I was a Teenage Gigolo

At the time, I had no idea how idyllic my childhood was. The city where I grew up, on the west coast and surrounded by water, still honored its past as a roaring boomtown, the stepping off point for two gold rushes, home of loggers, fishermen and miners ( and the whorehouses that siphoned off so much of the wages of those men, though that wasn't talked about much) Later, my city sold it's soul to the dot.com's, and downtown went from fascinating and a little rough, to sanitized for the nouveau riche'... but in those days, we weren't so full of ourselves.

Those changes were still far in the future, the summer after my eighteenth birthday. The roar of supercharged WWII Allison engines still echoed off the hillsides for weeks every summer, as the thunderboats skittered around their race course, throwing roostertails of spray (and occasionally flipping, sinking or catching fire) Kids still towed replicas of their favorite hydroplane behind their bikes across hot concrete, the neighborhood where we lived still felt like the vacation village it had been, before the floating bridge replaced the ferries that had departed from what was now a lakeside park.

That was the summer I first realized I might have something women wanted. I'd been on my high school's coed swim team for four years, and often rode my ten speed for hours along the lake. I'd given up my paper route years before, and started doing odd jobs for local businesses and individuals. Our home was in a middle class neighborhood of smaller houses with no view of the lake, but surrounded by neighborhoods made up of expensive, older, and much nicer homes, with lake views, belonging to both old money and the newly wealthy, so I was well paid for odd jobs. It helped that I'd learned Japanese/northwest style pruning from my grandmother, since many of the Japanese gardeners, who had cared for some of these yards for four decades (minus the the war years) were retiring. Those hours raking, mowing, riding, and swimming had evidently given me a decent physique. The Japanese hairdresser who's shop windows I cleaned, had talked me into a short, permed haircut that spring..."we make you look like Greek statue", and another salon owner had come out one afternoon to ask me to put my shirt back on as I cleaned her windows... since I was "disturbing some of her customers". I was tall, and I'd been shaving daily since I was fifteen, so I could pass for several years older than I was.

The village real estate office had given me several jobs, cleaning up and maintaining the yards of houses on the market, and it was at one of those jobs that my life changed forever.

My favorite team mate was slowly peeling off her racing tank, avoiding my eyes, and blushing as she stared at the stiffening erection that my wet Speedo did nothing to hide. Her nipples were small and pink, with aureoles no larger than a nickle, set on firm, perky breasts that pointed those hardening points upward. Slim and sleekly muscled, dark haired, with full lips I'd been imagining wrapped around my cock for years, she slid her suit over her hips to the floor, stepped out of them, and moved closer, reaching for my swimsuit..."Let me....

....and disappeared in a flash of light, as the full length mirror in front of me swung open, revealing its mounting surface to be a door, and the empty house I'd let myself into ( using my lockbox key) turned out to now have another occupant...an attractive older woman. In that split second before she turned and saw me with my erection in hand, I noted that she had the lean, tanned, and well kept look of the tennis club set, and the tennis dress she was pulling over her head as she entered the bathroom with me confirmed that. She was talking over her shoulder....

..."let me grab a shower and change, we can go to...DICK!"..as she turned and saw me, dick in hand, stunned as a deer in the headlights.

From the other room, another woman's voice, horribly familiar, coming closer....."Dicks? I thought you swore off those greasy burgers years ago."...

"Oh, Peter"...as the owner of the second voice spotted me past her friend. This was Mrs. Schwartz, Trudi Schwartz, the real estate broker who'd given me this job, and several others before. This was bad. Seriously bad.

"Peter? No, THIS is a dick "(slapping my hand away, grabbing my hard on firmly, and squeezing. "My husband... soon to be ex husband now, has a peter...no, maybe it's a willy. It's little, and soft...not like THIS...a tug and a squeeze this time.

I could smell enough liquor on her breath to think there may have been a couple martinis with her lunch. Maybe even three. She also smelled of sunshine, expensive perfume, and fresh sweat, and my dick, rather than wilting from embarrassment, got even harder.

Yeah, my name is Peter. Peter Parker, and just don't. Please. I've heard them all.

"With great power comes great responsibility"..."met any spiders recently, Parker?"....it gets really old.

