[TM] first time meeting with a guy when crossdressing

Hey all. I’m a first time poster so on this sub so please be patient with me. This is the true story of my first time getting fucked and also my first story I have written.

So some backstory. I’ve really liked crossdressing ever since I was young. I stopped for a long time but have recently picked it back up again and now I can’t stop. Started playing with toys, plugs, dildos but it never quite satisfied me. I needed the real thing so here is how it happened.

I was away for work so luckily I had a hotel room all to myself. Obviously because of this I took all my girly clothes and toys with me. After work my colleagues wanted to head out for some drinks but all I could think about was getting back to the hotel and getting dressed up to play with my toys. After more drinks than I should have had we ended up calling it a night and I headed back to my room very drunk but excited get dressed up.

I wanted to do it properly so I got myself all shaved, painted my nails, did my makeup (not very well) and put on my favourite black thong bodysuit, fishnet tights, wig and my super high heels. At this point I didn’t think that my toys would satisfy my enough so I put my plug inside me and decided to do something I had never done, go on grindr and see what it was like. I set up my profile and added a picture. Within minutes I had messages flying at me all asking where I was and what I was looking for, suddenly a profile stood out at me, it was a curious straight guy who wanted to dom a sissy/cross dresser. We talked for a while and he sent me a picture of his cock which was a nice 7inches and uncut. I decided right there and then that I had to have it.

So after talking for a little bit more and discussing what we both wanted to do I decided to invite him over . I gave him my hotel and room number and asked him what he wanted me to wear and gave him a choice of outfits. I had to change out of my bodysuit as my cock my leaking so much precum it was everywhere. He chose my nylon black stockings with a small Lacey black thong, my heels with a pink bodysuit. I slipped a black dress over it all to finish of my look. I slipped my plug out and put a bigger one in to get ready. I was so nervous at this point but he messaged me and said he would be 10 minutes so I told him the door would be open and to come in and make himself comfy. I went into the bathroom and waited. It felt like an a lifetime waiting but suddenly I Heard the door open and someone call out my name, I said hey and told him to sit down in the chair in the corner of the room. After a minute I took a deep breath and came out the bathroom and looked over. I couldn’t believe there was a stranger in my room and I was going to suck his cock !
He looked over at me and told my how hot I looked. He stood up and grabbed me on my hips and brought me in close to him. I couldn’t help but reach down and feel the massive bulge in his jeans. He told me to immediately get down on my knees. I couldn’t Believe this was actually happening after having fantasies for so long. I got down on my knees and undid his jeans and pulled them down to reveal a tight pair of pants with a massive bulge which was leaking precum. I had to see it so I pulled down his pants and out popped a shiny 7 inch uncut fairly thick veiny cock. It was dripping with pre cum. He sat down on the chair and I grabbed the base of his cock and started to slowly stroke it, I put my head over the tip and licked it, it tasted so sweet so I took the head in my mouth which made him moan and he grabbed the back of my head and pushed it down onto his cock. It immediately hit he back of my throat and I gagged. I loved it so I went straight back onto it. I was bobbing my head up and down trying to make it as sloppy and possible and I could tell he was loving every minute of it. He had his hands on the back of my head and he was pushing it faster and harder down onto his cock. He told me to get on the bed and lean my head back over the side so he could fuck my face. I did exactly what he said, I took my dress off so I was just in my panties, stockings, bodysuit and heels. He grabbed my ass as I jumped onto the bed and I turned over leaning my head back. He stuck his cock straight in and started thrusting it deep into my throat. It was so sloppy and wet that I had spit and precum dripping all down my face. He continued to fuck my face moaning all the time about how good it felt. Then he pulled it out and told me to turn over and get on all fours so I did this. he pulled my pants down and grabbed my plug and slowly slipped it out revealing my gaping asshole just waiting to be fucked, I felt him slip a finger in and then another one. He grabbed the lube and started rubbing it all over his cock and my asshole. Suddenly I felt the tip of his cock touch my ass and he pressed it against it and started to slowly push until the head was in. It was a tight fit as I only normally use dildos but after adding some more lube he was in. It hurt a little at first but after a couple of minutes he started to speed up his pace and it started to feel amazing whilst he was pounding me. I had avoided touching my own cock the entire time but now he was inside me I couldn’t help it. I was absolutely rock hard and I had never had so much precum dripping out of me before. The feeling of a real cock inside me was just amazing. He Pulled out and asked me to turn over he got on top of my and pressed his cock against mine and rubbed them together then slipped it down pushed it back inside my asshole. He continued to pound my hole and then he asked me to go on top. So I told him to sit back on the chair that he was on earlier whilst I lowered myself back down onto his hard cock. I was riding him like I had practised on my dildo. It felt so good and he was moaning whilst grabbing my hips. I keep riding and riding. He suddenly told me to stop or he was going to cum so I hopped off and told him I wanted him to cum in my mouth. He stood up and pushed my down onto my Knees with my back against the wall so I couldn’t go anywhere. He grabbed the base of his cock and shoved it in my mouth and started to fuck my face again. All the time he was moaning and I could hear his breathing getting heavier. Suddenly whilst his cock was the back of my throat I felt him tense up and then a splurt of hot cum went straight down my throat and then another and atleast another 6 more. I could hardly swallow it all and half of it burst out my mouth and dripped onto my own cock that was rock hard between my legs. He slowly pushed it back in and out twitching after having such a massive cum shot. He stepped back and looked at me on the floor covered it cum, spit and lube. He got dressed said thanks and left straight away not saying another word. I sat there for a while thinking about what had happened and started to stroke my own cock still covered in his cum which I used for lube. I put my legs up over my head and shot my load into my own mouth. I had the one of the best orgasms I have ever had in my life thinking about what had just happened.

So I hoped you like the story. This is all true. Would love to know what you all thought in the comments.

Source: reddit.com/r/gonewildstories/comments/jwfew3/tm_first_time_meeting_with_a_guy_when