I'm a Sissy ~ Luckily

My story … well … as my name suggest, I’m a sissy. I’m not complaining … just the opposite … it’s like a stroke of luck. I love it. Life would be so dull and boring if I weren’t. I’m really happy to be so special and wonderful.

So what is a sissy? Well, the dictionary says it’s a little sister. I like that. That suits me. I like being every woman’s little sister. Yes, that’s right … I like being a girlie girl. Now, don’t take a negative view of this. Please, stop being such a sexist! Being a girl is not only just fine, frankly it’s a whole cut above being a boy. Do you still think being a girl, being a woman, being a sissy is a joke? Then I feel sorry for you. You are one of the reasons I’m a Feminist. Not only do I think being a girl is just perfectly fine, I think it’s preferable. Yes, preferable. See, I made a conscience decision because I was born, and still am male. To be honest with myself, and the world, I love being a girl. Girl’s are just smarter, better, more fun and of course, prettier. So is it worth it to trade the male advantage of strength for the female sensibilities of pretty thing? Yes! I’ve had the opportunity to sample some things on both sides of the fence. Life has taught me some things about myself. I like chocolate, I’m a "bleeding heart" liberal, I like the summer, I like to live in the city and to visit the country, I like the color yellow (well, I like red, pink, gold, black, white, purple and warn colors in general), I love everything about women … and I like being a girl. Mostly women understand me. I don’t understand men who think being male is the ultimate and exclusive thing. I find men dull, boorish, unattractive and rather stupid in general. I love everything about women. Oh … did I say that already. Well, that’s okay, it’s worth repeating. I am truly a little sister in the world, looking up to all women for guidance, role models, inspiration, and frankly … adoration.

Okay, this gets old, but the question always comes up, so let me answer it here. Sex, what is my sexuality and preference. Easy answer, I love women. Men are icky, hairy, ugly, dumb and not sexy. That said, I don’t but into the binary codes of one being wholly and exclusively female or male, straight or gay. I like myself as a female person and I’m attracted to women. So, does that make me a lesbian? Can a male be a lesbian? Who cares. Let’s drop all the labels, they are just nonsense anyway. Emotionally, physically, sexually, intellectually, aesthetically, and romantically I love femininity … both in the persons I’m attracted to, and in myself. No, I’m not attracted to flannel shirt, tool belt, boot wearing butch women and yes, I am attracted to beautiful male to female transsexuals. One’s genitalia does not define, much less compensate for what is in their head, their heart and their soul. I like to judge a person by what is between their ears, not what is between their legs. Really, I’d to be judged the same way.

No, I’m not a transsexual. I am probably transgendered … which as I’ve been given to understand is a very vague concept that encompasses all forms of gender diversity from drag queens, to transvestites, from fetishes to transsexuals. In my case, a test I took on the internet defined me as person who is equally comfortable being either gender and able to freely move back and forth between the two. Don’t confuse self identity here, with sexual preference. Just because you see yourself at times as female does not mean your sexual preference magically conforms then to the make believe idea that women are universally and/or exclusively attracted to men. When I’m girl, I still like girls. A transsexual suffers from being male or, female as he case may be) and needs to live full time in the gender identify that they truly feel themselves to be. This is neither a desire, nor an option for them, it is a mandatory correction to an error that nature made at birth. I don’t need to be a girl … I just WANT to be!

Well, I’m not going to write my life story here then have nothing left to post in the future. If you have any questions, just ask. Don’t be shy. I’m not in the least embarrassed or ashamed of anything about my myself, or anything I’ve done. Sex is not taboo either. The problem with sex is not that we do it, it’s that’s we don’t talk about it openly and honestly. I have stories to tell, not just to get them out of my secret drawer and make them clean and healing experience, but because I know that I am so not alone. I’ve read, and I suspect this is probably pretty accurate; that at least 5% of all males crossdress regularly, at least 50% have done it at least once and about 95% have at least thought about it. So, it’s a pretty common thing. I know every male who has these feelings goes through a life of self doubt, shame, denial and confusion. The irony is that while the desires to crossdress are perfectly healthy, the ill feeling about it are not. I want to to stop feeling negative about it and start feeling good about yourself. I know it is not just a male problem. Every spouse automatically inherits their other half’s problems they day they get married … so there are all these women who also have to cope with, understand and deal with husbands, friends, sons and other males who have a very feminine affinity at times. Communication is like turning on the light in a dark room, it automatically makes the bogie man and fears go away. Funny thing is, once the lights are on, and the guy is recognized in his girlie self, most women tend to be very accepting and encouraging. It’s a little bit of a growing and learning process, but in the end women tend to have an appreciation and support of femininity that is very strong and affirming.

