My name is Christopher, I’m twenty-eight years old, and have my own apartment. I work for a company which furnishes custom programs for businesses. We build the programs in our office, then some of us have to go to the customer to implement it, train their employees, then monitor it for a few weeks to assure it operates properly.

While we’re at the customers, we look for improvements that can be made so we can expand the program, increasing our charges to them. This starts a cycle of going back and forth from the office to the customer for continual training and additional implementation. I like the job since I travel often, yet still spend time at my apartment. Most of my expenses are paid when I’m on the road.

This worked out well for me since I was a closet cross-dresser. I was brought up in a conservative family in a small town where everyone knows each other. I went away to a large college and saw a world that I didn’t know existed. My dorm mate was always watching porn on his laptop and was constantly showing it to me.

He often brought girls over and wasn’t shy about having sex with them with me still in the same room. My first experiences with the opposite sex were in our dorm room. Being of small stature, and I mean everywhere, my sexual encounters were not very fulfilling for me or my partner. I love the way girls look and dress, but lack the capability to satisfy them.

In my second year of college, I took two summer courses, staying at the dorm by myself. A few days into my solitude I found a pile of clothes left by one of the many girls who visited. I was fascinated by them and spent an hour trying them on. This was the beginning of my adventure into cross-dressing. However, I had few opportunities to dress during college.

In my senior year, I attended a job fair where I was offered my current job in a location 500 miles from home. They included moving expenses and three months living expense to get situated. It was perfect. I found an apartment in a complex overlooking the river with private entrances and assigned parking spaces in front of each unit.

During the first month, I purchased quite a collection of women’s clothes, intimates, and sleepwear. I spent my evenings and weekends dressed like a woman. My apartment had a walk-in closet with built-in drawers on both sides for his and hers. I used both, one for men’s clothes for work, and the other for women’s clothes when not working. Sometimes I packed some lingerie for sleeping when I had to travel.

While this was fun for a while, I felt confined since I dared not go out in public dressed in any feminine clothing. But I liked to spend all of my available non-work time dressed up. I was also yearning for some intimacy.

One day, when driving home from work in the office, I noticed an adult book store. It was just off the main highway, sitting back like its owner didn’t want to attract attention. I can see how I passed it before without noticing it. When I got home I looked it up on line. There was a website displaying some of their products and their “theater”. Their hours were from noon to midnight Sunday thru Thursday. On Friday and Saturday nights they were open until 2:00 am.

I decided to go that night. I had no idea what to expect so I put on a pair of lacy panties under sweat pants and a pull over shirt. I waited until dark to leave. It was the first time I ever went outside with panties on. I couldn’t believe how excited, yet scared I felt.

When I arrived at the book store, the parking lot was dimly lit. The entrance door was on the side of the building. I parked toward the back. I felt like a teenager going to buy some liquor. I stepped out of the car and looked around for a minute. Then, I walked across the parking lot to the front door, pausing and looking around, again, before opening the door. I stepped in like I was expecting someone to grab me and throw me back out. At first, it looked like a normal store. As I walked around there were all kinds of sex toys, outfits, condoms, and items that I wasn’t sure of their use. Next to the counter there was a door labeled theater. As I walked toward it, the man at the counter said,” Ten dollars for the theater”.

I reached into my pocket and found a ten. After I handed it to him, I heard a buzzing sound at the door. It must have been an electric lock. I opened the door, again, not knowing what to expect. It was quite dark inside with small night lights and lit up exit signs in a few locations. Someone in the dark asked me, “What are you looking for, kid?”

Taken by surprise, I answered, “I’m looking for the theater.”

He took my hand in his as he said, “I’ll take you to it.” As he led me down the dark hallway, I could see a row of doors on one side. Some of them were open so I could see video screens with porn on them. The man leading me asked, “What do you like?”

Confused, I responded, “What do you mean?”

He asked, “You know, do you like to suck or get sucked, fuck or get fucked; why are you here?”

I wasn’t sure how to answer so I innocently replied, “This is my first time in an adult book store. I just wanted to see what is in here.”

