Gigolo Jack's Surprise in 276

Ron Vincent shook his head as he viewed the information in front of him.

"You might be lucky with this one, Jack," he told me, his chubby face spreading with his grin.

"She's got a hotel room already booked. Specifically asked for somebody in his early twenties."

"How old's she?" I enquired, keeping my fingers crossed.

"Forty -hree, it says here," Ron replied.

This would be only my second client. My first had been a forty-two year old. Surely I couldn't be lucky enough to have another early forties looker like she had been.

"Anything else about her?"

"Blonde hair---Okay?" And his eyes sparkled. "Funny though. She's wants her real name withheld. It's down here. We insist on real names and addresses. But she wants to be known only as Tania."

"Tania---sounds exotic. Hope so."

Ron winked at me, "Maybe your reputation is getting out already, Jack. Your last lady has booked you specifically for next Saturday night."

Well, that was worth looking forward to. That was the lady who thought she might be frigid, but was anything but. What surprises could this one have in store for me?

If only I had known!

"The hotel is the Algonquin---so, pretty cosy. Time, eight thirty tonight."

"Straight to the room?"

"That's what it says---she must be pretty eager. Instructions are that you identify yourself by saying 'Room special service'. A cautious lady, maybe. Good luck."

And he treated me to the now familiar Ron Vincent leering smile. I winked back and walked to the door.

"Jack!" Ron called after me, and I turned to see him shaking his head. "Isn't there something you'll need?"

I frowned, "Need?"

"The room number, Jack. The friggin' room number."

"I could have asked for Tania."

"And got nobody. It's 276."

"276," I repeated. "Right. I'll try not to get lost."

I didn't get lost. But at first I wished I had.

At precisely eight thirty, dressed in blue sports jacket and dark grey pants, with a matching open neck shirt, I was striding confidently down the plushly carpeted second floor corridor of the Algonquin.

Confident because I was pretty sure that, having booked a hotel room, this lady was after sexual service and not just companionship.

At 276 I stopped, adjusted my jacket, put on my smile, and knocked discreetly on the door.

A rather husky female voice on the other side said, "Yes?"

"Room special service, ma'am," I quoted, anticipation already twitching inside my pants,

The door slowly opened, and the lady, standing there dressed only in a peach negligee revealing a fascinating suggestion of ample bosom stared at me, a mixture of dismay and horror on her face.

"Jack!" she gasped.

My own face must have been quite a picture as shock, disbelief and some little quirk of excitement, ran through me as I stammered, "Aunt Steph!"

I recalled my mother frequently talking about the family surprise when her thirty two year old brother, Phil, had married a buxom young nineteen year old.

When my mother talked it was generally to express her surprise that the marriage had lasted. "That Stephanie she's such a live wire."

What she had meant was that my Aunt Steph was a sexy bundle, but my mother was not the kind to talk in that way.

At how many family get-togethers through my adolescent years had I wistfully observed my Aunt Steph, swaying and swinging on the dance floor, ample breasts jostling to burst from the thin summer dress she wore?

Her hips would roll with such erotic fascination that I had to remain firmly behind a table to hide what was happening to me down below.

I recalled her leaning over me one Christmas asking for a festive kiss and my eyes had gazed into that exquisite fleshy valley as her dress dropped forward. Her kiss had been warm, moist on the corner of my uncertain mouth.

Now, here we were staring at each other with mutual confusion. It seemed like minutes but could only have been a few seconds before she grabbed my arm, and dragged me inside, slamming the door behind us.

"Oh, God," she sighed her head of trailing blonde hair shaking," Of all the bloody possibilities. How the hell are you into this?"

I told her as she turned away and went over to a low sideboard, "I think we both need a drink," she said firmly. "I have the wine opened, but at this point we need something stronger."

She held up a bottle of Jack Daniels and looked at me questioningly. Dumbly, I nodded my head.

The very act of holding up the bottle had dragged the material of her negligee off her right breast, and that gorgeous pink tipped mound seemed to be smiling at me.

Aunt Steph gestured to the sofa and we sat down, both of us taking quick sips at our drinks. The warming liquid quickly dispelled early embarrassment.

"Jack, you won't say anything about this, will you?"

