Jane Fucks his AssbySysiphusRock©
I remember the first time I was ass-fucked. It was Jane of course, who pushed the boundaries and opened up a whole new world of sexual exploration. Jane and I had been dating for months and the sex was spectacular. Every position, 4 or 5 times a day, for weeks on end. She started to complain that her pussy was sore, but then she would reach over and start stroking my cock and we'd be fucking again.
One afternoon, I finished work and headed over to her place. I knocked and there was no answer but I could hear soft moans from inside. I pulled out her spare key and opened the door. The moans grew louder. I followed them to the bedroom where Jane lay sprawled upon the sheets, a pillow under her ass, and a vibrator buried in her pussy.
"I couldn't wait for you," her voice husky.
Her fingers worked furiously on her clit and she came right then. Jane was the first woman I'd been with whose pussy actually ejaculated. Her back arched, lifting herself off the pillow, and her pussy squirted, forcing the vibrator out.
I jumped on to the bed and dove face first into her cunt. She gasped and came again, squirting out more juice which I greedily lapped up. She pushed my head away.
"Oh, I'm too sensitive, baby," she said. She reached down to feel my cock straining against my pants. "Ooo! But we need to take care of that, don't we?"
Urgently I pulled my clothes off. The moment my cock sprang free she gripped it hard, almost painfully.
"Not so fast. I have my toy," motioning towards her vibrator. "I don't really need this thing."
She pulled my swollen member up to her face and seductively ran her tongue over the head of my cock, purple and swollen.
"Mmmmmm, that tastes good," she purred.
I groaned. Jane loved to suck my cock and did so expertly. My previous girlfriend wasn't a big fan of fellatio so Jane's enthusiasm for the act had been a rather pleasant change of pace for me. In fact, she enjoyed it so much that I often never got to fuck her pussy. I groaned in delight, and tried to push the head of my cock past her lips, but she squeezed tighter and pushed me away.
"I don't think so, not today. You see, I had to masturbate because you were late, so it's only fair that you should have to do the same." She was stroking me now.
"But..." I began to protest.
"Either that or nothing," she cut me off. She knew the answer to that. "Roll over, on your back," she said sternly.
I did as I was told. I felt something wet and cool drip onto my cock and looked down to see Jane applying ample amounts of lube.
I hesitated a moment then slowly began to stroke my cock.
"Nice. Look how much bigger it's getting. I like when you perform for me."
I loved to hear her voice while I jerked my cock.
"Did you notice my toy," she asked.
I opened my eyes to look at the dildo. The top half was gold, the bottom half black and it measured about eight inches and was about an inch and a half thick. It was still wet with her juice.
"You know why I like it so much?"
"No," I grunted.
She twisted something at the base and it began to whir. She twisted again and it vibrated faster then slower, then pulsed.
"Because I can set it to whatever setting I want. Plus, it just happens to be the size and shape of your cock, so that's nice also."
She pushed it to my mouth.
"Lick all the pussy juice off."
I hesitated. The metal tip was cool and covered completely with her scent and flavor, which I just love to taste. She turned it to allow me to lick it clean.
Her eyes arched in surprise.
"Hmm. You're a talented cocksucker."
I suddenly became self-conscious of what I was doing and stopped.
"Oh, don't stop, baby, I like watching you. Go on."
She started pushing it deeper into my mouth, eventually all the way to my throat, encouraging me to "suck it good, bitch."
"Now you know what it's like for me, don't you?" She stabbed it into the back of my throat causing to gag. "See? Not so easy, is it, when I face fuck you."
I couldn't say a word in protest, but I also didn't stop stroking my cock, or move my head away. Instead I just tried to relax my throat and not gag.
"You're quite good at that aren't you," a bit of surprise in her voice. She smiled wickedly. "I think you are a natural cocksucker. Are you a fag?"
Hearing her talk dirty while stuffing a dildo down my throat was pushing me to the edge of orgasm. My hand worked furiously on my cock and I was ready to explode. She noticed and slapped away my hand.
"No, no cumming yet. I'm enjoying this." She worked the dildo in and out of my mouth quickly. "You know, if you like this in your mouth, you might like it in your ass."
Her eye looked at me quizzically. She had pushed my hands away from my rigid cock again and she took over, stroking me firmly.
"Tell me, baby, do you want this cock in your ass?"
She had stuffed the dildo so far in my mouth I couldn't answer, but I shook my head no. Jane squeezed my cock hard, making me jump. She leaned in and whispered in my ear.
"Are you sure baby? Are you sure you don't want that cock in your mouth in your ass?"
I shook my head no.
She stroked faster and then she stopped suddenly, just before I was about to shoot my load.
"Don't you want to cum? I'll let you cum if you let me put this little thing in your ass."
She started stroking again.
"Tonight, I'll let you fuck my ass," her voice was husky and her breath hot on my neck. She knew that would get me. I loved her ass, and I loved to bury my dick in it. We didn't do that enough as far as I was concerned.
"Okay," I whimpered around the vibrator in my mouth . My cock was so hard and needed to explode. At this point I would do anything for release.
She pulled the vibrator out of my mouth and quickly lubed it before I could change my mind. On a couple of occasions, while giving me a blow job, she had slipped a finger in my ass but nothing nearly as large as the dildo. She ran her slippery finger over my puckered hole, pressing slightly against it.
"Ooooohhhh. That feels like a virgin asshole. I'm gonna pop that cherry."
This sent my head spinning. I loved when she talked nasty. The nastier the better.
"Maybe... I'm not sure..."
"Too late, bitch."
I felt the cool metal of the vibrator pushing against my hole. It suddenly seemed like the biggest thing in the world.
"Better stroke that cock, bitch, or this is gonna hurt."
My hand frantically moved up and down my shaft.
"I think someone is having fun," she smiled wickedly.
I began to protest as my ass felt like it had been split open. I was sure I must be bleeding.
Cunt? She's taking this way too seriously.
"Ow, stop. That's hurting me."
"It's just the tip," mockingly repeating the words I say whenever she complains about my cock pushing into her.
I stroked my cock so hard, trying to create enough pleasure to counter the pain and not entirely succeeding.
"You're a fucking slut, and I'm going to fuck you like one!" With that she shoved the vibrator as far as she can up my ass and turns it on. "How do you like that," she screamed.
My cock jumped and starts squirting cum all over my chest and stomach, the first stream hitting under my chin. My ass pushed the dildo out.
"Nice, very nice," Jane purrs.
My heart is pounding in my ears and my cock has stopped squirting jizz, but it's still hard. A shudder of relief passed through me.
"How did you enjoy that," she asked as her finger swirls a puddle of cum on my stomach.
I tried to tell her I didn't enjoy it at all, but she knew that was a lie.
"I think we'll do this again," she grinned evilly. "In fact, I think from now on if you want to fuck my ass, I'm gonna get to fuck your ass."