There are two types of cross-dressers. The first are those who dress all the time. They are usually quite passable since they spend a great deal of time and effort. The second are wannabe women who live in a world where there are circumstances that prevent them from being full-time out of the closet cross-dressers. They are usually not passable since they cannot shave their entire bodies, grow and style their hair, purchase and maintain a female wardrobe, and/or learn and understand make-up. I am the second.

When I see a hot woman, I want to be her. When I watch pornography, I want to be the one getting fucked. I get excited when I see women’s undergarments. I love the feel of women’s intimates. Unfortunately, I live in a man’s world, working with men who respect me as a leader, looking to me for inspiration to perform their physically demanding duties. Any hint of femininity would topple my position on this ladder of financial success that supports my family and decent lifestyle. However, it doesn’t diminish my desire to be a woman and leaves me stuck between two opposite worlds.

Over the years I have taken opportunities to procure some women’s clothing, which I keep in my work shed, in a locked toolbox. I often tell my wife that I am working on a side job or helping out a friend, loading my car with some tools that includes my special toolbox.

I usually find a secluded area where I can change into my female clothes before going to an adult bookstore. I wear an overcoat to walk from the car into the bookstore, where I pay to enter the theater. Once inside the theater, I can take off my coat and walk around the darkened halls, booths, and viewing areas with no one paying particular attention.

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Each time, I progressed a little more. The first time, I wore a pair of lace panties under my jeans. Then I wore a bra under my shirt. Next, I wore stretch pants and a silk blouse. Probably, the fifth or sixth time, I added a pair of women’s flat shoes and breast forms in my bra. It was enough to attract the attention of one of the trolls.

I was sitting in the small theater area watching a video of a woman giving a blow job, when he sat next to me. I was already excited watching and wondering what it must be like to suck on a man’s dick. Suddenly, I noticed he had pulled his cock out and was slowly stroking it with his hand.

At first, I didn’t realize that this was an invitation. I couldn’t help but watch him as he seemed completely uninhibited in his semi-public display of masturbation. He looked at me several times, surely knowing I was aware of his activity. It also occurred to me that there were about twenty empty seats, yet he chose the one next to me. In fact, we were the only two in this theater area at the time.

Then, without warning, he reached over, took my hand with his hand, and placed it on his dick. It was quite warm from his ten minutes of stroking it. I rubbed my fingers around the tip of it, like a blind man trying to comprehend what he was touching. I looked up at the theater screen and became excited as I watched the woman jerking the man off in her mouth. I wrapped my hand around the shaft and started moving it up and down imagining I was the woman on the screen.

After jerking him off for a few minutes, he quietly said, “Why don’t you suck it for me like a nice little girl.” I wasn’t sure what to do. I was excited that he called me a girl and it was a chance to continue my fantasy that I was watching on the screen. But, I had never had a cock in my mouth before, not that I hadn’t thought about it. He didn’t give me much time to think before putting his hand on my head coaxing me down on him. It was decision time.

I parted my lips, sticking out my tongue, to lick the tip of his dick. His skin was soft and I could smell a hint of soap. It was coated with pre-cum, which was a light syrupy consistency, almost sweet tasting. It wasn’t bad, so I continued to lick it a little more.

He started pushing my head down a little further as he said, “Come on, baby, you can do better than that.” He pushed down forcing his dick into the back of my mouth before saying, “I know you want to deep throat it.” I started to gag and pulled him out of my mouth. He was wet with my slobber. I opened my mouth and leaned down on his dick, again. I started bobbing up and down while I wagged my tongue along his vein.

I knew he would eventually shoot his load, but I wasn’t sure I wanted it in my mouth. I didn’t know if there would be any warning or what he was expecting. However, I was starting to enjoy it and I knew I probably passed the point of no return.

After ten or fifteen minutes of bobbing, he started arching his hips up. Finally, he declared, “I’m getting ready to cum, where do you want it?” I thought to myself, 'it looks like I do get a choice. Where do I want it?' My last warning, “Here it comes.” I panicked, and pulled it out of my mouth, just as he started shooting his load.

It hit me in the face on my lips, cheeks, nose, and down my neck. He must have shot three or four streams. I couldn’t help taste it on my lips and smell the strong scent of it. It was thick, sticking, yet slowly dripping.

I thought to myself, 'What do I do now?” How could I walk around like this?' I would have to walk to the front, near the entrance, to get to the bathroom.

