Giving It Up

It was very late at night. My now ex-wife - “the bitch” - was upstairs fast asleep. I sat at the computer as I had for so many nights, for so many years, flirting, chatting and cyber-fantasizing with other men online. Men much like myself, pretending to be women in one room, the women our wives never were, or in another room, men who would never be again in this age of AIDS. Lately though, my curiosity had been getting the better of me. I had experimented many years ago, enjoying having my cock sucked or my ass eaten in a bookstore not far from where I lived. (Ironically, there is now a JiffyLube on the same spot!) But, I was too repressed to go any further. Now, night after night, I flirted with guys online, leading them and myself on toward a tryst only to back out at the last moment. Then lubing up my ass with my own fingers and drilling myself with a trusty, thick, hard, fake cock. Yea, teasing myself night after night, only to satisfy myself with a dildo. This night was different though. I had had to much to drink, I was too horny, too curious, angry, frustrated ... you name it. I wanted to be fucked.

A few nights earlier, I had met a guy online and hooked up in a nearby field engaging in mutual oral sex. That was a first for me. In my previous encounters 20 years before, I had only been the recipient. That evening, I willingly knelt in the shadows of a soccer field and sucked my first cock. It was a strange sensation. The shaft so hard and throbbing and the head so soft and spongy. I reveled in running my tongue over the head and into the slit, sucking hard on his length until he pulled away and sprayed his cum on the damp grass. This night, I sat and stroked my cock as I teased back and forth with J online, telling him of my exploits of a few nights past and boasting of what I would do if we should get together.

Suddenly, the desire began to overwhelm me. Why not? Why shouldn’t I experience my fantasy? Why not try it and no longer be curious? I was tired of lubing my own ass for a fake cock. Whether it was my own “itch” or the ouzo talking, I don’t know, but I found myself in my car, driving to this stranger’s apartment, stopping only to pick up condoms and lube along the way.

Before I allowed myself to think about what was going on, I had knocked on the door of his apartment. The door was opened by a cute 20-something guy in t-shirt and briefs. I admired his basket, his handsome face and his charm and stepped across the threshold of losing my anal virginity.

J was still online with a friend when I arrived, so I sat for a while as he finished his chat. I became impatient with waiting and went to kneel next to his chair so I could stroke his cock while he said his goodbyes. Not soon enough for me, he logged off and turned his attention to me. “Ready for your massage?” he asked.

“And whatever happens, too!” I responded.

J spread a sheet for me on the floor and got his lotion as I got undressed. “Here we go, finally” I thought to myself as I stripped naked and lay down on my stomach for him. J gave me a beautiful massage, working out my tension and apprehensions. I loved the feel of his hands as he caressed my ass, teasing me without touching my hole, my balls or my cock. After an eternity of enjoying his hands stroking my flesh, he asked me to turn over. He kissed me gently as his fingers found my nipples and tugged at them. His hands roamed over my front, as firmly and seductively as they had my back. My cock was rock hard and leaking pre-cum like mad. His hands finally found my cock and balls and I moaned deeply in response. Before I could recover his mouth covered my cock and I almost shouted. It was so hot and delicious getting sucked by J. I was so relaxed and excited at the same time that I was about to shoot. I stopped him. “I want to cum the other way,” I said, pulling my cock out of his mouth (reluctantly) and rolling over on my stomach.

J opened the tube of K-Y and I shivered inside with what was coming. I handed him a condom and looked at the size of the cock that was about to take me. It looked huge, though I guess it was not much bigger than my 6.5 incher. It didn’t matter. I wanted it. I wanted him. I wanted that cock inside me. I lay back down and closed my eyes, reaching back to spread my cheeks open for him. I felt him rub his lubed fingers up and down my crack and then circle my virgin, but horny anus. “Oh god,” I moaned as one slick finger slid inside me. My cock throbbed and leaked against the sheet as I held myself open and rocked back against his finger. Soon, my asshole relaxed and he slipped another finger inside me. “Yessssss!” I hissed and began to thrust my hips back in rhythm to his finger thrusts up my ass.

