Bring your swimming togs he reminded me a few days later before I was due to meet his step mother Jillian, at two in the afternoon. “You must be John, I have heard lots of good things about you,” Jillian told me as we looked each over. My initial reaction, a stunning, stylish woman, with reddish, blond hair and a ripe, size-12 plus body. She was sitting in a chair with her legs crossed, teasing me as I ogled her knees and thighs in heels and a short, back skirt.
“I will meet you boys at the pool in five minutes,” she told us after some stifled small talk. It must have been ten-minutes later when Jillian joined us, making a huge impression on me as she strutted to the pool in heels and a wrap.
“Take mommy’s wrap off me please Steve?,” Jillian asked as she looked directly at me. She was a knock out in her two-piece, white bathing suit, a wonderful contrast to her tanned body.
As we relaxed by the pool Jillian started to open up as she kept looking at my almost naked body in my skimpy swim trunks. “I want you to call me mommy John, far more intimate than Jillian. Steve always calls me mom, so it won’t be confusing.
“I don’t know if my stepson Steve told you, but I often ask about the other boys at the gym. One day I was teasing him by asking which gym boy had the largest cock. Guess what John? He nominated you. Are you really as big as he told me John? He told me when you are erect, showing off to the boys in the showers, you are ten-inches, and thick.”
A little while later, I was in a separate shower room when Jillian entered without knocking while I was drying off. “Steve was correct, you really do have a large thick, cock. “Would you like to show me if it really is ten-inches when erect? Yes?” Without waiting for an answer she tipped some oil into her hands and smeared some over my torso before she smeared more oil onto my no longer flaccid cock.
“Oh wow, that is magnificent, huge and thick, just fucking magnificent, my first ever ten-inch cock,” she whispered as she gave me an incredible hand job.
“Would you like to visit me tomorrow afternoon? I want to get to know you better. Steve will be at work until late.”
As soon as I arrived Jillian told me, “I want to be your cougar John. First up you have far too much hair around your cock. I am going to shave you to my satisfaction,” she told me as she squirted shaving cream over my pubes, with a hand holding my cock, the other hand shaving away what now days would be embarrassing amounts of pubic hair.
“I like that look John, your cock looks even bigger, now you have my signature over your erection, just a neat tuft. Tell mommy you like it.”
“I love it mommy, just love it,” I whispered, while she watched me shower to wash away the remaining cream and hair, around my erection.
“This is called fellatio, some call it a blow job,” Jillian told me as she stood me against a wall, facing a wall mirror. A huge discovery for me, fellatio from an older woman, a cougar was in an entirely different league to the two girls that had me previously.
“Would you like to fuck mommy John? Mommy has never been fucked by an erection as big as yours,” she asked an hour later. And what a fuck it was. I commenced missionary style, however, Jillian quickly turned me on my back, took control and showed me what cowgirl sex was.
Lots of questions for me in the afterglow. “Don’t be embarrassed to give mommy honest and truthful answers. How many girls have you had? Were they good in bed? Did they suck your cock? Has a man ever had you? Or approached you asking if they could suck your big cock?”
“Yes, they have mommy.”
“Did it happen?”
“Yes, mommy, while his wife watched.”
“Did you enjoy it?”
“Yes, I did mommy. Twice.”
“Have you ever had a spanking on your naked ass. No? I think I could turn turn you on by spanking you ass with a wire coat hanger, pleasure and pain, give you an erection. Has Steve ever told you I spank him when he is naughty? Sometimes I think he is naughty in order just to receive a spanking.
“You are mommy’s stallion, her thick ten-inch, fucking stallion,” she told me later while we fucked for the fifth time that day.
In the afterglow Jillian asked me if I would like to trim her pubes. ”You might not be old enough to realise the way a woman waxes or shaves the hair around her vagina can be a huge turn on for them and their man or men. Watching a man shaving me is far more intimate and exciting than a girl in a parlour waxing me, and wonderful foreplay for both parties.
“I have had the totally natural bushy look, The Bermuda Triangle, The Landing Strip, popular with Playboy models, a strip down the center of my my mons pubis, The Brazilian look, not a single hair in sight. Very popular with my girlfriends. The Martini Glass, The Five O’Clock Shadow look, The Postage Stamp a small, groomed square just above my clit., The Arrow look, telling my lover exactly where they were meant to be going without the need for verbal cues.
“Mommy’s current favourite look is the one Helmut Newton’s models preferred – a beautifully trimmed black triangle with a shaved gap at the edges. I do like that look,” she told me as she posed hands on hips, legs spread to flaunt it for me.
“Would like to trim mommy’s pubes, leave your signature, make them yours?”
“I want you to make you totally bald for me mommy, then I can watch your pubes grow and trim them to my satisfaction each week.
“Licking and sucking mommy’s bald cunt lips is so exciting for me, my first,” I whispered half an hour later, my hands under her ass.
