A few days previously my agent Ada had told me, “I have an older lady who wants to share you with her toy boy on Sunday. Does that work for you?”
On the Sunday afternoon I arrived at a lavish condo, a change from most of my assignments in expensive CBD hotels, carrying a small bag with some essentials for my sexual assignment - some cock rings and some spare jock straps. Trent, the toyboy met me at the door as we looked each other over. He was a pretty blond boy, very pretty, early twenties, though not quite the macho boy I expected. I was pleased at the attention he gave me and the way I was dressed in tight slacks and a jacket with just one button fastened, no shirt.
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 with lots of sexual fetishes.”
My agent Ada has a niche clientele of older women who enjoy watching their toyboy, 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.
That day wasn’t the first time I had entertained an older woman with her toy boy, though I had a feeling this was going to far more memorable than others.
“Suelen and I have been looking forward to your visit, me especially,” Trent told me with a nervous smile as he ogled my almost naked chest, then my crotch before he led me inside. I looked closely at him for a second time as we entered the condo. Is he really a toyboy or a young girl, either way he was incredibly pretty, honey blond hair in a pony tail, dressed in cut of shorts, so short his ass checks were on show. And the best pair of legs I had ever seen on a boy.
Would I be comfortable with this boy giving me oral sex, sucking my cock?, something he obviously expects with the arrangements I agreed to, I asked myself as he led me inside.
“This is Michael, Suelen,” he offered by way of introduction as Suelen appeared dressed as a wealthy corporate executive would. A good looking woman, size-12. a class act, just past forty, taller than average, bobbed blond hair, a good figure and ass and a beautifully cultured voice I learnt as she spoke.
“Trent is my protege, he is a very talented boy for one so young, he is more than twenty-years younger than me, He is also very experienced for one so young,” Suelen told me as we looked each other over as she settled on a couch and seductively crossed her legs.
“He took great trouble when making the arrangements for our meeting today. He wanted to ensure both of us obtained maximum pleasure, sexual pleasure, from your visit and our needs were met. He told me you have a very large cock Michael, something Trent and I both want to share. He also told me you are reputed to have an ass fetish Michael. I hope that is true.
“Now go and get dressed for Michael and I Trent, the outfit I picked for you earlier.”
Before he returned Suelen had taken the initiative as we were tongue kissing after she removed my coat.
“Well hello again Michael, I do like dressing up for our guests,” he told me as he appeared in heels, he wore them well, incredible feminine legs with well formed thighs, then a short, black cocktail dress, so short his ass cheeks were almost visible.
“We were not sure what I should wear for you today, Come into my dressing room and Trent can show you some of my outfits and help me change for you,” Suelen told me.
“What would you like me to wear for Michael and you Trent?,” she asked confidently. “You told me he is reputed to have an ass fetish, we both hope that is true.”
“What can you wear for me and Michael to showcase your magnificent big ass Suelen?,” Trent replied rhetorically as he lifted her skirt, slowly to expose her naked ass. “Forty-two inches of hips and ass for us Michael,” Trent whispered in a raspy voice.
“You know I love your naked body and big ass in nothing more than a tiny black g-string,” Trent told her as he handed one to her.
I had an almost full erection under my trousers as I watched Trent undress Suelen, these two people, with an age difference of 20-years, had huge sexual chemistry. She was tongue kissing me as he helped her on with the tiny black g-string, A wonderful naked body with forty-two inches of hips and ass showcased by the g-string.
I was still completely unsure of the relationship between Suelen and Trent as I recalled her words earlier. ‘Protege, toyboy, twenty-years younger than me, very talented, very experienced,’ as Trent turned his back and Suelen slid down the zipper and helped him remove the dress.
He was wearing sexy black, female string underwear, as he clenched his wonderful, firm feminine ass cheeks for me and Suelen before he turned to show us his average size erection poking out of his crotchless thong. His matching cup-less bra a nice extra touch.
“He is a cross dresser, I do like to please my protege, my toyboy,” Suelen whispered as she watched Trent pull my trousers past my ankles.
“Of fuck, so big,” they both muttered as they ogled my boner.
