Looks like a sissy

I have loved wearing female clothes and all the things female. Started about 4 or 5 years old. Just playing dress up till started getting in mom's clothes. This was the early 1960 She was milf and had really sexy girdles stockings , dresses, heels. So when everyone left, I was slipping into her things. Made me feel good to become female. As time moved on, my sisters get raided. And if opportunity happened to find me near other women's things, I'd have to try on. Couldn't stop because it makes me look the way i feel, FEMME. Well a few years into this pleasure. A girl entererd my life. She taught me playing. Nasty. We were 9 years old. Never told about how I wear girl clothes. She taught me and showed me what girl parts are for. Made my crossdressing much more fun, because I knew I was female in my heart
LOVE our time together, she played with all the boys. And when she arrived. I would enjoy ORALLY pleasures. Looking back I cleaned her and like it. More time we parted.
Still just wearing any time it was possible. Snap up friend mom, sisters things. Find stuff anything that gave me the femme happy feeling. Sometimes I'd wear outside when in the woods. Walking around girl
Often wearing under boy clothes. Progress to marriage and she same size. So into her clothes to get caught by her. Still did it. Her mom lost some things. Few others. I felt guilty, ashamed. Still every catalog, magazines, sales adds, went straight to women's things and make wish list. Divorce and moving on. Attempting TO stop dressing. Still happening. Finally surender to my female so
I can be happy some. Only this time into stores shopping for my own things. Taught myself size conversion, found what felt comfortable. Always stop somewhere after purchase to put on. I'm riding fully FEMME clothes. Stop places and walk around gurl. Create my female name. Diane Elaine bxxxxc. Woman. I had purchased s** toys and enjoy them. I spent most of my free time riding around as Diane and love it.
Then remarried came out in few months. Didn't always go well. She was bisexual so I can become her sissy lesbian lover. Sometimes her anger disappears some of my favorite clothes. So I started wearing her things. And any found that fit.
Now shopping for Diane Elaine is probably the greatest fun. But when dressed under his yet visibly see her. And I am buying female clothes.
Also going through breakup with my wife. I've been entering vacant buildings when caught in the rain. Found women's clothing and enjoy wearing
Sometimes a female clothes come around and mine.... It's kinda kinky nasty. Yet sexual and not bad. Sorry girls if something is missing
And with this breakup,
Diane Elaine bccccr is coming out more and it's scary yet pleasurable. I'm walking around female in town. And exploring her bisexual side. Found out recently how suck a mans xxx really feel and taste good. Still want female love, got to enjoy girl half my age recently. My wife dropped her off and went s** another man. They walked in on Diane all dressed. Never hid this time and it worked out.. I got to enjoy s** enfemme with pretty sexy young female that hardly know at first, yet actually accepted and encouraging my female dress and dreams. THANK YOU FOR ALLOWING ME TO CONFESS

28 Comments

  • newest
  • oldest
  • most replies
  • most popular
  • That writing is so bad I couldn’t even make it through. You should dress up and go to school.

  • On the weekend both of my parents worked two jobs, so I would stay with my favorite uncle.

    When I was 12 he gave me money to dress in girls clothes all weekend for him. Which I did.

    By 13, I was wearing sexy little bikinis, heels, make up and wigs for him. And he gave me more money.

    At 14, we would go out with me dressed as a girl. The beach was the best, as guys my age though I was a hot teen girl.

    On my 15th birthday my uncle offered me $500 every weekend to be feminine for him, and have a*** s** with him. Which I willingly did.

    BTW, he is a fantastic lover, with a large c*** and endurance.

    By the time I went to college, I had a ton of cash and no debt.

    I'm 22 now I'm my uncle's kept sissy play thing.

    He bought me a beach front condo with a great view and pays for everything.

    I love my easy life. All I have to by is my uncle's sexy sissy b****.

  • If you were wearing girls clothes at 12 no way I would have waited until you were 15 to f*** you, your sweet little pantied ass would have been mine at 12 I love to f*** young boys

  • WOW, sounds like a dream c** true. i LOVE wearing womens clothes. i have gone out and brought my own. Teeny tiny thongs and g-strings, garter belts, lace top thigh high stockings, short slutty little skirts and dresses and even 5 and 6 inch stiletto heels. i LOVE heels, heels make me sqHEEEEEEEL i squeal like a little b****. i would LOVE to be your uncles pretty little sexy cross dressing sissy f**.

  • My younger bother is a sissy, and I have let him suck my c*** and f***** his ass for years.

    He was 14 the first time, I was 17. He wore panties, a bra and wig. He was very sexy. Truthfully, s** with him, oral and a*** is better than any girl I have f*****.

    It been 2 years now, and I have no interest is women now.

    He's 19 now and is a full time sissy. Most mornings before work I have a*** with him, he doesn't want me to wear a condom, as he loves the feel of my c** filling his ass.

