Making of a Sissy

THE MAKING OF A SISSY

This story is about how I became a sissy after a long period of time never sure of my role with both men and women. First it's useful to have a clear definition of a sissy:

Wikipedia

"Sissy" (derived from sister), also sissy baby, sissy boy, sissy man, sissy pants, etc is a pejorative term for a boy or man who is not traditionally masculine, and shows possible signs of fragility. Generally, sissy implies a lack of courage, strength, athleticism, coordination, testosterone, male libido, and stoic calm, all of which have traditionally been associated with masculinity and considered important to the male role in Western society. A man might also be considered a sissy for being interested in traditionally feminine hobbies or employment (e.g., being fond of fashion), displaying effeminate behavior (e.g., using hair products, hydrating products, or displaying limp wrists), being unathletic, or being homosexual.

"Sissy" is, approximately, the male converse of tomboy (a girl with masculine traits or interests), but carries more strongly negative connotations. Research published in 2015 suggests that the terms are asymmetrical in their power to stigmatize: sissy is almost always pejorative and conveys greater severity, while tomboy rarely causes as much concern but also elicits pressure to conform to social expectations.

We can see that the role has been regarded as a negative rather than positive view of what is a sissy compared to the traditional gender roles. But the role has changed over recent years to mean different things for different people, especially who enjoy the sissy role.

I never knew any other view of a "sissy" as I grew up in a male dominated world where showing any kind of weakness as a man was frown up on and ridiculed. But the changes in culture made this role more acceptable with the onset of popular culture in music and fashion and gay politics etc. It was okay for men and women to crossdress on an ever changing stage e.g. pop icons, etc.

I got into wearing sexy lingerie and applying make up influenced by glam rock and musical theatre. It was "fun" but also reasonably safe. But in the main my sissy side was closeted and only came out in private rooms with willing partners. These guys enjoyed having sex with a shemale, especially without being "outed" as gay themselves. There were of course lots of bigots still around with the same negative attitudes towards anyone that they saw as different.

My own first experiences of being called a "sissy" was when I met Mistress Neve when I was 19, as she took control of both my body and mind for well over a year. She was an incredibly dominant woman, petite, long black hair and skinny. She had several tattoos of interconnected naked bodies on her arms and legs. Her finger nails were long and painted silver.

I was besotted by her and she could do anything with me at the time. She did teach me a lot about being a sissy as she forced feminized me and controlled all my sexual urges. I was put to the test in every way she demanded of her submissive slaves. I was still a virgin, never having had sex with a woman.

Mistress Neve was the first to introduce me to BDSM and CBT as well as Small Dick Humiliation (SDH) which was her specialty. She organised lingerie and sex toy parties for women groups and had me join her as her sissy assistant. She liked to force feminise me in pink silky panties and bras and flowery dresses with cute slippers. I had to wear a range of wigs, bling and learn basic makeup.

The parties would sometimes get quite risque as the women got drunk and begin to tease me about my small dick and smooth body. This was all part of Mistress Neve's sissy training I began to realise. I had become very pliant and obedient to her demands. Later I attended a sissy training course, ran by Mr Deal, which was very demanding on my own perception of my role as a sissy.

I only completed half the sissy course, passing three day long sessions only by a few marks. Mistress Neve wasn't very happy with my lack of commitment to the sissy cause. I was suitably punished not been allowed to cum for weeks and wear a cock cage. She eventually had me join her in sex sessions with her mature male and female clients, who liked to be dominated as she used various Bondage and SM methods in her cellar dungeon. My role was to assist her in these methods using toys and equipment, like pulleys and ropes. Sometimes she had me suck a client's cock while she whipped them all over.

This was all good learning for me as a submissive sissy slave. Over the months I began to understand perverse human nature when it came to sex. I began to see what role a sissy could do in a more positive, empowering way and it wasn't all about being used or abused but having some choice in the power game of sex relations.

Mistress Neve took on another assistant but she choose a 18 year old woman to help her at parties and sex sessions. I was beginning to be used less and less but only called for to attend sessions when she required me as a sissy bottom for guys wanting to fuck a pussy ass. Also Mistress Neve demanded I had tattoos inscribed on my body that said I was her submissive slave. When I refused several times she would get angry and made me wear a chastity device for days on end. She would constantly humiliate me in front of her friends.

