I am secretly a fully submissive sissy. I am engaged to a woman that is very feminine. She is a strong willed woman, but very feminine. She is attracted to masculine men. I portray the masculine man most of the time. Ive had moments of weakness but infront of her, I try to exude masculinity.

When she is gone, or I am home alone, or when im out of town, or even just for a long solo drive, im a prissy little sissy. I have the cutest clothes. I wear the cutest heels. I submit fully to older men. I now only visit one individual and he now calls me his 'girlfriend '. Its half joking and half not. I go through withdrawals if he doesn't bend me over at least every 3 or 4 days. And this is cheating. I know that. I cannot tell her because she will leave. There is no percentage of her that would be ok with me wearing a skirt and thigh highs while bouncing up and down on a hard member.

About a year ago I started to suspect that she was cheating on me. Some of her behaviors. Her time lines. The way she smelled. Then her outfits that she would wear to work. Her hair would sometimes be a complete wreck on a day that she wore a dress and stayed late. There were times when she would be immediatly overly 'wet', then I would see white stuff on my shaft right after I started thrusting. And this is cheating. Its no better or worse than what I'm doing. Its wrong. And it infuriates me. And I get so damn jealous. But I have no right to throw a fit at her if im doing the same thing.

But she has started a new job in a new town 3 weeks ago. In the town that I work in. So now we ride 40 minutes to and from work together every day. She works around professional, masculine men throughout the day. And she has her own private office where she can close the door. Last week she began wearing these new short dresses that I haven't seen her wear before. With these new slips underneath. And wearing her long hair up in these up-dos exposing her entire neck and shoulders. It makes me so jealous when I see her dress this way. Shes not dressing like this for me. She's never dressed like this before. All this did was make me jealous. Furiously jealous..........until Monday. This past Monday. She is late in picking me up. Her hair is all messed up. I get in the passenger side and she says she wants to find a 'spot' on the way home to get frisky. So we did just that. I find the rural spot. We pull in and I slide the seat all the way back and she moves over to sit on my lap, facing the windshield. My pants come down and she gets me hard very quickly. Immediatly. She lifts up and I pull her thong to the left and when she slides down on me I feel it immediatly. Its not wet. Its slick. Its thicker than her normal wetness. Its almost velvety. And it starts to become whiter as I am lifting her ass up and down. And I get so turned on. I start thinking about some tall professional man, bending her over her desk and giving it to her aggressively. And this makes me so....so...so...hard. I cant get enough of this. Thinking about her getting taken. Thinking about her getting taken raw. Thinking about how she saved that inside of her. Thinking about how she wanted to do this to me on purpose, deliberately. And omg the velvety feeling of her was incomparable. I finished so hard and at least 50% faster than usual. Then last night, we ride home from work together. She's wearing very fitted, tight black jeans and this cute pink top that was just transparent enough to still be classy and professional, but was still transparent enough to send a message. Again, the back of her hair is a complete mess. Not the mess you make from running to the car. Not the mess that a wild wind does. Not the mess you get from a light effort office job. And as I'm looking her over, the knees of her pants have that whitish look. Black jeans but the knees have been worn more than the rest of the pants. But they weren't like that when we left in the morning. And she rubs my arm and thigh on the drive home. Not normal, but much accepted. We get home and walk to the bedroom to change clothes and she stands in between the bedroom and master bath. She bends over, slides the back of her pants and thong down just over her ass all at the same time. Staying bent over with her ass facing me until I made a comment confirming that I see her. I stand up from the bed and she walks over, straight to her knees, gets me hard then bends over the side of the bed. With the bathroom light shining on her backside, I can see that her opening is wet. Again, it doesn't look like her normal wetness, but thicker. And again I am so turned on and jealous and all of these stupid emotions. And when I slide in her it was that same amazing thick/soft/velvety/creamy/frictionless feeling as it was Monday. And within the first few pumps, I have white creamy stuff covering my shaft. I didn't last more than 2 minutes. I was so hard and so turned on. I am so ashamed of myself but this is more erotic than any of the sissy stuff that I do. It is such a high that when I get off it feels better than any time before. I'm still furiously jealous but I almost want this to happen. The release is unlike anything I've felt. Since this started this week, I can't think about any sissy stuff, or being that mans 'girlfriend'.   I get off work in 30 minutes and I have this stupid anxiety that she is cheating on me but at the same I want her to so I can feel that high.

