By the time I was twenty-years old I felt sure I was far more sexually experienced than any of my buddies. I also knew I had the good fortune to be endowed with a much larger and thicker cock than any of my buddies. Confirmed in the change rooms of the sporting teams I played for, with surreptitious glances from other players my age and even older men in the team as well as the support staff. Receiving flattering remarks was always an ego trip.
I was barely eighteen when I lost my virginity to one of my mother’s friends Nancy, a woman twice my age. On several visits to my mother she had ‘accidentally’ seen my naked body when I showered. “Now that you are eighteen you are old enough for me to fuck you,” she told me one day as I ‘accidentally’ showed her my naked body.
A clandestine meeting soon afterwards. Incredible physical attraction. Nancy fucking me, teaching me. Fucking me again an hour later. Telling me I was a lucky boy to be so well endowed. Boosting my confidence and my ego when she told me I was far bigger than any man she had ever had. Even though she was married we found lots of time to be together.
Giving me my first head job, so good. Teaching me how to give her cunnilingus, explaining to me exactly how she liked to be licked to a climax. “My clitoris is the powerhouse of my orgasm, and the vast majority of the sensitive nerve endings that contribute to my sexual pleasure are located on the surface of my vulva, not inside my vagina.”
My sexual confidence was sky high the first time I licked and teased her to a climax. My sexual confidence even higher the first time she squirted for me. Nancy was a wonderful teacher and mentor. “Sex isn’t something you do. Sex is a place where you go. Ask yourself what do you want to experience there? Is this an experience, for you, an experience beyond the normal or physical level? Of deep connection? The only non-negotiable? Sexual pleasure should be the main course.”
Sexual pleasure invariably was the main course with Nancy. I was so spoilt learning about sex from Nancy. Nancy taught me talking dirty before sex, during sex and after sex can be a huge extra turn on. For the rest of my life listening to a woman telling me to, “Fuck my cunt, fuck my cunt, fuckamycunt,” while licking her clitoris, her pussy has been a turn on and an ego trip.
When Nancy informed me, “I told one of my bi-sexual men friends about you and how well endowed you are. He told me he would love to give you a head job. He wants me to watch. Would you like me to watch?”
I had always been bi-curious, and this was an opportunity too good to pass up. “Tell me some more about him?”
“He is twice your age. He has a wonderful body. And he is very talented.” Asking me again, “He wants me to watch. Would you like me to watch him blow your huge cock? Yes?”
A few days later Nancy was prepping me for my first blow from another man. She was naked apart from her heels and skimpy black lingerie, smearing oil all over my naked body, before sliding two oily hands along my erection.“When Rocky arrives I want you to tempt him, make him want you.” Teasing me when she asked rhetorically, “Are you sure you would you like me to watch another man blow you, suck your big cock for the first time? Yes?”
Moments later when Nancy opened the door for Rocky. I was standing hands on hips, flaunting my already rock hard erection for him. Wanting him to blow me, another step in my sexual education. My already rock hard erection straining as he threw his clothes off. His toned naked body and large thick cock, an extra stimulus for me. My was ego so pleased another man found me sexually attractive, also pleased his cock was not as big as mine.
Nancy kissed me with lots of tongue while Rocky was sucking my cock. Rocky was good, really good, doing things to my cock and balls Nancy had never done. A whole new vibe. My first three-way. The first time another man had sucked my cock. The first time a woman watched a man sucking my cock. The first time a woman talked to me while she watched a man sucking my cock. Talking to the man giving me my head job. Making suggestions. So good. I was so turned on with two pairs of hands pleasuring my body. The first time I had orgasmed for a man while a woman watched.
I was reminded of something I had read. Sex should momentarily rob you of your intelligence. Sex should make you a bit selfish and maybe even regress. Good sex makes you dumber. And great sex makes you really, really stupid. I was very selfish and really, really stupid for Rocky. And for Nancy.
Nancy told me I should set some goals for my sex life, just as I had done for my business career. Typing them into my computer for me while I dictated some of my sexual goals. Sex with a drop dead gorgeous woman forty years old. Sex with a drop dead gorgeous woman fifty-years old. Sex with a drop dead gorgeous woman sixty-years old. Nancy asking me, “Would like another man to be involved? That could open up a wide range of exciting, scenarios.”
Two years later my life had moved on, a new job in a new city with a new lover, Helen, ten-years older than me. Instant mutual sexual attraction the first time I met Helen.
