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Crossdresser Crosses Over for Good

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Crossdresser's first time with a real man.
998 words
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I certainly allowed myself be conned! So, I had a problem with my turn signals on my car back in early January. I was pretty sure it was the turn signal switch, but not sure. There is a site where sex ads are very prevalent. In the CD section it's mostly hispanic, and oh do the latino boys just LOVE us white cd's!! They are very relentless in their pursuit of us!! Knowing this and knowing that there are a lot of hispanics in the auto repair industry, I sent out this ad:

45 y/o CD Needs Easy Car Help.

45 y/o White Versatile CD needs easy car help. It should be a cheap and easy fix. I would like to come to your place and have you check it out. I don't have a lot of cash, but am willing to pay in other ways. ;)

At this point, some very brief background. I first started being attracted to cd/trans when the internet first came on. I was a normal, manly man. But I was just fascinated and it took hold. Damn internet shemale porn!! So, I started to get with cd's and they would suck me or ride me. Then, I started to suck and ride them. Then, I started dressing. Until I started dressing, I NEVER considered being with a "real man". But my 2nd night out dressing, I was walking down to street from where I parked my car to a club and some guy who was driving by slowed down and was checking me out. He was a younger cutie and an electric charge went through my body and my little clitty just JUMPED out of nowhere. I was shocked. The next night, I was at a club rubbing this cute guy's cock, but I couldn't understand he was saying and I ended up going to another cd's place to finish the night. Up until that point, that's the most I've ever done with a "real man".

Within the first 48 hours of posting the ad, I had a good 18 or so replies. I picked this one guy. He said he was pretty good with cars and to come to his house, around 1 pm. I dressed up and drove over to his place, about 25 minutes away in city traffic. It was unusually warm for a January in Chicago. I had my black sweater on, hot sparkly pink panties, short skirt, heels, wig, perfume, earrings, wig, the whole thing. Remember, I have no working turn signals. There was a very good chance that I would be pulled over if I switched lanes, which I had to do often. I was SOOO nervous I was almost panicking at the thought of being pulled over.

I arrived at his place on time. He looked at my car and figured it was the turn signal switch, but he didn't have one. So, we were done with the car. He invited me inside, his wife wan't home and he was alone.

I freshened up in the bathroom and came out to his living room. He asked if I still wanted to fool around. I didn't really know what to do, so I said yes. He sat down on his couch and unzipped his pants. I rubbed his cock through his underwear and then took his cock out. I started to suck his six inch uncovered cock. Bobbing my head up and down and trying to get as wet as possible. I think I was giving a very good blow job to him because he was moaning and I think he was close to cumming.

He stopped me and asked me to bend over on the couch. He put on a condom, we used some lube, and he started to enter me from behind. It hurt at first, and finally he was all the way in. He was pumping in and out of me and it was pretty painful. I was squealing in a really high girly pitch, but it was real. I was definitely enjoying the mental aspect as I kept visualizing what his cock looked like in my ass. Thinking back on the many times i had that exact view. But the actual physical part was not enjoyable. But I was letting him do what he wanted with me.

He then said to go to his bedroom. He had me lean onto his bed and entered me from behind again. Even though it seemed like the same angle, it didn't hurt, at all!! So, I started getting into it, moaning and encouraging him. He slapped my ass, calling me a slut, a hot for cock crossdresser and telling me to take his cock. I was enjoying this!! I was rocking back hard into him as I could take his cock easily. He then came in the condom in my ass. After some moments, he got dressed and told me I had to leave. I fixed myself up and showed myself out the door.

Basically, I didn't get my car fixed, got fucked by a real man for the first time, didn't get paid, I didn't orgasm, and ended up some of my own cum stained on my panties,. How that came to be, I don't know.

Now I am horny as fuck!! What an exhilarating experience!! I get into the car, drive around the corner and jump on a gay hookup app I have a young guy that wants me to blow him in his garage just 2 blocks away! I come around the back in his alley, but he ghosts me. I hang out for an hour of 2 in an incredibly horny and submissive state, don't get any real opportunities and drive home. My turn signal is still not working and it's rush hour. I do make it home without any problems and jump in the shower.

I haven't stopped thinking about getting dressed up and fucked by a real man again.

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AnonymousAnonymousabout 1 year ago

I love cum in me aswell as on me and.lots of I loved the story and want to go out and get gang banged I love multiple cock fucking me AMD face fucking me want to be whored out and dp me ill do anything any one have a suggestion for me

AnonymousAnonymousover 1 year ago

i wanted to be him and drink a mans cum without spilling any

AnonymousAnonymousover 1 year ago

To Trish & anonymous slut in 120 denier hold ups below I’m so horny for both your stories & would luv to meet either or both of u so we could have hot fun together as I want to be dressed up & used like both of u & to be the one using u. Luv both ur stories which make me hard & craving cock in Hampshire UK.

AnonymousAnonymousover 2 years ago

I love dressing like a slut being in my wet look suspender belt 120 denier hold ups patent ankle boots side tie panties with the motif Fuck Me on them. I compliment them with a black fish net bralet short black leather jacket and black long wig basically looking like a prostitute. I usually meet older married men who want no strings sex and the fun they got before being married just being sucked off and hot anal sex that they dont get at home anymore. Usually its either in my car or outdoors on a park bench whatever they need to excite them. Getting a warm load inside me tells me i hàve them turned on and getting the sex they miss and crave again. Im Paula a CD Slut in the UK

AnonymousAnonymousover 2 years ago
New Sissy

I am new to cross dressing and all that goes with it.How i love doing my hair and make up.But how i love getting dressed in womens clothes.I really love stockings garter belts thongs push up bras.I have found sexy heels and nice silk slip dresses.I have found a older couple who love to use me for their sex games.They have taught me how to suck cock deep throat and swallow cum.They both fuck me her with a strap on and him with his 7'' cock.He in joys doing ass to mouth on me and filling my mouth with loads of cum.They now like to tie me up and have me do oral on her while he fucks me.I now live with them and they both dress me and do my hair and make up.Oh and now i started to take whoremones and my breast are 36c and getting bigger.

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