Background:
I’m a closeted sissy. Day to day, I present as a straight male. I’ve been dressing for a few years now on and off. When I dress, I usually take pics to post & flirt with men online. My experience has been getting pegged (once), my dilido, and a one time play session with a man. I rarely, if ever, have the time to dress & play. I’m not into the degradation & disrespectful side of this kink.
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This is a pretty long (real) story, but I wanted to write out all the details. Enjoy!

About a month ago, I was able to travel for work which allowed me to finally have the time & space to be the sissy I’ve been craving to be. My goal was to go out dressed for the first time, and to find a playmate.

I was so excited. When I got to the hotel, I unpacked all my gurl clothes and laid out all the options. I took a hot bath and shaved my whole body for the first time ever. It felt wonderful to be completely smooth. Everything that touched my skin felt so sensual. I teased my hole with my plug, and slowly slid it in. It had been a while. I missed it. I put on a thong, and an oversized t-shirt & began to paint my nails.

As I was lounging around, I started to browse on Grindr. I instantly started receiving messages & pics from men. Not going to lie, I got very horny. The fantasies that ran through my mind…..I put my cage on. I wanted it to build. Back to Grindr…someone caught my eye. Let's call him Jay. He was visiting the area on a work trip. He was dark skinned, fit/muscular, and a few years older. We exchanged a few messages, and pics. He had a good looking 7in cock. I was drooling & smiling over it….over the possibilities. I asked him if he was into taking pictures/taking videos, but he wasn’t. I always think it’s fun, but I wasn’t opposed to just enjoying it. We agreed to message later on if we were free. We were both looking for some clean, safe fun.

Fast forward to that night. I spent a few hours getting ready to go out dressed for the first time. I was so nervous. The only reason I was doing it was because I was in a completely different state & LGBTQ friendly city. I tucked, and slid a lace black thong up my now smooth shaven legs. My best asset, so I’ve been told. Of course I had the matching lace bra to go with it. I spent some time putting on my makeup. I wore a denim skirt with sheer stockings & a top with a bomber jacket. I put my wig, glasses, & heels on, sprayed some perfume, and I was ready to go. I took a deep breath, grabbed my purse & headed out. I ended up going to a gay bar. I got to have a few drinks, and danced a bit. Unfortunately, I didn’t really get approached by any men but I guess I can’t expect that at a gay bar, right? This whole experience was a bit underwhelming, but at least I did it! It would be great to go out to a place where girls like me can be themselves.

On my way back from the bar, I messaged Jay. I was fully dressed, and didn’t want to let this opportunity pass. By the time I got back to the hotel, there was still no answer from him. I got to my room and started browsing Grindr. I was about to call it quits until Jay messaged me saying he was getting out of a show. I invited him over. He told me he was going back to his hotel to shower & then he’d be over. I appreciated him wanting to clean up before coming over. I prepared myself. I cleaned my hole, plugged myself, and put my cage on. I wore a corset, stockings, and a red lace thong. See my profile for pics of me & use your imagination :P

When he arrived, I had to go get him at the lobby. I put something on top & went down. Again, I was nervous. As soon as we locked eyes, Jay’s first words were “You look so sexy” and gave me a hug & kiss on the cheek. I was smiling so hard. We got in the elevator. He just kept starting me up & down. He proceeded to tell me how hot I looked. I spun around for him. He pulled me by the waist into a kiss. Thank god I had my cage on.
We got into the room and we started exploring each other with our hands. I turned around and started slowly grinding on him as his hands touched my whole body. He was infatuated with my ass. I slowly started stripping. I took off my top, and slid down my skirt, making sure my ass rubbed up against his now throbbing cock on my way up. I was just in my corset, cage, red thong, stockings, and heels…I took off his shirt and ran my hands across his muscles…abs…I started to unbutton his pants as he was kissing my neck and grabbing my ass…..

His cock felt and looked so much bigger than the pic he sent me. I started stroking his cock….fell to my knees…started kissing it…my red lipstick standing out on his cock. I ran my tongue all along his shaft until I got to the head..twirled my tongue around it before taking him in my mouth. I was so turned on by the moans he was letting out. I told him to take a seat on the couch. I began to give him a lap dance…shaking my ass on his cock. He slapped it a few times. I wanted him so bad.

I got back on my knees to service him like the good slut I wanted him to know I was. He liked when I stroked his cock while still having my mouth full. I kept eye contact the whole time as his cock got wetter and wetter. Every now and then I would take his balls in my mouth while still stroking his wet cock. He kept telling me: “Your mouth feels so good…you look so sexy with a cock in your mouth…your tongue is amazing.” It was so validating. I wanted more of him.

We made our way over to the bed. He threw me on my back and told me to open my legs. He started kissing my thighs while teasing my locked clitty. He took out the plug, slowly starting to play with my hole. He then proceeded to show me what his tongue and mouth could do. I was squirming with pleasure. I was moaning, grabbing the sheets….I needed him inside me.

“I want your cock inside me…I need you to fuck me”

He turned me over, grabbed the condom & lube…and started to tease my ass with his cock. He slapped it around a few times before slowly thrusting into me. He kept saying “your have such a phat ass…holy fuck, what an ass.” I could feel every inch of him inside me. I asked him to slap my ass. He took his hand and smacked both my ass cheeks as he started thrusting faster. Fucking amazing. The biggest turn on was him wrapping the corset straps in his hand to use as a handle as he was fucking me. I was so wrapped up in the moment that a few thrusts later, I had the biggest sissygasm I’ve ever had. I was face down, ass up and I moaned so loud into the pillow. He asked me if I wanted to stop since I came, but I said absolutely not. I wanted his cum.

I laid on the bed, and I started to ride him reverse cowgirl so he had a perfect view of the ass he loved so much. His hands were all over it as it went up and down on his cock. After a few minutes, he fucked me from the side & then missionary. My legs were on his shoulders as he fucked me. That sight…I lost it. I don’t know what came over me but I said “I’m your dirty slut, daddy….I’m your fuck toy…please give me your cum!” That brought him over the edge. He pulled out, took off the condom and cummed all over me...my caged clitty…and some even got to my face. We both laughed with pleasure and just laid there as I licked his cum off my finger.

That night, I was his fucktoy. And I fucking loved it.
We cleaned up. We chatted for a bit, thanked each other for a good time, walked him to the elevator, and we went our separate ways. It was such a great experience. I could not have asked for a better time, or a better man. He made me feel so femme in the bedroom. He was respectful, validated me throughout the night, and he brought out my slutty persona. This was my second time playing while dressed. I’m very selective, and like vet appropriately, but it’s totally worth it to get a good time.

I was so sore the next day, but it was totally worth it. The only thing that sucks about this is that I really enjoyed it, and now I want more lol Unfortunate part is that this is a rare opportunity for me. Maybe one day again in the future I’ll be able to have this much fun again…..

Hope you enjoyed my escapade…let me know your thoughts xoxo