My first sex as a crossdresser

AUGUST 2021

Here it is, and I can't believe it myself. Very strange. My first sex with a man in women's clothes looked like this...

I have a profile on xhamster for a long time. And there I met various men. There were many opportunities for me to lose this virginity of mine, really great guys and opportunities, but you know when you're not ready, it's all in your head. Now when I think of certain men who were really great. But what was I going to do, I just couldn't and I didn't have the opportunity and strength to break it. I had an account once at the KZO (KLUB ZA ODRASLE) which means (CLUB FOR ADULTS) but it was the funniest thing now that I remember. I opened an account just to turn men on and for them to send me compliments and to watch dicks. Moron. But come on, don't hold grudges, and on this occasion I apologize to everyone who may have sincerely wanted me back then and I deceived them. I opened an account the other day there on KZO again. Now it's a little more serious, but I have no firm intention to get to know and meet someone so quickly, or try something. Friend requests was coming, I liked them, nice messages, nice offers...

But let's get to my butt ;)

He adds me. The one that will be the first. I won't talk about him, where he's from, or me, where I'm from, because of privacy and the agreement between him and me, because I respect everyone's privacy and life and I don't want to harm anyone, not even myself., it's not for me, I love life and I don't want to hold a grudge against anyone and cause harm.


He says on chat , " let's switch to mobile and WHUTS UP so that we can communicate more easily", because I told him that I'm from the same area where he is from. Believe me, I have never given my private number to someone from this kind of hook up sites, but I said let's try to see how it is with someone who is from my place, maybe we don't know each other? We will see how I will lock the messages so that no one can see them...

We start correspondence, I turn off the computer and devote myself to him because I liked the fact that he is very nice and from my place, so I said this will be exciting... We started typing around 2 in the morning and finished around 4. Forgive me if I spread the story a bit, I am not experienced in writing and I really liked what happened to me so I want to share it with you. So, I'm already a little more mentally stable in this my secret and I know that I want to try with someone, even if I jerk off to him.

I can't do it like this anymore, can t whait and think any more should I try or no.

I want to try and find out if I'm crazy or if I made up my mind that I am a trans woman and it will pass me by or that I want a dick and that I am a trans woman, that's what I wanted to see, do I want to repent, how is that? Try to jerk off and blow a man, just out of curiosity, but in the last year and maybe 2 (STORY WAS WRITTEN IN AUGUST 2021), I've been experiencing myself as a woman and putting on clothes and taking pictures of myself, watching porn of WOMAN WITH MAN, TWO MAN, THREE MAN, GANGBANG AND ALWAYS WHEN WATCH PORN I WAS IMAGINING THAT I M A WOMAN IN THAT SCENE ENJOYING WITH MEN. ALSO WATCHING MORE AND MORE CD, TS, FEMBOY, SISSY, and imagining that I'm one of them. a A WOMAN WITH A MAN.

And while I'm looking at it I feel beautiful and it excites me to try it and see if it's for me and if I can do it, do I want to? I realized that I wanted to and told him after a lot of messages and learning that I don't know him and he doesn't know me, that I want to see him and that we meet in complete discretion.

He was a cop. Police man. That night he work night shift and he wanted to meet.

I was scared and worried when I saw a man in a police uniform in the picture that he send me on whuts up, mostly because my own brother is a policeman and our town is very small and surely the policemen know each other, I didn't mention my brother's name so that he might not find out who I am, but I told the names of some of his colleagues and he told me that he didn't know any of them.

He convinced me. I told him that since we were going to meet in the dark, he should never turn on the light in the car and not ask us to look face each other. He was very nice and convinced me that everything would be fine, that he was not interested in anything but sex with me because he really liked me in the pictures.

"Come". I told him. I myself don't believe what I said, but I don't want to retract my word.

And we agreed, that he will come to the appointed place and time.

