tagTranssexuals & CrossdressersLonely Man Becomes a Sissy

Lonely Man Becomes a Sissy


I am a 28-year-old male. I'm single and live alone. I work days and usually sit at home at nights and watch movies, and talk online. I do small buying and selling on Ebay for extra cash that I stash away for a rainy day. So most of my time is spent online. I use to be into rock music a lot and have had long hair since I was a teenager. I some how lucked out in the professional business world and got away with having a ponytail. I'm skinny and not very muscular. Now days, I'm more of a computer nerd so I don't get to tone up like when I was younger.

For months, I had been talking to an online Mistress. She lived in my area and I begged to meet her. To no avail, she would always say no. After the first 2 months, she asked for more personal information about myself. She wanted my hone address, phone number, clothing size, height, weight, work address, work number and work e-mail address. That's about the time she started taking things more serious.

A few days later, a UPS letter came for me. After I went back inside and opened it, I discovered it to be a pair of pink panties also with a letter from my Internet Mistress.

She wrote,

"Hello slut,

I hope you like your present. They are from "Victoria's Secret" and are not cheap, so I want you to wear them to work tomorrow and you better have them on when you get home. I will be waiting for you online and I will check you on web cam to prove that you still have them on. If you want to get my attention enough to be my full time slave, do as I say. Enjoy!



The next morning when I woke, I showed as usual and went back to my room and my cell phone went off saying that I had a text message. It said,

"Take a pic of you in your panties and send it back, you have 5 minutes!"

I had almost forgot the panties I got yesterday. I had left them on my dresser. I slowly put my feet in and slid them up my legs. My dick and my nipple immediately got hard. It was a wonderful feeling. Then I started to not like it, thinking it would make me gay. I took my cell phone and took a picture and sent it to the number that had sent me the message. I knew it was my Mistress; other wise I would have said fuck you! That day at work, I got more text messages from her too. About every 2 hours, she demanded that I take another pic of my panties to make sure that I was still wearing them. When I arrived home, I immediately got online to check e-mail and my Ebay account. My Mistress messaged me and said,

"Turn on your cam, stand up, and take everything off BUT your panties."

I complied and stood there feeling embarrassed but my dick started to grow.

"You look like you are enjoying those panties bitch, I hope so. I have a pair of them and they sure are comfortable. But you do look like something is missing," she wrote. "I know what it is. In about 30 minutes, you will get another surprise. When you do, message me online and tell me what you think!"

Oh shit, I thought. What next?

A little over 30 minutes later, the doorbell rang and it was UPS again. I accepted the even small package and went inside to open it. This time it was white lightly padded bra and white satin and lacy thong panties. I ran to the computer and sent a message to my Mistress stating that I received her package.

"Do you like them, aren't they pretty??" she replied.

I told her yes and what should I do with them.

"The same thing you did today. When you get up for work, you will put them on under your work clothes, and no boy undies over them. You will send me a picture from your cell when you first put them on. And every 2 hours you will send me of pic of you at work wearing YOUR new panties and bra."

She then logged off before I could reply to her. Normally at work we have to wear suit and tie, but once I get to work, I take my jacket off. If I'm to wear a bra under my white work shirt, everyone will see. I could tell the tomorrow will be a hot and uncomfortable day.

Throughout the day, I sent the pictures to my Mistress as requested of me. I am so lonely most the time and sex craved that I will go through this game until I get what I want. In hopes that it all works out, maybe I will get a home run with my Mistress. I was scared during the day that someone would see the bra, or feel it threw my jacket if the touched my back or chest. When I went to the restroom, I was scared that a co-worker would happen to look over and see my panties under the stall. I was shacking by the time I got home. Once home, I got online and was ordered to strip to my undies. As I stood there my mistress wrote,

"You did very good today. By doing this you have caught my interest and I would like to further my involvement with you. If you are still interested, I want you to do something for me. Go to the store and buy the reddest lipstick you can find. Then come back and get online. If you put the lipstick on for me and write "Mistress's Slut" on your chest, I will take you as my slave. But you have to go to the store wearing what you have on now. You can only put on your pants, shoes and button up white shirt. Make the choice, I'll be waiting."

