A guy I'm chatting to is into cross dressing (which I find totally hot) last night he asked if I was into 'sissy fun' but then didn't answer when I asked what it was. I am assuming it's some sort of cross dressing sex play but I don't really want to google it in case it's something I wouldn't want on my search history. Can anyone enlighten me please?
Hey,
So sissy play is basically a guy being an ultimate sub in dress. Allowing you to dom him completely. If that makes sense? X
Thanks Bsa. That does actually sound like something I would love to do! Woo hoo 
I think it's a great way for both to explore eachother and gives you a chance to really dom and be in control. Where are you chatting with this guy?
Hi Corset_is, I noticed your post in the other thread, "Where did you get your kinks?" and it describes the sissification fetish pretty much spot on, so I think you're safe in doing some searching/googling on it because it sounds like you're both up for it.
Basically it's another word/term for male feminisation, usually through cross-dressing, but with the added implication of a Dom/sub dynamic where the male is "forced" or "coerced" into doing it and him finding it humiliating. So the cross-dressing him can mix/overlap with orgasm denial, locking his penis in a chastity cage, using a strap-on on him, coming up with a "her" alter-ego that you dominate domestically/sexually, etc.
Note that this isn't a set in stone wall. You can explore all sorts of cross-dressing and feminisation play without an ounce of the Dom/sub aspects, but using the specific term "sissy" or "sissification" usually means that it's part of the fetish to some degree.
Hope that helps, but do some good research yourself, talk to him about it. If he didn't explain when asked up front he may be too shy/embarressed to say/explain it out loud. So tell him you've looked into it and are interested and excided to explore it with him, which may assure him and get him to open up more specifically about what he wants/what he's into.
Good luck, and have fun! 
Eager-2-Please you wouldn't happen to know of any good sites to check out? We have actually just chatted about it and he wants to be a princess but I have to pick him out a dress!
Corset_is wrote:
Eager-2-Please you wouldn't happen to know of any good sites to check out? We have actually just chatted about it and he wants to be a princess but I have to pick him out a dress!
There's a page on wikipedia called "Feminization (activity)" for a general overview with additional links to similar pages and categories etc. FetLife is a good community site for BDSM/fetish enthusiasts. If you navigate to "Groups" and/or "Fetishes" there's a search function where you can search the forums and other users tailored to match your interests. Also, you could try using the search terms in porn sites like pornhub and xvideos to get some visual ideas/inspiration.
Thanks Eager x
I have actually had a sissy experience in my late teens with a guy I met at uni. It made me feel empowered and he liked it as he had alsways wanted to try femanising himself.
Well as a starter I just wrote him some erotic fiction about what I would do to him in a Sissy Princess role play. It wasn't my best work as I don't think the evil queen came across as dominant as I wanted her to be but I shall wait to hear his verdict later and have demanded he sends photographic proof he enjoyed it 
Corset id love to have that sort of fantasy play but don't know where to start! Would love to have someone to swap the erotica with like yourself!
Bsa, it's something I started doing ages ago cos I find it awkward sometimes to express my sexual desires verbally. I write the stories to whomever I am dating at the time as an ice breaker to discussing what I want and based on their likes too.
I honestly have no idea where to start either, I suppose finding the right outfit would be a good start. 'She' needs a pretty princess frock and I need an evil queen outfit that makes me feel empowered.
That's a great idea to get all your fantasies out on the table. Is hot how 'she' wants you to dress her too and then dominate her. I for one would love to be involved in that meeting hehe
Sorry Bsa, we have already covered that topic...no third parties. Lol
I'm having a great time looking at costumes for us both. I really want 'her' to get this mini-dress princess frock I've seen cos it's a major turn on for me when he sends me pictures of him hard but dressed as a woman in a short skirt. I'm not a fan of dick pics but a little hint of his arousal is just so hot!
Well I got my review of my erotic story...and it was a BUG one, if you catch my drift 
Well I am glad 'she' liked it. Although I am extremely jealous not to of heard it to. I love sharing erotic stories!
It was very personal 😳
I don't like to admit that I enjoy being sissified by my wife in front of her lady friends and swinging pals. She dresses me in her underwear ( we are the same size ) a very short skirt, wig and make-up and parades me up and downto her friends.She often carries a cane or flogger and uses them often. Being a sissy is a great turn-on for me but I'm not allowed to show it even if we are on our own. Being a SUB to my wife is my biggest joy especially if she turns me into her sissy. I could write forever about our exploits.
Well please do Chisel...I am looking for ideas!
I've been there but he is obviously not worth your Time x