Jack the Gigolo’s Last Stand Ch. 01


Two years into my time as gigolo with Ron Vincent’s business of providing escorts for the mature lady I had acquired quite a reputation. A good number of the clients asked for me on a regular basis.

Having said that I’d had a few occasions which had ensured I kept my feet on the ground.

Like the buxom fifty two year old madam, all blue rinse and chins who only wanted to have cunnilingus but refused to touch me in any way.

It made for a very lengthy two hours of dipping my face in wet lard.

Then there was the ancient lady with wrinkles down to her ankles, who just lay there, legs apart, looking like some putrified starfish, and ordered me to hump her without any preamble.

I near exhausted myself on her. She became the only woman I never managed to bring to orgasm.

Still there were many pleasant surprises and getting paid for it had bumped me through business college with a very good qualification.

So, with what I had learned I was all set to break away from Ron and set up my own little private enterprise. How could I know that events were about to remove me from the business altogether?

And no, I didn’t get injured in any way—not physically anyway.

One day Ron Vincent asked me to call in because he had a special one for me.

When I arrived at his office I eagerly asked for details of this special. Ron just shrugged, “Beats the hell out of me. It’s one of your regulars, Dawn Soreen.”

“Dawn?” I said, very very puzzled.

Dawn, a forty two year old, had been my very first assignment. A beautiful, very mature lady, who feared she might be frigid. I had proved she definitely was not frigid. In fact she was one of the best lays I’ve ever had.

Over my two years we had met maybe five or six times, and I was pretty well attuned to her needs and desires. So I had to ask, “What’s special about this?”

Ron blew out his fat cheeks, “Her words, Jack. She asked for you and said it was for a special. More than that I do not know.”

“Okay, she’s pretty special anyway.”

Ron laughed, “Maybe I shouldn’t pay you for this one, eh?”

I nudged his pot belly, ” It’s my charm that keeps you in business.”

Of course, I hadn’t told Ron of my intended defection, and the possibility that I might take some of his clients with me.

“Where and when is this to take place?” I asked.

Ron glanced at the sheet in front of him “The usual. Her apartment. 8.00pm”

“No dining first?” That was different. All our previous meetings had started in some swish restaurant before returning to her luxury apartment.

And the time seemed rather early. So maybe it was special—a birthday, maybe?

Ron treated me to his impish grin as I left, “You must let me know the details of how special this is.”

I chucked him under the chin as I shook my head, “Client confidentiality, Ron. You made the rules.”

And I was gone.

At eight o’clock on the dot I was tapping gently on the door of Dawn’s apartment having negotiated the elaborate security system pertinent to these prime dwelling places.

When Dawn opened the door I was surprised to see her dressed in only a revealing peach kimono. Herluxuriant dark hair reached her shoulders and the glow in those wide sultry eyes made me believe that maybe there was something special about this one.

I had never met Dawn when she had not been fully clothed—at the start, anyway.

As I stepped inside I had to comment, ” Eager, tonight?”

She turned and her arms slid around my neck as she stepped in close, “You know I’m always eager for you, Jack.”

And her full lips meshed with mine, her tongue amatör porno probing along mine with a warm sweetness, her full breasts pressing against my shirt front.

From previous experience as we kissed I guided her towards the major bedroom, where we’d spent some passionate hours. But this time she stopped me.

“No, Jack. Not tonight. This time we’re in the second bedroom.”

“Is this the special?”

Her eyes gleamed up into mine, “No, that comes later. You’ll see.”

“Very mysterious, ” I said, but my words were crushed out of existence by her passionate kiss as we tottered towards the secondary bedroom, her hands already unbuckling my belt.

The secondary bedroom presented all the expensive finery of the main one. The only difference was it was a little smaller, but not much. The silken pillows and bed linen, all in peacock blue were every bit as elegant as in that other room.

Dawn was already pushing my pants down and I was a little overcome by her eagerness.

Gently I slid her kimono from her shoulders, and let my hands savour the smoothness and delicacy of her skin.

My fingers glided gently from shoulder to breast, never lingering. Shoulder, breast, belly. A continuous wave of sensuous caressing which I knew she liked.