So, sometime I’ll tell you about my childhood, my first time shopping for girl things, my first time seeing the "real me" in the mirror, the experiences I’ve had with others and the general joy and delights of such simple things as lingerie, make-up, hair, heels, frou-frou and so much more. Being a girl … is just … breathtaking!

You have to admit, I look so much better as a girl, and I feel so much better. And, as you get to know me, you’ll love me much better this way too.

CherrySissy CherrySissy
46-50, T
21 Responses Aug 15, 2008

You express my feelings. So far I haven't had the nerve nor the motivation to follow your footsteps. I wish I could.

Thanks your story helps me as well. It helps to verify how I feel inside myself also :)

Listen, they use to say be what you want to be... not to many people say that anymore because some took it to heart. I don't care how you want to live your life but I care not to hear a lot of gratuitous garbage that has no basis in fact. If you are a feminist it is because you have one huge blind spot. For my money the feminist outnumber (macho)males two to one in the egotistical jerk department! They have made it near a criminal offense for a woman to choose to be a stay at home mother. You think the jehovahs witness badger people about their religion... put a stay at home mother near a gaggle of feminazis! These jackasses actually look down on a woman who is dedicated to homemaking. Think I'm lying.... you can't rectify their claim to being out of the home as being enlightened with any claim that they support a womans right to be a soccor mom! It is contradictory!

hello,i have just met a guy who likes to wear womens clothes satin silky underwear etc,i want to know how i can enjoy this with him as i have never been with a guy who wants a girl but wants to be sissy to,he says we can take it slowly and its great fun but to be honest i have no idea what i should be doing to enjoy it,can anyone give me some ideas or tell me how to be x

I am a TOTAL sissy - feminine in every way! I began to explore my feminine side in earnest when I was 12 and tried on a pair of my mom's panties, lipstick, and high heels. I had long blond hair then and when I checked myself out in the mirror I was astounded! I had transformed from a skinny little nonentity into a sexy woman! The following year I went to live with my dad, who had been stationed in the Philippines. Our maid, Cresencia, discovered me dressing up in some of the female clothing and accessories left behind by one of his female visitors. Instead of being angry she encouraged my dressing up, eventually introducing me to her cousin who was a beautician for many of the bar girls and ladyboys who worked the clubs in Angeles City. Within 6 months, at the age of 14, I had my first job in a Ladyboy club. Because of my pale skin and blond hair, I attracted a lot of african-american men, and also a lot of well to do Filipino men. I was known as the American ladyboy. Sometime I plan to write my story in book form called: "American Ladyboy In the Philippines".

Cherrysissy..I have admired your writings and your ability to express yourself ever since coming across them. You truly are quite talented and intelligent and I thank you for putting into words the feelings that so many of us have always had . If your picture does you justice then you are also as beautiful outside as you are inside and isn't that what we all want. I know I do but time has taken it's toll on me and because I wasted it with others who would not or could not accept me and who made me feel horrible about myself. That was then this is now and thank God I met a Woman who has helped me become forgiving of myself and taught me the true meaning of love and acceptance. I hope you have someone to share the beautiful "girl" you are with because you have so much to offer in so many ways. I'd love to be one of your friends and talk more often.

there is nothing like strutting in a pair of five inch heels and a mini skirt.

hooray for you and hooray for me because i feel the very same way i think being male is very boring and i am really beginning to ahte being male more and more i wish and want to transform instanly and magicla into a girl and a little girl at that so i can begin all over once again as a girl and then grwo up at my own rate as a female i love like you say more and more what when and how girls are they get to be cute funny pretty and everything that is so just the oppoisite of blys and males i mean they get to wear whatever they wish male of female clothing and i want that optionso bad so yeah i am with you on this i would much perfer to be a girl person then to contiue as a male i just lve everything about being female and want to become a girl!<br />
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more later thank you for posting this please do not hesitae to contaact me on this page or via email at jleslie492@hotmail.com please sent me nay messages about this that you do wish to i am ready to talk about it at just about nay old time thank you Jay!

great story!!! you are beautiful!!

