My first night out as Sophi started in a casino parking lot. It took about thirty minutes of sitting in the car before I mustered the courage to get out. My nerves were going crazy and I was more than a little bit scared but even still, I was so turned on I could barely contain myself. My erection would have been raging out of my skirt if not for my chastity cage.
“I can’t believe I’m doing this,” I thought as I took the first few steps towards a night that would forever change me. My hands were shaking and my legs trembled as I walked through the parking lot of the Golden Nugget. The candy-pink colored hair of my wig brushed my cheek as I looked up at the entrance doors of the casino. My sissy cage was working overtime and I struggled to walk in a way that was normal and feminine. I almost turned back 3 or 4 times before I reached the entrance. My self-doubt was growing and even though I felt confident that I was more than passing (as long as I didn’t speak), I was still terrified that people would notice or laugh at me.
I picked a Friday night at 11pm on Fremont Street in Las Vegas for my first outing as Sophi (my online persona). I made the trip to Las Vegas alone and this adventure was its sole purpose. It was my first day here and I had spent the last 5 hours getting ready in my hotel room. I was shaved smooth and wearing my favorite outfit; a really flattering, tight blue skirt and a tight white top with bare-shoulders that showed a little of my stomach. I wore a black, c-cup bra that gave the illusion of small breasts and a matching g-string and garter-belt with black thigh highs that just peaked out of the bottom of my skirt. My make-up was subtle with an emphasis on my lips and eyes; both of which were larger than average and my most feminine features. My hair was back in a pony-tail with the bangs swept to the side and a couple of strategically loosed strands that were allowed to fall freely. I was worried that my pink wig was going to make me stand out too much but decided fuck it; I loved the way I looked in it, and if I was being honest with myself, I wanted guys to notice me. I had always fantasized about being dominated by a hot older man. To be made his sex slave, his perfect little sissy who’s only purpose in life was to please him sexually. I couldn’t admit it out loud but I was secretly hoping to meet a guy like that tonight and maybe he would take me back to his hotel room to ravish my virgin pussy…
At 25 years old, I had been cross-dressing in private for a couple of years now. I had a naturally feminine figure; about 5’6 and 115 lbs, with a very toned butt, strong legs and a well-defined stomach. My arms and shoulders were toned but not very big. People often thought I was younger than i was due to my soft features and large eyes. By this time I had gotten really good at my make-up and realized that I made a pretty attractive girl. I looked really good in dresses, skirts, and lingerie and when I wore them I felt incredibly sexy. All of this had been confirmed by the numerous guys I had made cum online in anonymous video chat roulette sites. I had become obsessed with making guys cum. Every time a guy cummed to me online it was like a huge, sexy ego boost. I could see and hear their desire for me and it turned me on in a way that nothing else could. Sometimes I would edge for hours on these sites and make dozens of guys cum. I would cage my little clitty and had worked myself up to a 5” dildo that I used to put on a show for whoever was watching. I had just learned how to orgasm from anal alone and I would do it for strangers online. They loved me and I was addicted. And like any addict, eventually I needed more. Although I fantasized constantly about the real thing, I wasn’t sure I was ready for it yet. So after much thought I decided the next best step was to simply go out dressed in public. I wanted a place where nobody would know me and cross-dressing wasn’t too out of the ordinary. What better place than Vegas?! I carefully made plans and gave my friends and family an excuse about going to Vegas for work. After months of planning here I was! Dressed head to toe like a sexy little slut, vulnerable and alone in one of the biggest tourist destinations in America. I was about to enter the famous Golden Nugget and explore crazy Fremont Street as Sophi.
