The Robertson's Sissy Ch. 20

It was 1:30 am when I woke to some moving and Lela's soft voice begging for me. I wasn't sure what was wrong but I rolled over to find her touching herself. Lela grabbed me and kissed me and whispered.

"I can't sleep. I teased you so much that now I'm so fucking horny," she whispered.

I grew pissed that she woke me just to tease me again, "Really Lela?"

"No, you win. I wanted a quiet night but now it's technically morning. Now I'm ordering you to finger fuck me," she panted in a lustful daze as she guided my hand between her legs. Her pussy was clammy and overly wet as I gently rubbed it. She moaned and clawed at me as I placed my hand under her neck and kissed her. My hand rubbing her sensitive little clit as her eager joke moistened even more for me . Her head melted in my hand as I slid my middle and ring finger inside her.

Soft moans escaped the mature beauty as I began forcefully finger fucking her. Sexually frustrated from the night of teasing I really gave it to her, causing my palm to smack and rub against her sensitive clit. She wouldn't let me escape her grip as she moaned in my mouth as we kissed. The sounds of her wet pussy being savagely fucked by my fingers filled the room between the grunts and moans of the woman. I paused briefly as my finger found her little g-spot and applied pressure before rubbing it. Her hand reached over and freed my cock and stroked it as I rubbed her soft flesh.

My cock was hard as a rock when I applied even more pressure. Her smooth legs began kicking as she held and kneaded her breasts. She began cumming as I kissed her deeply as she squirmed while her pussy clenched around my fingers. I slowed my assault on her g-spot as we calmed and kissed.

"Again. One more time," she begged.

Without warning I applied pressure back on her sensitive area and gave her what she wanted. This time took a bit longer but she was so horny that it didn't take much. She stroked hard and squeezed my cock tight as she came a second time. Slowly we calmed down when she released her death grip on my cock before grabbing my hand.

Slowly she brought my wet fingers to her mouth where she sucked them clean. This woman was killing me and I had enough of this teasing torture. I went to roll over when Lela held my wrist and rolled over the other way, wrapping my arm around her waist.

"I guess I'm a big spoon now," I joked as I shifted over and held her.

She giggled and pressed her ass against my hard cock and wiggled.

"Lela please. You won the teasing game you are playing. I can't anymore."

"You can't cum now. I want a big load on the plane. I'll stop teasing you now. Get some sleep."

It was hard to sleep now knowing I was going to get some action on the plane. She held up her end and stopped teasing me as we fell back to sleep. The alarm woke us hours later as we struggled to get up. I laid there as Lela woke up and turned the light on.

"Get up," She told me as I threw the covers over my head.

Lela ripped the covers off the bed and crawled on top of me naked from the night before. She began biting my ear and telling me to get up. I knew there was no winning this battle and rolled out of bed.

"Go wash the makeup off your face and take your collar off. I'll set some clothes out of you," Lela ordered.

I retreated to the bathroom and washed up before finding Lela dragging suitcases out of the closet. A pair of shorts and white T-shirt sat on the bed as I grabbed them to get dressed.

"Wait. Wear these," Lela said as she threw me a pair of yellow lace panties.

I didn't have the cock cage on so I didn't complain and got dressed. Lela went to the bathroom as I went to go eat something in the kitchen. She joined me wearing a yellow and green sundress which barely held her tits in. Normally her wardrobe was one size too tight but this was the opposite and I loved it. She knew I loved yellow against her tan skin. Each step she took caused her beige heeled sandals to click against the tile and her body to jiggle in all the right places. I helped her carry three large bags to the door which fit the stereotype that women pack way too much.

"Did you bring everything?" I joked.

"Two are your's and one is mine. Don't worry I got everything we will need," she said with a slightly devious smile.

"Come sit down," she ordered as she pulled out a kitchen chair.

I sat as Chuck joined us carrying his bag while Lela fixed my hair into a ponytail. As a woman long hair looked good on me but as a man I must have looked weird. It was only for the airport and plane so whatever.

Lela and Chuck talked about their arrangements when a limo pulled up to the house. I followed Lela outside and helped the driver with the large heavy bags. Loaded up and ready to go I joined the Robertson's inside.

