StepMother is beautiful but bitchy and she enjoys humiliating you accusing you of being a creep and masturbating under her roof. She loves seeing you squirm as she glances down at your crotch for evidence of your erection whilst around her.

One night when she’s out,  you sneak to her room to snoop. You find her vibrator and though it’s wrong start pleasuring yourself with it. edging yourself over and over thinking of her. Obviously being the little prick you are,  you get caught. You try to explain but can’t even speak. Oh oh… what will you do for me not to call your Father about this. For it to be kept just between the two of us…..Anything you want, you hear your self whimper…… Anything at all.

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Your job is on the line after you accidentally sent some gangbang Anal porn in a group email to the whole office. It was distressing for your female co workers and you’ve been summoned to The Chief HR Officer who has zero tolerance for inappropriate conduct objectifying Women.

She decides you must undergo a Sensitivity Training Programme. You will be in chastity and subservient to all female co workers. At the end of each day you will report to Her where She will be waiting for you wearing a strap on. The clip will be replayed and she will mirror it so you can understand the consequences of what females go through when you watch such depraved filth.

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You have to take a file to your intimidating but beautiful new Boss. She’s out so you enter and place the papers on her desk but notice the door to her private bathroom is open. You sneak in for a peep, surprisingly a pair of silky panties are on the floor. Pressing your face into the gusset, you inhale her sweet pungent scent. You are powerless to resist unzipping your pants and you start to stroke. Oh Bugger!  You hear a tiny click…..

Your heart pounds as turn around to see your Boss. You start to stammer as she locks the door behind her. Sitting on her desk she says. I knew damn well what a little pervert you were as soon as I met you. I just needed to prove it. Now I’ve got one over on you and you are going to do Me a few little favours if you don’t want this to go to head office.

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You are a new girl at an exclusive night club In  Southport. The head Madam offers to teach you the skills of hostessing. You believe that the job is just socialising but she keeps hinting that you could make really good tips and you suspect that there is more to the job than you thought, something feels dodgy. Surely this is not some type of Brothel

You decide to quit and tell her you want to leave. But she explains that’s not possible as  she has invested a lot of time in your training so you are obliged to work for at least one night. You try to leave but are tied up and blindfolded then and told VIPs are popping in tonight. If you do everything you can to please them then you will be allowed to go home at the end of the night.

Go to my Sissy page

Your ex is back in town and wants to meet up. You are surprised as you were not the best BF and amongst other things cheated on her several times. She looks sensational on line though so you ask her out for cocktails.  She’s totally changed, physically and mentally and you find her slightly intimidating but are excited when she invites you back to her hotel room “for old times sake “

You feel a bit dizzy when you arrive, maybe be all the shots she kept ordering. You must have flaked out as when you wake you are tied to the bed and she is  above you leaning forward with a ball gag. Let me help to shut up she says. Two wrongs don’t make a right but they make it equal right ? Then she pulls out a case and starts to get her equipment out. 

You have forgotten your allergy medication.  The only place open is the The Southport Kink Klinic where the nurse informs you she can only give you your meds after a quick checkup.

After she takes your heart rate then asks you more questions about your health. These become more and more personal and you start to feel embarrassed and humiliated.  Is how often you masturbate really relevant?  She then informs you saliva and urine samples are required and to remove your pants.  After this you catch her smirking before telling you she also needs a check the back of your throat, your prostrate and finally a sperm sample. 

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Usually with this Roleplay I spend half an hour feminising you in the boudoir then the Roleplay starts as I lead you into the examination room.  You started a new job at an office in Southport and were invited out for drinks with the girls after work on Friday. You admit you got a bit tipsy and must have blacked out because the next thing you know, you woke up in a cheap hotel bruised and aching between your legs.

My job as Matronatrix is to  reassure you that everything will be ok, check for swelling and take swabs for any STD’s.  Then to try help you remember what happened. Was it an office girl initiation or did you get spiked by a creep later on? I may use recollection techniques including hypnotic regression or a re-enactment to help you recall.  Sometimes Sissies have been caught making it all up for attention. Whatever happened Matron will get to the bottom of it.

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You are in Southport at cocktail bar with the boys and see the most gorgeous woman alone sipping white wine. She is a Goddess, way out of your league but you’re feeling brave after a few drinks so you go and try it on anyway.  You act quite cocky thinking this is the way to act in front of such beauty. Don’t show her you are intimidated.

You ask her for her number and to your surprise, she invites you to her hotel room just nearby. When you arrive at her place she ushers you inside & she shyly admits her secret….. she’s a bit kinky and hopes you don’t mind but its always been her fantasy to tie a man up and have her way with him. Like the gullible fool you are you agree…

You are a lingerie salesman and have an appointment with an important buyer in Southport. She is known in the industry as being tough, so when the model doesn’t show, you worry the order may be cancelled. When She suggests you model the  merchandise you are reluctant but she convinces you,  telling you you are not very masculine anyway so it will be fine. She then has you parading up and down while She films you bending over,  striking sexy poses and little dances to demonstrate the wearability of the lingerie.

