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I got to thinking about this topic after another discussion on here last week. Don't worry, it's not about the Metrosexual male and his bathroom full of products. :lol:

As most of you know I enjoy revealing my girly side from time to time, have done since I was about 10. However, aside from that there is actually nothing feminine about me........I weigh 215lbs and look more like Mickey Rourke than Mariah Carey. And this is the thing, I've noticed that most of my Sissy Sisters seem the same. Whenever I've met a Sissy, or even a TV (in male clothing) they always seem to be manly men, rather than feminine and girly. Could it be that the more masculine you are, or the more you are pressured by society to "Stop being a sissy and act like a man!" (especialy in your youth) the more you need to express the inner girl? My wife has always said that she thinks most men would like to dress as a woman at least once. I have a theory that inside every macho guy is a girl, just waiting to get out!!

So I guess the question is, how many of you lads have tried crossdressing in any shape or form? This could be wearing female attire for fun or sex games. Maybe you tried on your female partners undies out of curiosity, or wore a girly costume to a fancy dress party?

And girls has your male partner ever asked to try on your shoes, clothing, or wigs. Maybe they once asked you to put your make up on them.....things like that?

On a slightly different note, I was reading a magazine and spotted an article by a sex theropist saying she has noticed a huge increase in the amount of women using a 'strap on dildo' on their boyfriends and husbands. :unsure: So boys, be very nervous when your better half comes home from work and says "I've bought something to spice up out sex life hun." :lol:

Take care

Beth

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You're asking the wrong(or right?)person about this when you ask me :roflmao:

For me it isn't about being a sissy as such, though I tend to be that way in a lot of things. Women's clothing is prettier, sometimes more practical, sexier, sometimes a better fit, and my single preference when it comes to my clothing. My only male outer clothes are my work clothes, everything else I own came from the Ladie's department. And I haven't owned or worn guy's undies for almost a decade when I tossed my last pair of worn out tightey-whiteys in the trash can. I'm not a man inside and neither is my clothing :lol:

I've lived 24/7 for 2 months totally as a woman, though it was between jobs and I didn't have to work that way. I no longer have quite the figure for it but back then I looked really good with a little artificial help :D I absolutely loved it, and so did my FTM 'boyfriend' of the moment. It wasn't all fun and games, I had to deal with my adult family members, salesclerks, police, hateful people, people who wanted to do bad things to me, and a broken-down car like that. It was just me living my life from a different perspective and I got used to it as if it were meant to be that way. I 'passed' quite well, maybe 99% of the people who saw me and at least 85% of the people who I interacted with verbally had no idea that I had male parts or weren't at all sure about it and they treated me like a woman. I never lied if asked, but that only happened at a couple bars and once in a store checkout line :o That guy said I looked good anyway(sort of an offhand insult I guess, but it really made my day :lol: ) In the end after lots of therapy and a shrink who really didn't know which way to try to steer me, the decision was left up to me whether to transition or not. They said it was too close for them to make the call, and I almost did it(another long story). I wish I still had my 'girlish' figure since half my clothes don't fit me anymore :blush: I'm OK for now with the other things though it might not stay that way. Every day in my life I wonder if this is going to be the day that I can no longer stand to live like I am and bring me to the choice of transition or suicide. It's an uneasy feeling but one I'm now prepared to handle if it happens. Hint: It won't kill me! :)

I don't like labelling people but most guy CD's are part-time, want their male life as-is, and don't make physical changes to their bodies so they can do that. Some TG's do make changes and some of those are permanant changes, but almost all will at least shave all the 'manly' hair off. TS's have to make the changes to be who they are, and rightly so. Being trans and out to any degree requires some boldness, not exactly a 'sissy' trait, but not every TG wants to be out which is OK. It does seem that the more 'closeted' a TG is, the more sissyish their clothing choices are, and the more out we are the more we simply want to blend in unobtrusively. Those more true to what people tend to call 'sissy' often like making non-permanant changes(shaving, dieting, etc)but need to be able to go back to their roots later on if they wish. It all seems to hinge on whether this is a sexual fetish, for fun or inner peace, whether it is 24/7 or not, and how deeply the person needs to identify as a girl. There are so many exceptions to my observations that I know there are no rules or limits involved here, each person is different inside and out. That's a good thing ;) I honestly believe that nearly all guys have tried on women's undies at least once(but most won't admit it-an ego thing). At least 3/4 have similarly tried on a dress or skirt. At least half would do it far more often if they could overcome their own ego and the social pressure to always be 'manly' :o

