tagTransgender & CrossdressersThe Prostate Exam Pt. 02

The Prostate Exam Pt. 02


It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her.

She then persuaded him to confess some of his darkest fantasies and desires to his Doctor, always easier when you have 3 fingers deep inside a submissive males asshole. She'd ordered him to send her all his kinky email addresses and passwords for each and every site he used, Literotica, and the BDSM dating sites he used.

Every sub guy has profiles on some of these and she knew that being able to explore his likes, dislikes, emails, messages and profiles would give her his darkest, dirtiest secrets which he never shared with anyone. The secrets would be hers alone, to know and more importantly to exploit.

Her view was always make them vulnerable, make them very horny, make them eager and then as sure as eggs are eggs, subs always gave far too much information away. Just as she knew he would, Pete was no different. Persuading him to give her the passwords was far too easy, a sub with a gaping ass and a hard cock were easy meat for her to prey on.

She spent a good few hours sifting through the profiles, The FL profile provided a wealth of information, the people he was friends with, the messages he'd posted, the photo's he'd liked or posted.

Just from this alone she now knew that what she'd hoped was actually true, he was a fucking sissy, or at least had fantasies of being a "Latex Fetish sissy slut" as he called it. She knew he'd never be a convincing woman, but he could be a convincing fetish slut and she could put him to work as one, that was for sure.

She could see the sissy hypnosis sites he viewed regularly, the emails to Dommes and more interestingly to her, emails to Male Doms. These gave so much away about him, yes he obviously started with Fem Dommes, but her little slut to be, had also visited some Gay Masters too.

On these visits to Gay Masters he'd initially backed out of prospective meetings with Masters on the first couple of attempts, like a little scared sissy. She'd see to it that never happened on her watch as his Mistress.

So now she knew he was genuinely bi, even if he said gay scenes needed to be forced for his little slut brain to cope. In reality he was truly bi and just needed to be freed to be the best Sissy he could be.

One BDSM contact site he was on showed his many attempts to hook up across the world on his travels. But only a few were successful, one with a couple in Toronto, a Bi Master and his female sub wife. Judging from the pathetic apology from pete after the session, all the slut had managed to do was to suck the guy off and eat the cum, but didn't manage to go further than that in reality. As far as Megan was concerned that was just the first fence he'd jumped, she'd demand and expect so much more from him.

Then a session with a very gay, older Master from the North Island. The session with her slut dressed as a sissy was pretty hard core in the end, but again the emails stopped after the session. She was going to have to get to the bottom of this.

Finally what sounded like the most intense sessions by far were with a TV Mistress Dee in Sydney.

Megan had actually come across Dee before and shared a few messages with her. Getting in touch about her new sub might be worth it, as the silly slut had even posted photos obviously taken by Mistress Dee in the in the session.

So Mistress Dee might, at a stretch remember him. That would open some serious possibilities for the next time pete visited Sydney, but this time under Miss Megan's control.

She now had three people to follow up with and hoped she would have some answers before she spoke to her sub for the first time since the prostrate exam and forcing him to eat his own cum for her amusement and his training.

She sent the emails and messages describing her new sub, telling each of the three dominants what had happened in the exam session (leaving out the detail that she was a doctor and telling them she simply sessioned with pete).

She went into every little dirty detail about the sessions they had had with him (from the emails and his saved photos) and the messages back and forth and even attached the photos she found on petes profile on FL to try to jog their memories.

She'd barely scratched the surface of his profiles, but now categorically knew he was into forced cross dressing, full sissification, that he could easily be forced to suck cock, drink piss and even eat other mens cum.

She knew for many aspiring sissies and subs, that eating other mens cum was a very difficult hurdle to jump.

That many in her experience, baulked when they were faced with the reality of eating cum or even sucking cock for the first time. Even though they had expressed the desire to do it before a session started.

But his case was different, he was in simple terms a slut, a dirty little slut. Absolutely perfect and already experienced at jumping one of the crucial hurdles, she would continue to put in front of him as his training progressed.

