Crossedressed In Best Friends Mom Clothes 23 free porn video

Part 23


It was a long flight back home and I was very glad to have a seat in first class. I walked through the tunnel and into the airport. I went to get my suitcase and walked through customs. Then check my passport.

“Did you have a nice flight, miss?”

“Yes. Pretty long though!”

He looked at me and then my passport. “I bet! Well, you’re clear, miss. Have a nice day!”

“Thanks. Ehmm. I’ve got my car stashed in a hangar. Can you maybe help me get to it?”

“Sorry miss. But ask at the airport security reception. They might be able to help you!”

“Thank you so much. Bye!” and I went to find the airport security. It took me a while, but I found it. “Hello, sir. I’ve got my car stashed in one of the hangars here at the airport. Can you maybe help me get to it?”

“Please can I see your passport?” I gave it to him, and he looked at me and the passport. “And you remember what hangar?”

“Ahh...No!”

“Well then, I can’t help you, miss!”

“What if I tell you my boss is Lauren Lopez from the lawyer firm, Kings and Lopez?”

He looked at me like I was lying to him. “And you got any proof of that?”

“Not other than I am her maid!”

“Sorry, that’s not enough!”

“You wanna speak with her then?”

He had a smirk smile on his face. “Pff yeah, sure...let me talk to her!”

I picked up my phone and called her up. Of course, she picked up in no time. “Hi, Caroline. How was your flight?”

“Hi, sweetie. It was all good, but I’m standing there trying to get to your hangar and get my car so I can pick up your son. But this security man doesn't believe that I work for you!”

“Put me on speaker!” I pressed the button. “I’m on speaker?”

“Hello, ma’am. This girl claims that you're Lauren Lopez. And...”

He didn’t get to say anymore before Lauren started shouting. “Let me tell you one thing, mister. You better get my maid to her car in hangar B417. Clearance number is 10837721.

If you don’t get my girlfriend over there right now, I will talk to your boss, Kim, and get your ass fucking fired. Is that understood?”

His face became pale and his smirk was gone. “Y...Y...Yes, ma’am...I’m on it. Sorry for the inconvenience!”

Oh my god, yes. Lauren still had it. And it turned me on so freaking much, my sexy hot boss and girlfriend talking like that.

Then she said, “I’m going to dinner with Roger tonight to talk over your business and the team!”

I wasn’t even jealous. I was happy she was enjoying herself.

“Sounds nice, my love. Have a nice evening and say hi to Roger from me. And thanks again, Lauren, for the help!”

“Roger says hi. We both miss you! Looking forward to coming home to you, Caroline. Bye!”

“Please don’t say anything to my boss, ok? I’ll drive you myself!”

I nodded and smiled. “Yes, you do that!”

“Right this way, miss!” He took my suitcase and told another employee to cover the desk for him.

We walked through to the back and there stood like a security car. We got in and he drove me to the hangar. He quickly got out and gave me my suitcase. “Again, I’m sorry for the inconvenience, miss!”

I took my suitcase and put it in my light pink Phantom. Oh, I missed my car so much. I got in and took my heels off and drove out through the airport control gate. The same guy who let me in before my flight was here again, but this time he recognized me.

“Oh hello, miss. Is Lauren with you too?”

“Not today. She had some business she has to finish back in Germany. So I’ll be back sometime this week!”

“Well have a safe drive home, miss. See you soon!”

“And a nice day to you too!” and he opened the gate for me.

I got on the highway and rang Jaiden through the car’s Bluetooth. The phone rang, but a girl picked it up.

“Hello, Jaiden’s phone!”

“Ohh Hello...! You got Jaiden there?”

“Who is this?”

“I’m the maid!”

“Oh. That pretty girl?! Well, Jaiden forgot his phone here with me, but he took the bus home yesterday! Any chance you can pick up his phone?”

I really didn’t want to drive all the way over there, if he wasn’t there anyway. “Ehmm...I think I’m driving him tomorrow after school, ok?”

“Sure, that’s fine. See you then!”

“Yes, Bye!”

~*~*~*~*~*~*~*~*~*~

I finally got home to the apartment, parked my car in Lauren's parking garage, and took the elevator up. It was now 20:17. The elevator doors opened and I heard music playing from upstairs. It must have been loud if I could hear it all the way down here! I took my suitcase and put it in Lauren’s walk-in closet. I turned off the light. But when I did, I saw a weak light coming from between the carpet and one of her wall-mounted draw systems. I opened every drawer and looked through them. And in the 3rd one, I found a small button. I gently pressed it and it made a clicking sound, and the whole 2 cabinets next to it moved to the side, plus the draws. It opened up to a whole other room.

