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Introduction:

In a previous story, MY MOTHER AND HER SISTER, I told how I was eighteen when my mother first caught me masturbating in bed one morning. 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.

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 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.

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.”

“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? 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.

“Are you excited at the thought of my sister seducing you and fucking you while I watch this afternoon?,” my mother asked shortly before her sister was due as she watched me shower 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.

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.

“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 second 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, tongue fuck me? Or me eat her, tongue fuck her while she sucks your cock?”

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. These days I live in Sydney, Australia and work as a high-end gigolo or male escort (far more subtle than male prostitute) 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 realised 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.

A little while after my nineteenth birthday Lola found a reason to come stay with us for a week. Then I commenced spending my weekends at Lola’s condo, from Friday night until early Monday mornings. She taught me how to trim her pubes before she trimmed mine every Friday night as foreplay. “Less is more.”

Every Monday night my mother would ask me what her sister and I did over the the weekend. “Did she give you a blow job? How many times did you fuck her? Which way? How long for? Did she ask about me?”

One of the most exciting nights was when Lola invited my mother, her older sister around. A while ago while she was giving me a combined hand job and blow job I wondered if she was teasing me when she asked, “Perhaps you would like to watch her eat me, tongue fuck me? Or me eat her, tongue fuck her while she sucks your cock?”

I had often suspected they were lovers and they were very exciting. A huge sexual learning curve for me the first time I watched her tongue fucking my mother while I masturbated.

It was almost inevitable that I learnt Lola was bi. The first woman we shared, a girl my age, was a revelation for me on a Saturday night.

The sexual tension between Lola and I increased a few notches when she asked me if I was bi-curious. “You are so good looking, so virile and incredibly well hung, there are scores of men out there who would pay lots of money just to give you a blow job. Have you ever had a blow job from another man? You must have been propositioned?”

“No, I have never had a blow job from another man, though lots of propositions. The idea of another man giving me a blow job has some appeal for me. Do you think there are men out there who would pay money just to give me a blow job?,” I asked naively.

Little did I realise then, a ten-years later I would make a lucrative career as a male gigolo providing specialist services to mostly older, wealthy women, often with their man in tow who wanted to share me. My rules were the men could give me a blow job, nothing more or extra. as long as their lady watched.

“Felix is due here at eight,” Lola told me as she handed me ten, crisp, $100 bills. “He didn’t hesitate when I told him I insisted on watching and the rate was $100 an inch. “Is he really ten-inches?,” he asked. “Yes and thick, just a boy, fifteen years younger than you,” I told him as I showed him some pics of you on the phone.

“In case you are wondering what to wear for your first professional engagement, I purchased this for you, this sexiest, black, jock strap in the men’s boutique. “The boy in the boutique asked who the lucky man was. Two men actually, I teased as his imagination ran riot,” Lola told me as she oiled my torso, ass and then my balls and cock, before she helped me on with the new crotch-less jock strap, did up the clip at the side, then helped me put on a short black, sleeveless, silk shirt without any buttons. “You look hot, you have the makings of male gigolo,” Lola told me.

“Hi Felix, Michael is in the next room, come through. He has been looking forward to your visit. Is he what you expected and want?,” Lola teased as she slowly removed my shirt for him.

“Yes, magnificent, I have waited my whole life for a thick, ten-inch erection for my sexual gratification,” he gasped as I stood with my back to a wall as Lola sat on a stool to the side and watched him lick and suck my nipples before he hungrily devoured my erection.

Lola had promised not to say a word while Felix was blowing me. I had my hands behind my head soaking up the paid pleasure Felix was providing me, watching her for any reaction as I read her lips. “Oh wow, fuck, fuck, fuck, so good, so fucking good,” I could discern.

Felix was very good. “Your erection was just magnificent. Can I bring a friend next time?,” Felix asked as he departed.

Thirty-minutes later Lola and I were in the bath together as she washed me, with special attention to my flaccid cock. “You know by now I love a challenge, especially a sexually exciting one, so you do. My new challenge is to give you your second blow job for the day. How many men receive two blow jobs in one day, one from a bi-man and another from a bi-woman? Little did I realise then that would be a common occurrence for me in the not too distant future.