I slid across the cool leather seats until I was right next to Lela. She got me so horny the night before that I couldn't take my eyes off her and her breasts. She caught me looking a bit too much and immediately ordered me down in my submissive position. The limo began driving down the driveway as I laid across the seat, placing my head in her lap.

Like a dog she pet my head and played with my hair as her and Chuck continued talking about the flight and getting to the beach house. I guess she was back in her dominant mood so I did nothing but obey her. I was still tired from the night and easily dozed off. The scent of lavender on Lela's skin from the bubble bath the night before calmed me enough as I fell asleep.

I woke to Lela's finger stroking my face," Wake up princess. We are here."

I sat up just as the driver opened the door to let us out. We took our bags inside as Chuck went to the counter to get our tickets. Lela just stood there staring at me and with a huge smile as her body swayed side to side. She was like a little kid and I could tell she was overly excited to take me away. It was a good sign, if she was happy then I was happy.

Chuck got our tickets and we left our heavy ass bags with the crew before heading through security. Lela gave me a carry on bag which I placed on the x-ray machine before stepping through the metal detector. Lela already went through and waited for me as I cleared it the first time without setting the alarm off. On the screens I watched my bag go through and noticed a bunch of dildos and other sex toys in it.

The woman checking the machines had a smirk on her face as I grabbed the bag and turned to Lela who was fighting the urge to hysterically laugh.

"You can tell me next time," I embarrassingly whispered.

"Just be happy. I had to put the handcuffs and really kinky shit in the other bags. I also could have made you go through the detector with you little cage too," she giggled.

She was right, that would have been embarrassing as hell. I know there was a reason she was going easy on me but I knew it wouldn't last. We sat in our area and waited for boarding to start. Lela rested her head on my shoulder as everyone stared at the young guy with a weird ponytail with the bombshell latina. Not going to lie, I would have been wondering it myself.

Lela hummed in excitement as they announced the boarding of our flight. She popped up and I followed her and Chuck to get our tickets scanned and board. The plane was small, a single aisle split two rows of three seats. I followed them up the aisle as they waited for me to get in first. I got the window as Lela sat in the middle.

"Ugh. We booked this so late we couldn't find a good flight with first class. Good thing this won't be a long flight."

"Be happy we got the house on such short notice," Chuck replied.

I just sat there quiet as they bickered about everything. Staring out the window I waited until the plane started moving. Lela took out a small blanket and covered herself before resting her head on my shoulder. I put headphones in and tilted my head back and closed my eyes. I must have been sleeping well as I woke with my head on Lela's shoulder. She was hiding a book she was reading from others to see. When she noticed I was up she quickly closed it to show me the cover. It was a book on BDSM slave training. This is where her dominant behavior was coming from.

"Sorry you can't read any of this," she quietly laughed as she put it away.

Chuck was reading a newspaper as Lela pulled her blanket over my lap.

"I'm not cold Lela," I told her but immediately shut up when her hand grabbed my cock.

Like a surgeon she skillfully unbuttoned my shorts and freed my cock under the blanket without making it look like anything. Her soft hand gripped my flaccid soft and squeezed it gently until it was hard. I tilted my head back as her soft hand jerked me off as she chatted with Chuck like nothing.

"I'm sorry for teasing you so much last night. Wait. No I'm not," she whispered, "Warn me before."

She quickly turned back to conversation with Chuck as the flight attendant passed by. Her soft warm hand skillfully stroked each inch of me. I wasn't one for handjobs but Lela knew what she was doing. Her hand slid up and down my swollen cock, even stopping a few times to massage my balls. She tightened her grip around the base of my head and gave short tight strokes pushing me close to the edge.

Lela immediately backed off and denied me as she just held my cock still in her soft hands.

"You only cum when I say you can," she whispered.

I figured doing this in public Lela would want to be quick but I should have known better. She got a sick perverted high from doing this and was going to ride it out as long as she wanted.

Her masterful stroking continued bringing me to the verse of orgasm over and over. Each time she would let go and gently massage my balls until I calmed. Finally she had her fill and allowed me to release.

"Lela," I whispered as she quickly tapped Chuck's legs.

