Before I get into this story, I would like to cover an administrative detail. Many of my readers have been unable to locate my other stories. The following is a list of the story titles and they can all be found under Prolific Authors / Twonight:
Black Dorm World's Hottest T-Girl The Awakening Star Cruiser The Inmate Shocking Encounter Olympiad Turning 18 The Gamblers The Realtors The Kidnapping The Fluffer First Encounters
Please send feedback to twonight@excite.com. I really enjoy hearing about your first sexual encounter so tell me about it.
As I mentioned above, I really like to hear about my readers' first sexual encounters. I have gotten a lot of great stories. Although I can't vouch for the validity of them, I decided to share a few of them with others, with the names changed and no references which would reveal anyone's identity.
Ok, on with the story:
Garret's story:
The date was July 19, 2002. That was the last date that I could say that I was a totally straight man. I was a 29 year-old happily married man with a good job and a nice suburban home. Everything was normal, or at least as normal as that kind of life can be. That was before I met Tony.
Tony was a college kid who was working as a summer intern in our office. He was average height but had a nice build and a nice Italian look. Most of the female interns were after him and rumors flew about all the younger female employees that he was fucking. I had to admit I was jealous. Tony started hanging out at my office on a regular basis, just shooting the breeze when he wasn't delivering mail and supplies. I tried to pry some details out of him, but he just smiled and denied everyting. I wasn't buying it.
One afternoon, while my wife was out of town, Tony asked me if I would like to go for a drink with him after work. "What the hell," I thought. "I might as well take advantage of my week of freedom and have some laughs." I agreed and we met in the parking garage and took my van. We put his bike in the back and headed off to a local bar. I had never heard of the place, but I didn't know much about the downtown scene. It was pretty quiet when we got there, so we sat at the bar and had a beer. I was surprised that there were no televisions with baseball playing like most of the bars I was used to.
Tony and I just made small talk for a while and several more men came in. Pretty soon, the place was very crowded and the speakers began to blare a techno dance song. I was surprised that there were no women to be found and I asked Tony about it. Before he could answer, a man approached and asked me to dance. I had to ask him to repeat it and he did. Suddenly it all made sense. I was in a gay bar. I politely refused the dance, then turned to ask Tony why the fuck he had brought me to a gay bar.
"I wanted to get you drunk," he said.
"For what?"
"Because I want you to fuck me."
I was speechless for a moment.
"You want what?"
"I want you to fuck me. I wanna suck your cock. Then I want you to bend me over and fuck me."
"But I'm not gay."
"That's OK. I've been fucked by lots of straight guys when their wives are away. They get horny and I give them what they need."
I tried to be adult and sophisticated about the whole thing, but it was difficult. I declined emphatically and we left immediately. As I drove him home, we didn't speak. I kept looking over to see if he was checking me out. I imagined that he was looking at my dick, lusting after it. I have to admit that the thought of him sucking it was causing me to get a bit aroused, but I said nothing to Tony. As I dropped him at his apartment, he told me to feel free to call him if I changed my mind. He reached over and squeezed my partially erect cock and said, "I'd love to swallow your load." I asked him what made him think that I would change my mind and he said, "Because half of the married men that have fucked me turned me down at first."
I pulled away quickly and drove home as fast as I could. My mind was reeling. It was one of those evenings where you start out with one expectation and things take an incredible twist. I went to bed, prepared to sleep, but lay there for an hour staring at the ceiling. All I could think of was his mouth on my cock or my dick in his ass. I had tried to get my wife to try anal but she was deadset against it. I had fucked a couple of girls in the ass before I married Lisa and I really missed that feeling. I tossed and turned until I finally crossed that line. I picked up the phone and called his cell number. I figured he might as well be awake too.
When he picked up, I hesitated, then asked, "Is it too late to take you up on your offer?"
"No man it isn't. In fact, I'm almost to your house now."
"Why were you coming here?"
"I could tell by the way your cock was getting hard that you wanted it. I figured it would take you a couple of hours to get up the nerve to call. Just relax and I'll be there shortly."
About five minutes later he arrived. He was wearing tight shorts which showed off his hot ass and I couldn't help but picture my cock sliding up there.
"Damn, dude, you're ready to fuck me right here on the porch aren't you."
I was embarrassed, but he was right. I let him in and he immediately reached out and opened my robe. He reached into my briefs and grabbed my cock, then walked to the bedroom, pulling by my rapidly growing cock. By the time we got to the bed, I was hard as a rock. He quickly stripped, revealing a hot ass and a sizble cock of his own. He knew I was really horny and he didn't make me wait. His mouth engulfed my cock and swallowed it to the hilt. My wife had never gotten more than half of it in her mouth. Tony began to bob up and down on it, taking it deep in his throat, then almost all of the way out. I couldn't believe how good it felt. With each thrust, his tongue ran down the length of my shaft, then paused to lick my balls. His technique was phenomenal.
