Dirty Business Trip

Nicole pumped faster and faster. I ached to rub my cock, now hard as a rock, but I couldn't get my hands free. Nicole continued to talk dirty, calling me a whore and a slut and a horny faggot. I didn't care. I would put up with whatever insults she would throw at me, just so I could taste her come.

"Do you want my come in your mouth?" she asked, still pumping. I couldn't answer the question, my mouth was filled with her 9 and a half inches. I simply waited for the assault of liquid to fill my mouth. I didn't wait long. Nicole started making deeper strokes and the pitch of her voice dropped an octave. "Oh fuck yeah! Oh yeah! You dirty little slut. You lucky little whore. You get to taste all my come. Go ahead, drink it up, faggot. Enjoy my come you dirty little slut." With that, she pressed hard against my face and released herself in my mouth. There was so much come, it was all I could do to continually swallow. I could feel the come running down my cheeks. Nicole pulled out of my mouth, and stood at the foot of the bed.

"Oh my god. You do have an excellent little bitch mouth. No wonder Rebecca and Nicole like you so much. You are the perfect little whore, aren't you? And look at your cock, hard as steel. There I was fucking you in your mouth till the point where you couldn't even breathe, and that turned you on. Didn't it?" Nicole flicked my penis with her finger. It stung for a moment, but the pain quickly passed into pleasure. "I bet you want me to suck you off? Or do you want to fuck me ass?" She asked, slapping her ass with her hands. "Well, no such luck for you, lover boy. But I do promise that you will enjoy want is coming next."

Nicole slipped her body suit completely off, revealing her body. Her skin was white. She had a small shock of red hair right above her cock, but other than that was shaved clean. Nicole came around to the side of the bed, and climbed over me, positioning her ass right above me face. "Let's see what that magic tongue of yours is all about," she said, lowering herself onto my face. I stuck out my tongue, but my penis was aching for release, so I wasn't completely into it.

Suddenly, my penis was roughly being massaged. Nicole was using her feet to jerk me off while supporting herself above my face on her hands. The feeling of her feet against my cock revitalised me, and my tongue started working on her asshole with renewed vigour.

"Oh, that is good. Yes, push that tongue of your deep into me, slut boy. I can see by your cock that you like to lick ass, don't you?" Nicole wiggled her ass above me face and stroked my cock even harder with her feet.

After a few more minutes of this, Nicole shifted. She got onto her hands and knees, with her cock hanging down over my chest and her mouth above my crotch. Nicole pushed her ass back, and I had to strain my neck to get my tongue in her hole. Nicole started stroking my cock with her hand, and blowing on the tip of the penis.

Her ass closed and opened around my tongue and I dug deeper and deeper. Nicole continued to stroke me and blow on the head of my cock, only stopping occasionally to moan or hurl another insult at me. "Yes, that's it you whore. Push deep into me, slut!"

Nicole's stroking and blowing was working wonders on my cock. Nicole could see that I was about to blow and so just kissed the tip of my cock. That was enough to push me over and my come shot out and all over Nicole's face. Nicole stood up at the foot of the bed again, and looked at me sternly.

"Now look what you have done," she said pointing to the come that was running down her face. "You have messed all over my pretty face." A drop of come ran off her square jaw and onto her breast. "You are going to have to pay for this."

Nicole crawled between my legs, and I noticed that her cock was long and hard again. She reached over beside the bed and pulled a jar of KY jelly out. She opened the jar and spread some on her cock. She grabbed my legs and swung them up onto her shoulders. Then she took another dab of KY jelly, and spread it onto my asshole, using two fingers to spread it around my hole, and then pushing inside me.

My asshole jerked shut and pain shot up through my body. "Relax," Nicole said as she pushed her fingers in and out of my ass. "It doesn't hurt if you relax your ass and let it happen." With each thrust of her finger, the pain was intense. I couldn't imagine that she thought she was going to put her massive cock inside me.

"I don't know about this," I said weakly. I was powerless, and at the mercy of Nicole.

"Don't worry," she said, her voice taking on a soft tone for the first time since arriving in her bedroom. "I won't hurt you. It feels quite nice, you just have to learn to relax and accept it." She continued talking softly, her left hand gently rubbing my leg while her right hand continued to open me up. Soon the fear was leaving me and the pain had disappeared. "Now I am going to try three fingers," Nicole said, and I felt my ass open even wider.

