Dirty Business TripbyTravel_by_day©
Chapter 1: The Transsexual Hotel Encounter
"Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and her lips were painted a reddish-brown colour. As she looked at the card I watched the long dark lashes on her lids closely slowly over her huge, sparkling eyes. She slowly opened her eyes again, and reached for a box of cardboard cards sitting off beside her computer.
"Yes, Mr. James. I have your reservation here," her voice was low and gravely. She sounded like Demi Moore. I watched her as she punched a few keys on her computer, and I caught myself wondering what she looked like under the green business suit that all the hotel employees wore. "A non-smoking room," she confirmed, and went quickly about her business, printing off my receipt and getting my key card.
She stepped momentarily away from the counter, and I looked at her body. She wore a knee length dress, and underneath black stocking that showed incredible legs. I could feel myself rising in my pants, and pushed closer to the counter in hopes that no one would see the growing bulge in my pants.
"There you go. Room 327. An excellent view. I just need you to sign here indicating that you agree to the rates quoted," she said, pointing at a spot on my bill. She had long red nails and the ends of thin fingers. I imagined her fingers wrapping around the shaft of my hard penis, and gently stroking it. I quickly signed the paper, and tried to push the thought out of my head. I took my key, and let my briefcase fall down in front of me, hopefully covering what must have been a very apparent hard-on if anyone chose to look.
"Thank you very much," I said, smiling at the woman behind the counter. I looked down at her nametag, which was pinned on her amble bosom. "Chantal," said the nametag.
"You're welcome. Just let me know if there is anything that I can do to make your stay more enjoyable," she said, smiling back. Her teeth were perfect and white and straight, and her lips were full. I imagined those lips slowly moving over the head of my penis, and down the shaft until they had swallowed it whole. I could feel my penis pressing up against my briefcase, straining the fabric of my pants.
"Actually," I said, "I have never been in town before, and was looking for a nice place to eat. Could you make any recommendations?"
"There is an excellent sea food restaurant over on Williams, but it's hard to explain how to get there. Listen," she said, leaning closer to me which caused my penis to nearly burst the zipper on my slacks, "I get off in half an hour. If you would like, I could take you there. It's on my way home, so it would actually help me out."
"Yeah, great," I stammered. I could feel the tip of my penis moistening my underpants.
"Excellent. I will meet you in the lobby at 6:15?" She asked. I nodded, thanked her, and ran to my room. I threw my suitcase and briefcase on the bed, whipped open my slacks, and whacked off. My penis was so hard when I touched it, and it took only about 40 seconds until my come was splattering the sink in my bathroom. I can't believe how horny I had been. I collapsed on the bed, and calmed down listening to the radio.
At 6:15, I proceeded down to the lobby, and found Chantal standing by the door. She was still wearing her green dress, but she had taken off the accompanying green jacket and scarf to reveal a white cotton blouse, which had two buttons undone.
"Ready?" she asked, as she bent over to pick up her purse. Her shirt fell open slightly, and I caught a view of her breasts nearly bursting out of a red lacy bra. I could feel my penis start to rise in my pants again.
The restaurant was fairly difficult to get to, and when I pulled into the parking lot, I was concerned that I would have a tough time finding my way back to the hotel. "Chantal, is there an easy way to get back to the hotel from here?"
"You just go back the way you came," she said. I gulped.
"Listen, I don't think I remember how I got here. Let me make you an offer. Why don't you join me for dinner, and afterwards I can give you a lift home and you can give me directions to the hotel. How does that sound?"
Chantal smiled, and pushed her hand through her shoulder-length dark hair. "Alright, Mr. James. Those terms sound agreeable to me."
"Please, call me Alan."
Dinner was excellent. The food was spectacular, just as Chantal had promised. Chantal and I had an excellent conversation. Chantal was working at the hotel until January, when she was going back to school for architecture. As I was in construction, we had an excellent discussion about the business. The conversation was so good that I almost forgot that I was completely turned on by Chantal, and was only reminded when she would lean forward and I would catch a glimpse of her red, lacy bra.
After dinner, as we walked back to my car, Chantal made me an offer that caused my penis to stand straight up in my pants. "Alan, I know that our original deal was for you to drop me off at my house after dinner, however, I would really like to go back to your hotel room, if you don't mind."
