How i became sissy

[SissySusy]

Hi members,
i'm new on this site and wanted to tell you how i became first a cuckold and then as a sissy.
In 2005 I met a beautiful girl with a strong character. I started dating her and soon we started having sex, but having a small penis (and not very useful), i was asked to become a cuckold.

Aware of my problem, i agreed to become a cuckold and after living together for some time, we got married in 2010.
Initially everything went as usual, together at home after work, we went out with friends, she invited her two BULLS at home (separately) to have sex.

At a certain moment (in 2011), during an argument, I heard these things said to me:
- My BULLS are right, all you have of a man is your name!!
- you're not determined, and you're not sexually useful as a man!!!
I'll turn you into a sissy maid and I will be your Mistress,
If you want to divorce everyone will know about your small penis.
What is your choice?? YES? NO??

I accepted and was called sissy Susy.
Since my training as a sissy started , i made many mistakes (and received punishments too), but after twelve years, i fully accepted to be a sub sissy and my wife is my Mistress.

Some of the main rules set foe me :
- always locked in a proper chastity cage with longer urethral tube (the cage is taken off just to be cleaned but no masturbation is allowed)
- no hair is allowed on my body
- use makeup, wear women's panties , shoes and female clothes at home
- wear male clothes only when at work
- be a good maid and NO complaints
- after sex clean the Mistress and the Bull, if requested
- consider and treat the key holder n°2 "Mrs. Kate" as Mistress (serve Her and please Her when requested)
- respect, serve and please the Bulls that are real men and not just a sissy
- the sissy will ask permission to go out, change her clothes, meet people or use internet

Mistress is gentle with Bulls but very strong with me and keeps me in place.

Who has had a similar experience?

 

[Pampix]

I have almost the same experience but with a less "sissy" aspect but though with a
quite emasculated aspect, not being seen as man by my girlfriend and her lover(s).

I have been my whole life a bedwetter and wearing diapers for that. In the beginning my
girlfriend when she was very much in to love with me did not have a problem with this.
I have a rather small penis and got also ED and PE in the mean time what led to the situation
that my girlfriend did not see me more as a man. But rather as an impotent little not very male boy.

She started in the mean time to cuckold me and stimulated me in that not-manly role.

My feminsation is for me and my girlfriend more a kind of neutralization (being less a man)
and fulfilling a not manly role then a matter of appearance. So not especially wearing woman's clothes.

My girlfriend and myself agreed that the ultimate feminisation/neutralisation would be an orchiectomy and removal of my scrotum.

Till now we can check off:

- wearing overalls and short denim shorts
- body completely hairless
- having less and less PIV sex with her
- when having PIV-sex with her: only aloud to have sex with a condom while she was having bare sex with her lover
- getting problems wit erections because of the use of condoms and the psychologic and emotional aspects of the superiority of her lover
- my sexlife being more and more external to her: masturbation and having to use a fleshlite
- always ******** sitting as a girl
- having had a vasectomy (my previous girlfriend wanted that and then left me ...)
- 2 X a period of HRT but stopped it because of health issues
- chastity cage
- wearing diapers
- pussyfree almost 12 years
- almost impotent (ED & PE)
- never cumming wit a hard-on: two fingers or magic wand
- wearing plugs and mostly cumming wit somehing inserted annaly
- pegging
- clean my girlfriends female parts from the semen of her lover
- serve other men ( sucking and bottoming)
- doing chores (mostly only in my diaper and t-shirt)

 

[SissySusy]

I have almost the same experience but with a less "sissy" aspect but though with a
quite emasculated aspect, not being seen as man by my girlfriend and her lover(s).

I have been my whole life a bedwetter and wearing diapers for that. In the beginning my
girlfriend when she was very much in to love with me did not have a problem with this.
I have a rather small penis and got also ED and PE in the mean time what led to the situation
that my girlfriend did not see me more as a man. But rather as an impotent little not very male boy.

She started in the mean time to cuckold me and stimulated me in that not-manly role.

My feminsation is for me and my girlfriend more a kind of neutralization (being less a man)
and fulfilling a not manly role then a matter of appearance. So not especially wearing woman's clothes.

My girlfriend and myself agreed that the ultimate feminisation/neutralisation would be an orchiectomy and removal of my scrotum.

