My first cross dressing experience led to my first gay experience [MM]

This happened quite a few years ago when I was 19. Up until this event, I was pretty bi-curious but, coming from a small country village, didn’t have the means or ability to explore that curiosity. This happened my first year at uni.

I’d done my best from starting at Uni to be a social butterfly. I accepted any and all invites to party, spent probably far too much time in the pub and I made a lot of friends. There was one, we’ll call him Rick, who I was especially enamoured with. He was tall, muscly, with a little chin beard and long hair. We struck up a great friendship but I never had the courage to tell him just how attracted to him I was. I, for the sake of comparison, was a clear 6 inches shorter than him, rather slim and basically his exact opposite.

When Halloween came round, he was hosting a party with his flat mates. Within our group of friends we all discussed at length in the pub the costumes we could wear that would stand us the greatest chance of getting laid. It was all a bit juvenile, looking back. One of them was planning on dressing as a footballer, another was going to try and be a wrestler (the undertaker, I think), none of them were greatly imaginative. I was worse though, I couldn’t think of anything and it was stressing me out. One of the lads said something along the lines of “if you’re gonna be a big girl about it just fucking wear a dress”, which got a big laugh. Except for Rick, who just smiled.

It might have been the drink, but it gave me an idea.

The next day, after I got over my hangover, the thought of wearing a dress to impress Rick remained. I couldn’t shake it and, quite frankly, it got me excited.

I went into town and went clothes shopping. I found a dress I liked. It was a slim fitting, strappy red dress with a short skirt. It hugged my figure and, even through it felt weird to sneak into the changing rooms to try it on, it felt really great against my skin.

That night I was chatting on IRC with a group of online friends who were all bi or bicurious. I told them about the dress and my idea. They suggested I take it up a step and really put the effort in. For Rick. They suggested that I speak to one of my female friends, be open and ask for some help.

I was nervous, but it made sense. A couple of days later I was having a drink with Ellie, a student from my class, and I chickened out. Well, I didn’t tell her that I wanted to impress Rick, or that I was into guys, but I told her about my costume idea and asked if she could help with makeup and such. She agreed and also told me to find a wig, which she could style for me. She told me to go to her place before the party and she would make me over.

The day of the party came and I arrived at Ellie’s place, dress and wig in hand (I’d found a blonde wig in a charity shop). She told me to change into the dress, which I did. I was nervous to show her, but when I did, she laughed uproariously. I was annoyed, but she said that I made a terrible woman. She pointed out that I was still wearing my boxer shorts, which were just visible under the hem of the dress and my dick, while not massive, was prominently visible under the dress. She asked if I wanted to do it properly, and thinking of Rick, I nodded. She asked if I trusted her, which I said I did.

She walked over to me, lifted the dress to reveal my grey boxers, then whipped them down. I leaped back to try and cover my dick but she told me to just calm down, she was going to help. She went into the next room for a moment and returned with some scotch tape. She told me to think unsexy thoughts, before grabbing my dick and pushing it between my legs. She then taped it flat underneath me, which is a sensation I was not expecting, nor was comfortable. I complained about the discomfort to which she replied “welcome to being a woman”. When she finished with the tape she said that if I wanted to do it properly, I needed proper underwear. She went to her dresser and retrieved a pair of red, lacy panties and a matching bra. I slipped into them and they felt great, though the bra sat weirdly on me. She stuffed the cups with tissue paper. She also warned me that she expected them returned to her. Washed. I agreed. She redressed me and then sat me down at her dressing table.

Over the next hour she gave me a full face of makeup. Smoky eyes, blusher, red lipstick, mascara and eyeliner. She then put the wig on me, straightened it, and styled it into a cute updo, held in place with a pair of chopsticks (it’s how she normally styled her hair). I didn’t recognise myself when I looked in the mirror. She joked that I had a great face to work with and that I made a good girl.

For the final touch, she retrieved a pair of strappy heels from her wardrobe. They were a touch tight on me, but they fit. When I stood up I nearly fell flat on my face. She gave me a brief introduction to walking in heels then said I was ready to go. I called a taxi and thanked her profusely.

Half an hour later, I was at Rick’s front door, nervous as fuck but committed. I’d already gone this far, I wasn’t going to chicken out. I knocked on the door and he answered. He was dressed as a Roman centurion and he looked amazing. He didn’t recognise me at first and asked what I wanted. I said “Rick, it’s me” and he nearly fell over. He smiled from ear to ear and ushered me in.

