tagTransgender & CrossdressersThe Prostate Exam Pt. 03

The Prostate Exam Pt. 03


It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go further then he'd have to admit his true submissive nature and his dirtiest fantasies.

Needless to say he did ask her to go on, he admitted that he was a submissive at heart. She'd then given him a good hard anal fingering and he'd revealed the true depths of submissive tendencies and his worst fantasies to Dr Megan Sutton, or Miss Megan as he'd begin to know her.

Since that first visit he'd talked to her on Skype, been given his 13 new life Sissy rules and then let her down by fucking his Sissy asspussy with his 8 inch black dildo without her permission. She was now punishing him for being such a dirty little slut without permission.

Here he was dildo held balls deep in his slut pussy by his tight black lycra boy shorts, his little so soft clit being wanked continuously between his thumb and forefinger (she liked him to just use the tip of the thumb and forefinger to emphasize the pathetically small nature of his clit/cock) continuing his descent into sissydom.

He'd cum twice on her orders from his now flaccid clit, he was watching Sissy Hypno videos, that Miss Megan had instructed him to watch, all the while looking at Master V's profile (replaying in his Sissy mind, the events of the previous session he'd had with the Gay Master) as she had also instructed.

He breathed in heavily on the poppers each time the Sissy Hypno video told him to, his ass pussy full to bursting the pressure building with the big cock lodged deep in his Sissy pussy. His clit soft and soaked with his sissy cum and the boy shorts holding the dildo tightly in place, with his feet still on the desk.

He couldn't see Miss Megans face anymore, but he knew she might be watching and he had to cum again for her before the next two videos finished. His forefinger and thumb were a blur as they worked the foreskin of his clit back and forward, trying to coax one last orgasm out of his clit. Finally he shuddered for a third time, he had to get cleaned up for his family life to resume.

But first he knew he had to do one last thing, that was to clean the dildo once it was removed from his pussy.

He stood, licking his fingers clean of cum and pulled the boy shorts to one side allowing him to slowly withdraw the big black dildo from his ass. Covered in lube and asspussy juices as his asspussy hadn't been fully cleaned before the session and now he would have to pay for not being able to resist.

He stuck the suction cup base to the desk and kneeled before his dildo, and went to work. It was truly disgusting, but he knew she had everything taped and could ruin him. He simply had no choice and proceeded to do the job as best he could. As he managed to get 5 inches in sucking it clean, his Mistresses face popped back on the screen and said.

"Now that will make a perfect advert for your listing on one of the more extreme gay dating sites I've found. It's a brand new one that focuses on Hard Core Masters who look for raw potential pigs to train further and I think in you, I may just have one."

His mouth was still full of cock as he tried to say "No, please no, not that Miss." But all she heard were muffled sounds of pig pleasure.

He was lifting up off the cock to express his worries but it was not to be.

"Get back on the cock, cocksucker, take in at least 6 inches."

Whimpering like a true Sissy he did as he was instructed.

As he continued to gag, slobber and moan, she told him what she had in store for him.

"So you fly to Auckland for two days and two nights next Thursday, is that correct? Keep that cock in your throat as you answer slut."

"Yes Miss"" he mumbled as well as he could with the 5 inches deep in his Sissy throat.

"Right then you will not cum again for the next 5 days, I will see you here on Wednesday afternoon for an hour long examination as part of your preparation. You'll be given the last appointment of the day and then all the support staff and other Doctors will have left the surgery so we'll be here alone. That will allow me to be much more thorough with your examination. Don't shave until you come as I'll want to do that job personally to ensure that you are as smooth as possible."

"You told me that you sometimes wear pyjamas in bed, well you need to start to wear them every night to hide the panties I want you to wear. I don't want you to eat at all from Wednesday lunchtime. After the examination and prep you'll have to tell your wife you're not hungry and eat as little as possible."

He lifted his head from the cock and said.

"That will be easy Miss, my wife is out next Wednesday night for dinner with her friends and she won't be in until late, I'll only see her for 10 minutes after the session with you before she goes out. Then I'll be off to the airport in the morning before she wakes up." He then resumed his cock sucking hoping against hope that he hadn't pissed her off by stopping his cock sucking for the explanation.

