It was Friday night and I was so excited! For the first time ever my wife told me I was going to get a treat for being a good slave and I was allowed to go out with her and her friends! She was out running errands after work so I decided to make the most of my alone time and hopped in the shower.
I scrubbed every inch of my body with some manly smelling body wash, shaved my face and trimmed my pubes—just in case I was going to get lucky.
I towelled off and put on a dark blue button up shirt and my nicest pair of jeans. I ran some gel through my hair and splashed on her favourite cologne. Just as I was finishing up, I could hear her opening the door.
I heard multiple voices…well, that was odd.
I went into the living room to see a group of her friends sitting around on our couches, talking and laughing. She never brought friends over, only met up with them outside of the house. My wife (also my Mistress) was very possessive and I was not allowed to hang out with all her pretty friends…until tonight. I wondered what I did to deserve such a treat.
“Oh good, you’ve gotten ready,” my wife said to me.
“Yes, I didn’t want to waste anyone’s time,” I responded.
“You’re going to have to change, though. I hate that shirt,” she told me.
I was taken aback. She’d told me several times that this was her favourite shirt on me.
“Ok, no problem,” I said. “What would you like me to wear?”
She handed me a brown shopping bag that looked like it was from a nice boutique. “I bought you some new things just for tonight.”
I beamed. “Thank you, sweetheart!” I went into our bedroom, smiling all the way.
As I left the room I could hear all the girls giggling hysterically. I was too consumed with happiness to think anything was wrong. I must have made my Mistress very pleased!
My smile faded, however, when I opened the bag and pulled out a tiny, tight pink dress. It finally dawned on me. I should have known better. This was not a prize; it was a punishment.
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“Are you having some trouble in there?”
she yelled from the living room and the girls roared with laughter.
“No, no,” I assured her, “I’ll be out in just a minute.”
I stripped down and somehow squeezed into the dress. It barely covered my ass and I was showing off some seriously hairy thighs. I was mortified as I looked at myself in the mirror. But that wasn’t the end of it.
There was something else in the bag—a long blonde wig. I blushed hard as I pulled on the wig and tried to adjust it properly. It still looked crooked.
Terribly embarrassed and ashamed, I went back into the living room and all the girls started clapping and telling me how pretty I was, laughing the whole time.
My wife straightened my blonde wig and carefully but some bright pink lipstick on me.
“Time to go!”
she announced. The girls all got up and shoved me out the door.
The bright sunlight hit me and I fully realized how ridiculous I must look. My elderly neighbour lady saw me and gave me the dirtiest look I’ve ever seen. She was sitting on the porch with a friend and pointed directly at me. Her friend saw me and they both looked completely disgusted.
I was mortified and I knew it was only going to get worse from here.
Mistress informed everyone that we were going downtown and we all piled into her SUV. It was a 20-minute drive and I was nervously chewing on my lip so hard I made it bleed. The girls taunted me the whole way, telling me how pretty I was and how good I looked all dressed up as a girl.
When we got near their favourite bar, we had to park a few blocks away.
“Honey, I…” I trailed off, looking at her, pleading with my eyes.
She cut me off with the evilest look she had ever given me. I had no choice. This was my Mistress’s will and I must obey.
I reached for my sunglasses and she slapped them out of my hands.
“No no no,” she said, “we want to see your pretty eyes!”
I cringed. That was my last, desperate attempt to save some of my dignity with anonymity, but it was not to be.
The girls forced me out in front of the group so I could be seen more easily as we walked to the bar. A group of guys across the street whistled loudly and yelled,
“NICE BEER BELLY, TRANNY!”
I wanted to just crawl in a hole and never come out. The girls were roaring with laughter.
When we entered the bar, it was packed. I felt everyone’s eyes on me and I tried to pull my dress down in a futile attempt at hiding at least some of my body. A group of guys playing pool all turned to me.
“Hey, there’s a girl you might actually be able to get, Tom!”
one of them said so the entire bar could hear. Everyone in the place started laughing and I hung my head in shame. It was so awful.
“Go talk to her, Tom! Here, I’ll buy us all around. Get the pretty lady a drink,” the same man said and the laughter continued.
I guess Tom wasn’t one to turn down a free drink. He sauntered over to me, trying to hold in his laughter. “Well hey, pretty lady.”
I could feel the tears welling up in my eyes.
“What are you drinking?”
I swallowed hard and managed to squeak out,
“A scotch. Make it a double.”
At least I could order a manly drink.
“Oh no,” one of my wife’s friends said. “She wants something fruity in a pretty glass. With one of those little umbrellas. Pink, to match her dress.”
There was not enough alcohol in the world to make me feel better at this point.
Tom ordered me a strawberry margarita, told me to, “Enjoy, pretty lady,” and went back to his friends with his pitcher of beer.
We’d only been at the bar for 5 minutes tops. I gulped down my margarita, blushing hard.
“Don’t worry, honey. This is just the beginning. We have a whole night of fun planned!”
she grinned with a twinkle in her eye, and the tears started running down my bright red face.
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