Meeting a chat buddy Pt.1
I've been hanging out in chat rooms with lots of conversations going the route of "we have to meet" and they would always lead to the inevitable decision that we were too far from each other or my chat buddy or I chickening out when it got down to the details. I travel frequently for work all over the USA and finding a time and a place to meet is often an issue. Most often, it just came down to never being at the right place at the right time. That all changed on a recent trip. I was on my usual chat site and met a very interesting man with almost identical likes and dislikes. We were really hitting it off. Things got steamy and we even video chatted for about an hour as I coaxed him to cum for me. Then Stan popped the question that always comes up, "Where are you from?" and "Where are you tonight?. I mentioned where i was and got the all too common, "Damn, so far" which then led to him telling me where he was from. "OMG, are you serious?" i quickly replied. As luck would have it I was coming to his town in 2 weeks. We messed around with the idea of meeting each other and possibly hooking up. Before we ended the chat at about 4am, we exchanged emails I figured that was the end of that.
About a week later, I get an email asking if I was still serious. I was so excited when I read his message that I quickly replied that I really would like to meet him. Over the next week we made some plans for meeting in a local nightclub so we could see if we were as compatible as we seemed to be in the chat room. I was especially excited because he wanted me to dress as Josie. I spent quite a bit of time making sure I packed some nice feminine clothes that would make me as passable as possible. I didn't want him to be disappointed and I didn't want to embarrass myself. I chose a blond/grey wig that was age appropriate, a pair of woman's jeans and a nice blouse. I took with me a variety of panties and bras and stockings and a couple pair of high healed shoes. I also packed an assortment of toys just in case I would need them, as I always try to do. I even booked a motel room near the club just in case things went as I'd had hoped they would. I didn't want to invite him to the hotel I was staying at on business because of the fear of coworkers seeing me. And most importantly, I made sure to pick a motel that had smoking rooms, because we both smoked and we both shared an extreme smoking fetish. I also made sure to pack some sexy nighties and some naughty panties for the motel part of the date in case things went that way.
As I left for that trip, I was equally excited and nervous. I remember being so nervous that on my long layover, I went out and smoked about 6 cigarettes before getting on my second flight. When I arrived I made my first stop at the Motel 6 I had booked and staged the things I would need for my date there. Then I went to my business hotel and unpacked my man clothes and attended and afternoon of meetings. The date was that night. My coworkers always would ask me if I wanted to go out for dinner and maybe hit a bar or strip club and this week was no different. I declined as i normally did, but usually I was declining the invitation because I was wanting to get to my room, dress up like a gurl and hit the chat rooms for some late night fun. This night was different and they could sense it. One of my coworkers even asked my if I had a hot date or something. I laughed on the outside but inside I was tingling with excitement that he was right on the money. I called an Uber and made my way to the Motel 6 to get ready for my date. The Uber driver looked at me funny when she noticed I was going from a nice expensive hotel to a cheap motel. She even winked at me and told me she hoped my night would be fun. I giggled at her and went into my room and got ready. It took me a good hour and half to transform from businessman Joe to Josie. I kept stopping for a smoke break with my Misty 120s which would calm my nerves and, as usual, would make me feel more feminine. Finally it was time to make my way to the club. I had decided to go with a pair of my most trusted thongs, a matching bra, a pair of thigh high stockings, a loose fitting silky white blouse and the heals I was most comfortable moving around it, my 8-inch black platform block open toed heals. I made my face look as pretty as I am capable of, put on my shoulder length wig and some earrings a necklace and some bracelets and a silver woman's watch. Then I made the decision to put my clitty in a chastity cage and to plug my ass with a jeweled buttplug. When I called for the Uber driver I realized I was kind of screwed. Uber has my name and a picture on my profile. Damn! I quickly cancelled the ride and called a taxi instead.
