Cross Dressing
13 Apr 2017


Previous story in series: When your Girlfriend discovers she is dating a cross dresser.

My first true experience as Samantha.

At the time I was living and working overseas. To the outside world I was just your normal 21 year old really skinny guy living and working and enjoying life on the islands. Of course I had my little secret which I kept hidden from my colleagues and friends. Although I wore panties a lot of the time, I did not own much else as far female attire for fear of being discovered.

It happened one evening while I was working in a restaurant doing a photo program for the resort I worked for. I was taking pics of all the families and couples when I came across this couple in what I guessed was their early fifties. We got chatting and the guy told me he was a professional photographer and we chatted about my work there. He said that I should pop around for a drink after work and he would show me a few things and give me some handy tips to help me. He gave me their address and I thanked him and said I would stop by if I had time since I was only due to finish around 11pm. He said not to stress as he would still be up and then I thanked him, having no intention of stopping by.

When I finished at about 11pm we, I decided to have a couple of drinks at the bar. I left the restaurant at about 12:30am, feeling a little tipsy and climbed into my car. I sat there for a couple of minutes debating with myself and then turned the car on and pulled out of the parking lot. Before I knew it I was driving in the direction of where the couple were staying which was not too far from where I stayed but definitely not the way I would have gone home. I was thinking I would just drive by and see. When I got to their apartments I pulled over and parked. I noticed that the top apartment still had lights on. I am not sure why I got out but I did. I just stood there and lit a ciggie and quietly smoked while looking at the apartment with the light on. I could see that the apartment number was the one they had given me.

The next thing I knew I was standing in front of the apartment and listening through the glass door. I could hear the TV and then I could hear movement from within. I was about to turn and leave, thinking this was really stupid but then suddenly I found myself gently knocking on the glass door. About 10 seconds later the curtain is moved to the side and standing there totally naked is the guy from the restaurant. I almost ran. Then he is opening the door and I immediately stammer that I am sorry it is so late and I should go and......... He stops me and says it is ok. He says he was just watching a movie and having a drink and he invites me in. He walks away and into the bedroom and then comes back into the lounge wearing a gown to my relief.

I tell him I was just driving by when I noticed the light was still on. He tells me it is perfectly fine as he is a night owl anyway. He offers me a drink and I happily accept. We sit and he turns the TV down and we just start chatting. He is from Denmark and we just chatted about South Africa as he had never met anyone from here. Then I ask if his wife is sleeping and he laughs and say that it was his sister with him at dinner and not too worry as she has her own apartment below his. I was not sure what to say to this and thought I should be on my way soon as I was really starting to feel the effects of all the alcohol. I said I should be going but he insisted that I have one more drink. He says he has some photos he has taken that he wants to show me and to give me some tips. So I agree to one more drink.

He fixes us both another drink and then he goes off to fetch his photos. He comes back holding a thick photo album. He sits down next to me and I immediate notice that his gown has come undone and I can see his you know what. I am not sure what to do so pretend I can’t see anything. I am sipping my drink and the first thing I notice about all the pics in his album is that they are all of young men. All the pics are taken of men either on a beach wearing speedos or in a studio by the look of it where the guys are either very well dressed or in just their underwear. He starts telling me about how he finds young men and then creates portfolios for them to then use for modelling etc. He looks at me and says he would love to take my pics. I am adamant that that will not be necessary as I have no intention of ever going into modelling. He says that it is okay but he would still just love to shoot some pics. All this time I could not stop myself from stealing some hidden peeks at his family jewels I suddenly need to use the loo and excuse myself.

When I close the door to the loo I just stand there, shaking a little. I know I am more than just a little tipsy now and that I should go but I have also realized something else. Here I am sitting with a man whose family jewels I cannot take my eyes off and I have just realized that I am so excited by this fact. I am also very aware that I am wearing panties and that they have become exceptionally wet without me even knowing. I use the toilet to relieve myself from the alcohol build up in my bladder. I decide that I should go out there, finish my drink and then politely leave.

