Hung like a Grape Ch. 02

Anal

The story of our sissy heroine continues… We left things in the last chapter where a female coworker uncovered “Sherry’s little secret” and proceeded to humiliate and dominate her. This is part two of three. Thank you to those who reached out for suggestions and hope you enjoy this chapter. I am still new at this and appreciate any guidance either below or in email form.

*****

The party

Lisa felt a surge of power as she realized just how much of a wimp Sherry turned out to be. She had sensed something during the “Gals Night” that she was dealing with a small dicked sissy. She had noticed that the sissy had confidence problems and likely would succumb to her power at some point. Lisa had totally underestimated how quickly this transformation would happen. In one night, she was able to confirm her suspicion that “Sherry” had a tiny dick, got her to dress up in panties, skirt and blouse. She and her friends were even able to get pictures to prove it! Now she was ready to take totally take control. She was having a party the next evening so she had about 24 hours to seal the deal.

Stephanie and Kelly left around 10:00 that night; Lisa and Sherry sat down and talked. Lisa did most of the talking and filled up Sherry’s wine glass.

“OK Sherry, I hope you feel good about our new relationship. Things are really going to change now. You are going to stay over here tonight, and I am going to get you ready for the party tomorrow night.” She instructed me to go upstairs and we headed to her bedroom. She told me to get on my knees. I saw her go to her dresser and she got out a large black dildo and a strap on harness.

“Now I am going to need to break you in as a genuine sissy and make you my property. First thing, I want you to take the dildo and put it into the harness for me.” I immediately complied. “Now start licking the dildo, bitch.”

I started licking the dildo- up and down the shaft. Lisa then instructed me to twirl my tongue around the tip of the dildo so that it became very wet and slippery. bursa escort “Now start sucking it” she instructed me. I took the dildo into my mouth and started going up and down on it. I tried my best to put it all into my mouth, but it was very difficult given its large size. I also was working on not having my teeth touch it. My jaws really starting aching, but I knew this was important training. “Bitch, focus and get to work on that cock and look me in the eyes! You have to be able to tell what oral techniques please your man.” she shouted at me. I got back to work and looked her in the eyes. It was so humiliating to see how she sneered at me while I sucked on the dildo.

“OK, it’s time to take your cherry and mark you as mine. Lean over the side of the bed- rest your chest on the bed and kneel. She put some pillows under my knees to elevate myself, so she could enter me.

“Here’s some lube; put it around and inside your ass. I will need to stretch you out before the party tomorrow. Trust me, you’ll be glad I did. This dildo is what I consider a “starter” for the real thing.”

Lisa then pulled down my panties and hiked up my skirt. She positioned herself behind me and started to move the dildo towards my pussy. “Hold your cheeks open and beg me to fuck you.”

“Please Miss Lisa- fuck me with your massive cock. I am holding my cheeks open as a symbol of giving up control to you. Please take my cherry and make me yours!”

Lisa moved the dildo towards my ass; I helped guide it in as best I could with my hand. As the dildo entered me, I tried to relax but the pressure and pain were intense. Lisa pushed her hips towards mine and started forcing herself into me.

My eyes bulged in pain as she continued sliding the dildo into me. Inch by inch she took my soul away until she finally stopped. She was totally inside me and she started pumping in and out. She didn’t even have to tell me to groan like a whore. “Oh my God, Miss Lisa, please keep fucking me; it feels malatya escort amazing!” I meant it. After the initial pain, it felt so good I couldn’t believe it. I pushed back on her to get into a good rhythm; it was the most powerful sexual experience of my life up to that time. Lisa continued pound me for 20 or so minutes until we were both exhausted. She finally pulled out, leaving me with a gaping hole and an intense need to do it again. I begged to have her fuck me again but she wanted me to be horny and needy for the coming evening. She had me take the dildo out of the harness and insert it all the way into my ass for the night.

“OK bitch, it’s time for you to take a break and get some sleep. We have a busy day tomorrow. Don’t take the dildo out of your pussy until I tell you it’s okay,”

I woke up early the next morning and shaved and showered on instructions from Lisa. I pooped the dildo out (after instructed to do so) and I noticed it seemed to slide out easier. Maybe I was really stretched out. I was told to make sure I had no hair on my face. Lisa handed me the outfit from last night; panties, skirt and blouse. She instructed me to get into the feminine clothes and climb into her car; we were off to the mall to do some shopping. We got out of the car when we got there and walked into the mall. I was totally humiliated dressed in woman’s clothing but wanted to please my new Mistress. She told me not to say anything unless I was specifically told to do so. We went into Victoria’s Secret and an attractive clerk came right over.

“Hi- I’m Amy. How can I help you?”

“Hi Amy, I’m Lisa and this is Sherry. She is going to help me host a party tonight and I need something sexy for her. The sluttier the better.”

Amy picked up as to who was in charge. “OK, how about a sexy nightie? Let’s see what we’ve got that would fit her.” I cringed when they used the feminine form when talking about me.

“Perfect” said Lisa and we went over to the Babydoll section. çanakkale escort She handed me a very sheer pink nightie and held it up to me in the store to see how it fits. “Hold it up in front of you, Sherry” said Lisa. “I want to see how this looks on you. And stand over here in this open space so more people can see you.” Lisa then spoke to the ever growing crowd. “Ladies, this sissy will be hooking up with some hot guys tonight; she needs to be as sexy as possible.” There were about 20 women in the store who now knew my fetish. The giggling started. They gave me three more to hold in front of me and Lisa asked the women in the store to vote on which one I should get. They voted for the pink nightie.

“Hey Amy, can she try it on?” asked Lisa.

“Yeah, but she’ll need to go to the larger changing room.” said Amy.

So, I walked over to the room to try it on and was shocked to see about a dozen women come after me to watch. “Strip, sissy and pose for us” ordered Lisa. I did as I was told, and the laughing began to really kick in a big way and when I was naked they started howling. “Oh my God, have you ever seen such a small one?” Asked one. “Yeah, but it was on a newborn baby” commented another.

I had to do sexy poses for them after I had put on the nightie. I noticed most had gotten their phones out and were taking pictures of me.

After a while, the nightie fitting was finally done, and we paid for the purchase to the applause of everyone in the store. I put my skirt and blouse back on, left the mall and went back to her car. Lisa drove us back to her house. I spent the rest of the afternoon cleaning, dusting and vacuuming her house. At about five, the caterer arrived with food and after flirting with him, I paid him with my credit card, including a nice tip.

Lisa then looked at her watch and said “OK, Sherry, it’s almost six—time for you to get ready. Take a shower and here’s an enema kit for you to use. Make sure you clean yourself out completely; you don’t want to piss off any of the guests who will be showing up. Put on the new nightie and then apply a full set of makeup and spray on the perfume that is on the table.”

I did as instructed and went downstairs about 30 minutes later, just as the doorbell rang. I went to answer it and there were four large black guys at the door…

To be continued in part three!

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