With a firm grip on "Dick", Dorothy (as I found out later) dragged me out of the bathroom and into her bedroom, demanded I lie down on my back on the white shag rug, and after stripping off her bra and panties, knelt over my thighs, and began to stroke the head of my dick between her pussy lips, already slippery She didn't seem at all bothered by having her friend right next to us, watching. Trudi had an expression on her face that combined exasperation and arousal, which would have been funny if I hadn't been both scared and incredibly turned on.

"You won't come too soon, will you, Dick? I haven't had one like you in years, much less attached to a body like this"...as she ran her unoccupied hand over my chest and stomach. It wasn't clear whether she was talking to me, or the rigid appendage in her fist.

What she was doing felt reeeealy good, but I'd already jerked off twice that day (not uncommon for me at that age) so I felt pretty safe in shaking my head no, this whole thing had left me speechless.

"Oh good!"... as she rose onto her knees, guided the head of my cock into her, and slowly settled down, gradually engulfing me in her slick heat.

I'd had sex before; my girlfriend had her own apartment nearby, and we'd gone through "The Joy of Sex" together, but this was sooo much better. Two fumbling kids new to the whole thing didn't feel like this...not at all.

"Hold still, Dick. You're kinda big, and I need to take this slow, but I want all of you"...you can imagine how I felt to hearing that, as a young guy, from his second lover ever ( and first older woman) Dorothy leaned forward, and I could feel the head of my dick slide across the nose of her cervix and into the depths beyond.. She moaned as she settled fully onto me, bringing her clitoris into contact with my pubic bone, and began to grind..."Oh FUCK this is good!"

With disbelief, I realized that Trudi had stripped, and was kneeling by my head. She was a blonde version of Dorothy, tanned and fit, but not so slim. Wide hipped, buxom, and nicely padded.

"Peter. You've been bad, but we can work something out. I'm going to sit on your face, and I want you to lick and suck whatever you can reach. I'll let you breath...slap my thigh if I forget "...and at that, Trudi spread her pussy lips with her fingers, put her knees on either side of my head, and settled her pussy down on my mouth.

The next few hours were a blur of sex, three bodies in a dance of pleasure, in combinations I hadn't imagined possible. I fucked them both until my ejaculations were dry and my dick was sore. The two women pleasured each other any time my dick wasn't in one of them, and often when it was ( I learned later that they'd met at a girls private prep school, and had remained intimate friends) The two of them taught me more about how to please a woman than some men learn in a lifetime, and more about what my own body was capable of than anyone in the 40 years since....not all that day, mind you.

Some while later, semi-comatose in a pile on the floor, I realized that it was getting close to the time I'd be expected home, so I dragged myself to my feet and staggered to the bathroom. Coming home reeking of sex from "yard work" would definitely cause some awkward questions from my parents. A long hot shower later, dressed and ready to slip out, something told me to drape the two sleeping women with the coverlet off the bed. As I was tucking it in around them, wishing I could crawl back into that warm pile of female flesh, Trudi opened one eye..." You're a good kid, Peter, we'll talk soon"

A couple weeks later, we had an arrangement worked out, and a schedule of activities in place. About a dozen afternoons a month, I'd arrive at Dot's on my bike, towing the converted newsboys cart that held my garden tools, and bring it around back. Her house was on a steep slope, a double lot full of huge old rhododendrons on the upper side of Lakeview Drive, so it was unlikely that the frequency of my visits would be noticed, but the tools provided some cover. Those days were "tutoring sessions", when one or both of my handlers would screw me silly, while teaching me the variety of ways to bring women to orgasm, how make them feel cared for, and how to leave them sated and happy.

One day a month was a "Lady's Club day", where groups of women, picked from Dot's and Trudi's circles of friends, based on their dissatisfaction with their sex life and their ability to keep their mouths shut, would meet for a light lunch. I served, generally in minimal clothing or nude, with it clear that I was available for whatever the guests wanted of me. Donations were collected at the door to cover the meal, my services were extra. The take was split 60/40, with Trudi putting half of my 40% away in an investment fund for my future, the two of them splitting the 60%. I took 20% home as cash....still much more than I'd been charging for odd jobs and landscape work. I ended up banking a lot of that, too...my parents would have noticed if I'd bought a new bike or boat, or bought a motorcycle or car.

