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Chapter 31 by Luke575 Luke575

What does she have in store?

We all knew what it was

Her grin grew as she made eye contact with me and stared deep into my soul. She held her hand behind her back and stalked towards me as I gulped. One hand came up to gently caress my cheek while the other stayed behind her back. With a deep sigh she said gently, “Jenny, you could have so much fun and be so happy if you just listened to me. I never want to get rough or be mean to you, you just keep making things difficult for yourself. Think back, every time I have been mean to you, it was because of your own actions.”

I truly had no response to this. There was no part of me that could comprehend the warped world view she must have to genuinely believe that. Sure most of the time her aggression came after I said no to her or something, but the vast majority of those times it was because she was being ridiculous, not me! That being said, given our position now, it might not be the worst idea to go along with her for a bit, but I was still hesitant with her. Softly, I replied, “Steph I don’t want to get you mad, but with all the weird stuff going on lately, you’re scaring me. You kiss me, slap my ass, and do all kinds of stuff, but you locked up my dick, are making me dress weird and all that, how am I supposed to just listen to you?”

She leaned forward and touched her forehead to mine. “Oh sweetie, I don’t mean to confuse you, I just know you’ll be happier if you listen to me and do the things I tell you, even if they seem weird to you. It frustrates me that you can’t see it. Tell you what, do everything I say for one week, with no complaints, and I’ll unlock your little clit and I’ll never tell mom and dad what happened. You’ll even be able to stop listening to me, if you want to by that point that is.”

My heart leapt at the thought of freedom from this cage and her ****, but a week of compliance could spell disaster for me. Then again, if she kept holding this shit over me, I’d be doing that anyway, at least this way, I pretend to smile and I get to finally have my dick free. I was so horny by this point, there was nothing to do but agree. “Okay Steph, you have a deal, but please, don’t make me regret agreeing to this.”

She giggle and gave me a quick kiss that sent heat through my body. Despite all this, I still found her hot, and any contact got my caged cock jumping. Wait a second, just now realizing, did she call my cock a clit? Before I could think more on it or question it, Steph pulled me to the end of the bed and gently pushed my head down to it as she turned me away from her. She started pulling my shorts and panties down and I quickly went to stand and she barked, “down Jenny! We just agreed listen to me, now head down, ass up and relax.”

Reluctantly, I put my head down as she got me to my bare ass, shorts and panties polled at my heeled sneakers. Given recent events, I knew she would have her fingers in my ass soon, and as hard as it was to admit, I didn’t mind the thought. I justified it in my mind, plenty of guys like stuff in their ass, I mean we have prostates after all, but it still felt shameful to allow this to happen. I was so horny though after so long without cumming, and I knew how good it felt, and I agreed to listen to her, so all I could do was wait.

I kept my eyes trained forwards as I heard a bottle squirt behind me and Steph started speaking while she worked. “Now Jenny, we both know you liked it when I had my fingers in you, and I think it’s only right you explore that.” I felt some liquid squirt onto my hole as I shivered. “You might not know this, but they say an orgasm from your prostate feels way better than a regular one.” I felt what I assumed to be her finger pressing on my hole gently but firmly, the slickness of both her finger and my hole trying to coax it inside. “Relax Jenny, I just want you to feel good. Pretty soon, all you’ll want is to play with that pretty hole.” Of course I disagreed in my mind, I would much prefer to have my cock played with, but as this was my only option…I took a deep breath and felt the slender object slip in, forcing a gasp to leave me. “See, it feels good, and this is only the beginning.” Slowly she started working the finger further in, until it was to her knuckle and I felt a strange pulse through my body. It then started pulling out and I felt my insides clench to keep it inside. “Now that your a bit looser, we can do this sweetie.” A second finger joined the first and started working inside a bit faster. I was already breathing heavily and felt my caged cock jump as she got all the way in. She pumped her fingers faster and brought more gasps from me as I got used to the feeling. It felt like she was so close to something, but not quite there, without thinking, I bucked myself back and felt that something just out of her reach. I burned in shame at that involuntary act and Steph laughed. “Oh, so you do like it? I knew it. So I have one more gift for you so you can really enjoy the mall.” With that, her fingers came out of my ass and were quickly replaced by a hard object that slipped into my hole. It was thicker than her finger and went just a bit deeper. It must have been tapered as my hole closed around it. I turned around in the bed and faced Stephanie, panting and embarrassed, but so turned on. I felt pre-cum gathering in my cage and the object touch a special place as I sat on it. I let out a low moan as it did and saw stephanie smile at the noise.

“Oh Jenny, you’re in for such a fun week! Now come on, get dressed slut and let’s go.” With that, I pulled back on my shorts and panties and started walking with stephanie to the car. Unbeknownst to me, with the intruder inside me, I had a very feminine sway to my hips, but all I could think about was the pleasure I had felt, and wondered how I could keep my sanity for the week to come.

As we got to the car, Steph opened my door for me, and I blushed as I entered the car and felt the object shift as I sat down. We both buckled up and as we started our drive, stephanie started to explain the rest of our day to me. “First of all, we need to discuss who we tell people Jenny is…”

Who is Jenny?

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