Myself, I cannot be happy as a man 24/7 anymore. I am in between man and woman and relatively happy here except for the lack of potential soulmates for people like me :( I have met dozens of CD'ing guys who have a happy home life married to accepting(or at least tolerant)women so don't feel that bliss isn't possible, with the right person it definately is! Whew, that's longer than I wanted it to be so I'll end here with this: If you want to try something legal and not dangerous to your health, then do it. Find out what you like, what you need, and who you are. Never be ashamed of your true feelings because they are there for a reason. Live the life that you must while being realistic and smart about it. The grass isn't green anywhere sometimes, and you're going to just have to get used to it, so figure out how to live and be as happy as you can wherever you wind up then do it!

Bettypooh

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I am not necessarily a sissy, but I have always wanted to dress up like a girl, so I did so this Halloween. The best part about it was the fact that I did it in my army barracks when we were at Camp Shelby, MS. Talk about taking a lot of nerve to do something like that. I almost chickened out, but I have pictures to prove it! There is a pic on my page. lol diapermates.com/babyblue420

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I am not necessarily a sissy, but I have always wanted to dress up like a girl, so I did so this Halloween. The best part about it was the fact that I did it in my army barracks when we were at Camp Shelby, MS. Talk about taking a lot of nerve to do something like that. I almost chickened out, but I have pictures to prove it! There is a pic on my page. lol diapermates.com/babyblue420

Hehe, you appear to be enjoying that far too much Baby Blue. I bet you'll do it again!! ;)

Thanks Bettypooh for your informed post.

There is of course a world of difference between what you do and what I do, and a huge difference again between my crossdressing and say Baby Blue's or the guy that wears his gf's stockings for sex. I also believe that most guys have tried fem items at least once, or would probably enjoy it if they haven't.

I can't wait to see what the other guys say later.

Beth

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Now this is a conversation I can get into. Well I'm 33 and have long hair but a goatee and my wife can contest I like to dress girly at home. I look nothing like a woman though. And don't act in the least girly. When I was younger (15 to be exact) I went in total slut drag as a dare to downtown Cincinnati and got whistled at and such. Then when I was about 20 I dressed in drag for an all female sex toy party my sister was having...her idea lol. I've always stole my sister's and Mom's lingerie and wore it under my clothes. It was mostly for the feeling of the clothes. Anyway I've always leaned towards being a sissy once I found the internet but it seems as I've gotten older its kinda faded some. Although I still do own 2 pair of pink footed pj's. I love the color pink.

And as far as strapon's go....well I'm bi so I love the sound of them. I think more men would love the sound of them if they knew how great it felt. But just my opinion.

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Hehe, you appear to be enjoying that far too much Baby Blue. I bet you'll do it again!! ;)

Thanks Bettypooh for your informed post.

There is of course a world of difference between what you do and what I do, and a huge difference again between my crossdressing and say Baby Blue's or the guy that wears his gf's stockings for sex. I also believe that most guys have tried fem items at least once, or would probably enjoy it if they haven't.

I can't wait to see what the other guys say later.

Beth

haha yeah, I was. I'm not really into army guys, but you have no idea what I wanted to do that night. It turned me on so much! lol

Also props on Syne's pic, mad hot yo.

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If you see my penis, try to catch it with some cheese!

Ouch my head hurts!

Never crossed dress and have no desire to. The only way I'd do it is for sketch comedy. I can totally do the gap girls thing from snl. I get no pleasure from women's clothes, just the women wearing them.

