Cuckolding

One of my favorite assigments in my arsenal of services is cuckolding.
Its also on the very end of my straight spectrum of services.
Cuckolding is highly visual and a cool fetish, for me to be involved in. It takes a very strong man to watch and secure, there is a kind of homoerotic vibe to it though and more often than once has the submissive male turned out to be somewhat bi. Or atleast a muscle worshipper of sorts, kind of how some men live through athletes making them heroes.

Cuckolding is when a man watches another man fuck his wife or girlfriend, something that's his. I have done it many times but often I have to team up with a female that I bring to complete the fantasy. So I was so happy when I got contacted by a Jewish couple out of Brooklyn.
It was her birthday and she wanted to try out someone big. I got the sense that it was more his fetish but it is cool.
I saw some body pics of her and spoke to her on phone to confirm. We meet in midtown for a quick introduction. He and I only, I didn't see her but I had spoken to her but I was getting nervous. He asked me questions to see if I was normal and I passed. He said she got shy in last minute and he asked if it would be ok if we started slow with a massage. I agreed, I wanted to work. He took me to his black SUV and we rode out to his residence in Brooklyn. He was about 5'6 189 lbs in mid 30's and balding, nice guy.
The neighbourhood was all Jewish. Like Hisidic Jewish its the first time I ever been in a Jewish neighourhood and it was kind of cool,they must be some freaky Jewish people. THIS IS AWSOME I thought. He ushered me quickly into the apartment building.

A beautiful two bedroom apartment, very new. He told me that this was just a temorary residence while their house got built.
I was getting little nervous becasue the wife was nowhere in sight.
I got a rum and coke and while watching ESPN, the bedroom door opens and out comes this hot ass tall dark haired girl. She has legs for days, huge fake boobs and is dressed in a white bathrobe.
Her cleavege is out of this world and her face so young looking. The husband,Phil introduces me to his wife Rebecca. She is 19 years old ! I shake her hand as she is blushing and she sits down in sofa between me and her husband. Phil starts to explain the agenda, she is very shy I recon but keeps starting at my arms and chest making me flex subconsiously. I on other hand is feeling a rush of blood towards my lower regions and a familiar swelling as I try to keep my eyes on her face instead of her huge boobs that's attacking my focus. I fail miserably.

"I want you to massage her, while I watch, and strip for her. Be her private little present, can you do that?" I nod off course I can. I can't strip for shit really.
But for her I will do anything, I love nice boobs, fake or real. I don't care, she looks amazing.
" You have a big cock right? " he asks. Guy is a serious vouyer or bi, I nod as Rebecca lowers her head and smiles and blushes. " She wants to feel it and have you rub it all over her" he continues and kisses her.
Its strangly bizaree and kind of creepy, but I am already rock hard.
Another drink and I am ready to go, clocks ticking, time for a show.
Turn the TV on to 90's soul and I begin to undress.
Strip dance, do my best. Rebeccas eyes are focused on me and so are Phils. That makes me feel a little awkward. He starts to touch her and sneaks one hand under her robe, perfect titts, no bra. Someone has paid for that body. I could make allot of money with her as a live show partner, she is a doll.

I feel awsome when he leans in to kiss her and she stays focused on me. I don't care about him as I unbuckle my belt and her eyes turn big. Guess this is what she been waiting for, male escort tool.

"Ready for massage?" I ask her as I unzip and I am down to my white abercrombie boxers.
" Yes ( giggling)" Phil is touching himself. I point towards the bedroom.
They have a massage table set up already and oil.
Perfect.
There is this moment of silence as we all are waiting to get naked,watching each other. I am feeling butterflies in my stomach, since Phil is outstretched on bed watching me. Im going to put my hands on his wife in a couple of moments. Don't know how far I can go, what I can do. Its his wife for fucks sake and she is fucking hot. How the fuck did a 35 something short guy land an 5'8 vixen.
I start slowly pull of my boxers, she follows my lead and of with bathrobe.
" Where do you want me?"
I point to the table she is naked, my heart is pumping hard in my chest, thoughts racing. She has an incredible body, like perfect. I never seen anything like it." On your stomach" Phil doesn't exits for me anymore and is totally blocked out as I lube up my hands with oil and start massaging her shoulders. Gently at first, she gives out sounds as to guide me with the touch she wants.