I arrived at the club about 10 minutes late with dreadful sense that this was a big mistake and that Stan wasn't even going to be there. To my pleasure I found Stan waiting at the bar just as he said he would be. I was pleasantly surprised by his reaction of "Wow, is that you Josie?" and I think that same sense of relief that I felt that each of us had ACTUALLY showed up. We sat at the bar and aside from a few off looks from a few people that were giving me a good hard look over, the night went great. We grazed on a few apps and had lots of drinks. He was drinking bourbon just as he had told me he liked in the chat room and I drank a variety of pink and purple girly mixed drinks. We went outside for a few cigarettes while we were there. The fist time we went out we just continued to chat about all kinds of things. The second time, after a few drinks, the conversation started in the same direction our chat room conversations had went. The second trip to the smoking alley also involved some kissing and touching and a very close attention to the way we both smoked and the enjoyment that I got from him staring at me smoking. We kissed playfully before heading back inside for a few more drinks. By the time we went out for a third cigarette, I was stumbling a little and held onto him tightly as we made our way to the door. I was feeling very naughty at that point. We made out while we smoked and there was some very inappropriate public affection being displayed by both of us. As I finished my cigarette, I looked at him and said, "Let's get outa here!" He quickly finished his cigarette and quickly hailed a taxi. He asked if I wanted to go to another club or a park he knew of and I told him that I had gotten a smoking room at the Motel 6. His smile was big. "You naughty slut," he said. Hearing those words made me happy and he didn't hesitate to tell the taxi driver to take us to the Motel 6. We kissed and fondled each other for the 5 minute drive to the motel.
When we arrived at the motel, I held his arm as he helped me to the room. We stumbled in and Stan lit cigarette and then offered me a light as well. He noticed to stuff that I had laid out on the bed. Some sexy lingerie, some toys, a nightie, a fishnet body suit, a bottle of his favorite bourbon and a large variety of cigarettes. He took me in his arms, whispered "I love you" in my ear and started to kiss me. Through our chat sessions we both pretty much knew what each other liked and liked to do on a date. He told me he really needed to take a piss and winked at me and asked me if I cared to join him in the toilet. I smiled and nodded like a naughty school girl who just got asked to the prom. He dropped his pants and exposed his half hard cock that I'd seen pictures of and watched him jerk to an orgasm in our video chat. He motioned me to join him in the small shower. I started to take off my clothes and he stopped me. "No, you naughty whore, leave them on. I bit my lip and let him guide me to the shower where he guided me to a squatting position and began to piss all over me. I'd participated in toilet play before but never dressed. The feeling of his warm piss soaking my clothes was indescribable joy. I took a drag and looked into his eyes as he soaked my jeans and blouse in urine. I saw him smoking and in unison as he aimed his stream to my face I instinctively opened my mouth wide. I gargled his tasty piss and playfully spit it back at him. He responded by putting his cock between my lips and pissing down my throat. I happily swallowed it all. Soon I was sucking his cock. He occasionally would pull in from my mouth so I could take a drag and so he could slap me in the face with it. I was in heaven. Was this actually really happening to me? My head was spinning from the drinks I had at the bar but my body was responding to him with passion and lust. He slowly peeled away my soaked clothes until he noticed my caged clitty. "Very good girl" he responded as he flicked it with his fingers. I turned around and playfully shook my naked ass at him, teasing him and wanting him to discover my other secret I'd been enjoying all night. "You are such a fucking dirty slut" he said. He started slapping my ass playfully. He turned the water on in the shower and we made out while we washed the urine from my body and I would occasionally drop down and suck his cock to make sure he was staying fully erect. We dried off and he guided me to the bed and we picked out the outfit that I'd model for him. He picked a new pair of clean white thigh high stocking, my thin red see through nightie and my matching red heals. My wig and makeup had been ruined in the bathroom, so he asked me to wear the red middle of the back length red haired wig I'd laid out on the bed and retreated to the bathroom to freshen up my makeup and and get dressed. I was taking way too long for him and I could hear in his voice that he was growing impatient. Eventually, 3 cigarettes and 30 minutes later I emerged from the bathroom as fresh as could be. He didn't say a word, but his reactions said all that need to be said. He