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Ah, first real post in a while.. feels good.

Anyway.

I'm not that macho kinda boy... at all. I'm more feminine physically than I am manly, aside from the genitals and all. Today I had to act out a scene of my selection for my Drama final and I ended up dressing like a little girl and acting it out. I got comments saying "you make a good girl" and other things of the sort. I like that about me though.

If I was the manly-looking type, I would be very upset. I already have a ton of conflicting issues with my identity and all. I like my appearance. I can pull off a boy look whenever I need it or a girl one whenever I feel like a girl. My face is very feminine. I always shave. My hair is a lot like my mothers. I am trying to grow the sides out more and cut my bangs shorter like a little girl sort of hair style, but I dont want to screw around with how I look too much. I can't lean too much toward a girly look. If I had boobs, I could probably pass off as a girl if I had the right clothing and makeup and hair ties.

I am very afraid of my future. I fear that i'll develop a more manly appearance and I can't keep my hair too long after I get old because adult males cut their hair shorter or wear it in very manly ways. I don't want to do that sort of thing. If I dont look partially like a girl, I get anxious and question my identity. It's easier for me to play both roles. But growing up might change me in ways that restrict me from looking like a proper girl should. I just never want people to see me and think things like "manly man in girl clothes"... or even "man in girl clothes"... i dont like being called a man at all. I can tolerate boy. Male is fine. But i never want to grow up and be seen as a man.

But i'm sort of a worrier... and I tend to overanalyze and stress over the little things. I can't help it though.

To answer the original question: Yes. I crossdress. I don't like that term either though... i'm not really crossing genders... I am what I am, and what I am isn't a man.

-Sophie

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I am 5'10" and 165 lbs. My exgirlfriend (at the time) 6' and 180 lbs. After we split up, she moved out and left most of her clothes in the closet for about 3 months. I don't think there was anything that I didn't wear. We even had the same shoe size. That was an enjoyable time. Wish I could do that again.

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*Sigh* The ever present question. I would have to say that I don't look like the manliest man in terms of how a guy should look but people say I look scruffy since I have a lot of facial hair. I plan to shave my body clean (Except my head of hair of course. Its taking me forever to grow it as long as I want it.) in the very near future. I plan to as many call it crossdress but as Sophie put it, I don't call it crossdressing anymore either. I'm not really a guy since I think and act too much like a girl for my own good but I have the features of a guy. I think of myself as a separate entity all together. I enjoy wearing guy clothes sometimes (Like in cosplay and when I try to pose as a badass....not something I try on a regular basis) and I really enjoy wearing girl's clothes cause they set my mental state free on another dimension. I'm weird like that I guess.....

The Angel of Hope,

Alice

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I am very afraid of my future. I fear that i'll develop a more manly appearance and I can't keep my hair too long after I get old because adult males cut their hair shorter or wear it in very manly ways.

Ok I'm a 33 year old male and have hair down to my ass, literally. I never meant to get it that long. But women envy my hair and are jealous of it..lol. But grow it out when your older, its not a big thing.

I don't want to do that sort of thing. If I dont look partially like a girl, I get anxious and question my identity. It's easier for me to play both roles. But growing up might change me in ways that restrict me from looking like a proper girl should. I just never want people to see me and think things like "manly man in girl clothes"... or even "man in girl clothes"... i dont like being called a man at all. I can tolerate boy. Male is fine. But i never want to grow up and be seen as a man.

But i'm sort of a worrier... and I tend to overanalyze and stress over the little things. I can't help it though.

To answer the original question: Yes. I crossdress. I don't like that term either though... i'm not really crossing genders... I am what I am, and what I am isn't a man.

-Sophie

So Sophie do you consider yourself in the middle completely then? Are you gay/straight/bi? Do you just not relate to one sex or the other? I watched a show on Logo (the gay channel, I love that channel) about gender rebels. Who refuse to catagorize themselves in one or the other. I think its neat what we are and how we come about it. I used to hate who I was but I'm getting used to my own skin more and more. It helps my wife is accepting more and more of me.

