First Sissy Experience

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First Sissy ExperienceI accepted a new job in an executive role at a company in Kansas City and obviously with the new job came a new home and new neighbors. My wife and I were really excited to move into a very nice upscale neighborhood, we looked forward to getting “plugged into” our new community as well as get to know our new neighbors. What I could never had imagined is what “plugged into” would mean for me.We moved into our new home the first week of September and were warmly welcomed by the neighborhood with several couples stopping by to get to know us and offer to show us the best places for shopping, dinner and entertainment. We were really happy to meet couples our own age as well as several couples in their early thirties whom were just starting their young families. My wife and I are high school sweethearts, both just having reached 50 years old this past year. With the k**ds out of the house, we have been empty nesters for the past 5 years which allows more sexual freedom at home which has allowed for experimenting and talking openly about our sexual fantasies with each other as well as the possibility of bringing others into our bedroom. Having been married so young, neither of us had a chance to play the field or have other partners when we were young so we decided to explore swinger sites and found there are plenty of great swinger clubs in the KC area.We experimented by swapping with another couple at their home with the plan to live out one of my wife’s deepest fantasies of being with another woman. My wife is a sweet little vixen, five feet tall, 130 pounds with beautiful C cups and an ass that is any man or woman’s dream. As I watched my wife Ann go down on Christine (her new found friend) visions of what was to come could only be imagined. Fast forward to the first week of October and we are settled into our new home and have regular conversations with our friends in the cul-de-sac’ or in our yard. During one of the conversations our neighbor Kevin mentioned there’s a guys poker night on the last Friday of every month and wanted to know if I would like to join the group. I admitted I hadn’t played much poker in my life, but was certainly game if they would teach me along the way. Kevin said they would be gentle and we agreed to connect Halloween night for my first poker night with the guys.Halloween night we stuck with the tradition we formed after our k**ds moved out. We dressed up in costumes and drank while and handed out candy to the k**ds in the neighborhood. This Halloween we flipped the script with Ann dressing up as a man, specifically a prince, with me dressing up as a princess. Ann always shops and picks out the costumes and this year she went further than ever with the details. I was feeling good and loose from the liquor I had been drinking for the past couple of hours; in between handing out candy my wife and I were talking dirty and fantasizing about letting her take control in the bedroom while I was dressed as a woman. We had never done something like this before and I was intrigued by both her enthusiasm and my growing hard-on as I wore a pair of sheer lacy panties she had bought to make me feel the part of a princess.My outfit was more of a sexy princess than that of a Disney princess. I wore a light blue dress cut just above the knee with white thigh high stockings and a pair of three inch heels that were covered in silver glitter. I wore a short brown wig that really made my blue eyes pop. My wife went all out getting me into costume with fake eye lashes, press on nails, perfume and lipstick. In order to really get me to look the part she promised to swallow my load after the Trick-or-Treating was done if I would shave my legs, arms and cock. In the 30 years we have been married I could count on one hand how many times she swallowed so a little shaving certainly wasn’t going to stand in the way of a blowjob where I could cum down her sexy throat. While we were handing out candy our neighbor Kevin and his wife Sofie stopped by to remind me poker night was tonight at burdur escort his house with a eight pm starting time, he mentioned their k**s were staying over at friends house, but due to the late start we should just wear our costumes.I pointed out what I was wearing and said I would change, but Kevin was insistent that he would keep his pirate costume on and that I wear my costume because of the timeline to get started. He k**dingly rubbed and slapped my ass and said having a princess at the table would be a first. I certainly didn’t feel comfortable going to play poker with the guys dressed as a princess, but as Ann turned off the outside light to signify we were done with handing out candy she said it’s already almost eight o’clock and I should just head next door now while she and Sofie have a glass of wine at our place. Sofie gladly accepted Ann’s invite and Kevin and I headed next door. As I started walking across the lawn, Kevin asked if I could grab a bottle of Kentucky Bourbon from my place we had sipped on a few weeks back. I turned around to retrieve a bottle and he shouted after me to just come on down to the basement as the guys were already starting to arrive.I walked across the yard and back into my house and ran down to the basement bar and grabbed a couple of bottles of bourbon as I headed toward the front door I heard talking from our upstairs bedroom. I quietly