The Theater

This is based off my actual first encounter with a transsexual, and also my first trip to an adult theater back in March, just before the lockdown started. It certainly didn't go the way that I expected, but I still had a good time that day. I figured I would share my experience with my fans, although this is a slightly exaggerated version of what actually happened that day. Regardless, I hope you all enjoy, and please stay safe and healthy.

Whiskey

*****

I had been attracted to transsexual women for a long time...probably since my teenage years, to be exact. I had never actually been with one though, for various different reasons.

For one thing, I had been in a relationship for thirteen long years, and I wasn't the type of guy to step out and cheat. My father had done that to my mother more times than she could count, and I never wanted to cause anyone the same kind of pain, that he caused her.

So, I stuck it out. I married the girl I had been with when I was twenty five years old, and four years later, we were separated and on our way to divorce.

It was a messy split-up, I'm not going to lie. We knew it was over for a while leading up to her actually moving, but we tried to stay friends, so it hurt when she abruptly announced...the night before...that she was moving out and back in with her parents.

Fine, I thought, after four months had gone by. It's over, she left, she won't even talk to me anymore...I'll move on with my life and take this opportunity to start doing the things, that I have been putting off, for the last thirteen years of my life. One of those things being, going out and exploring my sexuality.

A friend of mine, who was a bit older than I was, had some experience with doing some of the things I wanted to do...and he had been with a few trans women, to. So, he offered to help me out and one day, he drove me to a theater out in New Jersey. I had obviously never been to a place like this before, so it was like walking into a whole new world when we arrived.

The theater was in the back of what looked like a convenient store. You pay five dollars to get in, and after inserting the money into a kiosk next to the entrance, a loud buzzing sound was heard, followed by a loud "click" that indicated the door was unlocked. I pulled the door open and stepped inside, to find that it was very...dark. I mean, really dark.

Of course, my friend had warned me it would be like this, but I was surprised to see just how dark it actually was. I stepped further inside and to my left, were the first two rooms. One of them, being larger than the other, had what looked almost like a table but was covered with leather padding. There was also a very long bench against the back wall in the room.

The second room was much smaller, and only had two benches on opposite sides of the room, as well as a single bathroom meant for men and women...and in-between, of course.

In both rooms, were big flatscreen TV's mounted on the walls, playing porn. The speaker system was cranked up nice and loud and the sounds of moaning echoed all throughout the long corridor that lead all the way to the back.

Since the first two rooms appeared to be empty, I followed the corridor back to the third room, which was actually the largest of them all.

It almost liked like a movie theater, with a huge screen mounted on the wall at the front of the room and rows of chairs that led all the way to the back. I stood in the doorway for a moment, taking in my surroundings, while my friend made his way to the very back room and left me to take things in on my own.

After a few minutes of watching a cute short-haired blonde on the screen, sucking a rather large cock, I felt a hand on my shoulder.

"Hey," my friend said, nodding for me to follow him.

"There's a trans girl back there, come on!"

I didn't have time to respond, before he moved behind me and gave me a bit of a shove, ushering me towards the last two rooms in the theater. When we got there, I saw a tall woman, with broad shoulders and long red hair. She was wearing a tank top and a short black skirt, with fishnet stockings, showing off her long and, well, toned legs. She smiled over at me immediately, and then moved behind a wall, to sit on a bench and wait for me. "Go talk to her," my friend encouraged me.

I nodded nervously, and stepped around the wall into a small booth, to join her on the bench. "Hey," I said, shakily.

"Hey yourself," she replied, with a smile. Her voice was deeper than I expected, and with the only light coming from the TV, I managed to get a better look at her than before.

Long red bangs fell over her face, and she brushed them aside, tucking a strand of hair behind her ear and clearing her throat before speaking. "Have you ever been with a transsexual before?"

"Uh...n-no, no, I haven't actually..."

"First time for everything, right?"

"Y-Yeah," I laughed, trying to get a grip on myself. "Actually, I've never even been to a place like this, either...so, I guess today is a day of firsts for me."

I sounded so corny, I thought to myself, shaking my head.

"Well, I'd be happy to help you get a little more comfortable," she smiled, placing a hand on my left leg. "If you're up for some company, anyway."

"Yeah," I nodded. "Yeah, that's okay with me."