“Would you like to meet to two of my friends, Katie and her stepson Neil? I have told them all about you. The are most attractive and they are very exciting lovers. Katie is forty, eighteen years older than her stepson Neil, they are both gender fluid. Would like to see some pics of them?”

“Very appealing, make it happen,” I told Lola as I scanned the pics. “I am fantasizing about her tongue fucking you while you give the boy a blow job.

Lots of sexual tension the next Friday night when Katie and her step son arrived. Lola and I were determined to tease them, and us, and to maximise our sexual pleasure. I was topless wearing a tight, low cut pair of jeans, my already semi-erect cock obvious. Lola was intent on playing the vamp and turning on a forty-year old step mother and her eighteen-years younger step son, just as I was.

I handed a bottle of oil to Katie, her oily hands on my naked torso while her boy and my lady watched was exquisitely tactile. Lola motioned for Neil to undress her. First her skirt, to flaunt her glorious ass, naked apart from a skimpy garter belt to hold up her stockings. “Worship my ass for me, your step mother and my boy.”

I had a full on erection with Katie’s oily fingertips teasing my nipples. Lola was watching closely as she slid down my jeans. “You are huge, your pics don’t do you justice,” Katie whispered as she wrapped an oily hand around my erection and stroked it.

“Undress your step mother for us, we want to look at her naked body while she gives my man a hand job,” Lola whispered before he slowly lifted her dress to reveal her naked body.

Exciting jet black pubic hair contrasting her blond hairdo, as Neil slowly exposed his step mother’s size 10-12 naked body for us. Good long legs, flat stomach, firm tits with sexy nipples. “You wanted to watch me tongue fuck Lola. Before I do, lick her cunt for me Neil.

“Oh fuck, so good,” Lola moaned as Katie tongue kissed her as Neil expertly flicked her cunt lips with his tongue.

“Have you ever had a hand job to match this one?,” Katie smirked as she edged me. “Do you like watching me hand fucking your man while my boy is licking your cunt Lola? Do you? Tell me.”

“Yes, I love it, his turn on is my turn on,” Lola moaned as Katie gave me a huge orgasm with her hand.

“I am going to tongue fuck you while your man and my boy watch Lola. Leave your heels on, you will be even more fuckable for me and my boy,” Katie told her. “I have never tongue fucked a woman while a man with a cock as big as your boy watched,” Katie smiled as I sat close enough for her to touch my flaccid cock.

“I love being licked and teased, love it,” Lola whispered as Katie licked her way up her thighs.

“I want to hold your gorgeous big ass in my hands while I tongue fuck you,” she told Lola as she raised her ass and placed one of her legs over her shoulder. Neil was standing close by stroking his erection as he watched his step mother - and lover - licking Lola’s engorged clit.

It was almost a reflex action as Lola reached out for Neil’s erection and he slid it between her pursed lips. By then I was teasing my second, full on, thick, ten-inch erection for the session with a fingertip. “I am impressed, your lady told me you could get it up twice in a session,” Katie told me as she looked up.

“Watch me tongue fucking Lola while she sucks your cock baby. And watch Roger masturbating for us,” Katie whispered just before her boy blew a huge load in less than two minutes.

They were tongue kissing as she slid a second finger into her and found her g-spot. Lola’s whole body was trembling as she had yet another orgasm, incredibly loud this time. “I love it. Watch me, watch, watch me squirt, so good, so fucking good,” she moaned as she squirted for three people.

Neil was holding my gaze and ogling my erection, licking his lips as Katie whispered, “Do it for mommy and Lola. One of your fantasies, blowing a big, thick cock of a younger boy while mommy and her lover watch.”

Without a word being said, I stood with my back resting against a wall, my hands behind my head with my throbbing erection pointing out a ninety-degrees. “Lick and suck his nipples,” Lola told him.

“My boy is good isn’t he? Have I taught him well?,” Katie teased as she kissed me. Next time can we fuck for you while you watch, before you fuck Lola?”

Little did I realise then that would be a common occurrence for me in the not too distant future.

