Hung like a Grape

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A small dicked Sissy is outed and humiliated.
1.1k words
4.09
96.9k
46

Part 1 of the 3 part series

Updated 06/08/2023
Created 04/01/2018
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This is my story; it is a tale of how my "little secret" was uncovered. I hope you enjoy it!

*****

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 (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 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 kind of 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 5 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 her room and she opened her dresser. "Let's see, your body is different from mine so I think you'll need a thong. 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 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. It was a short skirt that 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 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 lay down and 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 the party tomorrow night. There are a lot of guests coming over, including some hot guys. We need someone to serve us."

To be continued?

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14 Comments
b3tas1ss1b3tas1ss1over 1 year ago

Way too short. Seems rushed and unfinished.

Claudia69Claudia69over 2 years ago

Good start to a series,the story is making my little dickle hard in my panties...

tinalikesithardtinalikesithardalmost 3 years ago

I love this. Keep Going.

Tootight1Tootight1over 5 years ago
good story?

it is and it isn't. He's what 40 years old and doesn't know enough to tell them no pictures? He had a crush on her, and did what she said, or had to do, ok. After a bad marriage, why would he put so much trust in a woman again, hope springs eternal. Now he has to go back into work with all their pics spread who knows where, and think about his future. Does anyone think Blackmail is far behind, or maybe it's already too late. He has to leave and start over again, because of a woman he trusted. I liked what happened on a one to one basis, but that's not where the story ends is it?

SusanlynnSusanlynnalmost 6 years ago
Rushed but good.

You rushed a previously married man into a complete cross dresser in a matter of a few minutes. That’s not likely to happen. It took my mistress and the man who would eventually end up being my husband months to convince me to start my journey. Other than that, this has the possibility to end up very hot and sexy. I can’t wait to read the rest.

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