Chuck opened his newspaper wide as a blocker as Lela dipped her head in my lap. Her warm mouth encased my swollen head just in time for my cock to start pulsing wave after wave of pleasure through it. After all the teasing I wanted to scream but fought to stay quiet as she stroked me until finally my orgasm came to an end. Her plump lips created a tight seal around the base of my swollen head making sure she didn't spill any of the load she craved. Finished, she popped her head up just as the flight attendant walked by again.

She smiled at me knowing we almost got caught before opening her mouth and showing me a mouthful of thick white cum. She wasn't careful enough as cum spilt from her mouth down her chin and she closed and laughed. Swallowing as she wiped her chin clean before kissing my cheek.

"Thank you for last night. If you are good on this trip then we will see what happens on the way home. I think we have a private plane," she whispered with a smile.

She rested her head on my shoulder as I stared out the window at the landmass we were approaching. Not long after we started our long descent to the airport we landed without issues. We grabbed our carry on bags and departed the plane with all the other passengers before going through customs and getting our other bags.

Lela and I waited for Chuck who was getting the rental car for the trip. She didn't say much to me but kept smiling so I knew all was good. Finally Chuck pulled up in a black tinted SUV and Lela and I dragged the bags to the car.

"Put that blue bag in the backseat," Lela said as Chuck and I loaded the rest in the trunk.

With all bags loaded Chuck jumped in the driver seat while I grabbed the blue bag and joined Lela in the back. Immediately she started pulling everything out for Michelle to wear.

"Get naked," she ordered.

I thought she would wait but I learned to obey her every wish. I stripped off my clothes as she attached my chastity cage and secured my choker around my neck. She helped me with a very tight skirt before clasping the matching yellow lace bra to my panties. I stuffed my breasts in as she buttoned a tight red blouse on me. My sneakers were tossed in the trunk as she handed me a pair of black heels.

"Are we stopping to get food for the house?" Lela asked as Chuck pulled into a supermarket.

"Yeah, we'll get some food and alcohol. I don't know what might be there already."

"Just get some basic stuff. We can come back. I need to stay here and finish making this bitch pretty," Lela said as she opened her make up bag.

Chuck parked and left us as Lela took the time while we were stopped to do my makeup.

"There, Michelle is looking good again," she said as she undid my ponytail allowing my hair to fall free.

"Thank you Lela. You're the best," I complimented her as I knew she loved it.

"Come here," she ordered as she pulled my head into her lap.

"You were such a good girl last night. I expect that all the time now. See how great and easy things are when you are good?"

"Yes Lela. I promise to be good," I replied.

"Good girl. Now what is taking this asshole so long."

We waited as Chuck took an extra long time in the store. Luckily he left the car running with the AC on. Lela was getting bored and scooted across the seat to me. Her soft hand pulling my leg over hers while spreading them. She turned my face and kissed me as her hand slid up my very short skirt until it found my caged cock. Gently she rubbed it and stroked the cage.

"Do you like it when I play with your little clitty? From now on when you are caged it's called your clitty," she whispered.

My cock swelled in the cage and became uncomfortable but I knew the answer she wanted.

"I love it when you play with clitty Lela," I responded as my cock filled the cage to capacity.

Lela kissed me deeper as she held my cage and stroked it. The cage would move both my cock and balls at the same time allowing it to fill with more blood then cage couldn't hold. Lela lowered the strap on one shoulder of her yellow dress allowing one braless breast to slip out.

"Come here," she whispered as she brought my face to her exposed breast.

I took her erect little brown nipple in my mouth as she moaned in approval while stroking my clitty faster. It began to hurt but I was mesmerized by her soft firm breast as she fed it to me. I suckled her like a child until we were started by the truck opening.

"Oh shit," Lela jumped and pulled her dress back up.

"Sorry for the wait. I just got a bunch of stuff instead of the basics." Daddy said as he loaded up the trunk with tons of bags.

Lela and I watched him over the seat as her hand continued to rub my caged little clitty. My cock was red and ready to explode with pressure as Daddy closed the trunk and got back into the driver's seat.

"I hope you two didn't get too bored out here," he said knowing he took longer than expected.

"It's fine Daddy. I was playing with Michelle's little clitty," Lela giggled as Chuck watched in the rearview as Lela rubbed my caged member.

He laughed as he pulled out and Lela resumed kissing my neck. My hand found its way to the breast I was sucking and massaged it as Lela pulled off and scooted back away from me. Slowly she spread her legs and slid her sundress up her thick tan legs.

