Lonely Man Becomes a Sissy
Keywords: a, Sissy, Man, Becomes, Lonely,
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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!
Xoxo,
Mistress"
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.
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Keywords: a, Sissy, Man, Becomes, Lonely,