October 11, 2007

The Bet That Started It All..

Posted in Crossdresser, Domination, Fem Dom, Female Domination, Femdom, Feminization, Feminized Boys, Forced Fem, Forced Feminization, Forced Femme, Sex, Sissification, Sissy, Sissy Maid, Sissy Whore, Submissive, Tranny, Transformation, Transsexual, Uncategorized tagged , , , , , , , , , , , , , , , , , , , at 11:57 am by feminizedguy

July passed by, so did August & September.. It was in October when I first wore a dress.

It’s interesting how it all happened..

As u know Neha was studying fashion designing then (now she’s a designer and works in Amsterdam). One day when I was at her place watching TV, while lazing in her double bed, she came into the bedroom from the kitchen. She’d been on the phone for sometime, talking to a friend about her designing assignment. She walked in the room and kept her cell phone on the bed, went to the dresser and picked up a ruffle to tie her hair. I looked at her from where I lay, she saw me do so in the mirror of the dressing table. When she finished tying her hair, she turned to me and said, “U know something, you’d make a good model.”

I said : Yeah sure I would, all I need to do is work out for a few years and I’d be set for the modeling world.

She smiled and laughed.. there was some mischief in her laughter..

Neha : U could be one today itself, all u have to do is put on a sexy outfit, say a short skirt and a tube top.

I : Yeah, like that’s going to happen..!!!

Neha : You never know, what tomorrow might bring.

I : Yup, no one knows the future, but I know you’re not going to find me in a dress any day.

Neha just smiled and went to the kitchen.


A few days later, we were sitting in the living room watching TV. We started talking about something we saw & we both had opposing thoughts on the issue (wont be discussing the issue here). So we got into a wager/bet over it. The terms of which were, If I lost, I’d do whatever Neha wanted me to do and if she lost, she’d have to do whatever I told her to do. Seemed like a fair deal.


The next day in the evening, I went over to her place and to my dismay, I came to know I had lost the bet. As per the terms of it, I was to do whatever she said. I didn’t expect her to say anything radical, just thought she’d say something like, you’re going to treat me at barista or maybe something like we’re going to elevate, your treat.. And so, I was kind of ok about it. No major issues, I thought.

But what happened next, shook me up completely.

Neha said, you’re going to have a change in wardrobe. From now on you’ll be wearing what I tell u to, as long as I tell u to and whenever I tell u to.

I though to myself, I don’t have a bad dressing sense, I have good style. Good shirts, good t-shirts, good jeans and I wear them in good combinations too. Anyways, since she’s a designer maybe she’s got some style tips, so why not. I agreed to it.

Then she said, why don’t you change into something better now.

At that time I was wearing a sky blue polo (which happened to be my favorite polo) with blue jeans.

Anyways, I said, “Ok, What do u have in mind..??”

She said wait a minute, went into the bedroom.

Two minutes later she called out to me, “Come into the bedroom Mohit, I have something here that I’d like you to try.”

I walked into the room and there she was, standing next to the bed. On the bed was a dress. It was a black dress, one of those little black dresses that women love to wear. It was something like the one in the pic below. It had narrow straps with an asymmetrical bottom.




She picked it up from the bed and said, “Put in on”

I immediately said, “Are u kidding me..! I’m not gonna put on a dress.”

Neha : Oh yes u are..! U lost the bet fair and square. You have to wear what I tell u to wear.

Me : I may have lost the bet and agreed to wear what u tell me to wear, but I’m not wearing girls clothes. I thought u were going to make me dress up in menswear, in color combinations of your choice.!

Neha : Then u thought wrong. Your fault…!

I said you’ll wear what I tell you to wear. It may be anything I want you to wear. You don’t get to chose. I get to choose.

Now put on the dress.

She extended the hand in which she had the dress for me to take it from her. I was still not taking it from her.

She then came closer and placed the dress on my shoulder, and said in a stern voice, “Put it on..! A bet is a bet..! You lost it and now u have to rise up to the occasion. Wear the dress.”

I guess I was making a sullen face. It must have been really red.

I remember coz Neha then said, with a chuckle, “And it seems like u won’t need any makeup either, your face is already red.”

I just stood there, not knowing how to get out of it. I knew Neha wouldn’t let me off the hook easily. She always gets what she wants, I remembered.

Her voice shook me out of my thoughts, “Are u going to change into the dress by yourself or should I help u undress and get into your new attire…”

I resisted again, trying out all the excuses I could come up with but none stood their ground. Neha was to have her way, come what may.

I had no option but to give up, and so, I finally gave in.

She left the room and I started to undress myself, just then she shouted out from the living room, “And don’t forget to put on the bra and panty on the bed.”

I thought to myself.. What..! Hell no.. it’s bad enough I have to put on a dress, now this too.. I’m not going to wear any lingerie.

Just as I was thinking so, I heard her voice again, “You better wear them or else I’m gonna have to pull down your boxers and put on those panties on you myself..”

Something in her voice assured me she wasn’t kidding.

I undressed myself completely, put on the black bra and black panty. Had some trouble with the bra, but then got the hang of it. Wore the dress and came outside the bedroom. Neha was sitting on the couch in the living room.

Looking at me, Neha smiled & said, “My baby, u look like a model in the making. Don’t worry sweetheart, I’ll make u look better than any model. Come and sit next to me sweetie.”

It was then that I felt assured that this wasn’t going to be a one time affair, it’s going to be something that I’m going to be doing again and again..


To Read The Entire Story Click Here : https://feminizedguy.wordpress.com



1 Comment »

  1. hali said,

    i was blackmailed into wearing full girls undies to school: Bra, matching panties garterbelt, stockings slip under my guy clothes because these girls I dissed bad caught me messin around wearing sisters stuff at home,,,Random but frequent school inspections for runs,, punishments too ,,, plus if i EVEr dissed a girl, forgetaboutit.,,

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