If I go to the store like that, everyone will see my bra and see that I'm buying lipstick. I sat there and thought about it. Then I thought about how long it had been since I had been with a woman. Damn near 5 years. I need to do something. Even if it was weird in my book. I had never worn women's clothes before, except one time my mother's pantyhose as a dare by an old girl friend. She said that I had great legs and should wear the hose for her one day and she would fuck me. It seems that I do dumb shit for women. It was then that I decided I would do it. I need some attention. I pulled my hair out of the rubber band and put on some sunglasses and headed to the store.

Once at the store, I couldn't get out of the car. I froze. I then remembered a method they taught us at work to do after dealing with my customers. I closed my eyes, took deep breaths and counted backwards from 20. Once I hit 1 I felt better, and said fuck it and went inside. I walked quickly to the make-up aisle and went to the high-class cosmetics. After about 10 minutes, I found a lipstick called "Passion Red" and I knew it was the one. When I went to pay, the check out girl didn't really look twice at me. I did see her look at my bra through my shirt and kind of smile. That made me haul ass out of there after paying. I sped home and jumped on the computer. I sent an IM to my Mistress saying, "I bought the lipstick", and turned on my cam. By the time she accepted to view my cam, I had my male clothes off and sat there in MY bra and panties. I took a deep breath knowing that if I went through this, it would change things. I applied the lipstick to my lips as best as I could, then wrote "Mistress's Slut" on my chest and waited.

She replied with,

"Very good slut. Now that I know that you can follow my orders with out any hassle, you are ready for the next step. Wash your panties you are wearing now and wear them tomorrow again along with your bra as you did today. You will repeat your picture taking schedule and you will also wear them to bed. Since you have been so good, you will receive another gift today in a few hours. You will wear it to bed with your panties and bra and send me a picture of you via e-mail. Do this for the next few days, and by the weekend, I will have your next surprise ready for you. Until then, be a good girl and don't let me down".

And with that she logged off. As clockwork, a few hours later I heard the doorbell ring. I was still wearing the lipstick. I got so busy with my Ebay stuff that I forgot I was wearing it. So I freaked out trying to find something to take it off with. I ran to the kitchen and got a paper towel. Rubbed off the lipstick from lips and chest, through on my clothes over my undies, and ran to the door. By the time I got there, no one was there, but a small box was there on the porch. Grabbing it and running inside, I opened it to find a white satin and lace nightgown with a bow on the chest. That night, I put on MY new nightgown over my undies and took some pictures from my web cam and e-mailed them to my Mistress. I took 15 or so, cause I didn't know which one she would like. The next few days went like that. I would wear my panties and bra under my work clothes and take pictures with camera phone every 2 hours and when I slept, I wore the nightgown. All that time, I didn't hear from my Mistress. I hoped all was well. I just kept on until the weekend.

As I'm sitting around on my day off work, I here the doorbell ring. By the time I got to the door, the driver was driving off. I go to the door to find a package. I big box covered in packaging tape and it just says "Private, open alone!" I eagerly take the box and run to my bedroom. As I open the box I find a letter saying:

"Dear slut,

I want you to take the contents of this box and wear them for me tonight. You will need to be ready by 9pm. I will come to pick you up at 9pm on the dot, AND YOU BETTER BE READY, cause if I have to find you; you are in some FUCKING SERIOUS TROUBLE!!! Inside you will find a razor, shaving cream, baby lotion, rose scented body wash and perfume. I want you take a shower and use the body wash. And shave ALL of your body hair off, except your eyebrows and your long hair. For the long hair I have included some pretty smelling shampoo and conditioner to use. After the shower, use the baby lotion where you shaved and then apply the perfume everywhere! Inside you will also find some other items all in black as followed: black satin padded panties, thigh high sheer hose, padded bra, corset, size d fake breast forms with spay-on glue applicator, little black dress, and 4 inch locking strap heals. You are to wear ALL OF THEM!! Style your hair in a feminine way and put on jewelry also included: hoop earrings, necklace, collar, rings, and a cb-2000 chastity device on as well. Be sure to lock the pad lock on the CB-2000, and I have the key to it and the shoes. There are also a set of red long false nails that are to be super glued on and placed on each fingernail or you will be punished. Don't worry; I have the solution to remove the nails and the breast forms AFTER I'm done with you!! You are to apply your make-up that's inside and re-apply perfume. Place your keys, make-up and nothing else in the little black purse from inside the box, and make-sure you brush your teeth and take nothing else! If any of the clothes are ruined, you will have to wear that item from now on until I say so. Such as, a run in your hose, broken or chipped nails, bad make-up and hair. I will see you at 9 bitch.



