My First Night As A Male Escort

Ive decided to go full on anonymous because the next few stories I will post here are in fact non-fiction. Also these events have never left my lips until today and as you read on I’m certain you will understand why. I have placed a generic picture as my avatar so my identity is kept secret. I hope that doesn’t take away from the story for you, as the reader.

This is a story about my first night as a male escort.

A few years ago I fell into a terrible financial rut. I had lost my job due to downsizing and had a terrible time finding another job that even came remotely close to paying what I was previously making. The first few days didn’t seem so bad. I had a check coming and hope was alive and well. Before I knew it, the middle of the month began to creep up like a raccoon in predawn hours and my anxiety started to set in. To cushion my inevitable fall I began work at a grocery store in an attempt to make some money until something better comes my way. Sadly it wasn’t enough and the end of the month is now here. To paint a more vivid picture of my panic, I have no mom and dad, no real friends, and I’ve been on my own since fifteen years old. So getting evicted for me truly meant I would be on the streets. I knew some girls from the city that worked in exotic clubs and I asked could they put in a word for me and maybe I could bust tables as a second source of income. They were no help in that department but the did offer an alternative. Because this was our first time discussing anything concrete about their work, I had learned from this conversation that they also worked as escorts when they were not working at the club. They informed me that if I really needed the money they could introduce me to a few people they knew in the business. I didn’t ask any questions. It sounded fair enough already. Getting paid to be with a woman, no matter her appearance, was an easy deal assuming great hygiene was something that was valued evenly throughout the community. I was elated on the way home and by the time I parked my car I received a text. For the sake of protecting this person’s identity I will call him John. Yes, he was a guy. The text read “Hey I’m john. The girls said you would be waiting on my message. I hope i didn’t contact you too late.” I thought to myself this must be some kind of joke. But then the initial message was followed by a picture of his genitalia with a message attached asking if i could handle something that big. For the record it was an average size but I responded with question marks because i was confused. In retrospect, I understand there was also curiosity lurking in the depths of my brain. I had never been with another man before and had never made any plans for it, but I was certain the girls were playing a joke on me until he informed me that he had already received a few photos of me and he would be delighted to pay a thousand dollars to spend four hours with me the following night.

I threw my car in reverse and I drove to the liquor store around the corner from my place. I truly wanted to keep my morality out the decision making process. I did have someone whom i considered to be my girlfriend and up until this point I have always considered myself to be a heterosexual man. But I knew, with only a few days left to come up with rent, I would soon be a homeless heterosexual man if I did not take this offer. I drank until i became intoxicated and I replied yes. I created a completely different persona so I wouldn’t feel like it was actually me that was about to go through with this and we messaged back and forth for a half hour discussing what was to be expected upon my arrival to his hotel.

The next day had arrived and left and the agreed upon time grew near. I messaged him my ETA and he responded shortly with a “Great. I can’t wait”

My stomach began to turn I as realized this was about to happen in real time. I was nervous. I didn’t know what to expect. I had never been a sex worker and I’ve never dreamed of being “worked” by another man. I arrived at the hotel, stomach filled with these horrible little flutters. I gave myself a pep talk and sent him the message. “Im here.” He responded with the room number before I was able to conjure another thought.

I exited my car and found my way to his room. I took a deep breath and I knocked on the door. As the door opened I immediately became consumed with fear. He was a middle aged, normal looking, white guy, with a wedding ring. I thought to myself this has to be a setup. But against my better judgement, I entered the room and waited for him to tell me what to do next. He handed me a half gallon of whiskey and said “This should take the edge off.”

We made a little small talk until we both felt comfortable and then the awkward silence settled in. And that’s when it hit me. He hasn’t done this many times hisself. He’s just as green as I am. I’m not sure if it was his submissive attitude, the whiskey, or the painful uncertainty of what to do next, but something was born out of that silence and I became the initiator. I walked over to the bed where he was seated and i told him to tell me more about himself. As he talked about work, I unbuckled his belt, got down on my knees, and shoved him in my mouth. His words were replaced with moans of satisfaction and it seemed as if he forgot about his shy demeanor as he grabbed the back of my head and forced himself deeper into my throat. It came as a surprise to me how easy it was to perform fellatio. I just thought about how I would like it to be done to me and i massaged his dick with plenty of spit until he was fully erect and throbbing. He stopped me and confirmed if I was ready for things to get more physical. I said yes, thinking only of my reward, and I cautioned him to go easy because I had never done this before. He got up and put on a contraceptive. He added lube to the condom and subsequently to my asshole with one finger and then two. After a few warm up strokes with his fingers he asked once more if I was ready. I nodded yes. He pushed himself inside of me. First, just the tip. I jolted and pushed his thighs with my hands as a natural reflex. He told me to relax and began to push deeper inside of me. Slowly advancing his speed. His penis wasn’t huge but it wasn’t small and i felt every bit as his pelvis met my ass with a smack. I moaned and groaned as he continued to stroke me and i could tell he was enjoying the sounds as the pounding became harder and faster. So in an effort to speed up the process i focused and fought through the pain and moaned loud and sexy. It wasn’t long before i became turned on myself and maybe it was the taboo, but i found myself wanting to please him because I found pleasure in his uncontrollable twitches of the legs. I had maximized his level of pleasure and he was getting ready to explode like an atomic bomb. I layed flat on the bed and urged him to cum for me. I bit the pillow and anticipated more aggressive strokes. He smacked my ass and thrusted a few more times until he let out a series of loud grunts. He stuffed me with his cock and as i grunted from the force he filled his condom so much i could feel it swell inside of me.