It was dimmed and I looked behind me and there was a button on the wall that said ‘Close’. I pressed it and the whole cabinet moved back and I heard the draw slam shut. There was a little bed in here with a little fridge containing wine and sodas. I turned around and there was a huge computer screen in the middle and with 10 monitors on the wall. A whole audio panel underneath beside a keyboard and a mouse. I sat down in the office chair and moved the mouse and the whole computer lit up, plus the 10 monitors on the wall. There were like 3 of the monitors of my apartment. 2 monitors were of Jan’s apartment and the last 5 were of this big apartment, including one with me in this room. I bet this is how Lauren controlled all my livestreams. But is she keeping an eye on her son too? And Jan? That’s how she knew he was in my apartment! I saw Jan watching TV and eating some sort of microwave dinner. And then I saw Jaiden in the top corner monitor. I quickly found out how to control it, so I pulled the corner monitor screen onto the big computer screen in the middle. He was sitting by his desk listening to music. I put on the headphones and heard his room sounds clearly. He was sitting there in a pair of his mother’s black panties and her bra with some stay-up black stockings. Uhh, such a little naughty sissy boy, stealing his mom’s clothes. It got me pretty excited and I felt my tiny dick poking my Wolford pantyhose. I tried to zoom in, but I couldn’t see his computer screen properly. But I went into Lauren’s computer and I could split his screen into my screen. And as I did, I saw he was drawing an anime girl in pantyhose spreading her legs where you could see the pussy through the hose. And over the girl’s head stood the name, ‘Caroline’. He had drawn me with a pussy anime style! I touched my tiny dick through my pantyhose.

“Mmmm, Jaiden, that’s so sexy...”

I didn’t know that Jaiden was a drawing anime artist. And I saw a reference photo and it was me on his couch when we ate pizza that one time. I saw that photo on his phone that he’d taken those pictures of me when I fell asleep. Then the doorbell rang. And I heard the ring in his room too - I could hear through the headset. He quickly got up and put on a see-through black bathrobe. And that was also Lauren’s as I’ve seen her wear that before. Then he put his black stockinged feet into his mother’s pumps. He looked kinda cute and feminine, though he still had his short hair and no makeup on. He reached out a ‘GoPro’ camera and took it with him as he went out of his room and down the hallway. I followed him on the monitors, and he came to the stairs where he walked all femininely down, swaying his hips. Uhh, it reminded me so much of myself at the beginning of my crossdressing adventures! The doorbell rang again. He put the camera beside the TV and hid it. Then he walked over and pressed the elevator button. The doors slid open to each side and right there stood a short chubby guy. I zoomed in on both of them and I saw the pizza guy’s eyes open wide.

“Ehh...! Hi...! That will be 17!”

His eyes were wandering down Jaiden’s body in his mom’s lingerie. Jaiden stood there in a sexy pose with one leg lifted slightly so the bathrobe showed the top of his black stockinged leg, and his hands on his hips. The elderly chubby pizza man looked on the note on the pizza, but quickly looked back at Jaiden.

“Ehmm...17 dollars. Yes, that will be 17 dollars!”

Jaiden smiled at the pizza man. “Ok, come on in. I’ll just go check my wallet!” Jaiden turned around and swayed her hips as he walked over to the kitchen counter.

The pizza man took a few steps inside and his eyes followed Jaiden’s ass. The pizza man put the pizza down and slowly walked towards Jaiden while he rubbed his pants outside his crotch.

I saw Jaiden from another angle on another monitor and saw his eyes looking backwards without moving his head, not to get noticed. Pretending to find the money in the wallet and he leaned over the kitchen counter, showing his ass in the see]through bathrobe in his mother’s black panties.

“Oh, where did I put my bills in this stupid wallet?”

It all sounded so fake, but I loved watching Jaiden luring this pervert in! The pizza man unzipped his pants and pulled out his semi-erect dick. “Don’t worry...I’ve got time...”

“I know I put them somewhere here!”

He was now only one-step away from Jaiden’s ass. I pulled my skirt up and pulled my tiny dick out and watched and listened while I jerked myself. This was so much better than porn. Mmmm! Then Jaiden got a huge surprise because the pizza man spanked Jaiden’s black pantie ass.