I totally agree with you, I never understood why a woman would even think of sleeping with what basically amounts to a sweaty, hair covered rectangle of callosed flesh, ick, personally if I were forced to be straight I'd give up sex altogether, I mean I have a mirror, so if it came to that.<br />
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It's nice to see that a man has finally figured it out, and given up his brutish nature yet still holds onto his sexual preferences, if only more men could see the logic in what you've done, the world would be a much more beautiful place.

loved your story.I too love to dress and let my feminine side out. I don't get to do it as often as I would like to but as often as I can. Only a few know about my girlie side and don't judge me for it. I think every man has a fem side and most are afraid to show it. I LOVE my fem side. I am submissive and like serving dominant women. I've been dressing since 10 or 11, in my friends mom's clothes ,both of us. Our relationship evolved over the years and we remained very close and sharing. Forgive me if I went too long,this is my first time sharing this with others. Thanks for listening LOL

I am proud of you as well. I have to say, its difficult in these liberal times to be exactly who you feel most comfortable being. I remember so very clearly being ashamed of who I was, who I was attracted to, and suffering the guilt of it all. I believed I was alone. I believed no one else could possibly be feeling what I was. Then I began to question...why me?. <br />
I had to muster up the stregnth to just live and be as you are now. I stopped seeking the approval of others. For all intentional purposes I was born alone and will probably die alone.. (death is an individual experience). <br />
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I later after adapting to my new lifestyle found out a very close uncle of mine was crossdressing. He was so afraid to tell me for fear I would eliminate him from my life. While I was suprised at the secret I recognized from my own experiences that the most important thing you can give a loved one is support and acceptance. I may not understand, and I probably never will but I love my Aunt/Uncle whomever....lol.....<br />
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All the same I support and congradulate you! This was a great story to read. Thanks for sharing it. Good luck. <br />
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P.S. I've also learned a lot because Auntie has joined several organizations that offer support. I have witnessed the lack of support people receive from their loved ones and consider myself blessed. I believe my Aunt is a very attractive woman. And am happy that she has found a woman to accept and love her for who she is. They are building a beautiful life together and planning for retirement.

Cherrysissy, you are more mentally healthy than half of the straight men or women I know because you accept yourself and revel in it. And you are indeed, beautiful.

Cherrysissy, what an interesting story. Your joy and love of life seems to beam through in your words. You are happy with yourself and that clearly shines through also. I'm sure people instinctively like you for who you are, not in spite of it!

there is much of you i liken to myself<br />
but iam stuck in my nylon pantys that no female <br />
of lesbian or strait wants anything to do with me,<br />
iam not hairy ,icky or any of those other male traits,<br />
(i hope not) anyway i've several sisters but thats what they are ...............sisters, <br />
perhaps iam just ugly.<br />
any iam proud of you for having the preferance as to whom you spend time with.<br />

Type your comment here...


Wow girl what a great summary...very nicely said. It is great to be comfortable to be happy with who and what we are.

you go girl !!!

I've moved beyond that hype. I put away the masculine aspects that I was taught as a child growing up. I am female, no ifs, ands, or buts.<br />
I cry, laugh,love, think just like anyother genetic woman. I have monthlies with out menstruation. I get bitchy and fall hopelessly in love with a guy who lies to me and then there is nothing worse than a woman scorned. It is not about the physical, sexual or non sexual it is a mindset manifested at birth.

I am a heterosexual male who loves to crossdress. I find that crossdressing brings out the feminine side of me. I do it brecause I love women's lingerie and find it most arousing. Women's lingerie is soft, sensual, and very sexy compared to male underwear. I have been crossdressing since I was 9 yrs old. Don't ask me what got me started because I really don't know. All I know is that when I put on my first bra and panties I was sexually aroused and loved the way I looked in them. I had an immediate hard on and did jack off and climaxed intensely. I did and still do this and after I climax I do go back to my male role. I don't want to be a real girl, I just enjoy dressing up once in a while for sexual relief and to let my feminine side out. I guess you could say that I am a transvestite because of my lingerie fetish. I don't judge people for who or what they want out of life as long as they are happy with what they are doing and experiencing.