r/Sissy

Tonight I was wearing my blonde wig, I was fully dressed, plugged, and in chastity. I went out to the garage to get a drink fully dressed like I had done before many many times for years. I got in the garage and after 5 seconds of me being in there my brother walks In and turns on the lights to find me in pink lingerie with a blonde wig on with my head down because I instantly felt the shame. I instantly switched to boy mode and laughingly said brooo. He just started laughing saying what the fuck. I tried to keep my cool and said bro this is crazy (laughing to keep things as light as possible because wtf) he asked if it was a fantasy football punishment and I think I laughed and just said bro you gotta go I’m sorry you saw this. I have literally been dreading this moment for yearssss. Like this is my worst nightmare. I took my wig off and grabbed some jeans to cover up before I walked inside. He can hear me when I walk through the house so I lightly laughed a tiny bit to act like it’s no big deal and to hide the fact that I was freaking out. I had no idea what I was gonna do. I went back to my room and changed quickly and go up to his room. I figured I would tell him that someone offered me 500 dollars to send pics. And I also said a few other things about how I was so sorry he saw that and joked that that was probably the craziest thing he’s ever seen. I was really trying hard to sell this whole thing and I think I did a decent job. He just laughed and was saying that it’s okay and that “money is money”. I said yea exactly and then he just went back to normal and asked if I was still going to buzz my head (I had mentioned it before and was asking him if it would look good) I thought about it and said probably not. He said good.

I’m really paranoid that he doesn’t actually believe me about the 500 dollar thing and I’m wondering what I’m gonna do about this tomorrow. My plan is to just act like it never happened and I’m assuming he will too. Then maybe at some point, tomorrow or the next day, I’ll mention it and see how he reacts. Maybe if he asks questions about how I was “offered 500 dollars” I will be able to make more stuff up to really sell the story. Which I will probably be able to because I’m gonna be spending the whole day tomorrow thinking about it.

Anyways thank you for reading and please help me or give me any advice you might have because I really need some.

I’ve always been the dominant one in my relationships until now, but recently I have an overwhelming desire to suck cock. Not just to suck, but to worship cock. I want to be on my knees, the cock pressed into my face. I want to lick the shaft, the tip, the balls until it’s hard enough to slide into my mouth. I want to suck the head steadily until my saliva is running down the shaft, making my hands easily glide up and down as I work the head with my mouth. I want to take it deeper and deeper until I’m gagging and have tears running down my face. I want my head to be held firmly by strong hands and have my face fucked as I fully submit to the cock. Finally, I want to be on my knees, tongue out like a good little slut. I want them to shoot their cum all over my face and my tongue, then force the cock into my mouth again so I can suck out the rest of the delicious cum and clean the cock. Then I just want to be left alone, covered in cum like the useless slut I am. Maybe if you are reading this you could help me with this craving.

So wife and I were going at it. She had my hands wrapped to the door frame with her strap-on cock in my ass while I was caged. Very hot very aggressive. Then she tells me she told her gay coworker (work husband if he wasn't gay I guess) that I have bigger toys than her. Apparently he asked if I was a sissy. So she asked me and I made he hump me hard before saying I was. She likes my response and apparently also told him than I can suck cock deeper than her.

Idk what to do with this information but it makes me scared and aroused lol

Hi girls, I just wanted to share this quick little story! I was at work the other day, and I had my panties and cage on, as one does. I have an inverted cage, but there’s a little piece towards the top that sticks out. But I was scrolling through twitter and I started rubbing my and playing with the piece that sticks out, and I was totally rubbing myself like a girl. And before I know it, I’m spurting in my pants from rubbing myself like a girl. And I had to run down to the bathroom and clean myself up, because I was a bad girl 😈. Anyways, I’ve never done it before and it was kind of a milestone for me 🤭. Love you girls xoxox

what site do you trust to get you going crazy?
what are you generally watching when trying to reach a sissygasm?
i’m open for any good content sites :)

Title says it all dm me what you got and decide my fate

Hey everyone, first off thank you sooo much for all the support on my first post here it meant a lot. So anyway as an update I’ve been wearing my cage to bed all week and it’s soooo amazing even used my dildo some with it on. But anyways I finally got up the courage and got a fully girly outfit like wig, shapewear body suit with a thong back, mini skirt, makeup, and stockings. If this post does well I’ll do an update for you all when I get my clothes, but if not this post is for me bc I’m a happy sissy.

