How I Started Dressing and Feelings

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Crossdressing slut and how it began.
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When I was in my early twenties I was very much a ladies man and had sex with so many women. Later in life I realized that most of the woman I bedded were looking for a husband and did good work trying. I was so amazed at how eager they were to satisfy me in so many ways and in so many locations. It was not unusual to get a blow job in the car, even while I was driving. Some of them wanted sex outdoors, anywhere and I sure was not apposed to it, no sir.

One day I was at my mothers home to clear out her belongings because we had put her in a nursing home. I found a couple of her wigs and tried them on. It excited me and I went thru her lingerie and put on her panties and pantyhose. Wow, that really got me hard and I loved the feeling and the look as I gazed in the mirror. I masturbated looking at myself and imagining being a woman and being used by a man. I was hooked. I saved her things for later use.

I dressed in private on occasion and would have fantasies of pleasing other men. I started cruising parks for sex, since I knew that is where men went to have sex with other men. First time an older gentleman got into my car and took out my cock and gave me a wonderful blow job and I was thrilled to shoot my load into his mouth. He had me then jack him off and he shot a huge load all over my hands and his stomach.

After that I returned to the park and received blow jobs from lots of guys, young and old. Then I got curious about sucking cock and I started going down on other guys and giving blow jobs. Wow, that was so taboo but I loved doing it for them. It gave me the feeling of being a woman and then I knew why some women suck cock.....to please a man! Young guys and old guys, I went down on anyone who wanted me to satisfy them.

Then one day a guy told me he thought I would look hot as a woman. So my mind ventured to dressing again. I started out dressing at night and would stand outside my car in panties, hose, short dress and a wig, showing off my legs to anyone driving or walking by. I was a hit with my slim sexy legs. Guys would stop and walk up to me, some feeling me up and others taking out their cocks and pushing me down to my knees and I would give them head until they ejaculated into my mouth. Some would raise my skirt, pull down my panties and stroke me and then suck me.....I loved being a woman for anything.

I was so curious and wanting to be used like a woman and needed it inside of my pussy! The first time I was in the park at night and a black kid college age, came over and took out his cock and told me to show him my ass. I bent over and he ripped of my panties and played with and rubbed my ass cheeks and soon had his cock between my ass cheeks and was dry fucking me and soon shot his cum all over my ass and back. He moaned and groaned as he got off and I loved knowing he had used me.

The same night an older man got out of his can and motioned me over and I went down on him and then he pulled me up, bent me over and thrust his cock into may dry pussy and it really hurt me. I was not prepared for this...and he just pounded my pussy roughly and pulled out quick and shot off onto my legs. He left and I got back into my car because I was so sore from his pounding. As I sat there a guy came by my car and asked me if that was the first fuck for me? He had been watching. I told him yes and he talked about how I should prepare myself in the future by using something in my pussy to get used to the feeling. He gave me his number and told me to call him anytime and he would help me get used to it. I liked the idea and called him the next day.

He had me to his apartment the next day and had me strip for him and he played me on his bed and fingered my ass for awhile and then had a small dildoe inside of. me, giving it to me gently for awhile and then picked up the speed and was fucking me with it. He let me rest for awhile and then used a bigger dildo inside of me for awhile until I got used to it. We talked a lot and he invited me to meet him at the park the next week on Friday, a busy night at the park. He told me to dress like a slut because he was going to use me like a slut.

I met him there after dark and he had me walking around showing off my legs and ass, bending over and showing my naked ass. Men came over and Jim, my teacher and friend, would tell them to be gentle with me. Jim had me bent over my car truck and guys took turn fucking me until three of them had their way with my pussy. All used lubed condoms. Jim then had me suck him off in front pot others and I swallowed his cum.

After that I cruised several places at night where guys went to meet others for sex and sucked men off and was usually fucked by one or two also. I craved cock so much after my initiation and was never satisfied until someone would suck me off or jack me off.

I became very popular in those three locations, as everyone knew who and what I was when I parked my car close by. I even went to mens apartments or would meet guys in the woods for sex, satisfied two and three guys at once....;always along a creek next to a local park area.

I have so many stores to tell about being a crossdressing cum slut..

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AnonymousAnonymous5 months ago

Loved your story! I, too, am a lifelong CD, started young with my (girl) cousin dressing me in her panties and bras, then moved on to my mom's sexy things, girdles, hose, heels, wigs, pearl necklaces, oh, my, I get hard just typing that! Graduated to lifting panties and other hot items from cousins and girlfriends hampers then buying sexy things for my wife so I could secretly wear them! "Chrissy" has bought and purged so many hot, slutty outfits and shoes from thrift stores, always feeling guilty when I get rid of things then gradually growing a new set of slut wear! If you want to see pics, or maybe get together in Athens GA, horny4cum69@proton.me. Kisses,

Chrissy

AnonymousAnonymous5 months ago

Even though I'm happily married, I can't quit cruising for cock. I love cock much more than I like cunt. I'm a certified homosexual.

AnonymousAnonymous5 months ago

Could have been a really great story but turns out to be the Literotica version of drunk texting.

AnonymousAnonymous5 months ago

Meh!

BarebackingMichelleBarebackingMichelle5 months ago

I got started with other cd's and men the same way at public parks and parking lots . I also found I preferred older women's clothes to play in. I would shop at second hand stores for clothes and wigs and then go out and play. I love eating cum and I always offer to take their cocks in my ass pussy. I do this for hours or until I'm to sore to go on..

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