Who is Jessica

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I was surprised at how much free stuff she was giving me but nothing could have compared to what she did next. "Now, three more things before I forget." she said, holding up three fingers. She reached over to the register and grabbed a business card from a little stand sitting beside it along with a pen close by. She turned the card over to the blank side and started writing. "Because you decided to come here to start your journey into adulthood i'm going to give you this" she said as she wrote and slid the card over to me when she was done. In beautiful handwriting the card read 10% off the entire store for life with the initials ET at the bottom. I took the card and read it over a couple times before looking back up at her with a shocked look.

"Elizabeth Thomas, I own this store. Nice to meet you." She said with a proud grin.

I shook my head "I can't accept this, it's way too generous" I said, protesting weakly before Elizabeth cut me off with a wave of her hand.

"You can and you will. Like I said I own this store and I can give any kind of discounts I want. Now the second thing. Your chastity cage, if it doesn't fit properly you can come back and we will find one that fits you." I blushed even more as she talked about the cage I picked out. This beautiful woman knowing I was going to go home and lock my dick in a cage made a shiver run up my spine. I wasn't a huge fan of cuckold porn but every now and then the idea of a woman knowing I couldn't please her with my little dick so she goes out and finds a big man-man got my blood flowing. This was definitely one of those times. I nodded and looked down at the ground. The embarrassment of this whole situation was actually starting to turn me on. I was so lost in thought it didn't even register that she implied she would personally help me find a cage that fit.

"And the third thing." She motioned for me to come closer, so i leaned over the counter a bit as she leaned in as well, getting close to my ear and she whispered "I looooove dominating cute sissy boys like you, if you ever want to play or just need a key holder...call me" she whispered seductively and stuck her tongue out flicking my ear with it and then stood back up with a wicked smile on her face.

I stood there completely frozen. Not only was this gorgeous woman hitting on me, she also knew I was a sissy. It took all my will power just to nod one more time. She slid another card across the counter. This one only read "Mistress Elizabeth '' with a phone number. I took the card not knowing what else to do, I was also very curious. After I took the card she was back to all business like the last 30 seconds never happened. She told me My total for the toys, I paid with cash so as to not have a record that I was here. She handed me the bag of goodies with a wink

"Have fun cutie i hope to hear from you" she said, again adding a seductive tone to her voice. I had never really been attracted to women but I have to admit I was rock hard after this whole interaction. I took the bag from her and told her thank you. I couldn't get my mouth to say anything else. I walked out of the store and got back into my car. I just sat there for a few minutes going over what just happened.

I just couldn't believe it. That woman was not only interested in me sexually which is more than I've ever received before, but she wanted to dominate me which has been my dream for forever. For the second time that day I had to stop myself from making a stupid decision About my love life. All I wanted to do was run back in there, get on my knees and pledge my loyalty and servitude to that woman.

I forced myself to stop thinking about it and I turned the car on. I carefully backed out of the spot and got back on the road headed home. My mind raced the whole way back and my heart joined in the closer I got to home.

All I wanted to do was run to my room and start playing with all my goodies but I had to be smart about it. Dad was frequently gone during the day no matter what day of the week it was. I'm Not entirely sure what he got up to, but I didn't really care at this point. I parked in the garage. I didn't see dad's car so that was a good sign. I reached in the back and grabbed my backpack. I had put the bag of toys in there to keep them hidden and walked in the house.

"Dad! You home!" I called out and got no response. I was being extra careful though so I searched the house and when I didn't find him I sprinted to my room. I had gotten so lucky he was out. I flung my door open and barely remembered to close it before throwing my bag on the bed and emptying the contents. My toys tumbled out and I couldn't contain my excitement. I had no idea where to even start.

I finally decided what to do and stripped off my goth boy clothes. My small cock was rock hard yet again. I grabbed one of the costumes I bought. The school girl one. It had a small white top. One that tied in the front and barely covered anything. A very short plaid skirt. A white thong and a pair of white thigh high stockings. I shivered as I laid the outfit on my bed. I stared at it for a few seconds. This would be the first time I ever cross dressed and it felt like a huge moment to me.

I slowly got dressed in my new outfit loving every second of getting myself prepared.There was no way my cock was going to get soft enough to put on my cage yet so I grabbed the larger of the two dildos I bought and got down on my knees. I held it out, the head facing me like I was kneeling for a real cock and I slowly leaned forward and gave my new toy a kiss on the tip. That was all it took. I opened my mouth and started sucking hard on that fake cock. I did all sorts of things I had seen in porn. I sucked it, I licked it, I slapped my face with it. All I wanted was to be a whore for that cock. After a solid 10 minutes just sucking and drooling on that toy I pulled my mouth off of it, panting. My own dick leaking precum like a faucet. I wanted something in my ass.

I looked at my bed and grabbed the smallest butt plug I had bought and the lube as well. I was so horny by this point I didn't care that I had never had anything in my ass besides a finger or two before. I put a generous amount of lube on the business end of the plug and then I poured more into my hand before reaching back and massaging it into my hole. It felt so good I almost forgot about the plug. I reached back and slowly prodded my tight ass with the slick plug and after a minute of slow pushing it slipped into me and I let out the loudest moan yet. The plug sat so perfectly on my prostate that any movement, any wiggle, sent jolts of pleasure through me.

I crawled onto my bed squirming and writhing In pleasure. I started sucking on my dildo again and was lost in a total state of euphoria. I had never felt this good in my life. I felt so sexy and naughty. I flipped over onto my stomach and got up on my hands and knees. I held the dildo with one hand and kept sucking like I was sucking a guy off in my bed.

I was so consumed with my play and pleasure, that I didn't hear the garage door open and close. I didn't hear my dad call for me. I didn't hear him come up the stairs. I didn't hear him open my door. What I did hear was him yell out in surprise and slam the door behind him as he ran away. It just went from being the best day of my life, to the worst.

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chrono_h3chrono_h32 months ago

Liked the pace of the story. Good start. Looking forward to next part.

AnonymousAnonymous2 months ago

An enjoyable story, I am curious as to the next chapter to come. Will she give in to the mistress, will she go out dressed as a sissy with her dad to the steak house. Looking forward to reading some more on the voyage of discovery

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