Hung like a Grape Ch. 03

The story of our sissy heroine concludes... this is the third chapter. Lisa had pegged and tagged Sissy Sherry in the last chapter and took her shopping for new lingerie for the evening's festivities. She opened the door in a sexy pink nightie with full makeup.

I plan on concluding the tale here but that will depend in how well it is received. Thanks to those who reached out for suggestions and hope you enjoy it.

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The arrival

Sherry opened the door to find four large black guys standing in the doorway. She let them in with a curtsey, just as she was trained to do by Mistress Lisa.

"Welcome the party! My name is Sherry and I am here for your pleasure." They laughed and walked in; immediately groping Sherry's man boobs through the new nightie she had gotten earlier in the day. One of the others reached under the nightie top and felt her ass. He put his fingers into her ass; he was able to put two fingers in and move them around and Sherry moaned with pleasure.

They walked into the living room and saw there were four females there, including three co-workers (Lisa, Stephanie and Kelly). They were passing around a joint and instructed me to take a drag to help relax. Lisa then got up and said "OK, now Sherry here is an oral and anal virgin; two of you lucky guys get the honor of busting her cherry. I have given her some training but you will get to mold her anyway you want. Anyone want to begin?"

One of the them immediately raised his hand. "I'll start with a blowjob from this bitch."

I got on my knees in front of him and instinctively bowed down and kissed his shoes before taking them off. I then reached for his belt and undid it. I couldn't believe I was actually doing this! My little clit stirred in the panties that were part of the babydoll. I then unbuttoned the jeans he was wearing and pulled them down. Then it was time to take his boxers down. "Oh my God, it just keeps going and going" I said when I saw his massive cock. I immediately started kissing the shaft. "Suck that shit, bitch" he growled.

Even though I knew there was a lot of humiliation out of giving my first blowjob in front of an audience, I started twirling my tongue around the tip of his cock and started working down the soft underside. It started growing as I did. I could not believe how big it was getting. I started sucking with relish- up and down, in and out. I suddenly felt a hard slap on my face. "Bitch- I felt your teeth. Either do it right or I'll knock them out!" I opened my jaws more and tried my best to use my lips. I then remembered Lisa's instructions and looked up into his eyes. He had nothing but contempt in them at first but after a few minutes, he closed his eyes and seemed to enjoy it. I would use my hands as much as I could- his cock was much larger than the dildo that Mistress Lisa had used the evening before. He put his hands on my head and started moving me back and forth. I didn't think I could take the whole thing but I relaxed my throat to take it in. I turned my mouth into a pussy and tried to relax and let him fuck my mouth. Soon I felt him tense up and I could tell he was close to coming. He took his cock out and finished by hand. "Here is some more makeup for you bitch" he sneered as he shot a load on my face; then another directly into my mouth, followed by other and another. Some dripped on the floor and I instinctively got down and licked it up. I then kissed his cock and thanked him for the experience.

"OK, Kelly, did you get all that?" asked Lisa. I looked over and was shocked to see Kelly had a computer screen in front of me and the light was on where the webcam is located. Stephanie had gone over to another PC in the room—they had filmed the whole thing on Skype! "Yeah Lisa, we got it all and I've saved it as "Part one" of the movie. We can edit it later but it worked perfectly. I think she needs to freshen up her makeup before the next scene." I was handed lipstick and reapplied it and got ready.

"Next up is taking her anal cherry! Anyone want to start?" All the other guys hands went up. "Well maybe you can all participate—everyone get naked except you, Sherry." They all complied and lined up in front of me. I needed no instructions on what to do next. I started sucking each one to get them hard and horny. It was like the old TV show with the plate spinners- I would move back and forth to each one to keep them hard. "Get over to that couch, bitch and you had better be cleaned out." said one of them. I did as I was told and assumed the same position Mistress Lisa had shown me during training. I was glad I put the lube and taken the enema. Lisa came up to me and put a ball gag into my mouth so I wouldn't distract them. I felt his hands grab the top of my nightie and hike it up my back, then he pulled down my panties. I reached back and opened my ass cheeks as Lisa had instructed. He was not nearly as gentle as Lisa had been and his cock was a lot larger than the dildo. It seemed to go on forever as he forced his massive dick into me. My screams went into the ball gag and came out as a muffled moan. He was finally fully inside me. I felt his hands on my ass cheeks as he started pumping in and out. I could even feel his huge balls hit against me. After a few minutes, he started groaning and I felt his cock tense up and explode. He pulled out and I felt him slap my ass. That was my signal to turn around a softly clean off his cock. I did my most feminine reaction and licked as much as I could.

The others took their turns and fucked me like a cheap whore. They used me anyway they wanted and it felt so degrading but so sensual at the same time. I cleaned each one the same way as the first. The whole thing lasted about over an hour and I was completely sore when it was done.

Lisa came over and slapped me on the face. "Nice job, Sherry. Now I need to you to sign this release so we can sell the porn film we just made. Oh, and I almost forgot, there was an auction to take your cherry. But the guys refused to pay so I guess you will have to. Give me your ATM card and PIN; I will be making a little withdrawal to pay for it. I also thought I would give them a little tip for doing such a good job."

I couldn't believe what was happening. What had started as an innocent little "gals night" had quickly turned into a night none of us would ever forget. I paid others to humiliate me and get off. And something told me this was just the beginning!