Before I knew it I had walked all the way to the entrance of the casino and an older couple who had just exited, were holding the door for me. I made eye contact with the gentleman, still trembling, but he just smiled and said nothing. I smiled back and felt a little relief; I didn’t think he noticed, and if he did he didn’t care! The smell of smoke hit me as soon as I walked through the doors and I was overwhelmed by the amount of people everywhere. I had been afraid that at this moment, the music would stop and everyone would turn to stare at me. But instead, nobody seemed to notice. I made eye contact with a middle aged guy and he smiled and maintained eye-contact as we passed each other and then looked me up and down. I recognized that look of desire in his eyes. I had seen it many times online. I kept walking and smiled to myself. Maybe this was going to be fun after all :)
I made my way to Fremont Street trying not to make eye-contact with anyone else. My heart was still pounding and I was still very nervous. The night air felt amazing against my legs and the added space started to make me feel more at ease. A band was playing nearby to a small crowd. A bunch of 40-somethings in rock-star cosplay were playing 90’s covers. They were actually quite good. I stood in the back next to a tall, marine looking guy who obviously worked out regularly. He wore faded jeans and a fitted Louisville Basketball t-shirt. The crowd was getting tighter and our arms pressed into each other. I looked up at him and tried to apologize through the noise as he said something that I couldn’t hear.
“What?” I said, and he bent down to whisper in my ear,
“Don’t worry about it.”
Chills instantly went down my spine and my cock tried to stand upright. He smelled amazing, and I looked back up at him longingly. It was at that moment that I noticed a girl standing next to him and holding his hand. She was absolutely gorgeous; petite and blonde with a perfect body and beautiful face. I felt a little sting of jealousy as he went back to watching the concert. I waited for the band to finish a spirited version of “Sweet Child of Mine” and decided to move on. I looked back over my shoulder after a few steps to see the marine-guy watching me leave. I smiled and he smiled back. God, I was so turned on. I wanted to find a bathroom, unlock my clit, and cum so hard. Again, I was struggling to walk normally but now I was loving every second of it.
Over the next hour or so, I walked up down Fremont street. I watched a couple street performers and visited a couple of mostly empty souvenir shops. I had to check myself out in every window I passed. I looked hot and it was a little thrill every time I saw my reflection. Some guys were noticing too. Most people didn’t look twice but I definitely got a little bit of male attention. One guy even catcalled me! It was a bit of a surprise and in the moment I was too embarrassed to respond so I fled as quickly as possible. It made me feel really good though. I felt like I had accomplished my goal. I went out in public and found that I really liked it. I felt so liberated and sexy. I was so turned on that I was contemplating going back to my car so I could touch myself. My feet were hurting from the heels so I made my way back to the golden nugget and sat at a bar with one of the video poker games. I ordered a cosmo from the bartender, a middle-aged woman with tired eyes, and thankfully she didn’t ask for my ID.
I put $20 in the machine and had just played a couple hands when a deep voice said, “Hey Beautiful, i won a ton of money tonight. Want to help me spend it?”
He was probably in his late 40’s; brown hair with a receding hairline and a medium length salt and peppered beard. His eyes were deep brown and he was probably about six foot tall. I was instantly attracted to him. I kind of choked on my drink and eventually mustered an embarrassed, “What?”
“Hey beautiful, I won a ton of money tonight, want to help me spend it?”
“You know I’m a cross-dresser, rr-right?” I just splurted it out. I guess I felt like he had a right to know; I wasn’t trying to trick anyone. Fortunately, he didn’t seemed taken aback by that and laughed and said,
“Lucky me. I saw you walking around outside and I was hoping I would be able to talk to you tonight. You’re the hottest girl I’ve seen all night.” He leaned in closer. “I’m staying here at the casino. I’ll give you $200 to come up to my room right now.”
My head was spinning at this point. I desperately wanted to go but I was also really scared and nervous. I’d never been with a guy before and although I had practiced with toys at home, I was still very tight and not sure I could handle a real cock.
“I’m not a prostitute…but I must say I’m flattered. What brings you to Vegas?”
We chatted a little after that. I found out that he was here for a technology convention, his name was Mickey and he was originally from the midwest. He ordered a whiskey and we talked for what I think was about 10 minutes, but the whole thing was a kind of a blur.
Eventually he finished his drink and said, “I’m going up to my room to take a shower. It’s room 1007. I hope to see you up there. If not, well then it was nice to meet you and be safe out there,” gesturing outside to Fremont Street.
“I’ll think about it,” I said and then he smiled and walked away.
