Hung like a Grape

by sissysherry2

I was married for 13 years but the magic was clearly gone. We got divorced when I turned 40 and I moved away to start fresh. I got a job in an office that was full of women and very few men. I worked around a bunch of hot twenty something women who seemed to bond with me.

There were four of us; we called ourselves the ‘core four.’ There was Lisa (a tall well built and attractive blond), Kelly (a very thin brunette), and Stephanie (a very athletic woman). And me. We would go out after work for drinks and talk into the night. We seemed to be great friends, but I always wondered where it was headed. They started calling it ‘Gals Night’ and I didn’t really protest when they called it that. I was kind of honored to be considered “one of the girls.” After a few drinks, they would talk about guys and how much they loved big dicks. I blushed during this, and they giggled at me.

One day Lisa came up to me. “Hey, I was thinking of having some people over this weekend. Do you mind coming over to help me get setup?”

I always had a crush on Lisa, so I said, “Sure.”

She asked me to come by her place right after work on Friday. Since we typically wear blue jeans and casual shirts on Fridays, I didn’t think I needed to bring a change of clothes. I drove right over and rang the bell. Lisa answered and asked me in. She was wearing shorts and a skimpy T-shirt. I was wondering if something romantic would happen. My hopes increased when she offered me wine; I drank it right down eagerly. She and I had two more glasses of wine before we got to work.

“OK, let’s start around the pool,” said Lisa.

She asked me to sweep around her pool. As I got near it, I lost my balance and fell in. Too much wine. Lisa helped me out of the pool.

“It’s okay, I’ll put your stuff in the dryer, but it doesn’t work too well these days. Why don’t you take your clothes off now, and then we can go upstairs and get you into dry ones?”

I was quite shy and nervous about showing her my dick. I always knew it was well below average size. I would hide it in a towel whenever I would be in a locker room. It didn’t hang down like most dicks. It just rather sat there, nestled around my balls. Maybe it was the wine influencing my thinking, but I thought ‘why not’ so I took off my clothes right in front of her.

“Oh, my…” she exclaimed. “You’re hung like a grape!” She started giggling. “I’m sorry it’s just I’ve never such a tiny dick before.”

I didn’t know what to say; I just got embarrassed and looked down. I saw my little grape-sized dick. God, it was tiny.

“Let’s go upstairs so we can cover you up. But before we do anything, you need to take a shower. You’ll see a pink bottle near the shower. Put the lotion all over your body from the shoulders down and let it set 10 or so minutes. Then rinse it off.”

I did as I was told and was shocked when I watched all my body hair go down the drain. My skin burned, so I put moisturizer all over. It smelled very fruity but felt great. I then went into Lisa’s room, and she opened her dresser.

“Let’s see, your body is different from mine, so I think you’ll need a g-string. I only have this pink one. Here, put it on.”

I said, “Wait a minute! You want me to wear panties?”

Lisa replied, “Oh come on, it’s no big deal and who will ever know? Besides, it takes someone who has the self-confidence to do it, and I admire that.”

That convinced me, and I stepped into her panties and pulled them up. The fabric felt really good around my groin. I ran my hands over them.

“See, I knew you’d like them. I can’t even see a bulge in those panties. OK, let’s see I have jeans, but I don’t think they’ll fit you. Here try this skirt. It has an elastic waist.” I hesitated, but Lisa said, “Hey, it’s up to you, but I wouldn’t want to be walking around in just panties if I were you.”

She was right. I stepped into the skirt and lifted it up. A short skirt barely covered my panties.

“OK, we’re almost done. All we need to do is cover up those man boobs of yours.” Then she handed me a loose-fitting blouse. I didn’t even protest as I put it on. “I like that outfit,” she said. “Turn around for me, now walk over here. Your ankles should cross over when you walk. Good girl! Now let’s get back to work.”

When we got out to the pool, I was shocked to see Kelly and Stephanie were there. They saw me before it was too late to hide. They started laughing right away when they saw me. They told me to pose for them so they could take pictures with their cell phones.

“Hey, girls,” said Lisa as she took me by the arm. “It looks like the new girl has good taste in clothes.” They all laughed. “We’ve got to give you a real feminine name, how about Sherry?”

“Hey, you’ve got to see Sherry’s clit! Kelly, go to the fridge and bring out the bowl of grapes. I want to see something.”

They told me to lie down, pull up my skirt, and pull down my panties. When Kelly brought the bowl of grapes, Lisa took one out and handed it to me. “OK, Sherry, put the grape next to your little clit, and let’s see which is bigger.”

I did as I was told.

The grape was bigger!

The laughter was instantaneous and loud.

“Can you believe that…? Her clit is smaller than a grape!”

They got out their cameras and took some more pictures.

Lisa then brought out a makeup kit. “OK, Sherry you need makeup now. Let’s start with a nice foundation.”

She then proceeded to add blush, lipstick, eyeliner, mascara, and eyeshadow. When they were done with that, I was instructed to keep cleaning while they relaxed and drank more wine. They told me they to dust, vacuum, and straighten up things so it would look nice for the party. They called me in after I was done.

“Sherry, we think it would great if you could work for the party tomorrow night. Many guests are coming over, including some hot guys. We need someone to serve us.”


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 dick 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, and 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 ten 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’m 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’m 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. “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 me 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 ass pussy.

“Hold your cheeks open and beg me to fuck you.”

“Please, Miss Lisa … fuck me with your massive cock. I’m holding my cheeks open as a symbol of giving up control to you. Please take my cherry and make me yours,” I begged.

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 amazing,” I moned.

I meant it too. 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 to 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,” Lisa said. “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, 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’s 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.

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.”

About 20 women in the store 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 Lisa’s 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.


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 to 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 beneath my nightie top and felt my ass. He put his fingers into my ass; he was able to put two fingers in and move them around, and I 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 any way you want. Anyone want to begin?”

One of 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 baby doll. 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’s 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 the black cock and thanked the man 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, reapplied it, and got ready.

“Next up is taking her anal cherry. Anyone want to start?”

All the other guy’s hands went up.

“Well, maybe you can all participate, everyone gets 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 on 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 to my back, and 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 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 any way 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 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.


The End.


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