Ten years later I was living in Sydney, Australia and enjoying working as a high-end gigolo or male escort for an exclusive agency that provides for some very kinky people, even famous people with lots of sexual fetishes.

“I have two women who are keen to book a session with you Michael, Lola and her sister. They told me Lola is forty-five, five-years younger than her sister. They are a very glamorous pair of cougars,” my agent told me over the phone. “They asked more questions than usual. Is he really ten-inches when aroused? And thick, I told them. Is a session with him really worth that much money?, they asked when I took their credit card details. Does he get lots of bookings? Yes, he is my number one talent. Would two-thirty, this Friday in the Hyatt be suitable?”

A wonderful surprise when I arrived to find two very glamorous and vaguely familiar cougars in well above the knee, matching black cocktail dresses. “Hello Michael, would you like mommy to kiss you with the tip of her tongue while I watch you fuck her sister?,” she asked. “Or perhaps fuck mommy first?

“Doe’s mommy’s big ass still turn you on?,” she smiled as they undressed me after teasing me, while watching them remove each others dress. “Just for you baby, the high heels, black garter belt and stockings look with a matching cup-less bra. We both still remember dressing like that for you.

“Our bodies are not quite what you remember, though our asses are even bigger, our tits are a little saggier and our libidos are still sky high. You are not a boy anymore, your ripped body is to die for. Your ten-inch erection is even thicker than we remember.

“Your agent promised you can get it up twice in a session, still, like you used to for us. Mommy wants her boy to fuck her, she has never had a gigolo, and never paid for anyone to fuck her. And never had a cock as big as you.

“You are a very experienced stud now, you have learnt some very sexy moves, mommy likes it, very much. And your cock is like an iron bar.

“Before I watch you fuck my sister, titillate us by telling us about some of the clients you have serviced. Serviced is far more polite than fucked I think.”

“My agency caters for some very kinky people, even famous people with lots of sexual fetishes. A typical client is a woman in her mid-forties, often a business executive with a female or male companion, she or he might be her lover and/or minder. Amazing the number of times the second person watches me fuck her and then gives me a blow job afterwards while she watches. Some of the men have fantasised and waited years to blow a man with an erection my size.”

“Any famous women?”

“I can recall five or six CEO’s of foreign multi-nationals.”

“Can mommy do anything to get you ready for her sister? You are a very naughty boy. Perhaps a spanking? Or would you like to oil our big asses like you used to ten years ago? Naked apart from our heels?”

My mother and her sister were standing, legs spread, their hands on a wall for support, naked apart from their heels, as I commenced rubbing oil onto their still wonderful asses at the same time. “Our bodies are not quite what you remember, though our asses are even bigger, and our libidos are still sky high. Doe’s mommy’s big ass still turn you on?

“Your ten-inch erection is even thicker than we remember. Are you ready to fuck mommy’s sister now?,” she teased as they kissed with the tips of their tongues.

“Fuck me from behind with my big ass in your hands while my sister, your mother licks and kisses me. Just like we used to. Show us why you can charge so much money for your services. Your ten-inch erection feels even thicker than it used to be. So good, we miss you.”

“Would you like to take us to dinner in the restaurant downstairs Roger? I want to make it obvious to other diners we have been fucking all afternoon. No underwear for any of us.”

We walked in holding hands, me in the middle, my mother and her sister looking incredibly glamorous in heels and their matching short black, cocktail dresses. “Do we look fuckable? Is it obvious we are not wearing any underwear?,” mom asked, as she and Lola had every man, and most of the women, in restaurant watching as they crossed and recrossed their legs.

People at the tables close by were straining to hear every word as we relived the afternoon. They were straining even harder to hear when the two women commenced making plans for the rest of the night over desert. “We both want to share you. We want you flat on you back on the bed with your big, thick, ten-inch erection pointing to the ceiling. I want to sit on your erection, while Lola sits on your face. I want you to lick her, tongue fuck while my sister and I kiss with our tongues tips.

“And I want you to walk out of here with a very obvious erection,” mom told me as I settled the account. “That is awesome, huge,” she told me as we walked out holding hands, the centre of attention.

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