With pete she wasn't having to start at the very beginning, she could skip to much more depraved tasks straight away, how delightful she thought.

Pete knew nothing of her actions, he did though realize just how much he had given away, but didn't have the faintest idea of just how she would use it.

Now here he was utterly desperate to hear from her again, waiting for an email from her with his next instructions, his cock hard in his trousers, his asshole twitching in anticipation.

He checked his slut email for the tenth time that day and his heart leapt and his cock twitched as he saw an email from DoctorDomme in his inbox.

He breathed in deeply, trying in vain to settle his heartrate. He wanted to make the moment last a little while longer, to savor it. Since the sexual, deep prostate exam she'd given him, he'd built this moment up in his mind, was he about to get the true Mistress, who he had searched for and longed for years for.

As he opened her email he was breathing heavily and his cock was hardening in his trousers. He was both aroused and very nervous.

"Hello Pete, I hope you've been eagerly awaiting my instructions, in fact I just know that you have. It's time to start

your training proper now. I've found out a lot about you from your profiles, good little slut for sending those through.

Mistress Dee from Surrey Hills in Sydney, Master Ted from Toronto and Master V from Auckland all send their love.

Now sign onto Skype bitch, I wish to talk to you right now."

His heart was truly racing now, fuck he'd forgotten about Ted in Toronto,, who was much more into Corporal Punishment than pete would have liked, but if Miss Megan had talked to him or his partner she'd know that all he had managed to do was to suck real cock for one of the first times that night, and that he'd swallowed on command.

Ohh fuck there was even a photo of him sucking Masters cock on his Fetlife profile. Now he came to think of it he remembered the photo of him, with his head tipped back and a mouthful of cum, showing it to his Master before he was given the order to swallow.

Master V though had really used him extensively. It was the second time they'd met, pete remembered the first time in Wellington when he'd backed out like a scared little boi, when he'd run away with his tail literally between his legs.

But the second time he couldn't back out, he wasn't given any choice that time. Master V had instructed him to dress in his black leather corset, to padlock the laces together at the back so he couldn't undo it.

He'd instructed him to put the door on the latch in his nice motel suite, so that he was terrified some member of staff or another person other than Master V might come in to find him displayed as per his Masters instructions.

He'd been instructed to be shaved completely on his cock, balls and ass crack, to have a thorough enema and to lube his asshole well.

He'd then had him take a lot of poppers, then to text Master to say he was ready. The he was instructed by text to put on his ball gag tightly, to chain his thighs and padlock them to the legs of the foot stool he was bent over.

Then to hood himself and finally to padlock the wrist cuffs together under the foot stool and then to throw the keys to the other side of the room. Master V had also made preparations.

So this second time, there was no refusing Master V, there was no way he could refuse, just as Master V had intended. He'd simply walked into the open motel bedroom to find pete as ordered.

He locked the door and looked at his gagged, hooded, cuffed and chained slut over the low foot stool, kneeling with his legs held wide apart and with his asshole clean and lubed and ready for use.

Pete just heard him say "Good little Boi, now you're ass is fucking mine, God I'm going to enjoy making the most of this after you ran away from me last time."

To make sure he got his fix, he'd fucked pete hard for an hour or so before he even took the hood and gag off and then to ensure that he didn't hear any qualms from his sub he simply stuffed his cock deep down pete's throat.

The session was extremely intense and hard core, petes little cock was hard throughout the session giving away his true feelings, he was absolutely loving the pure degradation and humiliation.

But Master V was after true love and a 24/7 relationship, which pete as a married father couldn't even think about, even though the session had been one of the best of his life.

As for Mistress Dee, God he'd loved his two sessions with her, she was a statuesque TV Mistress, heavily into Gonzo porn and loved to film her subs in close ups, gagging on her 6 inch clit as she throat fucked them. Or to film their screaming faces as she plunged a big dildo into their sissy pussies.

She'd walked out of the dungeon in towering 6 inch platform thigh pvc boots, a leather corset and that lovely short black bobbed wig. She looked amazing, but very much out of place on the suburban street.

