I had recently lost my virginity to an escort I had found online. She was a pretty enough black girl who went by the alias of Dark Angel.

The thing I would soon realise was that having sex is like having Pringles: once you pop, you just can’t stop. The urge to have sex again was strong and difficult to ignore. Of course, I still had the same problems as before: going out in the world and finding someone to have sex with was a process wrought with obstacles I refused to face.

There was a simple solution: visit another escort.

I didn’t want to go back to Dark Angel. I realised that she was only doing her job, but with the clarity of post-orgasmic regret I realised that it had been cold and mechanical. I would have to try someone else. It didn’t occur to me at this stage that an escort is an escort, and any encounter would essentially be a transaction, and therefore could be expected to be cold and mechanical, business like. I was an idiotic optimist.

The horniness grew stronger and stronger, and eventually, almost an entire month after I had popped my cherry with a girl for hire, I decided to dip my toe back into one of the oldest businesses on Earth. I visited a different site this time. I searched and searched, and I forget what drew me to this specific profile. I do remember that I was soon to learn a lesson that I haven’t forgotten since.

I just realised how foreboding that sounds. Don’t worry, this wasn’t bad. Well, a bit embarrassing to tell, but not bad.

The name on the profile was Misty. She looked smoking hot in the pictures, despite having a “mature” tag. I just had to call. I was young and dumb and full of cum.

I rehearsed what I was going to say in my mind, and with a racing heart I dialed the number.

“Hello?”

“Hi, is that Misty?”

“Yes sweetie, how are you?” came the slightly deeper reply than I had expected. Mature had turned out to be an appropriate tag. Maybe she should have also included the fact that she had probably been smoking fifty cigarettes a day since she was six. Despite this, I pushed ahead bravely, motivated by my raging hormones and aching balls.

“Oh, hi. I, uh, I’d like to find out what your rates and services are please,” I stammered, slightly thrown.

She told me her rates and where to find her. She was a bit further away than I had originally planned, but I was a walking boner at this stage and wanted to find a warm and wet home for my aching cock.

I quickly got ready and hit the road. While on the way I worked on what I would say and what I would do. I had decided that while Dark Angel was fine enough, I felt somewhat embarrassed that she had been my first. Maybe this mature lady would take pity on me if I claimed to still be a virgin, maybe she would show me the ropes and make me a real man.

So, when I finally reached her door, I knew what I would say. However, I was slightly thrown once again when I got there. The lady who greeted me was clearly older than I had expected and showed a lot of mileage on her face. Look, she wasn’t truly ugly, but the shock of the discrepancy between expectation and reality was enough to derail my severe horniness for a moment.

Well, I was here. I had driven relatively far to get there, and I didn’t really want to go to the effort of walking out and finding someone else. I was going to get laid, and this was right in front of me. What’s the worst that could happen?

She showed me in and took me to the bedroom, where the bed was made, and a bag of goodies was on the side table. I could see wet wipes, condoms, lube, and some other things that aid in adult playtime. She started making conversation: what’s my name? what do I do? and so on. I think she sensed my nervousness, because I was somewhat intimidated by her.

Fighting my nerves, I decided to capitalise on the situation.

“Well, I have something to tell you and it’s a bit embarrassing,” I said while seated on the edge of the bed. She looked at me, and I realised I sounded like a person about to confess to syphilis or something.

“Er… I… this is my first time. I’ve never been with a woman; I’m a virgin.”

She looked at me in disbelief.

“And how old are you?”

“I’m twenty-two.”

I saw in her eyes she didn’t really believe me, so I decided to lay it on thicker.

“You see, I’ve been quite religious, and dating hasn’t really been that easy,” I started explaining.

“Okay baby, I understand. I’ll take care of you, okay?” She said, taking the bottom of my shirt and starting to lift it over my head.

“Let’s start with a massage to calm you down, okay?”

So, she helped me undress, and I was naked in front of my second escort in a month. She told me to lie down on my stomach on the bed as she got undressed. I kept an eye on her, and her body was thankfully as hot as the pictures on her profile had suggested. Considering her age, it was remarkable how smoking she was, although both time and past horniness might be helping me embellish the memory a bit. I must insist, however, that you believe one thing: she absolutely had a butter face. It was distracting, but so was her body and I decided to focus on that instead.

She started massaging me with baby oil, and the touch helped to calm some of my residual nerves. It also helped my dick grow harder under my belly as she started to rub her tits on my back. First, she lightly brushed my shoulder blades with her nipples, leaving me puzzled for a moment as I tried to figure out what was happening. She then rubbed her body up and down my back, dragging her tits all over my back and ass. It had the desired effect and I was soon lying on a red-hot steel rod that had recently been my cock.

And then a new sensation that took a moment for me to figure out: she was rubbing her pussy up and down my back and buttocks. It was very warm and had a hint of being damp. These sensations made me almost lose a load right then and there, but somehow, I held on.