She smiled wider, taking my hand and placing it on her leg, just below the hem of her skirt. I could feel her soft, smooth skin through the fishnet stockings as I began moving my hand up and down, gently stroking her leg. We were both quiet for a while, as we just sat there and watched the TV, a young brunette taking at least ten inches of cock, balls deep in her big, heart-shaped ass. At random, my new friend suddenly moved even closer to me and leaned in to whisper in my ear. "Are you horny?"

I felt her hot breath against my ear and it sent shivers up and down my spine, as I slowly nodded my head.

"Tell you what then," she said, sliding off the bench and pulling her red hair up to put it in a ponytail. "Why don't you lean back and relax...and I'll get down here, on my knees...and we'll just see what happens from there, okay?"

"Okay," I nodded again, my voice cracking slightly.

I leaned back and watched, as she got down on her knees right in front of me and giggled, reaching up to undo my belt and pull my pants down. I wasn't hard at the moment, but she took my six-inch cock between her hot, wet lips and began sucking on just the tip, in an effort to help wake my "friend."

Something was wrong though...

I sat there, as comfortable as I could get, watching as she sucked at the tip and massaged my balls, but nothing was happening. My dick remained completely flaccid, even as I switched my attention from her, to the porno that was playing on the big screen in front of me.

I closed my eyes and tried to relax more, tried to focus on the warmth of her mouth, but no matter what I did nothing seemed to be happening. "I-I'm sorry," I muttered.

"For what?" She asked as she took my cock out for a brief moment. I simply shook my head and gave a nervous chuckle, to which she responded by taking me back in her mouth again.

I had to admit, as embarrassed as I was at the moment, she was being really patient and understanding with me. I almost expected her to get pissed off and walk out on me, but she just kept going for a few moments longer, before finally pulling back again. "Are you okay?" I could hear, concern in her voice, and I sighed, more than a little annoyed with myself by now.

"Y-Yeah, sorry just...I guess I'm just really anxious?"

"Hmm, that's understandable," she smiled. "First time in a place like this. Maybe you're just not used to public sex. It happens to the best of us, honey."

I watched, disappointed, as she got back on her feet and let her hair back down, as I pulled my pants back up and fixed my belt. I couldn't believe this was happening to me. I had come here to have fun, to do all the things that I had been putting off for all the years, and when I finally get the opportunity to do that, I can't even get hard?

What the fuck was wrong with me?

Then I relaxed, thinking to myself that maybe there was still a chance for me to enjoy myself, in another way.

"M-Maybe we could, uh...you know...try something else?"

"Oh? What did you have in mind, sweetie?"

I was too nervous to even say it, but I cleared my throat and forced the words out. "I mean...I-I could do you..."

She paused for a few seconds before a big grin spread across her face and her hands moved to her hips.

"My, you're a curious one, aren't you? Well, if you're sure you really want to..."

"I do," I nodded, probably sounding a bit more excited than she may have,

anticipated. She didn't say another word, simply slipping out of her skirt, to reveal that she hadn't been wearing panties underneath. Unlike my own, her cock was fully erect. It stood at about seven inches and was uncut, like my own.

She stepped closer to me, as I stayed seated on the edge of the bench, and I leaned forward until her dick was right in my face.

I felt a hand moving through my hair, as she used her other hand to pull the skin back on her cock and rub the tip against my lips. I breathed in the pungent aroma, of sweat, and was only vaguely aware of the growing hardness between my legs. Funny that all it took to get me hard, was having a dick right in front of me like this, I thought.

I opened my mouth and she slid right in between my lips, pushing all the way to the back of my throat. My taste buds immediately came to life, all at once, as she pulled back some and my tongue slid over the head. It tasted salty and there was a slight hint of piss, though it wasn't so intense that it would have stopped me from what I was doing.

I allowed her to have control of the situation keeping her hand trained on my head, pushing her cock in and out of my mouth and triggering my gag reflex, every time she entered my throat.

I was actually doing it.

My first time sucking cock, and I was enjoying it just as much as I had always thought I would. It was just like all those fantasies that I'd had over the years, actually it was even better.

Gradually, I began to take control of the situation, grabbing her by the hips and pulling her deeper into my mouth. I started bobbing my head, sucking, gagging and slurping, spit running down over my chin as she moaned above me.

"Mmm, not bad baby...really enjoying this...aren't you?"

