Ok even though I’m on a swingers site and have done the threesome foursome thing and been to one or two party’s I would still consider myself fairly “Vanilla” when it comes to sex! Yes I’ve done Oral, Vaginal and Anal sex but then most people by the time they get to my age have. I had been chatting to Cathy on this site for a long long time and our conversations went from every day mundane stuff to some of the dirtiest filthiest conversations I have ever had, it was like one suggestion or comment from the other would spur on the other to say something that they wouldn’t normally have even thought about the normal course of events. One thing we often did as we were chatting was to send each other links to videos of the sort of thing we were talking about. I can’t speak for Cathy but some of the videos she sent me were a little shocking but in the context of our conversations also very arousing. We had met in the spring for a coffee and that turned into some back seat fun which was fairly tame but it was clear from both sides that the attraction and chemistry was there in abundance. Due to her commitments over the summer it meant she couldn’t get away from home for a proper meet in a hotel. Things settled down and in early October we agreed a date and I booked a hotel room. The atmosphere in the two weeks leading up to planned meet was nothing short of electric. The Hotel I booked was in was one I had stayed in before and I knew there was a sex shop within walking distance of the hotel, so armed with information I had gathered from our many conversations off I went to make some purchases. I knew Cathy would be bringing some of her own sex toys but I thought to myself why not add to the night, this night had taken so long to set up I fully intended to make the most of it! 10 minutes later I was leaving the shop with a bag, in this bag was a glass handled flogger, nipple clamps, some chrome chain, a riding crop and a Medium sized Butt Plug. I went back to the room and took all the items out of their packaging washing some of them and arranging them on the table by the bed. I then settled in down in the bar for a drink waiting on the call to say she was on her way. I was half way through my second drink when I got a text message asking me the room number , I texted back the number and got the reply,,,,, meet me in the room I will be there in 5 minutes. I ordered a bottle of wine, two glasses and asked the barman for an ice bucket as I was taking it back to my room. Shortly after as I was fumbling to get the key card in the door I realised that I was shaking in excitement! I set the wine down on the dresser but the ice had a dual purpose, into the ice I put the glass handle of the flogger and the length of chrome chain. I did one final check and as I adjusted the lighting to make sure it was just right there was a light knock on the door. I opened it and there she stood in a short jacket black leggings and knee high boots! Mmmmmmmm a feast for the eyes, I stood back to allow her to enter the room and as I closed the door she removed her jacket to reveal a gossamer thin white blouse with a black lacy bra underneath, I asked her if she would like a glass of wine, but as she put her arms around my neck and went to kiss me she said “No, just fuck me!” next thing I knew my mouth was covered by hers, her mouth was warm wet and inviting and as I put my arms around her back I could feel the swell of her breasts against my chest. Pulling her close she ground her pelvis against me and she could feel me growing against her which in turn made her grind harder and increased the passion in our kiss! I backed her towards the bed opening the first few buttons of her blouse as I went. As she backed against the bed she fell back, I straddled her while pulling her blouse over her head, her magnificent tits there within my grasp straining against her black lacy bra, I reached down squeezing her left nipple through the material while sucking her right nipple again through the lace, OOOOOOHHHHHHH came the low moan from Cathy’s mouth her hips squirming under my weight, reaching around her back I unclipped her bra and took it off her, her dark brown nipples were puffy and erect, mmmm I kissed both of them in turn. Reluctantly letting go of her boobs I set my feet back on the ground and stood between her legs and started taking off her boots, then her leggings and knickers, fuck! there it was her beautiful smooth pussy already glistening with her juices and slightly open so I could just see the entrance to her fuck hole. I’m thinking to myself I’m going to feast on that but as I dropped to my knees to taste her she closed her knees around my waist to stop me, I look up to see her staring at me through half closed eyes and she said JUST FUCK ME!, well it seems I did need telling twice but I wasn’t going to be told again, I pulled my top over my head and after grabbing