1. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Hello everybody...

    I am neu here, I would like to share a lot of stories with you. The stories would be about feminization, cross dressing, being with shemales, being a shemale , wife domination, strapon stories and so on.

    English is my second language, so be easy on me ... I am Italian.

    When you like my stories I will go on with this post. And as I said, I have a lot to tell, some are real and some are wild imaginations.

    So I am waiting to see if you are interested, then I will begin
    • Like Like x 6
    1. u want it to
      Let's hear what you got
      u want it to, Oct 11, 2018
  2. knighthood

    knighthood Sex Lover

    Jan 22, 2015
    let's see what you got
  3. sharkbytenow

    sharkbytenow Sex Machine

    Oct 23, 2011
    Bring them on
    • Like Like x 1
  4. Trick01

    Trick01 Sex Lover

    Jul 24, 2018
    Tick tock
  5. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Well.. I think I can start with the first story..

    How it all started?

    I will tell you a little bit about me. I am a 35 years old man, white and a bit chubby with a regular sized penis and round woman shaped hips.

    I all started ten years ago. I was 25 and till that time I only tried regular things, had sex couple of times with ladies, and watched regular porn.

    Well. I was very very horny all the time, I had a lot of sexual energy, even when I had a girlfriend, she was never enough. I would always jerk off to porn, and till that age it was regular porn.

    And slowly that was becoming more and more boring for me, till one day I clicked a video of shemale fucking a man in the ass. The shemale was Mia Isabella. Oh that amazing big cock, I couldn't get enough. I watched that video three times and each time I would blow a huge load. I think I found what I was missing. Shemale porn is now my thing, the best is when a shemale with a big cock fucks a man with a smaller cock that is not even erected. It feels like she is taking his manhood away from him.

    I watched that everyday to the point that it felt weird when I saw a naked girl without a penis.

    And naturally I found the femdom and the cuckold videos. Well when you are down that road it would be impossible not to find them.

    And the hard thing was that I had sooner or later to face the question, who am I?

    I started to notice that I am a bit chubby guy with nice round hips that any woman would want, I looked at myself in the mirror when I was naked and I said, well you can make a nice shemale. I laughed at first but this idea kept haunting me, I could not resist it anymore.

    That is when I started to secretly dress up like a woman. I was not that hairy, I needed a little bit shaving and a little bit makeup with a nice black tight dress with nothing underneath. And here was I looking more feminine than most girls I know. I also bought a butt plug, a prostate stimulator, and nice pink dildo.

    I cleaned up my new pussy before trying my new toys, and I hat my first hands free prostate orgasm. I felt that I turned into a woman, it was amazing
    • Like Like x 5
  6. Loretta Roberson

    Loretta Roberson Porn Star

    Apr 21, 2018
    discovering yourself can be hard and being honest about it can be even harder....thank you for sharing
  7. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Well I am still discovering, but I am not afraid of who I am. If I like dick I will say so.
    • Like Like x 1
  8. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Are you ready for the next story?

    Its about my roommate finding out about me being a sissy.

    Well I have to explain. At that time I shared an apartment with a high school friend. He was a nice guy. He only knew me as a straight guy. I figured that he will sooner or later find out about me. I was hoping for later. But it didn't work that way. Well it was a small apartment. Fingerling and dildoing myself became boring. I needed a real cock..

    What should I do. I asked myself.

    Well shemale prostitutes were very expensive. Although it was a perfect thing for me.

    So I think I have to date guys now that are into sissy boys like myself. So I started looking online.

    I found the perfect guy after a lot of sexting and sending nudes. There were only one problem, it has to be in my place because he lives with a girlfriend. He was curious to find what it is like to be with a shemale. When I am dressed up, I look exactly like a shemale.

    So I picked a day where my roommate is supposed to be out of town, and I invited the guy over.

    He wanted me to wear make up and fake long blonde hair just like the pictures, and wait for him totally shaved and naked.

