My work as a male gigolo has become even more exciting after I connected with two women, Agnes and Briana the founders of what is now a small chain of ‘glee clubs’, a euphemism to soften what is an an uncomfortable topic for some people, Premier League sexual activities.
“Some of our members will probably want you to meet and have a three-way with you and their lovers, female and male. Would that be a problem?, the founders of a small chain of clubs asked me.
Agnes and Briana were the founders of what is now a small chain of ‘glee clubs’, a euphemism to soften what is an an uncomfortable topic for some people, sex outside marriage.
They told me we call them ‘glee clubs’ so husbands and lovers won’t be suspicious of our real purpose. I had met them through an assignment my agent Ada had arranged.
“We were always good at organising things. Our members are always very discreet, We like to position our small club as the Premier League of organisations involved with sexual pleasure. They may expect you to do a range of things of a sexual nature you haven’t done previously that you may be uncomfortable with initially, such as sucking a transgendered man’s cock. Though bear in mind our members pay way over the rates and fees you have been earning with Ada.
“Some of our members enjoy the exhibitionistic thrill of having sex in front of other women. Others enjoy the voyeurism of watching other members having sex. Some members join our club to meet with new partners, while others go to play with strangers. Some of our parties are designed around a certain theme, like a masquerade ball or bondage.
“Some of our members will probably want you to meet and have a three-way with you and their lovers, female and male. Would that be a problem?”
I am Michael, in my late twenties, 72 inches tall, 168 pounds, a toned, fit body and genetically lucky to possess a large, thick cock, ten-inches when erect. I live in Sydney, Australia and used to moonlight as a gigolo or male escort.
That was before Ada asked me to work for her ‘exclusive agency’. “We have a wide ranging client list, males and females, and lots of constant work,” she told me as she auditioned me. “And we provide for some very kinky people, even famous people with lots of sexual fetishes.”
I quickly learnt Ada had a niche clientele of older women who enjoy watching their toy boy, lover or husband giving a blowjob to a younger well hung gigolo after they have watched her fucking him. It can be incredibly exciting for me if the woman is actively participating, a three-way, even more exciting if the woman has a sexy persona and a good body.
It wasn’t a problem for me visiting members of the glee club in their usually palatial houses, more often than not being picked up and driven there in a limo, before three-ways with them and their lovers, female and male.
The first time I had a member of the ‘glee club’. was memorable from the moment the driver drove the limo through the security gate into a huge estate with manicured gardens surrounded by a high wall, along a winding drive to a palatial house.
I was greeted by a young girl Cherie, around twenty-years old, a gorgeous size-8 blond, a super confident dolly bird, dressed as a schoolgirl in low heels and a short flared skirt who led me to a lavish bathroom before she handed me a designer bag containing some clothing.
While she sat and enjoyed watching me shower she explained the house was owned by a wealthy industrialist and his wife June. The husband was away and the wife wanted to entertain her lover and me that day while she watched. All the while trying to ascertain what her relationship with June was, who I hadn’t yet met.
I enjoyed flaunting my naked body for Cherie while watching me shower, teasing my cock for her, asking me lots of questions. “Are you really a stud for hire? Is your cock really big when erect? Bigger than most men? And thick? Is it true you enjoy men giving you fellatio, sucking your cock as long as another woman is watching? Is it true you can get it up two or three times in a session? Did June really pay you three-thousand to be here today?”
While Cherie helped me dry off she filled me in on some of the details for the day, “June told me to prepare you for her and her lover, to oil your body, to give you an erection,” as she smeared oil all over my body with her wonderfully soft hands, my back, my legs, my ass, my torso and finally my partly cock, taking great delight in teasing my cock to a full on erection, enjoying a young girl’s hands on my erection.
“June told me she was expecting a well hung thirty-year old man. She didn’t tell me you were that well hung though. You are awesome, huge and so thick,” she told me as she ran two oily hands along my erection, placing it against her arm for comparison.
Cherie sorted through the items in the bag, offering me a range of exotic cock rings from the bag, sliding the one she chose along my erection, then clipping to nonchalantly around my balls. Asking me which g-string I preferred as she helped me *********** the smallest one in the bag, clipping it on for me, my erection bulging out of it.
Tongue kissing me, telling me nonchalantly, “When June is finished with you she promised I could have you, fuck you. I have never had a man as big as you.” before she took my hand and led me to June’s bedroom.
Cherie made the introductions, “This is June and Janice, Jan for short,” as two women greeted me, June topless wearing a short leather skirt and heels, with a magnificent pair of tits on a size-14 body,
The other woman Jan, with her back to me, a slim size-10, topless, wearing heels, stockings and a garter belt framing her beautiful ass, before she turned to show me her even more beautiful, large flaccid cock, a wonderful match with her partners big tits.
June quickly took control, giving me her tits and nipples to lick and suck. Sliding my erection over one of nipples while Jan, her tranny lover slid her now impressive erection over the other nipple. Jan sucking the tip of my erection, touching her erection against mine. June indicating me to fuck her on her bed, surrounded by mirrors, with Jan alongside her.