She'd sauntered down the street to where she'd instructed him to wait. Her heels clacking on the pavement as his breathing quickened.

There he was in his business suit, fresh from a meeting as she came up to him, standing well over 6 feet tall and she'd stroked his face before she put a collar and leash on him out in the open and then led him back to his fate in the dungeon.

3 big burly working guys got out of a parked truck to go for a beer and for one horrifically sexy moment he'd wondered if they were part of the session, he was both horrified and frightened.

Instead they simply laughed, made a couple of jokes and he heard the words sissy faggot as they walked away. The start of the session was intense and it had got more extreme by the minute, when he'd finally cum he was completely in sub space.

The pictures he had on his profile on FL showed pete fully dressed as a latex sissy slut, heavily made up face, sucking cock, drinking piss, face smothered in cum all in glorious close ups. They also showed some very large butt plugs, dildos and balls going deep into his sissy ass pussy. Mistress Dee had really taught him a lot and stretched him a fair bit.

So just in that one sentence in Miss Megans email, she had him completely. She knew far too much about him, his limits and hates but more importantly she had photos of two of the sessions, incontrovertible proof of what he was.

Now pete genuinely realized he was in much deeper than he'd first thought. Shit now he was worried, but still so, so horny.

He was in his office at home out in the guest cottage, blinds already drawn. Cock straining against his briefs and jeans.

The unmistakable sound of Skype opening, brought him out of his thoughts. He saw that DoctorDomme wanted to add him and accepted her invitation.

Then the video feed came on and he was looking straight at her beautiful face.

"Hello slut, lovely to see you. I have to ask how did you feel when I mentioned your slutty liaisons from CS?"

"Knowing that you now know about them, both excited me and scared me Miss Megan."

"Good it should have, you really didn't tell the truth when I asked you to tell me your darkest secrets did you slut?"

"I did Miss Megan, I admitted to loving forced sissification and forced bi, eating cum and drinking piss, what did I miss out Miss Megan?"

He was almost pleading, not wanting to displease her, now even knowing the implications of doing that.

"Well slut I've seen all of your emails to the gay Masters you visited, you wanted to be forced, but you loved it, you needed it. You said forced sissification, but that's nonsense, isn't it?

You love to dress sexily don't you bitch, you love to be in your corset or your PVC body and your stockings, don't you slut?"

His head hung down and he simply whispered. "Yes Miss I do."

"You do what slut?" she was making the point to get him to voice out loud, his dirtiest proclivities. In her experience, getting this part over, no matter how painful, was a very big step in creating a perfect sissy slut to be used and whored out.

With this one though, she'd managed to get to this point so much earlier and easier than with any of her previous sissy sluts.

He may not look the part, far too heavy set, he'd never be anyway near convincing. But with the right outfit, many men who liked bigger ass pussies to fuck would enjoy the fetish sissy look, she'd find some guys who loved this sort of slut. That's what she was good at.

The outfits would have to be carefully chosen but she could already see this sissy slut in her minds eye, as a latex or pvc clad fetish slut. This was going to be fun for her, maybe less so for him.

"I do like to dress as a sissy Miss, I do like to be used by Gay men."

"What else slut, tell me it all."

"I love to be fucked by men, by TV's, by women with strap-ons, I just love to be fucked and stretched. I love to be made to eat cum, I love to be made to drink piss."

"So what are you slut???"

He pondered for a moment, trying to cover all the things he thought she wanted him to cover in one sentence.

"I'm a fetish sissy, gay faggot slut, a cock sucking, cum and piss drinking bitch Miss Megan."

"There, that's much better slut and I just filmed you saying that, so there is no way to back out even if you wanted to, which I know you don't want to."

"I now own you sissy, remember that above all else, I can end your life here in this small town.

I will be using you for some years, training you to reach your Sissy potential. How does that sound to you?"

"That sounds wonderful thank you Miss Megan." He meant it, he'd always wanted to be controlled.

