The sissy problem!

Jonbon_13 · 05-10-2019, 03:38 PM

Hi so I always go back and forth!
But first: I’m a young guy, with a GIRLFRIEND. I am athletic fairly masculine and like that look on the exterior. When I’m horny and alone or have free time I’m a sissy. Not full on but I have that mind set. I like to crossdress (love) I like to do it in semi public parks and forests and anything like that (love) I love the humiliation of it all the degradation and loss of manhood. Not sure how I feel about going past this BUT, I’m looking for new thrills always. Didn’t forget to mention diapers as well.

Problem: I go out in my wig, makeup, leggings, bra, sports top. And I look kinda half female, almost passable and I love it. Such a thrill. But once I jerk off the feeling is gone I want to be a man again. Until I’m horny again in a few days. So this is the problem. I need help I want to do more dares and more thrills. Like public pools or locker rooms or something else very creative without too much expose! But still crushing my manhood. I love to feel more sissy than I usually do. Idk how to accomplish this without taking the next step and meeting up with guys. Maybe I’m just a CROSSDRESSER and not a sissy? Idk but I need help.

What can you do?: too all masters, mistresses, switches and other sissies. Pm me PLEASE. If you have ideas or can help.

MASTER/MISTRESSES: I would love one that can help and wants to push me and be controlling but meet me within my limits a for now. Not handing out my kik right now I’ll wait on pms before I hand it out I want to find someone that wants to talk not just act. I want you too show me how creative and stern u can be as a master. In return I’ll do my best and as well your getting an almost passable sissy. I do pics and some vids. Want you to help me get the thrills back.

Kik me at panty.boi

sweetorsassy · 05-10-2019, 06:20 PM

Have you ever thought about involving your gf in this thing? Maybe she can be a part of it? Or do you just want men to be a part of it? Not sure what to say for you because idk what you're wanting

WeirdlyTurnedOn · 05-10-2019, 08:42 PM

I know exactly what you mean, and I just started taking a new approach to it. Even though dressing up turns me on because of the feminine aspect to it, I don't think of myself much of a sissy. Have you watched those sissification videos on any pornsite? I have and they don't appeal (totally) to me. I mean, some of it turns me on, but I get that shamefull feeling after beating one out to it. So what I'm trying to do now is embrace crossdressing as a part of my desire to incorporate some femininity into my personal life, while keeping the sexual part reserved for the dares. I'm trying to get less turned on by the clothes I wear and more at what I do with them. But I've only started recently so I can't give any feedback on how that's going to you. Hope this made some sense and hope you can help yourself as well.

Jonbon_13 · 05-11-2019, 10:59 AM

Thank you guys! Your all super helpful. And ya I think that's what I need is a new desire as I've kind of done all the risky cross dressing I can think of! I need to maybe push my limits and try new things with it and explore it! Maybe more humiliation would help?

If maybe maybe any master could help please please PM me and maybe we can workout a long term thing on kik

Jonbon_13 · 05-12-2019, 01:00 AM

Wanted to tell ppl I added my kik as I wasn’t getting any hits

05-10-2019, 03:38 PM	#1
Jonbon_13 getDare Sweetheart Join Date: Mar 2013 Posts: 264 Blog Entries: 1	The sissy problem! Hi so I always go back and forth! But first: I’m a young guy, with a GIRLFRIEND. I am athletic fairly masculine and like that look on the exterior. When I’m horny and alone or have free time I’m a sissy. Not full on but I have that mind set. I like to crossdress (love) I like to do it in semi public parks and forests and anything like that (love) I love the humiliation of it all the degradation and loss of manhood. Not sure how I feel about going past this BUT, I’m looking for new thrills always. Didn’t forget to mention diapers as well. Problem: I go out in my wig, makeup, leggings, bra, sports top. And I look kinda half female, almost passable and I love it. Such a thrill. But once I jerk off the feeling is gone I want to be a man again. Until I’m horny again in a few days. So this is the problem. I need help I want to do more dares and more thrills. Like public pools or locker rooms or something else very creative without too much expose! But still crushing my manhood. I love to feel more sissy than I usually do. Idk how to accomplish this without taking the next step and meeting up with guys. Maybe I’m just a CROSSDRESSER and not a sissy? Idk but I need help. What can you do?: too all masters, mistresses, switches and other sissies. Pm me PLEASE. If you have ideas or can help. MASTER/MISTRESSES: I would love one that can help and wants to push me and be controlling but meet me within my limits a for now. Not handing out my kik right now I’ll wait on pms before I hand it out I want to find someone that wants to talk not just act. I want you too show me how creative and stern u can be as a master. In return I’ll do my best and as well your getting an almost passable sissy. I do pics and some vids. Want you to help me get the thrills back. Kik me at panty.boi __________________ Likes: diapers, crossdressing, crossdress shopping, public and semi public, humiliation, degradation Dislikes: body writing, family, pain, permanent, etc... Limits: social suicide, blackmail, anything overly extreme 21 year old diaper sissy looking for dares and master Pm me if interested Last edited by Jonbon_13; 05-12-2019 at 12:59 AM. Reason: Added kik

