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This story is true. I promise. How can you tell? Because it contains humiliating details. I was 22 and a chronic virgin. A mixtur...


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 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 light bulb 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.


“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.)

I was rock hard in no time. Before I could process any more, she was unbuttoning and unzipping my pants. She reached through the front of my boxers

and pulled out my cock. Even the minimal touch and the air were making me extremely aware of how I close I was to the precipice of orgasm.


She stroked me a bit and I squirmed with pleasure and awkwardness. I didn’t want to cum too soon. I had paid good money, and this was my first time cumming from a girl touching my penis. I needed it to be slightly more meaningful.

“Um, can you stop a bit. I’m close.”

She looked up at me, with a smile at the edge of her lips.

“Okay baby, let me get a condom.”

Shit. Was this it? Was this the moment? But I had my pants around my ankles and she still had her lingerie on.

Shut up brain, logistics later, orgasm now.

She reached for the nightstand and took out a toiletry bag with various sexual goodies in, along with paper towels and condoms. Ripping open the wrapper,

she started rolling the condom down my cock, and suddenly I felt slightly inadequate. Was the condom too big for me? I’d never done this before, but was it supposed to have so much give?

Shit, did I have a small dick? Fuck.

Whatever, let’s get this over with.

She rolled it on all the way to the root and took my cock back in her hand.

“Do you want to cum baby? In my mouth?”

“Y—,” I choked a bit. Suddenly my throat was drier than the Gobi. “Y-yes. P-p-please.”

My tiny virgin brain was shutting down, and all I could comprehend was that it was finally happening. The goal was in sight.

She took my cock into her mouth and all I remember was how hot it was at first. My hand never felt like this. My dick tingled with the thrilling electricity of sexual stimulation as she worked my meat in and out of her mouth.

Time slowed for me, but let’s be honest, it didn’t last long. The sensation and situation all conspired to overwhelm me, and in a few short moments, I was filling the condom with my spunk while spasming and trying not to fall flat on my ass.

Holy fuck. That had been awesome. 

In a haze, I remember her taking the condom off and wiping me down with some wet wipes. My poor penis was so sensitive I jumped from the contact of the cold wet wipe and her slightly harsh touch.

The next thing I remember I was naked, kneeling over her on the bed. She was on her back, also naked, lying spread-eagled.

My cock, still rock hard (yay virulent virginity?) and covered in a fresh condom, was pointing straight at her wonderful ebony pussy.

Now, this was slightly awkward. The videos always made this part look easier than this felt. 

Was I supposed to spread my legs more to get further down? Why wasn’t I flexible enough? Shit, I knew I should have done more stretches.

Fine, whatever; let’s make this work.

I made the necessary adjustments and took my dick in hand. I started rubbing my cock up and down her slit, just like I had seen in the porno. 

Honestly, I wouldn’t be able to tell you what her face said at that moment (although I suspect an eye roll), because I was enthralled by what was in front of my eyes. My own cock was lining up with a real, in-the-flesh vagina.

This was it, this was the dream.

I finally came back to reality and started to push forward but to little success. Shouldn’t something be happening? I imagine she rolled her eyes once again at his point, as she reached down and grabbed my cock, lining it up properly with her entrance.

“Okay, now push,” she said with the utmost patience. Bless her saintly heart.

I pushed. Suddenly a kaleidoscope of sensations burst upon my senses. It was hot and wet and amazing. How did I know it was wet while I had a condom on? I have no idea. But that’s my story and I’m sticking to it. It was definitely a furnace.

That heat alone was my undoing, and I suddenly understood why masturbation felt so cold. 

My penis was home.

I pushed all the way to my root, and I paused, savouring victory. I was finally in.

This is the thing I had imagined countless times while jerking my lonely cock at night. 

I was balls deep in a pussy and I was going to fuck the living daylights out of it.

Well, that was the plan anyway.

I pulled out slightly and then started fucking her in earnest. Frankly, I wish I could tell you that because I had cum shortly before, that I lasted a long time and fucked her brains out, ruining her for other men.

Alas, this is after all a true story.

I pumped a few times and suddenly became aware of that tingling sensation in my dickhead that almost felt like the urge to pee.

Oh no. This was too fast; how would I make it last? What had I read? How? Think, dammit!

In my panic, I kept pumping, and I became a passenger to my instincts as my orgasm swept over me.

I froze as my cock spasmed in her pussy, filling my second condom of the day.

My mind was momentarily made of pink fluff as the high of the moment took hold and slowly faded away.

I looked down at her and slowly backed off. I was hot, sweaty, and feeling super awkward.

I took stock of the room around me and quickly made my excuses.

“Oh. Um, I should go.”

She looked at me knowingly, not deigning to answer my sheer bloody awkwardness.

I quickly got dressed and left.

Driving out of there like a bat out of hell.

I never saw Dark Angel again, and I never saw her profile advertised again.

I sometimes still think of her and my awkward first time with an escort from the internet.

Story by Jemal

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