Dirty Business Trip

I have returned home now, and am still deciding what to do about my new found love of the transsexual form. As I said, I am not sure if that week out of town makes me gay, or if I am still straight. However, last night I was at a bar, and talking to a woman, and I must tell you, that I kept hoping that if I got her home, she would slip out of her dress and I would discover a thick cock between her legs.

Chapter 2: The Bungalow

My name is Alan James. I work at a large restaurant chain in their construction division. I spend my time co-ordinating the construction and remodelling of the stores in our chain. Part of my job includes travelling to locations where restaurants are being built, and ensuring that nothing goes wrong.

I was recently in another town, and on my first night in town I hooked up with Chantal, the woman who worked behind the counter. She was an aspiring architect, and so we discussed the construction industry at length over dinner. After dinner, we went back to my hotel, and after some very hot and heavy foreplay, she peeled off her panties and revealed a great, big cock. I had never been with a transsexual before, but the experience was out of this world. And that was only my first night in town.

The next day I was at the construction site, but was distracted all day by the thought of Chantal and her rock hard cock in my mouth. It was tough trying to keep my mind on the job that day, but I did it and returned back to my hotel at 7:30pm that night. My message light was flashing.

"Hi Alan, it's Chantal," the gravely voice on my voice mail said. "I got off at 6 o'clock, and was disappointed that you weren't in your room. I would really like to see you again tonight. Why don't you give me a call at home." I quickly grabbed a pen and copied down the phone number that she gave me. My penis stiffened in my pants as I dialled the number.

"Hello," the voice on the other end of the receiver said.

"Uh, yeah. Hi. Is Chantal there?" I asked. I think I was having trouble putting together words correctly because all the blood had flowed from my brain and into my now solid cock.

"Just a minute," the voice said, and I heard the phone hit the desk. I sat on my bed waiting for Chantal to come to the phone, rubbing my cock through my pants. I so much wanted to break out my cock and whack off, but I didn't want to waste any of my sexual energy on solo adventures if I could be spending it with Chantal. Finally Chantal picked up the phone. I told her who it was, and she wasted no time in inviting me over. I copied down the directions to her house, grabbed my coat and sprinted out the door.

I must have been quite a sight, standing at the door of the bungalow with my cock straining 6 inches out in front of me, trying to pierce through my pants. Chantal opened the door, and she was wearing nothing but a baby-blue teddy and thigh high stockings. She raised her arms and ran her hands through her shoulder-length brown hair. Her arms raising caused the teddy to ride up just a touch, and I caught a glimpse of her cock and balls underneath. My own penis was about to pop open my fly. Chantal looked down at my pants. "I see you are about to explode. Let's get you inside and naked."

As soon as I was inside and the door was closed, Chantal was undoing my belt. Soon, my pants and underwear were lying at the front door as we made our way into the living room. The living room was dimly lit by candles, which danced light on the walls and the various painting of nudes by the great masters (obviously, they were prints). I peeled off my shirt, and took my place on the couch beside Chantal. We started kissing as she rubbed my cock.

She lay me back on the couch, and swung around so that we were positioned to perform a 69. She took my cock in her mouth as I pulled the teddy up slightly and revealed her cock and balls hanging between her beautiful, tanned legs. I lifted my head slightly, and took both her balls and cock in my mouth at the same time. I started working them with my tongue, and only released them once her penis had started to grow, and forced me to choose between either it or her balls.

Chantal pumped her mouth up and down on my penis, while her hands stroked down from my balls to the crack of my ass, and back up again. I took her erect shaft in my mouth, and sucked hungrily on it. Last night was the first night I had ever tasted come, and I was hungry to taste it again.

I came quickly, spraying my load into Chantal's mouth. She swallowed my offering, and then sat up, pivoting her hips so that her asshole was positioned above my mouth. I stuck out my tongue, and started penetrating her hole while she stroke herself off. My tongue moved in and hot of her wet hole, and soon Chantal was pumping furiously at her own cock. She started moving her ass up and down on my face, and groaned loudly as she ejaculated all over my chest. I pushed myself down the couch a touch so I could catch the last few drops of her come and lick her penis of the white juice. Chantal lay back in the corner of the couch and softly stroked her nipples under her teddy.

"I wish you had warned me you were going to come," I said. "I really wanted to taste it again."