“ARGH!!!” He quickly turned around and looked a bit frightened. That wasn’t what he expected. I could clearly see that in his facial expression. He got mad. “What the fuck are you doing?”

The pizza man had this smirky smile on his face. “What are you doing? Dressing all pretty for a visit from the pizza guy? You want this don’t ya?” He jerked his now hard cock right up against Jaiden’s leg.

“Sorry. I didn’t want it to go this far! I just like to be a little daring and be watched! Please leave right now!”

He jerked his cock with one hand and pulled Jaiden by his ass, up against his chubby body. “I can’t leave now! Look at what you did to my cock? It’s all hard seeing you dressed so nice for me! I know you teased me. Come on, touch my cock, I know you want to?!”

Jaiden blushed so much and looked shyly down at the ground. “I don't know! I better pay you for the pizza and that's it! I’ll give a good tip!”

He pulled the bathrobe off from one of Jaiden’s sides, touching that silky smooth skin with his chubby hands. “Mmmm...I don’t think that’s enough! Come on, touch my hard cock! It's been a while since I felt some real hands on it!” He grabbed Jaiden’s hand and forced it around his cock.

I could see that Jaiden didn't feel comfortable, but he slowly did it anyway. “Just like this?”

The pizza man was loving it and threw his head back. “AHH..., Fuck, yes...just like that! Faster! MMMmmm...your hands feels so soft...AH!”

Jaiden jerked him faster and so did I. I wish that it was Jaiden’s soft hands on my dick right now.

“Are you a good little sissy boy?”

Jaiden blushed, but he nodded gently.

“Mmmm...that's good! Ahh! You know what good little sissy boys do?”

He was still blushing, but shook his head this time.

“Mmmm...sissy boys, they like to suck a nice hard cock! You want to suck it, don’t you, little sissy? Ahh! My hard cock in that pretty mouth!?”

I saw Jaiden’s facial expression and he looked worried and said in a very soft voice. “Eh...I don't know...I’ve never sucked one! I think I’ll pass!”

My god, this was so sexy to watch Jaiden being such an innocent little sissy boy!

“I won't force you...! You can do it real gently if you like? Mmmm...why else did you dress so pretty for your pizza man? Come on, sissy?!”

I saw Jaiden bite his lip gently and slowly went down on his knees. He jerked it a little more as he looked at the pizza man’s hard cock, and then looked up at him.

“Go on, sissy boy...suck it! I can see you really want to try it!”

Jaiden slowly opened his mouth and gently licked the tip. The pizza man’s head once more leaned back as he closed his eyes. “OHH...! Mmmm, yes...Lick it good!”

Jaiden looked up at the pleased pizza man, and I could see it turned him on. Then he put his tip inside his mouth.

“God wow...AHH! Keep going, sissy...”

Jaiden also looked pleased with himself. I jerked my tiny dick so good as I kept watching them both. Then the pizza man slowly moved his hips, pushing his cock a bit deeper inside Jaiden’s mouth. Jaiden instantly got some big eyes and tried to move his head away a little. But the man just pushed his cock inside further, and it made Jaiden gag a little.

“Mmmm...you gagging on my hard big cock? Is it too big for a pretty sissy like you?”

He gagged like 4 times more, then Jaiden had enough. “I'm sorry, I can't! Yes, it's way too big! Let me just pay for the pizza?!”

But as Jaiden was about to stand up, the pizza man held him down by his shoulders and said. “No...I haven’t gotten a blowjob in fucking years! Now I get teased by a pretty sissy boy and you wanna quit?” He grabbed Jaiden's head with both hands. “Open that little slutty cocksucking mouth. You're not done here, SissyBoy!”

Jaiden shook his head and tried to push him away, but I have tried that too and men were just too strong compared to a sissy like Jaiden.

The pizza man held Jaiden’s head and pushed his hard cock inside again. And this time, he didn't hold back. With every thrust, Jaiden gagged, and his arms were hitting the pizza man's legs, but he wouldn't let go. After like 8 gagging moments, he pulled his cock out and let Jaiden catch some air.

Jaiden tried to speak as he gasped for air. “My god...Stop...! Plea...se...!”

...And then he forced his cock inside Jaiden’s mouth again.

My dick was rock hard watching Jaiden being used like that. Some part of me was feeling bad. But it looked so exciting and I knew from experience that the first forced cock-sucking was something special. Jaiden kept on gagging, but not as much as before. And I saw his throat expand as the hard cock reached the back.

“AHH...YES!! Good little sissy...Slut! I’m gonna fucking, AHH! Cum in your slutty mouth!”