"Now before we go on, I want to explain the new rules you will live by. I will send the list through on Skype and I expect you to read it carefully and keep a copy slut."

The message notification beeped and here was the list he would live by for his Mistress from now on.

1.Your pathetic cock is no longer a cock, now it's your clit for my amusement. We will both refer to it as your clit from now on.

2.You will only ever squirt from your clit when I command it. Every single time you cum you will eat that cum. Even if you fuck your wife, which I'm guessing is not that often, you will lick he clean of every globule after. Whatever you have to do to achieve this, make it happen.

3.Your asshole is now no longer yours, is it my sissy ass pussy to use and you will refer to it as such. I will determine when it is filled and what it is filled with.

4.There will be days when you will have to drink every last drop of your own piss and indeed some days all of mine.

5.Your ass pussy, your sissy nut sack will be shaved completely smooth at all times.

6.You will watch every Sissy hypno video which I send through to you.

7.You will not approach any other Mistress or Master unless I have instructed to do so.

8.You may like photos or add people on FL, but you cannot approach anyone without my orders or consent.

9.There will be two training regimes, an easier one for when you are at home and then a much more taxing one for when you travel.

10.I will purchase some of the things you need as a sissy slut, but I know I'll get paid back from your work on your travels in time as I whore you out. You will set aside $100 per month for required purchases.

11.You will bring your toy bag and clothes to your next examination with me at the surgery. Every kinky thing you have I expect you to bring to show me.

12.You will find some form of activity that gives you an excuse to be out of the house and out of contact from you wife, once every two weeks on a Thursday evening from 8pm until 10pm.

13.You will wear the panties I tell you to everyday under your work or casual clothes, no matter what.

"These are your lucky 13 rules, which you will live by, to ensure you are trained to reach your absolute potential as a Sissy Slut."

"Do you understand and accept all of your Sissy rules pete?"

He hesitated for a few moments and then nodded his head as he said "I do Miss Megan, I accept the rules as your Sissy."

"That's a good little Sissy slut, we're going to have so much fun and you'll love having me train your mouth and ass pussy over and over and over again."

"We'll also be adding profiles on 5 or six more extreme Sissy dating sites and the most extreme gay BDSM sites for your slutty Sissy persona, but all in good time. I'll obviously have access to any and all passwords to all of your kinky accounts."

"Finally you will start to exercise more and eat better and lose at least 10 kgs in the next 3 months, there will be major punishments if you fail to do this.

We need you to look better than you do now. You want to be the best Sissy slut you can be don't you pete."

This time no hesitation at all,. "I do yes Miss Megan, I really do." she had him, hook line and sinker, he was hers

"Excellent then I guess we are ready to begin Slut."

"Now get your 8 inch black dildo which I've read about in your emails and bring it here bitch."

He reached over to his toybag, which was next to him for just such an eventuality and got the lovely dildo.

"Well that's a perfect size Slut, stick it to the desk in front of the computer, making sure it's in full view of the cam and then drop your trousers and show me your clit."

He did as he was instructed as fast as he could he was desperate for release.

He stood there with his trousers around his ankles looking truly pathetic his clit as hard as it ever as straining upwards for attention.

"Put your fist around your clit snug with the base of it Sissy. I want to see just how small it is."

He carried out her instruction wrapping his fingers around his turgid clit, with just the head peeping out above his closed hand.

"Ohh how sweet it only just pokes out of your hand, no wonder you're a sissy, you could never satisfy a real woman with that."

"We'd better see if your cock sucking skills are more impressive, now drop to your knees and suck that cock, stroking your clit all the time with just your thumb and forefinger under the head of it, that's all you'll need for something so small."

She was making him focus on the finger and forefinger only to make him fully aware of how pathetic his clit was, to take away another little bit of his manhood in her transformation of him into a full sissy.

He did as he was told, taking the head of the black dildo in his mouth and slowly lowering onto it, holding just under the head of his clit and retracting the hood from it to get his pleasure.

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