I’ve been seeing this woman professionally. I mean, since my wife died, I’ve been missing sex. Now my wife wasn’t all that wild, but what I miss, mostly because I never got it, is wild sex.
So I heard about Sharla. The first time, she greeted me at her door wearing a flowery dress, and after collecting her $120 cash, she led me into a large back bedrooom. It was an amazing place. Dark, but I could see literally hundreds of sex toys hung on the walls, on counter tops, and stacked in the corners.
Sharla, who is short and skinny with tightly cropped curly hair, and so black that one would think she’s first generation African, has a reputation. That is, one never knows what’s she’s going to do. What sex toys she might use on a person.
My first time was so fucked up that I swore I’d never come back. The second, third and fourth times, same thing. Yet here I was. This time, she greeted me at the door stark naked. You’d think she’d be worried about the neighbors glimpsing her in the doorway. She didn’t seem concerned at all. When I asked, she laughed saying half of her neighbors, male and female, are her clients. “The other half hate my guts, so it can’t get any worse,” she laughed.
I was embarrassed just going in her door fully clothed. Like, ‘What must the neighbors think of me, knowing what Sharla does for a living?’
It was very enjoyable just seeing her young naked body. She has small tits with big super-black nipples. To me, that’s a real turn on. She keeps her vaginal area totally hairless.
She led me to her ‘dungeon’ as she calls it, and had me immediately remove all my clothes. Even though I had done it several times before, I still felt a momentary pang of reluctance getting nude in front of her, even though she was stark naked. I wondered what she must think of me. Probably that I’m ridiculously white. I really should get out in the sun more.
She had me lay face up on her table, and tied my ankles and wrists with restraints. She told me today’s safeword was ‘carrot.’ I well-knew that I’d better remember that, because if things got too intense, as they very well might with Sharla, I’d better remember the word!
My penis was not hard. Too much fear. I was literally trembling in fear at what she might do. And that, believe it or not, was the biggest attraction. Knowing she might do anything, and there was nothing I could do about, made me terribly horny.
Today’s lesson started with some very light interaction with a feather duster. I wasn’t expecting that. She kept it so light, that at times I couldn’t quite tell if she was touching me with it or not. She started on my cheeks, then my nipples, and finally my penis. The fear was still there, but I was now as erect as a man can be. Every time she touched my with that feathery thing, my cock jumped an inch off my belly. Then it got even harder, and stayed off my belly, sticking straight up. I didn’t even know it could get that hard.
With my restrained left hand, I tried to cop a feel of her vagina. She backed away.
I wasn’t looking at most of what she was doing, even though my head was propped up so I could see if I wanted. But I had to look when I felt a light but cold and wet touch on the very tip of my dick. She was holding a tube of KY and rubbing it around my peehole. Then, surprise number one, she squeezed the tube right into my peehole. I felt my urethra expand with the KY jelly squirted inside.
She rummaged around in a drawer for a moment, then grabbed a little contraption. She also had a bottle of hydrogen peroxide, and was sterilizing it. Seeing what it was, my erection weakened immediately, and I started trembling again. It was a three-pronged affair some wingnuts. It was just the right size to fit into a guy’s peehole.
And that’s what she did with it. She slowly and gently inserted it into my peehole. It stung a bit, but not too much. She left it there for a moment for me to get used to. Then she started turning the screws. Wingnuts, actually. The prongs moved away from each other. At first, no problem. It felt kind of nice having my peehole opened up like that. I could even feel the cold air in there, in a place where no one ever feels cold air. My penis, with a mind entirely of it’s own, grew rock-hard again.
Sharla continued to turn the screws. Now, it was starting to sting a bit. She continued to turn the screws to the point where I was wincing and I was saying, “Too much!” She laughed maniacally and continued to turn the screws very slowly. Oh my God, it was starting to genuinely hurt. She reminded me that I knew the safeword. But, I also knew from previous experience if I actually said ‘carrot’ the session would end immediately. On top of everything else, I was thinking about my $120. I didn’t want to waste it.
Just when I thought I couldn’t take any more, she quit turning the screws, and just left it there. My peehole was so stretched open! The pain was still there, but subsiding. With the thing still firmly embedded in the end of my dick, she had me scrunch up, momentarily lifting my butt off the table, and put a bunch of towels under me. She left the room for a while. This peehole spreader thing of hers was very much on my mind. It was still making me very sore, but also very horny. If she hadn’t returned when she did, I probably would have had a hands-free orgasm. I was wondering what it would feel like to have the contractions of my urethra thwarted by the gadget.
What she brought back into the room was a WaterPik of all things. One of those deals for cleaning your teeth with little blasts of water. She turned it on, and started squirting high-pressure thin spurts of warm water on my scrotum, which hurt a bit, but was also delicious. Then she moved up the underside of my penis, and finally was squirting it on the underside of the head of my dick. She had regulated the pressure just right, so it felt wonderful, almost like a highly-focused tickle where the water was blasting against my frenulum, then the head of my penis.
Then, Sharla did the unthinkable. She squirted the warm water directly into my pried open peehole. She was spraying it against the inside surface of my urethra. I felt some of the very warm, almost hot water go deep into my penis, but not so far as into my bladder. Occasionally it stung so bad where it was hitting my inner urethra that I felt what seemed like electric shocks. At the same time, I felt over-the-top orgasmic. She turned off the WaterPik, and I was cumming. My penis was wide open, so the cum didn’t squirt out. Instead, it flowed up, filling the hole, and then out and over the top of my penis. I felt the contractions against those prongs which were stretching my urethra open so wide, and it had a surprising effect. The orgasm kept going. The sperm had ceased flowing, but the contractions were continuing. After a few more, they subsided. Then they started up again. I had a minor second orgasm.
Giving me a minute to recover, she started loosening the screws. Boy, did that hurt! The sting as she released the tension was at least twice as much as when she was stretching it open in the first place. I guess one’s penis gets used to the pain and shuts it out. But now it was back full force.
Finally all the tension was gone and she slipped it out of my penis, which was now quite slippery with a mix of cum, KY jelly, and water. The towels she had put under me were sopping wet, and not the most pleasant thing to lay on, but that was the least of my worries. That’s because she had grabbed the shaft of my still hard penis in one hand, and was starting to rub the palm of her other hand over the tip. Over my glans. It was the worst tickle of my life. I couldn’t stand it, and said “Carrot.” She acted as if she didn’t hear.
“Carrot! Carrot!” I screamed as I pulled so hard against my restraints that my wrists were starting to ache.
“Oh, that safeword has expired,” she replied as she continued to rub my glans with the palm of her hand.
I was starting to freak out. This was just too much. My penis was starting to soften. I figured if it went entirely soft, she might stop. But it didn’t soften fast enough, and she just kept rubbing.
After a minute, she quietly said, “The new safeward is ‘turtle.'”
“Turtle!” I yelled.
Sharla immediately stopped. Then she untied my wrists and ankles and left the room for a few minutes so I could collect myself. I couldn’t even move so I just stayed on the table for a bit, my ass still propped up on the wet towels. It was, without a doubt, the most intense thing that had ever happened to me. Finally, I got up, got my clothes back on, and drove home, convinced that I would never, ever subject myself to that again. And yet, I have made an appointment for Thursday and I can’t wait to see what Sharla is going to do next. I have masturbated to wonderful orgasms remembering that occasion several times.