He put his arm around me chuckling as he said, “Wow, a virgin, it’s your lucky day kid. I’ll show you around. You can trust me. My name is Jim. What’s yours?”

I replied, “Chris,” immediately thinking afterwards that I probably should have used a different name.

“This is the theater,” he whispered to me. “It’s like a three ring circus. You have cross-dressers, gay men, men that say they’re not gay, but like their dick sucked by men, even a few real women on occasion.” Then we walked to the back where there were some black leather couches. “This is where you can fuck or get fucked. If you’re shy, then you can go to the booths in the hallway for a little more privacy.”

Next, we walked down the hallway past the entrance to the other end where there was another room with more couches, a round padded table, and a big screen monitor on the wall. “This is where the exhibitionists like to perform. You never know what, who, or how many will be in here. It’s quiet here tonight. The big nights are Friday and Saturday.”

He led me over to one of the couches telling me to sit down. He sat down next to me, put his arm around me, and said, “What do you think about the place? Do you see anything you would like to do? Would you like to play with my dick?”

I froze in horror stuttering out a subdued, “No.”

He responded, “No problem, let’s watch the video while you think about what you want to do in here.” As uncomfortable as I was, I still trusted Jim. We sat and watched the video. It was a woman getting it up the ass by a guy with the biggest dick I'd ever seen. As we were watching, a woman sat down on the couch next to us. A few seconds later, a man sat next to her. I watched as she started rubbing her one hand on his crotch. He pulled down his zipper and unbuckled his belt. She responded by pulling his dick out and jerking him off.

After a few minutes, she stood up in front of him, and got down on her knees. She put her mouth over his dick and proceeded to take the entire length into her mouth. Jim whispered in my ear, “Pretty hot for a cross-dresser, don’t you think?”

I couldn’t believe it. I replied, “Are you sure? She looks like a real woman to me.”

Jim stood up and took my hand, pulling me up, too. He walked over behind the woman, lifted her dress, and pushed my hand between her legs. He was right; I could feel a cock and balls. She, or he that is, didn’t flinch. She continued on with her blow job. Jim leaned into me and said, “Never doubt me. I know what I’m talking about.” We sat back down and watched the live show next to us. Although I’ve watched porn on the internet and television, it was so much more intense live, kind of like sports.

A few minutes later, another woman walked in. This time I could clearly tell it was a cross-dresser. Although he had a wig, he had no make-up or lipstick; he walked funny, and did not have any feminine features what so ever. He looked at the gurl giving the blow job and exclaimed in a poorly disguised voice, “Carrie, you’re such a slut.” Then, he got down on his knees behind her, pulled up both their dresses, pulled down both their panties, and started to put his cock in her ass saying, “I can’t get laid tonight, I might as well make your night, Honey.”

She responded with a long, “Ummm” as she continued with her blow job. Jim put his arms around me from behind as we both sat sideways on the couch looking on. He whispered in my ear, “Isn’t this fun?” Then, he kissed my ear and my neck. I had to admit he was giving me chills and my little dick was hard as a rock.

The poor cross-dresser was pounding the good looking one as the guy on the couch had both of his hands on her head. All three were grunting or groaning loudly. A few more people entered the room and began watching. Jim lowered his one hand from below my chest down to my waist. He slipped it into the waist band of my sweat pants along my side. I was too excited watching the live show to object. His mouth still on my neck muttered into my ear, “Nice panties, Chrissie. You know you’re hot?”

Damn, I thought to myself. How did I let this happen? Jim is seducing me. I thought I would be embarrassed to death if anyone ever knew I had panties on. Instead, I’m getting complimented and feeling good about it. In fact, I could feel my panties were a little wet.

A few minutes later, the man on the couch let out a huge groan as he must have cum in her mouth. She kept her mouth on his cock as the guy in her ass finished her off. He let out a long groan finishing with, “Carrie you’re the tightest ass in town.” He pulled out of her before pulling her panties up and dress down. Then, he stood up, pulled up his own panties and adjusted his dress a little.

The gurl got up and licked her lips. She made it a point to prominently make a swallowing motion as she said, “I love getting creamed in both ends.” Within minutes the room was empty, except the two of us.