This time, there wasn't any pain. It was an uncomfortable feeling for a moment, but then it passed. Now it felt strange, like I was taking a really long dump. There was no pain, just a feeling of movement inside me. Nicole pulled out her fingers, and my ass felt great. I felt like I had just taken the greatest shit in the world and pleasure engulfed my body. Nicole pulled herself closer to me, and pushed her cock inside.

There was a little pain, but Nicole started talking softly again and I relaxed. The feeling of her cock pushing in and out of me was odd, and I shift around my ass. Occasionally her cock and my ass would hit some magically mark, and my body would shutter with pleasure. Then we would pass it and the feeling of having to go the washroom would return. Nicole continued gently pushing in and out.

I started to get more comfortable with the cock inside me, and started to move my ass around more, trying to find that special spot again. Sometimes I would find it for a moment, sometimes I would hit a spot that hurt. After a couple of minutes of experimentation, I learned how I could move to maximize the probability of finding pleasure and minimize the probability of finding pain.

Nicole started to push faster and deeper. With each deeper thrust, I again had to experiment to find a comfortable position. But once I found the right position, it was okay getting fucked. Nicole's breathing quickened, and her face started to tense. I could tell she was close to coming. She started pumping harder and faster. I could feel my own cock starting to rise, twitching with each thrust.

"Oh yes," Nicole said, pulling herself out of me and taking her cock in her hand. The feeling of Nicole pulling out of me was even better than any feeling during getting fucked. It was like when you press really hard against your skin, and then release. The spot that just a moment ago you were making feel uncomfortable and painful is now the best feeling spot on your body. That's what my ass felt like. The feeling of the air against it was magically and my penis jerked up in reaction.

Nicole stroked herself quickly. She threw her head back and started to come. The juice flew onto my chest and stomach as Nicole pumped her cock in her hand. She fell onto the bed beside me, exhausted.

"So Alan, what did you think of that?" she asked, grabbing the keys for the handcuffs and releasing me.

"That was bizarre!" I said. "It was a mix of fear and desire, pleasure and pain. Sometimes I was frightened, and just wanted you to release me and let me limp away. Other times I was so turned on that I would have done anything you asked. You have a real talent for this!"

"Well, I am glad that you enjoyed it. Chantal and Rebecca were right though, you do have an amazing tongue. You can stick that tongue of yours in my ass anytime."

I got up and went to the washroom to clean myself off. I thought about jerking off to take care of my hard-on, but just then I heard the front door open and realized that Chantal and Rebecca were home. "No," I thought to myself, "I am not going to waste this hard-on on a solo adventure. Instead I pulled on my pants and shirt, and headed out into the main hall to greet them.

Chapter 6: Lover's Cave

When I exited the bathroom, I was thinking about all that had happened to me in just three days. When I arrived in town on Monday, I had never even thought of having sex with a transsexual before. Now it was Wednesday night and so much had happened. I sucked my first cock and licked someone's ass for the first time. I had developed a taste for semen. I had a three-way encounter with two transsexuals. I had sex in a public place. I had tongues, fingers and a penis in my asshole. And I had experienced my first taste of bondage. I walked gingerly down the hall. My ass was a touch sore, and I spread my legs a bit as I walked to give it some air. And my jaw muscles were aching from having swallow Nicole's nine and half inch cock. I couldn't believe something that large had been in my mouth. I couldn't believe that it was also in my ass.

Nicole was standing at the door, still completely naked, whispering something in the ear of Chantal. Chantal was listening intently, and then smiled. "Did he enjoy it?" she asked Nicole, while gazing right at me.

"Oh, he had a good time. If you want proof, look at the bulge in his pants." Nicole responded.

I looked down and noticed that my cock was hard and tenting out my pants. Despite all that had occurred in the past couple of days, my cock was still ready for more action. I couldn't believe that this was happening to me, but I couldn't wait to find out what was going to happen next.