"Discretion is our bye-word," I reassured her. "Anyway, we haven't done anything."

She placed her hand over mine and said,

"That's true---but you deserve an explanation."

"If you like."

She went on to tell me of how Uncle Phil was becoming less interested in the physical side of marriage these days. "He'd rather go off to his pool match, or his horse racing."

Then she got to the point, "Your cousin Dean is just a year younger than you, Jack"

I knew that well enough. Dean and I were good mates. We had footballed together, knocked around in the same teenage gangs. We got on well.

Aunt Steph took another deep gulp at her bourbon, "Jack, I've found myself watching him, ogling his lithe young body as he's ambled half naked around the house. Oh, please understand Jack----I've longed for him to do it with me. Please don't think badly of me."

Then she was on her feet the negligee flowing away from her generous tanned thighs as she went and poured two more drinks..

"It's all right, Aunt Steph. I understand." I said, trying to be kindly, even if I didn't fully understand her desire for her own son.

She placed the drinks on the coffee table and stood looking down at me, her eyes clouded under lowered lids.

"That's so kind of you, Jack. I asked for a younger man to try to eradicate these feelings. I can't stand the notion of getting old. That's another part of it. Do you think I'm still attractive?"

And she ran her hands over her breasts and down to her hips.

This was no time for any kind of falseness and I confessed, "I've always thought you were one of the sexiest ladies I've ever seen."

"Even now?" And as I nodded she leaned down towards me just like that Christmas of long ago, but now the negligee afforded a more expansive view of her breasts as her lips brushed softly across mine.

My hands itched to reach out and grab her to me.

She stepped back, gazing down at me, while a sensuous smile played at the corners of her mouth, "Why, Jack, I can see exactly what you think of me-----how sweet."

Her eyes were on my crotch and I knew I was bulging down there. Before I had time to adjust she had dropped to her knees and with a brief, husky, "May I?" she ran the flat of her hand gently over the straining material.

Her blue eyes looked up into mine, "You like that don't you?" Her fingers moved to my zip. "I think you need a little more space."

As she lowered the zip and her hand opened me up to search I just sat there wondering who was supposed to be giving the service here.

As my erection broke free she leaned back with a look of astonishment on her face,"My God, Jack. I've always thought you were a good-looking lad. But what you've got there would be known as being well-endowed. That is one magnificent penis."

And her fingers closed around it, with such expert gentility that I could only throw my head back at the thrill of it.

Then her head stooped and the tip of her tongue tickling over the smoothness of my cockhead made me gasp with pleasure.

"You men," Aunt Steph chuckled, "you just love to be pampered."

And so saying her lips enveloped my straining cock, and the head, so recently licked, was pushing around the area of her tonsils, before she drew back slightly to lavish more favours with her tongue.

I don't know how long I would have let her go on, but suddenly she released me and leaned back.

"I think it's fair to say you are up for this---whether we are relatives or not no longer matters. It is time you earned your corn."

With that she grabbed my hands and pulled me to my feet. My erection waving helplessly in the air as I was led into a neatly laid out bedroom dominated by a king size bed.

By the side of the bed she turned and faced me, a wicked grin lighting her handsome face. "You are being paid to pleasure me, Jack. I know you have the equipment."

Her fingers brushed feather light over my

erection. "But do you have the skills?"

And she allowed her negligee to slip from her shoulders and slide to the floor. This was the second time in my limited experience that I found myself totally overcome with admiration of the naked body of a more mature lady.

Skin, smooth and glossy as alabaster, breasts that swelled and only delicately drooped, and the curve from waist to hip had my hands reaching out in instinctive need to glide along the splendour of those contours.

She closed her eyes as my fingers began coursing down over her hips, across the flatness of her belly. In reality I wanted my skills to rise to her challenge.

Without opening her eyes she began undressing me with rapid jerky movements.

Occasionally she drew in a harsh pleasured breath as my wandering fingers, stroking her generous buttocks, briefly lingered at that rear entry, or, trailing round her pubic mound, suggested movement into her intimate valley before moving on up to tantalise her heaving breasts.

When I was naked she took a short step back, her fingers clasped around my penis, her eyes scolding, "Jack,are you being a tease?"

