So I wanted to tell you about what recently happened to me. I have been so wrapped up in wearing female underwear and clothes and making myself look more feminine as described in my first post that I decided to go out last night wearing some of these clothes, seeing if it would help me take my dream to the next level.
So first I came home from work and took of my cotton pink Hello Kitty panties that I was wearing during the day.. I showered and freshly shaved my legs to get them all smooth and looking good. then I slipped on a pair of my prettiest pink panties, they were boyshort panties with beautiful lace pink and gold flowers going down either side.. I was so excited!!! Then I put on a pair of pantyhose so I could feel the friction of the nylon rub against my legs as I walked. I got more and more excited as I slid the nylon over my legs. For added measure I put on a little mascara and just a hint of eyeliner to make my eyes look more feminine and hopefully someone would notice :)))
I first went to a casino on the strip and hung out there for a while with no results, I wasnt openly looking at men or flirting but if I saw one look toward me I would smile and see what happened. After being there for a bit I went to a small hotel that had a bar, this hotel is closer to an area just off the strip where there are a lot of gay clubs and my reasoning was that maybe there would be some people there since it was close to the clubs and maybe I would find someone who was getting ready to head over to the club. My guess proved correct :))) I went to this bar and ordered myself a mixed drink and a girly drink at that (a cosmo lol) and sat at a bar stool. I kept turning every few minutes to survey the situation and soon realized that every time I turned around this one particular man would turn to look at me. I was really nervous inside and a bit unsure of what to do so I kept turning back toward the bar for what seemed like an eternity when in fact it was probably 4 or 5 times over 20 minutes :)
Then it happened, I had turned toward the bar for the what seemed like umpteenth time when he came up to the bar and stood next to me to order himself another drink. He asked me what I was drinking and I told him and introduced myself trying to give as faint of a handshake as I could to send the signal that I was a submissive :). He asked me if I would like another drink and I said accepted his offer to sit down at a table where he was.
He was a visitor to Las Vegas from the midwest and he was here for a tradeshow like so many other people who visit this city. We made some small talk for a while about how is it to live here etc then he asked me.. It looks to me like you have eyeliner and mascara on, is this something you normally wear? I laughed nervously and told him that I was trying to explore another side of me that nobody here knows about. I could see that this excited him and he asked me if I wouldnt mind telling him what was that? Well.... Once I started, granted it started slowly and halting, unsure of who I was talking to but happy to have a sympathetic ear it began to come pouring out of me.. My desire to be feminine, to dress like and look like a girl and my thoughts and hopes for the future as far as my feminization goes. As I spoke his smile got bigger and bigger and I could tell he was clearly excited by what I was telling him so he asked me to come up to his room to fulfill whatever fantasy I wanted and not to worry that if I didnt want to do anything that it would be ok. My heart leaped at the thought but I politely told him that I would think about it because I wasnt sure and I didnt really know him (all the while I am kicking myself inside for not saying yes!!!). He didnt mind my rejection, he was a handsome man a little overweight but nice build in his mid 40's or so and he told me that it was fine and he wanted to hear more about my hopes and desires. So I kept talking about what it was that I was after, my love for high heels my love of pretty dresses and how I was going to achieve the girly look that I always secretly wanted to have. After about 15 more minutes he asked me again if I was sure that I didnt want to go upstairs with him, this time I accepted!!! I felt very proud of myself but nervous all at the same time.
So we went up to his room, it was only on the third floor so no time to think about it and back out girl lol. Before I knew it we were in the room. When we got there I stood awkwardly for a minute or two then he told me how pretty my eyes looked all made up now that he can see me in better lighting. OMG this made my heart jump inside and was something I always wanted to hear someone say! He pulled me close to him and told me that he would help me get through this because I was really a bit nervous. I have sucked cock before but not really with a stranger. He began to rub my shoulders a bit to loosen me up and he asked me if I was comfortable taking my pants off so he could see my panties and I did so faster than I would have liked lol. There I was standing in some strangers hotel room in just my pink panties and pantyhose!!!
He smiled at me and again told me how pretty I looked and began to unbutton his belt, it was here at last the moment of truth!! he dropped his pants and underwear to reveal a modest sized 6" cock with average circumference so I definitely wasnt disappointed at all :) When he put his pants on the chair next to the bed he came up to me closely and told me to get down on my knees and fulfill my desires. I was too excited to think and dropped to my knees and began to suck his cock. He moaned loudly and instantly his cock became rock hard. I would look up at him and he would alternate between having his eyes closed and looking down at me as I gobbled up his shaft. The more he moaned the hornier I got!!
Soon I had his entire shaft down my throat and my lips were pressed against his pubes. He would alternate between holding my head and face fucking me and removing his hands and let me work his cock. He began to give me directions which really turned me on and he could see this. He would tell me to stick my tounge in the slit of his cock and to flick the head with my tongue which I eagerly did. As I sucked him he began to get more bold and he began to tell me I was a good slut, OMG I thought I was going to cum just from him talking to me. I got very excited as he talked to me and by now my guard was down completely, I was totally under his control. He told me to stop sucking and stand up so I did and he told me to turn around so my ass was facing him. He began to rub his hands over my pantyhose telling me what a nice ass I had. I think my knees visibly buckled when he did that lol and he knew he could do anything he wanted at this point. He told me to take my pantyhose off so I did and then he began to rub my panty clad ass and slapping his cock against my panties. I was scared but totally knew what was coming next. He went into his suitcase and grabbed some lube and a condom and told me to say no if I wanted him to stop. He waited like a half a second then put some lube on his finger and slid my panties to the side, he began to coat my outer anal fold with lube then his finger went inside spinning in a circle and moving in and out as he prepared me for his cock. Next he told me to get on all fours on the bed and he put on the condom. He never took off my pink panties he just moved them to the side and began to move his cock against my ass. I could feel the pressure as he began to insert his head into me. For me its always painful at first because I havent done this much but I think I will have to get a butt plug to stretch myself out :))
Once he got inside me he began to go a bit deeper as he slowly worked himself in and out of me.. first one inch then two and by the time he had about 4 inches inside of me he just shoved hard one last time and buried himself up to the balls in my ass-pussy!!! OMG it hurt like hell but as soon as I relaxed a bit the pain went away and he began to thrust in and out of my ass. He was grunting fairly soon so I knew my ass felt very tight around his cock and I began to push back against him telling him that I liked it when he called me a slut. He told me I had a great pussy and that I should just become a total slut and whore myself out to men! I had been stroking my cock while he was fucking me anyway but when he said this it totally took me over the edge and I moaned deeply as I shot a huge cum load onto the sheets of his bed. I yelled that I was cumming and he began to pound harder and within a minute he said he was going to cum too. He came into his condom while he was buried balls deep in my ass and he shook violently as he came.
I turned around and looked at him and didnt know what to say, I just smiled and told him thank you. He looked back at me and told me that I was going to do just fine and that I am on my way to being what I want to be :)) We both cleaned up and I left the hotel walking just a bit funny but it was definitely worth it. This is a true story and all my stories about my sex here in Vegas will be true not fabricated in any way. Thanks for reading it :))