    Anal sex takes preparation, otherwise it would be messy and not fun. I think you know what I mean. I also jerked off blowing huge loads three times. I was very excited. That was also helpful for my feminine look, because my penis shrank to be less than one inch. I looked like a sissy bitch.

    In about 20 minutes he would arrive. I was shivering from excitement. I was blushing. Oh my God I want it so bad.

    As I seen in pictures the man had a thick long dick, and his body was also not bad.

    Nothing can go wrong now, I will have my first sissy experience in less than 15 minutes.

    Suddenly my roommate walks into the apartment. I must have miscalculated or something!!!!

    I was frozen, I can't explain that. He was also in shock, he didn't say anything, he just walked into his room. I put on a.rope and walked into his room. I said: I wanted to tell you about this. I am having a date today in about ten minutes. Please don't mess this up for me, this is my first time.

    He said: I saw you watching gay porn but I thought it is just a phase. Don't worry I am OK with it. You look pretty by the way.

    I was turning red as he said that. I said please keep it a secret for now. He said OK don't worry.

    The bell rang. I said that must be my date. I will take this to my room ok.

    I stripped naked again and welcomed my guest..

    Next time I will be telling you what happened on that date
    • Like Like x 1
  9. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    And now the guy was there. He was very nervous, I offered him a glass of wine to relax. He sat on the couch. I said that my roommate is there, we better move this to my room. He was OK with it. He wore a tight jeans an a nice white shirt. I could see his erect penis bulging in that jeans. We talked a little bit to break the ice. But the sexual tension was too high to talk a lot, I was also completely naked, in spite of my preparations my penis was hard again and dripping with precum. He stripped naked and started sucking my nipples. Oh God that felt great. Then he started kissing my lips, his tongue was so deep in my mouth. Then he went doun kissing my belly and then sucking my cock. I came in his mouth from excitement. I was very embarrassed by that. But it turned him on even more. He shouted: suck my dick baby. And I sucked his big thick cock, that was the best feeling ever.

    He told me to bend over, we noticed a sound behind the door. Omg !!!! That was my roommate jerking off...

    He asked if he can join us to just watch. I was not sure if I am OK with it. But my master said it is OK. So he stood there watching me bent over. My master wore a condom on his huge cock. He put some lubricant on his hand and smeared it on my asshole. I let a moan out. Then I felt his cock slowly penentrating me, that was the best feeling ever. He was gentle at first and in no time he was riding me so hard that I was screaming in pleasure. He started shouting take it you dirty shemale. I liked him talking dirty to me. My roommate was also enjoying the view. Now my master turned me on the back, spread my legs and started fucking me even harder. I came handsfree. He pulled out, took off his condom and started fucking my throat. In no time my mouth was dripping with cum. He fed me every drop that I spilled. We both laid down on the bed out of breath, then I felt another cock entering my asshole, Omg!!! That was my roommate, he started fucking me without a condom, I was in too much pleasure to refuse, my roommate had an even bigger dick, I could tell from the stretch feeling of my asshole. He was riding me so hard I nearly passed out. I came one more time. Then he pulled out an came on my belly. It was so messy, but amazing.

    My master was getting hard again. He wanted to ride me one more time. I pegged him to be easy on me, I was exhausted. But he was so excited to listen. He kept fucking and fucking for more than half an hour. At that time my roommate was fucking my throat. It started to hurt a little bit so we used more lube. This time he came inside of me. That warm felling of cum is unforgettable. And my roommate came in my mouth. Oh my God.

    We laid all three in bed moaning for ten minutes. Then we took a shower. And my guest left after giving me a kiss on the cheek....
    • Like Like x 3
  10. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Now is the weird part. How should we handle this?! Yesterday we were roommates
    , and now we had a fucking gay threesome.

    We must definitely talk about it. My roommate was a single guy, he was kind of a player with women. I think I am now one of his whores. I laughed thinking of that.

    We decided to pretend it never happened. In the next week's he braucht several girls over to our apartment.

    I think I was kind of jealous. It is very hard to explain why I felt that way. Anyway, pretending it never happened didn't work that well for both of us. I brought the same guy again couples of times to our apartment. And as much my roommate wanted to deny it, he was amazed by the way I look everytime I dressed up.