He laughed as he looked at me and said, “You’re a mess. Here is a paper towel to wipe yourself up, unless you want to stay like that for a while.” I took the paper towel and wiped my face and neck as best as I could.

I responded, “Thank you for the paper towel.”

He replied, “Thank you for the great blow job. I hope we can do this, again, some time, sweetheart.”

I smiled as I walked away saying, “Yes, I hope so, too.” I made a bee-line to the bathroom. I felt like a cheap whore trying to hide my dirty deed. Yet, at the same time, I felt like a woman getting the satisfying sex she needs. I threw some water on my face in the bathroom. This made my skin slippery as it reactivated the dried cum. It was like I put lotion on it.

As I dried it off with a paper towel, I realized my dick was hard and it felt wet. I reached into my panties to find it was coated with pre-cum. I wiped it with my hand, and then licked my hand. I had taken care of the stranger, but not myself.

I left the bathroom and went back to the dark theater. There was another video on the screen with a woman giving a first-class blow job to a well-endowed stud. I could put myself in her place now and it was making me hot. I was the only one in the seating area. I started to pull my jeans down, but it was difficult sitting in the seat, so I got up and walked to the back where I could stand. I pulled my jeans and panties partway down my thighs. I started jerking off as I watched the woman on the screen deep throating the man. I was beginning to wish I could have taken the stranger into my throat.

As I continued to watch and jerk off, another man walked into the theater area. At first, I stopped, thinking I was being caught. Then, I thought, this is what men do here. The man walked back and stood next to me. He pulled his sweat pants down to his feet, before stroking his cock. He took his other hand and started stroking my raging hard-on. I reciprocated by replacing his hand on his cock with mine. It didn’t take long before I was ready to explode. I declared, “I’m getting ready to cum.”

The man quickly got down on his knees and put my dick in his mouth just seconds before I let go. I couldn’t believe the intensity of my orgasm as I must have shot four or five loads into his warm mouth. He was holding my waist with his hands and held me still as my very sensitive dick finally started to calm down. Then, he withdrew his mouth from my softening member. He stood up, looked at me face to face, swallowed, licked his lips, and then smiled saying, “That tasted good. Do you want mine?”

I looked at the screen where the woman had just taken a load on her face. I thought about the satisfied look on this stranger's face. I thought about my earlier desire, then answered, “Okay, I’ll give it a try.”

He replied, “You’ve never swallowed? You don’t know what you’re missing. I’ll understand if you change your mind, though.”

He put his hands on my shoulders, prompting me to get on my knees. I pulled up my jeans and panties, before complying with his prodding. His dick was still hard and appeared to be of average length. I stuck out my tongue and licked the pre-cum from the tip. It was sweet and syrupy like I expected. I ventured my head forward, taking him into my mouth, letting his dick slide between my lips. When he was against the back of my mouth, I pulled back until he was almost out, and then pushed him back in, again.

I started the familiar bobbing motion back and forth. Each thrust forward; I tried to take him into my throat. This caused me to gag a little each time. I held my hands on his butt cheeks to help pull him into my mouth. He responded by putting his hands on the back of my head. Once or twice, he was able to force it into my throat a little. My mouth was becoming wet from my slobber and I was making a loud slurping noise. He was pulling me with his hands on my head as I was pulling with my hands on his butt. His rhythm was increasing. I was getting excited knowing he was getting close.

Finally, he pulled my head tight into his crotch as he grunted. I could feel his vein on my bottom lip and tongue pumping his cum into my mouth. Then, I could taste it. His headlock prevented me from doing anything but swallowing. This resulted in a slight penetration of his dick into my throat. He let up his hold on me after ten or fifteen seconds. I could feel him softening in my mouth.

As he started to shrink, I could taste his cum more. While I had already swallowed most of it, there was some left over that I think oozed out after his initial blasts. When he pulled out, I used my tongue to lick the remaining cum inside my mouth before swallowing it. There was still a strong taste in my mouth which I was starting to enjoy.

As I began to stand up, he wrapped his arms around my chest, helping me up. I’m sure he could feel my bra and falsies. When I was fully erect, he squeezed me in his arms. I felt another wave through my body as he rubbed his hands along my back over my bra and pushing his chest against my fake tits. He finished by asking, “Well, was it everything a girl likes?”

I said, “Oh yes. It was wonderful.” For a minute, I felt like a woman from head to toe. I was hooked for life.

More of my adventures in future chapters.