Jaiden couldn't do anything, but I saw him shake his head.

“Here, sissy...ARGHH!! Drink my cum...Bitch...AHH!”

I saw Jaiden’s eyes get huge as the hard cock shot his mouth full with the pizza man’s load. He pulled his cock out, and Jaiden fell on all four and spit all the cum out on the floor as he gasped for air.

“Oh my god! How could you?”

The pizza man zipped up his pants, “The pizza is on me! Order from me again if you miss a hard cock to suck!”

Jaiden spit some more cum out. “I’ve got you on fucking tape and I’ll show it to the cops. You violated me!”

The pizza man walked over to Jaiden and grabbed around his neck and choked him. “Where is the camera, you little bitch?”

Jaiden quickly pointed beside the TV. “There...It’s over there!”

The pizza man let him go, took the camera and pressed the button for the elevator. “You are more like a girl than you think. Acting like a little bitch while you were the one teasing me, with your pretty bra, panties, stocking and heels!? This was your own fucking fault, slut!” The elevator doors opened and he left with the camera.

Jaiden got up, took some paper towels, and cleaned the cum of the floor. He took the pizza and a can of coke up to his room. He sat down in his couch, and ate a slice and put on some music again. He didn't look sad at all. Then I heard over my headset him talk to himself...

“Oh my god...I just sucked a cock!” And he smiled.

He put his slice down and placed his each heel on the edge of the table, and spread his legs. I zoomed the camera in so I saw him straight on. And there he pulled out a semi-hard dick out of his mom’s black panties.

“Mmmm...! He saw me in mother’s lingerie!”

He started jerking his dick, and this time I could see it nicely. It was a bit bigger than mine, but nothing like a real cock. He jerked it as he slid his hand down his black stocking leg. Oh boy, he looked sexy sitting there on his couch playing with himself. I put my tiny dick back in my Wolford pantyhose again, and wanted to go meet him, so I pressed the button and the secret doorway slid to the side and the draws opened. I walked out and pressed the secret button in the one draw and it closed after me. I walked out into the living room and shouted for Jaiden.

“Jaiden! Are you home?” I heard a couple of bumps upstairs. I made myself a cup of coffee, and waited for about 3 minutes. Then I walked upstairs and down the hallway to Jaiden’s

door. I knocked with one hand as I had my cup of coffee in the other. “Hello, Jaiden?” Then I heard him.

“The door is open. Come in!”

I opened the door and saw him sit by his computer with a slice of pizza, but not in his mother's lingerie anymore. He had a pair of jeans with a black t-shirt and his sneakers on. I looked at his ankle and saw he still had those stockings underneath his jeans. And I looked at his chest where I could see the bra shape poking his t-shirt. He still had the lingerie on underneath. He saw me and his jaw dropped instantly.

“Hi, Jaiden. How are you doing, sir? He-he, close your mouth, Jaiden! You could stick a whole cock in there!”

He blushed so hard. “Ehh...! Sorry. Just forgot how beautiful you are!”

I drank a little of my coffee. “I called your cousin and she told me that you took the bus home. And you forgot your phone there!”

He sat down in the couch and took another slice of pizza. “Yeah, I had enough of her. What are you doing home already? Is mom with you?”

I put my coffee down. “Oh that pizza looks good! Can I take a slice?”

He nodded eagerly.

I took a good bit of it, and mumbled on as I chew. “Your mom had some things she had to finish. Don't know when she will be back. Something about a week. But she wanted to make sure you got to school!”

He rolled his eyes. “Yes of course she told you that! Well nice to have you home again. I really like your new hair colour!”

I smiled at him. “Oh thank you, Jaiden. I like it too! Mmm...good pizza! So what are you up to?” I flipped my Louis Vuitton heels off and put my nylon feet on the table. He took his coke and drank from it. As I saw his eyes all over my nylon feet, I couldn't resist asking him. “Oh man...My feet are so tired after being in those heels walking around the airport. Just to get my car back! I could really use a foot rub right now!”

His eyes got big. “Ehmm...I can give you a...Eh...foot massage?”

I laughed “Ha-ha...! That’s kind of you! But they are really smelly with being in those heels most of the day. Kind of you to offer though!”

He turned towards me with one knee on the sofa and one foot still on the floor. “I don't mind...Really. I give my mom foot rubs sometimes. Now they are smelly, so I’m used to worst!”

