We met through a dating site. Over the phone she told me she had been divorced for years and was in need of a man to give her some attention.
She told me she was fifty (fifteen-years older than me) a size 14, around 68 inches tall and still attractive.
At her insistence we met in a coffee shop so she could check me out as she was unused to face-to-face meetings with men on dating sites. She was dressed in a black shirt and very tight fitting white slacks with heels. What a pair of fabulous long legs with very well developed long thighs she had! She was the centre of attention and the male staff were mesmerized. “You fill those slacks beautifully,” several waiters and a customer told her.
My first impressions were creamy smooth skin, wonderful legs, but would an older woman turn me on enough to achieve a good erection. When she kissed me over the table for the first time the contact was electric and I immediately became semi-erect.
She was beautifully spoken and super-confident, as would be expected from the head mistress from an exclusive girls school. “I am in town on holiday for three weeks, I am staying in a hotel close by. I am very comfortable with you. Let’s not beat around the bush. I hear you are very well hung and I want you to fuck my brains out.”
As soon as we were in the door Mary was over me like the proverbial rash. Tongue down my throat, which really turned me on and gave me an instant erection. She had me undressed to my briefs in a flash, then pulled them down.
“Wow, hello big boy, what a cock and thick as well, magnificent. Lay on your back on the bed,” she instructed in a very firm tone.
“My legs have always been my strong point, and I can tell your cock likes them,” she smiled as she removed her slacks, then her shirt.
“My tits and ass are pretty good for a fifty-year old as well, I think.”
She was correct. A big, though very well proportioned and still firm ass with just a touch of cellulite (an extra turn on for me), flat stomach, tucked in waist and good large tits that were just starting to sag (another extra turn on for me) with big erect nipples. For her age, a wonderful hour glass figure.
She mounted my very erect cock and ever so slowly slid the full length of it into her very wet cunt lips. Nothing quite like a sex starved older woman who wants to fuck you silly.
As she slid up and down my full length and ground into me, her language became very coarse and rasping. “My cunt is sopping wet for you. Fuck my cunt big boy. Fuck it harder, harder, much harder. Give me every bit of your big cock.”
After three huge, screaming orgasms she remounted me so her ass was facing me. Watching a magnificent, full size-14 ass, sliding up and down your rock hard cock, while you are holding it with two hands and being repeatedly told to, ‘fuck my cunt big boy,’ was enough for us to orgasm together.
“For my age I am sexually naive, when I look at sex sites on the internet I realize what I have missed out on. I want you to satiate me sexually. Make my fantasies happen. I want to lose my sexual inhibitions. Teach me, be my sexual mentor, use me. Talk dirty to me. Make me your sex slave,” she told me in the afterglow. A real buzz an older woman asking those things of me.
An hour later we were in the shower together. Without saying a word I lathered up her pubic hair. “Your cunt is far too hairy,” I told her as I shaved her to my satisfaction, leaving her with a just neatly shaved fringe above her cunt lips.
“I do like that look, and the sensation of you shaving me is a buzz. I am learning from you.”
“I want to pleasure your voluptuous body with my tongue for your pleasure and mine. Put your heels on, stand with your legs apart and your hands on the wall,” I tell her as I dry her body with a towel. “I have an ass fetish, I love a big firm ass and yours is magnificent,” I tell her as I grasp her hips and kneel and lick, then kiss her glorious ass cheeks as she clenches it. “Magnificent, how long since a man worshiped your ass?”
“Never, never ever. I love what you are doing and the way you are doing it.”
“How big is it?”
“Forty-three inches.”
“And your tits, how big are they?,” I ask a few minutes later as I am sucking her large, erect nipples.
“Thirty-eight D.”
“They would look wonderful in a cup-less bra while suck I your nipples.
“You have brilliant thighs, they were an immediate turn on as soon as I saw you in those skin tight slacks,” I tell her as I lick the insides of her thighs. “Would you like me to fuck you with my tongue? Would you like me to lick your cunt so you orgasm?,” I ask without waiting for a reply.
