The Adventures of Sissy Madison Ch. 02

They all got into Kim's car ready for the trip. Haley turned around as soon as Kim started the engine looking Madison up and down.

"You are just sooo cute, I can't even get over it!" and with that Haley got out and hopped into the back seat with Madison.

"So do you like being all dressed up like this?"

Kent nodded but didn't say a word.

"Oh don't be like that" Haley encouraged "My uncle loves to crossdress too! He doesn't do it much around the family, but we all know about it. There is nothing wrong with it at all! I mean who really wants to wear boring boy clothes. Us girls get to wear all the cute stuff" nudging Madison.

Madison felt more at ease now and admitted "Yes I really do love it!"

"What do you love about it?" Haley prodded in an effort to dig in to Madison's desires and get her to say what Haley was fishing for.

"I don't know" Madison waffled "Just all of it I guess. Getting to feel cute, important, needed, and..." Madison dropped her head "I feel sexy, in a cute slutty way which makes me happy."

Haley grinned ear to ear. "I COMPLETELY understand how you feel! That's what I like about it too. Getting all dolled up for someone and then seeing their eyes light up when you show up is amazing. And then getting to thank them for taking you out and maybe buying you something is so satisfying."

"Oh my gosh I almost forgot. Thank you so much for the clothes Kim!" Madison said.

"Oh no honey, don't thank me. You have to thank Haley. She bought the shorts and top for you."

"Thank you so much Haley. I really like them"

"Ya? Well you're welcome, but let me teach you a little something. If you were really thankful then you would give me a blowjob like a good gurl."

Madison's eyes opened a little wider. She had already sucked one cock today, she didn't really want to suck another. "Well if that's what you wanted and had a cock then I..." Madison's sentence trailed off as she saw Haley smile wide and reach into her Hobo Michael Kors purse and pull out a hefty dildo. Not even close to as big as Wyatt, but not that much smaller than Tyrell. It was a beautiful dildo with perfect veins and even a nice little hole. She watched Haley put it in her lap like she had an instant hard on.

Kim looked back at Madison whose eyes were wide in disbelief. Kim laughed out loud, shaking her head said "Don't even act like you don't want to suck that cock! I saw you bite your lip you slut. You will do exactly what Haley says and be an obedient little bitch. Do you hear me?" as she slowly started to pull out of the driveway.

"Yes ma'am" Madison replied fixing her eyes to Haleys crotch now with her beautiful dildo tucked into her shorts just like Kim did.

"I'm going to teach you a thing or two about sucking cock! I hope you can make me feel as good as you made Kim feel. Now first thing is, I want you to take off those shorts so I can see your panties, no need to hide such a beautiful lace covered ass. Men love playing with your panties when you're giving them a blowjob."

As Madison slowly pulled her shorts off she realized she was going to be on display for whoever looked into their car. Her still caged clitty twitched in excitement. She worked her way over closer to Haley and went to put her mouth on the cock when Haley pulled on Madison's bra strap and popped it.

"Easy now there you greedy little whore! You don't just start sucking. Grab the base of my cock and give it a nice kiss. There ya go. Now you need to lick up the side of it and show me that you're grateful for the opportunity to suck my dick. Great job. Now you have to make me want it. Slowly put the tip in your mouth and just suck it nice and easy."

Madison did exactly as Haley was coaching her enjoying the feeling of a hard cock in her mouth driving down the road. Madison never thought that she would be giving road head in pink panties for anyone to see. She kept sucking and eventually Haley told her to start going deeper and deeper trying to deepthroat Haley's cock.

"Haha I think we have another customer that wants what I'm having!" Haley exclaimed.

Madison looked up not taking her mouth of Haley's cock to see a truck driver on the highway looking down on them smiling and cheering. Kim accelerated while laughing.

"Well don't stop slut" Kim demanded.