If my heart was racing before it was absolutely pounding now. Was I really going to go up there? What would happen if i did? He was much bigger than me so I wouldn’t be able to resist him if it went bad. I paced the casino floor for a while and eventually found myself at the entrance of the hotel part of the casino. 1007. It was just a little more that way…I decided I could find the room but that wouldn’t mean I had to knock and go in. I could feel precum dripping down my leg as I headed towards his room and I started to worry that I might cum prematurely and disappoint him. That thought scared me more than anything else! I realized that all I wanted was to please him. I wanted to be his and would let him use me however he needed to…I found his door and paused. 1007. Before I could stop myself, I knocked.
He answered the door wearing only a towel wrapped around his waist and let me in. I could see now that he was actually quite fit. His chest was hairy and muscular and his arms were huge. He had a little bit of a belly and thick legs. He was a god.
“I’m glad you decided to come,” he said with a smile.
I was too nervous to talk and I think he picked up on that because he took my hand and led me in. It was a nice room with a big bathroom, a dining area, and a big king sized bed in the center. We stopped at his bedside and he turned to face me. He was taller than I thought at the bar. Even with my heels on I only came up to his chin. I felt him wrap his arms around me and pull me close. I was melting. We made eye contact and he kissed me. Slow and soft at first and then gradually deeper, more passionate. I couldn’t believe what was happening. I had never kissed a guy before. My mind was exploding from sensory overload and all I could do was submit to the moment. His lips felt soft and amazing even if the whiskers were a little odd. His hands went up and down my back, beneath my shirt and onto my butt. He broke the kiss to tell me how sexy I was and I blushed. I didn’t want him to stop. I could feel his cock pushing against my stomach through his towel and found myself pushing against it.
I lowered my hands to his waist and undid the towel. It fell to the floor and his gorgeous, rock hard, uncut cock popped out. It was probably about 7” and thick. It was certainly bigger than my 5” sissy clit.
“Oh my god,” I said. I think it was the first words I uttered since I entered his room. I took it in my hands and begin to massage it slowly while we kissed. He moaned through his breaths and I could tell he was enjoying it.
“I want you to kiss it for me, baby.” he said suddenly. Obediently I dropped to my knees and admired it close up. Precum dripped out the tip and I eagerly took it in my mouth. It was big and filled my mouth completely. I reveled in the salty flavor of his precum and worked the tip while one hand ran up and down the shaft and the other fondled his balls. He moaned louder now and put his hands around my head, pushing himself deeper into my mouth. I gagged pretty hard and had to stop.
“Are you new to this, honey?” he asked with concern.
“Well yes, is that ok?”
“Have you had sex before?”
“Not with a guy.”
“Well, we have to make it special then.” he said and pulled me to my feet. “Let’s get this off of you.” He pulled my shirt over my head and begin to kiss up and down my stomach and neck. “So fucking hot,” he whispered. He was on his knees now and his hands were running up and down my thighs and I felt him spread my cheeks. This made my cock twitch and I moaned loudly. “What have we got here?” he said as he pulled down my skirt and exposed my caged clitty. “I love it when sissy is caged for Daddy,” he said and took it in his hands, gently tugging at it. “Do you want to cum tonight, sissy?”
“Yes, Daddy.”
“Be a good little sissy and I might let you cum. Where is the key? That belongs to me now.”
“Yes, daddy.” I pulled the key out of my purse and gave it to him. He put it away in his night stand and then picked me up with surprising ease and threw me on to the bed. He got on top of me and we started making out again. His cock was grinding against my lower abdomen and stomach and I could feel his power as I wrapped my legs around him. I was in bliss but also a little afraid. I had never taken any toy as big as he was and I could tell he would fuck me hard if he wanted to.
“Do you like this, honey?” he whispered in my ear
“Yes daddy,” I managed to say.
“We need to get you ready now.”
He turned me over and knelt down by my feet. His hands rubbed my thighs and my ass. He spread my cheeks and then spit on my hole. Out of nowhere he spanked me hard. It stung but I found that I liked it. He rubbed the outside of my hole with his finger and said “what a tight little pussy you have for me.” He then bent down and began to lick my pussy, alternating with his finger until he stuck one in.