“Do you like watching Michael licking and kissing my big ass while you are licking and kissing his erection Trent, ten-inches and thick for you? You know I love having my big ass worshipped. I can still remember the first time you licked and kissed my ass. It was the day you turned eighteen. Before then I used to tease you while you watched me shower.
Earlier as Trent led me inside I had asked myself, would I be comfortable with this boy giving me oral sex, sucking my cock? Something he obviously expected with the arrangements I had agreed to. Even then, before I had met his lady, there was a sexual vibe, I felt sure I would be very comfortable with him giving me a blow job. With Suelen involved it was a magical blow job, Trent was licking my erection while she and I were tongue kissing while I had a hand on her ass.
She was correct, Trent was a very talented boy for one so young as she watched on. He had me in the plateau phase, the period of sexual excitement prior to orgasm for what seemed like twenty five - minutes, increased circulation and heart rate, increased sexual pleasure with increased stimulation and increased muscle tension, my respiration at an elevated level.
“Do you like watching Michael licking and kissing mommy’s big ass while you are sucking his big cock Trent? After you have had him I want you to make him rock hard again for me, ten-inches and thick so I can fuck him while you watch, just as I promised you.
“I told you he was talented,” Suelen whispered as she licked and sucked my nipples, while I had a hand on her ass as Trent was licking and sucking just the tip of my erection, while he ran his thumb tip and a fingertip along the bulging vein in my erection.
Exquisite sexual pleasure as Suelen and I tongue kissed. “Swallow?, Trent asked “Yes swallow,” she replied for me as I had a tremendous, noisy orgasm. “I told you my boyDoggy style so you watch side was talented.”
An hour later after we watched each other shower Suelen told me, “You have probably worked out by now Trent is my step-son. We developed a sexual relationship the day he turned eighteen. I used to tease him while he watched me shower. He was like a raging bull as he grasped my hips and licked and kissed my big ass before he fucked me. We spent the rest of the day in bed together.
“It wasn’t long before I shared him with some of my girlfriends then some of my male friends. By the time he was nineteen with some help from some of my friends, male and female, he was an exciting cross dresser, and an accomplished bi-sexual lover. Though the one thing that eluded him, and me, was a man with a thick, ten-inch erection. I promised him that one day I would make it happen for him, though he might have to share with me.
“So here we are Michael, I want you to fuck me while my kinky step son watches,” she told me as we watched Trent teasing my flaccid cock with his fingertips. Your step mommy wants her boy to watch her fucking Michael’s ten-inch cock. He was rock hard for you, ten-inches and thick. Now I want him rock hard for me, ten-inches and thick.
“Before I fuck Michael I want you to watch him to give me some cunnilingus, you know what that is, it was me who taught you, while you suck him to a ten-inch erection for me. So exciting for mommy, my boy watching Michael licking my engorged clit, while he is working as a fluffer,” Suelen whispered as I sat on the edge of a chair, while she stood legs spread as I licked her, my hands on her ass cheeks while Trent was teasing my cock with his tongue, lips and fingers to a full on erection.
“Which way would you like me to fuck Michael for your sexual pleasure while you watch Trent?, Suelen asked as she teased my now wet, thick, ten-inch with her fingertips. “Let me guess? Doggy style, so you can watch from side-on and ogle Michael’s ten-inch erection while he has my big ass in his hands? Are you going to masturbate for us while you watch?”
Trent was naked, apart from his heels, as he sat on a high stool watching from side in as Suelen leaned her arms on a low table. “A big thick, ten-inch cock for mommy, are you pleased for mommy?,” she teased as Trent watched me slowly slide the full length of my erection into her with my hands on her big ass.
One of my favourite fetishes, fucking an older woman with my hands on her big ass while a young boy, a very pretty boy watches and masturbates.
Less than an hour later I was reminded when I asked myself earlier, would I be comfortable with this boy giving me oral sex, sucking my cock? I was very comfortable receiving my second blow job for the session from him as his step mother joined in. “Trent is my protege, he is a very talented boy for one so young, he is more than twenty-years younger than me, He is also very experienced for one so young,” she whispered as she watched her step son swallow.
“I did warn you we provide for some very kinky people with lots of sexual fetishes,” my agent Ada told me the next day after a short debrief. “Tell me some more about Trent? Oh wow, really? How exciting.”