I had never been approached so forwardly by a woman before, and I must say, I really liked it. "Of course I don't mind!" I said, and nearly ran to the car. On the way back to the hotel, Chantal's hand caressed my leg, running from my knee up to just below my crotch, and running back down again. My hard-on was larger than ever. Chantal wanted to go through the back entrance, because she was concerned about her co-workers seeing her.
"It's frowned upon for the staff to sleep with the guests," she explained. We went up the stairs to my room, and I put the chain on the door and the "do not disturb" sign on the door.
Once the door was locked Chantal pulled me close to her, and she ran her hands over my chest. I grabbed one of her hands, and pulled it up to my mouth. Her hands were almost the same size as mine. I sucked on her first finger, and she tilted her head back and let out a soft moan.
She pulled her finger out of my mouth, and started undoing the buttons on my shirt. I stepped back so I could look her over as she worked on getting me undressed. She was only about an inch shorter than me, but much skinner. I would guess that her waist was probably about 26 inches around, and her hips were not much larger than that. Her breasts, though, were quite large, and I moved my hand over to her shirt and undid the next button on her blouse. Her blouse fell open, and I could finally get a good look at her breasts and the red bra.
"Do you like them?" Chantal asked. "I had them done. I could have gone back to school two years ago if I hadn't had my breasts enlarged, but I feel so much more confident and sexy since the operation."
"I think that the doctor who did them should get an award." I cupped her breasts in my hands. They were firm, and her nipples were jutting at the material on her bra. I bent down and kissed the top of her breasts. The bra was a front clasp bra, so I undid the clasps and let the bra fall away. Her nipples were large and dark, and they had become hard with excitement. I took her left breast in my mouth, and let my tongue roll around her nipple. Once again, I heard her let out a soft moan.
Chantal was done undoing my shirt, and her hands moved up over my stomach and chest, and down my arms, pushing the shirt off with them. I let my arms hang at my side, and the shirt fell to the floor. Chantal's strong hands then moved back down my chest and stomach, and found the buckle on my belt. Soon she had undone my belt, the top button on my pants and my fly, and her hand was inside my shorts, rubbing my hard cock through my underwear. I moaned, and pushed myself hard against her hand. She wrapped her fingers around the shaft of my cock, and slowly stroked it.
I continued to suck and lick her nipple. She squeezed my penis, causing me to shutter. I took her nipple gently between my teeth, and pulled back slightly. Her hand released, and then grabbed my penis even harder. My pants slid down my legs to the floor and I stepped out of them. Chantal continued to rub my penis through my underwear, and I continued to lick and nibble on her breasts.
Chantal pulled away from me, turned around and walked towards the bed. She removed her shirt and bra, and I could see her naked back. Then she reached behind her, and unzipped her skirt. It feel to the floor, revealing a red pair of thong bikinis and black stocking that went up to her thighs. She lay down on the bed on her stomach and pushed herself up on my elbows. "Do you like my ass? Why don't you come over here and show me how much you like it."
I walked to the bed, lay perpendicular to Chantal and let my face hover right above her ass. I kissed one cheek, and then the other. I moved my hand up to slip off her thong, but she quickly turned over. "Mmm, not just yet," she said, and kept her legs tightly closed. "Why don't you lie back?" she asked.
I lay back, and Chantal removed my underwear. My penis sprung up at the feeling of air against it. Chantal blew on the tip of my penis, which caused it to jerk. She let her tongue roll down the shaft, and gently took my left ball in her mouth. She sucked on it for a moment, and then shifted over and sucked on the right ball. She then ran her tongue back up the shaft of my penis, and put her lips on the head of my penis.
Her mouth moved up and down the shaft while her hand massaged my balls. I raised my hips, pushing my cock deeper inside her mouth. Her hand slid down from my balls, and traced the crack of my ass. Her finger found my asshole, and pushed gently against it. My ass clenched around the tip of her finger, and my cock jerked stiff. I was washed with a fantastic felling, and let out a loud moan. Her finger pulled out of my ass, and her mouth pulled off my penis.