brought me to the bed, we both lit up cigarettes and we made out and I stroked him back to fully erect as he fondled and toyed with my anal plug. He knew from our chats that I loved to be talked dirty to. He did not disappoint me at all. "filthy whore" "cumslut" "sissy ******" "cocksucking bimbo" "naughty slut" "plugged cunt" "sissy slut" It all made me so fucking horny and eager to please him. Then he sprung something on me that we hadn't chatted about. He demanded that I call him Daddy. I'd never opened up to him about how much I loved this and I happily accepted his demand. "Yes Daddy," I replied. He made me put my long hair in piggy tails and I was now living out one of my biggest fantasies.The dirty talk continued with him saying things like, "I can't wait to fuck my slutty sissy princess" and "Daddy's going to make you his whore". He kept handing me cigarettes and demanding that I smoke, which I happily did. He was smoking too and the site of this man so fucking sexy smoking as we made out and teased each other. All I could reply with was "Yes Daddy" and "Please Daddy". He finally got to toying with my plugged ass and put me on all fours on the bed and started to try and pull it out. He must have been surprised by it's size because he said, "Holy shit princess, I knew you were a slut, but your cunt looks like it could take alot more then my 8 inch cock" he didn't even have to lube me up. He slipped his cock slowly inside of me as i moaned, "OH GOD DADDY, YES DADDY!" He was fucking me doggy style on the bed hard and deep, slamming the bed against the wall with each thrust. "God damn Josie, you fucking whore!" he screamed. "Oh God Daddy, MORE DADDY, FUCK ME HARDER DADDY." I could feel him adding fingers with his thick cock in my ass as i screamed for more. I was oozing cum from my caged clitty We were both making so much noise. I exploded with one of the best sissygasms I'd ever experenced and begged him not to ***************. At one point during this I noticed the room was completely filled with smoke and this made me feel so dirty and happy. I could feel his cock twitching and knew he as getting close. I started begging for his cum, "Please Daddy, cum for me" "I NEED your cum Daddy" In one quick movement, he grabbed me by the throat, spun me around and shoved his cock down my throat as he moaned and shot his jizz into my mouth and down my throat. I swallowed it all as he told me, "That's it my cumslut Princess, swallow all of Daddy's seed" We collapsed on the bed and lit the obligatory post orgasm cigarettes and cuddled on the bed. We both expressed how happy we had made each other and how we wished we could do this every day. We shared more and more fantasies we both had. I even sharewd with him how I'd love to be the sissy in the middle of a 5 guy gangbang. This went on for a couple more cigarettes until i finally passed out asleep in his arms.
I woke up with the light of the sun coming directly in the window. I quickly realized I was strapped down on the bed with belt and some pink furry handcuffs that I had packed. "what the fuck?" I muttered under my breath. i was very worried and frustrated. Mostly frustrated that I couldn't reach my cigarettes and lighter that were so close to me but unobtainable on the nightstand. "God Damn, what the fuck?" I said louder. Stan emerged from the bathroom smoking a cigarette and laughing at me. "What the fuck Stan, I think this is going a little too far!" "Come on Princess, doesn't it make you feel exactly how you want to feel?" he said. I had to admit, there was a part of me that was super fucking excited by this. "Could you at LEAST get me a cigarette?" "Sure Princess" he said, putting a Misty 120 between my lips and lighting it. I took a deep drag. That first morning cigarette has always been my favorite. He was running his fingers up and down my naked body, taking great pleasure at the way i squirmed when he pinched and pulled my nipples as i hungrily dragged on the cigarette dangling from my lips, ashes falling to my chest. "So Princess Josie, were you serious about the 5-guy gangbang?" I smiled and nodded. "But Daddy... I need to go to meetings today and be a man for my job... you have to let me go!" I pleaded. He took my now completely smoked cigarette from my lips and put another fresh one in it's place and lit it, "Thank you Daddy," I replied. "So here's what I think you should do Josie... I think you should call you boss and tell him you can't make it today... that you have a bug and a hurting tummy.... tell him that you are going to stay in your room and work through it" I watched as he paused to light himself a cigarette. "You are going to spend the day with your Daddy, OK, princess?" I thought briefly and when realizing I really didn't think I had a choice I nodded and told him, "Yes, of course Daddy" He had my phone and held it to my face to unlock it and asked me for my boss's name. I told him and he started to text him. He typed and typed and typed and finally I heard the 'sent message' noise from my phone. He put down the phone and started to uncuff from the bed.