Till now we can check off:

- wearing overalls and short denim shorts
- body completely hairless
- always ******** sitting as a girl
- having had a vasectomy (my previous girlfriend wanted that and then left me ...)
- 2 X a period of HRT but stopped itbecaus of health issues
- chastity cage
- wearing diapers
- pussyfree almost 12 years
- almost impotent (ED & PE)
- never cumming wit a hard-on
- pegging
- clean my girlfriends female parts from the semen of her lover
- serve other men ( sucking and bottoming)
- doing chores (mostly only in my diaper and t-shirt)

From what you wrote I can see that your situation can be considered similar to mine.
Since my sissy training started, the Mistress proved that I am useless as a man and this explains why I wear female clothes, a tiny chastity cage and often please her Bulls with oral and anal sex.
I do not wear diapers but the urethral tube in cage is a bit longer and it can be plugged/closed in the front and keep my panties always dry.
After almost 13 locked in always smaller cages and no sex, my penis became even smaller, shrank to 1 inch and no erection at all when when I suck cocks, or used for facesitting by Mrs. Kate (my keyholder n°2).

 

[droopy1]

I have almost the same experience but with a less "sissy" aspect but though with a
quite emasculated aspect, not being seen as man by my girlfriend and her lover(s).

I have been my whole life a bedwetter and wearing diapers for that. In the beginning my
girlfriend when she was very much in to love with me did not have a problem with this.
I have a rather small penis and got also ED and PE in the mean time what led to the situation
that my girlfriend did not see me more as a man. But rather as an impotent little not very male boy.

She started in the mean time to cuckold me and stimulated me in that not-manly role.

My feminsation is for me and my girlfriend more a kind of neutralization (being less a man)
and fulfilling a not manly role then a matter of appearance. So not especially wearing woman's clothes.

My girlfriend and myself agreed that the ultimate feminisation/neutralisation would be an orchiectomy and removal of my scrotum.

Till now we can check off:

- wearing overalls and short denim shorts
- body completely hairless
- always ******** sitting as a girl
- having had a vasectomy (my previous girlfriend wanted that and then left me ...)
- 2 X a period of HRT but stopped itbecaus of health issues
- chastity cage
- wearing diapers
- pussyfree almost 12 years
- almost impotent (ED & PE)
- never cumming wit a hard-on
- pegging
- clean my girlfriends female parts from the semen of her lover
- serve other men ( sucking and bottoming)
- doing chores (mostly only in my diaper and t-shirt)

My wife often makes me do my housework in just my diaper and plastic pants and a tee. It's very humiliating when one of her girlfriends stops by for a visit. I try to busy myself in the back rooms or the laundry till company leaves so I'm not seen. Sometimes she makes me hang clothes on the clothline outside where the next door neighbors can see me. They are college girls who rent the house next door. I can always hear them laughing and calling out to me from the gazebo in their backyard.

 

[Pampix]

My wife often makes me do my housework in just my diaper and plastic pants and a tee. It's very humiliating when one of her girlfriends stops by for a visit. I try to busy myself in the back rooms or the laundry till company leaves so I'm not seen. Sometimes she makes me hang clothes on the clothline outside where the next door neighbors can see me. They are college girls who rent the house next door. I can always hear them laughing and calling out to me from the gazebo in their backyard.

My wife often makes me do my housework in just my diaper and plastic pants and a tee. It's very humiliating when one of her girlfriends stops by for a visit. I try to busy myself in the back rooms or the laundry till company leaves so I'm not seen. Sometimes she makes me hang clothes on the clothline outside where the next door neighbors can see me. They are college girls who rent the house next door. I can always hear them laughing and calling out to me from the gazebo in their backyard.

Apparently your wife knows how to play tje game of humiliation. Doing chores in sissyclothing, in panties or diapered with only a teeshirt what makes it even more obvious is quite arousing. Is it visible through your sissyclothing that you are wearing a cage and or are wet?

 

[droopy1]

Yes she is very creative when it comes to humiliating me. She is expert at edging me and allowing me narrow escapes. Sometimes however she can be downright brutal. Way back in high school before we were even married she knew I was wearing a diaper and she panced me in front of the cheerleading squad. She wanted to make sure I didn't go out with other girls. It worked.

