I should be ashamed to tell you this story. But for some reason, I have to do it.
My name is Billy. I had just broken up with my girlfriend, Wendy, and I was feeling pretty blue about it. It was the summer after my junior year in high school I had just turned 18, and my parents were taking me on a trip to see colleges in the southeast. We were staying at a very nice resort hotel near Atlanta, my parents had gone off to play a few rounds of golf. I was alone with my moody thoughts by the hotel pool.
I had been a swimmer in high school-- not a great one, but good enough that my coach had told me to shave off all my body hair so I would have as little resistance as possible in the water. I had worked up a good tan, which set off nicely against my little white Speedo bathing suit. I had covered my body with oil and now, glistening, I had hoped this afternoon to find a cute girl by the pool. The only girls there seemed to ignore me, so I tried to lose myself in a novel. That's when I heard a deep male voice ask me a question.
"Is this chair taken?"
I looked up to see a big man with a broad face. He looked to be about 45 years old and in extremely good shape. I told him the chair was available, and e sat down right next to me. I had to admit it, he was extremely handsome. As he took off his robe, I saw his powerful muscular body. He was so much bigger than me, I felt like a girl beside him--- perhaps, in retrospect, too much like a girl.
We struck up a conversation. His name was Jim, he said, and he was here on business.
As usual at that time in my life, I wasted no time telling d him all about my breakup with Wendy. He seemed quite sympathetic and interested, leaning forward and offering me advice. As he made his points about how I should handle my pain, he kept touching my knee. I thought about moving my leg away from him or telling him to stop, but for some reason, I didn't.
The more we talked the more his hand simply rested on my knee. I felt a little uncomfortable at first, but soon I got used to it. He stared into my eyes as he spoke to me. He seemed very wise, with his deep voice, and I noticed his fingers were squeezing my thigh as he spoke.
I also noticed, to my horror, that my cock was beginning to harden in my suit. His long thick fingers were now sliding up and down my oiled thigh. I was finding it harder to breathe. My cock was now stiffening, it had formed a tent, and I knew he could see it. But I didn't try to stop him from touching me.
Fortunately, we were the only people by the pool at this point. That's when he took things to the next level.
"Well Billy," he said. in a husky half-whisper, "Want to come to my room for a drink?"
I decided that a little alcohol might relax me a little so I agreed. We both put on our robes, grabbed our stuff,and headed to the elevator. We didn't speak as we rode to the top floor of the hotel. As we rode I thought I felt his hand touching my bottom through my terry cloth robe. Why wasn't I telling him to stop?
We entered his suite, and I was impressed by how big it was compared to the rooms my parents and I had rented. We were in a living room, but the bedroom was someplace else. He asked me if I would like some bourbon and I nodded. He smiled, fixed us both a drink and we toasted our new friendship.
I finished my drink rather quickly, and he made me another one. As I began sipping it, he put a hand on my shoulder and looked deeply into my eyes.
"You were getting hard out there, Billy," he said. "Was I making you hard?"
I blushed and looked away.
"Look at me young man," he said, his voice now a little menacing.
I didn't like where all this was going, but I also didn't want it to stop.
"You have the kind of body that would make any girl happy."
"Show me again, Billy," said Jim. "Take off your robe and show me your body."
I know. I should never have slipped that robe off my shoulders. and let it fall on the floor. But it felt good to have him admire my body.
"Oh yeah," said Jim, "nice pecs, nice thighs, and what a tight set of abs!"
"Turn around, Billy," Jim told me. I did as I was told. I could feel his eyes on my bottom through my swimming trunks. I resisted the temptation to wiggle it for him.
"So smooth," said Jim.
I picked up my robe. This had gone far enough. Jim stepped in front of the door and tilted my chin up toward his.
"You're not leaving yet, Billy," said Jim. "I'm just getting to know you."
That's when he kissed me. Suddenly, I had my head tilted up and my robe had fallen back to the floor.