Chantal lifted my legs, and pushed them up in the air and back towards my head. My ass opened up, and Chantal's tongue pushed into my asshole. I had never had anyone do this before, and the sensation caused my penis to jerk violently against my stomach. I felt as if I was going to shoot right there on the spot. Chantal's tongue worked in and out of my asshole. I pushed myself against her face, wanting her tongue to dig deeper and deeper inside me. "Oh God. That's fantastic!" I said. Chantal responded, but I couldn't understand what she said with her face buried in my ass.
Chantal continued to lick my ass, and I couldn't take it anymore. "I am going to explode!" I said. I reached down and started to stroke myself. Chantal's tongue stopped penetrating me, and she moved up and took my penis in her mouth again. My hand fell away from my cock. She pushed up and down the shaft twice, and then pulled away from my cock. She looked at me with a bizarre look on her face, like a child about to get into trouble, and licked her first finger. She then moved back down on my cock with her mouth. I closed my eyes and let her expert mouth work my cock.
Suddenly, I felt something pushing against my asshole. Her finger entered me, and I was so surprised and turned on that I came without warning. Chantal took two shots in her mouth, and then pulled off and the rest of my powerful come shoot far up my stomach and chest. I had never blown my load so forcefully and for such distance before! Chantal let my come dribble out of her mouth and onto my cock. "My, my," she said. "You certainly were ready for that!" Her finger pulled out of me, and I lay back exhausted.
Chantal got up, and walked into the bathroom. When she came back she was carrying a face cloth which she had wet. She ran the face cloth over my chest, stomach and cock, cleaning up the come which covered my torso. "You really liked that, I guess?" she asked.
"You need to ask?" I replied. I sat up and kissed her mouth. Our tongues explored each other's mouth. She ran her fingers through my hair. I let my hands slip down her back, and along the outside of her thighs. Once I reached her knees, I ran my hands back up the inside of her thighs. She closed her legs tightly. "Not yet. Let's give you some time to regenerate," she said. So we continued kissing for about 20 minutes, while my soft penis started to grow. In 20 minutes it was as hard as a rock again. "Now it looks like your ready for me," Chantal said, and stood up.
She pulled my head to her flat, tanned stomach, and I kissed it. While I was kissing her stomach, her hands reached down and adjusted her bikini briefs. I pulled away from her stomach, and looked down at her thong. There was an obvious bulge between her legs.
"Oh my God! You have a cock!" I cried.
"Mmm, yeah," Chantal said, tracing the outline of her large cock with her finger. She slowly rubbed her cock through the fabric of her bikini, and it started to grow. "Does it bother you that I have a cock?"
"I don't know," I said, and I didn't. I certainly didn't expect this, and I had never thought before of having sex with a shemale. Chantal was such a beautiful and sexy woman, it had never even occurred to me that she might be a man. I have seen shemale prostitutes working in downtown before, but they had never looked like this! Those shemales looked like men in women's dresses. Chantal looked like a woman – a beautiful woman. She just happened to have a cock.
"No one has to know, if that's what you are concerned about," she offered. I hadn't even thought about what other people would think if they found out about this. I was still dealing with the shock that I hadn't realized. I always thought myself a pretty observant guy, but I completely missed this one.
"No, no. That's not a problem," I said.
"So, do you want to continue?" she asked. I wasn't sure. Chantal reached down between my legs and grabbed my cock, which was still rock hard. "It certainly seems like your little head has made its decision."
I leaned forward, and kissed her stomach again. I let my tongue trace down her stomach, through her belly button and over the fabric of her thong. I took her semi-hard penis in my mouth through her underwear, and ran up and down the shaft. It started to grow in my mouth. Chantal pulled back, and slipped her underwear off.
There it was, completely naked – a penis, dark, long and hard. The hair around the base of the penis had been completely shaved off. Chantal was circumcised, and the skin around the tip was darker than the rest. She swung around and lay down beside me on the bed.
I looked at her, from head to toe. Her beautiful, feminine face. Her large, bulbous breasts. Her flat stomach. Her long legs, covered with black stocking. And between her legs, an increasing long and hard cock. "Yes," I decided. "She is still beautiful, and I am still turned on by her."
I don't know if I am gay, or straight, or bisexual. I have never been turned on by a man, and have never thought before of transsexuals. But that night, in the hotel room, it all made sense. I lowered my mouth onto her penis, and started sucking.
