I was thirty-eight when I first met Carly, a divorced sexually naive woman in her early forties at a singles function. At first a little unsure of herself on the singles scene. As one of my male friends said, “She has been alone for too long.”
Carly was an attractive brunette, smartly dressed, taller than most women, slim, long legs with a good body and much better tits than I thought at first.
Our first date was an invitation for dinner at her inner suburban house. I assumed it was to be a dinner party, but it was just the two of us. After dinner and without any hint of foreplay she told me directly, “Let’s go to bed.” We did and the sex was very good for our first time.
It turned out Carly had only ever had one man, her ex-husband, and she was determined to bring her sex life up to speed. The first time she wanted to give me a head job while we were still in bed was awkward and clumsy, so I told her, “I will teach you how.”
The next time we were both naked, me sitting in a chair teaching her how I liked my nipples licked and sucked, a sure way to give me a boner before I taught her how I liked my head jobs.
Talking to her, my hands on her head, whispering instructions, with an absolute boner. She was so pleased to be learning from me, her ex had no interest at all in oral sex she told me. “Your cock is huge compared to his, and so thick when I make you hard, really hard.”
After half an hour she still hadn’t got her technique quite right. I was so close but she couldn’t quite get me over the edge. So I decided I would show her how to masturbate me. Giving her a tube of lube to smear over my erection, telling her to clench her hand tighter.
Then putting my hand on hers, showing her how I liked being masturbated to orgasm with her hand. Then two hands, telling her to kiss me when I was right on the edge. Then watching her wide eyed as she masturbated me to orgasm for the first time, so pleased with herself.
For her next attempt at giving me a head job, I was wearing my short black silk dressing gown, unfastened when I opened the door for her. Her eyes ogling my cock immediately. Then watching Carly change into something sexy for me. Totally naked for me before she put on a sexy black garter belt, then the stockings and finally heels. “I feel incredibly sexy for you in dressed like this. Am I turning you on?”
Telling her, “I am so horny. If you weren’t here right now I was going to masturbate while I fantasised about you.” A glass of grape fruit for her, I wanted her mouth wet, very wet, sloppy even, asking her to repeat the word purple ten times. Watching her lips form into the perfect shape for my head job, fellatio, a blow job.
“Tease me edge me, my big cock has never been this big and hard for you ever before. Look at that vein along my cock bulging for you, you did that. Tease it with a fingertip while you lick and suck just the tip of my erection.”
This time Carly was far more confident. Telling me, “I want you to cum all over my tits. Or would you like me to swallow? Not before I tell you to.” Then spitting on my erection, finding it exciting to see my reaction, then some extra lube for me.
Using her hands. One hand around my shaft, simultaneously moving her hand and mouth up and down my erection. Enhancing the motion, twisting her wrist back and forth as she moved up and down. Lots of lube. Using her other hand to gently massage my balls.
So enthusiastic, telling me, “I wanted to do this to your big cock the moment you first showed it to me. Do you like how this feels? Or this?” Looking up every so often to make eye contact, indicating she was enjoying herself as much as I was.
Teasing and edging me, Using her tongue to stimulate the head of my erection. Applying soft pressure with her tongue against my throbbing erection, moving her mouth up and down my rock hard shaft.
Changing the pace, focusing her tongue on the head of my erection. Using the tip of her tongue to lightly lick the top of the head of my erection in a slow circular motion.
Deep throating me, as much of my erection as she could take, far into her mouth, reaching her throat. So confident this time. Repeating, moving my erection back and forth in her mouth.
Tongue kissing me, totally in control, rubbing the tip of my erection over her nipples, arousing them even more, telling me, “I want you to cum all over my tits. Not before I tell you to.”
Making it a full-body experience for me, licking, sucking and chewing my nipples. Pressing a vibrator against her chin so the vibration passed indirectly to my erection. Carly has been doing her research, watching porn clips, she told me afterwards.