Each set she picks seems to become tinier and sluttier until you are wearing just stockings  She asks you if you are willing to go the extra mile, as there is just one more thing she needs you to do before she puts in a really big order

To read more about forced femme go to my Sissy page

You are an innocent college boy spending Summer in Southport to improve your English, your host is glamorous and very Milfy. She’s friendly but a little overpowering and seems to be giving you more chores each day. She starts asking you to bring her tea, toast and marmite in bed each morning and then starts insisting on foot and back rubs. Then She referring to you as her houseboy. You feel a little concerned but your English is improving and also you like feeling useful. Then one night she invites you to have a late supper with her, she offers you more and more wine. It would be rude to refuse….

You wake up in her candlelit boudoir, you must have passed out.  She is tenderly stroking your hair wearing nothing but thigh high boots, a strap on and a twisted little smile. 

Stepmother is the ultimate Milf, read more about her here

You are visiting the Beautician for a back, sac and crack wax followed by a massage. A new Beautician convinces you to try a new treatment and insists that you relax by inhaling her special aromatherapy oils. After a few sniffs your head spins, you  feel dizzy and start to lose control then pass out.

You wake strapped down to the bench, a hypnotic voice telling you through earphones that your destiny is to be a Sissy. You can’t move, see or hear but it seems like your face is being painted, your nipples massaged and electric currents are pulsating around your genitals.  You start to feel anxious but are just given more oils to inhale.  It’s easier to just give in and do what she says. 

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You are at Uni and looking for a part time job to supplement your grant. You hear about a new hotel opening and decide to try your luck 

The Female Boss explains that many guests are gender fluid so the staff uniform doesn’t conform to traditional gender roles and are you ok with that? The pay and conditions seem great, almost seems too good to be true and you reply that you are wear whatever uniform the club wants

The Boss takes you to the changing area where there are rails of clothing hanging up, everything seems to be in pink satin, lace or PVC and basically like old fashioned maids outfits with super high heels to match…….

Want to be my Sissy maid?

You are alone on a business trip in Southport and feeling filthy so decide to treat yourself to a sensual massage . You head to the location and are invited in and told to undress and shower then lie face down on a massage table. You then feel yourself being handcuffed to the table and as you look up you see the masseuse slip off her black silky robe to reveal her police uniform. She informs you that you’ve been caught in a police sting by a man hating bitch policewoman. I love catching scum like you She laughs, how sick is it that you feel entitled to just pay for a Women to be sensual. She then handcuffs you and informs you She needs to do a full cavity search to check for drugs. This might feel a little uncomfortable Sir She smirks as She pulls on her gloves and gets out a huge bottle of lube. She then pulls out a ball gag and pushes it into your mouth. After a thorough inspection She offers to give you a caution providing you do whatever She says till She’s done with you

You are lured to a temple and forced to pray at the feet of a Nun then made to worship them before She uses you as She pleases  in a Femdom ritual. Crucifixes, Incense, chanting and a baptism with Her holy water before She consummates your union to her church by bending you over her alter and forcing you to worship her strap on.

You’re in detention again, as usual you’re the only one there. Forced to sit in the isolation room bored as hell. You start thinking about the Milfy new French teacher who sent you there. She said it was for not concentrating, but who could focus when She was wearing a top you could see the out line of her nipples through. All you could think of was sucking her fat juicy tits. You get hard thinking of Her, She was so hot and She knew it but why did She have to be such a bitch. 

You go check the corridor, no one is around, might as well use this time productively and start stroking, you go to the school website and find her profile, her face looks so slutty and you bring your dick closer to your phone thinking indecent thoughts. You quickly get to the edge and it’s hard to not explode. You are in the midst of trying hold off your climax when you hear the door open just as you are squirt all over your phone. Its Her! I know exactly how I’m going to make you clean that up She says. 

It has been two years since StepMother married Father and  within two years She has taken complete control of the Southport country house. She has now started focusing on you. You dreaded and fantasised about spending time with her.  Just her voice made you tremble with fear or lust.  Now She wants to discuss something important. 

You go to your room and are shocked to see She has completely re decorated it. It was all in baby blue and lemon. seems like you are not ready to be in your big boy pants yet She says. I was doing laundry and what I saw is disgusting. There are stains in your underpants so we are going back to basics for now. She opens your drawers that had your calvins then filled with  adult diapers

It’s your first day of training at the Southport Kink Klinic as a new nurse with Nurse Von Kink. She informs you, unfortunately, there are no male uniforms so you will have to wear a female Nurses tunic for now.  She then hands you stockings and pink knickers and insists she helps you also put them on.

Unfortunately, you get an erection.  You try to hide it but she spots it twitching. She tells you the female tunic was just a first day initiation joke but seeing as you are obviously a pervert you will be kept in chastity and remain in the pink knickers until you can be trusted not to become aroused around the nurses. She will remove it and check on it throughout the day and if you can’t control yourself you will have to be securely tied up.