It had been over a month since I had seen Misty, my second escort and sexual experience. The whole affair had been revelatory, yet it had left me feeling guilty and I decided to abstain from any more working girl visits.

But, as I’ve alluded to before: once you pop, you just can’t stop.

Life briefly got in the way. I ended up going on a trip for over a week. With the busy schedule and the number of people I was with, I didn’t even have the chance to have my customary daily wank (to keep the edge off, of course). I was beyond horny.

When I got home from the trip it took me a day to settle, but I knew I would cave sooner rather than later. The sexual mania was building behind my eyes. I was soon to learn another valuable lesson (cue the foreshadowing “DUN DUN DUN” music).

The very next day, after work, I finally capitulated to what I was realising was some form of addiction. In a mist of arousal, I surfed the site I frequented for escorts. I had decided not to touch myself, so that I could have a larger amount of cum, a bigger orgasm to remember. In hindsight the expression “young, dumb, and full of cum” is a lot more appropriate.

I finally settled on a caramel hottie, at least her body seemed like it was from the faceless photos. She was close-ish and would be a nice warm place for me to rest my cock for an hour or so.

I made my customary call, noting that the voice on the other end sounded more bored and indifferent than usual. “Sweetie, honey, baby,” were becoming tarnished in my mind. It seemed that there was some kind of escort jargon book somewhere that they were all abiding by. No bother, I was about to get my rocks off, so who really cared?

After a quick shower, I rocked up at her place. It was a house she shared with other girls. Nicky, the alias of the caramel hottie, greeted me at the door in a skimpy satin dressing gown with what appeared to be very little underneath. She led me to her room, thankfully without sighting any of her colleagues or their respective clients.

When we finally got into the room, brighter than what I had come to expect, I had the opportunity to scrutinise her a bit further. Of course, I was still nervous, but I guess horniness and exhaustion from the long trip lent me some false confidence. So, I brazenly took in what she had to offer as she got her goodie bag ready (also something that seemed to be an industry standard) and slipped her robe off.

She was wearing a pair of frilly light-blue underwear with a matching bra. Her tits seemed to be a generous C-cup, hanging over a flat tummy and opposite a lovely bum. I would soon realise I was a bum man, and what I saw spoke to my lizard brain, bypassing my barely present consciousness. My cock twitched.

I finally looked up at her face, and it was okay. Thankfully, no butterface. She wasn’t as young as I was, or if she was, she had clearly seen more in her life than most, but she wasn’t ugly. I’ll be honest though, she might have been beautiful, but I was more interested in the area between her legs and the potential heat of her mouth than I was in admiring the face of what was essentially a stranger.

Nicky took my cash and instructed me to disrobe. I had decided that this time I was just going to go with the flow. No trying to convince anyone I was still a virgin. I needed to own my sexuality. Be a man, y’know? I got undressed and lay face-down on the bed, anticipating a massage.

What followed wasn’t much of a massage. She used some baby oil, she rubbed me a bit, but I had a raging hardon practically before I even touched the bed. Her perfunctory rub-down was just getting in the way at this stage.

Maybe she sensed my impatience, because she told me to turn over, and my dick nearly slapped her in the face. Or, at least, I like to imagine it almost did.

She quickly reached over and rolled a condom over my aching fuck-stick.  I felt disappointment twinge in my belly, I had hoped to go in bare for the blow again. Alas, I’d have to go out with a raincoat today (practice safe sex, kids).  I was tingling already, an ominous sign my over-loaded brain missed.

Without much preamble, she took my cock into her mouth and started working her way up and down the shaft. Her mouth was warm and wet, even if her technique was mediocre. During the misnomer of a massage she had taken her bra off. Her bare tits, the fact that my cock was in her hot mouth, and a week without touching myself conspired to surprise the hell out of me.

Out of the blue I was filling the condom and spasming like a seizure victim. I came like a fire hydrant for what must have been several long seconds, as shock clenched my belly and I tried to hold back mid-stream.

Soon I was spent, and she had realised what had happened. I could feel myself going red, no, magenta. She popped my softening cock out of her mouth, and I could see the end was bulging with my premature ejaculate.

“What happened? Did you cum already?” She said with incredulity, adding fuel to the fire of my humiliation.

“I. Uh. I. Um… It’s been a while, okay?” I tried to recover from the suddenly burning humiliation and shame.

It looked like she was holding back a good chuckle, which just made me feel more like shit.

With a wry smile she said, “You want to try again maybe? You know you can cum twice in an hour if you want…. If you can.”

Shit. Low blow.

“Of course I can! Just give me a moment,” I said, panicking.

I felt the slow creep of panic and despair taking a hold of my mind and locking down my libido. The only thing driving me forward at this point was sheer misguided determination not to compound the humiliation.

I was already soft, but she quickly grasped my cock and started to tug at it somewhat forcefully. It seemed she had decided that there was no time like the present. I’m sure she thought that if she could get me to cum a second time before the first half of the hour was even up, that she could capitalise on it.

At first the stimulation worked. I felt my erection returning, and I thought everything would be okay, but in the back of my mind I knew something was wrong. My confidence had been knocked a heavy blow, and this was moving too fast and rough for my liking.

My cock stiffened slowly, but that stiffness that feels like it’s lacking at the core. (Guys, I’m sure you know the type of boner I’m talking about. One that’s softer than your grandad’s porridge, held together with hope and a rubber band.)

Eventually she got me to a hardness that was just short of where you want to be. I reckon she thought her pussy could do the rest, or I would cum before that became a problem.

With the practiced dexterity of a pro and a pro in a hurry, she slipped a fresh condom on my floppy disk. She bent over the bed and said, “Fuck me.”

That phrase and stance alone would normally have sent my novice brain into overdrive and my cock through a reinforced wall. However, that was not to be this time. My embarrassed boner gave a twitch that resembled a shrug and stayed three-quarters hard.

I took up my position behind her and aimed my cock at where I thought her entrance was. With a softish cock, it was a bit more difficult than it would have been otherwise. She eventually had to reach back and force my rubbery worm into her quim by sort of folding it in.

The heat and the warmth of pussy paradise were there, but something had broken in my mind and my libido. My cock gave a slight surge, so I tried to capitalise and pumped a bit. With the new sensations I started to get harder and harder. Even then, it was a dissatisfying stiffness. It felt brittle and on the edge.

I felt like would never cum again in my life. I pumped until her ass jiggled. I pushed, I pulled, I pistoned, I fucked. I started to feel my erection die.

Shit. It wasn’t going to happen.

Eventually, I was so soft, the condom was falling off and I couldn’t stay in her pussy.

It was time; I would have to call time of death on this encounter. She knew it too. She turned around and sat down on the bed and started getting dressed.

With my face burning, I said, “I should probably go.”

What followed was what felt like the longest time it has ever taken me to get dressed. Eventually I laced up my shoes and stood up to see her waiting by the bedroom door, almost tapping her foot. She showed me to the front door, and I don’t even remember saying goodbye out of sheer embarrassment.

When I got into my car, I saw that I had stayed almost the full hour. Most of which had been attempting to fill my cock with blood. I had learnt a valuable lesson: don’t over do it after a period of abstinence. Also: don’t get in your own head.

This was sure to be my most humiliating sexual experience. For a while.

Join me next time, when my adventures expand to something more… exotic.