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A Sissy's Story

Well here I go. My story begins with me as a small child. I would lay in bed and imagine I was wearing frilly clothes. I don't know why but I knew boys weren't supposed to want such things but I did.I was dressed as a girl once when I was about 2. I was put into a dress and pictures were taken. I only saw the pic but I tore it up. I so regret it now, I would love to see it now. Anyway I fought it until I was 12 when I would skip school and wear my mom's clothes. That meant her underware , lengerie, dresses etc. I almost got caught when I left some of her nighties out and she asked us about it but both me and my brother denied it. She let it go. That scared me to quit for a while. Much later in my 20s I began discovering web sites and that rekindled my love of feminine clothes. I just wasn't brave enough to do much about it. So now here I am in my 30s and I'm at it again. I bought a corset, panties, and a baby doll nightie. I contacted someone from about this and my feelings. I was informed I was a sissy and it was ok to be a sissy. I've never called myself a sissy but that's what I am. It was hard to admit but it's true. So here I am taking baby steps toward sissyhood. This is my story thus far, thanks for listening.
southernbellesarah southernbellesarah 36-40, T 26 Responses Jan 2, 2013

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As a butterfly emerges from the chrysalis so you emerge

Nice story. Looks like you adjusted quite well. Love to see your pictures. Please add me.

Good story I'm trying to get there myself please add me

Sorry, but I disagree with this. I think we should encourage our boys to be what they really are, wether they be straight, bisexual, gay or whatever. I am lucky enough to have a very accepying family that are proud of the man I have become. I never rub my sexuallity in their faces though, it is private after all.

I hope you will use the upcoming Halloween season to adopt a "WTF" attitude and dress any way that makes you feel special and blame it on Halloween. No baby steps needed, go right to Head Mistress.
I love this season and have written about being able to do Sooooooo much more and get away with it.
May all your tricks be treats.

Hi Sarah. Sissy Kristin here. You will love sissyhood. It's so exciting to be girly and wear pink panties. I especially enjoy prancing around my place in my silky nightie. I watch sissy **** everyday to reinforce my sissy desires!!! I especially enjoy MtF transgender gurls and having sex with them. I'm always a bottom. Also having sex with another sissy like you is incredible. Hope we can be great friends!!!

I\'ve gone through several names and tgirl is what I\'m sticking with. I\'ve come a long way since this story. Check out my others.

Labels are too limiting-being yourself opens up so much more. As a cd who purged all of the 'good stuff' from my 60's-70' collection of mainly stockings, I am once again complete. Dressing completes me, calms me and energizes me. We have different levels of dressing. For me it is the basics since I do not feel like I can pass (except in my own mind) with essentials. Ya know warm bath, shaven legs, painted toes, garters, stockings, panties, bra, heels...nylon all of the way. Good for you to take the bold step to be out.

I have had three bra fittings. One at Dillards, one at a Lane Bryant, and one in Palm Beach County, FL. All of these were by women. Real turn on. Disappointed that the Lane Bryant saleslady just measured me in the middle of the sales floor and didn't even off my any privacy.

Mine were at spa I have stories on it here. They were great.

I have found 3-shops that offers full services. The most recent is only 30-minutes from my home. The others are 1 and 2-hours away. 2 of them are second generation main street lingerie stores from the 40/50's being run by the daughters of the original shop owners. One has a 50/50 mix of female and male clients. They do prosthetic breast fittings for mastsectomy woman making their focus on breasts second to none. The other shop is 100% crossdress, transgender and transexual oriented. Knowing that their history includes those stocking and lingerie shops that I lusted for in the 50's as a boy just adds to the excitement. Both women owners recall their mothers accommodating us through the lo 'back door' so as not to be discovered as dressers-great stories. On my last fitting for a red see-through bra Barbara told me how many prominent men come in wearing their finest under their suits.........dressing in 'steath mode' is quite stimulating.

Well, I guess I will share this with you since we both like to wear women's lingerie and have had a penis in our mouth's at one time or another. I would really like to see my penis in your mouth. Sorry, but you are a hot transgender women and I am sure your penis would enjoy being in my mouth as well.