“You are the first man to ever lick my cunt. And I like it,” she tells me as the tip of my tongue finds her engorged clit. “And love your hands on my ass at the same time.”
We fucked four times that day from two-thirty until late at night. When she went to the bathroom naked early the next morning, the site of her big ass had me instantly aroused. “Your big ass is magnificent, fucking magnificent,” I told her as I grasped her ass cheeks and fucked her from behind.
“I live not far from here in a penthouse. I have a spare bedroom, why not stay with me and save some money?”
“Show me your spare bedroom. Now your bedroom,” she asked as soon as we walked in to my penthouse. “Oh wow, mirrors everywhere and on the ceiling. “No need for the spare bedroom. Fuck me so I can watch in the mirrors.”
“Before we do I want to show you my sauna room.”
“Wow, enough seating for six people. And a hand-held, needle spay shower head. Do you fuck in here?”
“Only you,” I reply diplomatically.
“Good, do it now, right now,” she tells me as we undress each other, then soak up the steam from the sauna before I spray both of us with the needle head.
“What is the bowl of ice for?,” she asks as I re-enter.
“Foreplay and sexual pleasure for both of us,” I tell her as I run ice over her nipples with one hand and ice over my nipples, my balls and along my very erect cock with the other hand. “Your nipples like that, look at the size of them,” I whisper as I lick and suck them. “Heat and cold, is that good?”
“Yes, you are wonderful mentor, and I am a quick learner,” she tells me as she licks my nipples and runs ice along my cock.
“And this?,” I tease with ice in my mouth as I lick her cunt lips.
“I really have been missing out, that is a revelation and so fucking sexy,” she moans as I slide an icy tongue along and into her cunt lips.
When she sucked my cock with ice in her mouth she could not believe my reaction - and erection
Over the next three weeks we fucked at least three times a day with all sorts of variations.
Her first blow job was below par. “I have never ever sucked a man’s cock, teach me. Tell me what you want and like.” By the fourth day she had nailed it. Lips, tongue, fingers, lick, suck, blow, squeeze and twist with one hand while teasing and scratching my balls very lightly. Confirmed when she asked, “Do you want me to swallow?”
After a few days we were calling each other ‘baby’. I took her shopping and watched as she tried on cup-less bras, g-strings, high-waisted thongs, stockings and suspender belts. As part of our mutual turn ons we always asked the shop assistants, males and female, for their opinion. Invariably, “Wow, what a body.”
On the way home she wore her new stockings and suspender belt, no knickers and new cup-less bra with her erect nipples straining against her also new black silk blouse.
“Does my body look good in my new outfit? Do I look fuckable for you?,” she teased as soon as we were in the door as she removed her blouse, then dropped her skirt. “Does my ass look big?,” she teased with a big smile as she strutted around the room and flaunted her almost naked body for me.
One afternoon I oiled her totally naked body and licked her big nipples as I slid an oily finger along her wet cunt lips while she ran an oily hand along my erection. Twenty minutes of mutual edging before we orgasmed together.
“You like that don’t you, watching me pee with my legs wide open?,” she asked one day with a huge smile after a wild sex session as I watched while I showered. “Your cock was flaccid when I sat down. Look at it now.”
“Tomorrow a golden shower?,” I asked.
“Why not today baby? You really have made me lose my inhibitions, another first for me” she told me as I lay on the shower floor and she stood over me, legs apart and sprayed me.
“Today I want to make you squirt for me,” I told her one morning as we showered together while I washed her ass, (I can’t get enough of it). Half an hour later Mary was resting on a stool, naked apart from her cup-less bra and heels which barely touched the floor. “I want you to you squirt for me,” I told her, after two very wet orgasms on my tongue as I slid and curled a finger into her and found her g-spot as I continued licking her. “Two fingers baby,” she told me in her stentorian school mistress voice before I teased her by withdrawing my finger and letting her suck it.