When I walk back into the lounge there is Lars standing there with his camera in his hand. He smiles at me and says he knows that I did not want any pics taken but please can he just snap a few. I walk over, pick up my drink, take a sip and then look at him and say only a few. His joy is so evident. He starts positioning me and then steps back and starts snapping a few pics. Then he places my drink in my hand and takes a few more. Then he asks me to take off my shirt. I hesitate but he immediately assures me that it is fine and he won’t bite. Little did I realise the consequences of the simply removal of my shirt. After he has used the entire spool he stops to get another one. As a professional photographer he still uses spools as opposed to the newer technology of digital which was still fairly new. When he comes back I notice that his gown is now open and he is totally comfortable with it and has no intention of doing anything about it.

By now I can’t take my eyes off and I think he can see the effect he is having on me. He walks over and says to me. I want to photograph you in your underwear. I almost choked and said no way. He just smiled and said it was okay. I tried to tell him that I was different and that I felt embarrassed. He assures me that I have nothing to fear and then he drops the bomb shell. He says to me that if I am afraid because I am wearing ladies undies then I have nothing to fear. He must have seen the utter shock on my face and he says to me, that since I removed my shirt there is no longer anything to hide as he could now plainly see the frilly panty outline through my pants. The outline of frilly panties was so distinctive that not even the trained eye could miss the sexy little frilly panties I was wearing. In my inebriated state and with certain jewels on show, that thought had never even crossed my mind when I removed my shirt. “If you are going to wear ladies undies you should not wear white trousers that are in any way see through like yours are”, says Lars.

At the same time I was now also so damn excited but also so scared. Lars told me to just relax and sit and sip my drink for a while. I gulped it down and before I knew it there was another drink in my hand. Next Lars is taking my hand and making me stand. He bends down and removes my shoes, then stands in front of me and while telling me that it is all okay, he proceeds to slowly unbutton my trousers, unzip and then gently lets them fall to the floor. Then he slips them off my feet making me raise them one at a time, taking off my socks at the same time. Now I am standing there in all my glory. Wearing just a pair on cream silky and frilly lace little panties and nothing else. Lars proceeds to take another spool of pics of me in all sorts of poses.

By now I notice that something has changed with his family jewels. His cock is no longer just dangling there but instead is now looking more lively. I can’t seem to take my eyes off it and it seems to be growing by the second. It looks like it is standing at full attention now. I realize that I am also getting hard and that my panties are really getting wet. I have got my cock tucked in between my legs to hide my hardness and give me that real fem look. Somewhere I can hear Lars telling me how sexy I look and how pretty I am. Then I am back on the couch, sipping my drink again. Lars is next to me and then his hard cock is in my hand. I am stroking him, then his lips are on mine. My hormones are screaming in my head, his hand is between my legs. His tongue is in my mouth, this must stop but it feels so good. I want it but it feels so wrong. I am sitting on his lap, his cock pressing against my panties, kissing, fuck I am in heaven. He stands and takes me by the hand and leads me to the bedroom. I am on the bed, on my back, flashes from the camera, he is on top of me, I feel this sensation of cumming in my panties, the wetness, Lars hard cock in my mouth, feeling dizzy and............... At some stage I lose all memory.

When I wake up, it is with one of my worst hangovers. My head hurts like crazy, I am alone and naked. I can hear noises from the kitchen / lounge area. I eventually manage to get my head off the pillow. I can’t find any of my clothes, not even my panties. I find Lars’s gown and slip it on. I walk out into the lounge and who do I find, Lars’s sister Anna. I want to run and hide and she looks up and smiles and says good morning. I am not sure what to say as I finally manage a good morning back to her. Then she says that it sounds like I had a really good time last night. I must have blushed bright red and then asked where Lars was? She said he had just gone shopping and would be back in about an hour or so. I asked her if she had seen my clothes. She told me that Lars had sent them to be washed. God now I was feeling nervous. She offered me some coffee which I gladly accepted. But first I pop off to shower and then came back for my coffee. The first cup of coffee did little to alleviate my nervousness or my head ache.

While we sat drinking coffee we just chatted about the island and things to do and I was so relieved that she did not bring up last night. By my 2nd cup of coffee I started to feel a little better and then Lars arrived back carrying all his shopping bags. He walked in putting then down and smiled at me and asked how I slept. I told him I did not even remember falling asleep and he said that I just passed out. I mentioned my clothes and he just smiled at me and said he had taken care of it. After my coffee he takes me into the bedroom and empties the packets on to the bed that he has just brought back with him.

