“Phyllida is a titled, aristocratic lady with a much older husband living on a country estate in Hampshire. Before she became a titled lady by marrying an English Baron, she had something of a murky divorced past,” my agent Ada told me as we finalised the details of my assignment.
My first thoughts were a mature age English woman with a name like Phyllida had to be a classic, formal, upper class, refined and a complex woman in bed. And so she proved to be.
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.”
Phyllida was beautifully spoken, with a slightly patrician air, she was wearing heels and a backless ankle length satin dress, a slit up to her waist down both sides of it when I arrived, flashing her wonderful thighs in sexy stockings for me, her beautiful bare back an instant turn on for me, just as the dress clinging to the crack of her big ass was.
“My husband doesn’t trust me to travel alone so he insists on me having a minder,’’ she told me as her minder appeared, a gorgeous forty-year old women, slightly younger than Phyllida, their physical connection obvious.
Lucy the minder was an exquisite and very erotic part Asian woman, collagen lips, long shoulder length, straight jet black hair, dressed in a leather cat suit. Far from what I imagined the minder of a titled, aristocratic lady might be, or should be, fully expecting a tough looking ex-marine.
“Before we leave for home, me and my minder Lucy want to fuck a local man. We have never had a man as big as what your website describes. Will you mind if Lucy watches you fucking me? I promised her if you perform up to our expectations she could give you a head job while I watch afterwards, Phyllida told me, in total command of the moment
“I always think one of the sexiest things a woman can do to signal a man she wants to have him, to show she is ready for him, is to remove her earrings while looking directly at him,” she told me as she removed her earrings with her legs crossed, so confident, so beautifully spoken with her English aristocratic class as she handed Lucy her earrings.
“Another is for a woman to remove her stockings for him,” she continued as she sat sideways to me, lifting her dress to slowly undo the clips of the garter belt holding up her stockings, flashing her wonderful thighs above her stockings for me, before she motioned for me to slide her stockings off, my fingers enjoying caressing her beautiful bare thighs, just as she wanted.
“Another is to smile at him, lift her dress while standing and remove her knickers, flashing her pubes then let her dress fall,” she smiled as her knickers fell to the floor.
“I find it even sexier if a third person is watching, a male or a female, who expects to participate. Tell me Michael, what is it you think one of the sexiest things a woman can do to signal a man she wants to have him.”
“A classy titled English woman, a Baroness, your size to remove her backless ankle length satin dress, no knickers, to show her beautifully trimmed black triangle between her wonderful thighs, then turn her back to show me her magnificent, big, perfect ass. Before she undresses me, so I can show her the thick, ten-inch erection I have for her.
”Then the same woman with her magnificent big ass sitting on my erection with her back to me.” As she was shortly afterwards, while I admired her magnificent big ass, my hands all over it.
The minder did watch us fucking, all three of us enjoying the experience, Lucy sitting close by, her legs spread, watching her boss fucking me in a range of positions. The final position, Phyllida laying sideways on the bed while I fucked her from behind, with her big ass in my hands.
Lucy kissing and licking Phyllida while I fucked her. Licking her nipples and tits, sucking her engorged nipples, whispering to each other, their sexual chemistry a bonus for me as I edged Phyllida, a fingertip on her clit with my erection sliding into her. My body slapping against Phyllida’s big ass as she urged me on. “Harder, fuck me harder, my first ever ten-inch fuck.”
“I promised Lucy if you performed up to our expectations she could give you a head job while I watch. You excelled yourself Michael. May I watch her give you a head job? You should know English women are some of the kinkiest.
“Are you happy for me to watch my minder give you a head job?,” Phyllida asked as she showered with me, Lucy the minder sitting on a stool outside the shower watching us shower, while I teased my flaccid cock for both of them, wanting them both to watch me achieve a new thick, ten-inch erection for them.
Looking forward to the Baroness watching her minder Lucy giving me a head job. Not sure if the look on Lucy’s face was envy, jealously or downright voyeuristic sexual pleasure, while I wanted to maximise her pleasure.
Holding eye contact with Lucy the minder, wanting to impress her as she watched my cock growing for her, imagining what her head job technique might be while her boss, the Baroness, watched.
After we dried off I was sitting on a chair in front of a wall length mirror, my legs spread, working and concentrating toward becoming fully erect again, Phyllida standing behind me, talking to me, urging me to get hard for her minder, really hard, teasing my nipples with the finger tips of one hand as she gave me a finger to suck, both of us waiting for her minder to reappear after she told us she was going to dress in something sexy for us.
Then Lucy the minder re-appeared topless, smirking at me, licking her lips for me, a wonderful kinky surprise, Lucy was an incredibly attractive tranny.
Obviously. proud of her beautiful firm tits, in a short skirt, with stockings and heels, Phyllida greeted her with a passionate tongue kiss before she helped her remove her skirt, whispering, “Enjoy Lucy baby, enjoy for both of us, you always wanted to have a man his size.”
“Oh wow,” I muttered as I ogled and admired her huge, thick already erect cock and balls dangling out of her garter belt above the tops of her stockings. Far larger than the average man. Sliding my new erection over her nipples, before Lucy slid her erection over my nipples.
“Remember fellatio, a head job, is a gift, not something you demand of a slave,” Phyllida told me as she tongue kissed me, making me want Lucy’s head job even more.
Lucy’s head job, her fellatio, was a gift, while admiring her wonderful trans body and Phyllida’s naked body simultaneously. Lucy was intent on showing both me and Phyllida her skills.
Complimenting me loud enough for Phyllida to hear, “So big, so thick,” before she wrapped two hands around my shaft, moving her hands and mouth up and down my erection. Twisting her wrists back and forth as she moved up and down, applying lots of lube.
Phyllida standing behind Lucy, naked, grinding her pubes into her ass while stroking her erection while she watched her sucking my erection.
Lucy using her other hand to gently massage my balls. So enthusiastic, telling me, “I wanted to do this to your cock the moment you slid it into The Baroness, Phyllida, my boss and my clandestine lover.
Asking me. "Do you like how this feels? Or this?” Using her tongue to stimulate the head of my erection. Applying soft pressure with her tongue against erection, moving her mouth up and down my rock hard shaft.
Deep throating me, as much as she could take of my erection into her mouth. So far it reached her throat. Stimulating my other erogenous zones. Making it a full-body experience for me.licking, Phyllida sucking and chewing my nipples while Lucy was blowing me.
Phyllida standing behind Lucy again, naked, grinding her pubes into her ass while stroking her erection. Kissing me as Lucy had me on the brink. Thinking to myself, ‘I would have done this for nothing.’ Instead I have been paid a four figure sum of money.
So good with Phyllida watching her trans minder bringing me to orgasm, my second for the session. Kissing me, asking me, telling me, “Lucy is good isn’t she? She had me last night, fucked me with her erection. Not as big or thick as you.”
Her words echoing in my mind, ‘Fucked me with her erection. Not as big or thick as you,’ as I moaned, out of control, “Gunna cum, gunna cum, gunna cum.”
“Nice for your CV and your ego Michael,” Phyllida told me as I readied to leave, taking one last look at her naked body. “An English Baroness and a trans minder in one afternoon.”