“Two fingers baby, make me squirt for you. I have never squirted for any man,” she told me as I teased and edged her g-spot before she let go.
One day I asked her to phone one of her girlfriends as we were about to fuck. “How is your holiday going Mary? Have you met any men like you intended? What is all the that noise I can hear? Your voice sounds strained Mary? Are you alright? Are you having sex?”
“Yes, a man with a thick eight-inch erection is fucking me. He has fucked me at least three times a day since I arrived here.”
“Do you suck his cock? Does he lick your cunt?”
“Yes and yes. I have also discovered I am multi-orgasmic.”
Another day I found an excuse to spank her magnificent ass with a belt. “You broke one of my best wine glasses. I need to punish you.”
“Would a spanking make up for the broken glass? A really good spanking?,” she asked with a big smile. “I used to work in a spanking environment. And I have been naughty, very naughty with you. And I am not wearing any knickers to cover my big ass,” she teases as she lifts her skirt and slides them down over her ankles.
I still can’t get enough of her glorious big ass as I ogle it while she bends over a table and lifts her skirt to expose her naked ass. “I deserve a spanking, I really do. Harder baby, harder, much harder,” she is hissing as I use one of my belts. “So good baby, wonderful foreplay, I love it, you know I broke your glass deliberately.
“Now fuck me, I am so aroused.”
“I am well on my way to losing my sexual inhibitions,” Mary told me one afternoon in the afterglow of another session.
“I would love to watch you having lesbian sex. Another woman licking you to orgasm. And you licking the same woman to orgasm,” I told her with just that woman in mind.
“Make it happen baby, I would love you to watch. A long held fantasy. Will you masturbate for me while you watch?”
“I told Patricia all about you. She is due here at two-thirty to seduce you,” I told Mary two days later.
Mary was flushed and obviously excited while I watched her prepare for Patricia. “How old is she? What should I wear for a woman who is wants to seduce me? Are you going to join in? Have you ever fucked her?,” she had asked earlier.
“Ten years younger than you, a size-12 blond, she is bisexual with a very feminine body and really into oral sex. Wear your feminine best for her, heels, a high-waisted thong, a cup-less bra and one of my shirts. And yes and yes to your last two questions.”
“Do you think she will like me?,” Mary asked as I watched her dress and ogled her body. Before I could answer Patricia was on the intercom.
“I feel almost naked,” Mary told me with a wicked smile as we waited for Patricia to arrive.
“Good, she loves sexy naked bodies.”
“This is Mary, Patricia and this is Patricia, Mary,” was alI I said as the two women sized up each other, before Mary took her hand and led her to the bedroom.
Their sexual attraction and chemistry was amazing as I watched them kissing passionately as they undressed each other.
Watching Patricia sucking Mary’s nipples and her doing the same to Patricia had me erect immediately. And I did enjoy licking and kissing Mary’s ass cheeks at the same time for Patricia’s benefit.
Patricia was flat on her back when she told Mary to sit on her face as she grasped her ass cheeks and slid her cunt lips along her tongue. Her school mistress demeanor was completely abandoned as she repeatedly muttered, “Fuckamycunt, fuckamycunt, fuckamycunt.” Then she reached out for my erection and commenced sucking it.
Mary must have had three orgasms on Patricia’s tongue before she told her to watch as she used her hand to bring me to orgasm.
After we showered I watched Mary provide Patricia the most exquisite lesbian sex. “I was the school mistress in a boarding school with lots of women teachers. We had lots of spare time on weekends,” she told me later.
A few days before the end of her visit, I asked Mary if she would like to fuck another much younger, well hung man while I watched.
“Another of my fantasies, can you make that happen for me? Or is it us?”
“Us, I can make it happen, however the man I have in mind might want to have me as well as you. Would you like to watch another man suck my cock.”