Eventually, I stopped being readily on call and she lost patience and gave me an ultimatum to obey all her instructions or she would sack me. She decided after more refusals to end our contract. It took me months to get over my own feelings about my time with Mistress Neve. She had done such a good job of brainwashing me. I didn't know who or what I was anymore.

It was several months later that I began to feel better and more positive about myself and my role as a bisexual sissy. I had a few nice relationships with both guys and girls. Though the latter sex soon got bored of me in bed, due to my small size dick and they so wanted a "real man" to fuck. It soon became apparent I'd be nothing but my girlfriend's cuckold.

Over the next few years that was my role with the girlfriends I went out with. Yes, they liked me as a "safe" boyfriend, my "cute" looks but because I could never give any girl an orgasm. They demanded my tongue rather than my inadequate "pinky" to pleasure them. I didn't mind this minor role in reality, as I wanted my girlfriends to be happy and enjoy sex. Once they found a big cock guy they soon got rid of me.

So the more this happened, the more I turned to being a sub bottom for tops who loved fucking ass. Not only that but the more I began to crossdress the more guys wanted my pussy ass and girly attention. All it took was for me to accept this was my role in life to serve cock as a true sissy. But I needed to learn how to use my pussy ass and began that side of my training which involved focussing less on my dick and much more on my pussy ass.

I had more extra sissy training which included the hypno bambi sessions, this allowed my mind to be filled with the triggers that created all the obedience required to serve cock. Triggers like "good girl" and "drop for cock" etc made perfect sense for my sissy nature to react to and be in tune with a proper full time sub sissy role.

So after a number of years of following the journey of becoming a sissy, I finally made it through thick and thin. Nothing was ever easy. Nothing was taken for granted. All was hard work and at times very challenging. The following is a sort of ongoing diary, a list of sissy tales, moreso, an honest account of the many sexual encounters I have had over a long period of time leading up to being a full and proper sissy.

Sissy Tales

Returned from Mistress Clare this evening after another housemaid session.

Babygurl had to change like before in the utility room. Under strict instruction sissy maid tasks was to vacuum etc the interiors and wash and wax her BMW car.

After the car looked spick and spam Mistress ordered sissy to shower, lube and remove the clitty sleeve. There was a pink dress hung on the shower room door to wear. No knickers or bra a pair of white frilly ankle socks and pink plastic sandals.

Mistress told her maid to sit in the back of her BMW and wait. The car had those dark tinted windows where you can see out but not inside.

Mistress took her time getting in the car and without a word she drove out of her drive towards town centre. Babygurl asked her where she was going but she told sissy to shut up and wait. She drove around a big open park area as the light faded. Then on the corner of the road a tall man stood waving. She stopped and the man got in alongside sissy.

"Hi, how you doing honey?" He turned to speak to Mistress Clare and said: "So this is sissy Vivien you said you wanted me to meet, hey Clare?"

"Yes" she quickly replied "now get on with it l haven't got all night."

The guy took hold of babygurl and turned her over on the long back seat. He unzipped his pants and without a word slide his cock inside sissy's lubed pussy. Mistress slowly drove her car around the large park area the next twenty minutes until the guy had had his fill. The guy thanked sissy Vivien and as he got out of the car he blew Mistress Clare a cheeky kiss. She told him to fuck off and drove away as he stood laughing. Mistress told sissy she owed the guy a favour so that was the purpose of the drive and sissy should be grateful for yet serving another guy's cock.

The drive back to her home was long as she wanted to call in at a friend's house to pick up some package. Mistress Clare told babygurl she would give her lots of chances to meet nice guys whenever they wanted a sweet little sissy to fuck. And her house maid Vivien was now that girl. On arriving back at her home sissy undressed and continued house cleaning for another two hours. Mistress was very happy with her maid's efforts that she gave her two pairs of silk panties, a choker and a nice new hair brush.

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Just returned from Mistress Claire's housemaid duties. The three hours went quickly.

Maid Vivien cleaned all the windows frames and ledges inside and outside. Then mowed the lawn and tidied up the shed and garage. This took a couple of hours.

Sissy washed and cleaned up before knocking on the living room door and wait to enter.

