Bad Halloween Habits

Cindy and I got ourselves together and headed to the party my friend, Rob, was throwing. I had planned to attend because Rob was a musician and always seemed to be surrounded by scads of beautiful women. As we drove, Cindy slid across the seat and slipped her arm around me, resting her head against my shoulder as we drove.

"Greg, I can still feel your cum in my ass," she said softly, her right hand resting on my thigh. "It makes me feel all loosy-goosy!"

I smiled, glancing down at her as I drove.

"You felt plenty tight to me," I said, laughing.

There wasn't a parking spot in sight on the street where Rob lived. We wound up parking blocks away, and walking in our costumes. When we got to Rob's, we could tell the party was raging. Music was blasting, people were drinking, smoking who-knows-what, and some were sprawled out in chairs, couches, and on the floor, making out.

Almost immediately, a lovely young woman dressed like a vampire came up to me, whispering, "Sister, save this sinner." I jumped a bit as her hand slid down my back, gripping my ass rather tightly. I turned to speak to Cindy, but she was across the room speaking earnestly with a cute, slender, brown haired woman, also dressed like a school girl.

My vamp, who told me her name was Jessie, seemed really eager to have her way with me. She led me to a bedroom where two other couples were fucking on the floor. Jessie pushed me onto the bed and rolled me over. I looked over my shoulder, and she was smiling wickedly.

"I want to slip my tongue into your pussy, sister," she said.

She spread my legs and raised my dress, pushing it up over my ass. Gripping the elastic band of my boxers, she yanked them down and off. She slid her hands slowly up over my calves, thighs, and onto my ass cheeks. I could feel her hot breath on my ass as she spread them. My cock, despite recently depositing a huge load of cum in my sisters ass, was rock hard, pressing into the bed beneath me.

"Sister, are you ready to feel my tongue," Jessie asked, teasingly.

"Oh god, yes, please!"

I'd never been rimmed before, and when her tongue slipped down my crack and over my clenched asshole, I thought I'd faint. I gasped involuntarily as she swirled her tongue over my ass, teasing me mercilessly, then pressing hard against my opening. It almost felt like she was trying to fuck me with it. I tried to relax, tried to accept her intruding tongue. I opened my eyes and watched the two kids next to me as they fucked. The guy was on his back, eyes closed, hands gripping the girl's breasts as she ground herself on his cock. She wasn't moving up and down, but in circles, with his cock deep inside her.

All of a sudden I realized that Jessie's tongue had made its way into my virgin ass. She was fucking my ass with her tongue. Inarticulate gibberish spewed from my mouth as I was overcome with pleasure. I gripped the sheets desperately, trying to thrust my ass back against her lingual probe. All of a sudden, she stopped. The cool evening air seemed to rush over my still glistening ass. Then, I felt her climb over me, lay on top of me, and start to grind against my ass. It felt really good feeling her on top of me, and I pushed back against her. I felt her adjust her clothes, and felt her bare skin against mine. All at once, though, I realized that there was something amiss. Instead of the soft curve of a female mons, there was a significantly masculine penis rubbing against my ass.

"It won't hurt a bit," Jessie whispered, sliding her cock into the crack of my ass, slipping it lower until it pressed against my spit-slickened hole.

"Just relax some more, lover," she whispered, rocking her hips gently.

I opened my eyes again, watching the two kids on the floor. Now she was on her back, and he was on top, her legs over one shoulder, her knees pressed against one breast as he thrust powerfully into her. Her fingers grasping at his hips, trying to pull more of him into her.

Suddenly, I felt Jessie slipping into my ass. This was obviously destined to be a night of firsts. At first, the intrusion into my virgin ass seemed shocking and strange but, after a few moments, my ass relaxed even more and her thrusts began to awaken feelings in me I'd never known. I started to moan and shake like a mad man.

"That's your prostate, lover," Jessie whispered in my ear as she thrust more deeply into my quivering ass.

Waves of hot white pleasure shot through me, feeling like I was splitting apart into a million pieces. Jessie began to move faster now, fucking me harder, sending her cock into me with such force that my teeth rattled. Her breathing was ragged, and all of a sudden I felt her stiffen, her cock twitching and pulsing deep inside me. I knew she was cumming, cumming in my ass.

Consciousness slipped away, and I went spinning off into a blissful oblivion for a time. As mind and body reunited, and my vision returned, I realized that Jessie had departed, leaving me rather exposed and open. The lovers I had admired were gone now, too. The room was quiet, and I slipped into a restful sleep.