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My Sissy Boyfriend!

hi I was going to a party with 7 or 8 of my friends and my boyfriend was at my house as well, well while we were all doing our makeup downstairs my boyfriend found one of my dresses, some pantyhose and a bra and panties and went into the bathroom and put them on! well he forgot to lock the door to the bathroom and while he was putting on lipstick she walked in on him! she saw him and said oh sorry, then she realised who it was and she called come quick girls I've found someone you might like to see! to us. well we got up quickly and ran to the bathroom. he was wearing one of my really tight red dresses and could barely fit in it. we were all so shocked at first then we started laughing and he tried to take it off but because he wasn't used to wearing pantyhose he slipped on the bathroom floor and fell over. this made us laugh even more because the dress was so tight he couldn't even stand up and he wriggles around on the floor yelling "don't look at me!" which just made us laugh even more. I got out my phone and took a few photos of him and he desperately tried to cover his face but couldnt. he couldn't get up so we grabbed his arms and dragged him out of the bathroom. he tried to resist but there was 8 of us against one of him and we easily forced him downstairs to the kitchen. when we got there my dad saw him and him and his friends started whistling. we sat him down then my mum said I have a great idea, why don't you finish off his look then take him to the party like that! we all said yeah that's a great idea and he started crying. the puny cute sissy, we were giving him everything he ever dreamed of and he was crying like a little baby, and all it took was a little red dress. anyway we found him some of my red high heels to match his dress and slipped those onto his feet. the others wanted to put makeup on him but I said no makeup or a wig except lipstick because I wanted everyone to know exactly who he was and that he was a boy wearing a dress. once we were done he really did look great, we had painted his nails red and applied some brighter lipstick. when it came to time to leave he tried to stay in the house but with the eight of us we forced him outside. it was so funny because he was so embarassed and humiliated. when we got to the party everyone screamed when they saw him and started laughing. we also got loads of pictures to put on facebook so his parents and everyone at school could see what he had been up to. we told everyone exactly what he had done and how we punished him for it and we got a few guys to slap him on the *** when he walked past then we made him blow a kias back to them. this made everyone laugh and humiliated him even more. oh and the absolute best bit was that everyone could see that wearing the dress and the humiliation had given him and enormous *****! we made him come round my house every weekend and every time we dressed him up and paraded him through town while everyone laughed at him.
sissyboysgirlfriend sissyboysgirlfriend 13-15 26 Responses Feb 26, 2012

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I'm throwing out the BS flag here...

I'm a very masculine man that loves the feel and softness of ladies underwear and lingerie. It's very sexy. If I were in his shoes, (I'm not a sissy or even a sissy wannabe) I would have just played it up like I wanted to go out with you all as one of the girls and had a laugh with it. Would have been a little embarrassed but no way it would have gone anywhere like you girls did. But then sexually speaking it wouldn't have mattered what I was wearing because I pretty damn great in the sack and your girlfriends would have been asking to join in!

I to have been caught and humiliated. It was hard to live with at first but I have learned to deal with it. I have a hard time finding work now and have to clean houses of my girlfriends they pay me $3.50 an hour and I have to wear a maid outfit my girlfriend borrowed me money to buy. They say that is the going wage for a sissy maid. Sometimes there husbands take me in the back room and insist on other girly duties for me to perform on them.

You should insist their husbands pay for what they get

That's what sissy's are suppose to do, so enjoy your new life!

Why were you so cruel ?

lucky boyfriend

And tears or not he was probably very happy & not likely that he will ever stop wearing girls clothes

Thats the way I am, sometimes I don't like doing sissy acts, but I chose to be one and I'm never gonna stop either.

I think this was cruel and to bad he could not get even

Must mot have been too cruel if he kept coming back to her house every weekend to get dressed up knowing the girls were going yo show in public

Yes I'm that way, I always comeback for more sissy training even tho sometimes it can be cruel. I like dressing and acting like a complete sissy all the time, so I take my punishment and I let everyone know I love it.

good point

to my left I can smell the cologne bottle on my desk. To my right I can smell the cooking coming from the kitchen and after reading your story all I can smell is bullshit.

So obviously a fake story. Just say it's a fantasy and be done with it. No double dipping, George!

Good thing this is just a fantasy story. In real life it's not so funny!

I caught my Fiance wearing my peasant blouse and skirt looking at himself in my bathroom mirror. I leaned against the doorway and whistled at him, smiling, He said he just wanted to see how it looked on him as it looked great on me. I dolled him up. put one of my wigs on him and stood back and giggled, I had meant to humiliate him but when he lifted the front of the skirt and I saw how hard he was. I had second thoughts. We went shopping getting him his own outfits, nities,etc. We've been married now for five years. He loves crossdressing and I'm totally in Love with him. This makes him happy, He shows me constantly how much He Loves me. I'm completely okay with his cross dressing and sometimes we switch roles. I Love him dearly, He's very attentive to my needs. And because of it, we both have deep respect for each other.

It is great you support your husband and are away from the gender divide society tries to force upon everybody.

Glad you caught him when you did & helped him out of the closet & found it to be fun for you too

Glad to see more couple getting into this lifestyle. My girl Jenny has been with me for 10 yrs and I am happy to dress as a sissy girl everyday for me and for her.

And THAT'S how it's supposed to be in a marriage. You are quite awesome and the both of you are quite lucky to have each other and understand one another as well.

