The Robertson's Sissy Ch. 20

"Make sure you fuck her hard. She did something to piss me off in the car. I want to hear the bitch screaming from upstairs," Lela ordered before walking away and up the stairs.

Daddy grabbed my waist and the back of my choker as I braced myself. Daddy yanked me back on his cock as I screamed in pleasure. His fat cock driving into my ass until his hips smacked against me. I lustfully tore at my blouse as he pulled me back with another loud smack and scream.

I kneaded my breasts through the lace bra and it was times like this I wished they were real. Daddy didn't thrust his hips, instead he would forcefully sway my whole body up and down his cock. Choking me by my collar with each pull back. I struggled to stay on my heels as his cock fucked me harder and harder. Slowly my body leaned over the couch to escape the roughest of his assult but all it did was trap me.

Bent over the arm rest with my ass in the air Daddy fucked me as hard as he could and I wanted to cum. I was vulnerable like this and was completely turned on.

"Fuck me Daddy. Fuck my pussy!" I begged.

I screamed as his hips smashed into me as a strand of precum dripped from my chastity cage. I gripped the cushion and laid my head down as my brutal fucking contined.

"Well that's what I want to see," Lela's voice cut through my screams.

Daddy slowed a minute and I could hear her heels clicking against the tile floor.

"You might want to see this," Daddy laughed as he pulled my head off the couch by my choker.

Lela was standing there and took my breath away. Wearing the tiniest bikini I had ever seen. Thin black straps held tiny cheetah print triangles over each nipple. They were barely big enough to cover them and thin enough to where her perky nipples poked through. Though barely supported, her breasts sat up like the defied gravity.

The trend continued to her bottom where the small cheetah print was barely enough to cover her swollen pussy lips.

"You are so cute when you are being fucked like a whore. Is Daddy fucking you good princess?"

Daddy drove into me extremely hard again as I squealed in pleasure.

"You didn't answer me. Tell Daddy how good he is fucking you and what you want."

I squeezed the cushion and struggled to talk against the force thrusts as Daddy choked me.

"You fuck my pussy so good Daddy. Please cum in my pussy," I struggled with a red face.

"Shit Chuck. Let go over her neck. I don't want marks on her."

Finally he released my choker but pounded me even harder.

"Michelle, when Daddy is done filling your pussy go put on the bikini I left out, make us a drink and join me outside," Lela said as she stepped outside into the pool area, leaving me getting fucked.

Daddy had my thighs straddled as he massaged and squeezed my ass cheeks together. He began breathing heavy and I knew he was finally going to cum inside me. He fell over on top of me driving his cock as deep as possible as it pressed hard against my prostate. I wiggled with his cock pressed against it and tried hard to cum as his cock pulsed and began filling me with his warm seed. Subconsiencily I reached back and gripped his ass and pulled him into me and held him deep inside. I laid there and wait until he deposited every last drop inside my bowels as I caught my breath and wiped the sweat from my face.

Slowly Chuck pulled out of my ass and gave me a final slap before walking away. I took a minute to gather myself and slowly walk up the stairs to the bedroom. A large bed filled most of the room with a large bath and jacuzzi. Lela laid out a tiny bikini for me to wear on the bed. A little black g-string with black and white polka dot top. I striped naked and slid the tight g-string up my legs before tucking my clitty in.

The top was like all the other I wore. It hide my cleavge and tied around my neck. I wish I had real breasts so I could wear something revealing like Lela did. I secured my hair in a ponytail and gave myself a look over in the mirror. I was satisfied with my sexy yet sporty look and slipped on the black sandals and grabbed my towel.

I walked through the house down to the kitchen feeling sexier than ever. I made a pair of drinks as I felt cum leaking from my hole. I laughed at how much Daddy came in me and wiped up before walking outside in the blistering sun.

Lela was laid out like a queen and watched my every step through her dark sunglasses. She smiled as I approached and sat up to accept the drink I made.

"Thank you princess. Come sit," she told me as she moved her feet for me.

I was scared she might still be pissed at me and immediately apologized, "I'm so sorry Lela. I'm sorry if I was bad."

Lela just sipped her drink and stared before asking, "So did Daddy fuck you good?"

"Yes. He filled my pussy up."

"Was it so good that you came?" She asked.

"No. I wanted to but couldn't"

Lela grabbed my bottom and pulled it aside to look at my clitty, "Bullshit let me see."

My cock was red as hell and hurt from all the restraint. I couldn't see Lela's eyes but I could tell she was surprised as she immediately began taking it off.

"Is that better?" She asked as she stroked it.

"So much better," I replied as I took a sip of my drink.

"I've noticed you haven't been cumming a lot recently when getting your pussy fucked. We may need to fix that but for now we are on vacation. We will deal with it when we get back."

I watched as she sipped her drink before putting it down. I had seen this woman naked everyday but nothing compared to how she looked in this bikini. Her tan skin shined in the sun with small beads of sweat glistening. Her breasts were round and her dark little nipples peaked through and her bottom wasn't big enough like I had thought. Her swollen pink pussy lips hung out each side.

