I was a Teenage Gigolo

"You're a fucking machine...I can't come anymore, and my pussy feels bruised"

"Awww...tapping out so soon? I'm just getting started. Your mom would take me up the ass about now"

"Shut up about my mom! "

With a heave, I rolled her onto her belly, hooked my toes inside her ankles, and forced her legs wide, pinning her with my weight, dick still buried deep. Taking her wrists in my hands, I forced them wide as well, holding her spread eagled on the mattress as I ground my dick deeper into her.

"Fight me, princess...it makes me harder."

I could feel her strain, and try to roll, but I didn't give her more than an inch or so of movement. After she'd exhausted herself in struggle, I forced her two wrists down and back. Kneeling outside her thighs with my dick still buried in her, most of my weight still pinning her at the hips, let me free my hands to force both her wrists to the small of her back and take them in one of mine, leaving the other free to begin probing her slippery anus, while continuing short and shallow strokes in her slick puss. All the previous orgasms, and my thumb earlier, had loosed her sphincter some, and she was slippery with pussy juices, and I took full advantage, firmly massaging the ring of muscle, and eventually working my thumb into her to the base, and massaging her asshole from the inside, all the time stroking my dick in and out of her sopping pussy. Somewhere in there she stopped struggling, and started pushing back against my hand.

"You want my dick here, princess?

"omygodyes!"

"Use your words...what do you want me to do?"

"My ass, fuck my ass!"

"My thumb has been fucking your ass for, let's see...a good fifteen minutes now. I'm not sure what you mean... you'll have to be more specific"

"Your dick, I want your dick in my ass, you bastard!"

"Never didn't last very long, did it?"

"I'm going to fucking kill you if you don't put that thing up my ass this goddamnfuckingsecond!

"As you wish. On your knees, and push back against me" Even with both her asshole and my dick coated with her slick juices, and her ring well loosened, it was still a slow process to work my rigid length past the elastic ring of her anus. My dick is a bit over two inches across at the widest point, but tapers some toward the softer head, which eased things a bit. I kept a steady pressure against the slowly loosing ring, holding her hips to prevent her forcing progress too fast.. The moans and panting as she worked to embrace this invasion of her virgin ass made me even harder, which I would have thought wasn't possible.

Several minutes later, I was buried to the base in her rectum, and she was shaking and sweating under me. Time for act three. Rolling us into spoons again, I took the thumb that hadn't been in her ass earlier, slid it between her thighs from behind, and into her pussy, putting my fingers just above her clit, and my thumb on her g spot. My dick in her ass could feel the knuckle of my thumb, and based on the inarticulate noises she made as she thrashed, I was onto something. Wrapping my other arm around her chest to hold her still, and pinching a nipple, I started fucking her pussy with my thumb, grinding across her clit with the web of my thumb, all the time making sloow, short, deep thrusts with my dick, feeling her ring loosen and ease. She began to drive her hips back, forcing a longer stroke, and broke into a howl as the combined sensations overwhelmed her. I kept the rhythm going, and forced her through several more shaking, shrieking orgasms before deciding she was ready for a serious ass fuck.

"Enough foreplay, princess, I think you can take full strokes now...up on your knees"

With my dick still buried in her ass, we managed to roll from our sides to her face down, with me atop, then got our knees under us, and I put her in what I fondly call the "cat in heat" position...on her knees with her chest pressed to the bed, back dipped. This angle forced my dick head against the back wall of her ass and the base, on a deep thrust, hard against the wall between her ass and pussy, generating intense sensations for as both, so I had myself on the edge in just minutes. Meg wasn't making words anymore, but judging by the rhythmic waves of muscular contractions and bestial noises,she got a couple of strictly anal orgasms before, with a roar that was probably audible at the other end of that big house, I dumped what felt like a half cup of cum up her rectum.

In those days, I could often stay hard after an orgasm, and have a second one soon after, no softening in between. Occasionally, a third. On rare occasions, under especially exciting conditions, a fourth. This was one of those times. The semen I'd filled her ass with provided enough extra lube that her back passage stayed slick enough for me to use it to come twice more, and (after a visit to her bathroom for a careful wash) take her pussy one more time. Cuddling after that last time, rich bitch attitude gone, curled up, limp as a noodle in my arms, she allowed that she hadn't felt so thoroughly, wonderfully fucked since she took on five guys at a drunken graduation party.

We went on in a similar vein for years, and we did very well. The two salon owners from my odd job days joined my client list early on, bringing me other referrals. A couple years later, when my investment account (handled by Trudi, and including IPO's for businesses like Intel, McCaw, Cablevision, and Atari) had risen in value to well over 100 K (remember, this was the late 70's, that was a decent wad of cash in those days) I had paid off my college loans, and was able to pay cash for my first home, and soon after, rental houses in a nearby hillside neighborhood, then in transition from decades as inner city ghetto to valuable view properties. I repaired and landscaped these small homes ( often with adjacent vacant lots that could be picked up for a song) with the rents adding to my ongoing sex service income. Meg and I would get together a few times a month, any time we weren't seeing anyone else

Dot received the house in her divorce settlement, plus a nice alimony, and used her portion of our business proceeds to buy art glass, discovering Chihulli in his early years. Trudi used the added income to buy investment property, and kept me busy in my off hours maintaining the yards. I hired a few classmates at school to help with those, my schedule was pretty full.

That sort of work was actually a relief. There's only so much sex a guy can handle, no matter how horny... even with a few tricks up his sleeve.