I Dont Play Pickleball

I'm 66 years old, married, and semi-retired. I still handle a few cases down at the courthouse, and about a year ago I met a woman who has intrigued me. She is in her late fifties, recently (within the last two years) divorced, and quite attractive. We have developed a mutual attraction, without acting on it.

My sex life at home has gone stagnant, maybe sex on the weekend, in the morning when I'm not fully awake, and "hurried", like my wife just wants to get her "duty" over with. I miss the old days of sexual adventure and experimentation.

I am too old to start another relationship, but I'm not dead yet. I asked Sarah, the divorcee, to lunch, and she accepted. I took her to a private, out-of-the-way little place where no one would know us, or disturb us.

I told her I was looking for a friend, someone to play pickleball with, someone who would be my companion. She said "I don't play pickleball." So, I asked her to be my alpha-female Mistress.

I explained that I was interested in exploring female-dominance. I wasn't looking for pain, no S & M, but I was interested in being dominated. She seemed taken aback by this, and asked what, more specifically, I wanted.

I told her that I would eat pussy on demand and was curious to try eating a cream pie. I wanted someone to take control of my cock, to milk me, and make me come only at her pleasure. I was interested in being pegged, and to have my face ridden like a pony.

She told me she would think it over. I told her I would be happy to provide whatever she needed; lingerie, leather, latex, etc. That seemed to ease some of her concern, and she said, "Of course you will."

The first time we got together was at her office. She texted and told me to arrive shortly after three pm, when her secretary went on her courthouse run. I arrived at an empty reception area, but I heard her command that I enter her office and close the door.

I was ordered to my knees and told to crawl to her. She rolled her chair out from her desk, and I could see that she had lifted her skirt up over her waist and removed her hose and panties. She smiled slightly as she commanded me to crawl over and lick her pussy.

I quickly complied, and soon I experienced the satisfaction of pleasuring Sarah with my mouth as she leaned back in her chair, legs spread wide, her heels on my back, while she guided the back of my head with her hands and told me how to eat her pussy. She directed the location, the pace, the activity (licking, sucking, tongue-fucking), and coached me through three of her orgasms.

Then she told me to stand before her as she undid my pants and seemed pleased with my erection. She fondled me, stroking and cupping my balls, and brought me to the brink of orgasm.

Then she stopped. I was told to have my shaft and balls completely shaved from then on. I was directed to obtain a prescription for Viagra, so that I could stay hard as long as she desired.

Then she leaned forward and took my manhood into her mouth. She again fondled, and stroked me, bringing me quickly to orgasm, which she took in her mouth with no hesitation. Then she stood, and kissed me, pushing my own come into my mouth. We kissed until the come was gone.

She told me to get dressed and leave, but on the way home I was to stop at Victoria's Secret and buy her stockings, with a garter belt, and a corset. She told me to bring any toys I was interested in trying out, and next time I was to get a room at a local hotel.

The instructions caused my erection to try and return, something I hadn't experienced in years. I did as directed.

I'd purchased many sexual toys over the years, in hopes that the wife and I might try them out, but usually they just ended up in a big suitcase we kept under the bed. When Sarah mentioned toys I wanted to try, two immediately came to mind.

One was a strap on dildo that affixed to the chin of the wearer, me, with latex straps that went around the head to hold it in place. The idea, as I understood it, was for the woman to lower herself onto the dildo by straddling my face, then she could ride the dildo while my mouth would be strategically located to lick her clitoris. My wife had never even tried it.

The second was a Feel-Doe, a two headed dildo designed so that a woman could place one end inside her vagina, and the longer, other end, was placed at a near 90-degree angle. That way the woman could have the dildo inside her but use the other end to thrust into another orifice. It was marketed to lesbians, but they also said it could be used to peg a man.

I had gotten my wife to use it on me once. As dildos go, the Fee-Doe was slimmer, and very smooth, so it slid up my ass easily. Just the few pumps my wife had made into my ass had felt wonderful, but she didn't like it, and into suitcase purgatory it went.

