SissyStephen

I don't feel looked down on for being a sissy, although I keep my sissiness hidden. But if I had to pick whether people knew of my sissy side or my dl side I'd pick sissy. I dunno, but the diapers feel more taboo than wearing pretty things. But being a sissy is worth it. We get to enjoy all the great feminine things! Is there anything better than satin and lace? Or anything more comfy than a skirt? I love my sissy side!

I vote for diapers. I have tried pull ups and they are more convenient, but they leak way too easily. When I work I wear medline air active's, they have the stretchy tapes so you can actually pull them down and back up if you need to use a bathroom. Plus they are good at not leaking. I've done 2 wettings in them. I have never trusted them for a third. And they're discreet under clothes and don't make a lot of noise removing in a bathroom. So they're kind of good for when you don't want anyone to know you're diapered. But I really like plastic back diapers. That's kind of the fun of wearing them. Hearing that great 'crinkle' when you walk and hoping nobody else does, or maybe secretly hoping they do hear it and give you an odd look so you can get embarrassed.

^^I love that outfit! That is just the cutest!

Hi, sorry if this has been asked before on here, but I thought it might be a fun topic. I normally wear diapers to work. I have a job where I can't always get to a bathroom without pulling off of a job and driving a few blocks or more. Not that big of a deal, but I find it kind of annoying when I have to stop what I'm doing and travel to use the potty. Plus, I really like the sissyness (if that's a word) of wearing diapers. But ultimately I wouldn't wear them at work if it was just for play time. So when I do get the urge at work it's reassuring that I have that protection in case I just can't hold it any longer. But I have never leaked, I'm always worried that I will though. So I was wondering if anyone has ever had a leak happen when out and if it was embarrassing. I would love to hear the stories if you have any! -Hugs, Stephen

Normally I just wear shorts to bed. It depends on my mood. The other night I did wear my footy pajamas to bed but it was very cold and I wanted to be warm. There have been times when I have worn one of my baby doll nighties to bed as well. Normally though it's just shorts with some satin panties underneath. I don't wear diapers to bed. I can't wet when I'm sleeping, I have tried. I save the diapers for when I'm awake and can really enjoy them. If I try to wear something really sissy it just becomes a distraction and keeps me awake. I normally save that stuff for 'play time'.

I know this is an older post, a couple of weeks, but I wanted to put in my 2 cents. I consider myself to be a sissy. I love pretty dresses, like the ones at leannesprettydresses.com. I also really love wearing school uniforms, plaid pleated skirt with a white blouse and knee high socks, with either saddle shoes or mary jane's. I also love the sailor style of uniform, sera fuku they are called. That is probably my favorite type of dress. I also love satin lingerie, and wear satin panties on a regular basis. Sometimes though I just enjoy a nice skirt and blouse that looks older. So for me I run through all age ranges with my sissy wardrobe. So for me at least it's just a boy who likes dressing in pretty things. I never want to be thought of as a girl when I'm dressed in girls clothes. I want to be a sissy boy wearing girls clothes. It just adds to the wonderful humiliation factor. I remember once I went through a drive thru at a fast food place. I wore my normal clothes, but under a navy sweat shirt I wore a peter-pan collared blouse. The look I got from the girl at the first window was one shock and she was giggling as she took my money. When I pulled up to the next window to get my food that girl was hanging out staring at me, wanting to see the 'freak' wearing a blouse. It was the best! To me that's what a sissy is, a guy who wears not just woman's clothes, but really feminine looking stuff.

I wear boxers to bed most of the time. Hard to role-play when you're fast asleep, although there are times that I will strap on a diaper. I get hot easily though and I need my rest and can't sleep if I'm too warm. Sometimes I will slip on one of my nighties, or even some lingerie and enjoy that while I relax and watch some t.v. then when I'm ready to finally drift off to dream land I'll take that off and slip back on my boxers.

She's fine with it, it doesn't bother her. Sometimes when I tell her I'm off to change my diaper she giggles at me. She finds it cute at times, and I think there are times when it annoys her, if she's got other things on her mind. And on occasion I can even get her to change me, which I really enjoy. The nice thing is I have made the switch to cloth-like diapers so now I can be diapered and if I can tell she's not in the mood she just doesn't even know I'm wearing them at the time. Although right now I'm really annoyed because I bought some CVS cloth covered pull ups, and they are really prone to leaks. That's the last time I buy pull ups, there is just no substitute for tapes. I ordered some Medline air actives from idiaper.com but haven't gotten a shipping date from them yet, just the original confirmation. When I log in it tells me they are processing the order. So I think tonight I may have to run to walgreens or cvs and pick up some to get me by until the good ones come. I just can't use the pull ups anymore, I've already changed my shorts twice today.

Hello! My name is Stephen and I am a 34 year old sissy boy. When I was a child around 9 or 10 years of age I found out I loved wearing feminine things. I use to sneak my aunt's lingerie and wear it under my clothes. It felt so good against my skin! Well when I met my wife I was 20 and she 19. When we were dating I shared with her this part of my life and she took right to it, dressing me up. From then on we would on occasion play dress up and have a lot of fun. Through all this time I had never even thought to try diapers. I should point out also that about 12 years ago I started working for a utility company. My job has me going to people's homes and businesses to repair the service. What the service is isn't important, however the fact that at times I may not be near a bathroom is. There are times when I work in rural areas and may even be as far away from a bathroom as 30 minutes. When I'm on a job it's rude to ask a customer to use their bathroom if it is at a residence. A business is much easier as most have public restrooms but I still try to avoid it as it's not professional. So a few years ago I finally grew tired of the constant struggle to hold it until I could get to a bathroom. I had several close calls, and some where I didn't quite make it and messed and/or wet myself a small bit. There have even been a couple of occasions where I really messed and had to go home and shower. So I bought some diapers at the local Walgreen's and tried wearing them to work. WOW! It was great, I didn't have to worry anymore about messing myself or wetting. If the urge came on I would stay relaxed which I found made it much more easy to hold it. I knew that if I didn't quite make it I had the diaper to catch everything. It literally changed my life. I became more productive at work when I was diapered because I didn't have to stop nearly as often for bathroom breaks. Plus the feeling of the thick puffy diaper between my legs constantly reminded me that I was indeed a sissy boy. So here I am a diaper lover finally finding a place to call home and hopefully make some new friends! Hugs! -Steph