First of a two-part tale, although each piece can stand alone. Same setting as the story "Arlene's Long Spermfest Weekend," but a year previous...
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Lenny is just about the horniest bastard I have ever known. We had been buddies since seventh grade and I had watched him run through a string of girlfriends in high school, and I don't even want to think about how many deflowered cunts got chalked up to his name in our backwoods town in New Hampshire.
He wasn't particularly good looking or witty or charming or athletic or even well endowed - none of the things you normally would equate with success in the sexual arena - but he had a restless, unquenchable libido and an uncanny nose for sex, the erotic opportunity door cracked open just a sliver that would lead to some exciting, exotic sexual experience. And he was never one to be shy about forcing the door, if he thought the odds seemed even remotely favorable.
Back in high school I always heard about his adventures the next day, in excruciating detail, enough to make both my mouth water and at the same time curse my own rotten luck with the girls.
He generated enough daring, risky, sex-saturated stories to fill a couple books, and I could tell you details about his girlfriends' bodies and proclivities that they never would have suspected would be revealed to anyone else. Lenny Steinholz was not someone you could trust, but he sure made up for it in the entertainment category.
Now decades later, we sat sipping our afternoon beers on the porch of his rustic northern California summerhouse, with a nice forest-shaded view of the river fifty yards away.
I couldn't help but think about how we were still talking sex non-stop, just like the pair of horny, small-town, fourteen-year old boys we used to be, dreaming about how we might somehow be able to make life into a wet, wide-open womb waiting to indulge our pricks. He'd done far better on that measure than I.
His salt-and pepper hair looked good, receded some but not a lot. Nice casual plaid shirt, expensive shorts. His belly was out there, shoulders still broad, his legs pale and skinny, but his eyes retained the familiar glint. He didn't miss a trick, especially if the sniff of sex was anywhere near.
I had been small but wiry, and while my middle had expanded over the years, I was still way trimmer than him. But the hair was mostly gone and all gray now and I kept it cropped short, old-guy style.
I looked at the right hand surrounding his beer glass. Those long, careful fingers had been the first ones to stroke my penis besides my own, back in those excruciating, hormone-drenched, lethally frustrating years before we Scud-drove our pricks up our first conquests.
Back then in our small town being called a "homo" was about the biggest insult that could be hurled at another guy, but we never felt like we were in that category. We were just messing around, sexually open, perpetually aroused.
We didn't talk about it much, Lenny always said neither of us would be touching each other's cock if there had been a girl around, although we certainly entertained many fantasies about what would have happened if that had indeed been the case - say Amanda Phelps with her long breezy blonde hair, her shirt off, lodged in between our two raging pricks.
But he was right. We weren't attracted to guys or each other, just interested in playing with our pricks communally - "practicing" - seeing what these exquisite tools of pleasure could do, experimentally studying the whole arousal/erection/ejaculation cycle so we would be ready when "real' sex arrived, the sooner the better.
So the other guy's cock was just a placeholder, a last-choice port in a raging storm. Nonetheless, our little supercharged sessions together had still been plenty exciting and way better than masturbating our own tools to eruption, although we did a lot of that together too, watching each other spray our semen around the room, our camp tent, outdoors, wherever we were. It sure had been fun, excitedly perched as we were at the edge of our sexual event horizon.
After high school we'd gone to college at UNH, even roomed together off-campus for one year, but had drifted after that, each of us escaping our old stomping grounds as fast as we could.
I had only recently found out he had done law school, at NYU for godssake, which amazed me since he never seemed all that bright in an intellectual sense, but of course most of our discussions over the years had basically been his prick talking, and so he was probably smarter than I imagined when his cock wasn't getting all the blood-flow that might have gone to his brain.
He certainly had the requisite native cunning to be a lawyer. At any rate, he had gotten into financial markets and made his killing, and bailed out before everything went south around 2008 (and maybe before he got his own fingers caught in some dodgy investment cookie jar) to semi-retirement.
His economic situation compared unfavorably with my own erratic life as a journalist, my highest position having been second reporter for a newspaper in New Jersey. I wasn't poverty stricken but made it just barely into the comfortable range, now just doing freelance stuff.
The late-model seven-series BMW he drove had picked me up at the San Francisco airport and contrasted sharply with my well-worn Camry at home and my own marginal status.
The damn Facebook thing had brought us back into contact, and after a few months of communication, I found myself taking a cheap flight out from the east coast for a couple weeks' visit. It had been a long three-hour drive north to his hideaway, somewhere way back in the woods.
He said he split his time between this place in California and a beachfront condo in Florida, where he liked to spend his winters. He said there was a nude beach within walking distance. You could imagine I heard about that.
He complained he didn't like the shaved groins he saw at the beach, and we reminisced heavily about getting our hands down some girl's knickers the first time, feeling the alluring crotch hair, then smelling the intoxicating scent on our hands later, even if our adventures that night never got any further than a furtive grope.
