I don't know where I got the idea, but whatever possessed me to try it was a godsend.
You see, it's not so much that I'm a deviant or anything... but I've always had one little dirty obsession. I love the idea of anal sex. I love the thought of sticking my cock into a girl's tight ass and fucking her until I cum.
But I also like making a girl moan. I love pleasing a girl. And most girls won't even listen to me if I mention anal sex. So there I was. Stuck in the middle. I wanted to please the women I was with, but I also wanted hot, tight anal sex.
So when I finally found a girl who was willing to try anal, I was ecstatic. It was great. Her name was Stacy. And she was hot as hell. 5'4, brunette, tight lithe body. I could imagine my hard cock penetrating her ass. She sucked on my dick for a few minutes just to get it wet while I played with her pussy. By the time we were ready to actually do it, her pussy was dripping. I ran my fingers across her wetness, spreading it down to her asshole. I went down on her and sucked on her clit to try and make her wetter. The wetter she was, the easier it was going to be. I finally worked up the courage to stick one finger into her ass while I was eating her out. She squirmed and moaned, but it wasn't a good kind of moan.
"Ow." she said. "Be careful..."
I could feel her ass clench up a little bit. This was going to be harder than I thought. But it didn't matter. I just wanted to fuck her ass, and I finally found a girl that would let me. Slowly, I rubbed her wetness around her asshole, and inside of it. She made a face, but she didn't say anything. I led my cock up to her tight opening, and finally, thrust it inside. The head broke through the tight flesh and she yelped.
"Does that hurt?" I had to say after I saw the expression on her face.
"Yes... just be gentle."
I slowly pushed myself into her. She took a deep breath, but didn't say anything. I was inside her a good inch past the head. Then two inches. She groaned. "It hurts..."
I stopped where I was. "I'm sorry... I'm going slowly."
When she didn't look like she was in pain anymore, I pushed a little deeper. She grimaced again. Finally, I was all the way inside of her. It felt so good. It was so tight... and then...
"Take it out... it hurts."
That night, as she was falling asleep beside me, an idea came into my head. A friend of mine had once taught me how to do simple hypnosis. Stacy was already half asleep beside me. So I began to murmur in her ear.
"Just relax, and listen to the sound of my voice..."
Within minutes, she was in a deep trance.
"Stacy," I asked, "Does your ass still hurt?"
"Stacy," I was unsure if it would work... but it was worth a try. "I'm going to count backwards from 10. When I get down to 1, your ass won't hurt anymore. In fact, it will start to feel good. You are going to want me to give you anal sex. And when it happens, it won't hurt. Any pain you feel will instantly turn into pleasure. When you and I have anal sex, it will feel good. It will feel so good, you might even have an orgasm, just like regular sex. When I count down from 10, you will start to wake up. Once I reach 1, you will wake up, and you will want to try anal sex again. It won't hurt. It will feel very very good, and you will love it. 10... 9... 8... 7... 6... 5... 4... 3..."
Her eyelids started to flutter open a bit.
She rolled over and kissed me. "You know," she said, "My ass is feeling a lot better now... you think we can try again?"
Wow. I couldn't believe it actually worked.
She masturbated in front of me to try and get wet again. She had never done that before. Maybe I should try and do this more often, try and liberate more girls this way...
Finally, she did what I did earlier, and ran her hand down her wet pussy and into her tight little ass. She could only get one finger in because it was so tight, but she managed to spread the wetness deep inside. I gently slid my 8 inches into her pussy to get my cock as wet as it could be, and she moaned. I slid it in and out a few times, just to try and turn her on as much as I could, then I pulled it out and put it against her asshole. With one hand on my cock and another hand on her waist, I guided it inside. I felt the same sensation as I had before, as the head of my cock popped inside of her tight hole. She moaned.
"Wow... this actually feels kinda good."
I didn't reply, and slowly slid inside of her. She was so tight that my cock wouldn't slide in slowly, I would push, then it would suddenly give about an inch at once. Every time that happened, instead of wincing in pain like she did the first time, she moaned. Finally I was all the way inside. I could feel my balls brushing up against her legs.
"This feels really good." She said. "Fuck me."
That was all I needed. I pulled my cock halfway out of her ass, and I saw her face light up in ecstasy. I know if I'd done this an hour ago, she would have screamed in pain. But now she loved it. I shoved my cock all the way back in, up to the hilt, and she screamed, this time in pure pleasure. "More!" she yelled.
