Jack and Bernard and Jimmy

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Status: In Progress  |  Genre: Humiliation Sex  |  House: Stripping and Humiliation

Jack, a wily voyeur, sets up his re-occurring friend David, who drops by and takes his clothes off on a regular basis for Jack's pleasure.

Jack decides to spice up things by ambushing David. He enlists his friend Bernard, and his next door neighbor Jimmy to "drop by" during one of David's visits, Jack doesn't inform David that on this particular day, he'll be looked at, intimately, by three fully clothed men.
Jack knows David is already embarrassed by his naked visits but that David cannot stop doing them.
Jack plans to humiliate David to the maximum.

"He's a very wholesome, cute YOUNG man," Jack told Bernard over the phone. Jack was in his apartment in Manhattn; Bernard was in his office, also in Manhattan. Jack's neighbor, young Asian Jimmy, was alongside Jack on his couch, listening in since Jack had Bernard on speaker. Jimmy and Bernard were acquainted. Bernard was alone in his office; everyone else had left for the day.

Jack was a masculine businessman that worked from home. He resembled Tom Selleck. Bernard was distinguished, fey, a bit doughy and resembled the old queen aa the local gay bar who got loud during happy hour. Jack and Bernard were both in their mid-forties. They had been friends for a long time, but they had never been lovers. Bernard has longed for such a development, but he knew  he was not Jack's type.

"He just comes over and takes his clothes off and MASTURBATES for you?" Bernard chuckled over the phone. Bernard found this scenario extremely provocative. Bernard was strongly into CMNM fantasies. Bernard knew Jack had  the same fetish for this type of thing, and that this young man David was not the first to come over to Jack's and display his wares. There had been someone named Allen, Bernad recalled. Bernard never got to meet Allen, although he had prodded Jack to allow him to watch Allen "perform." They never got atound to it, Allen stopped visiting for some reason.

Jimmy, an excitable type, said, "Oh my goodness."

Bernard grimaced on his end. He had met Jimmy at an intimate get-together at Jack's apartment. Bernard knew Jack had platonic affection for Jimmy. Bernard found Jimmy somewhat unbearable, but he kept his mouth mostly shut about that.

Jack replied to Bernard, "Yes. That is our arrangement. You know I had that guy Allen do the same thing."

"Oh yeah, you're reading my mind, Jack, " said Bernard. "Whatever happened to him?"

Jack chuckled. "I had Jimmy here drop by during one of our sessions. It was totally spur of the moment. Allen couldn't handle two sets of eyes."

Jimmy squealed, "OH THE ALLEN OH MY GOODNESS!"

Bernard was aroused. "Tell me about this David."

"As I said," Jack continued, "He is very attractive and does not entirely seem to realize it. He is not exactly muscular, but he is quite masculine and has a fine toned body. His penis is smaller than you'll probably appreciate. He is very likable and I like to see him  naked. But his penis is not big. I know you are a size queen, Bernard."

Jimmy: "Oh my goodness I love small penis."

Jack went on, amused, to Bernard: "David is blonde. He has a magnificent ass, one of the best I've ever seen. He has a very nice pair of pecs and really lovely nipples. Believe it or not, he is shy, even he does this type of thing."

Jimmy: "Oh my goondess blonde, ass, nipples, shy."

Bernard said to Jack: "Take me off speaker."

Jack did so.

Bernard: "Can the ditz next door hear me now?"

Jack grunted. "I don't believe so."

Bernard sighed then he said: "What exactly do you have in mind, Jack? I will help in any way I can."

Jack confided, "I thought, I'd have him come over as usual and tell him in advance to leave the door unlocked, which is not our usual routine. We usually do not speak during these sessions, as I give him his instructions either by phone or through email. He has a very pleasant voice, kind of Andy Hardy-like, all innocent and such. It matches his personality, and especially, his naked body. He will probably be a little suspicious about the door aspect. I'll havel him disrobe as usual, which he does kind of slowly, and get on the mattress, nude, and then get on with his business. Then, you will enter. We'll time it perfectly. Be sure you wear a suit. I always wear a suit. The scene works better that way. Clothed man in a suit, naked man playing with himself shamefully. in the middle of the afternoon. The scene is usually at first a little tense, because he knows he'll be naked again and he'll have to cum. I think there's a little performance anxiety going on, which I find hilarious. But I'll tell you this, he ejaculates every time, and it is usually a big load of cum. He keeps his fucking specs on, and more than once he has hit them with his jizz. He wants to fade away when that happens. It's embarrassing for him, erotic as fuck for me. Then he hightails it out of here, looking kind of forlorn and used. I love it, Bernard. I just love David's humiliation and I want to triple it. Allen was strutting and more cocky, and it began to bore me. David can be continually humiliated because he doesn't realize how hot he is."