    One day he came to me and said: maybe we should not live together anymore. I know I am straight, but I keep finding myself wanting to sleep with you. I smiled and said: then do it. It would be our secret.

    So as that other guy disappeared and stopped replying to my texts. Till now I don't exactly know why. But that was a new beginning of me and my roommate long sexual relationship. It lasted over a year. He was not exclusive to me. But that was OK by me. It was not emotional. It was more sexual. And he wanted to convince himself that he is a straight guy with some special needs. He ended up getting engaged to a nice girl. I don't think he ever mentioned our little secret to her.

    He moved out of the apartment. So I was alone again. I started dating girls again, but secretly I kept dressing up. That was also easier now because I lived alone.

    It is me and the internet again. There were a phase were I didn't even know what I wanted sexually. I focused on my career. You can say I was sexless for about 8 months. I was almost ready to explode.

    I thought it is now time for a new sexual adventure. I had 2 weeks of. I decided to go to another town. I want to dress up in public. But not in my own town. So I was in hotel room for the next tow weeks. I went out in public wearing sexy woman's outfit, with high heels and sexy stocking. This time it was my natural hair. I was now a professional with make up.

    I went to a public bar looking like this. It took about 15 minutes for the first guy to buy me a drink. He wanted to take me to his place. I whispered to his ear: but I have a dick, is that OK ?

    I scared a couple of guys with this trick. It was hilarious. I felt that I am turning into a bitch. That felt kind of nice.

    It took a while before a man was thrilled to the idea that I have a surprise between my legs.

    He took me to his place. It turned out that he wanted me to fuck his ass. Well I did it. But it was not the best experience for me. He was very grateful. He even offered me money. I explained that I am not a hooker. I was a little offended. He said, with this body you can make a fortune. Actually, my friend wanted to do a gay party, and the main event is gangbang. I noticed that you wanted to get fucked, you are not very dominant. But you would be perfect for the party. And you can make some money if you will. I said : how many guys are we talking about?

    He said: about 5guys are active. And 10 will be probably watching and jerking off. Someone will take care of you before the party and dress you up. All you have to do is show up, suck, swallow and recurve dick.

    I said why don't u do it. U seem to like dick. He said the most guys are willing a ladyboy not a regular boy. And you seem perfect for it. I will also be offering myself there. But I am not suitable for the main event. Maybe a guy or toe will ride me. But the rest would be willing to ride someone like you.

    Oh my God what should I say. This is crazy even for me. But I decided to do it ...
    • Like Like x 3
  11. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    So the big day came..

    In about 4 hours the party starts. Jamie, the guy that I fucked last week, came to my hotel room to bring me to the event, it was supposed to be a preparation phase. I did my own preparation with ass cleaning, a little make up, and a sexy pink lingerie. I also put my chastity on. I am now more experienced. I can better control myself and my ejaculations.

    He arrived. As he saw me he was amazed. He said: I don't think u need much preperation. My cheecks turned red.
    I smiled and said, well this is not my first time.

    He took off my chastity and started sucking my dick. I said: save it for that party. He said: please fuck my ass again. We will make it quick. I said: OK, I guess.

    So we did it. I cleaned up and put my chastity on again. I was more interested in being fucked. Jamie loves also to get fucked. And by shemales.

    So we went to the place were that party should start in a few hours. It was a big nice apartment.

    Then a nice lady comes. She was tall with a very nice figure. She came with a sexy dress. Her body was perfect, except that she had relative small tits. I was a little embarrassed. I didn't expect a woman to prepare me.

    She said, hello I am Maria, I am Jamie's wife. I was shocked by that. I was turning red as she said : well take it easy man, I know you fucked my husband's ass, it seems to me that you like more being fucked. I nodded and as a tried to say something. She said: well let's see what you got.