“Yes, I would, that covers lots of my bucket list wishes, let’s do it.”
On the very last night of Mary’s visit she was dressed to impress for her fantasy man. I had just a tiny black jock strap under a shirt with the buttons undone. “Do you think he will like me?,” Mary asked as I watched her dress. Heels, a tiny black g-string and a cup-less bra.
“What exactly is the plan for tonight baby?,’ she asks.
I have organized Michael for us, note that I said us. He is in his late twenties, with a toned, fit body and a very large, thick cock, ten-inches when erect. You are are almost twice his age, he has a thing about cougars, and he loves big asses.
“You look extremely fuckable Mary, I want you to have one of my shirts over your outfit and flash it open when he arrives.
“Your turn on is my turn on Mary. I want to watch him fuck you.”
“I want to have a full on erection when he arrives. I want to tease him. “And afterwards I want Michael to suck my cock while you watch. My finders fee.”
Earlier that day I had told Michael, “I want to watch you fuck Mary with your ten-inch erection, so does she. Your turn on is my turn on. As soon as you arrive Mary is going to flaunt her voluptuous body for both of us, you especially.
“And afterwards I expect you and want you to suck my cock while Mary watches. My finders fee.”
“Three weeks ago I could only fantasize about this. I wanted you to make my fantasies happen. I wanted to lose my sexual inhibitions. I asked you to teach me, to be my sexual mentor, and use me. Talk dirty to me. Make me your sex slave, I told you,” Mary tells me as we wait for Michael. “Does he really have a ten-inch erection?”
Before I can answer Michael arrives right on time. With great aplomb, and without saying a word Mary flashes open her shirt and lets it drop to the floor, then turns her back and struts around the room to show Michael her glorious big ass framed by her g-string. An instant turn on for two men, both with an ass fetish.
“Wow,” is all Michael can mutter as he throws his shirt off, then slowly slides his jeans down to show Mary his large, thick, semi-erect cock. Mary and I are both watching intently as he strokes his cock as he ogles her almost naked body. Almost immediately he has a full, thick ten-inch erection.
“Yes?,” he asks Mary imploringly.
“Yes, yes, yes,” Mary replies as she undoes the clip on her g-string and it falls to her ankles.
“Which way?,” Michael asks.
Mary is very much in charge of the situation as she takes his erection in a hand and leads him to the window facing out over the city skyline. Just as she had done for me several times she braces on the window frame, legs apart.
“You are huge. Worship my ass before you fuck me.”
I am unsure how I feel about one of my friends fucking the woman I just spent three very intimate weeks with. Though I have enjoyed watching Michael fucking women in the past. Watching any attractive couple fucking is always a buzz for me.
At any time watching Michael fucking with his thick, ten-inch erection and the reaction he gets from the woman he is about to fuck is a very special buzz. Something I always get an erection from. The last time I watched he had an attractive size-8, forty three-year old with a good figure. Awesome, watching a huge cock in a small, very receptive woman.
“Later Michael, Mary first,” I whisper very aroused as Mary tongue kisses Michael as I slide my jock strap under my balls to flash my erection for him.
My erection is rock hard as I watch Michael grasp Mary’s ass cheeks and slowly slide his thick, ten-inch erection into her. “Is he good baby, is this what you wanted, ten-inches?,” I ask her as we tongue kiss.
Michael is well known for his ability to last - to fuck for - more than thirty minutes and he did this time with lots of encouragement from Mary.
Over an hour later Michael is paying his dues. I have my hands behind my head soaking up the pleasure with my erection between his pursed lips while Mary watches before she tongue kisses me.
“Another of my fantasies, sucking a huge cock while that man is sucking another huge cock,” she whispers as she commences sucking Michael’s erection.
I didn’t manage to last as long as Michael, though I did enjoy watching Mary blowing him as I talked dirty to both of them with my hands on her glorious ass.