Haley continued to coach Madison through some more techniques of twisting her hand and sucking simultaneously which made Haley moan nice and loud. No more than 5 minutes later after Haley was done instructing and Madison was working on her technique she heard Haley start to breath heavily.

"Oh ya baby" Haley said "Keep sucking nice and good like that. I'm getting so close! Now my little sissy, whenever I tell you I want you to grab my balls nice and hard and give them a really really hard squeeze. Keep going. Wow you are such a good little cocksucker. Oh goodness. Oh yes. Just like that! Squeeze my balls. Squeeze them you pathetic sissy! OOOOOHHHHHH"

With that Madison squeezed the Haley's balls as hard as she could and felt a salty liquid running into her mouth. She tried her best to deepthroat it to keep all the liquid in her mouth but couldn't. She kept the liquid in her mouth like she has seen on so many porn videos to try and please the ladies.

"Suck me dry Madi. I can't believe I just came in my panties from you!"

Madison sat up and smiled, white liquid dripping down the side of her mouth.

"Clean that up and show me what you have!"

Madison used her finger and scooped the rest in her mouth and opened up wide to show Kim and Haley.

"How does that cum taste sissy? I want you to keep it in your mouth for a little bit. Swirl it around and get a good taste of it. Don't you just love the saltiness and texture of a real mans cum?"

Madison's eyes were wide with disbelieve.

"Didn't think you would get such a tasty treat did you? That's my boyfriends cum. I saved his cum from the last 2 times we fucked so you could have it. I'm so happy you are enjoying this. I'm not too big of a fan of his cum but I knew you would like it."

Madison sat there with a mouthful of cum salivating. Another few drops came out the side of her mouth and stuck down to her chin. She went to wipe them up only to hear Kim yell "NO Leave it! That's the best lip gloss you can get! Alright my pathetic little sissy, you can swallow. BUT, you better enjoy that yummy cummy! I don't know when you're going to get more."

Madison ran her tongue through the cum in her mouth a few more times really enjoying the saltiness and the joy of satisfying Haley. She swallowed and smiled at the 2 women. Taking her tongue she ran it around her mouth getting the rest of the cum that was coating her mouth and swallowed that too.

"Yum!" Madison said.

Haley started putting her cock away and regained her composure. "I think we might need to get her the real thing here soon. Maybe after a few more practices we can get you a real cock to gobble up. Would you like that?"

"Um, maybe I guess I could."

Laughing out loud Kim said "You guess? Ha! You would. Not just for me, but you need it. You should see the smile on your face. You are only this happy when you get your little boi pussy pounded to hell and back. Haley look at her little clit. Is it straining in her cage?"

"Pull your panties down and let me see" Haley instructed. "Wow I didn't know it could get that big but its really trying to get out. Good thing we have that cage on there."

"Well get your shorts back on. We're almost there."

Madison looked outside only to see the South Star Mall come into view. Her heart fluttered at the thought of walking into a packed mall dressed like this with cum on her chin and no wig.

They all hoped out of the car and Madison readjusted her shorts and straightened out her top. She pulled some chapstick out of her purse and put a thin layer on. Upon putting it back in her purse she fumbled it and dropped it on the parking lot pavement. Without thinking she bent over and picked it up only to hear Kim and Haley laugh.

"Oh honey!" Kim said "You can't bend over like..."

"Ah, hup hup hup hup!" Haley stopped her. "I think she is perfectly fine doing that!"

With Kim laughing Madison quickly questioned what was going on.

"I dont get it! Whats happening?"

"Ok, listen here you little slut. Your plug is almost as visible as your cute little panties. For the rest of the day you are only going to bend at the waist to get things off the ground or off the bottom shelf. Do you understand me?"

"But that's..."

Slapping his ass hard and pulsing on the base of his plug Kim asked "Do you understand?"

"Yes ma'am" He responded.

"That's my good girl" Kim said as she kissed him on the cheek. "Now lets go shopping ladies!"