For her part she quickly removed my shirt and was subtly fingering my semi erection as we stood close to the bed.

“Not your usual rapid call to arms, Jack. I hope you’re not going to let me down. I need you to be particularly strong tonight.”

“Is this the special bit?”

She placed a finger on my lips, “No more talk of that. That’s for later.”

And with that she gave me a gentle nudge so that we both toppled sideways onto the bed, and began our now customary pattern.

Her turn. And I ran my lips down the length of her body, back and forth, briefly lingering at nipple and labia, but never stopping for more than a second.

This action I pursued for several minutes, while she lay panting slightly, her hands by her sides.

Then as my mouth settled more definitely on her nipples, my fingers ran along the crevice between her legs, the swollen lips moistening under my touch.

Next I took my lips down to find her clit, but before we reached that stage she had sat up and ducked her head down into my crotch, her mouth quickly enveloping my swelling penis.

My turn, but it had been reached surprisingly quickly. A break in our usual pattern.

More was to come, for as soon as she felt me swell under the ministrations of her tongue and lips, she released me and lay back.

“Inside me, Jack. Now, ” she insisted.

“But we–“

“Who’s the client?” she asked, using a joking tone that I had heard many times before, when she had wanted servicing in a particular way.

“Yes, ma’am, ” I said with mock subservience, and sliding between her spread thighs, I placed my penis in her soaking entrance.

“Jack, I want you to make me cum, without cumming yourself. Okay?”

The request surprised me. Why this eagerness to be done and why—? But not for me to question her motives.

I began thrusting into the deep, secure wetness, varying my strokes, short, then deep. As her breathing intensified I raised my body so that each stroke smoothed over her clit.

In no time she was gasping, panting and then growling, yelping and heaving her pelvis up against mine as her orgasm rocked her.

I kept on driving into her, knowing I could easily hold on as instructed.

At last she lay back, breathing deeply, her eyes glazed as they looked up at me, “Thank you, Jack. You didn’t cum, did you?”

I told her that anal porno I hadn’t.

“Oh, good. I’m so glad.” And she sat up, her eyes ablaze now with a strange excitement.”Now go and get yourself a good thorough shower.”

“What?” This was definitely away from the norm. Showering this early in the proceedings

“Go on, Jack. Just do it—–please.”

“Don’t you want to join me?” I asked. We had done this so many times.

“I’ll get one all in good time. Go on, quickly.”

Totally mystified, I went into the en suite, and had myself a refreshing warm shower.

With a large bath towel wrapped around my waist I returned to the bedroom. Dawn wasn’t there.

As soon as I called her name, I heard her response from the major bedroom, “Through here, Jack.”

Wondering just what the hell was going on, I strolled through the living area to the main bedroom door and pushed it open.

And that was the moment my whole life changed.

Dawn was there, sitting on the bed, and fully clothed. But beside her, dressed in the peach kimono that Dawn had worn earlier was —-well, how to put it?

Should I labour the cliches? She was just the most stunning girl I had ever seen, about my own age I guessed. But what was she doing here?

Something caught up in the back of my throat. My heart? Yes, here come the cliches.

I just stood there, totally stunned, mesmerised by hair, the colour of a late summer field of corn, eyes of palest blue, high cheek bones, and a bosom that thrust against the silk of the kimono.

And then there was the shy, slightly worried smile that played on full generous lips.

“Ah, Jack, ” Dawn said, getting to her feet, “I want you to meet my daughter. This is Rebecca—call her Becky. Becky, meet Jack. He’s just as cute in clothes as without.”

And with those words she grabbed at my towel and whipped it away.

Like some immature school kid I covered my groin with both hands, desperate that my action would somehow effect what this girl would think of me. Did that matter? Oh, God, yes it did. It mattered.

Yet, I noticed her eyes had hardly glanced at my exposed body, but were fixed on my face.

Dawn came up close to me, “Why, Jack, I’ve never known you be so shy and modest about your attributes.”

She handed the towel back to me and I quickly wrapped it around my waist. But I feared I’d already made a fool of myself.

Dawn was frowning at me, “Listen Jack, this is the special part of the evening.”

