My First Real World Sissy Experience

Considering I write about sissy erotica, I thought I’d share with you some thoughts on my first sissy experience many years ago. It will probably be the basis for a story in time. Even though I write about this type of thing, I just wanted to show that I’m also living it at least part-time. It gives me a lot of inspiration.

I had been flirting with a local pre-op TS over twitter and I had informed her that I was submissive. She said that we should have some fun. I was interested to experience it all so readily agreed. She wanted me to prove that I would be a good sissy, so she made me get into my chastity device, lock it up and stay locked up until we met. I still had the key but she text me asking for pics and messages/time stamps to prove I stayed locked up. I did and after the first couple of days I got used to it. Chastity had been something I’d played with on and off but it really does heighten your sexual feelings, it is well worth doing if that is what you are into.

Over the course of the next few days she would order me about in the evenings. Usually making me watch lots of gay porn as she told me I had to get used to lots of cocks. About ten days after we started, she text me and ordered me to report to her house immediately. I was freelancing at the time but luckily I could slip away for a few hours without any big drama.

She had been partying and her place was a mess. Her orders were to pleasure her and clean up her house. So I went there and dressed up in an outfit that she picked out and gave her a blowjob. It wasn’t an unpleasant experience although sadly she didn’t finish in my mouth. She pulled out and tried to fuck me but as it was my first time and she was huge, it wasn’t getting all the way in. This led to her giving up and getting me blow her again. Sadly she didn’t spurt into my mouth (which really disappointed me as I had done the work and wanted my cum reward) and didn’t even cum on my face, she just came over herself and cleaned herself up with a towel.

After this, I was ordered to clean her house and go. She didn’t speak to me again after that and stopped following me on twitter. I don’t know if it was because I was crap or because she found me unattractive or what. So a very curious and a tad unsettling experience for a first time.

I really didn’t mind giving head but I wanted to get my reward. Giving head was such a new experience that I really wanted to get the feeling of cum flooding my mouth, to feel properly submissive. Alas that wasn’t how it went down. I also didn’t mind her cock up my butt (what she could get up there) but felt this overwhelming sense that I needed to pee.

Actually experiencing this with someone was far better than getting excited watching porn alone. When you do that, often its an orgasm and then a sense of remorse. When you don’t get that post-orgasm come down, your remorse levels are a lot lower. Walking back home, my biggest regret was that she hadn’t cum on or in me. I try to use these feelings when I write because I know first-hand what it feels like, the first time you submit to a cock.

So yes, I wanted to share with you my first real-world sissy experience. thinking about it, I’m positive I’ll make it into a story but with a more exciting ending!

2 thoughts on “My First Real World Sissy Experience”

  1. OMG, that’s awesome that you (a) had the opportunity, and (b) had the courage to follow through. Too bad it didn’t end the way you wanted, but it’s something to build on, right?

    I bet you looked great, and a true domme would see your potential and develop it, not give you the cold shoulder. Still, those experiences do help shape our stories, and they’re what separate fantasy from plausibility. 🙂

    1. Very good points and clearly she wasn’t interested in me bar a quick shag. I suppose in a way that very much made me feel used like so many after a one-night stand!

      These days I look far better as I have much better clothing, wigs and gorgeous fake breasts but they’ll be more chances if I want them I’m sure. Although I am very happy in a relationship so maybe that chapter is over. Part of me yearns to feel hot spunk flooding down my throat however!

      I’m starting to write up a book (very) loosely based on what happened, it’ll have a much better ending than the real life version that is for sure.

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