tagTranssexuals & CrossdressersHow I Became Sissy Willow Ch. 04

How I Became Sissy Willow Ch. 04


It was now Saturday afternoon. Last night, after I'd returned home from work I had been dressed in women's clothes by my wife, Allie; introduced to her lover, Mike; been made love to by him myself; been subjected to physical and emotional torture by the two of them; and had it all captured on video.

This morning I had had all my body hair removed and had painted my own toenails while watching Mike make incredible love to Allie. I was then taken out in women's clothes; given multiple ear piercings (including a very real looking penis in my right ear); and sucked a cock through a glory hole in an adult video booth. All this was on video, except for the part where I found out that the cock in the booth actually belonged to Mike. Anybody watching the film would think it belonged to a stranger.

Now I sat in the rear seat of our car in disbelief that all this had happened in less than 24 hours. And, as the car pulled into our driveway, I knew that my adventures for the day were not over.

We went into the house. Again, I saw no neighbors, but still I felt in my mind that they must have been looking at me through their windows.

Once in the house Allie ordered me to make lunch for the two of them.

"How about grilled cheese and tomato sandwiches?"

Mike nodded his agreement. "Just two, willow. You may have tomato, but no sandwich. Girls must watch their figures, you know." Allie said.

As I made lunch, Mike and Allie had a glass of wine in the living room. I heard them laughing. I peeked in, and they were watching the video they'd shot of me. They were at the part where I was begging to have Mike fuck my ass. I blushed, and went back to making lunch. I was about to cut a tomato when I thought of the effect the juice would have on my white blouse. I went to a cabinet and pulled out an apron. It was one I would use while grilling. It was made of blue canvas and said, "Kiss the Chef." I thought for a moment, and put it back. I didn't want to be reminded of what I used to be, because it just made my current clothing and position more humiliating. Instead, I chose an apron that was more feminine. It was in pink gingham with a frill around it. It had been a gift to Allie, but she wouldn't wear it. It was too "girly" she'd said.

I finished making the sandwiches and brought them to Mike and Allie in the living room. Allie was massaging Mike's large cock through his pants. It was hard, and made quite an impression on the fabric of his pants (and on me!) The video was at the point where Gina, the girl who had pierced my ears, was playing with my nipples. I blushed, but again felt my cock stirring. Mike and Allie looked at me as I came in.

"Nice apron," said Mike.

I looked down, and returned to the kitchen to eat my tomato.

"Have a glass of wine, or two," said Allie. "I think you're going to need it."

I ate almost an entire tomato. Having had no breakfast, I was starving. I had two large glasses of Chablis. I really did need them at that point.

Mike called me to retrieve the dishes. I did, and cleaned the kitchen. As I returned to the living room Allie was removing the videotape from the player and replacing it in the camera.

"Upstairs, now, willow!" Allie ordered. I went upstairs, and hesitated at the top of the steps. "Into the spare room, willow," Allie said.

I went into our spare room. It held a desk and a computer. It was going to be another bedroom, but we never got around to finishing it. Allie and Mike shut the door from the outside, leaving me alone. I sat at the desk, and put my head in my hands. I still couldn't believe that what I thought would always remain my fantasies were now becoming reality, but were being taken far beyond anything I could have dreamed of. Of course, I still wasn't sure if I regretted the course of events, but knew that I had no choice regardless of my desires.

I played some solitaire on the computer, then checked my email. There was nothing but ads and spam, including one for a penis enlarger. I laughed slightly, then the tears started to flow at the irony of this ad coming to me now.

After a half hour Mike opened the door and said, "We are ready for you, willow."

He was still wearing the jeans and Rugby shirt he'd put on that morning. I followed into the bedroom.

There stood Allie, and my mouth dropped. She was wearing a black rubber corset with red side panels. The tight corset exaggerated her already wonderful shape, narrowing her hips and emphasizing her considerable curves. The effect was to create a classic hourglass shape, so desirable and attractive. The corset went to the top of her breasts, covering them and creating an incredible rubber-covered form of perfect breasts. No cleavage showed, and the corset had two wide straps that ran over her shoulders. The corset came only to her hips, and she wore no panties.

The corset had six garters hanging from it. Attached to the garters were black stockings that came up to cover her thighs. I could only see the thighs of the stockings, because Allie was wearing boots that came above her knees. They were black patent leather, with spike heels four inches high. Her hair was done up in a severe bun. Her makeup was heavier than I'd seen her wear before, with a lot of eye shadow and liner, and red lipstick that was as red and bright as the red in the corset. In her hand was a very mean looking paddle, about 18 inches long. It was black and made of leather, with metal studs on one side. It had a strap that went around her wrist. She was gently tapping it on the side of her boot.