a condom from my pocket dropped my trousers freeing my now painfully hard erect cock, I rolled the condom onto me, I then reached down and with my thumbs pulled open her pussy lips, bloody hell she was wet! her inner folds were glistening in the dim lights of the room. I positioned the bulging head of my cock at the entrance to her fuck hole causing her to moan OH YES give me that cock! I arched my back and shifted my weight to the balls of my feet and literally sank into her wet pussy. Oh god cried Cathy as she felt the full length and width of me fill her, I put my hands behind the back of her knees and pushed them up to her chest giving me the perfect angle to pump into her pussy. After a few strokes I got the perfect rhythm and stork combination going allowing me to draw out to the tip of my cock and slam back into her so hard my balls slapped off her ass on each stroke and her whole body shook. I don’t know how long this lasted but I knew my cock was getting wetter and wetter and Cathy’s screams were getting louder and louder as I slammed into her, then as I heard her scream OH FUCK YES!!!! I felt her pussy clench around me so tight it was like a fist griping me and she soaked my entire groin area as she squirted her way through her first orgasm of what was to be a very long night! I knew Cathy was a sensual woman but the way she came and the way her pussy clenched around my cock as she climaxed was something I’ve truly never felt before, it was amazing! So then for the awkward bit! Cathy is on the bed stretching and joining her hands above her head grinning like the cat that got the cream, (only she hadn’t got it yet) and there am I standing at the foot of the bed with my shoes and socks still on and my trousers around my ankles, no elegant way of doing it so I leaned back against the dresser got naked as quick as I could took off the condom and joined her on the bed. Sliding up against her I put my arm around her waist drawing her body against mine and coming face to face with her I say Hello Welcome to the Hotel ******** this gets a laugh from her in her beautiful throaty deep voice, I always think a woman is at her most beautiful in the afterglow of an intense orgasm and looking at Cathy now I’m thinking wow I’ve done well here. I go in to kiss her and get a very passionate kiss that draws me into her so that it is almost like we are breathing the same air, I find her nipple with my hand and as I roll and tweak it I feel her stir under me and here breading becomes more intense, we are breathing the same air and it is running out of oxygen as I am becoming light headed. I break away and take her other nipple in my mouth and suck it between my teeth sucking it into my mouth and gently biting down on it all the while squeezing and rolling the other one between my thumb and forefinger. I have never known a woman to react like this to nipple stimulation. I feel her legs opening and here ass grind into the mattress like her pussy is actively looking for stimulation all on its own! Time to move this up a notch, I reach into drawer to retrieve a blindfold I had hidden there and tell her to close her eyes, she does as told and I slip the blindfold on her and she gasps at first and then relaxes, almost in a signal of submission to me. I then reach for the nipple clamps that are combined with a gag that ties around her head putting it round her head I place the O ring gag in her mouth this causes her to let out a low deep moan, she may have said something but I cannot make out what. Settling myself between her legs I start to rub her still soaking wet pussy, getting a low moan for my effort, flicking her clit with my thumb I push one then two fingers into her wet hole hooking them to find her Gspot, this has an instant reaction and I feel her pussy clench on my fingers and her whole body stiffen and her ass lifts up off the bed, reaching up I take one of the nipple clamps and close it onto her left nipple this gets a scream of shock so as a distraction I push a third finger into her and start to finger fuck her pushing in and out of her hitting her clit with my thumb on every stroke, her tits are now bouncing with the rhythm and every time they move the clamp pulls against her nipple, after 30 or 40 strokes she again screams out drenches my hand with cum and clenches so tight with her pussy I have to stop moving my hand. I have never known a woman to react like this, it’s like her whole body has been taken over by pleasure, as she starts to come down from the intensity of her orgasm I feel her relax and I bend my head down and suck her clit into my mouth while removing my fingers from her pussy, her pussy is gaping open and soaking wet but as I flick her clit I see it contract and close before my eyes, I trace my tongue down the puffy lips of her labia cleaning all of her juice from them while savouring the taste. While doing so I