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ure a god awful ***** u should have supported him not humiliated him I hope he broke up with u

I've done almost everything a girl has done and been humiliated to the sky, so what could you do to me that I have not already done.

Everyone thinks we are mean, but think of this way. I was going out with my guy for two years and I never knew about his Xdressing. I was gonna be married to him just a week before I found him in my clothes.
Wouldn't you be mad and mean finding out about that. Now My Bobby is the sissy girl he wished so many years to be. I just gave him what he wanted.

Love it and I bet he did inside plus also he got to wear clothes that would be really precious to you plus your heels think you are a great girl x x x

Yes he wears dresses all the time in and around our house. He also wears slacks and designer skinny jeans with ladies tops over his bra and panties when he shops for grocery's and personal items. He doesn't own or wear anything a guy would wear. He wanted to wear girl clothes, so that's what he does now.
I think he looks stupid and ridiculous in his many dresses and petticoat he wears about the house, but he seams to like it. My girl friends and I like to humiliate him a lot when we are together. I don't think he like that too much, but that's part of be a sissy girl.

Those who think you are mean do not realize that most of the cross dressers her want to be caught, helped, humiliated, & accepted for our fetish, regardless of age
Thank you for being there for your sissy

It was wrong of him to hide that from you . Something as big as crossdressing should not be kept a secret because it going to be ok or not ok with the girlfriend and if the male does it behind her back in secret he is taking the chance of ruining the relationship. Something like this onle gets worse the longer he hides it. If she loves him then she will work it out with him because crossdressing is something that doesn't go away,,you cant just stop doing it .He was wrong by not confessing it to her when they first got serious and also by wearing her clothes without her permission ,so she had the right to punish him by humiliating him and could have done a lot more.

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I'm sorry but you are an awful *****! seriously

All I can say is that I am glad I don't have to be any part of all that, or witness it...but i guess to each his own. Like many things on EP, I just don't understand the appeal.

you are a very mean person we like to crossdress yes but we dont want to be paraded around and humiliated like this i love being in panties and bras and cute dresses makeup wig everything but for someone to force it just because you found out your bf likes it is mean and can cause a lot of problems to him in the future i agree with mattp1113 how would you feel

Well, I wanted to just cross dress at first, but after I was caught plenty of times, my girl was just fed up with my excuses, so she gave me my wish to wear girls clothes all the time. Later on she got bored, told her friends and they had to come and see me. Then they decided to take pictures and show all my guy friends too. Then even my boss where I worked. Soon I was fired from my job. I had no friends anymore. Everyone I knew laughed and humiliated me.
So after that I became a total sissy-girl for everyone. I wear dresses all the time even when out on the town. Everyone knows I'm a sissy and point and laugh at me everywhere I go. I have excepted my new life as a total sissy now.

A girl can wear pants but that's not crossdressing why?

Maybe it is, they just can get away with it more. My girl wear's cotton lingerie, mens 's skinny jeans and mens shirts when she is around the home. Maybe she's a FTM cross dresser. I am the one that wears the dresses all the time.

you should feel very proud little *****, ******* like your friends and your mother and your father's *******, to humiliate someone like that, I would like to give you a good kick in the ***

Hello, I'm Jennifer Lee. My girlfriend, Cindy and I caught my now ex-boyfriend, Bobby wearing my square dance dress and petticoat one day. We have since totally humiliated him to the sky. We took pictures and took them to his office and showed everyone. Bobby had to quit his job. We also showed all his buddy's and girls he knew too. They all disowned him and laughed at him too.<br />
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This happened several years ago and we have since trained him to be at our "beck n call". He still wears that same petticoat with several dresses now. I didn't want to wear the slip or dress after he had it on.<br />
He cleans our homes, does laundry, cooks and does outside tasks in his dress too. It's funny to watch him knocking things over with his dress as he swishes by. I don't know why a guy would ever what to wear those type of clothes, but he seams to be happy.<br />
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What you want to do is be dominate with your sissy, Youmake the rules and if he breaks them, you will punish him. I spank Bobby till he cry's. He will remember next time or else. You also have to give him a list of things to do during the day. Give him enough that he will have to rush to get them done. That way he will have no time to pleasure himself or have any kind of fun. I spank Bobby at least twice a week, sometimes more.<br />
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Let me know if you need anymore info on how to take care of a sissy....Jenny Lee

that's exactly where sissies should be, crawling around on the bathroom floor in a dress being laughed at by their girly masters. show that pervert whose boss and make him wish he had never been born. spank his sissy *** until it's blood red and drag him through town good girls bye (normally I end with kiss kiss but I can understand why no one would want to go near this freak let alone kiss him)

What the heck. This is not something to be proud of. It is cruel and mean. It us not a mental issue to cross dress. Now put yourself in his position but your forced to do that. How would you feel. Cross dressing is a way for people to express them selves not get humiliated.

And for this you are proud of yourself???? Talk about being sick...You disgust me!!!

And for this you are proud of yourself???? Talk about being sick...You disgust me!!!

thats what i call being scard for life

since when is trying on a dress a mental issue?

being mean is not a quality trait. your actions prove you would not be good with children if you cannot be kind with the people with mental issues. Cross-dressing is a drive to feel like a woman that extends from deep within the sole of a person. I would avoid people like you. there is no cure for being cruel and mean.