I had no clue that he had rubbed his mother's feet before. Maybe that's how it all started for him? But Lauren’s nylon feet had the best smell!? Oh, I got hard just thinking about them.

“Well if you say so. But if you can't stand the smell, then feel free to say no!”

His eyes lit up, and he nodded. I swung towards him on the couch and placed my nylon feet in his bent knees lap. And I could clearly see the black nylon ankle of his, but I guess he had forgotten because he rubbed my feet instantly as they landed in his lap. He looked at my nylon feet all the time.

“Oh my god, Jaiden...! Mmmm...you have done this before. Ahh, that feels good on my tired feet!” I leaned my head back and just enjoyed my foot massage. I heard him sniff the air. “What are you doing, Jaiden?”

“Eh...! Ehmm...! Nothing!”

I looked at him. “I remember when I saw those pictures of my black opaque pantyhose legs on your phone. Do you like girls feet?”

His face totally blushed. “No...! Why would you ask that?”

“Because you can't stop staring at my feet? And I'm pretty sure you just tried to smell my sweaty nylon feet?”

He had no clue what to say or do. He looked down at my nylon toes again and said “Yes...”

“Yes what? You like girl’s feet? Or you tried to smell them?”

He kept on rubbing my nylon toes, and god, it was good.

“Both! But you are like the prettiest girl I have ever seen, Caroline! You dress nice and always in pantyhose. That drives me insane! So this is the best thing that ever happened to me!”

“That's better. Feels good telling me the truth, right?”

He nodded.

“Go ahead and smell my dirty nylon feet!”

He just stared at me and looked like one who couldn't believe what he just heard.

“Now...Smell them, Jaiden!”

He pulled one of my nylon feet up to his nose and took some big sniffs. I saw a little bulge forming in his jeans.

“Oh Jaiden...you really enjoy that! Mmmm yes, get your nose in-between my sweaty nylon toes!” I felt his body shaking. “What a good little boy you are! Do you still wear your mother's panties?”

He stopped with his nose between my nylon toes and stared at me as his face turned red.

“No...”

I took my other nylon foot and gently rubbed it against his nylon ankle. “What is this, Jaiden?”

He froze for a moment. “That’s...That’s...”

I smiled at him. “That's your mother's nylon stockings isn't it?” He didn't say anything. So I pushed his sneaker off with my nylon foot. The sneaker fell to the ground revealing his black nylon foot. I looked at his nylon foot, and normally I'm not into guys feet, but his foot looked feminine although they could use a pedicure. I rubbed my nylon sole against his nylon sole and I saw his eyes roll back into his head as he started sniffing my other nylon foot again.

“My god, that feels Ah...Amazing, Caroline!”

“Mmm...you perverted little mommy’s boy! Like smelling your maid’s nylon toes?”

“Oh god yes...They smell freaking amazing!”

I smiled, “I can see that bulge in your jeans. Don't you think you should let it breathe a bit?”

He looked at me. “I can't! I am too embarrassed to show myself to you!”

I laughed at him. “Ha-ha-ha! Come on, Jaiden...let me see how cute you look in your mother’s panties and stockings? Show yourself, little sissy!” I felt his body twitch. “Oh...You like being called a sissy? Do you also have a sissy name?” I moved my nylon feet from his and rubbed my foot against his bulge instead. He twitched again and made a slight cough.

“EH...hmm...Janice...”

I saw him blush. “Oh that’s cute, Janice! Now Janice, take your fucking jeans off!”

He looked surprised, but gently got up and unbuttoned his jeans and slowly let them down. I saw his bulge poking the nice soft satin fabric of his mom's panties.

“Loose the t-shirt too!”

And he did. Now standing in front of me in his mother's lingerie.

“Sit down, Janice. I wanna see you play with that sissy cock!”

He sat down and his face was so red, but he gently pulled a semi-erect dick out. He almost didn't have any hair and it made him look so smooth and feminine. He pulled his foreskin back and a nice pink dick head shined.

“Ohh, what a nice girly dick you’ve got! Mmm...pull that sissy dick good!”

He looked at me shyly as he bit his lip a bit. “I can't believe you are watching me, Caroline! AH...AH...It feels so good!”

I stretched one of my nylon feet and rubbed it against his balls.

“AHH! Fuck...Mmmm...wow!”

I laughed again. “He-he. Are you already cumming soon? It sure looks like it! Don’t you fucking dare to cum over my pantyhose!”

He nodded eagerly, “I won’t I, AHH! Promise, miss! AHH!”

I could see he was so close already. I sat myself up, took a big slice of pizza and took a little bite.