    We go on out on dates and on couple vacations and everyone thinks he is my live in girlfriend.

    The relationship works for us. We both get the sexual satisfaction we want and need. And we love each other more than regular couple.

  • I think little boys dressed as girls are so sweet.

  • Their ass is any how, the toddlers love playing dress up too

  • Would have loved to know you at 4 wearing knickers, I would have sucked your d*** for you

  • Good for you. I adore woman's lingerie. Wearing a sheer nightie and silk knickers to bed. I also have a lovely supply of knickers and bras that I wear under my man clothes. Also mid fifties only been a sissy for few years. I feel amazing in girls undies. Have good range silky cotton thongs granny and period undies. Always wear nightie to bed. Got to admit it makes me feel like having a big co ck to suck. Never have done but really want a massive load of c u m down my eager man throat.

  • I'm exactly like you...I love wearing lingerie under my clothes, I prefer to sleep in my lingerie rather than a nightie. Unlike you I recently had the opportunity to fondle 3 men's pen*ses, and to suck one man's hard pen*s. I discovered I really enjoy that and would love for a guy to fu*k my virgin bottom.

  • I would love to have your bottom while you wear pantyhose with your butt exposed. Never did it before but it will be the first for us both

  • You are so lucky. I love my girly wear but so want a massive hard co ck to be rammed down my Sissy mouth. Never been there but wear my nightie and j*** off shooting a massive load of c** thinking about a hot creamy load of a mans c** filling up my eager sissy man mouth

  • You should stop fantasizing about it and do it already. there is nothing quite like dressing up like a prissy sissy lil f***** then taking a big hard d*** b**** deep in your throat and have the guy face f*** you like he would his wifes c***. then have him to c** all over your made up face or right inside of your mouth. i do LOVE me a big hot load of yummy delicious c**.

  • Well, you would love it. The feeling of a h**** man caressing your body while you are dressed in silky lingerie is fantastic, kissing and cuddling you while pushing his dxxk against you, seeing his yearning for your bottom. Then turning you around, lifting your dress and slip, pulling your knickers aside and thrusting his erection into your virgin bottom! You would squeal at first but you will soon get used to it. then when he takes your penxs in his hand as he is thrusting you will be amazed at the erection you get, the feeling is unlike any other, being fuxxed and masturbated at the same time is wonderful, it will make you feel like a real lady and want more!!

  • Yeah I would love it dressed in my lingerie having a mans hard co ck pounding my bottom. I would also be on my knees with my Sissy mouth open so he could pound my mouth and e******** his hot creamy load down my eager throat.

  • Would love to pound u while in lingerie. I spread your cheeks wide open and rim u first then take you on all fours.

  • I love wearing black pantyhose. They feel so good. I only wear them in the house . U should come over

  • You lovely darling. I am wearing my floaty double layer nylon negligee right now, I'm erect and thinking of you and I being together in our silky undies kissing and caressing each other, then I would pull my silky French knickers aside and enter your bottom, thrusting my erection and masturbating you at the same time. You would be my naughty girl.

    I live in the UK and often go out dressed in ladies clothes, I have long legs and long hair and a p**** to satisfy any sissy. I love sissies, I love the way they feel in their silky feminine clothes, the way they like my hands to caress their stockings, feeling our stockinged legs entwined as we grind together in our sexy silky undies.

    Please post again!!!

  • That sounds hot. I'm getting hard thinking about a c*** in my bottom while you j*** me.

  • Yes it does sound hot. Wish I had someone ass right now. I would rim it first

  • I'm so h**** right now and I want a c/----in my butt

  • That p**** needs my c***

  • I'll take that hot little mouth;)

  • Love to c** in little mouths

  • Baby ones for me

  • J
    J
    Here it is..

  • I know just how you feel!!! I have been into ladies lingerie since I was a young boy. I love the feeling silky undies gives me when I slip them over my body. I am now in my fifties and because I have kept myself fit and slim, taking care of my body with cream and staying out of the sun I can pass as a woman. I wear my hair long have long legs and a feminine appearance I can easily pass as a woman and I love it!!! I love men, I love them to caress and kiss me and lift my floaty skirt and push their xxxxx between my legs. I have a good size xxxx which is always hard when I am dressed. I love walking about when its breezy and my skirt lifts up in the wind showing my undies particularly in car parks where men are sitting in their cars and I know they are xxxxxxx off as I tease them. I walk close to their cars and often they expose themselves and I lean in through the window and m********* them. One or two get out and want to fondle me which I very much enjoy.
    The other day a guy got out and exposed a huge erect xxxx he lifted my skirt and slip pushed his xxxx between my legs simulating sexual intercourse and flooded my knickers with cxx I thought he would never stop then he got back in his car and drove away leaving me dripping in his jelly. Of course I loved it!! I hope I see him again.

  • Die you freak

Account Login
Signup
Is this post inapropriate?
Is this comment inapropriate?
Delete this post?