"Aren't you enjoying it?"

"Oh, I have a lovely feeling I'm going to."

She released me and flung herself back on the bed with open-legged abandon.

I lay alongside her, my erection pressed against her thigh, and we had our first deep kiss. And deep it was.

Her tongue meshed with mine, probed and electrified the insides of my cheeks.

Hands were wildly active too. Mine glided over shoulder, breast and inner thigh, searching across buttock mounds to finger at her darker aperture.

Her hands flickered over my penis and scrotum, and beyond to probe my asshole with delicate prods. But our hands never lingered.

They stroked, searched, stimulated, as though our whole bodies were vast erogenous zones.

The mutual deep caressing intensified our kissing. Tongues locked in combat, licked along tingling lips, were sucked to the back of eager throats.

At last, high on the passion of it all, I tore my mouth from hers, and ran my tongue down over her breasts,tickling at each nipple in turn, before taking one of those swollen protuberances into my mouth, sucking and lavishing solid licks upon it.

She moaned in gratitude as her mouth bit and sucked around my neck and across my shoulders.

I could not recall ever being so beyond control, not knowing what I would do next.

Without thought my mouth was moving, licking down over her belly, until my face plunged between her widespread thighs,into that wetness.

Some instinct drew my tongue to the start of her heaving crevice and the tiny button that was

already well risen there. I licked and sucked on it.

She groaned and I could sense her difficulty in holding her body still. Then her mouth closed hungrily around my throbbing penis. Her tongue licked, before her whole mouth enveloped and sucked me deep, deep to the back of her throat.

Her lips began pumping back and forward along my whole length.

Still sucking at her clit I moved my fingers back along her swollen labia allowing two to sink deep into her soaking vagina.

By spreading my hand I had one finger insert into her tight little anus. So I was sucking and

plunging her passages.

Her squirming became so intense that she lost her grip on my erection.

"Fuck me, Jack. Now. Oh, great God. Please."

And she pushed at my hips urging them downwards. I swivelled until I was lying within her generous thighs, stroking the incredible smooth skin that ran all the way to her delicious opening.

Reaching down she held my penis and guided it between her dripping lower lips. Gently I inserted my cock head into her vagina trying to gain some measure of control.

But instantly her vaginal walls were clutching at my cock and, unable to resist, I plunged deeper.

Every inch was like passing through multiple mouths, each eager to draw me on and in. So I drove deeper, then on instinct, deliberately I tried to withdraw.

Her screeching protest preceded my full length plunge deep into her. Back and in, back and further, and all the time the ridges of her vagina seemed to be feeding on my cock.

I pulled on her shoulders so that she came up and we were sitting face to face and she was bouncing on my straining organ, while I buried my face into those generous welcoming breasts.

Sudden shock made me realise that I was close to cumming---something I had always been able to control.

But the heat of our exchanges, her demands, the sheer thrill of being like this with a relative were getting to me.

I began to grunt as she heaved against me. Desperately I thrust her backwards and plunged deeply into her as her legs wrapped around me, and with some relief I heard her beginning to yelp and mew like a cat.

I knew that she was on the verge too, so I drew right back almost to her entrance and she screamed out, "Nooo."

Then with all the power that my bubbling semen was producing I plunged once more and felt my cockhead strike her cervix and my cum began spurting like a fountain.

At the same moment I was delighted to feel her delirious shaking and screeching as together we pounded our demented loins together. On and on it went---I felt I would go on cumming for ever, while she heaved and strained and cried out under me.

After a while we calmed, and my limp penis began to slip from her. Wetness ran thigh to thigh.

"Oh, Jack, you have the skill, all right."

"Aunt Steph," I reminded her, but grinned to keep it light. "You paid for it. And I would have given you that for nothing---years ago."

We laughed together, and she said, "I'll bet you weren't that good years ago."

I had to admit that this was very true. Then she asked, "Was I good?"

I had to be honest, "I haven't known such passion."

"Are we finished?" she asked her fingers touching my limp member.

"I'm open to persuasion---remember, it's your call."

She leapt naked from the bed, "I'm all sweated---let's shower."

