Hi, my name is Tony or maybe I should say Tonya . I met this knock out blond bomb shell “Sue” at my work place. On a scale of 1 to 10 she hit the 10+ in my book. She was everything that I always wanted in a hot sexy, slim, fit, girlfriend. We hit it off right away and moved in together after a year of dating. One night while sitting outside on our patio we started talking about our lives, past and present. I made a comment that some times I think life would be much easier just wearing a dress and staying home. She of cores dis-agreed with me.
Now we had talked about a lot of things and both of us had admitted to one another about things we wished we could do over. I confessed that I had slept with quite a few women in the past. Nothing that we talked about was crazy, nasty, or weird so when we turned in for the night I never thought about any of it again. Sue however must have been thinking about what I had said and tried to come up with a plan to manipulate me into doing what she wanted. Time had passed by since the talk, I am guessing about six months or more. We went out for the evening and she did not drink much maybe one glass of wine but I had way too many. Once back home I must have been in black out mode because when I woke up dressed in female clothing. Hung over badly laying in bed I reached down to adjust my cock and balls only to find I had panties on also. I sat up still groggy from the effects of the night before, I yelled what the hell is going on here Sue?
I started to freak out when she asked what was making me so up set? I asked what was this shit I had on? Dressed in pink something with garters and nylons with matching pink panties. Well dear she said with her hands on her hips, if your going to act like that you will be in it much longer so just culm down. What do you mean just calm down, why am I dressed like this? Well you’re wearing lingerie which you willingly put on last night and danced around in it. But why I asked? Because I asked you to put it on and you willingly agreed to it. I started to remove the panties when Sue said “No you don’t”. You better straighten up other wise it will be a long time before you get any sex.
Now not knowing what really happened I had to take her word for it. I asked how long will I have to wear this lingerie ? I will take your picture then you can get out of it or else expect to wear it all day. Not wanting to wear it all day I agreed to the picture which I had her guarantee that only she would see the picture. This will come back to haunt me at some later point in time. Sue told me to pose for the picture and she clicked off several before I could get out of the frame. Then she told me I could take it off. I quickly got out of the outfit and dressed in my normal clothes.
Every thing went back to normal I guess you would say at least for the rest of the month. When we went out this time I did not get drunk because I was afraid of what I may wake up to. I did get feeling good though and once my head hit the pillow I was out. I awoke to something heavy and confining on my cock. Reaching down I found I was chastised during the night. I was shocked and woke her up when I yelled ‘WHAT THE HELL”? Sue asked what was the matter? I asked why was I in chastity? Sue told me that I was going on about all the women I had. So since I can not trust you I will keep you in chastity from now on. Bull shit I said, no way am I staying in chastity! Well then I guess I will have to show your picture to they guys at work so your friends can see what you dress up as when your drunk. I knew it would come back to haunt me and I told her she did not dare do that. Try me, Sue said and I knew she meant it by the tone in her voice.
How long will I have to wear this I asked her? When I think it is time to take it off I will tell you but it won’t be any time this week. We will see how you behave maybe next weekend. I worked with it on and it was very discomforting I was always adjusting it. I begged Sue to take it off but she told me to quit asking or it would be longer. My demeanor had settled quite a bit over the next week and I was allowed to have it removed, However I had to put nylons on and a garter belt with heels. Then she wanted another picture of me or I had to stay locked up. Wanting it off I reluctantly agreed to her terms. I modeled it just as she instructed so she could get what she called a good picture.
Once I undressed but before she unlocked it I was informed that before bed I had to have it reinstalled again. At this point I was ready to agree to anything just to have it off. Once removed I took a shower and returned to the bedroom to get dressed. Sue was waiting for me and told me since I would be out of chastity I had to wear a black teddy with matching panties and nylons for the day. I tried to protest but did so very weekly and ended up dressing as ordered to. I put the suspender teddy on and slid the nylons up my legs as she instructed to prevent runs. When I pulled on the panties up my cock sprang to attention. Sue seeing this was not hesitant to point it out saying you like dressing like this don’t you? You get really excited and so horny dressing like this. You like it don’t you? I kept denying it but she told me that my cock says different. I stayed dressed like that for the rest of the day. By bed time I had the chastity cage put back on.
I did not know which one was worse but did not like cross dressing at all. I figured I would last as long as I could in chastity to avoid having to cross dress again. After three weeks I had to have it off and once again I had to cross dress for Sue before she would remove it. This repeated it’s self over and over until Sue told me that she wanted me to cross dress when ever I am at home. My demeanor is more pleasant when I am cross dressed and she would let my cock out if I did as she asked. I ended up doing what she requested of me since I was doing it any way. Now I find it natural to dress when ever at home. I am growing out my hair and have been taught a little make up. Sue told me that she will keep me out of chastity if I keep dressing and progressing as I am. She wants to take me out some time in the near future clubbing. I do look passible with a little help from her. I am looking forward to an evening out dressed as a girl, after all I have earned it.
Tony to Tonya
“SM” Sissy Maker