Mistress Clare sat watching porn on her laptop dressed in a purple silk dressing gown. She beckoned her maid over to her and ordered sissy to unbutton the overall and exposed her clitty for inspection.

"My l'd almost forgotten how tiny you are Vivien! You've shaven nicely around your clitty and little ball sac. Would you prefer a cage again or a clitty sleeve?"

Babygurl replied a sleeve was more comfortable than a cage which often caused rashes if on to long. Mistress Clare nodded and took out a small open ended latex sleeve from a side table drawer and handed to her maid.

"Put this on your tiny piss thing until Wednesday, when you return here for more housemaid duties. The sleeve will help shrink your clitty down to your foreskin. It will help my dear girl."

Babygurl slide the sleeve on her clitty and it felt tight but ok. Mistress Clare seemed satisfied with the sleeve and told sissy to go upstairs to the back bedroom and undress, put on a face mask and lie on the bed. A sheet and two long pillows lay on a super king size bed. There sissy nervously listened to voices from downstairs getting nearer. It was the voice of Mistress Clare ordering a man about and the sound of slapping on bare flesh.

"Get in there you sad old man...say another word and l'll whip you so hard it'll make you cry".

The man blurted out a few pathetic apologies as he entered the bedroom.

"Get on the bed next to Vivien and she will suck your wretched cock while l watch."

The man lay on his back sweating profusely. Mistress Clare ordered sissy to give him a blowjob while she intermittently slapped sissy's bare ass several times and then applied a lube shot in her pussy hole. The man grunted all the time sissy rolled her tongue around his fat cock. Mistress then pushed alongside and slipped a condom on the fat man's cock and said:

"Now climb on his cock sissy Vivien and ride the old man until he shoots his sorry load!"

Babygurl obeyed and sat on top of the man inserting his stubby hard cock in her pussy. Even though it was quite short and average length he had plenty girth to enjoy. He managed to hold off for over twenty minutes before sissy hit the right spot and then he unloaded his seed five or six shots. Mistress Clare laughed at the scene of sissy riding her fat client. She took the liberty of exposing her shaven pussy to the fat man to prove how sexy, untouchable and powerful a Mistress Domme she truly is.

Mistress told sissy to only take the mask off when leaving the room so not to see the man. But sissy couldn't help glancing sideways to see the man on the bed who looked in his early 70s.

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Babygurl did go with Master Ian to his gf's Mistress Clare last evening. He drove all the way there and back and we stayed just short of four hours. In that time Mistress Clare ordered both of us to strip off all our clothes and wear a small apron just covering our privates. Master Ian was given house tasks to clean and tidy upstairs bathroom, bedrooms and carpets and sissy downstairs kitchen, living room and stairs.

Mistress Clare walked around wearing high thigh boots and a sexy dark purple body suit. She held a short handled flogger which she used to occasionally use on our bare buttocks when inspecting our housework. The housework continued for nearly two hours cleaning kitchen cooker, surfaces and cupboard drawers etc. Then tidying and dusting the living room etc.

Master Ian did similar upstairs and when he finished she brought him downstairs to join sissy in the living room.

Mistress Clare said her subs had both done a reasonable job of cleaning her home but could do better. So she said our rewards would be for her to put us in bondage and she would play with us in turn. She told her bf Ian to apply handcuffs and ankles straps and blindfold babygurl. Then add a chocker and lead before caging sissy's clitty with a small chastity device. Mistress said it was difficult finding an extra small cock cage online for her sissy girl. Babygurl then was led out to the conservatory and chained to ceiling hook.

It was cold in the glass conservatory and sissy's clitty shrunk and nipples went hard with goosebumps all over. Meanwhile, Master Ian was given a good flogging as he bent over a chair near where sissy hung. Mistress made him count each stroke and say after each one how much he loved his dominant lady.

Then she turned to sissy and began a series of small strokes all over her naked body. Sissy wanted to get an erection but the cage stopped that and she felt only dribbles of precum were released from her clitty. For the next hour Mistress Clare had her fun with both Ian and sissy. She used a strap on with sissy to fuck her pussy and also she fucked her boyfriend's big cock while he rimmed sissy's ass.

