The Holiday Ch. 01

'Maybe you should go around like that,' she said and gave me a gentle nudge as we walked along the path that separated the town from the beach.

The man walking towards us was covered in tattoos, the skin between the ink bronzed with decades of Mediterranean living. He was completely naked and unconcerned. Possibly because of his age and being comfortable with himself, possibly because of the big cock that swung as he walked.

'I'm not sure I'm equipped for it,' I said.

She shrugged 'you have a nice butt. Maybe people would like to see that just as much, maybe he'd like to see it,' she said and turned her head towards the naked man.

'Would you like that?' I said, but she ignored me.

'I've been thinking about our arrangement and some changes I'd like to make,' she said.

I was just enjoying the warmth of some Mediterranean sun, a heat that lingered long after the sun had set. We wandered from bar to bar, stopping only for something to eat here and there. In a corner of the marina we found a boat that sold pitchers of sangria at candle lit tables. It was easy to enjoy myself with Linda, and I could never get bored of her Italian good looks. I suppose I'm a sucker for something different, though sometimes I wondered if she wouldn't get tired of my pasty Englishness.

We'd been dating for a while now, having discovered early on that we both had an interest in kink. We took it in turns to play the dominant and submissive roles, this weekend it was my turn to be the fuck object but as we were on holiday I thought Linda might like to postpone anything kinky for when we got home to our shared collection of toys. I didn't know that she'd brought plenty with her and had them waiting back in the hotel.

In the safety of our room Linda had me strip and shower while she watched.

'May I have a towel?'

'No, I like you wet. Get on the bed.'

I lay down in the middle of the double bed, the room was small and the bed took up most of the space. The under the bed ankle and wrist restraints were waiting for me. The straps needed a little adjusting before I was secured with arms and legs outstretched and unable to move. Linda stood at the end of the bed, she was wearing a black lace corset that only enhanced her amazing boobs. Just looking at her made me hard. She came towards me and straddled my cock, gently rubbing her pussy against me so I could feel her getting wet.

'I've been thinking,' she said, and slid up my body until I could reach her clit with my tongue, 'I've been thinking that we need to make some changes to our arrangement.' She pulled her hips away so I could answer.

'Okay,' I said, without really paying attention. Linda pressed her hips forward so I was able to work my tongue a little deeper.

'I don't think you're a natural dom,' she said, 'I know you try and everything, but it's not natural for you. That's not your fault of course, it's just the way you're made. So I think from now on you're going to be my slave.'

I wasn't sure if she was being serious or if it was part of the game. She got up and off me, denying me the pleasure of making her cum, drawing it out a little longer. She rummaged through the bag of toys we'd brought with us. 'I've got a couple of surprises for you, which you're going to have to learn to like.'

I recognised the first of them, a strap on dildo. We'd talked about the idea and she knew I was keen, I'd shown her some online that I thought looked good - with ergonomic designs to massage the prostrate. But this was something else.

'I know you wanted one of those unthreatening little jobs, but I decided that if you're going to be my bitch then I'm going to fuck you with something proper.'

I tested the restraints a little to see if there was any give, I was held fast. I could only watch her slip into the harness for the realistic rubber cock. Realistic up to a point, it was a lot longer and thicker than mine, at least 8" with a bulbous head and veiny shaft.

'Do you want to turn me over?' I said, hoping for early release from my bondage. She laughed. 'I saw you struggling, I'm not letting you out. Besides, I want to see the look on your face when I slide this into you.'

Linda took a couple of pillows from the bed and slid them underneath to prop me up, then she began rubbing lube from a squeezy tube onto the strap on.

'This is quite fun,' she said.

'I don't think I can take it, it's too big.'

'Oh I'm sure you'll manage, it will stretch you a bit but you'll soon get used to it.' She knelt between my spread legs and guided the rubber head, I could feel it press against me as she pushed. I could feel the muscles stretching to accommodate the thick head. I let out a groan with the hot pain of being stretched out of shape.

'Look me in the eyes,' said Linda, and I obeyed. 'How does it feel to be fucked by a girl with a bigger dick than you?' She pressed harder, the head entered all the way and there was a moment of relief. It was short, Linda thrust the shaft deep into my ass and I squealed. I felt full and on fire and the pain of being stretched wider than ever before, but it also felt good.

'Do you like that?' she said, 'do you like being fucked in the ass?'

'Yes, I like it.' I said between breaths.

'Are you going to be my little sissy bitch from now on?' She started fucking me harder, rocking her hips back and forth.

'Yes,' I said.

'Say it, I want to hear you say that you're my bitch.'

'I'm your bitch,' I said and she shoved the strap on deeper. 'I'm your bitch,' I said again louder.

Linda pulled out of me and I felt every muscle in my body relax in a euphoria of relief. Then she thrust it back in, hard, all the way, and I screamed.

'Just so you know I'm going to fuck you with this until you can take it all the way without screaming, then I'm going to get a bigger one. But right now I have that second surprise to show you.'

She got off the bed but before undoing the harness and removing the strap on she felt my ass with two fingers.

'My you really have been stretched, you're wider than I ever was after you fucked me in the ass. I bet I could almost fit my whole hand in you now.'

'Please,' I said, with a genuine begging tremble in my voice.

Linda laughed. 'Don't worry, that can be for another night. I want to introduce you to this.' She reached back into the bag of toys and produced something small and made of plastic shaped like a pickle.

'Do you know what this is?' she said, I shook my head. 'This is how I'm going to keep you in line from now to eternity. It's a chastity cage, would you like to see how it works?'

I shook my head again.

'Too bad,' she said.

Linda took the device apart to show me. 'This plastic bit goes over your soft cock, and these metal bars lock it in place with the help of this padlock. There are two keys and without one of them you can't get hard and you can't masturbate.'

My cock had gone soft with the ass fucking but when she took it in her hand I immediately stiffened.

'Oh dear, we're going to have to do something about this.' she said and waggled my cock in the air. 'I suppose it's only fair that you have one last moment to savour.' Linda leaned over to take me in her mouth.

'All you have to do,' she said with her lips so close I could feel her breath on my cock, 'is not cum. If you don't cum, I won't be able to lock you up and I'll let you go. I can't make it any fairer than that.'

I was lucky enough, up to that point, to have had a good number of blow jobs from a few different girls, but Linda's were undoubtedly the best. Her mouth was warm and wet and she used just the right amount of suction and tongue action. I tried desperately not to think about my cock going in and out of her mouth, to distract myself from the incredible sensation of her tongue on my skin. I really tried, but I just couldn't do it, it felt too good. I tensed, held it for a second, and then came in a gush of pleasure. The warm, happy feeling flushed through my body. I felt Linda put the plastic case over me and lock it.

'There,' she said, 'now that's done let me be clear about something, if you ever do anything to make me angry I will break the key off in the lock and superglue it shut. Okay?'

'Yes, okay.' There was nothing else to say.