"Mmmm," Chantal moaned, her eyes closed as she played with her left breast and cock. "Don't worry, you will have plenty opportunity for that tonight." I crawled over to the corner of the couch, and placed my lips against Chantal's. Her tongue flirted out of her mouth, and roamed the inside of my mouth.

We were kissing so intently that I didn't hear anyone enter the room. The first indication that I had we were not alone was when a pair of hands stroke my head. At first I thought it was Chantal, but I could feel Chantal's hands on my hips, pulling me close to her. I broke off the kiss, and pulled myself away from Chantal.

Standing behind Chantal was a tall blond with hair down to her shoulder blades. She had blue eyes and pale skin. She was wearing a red sweater that matched the colour of her lipstick and tight black riding pants. She placed her hands on Chantal's shoulders, and than ran them down into the top of her teddy, using her first finger to circle Chantal's nipples.

"I would like to introduce one of my roommates," Chantal said, smiling devilishly. "This is Rebecca. I believe that you talked to her on the phone earlier this evening."

"Hello Alan. Chantal told me all about your adventure last night. She told me that you have quite a tongue for exploring." Rebecca moved from behind Chantal and came around in front of the couch. I could see through her tight pants that she had a bulge growing between her legs. She walked up in front of me, grabbed my hands and placed them on her slim hips. "Tell me, would you like to explore this territory too?"

I looked over at Chantal. I wasn't sure how she would take this. Would she be jealous? But Chantal was smiling. "Go ahead. I bet the three of us could have an excellent time together."

I let my hands explore Rebecca's hips, than pushed them back and caressed her ass. I moved my hands up her back and underneath her sweater, feeling her smooth skin. "Ohhhh," she moaned. "You have such a soft touch." My hands moved around her sides and found her stomach, which was flat and soft. I moved my hands down towards the waist of her pants. I pushed my fingers inside her pants, and slowly started to pull them down. I pulled her pants down past her hips and then past her cock, which sprung out from between her legs. She had shaved all around her penis expect for a small triangle above her cock. I pulled her pants down past her knees, and Rebecca stepped out of them.

I kissed the inside of her leg, just above her knee, and ran my tongue up the side of her leg until I was about 2 inches from her crotch. Then I kissed the inside of her other leg, and repeat the action. I moved up above her cock, and kissed her just above her pubic hair. Rebecca grabbed my head and pulled me close to her. Her cock pressed up against my throat. It was hard and hot. I moved my head down just a bit, and took it in my mouth. I started by sucking the tip, pulling my mouth off and licking the head, and then sucking on the tip again. Soon Rebecca couldn't take the teasing any more, and when I put my mouth back on the shaft, she pushed my head all the way down her cock. I gladly accepted her full length, and started pumping up and down on her shaft.

Chantal got up off the couch, and walked around behind Rebecca. She knelt down, and slowly started licking the crack of Rebecca's ass. Rebecca, torn between the two sensations, pulsed her hips back and forth, alternately pushed deeper into my mouth and pushing harder against Chantal's face. Chantal firmly gripped Rebecca's ass cheeks, and pulled them apart, revealing Rebecca's tight hole. Chantal extended her tongue out as far as she could, and pushed it deep into Rebecca's ass. Rebecca moaned loudly, and pushed back, pulling her cock right out of my mouth.

I watched for a moment as Rebecca, her eyes closed and mouth agape wriggled her butt against Chantal's face, who was growing harder and harder by the moment. My own cock was starting to grow hard again, and my craving to taste come was mounting, so I took Rebecca's cock in my mouth again, and started pumping even harder. Between my mouth and Chantal's tongue, Rebecca couldn't hold out for long and soon she come hard into my mouth. Rebecca nearly screamed as she came and once she was done, she fell onto the couch beside me. Chantal, smiling and hard as a rock, took a seat on the other side of me.

The three of us sat on the couch – me completely naked, Rebecca naked from the waist down but still wearing her red sweater and Chantal in her baby-blue teddy and stockings. We didn't say a word, just breathed heavily and smiled at the thought of the ecstasy that we had all just taken part in. But I couldn't sit still for long. I had a fully erect penis between my legs that needed to be released, and two beautiful shemales to help.