I was in shock, I knew that my night I had planned of watching movies and chatting online was not going to happen. I went into the bathroom and did as instructed by my letter. I shaved all my body hair off, washed with pretty body wash and washed my hair with the girly shampoo. After the shower, I rolled my hair up in a towel and rubbed the baby lotion all over my body. I thought I was going to cum right there. Then I sprayed the perfume on me. The stinging from it on my freshly shaven genitals took my hard-on away. I put on the CB-200 since I knew I wouldn't have much time till I was hard again, and locked it in place. I slowly dressed trying not to fuck anything up. First were the padded panties that gave me a fake butt and hips, and then the breast forms. Before gluing, I put them up to my chest to measure about where they should go. Once satisfied, I sprayed the glue on the first breast and applied it, then the other. The weight and look and feel was insane. I now knew why women wore bras. If the didn't, they would all be hunchbacks. I quickly put on the padded bra and adjusted it so that it would support the weight of my new breast. Next was the corset. Thank god it had a zipper. Once on and zipped in all the way, it made me stand up straight and pushed my chest out, making my breast look even bigger and now with cleavage. I could barely breath. I then put on the thigh highs and clipped them to the corset. By this time my hair was dry. I tried to style it like some of the girls I see around the office. It took me about 30 minutes to get the make-up right. I was starting to get hard while tucked into my CB-2000. I was looking hot. I hoped that this was all worth the trouble or I was going kill my self or something. The dress was easy to get into. I realized that it fit like a glove and only because I now had a false female figure because of the breast forms, corset, and padded panties. I swished around in the dress for a little bit, trying to get use to it until I saw the clock. It was 8:15 and I wasn't ready yet. I pulled on the high heels, strapped them on, and locked the little pad locks on them. I practiced walking for a second or two and I was a natural or something. I just felt taller and couldn't see my feet because of my tits. I threw on all the jewelry and then sat down and super glued the long fake red nails to my hands. By the time I was done, it was 8:55. I went to my full-length mirror behind my door. I was in shock!! I was staring back at a beautiful sluty looking girl you might see at a Goth club. . My only concern was the breast forms that hung from my chest. It actually felt like I had tits! I even gave them a test tug, they wouldn't move and actually pulled on my skin and hurt to try to remove them. Then I thought about the chastity device, shoes and nails I was entrapped in. they were all stuck. How long was I suppose to wear this shit? I started to get really nervous as I looked at the clock and it was 8:58pm. I decided to take the purse, check my make-up and re-read the letter to make sure I didn't forget anything. I locked my door and went to sit on the curb.

She pulled up at 8:59 in a black BMW. The passenger door opened and I heard,

"Get in NOW YOU WHORE!!!"

I literally tried to run in the 4in heels to the car and got in. She said,

"Shut up, close your eyes and put your hands behind the seat."

I did as told and felt my hand being hand cuffed behind the car seat, and then a blindfold over my eyes and some sort of gag in my mouth and then was locked behind my head. It felt like a rubber ball stuck in my mouth. I tried to talk but the only thing to come out was "mmmmmmm mmmmm". I felt a sharp pain across my face. I JUST GOT THE FUCK SLAPPED OUT OF ME AND THERE IS NOTHING I CAN DO ABOUT IT!!

"I said SHUT THE FUCK UP BITCH!! Talk again and I'll drive you to West Hollywood and make you walk back dressed like at 12 noon and we'll see if you make it home with all those horny fuckers on the way."

I immediately said nothing and heard the car get put into gear and pull out of the driveway. Before we ascended, my seat was leaned all the way back and I was stuck lying down, and then a second pair of handcuffs applied around my ankles.