 

[droopy1]

From what you wrote I can see that your situation can be considered similar to mine.
Since my sissy training started, the Mistress proved that I am useless as a man and this explains why I wear female clothes, a tiny chastity cage and often please her Bulls with oral and anal sex.
I do not wear diapers but the urethral tube in cage is a bit longer and it can be plugged/closed in the front and keep my panties always dry.
After almost 13 locked in always smaller cages and no sex, my penis became even smaller, shrank to 1 inch and no erection at all when when I suck cocks, or used for facesitting by Mrs. Kate (my keyholder n°2).

My wife told me it's an insult to a man when a sissy tries to dress and impersonate a man. That's why I own no male clothing. She says I must be reminded that I'm not a real and functional man and proves it to me when she makes me watch her get fucked hard by her virile boyfriend while I'm in a frilly dress or a tee and diaper like pampix.

 

[LilSissyCuck]

Feminization and sissification was the obvious outcome when my wife decided that if we were to remain married, since I am not really a man I should become more of a woman

 

[droopy1]

Feminization and sissification was the obvious outcome when my wife decided that if we were to remain married, since I am not really a man I should become more of a woman

I'll bet that wasn't difficult to agree to.👗

 

[LilSissyCuck]

the initial male response from refusal, to reluctance, to acceptance has now cum to holes-hearted passionate enjoyment as a cock-loving slut

 

[Sigp220]

the initial male response from refusal, to reluctance, to acceptance has now cum to holes-hearted passionate enjoyment as a cock-loving slut

Good for you

 

[robbiewillsucku]

2025, Hello wantabe cuckold(s). I am Robbie in Norman, Oklahoma, a bimale with a nice c*ck and nice tits.

If you want her to fuck other cocks then after you fuck her - start licking her pussy clean - do this every time you fuck her then after the 10th time - while you are licking her pussy - I am fantasizing that you fucked a cock earlier in the day and I am licking his cum from your pussy. It is all about pleasing you not my cock. I am OK being a sissy cuckold.

I want you to try this on your wife or GF - do this every time when you suck her tit. Suck her tit like a cock. Bounce or bobb your head on her tit just like you would if you were sucking a cock. Do this at least once a week. Third week, start sucking her tit then tell her that you are fantasizing. Hoping she says what are you fantasizing about. If not, suck her tit like a cock then just say -- I am fantasizing that I am sucking your tit like a cock. Don't wait - you say - tell me to suck your tit like a cock. When she tells you to suck her tit like a cock -- sucked harder and deeper.

Three more weeks -- start sucking her tit then you say - tell me to ask --- May I please suck your tit like a cock cause I am a sub sissy faggot cocksucker. Repeat it often to yourself and to her while you are sucking her tit. Yes I am a sub sissy faggot cocksucker - yes I am sucking your tit like a cock. Dry hump her while you are sucking her tit like a cock and you might just cum on her leg or in your panties.

Email me back (robbiewillsucku at gm ail) and tell me how she responded and what you are doing now to please her.

 

[nicebiguy]

Hi members,
i'm new on this site and wanted to tell you how i became first a cuckold and then as a sissy.
In 2005 I met a beautiful girl with a strong character. I started dating her and soon we started having sex, but having a small penis (and not very useful), i was asked to become a cuckold.

Aware of my problem, i agreed to become a cuckold and after living together for some time, we got married in 2010.
Initially everything went as usual, together at home after work, we went out with friends, she invited her two BULLS at home (separately) to have sex.

At a certain moment (in 2011), during an argument, I heard these things said to me:
- My BULLS are right, all you have of a man is your name!!
- you're not determined, and you're not sexually useful as a man!!!
I'll turn you into a sissy maid and I will be your Mistress,
If you want to divorce everyone will know about your small penis.
What is your choice?? YES? NO??

I accepted and was called sissy Susy.
Since my training as a sissy started , i made many mistakes (and received punishments too), but after twelve years, i fully accepted to be a sub sissy and my wife is my Mistress.