The story of day #2 of my chat room buddy date will be coming soon. Thanks for reading.
About a week later, I get an email asking if I was still serious. I was so excited when I read his message that I quickly replied that I really would like to meet him. Over the next week we made some plans for meeting in a local nightclub so we could see if we were as compatible as we seemed to be in the chat room. I was especially excited because he wanted me to dress as Josie. I spent quite a bit of time making sure I packed some nice feminine clothes that would make me as passable as possible. I didn't want him to be disappointed and I didn't want to embarrass myself. I chose a blond/grey wig that was age appropriate, a pair of woman's jeans and a nice blouse. I took with me a variety of panties and bras and stockings and a couple pair of high healed shoes. I also packed an assortment of toys just in case I would need them, as I always try to do. I even booked a motel room near the club just in case things went as I'd had hoped they would. I didn't want to invite him to the hotel I was staying at on business because of the fear of coworkers seeing me. And most importantly, I made sure to pick a motel that had smoking rooms, because we both smoked and we both shared an extreme smoking fetish. I also made sure to pack some sexy nighties and some naughty panties for the motel part of the date in case things went that way.
As I left for that trip, I was equally excited and nervous. I remember being so nervous that on my long layover, I went out and smoked about 6 cigarettes before getting on my second flight. When I arrived I made my first stop at the Motel 6 I had booked and staged the things I would need for my date there. Then I went to my business hotel and unpacked my man clothes and attended and afternoon of meetings. The date was that night. My coworkers always would ask me if I wanted to go out for dinner and maybe hit a bar or strip club and this week was no different. I declined as i normally did, but usually I was declining the invitation because I was wanting to get to my room, dress up like a gurl and hit the chat rooms for some late night fun. This night was different and they could sense it. One of my coworkers even asked my if I had a hot date or something. I laughed on the outside but inside I was tingling with excitement that he was right on the money. I called an Uber and made my way to the Motel 6 to get ready for my date. The Uber driver looked at me funny when she noticed I was going from a nice expensive hotel to a cheap motel. She even winked at me and told me she hoped my night would be fun. I giggled at her and went into my room and got ready. It took me a good hour and half to transform from businessman Joe to Josie. I kept stopping for a smoke break with my Misty 120s which would calm my nerves and, as usual, would make me feel more feminine. Finally it was time to make my way to the club. I had decided to go with a pair of my most trusted thongs, a matching bra, a pair of thigh high stockings, a loose fitting silky white blouse and the heals I was most comfortable moving around it, my 8-inch black platform block open toed heals. I made my face look as pretty as I am capable of, put on my shoulder length wig and some earrings a necklace and some bracelets and a silver woman's watch. Then I made the decision to put my clitty in a chastity cage and to plug my ass with a jeweled buttplug. When I called for the Uber driver I realized I was kind of screwed. Uber has my name and a picture on my profile. Damn! I quickly cancelled the ride and called a taxi instead.