“ARGH! I’m...AH! Fuck...Gonna cum!”

I quickly took a hold of his erect dick and took my slice of pizza close to his cumming dick. He got a huge shock, But cummed so much in pure pleasure. I pointed his spraying dick over my slice of pizza and it filled the whole slice so good with hot cum.

“AHH! AH! What are you...AHH! Doing? MMMMMM!”

His dick became sloppy and I took a big bite of the slice of pizza. “Mmmm. That's such a juicy slice of pizza!” I said with a full mouth.

He sat there staring at me with an open jaw, me eating his warm cum from the big slice. His cum was so tasty and had this sweet flavour of youth.

I took another bite and said “So tomorrow, Janice, you are going to school or should I tell your mom that you dress in her panties and stockings?”

He shook his head. “No! Don’t worry, I’m going! Please don't tell her anything, ok?”

I got up and looked at him. “Good! Breakfast is ready tomorrow at 8:00, so be ready then!” He nodded, and I winked at him and said “Thanks for the pizza!” and closed the door behind me. And of course I ate the rest of the pizza on my way down to the living room!

I had a cold beer, and the rest of the night I watched some TV and went to sleep in Lauren’s bedroom. I was so tired of the flying that I didn't even take my clothes off.

~*~*~*~*~*~*~*~*~*~

I got up as I heard my phone ring. I answered and it was Lauren...

“Hi sweetie! How are you and Jaiden doing?”

I yawned and said “Ohh, it all went fine yesterday. We just saw a movie and ate some pizza. What time is it?”

“Ehmm...it must be around 6:52 there. You know he has to be in school at 9, right?”

I yawned again. “Yeah, thanks for calling, Lauren...otherwise I don’t think I would have gotten up! How are you doing over there?”

“It was a late night yesterday at the factory, but the trucks will be here soon...and those race cars are finished soon!”

Then I heard Roger in the background. “Are you coming to bed, Lauren?”

“What the hell are you together with Roger?” I became so jealous.

“Ehh...” There was an awkward silence. “You know how guys are?! He hadn’t really had time relieve himself sexually. So I offered him!”

“But...but...you are my girlfriend, Lauren? Really? And you’re just gonna fuck him?”

“Relax, hun. It’s nothing more than sex. You are still my girl!”

I really tried to relax, but it bothered me. Ok, if she wanted to play like that, it's on! “Ok, I'm sorry, Lauren. You deserve a proper cock for that sweet pussy of yours. And don't worry, Jaiden will be at school!”

“I knew you would understand, Caroline! And thanks for taking care of my boy! Gotta go...Kiss Kiss!” and she hung up.

I wouldn't mind at all if she got fucked while I was there watching her. But that she kinda did behind my back, just pissed me off. Now I was going to have some fun and try to forget this fucking phone call!

I stood up and went into Lauren's secret room to check up on Jaiden. And to my surprise, he was already up, and still in the lingerie from last night. But he stood over by the big glass wall out to the balcony. I zoomed in on him and saw him bend over, moving his head in a rhythm. I put the headset on and turned up the volume and I heard some slight gagging. He removed his head and I saw a purple dildo sticking on the glass window at ass height. Full of saliva, he turned around and let the panties down to his stocking’s ankle and spread his ass cheeks and slowly pressed his hole against the purple dildo.

“AHH...Mmmm!”

I heard a little pop.

“ARGH! Fuck!” and he began to push back and forth. “Oh my god...AH! Caroline...! OHH...Yes! You ate my cum...AAHHH!”

He was now thrusting himself on the dildo, and I could see his pretty feminine stockinged legs started shaking slightly. Oh damn, he looked sexy like that. He reminded me so much of myself when I started. Everything was so exciting!

“Argh...I wanna be Caroline’s...AH...Sissy Slave! Mmm Yes! God, I'm gonna...AHH! CUM!”

His legs buckled under him and I heard a big flop! And he fell to the ground on all 4’s, with the dildo still inside of him, and his dick oozing cum on the floor. “Holy...Fuck! AHH...MMMMM!” He slowly pulled the dildo out and his body twitched as he did so.

‘So that little sissy boy wants to be my slave? Mmmm, that's maybe not a bad idea!’

