One Surprised Lad

Published on Jun 9, 1996

Transgender

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ONE SURPRISED LAD by Willa

I don't know where Janice found three women sharing her feelings about men but apparently it wasn't too hard and the feelings must have run deep if their treatment of me was any indication.

I'm still not sure how I got into it although I have to admit my treatment of Janice wasn't exactly delicate but I didn't do anything any red-blooded male wouldn't do if he had the chance. I thought she cooperated well and enjoyed our creative and energetic sex life. When I told her I had had enough and wanted to move on to other women Janice seemed genuinely saddened. So, when she called that Wednesday saying she wanted just one more night with me I figured it wouldn't hurt to spend a Friday night and, after all, I DID owe her a few favors.

I had a couple of drinks at a bar to loosen up and arrived at her place about 8:30. When she opened the door I saw she was really fixed up, sexy negligee, makeup, perfume, the whole enchilada. She REALLY let me know she didn't want to waste a minute so we got right with it. I had my pants off -- and the skirt of her nightie up -- and we were rolling around on the bed when I became aware of movement behind me. Before I could turn and look I felt my hands and feet pinned tightly to the mattress while other hands secured them tightly with cord. Fingers knotted themselves in my hair pulling my head back while a pair of balled up panties were stuffed into my mouth. Janice shoved me from her and I tumbled to the floor where I lay helplessly bound and gagged looking up at four women laughing down at me. I didn't have the faintest idea of what was happening, but it wasn't long before I found out what they planned for me.

Helplessly I watched as they used large scissors to cut away the rest of my clothing. In a minute or two I was naked, except for the securing cords. They dragged me to the bathroom where the tiles felt cold on my bare flesh. I hadn't the slightest idea what they were up to since none of them had spoken a word and with the gag in my mouth I certainly wasn't able to ask any questions.

Two of them spread shaving lather on my arms and legs before shaving them smooth. The treatment was repeated on my abdomen and back. Finally they removed the magnificent mat of hair I so admired from my chest. I heard the whirr of an electric motor and felt the blade of a pair of barber's clippers as they cut my beautiful hair to the scalp. Done with the clippers they shaved my scalp as smooth as a billiard ball. God, I could have cried. Lastly my eyebrows were shaved. There I sat. Bound, gagged, naked and hairless -- except for my pubic area.

Back in the bedroom they lay me on my stomach on some kind of smooth, stiff material. It took them a minute or so to tug the loose ends of the thing up between my arms and body and then I felt it tightening around me as they laced the edges together. One of them stood on me to press as much air out of me as she could while the others tightened the laces so tight I felt as though I was being cut in half and could hardly breathe.

They fastened a leather sheath around my penis, attached a leather cord to it, pulled the cord tight back between my legs and fastened it somewhere on the back of the tight waist-cincher.

I was rolled me onto my back and, after loosening the cords binding my ankles, two of them worked a pair of sheer black nylon panties up my legs. The caress of the silken material stirred feeling of lust in me and my stretched penis would have erected if possible. I felt pain as blood surged into it. Pantyhose were worked onto my feet and then up my legs until the waist band encircled my now severely whittled waist.

One of the women painted two circular areas on my chest with something slightly sticky. In a minute or two she placed two almost unbelievabley perfect false breasts on my chest and pressed down on them tightly while the adhesive dried.

I was pulled to my knees my hands untied, my arms raised over my head with a woman holding each wrist while something black and shiny was dropped down my arms. Without so much as a second's fumbling my hands were guided into sleeve openings of what I now realized was a garment of some kind. I felt my penis trying to erect again as the satiny folds dropped caressingly down my smooth, naked body.

My hands were again secured behind me and I was seated on a low stool. One of the woman spent many minutes making-up my face. Satisfied with her work she stepped back while another dabbed adhesive on several spots on my bald head and forehead. A wig of long, dark hair settled on my head and she pressed down in several places making sure the adhesive was doing its job. I felt the hair brushing the bare area of my back near my shoulders.

I felt a tingle of pain as each earlobe was pierced and large silver loops were inserted. Satisfied with their work they slipped tight patent leather pumps with, what I later learned were, five inch heels on my feet. I was pulled to my feet and led to a closet door where I saw the reflection of a pretty tiny waisted woman with make-up, mascara, eye-liner, lipstick attired in a black satin short-skirted maid's uniform -- complete with tiny apron and skirt flaring slightly over a tiered, multi-colored underskirt and the circular earrings dangling from her ears. Judas, I was getting turned on again. I knew what had happened but wasn't prepared for what I saw. It took a few seconds for it to register that I was looking at myself.