"Ohhhhhh how perfect Sissy, we'll have even more fun than I thought on Wednesday then, Master V will be so happy that I can send you up completely prepared for use by him. What time will you finish work on Thursday? How early can I tell Master V you will be available for his use."

Now he was worried, what did she mean completely prepared, all she'd mentioned was the shaving which he was looking forward to, but what else did she have in mind.

"My last meeting is at 3.30pm Miss Megan, so I should be done by 4.30 or possibly 5pm. Normally I'd then go out for a drink and dinner with the guys at the meeting."

"Well not this time slut, this time you'll be going to see Master V at his place for an all-night session to pay him back for not being in touch sooner. He'll be paying me good money, so you'll do exactly as he wants on Thursday night and Friday night and also Saturday morning before you fly back down, do you agree to this slut."

"Yes Miss Megan I promise to be a good faggot Sissy slut for Master V as you demand. I will not let you down Miss Megan."

"You'd better not bitch, you do everything he says, no matter how nasty. You chose this by stuffing that fucking dildo in your nasty ass pussy earlier, you couldn't even wait. Just like the dirty little slutty sissy whore you are. So now it's time for me to whore you out to Master V."

"Now listen carefully, your homework this week, is to wear panties all day every day and also under your pyjamas at night, sit down to pee every time you go, you're no longer a man, so you no longer stand to pee. No touching your clit, I want those sissy balls full of sissy juice for Master V to enjoy."

"Yes Miss Megan."

"I expect you to be very horny indeed, don't you dare defy me on this Sissy, you don't want that much pain. Bring all your kinky wear and toys to the appointment with me on Wednesday night. Make sure you are well hydrated and that you haven't eaten at all since lunchtime. Try to go to the toilet to empty your bowels before the appointment, then ensure you drink 5 litres of water in the afternoon. Do you understand slut?"

"Yes Miss I understand all your instructions."

"Well fuck off then and get started."

"See you on Wednesday Miss Megan."

"You'd better bitch, you'd better."

Pete cleaned himself up and got ready for the return of his family, but all he could think of was the coming week and more so the end of the week. How would he last not being able to touch his clit for a whole week, shit he'd be desperate for release by the time he saw Miss Megan. Just as she wanted.

Megan was pleased with herself, extremely pleased. She'd only had this Sissy for a couple of days, but because he was already quite an experienced Sissy slut, all she had to do was get him/her closer to her true Sissy potential. Megan figured she was going to have a lot of fun doing that, in fact just todays session and the thought of what she would do to him at the appointment had her pussy dripping.

She couldn't wait to get home, she needed some release. Gaye the receptionist called out to say goodnight and to let her know she was locking the front door and that only Megan was left in the surgery, as was often the case at the end of the day. Thank God for that she thought.

She lowered her panties to her ankles and kicked them off, the aroma of her arousal wafted up to her nostrils, fuck she felt horny now, she reached over to the locked cabinet drawer taking out her girls' best friend the Hitachi Wand vibrator and held the head directly on her clit, turning it on and enjoying the vibrations immediately.

She dipped her fingers into her pussy above the head of the vibrator, lifting the fingers to her mouth to savor her beautiful musky taste, fuck she was going to make this Sissy a perfect slut, she was going to love educating her slut to please men, to worship both straight and gay guys and to love doing it.

It didn't take long for the powerful orgasm too rip through her and she enjoyed the shudders running through her body, the sensitivity of her nipples under her blouse. Resting for a few minutes before picking up her panties and using them to soak up her juices before putting the now very moist panties back on. The smell of pussy was pervading, her sub girlfriend would truly enjoy feasting on her pussy and being told of the training the Sissy was going to receive. Tonight would be one for a lot of orgasms.

Pete got himself cleaned up and ready for the weekend, he needed a little normality of family life too take his mind off the range of perverted thoughts running as a continuous loop through his brain.

