Crossdresser confession

Added: Eunique Covarrubias - Date: 07.09.2021 01:26 - Views: 33416 - Clicks: 7049

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. I 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.

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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 crossdresser confession. 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. 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 crossdresser confession 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 I 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. 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 myself 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 crossdresser confession I thought. 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. I can't explain why but somehow I just felt attracted to him.

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So we talked and exchanged pics, me dressed up and not dressed up. Finally he asked me if I wanted 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.

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Going so far 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 crossdresser confession 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. Crossdresser confession 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 crossdresser confession 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. 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. 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 crossdresser confession 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 sweatpants 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, in my best feminine voice, which really is pretty good. Not all nasally crossdresser confession you usually hear.

He offered me a drink which I declined, though I should have because my mouth was so dry from nerves I could barely get sounds out. He told me to go and sit down by him on the couch so I did. We sat and talked for a little bit and he kept mentioning how good I looked which just made me feel better and more relaxed each time.

With that he started kissing me again and I kissed him back. My one hand had crossdresser confession behind his back on the couch and my other had was on his chest. I loved the feel of his chest hair and kept rubbing my hands over it. Then it happened. He took my hand from his chest and moved it to his crotch. I could feel his hard cock through the pants yet another first for me. He took his had away and I continued rubbing it. After a minute or two he stopped kissing me and leaned back in order to pull his pants down.

Without missing a beat my hand was back on it stroking it. This was my first time touching one that wasn't mine, but I'd seen a lot of porn up to that point so I knew what to do. With his one hand he managed to undo the tie in the front of my dress. I lifted myself off of the couch so that he could pull it open. There I was When my hand was free, he pulled me on top of him and started kissing me harder.

At this point I knew what I was going to do. I stopped kissing him and started kissing him down his neck In this age of the internet, and having been on the receiving end a few times by girls I reached into all of my knowledge and did what I came there to do.

It started by kissing up the shaft and then up to the head. This giving my time to build up some saliva. With that accomplished, I switched to licking around the tip. Then up and down a few times until wrapping my whole mouth around it. It was so warm and hard in my mouth. A little bigger than average sized, definitely not porn star size. Up and down. You'd think I had done this a million times before but this was my first time giving a blowjob. And from his reaction he was enjoying it.

I imagined him being married and his wife not doing this.

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I imagined him desperate to find someone who would do it and be excited about it. And it was me that was doing it.

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He would put his hand behind my head to push me down further onto it, which I surprisingly was able to do, and alternating between rubbing my back. Even going so far as to unhook my bra with one hand very impressive. My alternating was between sucking his cock or jerking it while I licked and sucked on his balls.

Finally, he said the words I was worried about I have a few seconds to decide how this is going to end. Do I stop and he cums on me? Do I let him cum in my mouth and I spit it out? It was a decision my brain crossdresser confession to make but I wasn't stopping.

I doubled-down and was stroking him as I sucked. This was apparently more affective and within a few groans it happened. His body froze meanwhile I could feel his cock pulsating in my mouth.

Crossdresser confession

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