My gf at the time went to college with me and stayed the night before we had to drive to class. I decided to be sweet and got up and went out to get us coffee and breakfast and had it waiting when she woke up. I hoped in the shower and when I got out my boxers were gone. There was one of her thongs and a chastity cage outside the shower when I got out and I picked it up to go ask her what was going on (we really didn’t play outside the bedroom). She giggled and got started working me up, rubbing on me and asked if I would put them on and eat her out before we left for class. I did and ate her out until she was satisfied. When we were done I asked for the key and she said no. She said she didn’t cum and we didn’t have time to keep going and that I could take it off until she had an orgasm. I asked if I could at least take the panties off and she said no. I figured it was whatever so I put my clothes on and when drove us to class. We met up for lunch at the student center and she had some of her sorority sisters with her. They were giggling when they walked up and my face was blood red and I was pushing against the cage so much it hurt. She grabbed my hand and we went and all got lunch together. On the drive back at the end of the day I asked if she told them and she wouldn’t say. She put her feet in my lap while I was driving and was rubbing on my cage. She told me she wanted me to beg to eat her out and I laughed and gave her shit. She kept teasing and reminded me she wasn’t unlocking me until I did. I eventually caved and started begging to eat her out. She wanted more.. she made me beg to worship and rub her feet. She made me beg to wear panties more. She made me thank her for locking me and letting me wear her thong. Then she told me to thank her for telling her friends about it. My heart sank and I asked if she really did. She was fumbling the key around and told me she said to thank her while she pushed down on the cage with her foot. I felt my voice shaking as I thanked her…

I posted 3 days ago that I had 3 interviews and I had worn a thong all day for them. Even had some fun while on the phone in 1 interview. ANYWAY!! I got a job! I’m honestly happy that I did as I needed a better one. It still excites me that I worn a thong all day and did what I did. I’m honestly going to start wearing one on my important days! Might have brought me some luck.

Hello ladies this is part 2 to my mom catching me as a sissy. After she closed the door and went downstairs I immediately took the dildo out of my ass, jumped out of bed took my lingerie off, my makeup off and my wig off as fast as I could. My heart was beating so fast it was like nervous adrenaline I didn’t know what my mom was thinking in her head and it was killing me. I didn’t come out of my room for the rest of the night. In the morning everyone got home but they all left for work eventually but my mom called off because she was sick as I stated in the last post. She was at the dinner table drinking coffee when I went downstairs, I went up to her and said hello in a very embarrassed voice. I was turning so red I looked like a tomato she said “hey honey good morning”. I asked her if we could talk about last night and she of course we can. I asked her what she saw she told me she saw everything. My family in particular doesn’t really know anything about the LGBTQ+ community so she said it really caught her off guard but she was sorry she walked in without knocking. I told her that I liked men, I mean there was really no hiding it at this point I had a 10 inch BBC dildo up my ass with lingerie, a Chasity cage and makeup with a wig. She stood up and gave me a hug and told me it was okay and she loved me no matter what. That really meant a lot to me I didn’t think she would accept me for being a sissy… well I told her I was a femboy since that’s easier to explain which I kinda am. She did ask what I had around my penis referring to my Chasity cage… I again got so embarrassed but I had to explain to her what it was. She was very confused about the Chasity cage but she asked if it made my penis smaller I told her yes but I recently just started using it and that was my normal size. When my mom says this she means it in a motherly way so please don’t sexual this next part. She said she was sorry for not doing anything about my small size when growing up, her mood changed she turned to a more apologetic tone. What she meant by this was she thought she could bring me to a doctor growing up during puberty to help my penis grow but honestly it was just genetics. I explained this to her and told her it wasn’t her fault it’s just genetics. She had so many questions but it was all out of love she asked if I was trans but I told her I wasn’t. She told me she just wanted me to be happy and I should love who I love and dress how I want to dress. Honestly it was kind of emotional between both of us but I asked her if she could keep it a secret between us and she said “I would never out you to anyone sweetie” we hugged after this. She asked if there’s anything girly I wanted to buy she would get it for me. She told me at the end of the day clothes are just fabric so who cares what you wear which is so true. But after this hard talk she told me we could go shopping together and just tell my brothers and dad that I was accompanying her while she shops but in reality we were shopping for the both of us. Honestly it was an embarrassing experience but me and my mom are closer now since she never had a daughter in a way I was the closest thing to the daughter she never had.

I always want to do it then back out or get turned off at the first taste as it almost has a bite to it? But I love my precum so I have no idea and need advise

We talk a lot about straight guys who love sissies or those in our community who are still only into girls, but I’m curious how many of us are strictly into men? I am bi, myself.