“Oh my god!” I moaned. It felt so amazing. My cock was throbbing and I needed to touch it so bad.
“Good Girl.” he said as he inserted 2 fingers. This hurt a little but I was doing ok so far. He reached over to the night stand and pulled out some lube. He opened it and poured some down the length of my crack. I felt his cock begin to grind up and down as he pinned me to the bed, kissing me deeply. I pushed back up against him and moaned softly.
“Please daddy, I want you inside me.”
“Fuck yea you little sissy,” He said and grinded harder. His hands had been going all over me but now one stopped at my throat. He wrapped his hand around it but only applied a light pressure. “Are you ready to get fucked like a girl?” he whispered in my ear.
“Yes, daddy.” I said. I was scared but so fucking turned on that there was no way I could stop it now.
“This might hurt a little, honey, but we’ll go slow… ”
The grinding stopped now and he got up on his knees and put more lube on his throbbing cock. With one hand he spread me open while the other guided his cock. I felt the tip push on the outside of pussy. Slowly but with a lot of pressure and then all of a sudden, the tip was in.
“Oww, Fuck.” I said, pain shooting through me as I tried not to squirm. It hurt a lot. He was so much bigger than anything I had tried before.
“Just breathe, baby.” He said. “It will pass.” He bent down and kissed my check, his hands now over mine, fingers interlaced as he pinned them to the bed. We stayed like that for a while and my ass slowly started to feel better, almost numb. “Are you ready for more?”
“Yes Daddy.” I said and braced for more pain.
“Just relax, baby-girl, you’ll be in ecstacy soon.” And he went further inside me. It did hurt but not nearly as much. Slow and steady until his entire length was inside me. “You are making Daddy very happy, I want you to know. You didn’t think you be able to take all of me, but you did it. How does it feel?”
It felt…well…. it felt amazing! My rectum burned with pleasure that went all the way to my cock. I had basically been edging all night and I could tell i was close to cumming now. I tried to respond but was only able to mumble something that resembled a “Yes.” He wrapped one arm around my neck and grabbed my hip with the other to give him leverage. Then he started pull back out slowly. He almost pulled his cock completely out of me before he slowly went back in. One pump, then two and three. Each one bringing me closer to orgasm. I squirmed beneath him but he kept me in place with his strong arms and the weight of his body. Five pumps and I could tell I wasn’t going to last. Each one came faster now I was lost in the rhythm of his thrusts. All of a sudden my entire bottom half exploded in pleasure. It was the most intense orgasm I have ever experienced. I quivered uncontrollably beneath him for what must have been 90 seconds or more. Cum gushed out of my chastity cage and I could barely breathe.
“Good girl” He said, almost laughing.
He thrust a couple more times a little faster and a little harder, each one shooting new waves of pleasure through my body. And then he tensed up and he squeezed me hard. I could feel his cock pulsating in my ass as he came. When it was over I was almost in a trance. I could barely move and he collapsed on top of me, brushing my hair out of face and kissing me lovingly. We laid like that for what seemed like forever.
Eventually I got up and went to the bathroom to clean up. It took awhile for me to shower and get dressed again but when I came back into the room, I saw that Mickey was asleep. I grabbed the rest of my stuff and was leaving when he said,
“You were great, baby. Your money is on the table over there. Come back same time tomorrow if you think you’re ready for more,” he said with a mischievous look on his face.
“Thanks, but I told you I’m not a prostitute,” feeling a little embarrassed now.
“Take it! You earned it. There’ll be more tomorrow but you’re going to have to work a little harder.”
“I’ll think about it…Thank you for everything, I had a lot of fun.” I said and kissed him one last time. Then I left and made my way back to my car. I don’t remember driving home that night but I masturbated twice before I fell asleep. I couldn’t stop myself from wondering what he meant when he said I’d have to “work harder next time.” I knew I was going to have to find out…
Source: reddit.com/r/eroticliterature/comments/gnefb3/my_first_night_crossdressing_in_public
So incredibly sexy!