“Mmmmmmmm” was all he said as I fucked myself up the ass on his fingers.

“Oh god, more,” I moaned as my asshole opened for his fingers.

I heard the ripping of the foil packet as J said, “I think you need something bigger!”

My only response was to pull my knees up under me, positioning my ass for a good fucking. I reached back to stroke his thick hard cock with lube while he kept my ass ready with his fingers. For a moment, I wondered what I was doing here, face-down on this stranger’s carpet, begging him to fuck my ass. But, I wanted it, I needed it. God, fuck me now, I thought. I held myself open and moaned and sighed as I felt the slick head of his cock running up and down my asscrack. “Oh god, yesss...” I sighed as he toyed with my ass. His cock felt so hot and hard, so thick and long, all just for my asshole, I thought.

I felt the soft spongy head center itself on my needy asshole. “Oh fuck,” I moaned as the head teased in and out of my willing but nervous hole. Finally, I felt him center the thick shaft of his cock on my asshole and I lined up my opening with him and gently pushed back....

“Oh shit,” I whispered as I felt the thick head penetrate me. “I’m not a virgin anymore,” I thought to myself as inches of the hot shaft slid inside me. “Ohhhhhnnnnggg” was all I could say as I rocked back with my hips to swallow his length as he plowed forward up my ass. “Yessssssssssss!” I hissed as his cock filled me fully, stretching my hole open, rubbing my prostate from the inside. “Oh my fucking god!!!!” I moaned into the floor as I was deflowered and opened up and fucked and oh god it was sooo fucking gooood!!!! “I guess all those nights of practicing with dildos, vibes and beads were worth something” I thought to myself as my asshole opened up and pleaded to be fucked!

I heard my own voice begging J to fuck me harder. “Yess, oh god yes!” I moaned and rocked back into his plowing hips. “Unng, unggg, unnng, unggg,” was my only response to the sound of his hips slapping into mine, the slick slurp of his cock sliding in and out of my asshole.

I felt every thick inch of his cock as he stretched my hole. My ass opened and throbbed and squeezed his cock as he thrust in and out of me. I begged and whimpered and moaned as he built up from slowly fucking my ass to truly plowing my hole. My asshole burned with sweet pain as he took me and I scratched that itch deep inside. An itch that I could never relieve with a dildo or my own fingers. An itch that could only be relieved with real cock, oh my god yessss, fuck me yessssssss. Hot, hard cock up my ass. I felt his hands on my hips pulling me onto that thick shaft. I felt my asshole loosening and tightning around the length of his cock as it entered and left me. I could hear my own voice as if from outside myself, an endless litany of obscenities begging him to fuck me harder, oh god yes, sooo fucking goood, yessssss fuck my asss, oh yessss fuck me, oh god your cock is sooo goood, yesss, so big and hard and thick and long.... oh fuck yessssssss! Fuck my asssshole!!!!! FUCK ME!!

Finally, with a roar, he slammed into me one more time and I felt his cock throb in my asshole, emptying his balls of cum into the condom covering his cock deep in my ass. “Oh fuck” I moaned, “that was sooooo fucking hot!!!”

His softening cock slipped from my ass and I heard him rip off his condom. I was trembling on my hands and knees, my cock waiting to cum and my asshole still greedy. I rolled over onto my back and began to stroke my cock as I lifted my legs and opened my ass to him again. “Please?!” I begged and moaned as his fingers slid up my slick ass once again. J finger-fucked me until I came with a great shout, showering cum all over my belly.

“Shit, that was hot!” was his only reply as my ass-ring throbbed and squeezed his fingers. I never wanted him to leave me.

“Nnnnnnggg” I moaned as his fingers finally withdrew from my no-longer-virgin ass.

“Damn, I’m glad I’m not curious anymore,” was all I could manage to say.

I dressed. We kissed at the door and soon I was back in my car, with a sated cock and a very happy, sore and throbbing asshole on my way back home. “That was fucking great!” I thought to myself. Wonder if I will ever do it again......