Chantal walked up to me, took me by the hand and led me into her room. "So, I hear that you had your cherry popped tonight. And from Nicole's huge cock. You are quite an adventurer to take on so much. I remember two days ago the look on your face when you first saw my cock. And now you are an old pro." Chantal stripped out of the dress she was wearing, and put on a pair of jeans and a sweat top. She dug around in her closets for a moment, and pulled out a sweater for me. "Put this on, it's a little chilly out."

"Are we going outside?" I asked.

"Yes, I thought that after all the adventure that you have had, you might enjoy a quiet walk in the park tonight. Give you a chance to rest." The tip of my penis stung every time it brushed against my underwear, my ass was still stinging a bit and my jaw was aching. Maybe a nice, quiet evening would be a good idea. I pulled the sweater over my head.

The park that Chantal had mentioned was about a 15 minute drive away, north of the city. We took my rental car and I followed the directions that Chantal gave.

"This park is one of my favourite places," she confessed during the drive. "When I was a young boy – 12 and 13 – I was very confused about who I was. While all my other friends were playing football and wrestling, I was feeling like a real outsider. I used to ride my bike to the park – now that was an hour and a half cycle – just to get away from people. I felt fine as long as there were no people around. But if there were people, then I felt pressure to conform. In the park, I felt like I was a part a nature – a natural part of nature. With people, I felt like an outsider from society. I almost dropped out of high school to become a park ranger," she said, laughing. Her face lit up when she laughed. I reached over and took her hand.

Chantal pointed right. "Turn here," she said, and then continued with her story. "Anyway, when I turned 15, in my second year of high school, I was staying late after a gym class. I never liked to change when the other boys were in the change room. Part of me was afraid that I would get aroused if I saw them naked, and another part of me was afraid that they might get aroused if they saw me. I wasn't sure that I wanted anyone to be aroused by me. So I am in the change room, taking a shower when in walks the star running back for the school's football team. And he has a hard on.

"'Oh, I am sorry. I didn't realize anyone else was in here,' he says, covering himself up with his towel. But then he sees it is me, and drops the towel. He walks over to the shower beside me, turns on the water, and starts masturbating right there in the shower. I didn't know what to do. He looked over at me and reached out to touch me. I was so frightened, I ran right out of the shower, got dressed and didn't come back to school for the next three days. You know why I was so frightened? Because when I thought about him whacking off in front of me, and I imagined that he might be thinking of me when he did it, I got aroused.

"I was sure that I was gay, which depressed me endlessly. The last thing I wanted to be was a gay man. I returned to school the next week and of course the first person I run into is the running back. 'Listen,' he says to me, his voice growling, 'if you tell anyone about what I did in the shower, I will fucking kill you. Do you understand?'

"I was so ashamed and humiliated. I thought that he may have liked me, but then he threatens to kill me. I left school right after running into him, went home and packed a bag and ran away.

"I was out on the street for two days when I ran into my first transsexual. I was instantly attracted to her, not because I wanted to be with her, but because I wanted to be her. She was about 10 years older than me, but we became friends, and she asked me to move in with her. Over the next five years, she taught me everything that I learned about being a transsexual woman. How to walk, how to talk, how to dress, how to flirt with men and how to pick out the men who are going to flirt back.

"I am not proud to admit this to you, but during that time I was a prostitute. It wasn't that bad. Most of the men were quite decent, just guys with strange urges that needed a woman like me to fulfil them. During that time I got my breast implants and started taking hormones to appear more female. I even went so far as to meet with a doctor about sex reassignment surgery. But I still didn't feel right. I still felt like I was not me, but someone else. I had hoped that the sex change would erase those feelings.

"Then I meet Rebecca. She was as she is now, the most confident person I had ever met. She was a transsexual, but she didn't want a sex change. The more I talked to her, the more I understood what was wrong with me. It wasn't that I was a woman trapped in a man's body, and that all I needed was to cut off my penis to be happy. I wasn't happy because I didn't like the path my life was taking. Rebecca taught me to figure out what I wanted to do, and pursue it.

"I moved out of my loft downtown, and out to the bungalow with Rebecca. At the time, Nicole wasn't our roommate yet. There was another girl, Cindy. She's married now, to a nice straight man. Anyway, after searching my soul, and trying a number of things, I discovered that I wanted to design environments. I wanted to try and create a man made structure that captures the feelings and emotions that I feel when I am in the park. And as soon as I set myself on the path to become an architect, I lost the urge to have the sex change."

