Halloween prank made permanent Part 1

Posted in: TvTs

Last Halloween my girlfriend Sharlane decided that we would reverse rolls for costumes and she would be the man and I would be the woman. This was fine with me since I had long been interested in cross dressing and had done it in private but not out in public. Sharlane is great to pay attention to detail so she set out to make our costumes and us look for real. She is larger build and I am more slender so her clothes wouldn’t fit. The shopping came first and she wanted it first class so we went to the finest womens stores in the mall, her having me try on every dress or outfit that she thought I would look good in. At first the snickers from the high class sales girls bothered me and she knew it so she even made me step out so she could have them see me and get their opinion. Most were very helpful and made sugestions that my Sharlane agreed with. Finally after seven stores, twelve sales girls and one sales guy we decided I would go as a “French Maid” but not the typical French Maid she wanted me to be a genuine working and cleaning French Maid. Sharlane owns a cleaning business where five or six women clean as maids.
The high heels were my favorite since they were 5 inch stelletos but I learned to walk in them very fast. She also made me wear a thong instead of panties and loved to grab the back and pull them deep into my crack. This made her so happy it sort of turned me on even though it hurt a little. She had me get a professional wig, a long blonde one and it looked so real. My nails also were done professionaly as well as a pedicure. By now the girls doing the work on me had quit snickering but I was still somewhat humiliated and this turned Sharlane on even more. She had even thought of having me take female hormones months earlier so by now I had a 36C bra size and that was hard to hide at work since I work construction and boobs on a man just wouldn’t go over well with the guys.
Halloween finally came and she told me I wasn’t going to work at least not at the construction site. I protested that I had to and she ordered me to sit down shut up while she did my makeup and that she was taking me to work with her and the girls. She said some of them may be in costume and that she would introduce me as a new cleaning lady. She had previously taught me how to have a mostly soft feminine voice. I also think the female hormones did good on that I know they took away all of my facial hair and I enjoyed not having to shave everyday. I actually had to concentrate daily before speaking to sound manly on the regular jobsite. Wow with my slender build when I looked in the mirror I did look hot. That day she happend to be cleaning a very elite mens store. But I fit right in with the other cleaning ladies, only one other had elected to wear a costume and it was a scarecrow. I was cleaning in five inch stelleo high heals and such a short skirt puffed out by six white slips so far that I was afraid my rock hard erection would show while I was cleaning overhead. My girlfriend was really loving all the looks that the men customers were giving me. She was dressed as my regular construction worker job and they actully thought she was the boss man on the cleaning job. So they would go to her/him and ask if I was single and would she give them my phone number. Sharlane played it straight at first and said yes she is single but she won’t give her phone number out. When they got out of hearing range she just laughed so hard and was loving it that I thought the other cleaning ladies would catch on that I was a man in costume. After about the fifth man asking for it she gave me my new name of Shantae and put our our home number down for them to call. I protested because while I loved wearing these clothes I didn’t want strange men or any men calling me for a date. She enjoyed my protests even more and loved every minute of it. To one man whom she thought to be very handsome when asked for her to give him my number for a date she said well I will introduce you to Shantae right now and came over to where I was cleaning and sure enough he asked me out right there and when I said no thank you in my ladylike voice my girlfriend said “now Shantae this is the owner of the store that has always used my company and I think you should at least have a date with him.” I politely said no thanks and she gave me that “do it or else look” and said Shantae is just playing hard to get she would love to go out with you.” I graciously accepted to go out that night if my “boss” man could come along on a double date. This guy was not only believing I was a woman he was believing that Sharlane was a man.
I was scared and excited all at once especially when he said he had a sister that my boss could go with.
We both had to leave the other cleaning ladies right then and go shopping in that same mall since she had to get mens clothes and I had to get a sexy evening dress since he said we would be going to his clubs elegant ball for that night. Sure enough he came with limo and all. We had said we would both be at my house to save two stops. I never ever thought any man was a sexy turn on after all I am not gay. The lady however that he brought for my man dressed girlfriends date was absolutely gorgeous and I even felt a little jelous of her sexy dress wishing mine was more like hers. Now I thought it will be fun to see my sweetheart get embarrased by being not only dressed like a man but being with a gorgeous woman that I would have died for. I again was fooled she was not embarased at all and before the night was over had even put a few moves on her/his gorgeous date. They were even making out in the limo and Sharlane was feeling all over the womans body they were both getting so turned on. Well I had my hands full the opposite sense I was pushing back his hands and lips off of me and he took that as a challenge so he got more forceful and I thought Sharlane would help stop him since he thought she was my boss man. She just kept pulling clothes off of her female date. Once she did blurt out Shantae it’s OK give yourself to him! That was it I had had enough of this and I tried to make a manly voice and tell him that I was really a man in a womens dress. I thought that would cool him fast but he didn’t believe me and kept it up. By now my Sharlane was eating out her dates crotch and they were both so into each other. Finally to end this mess I pulled my dress up and my thong down and showed him my somewhat small penis. He got upset very upset and asked my girlfriend if she knew I was a man and had dooped him. She could tell by his anger that there was no need for both of us to catch hell so Sharlane said that she had just hired me as a cleaning lady that same day and she was as surprised as he was. I was shocked that my girlfriend of five years passing as a man would not stand up for me but would throw me to the wolves like that just because this man had money and influence and used her company for his business.
(to be continued)

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