Chantal could obviously see I was ready to go again, so she bent over and started to lick my nipples. They soon grow hard like pebbles, and Chantal's hand ran over my stomach and down to my cock. She rubbed her hand up and down on my crotch, causing my penis to rub up and down against my inner thigh. With my left hand I reached down between her legs and took her penis in my hands. With my right hand I reached around behind her, and let my hand rub up and down her back.

Chantal broke off from my nipples, and started kissing up my chest. Her tongue ran around my Adam's apple as her hand took a firm grip of my cock. I started pumping her penis with my left hand. My right hand creeped farther down her back until my finger was exploring the top of her ass.

Chantal's lips reached mine. Our hands stroked each other's cocks. Chantal repositioned herself so that she was straddling me, allowing my finger to slip even farther down her ass crack until it was pressing against her asshole. Chantal started to stroke my penis harder as I pushed my finger into her ass. We continued to stroke each other and kiss deeply as I finger fucked the beautiful, tanned shemale.

I could feel the come rising to the tip of my penis. My hips jerked up and down and I pushed my finger deeper into Chantal. She pushed back against my hand and pumped my penis furiously. I started stroking her faster, and she responded by pushing her hips back and forth, moving my finger in and out of her ass, and doubling the stroking action of my left hand. My come flowed from my cock and in the throws of orgasm I squeezed Chantal's penis. She yelped and pulled back. As I released her cock from my hand, her white juice jetted out onto my chest. Chantal made circles with her hips and pushed back against my finger as my come soaked my chest. She kissed me softly.

"I am sorry if I squeezed you too hard," I apologised.

"Oh, it didn't really hurt. I was just surprised. Anyway, the shock of the event made my shoot quite fiercely."

Rebecca was sitting beside us on the couch, smiling and getting hard again. She sat up straight, stuck out her chest and pulled the red sweater off her torso. Her skin was white and smooth and her breasts were small and firm with a small, light red nipple. I moved over to the other side of Rebecca, and took her breast in my mouth. Chantal moved closer to Rebecca, and took Rebecca's other breast in her mouth. Chantal and I sucked on Rebecca's tits as Rebecca lay back and rubber her crotch.

Chantal tapped me on the shoulder, and pointed down at Rebecca's hard penis. Chantal moved down and took the penis in her mouth, enveloping it fully once, and then pulling off. I did the same, opening my mouth as wide as I could, and pushing Rebecca's cock as far back in my throat as it would go. We continued tag-teaming Rebecca's cock for the next few minutes, each sucking it for a few seconds, and then letting the other take over.

"Mmm, that feels so good," Rebecca moaned. "But you two have to speed up. My cock is getting ready to explode, and if it doesn't soon I am going to have a serious case of blue balls." I nearly laughed at the thought of this beautiful, alabaster-skinned blond having blue balls.

Chantal took Rebecca's penis in her mouth. I slide off the couch, and positioned myself between Rebecca's legs, and started sucking on her balls. Chantal moved up and down on Rebecca's cock as I licked underneath Rebecca's ball sack.

"Do you like that?" Chantal asked Rebecca, who moaned a positive response. "Would you like even more to fuck me?" Chantal asked. Rebecca nodded.

Chantal got on all fours on the couch and pulled her teddy up over her hips, revealing her firm tanned ass. Rebecca knelt behind her, and worked Chantal's ass with her tongue, getting it moist. Once Chantal's hole was lubed up with Rebecca's spit, Rebecca pulled herself close to Chantal, and pushed her cock into Chantal's ass.

I watched for a few moments as a beautiful blond fucked the tanned brunette in the ass. Rebecca started pushing harder and she bent over Chantal's back. I looked at Rebecca's ass, which had opened up slightly. I moved in behind Rebecca and started licking and sucking the beautiful puckered hole between her ass cheeks. Soon the hole was wet, and had opened up wide in anticipation. I grabbed my hard cock and pushed it inside Rebecca's ass.

The three of us formed a doggie-style Conga fuck line. Chantal received from Rebecca, who was getting it from me. Soon we had a fluid motion of pushing in and out going, and the girls were moaning furiously. My cock pushed in against Rebecca's closing and opening ass and the inside of her ass was warm. I can't believe how great it felt to fuck someone's ass. It was much better than any pussy I had ever been in. It was tighter and warmer, and the action of Rebecca's sphincter closing and opening on the base of my penis heightened the pleasure.