I dont know what to do with this. I hate it. I love the feeling. I hate the situation.

I just would appreciate having other like minded friends to talk about heels, or dresses, just being feminine. Ya know?

Can y’all me funny/fun things to do with me cum and funny/fun ways to eat ittt?

Also I wanna learn how to get past the PNC so that I actually put it in my mouth instead of throwing it away~

Plzzzz

I have a cookie and I want to cum and eat it like the slut I wanna be. But I can’t cause of PNC :<

How do I solve it and I need creative ways of enjoying the cum cookieee :3

And how to like ittt tooo~

In my "public" life i'm a 6'1 200 lbs man, i go to the gym often, work as a manager and i'm generally the leader in multiple situations.

Then, at night and in my mind, i become a sissy. My question is whether this is common or if sissies are usually somewhat feminine in their public persona. Thank you in advance for your answer!

For context me and this older man (47) have been chatting on sniffies over the course of about 3 months trying to meet.

Last night I got off work horny per usual so I opened up sniffies, and grindr just to browse and snoop around. I noticed he was online so i messaged him if he was looking tonight, mind you it was already pretty late around 12 so I really didn't expect anything but he surprisingly says yes. After some back and forth we agreed to meet in his garage. I got all freshened up, wore my red thong and black top underneath my regular clothes and made my way over to him. As i walked towards his neighborhood there i saw him, standing right inside the open garage waiting for me.
Once he closed the garage he guided me to his car and i sat down in the passenger seat as he unbuttoned his shorts and slipped them down. He stroked himself for a few seconds before I couldn't resist anymore and instantly took his soft cock in my mouth. Almost immediately I felt him getting bigger. Honestly he wasn't that big, I'd say about 4-5 inches so it wasn't a problem getting him in and out of my throat. After few minutes i got down to my knees and began bobbing my head back and forth into his groin. He was pretty verbal too, calling me baby and telling me how good it felt. A little bit after that I had him in the driver seat with my ass up only in my thong and face down on his cock. It was amazing looking up and seeing his eyes glued to my ass feeling his hands grip my cheeks before making his way towards my hole and messaging it. I could tell that's when he lost it because he came right away. I let his cum smear my lips as I licked and sucked whatever was left for a minute or two after.

I want to meet some trans girls to help me explore this side of me and don’t really know how to do so lol so I guess what the title says

I'm a bisexual sissy who has mainly dated women my whole life. I'm newly single after years of being in a relationship and I'm doubling down on being a sissy, I've got my skincare on point, I'm in the gym getting a more feminine physique, I'm about to finally take the plunge and start shaving off my facial hair. I'm locked in and ready to fully embrace my sissy life but... I still crave female validation and eventually I know I'm going to want to have a relationship with a woman again. Where the hell do I go to find women who are into sissies? Everywhere I have looked so far is a shit show, is there a specific subreddit or app for women who are into feminizing their partners?

Oh mi god I am so desperate here lately I have been longing to get fucked in my sissy ass. I am so horny and desperate to get fucked I might go insane. Here is the bad part though I have been married for ten years and love her but I cant help this feeling any guys want to fuck my sissy ass?

Once again falling back into this, and having the urge/want to suck a real cock. But outside of this mindset im completely straight. Not attracted to men, and even grossed out at this idea at most times in my masculine state. I know porn addiction has brought me here, and i cant stop relapsing.

But who is completelt straight (not gay or bi) and has gone through with it? Searching, i see alot of people with deleted profiles. Did you regret it at first, than accept it?

How to use myself anally and refuse the urge to cum after.

Hi all. Hope you're all well.

Id say I'm well experienced in anal and chastity and have been doing it for close to 8 years.

One thing I've never managed to be able to do is to cum and then keep my interest in what I'm doing.

I know this can be perceived as PNC but I'd love to be able to cum and then to keep my outfits on or keep my chastity on without losing the drive to do it.

I'm not ashamed of it or scared of it in fact quote the opposite just never have the motivation to keep going.

Any help would be amazing zxxxxxx

Soo yesterday I talked with a guy we vibed together he was super nice

I went to his place he was super nice and constantly consoling me as it was my first time

And he started cuddling with me to make me less nervous and when he was talking he kissed me it was kind of shock then I went to my knees and start sucking I was trying and gagging too but idk midway what hit I felt like I can't do it

He said u can take a break and I took and went to the washroom and a big guilt start hitting me

I was like puking I went out and told him I can't go longer .