I pulled it out again and slammed it inside of her. "Harder!"
I did it again. And again and each time she moaned and dug her fingernails into my back. Finally, I started going at a good pace. She was moaning and squirming. Finally, she reached down with one hand and started masturbating right in front of me. She ran her engorged clit between two of her fingers, then reached deep inside of her pussy. I rammed my cock in and out of her tight ass. It felt so good... so tight... all of a sudden, I exploded inside of her. Cum sprayed out of her tight little ass as I pounded my cock inside the last few times. She moaned in orgasm as she dripped her own wetness down her ass cheeks to mingle with mine. I pulled out of her and collapsed on top of her. I could feel her firm breasts heaving against me as we both gasped for air. That was the most intense orgasm I had ever felt, and I could tell she felt the same way.
We fell asleep in each other's arms that night, exhausted after our short, but intense sex.
The next morning, I awoke to feel her fondling my balls. I had a huge case of morning wood, probably mostly because of what she was doing to me. When she saw my eyes open, she smiled at me. "Good morning sweetie."
I moaned, half because I just woke up, and half because what she was doing felt really good.
"Last night was amazing... I was just wondering if we have time for a repeat performance before class." Stacy smiled at me, and kissed my neck. Then she worked her way down. Before I knew what was happening, she had my cock in her mouth, and she was sucking as hard as she could. I moaned and pushed her head down a little more. She sucked, and I moaned again. Then suddenly, she stopped, and pushed me over so I was laying on my back. She went back to sucking for a minute, then she crawled up and started kissing my stomach and my chest. One of her hands grabbed onto my cock and started playing with it, then before I knew it, she was straddling me, and her pussy rested against the tip of my cock.
"Just relax baby... I know you're still tired. I'll do all the work this time."
She gently drove herself onto my cock. I watched it disappear into the warm wetness of her pussy. She started grinding a little bit, then a little more. It felt so good... but it wasn't the same as the anal sex last night. She kept grinding and grinding... and I could feel her getting wetter and wetter...
Then suddenly, she stopped. Both of her hands ran down her stomach, and rubbed along either side of my cock. She spread her wetness farther back, and into her asshole. Then she pulled herself off of my cock, and repositioned herself. My cockhead rested against her asshole, and she grabbed my cock in one hand, and guided it into her tight hole as she sat down with all of her weight. We both moaned as I penetrated her deep inside her tightest hole. She started grinding again, and it was pure heaven. My cock slid in and out of her ass, and she moaned like a whore the entire time. I couldn't let her do all of the work, so I started pumping up and down, bouncing her on my cock.
Yesterday, she would have been in sheer agony. Now she was in ecstasy. Her tits bounced up and down as I fucked her tight little ass. My hands grabbed onto her ass cheeks and helped bounce her up and down even harder and faster. She moaned, and screamed, holding on to me for dear life.
"Fuck my ass!", she screamed, "Harder! Harder! Fuck me!"
I had never heard her talk that dirty, even when I was fucking her the regular way.
So I did what she asked. I fucked her ass harder and harder, and each time she screamed louder and louder. Finally, I rolled over and pinned her to the bed, facefirst. My cock found her tight spot again and penetrated her from behind.
"Oh yes... more... more!" she moaned into the pillow.
I pushed myself in a good four inches... then pulled out two... then in again... then out... then in... then out... finally I was up to the base of my cock in her ass. She buried her face in the pillow to keep from screaming in pleasure again. I pulled almost all the way out, then forced my way back in. I could feel just how tight she was... she had barely lost her anal virginity, and I was already fucking her hard. Her ass wasn't ready for it... but because of the hypnosis, every second of pain was pleasure before she even had a chance to feel it. She loved every second of it. Every time I forced my way into her tight ass, she felt like she was on the verge of orgasm.
So I fucked her harder and faster, and harder and faster. Finally, I felt her convulse in orgasm. I kept fucking her, harder and faster. She moaned into the pillow, and the orgasm continued, as I fucked her over and over again. I could feel her quivering in exhaustion as I gave her an orgasm that just wouldn't stop. Finally, the orgasm came to a crashing halt as I had my own deep inside of her. My juices exploded from my cock, making her scream one last time.
"Oh god... oh my fucking god..." She was at a loss for words... and so was I. "Oh god... baby... let me know when it's up again... I want to do it again..."