Rebecca came first. Chantal pulled away, white come dripping out of her ass. Chantal stood up and walked around to the other side of the room, so she could watch as I pumped in and out of Rebecca. Rebecca, now free to concentrate on my penis in her, started moving her hips side to side. With the added motion, it didn't take long for me to come in Rebecca's ass. I bucked up, nearly bending over backwards in an attempt to bury myself deeper inside Rebecca as my come spilled out inside her.

We were done for the night. Chantal went to get us some water as Rebecca and I relaxed on the couch.

"You were excellent for only a second time. Are you sure you haven't sucked a cock before?" Rebecca asked.

"No. I guess I just have received enough blow jobs that I know what works and what doesn't work. I think that's one of the great things about being with you and Chantal. I have never been with women before who knew how well to please a cock. Obviously, you and Chantal would know what it takes to please a cock because you have one."

Rebecca laughed. The conversation turned from sex talk to small talk. Rebecca was a interior decorator, and we discussed the design of restaurants until Chantal returned to the room. Rebecca took a sip of her water, and then got up to leave. "I had a great time tonight. Alan, I would like to continue our discussion some time about design. How long are you in town for?"

"Just until Friday," I said. Suddenly I regretted the fact that I couldn't stay in town longer, and continue to see these two intelligent and sexy shemales.

"Where are you working?" Rebecca asked.

"Down at 8th and South line."

"I have a client that I have to see tomorrow on 8th and Renard. That's just 4 blocks away. My appointment is at 11 o'clock. I should be finished up by noon. Would you like to grab some lunch?" Rebecca asked. She was still completely naked, her cock soft between her legs. What an odd scene, I thought.

"Okay. Just pop by the construction site. I will be in the trailer."

Chantal and I finished our glasses of water, and got dressed. I put on the clothes that I had worn to the house. Chantal changed out of her blue teddy, and put on a casual white summer dress that highlighted her excellent tan. "Are you hungry?" she asked, and I realized that I hadn't eaten since 1 o'clock in the afternoon, and it was already after 9pm.

"Yes. After all that activity, I am starving." Chantal prepared some pasta, and we sat down in the dining room and had a wonderful conversation about our favourite architects.

After dinner, we proceeded up to Chantal's bedroom. Chantal stripped off her summer dress and stood naked before me. I pulled off all my clothes, and we embraced. I lay back on the bed, and Chantal climbed on top of me. She took both our penises in her hand, and stroked them against each other. I sat back and let the feeling overtake me. Soon we both came.

We settled underneath the covers of Chantal's bed, and held each other until we fell asleep. The next morning, I drove Chantal to the hotel. She proceeded in, and I waited 5 minutes before following. I grabbed a quick shower, changed, and head right back out of the hotel to the work site. All the way to work I couldn't help but look forward to both my lunch with Rebecca, and whatever erotic pleasures awaited me that night with Chantal. Usually travel is such a pain, but this was turning out to be one of the best trips I had ever taken.

Chapter 3: Lunch with Rebecca

The construction site positively stopped when Rebecca pulled up. I was standing outside the trailer discussing vinyl versus cloth seating with an extremely cost conscious regional manager when the Mazda Miata pulled onto the site. And out stepped Rebecca, and the regional manager stopped nattering about his budget and stared.

Rebecca was wearing a navy pinstripe business suit. The skirt on the suit was raised about 4 inches above her knee, showing off an excellent pair of legs housed in a pair of silk blue hose. She was wearing 2-inch heels, which gave an even better shape to her legs and rounded her ass out even more. Underneath the blue jacket of her suit she was wearing a ribbed t-shirt the clung tightly to her body. As she stood from her car, she jacket flipped open and you could see that she was not wearing a bra, the tight top tracing even line of her small but firm breasts. She did up her jacket and started to walk towards the trailer.

Ever eye followed her. Construction is a very male dominated business, and it is a rare occasion where a woman shows up on the site. It's even rarer when the woman who shows up is a tall, good-looking blond. Rebecca's long blond hair bounced against her back as she walked towards me. I looked around. Inside the partially built store, 3 carpenters that had moments earlier been constructing a counter top stood and watched Rebecca's long, confident stride. Beside me, the regional manager gulped and shift uncomfortably. On my other side, the head contractor smiled and puffed out his chest. Rebecca walked up to me, and in European fashion, kissed each of my cheeks. "Bonjour, mon aime. Are you ready to go?" She asked, keeping her gazed fixed on me.