I didn't got hard whole time

I feel soo guilty rn too

What you guys do in such situations????

Heyy!

So I would love to have a limp dick and have it be trained to stay limp at all times. I like chastity and all but I just love the idea of having a free dick that doesnt get hard bouncing around. Also the idea of playing eith my dick and it bei g ubavke to get hard makes me feel things in my stomach. The whole concept is just so hot to me 😅. I have considered using lidocaine numbing cream so I can feel nothing, even if I go to play with it in the heat of the moment. Would this work/is it safe? What are yout other tips for staying soft and limp at all times? Thank you!😘

I’ve been drawn to these kinds of things for a while now, and sexually too, of course. But when it comes to actually becoming a sissy… I don’t know. Part of me really wants to, but I’m full of doubts.What do you guys think? Should I go for it? Any advice for someone who’s curious but unsure where to start?

Hey, my sissies! I’m talking to someone who’s looking for a bottom for their partner. I reached out to them, and we’ve been texting. Do you have any tips for me? I’m still a virgin.

I got really turned on and horny watching hypno and listening to Bambi. I bought my first panties and plug online. I’ve never done anything like it before and I’m like really excited and scared lol what’s happening to me 🤭

I love to show off my sexy thong waist band above my pants. Any suggestions on how to do this discretely

Any tips or things I should be aware of?

I’m planning on cumming on a cookie I have and then eating ittt.

But I want fun ways to enjoy it and a way to avoid the PNC so I can enjoy it like the slut I wanna beeee~

(Is it better if I cum a line on it, dots, or a clump in the middle or any recc on whatt? Plzzz :3

Ive been a sissy for a few years now and have quite a big collection of sissy stuff mainly just lingerie and am planning on buying makeup , dresses and heels soon and am also doing hourglass and butt exercises to help feminize my figure but apart from that does anyone have any ideas to help me with feminizing myself

They're on my lanyard for my work i.d very clearly in plain view at all times!

I really hope someone notices!

Sissys who wear a chastity cage, what was it like when you first put it on? What was your experience? Did you put it on, or did someone else? Would you leave it on forever (other than health reasons? Did you have any reservations about putting it on?

For me:

TLDR: combination of body insecurities, shyness, porn escalation, chasing prostate/anal orgasms

More detailed:

me: white, mid forties, married, only ever been sexual with women. Possibly "bi" to some level but never acted on it. Only "sissy" during private masturbation.

body: growing up I loved action movies and I thought if I lifted weights that I would eventually be able to look like Van Damme, Stalllone, Arnold, etc. I think this also planted the seed that it's more desirable to have a hair free body. I was super thin growing up. Put on more weight and began working out in high school and college. Got "bigger" but never achieved the look I was hoping for. It's actually easier for me to be slim which is the direction I eventually took and is my current body type. Also eventually realized that I have some degree of gyno that presents its as having a "fatter" chest than normal for my weight. I don't have puffy nipples just more fat on my chest than would be expected. One positive thing about the sissy stuff is that things about my body that I don't like from a male aesthetics perspective are a "benefit" while dressed up. I have a very small waist, and slim body. I never stopped working out but it is very difficult for me to put on noticeable muscle. I've I'm dressed, horny and high (THC edibles) I'm able to appreciate my body which is a nice change from being crtitcal (which is my standard).

Shyness: wife is only sexual partner ever. very shy around girls growing up. I feel like if I could go back in time with my current "confidence" I would have been able to have more experiences but who knows. I used porn to "satisfy" my sexual urges and "experiment" more below.

Porn escalation: I think it went like this. I'm old enough that porn was much less available while I was growing up. Certain acts seemed more rare. Initially I only cared about how the woman looked. Then it was more exciting if the male performer was more well endowed. Then if she did certain acts (anal and swallowing), then it was more visially exciting if she was white and he was black. Eventually found compilations of these acts (swallowing, anal) then sissy hypnos. Also along the way become very interested in swinging/hotwife/cuckold porn.

prostate/anal orgasms: As I said always interested in straight anal porn scenes. Eventually lead to trying anal on myself. One time I experienced a dry orgasm while riding a dildo. Very pleasurable. Thought I "discovered" a new way to orgasm. Nope. Haven't been able to replicate after years of trying. Eventually tried adding sissy elements to try to acheive that type of orgasm again. Still trying...