“Today I want to teach you the finesse and finer points of cunnilingus, licking my cunt to orgasm with your tongue,” Jillian told me after a few meetings. “If it’s done just how I like it, I lose control, I go into a euphoric state. I can’t help what I’m saying, I love it so much. You realise I have just laid down a challenge for mommy’s boy?”
Jillian was am outstanding teacher and I soon learnt how to make her lose control, go into an euphoric state. “Think of your tongue like the fluttering of gentle butterfly wings or like a thick wet magic marker carefully drawing a still-life. It’s better to be gentle and methodical than too rough or overly acrobatic.”
The first time she moaned, “Fuck my cunt, fuck mommy’s wet cunt, fuckamycunt, fuckamycunt, while I was licking her to orgasm was really something, with my hands under her ass.
I quickly learnt Jillian loved some dirty talk while I was giving her cunnilingus, almost as much as I did. “There is another man watching, he has a huge erection, bigger than me, he wants you to suck his cock while I am licking you to orgasm, multiple orgasms.”
Or, “There are two men watching, they both want you to suck their cocks while I am licking you to orgasm.”
Or, “One of your girlfriends is watching. At this moment she is so jealous watching me fucking you. Her man is watching as well. They want you to watch them fucking while I lick you to orgasm.”
Jillian took me shopping for cock rings and took great delight in asking the female shop assistant, “Mommy’s boy is very well endowed, what model would you recommend for him?,” before she paid for four different ones. Are you sure they will be big enough and fit him properly?,” she asked as the shop assistant wondered my a mother would be buying cock rings for her twenty-one year old boy.
It was around a month later when Jillian told me. “Mommy would like to introduce you to some of her girlfriends. I have told them all about you, my ten-inch stud, my fuck boy. Some of them want to watch you fucking me. Some of them you could fuck while I watch perhaps? Would mommy’s boy like that?”
A week later, the first of her girlfriends was a voluptuous brunette, Elaine, early forties. “We are old friends,” Jillian told me after they tongue kissed, and she commenced undressing her as Elaine and I held eye contact. “I explained to Elaine I was your cougar and you were my stud. She was fascinated, though unbelieving when I told her how well hung you were and how some days we make love and fuck five times a day.
“Elaine has always wanted me to watch her fucking another man, though the opportunity hasn’t arisen until now. And I have always wanted to watch her fucking another man.”
“Would you like John to finish undressing you Elaine?,” Jillian asked as she stood hands on hips in her sexy black lingerie, a thong and bra.
“You know I would Jillian, I am so pleased you set this up for me,” Elaine told her as she beckoned me, before she tongue kissed me. “I have never been undressed by a twenty-one year old boy. Take my thong off first. Is my ass big? Do you like it? Now my bra? Do you like my tits?”
“Elaine was fascinated, though unbelieving when I told her how well hung you were John. Let’s show her,” Jillian told us as she removed my shirt, then my slacks. I already had a full on erection from looking at Elaine’s voluptuous, naked body before she removed my sexy, black jock strap.
“Oh wow, fuck, I am almost speechless, he is huge Jillian. Where did you find him? You bitch.”
“I have never fucked a twenty-one year old boy,” Elaine whispered, while I was on my back, as she lowered herself onto my rock hard erection.
“Would you like mommy to kiss you and tease you while I watch Elaine fucking you? You are cheating on mommy. But I like it. And I do like to please mommy’s boy and my girl friend.”
It was months after I first met Jillian when she asked me. “Do you remember when I asked, has a man ever had you? Or approached you asking if they could suck your big, thick cock? You told me yes, while his wife watched and you enjoyed it.
“I would like you to meet my old friend Noel. He used to work as an expensive, high end male escort until his plumbing gave out. These days he caters for a very *********** clientele and is even more expensive. He is incredibly talented. Want to see some pics of him?”
I was amazed at Noel’s appearance, an attractive, long haired blond, masculine, slim man in his early forties, wearing nothing more than a black leather, male thong, hands on hips, in the first pic. In the second pic, his face beautifully made up as a female with collagen lips, the same male thong, hands on hips.
A few days later Jillian told me, “I want you naked under the short silk dressing gown I gave you when Noel arrives. Wait in the room next door until I ask you to come and meet Noel. I want you to tease mommy and Noel by flashing your gown open to show us your big, thick cock.”
I could hear Jillian and Noel making small talk before I heard my cue, “John, come and meet Noel.”
“Oh fuck,” I whispered to myself when I sighted Noel, his face beautifully made up as a female would, his collagen lips smeared with lipstick, wearing female heels and leather slacks, topless, hands on hips.
“Well hello big boy, I am going to enjoy you, you will be a huge challenge for me,” he told me in a soft feminine voice, while just as Jillian had asked I teased her, mommy, and Noel by flashing my gown open to show them my thick, still flaccid cock.
“Do you want mommy naked while I watch Noel give you fellatio,” she asked as she motioned for Noel to remove her dress, naked underneath it. “An extra turn on for mommy’s boy, watching another man undress me for the first time.”