One Friday night Helen had her back to the wall, she was naked apart from her stiletto heels and a cup-less bra. She had her legs spread, thrusting her hips forward, her ass was more than 12-inches from the wall, her arms upright over her head. Her almost bald pussy the centre of attention for me and a naked young man, a teenage boy.
A minute earlier she had been standing facing the wall, her hands on the wall for support, flaunting her magnificent big ass for her twelve-years younger teenage boy. Living out one of her sexual fantasies, and one of mine, oral sex from a teenage boy. Age wise the teenage boy was just that, a teenager. His toned muscled, six pack body that of a well built man. His already huge, thick, erect cock was an obvious visual turn for Helen, and for me. His cock was far bigger than mine. An exciting visual turn on.
For the past week Helen had been asking me if I could handle another man, a teenage boy, giving her sexual pleasure. “Of course I could. Who is he?” I told her brashly, eager to pander to her sexual wants and needs. And pander to my sexual curiosity.
“Jacob has been recommended to me by one of girlfriends.”
Before the teenage boy Jacob arrived, I was hoping he would be a sexual turn on for my voyeuristic side as well as for Helen. He was an instant turn on for me, a bi-sexual turn on for my voyeuristic side, a huge turn on as soon as Helen told him, “Undress for me, for us, put your clothes on that chair.” Ever since I met her, size had always been important for Helen. And for me, relishing the opportunity for me to compare my cock to other men and boys.
“Can you handle another man, a teenage boy, giving me sexual pleasure?”
“Yes I can. I love watching the boy licking you out while I am kissing you with my tongue.”
As I grew older I hadn’t forgotten the goals Nancy helped me set. The goals for my sex life, just as I had for my business career. Sex with a drop dead gorgeous woman forty years old. Sex with a drop dead gorgeous woman fifty-years old. Sex with a drop dead gorgeous woman sixty-years old. Along the way I had also learnt some of my women were bi-sexual
I was attending a business related cocktail party when I met April, a forty-year old woman while she was talking to a woman around thirty-years old, the same age as me at the time. She asked me if I would like to have a drink with her and the woman at her nearby apartment. Why not? Less than ten-minutes later we were in her condo.
April excused herself while the other woman and me were chatting and drinking some wine. When April returned she was wearing a sexy, black negligee. I couldn’t believe it when she let the negligee fall to the floor, to expose her almost naked body. Apart from her heels she was wearing stockings and a garter belt, skimpy knickers and a cup-less bra. A favourite sexual fantasy playing out in front of me.
I asked the other woman to hold my glass, before I knelt in front of April, sliding her knickers down to her ankles before the other woman watched me give April cunnilingus. When I was twenty-years old I could barely spell the word, though even then I knew what it was. Now, years later it was so exciting with another woman my age, watching me giving cunnilingus to a forty-year old woman, fucking her with my tongue, bring her to a climax. I can still remember the hard on I had while the other woman watched.
When I was thirty and sexually experienced beyond my early imagination, the thought of having sex with a fifty-year old woman was a current, sexual fantasy for me. Over the last ten-years I have become far more sexually sophisticated than I was when I met Nancy.
Liz was a dream come true, a full size-12 glamorous brunette woman, a woman, definitely not a lady. She exuded sex and sex appeal, talking constantly about sex, (“every pay day I have my pubes waxed”) and her sexual conquests. She had the fire and passion of her Spanish parents. A longer than usual courtship before she asked, “Don’t you want to fuck me?”
After we fucked for the first time I couldn’t believe her ass when I saw her body fully naked for the first time in the shower. Her waxed jet black pubic hair over her incredible thighs. Deliberately flaunting her ass for me, aware she had a killer ass. I was lost for superlatives, any degree of comparison to describe the quality and quantity of her ass in comparison with other asses. Her size-14 ass on her size-12 body was better than magnificent. So big, so firm, flawless skin, no dimple marks. I had to have it right then. Worshiping it, licking it, kissing it in the shower. Fucking it on the bed, while she told me to, “Fuck my ass, fuck my ass, fuckamybigass. Fuck it harder, harder.”
Liz was a Libra and the sexist woman I have ever known with brilliant thighs and as I had told her countless times, ‘the world’s best ass’. Forty-three inches of magnificent dimple free beautifully proportioned and formed flesh.
