Dressing for Pleasure

Of course I knew the day would come. I secretly hoped the day would come.

After a year or so of going out with a woman nicknamed Slim, I knew she would turn the tables on me. She had threatened as much when we first started going out.

Slim. She was 14 years older than me, a woman in her late 30s. I was young, nubile, and eager to serve.

In general, I heartily approve of older women having younger boy toys. Somebody has to teach them. Slim was pretty good, but had too many other issues in her life for us to be long term. She could have owned me for the rest of her life if she wasn't more than a little messed up herself.

I met Slim at a friend's party. She was wearing a very low cut dress, dark blue sequins at the top over a black skirt, and was sitting down next to where I was standing. She caught me looking down the front of her dress. She said she sized me up right there, knew she could have me if she wanted me. She was, of course, right.

We started going out. A Dom/sub relationship, part time, was established. But I began to annoy her a bit. Being eager and young, I was always trying to run things from the bottom, especially when it came to her attire. I was like a broken record in those days, yet bad at communicating.

What I wanted to let her know was, here are the keys to the kingdom. If you're wearing boots and black stockings, I will fall over myself in obedience, lust will make me the most pliable toy you have, and my limits will fade.

What I said was "Are you going to wear your boots? I like when you wear a garter belt and stockings. I love high heels. I like it when you wear those leather gloves." On and on I went. I am sure I would have spent a lot more time gagged if she did not have better uses for my mouth.

So early on, when I was whining about what she should wear, she warned me that if I was so obsessed with women's clothes, maybe she would dress me up some time.

The thought both scared and thrilled me.

I had tried on women's apparel before. Nothing about dressing up as a woman thrilled me particularly. It isn't an activity I spent a lot of time with.

This threat came up a couple more times. Then one day we went shopping.

We did not go any place special. J.C. Penny's as I recall. There she bought a plain white garter belt, very utilitarian, with metal hardware and a pair of white stockings to go with it. She also bought panties and a satin cream colored camisole top.

She did not announce in advance that these items were for me. We were just going shopping. Slim was nearly 6' tall, so just a few inches shorter than I was, so buying items that fit me would nearly be the same as buying items that fit her.

When we got home though, I did find out what was up. I was told to strip in the bathroom, then come in the bedroom when she summoned me.

She left me waiting for a while. (There is nothing that builds up anxiety or worry in a slave like just waiting for something to happen. Never be in a hurry.) When she finally summoned me into the bedroom, arrayed on the bed were her new purchases. I thought she might be wearing them, but instead she had shucked off her jeans, put on a skirt and a pair of her boots, both black. She also had a riding crop in her hand.

She said, "You are always telling me how to dress, now I am going to let you experience it."

I was told to put everything on.

The white stockings had seams down the back. I did not notice this as I put them on, but she did. I was directed with the riding crop to keep them straight. I ended up taking the stockings off and putting them back on again after a few swats aimed at my awkward adjustments.

The stockings on, I fumbled with the garter belt. In this she had done me a favor. The big shiny metal hardware was easy for me to deal with. I was able to get the garter belt on and attached to the stockings almost right. One garter was twisted. The crop demanded correction. I redid the garter.

Then I pulled on the white panties. They were opaque and of a silky material, with lace about the waistband and leg holes. My hard cock bulged in them. Yes, I was excited by this. The panties soon betrayed the stain of anticipatory pre-cum.

Then the satin camisole went on. This was a bit small on me, which made it tough to get on without ripping it, and I dared not do that. The crop again encouraged me along, biting at my ass and thighs if I was slow.

Then I was dressed. She walked about, appraising my efforts. I was sloppy, awkward, and slow. I would need a lot of practice I was told. But I had done well enough to earn a reward.

A reward!

She brought out a box. In it was a pair of black patent pumps. They had 5" heels. They had locking straps that went around the ankles. They were in my size. "Put them on" she said.

I did, carefully sliding my feet into them. Before I could stand up she knelt, fastened the hasps on the ankle straps and padlocked them.