I ignored her and just kept sucking, until she pushed me back, her cock slipping from between my lips and leaving me disappointed. "Take off your pants," she instructed.

I didn't know what she had in mind, but I obeyed, quickly removing my pants and revealing how hard I was now. She noticed right away and licked her lips. "Look at that," she smiled. "You're little friends finally awake."

"Looks like," I chuckled, reaching down to stroke myself.

She sat down beside me on the bench and pulled me close, until my head was resting in her lap, and I wrapped my lips around her cock and resumed sucking. Laying stretched across the bench, my head bobbing up and down in her lap, she laid her hand on my back and slowly moved it down until I felt her fingers tracing lightly over my ass. I felt them slide between my cheeks and her index fingers gently teased my virgin hole, lingering there for a few seconds, before she carefully pushed it into me.

I gasped, then released a low groan, as she pushed it in until she was knuckle deep in my ass. All the while, I continued sucking her dick, getting more and more into it as I went along.

"That's a good boy," she moaned. "Do you like my finger in your ass, baby?"

"Mmmfff," was all I said, my voice muffled by her cock.

"Mmm, I bet you do. I bet you've been dreaming of a moment like this, for a very long time now. Lying awake at night, fantasizing about a beautiful girl like me, with a big fat cock to suck on...well, guess what honey...I'm the answer to your dreams. You don't have to fantasize anymore, because I'll make it a reality for you."

Fuck, she was so hot.

Everything she was saying to me seemed to make this whole thing, that much more intense. She pushed her finger in and out of my ass, while I continued going down on her, and eventually, she started trying to work a second finger into me. It took a few seconds and I could feel myself being stretched out, causing me to moan loudly, humming against her cock. Once she had the second finger inside of me though, I couldn't help but start to shake, as she started thrusting them both in and out, faster and faster.

I was getting much more than I had originally expected, when I first came to this place.

At some point, someone walked into the booth with us and started watching. I didn't know if it was a guy, or a girl, or another trans woman even. Hell, it could have been my friend that brought me here, for all I knew, but I didn't even care. I paid them no attention, though my partner seemed to be having a nice little discussing with them, about how good of a cock sucker I was and how tight my ass was.

"Are you going to fuck him?"

It was a female, I realized, by the voice.

"Hmm, I'm not sure yet...f-fuck...I'm gonna cum, if he keeps this up though."

That's exactly what I wanted.

And I wasn't far behind her either. I had been stroking my own cock, the whole time, and between her fingers gently massaging my prostate, my hand wrapped around my dick, and the taste and smell of her dick, I could tell that I was getting close.

She pushed my head all the way down suddenly and I heard her gasp. She tensed up, lifting her ass off of the bench and groaning loudly and that's when I felt the first shot of cum hit the back of my throat.

It took me by surprise, even though I knew she was almost there, I hadn't expected it to happen so soon. The second shot splashed across my tongue and I moaned, loving the warm salty flavor. She unleashed another rope, and another, firing off a total of seven thick ropes of cum and I swallowed every drop of it, licking her clean.

As I was busy taking the last few drops of her cum, my own dick began to pulse in my hand and I moaned like a bitch, as I covered the leather bench with my own bodily fluids.

When it was over, I pulled back and gasped for air, spit and cum dripping from the corners of my mouth. I wiped it away and laid back on the bench, sweating and panting, my cheeks flushed red.

She stood up and I watched, as she began putting her clothes back on and fixing herself up, before grabbing her purse and smiling down at me. "You were great," she whispered.

"A-Aren't you...going to fuck me?"

I'd heard her talking with that woman, who had at some point, disappeared without me even noticing until now. I knew she wanted to, and honestly, I wanted it to. Her fingers had been enough to make me curious, to see what something bigger would feel like. She giggled, before reaching into her purse and pulling out a pen and a piece of paper to write her number on.

"Not today, honey," she said, as she handed me the paper.

"But if you want to give me a call next week...maybe we could take things a little further."

I sat up, looking at her phone number and nodded my head, as she slowly walked out of the booth and left me there alone. I was finally catching my breath, the taste of her cock still in my mouth and I smiled to myself.

After all these years, I had finally made my fantasies a reality.

This definitely would not be my last time at the adult theater, and I was really looking forward to meeting up with my new partner again.