I used to love watching her shower and admiring her naked body before I helped her dry off. Bonus physical attraction. Sometimes I would kneel in front of her and lick my way up her inner thighs before licking her cunt lips. She used to especially like having her clit stimulated before we fucked.
Now that I am forty and sexually experienced far beyond my early imagination, the thought of having sex with a sixty-year old woman was a current, sexual fantasy for me. Over the last twenty-years I have become far more sexually sophisticated than I was when I met Nancy.
I have seduced and been seduced by countless women. Some men even. Every one of them with different and wonderful sexual needs and requirements. At forty I was proud of my ability to last, hold out, delay my orgasm, while having sex, even with another woman or a man, a third person partaking or watching.
As soon as I sighted Sylvia she met my criteria, a blond, class act, beautifully dressed to highlight her wonderful, shapely body. Her heels accentuating her long legs. Taller than average, with a wonderful confident bearing and a size-12 body with an incredible hour glass figure. Though I was unsure of her age.
She was easy to talk to, explaining to me she immigrated from Denmark as a very young girl. She had been widowed a year ago, after almost forty years of marriage, the only man she had ever had. Some quick mental maths, even though she didn’t look it, she must be sixty.
Sex with an attractive woman that age was a long held sexual fantasy for me. Wondering if a widow her age, had any interest in sex. I chose the moment to ask her. “A delicate and important question for you Sylvia, since becoming a widow have you had interest in sex?”
“Only with my vibrator while I watch porno movies. I am out of touch with what people do for sex these days”
“When was the last time?”
“This afternoon, sitting in front of an antique mirror, watching myself.”
“Were you naked?”
“No, I look sexier my new black, lingerie, a cup-less bra, stockings, heels and a garter belt, no knickers.”
“Did you climax?”
“Of course. Twice, so good while I fantasised about sex with a much younger man,” she told me confidently as she held my gaze.
We arranged a lunch date the next day. Flirting with each other over the table. I couldn’t help asking her, “Are you wearing your new black, lingerie today?”
“Yes, I am. A cup-less bra, stockings, heels and a garter belt, no knickers. Would you like a coffee in my condo?”
As soon as we were inside the door, we were kissing passionately, undressing each other. She had a magnificent body, her body a Danish delight. A pornographers delight. Beautiful flawless skin, wonderful long legs, magnificent hips and ass and beautiful firm, big tits with sexy nipples.
She was naked with one foot on a low stool, her legs wide open for me, “I have always wanted a much younger man to lick me like that. Lick me to a climax. Like that. Just like that. Before he fucks me. Fucks me all night.” We did fuck all night. And many other nights.
A few weeks later, a touch of deja vu, when Sylvia informed me, “I told one of my young bi-sexual men friends about you and how well endowed you are. He told me he would love to give you a head job. He wants me to watch. Would you like me to watch?”
I hadn’t had a head job from another man for so long. When Sylvia showed me some pics of the young bi-sexual man, she was watching me for my reaction. Telling me again, “Charles would love to give you a head job. He wants me to watch. I would love to watch him give you a head job. Would you like me to watch?”
She had more than a dozen pictures to show me. Each one more erotic than the last. Each one more exciting and tempting for me, for my bi-sexual side. Charle’s naked body was to die for. A huge turn on for me while my lover was showing me his pics.
Telling me again, “I would love to watch Charles give you a head job. Would you like me to watch?” Teasing me, “Would you be able to get a hard on for him? Achieve a full erection for him and for me while I watch.”
Less than a week later Charles had little interest in Sylvia’s almost naked body while I admired his naked body. His pics didn’t flatter him as much as they should have. “Charles wants to give you a head job. He wants me to watch. I would love to watch him give you a head job. Would you like me to watch?”
It was head job with a difference. An incredible head job from a renowned twenty-five year old, bi-sexual misogynist who was strongly prejudiced against most women. Sylvia did watch, tongue kissing me while he did wonderful things to my erection. Teasing and edging me to a mind blowing bi-sexual orgasm.
The next day Sylvia was determined to replicate the head job Charles had given me. Asking lots if questions. “Was that the first time another man gave you a head job?” Facetiously asking, “Did you have trouble getting it up for him? Have any other men had you? Have they?”
“A gentleman never tells Sylvia. Though right now I didn’t have trouble getting it up for you, while you are teasing and edging me to a mind blowing orgasm. You are so good. The best.” Letting my guard slip, “Better than any man.”