As part of my job de***********ion I had given a tranny fellatio, a head job, sucked a tranny’s cock a number of times, invariably with another female or male watching. Though never while fucking another woman as I was that day.
So much more exciting with a young girl watching, a girl who wanted to have me later. My introduction to premier League sex. My ego and my libido sky high while Jan and June talked to each other. Cherie sitting close by watching intently.
Later I was sitting on the floor with a cushion under my ass when Cherie stood in front of me, naked apart from her heels, her gorgeous young legs spread for me, while I admired her small pert tits and all over sun tan. “I told you June promised when she was finished with you I could have you, fuck you. I have never had a man as big as you.”
Whispering loudly, “Fuck me with your tongue while my aunty and uncle watch,” as she offered me her beautifully trimmed cunt lips. Our only contact the tip of my tongue on her clit while she was looking down to watch my cock growing for her.
And have me she did with June and Janice watching. Telling me in a whisper, “I have never fucked a man as big as you, and you are so hard for me,” as she licked and sucked the tip of my erection.
Laying me on my back on the floor, Cherie sliding her tight wet cunt onto my erection, using me, fucking me for her sexual pleasure with her aunty and uncle watching.
Shortly after Cherie and me commenced fucking, Jan (Janice) gave June her cock to pleasure. A wonderful extra turn on watching an incredibly sexy woman giving a head job to her tranny lover. Her second head job for the session. A group four-way. This really was Premier League sex.
A week later a I was in a lavish penthouse in the centre of Sydney overlooking Hyde Park and the harbour, to meet my new client, a member of the ‘glee club’.
When I arrived, two young boys, barely twenty-years old, almost naked wearing skimpy black leather male g-strings, greeted me at the door. Both with obvious all over sun tans as I ogled their fully exposed ass cheeks.
Explaining with a wicked grin they were Elaine’s financial advisors as they led me inside to meet Elaine, both boys with a hand on my ass, accidentally brushing my crotch as we walked.
Wonderful first impressions, my client Elaine was an exciting, glamorous brunette cougar woman, with a very fuckable body, laying on a couch. She must have been close to fifty, wearing a floppy black hat, leather gloves, a full length black leather coat, open enough to show some wonderful cleavage, her legs cased in black stockings, crossed to show lots of wonderful bare thigh above her stockings. The reason for the gloves didn’t become apparent until later.
“Hello Michael, welcome to my penthouse, you have already met my two boys. They helped me prepare for you. Do you like what they chose for me to wear for you while they watch me seduce you? They have a thing about black leather, so do I.”
The two young boys, barely twenty-years old were standing alongside her, ogling my almost naked body as they watched me undressing for Elaine, and for them. Always a buzz showing my large cock to a new female lover, an extra frisson for two young boys at the same time.
Elaine had forewarned me she wanted to watch her toy boys have me, give me a head job, after she had me while her toy boys watched. Asking me on the phone to confirm I was okay with her request while I looked at the pics of her toy boy’s she had sent me.
Telling her, “Yes I would be fine with your request,” as I studied the pics. The final pic of the woman Elaine and one of her boys, his huge cock between her lips, while the other boy was watching and masturbating.
Elaine looked so fuckable laying on her back on her bed, naked apart from her heels and black leather gloves. The two boys close by on either side of the bed, my exhibitionist streak enjoying Elaine and the boys watching me stroking my erection to a full thick, ten-inch erection for the three of them. The three of them watching my slide my cock ring on, clip it around my balls.
The boys watching Elaine and me kissing passionately, licking and sucking her nipples and tits. Briefly tongue fucking her, one thigh over my shoulder. Elaine moaning, “Oh fuck yes, give it to me, fuck me,” as I slowly slid the full length of my erection her.
Glancing up as the boys released their erections from their leather g-strings, Elaine reaching out to grasp each of their erections with her hands in soft leather gloves. Masturbating the boys as I continued fucking her. Making sure the boys could see almost my entire erection sliding in and out of her as they watched me fucking Elaine.
Continuing to fuck Elaine long after she bought the two boys to orgasm with her leather gloved hands. The boys watching in awe as she had three small orgasms before we fucked in a frenzy, both of us wanting to orgasm in sync. Talking dirty to each other, building to a noisy crescendo before we orgasmed in sync, hardly aware of the two boys watching with new erections.
A little over an hour later we were all showered and refreshed. Elaine naked apart from her heels and a black leather jacket. She had found a black leather g-string for me to wear, a lovely feel with my ass exposed, the boys also wearing their black leather g-strings.
Elaine had forewarned me she wanted to watch her young boys have me, give me a head job. Something I had been perversely looking forward to after I had confirmed over the phone I was okay with her request.
Wonderful sexual tension as Elaine and me were sitting alongside each other on her leather couch, the feel of the leather on our bodies with naked ass’s an added frisson. The boys sliding on black leather gloves as they stared at me.
