My Favourite Life

January 10, 2007

A Night in Town

So I was reading some other posts centered on D/s and BDSM experiences that had been initiated online. As I have mentioned, I was into that, but it no longer interests me much these days—rather in the way of been there, done that. Well, I was recalling a particular time when I met this woman on the Internet. It was when I was ending my first marriage and just having some fun.

We had been chatting online and over the telephone for several months by that point. She, too, was married in a marriage she wasn’t thrilled about, but she didn’t want to leave the security of her marriage. Finally, the time came that we would meet for a long weekend under the guise of her attending a supposedly work-related seminar in Boston.

Since her husband had seen her off, her arrival outfit was a simple navy suit ensemble—a mid-length skirt, a shear blouse, a jacket, and low pumps. She was in her early 30s and inexperienced in Internet “dating” and the whole D/s thing, though she had had experience in extra-marital sex vis-à-vis those swingers’ newspapers. We had both had recent AIDs tests we had exchanged by email.

In consideration of her situation with her husband, I allowed her to wear the business suit, but I told that sometime her between getting on the plane and meeting me, she had to lose her underwear and the jacket. She was not to carry these thing. Instead, she was to store them in her carry-on luggage.

When, she got off the plane, I could see immediately that she had complied—save for the panties, which I was determined to see if they were gone, too. We grabbed something to eat at the aeroport and got her bags from the luggage check, and then we walked to my car. Once we got to the car, I needed to know she had complied with the rest of my request, so I asked her to hike up her skirt. She lifted her skirt and quickly pulled it back down. I reminded her that would cost her. I ordered her to lift her skirt until I told her to drop it. I made her stand like that for about a minute. Luckily for her, there was no one around who could see, but she was still nervous.

Satisfied that she was serious about continuing, we drove to the hotel we reserved in Back Bay. I had already checked in before I picked her up, so we just went up to the room. I told her to lose her skirt and blouse. She wasn’t shaven. I knew this in advance, and this would be the first thing to remedy. I told her to take a bath to relax but not to get cover herself unless I gave her permission to do so. I told her I would be going to get some wine and would return shortly. What I didn’t tell her was that on the edge of the tub I had left some shaving cream and some razors.

I was gone for about an hour, knowing it would probably take her that long to relax and shave. I was right. When I returned she was just then finishing up. A glass of wine I had poured for her was waiting. She drank it and then drank some more.

I told her to lay on the bed on her back with her arms and feet at the bed corners, spread-eagle, and we talked about her freshly shaven pussy. To her, it was shocking. More than that she was wondering what she would tell her husband—why she would return from a business trip with a shaven pussy. I just told her to touch it up when she returned and tell him it was for him, but she didn’t think he was into that, as he had never asked for it. As it turned out, she was right. He thought it looked “ridiculous.” To each his own, I guess.

Now, we were ready for action. I cleared off the desk, and with her facing it, I tied her ankles to the legs. Next, I tightened some clamps onto her nipples and pulled the chains down to secure them to the desk. Then, as I leaned her over the desk and tied her wrists to the other legs, I reminded her she had been disrespectful to have hidden her pussy in the parking lot without permission. She was going to have to take a bout with the flogger, but that wasn’t my main goal. After a few light flogs, she knew what I had in store when she felt the cold Slippery Stuff being massaged around and in her asshole.

I worked in one then two and then three fingers into her ass. I put some lube on my cock and I thrust it into her shaven pussy unexpectedly—I couldn’t resist giving it a try—while I continued to prepare her ass with a fourth finger. After a short while, my fingers were replaced with my cock. Her husband didn’t like anal sex either, though she had had anal sex before. It wasn’t a regular thing for her, but seems to be pretty much a requisite for D/s play. I teased her that I was going to come in her mouth, which she protested. I am not into that, but it made a good set up. I didn’t cum in her mouth, but I did finally cum in her ass.

Then I untied her and retied her face-up on the bed. It was time to deliver her some orgasmic pleasure. First, I ate her until she came twice, but then I brought out the power tools. I had with me—among other things—two vibrators, a dildo, and a butt plug. This was in addition to an assortment of whips and chain sorts of things. Plus I had some candles for hot wax. I’m not big on dildos, but butt plugs can come in handy. I love vibrators!

My goal was to make her cum until she couldn’t take any more. She was very orgasmic, and it was fun watching her writhe in pleasure. Once we began, she had many orgasms in rapid succession, but once we got going, they started to get spaced apart more and more, each in turn weaker than the last. Then she had had enough. She didn’t want to cum any more, but I wasn’t done. I switched to the more powerful vibrator/back massager. She was to the point that her last orgasm had been over five minutes before, and she thought she couldn’t cum again, but I knew better. I kept the vibrator on her tenderised clit relentlessly. She kept on saying she couldn’t cum again, but I wasn’t giving up. Finally, and in a flash, she did cum, and it was huge. The convulsions were amazing. I had had enough. After I untied her, she stood up and could barely walk. Her muscles were like rubber for quite a while then.

I needed to wash. My cock had been in her ass, so I wasn’t planning to put it anywhere else until it was clean. Of course, she would do the cleaning, but I wanted a massage first. She oiled me up, and gave me a nice relaxing back massage. Then we left for the shower where she washed me. She left my cock for last. As you might well guess, cock-washing tends to have some side-effects, so I decided I was clean enough, and the side-effect had to be addressed.

We returned to the bed, and she went down on me. She was pretty good. According to her, her husband didn’t like receiving head either. Whatever. She had been practising somewhere—not the best but adequate. Since I had cum not too long before, it took quite a while of sucking before she got me off. After about twenty minutes I came hard in her mouth. It wasn’t a large volume, but it was a strong orgasm.

We were done for the night. She washed up herself, and we talked a bit. I reminded her she was not allowed to get dressed until I gave her permission. This was the end of day one. The next day we would go out on the town, and then following day she left. We ended up meeting 4 or 5 other times. She returned again. I met her there twice, and we met in a neutral city another time. That was that.

This was over ten years ago. We still exchange emails every now and again. She is still married to the same guy, and still enjoying extra-marital sex whenever she can. She has more sex outside the marriage than inside, and he seems, frankly, to be none the wiser.

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