Meeting a Client as a transgender

Spread the Love

Meeting a client as an escort result in an unexpected situation.

I sat at my computer, rereading the most recent message he’d sent me. “Put on something red, knock three times, and I’ll be wearing a mask.” I’d started going to clubs while cross-dressing a few months before. On a few occasions, I’d met a guy and we’d ended up fucking; once in the club toilets, but more often than not, I’d return to their place. Most of the time, however, no guys seem interested, and I would leave the club disappointed and horny, so I needed a better way to get what I wanted.

When I was searching the internet for a better way to meet guys, I came across an escort website. I thought it was a brilliant idea. I’d get to meet guys, have sex, and be compensated for it. What could be better? I did make it clear what I was, however, because I didn’t want them to pay thinking they were getting a woman. Julie is the name I came up with for my escorting side. Doug, my male name, is a far cry from mine.

I’d already met with a couple of guys looking for blow jobs through the website. I’d met them both at their home. I couldn’t do it at my house because I shared it with my twin brother Dylan. Our lives had taken such different paths up to this point that you’d never guess we were twins. Dylan was as straight as an arrow, went to the gym, and participated in a variety of sports, so he was quite well built and athletic. He was always bringing women home with him. I was bisexual and pretty skinny, but I did a lot of cycling, so I had an arse that guys couldn’t get enough of. I’d dated a few women, but nothing like the number my brother had. After my last breakup, I started messing around with guys and discovered that I enjoyed sucking dick and being fucked.

I changed into the lingerie I’d chosen to suit the client’s tastes: a red satin and lace basque with matching panties and stockings. Since becoming an escort, I’d purchased a silicone breastplate. It was a significant improvement over my previous breast forms, and they felt and moved almost exactly like the real thing. I applied makeup and put on a shoulder-length wavy bright auburn wig. I put on some red stilettos, stood up, and examined myself in the mirror. I liked how I looked like a woman at times.

It was summer, and the hotel where I was meeting my client was just around the corner, so I threw on my long coat over my outfit and left my room. As I walked downstairs, I glanced over at my brother’s bedroom door and wondered who he had been seeing during this time. I was well aware that she was a screamer. I exited the house, locked the door behind me, and proceeded to the hotel.

As I entered the hotel’s foyer, I went straight for the lift. I checked my phone for the client’s room number and pressed the fourth-floor button. I dashed off to find the room as the lift door opened. A mirror was just to the side of the door. I looked into it, adjusting my hair a little and letting a few waves fall around my face. I took a deep breath and knocked three times as I stepped back in front of the door.

“It’s unlocked, please come in,” I heard from behind the closed door.

I twisted the handle, pushed open the door, and walked into the dimly lit hotel room. It was a fairly standard room, with a bathroom off to one side as you entered, a table and chair on one wall, a window that probably couldn’t be opened very far on another, and a double bed on which the client was sitting. He was wearing a mask, as he had promised, covering most of his face but leaving his mouth exposed. Aside from that, he was naked, his hand wrapped around his dick, slowly moving up and down as I walked in.

“The money’s on the table,” he said, pointing to the opposite wall of the room from the bed.

I gave him a friendly smile before moving over to the table and counting the money he’d left there. Everything was in order. I slowly unzipped my coat, pulling it down just past my shoulders, standing with my back to the bed. I looked behind me and noticed the client staring intently, still holding his dick but too preoccupied to play with it. I let my coat fall to the floor, revealing the lingerie I’d carefully selected, while still looking over my shoulder. His jaw dropped a little and his eyes widened.

“Damn,” he muttered.

I turned around, smiling, and saw his eyes widen even more. As I approached the bed, I noticed him becoming sterner as he examined me from head to toe. I climbed onto the bed on all fours and positioned myself in front of his crotch. I gently moved his hands away and replaced them with mine.

Meeting a client

“Let me handle that for you,” I said while gently caressing him and looking into his eyes.

A huge grin spread across his face as he adjusted his position to make himself more comfortable. I leaned in close to his balls, moving my hand up and down his shaft. I gently swirled one of his balls around in my mouth. He seemed to enjoy it, as evidenced by a slight moan. I took his other ball into my mouth and did the same thing with it because I didn’t want it to feel left out. I moved on to his gradually hardening dick, licking up his shaft towards his head, which I teased a little before licking down towards his balls.

He clearly couldn’t take any more teasing because he was quickly adjusting himself so that his dick was pointing towards my mouth, implying that he wanted me to suck him. I took the hint and placed the head of his penis in my mouth, wanting to give the client what he’d paid for. I moved my tongue around, concentrating on the most sensitive areas. The client shifted again, this time placing his hand on the back of my head and gently nudging me to take more of him in my mouth, which I did.

He wasn’t fully erect, but he was still a good mouthful as I took him all the way in and paused for a few moments, feeling him harden in my mouth. I drew back until only the head was in my mouth before lowering myself all the way. I got into a habit of taking him all the way in, drawing back until he was almost out of my mouth, and then swallowing the entire length again, all the while feeling him become harder and harder in my mouth.

When I struggled to take the full length down my throat, I knew he was fully erect. I persisted, and then spit it produced in my mouth helped me deepthroat him. This went on for a few minutes until he asked me to stop. I took his dick out of my mouth and looked up at him, slightly disappointed.

“Is there something wrong?” I inquired.

“Certainly not!” he exclaimed. “I just want to try something new. Lie down near the edge of the bed, allowing your head to hang over the edge.”

