How I became a Sissy 01 by PiaSissy73

Well, it all started way back…I was 25 years of age…single by choice for about 4 years…and I was wild. I lived alone…went out 3-5 times a week and I changed girls at least once a week. I was young, carefree and I loved girls and women of all ages…I had young girls barely 16, I’ve had mature women around 40 to 50…and everything in between. Well, I enjoyed myself and I felt free like a bird. And that’s when I met Karmen. Well, actually I have seen her before. She was the girlfriend of one of the regulars at the bar where I sometimes sang and played the guitar. But that night I really noticed her for the first time. She was alone at the bar and she wore a long, floating, white summer dress. From the right angle and her standing in front of a light, the dress was just a little bit see through, so I was able to catch some split second glimpses of her slender body with that long legs, sexy hips and firm tits. With her long, blonde hair, she looked like a very sexy angel. I couldn’t take my eyes off her and of course she noticed it. Now as a rule I never went fishing at local waters, if you know what I mean, and especially I kept my fingers from already taken girls there. I just didn’t like the drama. It was much easier to go to a bar at another town, get a girl there and then go to a different town the next week. But I had no rule against looking and a little flirting. So I kept on enjoying her sexy appearance and we even smiled at each other across the room from time to time. Then I went to get another drink and suddenly she just stood next to me. „Do you like what you see?“ She asked. But the music was pretty loud so I turned to her and asked back: „Pardon!?“ She leaned nearer to my ear and said: „You can’t stop staring at me. So, do you like what you see?“ I answered: „I really like your dress!“ She started laughing. „Oh well, I think you are way more interested in what is underneath that dress!“ I looked at her and said: „Ya well, if you wear a dress like that, you should get used to guys staring and wondering what is underneath.“ With a sexy smile she answered. „Oh, I am used to it. In fact, I quite enjoy it. That’s the whole point in wearing that dress in this lighting.“ I laughed. „I like your attitude. You’re quite bold for a girl your age.“ I told her and she answered with that sexy smile again: „Well, I’m old enough to know what I want!“ I didn’t know exactly then, but she was just 19 at the time. „ So it seems!“ I said. She looked at me and said: “In fact, I am meeting a girlfriend tonight. We are going to a club. And I want you to join us!“ I hesitated a little bit, because it was against my own rules to mingle with someone from my home town. But I figured it’s not like a date, there’s gonna be her girlfriend, so it’s more like just going out as a group. And there was something in the way she said it, so confident, not as a question, almost as an order. I just couldn’t resist.

So I agreed, and half an hour later I sat next to her in her car. „You already had some drinks, so I am driving!“ she just stated and I really had no chance to disagree. We went to pick up her girlfriend and when we parked in front of the house she said: „Get out, she’s not ready yet. So, we’ll have a drink at her place until she gets dressed.“ So, we went upstairs to her girlfriend’s apartment. When the door opened I was a bit surprised. Her girlfriend was about 30-35 years old. Very attractive, with short black hair, beautiful, big, dark eyes and a heart melting smile. She was gorgeous, just not what I expected. She was not a girl…she was a woman! „Hey, come in you two.“ She said and Karmen introduced us when we sat down in the living room. „Listen, you two.“ Diana said. „I already had a little bit of champagne and I’m really not in the mood for a club tonight. What if we just stay here, have some drinks. I’ll put on some music and we have our own little party?” Again I was surprised by the turn of events, but again I had no saying in the matter because Karmen stood up, went over to Diana hugged her and said: „Great idea! I love our little parties!“ And then the two girlfriends kissed. And I mean they really kissed, long, deep and passionate. And while they were kissing, their hands explored each other’s bodies. I felt like I watched a really hot movie. Then Diana said: „Okay, if it’s a party, I’m gonna dress up appropriately of course. You two just get started. Karmen you know how to put on music, dim the lights, oh, and there’s champagne in the fridge.“ Then she disappeared, Karmen put on music, dimmed the lights and went to the kitchen. She came back with a bottle and three glasses and put it all on the table. I just sat there and couldn’t believe what happened. „Come here, I wanna dance.“ She said. Of course I stood up and went over to her. She was already moving her sexy body to the slow rhythm and I again couldn’t take my eyes off her. She stepped nearer and before I knew it, she pressed her body against mine, her hands caressing my back and we slow danced. Of course my own hands started to explore her slender body, too. She felt so good, so hot and my hands wandered up and down her back, then a little lower to her firm, juicy ass and I started to feel some movement in my cock. „Nothing!“ she suddenly said. And I asked „ What, nothing?“ She grabbed my face, put her lips close to my ear and whispered: „You are wondering, what I wear underneath that dress. It’s nothing…absolutely nothing!“ Now my cock was hard. And since she was rubbing her hot body against mine, she knew it…in fact, she felt it.“Oh, look at you two. Already in the mood!“ suddenly Diana said. We glanced at her and she looked breathtaking. She wore a really tight and short latex dress, long latex gloves and stood on extremely high heels, all in shiny black. Her dark hair was combed back with a lot of gel and with her really sexy make up and dark red lipstick, she looked like a model in a fetish magazine. „Oh, come on!“ Karmen said. „Now I will have to change, too. Or you are totally gonna out stage me here. Take over here, I’ll be back soon.“ Then she let go of me, left for the bedroom and before I knew it, Diana took her place, dancing with me. And she rubbed her body on mine just as tight and close as Karmen did seconds before. I felt like in heaven. Her body felt sensational in that smooth latex and I couldn’t help but caress and rub all over her back and ass. She did the same and my hard cock was rubbing against her thighs. I lost track of time, but suddenly Karmen re-entered the room in exactly the same outfit as Diana’s, only in red. She joined us and we danced in a little tight circle. I had one gorgeous, sexy latex goddess in each arm. Then Karmen and Diana started to kiss again…right in front of me. I watched their tongues explore each other’s lips and mouths. Suddenly they let go of each other and I felt Diana’s hot lips on mine…her tongue started a wild dance in my mouth. After a while it was Karmen’s hot and passionate kiss I felt. At some point we kinda kissed all three of us at once. „You should get rid of your clothes!