Making of a Gigolo

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Young man finds aptitude test getting a physical.
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Rex Siter
Rex Siter
287 Followers

I'd learned my sexual prowess in the hands of Sadie, our married neighbor. Since I'd turned eighteen she had been my mentor. I was pushing twenty when she told me she was leaving the area because of her husband's health.

I was devastated. Sadie looked into my sad eyes, "I really believe you're good enough to make yourself a little career out of your abilities."

"A career?" I asked, as she reached to the bedside table and held out a small card.

'MANON' I read 'Discreet service for ladies with taste.' There was a telephone number.

"It's run by a friend of mine. Ask for Ron Vincent." Sadie whispered, her fingers stroking my belly, as she told me exactly where this establishment was.

"You'll learn much there, Jack---and I do believe you could set up for yourself. There's a host of lonely ladies around. Don't waste your talent." Then her fingers stroked over my semi-erect cock. "And don't waste it now."

. Within a week I found their house empty. My sex tutor had gone. And for a while I felt desperately deprived by her absence. I was about to start at the local university and the more I went into it, the more I realized that money was going to be very tight. It was then I found Sadie's card in my shirt pocket.

Was there really something in this for me? Getting paid for making women happy. Too good to be true? I had to find out. So I rang the number on the card.

A fruity female voice answered and I asked to speak to Ron Vincent.

"Mr. Vincent is extremely busy. You can make an appointment you like." I imagined some fat biddy all tight lips, too much make-up and thick spectacles. But I made an appointment for the following afternoon and hung up.

I was there promptly the next day. The office was up a lane just off one of the main streets in the city. A narrow staircase led to a landing with three doors. 'Manon' was the clear black and white sign on the first door on the left. I knocked and entered to find myself in a small office with a desk, a leather bench, and behind the desk a severe looking blonde, haired pulled back tight, face scowling her suspicion. "Can we help you?" It had been her voice on the phone. Well at least she wasn't fat and didn't wear spectacles.

I told her I had made an appointment to see Ron Vincent. She gave me a stare that made me feel as though I was something that had crawled out of a dead rat's belly. Then she picked up her phone mumbled something, listened, gave me another cold glance as she put the phone down. "Mr. Vincent will see you in a few minutes. Sit there." It was a command rather than an offer as she indicated the leather-covered bench. Watching her pounding on her keyboard I wondered if such a severe woman could ever have a lover. Little did I know.

From time to time she would glance up at me and her head would shake imperceptibly.

Ron Vincent turned out to be a little chubby man who instantly had me thinking of Danny De Vito. Bright and cheery he asked me a few general questions about myself, said he rarely found younger men really up for the job but added that anyone recommended by Sadie must have something to offer

"And I do have some clients who ask for------something younger." His small eyes glowed as he added, "There is a test which all new applicants must go through---a suitability trial if you like."

He stood and walked to a large mirror on the sidewall. I followed him. He dabbed at a couple of switches alongside the mirror and the next second I was staring into a small room containing a large bed, a stool and a small table on which stood a bottle of wine and two glasses.

"Our testing room. In a few minutes a lady will be seated on the edge of that bed. I want you to imagine she is a client demanding to be physically satisfied."

He looked at me. "You have any objections to being viewed in action?"

I was just a little taken aback by the suddenness of it, "You mean---now?"

"If you're up for it." His glance and lascivious smile made it quite clear what he meant.

After only momentary hesitation I agreed. "Good," Ron Vincent said, and he nodded towards a door alongside the see-through mirror. "A little room through there for you to strip down to your

underwear. Then through the other door and you'll find the lady waiting. Just stay cool, son."

I didn't like being called 'son', and I wasn't sure I was going to be able to go through with it. But as I stripped down in the small, neat changing room I began wondering what the woman waiting on the other side of the door would be like. Some old biddy, I guessed. Just to test me.

Down to my boxer shorts I tentatively opened the other door. and stepped into the bedroom, very aware of the large mirror to my left.

Sitting on the edge of the bed was a lady, blonde hair down to her shoulders, dressed in only a short silken slip. My first glance told me that the silk clung to a very delectable body, generous of breast and thigh.

