Copyright© 2003 by Carlos Malenkov
Bobby knew his place in the world. He was a bottom. He was the one who got on his hands and knees and presented his ass. And mostly, he liked it that way.
Oh, once in a while he'd switch and be the one doing the inserting. Bobby was actually quite a skilled cocksman, and he enjoyed the turnabout. But bottoming was his real talent. "You're a natural born receptacle," Norm would tell him. "Your butt was made for fucking."
On a hot day in July they were out swimming and sunbathing. It was an equal opportunity beach, with both straights and gays out in force. This made for quite an interesting mix.
A sudden wave caught Bobby from behind and knocked him off his feet. He was spitting out salt water and sand as Norm helped him up and slapped him on the back. A group of laughing women walked by.
"Hey, look at them depraved dollies, Bobby, old boy. Betcha you wouldn't know what to do with that kind of meat."
"You think? Look, my equipment is every bit as good as any their boyfriends have got. Who says I couldn't... ?"
"You're a wacko, Bobby. We've been together -- what -- two years now? Your ass is what I stick my equipment into. And you're saying you could make it with a woman? Whoa, baby, dream on!"
"Damn it, Norm. I'll prove it! What's it worth to you if I can get one of them girlie girls in the sack?"
"Bobby, old fellow, if you can pull off that stunt, I'll let you top me every day for a month straight. How's that hit you?"
Well, why not? He knew the right moves, more or less. Hey, sticking it into a cunt couldn't be all that different than into an asshole, could it now? Only trouble was, that was virgin territory for Bobby. He had never even kissed a woman.
"Hey! 'Scuse me, ladies. Would one of you care to volunteer for a scientific experiment?"
A tall blonde turned around and favored him with a steely-eyed glare. Her two friends giggled.
"Now that's the sorriest excuse for a pickup line I've heard in years. What next? You're gonna offer me a role in a movie?"
"Truly, Julie. It's in the name of science. I -- "
"You've got the wrong woman. Julie's the one who ran off with the crown jewels. Your crown jewels. Get lost, asshole." Blondie and her friends began to walk off.
"Wait! I know the secrets! I can -- "
Norm tried to cheer him up. "Hey, sweet guy, you can't just walk up to a woo-man and expect her to lose her heart to little old you just on account of your pretty blue eyes. There's a whole song and dance you gotta go through. Taking them out to dinner, entertaining, and all that bullshit. More trouble than it's worth. Believe me."
Bobby was thinking on it later that afternoon. He was flat on his stomach with a beach towel underneath. They were in a secluded cove behind the seawall. Norm was on top of him -- deep inside him in fact.
"Damn it, I do know the secrets. I know as much about ass-fucking as anyone. I could bring a woman unimaginable pleasure like that. If they'd just listen... "
"What's that you're mumbling, Bobbie? Want me to pump faster?"
"No. Push all the way in. Deeper. Yeah, that's good. Now stretch out flat on my back and don't move. Let's see if I can make you come just by squeezing. I'm gonna milk you dry and make you beg for mercy."
Just as Bobbie felt Norm shudder and groan to the accompaniment of the familiar throbbing and wetness high up in his gut, he thought he heard clicking sounds. Turning his head to one side, he saw a woman standing there. She was snapping pictures. It was Blondie.
"Would you mind holding that pose, darlings?" she said. "I'm a photojournalist doing a spread on modern mating customs."
As Bobbie and Norm struggled into their swim trunks, the woman continued to shoot. Norm walked over to her and held out his hand for the camera.
"What's your game, dame? Blackmail? Or maybe you're just a plain vanilla peeping tom. Give."
"It's the other guy I'm interested in, the one you just finished shtupping. Shove off, dickhead, so I can talk to him for a moment or two, and I'll let you have the roll of film afterwards. Or I can send you a set of custom prints, if that's what you'd prefer."
Norm spit into the sand, then walked around the seawall, leaving Bobbie alone with her.
"Why didn't you just come right out and say you were a queer, 'scuse me, gay interested in some female booty? That might even have worked. It so happens that I've been fascinated by anal for a good long while. My boyfriend won't go near my butt, thinks it's dirty. Goes without saying that he won't let me near his own, either. I'm Lissa, by the way."
"Pleased to meet you. I'm Bobby."
"Well, Bobby, what say we get together some time and discuss topics of mutual interest?"
Bobby's hands were shaking. He felt like a teenager on his first date. He had doused himself with way too much of Norm's best cologne and the too-tight shirt collar was chafing him. There were beads of sweat trickling down his face. He stood in front of the cold, uncaring intercom box.
C'mon, fella, push that button. The worst that could happen is that she's been putting you on and gave you a phony address. So what? A little humiliation never killed anybody.
The loud buzz almost stopped his heart.
"Come on up, Bobby. Sorry to have startled you. Saw you on the videocam as you walked into the outer lobby. It's 7E, on the seventh floor."
The door opened at his knock. Lissa had on a casual outfit -- shorts and a halter top. Bobby felt self-conscious in sports jacket and tie.
"No thanks, Lissa. My friends say I'm spaced-out out even when stone cold sober."
"I can understand why. Say, you must be awfully hot in that monkey suit. Wait. I'll get you something comfy you can slip into." She disappeared into the next room.
Bobby felt much better in the gray silk bathrobe. It was three sizes too large. Must be her boyfriend's.
She had on a matching robe, but in a bright shade of magenta.
"So, let's talk. I can't say I'm much interested in you as a person -- sorry about that -- but fill me in on what you know about anal lovemaking."
"Since you have a disconcerting habit of getting straight to the point, Lissa, let me ask you what you know about it, so I know where to start. Have you ever actually done it?"
"About three boyfriends ago I gave it a shot. The guy had never heard of lube, and anyhow, he was a clumsy idiot. All his fumbling efforts only got him partway into me before he shot his wad. It hurt a lot, and that spoiled it for me for a good while. Since then, well, I've done some reading about it, but there's been no action."
"Yes. And why are you so obsessed with, well, sodomy?"
"Are we getting biblical now? Or just witty? For a gay man you seem to be pretty damn sure of yourself when you're in the company of a woman. I like that.
"You see, Bobby, I don't really get very much out of so-called normal sex. Actually, the only way I can come is by rubbing my clit. (You do know what a clit is, don't you?) Even then I have to stick a finger up my... my ass. I'm highly sensitive in there. It seems to trigger me somehow, to push me over the edge. Now I want to feel a real cock... inside me, inside that place."
"As it happens, Lissa, I've done a few asses in my time. Mostly, though, I get my own ass done, as you might have figured out by now. Anyhow, I know all sides of the deal, top and bottom both. For a start, let me show you a couple of relaxation techniques."
"That's a good girl, push outward, as if you were on the pot and doing a 'number two.' Gently. No need to strain. This unlocks the sphincter ring. See how easily a finger slips into you. Now another. It's Mother Nature's little reflex for expelling waste out of your gut. It also opens you up... and gives access to the dark inner mysteries."
"Dark mysteries, huh? You have the soul of a poet. You know that, Bobby?"
"The poet is exploring the darkest of your mysteries. Now I'll stretch you by rotating the two fingers inside you. How does that feel?"
"Not too shabby... actually quite nice. Kind of like being gently pried open. Wide open. What's next -- being turned inside out?"
"Let's not rush things. I'm lubing you inside, as well as stretching and loosening you at the entrance. Don't like to use this cheap petroleum jelly stuff, but that's all you had in that fancy medicine cabinet of yours. It'll work okay for now, though."