I arrived at the club about 10 minutes late with dreadful sense that this was a big mistake and that Stan wasn't even going to be there. To my pleasure I found Stan waiting at the bar just as he said he would be. I was pleasantly surprised by his reaction of "Wow, is that you Josie?" and I think that same sense of relief that I felt that each of us had ACTUALLY showed up. We sat at the bar and aside from a few off looks from a few people that were giving me a good hard look over, the night went great. We grazed on a few apps and had lots of drinks. He was drinking bourbon just as he had told me he liked in the chat room and I drank a variety of pink and purple girly mixed drinks. We went outside for a few cigarettes while we were there. The fist time we went out we just continued to chat about all kinds of things. The second time, after a few drinks, the conversation started in the same direction our chat room conversations had went. The second trip to the smoking alley also involved some kissing and touching and a very close attention to the way we both smoked and the enjoyment that I got from him staring at me smoking. We kissed playfully before heading back inside for a few more drinks. By the time we went out for a third cigarette, I was stumbling a little and held onto him tightly as we made our way to the door. I was feeling very naughty at that point. We made out while we smoked and there was some very inappropriate public affection being displayed by both of us. As I finished my cigarette, I looked at him and said, "Let's get outa here!" He quickly finished his cigarette and quickly hailed a taxi. He asked if I wanted to go to another club or a park he knew of and I told him that I had gotten a smoking room at the Motel 6. His smile was big. "You naughty slut," he said. Hearing those words made me happy and he didn't hesitate to tell the taxi driver to take us to the Motel 6. We kissed and fondled each other for the 5 minute drive to the motel.
When we arrived at the motel, I held his arm as he helped me to the room. We stumbled in and Stan lit cigarette and then offered me a light as well. He noticed to stuff that I had laid out on the bed. Some sexy lingerie, some toys, a nightie, a fishnet body suit, a bottle of his favorite bourbon and a large variety of cigarettes. He took me in his arms, whispered "I love you" in my ear and started to kiss me. Through our chat sessions we both pretty much knew what each other liked and liked to do on a date. He told me he really needed to take a piss and winked at me and asked me if I cared to join him in the toilet. I smiled and nodded like a naughty school girl who just got asked to the prom. He dropped his pants and exposed his half hard cock that I'd seen pictures of and watched him jerk to an orgasm in our video chat. He motioned me to join him in the small shower. I started to take off my clothes and he stopped me. "No, you naughty whore, leave them on. I bit my lip and let him guide me to the shower where he guided me to a squatting position and began to piss all over me. I'd participated in toilet play before but never dressed. The feeling of his warm piss soaking my clothes was indescribable joy. I took a drag and looked into his eyes as he soaked my jeans and blouse in urine. I saw him smoking and in unison as he aimed his stream to my face I instinctively opened my mouth wide. I gargled his tasty piss and playfully spit it back at him. He responded by putting his cock between my lips and pissing down my throat. I happily swallowed it all. Soon I was sucking his cock. He occasionally would pull in from my mouth so I could take a drag and so he could slap me in the face with it. I was in heaven. Was this actually really happening to me? My head was spinning from the drinks I had at the bar but my body was responding to him with passion and lust. He slowly peeled away my soaked clothes until he noticed my caged clitty. "Very good girl" he responded as he flicked it with his fingers. I turned around and playfully shook my naked ass at him, teasing him and wanting him to discover my other secret I'd been enjoying all night. "You are such a fucking dirty slut" he said. He started slapping my ass playfully. He turned the water on in the shower and we made out while we washed the urine from my body and I would occasionally drop down and suck his cock to make sure he was staying fully erect. We dried off and he guided me to the bed and we picked out the outfit that I'd model for him. He picked a new pair of clean white thigh high stocking, my thin red see through nightie and my matching red heals. My wig and makeup had been ruined in the bathroom, so he asked me to wear the red middle of the back length red haired wig I'd laid out on the bed and retreated to the bathroom to freshen up my makeup and and get dressed. I was taking way too long for him and I could hear in his voice that he was growing impatient. Eventually, 3 cigarettes and 30 minutes later I emerged from the bathroom as fresh as could be. He didn't say a word, but his reactions said all that need to be said. He brought me to the bed, we both lit up cigarettes