Jacks Bet (Top Tier Crossdressing Story Reward)

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Jacks Bet

With Kali pushing on my back, forcing me into the living room, I had to make it look like I wasn’t totally into this.

“Steady on,” I say, trying my best not to fall over in her glossy black high heels.

Having lost the bet to Zack, we’d agreed the loser would spend the day as a woman. With cross-dressing being my secret passion, I loved the idea! Still, neither Kali nor Zack knew, so I really did have to make believe that I wasn’t happy.

“Looking s*xy Hunny!” Kali cheers. “I don’t mind watching you work those *exy legs, sugar!”

“Don’t say things like that,” I reply, pulling my black cocktail dress down as far as I could.

Kali kept telling me how well everything fit me as she was helped me dress like this. I knew a lot of her stuff fit my body, having secretly borrowed much of her stuff previously.

Having to hide my joy at the situation, now that was actually the hard part. They’ve given me the perfect excuse to get pretty and not feel guilty about it!

The dress we choose was actually very pretty, with soft black lacing on the shoulders and a sweetheart neckline. With the skirt only coming to my tighs, we had to get creative with my und*rwear. To stop any…wardrobe malfunctions.

“Here he is!” Kali shouts as we enter the living room. “Isn't he beautiful!”

Fighting the urge to strike a powerful feminine pose, Zack looks at me and laughs.

“My days Jack,” he chuckles and points. “Did Kali make you shave your legs?”

Blushing, I look down at my silky smooth legs. I wouldn’t tell either of them, but I loved how they made me feel.

“Yeah……,” I answer back with a convincingly sour tone. “It’s going to take months for my hair to grow back”

“You know,” Kali says as she turns back to me and smiles. “Some women like it when a man is clean and fully shaved.”

Nudging me with her elbow, she looks me up and down. “Feels good, doesn't it!”

“No way!” I complain. “I feel….. so exposed!”

“Argh yeah,” Zack whines as he looks at how short my dress is. “Make sure you do us all the courtesy of sitting with your leg*s shut!”

Going slightly red, I felt like lifting my skirt up and flashing him. Did he think I was just going to go commando in a dress like this? I’m not Scottish!

Having said that, I’m glad it’s me dressing up like this and not him. He wouldn’t apricate the feeling of silk pant*es holding in his j*nk as I do.

“Dude,” Zack continues as he gets up off the sofa and ambles towards me. “Are those…..?” he points at my ch*st.

“Brea*ts?” Kali interrupts with a small clap of her hands. “They sure are! I ordered some for the loser. Just my little way of ensuring one of you got the real female experience!”

Standing on the spot and giving them a small bounce, we all watch as the br* I’m wearing struggles to contain them.

“Wow,” Zack says as he pokes one of them. “How does it feel to have your very own?”

“Don’t touch them!” I sarcastically whine. “Remember, the bet was the loser had to be and act like a woman! You wouldn’t just poke Kali’s brea*ts now….would you?”

Folding my arms and pouting, Kali stands shoulder to shoulder with me and clicks her fingers.

“Yeah boy,” she growls. “Why you gotta be like that with us girls?”

Zack rolls his eyes and backs away.

“Also, who’s wig is that?” he asks pointing at my perfectly styled hair. “It’s giving me the creeps!”

“The creeps?” I ask him, a little offended. “What do you mean?”

“Yeah,” he continues as she reaches to feel what my hair is made of. “With the make-up, dress, and the hair, you look very feminine. Almost……dare I say it…..se*y. Knowing it’s you under all that Jack, it’s giving me the creeps!”

“Should I take that as a compliment?” I ask as I shrug my shoulders at Kali.

“I think so!” she answers, holding back the laughter. “Jacky’s giving Zacky a b*ner!”

“Jacky…?” I say laughing at her b*ner joke.

“I don’t have a b*ner!” Zack angrily replies! “

“Whateva dude!” I playfully reply, snapping my f*ngers, just as Kali had.

“Well then….Jacky,” Zack says with a grin, putting emphasis on my name. “How about you start living the female experience and go make me a sandwich.”

With his comments failing on death ears, I turn to look at Kali’s face. She wasn’t impressed. I can see the cogs in her mind turning. She’s about to give him a piece of her mind.

“He can’t go make a sandwich wearing that dress!” she complains.

Nodding my head in agreement, I playfully curtsey.

Throwing himself down onto the couch, Zack looks at me and shakes his head.

For the rest of the day, myself and Kali just continued to gang up on Zack. It was great fun! I really felt like we bounded. It was like she finally had another girl in the apartment. I was trying not to enjoy myself, but it was next to impossible. Hopefully, I haven’t given myself away!

As the night drew in, we ate dinner together and started to chill in front TV. I’d worn Kali’s dress and heels all day, and I was getting a little sad that I’d have to take it all off soon. I’d have to stop living my truth, and that kinda made me sad.

Looking down at the time on my phone, the night was young. I wanted to go out dressed like this, but I knew if I mentioned that to either of them, they’d get suspicious.

Making my excuses, I headed to the bedrooms. Sneaking into Kali’s room, I needed to borrow a few more things before I sneak out.

Taking the chance to freshen my makeup, hair and spritz some perfume, I grab a purse to borrow.