The main thoughts were of serving Master V again, kneeling before him as Master V put him in some sort of bondage to ensure he could control him, he had no idea what the prep with Miss Megan would involve, he longed to be able to shave soon but he had to wait. His clit was hard most of the time as he wasn't allowed to relieve the pressure.

He'd failed to follow Miss Megans' orders once already, he didn't intend to make that mistake again. As he went about his family weekend he enjoyed the silky touch of his panties on his clit and between his ass cheeks, riding against his ass pussy.

The week passed so, so, slowly he was desperate to talk to Miss Megan, to hear her voice to lust after her, but she starved him of any attention, he checked his slut mail and various profiles every day, most days multiple times, but no updates at all.

He felt as though he was being starved of attention, which was just Miss Megans intention she wanted him to feel a desperate yearning, to ensure his complete subservience and compliance.

Megan might not have talked to pete her sissy slut, but she'd had long detailed conversations with Master V. He really did want this boi to be his, she'd explained that was out of the question for now. But she also said said that she'd be very happy for Master V to use her Sissy much more aggressively than last time and that the sissy slut wouldn't have any limits which Miss Megan had not set out for Master V.

She asked Master V, what it was that he'd like to do that he hadn't done last time he'd had sissy at his mercy.

"I want to break his little sissy mind, to make him a mindless fucktoy whenever he sees me, to get him to the stage over time where he craves my spunk, where he sucks my cock without being forced, but actually with a desperate hunger. I want him to be my toilet in time."

"Woah there V, that's not on the cards, a urinal yes but not a full toilet, well, at least not for now. Can you accept that."

"I'll have to Megan, it's your toy not mine, although I hope it will be mine again for good, one day. Can I turn it into a urinal for use by more than just me, I'd like to have her in service as a urinal for few hours?"

"OK but who do you want to use him with and tell me more about how you'll turn him into a urinal, or will he just be tied up and pissed on?"

"God no Megan, that wouldn't do what I want at all. I want him totally desperate for release, initially thinking how he can escape. To be properly broken in, I need him to realize that there is no release at all, that it might go on forever. To get him to the stage where he simply gives in to the inevitability of constantly drinking more and more piss. In the end he'll become it in his mind, he will be a urinal, with no other purpose." Master V was smiling at the thought.

"That's when the fun really begins, when you see them stop struggling and they just go on autopilot, when you see the tears stop and the eyes glaze over. Then when I finally release him, he'll beg to do anything to please me and not to be put back into urinal service again. When I say anything I mean anything, he'll be a total slut for me and then for you when I return him, or should I say her." Master V was enjoying telling her this and his cock was rock hard at the thought of his revenge on pete, fuck he would enjoy this and push the limits all the way.

"If I remember properly, pete sort of liked the idea of a bit of forced piss drinking, but he really didn't like the reality. That's why this will break him in seriously. He'll make a much more subservient slut for you after this training I promise."

"I've seen it before with arrogant bratty bois, thinking they'll love it, professing their love to be a truly dirty slut until the reality hits them and then they hate it and want to back out. Then you see them struggle against their bonds, and sob and cry, over time though as they are forced to drink more and more, reality sets in and rewires their brains properly. "

"Shit it sounds like he'll be taken well beyond his limits. I have to say I think it's just what he deserves after your last time with him. Itshould help his long term training if you're right V. But will he cope." Miss Megan was both turned on and slightly concerned about what she was hearing.

"Megan, you don't want him to cope, do you, you want him to be broken and to completely embrace being a total slut, yes?"

"Hell yes, I do, I want the perfect sissy slut, one that never ever questions the dirtiness I demand of it."

"Well that'll be exactly what I will send back to you, an absolute whorish sissy slut. The urinal is just the start of the training I have planned though, I want to get more from your slut boi. I've been thinking about this for the last year and I intend to have my fun."

"So what's your plan, will it be a full recycling urinal?" Megan knew a fair bit having read stories on Literotica of full recycling toilets, but she'd never tried it... Yet." Just talking it through she was getting more and more moist, she loved the way this Masters dirty mind worked.