Now I had to walk around. I fell back on the bed on my first attempt to stand. The second attempt had me upright but wobbly. Then I was given walking lessons. The crop again lashed out as I was instructed in how I was to walk. Graceful steps, one foot in front of the other, move my hips, show her what a little slut I was.

She made me practice for well over an hour. After I began to get good, she sat down and just watched, relaxing as I strutted around at her command. She had me sit down and stand up again for a while. Then more walking. To this day I can walk in high heels without much effort. I get little or no practice, but that day of training still sticks with me.

Eventually I was deemed adequate, then told we were onto other activities. Off came the panties.

Back in the bedroom, my home made spreader bar came out. It was a 3' dowel with an eye screw in either end and another in the middle. Leather fleece lined cuffs were put on my wrists. I was told to lay in the center of our king sized bed.

The spreader bar was clipped onto the straps of the high heels. Another double clip help me wrists together at one end, then my wide spread legs were pulled up and clipped to the wrist cuffs with the other end of the clip. So I lay on the bed, wide spread legs in the air, ass exposed.

Then she began to finger my ass. She was applying lubricant to it. She inserted a finger, then two, loosening me up. She had done that before, done it so well as to prostate milk me unintentionally. This time though she wanted to use more than fingers.

A nice, new, blue vibrator came into play. Made for ass play I suppose, it was rippled. She turned it on and let it slowly loosen up my anus. She had found I had trouble relaxing myself for penetration, but a vibrator seemed to do the trick. With some patience, she had slowly slid the whole vibrator into me and began moving it in and out.

She was so gentle yet firm with my ass, I loved her for that. Later, another woman would try to penetrate me with a dildo by just cramming it in me with out any, what I will call, anal foreplay. I screamed. My ass ached for days. I'll put my ass up for use, but warm it up please before going nuts.

And, leaving the vibrator in my ass, she came up and kissed me, whispering in my ear in her husky, bedroom voice, "Who is my little slut?"

I was. I had felt awkward, self conscious, foolish, and embarrassed putting on the clothes, but now I felt awesome in them, horny, slutty, and being screwed in the ass by a beautiful Goddess.

"I am Mistress" I said softly.

"I know," she replied in barely a whisper, the proceeded to straddle my face to take her own pleasure from the situation. She always rode my face roughly. There was no need for me to do anything other than press against her. She wasn't interested in my mouth, except as a warm up. I might suck on her clit for a short bit, but once she got going she wanted to get herself off on every contour of my face. It could be brutal at times, like being alternatively punched, crushed, and smothered, with her thrusting and grinding herself on my face. I have never felt so used by a woman as when she used my face as her sex toy. And I have never felt so satisfied having myself used in any way. She did not hold back on expressing her pleasure when it was good for her.

Eventually she rolled off of me, my face slick with her juices. She lay there for a bit, breathing heavily at first then calming down. Finally she sat up to examine me, still legs in the air. She smiled and reached over to turn the vibrator up a notch. Pre-cum was dripping from me. She looked at my full hard on and said, "I'd like to ride that too, but I know you would last about a second and then I would have to beat you. I'm too tired now to beat you."

She sat up and ran a hand over me thighs and butt cheeks, appraising the redness, tracing especially interesting welts with a finger tip.

"I suppose you've had enough for today."

She picked up the panties I had been wearing from the bed, draped them over my cock, grabbed it firmly and stroked it about five times before I was shooting my load and moaning for her to let go.

I was instantly so much butter. She unlocked me and let me lay on the bed. The cuffs, bar, and shoes went on the floor. She cuddled up to me, kissing me, stroking me, and telling me what a good little slut I had been, for a first timer. Eventually we wanted to sleep. I removed her boots for her, always my job, and then she undressed and got into bed.

I started to try to get out of the camisole, but she stopped me with a word. "No! Clean yourself up a bit, but come to bed dressed as you are. You'll have better dreams."

I had sexy, wonderful dreams, I must admit. And in the morning, I wasn't just sore from her crop or her using me. My legs were sore from walking around in high heels for so long. But all of it was good soreness.

Now, years later, I dream about being used like that again. I still have the high heels. Who wants to see if I can still walk in them?

See what you've done Slim!