“ Karmen suddenly said. „They don’t really fit in tonight’s ambient!“ Then the two latex goddesses started to undress me. And they didn’t stop until I was completely naked. Karmen then put her right latex hand between Diana’s legs and started to finger her pussy. Then she came to me and put her middle finger straight into my mouth. I smelled and tasted Diana’s pussy juice…it was heavenly. Then after fingering Karmen for a while, Diana did the same with her latex middle finger. The smell and taste of Karmen’s pussy was just as intoxicating and I fell in kind of a trance. Everything happened really fast, or maybe I just lost every sense of time and space. But suddenly I was lying on my back, Karmen sitting on my face and I was licking and sucking her juicy pussy. Diana meanwhile sat on my cock and started a wild ride. When I felt Karmen squirting all over my face in her first orgasm that night, I couldn’t hold back anymore and shot my sperm in Diana’s pussy. Diana then stood up, sat on the couch and spread her legs wide. Karmen crawled to her and started to eat out her pussy. She sucked all of my juice out of her and I watched fascinated, how Diana moaned and screamed in an everlasting orgasm. Then Karmen stood up and started to kiss Diana. And they started to swap the hot sperm, Karmen just sucked out of Diana’s pussy. Suddenly they stopped and both looked at me. „We share everything.“ Karmen said and I had a grin on my face. Then they stood up, came towards me and Karmen continued: „ Oh, I mean we all share everything.“ And then she gave me a long deep kiss, during which she let my sperm slowly pour into my mouth. That was the first time I tasted my own cum. And it wouldn’t be the last time. We fucked, sucked, licked, kissed all night long and in all combinations. And we shared all of our juices a few times more. At some point we just fell asleep. The next morning, after a good shower and a little breakfast, Karmen drove me back to my car. „You did well.“ She said. „I might consider letting you join us again!“ I was speechless and still tried to wrap my head around what happened the previous night. „Call me tonight at eight.“ She said. „I’ll decide until then! Now get out, I need to go home and get some more sleep!“ So I got out of her car. She drove away and I just stood there. I leaned against my own car and lit a cigarette. As I was standing there in kind of a dream state trying to get a clear head, I suddenly heard a voice: „She’s not for you, you know!“ I turned around and saw her boyfriend, or former boyfriend. Well, I actually wasn’t sure, if she is still with him or not. I said: „What? Who? What, did you say?“ He looked at me with kind of a desperate look. „You can have every girl you like. I’ve seen you, changing girls like underwear. She’s gonna break you. Better stay away from her!“ Then he turned around and disappeared. Well, that was weird. I finished my cigarette and drove home. I wasn’t sure what to do, I just tried to relax, watch some TV. Just having a lazy Sunday. But images from last night just kept popping in my head and I started to smile. „Wow, that really happened!“ I said to myself. I mean, I had some great nights with other girls, but that was a whole other level. And I had the chance to do it again. I had to call her. That was simply too good to miss out on it. But then I remembered the guy. „She’s gonna break you!“ he said. What the hell was that supposed to mean? I thought about it and figured he was just jealous. She left him, he didn’t take it well and now he’s trying to get her back, or something. Well, I even understood him. Who would wanna lose a girl like her? If he had, what I had last night on a regular basis, then he would be crazy to just let it go. Well, he tried, but he couldn’t scare me off. At eight that night I called her. But she didn’t answer the phone. I tried again a little later and then again, but she didn’t answer. I tried again the next day and the day after, but still no answer. So, I figured she moved on. It was a fun night, thank you, next! Hmm, it felt strange to be on the receiving end of such a treatment. I mean, I’ve done exactly the same like a million times. So, I said to myself: „Don’t be a pussy. She moved on, so you move on. Everything is cool.“ I decided to go out on Thursday. You know, new week, new girl. Back to business as usual. But somehow it didn’t work out as planned. I mean, I went out, I found a girl, she was sweet and sexy and really into me. But while I was talking to her at the bar, I couldn’t help but think about Karmen. I took the girl home and fucked her. „Hey, I wanna come in your mouth!“ I said while I was taking doggy style. „Ya, okay!“ she answered breathlessly. And then I said: „But don’t swallow it, keep it in your mouth. I wanna share the cum with you.“ She seemed to be confused: „What do you mean, share it with me?“ she asked and I said: „You know, kissing and swapping the cum from mouth to mouth.“ In a split second she stood up and looked at me in disgust: „What are you? A freak? …. Or are you gay? Why would you wanna get cum in your mouth?“ I laughed and said: „Well, why do you take cum in your mouth?“ She almost screamed :“ Ya, but I’m a girl! Are you a girl? Or are you gay? Only girls and gays do that. And freaks!“ Then she started to grab her clothes, put them on and stormed out of my apartment. I didn’t go out that weekend; I just wasn’t in the mood. Another week later on Saturday my phone rang. It was Karmen. I answered and just wanted to start asking her, why she didn’t answer my calls. But she just said: „ Be at the bar tonight! Or better, wait in front of the bar at 9 p.m.!“ Then she hung up. Of course I was waiting as ordered, she picked me up, we went to Diana’s place and had another great party. During the next two month we spent almost every night together. Some with Diana, some at clubs, where we met other girls and took them home, but most just the two of us alone at my place. At some point I realized, that she kind of lived with me. It was great. Without really talking about it, we were in a relationship. In a very open and hot one, but in a relationship.