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Double Down
In my introduction to the forum, I mentioned that I had always wished my mother would decide to start making me dress in cute girls' clothes from now on, though keeping me looking like an obvious boy. To that end I had formulated (and subsequently discarded) a plan to put that into effect. I'm not sure how it would have played out, certainly not like anything i truly would have desired; fantasy is always so much different than reality when it comes to these things. Plus, at the time, mom was very religious. Her church (our church, though I never liked going) might have squelched things. alas, i think it all may have just been a long gestating fantasy that started in the mind of my younger self ...

Mom had a punishment system she called Doubling Down. Her version wasn't so much based on the Blackjack terminology, but rather more to the idea of doing something more, or to excess. She may have gotten the idea from those TV shows or after school specials where a parent caught their kid smoking, so to teach them the error of their ways forced them smoke an entire pack, or even an entire carton, of cigarettes. I'll give three of my more strong memories of such punishments ...

I was about 11 or so at this time. We had a backyard pool. Mom had told me with no uncertainty that I was not to go swimming on a particular day. The reasons for the edict fade to murkiness but the strong directive remains in my mind. I decided I could sneak a bit of swimming in with my pals while she was at work. My sister was at some church camp, so no one was going to be there to see. I called a couple buddies over and we roughhoused and swam and played air ball (jumping into the water trying to catch a football in as goofy a way as possible). Everyone left long before she got home, even long enough for the water of the deck to dry into nothingness.

I thought I was in the clear until the next day she cornered me as I was eating my breakfast cereal and watching cartoons. She asked if i had gone swimming the day before. I  didn't answer. Getting caught lying was usually worse than whatever I did wrong, in her eyes, and enhanced any punishment. I figured she already knew, somehow. So I said yes. The exacts of my talking to is lost in the fog of time, but the punishment meted out fit with her Double Down ideas ...

"Since you decided you could disobey me and go swimming when I explicitly told you not to, Christopher, you must really want to be in the pool," she sternly spoke. (I am not exact on her words but I'd bet moneyIi am extremely close to what they were here.) "Since you love swimming and being in the water so much, today you will do exactly that. You will stay in the pool from now until bedtime for disobeying and being a bad boy."

She also always called me by my full first name when in trouble and under punishment. She would go back to using Chris when I was done being punished.

I was made to put on my swim trunks (still damp and I bet this was how she found out) and a tshirt. I was allowed a ballcap, too. Then into the pool I went. I didn't have to swim the entire time, and I had the various pool toys to amuse myself, as well as floats and such. I was allowed out to use the bathroom, but I ate my lunch at the edge of the pool, and my dinner. She relented and allowed me to get out when it got dusk (about 7pm at that time) but after a hot bath, I was put to bed. I was so wrinkled and soaked I didn't want to go swimming for weeks.

A second example was I was told not to watch cartoons when I got home from school and to do my homework first.

I did for a while, then decided to watch the cartoons and then do homework after or during. I think I was around 9. What I didn't know was my sister found me out and let it go on for a week or so before telling mom. When Mom confronted me, I told the truth and punishment was meted out.

"Christopher, for not following instructions for at least a week, I am Doubling Down and forbidding you from any TV after school for TWO weeks. And, on Saturday, you will only watch cartoons and not go outside to play until the cartoons are done and you have done all your chores for the next month. Also, your sister gets to choose what cartoons you watch."

Sis chose the dumbest cartons meant for really little kids or the girliest ones on. (I kind of didn't mind the girly one too, too much, if I'm honest.)

A third example when I was 12 involved the last piece of chocolate cake left in the fridge for my dad. We all knew it was saved for him. I ate it anyway. Then, when my sister and I were asked if we ate it, I lied. Not sure how she knew it was me. Again, I got a stern announcement of my punishment.

"You've been a bad boy, Christopher. Not only did you eat the cake that you knew was saved for your Father, you lied about it. Since you seem to love eating chocolate cake so much, I got you a whole cake all for my lying piggie boy."

She handed me a large slice and a fork and told me to eat it. I was actually kind of happy and thought i got one over on my mom. Free cake? and all for me? Sweet!

