My First Crossdresser

Monday

A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera. Now I had always be intrigued by crossdressers, and I myself was Bi-Curious, so I said Heyy. And I sat nervously waiting for a reply that came quickly. My cock sprung to life as started messaging each other, and then he asked if I wanted to come to his flat on the floor below. My heart pounding, my cock twitching, I quickly got changed, into black jeans, a t-shirt and a purple hoodie.

I went downstairs and knocked on the door. "Come in." I entered his flat, I was scared and nervous, but there he was, he wasn't dressed, he shock my hand, and we talked. At this point I was a little disappointed and horny. We just talked and bonded, talking about my degree and his passions. He then suggested we meet another day, I said Wednesday as I was free and wanted to enjoy my time. He then told me his name for himself as a girl was Leanne. His male name was Alec.

I went to my flat, my boner raging I undid my jeans and grabbed my dick, and started to pump horny, and blue balled. Looking forward to Wednesday. About one hour after I came, a message came up on grindr, he wanted to meet saying he was dressed, asking if I wanted to meet, I was so scared, but I wanted a new experience, so I said yes. I wanted to impress my interest, so I put on a pair of red see through panties, the only clothes that I own.

I went down to his flat I stared at his door wondering if I could go through with this. No one had ever seen me in my panties, and he was also not very experienced, both being Bi guys. I knocked, no answer, then I heard some shuffling and the door opened, just a tiny bit before Leanne opened it fully. I stood in awe of her. She was wearing fishnet stockings, a black dress, and purple wig. All I could say was "Wow, you're very attractive."

"So are you." And then we kissed, I melted into her, my dick and her bulging, I grabbed her and she was grabbing mine. Then we both realise that the door had remained open, we were both too excited so she closed it, we were both intoxicated with each other. She undid the zipper on my hoodie, and my belt buckle her hand brushing against my panties and my touching my dick. I was thinking can someone find me this attracted, and then she moaned my name Jay, I grabbed her cock through her underwear. Neither of us had impressive sizes, me being six inches, hers being five. She grabbed my hand and pulled me into the kitchen out of the hallway.

I was pulling my jeans down, she wanted to pull my panties down, but I wanted her to see them. Leanne I moaned, as my phone got chucked on the floor we didn't care. I was wearing nothing and she still not lost any clothes. I then pushed her onto the sofa. I sat on her lap kissing her, on her neck, worshipping her. Kissing her then I took of her dress and too her nipples in my mouth, my cock was straining against my panties. Leanne said "Wow nice panties." I was about to undo her cock, when I started to kiss her feet, I love the stockings. I then took her in my mouth my mouth feeling up her body as I could feel her in my mouth. I kept hearing her groan for me, as she came in my mouth. It was then my turn as I sat in the sofa as she took away my cock from my panties and when down on my me, I never had a blowjob like this. I came almost instantly, and violently. "I felt that." Leanne says.

We kiss and snog as I get up to find my clothes thrown throughout the flat, as I leave she waits by the door, and gives me a kiss that gets me twitching again, I knew I had to see her again

Friday

We have been messaging, but I was a virgin, and always imagined myself to be a bottom when it came to gay sex. So I asked her as she was a top, if she wanted to come up to my place, as I have a bed and we could spend some time together, yes she responded, as I clean my ass out to be prepared to entered for the first time.

I said it was ok for to come up, but wasn't dressed, instead she would be Alec. Even better for me. I put on the same pair of panties that I wore on Monday. With a long top over me, I wanted to feel like a girl. I open the door, and he comes in we kiss and move straight into the kitchen no playing around, this time. He took my top off quickly, my heart pounding, as my panties came off, I put them in the corner as I saw him take off his clothes, I grabbed my dick and began to rub it as we were both nude we headed for the bed snogging each other. He grabs the covers and pulls them over our bodies. Our tongues still battling each other. He grabs my dick with his hand and puts it with him and then starts grinding I moaned loudly not giving a shit about my neighbours. I could cum right now.

That's when he turns me on my side no lube, no condoms. I start to massage my dick. "Let me." He touches me. I can feel his finger pressing against my virgin hole. Massaging it. It enters, it feels weird yet relaxing, he tells me to relax as he removes his finger and slowly inserts his dick. I grunt, and he asks if I'm ok. I just moan, my dick is hard, as he enters me. He's feeling me out, pushing into me. I want him more. Just as I was hoping he would go faster he takes out his dick and gets into the missionary position, he re-enters me, his mouth on mine, my ass in the air I moan his name as I cum, as it oozes out of me. I then make him lie down, as I straddle him, slipping his dick into my now non-virgin ass as he groans, and finishes, we lie in each other. Sweat pouring down too tired to say anything. He then gets up and leaves, another kiss as he goes.

I couldn't stop thinking about him, but he never came back on grindr, until 4 months later. He also moved buildings the next week that we met. I was so excited when I saw him, messaging him, thinking about him. But he turned down my advances right away, leaving me with an experience I'll never forget.