walked up the stairs and found our bedroom door slightly open and peeked inside, to my surprise Ann was in an embrace with Sofie with both of their hands exploring each others bodies. I stood there watching as my wife starting sucking the young thirty something housewife’s breasts as I took a couple of swigs from the bottle of liquor, before I knew what I was doing I had my skirt pulled up and was stroking my six inch cock through my white lacy panties. I was torn between staying and watching my wife live her fantasies out with Sofie or going next door to play poker. Realizing we have a Ring camera in our bedroom I knew I would be able to see the escapade later, feeling really buzzed between the liquor and the sight of my wife with a very sexy woman I reluctantly headed back over to Kevin’s. As I walked into Kevin’s house I could hear conversations in the basement so I headed straight downstairs. As I walked into the room I was welcomed with cat calls and whistles. I blushed in embarrassment and hurried over to take a seat so the guys wouldn’t be able to get a really good look at my entire costume. Before I could sit down Kevin said hold on a minute princess, you need to show the guys your sexy costume. I looked him in the eyes and saw a look of a man in charge and he said I mean it, show them your outfit! I spun around to show my dress off and as I did the material caught a little wind and my skirt came up enough to show off my sheer lacy panties. Kevin reached out and grabbed my arm and said wait a second princess, are you shaved? I blushed and said yes I was, but before I could tell him Ann had enticed me to shave in exchange for a blowjob Kevin had already grabbed the elastic band on the front of my panties and pulled them down to expose my half hard cock. As I looked down to see my panties firmly in Kevin’s grip I noticed my half hard cock was resting across the top of his hand and my precum was freely leaking on him due to the excitement I had just witnessed between Ann and Sofie. Kevin looked up at me with his I am in control eyes and said the sissy likes being dressed up as girl, looks like you like being a sissy don’t you. I don’t know if it was the alcohol or just being so horny after seeing his wife half naked, but I just stood there in my outfit not saying a word. Kevin let my panties go, I felt the material from my satin dress fall to cover my semi-hard cock that was now partially protruding from my lace panties. Kevin put his hand out in front of him about waist high and ordered I lick the precum off his hand. I felt my body spiraling out of control and without caution I dropped to my knees and starting licking escort burdur the top of his hand. As I ran my tongue across his hand he said I have a better use for that sissy mouth and he stood up and undid his belt. For that moment I was absolutely scared to death and excited to the point that my cock was straining to be released from my panties. As I looked down I could see my precum was starting to soak through my satin dress.As Kevin put his cock to my lips I could not contain my tongue from slipping out to explore the head of his cock. He looked around the table and told the other four men that we have a little sissy that wants to be used. His words were burning into my brain……. his wife says this is a fantasy of his and we are all about to make it come true for the little sissy whore. As I licked Kevin’s cock he told me Ann had shared my fantasy with Sofie over a few glasses of wine a few weeks ago and the guys had all agreed that they would make my fantasy come true. Kevin stated I would not be allowed to tell anyone no regardless of what they wanted of me – tonight I was going to be a sissy whore for the first time in my life and if I was any good this would be my job every month to service the poker club. As my brain fought with how I was raised and what I really wanted at my deepest core I opened my mouth and let Kevin’s seven inch cock slide deep into my mouth. For the first time in my life I was sucking a mans cock, the smell of his cock was exhilarating! He had spent part of the evening walking around in a costume that didn’t allow for much air flow so there was a kind of manly musky smell that permeated my brain. The taste of his cock was like nothing I could have imagined; salty and sweaty yet something about it made me loose my mind into ecstasy. As I sucked his cock he grabbed the back of my head and started saying take it deep sissy! Show your new daddy how much his little girl likes to suck cock. All I could think about was that I was on my knees in front of five men sucking cock dressed like a princess and couldn’t wait to see what they were going to do with me. As I sucked Kevin I felt my hand being directed to another cock, as I looked up I noticed it was another neighbor named Bill. Bill is 62 and in pretty good shape for his age, his cock was much shorter than Kevin’s. Bill’s cock was thicker than Kevin’s, but only about four and half inches long. As I looked up at Bill with a mouth full of Kevin’s cock Bill ordered me to stroke his cock. Only a second later Mike was standing in front of me with his cock in his hand pointing it toward my mouth. I looked toward my daddy Kevin and his eyes said I was allowed to suck Mike so I released Kevin’s cock and took a hold of Mike’s six inch cock. Mike’s cock was leaking precum as I stroked it, as I looked up into his eyes he knew he too owned me and he said start sucking