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Crossdress and public walk dare

Hello there,

I would like to dare myself crossdress and walking at night when nobody at the streets.

Please leaves the comments what should I wear? I will buy the clothes and shoes for every comments posted to dare myself.

Next Confession

Male/female/male

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14 Comments

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      • I recently tried cross dressing. I put on a flowery skirt, no underwear, a matching top. I wore knee high hose with some ladies shoes, and finished it off with a necklace
        At first I stayed in the house, but eventually went to the large box store and bought some milk
        It was exciting having ladies see me dolled up; knowing I had nothing on underneath the skirt.

      • On my first night out I wore really silky sheer jet black pantyhose, a tight form-fitting mini skirt, simple tight black top that showed my little tips and hard nipples, and five inch black stiletto pumps. My wig was a black bob, and I had learned how to do the whole make up thing well, with smoky eye shadow and glossy wet look lips.

        I walked out to the car past a few neighbors walking, and somehow took the chance to go to the nearest corner store fully dressed, giving a little flirtation to the few men in there.

        But the amazing part was driving to a second store in a black area (this was Savannah Georgia). I got out of the car and took pictures first with the station in the background from a field behind it. Then drove in and saw a super sexy older black man sweeping the walkway. He worked his way over clearly to get a better look at me. When he got next to the door and I gave him a nice look at my mile long legs, I opened the door and in my best girlie voice said “excuse me sir... I have a terrible cramp in my calf. As he smiled and leaned down I dropped my heel from my sexy foot and looked him right in the eyes and grinned “what I REALLY want is a nice sexy foot rub!”

        After a few minutes in which I fell in love with this sexy stud’s caresses but feared a cop or someone coming by, I again looked at him most likely with a crazy sex look in my face, and said “how about I rub something of yours now...?”

        We drove to a secluded area, and a half hour later I was driving home with semen stains all over my stocking-covered thighs while enjoying the delicious taste of black cum. Almost as much fun was totally worshipping his big black balls with my lips and tongue.

      • I love walking about at night in the summer in a skirt, blouse, stockings, and heels

      • My name is Cassie I am a sissy crossdresser and I go out dressed day and night. And no one seems to care. It's so much fun I love been a dresser

      • Fabianschulz@hotmail.be

      • Wear a shirt and tie with a plaid skirt and a ladies cardigan...Knee socks and mans shoes

      • Wear the same thing I would wear. A short, tight mini that shows off my big ass, black fishnet pantyhose with a seam up the back, 5 inch killer red heels, a really tight reveling top that fits the tit's just right. I walk in the park at night. I get excited just thinking about being out dressed like that. Lots of guys try to hit on me, but I don't want a boyfriend, I just want that dick.

      • I'm a guy that is wishing I could look more like a girl and then have a few guys to think I was a girl and then have me suck on there cocks and then have me Bent over and have a great big hard cock in my ass and I would love to have it happens to me weekly charlie horny

      • I want to be dressed up as a girl and I could walk with youand end up at the bookstore looking at the guys that want a head job and I can't stop thinking about it .

      • Wear a short A Trim Red short dress, black red laced panties and red garter belt with sheer black stockings. Do a walk in the park on a soft windy day so your dress will lift up to show what is under it. Then have fun with those lucky naughty's out there.

      • Yellow print "A Frame" dress with a red sash. Sheer stockings with garter belt. Short heels. Wait for a morning with a light breeze so that your dress will lift up to show your gorgeous legs. Oh yes!, of course honey you don't want to wear panties. Tell me where you are and I'll cum and have some fun with you.

      • Little black dress, sheer black stockings and a garter belt. Lastly skimpy black lace panties. As for shoes 3 inch stiletto heels. If You feel really naughty don't wear any panties!!!!! Good luck & be safe.

      • I walk in the mornings before work wearing mesh leggings with fishnet pantyhose underneath.

      • I wouldn't take the risk, too easy to be assaulted.

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