My mouth dropped open in a combination of awe and fear.

"Close your mouth, willow dear." Allie said. "I may or may not use this paddle on you. And if I do I may or may not use the studded side. That is up to you."

I now knew some of what had been in the bag from the bookstore.

Mike came up behind me. He started to kiss my neck. I nearly melted. As he was doing this he unbuttoned, and then removed, my blouse. I stood there in skirt, bra, hose and heels. Mike then placed a wig on my head. Not the blond, curly one from before, but a short black wig with very fine hair. The front of the hair was swept slightly forward. He then moved to the rear of the video camera, which was on a tripod.

Allie strode toward me and said simply, "Kneel."

I did.

With the paddle she gently pushed my head down till the bottom of my wig was touching the toe of her left boot. "Kiss it," she ordered.

I began gently kissing the toe of the boot. "No, willow," said Allie. "Not a friendly kiss. A passionate one. You are going to make love to my boots."

I wrapped my hands around the back of the boot and started kissing the toe as though it was a lover, rather than just footwear. I used my tongue, and moved my head around.

"Good," said Mike from behind the camera, "but show more tongue."

I started alternating between passionate kisses and licking the leather. Though it was patent leather, it was still soft and flexible.

Allie gently tapped my rear with the paddle and said, "Start your way up dear, but slowly."

I worked my way up from the toe to her ankle and shin. I still was kissing the boot like I was in love with it, and licking it as well. After several minutes I'd reached the top of the boot. I knew to stop, rather than venture to Allie's thigh without her permission.

Allie used the paddle to force my head down to the toe of the right boot. I knew what to do without a word from Allie, and repeated my oral love making on this second boot. I again stopped at the top, and leaned back, still in a kneeling position.

Mike moved a chair up behind Allie. She sat down and crossed her left leg over her right.

"Suck the heel, willow, like you sucked that stranger's cock in the video booth." I knew this remark about a stranger was meant for the video camera.

I lifted her foot to my face and started to suck the heel as she had ordered. I licked it, then began taking it in and out, in and out. The bottom of the wig swung back and forth as I moved my head in and out. After a while Allie reversed her legs, and I began the same process on the other heel.

"Stop!" ordered Allie. I did, and returned to my kneeling position, head down.

Allie stood up from the chair and walked over to the dresser. From one of my drawers she withdrew a pair of breast forms. I wondered if any of my old clothes were still there.

She showed me the rear of the breast forms. They were hollow. Extending from the center was a post. On each end of the post was a clip. The other end attached to the inside of the breast form. I knew the purpose of the clipped end, and cringed visibly.

"Do you like them?" asked Mike. "I made them myself at the theater. We always have falsies around for guys who play women's roles or drag roles. It was simple to add the posts and clips. I'd say they were a 'C' cup size."

Allie reached down, pulled one cup of the bra out, attached the clip to my nipple, and replaced the bra cup. Luckily the tension on the clip wasn't that strong. If my nipples hadn't already been sore this wouldn't have hurt. As it was there was a constant pain in that nipple. Allie then repeated the procedure on my other nipple, and both were in pain.

"Stand up and look in the mirror, willow," Allie ordered.

I did so, and a very pretty young lady, with short black hair and nice figure, including well-shaped and nice-sized tits, looked back at me. I think I was falling in love with myself! As I was transfixed by the reflection Mike came up behind me. First he removed my skirt. Then he caressed my new breasts. The feel of his touch was transferred directly to my nipples by the posts and clips.

I purred from the pleasure this gave me, and started to melt into Mike's arms. As I did he pulled me back into the chair.

He placed my hands on the arms of the chair, and produced two leather straps from his back pocket. My arms were strapped to the arms of the chair. Allie produced two more straps; Mike took them, and secured my ankles to the legs of the chair. There I sat, in bra, panties, and hose and heels. Despite my predicament my cock was very hard, probably due both to my excitement of actually having "breasts" and the pleasure Mike had given me when he caressed them.

Allie walked over to the dresser again, and again opened my drawer. She took out what looked like a black leather athletic supporter. I couldn't see it clearly, since it was in front of her, hidden from my view. She asked Mike to give her a hand. He knelt down and helped her lift one booted leg up and put her foot through the strange leather harness, and then he helped her put the other foot through as well. Together they shimmied the strange harness up the boots, over her thighs, and up to her waist.

"Ready, willow?" asked Allie.

Then she turned around. To my utter amazement there was a cock sticking out of her crotch. It was about 10 inches long, and realistically shaped. It was only slightly darker than her own skin color. If I didn't know better, I'd have sworn I was looking at a shemale with a large cock, rather than my wife with a dildo attached to a harness.