My second glance shook me. I hadn't recognized her with her hair down but it was the same severe secretary that had greeted me. She leaned back on her hands, her face tight, her head shaking, nipples thrusting at the tightened silk of her slip. "Why do I always get you young kids? I suppose you're another one who thinks he can fuck like a man?" She sighed and lay back opening her legs so that the silk rustled, and I glimpsed smooth high inner thigh.

"Come on, then. I guess we'll have this over in about forty five seconds."

Her smugness almost got to me and I had an urge to jump her bones there and then. But the man had said, 'Be cool', so I was cool. I strolled to the table and poured red wine into each of the two glasses and carried them to the bed, holding one out to her. "No hurry is there."

Giving me a funny look, she sat up and took the wine, "Nervous, are we?" she smirked, but I caught her eyes appraising my body. " I guess you're better built than most. But that proves nothing."

We sipped our wine and I struggled for something to say that wasn't too crass. "You look better with your hair down," I ventured, deciding gallantry was what Ron Vincent would be looking for.

"Think you can get your pecker up?" she asked sarcastically.

I took another gulp at the wine then deliberately placed the glass on the floor and ran my fingers slowly up her arm. "Let's see," I said, allowing my fingers to trail around the smooth skin of her shoulder, before pushing the strap of her slip down. Her eyes glared at me contemptuously.

"Some kind of lover boy, are we?" But I thought I caught a catch in her breath as my fingers strayed down the exposed swell of her bosom. It occurred to me that she wouldn't be doing this if she didn't like it. All I had to do was to play this love song in her key, as Sadie had so often advised me.

With my other hand I reached across and took her glass, quickly placing it beside mine. Then I slipped her other strap and allowed both hands to trail down over each generous bosom, pushing away the silken material until her pink nipples were pointing at me. My thumbs stroked over each nipple and she turned her head towards me. I moved to put my lips on hers, but she turned her head away. "We don't kiss," she hissed, "Didn't Mr. Vincent tell you?"

He hadn't, but I didn't answer her. Instead I dropped my head down so that my lips played over her breasts, and I heard her breathing quicken. Tentatively my tongue licked around her nipples and I felt them begin to engorge, just as I felt the rising inside my shorts.

"Let's get more comfortable," I urged and gently gripping her shoulders I lay her back across the bed. Her look was still slightly contemptuous as I leaned towards those magnetic breasts I remembered another piece of Sadie's advice. "The right words can soften a lady's heart. Praise and admiration always help."

My lips trailed again across the delicate underside of her bosom. Nuzzling around her nipple I murmured with deliberate huskiness, "Such wonderful breasts."

Her voice remained hard, "How many have you had---momma's and one other?"

I might have taken that badly but kept my cool by saying, " And your skin is so tantalizingly smooth." I licked and sucked at her nipples while I allowed my hand to stray down her belly, pushing the material of her slip down and away, I fingered gently round her navel.

"We haven't got all day," she choked, but I caught the catch in her voice, and my hand spread in an increasing circular movement around her belly, without ever relaxing my mouth's attention to her nipples.

As my circling hand touched her pubic area, I was aware of her muscles tensing momentarily. My fingers strolled over and through her silky bush until they were just touching the start of her crevice. I deliberately played one finger at that single delicate spot, never venturing any further. "A little teasing never hurts." Sadie's voice sounded in my head. And I listened for, and heard, the change in breathing---it came quicker, more gasping.

Slowly I moved my lips down from her breasts, over that rounded belly towards where my finger played. As I did that, I murmured, "I'm going to make you cum and cum again."

"In your dreams, little boy," she gasped, and it was a gasp. I felt like asking her if she wanted to bet.

Nuzzling through her pubic hair I remembered again Sadie's advice, "When you go down on a woman remember to treat it as you would that first sip of your favorite wine. Show that you savor it."

Savor it? I always savored it. So my first gentle sip was to replace my finger with the tip of my tongue on that delicate little crevice. Her thighs were still tightly clamped together but, as the point of my tongue probed into that secret flesh, I felt her tremble and her legs opened, allowing my fingers to trail along those hidden lips.

Her hands had been clamped down by her sides but, as my tongue flicked at that secret flap that hid her clit, I felt her fingers pressing at the back of my head, and she gave out a low moan of pleasure. Maybe the hard work was over. My tongue sought out that little hard button showing itself through the folds. I tongued it and savored it, as Sadie would have wished and was delighted to hear my companion's cry of, "Oh, My God."

