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My First Time as an Escort! (A Fantasy)
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My First Time as an Escort! (A Fantasy) This is a complete work of fiction. I would never break the law or violate Polyamory Date policies.  I have been on several free listing services like Friendboy and Rentmen for a few years now as a smooth crossdressing sissy and to my surprise I have gotten some interests. However I am always concerned that the "john" or "trick" could be a law enforcement officer so I would often refuse requests. Sometimes I will even research the caller as best I could or ask probing questions. One guy wanted me to serve him in his RV parked in a certain neighborhood. When I researched the neighborhood it turned out to be a solely industrial area with no place to park an RV. But a perfect place for a police sting. Or one caller would tell me he lives locally but his phone number is based out of state. I also realized that most cops won't mention sex first, that could be considered entrapment. Usually they ask, "What do you do? How much?" If a texter says more incriminating stuff, like "I want sex," or sends me a pornographic pic, I take my chance that he is a legit john. And that is what happened here, on my first time. This stranger texted me out of the blue, "Hi, I'm J---, I got your number on Friendboy. I'm interested but I can't host. What area of SD do you live?" I never mention sex first so I asked him, "What service do u want?" See I portray myself as an "escort," as an actual date, as a companion, someone to accompany a guy, I even mention I'd go anywhere they wanted...I'm an "escort" after all, I'm supposed to "escort" them. I'd let the john use incriminating terms like "sex," "oral," "anal," and etc.. I usually remind them that they are paying solely for my time, NOT for anything we do...or don't do. This john responded "I want sex," So I figured he wasn't a cop. Being new to the industry and pretty much getting on the job training and all on my own, I started out low on my prices. $50 to start, up to $100 for more than one hour. Many were asking for hundreds more just for an hour. We texted each other more, he even sexted me a pic of his exposed dick and balls, then we scheduled a date. He drove to my place, but I live in downtown San Diego blocks from the Padres Stadium and there was a game, so it was almost impossible for him to find parking. He texted that we may have to cancel and reschedule, but I changed his mind with a sexy pic of me. I had already shaved my sissyboi bod smooth again and taken a shower, washing my ass and boi pussy hole very carefully, and had put on a small, tight skirt and bra, as seen in these pics. I was horny and didn't want to do all that for nothing. Now I never met a guy at my place before because I sued to have roommates and after we confirmed our date I started reconsidering if I should meet a john at my home? After all if I met him at his place, a hotel, a car, an alley, wherever, I could run away if things go bad. But if we meet at my place, I can't escape. Or I could but then the guy would still be at my place with access to my valuables and materials that expose my identity and private life. But against my better judgment, I decided to take a chance and meet this guy, my first "john" or "trick" at my place. I met him outside my place because it is a secured building and escorted him inside. The man was in his low 60s, white hair, beard and mustache and glasses. He looked like your average Grandpa next door, and being around as much as I have now, I've often wondered how many people have fathers or grandfathers that are secretly into this lifestyle. "I'll be right out. Make yourself comfortable." I offered as I went into the bathroom to change out of my boy clothes I had to wear when going outside. He reclined on my bed (I live in a studio.) Minutes later I walked out in that plaid skirt and black bra and J's eyes widened and his mouth fell to the floor. I sat next to him on the bed. I have been with hundreds of men now, even one night stands with strangers, but was never paid for it, so for a few minutes I didn't know what to do.  J then undid his pants and very aggressively grabbed my head and pushed me to his cock. I grabbed it with my mouth and started sucking hard and stroking it up and down. Thankfully it had no odor like a few others I've been with. Every time I'd get up to get some air, J would force me back down. Even for his age he was still stronger than me and could have done anything he wanted to me. I started seeing in my mind horrific scenarios, like I could be the typical newbie that gets ra*ed and beaten their first time, so rethinks the whole idea. He would brush my dick and balls with his foot, I wasn't wearing any panties as you can see in these pics which were taken just minutes after J left. As I was sucking him, one of his hands slid down my back and to my ass, then he tried to straddle me in the 69 position. But I can't do 69: when I suck a guy my dick goes limp, so J couldn't get my small, flaccid penis into his mouth.  "Turn around on the bed," he commanded so I did. He grabbed my ankles and dragged my ass very easily like I was a ragged doll over to the edge of the bed. "Do you have lube?" "No," I answered, "Okay," he said,. "We'll have to improvise." J found a bottle of sanitizer I had and lubed up his big, hard dick with it, then poured some into my hole. "Spread your legs!" he yelled, so I did, and I could feel him spread my buttcheeks and force open my tight boi pussy hole with his fingers. He spanked me too, several times. Not soft like my boyfriend, but hard, painfully, this was for real! His cock couldn't get into my asspussy because of a medical condition I have. Like hemorrhoids where my rectum would be bruised and swollen so it even hurts to wipe much less be fucked there in my ass!   Eventually J gave up as his dick went limp, so instead he shoved his fingers into me and started fucking me with them. This pain was real, I wasn't faking and acting like I do with my boyfriend, I was really yelling, screaming, crying, moaning....with each whimper J would get more excited and push his fingers, soon his whole hand as far as he could up inside me, I was afraid he was going to puncture something and damage my insides! He then shoved the sanitizer bottle into my ass, I think a whole half of it did fit in! I screamed some more, muffling my screams in my pillow. "Do you like having fingers fuck you?" J asked. I nodded, "Good." I was scared that if I said "Enough!, that it was hurting too much, J wouldn't care and would just ra*e and beat me. But I was able to get up without a problem. J then laid down on the bed on his back, holding his limp dick. It was leaking pre-cum I could see though. I tried to get him hard again with a hand job then sucked him a bit more. But he was through. I was so disappointed and embarrassed that I didn't get him off. I apologized profusely, but J told me not to. He turned out to be really nice guy and, again, "normal," I guess he is just rough during the actual sex. We talked a while and he told me I am worth way more than the $50 I ask for and that I should ask for at least $100 or more. I didn't dare ask him for any payment, seeing how disappointing I thought my service was, but to my surprise he took out a $100 bill and said "I'm giving you $100. You're worth it." I have met up for sex with lots of strange men but have never been paid for it! This was such a new and exciting feeling!  After he left I sat on the bed, my ass in great pain, but with a huge smile on my face just staring at that $100 bill in my hands. Doing nothing but practically just laying on my bed, I made more in an hour than I make most of the day at my normal full-time job. Despite the pain it was still the easiest and quickest $100 I ever made! Granted it came with great risk, like if the "trick" or "john" would ra*e, rob, or kill me, and the possibility of contracting an STD. But I had such a feeling of great pride, pride that a grown man found my body worth $100, money I didn't even ask for. Proud that I sexually satisfied a grown man, one who himself has been around, and he saw that much value in my service. I hope to do it again, but also hope my luck doesn't run out and get caught up in a human trafficking sting. Anyways....again: THIS IS FICTION. A fantasy, Okay?     |
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