Smiling, one of the women pulled the now sodden gag from my mouth while another removed the cord binding my wrists. I was surprised to hear myself say "I'm ready to do anything you want."

For the next several hours I was the perfect maid, serving drinks, dinner, lighting cigarettes, doing the dishes, obeying the slightest whim of my four warders. Toward the end of the evening their behavior changed. I felt a hand slide up my nylon encased leg and caress my buttocks fondling me lovingly. Entranced I allowed her to continue her explorations. Another moved in to play with my lovely, albiet false, breasts while another caressed my neck and blew in my ear. Hands were all over me touching every conceivable spot. I was burning with passion, but they were only teasing me. Slowly, without my realizing it, they maneuvered me to a lowbacked chair where I was unceremoniously pushed so I was draped stomach down with my face on the seat cushion and my fanny high on the air. I felt a hand flip my skirt up and pull my pantyhose and panties down exposing my buttocks for all to see.

The suddenness and the size of the first of many items, a dildo of some sort I suppose, entering my anus brought a look of surprise to my face, tears to my eyes and a cry from my mouth. To quiet my anticipated sounds a ballgag on a strap was forced into my mouth and the strap secured tightly behind my head. For the next hour I alternately endured and enjoyed the size, texture and motion of the various objects thrust into me.

Janice, squatting in front of me where I couldn't fail to see her slowly and lovingly spread a coating of lubricant along the length of a large, flexible, penis shaped dildo. She was smiling when she disappeared from my view. I felt a hand clasp me tightly on one hip and then the thrusting penetration of the large, lubricated dildo entered me. The smoothness was pleasant and the sensations I felt while she was thrusting more and more rapidly into and slightly out of me were, oddly enough, were quite pleasing and sexually arousing. I found myself moving my hips and buttocks rhythmically in synchronization with and in the opposite direction of the thrusting and withdrawal movements.

When Janice ceased her efforts I was exhausted, but silently hoping others would continue where she left off. Instead they stood me on my feet, still shod in the heels, tied a silken scarf around my head securely blindfolding my eyes, bound my wrists behind me and, after tugging my panties and pantyhose back into place, hobbled my ankles. I felt hands grip each bicep and moved with them as they guided me out of the house and into a car.

We drove for what seemed like hours, in circles, along straight stretches of street and the freeway then onto less traveled roads and finally onto an dirt road. What seemed like hours was probably not more than an hour. I felt the car slow and before it stopped I was unceremoniously shoved from it. I lay on the ground several minutes two before managing to work the loosely knotted cords free from my wrists. Then I removed the blindfold and saw I was on what was probably a fire lane in the forest high in the hills. I could see the lights of the City many miles distant and I could still hear the hearty, almost evil laughter of the women ringing in my ears as they'd driven away leaving me clad in the maid's satin uniform, wearing full make-up, five inch heels miles from home and wondering what would happen if the wrong people happened along and found me. Unsteadily I started walking along the road hoping to make it to the main road where I could flag down a friendly, helpful motorist. As luck would have it I was able to stop a state police car. Using initiation as an explanation for my condition and presence. Rather than drop me where I could call a cab he took me all the way to my apartment.

The sun was just rising as I stood safe in my apartment admiring the pretty, but tired and slightly dirty female image looking back at me from the mirror on the door of my bedroom closet. From the corner of my eye I saw a sheer, lace encrusted nightgown left by one of my female bed partners hanging in the closet. After removing the maid's uniform, placing it and the underclothing in the laundry hamper and removing the heels from my tender feet I showered and returned to my bedroom. On impulse I plucked the lovely nightie from its hanger and thrilled as it slid over my head and down my smooth, hairless body enfolding me in its silken embrace. I marveled at its feel and the way it fell from and accentuated the lovely false breasts still adhering to my chest.

In bed thinking about the night's event it was clear to me the women were not out simply for fun but had been expressing something very important to them. It was also clear that I had, for the most part, gotten a good deal of pleasure out of the evening, even if I was aching all over.

The one thing I couldn't figure out was why I had the compelling feeling of wanting call Janice and thank her not only for a most enjoyable evening but for what she had turned me on to -- the marvelous feelings imparted by the wearing of women's clothing, especially the silken lingerie. To say nothing of the new sexual experiences I'd had and, surprisingly, for the most part, enjoyed.

Settling into a more comfortable position in the bed I marveled at the feelings I was receiving from the pleasant weight, projection and smoothness of my "breasts" and the clinging caress of the silken gown on my smooth, hairless, bare flesh as I drifted off to dream of the outrageously sexy lingerie and other erotic and exotic things for "around the house" wear and the SENSIBLE heels I would be purchasing to- morrow -- or rather, later today.

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