You know it's bad when reddit is the only way to tell someone
These event and situation that I bring up I will try to keep in chronological order. After a week of deleting before posting and a few unsaved drafts I finally had to post this. But with it recently just coming to light in my Rl world I'll try to make a good read. So I had a Real life get off my chest moment. I will with a little background about me that's relevant to this read. I considered myself 99% straight white guy. Popular in high school and never had a problem getting women or keeping them. But ever since I was around 7-8 I always enjoyed wearing women's panty. They just seemed like I was supposed to wear them. Now I would probably do this maybe once or twice a year. I even thought it was weird but never found myself attractive to guys in a sexual way or anything that would make me think other wise. I'll mention I'm in my late 30s now so at that time it wasn't a common thing to see or hear about. Fast forward a few years. And the Maury show with the trans dudes who look like girls show up. And I was super interested in how that works lol. On top of that I'm just getting into porn. Which was starting to slowly mix in trans porn and sissy hypno stuff. Again would swipe by it and think nothing off it. Until I seen a trans porn that I thought was a girl and it baffled me. And got me thinking that if guys can become girls then I can wear panty every once in awhile and it be ok.
Fast forward a few years same scenario of me wearing panty every now and again. Trans porn and sissy porn is getting mixed in more often then before and I find myself watching it and enjoying the idea of being the alpha to a weaker male who dresses up and submits etc. that continues until about 13-14 age where one night I'm out doing blow and drinking with some of my boys and I strike out with the girls that we were with that night. Pretty sure it was bc of the blow and not being able to get fully hard lol. Well I get home and sure enough my sister has her laundry near my room and it's got some super slutty stuff . I immediately eye a tight fitting sun dress and pink thong. And put it on, but this time was different. I'm a skinny kid and not much body hair. And for the first time have the thought that I wanted to be the sissy in those porn videos. I want to get an alpha male to use me how he wants. So my smart idea was to go on Craigslist and post me dressed up in my ad. Well after sifting through around 40 emails of straight weirdos I landed on an email that said he was 25 and didn't come of to me as weirdo. Even tho part of his add said he had blow and would give me 300 bucks just for showing up. So I say fuck it and risk it.l, and tell him to meet me up the street. I love in upstate NY so even with the street lights it's dark in the city. So he meets me at the spot a few hours later. And me being dressed in a bright colored skirt/ dress and thongs on. With a marching tight t shirt walk down and meet a stranger. Open the door and immediately tell he's not 25 he's at least mid 40s. Starts off ok and actually normal conversation. Then he wanted to get down to what I have promised him in the emails. Which sounded great at the time but not so much when I had to perform. So after a few lines I attempted to do stuff with him but just was too nervous and wanted to back out. That's when things went sideways. He told me that the only thing protecting my stuff was a tiny dress and pink thong. Which at that time I realized I'm with an older bigger guy who wants what I promised. So I caved in and gave myself up inside of risking getting hurt or worse. I'll spare the details( pm me if you wanna hear them ) but basically made me do a bunch of stuff that I hated . Then dropped me off and paid me like the hooker I was . For weeks I felt super dumb and bad I let it happen. And didn't even dress for awhile after that. But one thing that I did take with me from that was the rush and sexual feeling it gave me after wards. Being used and no listened to by a bigger older male(alpha to me ) and to this day I still whack it sometimes to that situation.(Don't judge I know . Never said I wasn't fucked up) Fast forward to my early 20s I met a girl and were dating for awhile. I end up dressing again and meet up with a trans girl. Who to.me was hot but she was so hung and I couldn't turn her down. This started my second phase of life of a sissy. I didn't wanna a dude I just wanted a dick and the prettier the trans the more I'd be willing to do. So gf finds out that I'm dressing and eventually meeting trans . She acts cool about it for a few weeks. Until we are drunk one night and getting ready to bang. She asks me to dress up for her. I say no problem take a few photos and nothing else weird happens. I only mention this bc of the pattern I've created throughout my life. We end up breaking up and she tries to blackmail me with the photos but I called her bluff and said post the pics. She did and I was able to easily explain the situation to the boys and anyone else it would affect.
Fast forward to my mid 20s and I meet my wife. We hit it off and everything is great until our first pregnancy. I never got caught dressing until then. I got sloppy and had some emails from an ad I posted and never deleted. She called me out and I gave a bullshit answer. That she half believed. We got through that but every now again I'd get sloppy and leave her things and clothes in places that wouldn't make sense. This isn't a flex my no means but I only seen one tranny in the 12 years I've been with her. I felt so bad but the hottness factor of this trans was off the wall. Compiled with my self saying it was ok bc it was so long since I did it and her being difficult during a pregnancy. (Again I'm the piece of shit for this , just being brutally honest with this post) So we get through that and I eventually catch on to her hinting at things of me being a sissy. This goes on for years as just a "joke". Until last week when I was doing some blow and drinking and got the brutally honesty portion of the high I was feeling. And decided that was the night I'd spill my guts about everything. I sat her down and told her everything and then some every detail every time I think that way. And she was great about it. It just clicked for her , basically she loves me enough to understand why I was so fucked and being ok with it. Ok , so if your still with me on this post and read this far I promise this isn't a straight guy turns sissy post(well not fully). I wish it ended there , now it goes off the deep end.
She told me when we first started dating that she had a family friend that diddly her when she was young. But I never proded or poked past what she would say to me. Very vague and who am I to ask any questions. Well she opens up about it all. Again I'll spare the details but something made me shake in my bones... When she describe the family friend it was super specific. How she said it also , billy-bob Thornton looking. With a lazy eye and tattoo ( will be vague about this bc I don't want him to be identified for reason I'll share in a minute.) but the tattoo is something super specific and uncommon to have and where it was on his body was even more rare. Basically a 1/1 type of marking.... Now alarm bells are going off in my head did the same guy sissy both of us . She live 3.5 hours west of me at that time. So we start playing detective and it didn't take long for it to be known that it was the same guy. So she breaks down, I figured from the trauma as a kid. But she tells me he found out her location a few years ago and introduced himself again at the store she was shopping at. She explained to me that it was like she was back at that age it happened, felt helpless and couldn't do anything even tho she probably could. Then she explains that's he has her do stuff with him when he's in town. So trying to be understanding in a fucked up situation. I tell myself that I couldn't fight him off when I was young and if I was in her shoes I'd probably do same thing. Me being the almost 40 bigger stronger guy now. Mind you it's been 25 years+ since I've seen him. He's gotta be in his 60s. So I set a meeting for the three of us to end this situation we have. Well I met him he's this old fragile man and he had me feel.like I was 12 again immediately. I couldn't get rough I just froze and listened to what he was saying. He told us it wasn't gonna end. And that he wanted a threesome with us now whenever he's In town. Again I'll spare the details but it's wild what this old man asked us to do to our faces. So I finally get some courage up and say no way can't do that anymore. He tell.me flat out that he would expose the situation even if it's harms him with jail time... So now I'm in a bind bc he knows I don't want this story to be public. And my wife is already on board with all of it. So yeah here I am confronting the man would did stuff to make me a sissy 25+ years ago just to have him make me a bigger sissy... Wish I made this up but it's all true unfortunately.... But thanks for reading. You guys don't know how good this feels to type out and tell my side of the story to anyone and everyone. Hope my story helps someone out there