    I put a sexy white dress and a jacket over that pink lingerie. I took them off, schowing my crotchless lingerie, and of course my chastity. She grabbed my caged penis and said: now I understand my husband's opsession about you. I said: but I don't stand a chance considering you as his wife. She said: we are open in our relationship, I knew that he loves dicks, therefore I am also allowed to bring other guys here. I have needs you to. I also fulfill his needs with my strapon collection. She smiled as she said that. Recently he wanted real dicks though. And you were not enough for him. He needs an alpha man. Not a sissy like u. Today he will be gangbanged. And I think you will be my treat. If you are a good girl, then you are also allowed to join the gangbang.

    She stripped completely naked. Then she braught a medium sized strapon, and put it on. I was totally amazed by herr look.

    I said: what about the preparation. She said you don't need any, you are more of a girl that I wished you to be.

    She told me to follow her to the bedroom, she tied me up there and went away for about half an hour....

    I heard her and Jamie fucking in the living room, then she came to me, sat on my face, and let a warm cum directly into my mouth. She said that's not Jamie's cum. This is Jack, my lover. Jack and Jamie joined in. Jack was completely naked with an amazing body and a hard thick dick. Jamie was also caged and dressed with women's lingerie.

    I was told to swap cum with Jamie as Jack was fucking Maria very hard she was screaming. Her strapon was still on. She had a very strong orgasm, so that she was shaking.

    She said, now is your turn sissies. She started fucking me and Jack started fucking Jamie. Oh my God I'm cumming.. Ohhhhhh.

    Jamie ate all my cum. Then I ate Jack's cum out of Jamie's ass.

    Maria looked at us and said: keep it up bitches. The party hasn't started yet....
    • Like Like x 4
  12. Captain_Assman

    Captain_Assman Sex Lover

    May 24, 2013
    very hot stuff ;)
    • Like Like x 1
  13. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    I was totally messy from all the jizz, I wanted to take a shower, so I did.

    My pink outfit was a total mess now, my make up needed fixing. After the shower Maria took a good care of me, I was looking perfectly clean and sexy again. Jamie and Jack also showered, probably together. I love the idea of a man and his wife sharing a cock. I said to myself, maybe one day I will be like Jamie, that's the dream.

    I was now totally naked. I only wore my penis cage. My hair never looked prettier, thanks to Maria. I will stay this way.

    The guests started coming, all of them normally dressed. The most of them showed interest in my naked body. But it was still a talking and drinking phase.

    Jamie was not looking bad either. But he doesn't stand a chance against me, I thought to myself, but I was clearly mistaken, he turned to be more of a slut that I ever expected. Looks are not everything in that game.

    Maria came and announced: well the game begins now, we have here to nice treats for you, one is my slutty husband, who would like to see some of you fuck me as he is being fucked, and the other is a nice femboy that I guarantee u you won't regret riding.
    The ones that are just going to to watch are also welcome, but they also have to strip naked, so let the game begin....

    Jamie didn't wait for someone to come to him, he rushed into the crowd and started sucking a punch of guys off. He was really good, they were very excited from his performance.

    He was literally stealing my thunder. As I started to get jealous, tow guys approached me, I started sucking one of them, the other was licking my asshole. In no time I was being fucked from both ends. There were aline in front of me, and a line behind me.

    One guy after the other fucked me in throat and in the ass. Then they gathered around me and started cumming, one after the other. I don't know how many loads I swallowed that night, well I thought for a moment there that this is crazy, I can't handle this anymore, this is too much, but then I saw the biggest cock I have ever seen in my life, and as I looked up I have seen boobs, what!!! A real shemale is here.. Maria whispered to me, you want that cock, don't you, I said hell yeah. She said then go get it. I was on my knees sucking her monster of a cock and pegging her to fuck me in the ass.

    She held me, threw me into a couch, spread my legs, and started stretching my hole with her amazing cock. Everybody was watching this. That got me very excited, Maria took off my chastity, my cock grew directly big, it was about to explode with cum. Jamie started sucking me, I came in his throat, he swallowed all of it. Then the shemale started fucking Jamie, he also came handsfree. She had a penis of steal, I think she can fuck all night. Only one can make her cum, Maria said, then she jumped on her cock and started bouncing. The shemale totally came in her pussy, Jamie and I were fighting to lick it off her pussy, so we shared it...

