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 work as a gigolo or male escort for an exclusive agency that provides for some very kinky people, even famous people with lots of sexual fetishes.
Ten years ago I was still very naive in matters sexual, though even then I realized my cock was much larger than other boys my age when comparing in the locker rooms of my sporting team mates. Boys will be boys and a number of them made lewd and suggestive, though flattering comments about my equipment.
I was eighteen when my mother first caught me masturbating in bed one morning before I left. She didn’t say a word and I can still recall her flushed cheeks and the lustful look in her eyes.
After that I often made a point of leaving the bathroom door open, hoping my mother would look in. The first time I was aware of her looking in I made a point of not looking at her, while I teased my cock to a full erection. By the time I ejaculated she was gone.
After a few weeks, Saturday morning became a tacit, regular fixture for us while she watched me masturbate wearing her dressing gown while she waited to use the shower. Any pretext of making out we knew each other was not watching each other was abandoned, though not a word was spoken as we held eye contact. After the second week she would let her dressing gown fall open and stand with her legs spread to show me her tits and pussy. I was too naive then to appreciate the way she trimmed her pubes in a Mohawk style.
The next week she was wearing heels for the first time as I learnt what an extra turn on a semi-naked woman can be in heels could be.
The first time she watched me ejaculate was a moment I will long treasure, as I teased and edged myself. Still not a word spoken, though I was almost embarrassed as I groaned like a wild animal. As she helped me dry off after, it was the first time she had spoken to me while watching me. “That is very naughty, but so exciting, I do like to watch my big boy enjoying himself. Would you like to watch me shower? Can you get it up for me again while you watch?” I did, and it was so good.
Lola, my mother’s divorced sister was a frequent visitor, they were very close, especially in summer when she came to share our swimming pool with us. By then it was obvious to me Aunty Lola had a strong interest in me as she paid special attention to me and asked lots of questions.
“Forget the Auntie Lola bit, just call me Lola from now on, I am five years younger than your forty-year old mother,” she told me on my nineteenth-birthday as she kissed me with the tip of her tongue and handed me a parcel. “Show your mother and I your presents. You can wear the white jock strap next time you play sport. Is the black bathing costume your size?” The last item was a very expensive and sexy male g-string, something I had always wanted to own, but couldn’t afford. “Better not show that one to your mother,” she smiled.
“Your mother told me she caught you masturbating. She told me you are very well endowed. Such a waste when I could have helped you,” Lola told me as my mother went inside for something after she and Lola had a terse, whispered conversation. “Is the black bathing costume your size?,” she asked again. “I want to see it on your body Michael. May I please? I won’t look while you change. Or would you like me to look?,” she asked in an agitated tone.
“Yes, look,” was the only response I could muster in my excitement as I let my bathing costume fall to my ankles and flaunted my semi-erect cock for Lola. “Your mother was correct, you are a very well endowed boy,” she told me with a lascivious smile as she watched me slide my new costume over my cock.
“Would you like some oil on your body?,” Lola asked as we could hear, then see my mother returning wearing a pair of high heels and a fresh, skimpy two-piece bathing costume.
“So pleased my boy and my sister are getting along so well. Lola has always had a soft spot for you,” my mother told us as she watched me laying face down as Lola oiled the insides of my thighs, then my back. “That is very naughty Lola, you always were a tease. Though I do like watching you oiling my boy’s athletic ass. That is a kinky turn on for me. You have oiled my ass here by the pool many times, and I yours, but never with my boy watching. Do you think he is old enough to watch now?”
From that moment on I have had an ass fetish. Prior to that moment I had never taken a lot of interest in any female’s ass, always preferring tits and legs. I had seen my mother kiss her sister platonically many times, though never with the intensity as they were kissing then. I will never forget the look on my mother’s face as she looked at Lola and asked in a whisper, “Do you think my boy is old enough to watch?,” as she turned her back and Lola slowly slid the bottoms of her swim suit over her heels.
Nineteen-years old and for the first time in my life, a sudden realisation my mother had a magnificent, big, dimple free ass with no bikini lines, and she knew how to wear high heels to show it off. “That is very naughty Lola, oiling my big ass while my boy watches,” she whispered as she looked over her shoulder at me and clenched her ass cheeks for me. “Do you like mommy’s big ass? Do you have an erection for mommy? Or an erection for my sister? Or for both of us? You are old enough to tell mommy now.”
I was too embarrassed at that age to tell her the erection I had right then was like no other I had ever had, like an iron bar, throbbing to the point of painful and leaking pre cum.
“Would you like my boy to watch me oil your ass Lola? Would you like to watch me oil Lola’s ass Michael?”
A wonderful surprise for me, my mother’s sister also had a magnificent, almost identical ass.
“Would you like my boy to oil your ass Lola? Would you like me to watch my boy oil your ass Lola?”
“Yes I would. Now would be a good time for him to wear the very expensive and sexy male g-string, I gave him. Show your mother and I what it looks like on you.”