Then whispering, “I want you to cum all over my tits. Or would you like me to swallow? Swallow yes?”
In between our bouts of erotic love making, a new hairdo for her. I took her shopping in lingerie shops. For the first time in her life Carly was wearing garter belts and stockings, cup-less bras, feeling good about herself while wearing them for me. Turning me on at the same time.
Watching Carly having her pubes waxed for the first time in the back of the lingerie shop, smiling at me, asking if I liked watching, a real turn on for us and the woman her age doing the waxing before she watched me have my pubes waxed. Fucking like rabbits as soon as we were in the door.
After nine weeks Carly was barely recognisable as the sexually naive woman in her early forties I first met. A huge sexual learning curve for her. She is a very eager and quick learner, Every time we meet she is even more fuckable and sexually skilled. Skilled at fitting my cock rings for me, clipping them under my balls.
Watching her pee, a little embarrassed the first time, but after a while turned on by me watching her pee, kissing her while I watch. Teaching her how to give me a golden shower. A huge turn on for both of us.
A complete make over, clothes, hairdo, now sexually confident, a wonderful lover, her conversation in bed an extra turn on, dropping the c word and the f word with great aplomb. So good when she whispers, “Fuck me, fuck my cunt, fuckmycunt, so good.” Enjoying me taking nude pics of her and pics of us both in the mirror. When we meet at her house now she greets me at the door wearing heels and almost naked, proud of body.
Asking her lots of questions, tempting her, tempting myself while giving her cunnilingus, tongue fucking her. “Another man with a huge erection, bigger than mine is watching. You could be sucking his cock while I am tongue fucking you.
“One of your girlfriends wants to tongue fuck you while you give me a head job. Women are always better at tongue fucking another woman than men. I would love to watch.”
“I told one of my girlfriends about you, about us. She asked if she could watch me fucking you?,” she told me a few days later. It wasn’t long after the same girlfriend, another suburban housewife was watching us fucking, a woman around Carly’s age, Carly determined to show her new sexual side to her. For a few weeks in the lead up Carly had been asking if another woman had ever watched me fucking my previous lover.
“Another of my unfilled fantasies. Two actually, another woman watching you fucking me, and another man watching you fucking me.”
“I feel like your sex toy,” I told her when she confirmed she had organised another woman to watch us fucking.
“You are, I have a lot of catching up to do.”
Kate was far more glamorous than a typical suburban housewife when she arrived, dressed in heels and a short black, backless dress, Carly and her kissing when she arrived, Kate obviously excited at what she had come to watch, just as Carly and me were. We were both naked underneath our matching short, black silk dressing gowns.
“You are a different woman to the suburban woman living just up the road, I knew up until recently, Kate told Carly as she removed her gown, kissing her as she did. “Oh wow, a far different woman, look at you. What a body, so fuckable, and I love the way you wax.”
Then removing my gown, ogling my body, telling me, “Carly told me she wants me to watch you fucking her. She also told me she wants me to tongue fuck her while she gives you a head job.”
Carly and Kate were tongue kissing, as I undressed Kate after she asked me to. She was completely naked under her backless dress, hands on her hips, proud of her body, good legs, even better hips, ass and good tits.
“My man would love to watch me tongue fucking you Carly. We lived so close to you for years, without you knowing I was bi, what a waste,” Kate told her as Carly was sitting in a chair, Kate’s arms wrapped around her legs, receiving exquisite cunnilingus from a woman for the first time in her life.
Reminding me, as she looked up, “Carly wants me to tongue fuck her while she gives you a head job. Before I watch you fucking her.”
The best foreplay ever before Kate watched me fucking Carly from behind, resting her her hands on Kate’s shoulders for support, the two women tongue kissing, while Carly moaned, “What a fuck, what a fuck,” all three of us so comfortable in the shower together afterwards before Kate had Carly again.
