First in the AssbyKrazy35©
I had never let a guy fuck me in the ass before, so when I decided to let my boyfriend Paul do it, I was nervous as hell.
Paul and I had been dating for almost six months. Of that time, we had been having sex for about four months. We did it in all different positions and performed oral sex on each other regularly.
Paul's first hints to me that he wanted to poke me in the butt was when we would watch a dirty movie together. It seemed he always cued up the anal scenes, and whenever one came on, he would watch intently.
Later when we would make love, he would tickle my ass with his finger. He never put it in, but his teasing of my tight backdoor, always drove me to the very edge of orgasm.
One day while he was eating my pussy, and I was lost in the pleasures his mouth was creating, he began to rub his finger on my anus again. It felt good and I was out of my mind with lust. "Stick it in." I hissed.
I couldn't believe I said it and apparently neither could he. He stopped licking and said "Are you sure?"
I reached down with both hands and spread my ass cheeks and said "Don't make me beg."
He slid his finger into my pussy, getting it good and wet. Then he put it against my ass and eased it in. I couldn't believe how nasty I felt, letting him finger my ass, and I couldn't believe how good it felt. I began cumming right away. My sphincter tightened around his finger and I pulled his face back to my pussy. I ground my pussy hard into his face as I came and came.
I think I decided then and there that I was going to let him have my anal cherry, but later when he was doing me doggie style and he asked me if he could, I chickened out. I told him no, and even though he pouted a little, soon enough he blasted a huge load into my pussy.
A few times after that, Paul finger fucked my asshole, and each time I came quickly and hard. I had to try his hard cock in my ass. I just had to have it. I knew it would hurt, but I didn't care.
The next time I went by the local sex shop, I stopped in and bought a bottle of industrial strength lubricant. My pussy got wet just thinking about the evening to come.
I called Paul at his office and invited him over to my house for dinner and 'dessert'. When he said he'd love to, I could tell he thought he knew what I meant. Of course, he didn't know the whole story.
When Paul arrived, I was wearing my black lace teddy. He gave be a big grin and said "You look great. Let's skip dinner and get straight to dessert." Then he tried grabbing at me but I alluded him and said "No, No, No. I spent time cooking you a nice meal and your going to eat it."
He gave me his best puppy dog eyes.
That's when I grabbed the bottle of lube and said "You could do me a favor though."
"Anything." he said quickly.
"Warm this up while we have dinner." I continued, flipping the bottle to him.
He caught the bottle and held it up. Looking at it with a puzzled look he asked "Why am I warming this up?"
"So it won't be cold when you lube up my ass, silly." I said turning and going into the kitchen.
"You mean...?" He started
"After dinner." I interrupted
Dinner was interesting. Paul ate his salad quickly then had to wait on me. I ate slowly. Partially as a tease, but also because I was nervous about letting him do this. Paul ate his main course more slowly, I guess he figured rushing wasn't going to help. He had a hard on the whole time he was eating.
When I finished my meal, I walked to his end of the table and bending down whispered "Are you ready for desert?"
He damn near jumped up from his chair and swept we up in his powerful arms. Kissing me deeply he carried me into my bedroom.
As he sat me on the bed I reached up and unbuckled his belt. I worked the snap and zipper on his jeans. Since Paul never wore underwear, his hard dick flopped out at me. I sucked it into my mouth as his jeans crumpled around his ankles.
Paul gave a low growl and removed his tee shirt as I began bobbing my head on his pole.
I only sucked a few times when Paul pulled away from me. I slid up further on my bed as he removed his pants from his ankles. I couldn't help but think he must be excited about fucking my ass because he has never stopped me from sucking him.
I reached down and unhooked the crotch of my teddy and gave my wet pussy a little rub as Paul began to climb onto the bed. Then he stopped and climbed off, fumbled in his pants pocket and pulled out the bottle of lube.
He climbed on to the bed directly between my legs and buried his face in my snatch. He was an excellent pussy licker and soon enough I felt an orgasm building deep inside me.
I pulled him up to me and kissed him deeply tasting my juices on his tongue. "Are you ready?" I asked.
"Hell yeah!" He said.
We moved around so that I was on my hands and knees in front of him. He squirted the lube directly onto my virgin asshole. It really had warmed up in his pocket, although I shivered in anticipation.
He pushed a finger in me and I shook with an instant orgasm. Paul worked the lube into my ass as my orgasm continued. I tried to relax as the spasms in my pussy subsided. Paul slid a second finger into my ass. He had never done this before, and before I knew it, he had worked in a third.
Just as I was about to cum again, Paul pulled his fingers from my ass. I looked back over my shoulder in disappointment, and watched as he applied more lube to his hand. My disappointment turned to pure longing as I watched him rub the lube onto his hard cock.
He noticed me watching him and gave me a grin moving closer and rubbing his dick on my asshole. I forced myself to relax as I felt him begin to push. Even with all the lube, I was beginning to doubt he was going to get it in, when all of a sudden the bulbous head popped into my ass. Paul held still as my sphincter adjusted to the invader. The pain was intense, but there was no turning back now. I pushed my ass back toward Paul, slowly taking inch after inch of his cock into my tight asshole.
It felt like his cock was ripping me in two but I didn't stop pushing until I felt his balls against my pussy. Paul held his cock deep inside me. My ass slowly began to adjust and the pain slowly began to fade as Paul finally began to pull out.
I moaned as he began filling me a second time. This time only a twinge of pain remained, the rest had been replaced by a pleasure, more intense than any I had felt before. By the time he hit bottom, my orgasm rippled through my body. My whole body spasmed as I let out a squeal of pure ecstasy. I came and came around Paul's hard thrusting cock.
To his credit, Paul fought off the urge to cum while my muscles milked at his dick. Only a few strokes after my second orgasm subsided, I felt my third begin to build.
Paul's breath was coming in short gasps. "Do it!" I yelled "Fill my tight ass with your cum!"
"Oh God." he grunted pushing his cock deep inside of me and shooting his spunk deep into my bowels. His spurting cock set me off as I came again. He reached below me and squeezed my breasts hard increasing the intensity of our shared orgasm.
I collapsed onto the bed as he pulled his softening dick from my sore asshole. We laid there together, gasping for air and recovering for a few minutes.
I rolled over and kissed him reaching down and gently stroking his flaccid member. After only a moment or two it began to respond to my touch.
Paul said "I don't think I have the energy."
"Relax stud," I replied "I'll do all the work."
A few more strokes and his cock was ready for round two. I straddled his hips and pointed his hard cock directly at my dripping asshole. I let my weight down and impaled my self on his stiff pole. This time there was no pain, only pure pleasure.
I lifted myself up and let myself down. Right away I knew my orgasm was only seconds away. Sure enough it only took a few strokes and I was cumming hard. I bounced and wiggled my ass all through my orgasm as Paul reached up and roughly squeezed my titties.
I stroked my own clit and had multiple orgasms or maybe it was just one long one, I'm not sure. Since Paul had already cum once, he lasted much longer this time, to my pleasure. I rode him for what seemed like hours until finally I heard him begin to moan. A few strokes later he shot a second load deep in my ass, as I continued to cum.
Paul's cock stopped shooting and I collapsed on top of him. I kissed him and held him as his dick softened and eventually slid out of my ass.
The next day I was so sore I had trouble sitting, but it was worth it for all the orgasms I had.
That was my first time, but certainly not my last. As a matter of fact, that's why Paul and I broke up. Turn's out I almost have to have something in my ass to cum, and I know I like anal sex much more than in my pussy.
Oh well, I've found a lot of guys since Paul that don't mind pounding away at my cute little backside.