    Well that is most of what happened.... Now I must tell you about the days after the best day of my life......
    • Like Like x 2
  14. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Then I was back to my town, started working again after this 2 weeks holiday. A holiday that I will not forget my whole life, it kind of changed who I am, and I was OK with it.

    I started dating again, men and women, I was looking for the perfect woman, a woman like Maria, a woman who is so sexy and feminine, but yet dominant and willing to fuck, such women are extremely rare.

    I am also rare I think. Well there were always different phases, in some of them I was acting like a regular straight guy, in others I acted like a slutty girl. I don't want here to deny any fact about being gay, it is clear to me, I love dick, and I am comfortable with that, but I also love boobies and pussys. I am a lucky guy I guess. But I must say, when it is about emotion, I like girls, I am just sexually attracted to both.

    It is always good to discover how you feel and what you want, therefore I was looking for a woman that can understand all of that.

    I was in a couple of relationships that ended not well after I explained about my sexuality. I gave up on relationships and just started playing around. And as I said, sometimes as a man, sometimes as a femboy.

    As I write these stories my underpants get always wet with precum.

    One day I was feeling lonely. I entered a website for random video chat. I dressed up, put a mask on my face, and opened this video chat. And started seeing one man after another, most of them were stroking cock without showing their face. I had my dildo collection to play with and give these losers some good time. Then something amazing happened, one of them showed his face, oh my God it was John, my neighbor.

    John was a nice guy, he lived in the apartment next to me. I never thought he was gay, this thing is always a surprise, the media puts a lot of stereotypes on gay people. Then I thought of something crazy to do. I put a robe over my sexy dress. I knocked on his door, he opened the door after a while. I said, are you alone? He said yes. I came in, took my robe off, showing the tight short green dress. He was shocked looking at me. I saw his penis growing in his shorts. I said, both of us are horny and lonely, let us have some fun. He was not sure, he was totally embarrassed, he said you can not just knock on my door and ask me to fuck you, I took off his shorts as he was saying that and started sucking. Ohhhh that feels so good. I haven't had a cock in more than 4month. He laughed and said, OK you made your point. He was very hard. It took me 5 minutes of sucking to make him explode with cum. Oh that was a huge thick load, I ate every drop of it. He said oh my God you are a slutty sissy. That turned me on, I was also dripping with precum. Then he started sucking my cock, he was also very hungry. He sucked and sucked till he was hard again. He fucked me on the living room, doggy style, my favorite position.

    He was moaning loudly and taking dirty to me, I also blowed a huge load, I also ate my own cum, when I am turned on, I am the dirtiest sissy slut. He came again in my mouth. We took a shower together, fucked again in the shower..

    He looked at me and said. Well that is a game changer, knowing that there is a sissy whore next door, see you soon......
    • Like Like x 2
  15. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    My sexual affair with John lasted a few months. It was amazing to have him next door. We did it a couple of times every week.

    He was really amazing in bed. He knows exactly how to feed my ass pussy. I started making more effort to look sexier for him. He is a very good fucker. We talked also a lot about our sexuality. He was bisexual. He wanted to end up with a girl eventually. I told him that he will make his girl very happy. Ohhh the way he sucks on my nippels, the way he fingers me, the way he runs his tongue on my body, the way his cum tasted... And of course tye way he rides me. I felt every time with him that I want to be a girl forever. A naughty slutty girl knocking on his door every time she needs to be spanked and fucked. We did a lot of role playing. My favorite was the slutty schoolgirl.

    His dick was medium sized but he surely knew how to use it.

    Things ended with him as he had to move out of town. We decided to make our last time together amazing. And we did...

    I was wearing the sluttiest make up and jewelery and nothing else. We fucked all night in every possible position. I was filled from both ends with his delicious creamy cum....

    It was very sad that it has to end. But when something ends it is the opportunity for a new adventure, I told myself..