We were done. He backed out of me and pulled of the protection we used and he realized i was fully erect. He said he had never had a man inside of him and he wanted to give it a try. My penis was much larger than his but I am also 10 inches long and pretty thick. I’m not bragging but to give you a better picture I want to leave out zero details.

He was eager to try and it was on his dime so I agreed. I had never penetrated a man before, but I figured, what the hell, I’ve come this far with experimentation, might as well go all the way. I reached over and grabbed another condom from the tiny desk next to the bed. I rolled it down from the tip to the base. He lifted his legs up towards the ceiling and put his lube-covered fingers in between his cheeks. He grabbed me and inserted me into him. He had definitely done this before. He was tight but not like I expected and his pulling me in suggested he didn’t have to adjust much to the painful motions as I did. I felt no difference in physical pleasure from what I could remember while fucking my girlfriend. Although I’ve never been inside of her ass I assumed it was similar. Nonetheless the stimulation was riveting and I found myself stuffing him with so much force he stopped me and took a break. Apart of me wanted to give him some of the pain he caused me. And strangely another part of me wanted to fill his entire ass up with my cum. He invited me inside of him again and I rushed in without hesitation. I then flipped him over and I fucked him until I collapsed on top of him from cumming so hard. This was wild and I knew it, but I was here so I might as well enjoy it. I have three hours left. We wash up and sit on the bed. Talking to each other seemed to become more awkward after sex which is never the case with women in my experience. My ass was in pain and I was beginning to think I wouldn’t last the entire evening. When I voiced my thoughts aloud, he reminded me of our deal and further mentioned that he would only be inclined to give me half of the amount agreed upon. I thought that was fair. I put on the rest of my clothes and he stopped me. “Wait.” He said. “Are we not going to go again?”

As he handed me eight hundred dollars, a gratuitous version of me felt not only obligated, but kind of excited to go again. He pushed me on the bed and shoved his dick in me for more. It felt better this time. I kept coming close to ejaculating as he stroked me. I decided to have fun more fun with it and let him treat me like a woman as he spanked my ass and kissed my back as he adjusted his speed from fast and aggressive to slow and sensual. He then pulled out of me and asked if i would suck his dick like I really wanted to be there. I became more aroused as he complimented me on how much better I was at this than his wife. I stroked his dick with my hand and mouth simultaneously and in a moment of heated passion I told him to finish in my mouth. He jolted after hearing my command. He forced the back of my head against the wall and face fucked me repeatedly. He screamed his announcement and he was going to fill my mouth. I could tell by the amount of energy he gathered with every thrust after. As he roared I felt the warm, creamy, surprisingly neutral tasting substance leave his cock and flow into my mouth. Small jerks let me know he was still having and orgasm so i held still while he continued to cum in my throat. Some of it went down involuntarily so when i looked up at him I decided to give him a show. I nudged the excess from my chin into my mouth and with a bit of theatrics I swallowed his cum and opened wide so he could see it disappear. He then kissed me and said “Thank you”. I put on my clothes and walked with a bit of shame radiating from my aura. I made it to my car and I sat in silence in the parking lot for a few minutes. I counted the money again almost in disbelief of what just happened. Then as I thought about it, I again found myself becoming aroused. I told myself to forget it ever happened but it was one of the best orgasms I have ever experienced. I was falling victim to a siren song calling me back to the room but just for fun this time. I felt bad for taking money for something so exhilarating and the way he came alive while he was cuming inside of me made me happy. It made me feel wanted and appreciated for once. I knew the only way to stop myself from going back was to admit that I liked it. And I mean really liked it. If it wasn’t for the pain i would put the experience in my top five sexual encounters. I placed the money in my glove compartment and I looked around. I was either going to go back and explore or masturbate and fantasize about him one last time. I rushed home to take a shower and I masturbated 3 times before I went to bed. I wasn’t sure what he had done to me but I couldn’t get him out of my head. Mainly because I could still feel him in my ass. The next morning I woke up and told myself I would never speak of this again. And I didn’t until today.