His Debut

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His initiation, as told to my shrink.
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estragon
estragon
46 Followers

As told to my shrink.

I made sure he was eighteen. I was at the birthday reception his mother had for him at Church. I remember when his mother and her husband went to Russia to fetch him and his sister over here to adopt them, and I was present when they were baptized. When Father Bert addressed them in Russian, their faces lifted up to him.

The Russians were offloading their unwanted children at that time, and you had to take two. His mother couldn't have children because her uterus had been removed when she was much younger, and she wanted children. Her husband went along with her, as he did with most of what she did, barring attending Church. He was a Northern Ireland Protestant turned atheist, and we were way too Catholic for his taste. But he was at their baptism and didn't object.

Long before she married her husband, his mother had the hots for me. She told me so, grabbing my hand and confessing her "sheer lust".

I very carefully saved the moment for future masturbatory fantasy, but gently declined. I was getting good pussy at the time at home. She was the repentant-sinner type who might just spill the beans, and that spill would make Exxon Valdez look like a picnic, at least as far as my wallet was concerned, because Wifey Charlotte would take me for every centavo I had or was ever likely to have. Plus child support.

And I doubted his mother was that good of a fuck. But I never found out.

But we were friends, and I saw her and such of her children as she could dragoon into showing up at Church. Her daughter, the elder of the two, manifested in the clearest way that she would only attend if threatened with grievous bodily harm. She came out rather noisily at the age of sixteen, to no one's surprise, and had Mommy arranging sleepovers with her kaleidoscopic array of girlfriends.

Mommy was searching out gay-friendly colleges for her dyslexic elder child, found one, and shipped her off with a disillusioned tear.

Son Raffi was two years younger. Mommy could get him to Church, as he loved to sit and gossip with the elderly ladies, and exchange extravagant hugs with them. He knitted beautifully. It looked like Mommy had indeed gotten two for the price of one, courtesy of perestroika, glastnost, and the Yankee dollar.

He and I used to serve at Mass occasionally. I was very careful to stay two feet away from him at all times. If divorce was disastrous, jail was suicidal. We exchanged formal handshakes at the Peace, rather like two diplomats who detested one another.

His slight lisp was charming, but we only spoke when it was unavoidable. I was, however, aware of him, and he was aware of me.

The ceasefire held until the magic moment.

"You're graduating soon."

"Yeth."

"Have you chosen a college yet?"

"I'm dethiding between Oberlin and Hampshire."

"Good schools. I'm sure you'll do well wherever you go," I said, pouring on the clichés. "I suppose you'll be celebrating graduation."

"Yeth." He looked down, blushing slightly. He was blond-haired, one of the fair-haired Russians. "I thuppothe you know I'm gay."

"I'm not very bright, but I figured that out."

"Oh, you're bright enough, Chethter. You've been watching my ath thinthe I wath a little kid. Now I'm legal, you can do thomething about it."

"Let me think about that and get back to you."

"I'll keep the light on for you."

OK, now that my kids were grown, employed, and both living fifteen hundred miles away; and now that Charlotte was just as glad to get the sex part of our lives behind her (in the wrong sense of the phrase) and had fewer options if she bailed on me now; and since Raffi was legal and jail was off the table--why not?

Now since I am a hypocrite and a double-dealing scumbag, and have no illusions or pretensions, all I have to do is cover my tracks.

Richard M. Nixon, along with others, learned that this is not so easy.

So I set to work. Two business trips (one actually legitimate) gave me an excuse to miss a Friday night at home occasionally. I figured a few bucks spent in this way wouldn't unbalance the family budget enough to cause domestic interrogations. No e-mails and no cellphone calls, text messages or any other easily traceable electronic breadcrumbs. Raffi was interning at a fashion mag that summer, and meeting him on a busy street corner for no more than two minutes would arouse no suspicions.

Plans made, excuses made, room reserved at a big anonymous downtown hotel with a credit card only I could access and then only online, I got the cash for the necessary purchases. Top-shelf Astroglide, a couple of plastic tie-downs, top-of-the-line electric hairclipper, shaving cream, good-quality throwaway razors, toothpaste, toothbrushes, mouthwash, liquid baby soap and a really good enema bag; oh yes, and a few Band-Aids, just in case. I carefully planned for every contingency.

