Understanding the route cause of my sissy problems

Hi,

I am currently struggling with sissy desires and wanted some advice to understand what is causing these problems.

From a young age of 5-6, I would look at shopping magazines and stare at the lingerie pages but I had no idea why it felt good to look at them. I discovered masturbation at age 10/11 initially by just rubbing myself against sheets.

As I got older into age 13/14, I started trying on my mum's lingerie when no one was home, in my head it was sort of a way to get closest I could to sex, I would wear her bra and thong and rub myself against the corner of the bed with a pillow whilst simulating the action of sex.

Whilst this was going on, I was desiring females, at school, on TV, in public, all I could think about was having sex with a woman, what it would feel like, however I was a very geeky and overweight child, didn't have many friends and was always shy to speak to girls.

As I got older, I started watching porn but most of these years it was just regular male on female porn, the only thought that would turn me on is having sex with a girl, however I started to sense a shift, I slowly started trying other things such as babydoll and heels from my mum's cupboard, I would put a pillow underneath me on the bed and pretend I was riding although in my head I didn't think I was riding a penis and the thought of another man or his penis would revolt me. I didn't understand why it felt so good, all I knew is any chance I would get home alone, I'd run for lingerie and heels and masturbate to regular porn. Between ages 14-17, I was usually always rock hard, but as time went on, I would start to pre-cum very quickly and lose my erection, although I never thought anything of it. I was also quite worried about my penis size, it didn't grow as much as I thought I would as I got older and it's remained to this day at 5.5 inches fully erect.

Eventually I was so sick of being a virgin, around age 18, I went to a escort for the first time as I was still too insecure and fat to speak to real women, I went to the escort and came within a minute of receiving a blowjob, couldn't stay hard after I came and felt so bad after the experience, but this was only the beginning, this was the beginning of 4 years of visiting escorts, eventually having penetrative sex (which felt good but I wasn't able to sustain my erections so I didn't get to enjoy it as much as I thought I would), I would also ejaculate within 30 seconds of penetration. I once went to a escort and my penis size became a massive problem as I couldn't keep it inside of her and she had to keep moving positions and eventually said you have no idea what you are doing - she was right, I was a desperate guy who never really got to explore a woman, have a real genuine sexual experience.

I was about 22 when I eventually had my first girlfriend, I went to gym, got into shape, found myself becoming a relatively attractive guy which a lot of girls wanted to speak to, but I was too nervous to take any girl all the way, with my main insecurity being worried about my penis size or whether I'd ejaculate within 30 seconds. I was confused because when I was in my teens, I'd masturbate for 5-10 minutes without ejaculation quite easily, but as time went on, my masturbation sessions would end within 2-3 minutes.

The porn I was watching started to change during this period, I would watch a lot of porn where the woman would be submissive to the guy, she would be screaming of pleasure, I would look at her and be like wow, I'd love to get pleasured the way she is but I was looking at it initially from a male's point of view, I started to view a lot of anal porn and that's where I first came across a sissy video where a man was dressed as a woman and getting penetrated by a dildo.

It fascinated me at a time where I had just got into a long-term relationship but for religious reasons, we weren't able to have sex. The fascination of watching this type of porn lead me to using a cucumber in my bedroom and sliding it into my back passage to try and re-create what I was seeing on the scene, I wanted to see how it felt as I read up a lot about the prostate, and this is where all the problems began. It felt SO SO good, I had the cucumber in between a pillow and I was riding the cucumber in my bed, every time it went in and out I felt a wave of pleasure in my body and I didn't know how to react.

I began immediately experimenting further, booking hotels, taking cucumbers and coconut oil, alongside some of my mum's old lingerie which she wasn't wearing and her older pairs of heels, however, each time after I came I felt absolutely disgusting, the smell of faeces, the sight of me looking back at myself wearing lingerie after I came just sickened me, I threw the stuff in the rubbish and went home but the desires only grew.

Suddenly, I found myself watching sissy porn all the time, heading off to hotels, but this time I bought myself dildos, numerous sets of lingerie, bras, thongs, high heels, stockings, thigh high boots.

I used to sit in the moment and take pleasure from just walking around the hotel room in a full set of lingerie and heels, imagining that I was a woman who was about to get put on the bed and receive a pounding by a man.

I would ride the dildo for hours and absolutely love the pleasure I was getting, alongside imagining I was a women, I would moan and groan loudly as if I was getting pleasured by a man, but then I would get tired and start masturbating with my penis, once I ejaculated, I felt absolutely disgusting, but then, 30 mins later in the hotel, I'd put all the stuff on again and go again until my ass felt like it was hurting or I saw any blood. Then eventually I'd throw everything away the same night, and repeat the process again, wasting thousands of £s over a span of 3 years on hotels, lingerie, sex toys, heels. I'd even do things like buy condoms, fill them up with my cum and let it drip over my stomach to pretend that I had just had sex with a man and he threw his condom off to go inside of me raw.

I'm currently in a long-term relationship with a woman I want to marry, however I'm worried about how my desires will affect my sex life, I still struggle to stay hard, I start pre-cumming within mins and go soft, I ejaculate within 1-2 mins and I'm scared I won't be able to satisfy her.