I ate that piece and another she offered after. By the third piece I was feeling sick. I cried and couldn't finish it so she gave me a choice: I could finish eating that piece, or she could smoosh it in my face and i had to keep it on until my Dad got home. I took the smooshing. Dinner was ... another piece of cake. In the end of that day and for breakfast the next morning, I ate four big slices of cake and had that one slice smooshed in my face and the last slice placed down the front of my undies and smooshed when i refused to eat it for lunch that next day. (I was allowed to change within maybe 15 minutes.)

But that wasn't the end. Oh, no. I had lied. And my punishment for that was going to be a while in duration. No matter the meal, I was offered a slice of chocolate cake for my dessert. "Eat you chocolate cake, Christopher!" Even if some other dessert was given to the rest of the family. I didn't have to eat it, but that was my only dessert option for the next month or so. She even took my sister and two of her friends and myself out for ice cream one day. I thought everything was over ... until she pulled a foil wrapped slice of cake from her purse for me as she sent the girls up to order ice cream.

So, from those and other less traumatic experiences, i formulated a plan to get her to dress me up in girls' clothes when I was about 12 or so.

I was sneaking into my mother's and sister's clothes since I was about 9 (and my sister's stuff from maybe 7 or so, when I found things in the bathroom). I had never been caught. I was careful, meticulous, dare I saw ninja-like and detail oriented on how I found things. I even checked for booby traps like strings or items stacked or attached together before I touched them. All because mom;s punishments (which included spankings and groundings depending) made me paranoid. I was never caught.

But ... what if I was caught?

I had been exploring my own sexuality for a while by then, and I am sure my personal fantasies and the feelings I was giving myself through my self escapades fed into my delusion of what would happen.

I suspected mom would want to embarrass me for dressing up in my sister's and her things by telling people what a sissy I was and making me wear them in front of family, maybe even taking me out in public in something of my sister's. But, being caught would likely only entail a one-time dressup embarrassment. I wanted something more long term.

I wanted her to Double Down.

I decided that I would have to stop being so careful and to leave hints and clues of what I was doing. I'd need to leave things out of place or in the wrong spots. Stretch panties out a bit, possibly even tear or get something dirty. I would even make sure to leave the Sears and Wards catalogs somehow marked to the girls' clothing sections to be found ... I was always taking them into the bathroom with me to "look at the toys and electronics and stuff." I even considered making a "diary" to be found listing weeks of me dressing in their things with notes about what i wore and how i found it to put it back. I would keep up not being actively caught dressed up, however.

After a period of this, I had hoped to be found out and confronted. Then, I was going to lie and hold out on that lie as long as I could. This way it would compound the punishment I imagined would be forthcoming and mom would force me to wear girls' clothes in public for twice as long as she thought I had been doing it in secret. I also knew if she did that, she would not allow me to look like a girl but would go out of her way to make sure I looked like nothing more than a boy wearing girl's clothes!

I imagined after she confronted me and I lied about it, she would pull out the evidence or the damaged clothing, the traps she may have set, the catalogs, most damning, my diary detailing weeks or months of playing dress up in their things. Then she would lay down her punishment ...

"I cannot believe my son is a sissy who likes dressing up in girls clothes in secret. I am ashamed of you, Christopher! You need to be punished so you learn you've been a bad boy wearing our things. Since you seem to like dressing up in girly things when no one can see you for at least the last month or so according to this interesting little diary of yours, you are going to be wearing girls' clothes in public for at least the next three months! I am going to put you into your sister's clothes and take you out where ever we normally would go, Christopher. The grocery store, to church, to the movies, the mall, even to the arcade you like so much.

"You will wear whatever I or your sister picks out for you to wear. So many cute skirts and blouses, and dresses, and shorts sets, and cute jeans and tops. You'll learn to walk in little heels and have bows and barrettes in your hair. And maybe even makeup and nail polish some times. I saw you wrote you wanted to try that but were too scared you'd get caught. Well, you've been caught, Christopher. And now you'll get to wear everything out in the bright light of day in public. No more hiding and sneaking into our things in the house.

"Don't cry, Christopher. I'm not going to make you look like a girl. You are going to look just like you are right now ... a boy. Only you will be dressed in your girlish outfits for everyone to see. Won't your friends and other people think how hilarious it is to see an almost teenage boy dressed in cute girls' clothes? We can even go shopping for some of your own outfits at the mall? I can tell the sales girls how much my teenage boy loves wearing pretty clothes and ask them to help us pick out a few things for you to try on. who knows? Maybe we can even get you a whole new wardrobe for when school start back!

