My First Time Shemale Sex
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I've been intending to tell the story of my first time shemale sex for a while, so I hope this turns you on because it's something I will never forget.
I had been looking at shemale porn on the net for a while and found then when I watched shemales fucking guys I got particularly turned on, my cock getting harder than I could ever remember.
I began to browse shemale escort sites for knowing I had to try shemale sex even if it was only ever going to be a one time experience. I read profile after profile hoping to find someone understanding and that is exactly what I discovered in Penny.
She is a busty blonde shemale with a big cock, but very feminine looking who seemed to understand the mixed emotions of guys about to try shemale sex for the first time and I knew she would be the one. I didn't call there and then though, but I kept returning to her profile, looking at her sexy shemale pics of her in various outfits until the day I knew I had to call and book an appointment. Once I had called I was commited and even if nerves got the better of me on the day, I would be chatting face to face with a real shemale. I still wasn't sure if anything else would happen.
On the day, I drove to Penny's house and she answered the door wearing her little black dress, gloves and looking even more stunning than her pictures. She could see I was nervous and took my hand in her gloved hand and pulled me inside. My mouth was so dry, I could barely speak so she fixed me a drink and we began to talk.
Sitting on the couch, I explained my feelings and told her that the fantasy that turned me on the most was the idea of picking a tgirl up in a bar, believing her to be a real girl, then going back to her place and being seduced, before she got a little dominant, handcuffing me before revealing she was actually a shemale with a big cock. The I would be forced to have sex with a shemale for the first time. Penny was very understanding of my fantasy and said she believed she could pull a guy in the little black dress she was wearing. I agreed that she did look stunning.
Penny leaned over and began to kiss me on the lips and I felt my cock twitch as her hand rubbed the inside of my thigh as we kissed. I still didn't know if I could go through with this, but when Penny stood up, took hold of my hand and led me towards the stairs, I followed her to her bedroom. Entering her bedroom I saw a big four poster bed and Penny led me onto it, climbing on top of me before resuming kissing me.
She kissed me on the mouth before kissing my face, neck and began to kiss her way down my body. She undid my pants and as soon as she had freed my hard cock, her mouth opened and she began sucking my cock. I remember thinking at the time that I was finally having my cock sucked by a shemale.
Penny sucked me for a while then letting my cock slip from her mouth, she began to kiss her way back up my body. I was so carried away, my head spinning, I didn't even noticed as she pushed my hands above my head, under the pillow, where she had some special restraints already waiting. They were handcuffs but the joining chain had another attachment on them that fastened them to the bed, but allowed them to spin. I didn't know then, but this allowed Penny to move me however she wanted me without having to unfasten the handcuffs.
Now I was hers for the taking, but she didn't rush this bit. Instead, she removed my pants leaving me naked from the waist down and then stood up to remove her little black dress. Now she was wearing just her gloves, bra, panties, stockings and high heels, all in black. This was when I was at my most nervous, but the restraints prevented me from moving.
Climbing on the bed, Penny turned me over so I was face down then straddled me. She began to massage my shoulders, stopping only to plant little kisses on my back or blow softly on me, teasing me.
Penny kissed all the down my back until her face was level with my butt, then she began to trail her tongue over me, running her tongue right down into the crack of my ass. I wondered what was going to happen next when she stopped, but soon, she was parting my legs so she could use her tongue on my ass. I had never had this before and I felt quite tense, so to break it up, Penny stopped and rolled me over onto my back again.
Straddling my chest, her shemale panties were close to my face and she knelt above my head before pulling those panties to one side, letting her big shemale cock spring into view. It must have been eight inches and now her gloved hand was holding it, pushing it towards me.
“Open wide, there's a good boy” Penny commanded and without even thinking, I opened my mouth to her shemale cock. Penny pushed the end of her cock into my mouth and used her other hand to ease my mouth shut around her cock. Now she held her cock in one hand and took hold of my hair with ther other hand, giving my hair a tug. “Suck it bitch” she ordered.