We arrived at the park, and I shut off the car. Chantal got out, threw on a knapsack and walked into the darkness. I followed here. We walked for about 30 seconds along a dark path before we came upon a clearing. Along the north side of the clearing was a 30 foot cliff, and along the top of the cliff I could see a few fires burning. "Campers," Chantal explained and continued through the clearing towards the cliff.

When we arrived at the base of the cliff, we were standing at the entrance to a small cave. It was about 30 feet deep and 10 feet wide. Chantal took out a flashlight, and shone it inside the cave. There was fire pit and old bottles lying around the cave. "The teenagers like to come here to drink. It's a school night, so there won't be many around." Chantal proceeded into the cave and walked to the back. I followed, nearly tripping on the uneven floor a few times.

Chantal climbed up a couple of rocks, and disappeared into a 3 foot by 3 foot opening about 6 feet off the ground. "Come on up," she called. She poked her head out, and shone the flashlight down the rock slope so I could see where to put my feet. I climbed up and entered the small opening.

There was a tunnel that was about 6 feet long, and it then opened up into a small cave that was about 4 feet high, 8 feet deep and 4 feet wide. Chantal opened her knapsack and pulled out a blanket and 4 candles and candleholders. She lay the blanket on the ground, setting all four up at the far end of the cave. Then she lay on the blanket and motioned for me to join her.

It was a tight squeeze, but I managed to shimmy in beside her.

"This is Lover's Cave," Chantal said, putting her arms around me. "When I was in high school, this is were the kids that were dating would come to make out. Obviously, when I was in high school I never came up here."

Chantal closed her eyes, and lay her head on my chest. I kissed the top of her head. The cave was getting warmer. It didn't take the candles long to generate heat for such a small space. With the candles, the sweater I was wearing and Chantal cuddled up beside me, I started to feel beads of sweat developing on my forehead. "Whew, it's getting hot in here." I said.

"Well," Chantal said, "we can't put out the candles, because they we wouldn't have any light. And we can't move farther apart, because there is no where to go. So that leaves only one option. We will have to get you out of those hot clothes."

It was a struggle getting undressed in such a small space. But soon our clothes were off and flung carelessly towards the mouth of the cave. I was completely naked, and Chantal was wearing nothing but her bikini briefs. We started kissing. My hands caressed her soft dark hair. My left hand slid down from her hair towards her breast. I took her breast in my hand and gently played with the nipple. The nipple started to become hard as I fingered it.

Chantal's hand found their way down between my legs. My penis was partially erect, but was aching for a lot of action over the past couple of days. Chantal was gentle with it as she stroked it and it responded by growing in her hand. Our kisses become deeper and more intense. My left hand moved down from Chantal's breast and into her briefs. I found her penis, which was getting hard, and let my hand stroke it. Chantal's mouth opened to let out a moan, but I pushed my tongue deep into it so it wasn't heard.

We sat there for a while, kissing and stroking each other. I slowly moved myself on top of Chantal without breaking our kiss. My hand slipped her briefs down around her thighs and our naked penises touched. I rubbed our cocks up against each other by circling my hips back and forth.

"Rub it against my balls," Chantal said, only breaking our kiss for a moment. With my hand, I bent my penis so it was facing down and started rubbing my cock up and down between her legs. She closed her thighs tightly around my cock, and started swaying them back and forth. With my cock trapped between her legs, I started pumping up and down. It was just like fucking a woman in the missionary position.

I could feel Chantal's hard cock bouncing up and down between us. Her hand moved down and she grabbed the base of her cock with two fingers. She then batted it up and down between us, first hitting my stomach, than hers, than mine again. I continued to pump between Chantal's legs.

The cave was getting even hotter and soon we were both covered with sweat. But I didn't care. I continued fucking Chantal's thighs and she continued to play with her cock. The feeling was heavenly.

But the heavenly feeling had to come to and end. And come to an end it did. After I came, I started to get up, planning on moving down and finishing Chantal off orally. But she held me tight. "No, stay on top of me," she moaned breathlessly and as pulled me close with on hand and continued to masturbate with the other. And so we continued kissing and I caressed her hair until she came, covering both her and my stomach with hot come.