Her voice lowered as though she didn’t really want her daughter to hear. “She is still a virgin. And I can’t abide the thought of her first experience being in the clutches of some macho idiot, full of his own importance, caring only about his own pleasure. I want her to have a positive attitude to sex.”

I was listening but could not take my eyes off Becky, who sat now with her head down, as though embarrassed by what her mother was telling me.

Dawn was going on, “Look what happened to me. She needs her first experience to be a good one. And you can do that for her. Jack. You can show her how thrilling good sex can be, “

My brain could hardly take in what she was saying. She was offering me her daughter. More than that, her daughter’s virginity.

This stunning girl was there for me! So why did I feel so horrified? Why wasn’t I panting to get started on this delicious task?

Dawn patted my shoulder, “I’ll leave you together. Be gentle, Jack. But I know you will be.”

She stood for a moment in the doorway, “Oh, and there’ll be nothing to break through. She’s ridden horses.”

Then to her daughter, ” I do envy anal breakers porno you, darling.”

And she was gone.

Becky raised her eyes to mine and something melted inside me. I just stood there, gaping like an idiot.

“How do we start?” Becky asked, and her voice had the soft huskiness that matched everything else about her. “Do I take this off?”

She shrugged one shoulder free of the kimono, a tanned rounded shoulder sloped down to one delectable breast, its pink tip seeming to reach up towards me.

“No, please don’t.” It was my voice, stopping this beautiful girl from stripping. Was I crazy?

“You want to take it off?” she asked.

Rousing myself out of my stupour I sat beside her on the bed.

“Is this what you want?” I needed to know.

“Mother thinks—“

“Never mind what mother thinks. Is it what you want?”

“I’m nervous. I don’t know. You look very nice.”

“And you look terrific.”

“My mother said you would show me everything.”

“Becky, are you here of your own free will?” The question had to be asked.

Her eyes moistened as she answered, “Not really. Why are you asking so many questions? Don’t you want me?”

Want her? The thought pounded through my brain, Oh yes, I want you. But then added that fateful extra word—Forever. That’s the state I was in.

I leaned towards her and placed my lips gently on hers. Her mouth, full and soft, responded, while her eyes remained wide and uncertain.

Gently I raised one hand, intending to rest it on her shoulder, but on the way up it somehow connected with her bared breast, and lingered on that incredible round silkiness.

She gave a sharp intake of breath and her face pulled back from mine. She said nothing but I could see the confusion in her eyes.

“It’s not right for you like this, is it?” I suggested.

She shook her head, “I wanted the first time to be good, but with someone I knew and liked.”

I drew in a deep breath, “Would you like to get to know me?”

“What do you mean?”

“I mean, have dinner with me, tomorrow, the next day—next week—whatever suits you.”

“I’d like that—only—“


“This kind of work you do. It’s a bit—“

I took a deep breath before saying, “Don’t worry about that. I’m getting out of the business anyway.”

Yes, it was a lie, but only a little one. I didn’t know at that moment that it was actually the truth.

“But what about mother?”

I had to think about that. “Tell her you enjoyed it. But go get a shower—that’ll disguise the fact that we’ve only talked.”

She gave me a grateful smile, “Thank you, Jack.” And there and then we arranged to meet the following night.

As she vanished into the en suite she dropped the kimono and I had a momentary tantalising glimpse of her slender seductive curves.

By the time there was a tentative knock on the door I had done a few press-ups. So that when Dawn responded to my ‘Come in.’ I looked red-faced and sweated.

“Where is she” Dawn demanded.

I indicated the shower.

“You’ve done it? That was fast, ” she said suspiciously.

“We both came very quickly.”

“I didn’t hear anything.”

“Were you listening?”

She looked rather flustered, ” No but—well–“

“It was a very quiet affair, ” I lied, just as Becky came from the en-suite towelling her hair, and wrapped in a thick robe.

“How was it, darling?” Dawn asked.

“Marvellous, mother. I couldn’t have guessed it would be so—–quick”

Our eyes met briefly, secretively sharing our deceit.

“I told you he was good, darling.” Dawn said.

I wouldn’t admit to myself at that stage just what was happening to me. All I knew was that I had to get to know this girl who had been thrust into my life.

Just how Becky and I made out is reserved for the second part of this tale.

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