This story is true. I promise. How can you tell? Because it contains humiliating details.
I was 22 and a chronic virgin.
A mixture of being somewhat timid and overtly religious until that point had prevented me from advancing far with the opposite sex.
Of course, being religious didn’t mean I had been a good boy the whole time. I had had my fair share of sexting with strangers I had met in chatrooms, hours of porn surfing under my belt, and many, many more hours spent tugging my cock to the stories on various sites.
It was at this time, after years of deep frustration had finally built to a breaking point, that I finally had an idea. You see, it was the culmination of years of tentative exploration and mild thrill-seeking. I had built up from internet porn to actually walking into a sex shop. I know, right. What an adrenaline junkie. After that, I had hidden porn in my room and even invested in a fleshlight.
The natural next step was actual sex. But how?
Cue the brilliant “CHING” sound with a lightbulb above my head: escorts!
Yeah, I decided the most economic way, without having to take the risk of socially humiliating myself, was to pay an anonymous stranger for sex.
Being a pussy who sorely lacked pussy, I did my research for a few weeks until my libido finally made my decision for me. I had been frequenting a few sites, but I finally settled on one with a relatively good review system. I picked a girl who looked like my type from the faceless shots, and with my heart racing in my chest, gave her a call.
“Hello?”
“Hi, is that Dark Angel?” I said. Of course, it was an alias.
“Yes sweetie,” came the not unfriendly yet terse reply.
Now was the time to go for it. I had practised it in my head.
“Hi,” pant, pant, “I’d like to find out what your rates and services are please.” Wheeze. Sweat. Panic.
The thrill was already getting to me. I felt a stirring in my pants. What an amateur.
“Okay honey, I charge 300 for half an hour, 500 for an hour. I do kissing, cuddling, full girlfriend experience. Everything goes except Greek. If you pay for an hour you cum twice.”
It took me a moment to process everything. I knew what I wanted.
“So, um, when are you available?” I asked with my heart in my throat.
“When do you want to cum see me, baby?” Came the sultry response. You could practically hear her spelling out the word “cum” as she said it.
Shit, what to say?
“How about now? Where are you?”
“No baby, not now. Give me half an hour sweetie. I’ll text you the address. Call me when you’re at the gate.”
“Oh, okay. That’s perfect. I’ll see you in half an hour. Bye.”
Fuck me, it was about to happen. My adrenaline had slightly calmed down. I panicked for a moment, then tried to get a hold of myself. I needed to shower. I needed to get going and draw money. I also needed her to send me the address.
Somehow, I got through the next half-hour and soon found myself calling her again outside her gate in my car.
“Hi, it’s me. I called you earlier, I’m here for the hour.”
“Okay baby, I’ll open for you.”
My heart tattooed against my chest.
Another blur of motion and sound and I was being led down a seedy hallway to a room. The house was decent looking, maybe slightly run down and unfurnished in the common areas. She ushered me through a door and closed it behind us.
The curtains were drawn, giving the room a red glow. There was a bed and a side table, and that was it. I had an opportunity to look her up and down.
An attractive black girl stood there in lingerie, garters, and high heels. A bit thinner than the photos indicated, but she had a pretty enough face. She was also about a head shorter than me, even with the heels, and I’m not exactly tall.
She looked at me expectantly. I knew what to do, I had done my homework. I reached into my pocket and took out the envelope containing the cash.
“An hour is fine, right?” I asked.
“Sure, give me a moment, I’ll be right back,” she said leaving me in the room. “Make yourself comfortable.”
Comfortable? How? I was a bundle of nerves and I was wondering if I was about to have an aneurysm. So, I sat on the bed, reached for my pants, thought better of it, and just sat there. I considered kicking off my shoes, but I didn’t want to be presumptuous. Of course, never be presumptuous with the person you just handed money to in order to fuck them. Makes sense.
The click of heels indicated her return. She came in and glanced at me sitting on the edge of the bed but didn’t comment on my state of dress. That being, fully.
“Um, so, I have to tell you something,” I blurted out. Great, way to mess things up before you start, you dolt, my inner voice berated me.
She looked at me quizzically, clearly giving me the benefit of the doubt for a few moments.
“I, um. I’m a… this is my first time doing this,” I finished lamely.
“Oh, that’s okay honey,” she said. Yet, in her eyes, I could see her thinking: great, just what I needed today.
She walked around to the foot of the bed and took me by the hand, indicating I should stand. Facing her, the height difference was more pronounced than I remembered. She led me around to the side of the bed and sat at the edge and spread her legs, pulling me between them.
She started massaging the front of my jeans and I nearly died from anxiety. Someone was actually stroking my penis, almost touching it directly, for the first time in my life. Well, second, no, third. (Maybe I’ll tell those stories another time.)