and we made out and I stroked him back to fully erect as he fondled and toyed with my anal plug. He knew from our chats that I loved to be talked dirty to. He did not disappoint me at all. "filthy whore" "cumslut" "sissy ******" "cocksucking bimbo" "naughty slut" "plugged cunt" "sissy slut" It all made me so fucking horny and eager to please him. Then he sprung something on me that we hadn't chatted about. He demanded that I call him Daddy. I'd never opened up to him about how much I loved this and I happily accepted his demand. "Yes Daddy," I replied. He made me put my long hair in piggy tails and I was now living out one of my biggest fantasies.The dirty talk continued with him saying things like, "I can't wait to fuck my slutty sissy princess" and "Daddy's going to make you his whore". He kept handing me cigarettes and demanding that I smoke, which I happily did. He was smoking too and the site of this man so fucking sexy smoking as we made out and teased each other. All I could reply with was "Yes Daddy" and "Please Daddy". He finally got to toying with my plugged ass and put me on all fours on the bed and started to try and pull it out. He must have been surprised by it's size because he said, "Holy shit princess, I knew you were a slut, but your cunt looks like it could take alot more then my 8 inch cock" he didn't even have to lube me up. He slipped his cock slowly inside of me as i moaned, "OH GOD DADDY, YES DADDY!" He was fucking me doggy style on the bed hard and deep, slamming the bed against the wall with each thrust. "God damn Josie, you fucking whore!" he screamed. "Oh God Daddy, MORE DADDY, FUCK ME HARDER DADDY." I could feel him adding fingers with his thick cock in my ass as i screamed for more. I was oozing cum from my caged clitty We were both making so much noise. I exploded with one of the best sissygasms I'd ever experenced and begged him not to ***************. At one point during this I noticed the room was completely filled with smoke and this made me feel so dirty and happy. I could feel his cock twitching and knew he as getting close. I started begging for his cum, "Please Daddy, cum for me" "I NEED your cum Daddy" In one quick movement, he grabbed me by the throat, spun me around and shoved his cock down my throat as he moaned and shot his jizz into my mouth and down my throat. I swallowed it all as he told me, "That's it my cumslut Princess, swallow all of Daddy's seed" We collapsed on the bed and lit the obligatory post orgasm cigarettes and cuddled on the bed. We both expressed how happy we had made each other and how we wished we could do this every day. We shared more and more fantasies we both had. I even sharewd with him how I'd love to be the sissy in the middle of a 5 guy gangbang. This went on for a couple more cigarettes until i finally passed out asleep in his arms.
I woke up with the light of the sun coming directly in the window. I quickly realized I was strapped down on the bed with belt and some pink furry handcuffs that I had packed. "what the fuck?" I muttered under my breath. i was very worried and frustrated. Mostly frustrated that I couldn't reach my cigarettes and lighter that were so close to me but unobtainable on the nightstand. "God Damn, what the fuck?" I said louder. Stan emerged from the bathroom smoking a cigarette and laughing at me. "What the fuck Stan, I think this is going a little too far!" "Come on Princess, doesn't it make you feel exactly how you want to feel?" he said. I had to admit, there was a part of me that was super fucking excited by this. "Could you at LEAST get me a cigarette?" "Sure Princess" he said, putting a Misty 120 between my lips and lighting it. I took a deep drag. That first morning cigarette has always been my favorite. He was running his fingers up and down my naked body, taking great pleasure at the way i squirmed when he pinched and pulled my nipples as i hungrily dragged on the cigarette dangling from my lips, ashes falling to my chest. "So Princess Josie, were you serious about the 5-guy gangbang?" I smiled and nodded. "But Daddy... I need to go to meetings today and be a man for my job... you have to let me go!" I pleaded. He took my now completely smoked cigarette from my lips and put another fresh one in it's place and lit it, "Thank you Daddy," I replied. "So here's what I think you should do Josie... I think you should call you boss and tell him you can't make it today... that you have a bug and a hurting tummy.... tell him that you are going to stay in your room and work through it" I watched as he paused to light himself a cigarette. "You are going to spend the day with your Daddy, OK, princess?" I thought briefly and when realizing I really didn't think I had a choice I nodded and told him, "Yes, of course Daddy" He had my phone and held it to my face to unlock it and asked me for my boss's name. I told him and he started to text him. He typed and typed and typed and finally I heard the 'sent message' noise from my phone. He put down the phone and started to uncuff from the bed.
The story of day #2 of my chat room buddy date will be coming soon. Thanks for reading.
1 year ago