I nodded and did as he instructed. I licked my lips in anticipation as he climbed out of bed and positioned himself in front of me, his dick at my eye level. He teased my lips with his dick, and when he drew back, I instinctively tried to move my head back to get my lips around it.

“You want this, don’t you?” he asked, laughing.

“Yes…” I moaned, enthusiastically nodding.

He responded by putting his dick between my lips and, as I took a deep breath, he pushed inside, moving down until his balls were touching my face. He stayed like this for what seemed like an eternity before slowly pulling back and withdrawing from my mouth, leaving a spit string between my mouth and his dick. It took a few seconds for me to regain my breath, and I took another deep breath just as he stuck his dick completely down my throat again.

This time, he reached over and placed his hand on the bulge in my pantyhose, which was barely covering my rock-hard erection. He began to rub me, and I let out an involuntary moan or tried to. With a large dick shoved down your throat, it’s difficult to make much noise. Instead of rubbing me, he stood up and placed a hand on each of my breasts. He pulled out of my mouth again as he did this, allowing me to take a quick breath before plunging back in.

Rather than remaining in a position deep inside my throat, he pulled out but not before thrusting in deep again. As he fucked my throat, he quickened his pace, and I couldn’t stop myself from rubbing my penis through my underwear. As he began to thrust as hard and deep as he could, I could feel spit dripping from my mouth and down my face. He was fucking my throat so hard that the bed began to move slightly with each thrust, eventually colliding with a tall lamp that fell over towards the window and pushed the curtains aside, allowing a small amount of outside light to enter the room and land on his leg. Then I noticed a mark that looked very familiar.

It was a birthmark that looked familiar because I have the same one on my leg. It was a dark smudge that, when viewed from a certain angle, resembled a bird. My eyes widened in horror as I realized only one other person could have a birthmark identical to mine. Before I could react to my realization, his grip on my breasts tightened and I felt his dick pulse in my mouth as he shot a huge load down my throat, forcing me to swallow my twin brother’s cum.

We both remained motionless for what seemed like an eternity, Dylan panting heavily and be unable to take a breath with his softening dick still down my throat. He eventually let go, allowing me to breathe again. As he collapsed onto the bed next to me, I remained with my head hanging off the side. I was still reeling from what I’d just done. Even though it was completely unintentional, I’d sucked my own brother’s dick and made him cum, swallowing it all. As I lay there with the taste of his cum in my throat, a million thoughts raced through my mind. I’d never been so perplexed in my life. I’d just learned that my brother had hired me as an escort, with neither of us knowing who the other was, and I’d sucked him off. When Dylan spoke up, all of these thoughts were still running through my head.

“That was fucking incredible. I don’t usually see the same person twice, but I can’t help myself with you. Why don’t you come over to my house tomorrow? I’m dying to fuck that arse.”

“Sure,” I responded before my brain had a chance to respond. I couldn’t believe I’d agreed to be fucked by my brother. What was the matter with me?

“Wonderful, same time?” he inquired, and I nodded. “Cool. If you need to freshen up before leaving, feel free to use the bathroom.”

I mumbled a thank you as I took the money from the table and my coat from the floor and entered the bathroom. I looked into the mirror, my heart pounding and my hands trembling. I took a few deep breaths to relax and noticed that my mascara had dripped a little down my face. Given how hard Dylan had fucked my mouth and how much spit had dribbled down my face, it had held up remarkably well. I took a makeup wipe from my coat pocket and wiped the mascara off my face to look presentable on my way back through the hotel.

I stepped out of the bathroom, put on my coat, and turned to face the bed. He had already dozed off. I walked over to the door, opened it, and then quietly closed it again after passing through. I didn’t make it more than a few steps before collapsing into a seated position against a nearby wall, head in my hands, my mind racing with what had just happened. One thought, in particular, stood out among all the others in my mind: why was I still rock hard? I knew I’d just had my brother’s dick down my throat, but I was still so turned on just remembering the taste that I knew if I even touched my dick, I’d probably explode right there and then. Worse, the more I reflected on it, the more I wanted to do it again. I couldn’t help myself, as wacky as that sounds. If Dylan had fucked my throat for a long enough period, I might have just cummed without even touching myself. Who knew my brother could be such a jerk? It’s no surprise he never seemed to have a problem finding a girlfriend; I wouldn’t blame any girl who got a taste of that dick for wanting to keep coming back for more.

I gathered my thoughts, stood up, and returned to the lift. I was in a trance as I walked the short distance home, still thinking about what had happened. When I got home, I went straight to my room and sat on my bed. I closed my eyes and replayed my encounter with Dylan in my mind. As I remembered sucking Dylan’s dick, I couldn’t help but stroke myself. I couldn’t take more than a few strokes before my stomach exploded. I placed my hand on my stomach, smeared some of my cum on my fingers, and placed them in my mouth, swallowing my load while imagining it was Dylan’s. I promptly fell asleep as a result of this.

The next day, I awoke late. I checked my phone and saw that I only had a few hours until I was supposed to meet Dylan. In his bedroom, I could hear him working out. I swore aloud; the plan had been for me to get ready while he was at work and then go out for a bit while we waited for our meeting, but I couldn’t do that now. I called my friend James, who thankfully agreed that I could go around and change at his place. James was aware of my transgender status, and we had fucked a couple of times while I was dressed, but that’s a story for another time. I threw a random set of lingerie into my bag, along with some heels, makeup, and a dark red French braided wig, and dashed to James’ house. I hung out with him for a while after getting ready there until it was time to return home to Dylan.

Read on Part 2

Your comment
© 2024 Fifty Escorts