I would talk to someone on Grindr about hooking up, everything goes well, and then they tell me that they also want to suck my cock. In itself, of course, that's not something inherently bad, but in my mind, I want the men that I suck to not even think about sucking cock.

If I hear that they are versatile or that they also want to suck, it feels like they get less dominant and I lose interest, since I want someone who is sure that he only receives blowjobs, not gives them.

Even if I reject their offer to blow me, and they say "ok, no problem, then you can be the only one who sucks my cock", I kinda lose interest. Even if in our interaction he is fully top, the idea that he wanted to suck my cock turns me off.

Does anyone else feel the same?

29 year old sissy/trans girl that loves talking about cute dresses,heels,makeup, and anything super girly and slutty hehe!

Hi, I want to start my journey by buying some things, but I don’t know what. I would for some suggestions on clothes and toys I should buy

Girls, so I’ve like reeeaaalllyyy committed to locking in now. No more gross PNC or purges. A really good way to like augment or whatever is to like get body mist. Victoria Secret has like a great deal for three lotions or body mists for like 33 dollars. So I’ve got a post shower Coconut Milk Rose Hydrating Lotion, Pure Reduction Shimmer Fragrance Mist, and like Midnight Bloom Fragrance Mist.

There is like very few things that get and keep me in a total sissy mindstate more than applying the lotion after the shower, then choosing a mist and doing the spay and walk (for the new new girls in here that’s where you spray it in front of you and then walk through the mist). I can’t recommend it enough and slowly but surely my room is like totally changing the energy to sexy and feminine as the scents work their way into my stuff!!!

That’s like all babes!!! 😘

I'm finally starting HRT in a few weeks, I'm so excited!!! This is a huge step 😁😁

Having talked to many sissies here, it’s clear a lot of men are only interested in us to relieve themselves and not actually listen to what your gurl wants.

Now before anyone says, no we’re not asking for romantic dates and getaways trips, but just someone who makes us feel utterly feminine and even better, not masculine at all. Yes those are a bit different.

Soo, I created acc in grindr trying to find a partner, and all I was getting was hundreds of unwanted dickpics (if thats what girls get normally, I do not envy them), but thats not the point. I’ve got talking with a few nice guys, and it was awesome. I invited one of them for a movie and he said YEAS!!! But then it turns out he lives in other city. fuck.

So, can I regulate grindr so that it would show me profiles only nearby me? Its just really disappointing :(

Hello! I’m a 26M who first got intrigued by crossdressing when I tried on my mom or sister’s panties or bras or necklaces on occasion when I was maybe in middle school (as I’m sure many did), but didn’t really get into it more seriously until college when an ex wanted to try pegging me. Until that point, I’d never questioned my gender or sexuality. I truly believed that I was just a typical cis het dude. But that experience led me to an interest in trans porn and that all brought back the crossdressing interest.

I went through multiple cycles of buying fem clothes and then purging it all throughout college, unsure of what I liked so much about it. Did it make me feel sexy? Did I just wear what I wished my partner would wear? Did I want to be a girl? Did I just want to be a submissive guy? Was I a CD? A sissy? Trans? Just a guy with a taste for fem styling? Was I bi? Gay? I had no idea anymore. I didn’t have a general interest in men, I didn’t find them attractive, but when I dressed fem I wanted to be desirable to men for some reason.

Eventually, I craved for someone else to see my fem side, for an NSA stranger to see me and sexualize me and want me as a fem person. I met up with a few men, sucked a few cocks, and eventually had sex with one while on vacation. I took a full fem outfit on the trip for this specific purpose, then threw it all out at the end of the trip. It satisfied something in me but idk what. I didn’t suddenly see men any differently, I still wasn’t attracted to them, but I did like how it felt to dress fem and be desired for it.

These days I still crossdress in secret on occasion, but I’ve at least expressed to my current girlfriend that I have a slight interest in trying some fem stylings and we’ve even tried out pegging. She’s very open to these things but I don’t know how open I want to be about my level of interest. I do still find myself going through cycles of craving to dress feminine, to feel feminine, to be desired for my feminine side (more often than I’d like to admit). On occasion, I also still have that specific craving for a man to want my feminine side and treat me as his fem sub.

I don’t know where this leaves me. I want to just ignore it or maybe just feed the desire a little by wearing a skirt on occasion around my gf or something, but I’m afraid I’ll always want more. Am I just a crossdresser? Am I a sissy? Idk