For the first time in my life, two women, both twice my age, were looking and admiring my naked body and throbbing, thick, ten-inch erection as they watched me try on my new g-string for them, the first one I had ever owned. It felt wonderful on my naked body as Lola helped me slide my erection through the tight opening at the front of it, then two tight straps over my ass cheeks before she clipped the sides of it.
“That is very naughty Lola, don’t stop, I want to watch and enjoy. I knew my boy was hung, he must be ten-inches, and so thick. Would you like mommy to kiss you with the tip of her tongue while her sister gives you a blow job? Has my boy ever had a blow job before? No, never ever? Why not?”
That was my first lesson in being teased and edged by an older woman while receiving a tremendous blow job with another aroused woman, my mother, watching.
“Lola is coming to to visit us again next Saturday in the early afternoon,” my mother told me a few days later. I was aware of them having a few animated phone calls during the week while my mother looked my way at the other end of the house. Were they discussing me? Perhaps they were feeling guilty?
After one of the phone calls my mother asked, “Do you feel comfortable with my sister? She is very impressed with you. You know we are very close as sisters. She is sixteen years older than you. You know why I am asking don’t you?”
“No why,” I asked, though not as naively as my mother thought. “Why are you asking?”
“My sister Lola wants to seduce you and fuck you while I watch. Would you be comfortable with that?”
“Do you really want to watch, while your sister seduces and fucks me?,” I teased full of anticipation. The expression on her face was sufficient response for me.
“Lola and I both agree you cock would look even more impressive without so much hair around it, less is more,” my mother told me as I readied to shower early on the Saturday morning. The vibration from the electric shaver was a new whole new sensation for me as she shaved me, while she worked her way around my erection. “Are you excited at the thought of my sister seducing you and fucking you while I watch this afternoon?,” she asked as she watched me shower
“Very excited, incredibly excited, extremely excited, show me some skin,” I whispered as she dropped her dressing gown for me. “I adore your naked body in heels, a wonderful turn on for me,” I told her, as she watched me edge myself to orgasm.
“Are you excited at the thought of my sister seducing you and fucking you while I watch this afternoon?,” my mother asked again shortly before her sister was due as she watched me shower again in preparation. “Which way do you intend fucking her?,” she asked nonchalantly white she dried me off. “Lola and I want you to wear these for her,” she told me as she handed me a tiny black, crotch-less jock strap and cock ring I had hidden away in one of my drawers.
“Your shaved cock looks sensational in those she told me, I have watched you masturbate in those without you knowing. Or perhaps you did know?,” she smiled as she helped me on with the jock strap, and a pair of jeans, before she rubbed oil over my torso. “I want you to be topless for my sister when she arrives,” she whispered as she teased my nipples with her oily fingertips. How inhibitions can vanish in such a quick time I mused as I fought to hold back my erection.
Kisses all round when Lola arrived, my turn first, as she tongue kissed me in a way none of my teen girlfriends ever had. The way my mother returned her tongue kisses was a lot different to the platonic kisses I had seen in the past. She looked sensational in a short black, cocktail dress, almost identical to the one my mother was wearing.
Like most teenage boys, my long held fantasy while being seduced by a dream older woman, was the high heels, black garter belt and stockings look with a matching cup-less bra. Lola didn’t disappoint me after she motioned for me undo the zip at the back of her dress and tongue kissed me as she stepped out of her dress while my mother watched on. I lacked the confidence to tell Lola her gorgeous big ass and the beautifully trimmed hair on her cunt lips, both framed by her garter belt were an absolute turn on for me.
“You really are a big boy, huge,” she smiled as she dropped my jeans over my ankles and stroked my erection poking out of my jock strap.
“Is this what you wanted?,” my mother asked as she handed me my cock ring as she and her sister tongue kissed while both of them watched me slide it along my shaft and clip it under my balls.
My fantasies were doubled when I watched Lola undo the zip at the back of my mother’s dress while they kissed with the tips of their tongues, before it dropped to her ankles. Similar to Lola, her high heels, black garter belt and stockings look with a matching cup-less bra were a huge, bonus turn on for me, a nineteen-year old boys erotic dreams come true.
“You are not a boy any more, so fuck me long and hard, from behind with your hands grasping my ass.” Lola whispered as she lay on her side on my mother’s bed, while my mother watched. She was incredibly agitated as she watched me slide my rock hard, thick, ten-inch erection into her sister. My mother was making strange, hissing noises as she watched me kissing her sister while fucking her.
“That is so good, we should have done this before Lola,” my mother whispered as she and her sister were kissing with the tips of their tongues as I increased the tempo of my fucking. “Harder, fuck her harder, I love the noise, and I love watching my boy fucking my sister with his big, thick cock, harder, harder, harder.”
That night my mother and I and I were in the bath together as she washed me, with special attention to my flaccid cock. “You know by now I would love love to fuck you, but that would be very naughty. You also know I love a challenge, especially a sexually exciting one, so do you. My new challenge is to give you your third orgasm for the day. Which would you prefer, a hand job or a blow job? Or a combination?
“So pleased you chose a combination. Would you like my sister to visit us again next week? Perhaps you would like to watch her eat me? Or me eat her while she sucks your cock?”