I don't know, just believe me, how to describe that moment when I have to go and meet with him, so I take a black skirt ( oh how mcuh preaty was that black skirt on me and her material), and a nice mesh blouse, orbit gum from the table and mobile phone and turn off the light in the room and go...Try to imagine what it was like in my stomach when I leave the house...my stomach is literally BURNING. I left wearing my men's shorts and T-shirt and went to where we agreed. ( APPOINTMENT WAS IN THE WOOD) behind my house around 50 m from my house, because I live in village). We was in contact all the time and I explain to him which street and where to turn his car to find me. I huffed in some bush in darkness and changed my clothes. I put on a black skirt and that blouse and hided in bush again. I was waiting for him to come. I hear a car, I said here it is. The stomach starts to growl again.

You know that thing you remember when you were little and your stomach churns when you have to go on a date as teenagers with him or her? AHH that feeling... So excited...

I see his headlights of car and I say in the message please just turn off the headlights when you get here...

He arrived in a police car dressed in a police uniform. He worked the night shift.

He turned off the headlights and came close to me. The engine turned off. I get up from that bush and walk towards him in the car in the passenger's seat and I think "will he like me" "has he seen my face?" I offered my hand and he said, "hi" "hi, how are you..." We chatted about something, believe me, I don't remember...and then he said he would do what we talked about through text messages, and he did.

He leaned back in the seat, pulled back, lay down and took off his pants and underpants...I saw his cock. I was under stress that no one would come by, because this is all happening in my place near my house, I was affraid noody will see me because that time I didnt have long hair like now, I was like a femboy, and I was spinning all the time looking around me if someone will see me, it was around 03:30 at night, and at one point my hand went towards him, I touched his dick...and now I sigh and leave without thinking, I just broke and started to kiss dick, I started blowjob...

The thought goes through my head "hey that's it, here you are, sucking cock, wow" Stress doesn't give me peace and I'm afraid that someone won't come by because I was nearby, not far from where I live... I continue to smoke his cock and he's already high. Nice dick. Thicker. A little bigger and clean, tidy. Beautiful, I said to myself and continue to blow and enjoy his dick. Even though I didn't know what I was doing and how I was blowing, I tried to remember those porn videos and how those women blow, and so I tried, then jerked off a bit, then I tried to swallow it but I couldn't, so I choked, and I was so confused I told him "I can't put the whole cock in my throat" then he says "don't worry, enjoy yourself, just relax, do whatever you want".

He was great to me, he relaxed me and told me to enjoy myself... I was crammed on my seat in my skirt, I was blowing him, and now he was putting his hand on my ass and caressing it like that over my skirt... It turned me on even more and I gave him a blow and lick him, then I lick his balls then I try to suck them, then I try swallow him whole and then I choke again...

And all the time I was confused and I couldn't mentally relax as much as possible, but I tried to enjoy myself and be relaxed... It was very nice somehow even though I was tense... Then he suggested that we try it. I said "I don't know if I'll be able to, I'm not sure, but I'd like to try" and so we agree to try as much as we can, if it doesn't work we'll stop. He gave me a condom and I put it on him, and smoked a little again, I got even more horny...

Then he went outside to his door, got out and told me to go out too, he open door of his seat and told me to go out but I was afraid that someone wouldn't see me even though it was dark. What I'm going to do is stronger than me, that fear of being caught. And he said that I don't have to go all out, only my legs, and the rest of my body inside, to be there on the seat, and that's what I did and I liked it, no one could see me , and even if he did, he wouldn't have seen the face, and he would have thought it was a woman, and that was it.

And so I relax and he starts to set me up... Oh, that feeling of his cock rolling around my ass, I don't believe I'm going to take it. And I wait, he pushes him slowly.. It hurts a little and he stops... He repeats it again and now he pushes the head, and I sigh and say slowly please, of course he continued slowly and was very careful and patient with me. And so little by little he enters me now and starts beating me, then it hurts me again, we stop, then he thrusts into him again and slowly beats me...He was pounding me like that and beating me slowly for a while...I was like in a dream.