“You are a challenge for us Michael, we have never had a man as big as you,” one of them told me as he slid my cock and balls out of the opening in the leather g-string. Teasing my cock to erection with his soft leather gloved hands. The other boy alternating teasing my erection with his gloved hands. Sucking my cock simultaneously. So good, a completely new sensation with a cougar woman watching her boys.
Elaine kissing me with her tongue while she watched her boys. “Are they good Michael? Have I trained them well?”
All I could manage to say in response was, “Incredibly good, so fucking good,” As they teased my erection. I had never had a hand job from two boys wearing soft leather gloves smeared with lube.
Elaine kissing me again with her tongue while she watched her boys. Asking again, “Are they good Michael? Have I trained them well?,” while one of the boys was deep throating me. Premier League sex.
The following week an assignment with another ‘glee club member’ in an eastern suburbs waterfront mansion. Cressida was a most attractive brunette woman in her forties with a voluptuous body. She had a boy and girl with her, just over twenty-years old.
Brief introductions, the three of us realising we were here to explore and experience Premier League sexual pleasure at Cressida’s request. Unsure how it might play out, or what she expected, waiting for someone to take the initiative.
The young girl undressing me without saying a word. Teasing my cock with her fingertips, arousing me. The young boy ogling my engorged cock while undressing Cressida our hostess. Her voluptuous body looked so fuckable in heels and skimpy black lingerie after the boy helped her remove her dress. Cressida and me looking at each other, lusting after each other, she had obviously set this up as foreplay for the four of us.
Cressida undressing the boy while I watched, with his girlfriend watching on. The three of us admiring the boy’s toned, naked body and large erection. Cressida motioning for me to undress the girl. My cock reacting to her young, naked body, firm tits and gorgeous tight ass.
The boy and girl fucking like rabbits without any further foreplay while Cressida and I watched, two voyeurs turned on by a young couple making love and fucking. Wonderful foreplay for us watching twenty-year olds fucking. Both of us admiring their young tight bodies.
Cressida’s hand on my erection, as I teased the insides of her silky thighs, kissing with our tongues while glancing at the boy and girl making love and fucking, almost oblivious to us. They were obviously very experienced together, changing positions to heighten their sexual pleasure. The girl whispering, “Fuck me, fuck me, fuckame,” before she orgasmed in sync with the boy.
“One of my girlfriends told me about your ass fetish Michael. Does my ass look big? Do you like it?,” Cressida asked as she stood so I could lick and kiss her generous ass cheeks poking out of her skimpy thong.
“I love it, magnificent,” I told her, my hands grasping her generous hips, the boy and girl watching goggle eyed as I slid her thong to her ankles. Licking and kissing her magnificent ass some more. Briefly satisfying my ass fetish.
Cressida turning around, legs spread in her heels, whispering, “Fuck my cunt with your tongue.” Grasping her hips as I licked her shaved pussy. So good, this woman was so much more than an exciting sexual challenge.
Fucking Cressida doggy style while the boy and girl watched, Cressida enjoying them watching even more than me. Talking to them, asking if they liked watching. An extra turn on for both of us. The boy watching with a new erection. Changing to missionary position, the girl telling the boy, “He really is ten-inches, and so thick, as I slid the full length of my erection in and out of Cressida for their benefit.
So pleased I managed to bring Cressida to orgasm twice with my erection deep in her, before I orgasmed, so good with the boy and girl watching and enjoying.
In the after glow Cressida led the three of us to another room, a combined shower and sauna with wooden seats. The four of us taking it in turns to run the hand held needle spray shower over each other’s naked bodies. Cressida the hostess, choosing the boy first up, running the needle spray over his ass, his nipples before focusing on his erection, then over her pubic area, a subtle hint for the boy.
When it was the girl’s turn to use the needle spray she turned it on my ass, nipples then my flaccid cock, alternating running it over her pubic area. Quickly gaining a new erection while Cressida and the boy watched on. Handing me the needle spray, running it over her nipples, cunt lips, then her ass. Licking and kissing her beautiful young ass cheeks. Briefly satisfying my ass fetish again.
Wonderful sexual tension, kinky sexual tension, the boy and I sitting side by side on the bench seat, admiring each other’s erection. Cressida smiling and nodding her approval as the girl eased herself onto my erection, her back to me so I could grasp her ass, her boy watching, not sure if he was envious or jealous as I studied the look on his face and his rock hard erection.
Cressida moaning, “Fuck yes, yes,” as she lowered herself onto the boy’s erection, her back to him so he could grasp her ass. Leaning over to kiss me while fucking the boy. The girl leaning over to kiss Cressida while she was fucking me. One hand on the girl’s ass, the other on Cressida’s ass, an incredibly exciting four-way.
Other than an exciting and kinky sexual relationship, I never did learn what the connection was between Cressida and the girl and boy, a couple half her age. Perhaps I might find out when I visit again soon for Premier League sex?