I put my lingerie purchases, plus the Feel-Doe and the chin dildo, into a box and put them into the trunk of my car. I threw in some other items: cock rings, both silicon and steel, lubricant, a blindfold, two ankle and two wrist restraint cuffs, along with old pantyhose for tying.

I already had a Viagra prescription, but I got a re-fill, and I spent half an hour shaving my shaft and balls. I got carried away and shaved my entire pubic area around my dick, I hoped that Sarah would be pleased. I liked the way it made me so conscious of my cock.

It was almost a week before Sarah texted again. I was to get a room at a nearby hotel, again for three in the afternoon, and be waiting for her arrival. I was to text her the room number. While waiting I was to strip, shower, touch-up my shaving (both to my face and my cock) and have a Viagra pill in me.

I got the room, and they let me check-in at two. I popped the pill, and showered, going over myself with a razor, getting very smooth. I had the box with the goodies on the table, and it was very hard to not play with myself as I awaited her arrival.

At precisely three there was a knock on the door. I opened the door and let Sarah in. She was wearing slacks, and a blouse. Just hearing her knock, and the anticipation, had caused my dick to harden. Sarah looked at me, and my erection, said "Good boy!" and she again began stroking, and fondling me, "Nice and smooth!"

Before she went too far, she commanded me to undress her. I unbuttoned her blouse, and removed it, then I unhooked her bra. I took each nipple in my mouth and sucked it, I couldn't help myself, then I unbuttoned her slacks and lowered them. She sat on the bed as I knelt before her and removed her shoes and slid her pants and panties off of her. I reveled in her naked glory.

She put her foot in my mouth and ordered me to suck her dainty toes. While I did this, she grabbed the box and looked through it. "Nice. Interesting" were her comments as she investigated what I had brought.

She turned away from me and got on her hands and knees on the bed, scooting to where her knees were right at the edge. "Eat me!" She ordered, and I spread her ass cheeks with both hands as I leaned my face into her from behind. I worked her pussy again, as she told me what to do. When she told me to lick her asshole, I didn't hesitate.

I licked, and tongue-fucked her little brown hole like it was filled with ice cream. After a bit, she bade me stop, and she told me to put on the chin dildo. I had tried it on before, but I had never actually used it. I got it on, and lay on the bed beside her, face up.

It was a glorious sight to watch her lowering her sopping pussy towards my face, astraddle of my head, and I could feel as the dildo slowly penetrated her. She took her time, occasionally rising back up, only to lower herself further, until she finally bottomed out against my face. She leaned forward, putting some weight on her arms, and it brought her clit directly into contact with my mouth.

I didn't need her to tell me what to do, I began sucking, and licking her engorged clit, and she began humping that dildo and my face. I could feel her juices flowing down the dildo, into my mouth, and over my face, it was very erotic. She rode my face through several possible orgasms, (she would tense, then relax, then begin anew) then she slid down and placed one of the silicon cock rings, the adjustable one, around my substantial erection. She pulled the ring tight then lowered her pussy over my cock.

I was in heaven! Her pussy was so warm and wet, and tight. She humped me easily, seeming to thoroughly enjoy the feeling of me inside her. Although I was very excited, the cock ring allowed me to last a long time, and she came again riding me. I could feel the pulsations in her cunt as she came, and she moaned "Yes, Yes!"

After she relaxed, she lifted off me, and removed the dildo from my face. She then sat back down on my face "Gently now." She said as I licked her vagina tenderly, and slowly. I felt her hands on my cock, and I heard her say "Come for me now." She began a milking motion with her hands, drawing the cum out of me. It didn't take long. I shot several ropes of come up into the air, and I felt them land on my chest. "Very good!" She cooed, and she rubbed my come into my chest.

Afterwards we talked, like regular people. I told her I had loved having her in control, and she admitted that she really liked it too. She took the box with her and told me we'd meet again in a bit.

It's been two weeks now, and I am on constant sexual edge. I keep my cock shaved, but I don't allow myself to come, because I want to be ready for her when she beckons. I've been practicing taking a dildo up my ass in hopes she will peg me soon. It's hard to think of anything else.

She texted!