insert my thumb into her ass just so she knows I haven’t forgotten about that. I move up the bed and kneel beside her head and tell her to open her mouth, she does as instructed and I place my cock into her mouth and she closes her lips around me sucking me in and flicking the slit in my knob with her tongue this has the desired effect and within seconds my cock is rock hard and bulging. There is still one clamp attached to her nipple so tweaking the other one I attach a clamp to that to, as I do so she gasps and my cock pops out of her mouth. I grab another condom and roll it onto me then then I kneel between her legs again, I take a pillow and place it under her ass giving me better access to her pussy, getting confortable I rub my cock up and down the slit of her pussy using the juice as lube I smear it all over her clit and using the top of my knob I rub up and down her slit flicking off her clit each time, this drives her wild and I increase the speed and pressure and within a minute or two Cathy is screaming herself through another intense wet orgasm. At this point I can feel the heat radiating off her pussy and her lips are red and swollen I tell her to get on all fours and she does, I put further pillows under her hips and tell her to relax, this had the effect that she is lying on the bed face down but her ass is pointing up in the air. I get off the bed and retrieve the chain from the Ice bucket, kneeling behind her I put one hand on her ass keeping firm pressure on her I then use the other hand to feed the ice cold chain into her pussy link by link, when the first link goes in she screams and ask what the hell is that I slap her firmly on the ass and tell her to be quite, as I feed the rest of it into her I feel her relax and moan with the pleasurable sensation of the cold chain against her hot pussy! I leave some of the chain hanging from her pussy. Now I’m going to have some fun with her ass, Cathy has been telling me for months how when the time is right there is nothing she likes more than a good ass fucking, and this seemed like the right time to me. Grabbing some lube off the bed side locker I put a dollop in my palm and rub it over my condom covered cock smearing it all over and giving it a few strokes to get it back to full hardness. I take her hands and put them on the cheeks of her ass and tell her to hold open her ass for me, this she does giving me a wonderful view of her puckered ass hole and her pussy with a few inches of chain hanging out of it, I put my bulging knob at the entrance to her tight hole and feel her stiffen, I apply gentle pressure and open her up and bit and then stop, with just the tip of my finger I push down on the shaft of my cock adding a little pressure to her ass and getting her used to the sensation, after a moment or two I feel her relax and I push the rest of my knob inside her tight hole, OHHHHH she cries in a mix of pleasure and pain so again I stop and give her a moment to get used to the “Full” feeling. I then take hold of her hips and push the rest of my cock deep inside her hole all the way in one fluid stoke causing here to scream into the pillow, I’m slightly worried at this stage that I’m hurting her but as I draw out to my full length she pushes back on me and I take that as my go for it. Pulling her by the hips and trusting forward with my pelvis I ram my cock deep inside here and she screams again this is a scream if pure pleasure and I love it, I just go for it and the harder I bang the more she screams and the more she pushes back on me, I pump away as hard as I can and I am drenched in sweat from the effort, I can feel my cum building up and I feel my cock getting harder and bigger inside her, I don’t ever remember being this carried away in a moment! it’s like I’m in a frenzy, my cock starts to twitch and I scream as I feel my cum explode and shoot past her tight ring piece. This sets Cathy off and her whole body begins to shake as another orgasm takes over, ramming my cock as deep as I can in her ass I reach between my legs and take hold of the chain and slowly pull it out as Cathy continues to shake and orgasm, it’s almost like she had forgotten then chain was there as when she feels it being pulled out of her she totally loses it screaming shaking and squirting all over my hand legs and balls drenching both of us! I stand back on shaky legs and look at her ass gaping open and think whooo this is intense, as I turn to head for the bathroom I notice the flogger sticking out of the ice bucket, I grab it and slide the ice cold glass handle into her ass and as I do her whole body stiffens and her ass clamps around it, I then notice the nipple clamps are still attached so I grab the chain that’s joining them and gently pull them off her nipples, this sets her off moaning and shaking again and I turn and head to the bathroom to shower This is going to be a long night !!!