By the time she had finished with both her subs she had them totally under her control as they whimpered like spoilt dogs at her expert methods. Master Ian drove sissy home without saying much but he knew that sissy would return to his gf's house again for more of her dominance.

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Evening visit to new Dom Susan who had one of her young girls with her to see her babydick. Susan wanted her assistant Kathy (who works in one of her shops) to see how to treat a sissy. So it was embarrassing to strip naked in front of Kathy who laughed at your babygurl's undersized clit and smooth body.

She asked if sissy ever desired a woman and if she wanted to fuck Kathy. Of course sissy nodded and smiled at her suggestion. Kathy said she'd like to see how sissy would perform with so little an appendage but she'd love to embarrass her boss's housemaid. So sissy spent a couple of hours house cleaning and afterwards Susan ordered sissy to shower and go to the bedroom where Kathy was lying on the bed half naked.

She told sissy to lie next to her and stroke her body while she played with sissy's clit and balls. She got babygurl's clit erect quite quickly and then went down on it with her mouth wide open taking all few centimetres inside. Susan stood at the door watching as Kathy sucked the clitty slowly making sissy groan. Kathy knew when to stop so to prolong the orgasm and made sissy eat her shaven pussy. While sissy had her tongue deeply inside her cunt she felt Susan come up from behind to lubricate sissy's pussy. And then without a murmur Susan slid a long hard strap on into her babydick girl.

FUCK! It went in deep inch by inch until her belly button pressed against sissy's back.

Susan began several long deep thrusts shouting out to sissy to work her tongue deeply inside her assistant's pussy until she could hear Kathy spurt and cry out with pleasure. This sissy did until Kathy had several wild orgasms and Susan was satisfied with the result. She rammed her strap on until sissy had an anal orgasm and Kathy watched with glee at how much cum shot our of suck a tiny clit for a penis she later said laughing. Susan made sure her babydick maid thanked her assistant Kathy for the privilege of serving her.

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Last evening Madam Susan called to tell sissy to come to her house as the Tuesday visit was cancelled due to unseen circumstances she said. So on arrival sissy was given a long list of house duties and to start immediately whilst she went out for a couple of hours. On her return madam Susan and another young girl called Sam inspected all the rooms until satisfied. Sam then took sissy to shower in front of her which was embarrassing as she then proceeded to shave off all your babygurls pubic and body hair.

She laughed as she pulled sissy's clitty in her hand while the other hand shaved off all the hairs until completely clean.

"There now that's more like the babydick you really are!" exclaimed Sam.

She threw a towel at sissy and told to follow her into the bedroom where Susan was waiting. She had a paddle in her hand and ordered sissy babygurl to lie face down on the bed next to Sam who tied sissy's wrists and ankles so she was spread eagled. Then Madam Susan began to flog sissy.

Meanwhile Sam teased sissy about the size of her tiny clit and bit her ear as the flogging continued. After several strikes Susan got on the bed and began to make love with Sam. Sam and Susan fucked for the next hour next to sissy who could only watch the two in a long scissoring until they had their orgasms. Susan untied sissy babygurl and said that's how a woman needs to be treated and sissy might have learnt a good lesson by watching how it's done.

Babygurl nodded and understood, then got dressed and went home with a shaven clitty and sore bottom

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Master Steve called for me to visit him. He lives in nearby town in a large house.

On arrival a young guy invited me inside. He took me into the living room where Master Steve was waiting.

"Hello, you're Tom's sub?" I nodded.

"So you're wanting to try a mature top?"

I replied "Tom told me you wanted me to serve you Sir".

"

No he's got it wrong... you're here only because you want to be".

"Yes Sir, l guess so".

Master Steve looked irritated at me and instructed his boi:

"Take him to my room...by the way, have you been here by before? What's your name?"

"I was here last year, with Tom. Sly's my name".

He retorted: "I don't remember you."

I followed the young guy to the back of the house through a long dark corridor. He said to call him J. He looked no older than 18. Medium height, slim, blond. He wore grey flannel shorts and blue stripped t shirt. We entered a large room in semi darkness. There I saw a long bench with straps, a large table with toys, etc, 3 chairs and ropes, hooks and pulleys hung from the ceiling. J told me to strip naked while he turned a heater on in the corner. He was very business like. l nervously removed all my clothes. J took them off me to place on a chair.