It had taken so long to get ready that the party was already in full swing. I caught most of the male attention when I walked in and I must admit, i really enjoyed it. Rick said I needed to catch up, so he poured me three shots of vodka and I downed them all.

Most of the party was uneventful. A couple of guys tried to hit on me, until I opened my mouth and they realised I was a guy. I kept noticing Rick noticing me throughout.

As the party began to wind down, I was quite drunk. His flat mates had all pulled and were busy in their rooms with their respective conquests. I was in the kitchen pouring myself a drink when I felt a hand on my ass. I turned to see a slightly drunk Rick, feeling me up. I immediately felt butterflies in my stomach. He whispered in my ear that I looked very sexy. I told him he was drunk, to which he replied that didn’t change that I looked sexy. My taped up cock immediately started to pulse. I started to say something flirty but Rick shut me up by kissing me. His tongue jumped into my mouth and his arms wrapped around me, I just melted into his arms. He took my hand and led me through the wastrels of the party and to his bedroom.

He locked the door and kissed me again. I could feel his cock pressing against my stomach through his tunic. As we kissed he took off the plastic centurion armour and lifted the skirt bit of his tunic (apologies, I don’t know what it’s actually called). I reached forward and grabbed his thick bulge. He asked if I wanted it. I was completely entranced (and a little drunk), I didn’t say a word. Instead I got down to my knees and pulled his boxers down. His meaty cock looked so good. I couldn’t believe I was staring at a real life cock for the first time. My mouth watered, I wanted it. I grabbed it and greedily wrapped my lips around it.

I tried to remember everything I’d ever seen in gay porn. I sucked hard and ran my lips up and down his shaft while wanking him with the same rhythm. He seemed to like it, he was moaning. He placed a hand on the back of my head and forced me further down onto his cock. I gagged, but I did my best to keep sucking, only releasing for air when I absolutely had to. I was in heaven. Even the tape tearing away from my skin as my cock hardened didn’t distract me from giving the object of my desires a blow job.

After a few minutes, he pulled me off his cock, lifted me off and kissed me again. “Bend over”, he said. I was elated. I reminded him that I’m a guy, and his friend and asked if he really wanted to fuck me. He said yes, and repeated how sexy he thought I was.

I climbed onto his bed and he lifted the bottom of the dress up, then pulled Ellie’s panties down far enough to expose my asshole, but he didn’t pull them off completely. He placed his cock in my ass crack and humped me. It felt amazing. I was so turned on. Then he pushed his large bellend against my asshole and I immediately felt pain. I moved away and asked if he had any lube. He said he didn’t, but he had an idea.

He spat directly into my asshole and I yelped slightly. It felt so weird. Then he slid a finger into my ring, which didn’t hurt, but felt so strange. Not in a bad way, just unexpected I guess. When he was satisfied he returned his cock to my hole and pushed again, this time slowly. It still hurt like hell, but the spit and his finger made it more palatable.

I grunted as he started to fuck me. It was really painful, but then my ass got used to his cock and began to relax, with pain giving way to pleasure. I’d never had anything in my ass before and his cock was not what you’d call a starter dick. It felt like he was going to tear me in half, but I was loving every second of it.

I pushed back onto his cock and told him to stop being gentle and just fuck me. He didn’t have to be told twice and he began to pound my ass. I moaned and grunted, occasionally screaming, as he fucked me like a little slut.

It didn’t take long at all before his cock hitting my prostate caused me to cum. My cock had worked itself completely free from the tuck job Ellie had done and I filled the front of the panties with my cum.

He began to grunt harder and I felt his cock swell in my ass. Without any warning he came, deep inside me. I nearly came again feeling his hot seed filling me up. After a moment of perfect stillness, I felt him slide out of my hole and he collapsed on the bed next to me. We kissed deeply again and we both fell asleep in each other’s arms.

I slept the deepest sleep of my life. In the morning, I woke up and he was still asleep. I borrowed one of his hoodies and a pair of sweats, changed out of the now soiled dress and underwear and called a taxi to take me home.

He called me later that day to say he had an amazing time with me and asked if we could go for a drink, just us. I ended up dating Rick for a couple of years through Uni. I also began to explore cross dressing, which I still do to this day.

Source: reddit.com/r/gonewildstories/comments/fc3akt/my_first_cross_dressing_experience_led_to_my