Any, I live in Florida and about five years ago I found a transgendered clothing store about a hundred miles away from me. I parked my car just down the street and entered the store. I was greeted by Andrew, the store owner and very effeminate. After looking at various wig, shoes, and lingerie, I found myself staring into a display case with silicone breast inserts and foam breast forms. Andrew approached me and asked if he could help me. I then found that courage to say, "I would like to try on a pair of silicone breast forms. I have a bra in my car." Andrew smiled, lightly padded my buttocks and said, "Go a get your bra." I ran to the car and was back in less than a minute with my bookbag and my wife's tan Structure bra. Andrew said, "We don't have much time" and quickly led me into a dressing room. My penis hardened in my white satin Victoria Secret panties. Andrew the appeared in the room as I was taking off my shirt and opening my backbag. Before I knew it, Andrew was standing behind me and placed my arms through the bra straps and hooking it behind me; this was the first time anyone had seen me wearing a bra. Andrew left the room and was back in a flash with a pair of at least size 10 breast forms. He quickly placed them in my bra's cups. The breast forms felt heavenly and made my penis stir. Andrew then smiled at me and began rubbing my penis through my jeans. Andrew then began to unzip me pants! I then asked Andrew for a wig. He dashed out and returned with a brunette wig. He then pulled down my jeans and saw my panties and smiled. I then reached into my pocket and handed Andrew a condom. He smiled, sank to his knees, and expertly rolled the condom onto my hardening penis. Andrew then began to give me the best ******* of my life. He swirled his tongue a lot, bobbed up and down like a real woman or very gay man. Andrew then reached up with his hands and began to firmly squeeze MY BREASTS! Get my penis sucked and breast squeezed was great. Andrew then looked into my eyes and continued sucking me like the wonderful transgendered woman he was even though he was wearing any female clothes. After several minutes of pure passion, I came very hard. Andrew then smiled, cleaned me up, and removed the breast forms from my bra. Sorry if this was too long, but it was true and really happened. Jen

Interesting. I went for a bra fitting. And it was great.

Nice ...Love reading that...

Would you like to hear what happened to me when I went to a transgender store about five years ago and asked to try on a pair of silicone breast forms?

Thank you. You are so sweet. If it works out, I will give up my bi-side forever. I have had to keep this from her and am sad of my own actions. I haven't been with any women. I have had a few discreet bi encounters a few times a year and have practiced safe sex, oral. Do you like sucking on a penis? I do. Hoping this works out.

I do indeed. Been a while but yes.

Do you think she will blow up at me? She is accepting of the panties. Do I just tell her that I have been fond of panties and bras since I was a teenager? I can imagine doing my wife while wearing a bra and breast forms. It would be awesome. Thanks, you are very good looking. I love your pretty face, your nice make-up, and sweet wig or is it your real hair?

I wish but it's a wig. She likes this fem side or she wouldn't buy panties for you. So just be honest with her.

Dear Sarah, you are very good looking. Love your make-up. I just ordered my first pair of silicone breast forms. My wife doesn't know about my desire to wear a bra or breast forms, however she does know, approves, and purchases panties for me to wear. Hopefully, I pray, she will be accepting of the bra and breast forms and not blow up at me.

Talk to her. She might not care.

great story wish u were my sissy

From what I can tell from your profile pic you are a very cute sissy.

i thank you honey

Welcome Sarah to the wonderful world of feminine exploration and discovery! That moment when you accept who you are and begin your journey is a very special time. If you make it a prioirty to continually develop your femininity to the fullest, you will experience a special richness throughout your life!

what about your **** balls? Does your **** get stiff when provoked or your nuts give out cream?

Yes very much so.

Fabulous sweetie

Will it's a small world isn't it.There's lots of the sissies in cross dressers or whatever you want to call us . This is a wonderful site and there are a lot of people who can help you. I can help and there's lots the people with more experience also stay pretty.

I started borrowing my mom's stockings and garter belt when I was 12.

It was so risky sneaking them out of her room!

I thought I was the only one in the world who did such things.

Thank you so much . It does feel so nice.

Good for you!!! Join the rest of us sissies! Being a sissy can be a lot of fun and rewarding. Do what you like, my saying is(no one pays your bills but you so do what you like and be what you want to be). It's your live enjoy it. By The Way Your Looking Good!

That's great, I too was sissified my whole life. I became a sissy at 10yrs old from my sister dressing me as a girl and telling everyone she knew. I grew up wearing girls clothes and being called a sissy. Let me know, I can help you transform.

Hi, you asked me what my sissy dress look liked when I get completely dresses if you want a picture of it give me a text back

Thanks for the story like you I went through the same feeling about dressing up until I found websites like this one we are not alone in our feeling if it feels good to us Today I plan to dress up completely like a sissy girl and enjoy !

I hope you have a beautiful time. And thank you for the encouragement.

What does your dress look like. I don't own one yet but plan on getting one. Well I take that back I bought a red satin dress but it doesn't fit propper. I was at an antique store and I panicked. Rookie mistake I guess. It's very pretty though. Have you dressed long?


Do you go out. Or in private.

Went out for halloween walking around and do in private

You can find pretty sissy dresses at Romatic Sensations .com that's where I got mine and I love it very fem