Jim’s hand was still in my sweat pants slowly rubbing my panties. My dick was still hard and a little wet. I turned toward him causing his hand to rub across the front of me to the other side of my waist sending a bolt of electricity through my body. He exclaimed, “You’re wet. Are you sure you don’t want to do something? You can take it slow. Maybe just feel my cock. I really like you and I don’t want you to do something you don’t want.” His hand was still rubbing my waist.

I felt like the virgin I was. I felt innocent, yet wanted to break this barrier. I felt like it was a natural reaction when I reached for Jim’s waist band. As I began to pull it down, he lifted his body up allowing me to pull his sweat pants down below his knees. He kicked his feet a little dropping them on the floor.

His dick was already standing at attention. I put both of my hands on it. It was warm and moist. I ran my hands up and down it enjoying the feel of it. I rested my head on Jim’s shoulder as I continued to message his member. He put his arm over my shoulder and rubbed his hand on the top of my back. His other hand was still on my waist. The feeling of intimacy was intense and unlike anything I ever felt.

I could only use my right hand as my left hand was pinned between us since leaning on his shoulder. I used my fingers to feel the details of his cock. I felt all around his tip, his slit, his vein, and every part of the first dick I ever touched, other than my own. It was like I was a blind man trying to make a mental picture. I had to use more of my senses. I moved my head down his chest, across his stomach, and looked at his cock close up. My body was now lying across the couch on my stomach. His hand that was on my waist was now on the cheek of my ass. This sent another bolt of electricity through my body. I didn’t realize how sensitive my ass was as it responded to his soft touch.

I now had both hands on his dick, again. My mouth was within inches of it. In what was another natural reaction, I stuck my tongue out and licked the tip. There was a large drop of pre-cum on it that I could taste. It was almost sweet and the consistency of a light syrup. My tongue was more sensitive than my finger tips. I started using it to explore the details that I previously did with my fingers. My thought of the tongue as a touch sensor rather than a taste sensor just changed forever.

I began to take his dick into my mouth so I could slide my tongue along it better. It was such a natural act. My lips now joined in intuitively. I couldn’t process the entire experience, feeling like I would need forever to fully appreciate this wonderful act. As I continued to move my head up and down, I could feel Jim starting to respond to the stimulation. I knew he would eventually have to ejaculate and wasn’t sure what I would do. But, I was surely caught up in the moment and didn’t want to stop. His continued hand motion on my ass was also stirring sensations never before experienced.

Jim warned, “I’m going to cum soon, what do you want to do?”

I was too far into this to not complete it. I pushed my head down, taking as much of his dick into my mouth as possible. It was pushing against the opening of my throat. I instinctively started to suck as I backed off a little. I never had such a feeling of want in my life. I moved up and down in a frenzy while maintaining suction.

I could feel his cock pulsate as the strange new taste filled my mouth. It was different than anything I ever tasted before. It was thick and emollient. Jim’s legs were tense, his one hand was squeezing my ass, and his other was on the back of my neck. He was breathing heavy as he quietly proclaimed, “Wow, are you sure that was your first time? You were great.”

I sat up and moved my tongue around in my mouth to feel and taste the results of my effort. Since it didn’t taste so bad, I decided to swallow it as Jim watched me. He gave me a big smile. “You have to give me your phone number. I have to see you, again.”

Then, he pulled me into his arms and just held me for a while, rubbing my back. Afterward, I got up and helped him into his pants. He said, “Maybe next time you can dress up for me. Will there be a next time?”

I replied, “Yes, I think there will be. You’ve made me very comfortable and I enjoyed it. Let’s go find something to write my number on.” We walked out to his car and I gave him my phone number. I waited until he drove away before I went to my car. As I walked to my car, I realized I was quite wet from my own oozing pre-cum.

On the way home I was already thinking about how I could dress for my next rendezvous. If I was this thrilled wearing panties under my sweats, I could only imagine the thrill of wearing a complete outfit outside my apartment. The bookstore could provide this opportunity. It seems everything was acceptable there without any embarrassment. This was the start of my next level in cross-dressing which would now include sex.

More to come……