There lying on the bed is a dozen or so pairs of panties, some stockings and suspenders, a corset, a couple of really sexy bras, 2 mini skirts (1 white & 1 black) and 2 blouses, a pair of white satin almost see through shiny shorts and a pink vest that looks very feminine and a couple of other tops. I am just staring at everything and he tells me that he had to send my clothes to be washed, so he has bought me some things in the mean time. I am almost speechless but eventually I say to him that I cannot go out dressed like a girl. He tells me not to worry we won’t be going out much.

He selects some pink panties, the white shorts and pink vest and tells me to put these on and then to join him in the lounge. I do so and when I walk into the lounge he is sitting there with his sister. They both look and watch as I walk in. I am so embarrassed that his sister is there. He looks at her and says to her, “Didn’t I tell you how sexy he was?” She just looks at me and says to him. “Yes you were right but you mean she”. I am standing there and I am very aware that the white shorts do very little to hide the fact at all that I am wearing sexy pink little panties. In fact the shiny fabric of the shorts is enhancing the pink fabric of the panties and you can clearly see the frilly lace trim.

Lars then says to his sister that she should get her things together and I ask where they are going. He then says to me that we are all going to the beach. I tell him that he said we were not going anywhere and besides I don’t have anything to wear to the beach. He looks at me and says, “We know that.” But this is a special beach so don’t worry and we will be driving there so no one is going to see you anyway. Now I am so god damn nervous.

When we leave I run to the car hoping that no one can see me. They then drive to this beach, which I discover that unless you know where you are going, you will never find it as there are no signs and barely even a road. You eventually arrive at this beach that is so secluded and I notice that there is only one other couple about 100m down from where we are standing. Lars explains that it is a nudist beach and that the public does not know about it.

So there we are, Lars and his sister Anna strip down naked and lay out their towels and lay down. I am gob smacked and just look and eventually sit on my towel but fully clothed. Although there is only one other couple on the beach and I can hardly even see what they look like from there but I can see that they are naked too. Eventually Lars says to me that I should relax and undress. I eventually strip down to my panties but cannot go totally nude, so I end up lying there in my panties. I am lying between Lars and Anna.

Then Lars leans over and says to me. “I was telling Anna earlier about our evening. I hope you enjoyed it as much as I did.” I was not sure how much he had told her so I said that I had. He tells me how much he likes what we did together and especially how I sucked his cock the way he likes. Now I look at Anna but she is just lying there on her towel, eyes closed but with a smile on her face. I look back at Lars and now I see that he is touching his cock and he is semi hard. He continues to play with himself and he gets harder. Now he is rock hard and stroking while he is looking at me. His tongue is licking his lips and he leans over and kisses me. He takes my hand and next thing I know I am stroking him right there on the beach. Then he pulls away from kissing me and whispers in my ear that he wants me to suck his cock right now. He gently starts to lead my head down to his waiting cock. I change my position so that I can get at his cock better. I look down the beach to check on the other couple and they are not even looking in our direction.

Then his cock is in my mouth. He is holding my hair and guiding me very slowly. Moaning a little as I tease the head. Lots of licking and teasing just the head before taking his hard cock in my mouth. Then feeling a hand between my legs. Feeling my hardness in my panties. Concentrating on Lars’s cock and hearing his moans of pleasure and then realizing that it cannot possibly be his hand between my legs from his position. I stop long enough to look up and discover that it is in fact the hand of Anna that is touching me in my panties. Our eyes meet and she smiles at me. Fuck I realize I am in heaven and I go back to pleasuring Lars’s cock. It took about 10 min to make him explode. His cum all over my lips and face and his belly. I taste his cum.

By now I am so close to cumming in my panties from the attention of Anna. I turn over and face her. She leans over and starts to kiss me. Her hand now urgently fondling me in my panties as we kiss passionately. She takes my hand and places it between her legs and I discover that her pussy is fucking wet. I am fingering her, first with 1 finger and then with 2 fingers inside her pussy and then alternating between that and rubbing her clit. She suddenly tenses and cums so hard and makes so much noise I was convinced the people down the beach had heard her. It took me all of 30 seconds from that point to explode in my panties. Her hand continuing to stroke me in my panties and rub the oozing cum everywhere.