"Thick crotch hair and bra-less tits. Man, we had no idea how good it was back then until all that was long gone. Know what happens when a shaved cunt is a week overdue?" he leveled a challenging stare at me.
Somehow I didn't want to answer, he'd obviously experienced this little event more than occasionally.
"Feels like fucking sandpaper," he snorted when I didn't respond.
"You mean 'fucking' sandpaper, or fucking 'sandpaper'?" I asked.
"Stubble rough on your prick or your lips, either one, both," he continued. "Give me a nice thick, soft, luxuriant crotch thicket with fluids all over it any day, well lubricated, spread inviting lips in the middle, smelling of sex, now you're talking." His eyes gleamed.
"Yeah, but nowadays you can see girls in thongs on beaches." For some reason I didn't want to yield completely to his nostalgia.
"Back then they were known as 'G-strings' and you only saw them at topless bars and strip joints. Now they are all over. Ass cheeks are out there in the open to ogle in a way never possible then. Even women with short skirts will wear them now, and you can get a glimpse sometimes if you're lucky. Plus, if it's a quickie, maybe in public, you can just push the string aside and do the penetration thing. Much easier than getting panties off or out of the way." I tried to make it sound like this was a common occurrence for me.
"True, true. Point taken, not all fashion change is bad," mused Lenny. "But halters? Remember them? Bring them back. A bare set of shoulders and some nice boobs moving around inside soft, clingy fabric? And still give me a sweet silky triangle of bush-hair, that's my idea of a good time."
"Remember Sue Jackson?" he leered. "Now there was a cunt with some serious hair."
Sue had been a large, fetching dark-haired wench with big hips and a big chest. I had heard plenty about every possible aspect of her vaginal attributes (tightness, texture, ability to absorb every pint of sperm Lenny deposited into her) after he coaxed her into a regrettably short liaison. But Lenny's short-term attention span and reckless roaming eyes always led quickly to another new conquest in those days, and they probably only coupled a dozen times.
He shook his head with the memories.
"Ever do a reverse tit-fuck?" he asked me suddenly.
"'Reverse tit-fuck?' What the hell is that?" I never knew what the guy was up to.
"With Sherry," he said, referring to who I believe was his second wife, "I loved to straddle her meaty chest and poke my cock up at her mouth while her big soft boobs made a nice valley for my plow. She'd tongue me on the upstroke and I'd either end up coming on her tits or I'd face-fuck her mouth. Come on man, I know you have done that."
"Sure, sure. I love sitting on a nice chest. Everyone I have done it with has enjoyed it. Several said it felt nice to have my penis 'mark' them, feel it rub up and down their face and boobs. But what the hell is a 'reverse tit-fuck'?"
"Okay, same scene, you just turn yourself around, so you're facing her feet. I suppose you could call it a 'cowgirl tit-fuck' if you're a stickler for terminology. You ride her tits, which she holds together, and you can cram your balls into her mouth to get suckled for some variety while she plays with your rod. Sherry loved mouthing my nuts. That alone almost made living with her for those years worthwhile."
It was not hard imagining him doing this. I had obviously never met Sherry, but he had described her as having wide dreamy eyes and a big chest that throbbed with sensuality. Of course her boobs attracted no end of male interest, and oddly enough, since they were basically the reason Lenny married her, they ended up being the cause of their split up.
Turned out she liked tit-fucking enough to do it with more than the one guy she was married to. It wasn't as if Lenny had been Captain Commitment himself, but like a lot of guys I know, he had a double-standard and he got bent out of shape when he found out someone else's sperm had been glazing her chest.
They apparently had parted with a ferocity that still reverberated, so it made his fond reminisces of their little sexual adventures all the more surprising.
" 'Course a reverse tit-fuck can turn into a sixty-nine, and we did that plenty too, my tongue buried in her furry, aromatic crotch while she drained my balls with her mouth on my pumping cock," he mused.
"Sometimes it was just an appetizer, but mostly it was fun just to plow her chest while I straddled her and looked at her gorgeous crotch, get my balls sucked, and then I'd hump a load of semen out between her boobs onto her belly."
"Fifteen more minutes of playing with her and I'd be fucking hard again and I would be back on top of her, missionary, my sperm squishing around between us. We'd have ourselves a nice leisurely second course."
He gazed off in the distance with a smile I couldn't quite identify.
This always had amazed me too. He had the ability to get hard again almost immediately after ejaculating. Even as teenagers fooling around together, he could jerk off two or three times in succession, while I was always done in by one.
"One night I reverse tit-fucked her, emptied a sticky good load out onto her stomach, and then plugged her belly to belly, straight away, sperm squishing all over the place and she came twice. Then before knocking off for sleep and after I pissed, she sucked me off again just on principle. Ha! Three times in an hour! Those were the days."