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I mean I am 6 foot 4, heavyset with size 14 feet, so dainty I ain't. I don't really have what I'd call a feminine face, although having said that if you get a picture of me and of my youngest (older) sister, our faces all but length are completely identical. There's a photo in particular that confused me when I was house sitting for her, a picture of her in the maternity ward with her child, and I couldn't figure out when I had done that. It wasn't me, but it's only the clothes that gave it away.

I think I'm still in a transitional stage, I mean I've been asking myself the question for years, pretending it didn't exist. I didn't exactly have a great high school experience, I was ostracised for my looks, my ability, my intelligence and my height. Frankly I had two people who I could call friends in that place, but I noticed that all friends out of that place were female.

Funny enough that's very similar to my own experience. I also had a terrible (violent) time at high school, and couldn't wait to leave. And like you I never really looked like a girl, as such. I was very skinny as a kid, but tall. I had very long hair for most of my teen years (because I'm into hard rock, not to look girly) so that helped. But I don't think I could have ever passed for a real female......certainly couldn't now, I have great legs and small feet but that's about it.

I've never really been turned on by girls clothes, more of a fascination really.......they do have such great choice, compared to guys. Like you I've always had almost all female friends (I was the little kid that would go and sit with a group of older girls during football practise, because what they were talking about was more interesting than playing football lol.) Most of the guys my own age would mess about doing silly things like putting water balloons on another kids seat, or telling us they had had sex with ten girls in the school (even though you knew they were still a virgin.) The girls just seemed more mature, and less full of bull. In later years this paid dividends, because I always found it easy to approach girls, say in a bar and talk to them........whilst most of my male friends would hang around trying to think of smooth 'chat up' lines that would get them laid.

I often think it didn't help that I was so pressured by my parents to conform to a male stereotype. My parents are very old fashioned and have a very clear idea of the difference in male and female roles. I'm the oldest son, so my dad expected me to be a carbon copy of him and his dad. Now my dad is someone who truly believes that you shouldn't swear in front of a woman, or that guys don't need to cook, because that's a womans role. Unfortunatly he also believes that if a guy does anything even slightly fem it makes him gay (believe it or not he once had a go at me for keep saying "Take care" to people when I was saying goodbye, he said "That sounds gay.") He also hates it when I hug my friends, he wouldn't even hug me on my wedding day and shook my hand instead lol. Thank god he never found my girls clothes, I would have been homeless!!

I hope some of the girls reply, will be interesting to hear if they ever had a partner that expressed his girly side.

Beth

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I'm not anywhere near most of you who answered, but have an answer which combines this question with the one asked in another post about those who came to diapers later in life.

I was the youngest of three boys and my mom wanted a girl. No, she didn't dress me girly or treat me that way, but as I grew up I had few close male friends. I wasn't a classic sissy - played with cars and trucks, etc - but still would hang out with mom whenever a friend came over and I'd sit and listen in to their conversation. I always felt I had a little bit of the 'girly' side. In H.S. I had several female friends - more friend that 'girl-friend'.

In seventh grade, I got this fascination for girl's gym suits - back then the girls at my school wore the two piece suits - skirted thing with separate bloomer panties underneath. Partly because there weren't boys my age in the neighborhood, I'd hang out at a neighbors house where there were three girls - each a year apart and my age. I'd LOVE it when they did their ironing in front of me and ironed their gym suits - or when the gym suits would hang out on the clothes line. I used to love even looking at the printed announcements at school, telling the girls to be sure to bring home their gym suits (and bloomers) to be washed and ironed - just the words were exciting to me!

At the end of 7th grade, a pair of bloomers somehow made their way into the waste basket of my classroom and I was the lucky one to bring that trash to the custodians office to empty the trash...naturally, I scoffed up the bloomers and brought them home with me. I'd wear them whenever I got a chance. Finally, guilt led me to get rid of them, but I couldn't rid myself of the love of them.