"I can show them your "diary" and how you have been wishing for a pink IZOD polo and a paid of cuffed denim clamdiggers and white Keds that you could wear to school. Or how you love the bubble jumpsuits some girls are wearing and wonder what it would feel like to wear one to a school party? Oh! Or maybe how you wished you could have your very own Laura Ashley dress to, how did you put it? "To swish around in as I walked around outside and to church." And the one about how you wished you had your very own ruffled tunic and legging set to wear to the park for a picnic and to play in. Well, my sissy boy Christopher, you will get to experience all of it!"

But, I chickened out.

I likely would have had a severe spanking, hd people told of my perversion, and been grounded and had locks put on everything so I couldn't get into it anymore. Or maybe even something in between the two, but i was as scared of success as failure.

Alas ...

(please don't think my mom was mean. She was very loving and generous and kind except when it came to punishments and especially for lying. I loved my mom very much and she loved me more than I could ever know.)

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What an interesting piece, Daughterboy. The part about the chocolate cake did remind me strikingly of the famous scene out of Matilda (though I hope your mother was nothing like Miss Trunchbull).  Wink 

Speaking as someone who underwent both petticoating and nappy punishment as a child I can attest strongly to their effectiveness though I wasn’t especially amenable to it at the time as I was still misguided and concerned about what my friends would think (which in the remodelling of my lifestyle since, I have been able to put right. 

In any case it sounds like the punishments that were meted out in your case were very effective (something that mothers seem to be experts in) and is it possible that she even knew how you would really prefer to be punished and though it was never mentioned avoided such methods for that reason?
(12-30-2020, 06:02 AM)Girlygirl Wrote: In any case it sounds like the punishments that were meted out in your case were very effective (something that mothers seem to be experts in) and is it possible that she even knew how you would really prefer to be punished and though it was never mentioned avoided such methods for that reason?

Mom was great except when it came to punishments. Then she was brutal, at times. She showed her love in so many other ways, though.

Her punishments definitely kept me on the straight and narrow ... usually. The fear of punishment was a great deterrent. However, I an even stronger desire to not disappoint her. This is not to say I never got into trouble, but the things I did do that were against her wishes and rules were done in such a way she never knew. 

Still, the thought of what might have happened had I ever been caught crossdressing feeds my fantasies to this day.
Wow Daughterboy, you’re a great writer, I thoroughly enjoyed reading those experiences even it was not fun for you at the time and don’t you know I emphathise with your attempt to be caught and dress as girly boy, however just like you I chickened out.
(12-30-2020, 01:35 PM)afp Wrote: Wow Daughterboy, you’re a great writer, I thoroughly enjoyed reading those experiences even it was not fun for you at the time and don’t you know I emphathise with your attempt to be caught and dress as girly boy, however just like you I chickened out.

Thank you, afp!

That deranged machination I devised has fueled my fantasies for decades. LOL

I've chatted with others about it in the past, but that was the first time I put it down in text. (Though I spruced it up a bit and reposted it elsewhere as I quite enjoyed writing it and wanted to share it even more!)
I used and still use a variation of this method on my sweet sissy hubby.  He has learned that when he objects and throws a fit about some new requirement it will lead to him doing the required plus a little or a lot more.  That is determined by me.  I tolerate and expect mild resistance on many things i have done in the sissifying process but direct disobedience is not tolerated.  For example when i first started making him wear a bra in public.....  he threw a monster fit. and we ended up just staying home.  But, a week later we were out to dinner with him wearing a bra and light make up and perfume.......   Sooner or later i always get my way and he is learning...
It sounds like you have a very effective method, Sissy’s Wife. And of course, while each event may be embarrassing at the time they gradually get used to it and it is superseded by subsequent events. So for instance when compared to a requirement to dress in full women’s attire, the prospect of going out in a bra and light makeup would possibly be quite appealing. 

Hopefully though he will eventually join the sissy club and come to enjoy his newfound role and attire like so many on this forum.  Big Grin
Well, on occasions when he knows he has overstepped as far as his objections or somehow acted in a totally unacceptable macho way.  I have come home to find him taking the initiative to dress and act in a totally feminine way as a method to apologize for his male actions..  I find it thrilling and adorable and sexy and show my appreciation for his efforts in a very thrilling and exciting way for him..  He will be blushing soo furiously when he presents like that but it just makes me melt to see him trying soo very hard to please!

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