Crossdressing confessions

Added: Collette Leath - Date: 09.12.2021 14:25 - Views: 29939 - Clicks: 1861

I am 26 year old. I always been fascinated by girl's outfits. Whether it was mom's, sister's or my gf's. I secretly wore their lingerie when they were not present. I visited gloryhole every weekends. Crossdressing confessions love the taste of cum. I love licking precum of black cockgagging over cock.

One day i wore my gf's panty inside my jean went to gay theatre, there i got fucked by three guys. Then we breakup. Now i am alone. Part of me has always wished I was a girl. When I was a teenager I would sometimes take my sisters' clothes when I was home alone and try them on.

I loved the way the soft and satiny material felt. When I got older I started becoming bi-curious, I would chat with guys online and send pics of myself, often times in my sister's clothes. All the guys loved it and it made me good, being looked at like that.

I especially loved when older guys would lake with me.

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The idea of a guy old enough to be my dad excited me. I started getting a little bit bolder and bought a wig and makeup and even some nail-polish. I'd watch tutorials on youtube on how to do makeup to look more feminine. Thanks to Amazon I was able to eventually expand my secret stash to include some clothes so I wouldn't have to "borrow" from my sisters. I got a bra and panties, some thigh-high stockings which come pretty high on my short legsa pair of heels and a pretty wrap dress that came right above the knee.

I'm not a hairy guy so Crossdressing confessions never had to worry about facial hair, or really body hair for that matter. So much so, that my parents never even noticed the times a shaved my legs, or if they did, they never mentioned it. I loved the responses I was getting and had so many guys wanting to meet up.

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Finally I decided to just go for it. This wasI was 22 and in good shape, thin but not muscular. I am only 5'4" with blue eyes and dirty blonde hair. My parents were going away for the weekend and my sisters planned on being with their BFs so I had the place to myself. Having a full weekend to crossdressing confessions I decided to jump on the opportunity.

I setup a new profile on Grindr, identifying as a CD and posted some of the pictures I had taken. OMG the responses I received. I guess I looked better than I thought.

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So after chatting with a few guys throughout the day I eventually hit it off with an older guy who lived a few towns over from me. He said he was 46 and he was 6 foot He was a big burly buy with a hairy chest and neat beard.

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I can't explain why but somehow I just felt attracted to him. So we talked and exchanged pics, me dressed up and not dressed up. Finally he asked me if I crossdressing confessions to come over to his place that night. I was terrified and excited at the sometime, when I wrote back, "Yes. I still had a few hours to get ready so I took my time. I went and took a shower, taking the time to carefully shave my entire body.

Going so crossdressing confessions as to use my sister's moisturizer so I was soft and smelled nice. Next I painted my nails so that they had time to dry. Since no one was home I decided to live it up and do my makeup and hair at my sister's vanity. It was nice not having to sneakily try do do it in my room. I took my time and was able to do it flawlessly. I was able to style the wig so it wasn't just some mat of hair.

It actually looked like it did online, when I bought it. Now time to get dressed. I put on the pushup bra I had bought and put those inserts in it, so it would kind of give me cleavage. The rest I used makeup to give the illusion you can learn anything from youtube. I put on the panties, tucking my penis down, as I had been practicing, the thigh-highs and my dress.

With no one home I could use the full sized mirror in my parents room to finally see me, and not as a crappy selfie. I was shocked. I looked like a girl. From a distance I would probably be confused with one of my sisters. I was counting on that because I now had to leave the house, dressed like this. Thankfully it was winter and got dark early, so if any neighbors saw me, they wouldn't realize it was me. Around 10pm I got the text, "You can come over now.

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They consisted of parking at the end of the block and texting when I was there. Then I was to start walking up a few houses and he would al me. So I drove and parked at the end of the block. It was a dark street. Street lights were overgrown by trees so you couldn't see house s. So, I sent my text and started walking.

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After passing the second house I heard a, "psst" but I couldn't see where it came from. Then he used the flashlight on his phone to get my attention. He was behind the fence on the side of the house. I walked up the dark driveway, and over to him and he let me in through the fence. He greeted me and said we had to be quiet because his wife wasn't home but his kids were sleeping.

By this point you could pretty much see my heart beating through my chest. Here I am, at a strange person's home, no one knows I'm here, and I dressed as a woman about to do, who knows what. And yet with all of this I followed him through the fence, down some steps into what seemed to be the basement. When we went in and he turned on the lights it looked like an apartment or maybe a mancave. It was too small for a family so I'm guessing that they rent it out and they just didn't have a tenant.

He closed the door behind me and came over and said he was glad I came over and put his arms around me and started kissing me. I had never kissed a man before but today was going to be a day of firsts. It also felt nice because it was winter and I was in a thin little dress.

He said I looked beautiful and that he loved my outfit. He was in a pair of black crossdressing confessions and a robe that was untied so his chest was out. He said that if he didn't already know he would have sworn I was a woman, which made me happy. I said thank you and that I was glad he liked it, crossdressing confessions my best feminine voice, which really is pretty good.

Crossdressing confessions

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