I had never been kissed by a man before. It was such a sweet, soft kiss. My mouth opened to accept his probing tongue. I felt his hand cup my firm, round ass through my swimsuit. My cock grew stiff against his thigh.
The bourbon combined with the lust to make me want what was coming next, I guess. When Jim pull ed down my swim suit, I felt a sense of excitement. Peeled free of all my clothes, I was naked now. A man old enough to be my father was kissing me, inspecting me and feeling me up.
"You shaved your cock," said Jim, stroking it up and down. "You look like a little boy."
He was patting my ass now, lightly spanking me. I felt my cock wave stiffly before me.
"No," said Jim. "You're more like a girl, like a girl who needs a good fucking."
I felt myself swooning in his arms.
"I need to get you wet now, don't I?"
Jim's fingers,covered with a greasy substance were now probing around my ass. I squirmed to free myself, but he was holding me tight.
"Hi, Wendy," said Jim, staring into my eyes as he slid his fingers in and out of my bottom. "Want to go out with me?"
His mouth clamped against mine as his fingers wiggled against my sphincter, and I felt my cock pulsing lewdly in front of me. Jim was mocking me now, but I was ready to be taken like a girl, just as he was getting so hot treating me like one.
Jim pushed me to my knees , and then he stripped naked. I gasped at the sight of his cock-- so much longer and thicker than mine, his balls so big and hairy.
"Suck me, Wendy," he said, guiding my head to his cock. I began by licking his shaft. He groaned as my tongue glided over the bulb of his cock. When my lips engulfed his knob, I felt it pushing against the back of my throat.
"Such a sweet little cocksucker," Jim muttered. I felt his cock stiffen more and more inside my mouth.
I was trying to prepare myself for his orgasm. I wasn't expecting him to scoop me up in his arms and carry me into the bedroom. He kissed my mouth again as he lay me on the bed.
"Roll over and show me your ass, Wendy," he said.
I lay atop the blanket with my ass hiked up a little.
"Such a pretty little bottom," he said. "Wiggle it for me, Wendy."
I felt my hard cock throbbing beneath me. He started spanking me harder now. I winced in pain, but I loved every dirty second of it.
"You're my little whore now, Wendy" Jim said. "Aren't you?"
"Yes sir," I said.
"Then get on your back and spread your legs for me."
I felt him pack more lubricant up into my ass. I knew what was coming next.
He mounted me like the girl I knew I was . I winced in wicked pain as he entered my virgin ass for the first time with that hard tool of his, but soon, I was riding on his big thick stick, grabbing his ass and kissing his mouth. I had become his girlfriend and he had become my lover.
"Don't you wonder who's doing this to your Wendy right now?" he whispered cruelly into my ear as his cock plowed my ass. "Don't you wonder whether she's cumming harder with him than she ever did with you?"
My cock, meanwhile, was swelling and straining, and I was ever so ready to cum. He muttered such nasty things in my ear about what a slut I was and how hot my pussy was, and that, coupled with the masterful thrusting of his cock, were taking me over the edge.
Without being touched, my cock exploded in an orgasm that sprayed semen onto the chest of my lover as he continued to fuck me hard and fast.
"Good girl," he said.
His cock was so stiff and big inside me.He was grabbing each cheek of my bottom in his big hands and thrusting now with an urgency that could only mean one thing.
"Take my cum, you little Bitch!" he roared.
With a loud groan he rocked back and forth a couple of times more and I felt his penis spew his seed deep inside me. I curled my legs around his back and let him fill me up.
A few minutes later, his cock slipped from my ass, and I felt his cum oozing down my inner thighs.
He kissed me again, then grabbed the shaft of my cock.
"You know why you lost your girlfriend?" he asked, "Because you fuck like a girl."
I hated to admit it, but he was right.
Later that night, after my parents had gone to sleep, I went back to his room. This time, however, under my jeans, instead of my underpants, I was wearing a lacy pair of white bikini panties I had stolen from my girlfriend.