05-10-2019, 06:20 PM	#2
sweetorsassy Member Join Date: Mar 2016 Posts: 31 Blog Entries: 3	Have you ever thought about involving your gf in this thing? Maybe she can be a part of it? Or do you just want men to be a part of it? Not sure what to say for you because idk what you're wanting __________________ Follow this link to my likes, dislikes, limits, toys http://www.getdare.com/bbs/blog.php?b=77775 All toys lost in move. Household items only. Punish me for bad habits https://www.getdare.com/bbs/blog.php?b=89529 Kik sweetorsassy789

05-10-2019, 08:42 PM	#3
WeirdlyTurnedOn getDare Sweetheart Join Date: Jun 2016 Location: Chilling at home, waiting for dares Posts: 274 Blog Entries: 1	I know exactly what you mean, and I just started taking a new approach to it. Even though dressing up turns me on because of the feminine aspect to it, I don't think of myself much of a sissy. Have you watched those sissification videos on any pornsite? I have and they don't appeal (totally) to me. I mean, some of it turns me on, but I get that shamefull feeling after beating one out to it. So what I'm trying to do now is embrace crossdressing as a part of my desire to incorporate some femininity into my personal life, while keeping the sexual part reserved for the dares. I'm trying to get less turned on by the clothes I wear and more at what I do with them. But I've only started recently so I can't give any feedback on how that's going to you. Hope this made some sense and hope you can help yourself as well. __________________ Just here to have fun with some simple dares, Straight M, 19. Likes: Public toilet, crossdressing and underdressing, hypnofiles, games and hidden-public. Dislikes: Spanking, toothpaste, wedgie and too messy. Limits: Pain, anal, scat/piss, permanent/curse hypno files, pics, public, family/friends and disgusting stuff. Love some light crossdress, just here for simple and fun dares to give me pleasure. Pics on my profile :3 My PM dares!

05-11-2019, 10:59 AM	#4
Jonbon_13 getDare Sweetheart Join Date: Mar 2013 Posts: 264 Blog Entries: 1	Thank you guys! Your all super helpful. And ya I think that's what I need is a new desire as I've kind of done all the risky cross dressing I can think of! I need to maybe push my limits and try new things with it and explore it! Maybe more humiliation would help? If maybe maybe any master could help please please PM me and maybe we can workout a long term thing on kik __________________ Likes: diapers, crossdressing, crossdress shopping, public and semi public, humiliation, degradation Dislikes: body writing, family, pain, permanent, etc... Limits: social suicide, blackmail, anything overly extreme 21 year old diaper sissy looking for dares and master Pm me if interested

05-12-2019, 01:00 AM	#5
Jonbon_13 getDare Sweetheart Join Date: Mar 2013 Posts: 264 Blog Entries: 1	Wanted to tell ppl I added my kik as I wasn’t getting any hits __________________ Likes: diapers, crossdressing, crossdress shopping, public and semi public, humiliation, degradation Dislikes: body writing, family, pain, permanent, etc... Limits: social suicide, blackmail, anything overly extreme 21 year old diaper sissy looking for dares and master Pm me if interested