As an adult and a teacher, I'd love to watch the girls out at gym class - or even sometimes when they'd wear them in the halls for some reason! Of course the styles had changed and I longed for the bloomer style, but they all excited me. I somehow found catalogs and began ordering a few. I'd picked up one or two from lost and found - and at one point, got up in the middle of the night - careful not to wake my wife - snuck out and down the street several houses to steal a gym suit off a clothes line. I'm not proud at all of that part, but it tells you how desparate I was! At the same time, I'd begun buying panties too - I reasoned that I wasn't getting the full experience. First, I went with cheap granny pants, then decided I'd like the feel of slinky, silky panties better. Eventually I went on to bras as well and finally bought some breast forms instead of socks! I never felt really drawn to dresses, etc, though I've got a cute little skirt I like to wear now and then (in private...) - my wife once said she'd walk out in a flash if she ever caught me in her underwear - and I don't think she'd make a distinction if I'd bought it for myself!!

The diaper part came in after searching on line for 'gym suit' and running across the story 30 days in diapers...the character is put into a leotard over diapers and it got me thinking about diapers...I still have many pairs of 'sissy panties' but don't wear them now as much because I wear diapers so often (when not around my wife/family). I still have one gym suit I like to wear OVER my diapers from time to time.

Now, I'm not sure where this puts me on the spectrum. I do feel a pull to the feminine side...I wonder what real breasts would feel like...I love the feel of girly panties...I don't look the part - very hairy body, bald head and full beard...although I'd been told many times when younger I'd be a cute girl...ahhh...oh well...at age 61 it's a little late for what-if

diaperpt

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In seventh grade, I got this fascination for girl's gym suits - back then the girls at my school wore the two piece suits - skirted thing with separate bloomer panties underneath. Partly because there weren't boys my age in the neighborhood, I'd hang out at a neighbors house where there were three girls - each a year apart and my age. I'd LOVE it when they did their ironing in front of me and ironed their gym suits - or when the gym suits would hang out on the clothes line. I used to love even looking at the printed announcements at school, telling the girls to be sure to bring home their gym suits (and bloomers) to be washed and ironed - just the words were exciting to me!

As an adult and a teacher, I'd love to watch the girls out at gym class - or even sometimes when they'd wear them in the halls for some reason! Of course the styles had changed and I longed for the bloomer style, but they all excited me. I somehow found catalogs and began ordering a few. I'd picked up one or two from lost and found - and at one point, got up in the middle of the night - careful not to wake my wife - snuck out and down the street several houses to steal a gym suit off a clothes line.

diaperpt

I had a bit of fascination with the girls in their gym kit too. In my school they used to wear navy blue leotards with these kind of little attached skirts, and like in your school they used to run about the school halls in them. Unlike you I never managed to get my hands on one of those uniforms. :( I'm sure I've told you guys this story before, but when I was about 13 we went for football practise on this freezing cold afternoon.......snow on the ground everything. Anyway, when the practise was over we went to the shower room and the water was freezing (I don't think the boiler was on) so we told the teacher and he was sort of "I don't care, get in there and get showed." So in order to pretend we had showered we put our heads under the water, just to make our hair wet. When he realised what we had done he was furious and shouted something like "Any boy that's scared of a bit of cold water can go and join Mrs Bee's class." Now Mrs Bee was the teacher that took the girls for netball practise, which was indoors and they had nice warm showers. Obviously none of us took him up on the offer (even though I was crossdressing by then) but you bet I often remembered that. :lol:

I don't remember stealing girls things, but I did steal baby stuff when I was in my teens......and no, I'm not proud of it either. Back then my crossdressing and baby side were not really connected. I used to dress as a girl my own age for comfort, because I actually wanted to be one and not a boy. But baby stuff was just a sexual kick that I did when I felt horny (which was often) and then it was a kind of generic baby, neither male or female in paticular. It was many years before I combined the two.