Friday afternoon to Saturday morning. Raffi could spin what story he liked to the parents; short of telling the truth, he could say whatever. I gave Wifey the same story I'd give her three times before, and she took it at face value.

Now when you set up an assignation at a hotel, dear Shrink Noelle, you don't walk in holding hands. You get two keys, go up to the room, drop off the rollerbag with the goodies, go downstairs, meet the hookup on a streetcorner and discreetly pass the second room card. You tell the hookup to go into an elevator with a mob of people, like a bunch of tourists coming back from a day's sightseeing, go to the room and enter quickly.

Yes, there'll be a video from the surveillance cam, but it will last under fifteen seconds, and unless you're planning to imitate Joram van der Sloot, you don't care.

Together at last. No reason to talk. I just pull him to me and we exchange an open-mouth kiss. Time for a toothbrushing session, though. I have this clean fetish.

I make sure he carefully brushes his teeth and washes his hands.

"Now it's housekeeping time," I say, and start to undress him. Off comes the Henley shirt, the low-end designer jeans and the sneakers. His undies are worn and could use a wash, but at least he hasn't jerked off in the last hour.

What a nice, ivory, uncut dick! And a good ball sac, plenty to grab one's attention and other things. Plenty of blond pubic hair, though. Got to deal with that.

"Sit on the toilet."

"Like thith?"

"Farther forward. I need to get at your pubes and your junk."

He obliges. I start with the clippers, slowly, carefully, cleaning as I go. Leave a landing strip on the pubis, but get all the hair on his balls and around his dick. That calls for some Gillette and a steady hand.

"Fuck, I should have bought some aftershave. But then again, the stuff tastes awful. You'll survive without." Scrape carefully. Too much shaving cream is just enough.

"Get in the tub."

He does. I turn on the water, take the Euro-style detachable showerhead and clean off the shaving cream and whatever lingering hair didn't get caught by the razor. Turn off the water and order him, "Turn around, bright eyes."

He does. "Bend over." Shaving his ass is precise work; I turn on all the lights, apply much more shaving cream, and work carefully. No nicks or cuts, and no left over nasty-tasting shaving cream if I want to rim him.

The Russians really put one over on his mom. The scar down the center of his chest, where she had to pay to replace half his heart, looks like World War One in Flanders. Well, I won't have to look at that much where I'll be going. Dry his junk, and we're ready to go.

I've turned the A/C to "low". I hate being cold. I hate having the hookup look like a recently plucked chicken.

I put him on the couch, leaning back so his ass and balls are hanging down and his feet are on the ground. I undress carefully, hanging up my clothing and making sure there aren't any wrinkles. I sit on the floor in front of him, and go to work--or to pleasure.

I very carefully lick the inside of each thigh, avoiding any contact with his junk. I butterfly kiss across his pubes, and pull a little at his landing strip with my fingers, causing enough pain to get his attention.

His dick is stiff, so time for the first course. Now everyone talks about deep-throating. That's fine if you like that sort of thing. I don't, and as I'm paying, we'll do it my way. Carefully pull back the foreskin, lick off any smegma, swirl tongue around dick, swirl mouthwash and spit into coffee cup thoughtfully provided by the hotel, and go to it.

He's moaning as I suck him, not taking it all but concentrating on the mushroom and the glans. Plenty of saliva, plenty of tonguing, play with the balls, giving them a light squeeze to keep his attention focussed.

Now suck hard, he's going to come. More saliva, more motion, and as he tries to sit up to grab my head, I wait for the first spurt of cum and bite his dickhead, and bite and bite as he comes.

A natural! He comes like a firehose. Some guys don't like the toothy ending. Too bad for them. I didn't mention I had the thugshocker ready. It's highly illegal, but does curb the overenthusiastic to the extent of 50,000 volts.

"That wass wonderful," he gasps.

"The best is yet to come," I reply, smiling. "Have you ever been fucked?"

"No."

