Trust fund twink pt.2

I knew that the best way to do this would be to take control. Some people say that a new bottom trying anal for the first time should be on top so that they can control the pace. Well if that works for some people then fine, but I think more people give up too easily that way. I say they are better of giving up control to a top who knows how to treat someone on their first time.

What the first-time bottom needs to know is that they are going to experience some new sensations and that the most important thing is to relax. They may be confusing sensations, and there may be a little pain, but if they just relax through it, the pleasure will overtake the pain and will become incredible.

These things I explain to my trust fund twink, as I absently run my hand up and down his body. My words are true, but they only work if they are conveyed with confidence. Confidence that engenders trust. Trust that allows relaxation when the strange new sensations occur. I have a gift for creating that trust it seems. My cock is longer and much thicker than average and experienced bottoms have struggled to take it. The first timers that I prepare with my words while they lie there, wide eyed, in my strong arms, they always take it all – and they enjoy it! And so it was with my blond haired boy, as he lay on his back, legs resting on my shoulders.

I looked into his blue eyes as I teased his hole with my hard cock. Gradually I applied a little pressure and the head pushed inside ever so slightly.

“Just relax, remember I can stop if you need me to. I’ll start gently.” I felt his hole loosen and I pushed the head of my cock a little further in, as I rocked my pelvis slowly back and forth.

I took his own stiff dick in my hand and caressed the tip with his slick precum. The distraction of that relaxed him further and suddenly I was in.

His eyes widened as he sharply drew breath. I paused just for a moment, before repeating my encouragement to relax and resuming my gentle back and forth movements, deeper now. His face flickered between surprise, and uncertainty for a few moments, as I continued to probe deeper into his warm passage. I withdrew a little and picked up the pace. Faster thrusts, pushing upwards towards his prostate. The surprise was back, this time accompanied by a growing childish grin that told me all I needed to know.

Before long he was taking my full length in deep thrusts that made him groan with pleasure. I relished the animalistic abandon that I could now allow myself as I ploughed him deeper and harder. All the time he took it with that big stupid grin on his face, broken only by the O his mouth formed when his moaning was too much to be done through a grin!

I rolled him onto his side, allowing myself a little more penetration. As I thrusted in this new position, my cock roughly pushing past his prostate again and again, he found himself surprised once more. Gasping and writhing, ribbons of cum shot out from his dick, without the help of his hand. Damn it was hot! I pulled slowly out and soon I was shooting my load across his body.

“Do you want a towel?” I asked.

“Can we not clean up yet?”

Fine with me. He lay there in my arms, covered in my cum. An expression of blissful satisfaction on his face. He closed his eyes, half sleeping, and I nearly dozed off myself.

We talked a while before he took a shower. That was at the end of the last university term. He went home for the summer. The new term has just started. I wonder if he will be booking me again.... I wouldn’t mind....

Trust fund twink pt.1

So I get a text one morning:

“Hi. I’ve never done anything with a guy before and I want to try. I have a girlfriend so I need to be discreet. J”

These sort of texts always put me in two minds. I love inexperienced guys. They’re so full of excitement and nervous energy. The slightest touch of my hand causes a gasp or a shiver. The confusion of surprise and joy writ large on a face as I introduce a guy to a new pleasure for the first time. The power that comes from controlling and directing all that raw sexuality and lust.... mm mm mmmm.

The downside? These are the guys that are most likely to chicken out at the last minute. To cancel a booking hours or minutes before, or simply not turn up, leaving me sexually and financially frustrated.

So, keeping check on my excitement, I text back. More details emerge. He is 21, a student. Another double edged sword. I like a young client, but students never have any money.

“Have you seen my rates?” I ask?

“Yes, no problem.”

A student with money to spend. He’s either desperate or rich. I find myself wondering if I’m hoping for rich so that I don’t feel guilty about exploiting someone’s desperation... or if really it’s just hope for a repeat customer... is this job turning me mercenary?

We arrange a date.

He cancels.

Figures.

 He arranges another date.

People get a second chance. Things do genuinely come up that can’t be helped. I hope he doesn’t make me consider a third. I’m sure there are guys out there who get off on making a booking and then standing you up. A power game? Too much time on their hands? Kids messing about? I don’t know.

Well, the day comes around and he’s on his way this time. He sends a text to say he’s parked. I look out the window as I text back the house number. A slim young lad dressed in cotton tracksuit bottoms, well fitting (but not tight) t-shirt and a beanie hat steps out of a shiny Audi TT. Rich then, that’s nice. Apart from the car, he couldn’t look more like a typical student if he tried. That’s very nice.

He gets to the door and I let him in. His name is written in big letters across the front of his t-shirt.  Did he have that printed or is it a brand? I’ve always been oblivious to fashion brands. Is that his real name, I wonder, or did he pick his client name from his t-shirt? Escorts rarely work under their real names. I don’t know how many clients give false names, it hardly matters to me, but maybe that was his. Either way, it makes me chuckle inside... best to keep the chuckling inside. I see a lot of things that amuse me but it isn’t good for business if you laugh out loud at someone’s kinky secret or exotic-fruit-shaped penis, so I got rather good at keeping a straight face.

