished my cup of coffee, and was putting on my coat to leave the house, when I heard him approach me from behind. In just a second, I could feel him pressed against me from behind. I felt his huge hardon against my ass as he held me in his arms for just a moment. I wanted him so bad at that moment that it almost hurt. He kissed my neck, licking his way up to my ear. And then he spoke again.

"Don't worry baby. It is going to be so good tonight. I promise. And tonight when you get home from work, I will already be home. As soon as you walk in the door, I'm going to undress you and fuck your ass."

Ok, now imagine going to work after getting turned on the way I was and then hearing THAT. Do you think you could be the slightest bit productive at your job? I don't remember much about that workday, except for the fact that I was completely and totally useless. And that every time I went to the bathroom, I was surprised at how wet I still was. And most of my uselessness was based on the fact that I couldn't think about anything else but what was going to happen when I got home from work.

The day finally ended and I got home uneventfully. As I walked in thedoor, I could smell the candles burning. Romantic music was playing and I could hear the shower stopping as I closed the front door. He yelled down the hall that there was a bottle of wine open in the kitchen and that he would join me in just a second. Kicking off my shoes as I went to get myself a glass of wine, I had only had a small sip when I felt his arms around me. Loving the way he smelled when he had that "just showered, still a little damp" thing going on, I was leaning my head back against him.

He was kissing my neck as I felt him turning me around, and kissing me deeply. "Welcome home," he said and kissed me again. Kissing him back, I greeted him like-wise. He set my glass down on the counter and led me by the hand into the bedroom. Kissing me again, he began to make good on the first part of his promise. Unbuttoning my shirt slowly, he tossed it on the floor as soon as he pulled it off me. My bra was off quite quickly as well. I was back to where we had started that morning, naked from the waist up. We were in each other's arms, kissing and stroking each other slowly. I became aware that I was being led slowly back towards the bed. I sat down when the back of my legs hit the bed. He sank to the ground in front of me, and reached under my skirt. Gently he began to remove my thigh high stockings. When my knee was naked, he kissed it and sucked on the skin, as he finished removing the nylon. The other leg got the same careful attention. He stood up and helped me to my feet, unzipped my skirt, and not very gently pulled it until it dropped to my feet.

Smiling at him, I couldn't help noticing how nervous I felt. Since he had made good on the first part of his promise, I had to assume that he planned on keeping the other half as well. Part of me was simply terrified, the other half was turned on beyond belief. I was so wet, I could feel it on my inner thighs. The only thing I could think to say to him at this point was "You did tell me that it won't hurt, right?"

As he laid me back on the bed, and was burying his head between my legs,the only thing he said before he went to work with his tongue was "I promise nothing will cause you any pain this evening." It didn't take any time before I was on the edge of an orgasm again. The only difference from this morning was this time he didn't stop what he was doing. I nearly cried when that first orgasm hit me. I was cumming harder than I had remembered doing so in a long time.

I was still recovering from the effects of that orgasm when he gently turned me over, and showed me how to lean forward on a pillow. "We need to get you so relaxed," he kept telling me. I was almost kneeling, with my arms cradling my head on a pillow, my ass all up in the air. I started breathing slowly, just listening to his voice as he talked to me and casually reached for a bottle of lube that was sitting on the night table.

I assumed he was putting the lube on his dick, so I was a littlesurprised when I felt him slowly push a finger into me. "Just relax
baby, you are doing so good" he told me. I could feel myself growing used to the feeling, and started being soothed by the sound of his voice. With one hand, he was stroking my body softly. My ass, back, thighs, I could feel all my muscles relaxing at the touch I knew so well.

When I first felt his cock at my ass, I tensed up for just a second. His voice soothed me, telling me not to be scared, that it was going to be ok. I finally had to concentrate for a second and force myself to calm down. When I felt my muscles relax, I felt him push inside me slowly. I just about came off the bed, it was such a bizarre feeling. Unlike regular sex, I was so much more aware of being filled up. As soon as I was starting to acclimate to the differences in sensation, I felt him start to move slowly.

He never rushed. It went so slow. I could feel everything. After a few minutes, I started thinking that it was a not too unpleasant sensation. "Grab your vibrator. Its next to you under the other pillow." I reached under the pillow and grabbed it in my hand. I pulled it out and held it behind me to show him that I had it. "Well I think you know what to do with it." Looking back at him over my shoulder, he nodded at me. I slid it slowly inside of me. I couldn't believe how filled up I felt. As I was trying to get used to that feeling, Steve poked me gently and said "Well? Turn it on baby." I thought about it for just a few seconds and decided "what the hell" and switched it on-HIGH!!!

I am almost positive I came the second I felt the vibrations from my pussy combined with him sliding in and out of my ass. He had been so gentle, holding himself back forcing himself to not rush for my sake. As he felt my body quiver from the shocks of my cum, that seemed to be his cue to step up the pace. The thrusts started coming a little firmer and quicker. I heard his breath quicken and I felt him grab hold of my hips roughly. The vib was still running and I found if I moved the right way, I could feel it against my clit. As he started fucking my ass harder and faster, I was rubbing my clit and feeling the vibrations inside my pussy. I felt myself tense up again, the excitement building. I had finally found my rhythm and was rocking the right way with him. When my ass started moving with him, he just about went crazy. He was fucking me hard and fast, and I realized I loved it!

From the sounds I could hear him making, I knew he was going to cum soon. I moved my hand so that the vib was running directly on my clit. In no time flat, I was completely caught up with him. I surprised myself that I was suddenly begging him to fuck me harder. I think I shocked him too, but he did his best to accommodate me. I think I started howling about a moment before he did. It was just incredible!

So now you have the story of a former anal virgin. And I have 2 final thoughts to share with you. First, I honestly don't know how I went as long as I did with out anal sex. Second and finally, it wasn't very long at all before I was the one asking him to fuck me THERE.