"Just incase, I don't want you to try to get away now, you are all mine until I'm finished with you!! You are going to my special girl for as long as I wish. I hope you got a good look at your house, work, and friends, cause who knows when you'll see them again!!"

That scared the shit out of me! How long would this go on for? I knew I was completely at her mercy. I had no I.D. on me. I had to be at work tomorrow afternoon and I was dressed like a woman and bound in a car!! I had no idea where we were going and how long we were driving. The music was turned up so loud; nothing could be heard but metal music and the car engine. It seemed that we drove for about an hour, because of how many songs I heard. Each song was an average of 3 to 4 mins long. So I figured 1 hour. If I was an hour from home, I could be anywhere and have no idea how to get back home even if I DID get away. For some reason this all started to excite me by the strain in my chastity device. My penis started to hurt in its cage. Suddenly, the car stopped and the music and engine went dead and I heard,

"Ok cunt, we're here!"

I felt some thing applied to my dog collar that tugged on it. A leash I thought! And my cuffs on my hands and ankles taking off. I was pulled out, and pushed against the car and my hands pulled behind my back and re-cuffed.

"If you fucking run out here you won't get far at all dressed like that! You sissy bitch! Look at you! You like this don't you? You love being a girl, you want a dick in your mouth huh!" then she started laughing at me.

This set my penis into shrinking into new depths. I was so embarrassed.

"Only sissy slut whores dress like that, and that's what you look like, hahahaha, my god! You mind as well get fitted for wearing dresses all the time, cause you are no kind of man at all, just a bitch that's about to get put in her place."

Most the things I had on were pad locked, the collar, the heals, the cb-2000. I was proper fucked. What have I got my self into? I was getting dragged because I couldn't keep up as the heels were hard to walk in and I couldn't see. I felt myself step up into a porch of some sort and I heard, "don't move!" I then heard a door being opened. I was pulled inside and I heard her slam the door and lock it

"That also has a key, so you are locked in too!" she yelled at me.

Being tugged again into some candle smelling room and then pushed down onto my stomach. I felt my ankles handcuffed again and the leash lock onto something in front of me and I was stuck bending over what felt like a bed with my hands behind my back and my ass in the air.

"Sit tight, hahaha", I heard her say and then leave.

Then, it felt as in one instance, my ass was set on fire by a great impact. I was being spanked!

"Count them you fucking cunt!"

Goddamn she could hit. I was crying!

"You fucking pansy, I wasn't even trying to hurt. Aww, look! The little girl is crying. Are you going to run to your mommy little girl?"

WHACK!! She started unloading on my ass!! I counted up to 6 and the pain was so great that everything went black and I passed out........................

When I awoke, I was spread eagle on the bed, tied down, and stripped down to my corset, bra, hose, breast forms, heels, and ball gag. All I could see was my hair in my face and my tits. I could see my delicious Dom. she was beautiful. She was wearing exactly what I was wearing. Same corset, and hose, and was holding a riding crop and grinning from ear to ear! I felt a pain inside my ass, as if something was inside me. And just as I tried to look down to see what was going on, I figured out what it was when it was turned on. It was a vibrating dildo!! She started it on slow and pushed it in and out of me gently. It surprisingly felt great. I rolled my eyes in the back of my head and enjoy what was happening.

"Do you like that bitch? Do you like getting fucked by your Mistress? I bet you wish it were a real dick, huh! You're such a fucking whore. You want it bad don't you? You want to be fucked by a big black man! Shall I continue?"

I whimpered out a muffled yes, and then she turned it up, it seemed like full blast, shoved it as far as she could inside me and said,

"There you go cunt! Now your little pussy is filled with that monster cock! I'm now going to take off your gag, don't say a word or you'll never go home again!!"

The gag felt so great to be taking out. I had no idea how long I was out for, so I had no idea how long I had been in bondage. As soon as I adjusted my jaw and tried to get it comfortable I heard,


I felt something enter my mouth, long soft and thick.

My madam said, "Suck it! Suck that dick bitch like you know you want to. Do it for me and I'll do the same for your sad clit you call a cock!"

I imagined girl friends I had had sucking my dick, and tried to imitate them.

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byrebeldoll© 7 comments/ 147338 views/ 37 favorites

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