Then off for a swim and rinse in the sea to cleanse all the cum from my tingling body. We spent about 3 hours on the beach. After our first session there was just lots of touching and teasing that took place. Then it was time to leave for home. On the way back Lars says to me that we just need to make one quick stop. We are driving through the town and he stops outside a photo developing store. He gives me some money and the receipt and tells me to go and pick up the spools he dropped off in the morning, they still have photo labs to develop film. I tell him that there is no way I am going in there dressed like this. He tells me that if I don’t then he is going to make me walk back to the unit from there. I look at him and he is smiling and I realize that this is all a game and that I am actually enjoying it. So I look at the shop and see there are no other clients inside. So I quickly get out and almost run into the shop.

This young guy of about 25 comes to the counter and I give him the slip. I see how he is eyeing me up and down. There is no way he can miss the fact of what is hiding beneath my little silky white shorts. He comes back smiling and holding 3 envelopes of photos. He tells me how much it is and smiles at me as he asks if I would like to check them. I say noooooooooooooooooo as I am certain that I already know that they were the pics taken last night showing me in all my glory. And I am not sure if there are photos in there that I don’t remember. As it turns out later, there were some taken of me with a roaring hard-on sticking up and out the side of my panties along with a few of me sucking on a very hard Lars cock. So for the guy in the shop there was no hiding the fact of who I was. When I got back to the car both Lars and Anna are laughing at me and Lars says, “Good Girl”.

That night was spent at their unit. I was introduced to the rest of the clothing from the morning. I was made to dress up in white panties, whites stockings with suspenders, white bra and white mini skirt. Blue blouse and then the makeup and nails done by Anna. At that stage I used to have long hair that I wore in a pony tail, so it was easy for Anna to style it to bring out the real fem look. Then the surprise was the box that was placed in front of me once I was all dressed and made up. A pair of 5” high black strappy heels. I nearly had an orgasm right then and there. Then I was made to walk around the unit and out onto the balcony like that. Took quite some time to get used to the heels.

A couple of drinks later and then I was handed over to Anna for the balance of my transformation. I was taken into the bathroom where Anna had run a bath. I was helped to undress and then I was ordered into the tub. Anna then proceeded to remove all the hair from my not so hair legs. At first I tried to protest but without too much conviction as Anna proceeded to also shave me under my arms and to make sure that by the time I climbed out of the bath, all hair that defined me as a man had been removed and I now sported the perfect female body including a neat little triangular tuft of hair above my clitty cock. I instantly fell in love with my new look in the mirror.

We had dinner sitting out on the balcony that night. All through dinner I was asked how it felt to be a girl and how it made me feel. I could not get enough of how I was feeling and the reaction from both Lars and Anna. They were amazing and made sure that I never felt awkward at any stage. After dinner came drinks and then the fun really started. We ended up dancing and drinking and with lots of touching and teasing. First Lars, then Anna and then both together.

Before I knew what was going on we were sharing the kissing, then I had Lars’s cock in my mouth and Anna had mine in her mouth at the same time. She had my cock slipped out the side of my panties and she was giving me so much pleasure. I was moaning so much and all the while I had Lars’s hard cock in my mouth. Then Anna is pushing me onto my back and taking my hard cock and sitting on it. Her pussy is so damn wet and she starts to ride me. Then I feel Lars doing something to my pussy and next thing I know, his finger is up me and he starts to slowly work my tight pussy. By now Anna is really starting to ride and grind her pussy on my cock and I can hear her getting really close. I am going through the roof with a finger working my pussy and Anna working my cock with her pussy and suddenly I can’t hold back and with a little slutty scream I explode and this sets Anna off who must then have cum for a full minute or so. She was grinding so heavily on my cock I was worried she might hurt me.

Eventually we disentangle ourselves and just when I think I will never experience anything quite like that again, there is Lars with his hard-on standing and smiling at me. He kneels on the bed, pushes my legs up and back so that my knees are on my chest and he slowly enters my pussy. Very slowly he pushes into my pussy and I realize that my pussy is so damn wet too. I can’t even remember how it got so wet. He takes his time, very slowly fucking me and then Anna is back and she has got my cock in her hand and she is gently stroking. She leans down and starts to kiss me. Now I can feel myself getting hard again and can’t believe it as I have just cum.