While my lips massaged her little button my fingers felt the wetness seeping from those lower lips and I slid one finger deeper into that delicious smooth moisture. As I did that I became aware of her other hand reaching out to touch my belly and slide under my shorts. Her fingers circled my navel, setting up a delicious tingle on my skin, and it was at that point that she had the surprise of touching the tip of my burgeoning cock.

"What?" she moaned, surprised to find it extended that far up my belly. Immediately, her fingers scuttled along and around its length. "God, lad, you're well hung."

"All the better to fuck you with," I said, before nuzzling back at her engorged clit, and spreading my fingers so that two probed her inner depths, while a single finger drifted to caress around her tight asshole. She gave a sharp intake of breath as that finger began to insert itself into her tight rear aperture.

Her hand pumped fiercely on my erect cock, expecting me to cum as she had said I would. No chance. Lapping at her delicate bud I set my fingers sawing in and out of the twin openings relishing the tremors that were starting in her limbs. Her voice was making strange bleating noises and then her whole body heaved, a mewing, hacking sound escaped her lips as she went into orgasm, her whole pubic area lunging up into my face.

Her fingers pushed down on my cock, "Put it in me. Put it in me. Fuck me, you bastard."

I sat back and let her roll around in her frenzy, her eyes wild upon me, and her hand yanking at my cock.

As she subsided I whispered, "Stage one---now stage two." And I leaned down and begin licking at her clit once more. It was bigger and soaked with the wet of her cumming.

"Oh, God," she gasped. "What you are doing to me?"

"Pleasuring, ma'am." I murmured, through my busy lips, which I now ran along her soaked labia.

"I can't---can't take ---"

But I could tell by her breathing that my licks were having their effect. And as she lay there panting I swung my body round so that I could roll between her trembling thighs. She spread them willingly and I placed my cock head at her gaping entrance.

"Do it," she begged. "Do it."

I slid into that smooth soaked opening up to about three inches, before slowly withdrawing a couple of inches. Her hips heaved up and I gave her a further two inches before withdrawing to her labia. Her hips bucked frantically and at this point I drove my shaft full length, deep along her clinging vaginal walls. She moaned out loud. I gave her a few more full-length thrusts, saw her eyes roll up under her lids. Adjusting my position slightly I ensured that my heaving erection slid along her clit and G spot. My right hand fondled her left breast as I felt her hips lift and her head began to rock from side to side as another orgasm hit her. Yelping and bucking she came with amazing force, her whole pubic region grinding against me.

As she calmed down her eyes opened and she looked up at me with an entirely different expression, "Oh, my God, where did you learn to---"

"Not finished yet," I told her and began pumping into her with my own balls beginning to demand release.

"You haven't cum yet?" she breathed in amazement, and her eyes closed as my thrusts began to have their effect on her again. This time I quickened the action, feeling the walls of her vagina sucking at my rampant cock. Faster, harder and deeper I plunged and she began responding again. Her mewing noises got louder and louder until she was all but screaming out her orgasm as I felt my own ejaculation approaching.

We hit it together, pounding and roaring as wave after wave of semen pumped up into her depths.

When she'd calmed she murmured, " You were a surprise."

"Not to me, I wasn't."

"Can we do it again sometime?" she whispered.

"In your dreams, lady." I said, withdrawing from her, seeing her eyes gazing at my fast reducing, dripping dick.

"Hell, that's some weapon you've got there," she sighed.

When I dressed and saw Ron Vincent he shook my hand and offered me a job. "Hell, son, that was some performance. I think you'll make our ladies very happy."

I was on my way to being a gigolo. Gigolo Jack. Watch out for my future experiences.

Rex Siter
Rex Siter
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AnonymousAnonymousover 4 years ago
PREQUELS & SEQUELS

The prequel for this story is

Lessons from Sadie.

See my comment at the end of Lessons from Sadie Ch. 05, for a listing of all the sequels.

Paul in Oklahoma

roveroneroveroneabout 6 years ago
Really enjoyed it...!

started sequel first, then backtracked to read this first

follows my dictum-ALWAYS get them off first, at least once

snathsnathalmost 11 years ago
Welcome the dictums

Dictums stated in this sweet piece of story should be very useful for the men at work.

AnonymousAnonymousabout 19 years ago
Marvellous!

A nice beginning of a hopefully long novel!

Let him serve all those lonely hungry older ladies in town!

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