I offer the student a seat and a drink. He takes a beer and sits nervously.

He’s rather good looking, in the slightly horsey inbred I’ve-got-a-double-barrelled-name-and-I’m-468^th-in-line-to-the-throan kinda way. His nervous smile shows off perfectly straight, perfectly white teeth. Bright blue eyes and pale skin put my money on blond locks under that oversized beanie.

“Shall we get the business side of things over with?” I ask, “So we can get on with the pleasure?”

A pretty corny line I suppose, but I use it all the time. The most delicate way I’ve come up with to remind the client that I take payment upfront if we’ve not met before. If you’ve got a better way then let me know!

“Of course” he flusters slightly, as if he’s committed a social faux pas. There’s no reassuring the nervous ones, until they get what they came to me for. Better not to drag out the preliminaries too long.

He’s standing now, having retrieved the money from his wallet. I step closer to him and caress his neck gently with my hand, guiding his lips to mine for a tentative first kiss. There is no resistance. I kiss harder, pulling his body in to mine. His arms wrap around my waist and we kiss with passion. I move down to his neck with my lips. As my hands are feeling his lean body through his t-shirt, I make a trail of kisses down the side of his neck that makes him groan.

Clothes start to come off as his nerves are forgotten in the heat of passion. His body is lean, verging on skinny. A fair treasure trail of hair (matching his blond locks – I was right!) runs down from his navel and disappears beneath the waistband of his boxer shorts. I push him onto the bed. My kisses cover his body. Lingering on his nipples I elicit a gasp of surprise. “Your girlfriend never done that to you?” I wonder silently. Best not to mention girlfriends in these situations!

My fingers trace the edge of his boxers, skipping just under the material in a teasing manner that makes him squirm. I kneel over him as I do it. By now he is staring at the outline of my hard cock, straining against my underwear.

“Why don’t you have a go at exploring my body?” I suggest. He nods eagerly and I lie back on the bed.

“Just let yourself be guided by instinct, explore what it’s like to touch my body, see where your hands take you.” I’m in no hurry. He’s paid for two hours.

It doesn’t take long til his hands are dipping into my underwear.

“Can I suck it?” he asks tentatively. I don’t get these clients that think I’m going to say no to a blowjob!

“Of course” I say, removing my underwear.

I can tell from is technique (or lack thereof) that he’s never done it before but he manages to avoid the cardinal sin of teeth and actually starts improving after a while. More kissing follows, by which time he’s lost his boxers revealing a nice firm 5-6” dick and a cute round arse.

“So how far do you want to go?” I asked. His face flushed. Having seen his lovely arse, and knowing that it is virgin territory, I really want to be the one to pop his cherry. But this is work and I’m certainly not going to pressure him to do what he doesn’t want to do. The client comes first. A happy client might mean a regular client and that means stable income. I see that he’s struggling for the words he wants. When they come I can’t help but smile.

“Do you have condoms?” Is the pope catholic? As surely as the pontiff would deplore them I just as surely always have condoms with me. Let’s forget for a minute that if the pope were aware of this little scene the condoms might not be at the top of his list of objections....

“Always. You want me to fuck you then?” There’s no risk he might have been thinking of fucking me... he’s seen my ad and it’s perfectly clear. “Don’t worry, I know how to be gentle.... at least to start with.” I’m sure my grin when I say stuff like that is positively wicked, but it never seems to put anyone off.

“If that’s ok?” He says. I suppress a smirk.

“Yeah, that’s absolutely fine” I say in self conscious understatement. Sometimes I love this job.

To be continued...

An introduction

I’ve been working as an escort for over a year now. Only my closest friends know. This blog is an outlet to tell some of the stories of things I have been involved with along the way. And, boy, are there stories! I already have my first six titles in mind. Some things will be changed slightly, or left out, to preserve my anonymity and that of my clients, but everything written here will be as accurate an account of a true happening as I can make it. I don’t intend even to reveal where I live. Should you wish to contact me you can do so through this blog. If you wish to hire me for my services then that can be arranged. If you just want to get off on reading my adventures, that’s fine too.

I am dominant by nature, strictly a top, and that is how I advertise myself. I am late 20’s, tall, hairy and dark haired. I’m built like a rugby player and I keep fit. Oh, and not forgetting the asset people ask most about: my cock is 8”, very thick and has variously been described as “gorgeous”, “very suckable”, “awesome”, “the biggest thing I’ve ever taken”, etc, etc.  Naturally I attract the submissive type and this suits me. I also attract all sorts of fetishists. A year ago most of that fetish stuff was new to me. Now it is second nature.

Be warned that some of these blog entries may get pretty graphic and explore the darker side of sexuality. The clues should be in the titles if you want to read selectively.

Warnings over, my first proper entry will follow soon. It’s pretty vanilla to get us started. If you’re looking for the dark stuff, don’t worry, it’ll be there soon enough!