This seemed to go on forever. I am not sure how long Lars spent slowly fucking me while Anna kissed and stroked my cock but I do remember this sensation starting to build and build in me. It was as if every nerve in my body was been touched and teased at the same time. It kept building and building, driving me to a place I never been before. I was now moaning like a real little slut and could feel Lars starting to move a little more frantic now. And then it happened. He exploded inside me and my whole body shook as I experienced an orgasm that started in my toes and exploded up my entire body and went on and on and on. I had no control what so ever and it went on even after Lars had pulled out. It took me at least 5 min to calm myself and collect myself before I even realized that both Lars and Anna were sitting there looking at me and smiling. Anna had a glass of water and was telling me to drink some.

It took another couple of minutes for her to explain to me what had just happened. My second orgasm was not with my cock cumming and exploding seamen everywhere but rather I had just experienced a true anal orgasm. She explained I had just experienced an orgasm as a girl would except with my anus and I thought she was joking but she went on to explain it to me and to explain that women can also experience an orgasm from anal sex. I just lay there exhausted trying to comprehend what had just happened. We all spent the night in the same bed that night. I slept like a baby.

I ended up spending 14 days and nights with Lars and Anna. Night 3 was the most daring and exciting of them all in that first week. After what had happened the previous night with the orgasm of the century, I was virtually putty in their hands and open to just about anything that they suggested.

So when the next day arrived and they told me that they were taking me out to a club that night, I pretended to argue for all of 2 seconds. We spent the day relaxing around the unit and the whole day was spent teasing me about how they were going to dress me and where they were taking me and how many people there were going to be. They kept saying that they also had another little surprise for the evening. No matter how much I begged or what I said they would not tell me.

We had an early dinner around 7pm and then I was told to go and shower and start getting ready. Anna came in and did my makeup and hair after the shower. Then I was told what to wear but I was told to leave the panties off. So there I am fully dressed and waiting for them to get themselves ready but no panties. I am thinking that they are going to take me out wearing no panties. I am already so hard and thinking I cannot go out like this. There is no way to hide my hard-on.

Then they are ready. To my relief Anna walks in with 2 pairs of panties. She says to me that I will be needing both. I look at her and ask why? She says I will soon find out. Then in walks Lars and he has his hands behind his back. He walks over to me and tells me turn around. He then says to me that I must bend over. I do as told. Then I feel him lift my skirt and then he is putting something up my pussy. He tells me then that he is putting a butt plug up my pussy. He has lubed it and it slides up my pussy easily. He tells me that he wants me to experience the same orgasm I had the night before and that this will help. Then he tells me to put the first pair of panties on. They are really tight. Anna explains that this is to keep the butt plug properly in place the whole night. Once they are on she pulls them up my crack like a thong to properly secure and wedge the butt plug up my pussy and hold it in place. Then I am told to put the second really sexy pair of panties on over the first. Now we are ready to go.

We arrive at the club. First thing I notice is that there are so many people. I am so scared but Lars and Anna are calming me and telling me that there are all kinds of different people at this club. They eventually get me out the car. We walk into this club and I realize that they are right. It is full, no one is staring at me and I notice there are guys dancing together, girls together and then just lots of people. I realize that the club is gay friendly. I get a few glances from guys as we make our way through to a table. We have to stand at this table as there are no chairs available but it is one of those tall tables anyway. Lars goes off to the bar and comes back with drinks. Soon we are just relaxing taking in the scene. Lars takes my hand and leads me onto the dance floor. We dance a little and then go back. I realize that nothing has happened and really start to relax and enjoy the experience. This is the first time I have been out in public fully dressed as Samantha.