This is fucking hot, I slowly work my way down towards her apple bottom, I want to make this last. I want to be the best masseur she ever had, I want to come back !
She presses her butt up a little in the air as I start working on her cheeks. Inbetween her legs, up and down her inner thighs.
Suddenly Phil appers in the picture again. He has pulled down his jeans and is jerking off and making noises." Baby touch his cock, touch it" he pleads. Destroying the fantasy of me and Rebecca being alone. Normally I take pleasure in being watched but not now, not with her. This sucks and I think Rebecca thinks so too as she turns her head towards Phil.
" I don't want to" I am getting softer as it feels like my inflated cock suddenly been pierced by her words, but then she continues" not while your her baby, does not feel right. This was supposed to be about me, could you please leave ?" Wow what did I start? I don't know how he will react? Will he be pissed? Crushed? I suddenly feel a sting of symphaty for him, like he is sidelined before the big game. This is his fantasy as much as hers I figure. Will I have to fight with him? Will they fight? Most of all will I get paid if he decides this is bullshit ? Phil looks at me and at her I raise my shoulders, "it's the same for me, Phil I mean, im a masseur so.." What am I supposed to say? On one hand I want to be alone with her but not so obvious and buisness first he has the money stay loyal to the money.
Phil smiles half defeated" anything for you baby, anything for my darling." Jumps up and pulls up his jeans and kisses her while watching me " I will be just outside incase you need me hunny? Ok?"
"Ok baby, love you"
''Love you "
He leaves door open half cocked as he leaves.
As soon as Rebecca hears the TV volume change and turn back to ESPN she turns around.
Shaved pussy with a string, I love it, mountain peak type breast perfectly round like a plastic mannequin. She spreads her legs a little, I take that as my que to lube up again. Drip some oil in my hands.
I am massaging her shoulders, down between her breast, standing with my cock next to her face. This is amazingly hot and I am instantly hard again. I just want to be a beast and shove my cock in her mouth cum on her tits but I am shy suddenly. Her fucking husband that hired me is in next room.

I start to massage her between her legs, inner thighs, she pushes her pussy against me. Its hard to control myself. I can't belive I am getting paid for this ! I keep thinking, touch my cock, please touch my cock ! I don't know what psychic powers I have but as soon as I move to the "happy ending part" she feels me up.
God my cock feels so good in her hand. She strokes me slowly, milking my cock keeping tempo as I insert my fingers in her and play with her clit with my right hand. I meet her eyes and she moves her right hand to her lips and leans forward, about to suck my cock but stops. "Hunny is everything ok?" Fucking Phil man, dude I am about to get head ! She says yes everything is perfect. He asks what we are doing. She just shakes her head apologetichally to me. I smile," Hunny is his dick bigger than mine?" I hear pleadingly form the adjecent room, that almost makes me laugh, Rebecca also, but its so sweet and innocent. " No baby, not at all", she then rolls her eyes backward, leans back and lets me continue to work her.
I press my fingers deeper and push down on her stomach as I pump my fingers deeper in her wet pussy, while massaging her clit with my free hand. She starts to bite her lip as she humps me back, faster and faster breathing heavy. I feel her contractions as she burries her nails in my ass and the side of the table. She comes, not loudly, she could have but out of respect for Phil I think she didn't want to. I did notice how the volume on the TV got louder and louder as she got closer.
Poor Phil, its always like that. When your trying to block a sound out that sound gets magnified, I feel for him. Maybe he wasn't ready for this after all.

She looks at me and smiles as I pull out my fingers and lick them, she tastes like strawberries. She is resting herslef on her forearms and glows. I want to cum and start jerking of, I can cum fast. She watches me, smiling. I put one finger against my lips, "hush". I move my cock against her breast boldly and she pushes them togheter for me. Leans forward, I cum all over her perfect tits and she rubs it in so it won't show. I don't tell her she got some of me in her hair also.

Done, that was fucking hot. I dress and she puts the robe back on again.
We join an ESPN watching Phil in livingroom.
Its a weird silence, my fee is on the glass table seperating us. I have another drink that has been prepared for me on the table, atleast he is a good sport. We chat and I say that I would love to come again and mention that I know girls also for couples massage. I say that to make Phil feel better but he says no, this was perfect! I suddenly understand, he is a cuckold, he has all the money, all the prestige and does anything for his honey.

She gets to play and be with others. As long as they do it together. I thought he was upset, but he loved it, the humiliation, submissiveness.
"Next time I want you to fuck her" he says, I almost choke on my drink and begin to cough. " Next time I would like to do that too" I say.
" Would you like that baby? To fuck him, his big cock? "
She looks at me and smiles kisses him on cheek. This is insane, but strangly hot. I ask what he does, he is a lawyer she models. I nod to that. They all modell when they are young and hot but she could pull it off. She is just a glamourized sugarbabe I figure. But Phil jumps up he can maybe sense I don't belive him and goes into his home office.To pop out as suddenly with a headshot and a couple of photos.

Playboy fucking photos!!!!
She is in Playboy!!!
Fucking cool, I just got paid to be with a girl people would pay for.
I try to look blaze as I go through the photos but im starstruck. My first mastrubation was to my dads hidden Playboy magazines. Fuck many guys first mastrubation was. I want to ask so many questions about the mansion, if she meet Hugh Hefner, the grotto. But I can only stare at photos, blank, mind fucked.

Eyes movin back and forth between Rebecca and the images with open mouth in amazement.This is so cool.
She signs one photo for me and kisses it.

I can't wait to tell all my friends about this.
I am the man. Before I leave, Phil asks me, " hey you do coke? You party?" I don't know what to say don't want to blow my chances to come back by being a junkie I done cocaine before allot to extent I ended up homeless.
So I ask why? He says she gets it for free all the time but does not use it so I can have some.

This turning out to be an amazing night !