Jimmy fidgeted: "Allen was vain. HUMILIATION OF DAVID. OH MY GOODNESS!!!"

Bernard: "Wow. How do I make my entrance?"

Jack: "We'll iron that out later. I want to do it in a way that startles David as much as possible. I desire to see the look on his face when he realizes it won't be just me seeing him naked. Seeing him masturbate. Seeing him degrade himself in front of clothed men. He usually begins by touching himself from head to toe. I make him play with everything available. Nipples, arms, all of it. Initially, he is quite awkward even after doing this so many times. I think he feels cheap doing it, which I love. He blushes, profusely."

Bernard chuckled. "I understand. Sounds yummy. Can I touch him, this David? Since you never let ME see Allen." Bernard pouted on the petulance.

Jack laughed and said, "We will play that by ear. You will probably want to touch him. His skin is gorgeous, no tattoos, and he will be humiliated if he is touched. by a total stranger, I rarely touch him, although I have. I think he wants me to, so I make myself refrain. It is not always easy. I want you to make fun of his body as you see fit. Humiliate the fuck out of him for being naked."

Bernard: "I thought you said he had a nice body."

Jack: "Oh, he does. But he will be nude, we all will be clothed, so naturally he will be at a disadvantage. And it will add to his humiliation. THIS IS ABOUT HUMILIATiION, BERNARD. Dave's penis is small. He could probably drop off two or three pounds, and I think he is highly sensitive about all of that. You know how these young guys are about their bodies nowadays. David does have limits. He won't defecate in front of me. It's kind of incrredible David is single. Let's face it, both of us are into humiliation scenes. Opportunities like David are rare."

Jimmy burbled "OH MY GOODNESS!"

Bernard, after a pause: "I love this already. I'm hard as a rock. Is the ditz going to be involved?"

Jack, who was also hard: "Yes. It will humiliate David even more. It totally humiliated Allen. i WANT TO HUMILIATE DAVID COMPLETELY, BERNARD."

Bernard: "Very well. So do I. What are David's tits like? You know I like the titties."

Jack: "You will not be disappointed. They are quite enticing. All of David's skin is nice. He has a moderate tan usually. A tanline too. I wouldn't like an all-over tan. One reason I got disenchanted with Allen because it became obvious he was prancing around Fire Island naked with no swimsuit. I think you also will enjoy David's pert asshole. It is hairless and always always clean. I think he scrubs it before he comes over because he knows he has to show it. And the juxtaposition of David's tan with his milky white ass....well, you get the drill."

Bernard was wet. He most certainly DID get the drill. He liked milky white ass on naked men.

Jimmy: "ASSHOLE! Humiliate.Skin. David. OH MY GOODNESS!"

Bernard: "I can hear Jimmy caterwauling. God, she's so insane. David shows his asshole, does he." Bernard wanted to hear as much as he could today about David's asshole.

Jack: "Yeah, but not very willingly. It is obvious it makes him uncomfortable. So of course I have escalated it. I make him play with it. That was like pulling teeth initially. It's obvious to me it is a virgin hole, although it can expand. That's what makes it hotter. You should see him finger and pucker it. It's hilarious. He's clumsy doing it. He hates it but he obeys me. He can't help his own lustiness to show off his naked body. I've got him trained pretty well. I enjjoy looking at his naked body because he is always always shy. It's psychological as well as crotic. Youl will enjoy yourself. You will certainly not be bored. Mark your calendar the weekend before Christmas. Probably that Saturday."

Bernard: "Consider it done. Wait, is David employed?"

Jack: "I believe so. He's always groomed and always has nice clothes on before he takes them all off. You won't care if he's employed once you see him in the nude flat on his back with his legs spread and his scrotum in full view. His scrotum is fascinating to me. Floppy at first, then as he arouses himself, he tigthtens. And his handsome blushing face. And those tits. You will like David's tits, I guarantee it. And his armpits. David has the most exquisite armpits. Very little hair in them, but they are so beautiful and nuanced. Just lovely. And he doesn't even seem to know it, Bernard. And when I switch on the lamp, you can see every inch of David, naked, in detail. I have told him afterwards how much I can see when I swtich on the lamp, and I can hear the embarrassment in his voice or in his emails. I hold nothing back in my morning after reviews of David's shows. When I put on the lamp, you can see his fucking veins. You can see evertying. So naked. You like rectum? You're about to see a lot of rectum. The lamp shows off ALL of David."