I don't think I was very good at first, but Chantal provided direction. "That's it. Good. Open your teeth a bit, you don't want to scrape the penis. Yes, Yes. Try going farther down the shaft. That's it. Breathe through your nose. Mmmm. Yes. Now take my balls in your mouth. Ow, ow. No gently. Gently. Yes. Yes. That's it. Lick the shaft. Yes. Now lick the head of the penis. Mmmmm. Run your tongue around the tip. Yes, that's it. That's it." Eventually I got the hang of it, and Chantal's directions were replaced with a serious of moans and grunts.
After about 5 minutes of sucking and licking, Chantal asked, "Would you be interested in tasting my come?"
"I don't know. What does it taste like?"
"It's both sweet and tart, like eating a lemon and sugar at the same time," she said. "You don't have to swallow if you don't like the taste."
"Okay," I said. The only time I had tasted come before was when there was residue left on the lips or in the pussy of a lover. And I don't recall being adverse to the taste then.
"Alright. Put your mouth over the tip of my cock," she said. She took the shaft of her cock with her fist, and started pumping up and down. I kept my mouth over the head of her cock, and used my tongue to flick at the tip.
She came quickly, grabbing my head and pushing it down over her cock and the come hit the back of my mouth. The initial taste was sweet, but it caused my lips to pucker. I let the come slide down my throat, and swallowed it all.
"Oh, you decided to swallow. You are going to be very popular with my friends," she said. I hadn't thought to that point what this meant past this night. However, that comment got me thinking about what I wanted from a relationship. I've had a number of relationships with woman, and they never seem to turn out the way I want them to. I can never get close, emotionally or mentally to a woman. Maybe my answer was here. Maybe I needed a woman who knew (at least partially) what it is like to be a man. Maybe I should start dating transsexuals full time.
Of course, I was jumping ahead of myself. Chantal brought me back into the moment by kissing me on the lips. We kissed deeply. I lay back on the bed, and Chantal crawled on top of me. After 5 or 10 minutes of kissing, I could feel Chantal's cock starting to grow again. Soon our hard cocks were brushing up against one another. I grabbed her hips and pulled her against me. I started humping against her cock.
"You're moving like a bucking bronco!" she exclaimed. "You seem like you are ready to fuck." Chantal pulled herself off me, and lay on her back by the side of the bed. "Get off the bed and kneel between my legs," she said. I knelt down, and my cock lined up perfectly with her ass. Chantal's hands grabbed my cock, and slathered it with jelly. Chantal had reached behind her and grabbed a jar of KY out of her purse. "This will help you enter me," she explained.
With Chantal's guidance, I pushed my cock into her ass. It gripped my cock tightly, and was warm. I pushed slowly at first, but then Chantal started urging me to fuck faster. I started pumping faster, and faster. Chantal started moaning. I cock slipped in and out of her ass, my balls slapping up against her butt cheeks. Chantal reached down and started playing with her cock, keeping it hard and erect.
It didn't take long before I was shooting my load into Chantal's ass. I pulled my shrinking penis out of Chantal, and looked as my come dripped from her beautiful asshole. "I want you to put your tongue in there and clean me out," Chantal said.
"Lick me. Drink your come from my ass. Fuck me with your tongue!" So I licked the come that was running down the crack of her ass, and then started slurping and licking the asshole itself. At first, it was juicy with come, and the slightest touch caused it to come cascading out into my mouth. But soon I had to push my tongue deeper and deeper inside Chantal to taste the come. Chantal pushed against my face.
I could smell Chantal's balls as I licked her, and I longed to have her cock in my mouth again. I watched Chantal's cock get harder and harder, and soon I couldn't take it anymore. I abandoned her asshole, and wholeheartedly pumped my face up and down on her penis. This time, Chantal didn't need to provide any direction. She simply let me work her cock, balls and asshole with my mouth. After another 10 minutes of my tongue treatment, Chantal came and I swallowed every last drop.
That was the end of my sexual adventure for that night. Chantal and I held each other and kissed until we fell asleep in each other's arms. The next morning we both awoke with hard cocks, and once again pleased each other. I stayed at that hotel for a week, and in that week not only meet Chantal, but her two transsexual roommates as well, and the four of us experienced some of the most pleasurable sex I have ever had.