I saw him take the lingerie off, and I quickly got out of Lauren's secret room and closed the door behind me. I went through Lauren’s clothes and found a pair of red-laced G-string panties and a matching bra, and a red pair of nylon pantyhose. I folded it nicely and went to the kitchen and made myself a fresh cup of coffee. I then texted Jaiden’s teacher, telling him that Jaiden felt ill and probably wouldn't come to school this week. I got a text back that thanked me for the info and wished Jaiden well. I sat down at the kitchen table and drank my coffee, and not long after, Jaiden came down in a white normal bathrobe. I looked him up and down, and he saw me.

“You don't have your mother’s lingerie on today, Jaiden?”

He sat down at the kitchen table, as he blushed. “Ehh no...Not in school!”

I smiled at him as I got up. “Sure, I can understand that! A bit too risky having it on in school. So what do you want...Toast or cereal? And want a cup of coffee too?”

“Cereal, that's fine! And yes, a coffee would be nice. Thanks!”

“Sure...coming right up!”

I put the cereal, a spoon, and a bowl in front of him and he took some. I went back to make his coffee and he sat with his back to the kitchen. So I reached down my purse and picked up my hormone drops and put like 10 drops in his coffee and put it away again.

“You use milk or sugar?”

“No. Black is fine, Caroline. Thanks though!”

I put the coffee down beside his bowl. “There you go, Jaiden. Enjoy!” and I sat back down again, took my phone and read some news. Every time he drank from his coffee, I looked at him and smiled. “Good coffee, right? He-he!”

He smiled back “Mmm yes, it's delicious! Just what I needed!”

I was grinning from ear to ear, and he drank the rest of it.

“Well I’m gonna hit the showers and get ready for school. Thanks for breakfast, Caroline!”

“No problem. I'm just gonna go down and get something in my apartment, but I’ll be right back and ready to go, ok?”

He went upstairs again, and I took the elevator down to my apartment. I unlocked the door, and as I walked inside, I saw my pantyhose spread over my couch. What the hell? I for sure didn’t leave them there! I walked into my bedroom and again I saw the sexdoll in different clothes. It was now in a pair of black nylon pantyhose with the doll’s dick sticking out through a cut hole, And a black bodystocking on. The doll was on her knees with her face planted in my pillow right in the middle of the bed. I saw a lot of dried cumshots on the sexdoll’s pantyhosed ass. I bet Jan has been in here fucking my doll while I was away! Right now, I am here for something else. I went through my draw and found what I was looking for. My stainless steel gold plated chastity belt. I grabbed it and also took one of my diamond butt-plugs with me. This was black with a purple diamond, medium-sized. I put it in a small plastic bag and went out of my apartment and locked the door again. But I guess it wouldn't help anyway. I turned around, and sure enough, Jan was standing there right in front of me.

“Oh wow, Caroline, you look so fucking hot! I like your dark red hair! You are making me hard already!” He looked me up and down. “Amazing pantyhose...”

“Shut up! I know you have been in my apartment! Leave me alone, you sick bastard, or I’ll go to the police and report you for trespassing!”

He quickly got a sad and hurt look on his face. “But...”

“But fucking what? You thought we had something special going? Guess what? We don't! If you go through that door again, there is no second chance. Got it?”

He nodded gently, “Yeah, sure...!” He walked back to his apartment and closed the door.

Phew, I really hope that is that with Jan. I had too much with my maid job and soon started my pantyhose company. No more time to fool around. Not with him at least! I took the elevator back up. I’d grabbed the red nylon pantyhose red lace G-string and bra with me, and went into Lauren’s bathroom and found some shaving gel and a razor. Then I walked up the stairs and into Jaiden’s room. As I entered, I could hear him sing in the shower. The bathroom door was slightly open, so I gently took my heels off and tiptoed into the bathroom. I was right next to the shower curtain. And with one swipe, I pulled the curtain away. He got a huge shock and turned around, and he actually screamed like a girl.

“ARGH!”

I took the showerhead and unscrewed it from the hose. “Turn around, Jaiden!”

He looked so surprised at me. “What...Are you doing?”

“I said, turn the fuck around and bend over!”

He realised that I meant it and he slowly did as I told him to. I pushed the hose between his ass cheeks and found the hole.

“ARHH!! Ohh my...”

I filled his insides with water for like 6 to 8 seconds.

“Feels so...AH! Weird! Stop!”

I stopped and pulled the hose out again. “And now you go to the toilet! Do that 2 more times and then shave every hair on your body. Got that?”

He quickly jumped out of the shower and onto the toilet as he nodded to me. I walked out of his bathroom and sat down by his computer. I heard different noises come from the bathroom.

“Uhh...Aahhh...Mmm AOHH...”