Jimmy was beside himself with glee: "RECTUM OH MY GOODNESS!!!!"

Bernard asked: "What would David say if he knew we were having such an explicit conversation about his naked body?"

Jack laughed: "I imagine he would get very drunk. Didn't I tell you he's a bit naive? He has no idea I discuss our sessions. I've deceived him into thinking the entire set-up is utterly private."

Bernard was aroused and his hard-on was almost painful. He unzipped his fly. Bernard remembered that big lamp in the corner. He said to Jack, "Keep me posted. I am salivating."

Jack giggled. "Don't worry, we'll talk again before we do this. But I think you get the rodeo. Don't forget, I want you to insult him when he is naked. Don't totally overdo it, but I want you to make fun of the situation he's put himself in."

Bernard chuckled, said "I am your man,," hung up and masturbated in his office. Wow. I can't wait for THIS, Bernard thought. I get to humiilate a good-looking younger man. Nuanced armpits? Show me the money. Bernard had a slight fetish for armpits as long as they were maintained hygienically. And he was looking forward to seeing David's rectum. Bernard's fetish for male rectum was not slight. It was enormous.  Especially virgin rectum, and this is what David sounded like. Bernard began to rehearse potential insults he'd use to taunt the naked David.

After hanging up with Bernard, Jack then elnlisted Jimmy's aid in his humiliation scheme of the unsuspecting David.


Jack gave Jimmy money to buy Daavid a special Christmas sex toy. Jimmy giggled. "You don't have to wrap it," instructed Jack. "But make sure it is in the package so he'll know it's never been used." Jimmy screeched, "OH MY GOODNESS!"

Jack would have to consult with Bernard about the sex toy in another hot phone call.

Jack smirked. This was going to be classic. He remembered that David's armpits were oh so sexy. When Jimmy finally left, chattering excitedly on his way to his own apartment down the hall, Jack masturbated thinking about David's body. David's armpits. Daavid's huymiliations. And of course, the rest of David, naked, exposed, embarrassed, since Jack had seen all of bashful naked David, so much so that he could summon the imagery within seconds, and vividly. Jack realized that he had probably and possibly seen David in the buff more than David himself..

The average but enticing penis, perfectly circumsised with an alluring urethrra and visible glans below it. The scrotum that tightened as David approached his orgasms. The unmistakably male butthole. The ass cheeks, pale and vulnerable. The titties, developed but still a little squeezable. The nipples that red and hard and perky. David's handsome cute face when it blushed as he showed himself naked. The explosive porcelain cum loads David shot on his nude body, through the air,  when Jack had switched on his giant lamp to expose David to the max. But David's armpits really got Jack wild. They were boyish and at the same time manly. Jack moaned. He growled as he shot his load.

For a fleeting second, Jack felt a tinge of guilt at the prospect of hosting this upcoming event tor the degradation of poor David, who would be naked (again). Then Jack smiled to himself and had a cocktail. He realized Bernard would be a little vicious as he drooled over David's nudity, and that Jimmy was gonna be like a child with a new toy (a naked, vulnerable David being the toy).

Jack realized he had never sucked David's bared armpits. That was an incredible oversight that would soon be amended.




Submitted: July 03, 2022

© Copyright 2022 davey. All rights reserved.

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Add Your Comments:



I enjoyed 'Jack's Lewd Surprise' so it's nice to get the 'back story.' Thanks.

Tue, July 5th, 2022 9:34pm


You're welcome. It brought back memories, I'll tell ya.

Wed, July 6th, 2022 1:44pm


Where is the sequal, I want to find out what happens

Thu, July 21st, 2022 2:53am


Jack and Bernard and Jimmy IS the sequel (or more accurately, the prequel).

You can find "Jack's Lewd Surprise" on the same website. It's a few months old, so you'll have to scroll down in the content section.

I hope you enjoy it.

"Jack's Lewd Surprise" was written first. "JBJ" was a follow-up.

Thanks for your feedback. Always appreciated.

Thu, July 21st, 2022 10:54am


But yoy didn't get to the part where David comes over

Sun, July 24th, 2022 12:30am


David comes over in the story "Jack's Lewd Surprise."

Believe me. I know. I am David. The story should still be on the site.

"Jack and Bernard and Jimmy" is my imagination on how those three guys planned my ambush.

"Jack's Lewd Surprise" was posted months ago, but last time I looked, it was still there, much to my embarrassment. But I thought it was best to share with anyone who might want to hook up with voyeurs.

You will get what you ask for.

Sun, July 24th, 2022 4:21pm

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