Doctor in My Hole Part 2

Thank you to my readers for their suggestions following Part 1. After my session with Richard, I admit to being scared by the prospect of meeting him again and on his orders, i.e. dressed in women’s underwear, something I disliked let alone entertained. It was this specific condition of his that left me wretched for several weeks. I pondered just returning to see him but instead I called him to see if he would relent.

Richard was quite aloof when he answered his mobile. I believe he recognised my number. It seemed that he just wanted to get straight to business and he asked me if I wanted another appointment and whether my imaginary anal blockage had recurred. I went along with his fantasy and said, yes to which he then stated, ‘I have an appointment window in three day’s time at 7pm sharp. But…if you do not come with your lady’s attire I will turn you away. Understand?’

‘Look,’ I said, ‘I have a bit of an issue…’

The phone went dead. I called back and when Richard answered, he was clearly angry.

‘What don’t you understand about conditions? They are there for obeying. No women’s underwear, no appointment. Well?’

I relented and agreed that I would be there as per his conditions. For several days I pondered how I could get some stockings and knickers but internet shopping, though the most anonymous course, would take too long. Instead, I rooted around in my wife’s drawers and found some sheer holdups and lace knickers. I removed them, knowing she was bound to wonder where they had disappeared to but thought I might get them back without her noticing.

Come the day, I called on Richard, clutching a sports bag full of my wife’s underwear. He was very cold again and simply waved me into his surgery.

‘Get in there quickly and get undressed. Have you brought the underwear?’

I confirmed I had to which, Richard replied, ‘Hmmm. You have quite a problem don’t you?’

I hurried into the chilly surgery and behind a screen, I undressed. From my bag, I took out the first stocking. This just felt disgusting but I managed to hop up and down while pulling it on. I then did the same with the other. My legs felt weirdly encased. The knickers were ludicrously skimpy and far too tight, hardly encasing my balls and cock. I stood there for what seemed an eternity until the door opened. Richards soon appeared from behind the screen and shouted in horror.

‘You look awful! Look at your legs. Have you shaved?’

I had no idea what he was asking. He ordered me to take off all of the underwear and then he returned with an electric razor, some soap and blades. Richard ordered me to sit down on a nearby stool and without asking, he commenced shaving my legs with the electric razor. He then lathered me up and used the hand razor to complete the job. In no time, he was finished and then he hesitated while looking at my groin. ‘That has to come off too.’ He gripped my cock and started shaving my balls. He then asked me to stand and bend over. Slowly he moved the electric razor between my legs and across my hole. I admit it was a huge turn on. When I turned around, I had an erection.

‘How many times have I told you to stop your hard-ons?’

Before I replied, Richard slapped me hard across the face. He then ordered me to turn around and bend over. I knew what was coming. A huge whoosh sound came from behind me and then I felt the sting of Richard’s cane. Then a second, third and fourth whip came lashing down on my bare buttocks. ‘Two more,’ said Richard, ‘and then put on the underwear again.’

My erection subsided and I proceeded behind the screen again, where I pulled on the stockings and knickers. At this point, I half wondered whether to end the meeting but something inside drove me forward. When I emerged, Richard ordered me onto his surgery bed. In no time, he shackled my hands to my side, secured my legs apart and in the air and then fastened a tight collar around my neck. Like before, he passed his hands over my chest and stomach, humming as he did and making various observations like, ‘that doesn’t sound good. Another obstruction.’

Richard’s hand eventually wandered to my cock. He lifted it up and asked, ‘Have you considered what I said before about being castrated chemically or otherwise. I can give you injections to stop that futile erection too; it’s really becoming a nuisance isn’t it?’

‘Yes doctor,’ I replied meekly.

‘Well, do you want castrating?’

‘I don’t know doctor,’ I strained to reply.

‘At the end of the day there is little I can do for you unless you agree. You are a faggot aren’t you? A little queer desperate to serve other men with your hole. You need to be feminized but…. the choice is yours.’

Richard leaned over and wiped my brow. He then placed a collar around my neck to a chain attached to the bed. I could look up a little, just enough to see the TV he had positioned beside me. He turned the TV on and to my horror, I heard the door to the surgery open. I strained at my leads and looked up. A man appeared above me. He was bald with a goaty beard and like Richard, was dressed in a lab coat.

‘Meet Frank,’ said Richard. ‘He is a doctor, too.’

I felt really uncomfortable at this point especially when Frank started examining my body like Richard had done earlier. His touch was careless and rough. He pressed down sharp upon my belly and said,’ An obstruction Richard. Just here.’

‘Appears so Frank,’ agreed Richard.

I was about to cry halt when Richard inserted some kind of bung into my mouth and fastened it around my head. My mouth could not close despite my biting down on the bung. I was muted.

Richard urged me to look at the TV next to me. I turned my eyes and saw Frank holding up some kind of snake-like long dildo. He was lubing it and then Richard filmed with his camera pen as Frank moved aside my knickers and inserted it into my anus. The head was broad and I screamed out though this was muffled by the gag in my mouth. Several times, Frank twisted and turned the dildo until the tip entered me much to my relief. He then pushed it in and out until the dildo had travelled several inches inside. To my surprise, Frank got to my second sphincter and pushed hard. The pain almost made me faint. He laughed aloud and continued pushing. It felt as though the dildo was inside my stomach and the pain just got worse. I tried to scream but the noises flowing from my throat only served to excite Frank.