Allie walked towards me. "Mike thinks you have the makings of an excellent cocksucker, willow. But I think you need more practice."

She moved toward the chair, and stood directly in front of me. She took the dildo in her hand and rubbed it up and down my cheeks.

"Do you want it, dear willow?" she asked. "Tell me how badly you want to suck my cock!"

"Yes, I want to suck your cock, Allie. I want to feel you in my mouth. I will do whatever you ask, and if that includes sucking my wife's cock, I will do so."

"Are you my sissy husband?"

"Yes, I am your sissy husband."

"Do you want to be a great cocksucker?"

"Yes, I want to be an excellent cocksucker."

"Are you ready to practice being an excellent faggot?"

I hesitated. That word was one I hated. I would never use it to describe another person, as it was just so mean and derogatory. Allie knew this, too, and it hurt me that she would use it to describe me. Sensing my hesitation, she began to question me.

"Did you suck Mike's cock?"


"Did Mike fuck you in the ass?"


"Did you suck the cock of a strange man in the video booth?"


Allie slapped me hard across the face, then leaned down to whisper in my ear. "Remember, willow, you did not know whose cock it was when you started to suck it. And Mike is not on the camera in that scene. Reconsider your answer, dear."

"Yes, I sucked the cock of a strange man," I said.

"Well, I guess that makes you a faggot, doesn't it?"

I softly replied, "Yes." I wondered if that didn't make Mike one too, but was smart enough not to say anything.

Allie again took her 'cock' in her hand, and started to stroke it up and down.

"Ooh, I think it's hard now, just the way you like it. Suck my cock, sissy willow, and show me just how good you are."

Allie strode to me, and positioned herself, standing between my legs. She put her hands behind my head and pulled me towards her 'cock'.

I took it in my mouth, and just held it there. Allie, still with her hand on my head, started moving her "cock" in and out of my mouth. Thrusting her hips, she shoved the dildo in and out, not allowing me to take any initiative. She kept pushing it, pushing deeper and deeper. Finally she shoved it all the way in, and kept it there. I felt like gagging, but was able to suppress the reflex by shifting my head a little, allowing the 'cock' to slide into my throat.

"Ooh, that feels good, doesn't it, willow?" asked Allie. "Oh, you can't respond, can you? But I see your little cock is very hard, so I guess that means yes, dear."

Allie slowly slid the dildo out of my mouth. "Now, willow, suck it on your own."

I kissed the head of the dildo, and then slid my tongue along its shaft, and licked all around the head. I then started going down on it, moving my head back and forth, forcing the dildo deeper by my own choice. I was not being forced; this one was for my own pleasure. And I loved the movement of the hair of the wig as I moved my head in and out. Just as I was in a near state of delirium from this activity, Allie stepped away. I instinctively leaned forward as she withdrew her 'cock', following it with my mouth open.

Mike and Allie both laughed. "She really does want that cock, doesn't she." said Mike. "Maybe I'll give her another chance with a real one."

"Not yet, Mike dear," said Allie. "I have other plans first."

She walked over to my chair, with her 'cock' bobbing, and started to stroke my own cock through my panties.

"Would you like to cum, willow?" she asked. I nodded, with my head back and eyes closed.

Allie held out her hand to Mike, and he handed her a shoe -- one of Allie's own high heels. She pulled my panties down, freeing my cock. She slipped the shoe onto my cock, so that the head went into the toe. Then she started moving the shoe up and down on my cock. The friction was driving me close to the edge. I started bucking with my hips, driving my cock deeper into her shoe. When Ally bent down and kissed me on the ear, I lost it, and came forcefully into the high heel. But I was not allowed to rest for a second. Allie immediately put the shoe to my mouth. I didn't need any directions. I licked my own cum from the shoe, and swallowed it all.

Mike turned off the camera, and said, "Damn, that was hot!"

Allie smiled. "Yes, we will have to work hard to top this. But I have some ideas."

Mike came up behind her, and started kissing her neck and fondling her breasts through the rubber corset. "Yes, I'm sure you do," he said, "and I can't wait."

Sitting there bound to the chair, I was sure I would not have to wait. But I wasn't sure if her ideas were ones to wait for, or dread.

Thank you to those who took the time to send me their comments and suggestions. Please email me your comments, good and bad, to the address in my profile.

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by Anonymous

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by Anonymous03/03/18

Oh I remember the first time a Man realy wanted me

, when he held me in his arms and kissed me, I melted like a girl. Yes I had been a faggot cock sucker for a long time but no one want me as a lover. He did and I was so happy. He picked me up inmore...

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