    A few weeks after that, I received a phone call that changed my life....
    Last edited: Oct 22, 2018
  16. luvtoget freaky

    luvtoget freaky Amateur

    Jun 10, 2016
    Damn!!! I had to rub one out reading this!! Great story!!
    • Like Like x 1
    1. Chrississy
      Thank you. It will get even better
      Chrississy, Oct 25, 2018
  17. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    The phone call...

    It was Maria calling me. You remember her. She is the amazing woman who opened my eyes of the world of female domination. When I am lonely, I still to this day jerk off to flashbacks from that amazing night that I had in her place.

    And she was calling me. What did she want. I answered the phone. She said that she is in my town and she wants to meet up with me. I tried to ask what she wants. She only said please we need to meet up. I would not say no to her.

    So we met. She looked a little bit nervous. I said: what brings you to my town. She said: I wanna talk to you about something and I am a little bit embarrassed. I said you can tell me anything.

    So she told me a long story about Jamie. Bottom line is that Jamie left her and she needs someone else for her events. You know her gangbang events. She was asking me if I could do it at least once a month.

    I told her that would be difficult since our towns are not that close and with my actual jobs I needed to work at most weekends.

    She understood that I couldn't do it. I asked her why are you in this town. She said, I wanted to see you and I was hoping to have some fun with you. Ever since that event she could not stop thinking about me, she said.

    Wow!!! I couldn't believe what I am hearing. That is amazing.

    What do you have in mind, I said.

    She explained about having a girlfriend in town who shared the same interest in doing sissy guys. She wants us to have a three way, where they do the fucking.

    I had a thousand questions. But I would not say no to such an offer.

    We dicided on date to meet up at this girl's place. Her name is Claudia.

    I was wearing sexy panties, pink chastity and a shiny butt plug.

    And I put normal guy clothes over them. I was feeling nervous again.

    I knocked on the door. And tow amazing girls were waiting on the other side with big strapon on. You know from previous stories how Maria looked like. Claudia was yet sexier. There is something about the way she looked at me. She had an evil amazing smile looking at my caged penis. She was also more wild and violent. She talked very dirty to me. I almost forgotten that Maria was there, and I could tell that she was a little bit jealous. I could tell because she started being more aggressive when she had turn to fuck me. It was an amazing experience for me. I was jumping on the strapon of Maria in reverse cowgirl position. Claudia was slapping me, squeezing my nipples, spitting on me and then she pulled me away and took over. I was laying on the back spreading my legs and melting from pleasure. I did not want it to stop. It felt amazing......
    • Like Like x 1
  18. Chrississy

    Chrississy Porn Surfer

    Oct 11, 2018
    Maria took my chastity off. She wore black gloves, started fingering me and jerking my cock. Claudia was sitting on my face letting me lick her nice pussy and asshole. I came in less than 3 minutes.

    I heard a knock on the the door. Claudia looked and me and said: now you get to see a real man fucking us you little sissy whore.

    And damn!! He was by every definition a real man. Very muscular with a thick long cock. My dick was starting to get hard again looking at his gorgeous body.

    Claudia laughed at me and said: look at your clitty growing by looking at a real cock. Do you want to suck it. I said yes please. She said your turn comes when we have enough, and when you are a good sissy boy.

    He took a quick look at me and then started making out with Claudia. The both girls were taking turns sucking his amazing cock.

    Then he started fucking claudia. That was amazing to look at her taking that cock. Then it was Maria's turn. This strong man was able to bring both girls into orgasm without cumming. Wow!!!

    Fuck my ass master, I shouted. He was not into that. What a loss!! Claudia started sucking him till he came all over her face and titties. She had amazing round titties with big pink nipples.

    I was allowed to clean up his load out of her titties and face. I swallowed all of it.

    That turned him on again. In less than 10 minutes he was hard again.

    What the hell, I will fuck you, he said.

    Oh thank you, please fuck me, I said.

    And damn he was a perfect fucker. My cock is dripping thinking about this.....