I met Richard on the net and we Skyped a few times. He seemed decent and when we Skyped he always broadcast from a room that looked like a surgery. He wasn’t a doctor but asked me if I would indulge his medical fetish. I wasn’t sure but then life is too short? I arranged to see him and a few weeks later, I drove to his home.

Richard’s bungalow is in the sticks and when I called to see him, he answered the door wearing a smart suit, shirt and tie. Unlike our conversations on Skype, he was very formal when he invited me in and directed me to the surgery-looking room. I looked around at a medical examination bed, tiled floor and cabinets with various erotic instruments.

‘Like it?’ he asked. ‘It used to be a Dentist’s home surgery and when I saw this I just had to buy the place.’ Richard then quickly turned back to the ‘Doctor’.

I have never indulged in roleplay so I took Richard’s lead. ‘What is the problem? I think you said that you are felling unwell and might have some sort of anal blockage,’ he insisted. ‘Right, undress and hop on here,’ said Richard as he patted the bed.

I undressed behind a screen and emerged fully naked, covering my cock with a trembling hand. Richard told me to lay on the bed and I did as asked. Its leather covering was cold on my skin. Richard approached with handfuls of chains and restraints. He slotted these through the bed frame and then lifted my legs onto two steel stirrups at the end of the bed, lifting my arse about an inch off the bed. By now, I was feeling more than a little exposed but this grew worse when Richard attached the straps of the restraints around my ankles. To the leather straps, he attached some more chains and on the opposite ends, fastened these using straps, to my wrists. He then pulled them tight, forcing my hands down onto the bed and pulling my legs back as far as they would go.

Richard appeared again, holding a clipboard, checking what he imagined were notes.

‘Hmmm, we need some questions answered. You think you are bi. Have you taken a man’s cock in your mouth?’

‘Yes,’ I answered.

‘I see. And did he ejaculate in your mouth?’

‘Yes.’

‘Swallow his cum.’

‘Yes…’

‘Doctor?’

‘Yes, doctor.’

Richard then placed a cold stethoscope upon my chest and moved it around, listening as he proceeded. He then placed two fingers across my belly and proceeded to tap them with his free hand. I found this amazingly erotic and was so turned on. I loved his touch and the surgical way he examined me.

‘You have an anal blockage alright,’ he pronounced. He then lifted my cock with disdain. ‘And has any man masturbated this to conclusion.’

‘Yes,’ I replied.

Richard tutted with disgust. For a while, he lifted my testicles and cock, closely examining it until the nervousness made me hard. He disappeared and returned with a large spoon, chilled, which he placed on my cock, stating that he disliked patients getting aroused while he examined them. Richard then placed a finger upon my entrance. ‘And this hole. Has this been penetrated?’

‘Yes.’

Fingers or cock?’

Both, Doctor but never bareback.’

‘Good.’

Richard wrote something on his clipboard and moved to the foot of the bed. I watched him look along the length of my upturned body.

‘I will deal with your blockage soon but my conclusion is that you are totally gay. You are a girlie little queer. Do you agree?’

‘Yes, Doctor.’

‘Long term, my suggestion is that you have your testicles removed or neutralised through d**gs. You then must have injections to feminise you. In the short term, you should wear female underwear around the house, find some high boots to fit, shave all of your hair off your body and learn to wiggle that pretty arse. You are wasted as a man.’

‘OK Doctor.’

‘So when we meet again, you will wear women’s underwear, stockings and boots. You can wear these under your men’s clothes but that is what I require. Now let’s look at this obstruction.’

Richard’s cold finger penetrated my anus. He was gentle but then started corkscrewing his finger until it penetrated knuckle deep. He removed it and lubricated all of his fingers. Two went back in and this time he was rough. I yelped and he reported that he’d located the blockage.

‘I’m going to insert an inflatable dildo,’ he advised. ‘I need to see in there.’

Richard returned with a surgical tray on which was a speculum. He inserted this into my arse and expanded my hole. He then filmed it and transmitted it by Bluetooth onto a screen opposite the bed, all the time providing a running commentary. In went the dildo and then the pumping started. I felt my arse getting a gentle stretch and then it grew more until pain replaced pleasure. I wanted to piss and shit but Richard assured me this was a natural reaction and the pumping continued. The images on the big screen were amazing and I saw how my hole had expanded to around 2.5cm wide and was growing until we got to around 3.5cm and the hole appeared cavernous.

For about 10 minutes, Richard played with the dildo moving it gently in and out, watching me squirm under his touch. Occasionally, he squeezed hard on my nipples until I yelped and then he’d return to the dildo, fucking my hole in and out. He disappeared from view and when I looked up at the screen, I saw him unfastening his white lab coat. From behind, he exposed a monster thick cock. I turned my head and instantly, Richard pressed the cock head against my mouth.

‘Open up you fucking sissy fag.’

I did as asked and sucked hard on Richards erect cock. I felt vulnerable and every time I got an erection, out came the spoon to quell my ardour. After a long mouth fucking, Richard moved to tighten my bounds and then he removed the dildo and speculum. I felt my hole twitch involuntarily. Then his fingers rolled around my hole, applying some numbing agent. I was grateful for the relief. Then the pressing of his cock against the outer skin. I looked between my legs. Richard exposed his muscular body and showed me his erect cock. It was huge.

‘I’ve opened your slut hole for you.’ He then moved the tiny handheld camera to my hole and in the screen I saw it open and move back and forth.

‘Push out as hard as you can,’ ordered Richard. I complied until I felt the tip of his cock push through. So far so good. He then pushed harder and the pain was severe. Repeatedly, Richard told me to push out and relax but he shoved his cock fully in. I panted with the pain, hardly able to gain my breath.

‘It’s here. The obstruction. I feel it.’

Richard then thrust hard, lifting my legs off the bed. He started to fuck me and for about fifteen minutes, he thrust me slowly, sped up and repeated. All the while, he crushed my cock whenever there was a sign of an erection. Richard then inserted a finger alongside his monster cock, opening my hole to its widest I have ever known. He started fucking me with this finger and then joined in with his cock. The pain caused me to writhe in agony until pleasure took over at some point. I was so lightheaded by now I was close to passing out. He then screamed ‘I’m cumming in your fucking hole. I’m cumming.’

I felt Richard shoot his load into me. It really struck the sides of my inner ass with such force. Ive never felt anything like that before.

After Richard removed his cock, he unbound me. He wasn’t one for kissing or pleasuring me. I dressed, and only then appreciated that he had bare backed me. I felt compromised, dirty and used. As I pulled on my shorts, I felt his cum ooze out of my hole which by now was swollen and still recovering its elasticity.

When I was fully dressed, Richard appeared, still playing the role. ‘When you get home, I don’t want you to shower for a day and hold in your shit for as long as possible. No wanking for three days. The obstruction will then clear. I will see you back here same time next week. By then I want you fully shaved. I want you in stockings, a suspender belt and high heeled boots. Here is an internet site you can purchase all of these from in a few days. When you come back I will look at that blockage down your urethra which I have instruments to clear.’ He opened the door to his surgery in a theatrical manner and reminded me again, same time next week and don’t forget to dress.

I couldn’t do what Richard asked, when I got home. My arse ached with the fucking and expansion. I released his semen from my ass and wanked off, exploding as I lay in a soothing bath. Now I want you to decide should I go back to him and do as he demands. Let me know. Ive got a week to decide.