"All you got to do to like it is try it. But first, get some rest. I'll order dinner."

"Can I eat you?"

"Maybe. We'll see." I frankly do not like being eaten. I prefer throwing a solid fuck into an ass or pussy, as the case may be.

Carefully getting dressed, I head for the big avenue outside, find a reasonable takeout, and bring back dinner.

He can't keep his hands away from me. I very sternly tell him to concentrate on dinner. He gets playful. I tell him to cut it out or he's gone.

Now when dinner is over, and he's recovered from orgasm number one, I clean up after the meal, clean myself, and start to clean him up.

Did I mention I prize cleanliness?

So into the bathroom for him, a thorough handwash and cockwash, and now to deal with the inner man. I fill the enema bag with warm, mildly soapy water, lube the tip of the syringe carefully, and bend him over.

Giving someone an enema is almost as good as fucking them. You have all the control. They are submitting to you utterly. And you alone can give them the ultimate release--an explosive emission of shit.

He must be bursting. He's grunting and spasming. I pull out the syringe, and sit him on the pot. I reach down, grab his balls, and squeeze. "Now!"

I hear the cascade of water, interspersed with the concussion of shit. I flush while he sits there. No need to get housekeeping up with a plunger. More shit. Finally just the last dribble.

I pull him up and turn him around to wipe. A tiny soap bubble pops from his asshole. "Bend over," I order, grab a big wad of toilet paper and go to it.

Shit on my dick disgusts me, and forget about shit on my tongue!

We walk back into the room, and he asks "May I thuck you? Pwease?"

I strip, and give him a chance. He isn't bad, I suppose, but I really don't care for it. You know all the porn stories make a big deal about blowjobs, but they're overrated. Like fancy French restaurants.

Now fucking someone up the ass is something else. Wifey only let me do that twice, and that was thirty-five years ago. Fantasy and jerking off may be all well and good. But at the end of the day, easing my Ricardo into a well-lubed, well-cleaned, tight little rosebud of an anus is better than anything.

Raffi delivered the goods. "No one ever did that to me before," he said.

"I'll go slow, I promise. Now get on the bed and lie on your side."

I figured the Spoon Rover Anthology was the way to go, and put down some towels in case things got intense (when you open them up, any residue of the enema can spill out, and it's messy). I got the Astroglide, filled a finger and inserted.

Raffi grunted. Pulled out finger, lubed more extensively, inserted more intensively. A moan this time. Good.

Time to double up. Two fingers loaded with lube, and a firm thrust past both knuckles. I felt a solid anal "wink" from his sphincter, but no objections from the owner thereof. Time for Mr. Brown, that great old Chicago pitcher Mordecai "Three Finger" Brown (honest, there was such a guy). Three fingers with lube and good wishes, thrust home in the style of Cyrano de Bergerac.

"Ohhhhh."

Why delay? I lubed up the essential implement, spread his cheeks, and inserted. Slowly I penetrated, going only perhaps a quarter-inch at a time, giving him time to adapt and adjust, to become better acquainted with the way he would be spending the best part of his adult life.

Oh, so tight! He was a virgin, and I was in no way minded to miss this opportunity to go where no man had gone before. I began to thrust seriously, and reached around his slender hips to grab his dick and rub it. I doubted he would come from this, but I showed my heart, as well as my cock, was in the right place.

I was able to get my fingers on his balls as I started to come. I gave them a squeeze and buried my shaft in his colon, squirting a good load and screaming. I love sound effects.

I guess I impacted his prostate, because he shot a round in a good cause as well.

He wanted more, but I wanted sleep, and we parted in the morning, early. I dumped my equipment in a sidewalk garbage can, and went home.

He went to Oberlin. I never saw him again.

My shrink remarked, "All right, Chester, now was that another fantasy or was it real?"

estragon
estragon
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3 Comments
AnonymousAnonymousover 11 years ago
I agree....

Chesther, with the firsth comment. Pleath get an editor. Thanksth!

estragonestragonover 11 years agoAuthor
The Funniest Comment I Ever Got

Laugh Out Loud.

AnonymousAnonymousover 11 years ago
You need an editor.

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