She soon flipped me over and my cock sprang to attention. She was kneeling between my legs, and she was staring up at me past my cock. Butterface or not, this was more than my recently de-virginised brain could handle. She started lightly fondling my balls with one hand and took my shaft in the other.

“You want me to suck it, baby?” she asked coyly while focusing on my purple little head.

“—,” I barely croaked out a sound.

She took that as a yes and started licking my cock up and down. Interesting, she didn’t reach for a condom like the last one. Maybe it wasn’t a compulsory blowjob tool after all.

“Just tell me if you’re about to cum,” she said, pausing as she continued to lather my fuck stick with her saliva.

“Uh, um, okay,” came my eloquent response from a brain overloaded with sensations and disbelief.

She licked up my shaft again and finally took my head into her mouth. The sensation was almost indescribable. The heat and the wetness were overwhelming. It occurred to me in the heat of the moment that such simple sensations, when felt elsewhere on the body and at other times could never have the same effect that they were having on me now. Odd.

I could feel my balls bubbling as she took more of my dick into her mouth. I was quickly approaching the edge and I wanted this to last a bit longer, but I also remembered what she had said.

“I’m — I’m close,” I was able to sputter out with effort.

She immediately took me out of her mouth and helped me ride the edge of orgasm. Clearly, she knew what she was doing. She swiftly reached over and took out a condom. She unwrapped it and rolled it over my cock so fast I didn’t realise what had happened. 

She kneeled over me and aimed my dick at her pussy. After a moment of calibration, she sank down and my dickhead was in her cunt. As she lowered herself further, I realised that I would soon give her indisputable evidence that I was a virgin as I had claimed. It was a moment of bliss, and she was able to lift herself up and lower down once, and then I was ejaculating my very soul into the condom. I came so hard I was worried I had ruptured the rubber, and for a moment I panicked slightly, then I remembered she was probably way past being a pregnancy risk.

Of course, she knew immediately what had happened, as I stiffened and lay there spasming with what I can only imagine was a hideous and unsightly “O face” expression.

She slowly got off my still-hard cock and knelt beside me, reaching for a wet wipe. She took the condom off and started to wipe me down. The only problem with this was that I was extremely sensitive, having just cum hard enough to forget my own name.

The warm glow of post-coital and post-orgasmic bliss was quickly interrupted by the harsh sensations of a cold wet wipe being dragged across my frenulum. This had the effect of softening me up in no time and getting me to squirm like a naughty child.

“Oh, sorry,” she said, as if she had forgotten how sensitive men can be after cumming.

It was fine though. She was touching my dick, and in my mind that was still a novelty to be treasured.

She soon let up with the cleaning routine and cuddled up to me in my once again semi-comatose post-orgasmic state. What is it with us men and almost losing consciousness after cumming? My brain was fluff and I had to fight the urge to fall asleep right there. Thankfully the scent of stale menthol cigarettes kept me awake. Talk about mature.

Despite the cigarette smell and the alleged exhaustion, I had a naked woman in my arms and my body was all too aware as was my brain. I felt a stirring, and soon I was standing at full attention again. It was as if I hadn’t had an orgasm and my cock was begging to be relieved.

With Misty cuddling up to me and drawing circles on my belly, this development did not escape her attention. Her fingers teasingly traced a path down my belly, along the garden path, and started caressing my pubes. I had read a lot of erotica at this stage, and I was no stranger to the concept of the tease. It was here that I caught a glimpse of the real value and feeling of the tease in action.

She didn’t immediately grasp my dick, she first skirted the issue, the raging and almost purple issue at this stage. She tickled my thighs, lightly brushed my balls with her nails, and even curled my pubes around her fingertips.

This had the desired effect, and I would probably have followed her every command, dick first at that moment. I was energised and horny, and I knew what I wanted. Yes, I wanted to fuck, but there was something I had been incredibly curious about first.

I broadened my attention again, after having it zeroed in on my crotch area since she had focused there too. I lightly touched her shapely hip and started brushing lightly up and down her smooth skin. It truly was remarkable the state her body and skin were in. She was rather pale with red hair, and light pink nipples on what were probably modest B-cups. While lying on her side, she had been teasing me, but now grasped my cock and slowly started to jack it up and down.

While I had been brushing her smooth skin, I had started tracing circles up and down her hip. I didn’t know exactly how to proceed, so I decided on just asking.

“Um… do you think you could show me something?” I said, not sure exactly how to word it. Could I be crass? Did I need to use the technical term? I wasn’t sure if I should ask: May I eat your pussy? Or May I please perform cunnilingus upon you, my dear?

I decided on my wording and said, “Do you accept oral?”

She looked at me for a moment. I’m not sure if she was weighing me up or just toying with me, based on the dick play, probably the latter.