I really didn't have much option as her hips pressed more and more of her big shemale cock into my mouth. I watched as little by little her cock slid into my mouth. Penny relaxed for a second so she could remove her bra, freeing her large enhanced tits which she began to rub. I looked up her body and realised this is what I had fantasied about. Here I was laid back sucking on a shemales cock as I looked up to her large tits and pretty face.
With my mouth full of cock for the first time, I watched as Penny removed her gloves, pulled her cock from my mouth and laid down on top of me as though she was going to kiss me again. Her hands delved under the pillow and I wondered if she was going to undo the restraints, but neither was correct. Instead, when Penny pulled her hands out from under the pillow, she was holding a tube of lube for my ass.
Penny turned me over, this time moving me around like her toy until I was on all fours, completely exposed to her. She was behind me when I felt her finger start to work lube around my ass, slipping a finger inside my virgin hole to make sure I was ready for her shemale cock. I was surprised how long Penny took lubing my ass, working at my hole with first one finger, then two, applying more lube as required.
My head was spinning more than ever now but when Penny knelt behind me, I almost passed out in anticipation. I could feel her hands spreading my cheeks, her experienced shemale cock hard enough to need no guidance from her hands. I felt the tip touch my ass - I hadn't even noticed her put on a condom - then immediately press harder against me until my sphincter gave way, the head of her cock now inside my ass. I gasped out loud and the feeling made me pull against the restraints.
I expected Penny to say something, but she remained eerily silent as again she pressed her hips forward, forcing more of that shemale cock inside my ass. She pressed more and more, so I could feel her slowly filling my ass with her hard shemale cock. Once she was all in, she began to slowly pull out again. I could feel her cock inching out of me, the feeling so intense I didn't know what to think.
With Penny's big shemale cock almost all the way out, she began to press it back inside me again, this time a little faster, once again, never relenting until she was all the way inside my ass. No sooner had she got all the way in, than she was pulling out. This seemed to last ages as she drilled her shemale cock into me, then pulled almost all the way out, each time, getting a little faster and still she hadn't uttered a word, until now.
“You like that don't you bitch?” she asked.
I couldn't speak, my mouth was too dry so I nodded.
“Good” she continued “because now you are going to get really fucked by a big shemale cock.”
With that, she began to pump her cock in and out of my ass, faster than she had done previously, pressing all of her girly cock into me then pulling almost right out before driving that eight inch shemale cock of hers back into me. I could barely breath as I kneel their handcuffed, forced to endure the onslaught on her cock in my ass.
From time to time, she slapped my ass as she pounded in and out of me for what seemed hours but most likely was no more than 30 minutes. Suddenly her body stiffened and with her shemale cock buried in my ass, her cock twitched as she began to cum, my asshole flexing as her cock throbbed in my hole, filling the condom with cum.
Once she had finished, she told me to straighten my legs, laying out face down but she never pulled her cock out. Instead she let me feel that big shemale cock in me as she kissed my shoulders again.
Eventually, her flaccid cock slipped from my ass, but to me it felt like it was still there. She turned me onto my back and kissed me on the mouth before moving down my body, taking my own hard cock into her mouth.
I watched as her pretty face bobbed up and down on my cock, but the whole experience had turned me on so much, I don't think I even lasted a minute before my cock erupted, flooding her mouth with my cum, which Penny swallowed.
Penny now undid the restraints and I stood dressing, my legs wobbling beneath me.
“I hope I lived up to your fantasy” she cooed.
“For sure” I replied.
Even though I had enjoyed my first time shemale sex, I still didn't know if I would do it again, so I headed home to relax, my mind still reeling.
Over the next couple of days, I never stopped thinking of my first time shemale sex and now as I dialled Penny's number again, I knew I had another shemale fantasy I needed to fulfill.
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