Don't Tell Mumbystarbelliedboy©
Note: This is a story I wrote many, many years ago. I've cleaned up the spelling and grammar, but otherwise left it as it was.
"We're going, then," my mum called up. "We'll be back sometime late this evening."
"OK, bye," I replied, then listened for the door to shut. When it did I climbed on the bed and gave Lisa a kiss.
"What would you like to do now?" I asked her, searching her blue eyes.
"Well, we've tried so many positions," she replied. "I'd like you to break my anal virginity."
"OK, if you like."
I pulled her trousers and knickers off and flung them in a corner, then as I stripped off she took her top and bra off, shaking her long blonde hair out of her face to cascade down her back when she finished.
"We'll need some strong lubricant for this, because I don't want to hurt you." I told her.
"I know, and it has been provided for," she replied, getting up and rummaging in her bag. She pulled out a tube of baby oil. "Will this do?"
"That's perfect darling," I replied.
She passed the bottle over to me. I poured a bit on to my hand and began to rub it on her breasts, circling her nipples, massaging her neck, then down around her pussy. Then she poured a bit on to her hand and masturbated me a bit until I was completely hard.
"Now, get on the bed on hands and knees."
She did so, and then I knelt up behind her and rubbed a bit of oil into her buttocks, before pouring a good deal into her arse hole. I put a bit more on my penis and put the bottle down. Gripping her hips firmly with both hands and resting my dick on her sphincter, asked her:
"Ready? Do tell me if it hurts and I'll stop."
"OK." She replied.
I pushed my hips forwards, slowly. My cock forced through her tightest hole, squeezing firmly. Lisa let out a moan of pleasure, so I pushed onwards, feeling the tight ring of muscle work its way up my shaft. The tip of my penis moved through the soft tight tube, lubricated by oil. Finally I had gone all the way in, her ass touching the tops of my thighs.
"This OK for you darling?"
"Yeah, it's wonderful!" she replied. I withdrew very slowly, until her sphincter was just below the head of my dick. Then I pushed in again. I continued like this for a couple of minutes, then leaned over her back, grabbed her tits and pulled her on to her right side. I pushed my left leg forward moving hers with it, but kept mine and her right leg straight, so I could still enter her. In this position I could kiss her neck and nibble her ear. Still holding her breasts, I got back in the rhythm of entering and nearly withdrawing. Lisa clasped my hands holding her with her right hand, and moved her other hand down to pull her buttocks apart. She began to make sounds of pleasure: "Mmmm".
Then an idea occurred to me. I withdrew completely and rolled Lisa on to her back. I held her legs up towards her head, and then forced my cock back into her, so that now I could look at her while I did it. Her mouth was wide open, her eyes closed and her cheeks blushed. I pushed through as far as I could go and then almost came out again, going a little less slow than I had been. Then she pushed me over backwards and sat on top of me, leaning back on her hands, lifting herself up and down. Unfortunately she didn't feel like continuing for very long, so she slowly turned around to face the other way, with my penis still inside, producing an amazing sensation as her tight flesh spun slowly over the tip.
I sat up and pushed her back on to hands and knees. I pulled almost out and then back in again, going more steadily. Lisa began moaning louder and more often, and moved her hand down to her cunt and began masturbating herself at the same time. She began to shout, "Ooh! Aah!" so I knew she was nearing orgasm. I began to go faster, coming right out and then ramming my way back up her arse.
Faster and faster, my cock getting hot from the friction of her sphincter, and my abdomen getting hotter as I neared ejaculation. Lisa was screaming with pain and pleasure, her back becoming slippery with sweat. I started to grunt loudly as well. Lisa let out one final, long, loud scream as she orgasmed and I forced my cock hard up her arse and ejaculated, cum filling her anus and squirting out the sides with each of my eight spurts.
I pulled my dick out and we both collapsed on the bed. We kissed and then wiped the worst of the oil and semen mixture that covered my penis and was dribbling from her arse hole, before falling asleep together.