Richard hovered his camera pen over my belly. Frank told me to look at the screen. ‘See this. Watch this baby coming through!’ He pushed and wriggled the dildo until it bulged in my lower belly. ‘God no,’ I said to myself. He is destroying me. I was helpless. Frank started to push some more and again told me to watch. I saw him angle the dildo upwards until it pushed my belly up, just under the navel. Up and down it went, Frank laughing all the while. I felt as though I was going to shit my innards out when Frank started to take the dildo out. Occasionally, he would move it up and down or wriggle it to make my belly bulge. As it passed my sphincters, I screamed muffled cries. Richard then attached a funnel to my gag.

‘We are going to have to unblock from the mouth first. Your obstruction is so deep.’

I wondered what on earth was in store when suddenly I saw Frank feeding his thick limp cock into the funnel. In seconds, I felt the piss straining through into my mouth. I tried to halt it but Richard grasped my collar and squeezed. I involuntarily drank Frank’s piss. He stopped and then on Richard’s orders to fill every hole, Frank pissed into my nostrils and ears. The hot piss burned my mouth and face.

Richard then looked over at me. ‘We are starting the lower flush now.’

I looked at the screen as Richard passed his camera pen to Frank. I saw the funnel removed from my mouth and inserted into my arse. Richard leaned over and with a semi hard cock, began to piss. He seemed to continue for minutes, filling my arse with his hot piss. When he stopped, Frank somehow mustered more piss and continued filling me. A bucket was then placed between my legs. I was instructed to hold the piss for as long as Richard ordered. Finally, I could not hold it anymore and it gushed from my hole into the bucket.

Richard looked over at me. ‘Did I say release,’ he asked. I shook my head. Richard looked at Frank and nodded. I looked up at the screen and saw a cane whipping down on my belly. Richard then lifted my cock. ‘No!’ I tried to scream but the cane came down on my balls. The beating lasting ten strokes by which time I could hardly breathe due to the pain. Richard zoomed in on my balls with his pen. I could see lash marks and blood. My balls felt as though they would explode.

Frank joined Richard between my legs and I guess the rest was inevitable. Frank started masturbating furiously until his cock was enormous. He unbuttoned the rest of his lab coat and without sympathy, he pushed his cock into my unlubricated hole. The stretch took my breathe away again and my back arched against the restraints but it was no use. Frank remained inside me for probably half an hour. He pulled his cock out, plunged it back in, bent his knees to twist it inside my hole and stretched my ass to the limit. I felt as though my hole was broken when Frank finally came. He reached over and squeezed my neck so brutally while cumming that I nearly passed out. All the while, Richard looked deep into my eyes. Then I saw him unbutton his coat.

My ass was sore and felt broken when Richard entered. He was much slower in his movements but then built into a crushing orgasm. I felt his sperm shoot inside me over and again as he pumped his cock into me, all the time encouraged by Frank, ‘Fuck him, Richard, fuck the little slut. Fuck his sissy hole.’ When Richard started to cum, Frank leaned into my face and said, ‘There you go. l there you go.’

To finish the job, Frank entered me again, this time half limp. I don’t know where he got it from but again he mustered more piss and emptied out inside my ass. At the same time, Richard pissed on my chest, his squirts of urine ejaculating across my aching, whipped belly.

When they had finished, Frank disappeared and Richard unleashed me. It was all too much. I started to cry while sat on the side of the bed. Richard approached and put his hand around my head. He caressed me, reassuring me that it was OK and that I would be alright. I then felt him move aside his coat and there again was an erect cock. I took it in my mouth and sucked until Richard came into my mouth. He walked away and washed his hands before leaving the room. Frank then stroemed in.

‘Where the fuck are you going?’ he asked aggressively. ‘Lay down you fucking slut.’ I then watched as he pushed his cock into the tops of my stocking. He wanked himself furiously until I could see spots of cum pushing through the stockings. He grunted loudly as he wanked himself to finish and then he walked away.

I had no idea what to do so I took off the underwear and placed it in a bin in the surgery. I dressed and went to leave. As I pulled on the door know, a hand came over my shoulder. It was Richard.

‘You’ve done well today. That was a surprise for you but I know it’s what you craved for. Two men fucking your mouth and ass, pissing on you and degrading you.’

I nodded because he was right. I needed it that way.

‘When you return…because you will, I want you to come with some more lady’s underwear but this time I want you to buy them from our local corner shop, you know the one with the nosey shopkeeper. She’ll know you are buying them for yourself because you’ll ask for large size to fit a man. Have you got that?’

I nodded in agreement, shocked at what he had in store.

‘And you need to think about castration. Once you’ve made up your mind, I want you to tell your wife that you are now gay and that you are no longer in need of spunk and a cock so you might as well rid yourself. If you don’t, remember, I have you on a recording of all that we have done today.’