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Chapter 33
by
Luke575
Where do they go first?
Well they go into the mall
Stephanie’s mood seemed to hit new heights after I kissed her cheek. She was so excited that before I could even get my bearings we were hand in hand walking into the mall. It was strange walking in the heeled sneakers and with the plug inside me, especially when trying to keep up with stephanie, but I was quickly growing accustomed to it enough where it wasn’t the only thing on my mind.
From looking at myself in the mirror before we left, I knew I looked good and unfortunately very much like a girl right now. But that didn’t prepare me for the looks I got when we crossed into the mall. Part of me was terrified I would be instantly found out and it terrified me. What I hadn’t been prepared for was for everyone to be fooled so easily. In a weird way, it hurt my pride that no one seemed to come close to noticing the man underneath these clothes. Not only was he not noticed, but as we strolled through the mall, I noticed more than a few men crane their necks in my direction and watch my ass.
I blushed as a man whistled at me and stephanie squeezed my hand reassuringly. “Don’t worry babe, you’ll get used to it. You look so good right now I’m sure all the guys, and a few girls, will be staring at you and wishing you were theirs.” As she finished she pulled me around a corner and gently pushed me against the wall. She leaned in and whispered, “but they can’t have you, you’re mine Jenny.”
She leaned in and kissed me. This one was different than the other times. Previously it had been lustful and urgent and I had no way of processing. It was like she had been assaulting my mouth. Now however, it was more tender. Her soft lips met mine gently at first, as if testing the water of doing this when not in a charged environment. Just that small bit of contact set my cock to jumping in its cage and I quickly kissed her back. Leaning into me, I felt her tongue moving into my mouth, quickly over powering my own. Her hands started roaming my body as she pressed me firmly against the wall. She explored every inch of my mouth as excitement shot through me and her hands kept sliding lower down my body. They found purchase on my ass and she gave it a firm squeeze as I gasped into our kiss. She pulled her head away while continuing to grope me and whispered, “Jenny, it’s so hot seeing you like this.” Her mouth left a gentle kiss on my neck as a finger slid down the back of my shorts. “This is how you should’ve always looked.” Another kiss to my neck as a finger made contact with the plug. “Haven’t you felt better doing these things with me than anything before?” Her finger pressed on the plug, driving it deeper inside of me. I couldn’t help but release a quiet moan and grasp her tightly as she continued to press harder. “Answer me Jenny.”
Quietly, but urgently I replied, “yes Steph I have. But it’s so wrong. You’re my sister and I’m a man. We shouldn’t be doing this, and I shouldn’t like it.” As I said this I felt some resistance growing inside of me, this was wrong and I couldn’t be swept up in all of this. I just needed to survive a week, that’s all.
Sensing my resistance, stephanie gently bit my ear, eliciting another gasp as a shock of pleasure shot straight to my now leaking cock. Then, as I still basked in that, she pulled out her phone and pressed a button that shook my whole world. The plug inside me started vibrating, hitting new and tender spots within me. My knees started to grow weak and I clutched onto stephanie as I struggled to contain my moans. More and more precum soaked my panties as I silently begged for release. I breathed heavily as I clutched stephanie, staring deep into her eyes, praying she would grant me release. I felt something building deep within me and started pushing myself against the wall to try and get the plug deeper. I knew I shouldn’t, but I had to!
Seeing my desperation, stephanie kissed me deeply again and I drank in her kiss. My entire body was alight as she pulled me in even closer and whispered huskily, “you will get your release tonight, if you’re a good girl today.” Suddenly, she turned off the plug and I almost wept in frustration. I thought we were getting somewhere and she pulls this?! I couldn’t hold my tongue any longer.
Near tears from her shifting attitudes and constant sexual torment, I said quietly but with anger and hurt seeping through my words, “what the hell stephanie? Why do you keep doing this to me? Whatever I did, I’m sorry just please, stop torturing me.”
A tear slipped down my cheek and I felt stephanie wipe it away gently. I looked up at her and saw her eyes tearing up as well. “Jenny I don’t want to **** you at all. Please believe me, all of this I am doing for you. So you can learn who you truly are and be happy. I promise, if you just bear it for a little while longer, it will all make sense and you will be happier than ever.” she kissed me chastely on the forehead and took a deep breath, then a step back. “Tell you what, I think this has gotten a bit on top of both of us. I’ll leave it up to you, you can come with me to the salon, we can get our hair and nails done, get a bite to eat afterwords, go home and have some wine and explore this side of you. You might think it’s all my fault you’re dressed like this and even enjoying part of it, but you know deep down it’s something that’s always been a part of you. Or, we can call off this deal. I can bring you home, we can get you your normal clothes back and I’ll pretend nothing has happened. The question is, do you trust that I want what’s best for you enough to give this a real shot?”
Does he trust her?
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Bitch of a step sister
Trapped and hypnotized
My step sister was always a bitch. She always made fun on me for not being a mans man, for liking to keep to myself and mostly for my thick ass. She just came home for summer vacation and began the process of turning me into her unwilling cock sleeve.
Updated on Feb 10, 2025
by Luke575
Created on Jun 17, 2021
by Luke575
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