First Time – Surprise Shemale

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First Time – Surprise ShemaleI’m an eternal masturbator. I’ve always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this? Perfection. Then cam the webcam. I found a couple of sites where you could interact with such beauties and chat and wank in unison. I only ever fantasized about this, as I’ll tell you now, I am straight. The idea of man on man totally turns me off. Shemales however were totally different, yet totally unattainable. For me at least.I used to go on regular trips to Amsterdam with my mates, and we’d all get drunk, spliffed up and go for a wander around the red light district. Somtimes, when we were all no longer capable of walking we’d make out way back to the hotel. The thought of these women was too much and with a raging hard on keeping me sober, i’d sneak out and partake of the Windows ladies.One such time, there was a mob of about 12 of us. I took one such opportunity to sneak off. I wandered around and found one particular corner with this amazing, buxom, leggy brunette. She was dressed in a corset with thigh high patent leather boots (another of my turn ons). I wandered up to the door and was welcomed inside. What an absolute beauty. Tall, flawless skin, and dressed to kill. I nearly bust a nut on the spot.”Have you been to this part of Amsterdam before?” she asked.”Oh yes, many times” I replied”Good” she purred.”What would you like to do”?”I’d love to lick your ass” I spluttered. I was thinking this but hadn’t really thought about it before. “Of course” she said. Wow. what a dream come true.We dispensed with the paper work and I started to undress. She started to take her clothes türbanlı aydın escort off but I asked her not to as I loved the look of what she was wearing. She happily obliged and waited patiently while I de-robed.She beckoned me to lay down and started playing with my dick, which was getting on its way to full mast. Then she positioned herself above me in my favourite 69 position, slid on a condom and started to suck my rigid cock. And there above me was her beautiful asshole, her panties pulled aside enough so I could see its puckered delight. I dived in and she immediately reacted, very positively, while she worked her mouth and tongue up and down my cock. I was in heaven. Such a delight to behold such a gorgeous woman and have her suck my cock while I licked her ass.After much munching and sucking and tongue flicking, she lifted away from my cock and moved away from me to sit beside me.”How was that”? she said, wiping her lips.”Amazing. Fantastic.Like, wow” She laughed gently at my reply.Next she picked up a dildo that was beside her and started licking and sucking it. Wow (again). Then she put it to my lips. “Go on, suck it”. I duly obliged. and started flicking my tongue over the end and then sucking it deep. “Thats it, oh my you are hungry” she giggled. She then put the dildo down and whispered in my ear “Would you like to suck my cock”?I was stunned. What? How could this vision of beauty have a cock. Don’t get me wrong, i’d seen many shemales on my PC, via webcam, in pics and video. But I’ve never, ever been so convinced I was with the hottest female on the planet.”Yes?” hoping that it was the right answer. Then came the ‘great unveiling’. From out of her thong she pulled this amazing piece of meat. That for me there was the single greatest vision I had ever had the pleasure to witness. This stunning, sexy, voluptuous woman, with a cock. I was about to wrap my lips around it there and then, but giggling she pushed me gently back and türbanlı aydın escort bayan said “Hey, slow down. Condom first”. These were the days of super safe sex, so of course that was absolutely the done thing (like when she went down on me). She slid on a rubber and then sat back, as for the first time in my life I began to give head. I started with the usual places that I like to be licked and sucked on and this was obviously the right thing to be doing, as she moaned her approval. I couldn’t believe my luck. Totally at random I picked this corner of Amsterdam and had picked this lady out of all of the windows nearby. I got a bit over excited and nearly gagged myself a couple of times, which she loved.Again she gently pushed me back and leaned in close to whisper. This time she said “would you like me to fuck you?””Yes” was my sub second response. Then 2 seconds later I said “But i’ve never done… this.. ” pointing at her cock “.. before. so please be gentle?” She laughed out loud this time. “Of course I will””She positioned some cushions and asked me to lay on them. As I lay back she lifted my left into the air and propped some more cushions under my ass, to give me more ‘lift’.Then cam the moment of thruth. She started to rub the end of her cock against my pliable, yet virgin ass hole. She rubbed in some lube, positioned herself again and said “Ready?”. “Oh yes. Please fuck my ass”. She smiled and started to push herself into me. The feeling was sublime. she started to withdraw after only an inch and then pushed in again, slightly deeper. Then back out again and deeper still. This carried on until she was balls deep in my ass. My head was back while I was taking in all that had happened and was now happening. slowly but surely she started to fuck me. My legs in the air, me holding them behind my knees, and her kneeling in front of me sliding her cock in and out of my ass hole. I was in heaven. The pumping got progressively harder türbanlı escort aydın and slightly quicker. I was being fucked. I still had the condom on from our earlier 69 but my cock was limp. She took it off and reach to a side table (still fucking me) for some lube and applied it to my cock and started to wank me. She kept up a steady rhythm, pounding into my ass, and now my cock was beginning to harden again. She got me rock hard in no time and I was now in double heaven, being fucked and wanked simultaneously. I could feel her cock bashing against my prostate and my cock was dribbling pre-cum like mad. Then I started to feel the welling up of spunk, the gradual rise of semen and cum juice. That familiar feeling when you know you’re on your way to orgasm. Only this time it was different. It started at my toes, up my calves, my thighs, right through my group, up my belly, mid-riff, chest, shoulders and finally head. My eyes were bulging out of my head, my whole body was screaming out and as I looked into her eyes she knew what was going to happen. I panted out “I’m… going… to…” and then it happened. I came.I didn’t just have ‘an orgasm’ my whole body, my sloppy wet, well fucked asshole, my raging cock all exploded and shook as semen shot up my chest. As her cock pounded against my prostate and each shot of cum and each gasp of breath hit me, well… I’d never felt anything like it. I was most probably shouting/screaming or moaning, VERY loudly as she slowed down the pace as my orgasm subsided. I lay there spent and she said “I don’t need to ask if you enjoyed that” as she pulled off her condom. “Fuck” I exclaimed, panting for breath as she moved over to a nearby sink to wash her cock. Once I re-gained enough composure, she beckoned me over to wash my cock and well lubed and now looser ass hole. I stood and looked at her like I was a zombie, totally speechless. She giggled and asked me if she’d like me to invite her genetic girlfriend in for some more fun. Now if she had asked me that to start with I would have jumped at the chance, but I was spent, physically and financially too (my wallet was empty). I declined and started to get dressed and I tried to mumble my thanks. As I left she pecked me on the cheek and said “come back soon”. I never did see her again, and i’ve never had such an amazing orgasm either.I keep trying though 🙂

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