"Exactly, but there won't be any mention of the urinal training at first. I'll get her dressed in the corset you mentioned. I have some lovely breast forms which I'll glue on, I always think gluing makes them feel semi-permanent in a sluts mind."

"The strings of the corset tied off tightly enough to really heighten sissies breathing, then I'll padlock the strings. At this stage she'll just think she's going to be dressed up to then serve me, she won't know about any others. She'll be so horny as this happens."

As he was telling Megan this he was thinking of the horny thoughts that would be running through sissies mind, she'd already be thinking about a nice sensual but firm session with him, little did she know, dumb slut.

Megan replied "Her clit will be straining against the panties which I'll have locked her into on Wednesday evening, ohhh I should have mentioned I'll take a photo of the serial number of the plastic lock to send through to you, not that I think she'd have the balls to remove it."

"Great I love those little locks, the little sissies and bois feel that once they are on only a Dom or Domme can remove them, they're perfect." He really did like this Dommes attention to detail, it would be fun to work with her on this project.

"The important thing is I want her to be completely horny at this stage, she'll still be her panties from travelling up and I presume you're thinking of plugging her for the flight?" Master V wanted to include Megan so that she was completely bought into what was going to happen, he didn't want any come back on him.

"Yes I'll have her sissy nuts pushed up into her body and taped in place and a piss condom for her so she can pee sitting down on the flight, as all sissies should. I'll have locked her into the panties, the afternoon before, as we discussed."

"So she'll be absolutely desperate to get free of them. Of course I'll also plug her with the Hush plug we discussed, the electric one that works on blue tooth, in case you want to have some fun while she is at business meetings that day. She's only flying from the small domestic airport in the South Island so no metal detectors on the flight up."

"Bloody perfect, so the plug can be set to vibrate when I want and all remotely via Bluetooth and wifi is that right?" Master V hadn't come across these new plugs but loved the sound of them.

"That's right V, such a cool piece of kit, its only 1.75inches in diameter, but is designed for longterm wear. I'll send you the app and put the app on Sissies phone, so that so long as her phone is on the network you can send messages to her phone and control the plug completely remotely."

"The coolest thing is it's super quiet but has really powerful vibrations they designed it that way. You can have her pussy, seriously well prepared for use once you open her up later. I'll send you through the instructions, all you have to do is text through the commands, it's bloody brilliant. You can even set it to respond to sound, so if she's at the airport and they announce a flight you can set it to go off with every announcement. I won't explain any of this, so the first time you set it off will be a real shock to her."

The two of them were loving feeding off each other, all the kinky ideas, even though he was Gay, she was coming to really like the way he thought, seemed like the start of a beautiful relationship.

"Fantastic, this is going to be so much better than the last time I had the slut, although I really did enjoy that, it's just the look in those beautiful come to bed blue eyes of hers, the pleading, I go weak at the knees just thinking about the last time."

"Well V, it sounds like this time will be a lot more fun and be a much better training session for my slut." Just a gentle reminder to him, that the sissy was hers, not his, he was simply renting the slut for some time.

"Great, so once I have the corset on her, I'll release her from the lovely training panties you told me about, then the fun really starts, she'll be desperate to have the plug out and have a shit, so I'll allow that so she starts to think of me as her saviour."

"As I unlock her panties and take them off and say to her to use the loo, she'll be so grateful I may just have her suckle my cock as she sits emptying her bowels, although if she's as good as you think she'll be, she won't have eaten will she? So she might not have much to shit out."

"She better not have, those are her instructions, I'll make sure shes's completely empty on Wednesday night and tell her she can only have smoothies on Thursday before she sees you.

"So she'll need some protein by then, she'll be starving, unless you want to keep her that way to keep her weak?" Megan was getting hotter and hotter as they discussed the session, she wanted to know as much as possible."

"I think having her as light headed and weak as possible, through lack of food is ideal for what I'm after, that combined with a whole lot of poppers should have her in exactly the befuddled state I want." Master V was imagining how pete would feel as he let her go to the loo.

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