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This story is fairly short. I was looking for my first guy to be an average size circumcised cock but I wanted a girly man. I got a lot of replies. Lots of cross dressers. Sissies and other types. Too cunfusing for an older curious guy. Is no one else slightly older and confused by all the terms? Fuck! I sure am. It's true. I do like what they call sissies closet fem dressers but god there's a specific title? I'm okay with a guy wearing panties and a bra. It's my kink.
I kinda was looking for an average cock, not some huge whopper. A nice 5-6" with a nice head to play with. All I wanted to do was suck him off. What a fucken nightmare. I met three guys at one bar. They came in not knowing about each other. I sent two away. The final one I told him if he liked me, lets go. He smiled. Perfect. He was girlie but not dressed girlie. Maybe a little. Womens eyeliner. When I followed him I noticed he had a really nice ass and hips like a woman.
As we walked I told him he had a great ass. He says, that's what I hear. It's just the way I'm built. We got to my car. He moved the bottom of his shorts aside and pulled them up. It revealed his cock. He asked if he could pull his shorts off. By all means. Go ahead. He shrugged his shorts off. He said, you're really going to suck my cock? I nodded. He said god I've been wanting this for years. I sucked his soft supple cock. It swelled and the precum coated my tongue. He came very quick, sorta premature. It was a small load and super sticky. I swallowed it and it was just what I'd fanatasized about. Perfect. He wanted to kiss me. That wasn't part of my fantasy but we did, it was okay actually, he was a good kisser and it felt like kissing any girl. Then he returned the favour and sucked my cock ell. It really was mind blowing. Not as intense as the rush when he came in my mouth but seeing my cum in his mouth, and watching the smile on his face as he swallowed was super hot. My cum was on the edges of his mouth and on his chin. He got out and looked back. We should do this again sometime, I love you. Cute but he was a cock to suck. I told him I'd be in touch.
I didn't contact him. I realized I like men I don't know how I do it but I feel them out extensively making sure they're first timers. I love sucking newbies cocks. They lie to themselves about not enjoying it sometimes, or, they say they don't know why they're doing it. I hate to tell them but it's cause she feel the need to experiment, see if you picked the wrong side due to social norms. I love fucking women, eating pussy, always have. I knew I had a curiousity about holding a cock. Then I wanted to put it in my mouth. I wanted the man to be scared about doing it as I was going to be fucked up too. I love the excitement of a man having his first time. They always seem to come quicker and are sometimes harder to get erect due to guilt. I talke to them and lie saying it's my first time too, that usually take the anxiety down. Then they come easier and have a better orgasm.
The second and third guy I met were great. They were both on the fence and perhaps headed trans or cross dressers, I dunno anymore? The third guy was perfect. Panties and a bra under a normal guys outfit. He had a butt plug in and he turned it on when I sucked him. He really filled my mouth. It was great. This time I wanted to complete my gay urges. I wanted to feel a cock in my ass. This guy was more than eager to fuck me. My balls already ached. I needed to cum badly. I leaned over my front seat and he fucked my virgin ass. He unloaded in my ass and I came on the back of the seat. I had to stop and get some cleaners to clean the cum off the seat. This guy asked to see me again. I said yes to him!!!
When I went home the wife asked why I was walking odd. I told her my underwear elastic was rubbing me. She just smiled. Well you better ditch them!
I met up with him several more times. We met at his place. He became the bottom and I fucked his ass. He was now dressing in stockings and a bra, sometimes heels, I loved it. Then he wore old school garters and stocking and very high heels. Sometimes he'd come to the door wearing a french maid outfit, he knew I liked that sort of thing and he really get fucked. He sort of looked like a slut ragged Anne doll. Very slight young man. He was great sex. It lasted quite a while. I broke it off when my wife wondered why I went missing so much. I can only fake beers with the guys so much. Plus, she wasn't getting as much sex so, taking a break gave her a sex life again. :)
I quit men for a while. I starting to look again. I like warm cum in my mouth and a man's ass flexing in my hands with a nice smile after. If they let me fuck them that's great. I'm not a bottom, I figured that part out. I'm good with just jerking off on them, any area although I like to see my cock on the lower back of a guy. I tried a trans but the mindset isn't right. I like a straight guy hiding that he dresses in womens clothes behind closed doors. I used to put my mom or sisters pantyhose on up to my knees and jerk off. I didn't know why, I still don't. Yup. Again soon. I'll let my gay urges out. Heaven help the first guy. I'm going to suck him dry. LOL
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