I was resting against a high stool, my legs spread, after Jillian removed my gown while Noel ogled my cock. “Noel used to work as a high end male escort. Now he caters for a very *********** clientele, he is incredibly talented, you are are lucky boy,” Jillian told me.
His hands were so soft on my naked body, before he licked and sucked my nipples, expertly teasing my cock with his fingertips. “I am not a tranny, just a red blooded, macho male who loves to please hung men and boys. Purple, purple purple,” he told me in a whisper. I didn’t realise it then, but repeating purple is the prefect word to form your mouth into a perfect O shape for fellatio.
“I promised you he was hung, and thick Noel,” Jillian whispered as she watched him tease me to a full erection, before she slid her favourite cock ring along my shaft and he watched her clip it under my balls.
I had never had my balls licked and kissed before then. So good, what have I been missing? His collagen lips smeared with lipstick were an extra turn on as he left smudges of lipstick on my erection after he commenced working on it.
He was rolling my balls around in his hand while he sucked my erection. Focusing on my balls with his mouth, a hand working on my erection as he licked all around my balls with a broad, flat tongue. Taking each ball in his mouth for a a few seconds, licking between my balls,
“Teasing me. What do you like better? This? Or this?” Moving his tongue around on the underside of my erection while doing basic up-and-down maneuvers. Pointy tongue, licking up and down, side to side.
Holding the base of my erection in his hand while moving his wonderful collagen lips back and forth over the ridge between the head of my erection and shaft, moving barely an inch.
Basic strokes with his hand and mouth, turning his wrist back and forth as he moved up and down. Gently slapping my erection on his tongue. Rubbing my erection over his lips, face and nipples. Alternating between using his mouth and using just his hand.
“Mommy loves watching a talented man giving her boy fellatio, a blow job. My boy’s erection is so hard for him,” Jillian told Noel, standing behind me, teasing my nipples with her fingertips.
“Mommy can tell you are close to orgasm for Noel. Would you like mommy to tongue kiss you, increase your sexual pleasure. And hers. So close, you are so close, she whispered as I fought to hold back my orgasm.
“Don’t hold back baby, do it for Noel and mommy,” she whispered as we passionately tongue kissed while I groaned and shuddered to an orgasm like no other.
Jillian never ceased to amaze me with some of the wonderful kinky turn ons she came up with. “Have you ever had a spanking on your naked ass. No? I told you not long after I first had you, I thought I could turn turn you on, give you an erection, by spanking your ass with a wire coat hanger, pleasure and pain. Mommy is going to wear her black leather dominatrix outfit for your spanking.”
I hadn’t seen Jillian in her her black leather dominatrix outfit before. “You look sensational in leather and heels mommy. Even more sensational,” I whispered as she turned to show me the slacks had no ass.
“I saw you looking at that young girl, I am going to discipline you. punish you. “You are mommy’s stallion, her thick ten-inch, fucking stallion. Not some girl’s half my age. Stand with your hands on the mirror for support, spread your legs, mommy needs to punish you, wants to punish you, pain and pleasure. Lots of each.”
She had folded the coat hanger into double, length wise so there were two pieces of wire about an inch apart. Are you looking forward to mommy spanking you? You know mommy is,” Jillian told me as she teased the two pieces of wire over my naked ass
Then, swish, pleasure and pain as the modified coat hanger hit my ass. After a short interval, deathly silence before another noisy swish. Jillian was standing side on now so I could could see her beautiful, naked ass bulging out of her leather slacks.
“You are mommy’s naughty boy, I think you like mommy punishing you, your cock is much bigger than when I commenced punishing you,” she whispered as I ogled her naked ass in the mirror before another swish.
“Would you like mommy to do it harder next time?” Without waiting for me grunt yes, another swish, wonderful pain and pleasure, as my cock responded.
“Look at your cock now, almost fully erect for mommy. Two more and I expect you to be fully erect for mommy. Brace yourself, clench your hands.” I hardly heard the coat hanger as it barely touched my ass. The noise of the next blow on it’s way was far louder than those before.
I had licked and kissed mommy’s ass countless times before then. Licking and kissing her ass after my spanking, still feeling my pain with a throbbing erection, with her legs spread, her hands behind her head, her ass bulging out of her leather slacks after she wiped cream over the welts on my ass and told me she had made me bleed was wonderful foreplay to the fuck we both wanted and needed.
The fuck Jillian and I enjoyed after that was absolutely, beyond de***********ion.
In the afterglow Jillian told me “Mommy would like to introduce you to some more of her girlfriends. Next time two of my girlfriends. You could fuck one of them while I watch. While you watch me having lesbian sex with the other. Have you ever watched two women making love, having lesbian sex? Would you like that John? Could you handle that John?”
I could, and I did, though that’s another story, Alexa and Allegra were very exciting for both me and mommy.