"You look amazing Lela," I complimented her.

"Oh thank you. You are such a good little sissy," she happily said as she put her drink down and grabbed a bottle of oil.

I watched as she pulled the strings on her top and tossed it on the stone floor. She laid back and straighted her legs as I watched her little bikini bottom get swallowed by her pussy.

"Come her and massage me," she ordered as she held out the bottle of oil.

I would never turn down an opportunity to get my hands on her and quickly walked over and took the bottle. I poured a large glob on my hand and began working her shoulders, her skin was hot to the touch in the afternoon sun. Lela sighed in comfort as I worked her soft skin down her arms before running both my hands down the center of her chest and through her cleavage.

I stepped to the side and worked the rest of her chest. Each breast got worked with both hands with extra attention given to her now ecert nipples. Lela moaned softly as my finger passed over them. I walked down and knelt on the chair between her legs and rubbed oil over her toned little stomach, passing my hands down to her tiny little bikini bottom.

I paused and applied more oil to my hands before moving to her legs. From her gloriously thick thighs down her toned calves I worked her soft skin. Lela squirmed as I moved up her inner thighs to her pussy before smiling and grabbing the strings on her bikini bottom.

"You missed a spot," she giggled as she pulled the strings causing her tiny bottom to fall off.

Her pussy was wet in the day's sun and even more as I rubbed her with my oily hands. Lela gripped the arm rest and moaned as my soft hands gently rubbed her most sensitve area. It suddenly ended when Lela began to roll over on her stomach.

I stood up and allowed her to stretch out, her round mound of ass looked ever bigger as she laid with her legs closed. I re-oiled my hands and worked her legs from the bottom up to her fine ass which I decided to leave for last. Straddling her thick thighs I ran my hands up the small of her back to her shoulders. On the way back down I slid my hand down her side making sure I each hand passed across the side of each breast.

I applied just a bit more oil to my hands before placing the bottle down and began working her perfect ass. Lela moaned as I jiggled and tightly kneaded each cheek. Raising her ass up she invited me to do more as I slid my hand between her legs and gave her pussy more attention. My cock began to grow as it rubbed against her oily ass.

Lela moaned as I worked my fingers up her crack and gently rubbed her anus. Lela wiggled her ass against my finger as she reach down and grabbed the bottle of oil. My semi hard cock now rest between her ass cheeks as I worked her lower back. I continued my massage as she applied a tiny bit to her hand before reaching back and stroking my semi hard cock.

"Do you want to cum my little princess? I feel bad that Daddy fucked you so hard and you didn't cum," she asked as she stroked my oily cock.

"You know I do Lela."

"You were a bad girl in the car earlier. If I forget that ever happened then what are you going to do for me?"

"I can pamper you all day? Let you fuck my pussy all night?"

"No. Both of those are going to happen either way,"

"Well what do you want?"

"I want to go out to the club and go dancing tonight. Tell me you want to take me out and dance,"

"I don't dance though, especially in high heels,"

Lela looked back and lowered her sunglasses, "You know I am trying to give you a way out not to mention I can just tell you we are going."

She was right and I knew what I had to say, "Lela I want to go out with you tonight."

"And?"

"I want to take you to the club to go dancing," I told her.

"Thank you. I can't wait. Now do you want my titties or ass?"

Normally I would never turn down fucking her tits but her ass was right there teasing me and we hadn't done anal in a while.

"I want your ass babe," I told her as I massaged her oily ass.

Lela stopped stroking my cock and placed it between her soft ass crack and began sliding it up and down her oily crease. I held my cock straight and began pushing against her hole to penetrate her.

"Wait! Stop!" She giggled, "Not anal. Fuck my ass like you would my tittes."

I was disappointed but her ass was so perfect that I didn't mind. Lela continued to laugh as I held my hard cock between her glorious ass and began thrusting up and down the length of her crack. She moaned each time I passed of her tight little hole. I squeezed her ass together causing my cock to almost disappear as Lela began twerking and bouncing her ass.

She felt so soft and my cock head swelled as she reached back and held my hands as I squeezed them tight while thrusting. Pulling my hands off her I gripped her waist while holding the base of my cock tight inside her. The talented woman clenched her cheeks tight and relaxed over and over while twerking each cheek separately. My sensitive head was trapped in the soft flesh assault and I felt my orgasm near.

I gripped her ass tight and resumed thrusting as I told her I was cumming. A wave of pleasure passed through me as rope of cum sprung from her crack and up the center of her back. A second went further landing up on her left shoulder followed by quick endless spurts which coated her lower back. My cock rested as the last bit formed a pool of cum in her ass crack.

"My little princess cums so much. Get a towel and clean me up," Lela ordered completely satisfied.

I climbed off her and grabbed a towel and wiped down the large mess I made on her before finishing it with a kiss on her cheek.

"You never cease to amaze me Lela," I whispered to her.

"I think I should get a thank you kiss."

Leaning over I kissed the fabulous woman's soft plump lips as she giggled.

"That was nice but my mouth didn't make you cum," she laughed as she wiggles her ass.

