Jamie's Descent Pt. 04

'What,' I whimpered, trying to look back at her over my shoulder. I was becoming really scared now and started to shake.

'Bend over slut, I said,' and she smacked me again on the bottom, pushing me forwards so that my chest was flat against the tabletop. With my hands bound I could not stop her and lying across the table like this, I could not move.

'Miss Fiona. Please don't do this,' I begged her, my voice squeaking with fear.

'But you said this is what you wanted, didn't you?' she hissed in my ear.

I could feel her very close behind me as she whispered, 'You should always be careful what you ask for, because you might just get it.'

She laughed as she said this. She moved round the table to stand in front of me and I felt sick as I saw that she was now wearing the strap on. It jutted out six or seven inches from her groin and she posed in front of me, as if modelling the phallus for me.

'Don't you like it then, slut?' she pouted as if disappointed in my reaction.

'You liked it so much two days ago Vanessa thought you would swallow it.'

My heart sank as I realised this was the same strap on that Vanessa had used in her office two days before; the one that I had swallowed deep into my throat after she had caught me looking at that ladyboy website. 'Maybe you want to kiss it again?'

She pushed it up against my lips and I tried to move my head away. She persisted and began to push it harder between my lips. I had to give in and I let it slide into my mouth.

'Suck it good, slut. You want it to slide in easily into your virgin pussy don't you?' she asked almost innocently.

I stared at her and tried to say something but with the rubber penis in my mouth I just made meaningless noises. She slid it out of my mouth and I said, 'Miss Fiona, please don't do this.'

She scowled, 'I don't think you're being anywhere near grateful enough. I can't stand all this whining, either.'

She stood behind me and grabbed my hair; pulling my head up I opened my mouth to ask her to stop and she pushed something into my mouth. It was a hard rubber ball that she secured around the back of my head with an elastic cord. I stared to gag and she said, 'Breathe through your nose.'

My jaws started to ache almost immediately with the ball gag in my mouth and I slumped forward, defeated, onto the table. I felt Fiona's hands on the back of my panties, sliding her hands over my bottom. She began to rhythmically knead my cheeks with her hands. This had the effect of pushing my cock against the table and unbelievably I found myself getting hard again.

Fiona began to ease down the panties, pausing to slide her finger up and down my crack. I tried to push away from her finger, which of course pushed my cock more firmly against the table. Back and front I was being assaulted. She moved my legs apart with her knee, opening me up even more at the back. Her finger started rubbing against my hole and she began to slide her finger inside, gradually increasing the pressure so that her finger began to slide deeper and deeper inside me. I began to wriggle with the feeling of her finger inside me and that only made it worse.

'We have to open up that tight little virgin boy pussy don't we,' she said, 'we don't want any accidents when you get this big cock inside do we?'

I could no longer think straight. Fiona's finger was now fully inside and it seemed she was filling my insides. Between her finger at the back and the table at the front I was being torn apart with sensation. I was losing control completely and my cock was now as hard as it had been all day. I realised that she had now slid two fingers inside me and I now began to feel less uncomfortable as I became used to having her fingers there. I had stopped moving away from her and almost against my will I felt myself moving backwards against her hand.

'Oh, so we do like this then,' she purred as she felt me wiggling backwards. 'I knew you would, you little pussyboy.'

I could not stop myself from pushing back to get as much of fingers inside as possible. Fiona started to push harder and I felt her fingers move in and out of me. She was finger fucking me and I loved it!

Suddenly, she pulled her fingers out and I felt so empty as her fingers left a vacuum in my ass.

'There, that's opened you up nicely,' she said. I felt something cold being applied to my hole and I realised that this was some kind of lubricant.

'Don't worry, baby. Here comes your new lover.'

As she said this I felt something much harder and larger than her fingers at my passage.

'Relax, relax, relax, my little sissy,' she cooed as she began to push harder against my hole.

'Relax, try to pretend you're having a shit and push downwards,' she said as the tip of the dildo began to move inside my ass.

She rocked backwards and forwards, gently at first and then with increasing pressure as the phallus began to move past my ring and deeper into me. This started to hurt and I close as my eyes as tears of pain welled up into them.

'Urnghh, mmggrgh,' was all I could manage to say through the ball gag. 'Easy tiger,' said Fiona.

Fiona eased back and then moved forwards again, the dildo again pushing past my ring. This time it wasn't so bad but I still bit down against the gag as she continued to push it deeper inside me. Suddenly, it was inside me and the pain began to ease a little. Fiona paused again and I felt her bend down to give me a kiss on the back of my neck.

'That's so good, little sissy. You've been very brave. Now, you get your reward, you get to cum.'

With that she started to rock forwards and back so that the rubber cock started to move within me. I squealed again through the gag and Fiona rubbed her hands across my back in a soothing way.

'Sssh, sssh,' she cooed as you might to a baby.

She continued to rock in and out and slowly the pain ebbed away as I got used to this thing inside me. How long Fiona did this for I don't know and just when I began to feel the pleasure I can't say. But somehow and sometime I began to feel that this wasn't so bad and then I started to feel aroused by what she was doing. I realised that the cock was massaging my prostate and that if I pushed backwards I realised I could make this feeling even better. I started to move back as Fiona thrust forwards and the feeling of pleasure began to grow.

'Good girl, I knew you would love this,' said Fiona her hands still massaging my back. 'You were made for this, little sissy. This is what you want, isn't it? But you want a real man's cock next time don't you? You want to bend over in front of some stud with a prick that's as hard as a steel pipe. You want to beg him to fuck you, you beg him to let your ride his monster cock. You want him to drive his throbbing dick into you, so hard that at first you beg him to stop and then you beg him never to stop. You want him to fuck you forever.'

All through this Fiona increased her pace and she was by now fucking me hard and fast. All I could feel were the waves and pan and pleasure that were washing over me. I was being overwhelmed with sensation and I could feel that wonderful warm feeling that builds in your groin, as you know that you are going to cum. I could feel my orgasm grow deep within me and suddenly I felt myself tense and then my cock exploded. I could feel myself cum and cum. I had never had such an orgasm in my life. It seemed to go on and on without end. Fiona was now pumping furiously and she cried in triumph as she saw me cum.

'Yes, yes, yes. You're a real sissy now. You're a real pussyboy.'

She stopped fucking me and pulled out of me. She reached round and pulled off the ball gag. I slumped forwards onto the table, physically and emotionally ravaged by what I had just gone through. Fiona grabbed me by the hair and pulled my head up. I looked through only half open eyes and saw a small red light high up on the wall.

'Smile,' said Fiona brightly, 'you're on candid camera.'

Vanessa and Lisa watched the video feed as I looked straight at the camera. They saw my wild, make up smeared face, slack with exhaustion and spent lust. They saw me try to say something and then Lisa clicked off the feed. They had worried if Fiona had gone too far when Jamie blacked out but in the end it had worked out really well. It had turned into one of their best ever set ups. The film of the whole session, captured on the three secret cameras in the room, would be edited and on the website later that night. The two women knew that this one would get a huge number of downloads.

'This always makes me so horny,' said Vanessa, her voice low and dark with anticipation.

'Me too,' replied Lisa, her hands reaching out to unbutton the other girl's blouse as Vanessa leaned across to part Lisa's lips with her tongue.