You know how bachelorete parties tend to get wild, and how women at male strip clubs incite each other to quite unladylike levels of raunchy behavior? The tennis club set was no exception. Ice queens in impeccable makeup and designer dresses, wearing shoes that cost as much as one of my parents house payments and jewelry you could trade for a small car, would suck me hard at the table, push me to the floor, hitch up their dresses, and ride me to a series of grunting orgasms...all in full view of a dozen other women, some of whom they'd just met.

The "ladies club" luncheons were also where we encouraged women set up private appointments with me, through Trudi, at $50 an hour. To give you an idea, this was the year the federal minimum wage was raised to $2.00/hr, you could buy a brand new Super Beetle for less than $3K, a mid range mortgage payment was about $400, and gas was 53 cents a gallon. My take home from these private sessions, was $10 an hour, with another $10/hr going into a savings account. Many of these women often paid $30 for an hour at a hair salon, so what we we asking didn't seem out of line. No one complained, several even tipped me, and a few sent me Christmas cards with $100 bills in them.

We had some good times. Often I'd do some sort of show after lunch, and we tried to keep it fresh, since many of the women attended regularly. It always surprised me how much some women liked to watch me stroke myself to a full erection, oiled and rigid, and then stop without ejaculation, my dick bouncing with my pulse, so hard it would slap my stomach as I walked through the audience on display. Some of them liked to take me in hand at that point, work me back to the edge, and try to hold me there. Others would bid on who got to finish me off, or pay for ten seconds, each one trying to make me come during their turn, by any means whatsoever, and claim a free hour with me as the prize. Sometimes we'd take bids on which of them got a chance to take pleasure from my mouth as others were using my dick, or tormenting it. We'd have women volunteer to be part of the show, and I'd demonstrate what I'd been taught, bringing her to a series of convulsive orgasms with my hands, mouth and cock. When I told my handlers that I could suck myself off, and demonstrated, they made that a regular part of the show, with the audience bidding on who got bring me back to rigidity and ride me afterwards.

It was during one of my tutoring sessions with Dot that things almost fell apart. We'd had one scare,when the neighbor across the street caught on that something was going on at Dot's place, but we comped her with a couple hours of my time and made her a member, which took care of that concern. The big scare was when Dot's daughter walked in on us. The house was big, and teenage girls don't have much use for their moms as a rule, so maybe we got careless. Dot was in her favorite position, cowgirl anal, with me on the floor, when the bedroom door burst open " Hey Mom...EEEEEW...MAAAAWM!!!

"Not now, Margaret, you can see I'm busy. You have been asked to knock"

Margaret (Meg at school) was the swim team mate I'd been lusting after for years, starring in so many of my jerk off fantasies. I hadn't realized Dot was her mom (this was Dot's second marriage, their last names weren't the same)

"Ewww...just...Omygod! Is that Peter?!!"

"Margaret!...OUT!..we'll talk about this later"

We did negotiate an arrangement. Meg threatened to expose the whole thing (she hadn't been as oblivious as Dot had imagined) so in spite of Dot's discomfort over sharing me with her daughter, I ended up splitting my afternoons at Dot's between the two them. They did insist that I shower before leaving Dot's bedroom for Meg's. Understandably neither wanted to smell the other on me.

Well, there was that one time, a couple months later, but otherwise...yeah, I showered.

That first time, knocking and entering the bedroom of the girl I'd so often fucked in my imagination, never expecting to actually do so...that was weird. I think that Meg never saw me as boyfriend material, I'd been friendzoned years ago, but here was a chance to get sex with someone who knew what they we doing, and I think the sense of power she had over me added something for her. Meg could be a very demanding lover, and she wanted to try everything. There may even have been some competitiveness with her mom...(ya think? ) If this hadn't been the girl of my fantasies, I couldn't have kept up, even using every trick Trudi and Dot had taught me. Eventually we wore the edges off, and we've remained friends to this day...all four of us, actually.

But that first time...

"Come here and eat me out, Peter"

"Not even a hello and a kiss, Meg?"

"Don't get uppity, slaveboy, do me good or pay the price."

I'd figured out how to handle demanding women by this point.

"Yes'm"...as I crawled onto the bed between her thighs, slid my hands under her knees, and grasped her wrists.