“Yes, I do. Do you want me to show you how?”

“Yes, please,” I responded, trying my best not to jump out of my skin with excitement.

Of course, I was no stranger to porn and erotica. I had a fair idea of the female anatomy, and I thought I knew enough to at least be a competent beginner. I also knew I could tie a cherry-stick into a knot with my tongue. So, I was riding the thrill of excitement and nervousness, while quietly confident in myself for the first time in this wider sexual adventure.

She told me to go to the foot of the bed, while she took the centre of the bed with her head on the pillows. She lay flat and opened her legs enough that I could crawl up between them. I got in real close and had my first close-up of a pussy that wasn’t just light on a screen. One of the first things I noticed was that she was indeed a natural red head, although maybe not necessarily the shade she currently had on her head.

Because of the time gap between this event and my current retelling of it, I must admit that some details have escaped my memory from this seminal moment in my manhood. I do remember a few impressions though.

The first was the scent of a cunt. Hers was clean and I had never smelt the like before. It’s difficult to put into words without sounding disgusting, but those who know might understand what I mean, and those who don’t just have to take my word for it that it’s not as gross as it sounds.

As I approached the scarlet landing strip, I breathed in. The aroma was like a bouquet of raw meat, musk, iron, pure desire, and something else that I will only ever associate with the intrinsic smell of a pussy. I wanted nothing but to put my mouth all over it and devour it until someone came.

Thankfully she didn’t condescend to giving me an anatomy lesson. I knew what was where, and I had a plan based on my extensive “research”.

I decided to emulate my current mentor and opt for the tease tactic. At first, I stared at the prize, silently promising the cunt staring back at me that I would get there eventually.  Then I kissed her thigh, lightly, sensuously. If I focused on her luxurious skin and amazing body and avoided her face, it was a lot easier to get into everything.

I slowly trailed kisses up her thigh right to the junction where her leg met her crotch and kissed into that hollow too. She was clean, but there was a faint aroma of feminine sweat. This struck me in my libido, and I knew what animal magnetism was at last.

I mirrored the trail of kisses on her other thigh. I soon became bolder as I realised she was waiting for my next move. It was working! I kissed back and forth from thigh to thing, hollow to hollow. I knew I was getting unbearable, and just as she was about to say something I stopped.

I centred my face with her pussy and looked at it intently, daring it to give up its secrets to me. I then was struck by inspiration, and lightly blew on it, as if I had a spoonful of hot soup. She squirmed slightly and told me to stop teasing her. Fine, have it your way, I thought.

I slowly approached the mound of desire and stuck my tongue out. I ran it from the bottom of her slit to the top, tip first, tentatively tasting and exploring the texture. A century will pass, and I will never forget the texture of a pussy on my tongue. They’re all unique in their own way, but they all also share something fundamental that I just don’t possess the eloquence to describe.

The taste was surprisingly subtle and reflected the smell I had experienced earlier. The warmth just past the outer lips (labia majora, who said porn wasn’t educational?) was surprisingly intense and alluring.

After this, I remember less and less. I know I started testing the dexterity of my tongue, I focused on her clit, and I elicited at least a fake orgasm out of her. My biggest concern was, “Was it okay though?”

To which her response was, “Yes! Wow, are you sure you’re a virgin?”

I knew there was some bullshit in that statement, but she planted a seed of confidence I will always fall back on in times of desperate need and low sexual self-esteem.

Somewhat pleased with myself and with some swollen lips from sucking and a tired tongue from licking, I sat up with a raging boner. She soon had a condom rolled all the way to my balls, and her knees almost at her ears.

“Come on, I want you inside me,” she said as I tried to focus on her pussy and tits rather than the face that insisted on confronting me.

I’d like to say that I lasted long, but we all know the mantra by now. But, since we know what kind of story this is, let’s play it out.

I knelt between her knees and grasped my cock in my hand. I rubbed it up and down her slit and realised what had been missing with Dark Angel: natural arousal. At least I had gotten that right.

Misty scolded me for wasting time, and grasped my cock, basically pulling me into her. What I thought was horniness, turned out to be prudent time management. My hour was almost up, and she needed to get me out the door.

I entered her again, once again revelling in the heat of a real cunt. I pumped for as long as I could, looking at her face occasionally to try and keep my nut in its shell, but to no avail. I soon came into the condom, slightly reduced in volume this time.

Sweaty, I quickly got dressed and was ushered out of the door with hardly a moment to say thanks.

It was only on the way home that I was able to revel in the afterglow, realising I’d need to brush my teeth and wondering if I had any mints to take away the after taste of what had just happened.

Sure, I had told her she was my first, but truly, Misty was my second.

Stay tuned for the next chapter in my sexual development. All I’ll say for now is expect some premature humiliation.