When Carly’s birthday came around it was a perfect opportunity to stretch her sexual boundaries, our sexual boundaries. Recalling her second unfilled fantasy, ‘another man watching you fucking me.’
“I am going to email you a list of options I have for your birthday. Let me know your preferences. Don’t be too greedy. You can choose just one option.”
“Do they involve sexual options?,” she asked.
“Of course, I live to please you.”
1. I could organise another man for your sexual pleasure.
2. I could organise another man for our shared sexual pleasure.
Carly phoned me after she received my email. “Number two is very appealing, another man for our shared sexual pleasure. I told you I wanted another man watching you fucking me. Does that imply a new man could tongue fuck me while I give you a head job? Does it also imply a new man could give you a head job while I watch? Does it also mean a new man could give you a head job while I give him a head job?”
“It’s your birthday Carly, I live to please you,” I replied without setting any time frame, though her birthday was close.
The next time we met I decided to tease her, and myself, with no mention of the options I had offered her. Asking her lots of questions, tempting her while giving her cunnilingus, tongue fucking her.
“Another man with a huge erection, bigger than mine is watching. You could be sucking his cock while I am tongue fucking you. Perhaps you would like to share another man with me? You could suck his cock while he sucks my cock.”
That one really sparked her interest. “That is one my absolute top sexual fantasies. I have always wanted to watch a bi-sexual man give another man a head job. Then a direct question, it must have been the inflection in my voice that sparked her response. How old were you when another man gave you your first head job?”
“A gentleman never tells,” I told her teasingly, our relationship on the cusp of a new and exciting direction.
“Organise it for me, for us, I want it, so do you,” she whispered as she passionately kissed me, her hand on my aroused cock.
“I will organise it for you, for us, you want it, so do I,” I whispered as I turned on my computer to show her pics of some of my male associates. “Choose for us, for you, for me,” letting her scroll through naked pics of three naked men in their thirties, all wth six pack gym bodies. The first pic of each man naked in front of a wall length mirror with a flaccid cock, their ass showing in the mirror. In the second pic the men with an erection.
“Your male associates all have a similar appeal, muscly six pack bodies, and wonderful erections. Did you take the pics?,? Carly asked as she scanned through the pics a fourth time. “Can we have number four please?”
“Why did you choose Milton?,” I asked, pleased that she had, second guessing her answer.
“You know why, he had the biggest flaccid cock and the biggest erection, bigger than you. Are you really going to share another man with me? Let me suck his cock while he sucks your cock?,” she asked as she watched me send him a text.
‘My new lady Carly wants to share you me for her birthday. She was impressed with your pics. She wants to watch you suck my cock while she sucks your cock. Pics of Carly nude attached. Next Friday night.’
An almost instant response. ‘Tell her yes and happy birthday.’
The next Friday night Carly asked again, “Are you really going to share another man with me? Let me suck his cock while he sucks your cock.” This time Milton was standing alongside us.
Carly had a hand on my erection and Milton’s at the same, the first time in her life she had two naked men. Comparing our erections, touching them together, before she commenced sucking Milton, running her hand along my erection at the same time. I liked it, wanting to be rock hard for Milton when he has me, for him and for Carly specially.
Milton had his erection pushed against his torso, teasing just the tip of his erection with the tips of his thumb and fingers as Carly licked his balls. Her hand on his erection, rubbing it over her nipples, something she learnt from me.
So exciting watching my lady Carly giving a head job to the man who is going to give me a head job, only the second man ever to receive a head job from her. And me the first man she has ever watched receiving a head job from another man.
I was so pleased the arrangements Carly requested were in play. So turned on watching her give Milton a head job while receiving one from him.
Milton had Carly’s complete attention as she watched me feeding my erection between his lips, his only other contact two wet fingertips on my balls. He was on a chair leaning back at forty-five degrees, as Carly watched fascinated, forty plus and until now she had never watched a man giving another man a head job.
The sexually naive woman I have have been nurturing for months is now a pornographer’s delight.