Throwing in my keys, phone, and a little bit of money, I sneak to the front door. Reaching for one of Kali’s leather jackets, I throw it on and slowly open the door.

As I exit our apartment, the clicking noise of my heels on the tiles wasn’t making it easy to sneak away. Eventually, I made it outside without alerting anyone.

As the cool nighttime breeze wafted up my skirt, I had a surreal moment.

“What are you doing Jacky?” I ask myself as I pull the leather jacket tight to conceal my brea*ts. “People are looking!”

With every step of my heels drawing attention to myself, I start pacing down the street. I didn’t quite realize till now just how exposed women must feel when dressed like this. All I’ve got to keep my warmed and covered is a tiny little dress and a jacket.

As I continued ambling down the street, with my arms folded tight, I found the heels really starting to dig in.

As I look down to check my feet, I stumble and fall

“Whoa!” a gruff male voice says as he catches me mid-flight. “Be careful, little lady.”

As his large strong hands grip my side, he helps me back onto my heels. Looking up at him, I go super bright red.

“Errm,” I mutter awkwardly, putting on a feminine voice. “Thank you.”

His chiseled jaw, rugged good looks, and board shoulders make me feel pretty intimidated. He’s much taller and bigger than me. The man is stunning.

“Well now,” he says, looking me up and down. “Where’s such a pretty young lady going at this hour?”

“I-I don’t know….,” I reply nervously. “Just thought I’d go for a walk.”

He looks down at my heels and laughs.

“Now I’m no woman,” he states with a grin. “I don’t suppose it’s easy going for walk-in shoes like that.”

Letting out a nervous giggle, I shake my head.

“Hop on!” he cheers, holding his back towards me. “Let me do the walking!”

“Nah,” I reply, hoping he hadn’t yet realized I was a man. “I’m ok.”

Without a second's hesitation, He picks me up and throws me over his shoulders. As my entire body hangs, I can’t help but laugh. I’d always had dreams of being treated like this one day. Being seen and treated like a lady.

“Let's go get a drink,” he says, holding me tight. “My treat.

Some agonizing minutes pass, as every so often a gust of wind blows up my dress. Lucky for me, he couldn’t see up.

As we reach a bar, he pushes open the door and places me back down onto my feet. He then gently brushes the hair from my eyes and smiles.

“Go take a seat,” he insists, pointing at an empty table. “I will get some drinks.”

Nodding in agreement, I head over to the empty table. With every click of my heels, I could see the men in the bar checking me out. I’d never felt so uncomfortable, but excited in my whole life. Did they know…or did they see me as the se*y woman

“Here you go sweety,” he says, handing me a small glass. “I hope you don’t mind Jack Daniels and Coke.”

“Don’t mind…?” I say, sipping my drink. “It’s my favorite!”

“Good!” he smiles, allowing me to see his perfect teeth. “My name is Andrew, what's yours?”

Taking another sip of my drink, I tuck loose hairs behind my ears and smile.

“It’s Jacky,” I answer.

“Well howdy, Jacky,” He replies. “Can I just say, you gotta be one of the most pretty women I’ve ever seen.”

Blushing like crazy, I knew I was in for the night of my life!

With it going by like a flash, I quickly became apparent just how much myself and Andrew had in common. He loves baseball, he’s a massive fan of action films, and he even likes country and western. That’s not even the best part! He’s been living in a tiny home for years. I’d always yearned for that lifestyle. To be free and go where ever I wanted!

After a few more Jacks and Coke, He’d invited me out to look at his tiny home on wheels. As we approached, it was just how I’d imagined mine to look.

“This is incredible!” I exclaim as I stand in awe of it.

As I turn to face him, Andrew gently grabs my sides and pins me up against the side of the home. Softly, he presses himself against me.

“Your incredible,” he whispers softly into my ear, as he strokes my hair.

Now powerless to do anything, I found myself excited, rather than scared.

Staring directly into his big blues, our faces inches closer and closer. Before I know it, we are k*ssing passionately. He tastes like cigarettes, but I didn’t mind. His kisses gave me goosebumps

“So sexy!” he continues to whisper, as his searching hands find their way to my a*s.

With a grab and squ*eze of my a*s, his wandering hands quickly move around to my tighs and up towards my crot*h.

“Wait!” I squeal, hoping to stop him before he finds my co*k.

As his fingers gently touch my b*lge, I feel real terror fill my soul. How was this guy going to react!?

“Interesting,” he comments and looks me deep in the eye.

Hoping the guy doesn’t snap me in half, I go to utter an apology.

“It’s ok,” he says, gently k*ssing my lips. “Don’t look so worried. I’m into this if you are!”

As he kisses me once again, my mind starts racing.

One side of me was super h*rney and has always dreamt about this moment. This guy is almost perfect for me. Thinks I’m sexy, doesn't care I’m a man and we are into all the same things.

The other side of me doesn’t want to be a sl*t! I’ve just met him and that’s no reason to sleep with him. I also would like to see him again. Do I really want to be giving it to him straight away?

“Are you coming in?” he asks politely.

“I…..,” I freeze.

I had no idea what to say or do! One thing is for sure, I could totally understand the pressure on women in this situation.