We danced and partied for a good couple of hours. I even had a guy ask me to dance which I declined as I was so scared. The whole time we are there both Lars and Anna kept reminding me who I am and making sure that I was constantly kept aroused which was not difficult. Lars would stand next to me and often slip his hand under my skirt and have a quick feel. Eventually I was so wet that my precum had soaked through both the panties. Eventually at about 12am Lars leans over and says to me that it is time to start thinking about leaving but there is something we need to do first. I look at him questioningly. He comes and stands behind me and whispers in my ear to spread my legs a little. I do so and then I feel his hand under my skirt and then he is feeling me in my panties. While we are standing there looking at what is going on he starts to gently rub and fondle me in my panties. Anna seems to know what is going on and comes to stand on the other side of me. They start to talk across me, about me, as if I am not even there. She is asking him about how hard and wet I am in my panties. He is telling her exactly what he can feel. Between rubbing my hard clit in my wet panties he is gently applying pressure to the butt plug which I can feel deep inside me. She is asking if he thinks he can make me cum in my panties right there and then. He is telling her that is going to try. They keep talking about this little slut and whore and what they think and what they are going to do to her and guess what. Not even 5 minutes and Lars has me exploding in my panties as my knees go weak and I am forced to hold onto the table. I struggled so much to just hold it together so that other people did not see what had happened. Then Lars takes his hand and licks his fingers and then says it is now time we can leave.

We got back home at just after 1pm. This time it was straight to the room. My panties were not removed at all to make sure that the butt plug stayed where it was. There was lots of urgent kissing and touching and sucking. My cock was released out the side of my panties and Anna helped herself to an orgasm pretty much as she had the night before. It was decided that she would get the chance to milk my cock this time which she did with a great BJ. She lapped up every drop she could milk from me. I could not believe how easy it was for them to make me orgasm again so easily. I was then fed Lars’s cock to start working on. While I was doing this Anna went to work on my pussy. She removed both pairs of panties and very slowly started to work the butt plug in and out my pussy.

It did not take long to get me moaning and begging for more. Still they persisted with the teasing. Anna told Lars that I was already wet and now starting to get very wet on my own and that I would be ready soon. Lars then told me that we would not need to use any lube tonight as my pussy was now producing its own pussy juice for lube. I was not sure what he was talking about. I just wanted so badly to feel him inside me at that point. I was almost begging.

Then he was ready. This time he wanted me from behind on my knees. So there I was, on my knees and suddenly I feel Lars feeding his hard cock up my tight pussy. I was so wet that it was not sore at all as it had been before but he still took his time going very slowly until his entire cock was inside me. Then he really took his time and very slowly started to fuck me. Again Anna gave a helping hand and was stroking my cock. As before my whole body seemed to come alive and start to tingle. This time I knew what was coming but still I could not stop the sounds coming from me as my pleasure went higher and higher. Then Anna was under me sucking on my hard cock and I could feel Lars getting faster. This time the build up was slower for me and I knew when I was going to explode this time. I could feel it building and when I knew it was there I just let myself go. This time I knew I was having an anal (pussy) orgasm and allowed it to just take over my whole body. I collapsed afterward but unlike the previous night, I was able to lie there and really appreciate what had just happened. It was the most amazing time of my life up to that point.

The next day Anna Flew back to Denmark leaving Lars and I to spend the next 10 days together alone. Those 10 days would be some of my happiest ever. Lars taught me to accept and to embrace all that was Samantha. I became comfortable being dressed in my skirt and little girlie tops when the young cleaning lady came to clean. She would just smile at me and go about her chores and I no longer felt like I had to run and hide.

Lars and I spent a lot of time on the beach in those 10 days and did a fair amount of touring to remote and secluded parts of the island. He took me shopping and had me trying things on in the shops which was a new and very exciting experience for me. There was plenty of touching and caressing in the car trips and lots of yummy cum shared along the way. There were a number of romantic dinners with me out and about fully dressed. There were some stares and hushed conversations but mostly it was just the 2 of us totally enjoying each other’s company. Twice we visited the same night club we had been to with Anna where we danced and spent hours with lots of teasing which resulted in some mind blowing sex when we got back to his apartment. I had taken 2 weeks off work so was not worried about having to be up early each morning.

Lars spent a lot of time teaching me what he liked and more importantly for me was how to act and accept and to embrace Samantha. We would sometimes just spend a couple of hours just kissing, touching and teasing and the pleasures we would experience from this would sometimes surpass the act of just having sex. And then all too soon it was over. Lars was returning to Denmark. For me that experience was a defining moment in my life as Samantha was finally born and set free in a sense as she may never ever have been allowed to experience that side of herself had she not met Lars at that point in her life.

So a huge thank you goes out to you Lars and to you Anna. Kisses.

Next story in series: When your Girlfriend discovers she is dating a cross dresser.


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