"Oops. I forgot to wear panties this morning," she giggled as she told me to come with a finger.

I wasn't allowed to eat her yesterday and couldn't wait to taste her. I leaned over and slid across the leather seat until I was face to face with her wetness. The warmth of her body radiated against my face as the aroma of her aroused pussy put me in a hypnotic state.

Lela's hand on the back of my head pushed me down the final few inches as I tasted her. Gentle long licks up the entire length of her as she moaned in approval.

"Really you two?" Daddy asked from the front.

Lela moaned back, "I can't wait for the house."

With her pussy licked clean I focused on her sensitive clit. Sucking it while I held her smooth tan thighs. Lela moaned as my tongue poked and got rough with her little button. I knew I was doing a good job as her hand held me in place, not moving. Like a punching bag my tongue beat it as her pussy leaked her irresistible fluid. I gave her another long lick which caused her body to shiver.

"Lay down. I want to play with your clitty," Lela panted as she pulled me off.

I rolled over on the seat as Lela dropped the straps on her dress and allowed her firm breast free. She straddled my face and looked at Chuck.

"Having fun Daddy?" she giggled.

Before she lowered herself on me I caught a glimpse of Chuck, cock out and stroking as he drove and watched. Lela lowered herself as her round ass swallowed my face. Twerking on me and laughing before leaning forward in a 69 position.

I kneaded her magnificent ass and attacked her pussy with my tongue as she licked and bit my cage cock. She moaned as she roughly played with it as her ass suffocated me with no mercy. Occasionally she would pull off slightly and rub her bare breasts down over my cock before shaking her ass in my face. She loved being in complete control and I loved when she sat on my face.

I buried my tongue inside her as she rode it to orgasm, crying as she came on my face. Gently she kissed my cage as she calmed down before sliding off me and fixing her dress. I sat up next to her as her hand began stroking my cage cock again. It hurt like hell and I couldn't take it anymore.

I grabbed her wrist and pulled her hand off but that infuriated her as she slapped my hand and squeezed it hard while staring at me with fire in her eyes. Luckily Chuck broke up the moment before I got myself in trouble.

"Michelle come here and finish Daddy off," he ordered with his magnificent cock in his hand.

I leaned forward to climb over the center console when Lela yanked me back by my skirt.

"We are almost at the house. Just wait."

I stared out the window at the palm trees and water as Lela continued to torture my cock. We pulled down a private street and drove to the end where a large white beach house stood. It wasn't huge but was very well kept, secluded and private.

"We are here!" Lela announced as she let go of my cage and hopped out.

We each took a bag and followed Chuck inside. Right through the door sat a decent sized kitchen to the left while straight ahead opened up to a large living room. Two of the walls were completely made of windows. The far one overlooked the beach with a porch and access point while the other gave access to a large pool area surrounded by vegetation and palm trees for privacy.

"Go help with all the bags and groceries," Lela ordered me and snapped me out of my daze.

Slowly I unloaded the car, careful to carry the heavy bags in my heels. Chuck got the bigger bags while Lela stayed inside and put the groceries away. I grabbed the last bag and shut the door, carrying it inside to the sofa before bending over and it putting down. I wasn't able to stand back up when I felt Daddy's strong hands on my waist.

Slowly I stood upright as he pulled my skirt up before forcefully bending me back over with a hand on the back of my neck. I let out a slight shriek at his forceful nature. I gripped the arm rest of the sofa as I heard the zipper and buckle of his shorts. I knew what was coming and after the car ride I wanted it.

I felt my little yellow panties get pulled tight across my ass as a warm drop of spit landed in my crack. His soft cockhead ran up and down my crack as he spit more and smeared it over my eager hole. Without warning he pushed inside me causing me to jump and shriek.

"Really Chuck?" Lela yelled from the kitchen as she heard me squeal.

"Listen, I watched her blow a load in my wife's mouth and then eat her out in my car. It's my turn," he responded as he slid his entire length inside me.

I stood there holding the arm rest as my legs were tight together, balancing on my heels. Daddy's strong hands rubbed my tight little ass as his fat cock began working me. I moaned as Lela walked over and slapped my ass hard.