I really wanted to fuck him, but the feel of his hot mouth was just too good to pull out. I usually have pretty good staying power, but this was just too much. I knew I was about to explode and I warned him. Instead of pulling off, like my wife always did, he sucked even harder. In a matter of seconds I was blasting his mouth and throat with a river of sperm. He moaned as he sucked more and more semen from my long, hard shaft. I had never had a blowjob like this in my life. Women always shied away from swallowing my load. Tony was swallowing it like he was dying of thirst and my cum was water. He kept sucking and sucking until he had every drop.
He looked up at me, with my cock still in his mouth. I expected him to pull off and leave but, instead, he just curled up with his head on my thigh and my limp cock still in his mouth. He fondled my balls and ran his tongue up and down my shaft, being careful not to lick my overly-sensitive cockhead. Only a man would know to avoid that. I ran my fingers through his dark black hair as he gently caressed my balls and shaft. I knew now that he was going to get me hard again so I could fuck him. I was amazed at how well he could read my thoughts and anticipate my desires. He pulled off my dick and began to stroke it as he licked my balls. Then he really surprised me by licking my asshole. Not only did he lick it, but he began to force the tip into my hole and wiggle it around. I hated to admit, even to myself, that this was getting me really hot. I guess my cock gave me away as it began to grow rock hard. He replaced his tongue with the tip of his finger as he went back to sucking my dick. That extra stimulation made his cocksucking even better, but I was ready to fuck. Again, he anticipated my desires as he rose and asked, "Are you ready to fuck me?"
"God yes!!," I replied.
"Ok cowboy, here's how it works with me. I don't want you to make love to me like you would with your wife. I want you to fuck me. I want you to mount me in any position you want and fuck the living shit out of me. Don't worry about hurting me and don't worry about my pleasure. My pleasure will be having you use me as a fucktoy, a hole to pleasure yourself in. When you cum, feel free to shoot it up my ass or stick it back in my mouth. And when you're done, you can fuck me again and again. As long as you can get hard, you can fuck me again. I'm yours to use until you are done."
I couldn't believe my ears. It was like a dream come true. Since I was already on my back, I had him lube me up and sit on my cock. It took a little work, but soon my big cock was buried in his ass. He sat there for a moment, rubbing my chest as he adjusted to my big dick. Then he began to bounce up and down, slowly at first, then very rapidly. When he lifted up, my cock came very close to slipping out before his ass came crashing back down and swallowed it up again. The tightness of his ass was incredible and I loved watching his big dick waving as he bounced. He was rock hard himself so his dick didn't flop. It just waved slightly like a conductor's baton. I thought that was appropriate because his ass was like a symphony of sensations on my dick.
After watching his cock for a while, I just had to touch it. I had never touched another man's dick and I have to admit that it was strange when I first grabbed it. Tony moaned deeply as I stroked it with each of his bounces on my cock. It felt soft and hard at the same time. I loved the feel of it. I imagined how it would feel in my mouth - how it would taste. I was quickly brought back to reality as Tony flipped on his hands and knees and waved his ass at me, as if to say, "Mount my ass and ream me out." I positioned myself and slammed my cock home with a vengeance.
"Oh yes!!!," he screamed. "Fuck my ass like the cheap whore that I am. Slap my butt with your big balls."
His dirty talk was contagious.
"Take my cock in your slutty hole, bitch," I yelled. "See what it feels like to get buttfucked by a real man, instead of those queers you hang out with."
I was slamming the living shit out of his ass and he was thrusting back to meet each stroke. This went on for a while until I got the urge to flip him on his back. He eagerly accomadate me, bringing his knees up to his shoulders and giving me easy access to fuck him like a woman.
"This is a better position for a bitch like you, on your back and looking me in the eye while I fuck that pussy ass of yours. Tell me you're a fucking cunt."
"Oh yeah. I'm a total cunt."
"Tell me you're a cocksucking whore."
"I'm a cocksucking, cum swallowing whore."
"I'm tired of looking at your slutty mouth. Get on your stomach."
With that he flipped over and lay flat on his stomach. I straddle his ass and sank my dick to the bottom of his ass. Then I began to ride him harder than ever. With each downward thrust, my flesh slapped his with a loud smack. He tried to raise his ass to meet my thrusts, but each time I slammed his ass into the mattress. On and on we went until I sensed the arrival of my orgasm.
"I'm gonna cum in your ass now bitch. I want you to squeeze my cock and make me cum hard."
His ass muscles tightened just as I began to unload hot semen in his ass. There's something about coming while fucking really hard that is so exhilirating. Cum seems to shoot much harder and the orgasm is so intense. For what seemed to be a lifetime, I continued to fill his ass with a hot, sticky cum cocktail. When I finally pulled out, I shoved my cock directly into his mouth and told him to clean me up. He began to lick and suck me clean. As tired as I was, I knew that I just had to fuck him again. I might never have this chance again and I was determined to make the most of it. He looked me in the eyes and asked if he should leave now.