I am still extremely attracted to women, but, even as I'm typing this, I'm getting so turned on and leaking in my boxers, I don't know what to do about these desires.

The thought of a relationship with a man makes me feel sick, I have 0 attraction to another man's face or his body small things like seeing another guys feet or smelling his breath makes me absolutely sick, but at the same time, the idea wrapping my legs around a man and having him penetrate and pound my prostrate whilst I'm dressed up in my favourite lingerie and heels is literally all I can think of. The thought of giving oral sex to another man and having him ejaculate in my mouth drives me crazy, or having multiple guys ejaculate inside of me, I want to experience it so badly but I'm scared that if I do it once, I won't be able to go back, because once I experienced anal, it drove me crazy for more.

For the last few months, I've had to stop myself from going back into the cycle, I have images of wanting to buy things like buying acrylic nails and spreading my ass cheeks open with them, booking a male escort to have sex with me whilst I'm all dressed up. So far I've managed to resist going all the way, but I find myself masturbating to sissy porn regularly still.

I tried stopping masturbation for 30 days, it did dull the desires a lot, but as soon as I saw a woman in the street with a pair of heels and stockings, all I could think about was wearing them myself, I used to get such a kick out of putting them on, stroking my legs up and down in the mirror and taking pictures of myself at sexual angles.

My initial thoughts are that lingerie and high heels are my biggest problems, for some reason I just feel so good wearing them, in an ideal world, I'd want to have sex with a woman all the time but be fully decked out in lingerie and some thigh high boots. I can't explain what it does for me, it's difficult to understand. Sometimes I will grab a thong and some heels, go to the mirror and just be so satisfied at the sight of my bottom looking round whilst a sexy piece of underwear is wrapped around it, whilst my feet are covered by these shiny heels and my legs are all arched up. But then for me the thought of getting pleasured through my ass also gets me so horny, for me riding a dildo felt like the ultimate all round pulsating pleasure running through my whole body, and some days I feel like sharing that energy with another man but with a real live wet penis is all I dream for.

Sorry for the length of this post, I just felt like my story needed explaining from the core.

 

Thanks for the replies guys:

The anal orgasm is something that I'm struggling to my head around, I love regular penile orgasms, but I just find a new level of pleasure when I do anal orgasms, the problem is the soon as I do anything anal related, I want to wear lingerie and start having thoughts of sex with men, I can't disconnect the two.

I'm very scared of falling into the trap of having sex with a man and never being the same again, I do know what I need to do, but I'm struggling to let go of the pleasure I get from this behaviour, and I don't know how to. I know that after I've done it I feel terrible, but like I said in my earlier post, if I'm on a hotel and I've just had a regular orgasm to get off, I'll chuck the lingerie back on and start riding the dildo within 20 mins because the desires have returned.

I have gone like 30-40 days without masturbation or porn, but even after that, the desires still exist in my mind.

There is one another thing that bugs me, I feel like whenever I hear something about penis size and women wanting bigger penises, I feel like I can't pleasure a woman with my size, the thing of if you can't beat them, join them, if I can't give the woman that size, then maybe I should take a 9 inch instead and let that pleasure me.

I do feel like, if there wasn't this stigma around penis size, or if I had a bigger penis, I wouldn't be as severely drawn into this sissy behaviour. Don't get me wrong, having a 5.5 inch penis is better than being stuck with a 3/4, but it always leaves me with a sense of disappointment when I see it.

 

Also, I read a few stories from the links you guys sent and I'm intrigued by the different ways this desire can be born.

When you start watching trans/sissy porn, this definitely causes it get worse, but... my early desires of wanting to do the action of wearing lingerie or "riding" as if I was a woman, came when I was taking it out of my mum's cupboard at a young age.

At this age I didn't have much exposure to porn other than topless pictures of women. I think I watched my first regular porn video 3 years after I began to crossdress and masturbate, and my first sissy porn experience probably 8-9 years after I began to wear women's lingerie. So that desire to act or dress as a woman was building without the severe porn for a long time.

 

Hi, thanks for the words, I need to hear stuff like this in order to click me out of recent feelings I've been having.

I haven't crossdressed or done anal play in a while now, and I managed to go nearly a month without masturbating.

But during that month, my cravings for sissy behaviour kept building and building, and I eventually gave in and went immediately to watch sissy porn.

And in the last few days I've been spending hours searching for lingerie and heels to buy, and watching sissy porn again regularly, it feels like the month of no fapping intensified my thoughts of wanting to be a sissy, I've even had thoughts of what it would be like to be a sissy escort, I cannot believe I'm getting thoughts like this.

 

I am still extremely attracted to woman, I have had sex but each time it's been very bad, I ejaculate within a minute and I can't get hard again. Also again my size was a problem because at some points my penis would just fall out of the girl.

The sissy behaviour started when I realised I couldn't pleasure a girl, wasn't big enough or couldn't last long enough.

 

I'm not sure, I have 0 interest in ever wanting a love relationship with a man. But I have desires to have sex with men.

Prefer to keep chats on public boards.