Beth

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Just wondering, since all humans actually start out as female in the womb, could it be that this carries over in some males more than others, which is why a boy may want to dress up as a girl. I've worn panties and a bra filled with silicone breasts, (used as breast replacements for females), it's kind of fun but still not sure I would want to be a female fulltime. You ladies have it so much tougher than guys when it comes to clothes, make-up, bearing children...just about everything really. I can't even imagine what it would be like to put up with your monthly friend for 30 years, I'd go crazy. How anyone can say that women are the weaker sex should try it for some time. Hats off to all the females here. I'll remain a male and be happy with it.

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So Sophie do you consider yourself in the middle completely then? Are you gay/straight/bi? Do you just not relate to one sex or the other? I watched a show on Logo (the gay channel, I love that channel) about gender rebels. Who refuse to catagorize themselves in one or the other. I think its neat what we are and how we come about it. I used to hate who I was but I'm getting used to my own skin more and more. It helps my wife is accepting more and more of me.

I consider myself a male and a girl. Woman I can tolerate.

I do not consider myself a female or a man. Boy I can tolerate.

I have two completely different personalities. My normal self, and Sophie.

My normal self is very outgoing and loud and fun and hyper and all. That's my boy side.

Sophie is my girly side, and when i'm in a girly mode I am much more shy and anxious and timid.

I can frequently differentiate between the two and often control which mood I am in, but there are always those times where I can't. It's usually the people I'm around, how my day has been going, and what is on my mind that puts me in my boy or girl mood.

I like to say I have multiple personalities, because when I switch between them you can see the difference incredibly. The conflicts start when i'm in between; half as one and half the other. I get really upset. They're not split personalities or anything like that because I am fully concious of each of them and have a good amount of control over which mood I'm in, except when my emotions get the best of me.

If you ask if I'm a boy or a girl, I wont answer. If you ask if I'm a male or female I will tell you male. To me, the concept of male and female means physically. Boy and girl seems like a more personal term.

And finally about my sexuality. Unfortunately, both of my personalities have different sexual perferences.

My boy side is asexual. No interest in sex what so ever. Completely neglectful of it. No desire.

My girl side is bisexual. I like both genders then, but I still favor girls... but I call it bisexual nonetheless. I'd kiss a boy in my girly mode.

Another interesting fact about myself... as a boy, since i'm asexual, I think of sex as nothing important. To me, kissing is the ultimate sign of affection. In a girl mode I don't find kissing that big of deal at all. Sex seems like a big deal to me though in my girly moods.

I am way too complicated...

...but I hope I answered your questions.

-Sophie

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The strap on thing may be fun.... As for something girly I've tried that before. Doesn't do anything for me. Although I shaved my legs for the first time today. Kinda like the feeling. Its all "airy."

~Brian

We've often spoken about it Brian, but never having done any anal stuff I'm kinda scared to try it. :( It does feel great when you remove the body hair doesn't it, especialy your pubic hair......makes for great sex.

Beth

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We've often spoken about it Brian, but never having done any anal stuff I'm kinda scared to try it. :( It does feel great when you remove the body hair doesn't it, especialy your pubic hair......makes for great sex.

Beth

Don't be scared. Just start small and work your way up. Will be an awesome feeling for your missus, puts her in a complete position of power that's for sure.

~Brian

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I'm not passable as a girl, but I wouldn't mind if I was, I always liked dressing and fem things, but I gave the impression that I was all male, but I'm sure some people seen thru me, I was asked, more than once if I was gay and had to lie and say no, just to live and let live.

I wish I could pass as a girl I would go for it if I did, but all I can do is dress up on my own.....

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I'm not passable as a girl, but I wouldn't mind if I was, I always liked dressing and fem things, but I gave the impression that I was all male, but I'm sure some people seen thru me, I was asked, more than once if I was gay and had to lie and say no, just to live and let live.

I wish I could pass as a girl I would go for it if I did, but all I can do is dress up on my own.....

That's the same for most of us beallucanb, I think a guy has to be really fem looking naturally to make a convincing girl.

Beth

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