you little princess. I sucked Mike for about three or four minutes before he grabbed the back of my head and started face fucking me like I was a back alley crack whore. As I tried to pull back from his cock he only pushed my face harder into his groin, as I gasped to get a breath of air he started shooting his load deep down the back of my throat. As his hips slowed their bucking against my face I pulled about half his cock from my mouth, Mike was still shooting stream after stream and even though I did my best to swallow it cum started pouring from my mouth onto my satin dress and my stocking covered knees.Before I could gain my composure Bill was pushing his cock into my abused mouth and after about 30 seconds pulled out and came all over my face and wig. He gently pulled me to my feet and pulled my dress over my head leaving me standing in 3 inch high heels, white thigh highs and white lacy panties and a white bra. He looked at me and said you are a beautiful little cock sucking sissy princess that I can’t wait to help break in! My mind immediately went into overdrive! What did he say, what did he mean?Before I could wrap my mind around what he said Kevin was standing burdur escort bayan in front of me, he kissed me deeply and said time for your next lesson sissy. Kevin pushed me back down to my knees and stood over me. I looked up at him waiting to be told what to do, he stepped up to me and started tea bagging me. I licked his musky balls as he pulled them up out of the way and pushed my head toward his asshole. I have never eaten a woman’s ass let alone a mans, but obviously no wasn’t an option at this point.As my tongue explored Kevin’s ass he was moaning and calling me a dirty fucking sissy whore. I was in heaven wearing women’s lingerie licking a mans ass after just swallowing my first load of cum. As I was lost in heaven I felt a hand free my cock from my lace panties. With my face still buried in Kevin’s ass I couldn’t look at who was stroking my cock, but I could hear another familiar neighborhood voice. This time it was Carl’s, Carl is a black man whom lives across the street from me. Carl stroked my cock for a few minutes and then abruptly stopped. As Kevin stepped away I felt myself being lifted up as though I were a rag doll. I opened my eyes and noticed the event was being recorded on several cell phones, but at the moment I didn’t care! I was so turned on I would not have stopped if this were a live feed on the ten o’clock news! I looked around and noticed it was Kevin and Mike pulling me to my feet. Kevin turned me around and bent me over the table, he pulled my sissy panties down to my knees and before I could respond he had spit on my asshole and started rubbing his thumb up and down over my tight pink virgin asshole. I was feeling good having Carl resume stroking my cock as Kevin pushed his thumb into my tight asshole. I let out a gasp as Kevin’s thumb entered into my ass, but my body could not be denied. I felt myself push back against Kevin’s thumb which was all he needed to see to know nothing was off limits… including my virgin ass.I felt Kevin’s hot spit running down the crack of my ass and then I could feel his cock sliding up and down my crack before he started to push against my asshole. He told me to exhale and relax, I let out a breath and he pushed his seven inches in like he’d been there before. To explain the pleasure and pain all happening at once is futile, all I can say is I wanted to be his sissy whore with all my being. As Kevin plowed into my ass Carl released my cock and turned my face sideways so I could suck him off. I was in pure ecstasy being owned by two men at once. With a fat eight inch cock in my mouth and a seven inch cock in my ass, without even touching my cock, I started shooting my cum onto the tile floor. As I was cuming, Kevin started groaning and his hips bucked a final time before he started shooting load after load into my ass. Before I could gain composure I felt Carl entering where Kevin had just exited. The thickness of Carl’s cock was so big I let out a moan that everyone in the room knew could only be pure pleasure! As Carl slammed my backdoor Kevin stepped in front of me and grabbed my cheeks and forced my mouth open to give me ass to mouth. He ordered me to clean daddy’s cock off like a good sissy! As I sucked his dirty cock I felt Carl explode in my ass which caused me to gasp around Kevin’s cock which to my surprise caused him to come again!As Carl pulled out he ordered me to lick my cum off the floor, I did as I was told and was then ordered to pose for pictures. While wearing only my wig, high heels, bra and thigh highs I was made to wait on the poker players bringing them beers, bourbon and snacks while sucking cock and letting them all take turns abusing my ass as they chose. I was told I am to be back monthly, but as their sissy princess servant.After two of the guys left at eleven pm I was ordered to give Kevin, Bill and Carl one last blowjob and then take Kevin and Bill’s cocks up my ass before I was dismissed a little after midnight….. until the next poker game. I walked the walk of shame crossing Kevin’s yard as I walked to my house covered in cum, wearing only three inch heels, a brunette wig, a pair of white thigh highs and a bra while carrying my cum covered sissy dress….. I realized this was the best night of my life. I am truly a sissy princess cock sucker!

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