"You'll leave when I'm done pounding that whore ass of yours and not a minute sooner. Got that?
"Yes sir!"
"Lick my ass some more cuntface."
His tongue felt even better now because he had some of my cum on it and it made it easier for him to slide more tongue in my ass. I made him tongue my ass for a while, then I straddled his face and had him lick my balls and shaft. I suddenly felt the need to pee and told him I would be back after I took a leak.
"You don't have to leave for that," he said. "Just stick it in my mouth and make me drink it."
I was repulsed at first, but in the mood I was in, nothing seemed that crazy. He encouraged me again, so I lay over his face and crammed my cock in his mouth. It took me a minute, but the urine began to flow. I was really pissing hard and he had trouble keeping up. I slowed myself to let him swallow, then began to piss again. He finally got every drop down and licked me clean.
"Thanks for putting your fluids inside me, sir," he said. "I want to swallow all of your juices."
I rested as he continued to lick and play with my dick. Suddenly I had an interesting idea. I went to the closet and got my wife's merry widow outfit with the crotchless panties. I threw it at him and said, "Put this on bitch. If you are going to act like a cheap whore, then you should dress like one." He eagerly obliged, even donning one of her blond wigs. I have to admit that he made a very attractive woman and I was eager to give this slut another ride. I fucked his ass again causing the sperm from my previous ride to gush out as I penetrated him to the max. When I fucked his ass from behind, his cock hung from the opening in his panties creating quite an erotic site. Seeing this person who looked every bit like a woman, except for this long, hard cock dangling below, made me want to fuck him even harder. I finally shot another load in his mouth, after slapping him several times with my hard cock.
I reached underneath to feel his hard cock coming through the open crotch and I was stunned to find that he had cum while I fucked him. I never even noticed. When I found it he became very apologetic. I reassured him that it was OK, but I made him lick his cum off the sheets, which he did eagerly. He asked if he should leave now, but I told him no. I told him to leave the merry widow on and get into bed with me. I spooned him with my arm around him and told him to go to sleep. I was still naked and my cock was pressed against his ass.
About 4AM, I awoke to find my cock as hard as a rock. Tony was still asleep, but I just had to have some more ass. I raised his leg and pressed my cock against his asshole. He unconsciously pushed back to meet me and my cockhead slipped into his ass. That woke him with a start, but he quickly recovered and pushed back to take all of my cock in his ass. When it bottomed out, I made him stop and not move. He was confused, but did as he was told. I lowered his leg and just lay there and enjoyed the feel of my cock safely buried in the depths of his ass. I reached around and began to stroke his cock which, by now, was very hard. He moaned and writhed as I stroked him, causing his ass to rub my cock and get me more excited. I flipped him on his stomach and pounded the shit out of his ass for ten minutes, erupting in his ass for what seemed like the 10th time. When I finished, I stayed on top of him. He didn't understand, but I told him to just stay there. My cock softened but was too deep in his ass to pop out.
I stayed on top of him for a good thirty minutes, until my cock started to show signs of life again. I didn't think it was possible, but I got hard again. As soon as I was hard enough to ride him, I began to pound his ass again. He moaned deeply as my thrusts caused cum to pour from his ass and drip down his balls. I was exhausted, but I kept humping as long as I could. Just when I thought I was going to pass out, I shot another load of cum in his ass and rolled over on my back. He dove on my cock and licked it clean, smiling as cum ran down his chin. I felt his cock and noticed that he had gotten very hard as I fucked him.
I couldn't resist the urge anymore and I dove on his cock sucking it like a vaccuum cleaner. He didn't last thirty seconds before shooting his load in my mouth. The taste was not good, but it was exciting to taste and feel his cock in my mouth and I was proud that I was able to make him cum in my mouth. After that, we both passed out and didn't wake until 8:30 in the morning. I started to rush around and get to the office, but then I saw his naked ass on the bed. I walked to the phone, called the office, and told them I was taking a vacation day to deal with a personal affair. I smiled as I finished the call because he already had my dick in his mouth. I mentioned that I had to pee and he just smiled and took my dick back in his mouth.
About a year later, Tony began living as a woman. He got breast implants, took hormones, and changed his name to Antonia. I have continued to see him through all of the changes and I still can't get enough of his ass except, now, I get to feel a sexy pair of tits when I fuck her. It's the best of both worlds.
As always, send comments to twonight@excite.com. Check out my other fiction stories, Olympiad, The Gamblers, Black Dorm, The Awakening, The Inmate, Turning 18, The Gambler, The Realtors, The Kidnapping, The Fluffer, and Star Cruiser - and my nonfiction Shocking Encounter and Tess' story - World's Hottest T-Girl.