"Wha...?....oooohyessss"... as I laid my tongue at the lower end of her vaginal opening, already shiny with her juices, and drew it slowly up her inner lips, flicking it across her clit at the last. Then again. And again. She made a halfhearted attempt to free her wrists, but as I got a sense which spots felt best to her, how they evolved and moved, and the rhythm that pushed her upwards, I soon had her grinding against my face, and somewhat less in charge of things. I'd been well instructed on how to sense a woman's impending orgasm, and as I felt hers approaching, I shifted my rhythm just slightly, stopping her climb just short of the cliff, holding her hanging. After I felt her lose the moment, I shifted back to the most effective rhythm again, until I felt her near the edge, then just slightly changed the pressure and location of my tongue. After about a half dozen of these cycles, she had stopped demanding and started begging...or as best as I could tell by her tone of voice, she wasn't making words anymore.

That was when I released her wrists, slid a couple fingers into her pussy, found the spongy bulge of her g-spot, and while keeping a firm, circular pressure on it, shifted my tongue yet again.

AaAaaaAaahh!

Oh, that worked. Time to push her over the edge. I put a firm pressure against her anus with the pad of the thumb of my other hand. Slippery with the flow of her juices, her puckered little hole yielded, clenched, yielded again, as I massaged her g-spot and relentlessly tongued what I'd found to be the most effective pattern, a clockwise circle around the tip of her protruding clit. With a shriek, she drove her ass down to the base of my thumb, and pulled my face hard against her crotch. Humping my thumb, grinding against my face, we rode wave after wave of orgasm, until she collapsed semi conscious.

Later..."How the FUCK did you know to do that?"

"You mean the tongue, holding your wrists,or the tease?"

"The tease? The TEASE?! You mean you pulled me back from the edge six fukin' times, ON PURPOSE?! Do that again and I'll, I'll...."

"But you liked the end result, didn't you? You came hard."

"Maybe."

"You know what I mean, bastard...your finger...there."

"You mean my thumb in your asshole, Meg? You did seem to like that. I just knew, somehow. I think you want a cock there"

"Never yours, bastard, you're too big"

"Your mom seems to manage alright"

"Fuck you"

"Sure, if you're up for it"... gesturing at my raging erection.

"Do me, slaveboy"

Meg was slim enough that I could easily lift her ass onto the tops of my thighs as I knelt on the bed, positioning her clit under the tip of my cock, as her splayed legs opened her wide. With a roll of my hips I could slide the length of my cock up her still slick slit, so I did so, slowly...several times.

"You want this?"

"What-ev-errrr"

Clubbing her clit with the rigid length of my boner changed that valley girl sneer in a hurry, to an expression of disbelief and shocked arousal.

"You want this, my queen?"

"Fuck yes"

Rolling my hips back put the head of my dick at her opening, and rolling forward drove half its length into her in a moment, as the angle forced the crown across her still swollen g-spot. Her response was gratifying. More so when I repeated the motion, rolling my thumb over her clit at the same time. A few more repetitions had her trying to drive me deeper, but her position atop my thighs made it easy for me to frustrate her attempts.

"You want more, princess?"

" You fucker...Yes!"

Keeping my erection half buried, I swung one of Meg's legs up and over, rolling her off my thighs onto her side, burying my dick deep as I knelt behind her, pulling mostly out, then slamming into her again. This angle drove my cock head hard across her g-spot with each thrust, then slipping across the tip of her cervix as I buried myself in her fornix, probing the innermost depth of her vagina. Her tiny, tight, almost boyish swimmers ass let me drive deeper than was possible with the more mature posteriors of Dot,Trudi, or most of my clients.

Remember, this was the early 70's, still an extension of the sexual revolution of the 60's, before AIDS or antibiotic resistant STD's, and every sexually active woman was on the pill. In those days, condoms were for truck stop prostitutes and street walkers.

Each out stroke wrung out a moan, then a grunt as I slammed home, rising to a wail as I spooned behind her, pulled her upper thigh back, straddled her clit with a couple fingers, then moved her mound in small circles. I'd come twice with Dot earlier, so I wasn't in danger of blowing my load anytime soon, in spite of the way her tight and slippery pussy was clenching around my dick, so I was able to maintain a relentless rhythm of deep strokes as she had a series of shivering orgasms.