Then I got turned on, so I started to twist, to thrust myself into him, hitting my butt against his body. I bent my legs, one in the knee, then I kneel on the seat with it, and then I put them together and like that, I remember how those chicks got in position, and so did I...Then I turned around to see how my ass looked like while it was pounding, and I saw those cloths on me, and it's like I'm looking as a woman...

I liked a lot how I look from behind in those clothes as a woman and with cock in my ass.

Then he put his finger in my mouth so I could blow him, mmmm uhhhh I blew his finger and he fuck me I enjoyed it, he has really good fucking me, it hurts a little bit but nothing terrible...

Then he pushed two fingers for me to blow and then he grabbed me around the stomach and fucked me like that, then he told to me "hey little one, should I cum in you or jerk off, but you know what, I have to be a little harder now, so I can cum, in the end I'm going to fuck you stronger and harder a little bit, if it hurts, then we will stop it." "Come on, I told him, do it and try, and if it hurts, we'll stop".

I wanted him to cum in the butt, because he had a condom, so why not, just how will it be, will the pounding hurt me a little more at the end? "It doesn't matter, I'll hold on, I guess" I say and he and I both laugh :) And so he fucked me now harder, I hear him sigh like a man, he's getting ready and at the end I hear him yelling loudly...

He squeezed my hips, squeezed them and he probably had no idea that he was squeezing me a little harder, but that squeezing turned me on even more and his strong beating...I suffered but it was nice for me, I wanted to endure him cumming in my ass to satisfy him with my ass, my role of being a woman turned me on and I felt like a woman all the time in all those clothes and having sex with a man that moment was my dream, all the time, that I was going to satisfy a man I enjoyed in that...

He was fucking me now harder and harder, and he was shouting louder and I was all turned on listening and waiting while he nailed me... At one point he stop , so stucked into me, and I said "uh, it's over" he said "yes, it's over" with a sigh...

Wow, I thought in myself, great, I'm so glad I satisfied him...

SMILE ON MY FACE :)
(Smile, because I felt so horny, fucked up on the driver seat in a wood at 04:00 in the morning, summer time, all dismantled my ass and my hips was wide open, and my hole stretched...) I WAS FEEL WONDERFUL.

He pulled it out cock and started to take off the condom... I straightened up and took my cell phone from the car, I was only looking to run away as soon as possible. it dawned on me that someone could see me, he smiled and said "don't worry baby everything will be fine" and as I was leaving I told him "I'll see you later, I'm sorry I have to go" and I didn't turn my face so he wouldn't see me, and I I saw that he was bald and big... I left and he greeted me and said "what's up little one, we'll see you again?" or something like that, honestly I don't remember, I took my t shirt and shorts and a little further on I squealed again to change my clothes and hide those women's cloths in a bag and hurried home.

I came home and sat on the bed... He left and texted me after a few minutes. "Was everything okay, little one?" I said, "yeah, great, thank you for being good to me and not being a crazy person, and it was everything's okay, I felt amazing"

I didn't expect a message as soon as I got home and I was very pleased that after about 10 minutes he texted me and asked how I was.

I was glad he turned out to be fair and correct towards me and more than enough. The only thing that mattered to me was that he was normal and that I returned home safely.

"Good night little one, sleep well"
"Good night you too"

I was thinking how am I going to sleep now after all this :)
I'm smiling and I can't believe what I've done...

But when he say "a little one" to me, calling me girly nicknames, I don't know what to tell you, feeling beautiful ;)

While I was siting in a chair after, I thought in myself, "hey you a man just fucked you, what you did"?

Then another thought came in my mind and that thought showed me picture when I was blowing his cock in a SKIRT and a picture when he was fucking me outside from behind, that picture in my mind, when I TURNED my head TO SEE HOW I LOOK FROM BEHIND IN THOSE DRESS AND I SAW MY BODY WAS SO GOOD IN THAT AND I FELT SATISFIED WHAT I SAW, me FUCKED like a woman and I realy felt like a WOMAN just in a short time. THAT PICTURE MAKE ME SMILE and I said to myself "CRAZY ONE" go to sleep :)