Some of the main rules set foe me :
- always locked in a proper chastity cage with longer urethral tube (the cage is taken off just to be cleaned but no masturbation is allowed)
- no hair is allowed on my body
- use makeup, wear women's panties , shoes and female clothes at home
- wear male clothes only when at work
- be a good maid and NO complaints
- after sex clean the Mistress and the Bull, if requested
- consider and treat the key holder n°2 "Mrs. Kate" as Mistress (serve Her and please Her when requested)
- respect, serve and please the Bulls that are real men and not just a sissy
- the sissy will ask permission to go out, change her clothes, meet people or use internet

Mistress is gentle with Bulls but very strong with me and keeps me in place.

Who has had a similar experience?

Lucky you, I was sissified to. Was so right for me because I soon fell right into it. Right where I belonged.

 

[nicebiguy]

the initial male response from refusal, to reluctance, to acceptance has now cum to holes-hearted passionate enjoyment as a cock-loving slut

I think it's pretty hard for us to try and deny. Once I accepted it I felt it's right where I belong, feels good not fighting it too.

 

[paulhallirl]

I have almost the same experience but with a less "sissy" aspect but though with a
quite emasculated aspect, not being seen as man by my girlfriend and her lover(s).

I have been my whole life a bedwetter and wearing diapers for that. In the beginning my
girlfriend when she was very much in to love with me did not have a problem with this.
I have a rather small penis and got also ED and PE in the mean time what led to the situation
that my girlfriend did not see me more as a man. But rather as an impotent little not very male boy.

She started in the mean time to cuckold me and stimulated me in that not-manly role.

My feminsation is for me and my girlfriend more a kind of neutralization (being less a man)
and fulfilling a not manly role then a matter of appearance. So not especially wearing woman's clothes.

My girlfriend and myself agreed that the ultimate feminisation/neutralisation would be an orchiectomy and removal of my scrotum.

Till now we can check off:

- wearing overalls and short denim shorts
- body completely hairless
- having less and less PIV sex with her
- when having PIV-sex with her: only aloud to have sex with a condom while she was having bare sex with her lover
- getting problems wit erections because of the use of condoms and the psychologic and emotional aspects of the superiority of her lover
- my sexlife being more and more external to her: masturbation and having to use a fleshlite
- always ******** sitting as a girl
- having had a vasectomy (my previous girlfriend wanted that and then left me ...)
- 2 X a period of HRT but stopped it because of health issues
- chastity cage
- wearing diapers
- pussyfree almost 12 years
- almost impotent (ED & PE)
- never cumming wit a hard-on: two fingers or magic wand
- wearing plugs and mostly cumming wit somehing inserted annaly
- pegging
- clean my girlfriends female parts from the semen of her lover
- serve other men ( sucking and bottoming)
- doing chores (mostly only in my diaper and t-shirt)

Just curious - did you get the orchiectomy?

 

[robbiewillsucku]

2025 - How I grew my tits:
When I was in my late 20's I dated a nurse that loved to suck my cock with one requirement - she would finger my ass every time she sucked my cock. Soon she had me hooked on that feeling and she had me and my ass under her control and my ass would open for her and respond like a pussy for her. That how I really started being a sissy. That is how I was trained to have a sissy-pussy.

My lady friend for the past 25+ years, would suck my tits and finger me almost every night for years. Yes she would buy me panties. Yes she would peg me with a strapon cock. Now she tells me to suck her tit like a cock.

Also I would take my standard cock pump and pump my tits. Put the hard plastic tube on my breast and pump and hold for 10 minutes on each tit X three times a week. I have never taken hormones.

I have nice tits but I want larger tits and I want larger areolas. If I had the right play-mate I would be on hormones.

Interested info - https://lactatingfox.wordpress.com/2022/01/15/11/

How would you make my tits larger? Females -- Tell me how you would play with me? Do you like using a strapon? Us sucking each other nipples? Yes I like sucking cocks and I like 3 ways. Males you have to wear a condom if you want to fuck my sissy-pussy.

When can you host? I do like hot chat and I chat most mornings about 6 am central time on google-chat as robbiewillsucku@gmail.com

Robbiewillsucku at g m a i l in Norman, Oklahoma

robbiewillsucku@gmail.com

Jan2025, for the past 60days, I have been taking Saw Palmetto and Fenugreek and Pueraria Mirifica - my tits are getting alittle fuller - my lady friend notice my tits were larger in photos - I have 60 more days of pills so I am hoping for larger tits.

tell me more - show me more - where are you located? when can you host? How will you play with me?