I looked through his computer as he took some time in the shower. I looked at recent files and found the anime picture of me, and also another one with us both anime style, but him sucking my nylon feet. I then saw a video called ‘She ate my cum’. I clicked it and saw the video from this morning where he fucked the dildo against the glass wall in his mother's black lingerie. He looked so cute, and of course, it turned me on seeing it straight on. He came out of the bathroom like 15 minutes later, and he saw me sitting by his computer and saw his self-made video on the screen. I looked at him and smiled. He totally blushed, but froze in front of me butt naked.

“Oh Jaiden! What a naughty little boy you are! Did I make you so horny yesterday eating that sweet cum of yours?”

He didn't say anything, but just nodded.

“Or should I just call you Janice the perverted sissy boy? You know what I do with little sissy boys who can't control their lust?”

There came a little sound. “No...”

“Say what? I didn't hear that?”

He made a slight cough. “No miss...Ehm, I don’t know!?”

I stood up and got right in his face as I whispered in his ear “I lock their tiny sissy dick up, and plug that tiny pussy. Got that?”

He just froze again and barely nodded.

I pulled out the chastity belt and unlocked the little padlock. His eyes got big, but I stuck his penis inside it, then grabbed the ring and locked his balls to it, and clicked the tiny padlock close.

“Good sissy! Without complaining! Now go find some lube! I know a horny little sissy has some as I just saw you fuck that dildo!”

His face turned red again, but he opened the draw in his computer desk, and there was a tube with lube.

“Mmmm, that's it! Now let me plug that tight sissy pussy for you!”

He automatically turned around and bent over. I lubed 2 of my fingers and pushed them gently inside his pussy.

“AHH...Mmmm!”

“Shh...I don’t wanna hear fucking pleasure sounds coming from you. Understood?”

He nodded.

I pulled my fingers out his clean asshole and then lubed the dildo. “Now stay calm!” I pushed the lubed butt plug against his hole and I felt it expands.

“Mmm...! Sorry miss!”

I pushed it harder in as he made a sound.

“Argh! It hurts...”

“Then be a good sissy and shut the fuck up!”

I felt him trying to keep his mouth shut, but as the dildo slipped in, he made a loud moan.

“AAAHHH! Mmm!”

I saw a long ruler on the table and smacked his ass. Again, he screamed like a girl.

“ARGH!!!”

His hands were caressing his ass which I just smacked.

“Get those fucking hands away! You made 2 sounds of pleasure! You deserve another smack. Come on, turn around!”

He stuck his butt out a little and closed his eyes hard and I smacked it again. He made a sound, but nothing like a scream, this time he held it inside.

“Much better! Now put this on!”

I threw his mother's G-string, bra, and red nylon pantyhose onto the floor in front of him.

“But I’m going to school? I can't wear that?!”

“So you would have worn a chastity belt and a butt-plug up your sissy ass, and you complain about the lingerie?”

“But you are pretty intimidating when you boss me around, so I better obey! I don't really wanna get spanked anymore! Putting those red nylon pantyhose on will most likely be seen by others!? I'm getting teased enough at school!”

I stood up and went to his closet. “You're not going to school this week! I called in sick for you!” I found a pair of black sweat pants and grey hoodie. “Now get in your mother's G-string panties and bra. Then put on those red nylons, and this!”

He did. “You called in sick? But why?”

“I need your help with something!”

He put the red panties and bra on and sat down on the couch and put those red nylon pantyhose on. They looked really nice on his legs. I clicked the pictures he has drawn on the computer. And he looked over.

“I know what you want deep inside!”

He blushed as he saw the anime pictures he had drawn of him sucking my pantyhose feet.

“You drew this, right?”

He nodded, “Ehh...Yes!”

“Those are really amazing! I could use someone who can draw like that! But I can see in this picture where you are sucking my nylon toes that you almost worship me, right? You wanna be my good sissy slave?”

His body twitched, and quickly turned away and put his sweatpants on. “I...I...Didn't know that you...found out all this stuff about me! I feel ashamed and so fucking embarrassed, Caroline! I wish this never happened!”

He eyes teared up and I picked up the ruler again. I walked over to him, pulled his sweatpants down his bum, and smacked him hard twice.

“Stop talking like that! If you wanna be a good sissy, then embrace your deepest desires! I need your talent as a drawer. I tell you what that's about when you're trained as my slave! Got that, Janice?”

He caressed his ass and nodded.

“Good! Now put on the hoodie and let's go shopping!”