Inside a minute we were facing each other under the hot steaming shower, our soaped hands sliding sensuously down each others bodies.

I lingered for a while on the wonderful swell of her bosom, circling and gently squeezing while her hands worked over my chest and around my back onto my buttocks.

As my hands moved down over her belly I noted the expectant smile on her lips, and as I soaped into her pubic hair her thighs parted invitingly.

My hand slithered snake-like between her legs rubbing intimately over whole private area. I let the flat of my hand rest there and I pressed upwards. Rubbed, then pressed again. Very aware of the opening that waited hungrily there.

Her eyes closed and she moved her face to mine to be kissed and as our lips meshed I felt her hand rubbing over my groin, closing around my testicles, as my cock rose in anticipation.

She broke the kiss and muttered through the tumbling water, "Ah, he's awake again."

And she slid downwards her mouth sucking and licking down over my belly until her tongue was once again lavishing its generous favour to my cock head.

Within seconds her mouth had me totally enveloped, her lips pressing hard along my shaft.

All I could do was stand there and enjoy her ministrations as the water streamed over us.

Wow, I had a relative who certainly knew how to use her mouth. Her head was moving furiously and I knew she was trying to make me cum.

Firmly I placed my hands on her head and eased it away from its work.

The water streaming over her face could not hide her look of disappointment.

"Don't you like it?" she gurgled.

"Love it. But you're the client. Let's dry off and try the bed again."

She shrugged and we quickly towelled each other down and hurried to the bed.

But that was all the hurrying I did. This time I was determined to show Aunt Steph just what I was capable of. And that meant taking your time.

We had a long passionate kiss, while my fingers stroked her breasts, and my fingers dallied over her nipples.

Her own hands groped for my erection, her fingers rippling up and down from head to balls.

After a while I slid my fingers between her legs and checked her readiness. Just as moist as I'd hoped.

Gently I rolled between her thighs and she gazed up at me with some surprise.

"Rushing it?" she asked.

"Not at all," I replied and moved sufficiently to enter her, but only by inches.

She leered up at me and heaved her body in an attempt to draw me deeper. But I was in charge here.

I held her and made only minimal movements just inside her vaginal lips.

When it was time I moved deeper, but resisted the pull of what felt like suction pads. Smoothly I drew back then forward, back again.

At no time was I more than halfway into her. She began to pant, wriggle and exert her muscles to draw me on.

I made my movement faster, proceded to about three quarter depth. A lovely juiciness abounded there.

And now I raised my body so that my erection was tracking across her clit with each increasing stroke.

Deeper again, and faster. Her legs spread wider. Then raised up, feet in the air as her body arched and I sensed her approaching orgasm.

"Yes, yes," she gasped. "Cum now, cum now----"

I gave a full length plunge which took her over the edge and I luxuriated in the feel of her whole body in the throes of her orgasm.

I just kept my steady rhythm, while her vaginal walls gripped at me.

As she quietened she whispered, "Was that as good for you?"

"I liked it," I said lightly, and began heaving into her with deeper strokes.

"What?" she gasped. "Haven't you----done?"

"Should I have?" I grinned down at her and plunged and withdrew, plunged and withdrew.

I made a circular motion of it, making it seem as though her vaginal walls were expanding.

"Jack, oh Jack I don't think I can---cum again---I don't---"

I continued the steady, deep, hard thrust into her and suddenly allowed my cock to slide back until only the head was inside her.

"You're not stopping now, are you?" she whimpered.

"I thought you said---" But I didn't finish what I was saying. Instead I gave a vigorous push deep into her, reaching for the very depths of her. Again and again.

Now I quickened the pace, heaving at her so that her buttocks rose from the bed.

In no time she was gasping and heaving against me once more. Animal noises burst from her lips and this time I'd allowed myself to build up enough steam to ride it out with her.

So we were gripped in a mutual frenzy of

ecstatic climax.

"My God, Jack, I've never, never cum like that"

"Think I've cured your kinky urges?" I asked.

She looked up at me with a frankness that I had to believe, "I think anybody else is going to be a disappointment from now on."

A guy could get a big head in this game, but I was to learn that it is wise to know your limitations.

But this time it had been a good one----relatively speaking.