I didn't need anymore hints as to what she wanted as I leaned over her large oily ass and spread her cheeks. Leaning in I approached her tight puckered holes and pressed my lips to it, kissing her over and over.

"That's good but I'm not done with you slut. Pull your chair under the umbrella and get naked. You've had enough sun for the day."

I followed her orders and pulled my chair in the shade. Lela Pulled her chair next to mine but kept hers just enough in the sun. I stripped naked and laid down. I had just put this bikini on and figured Lela just loved to dress me so that she could undress me.

The still naked woman grabbed the bottle of oil and straddled me before pouring oil down her body. She then leaned over me and began rubbing the oil over me with her naked body. We had done this once before in the pool area back home and I loved it.

She turned and poured oil on the ass I just abused before rubbing it up and down my stomach and chest. Her big ass made quick work of spreading the oil while she moaned at her pussy rubbing agiant me. She then rolled me over and kissed my neck as her soft breasts rubbed against my back. Her hard nipples added extra sensations as she rubbed up and down my body.

"Lay here with this oil. It will male your skin extra soft, womanly soft. No more sun though. It's a lot brighter here and I don't want you burning. Oh wait I almost forgot your little pussy."

With that her finger pressed against my hole and worked me to almost instant arousal. I moaned as she laughed and gave me a playful smack before climbing off and tying her little micro bikini on. I stared at her as she sat in her chair catching the sun. I couldn't get over how damn good she looked in it. She caught me staring and smiled before reaching over and grabbing my hand and holding it.

"Stop being so cute," she told me.

I just laid there and held her oily hand before closing my eyes and drifting off. We stayed there a while before Lela had enough sun and we jumped in the pool together. The sun began to go down but the water was extremely warm from the hot day. We played around with each other in the water before making our way to the edge of the pool overlooking the beach.

I held her curvey body tight against mine as we watched the sun set from the pool and kissed.

"I can't wait to go out with you tonight," she told me as she wrapped my arms around her and leaned back against me.

As the sunset and the pool darkened we dried off and went inside. The cool house gave me goosebumps on my wet skin but was fix as we stepped into a warm shower together and washed off. We wrapped ourselves in towels as Lela sat me down and did my make up for the evening as well as styling my hair. Long and wavy with dark makeup looked amazing on me..

I followed her out to the bedroom were she dug through the suitcase and pulled out tonight's outfits. Black satin bra and panties with matching thigh high stockings. I loved satin and quickly put them on and fixed my breasts as Lela put me back in chasity. I didn't complain, I knew not to and from what I've seen she had been generous with it. I had heard of slaves who were left in chasity for months.

Along with the satin thong she gave me a pair of the butt lifters we bought recently at the mall. Each side of my ass was hugged by the fabric and lifted up. She then helped me with a tight light blue dress which was way too tight and way too short. I stood up and noticed the dress already riding up my ass exposing my bottom which Lela rubbed.

"Babe. You have such a nice booty tonight," she said in awe.

"Lela this is too short babe," I complained.

Lela always had an answer and reached under my dress which had thin straps near each hem which attached to my stockings. It was a tug of war between my stockings and dress but it held it just below the bottom of my ass. While she was knealing she took the time to secure a pair of black stilleto heels on each foot.

We stood together in the mirror as she played with my hair, causing it to fall and bounce over my shoulders. The dress hid any cleavge but was so tight that every curve was shown and my ass stuck out on my small frame. This was the best I had ever looked before and Lela picked the right moment to do so.

"We really need to find a way to get your real tits," she said as she adjusted my breast to make them look bigger, "Relax a bit while Momma gets ready."

With that she stepped into the bathroom while I stepped out on the balcony and watched the ocean waves in the dark. Other than the waves crashing is was completely quiet, secluded and peaceful. I sat there and waited while thinking about how happy I was being with this woman. Maybe I should come out to everyone and get the real tits Lela wanted.

I quickly shook that idea out of my head, I couldn't. I thought about going out with her tonight and was excited and nervous at the same time. This was my first real step into the real world as Michelle and I was nervous to try dancing in these heels and tight dress.

My thoughts were interrupted by the sliding door behind me as Lela joined me on the balcony. She took my breathe away as she normally did. Wearing a similar black dress as I did except hers was strapless as her perfect breasts pushed out the top. It was almost as short though she didn't wear any stockings on her shiny tan legs. Her ass look enormous and stuck out like a shelf. My latina MILF was blacked out completely except for her ruby red lipstick. We almost looked like twins though I couldn't come close to her beauty, curves and sex appeal.

"Lela, you look fucking incredible," I complimented her with a kiss.

She joked, "I know you are so lucky to dance with me after dinner. Come Chuck is waiting."

The two of us made our way downstairs as our heels clicked down the wooden steps. Chuck was waiting for us dressed up in a casual suit type jacket.

"Wow. I am such a lucky man tonight," he said as he checked us over.

Lela approached him and gave him a kiss on the cheek as she greeted him before looking at me to followed her lead.

"Good evening Daddy," I greeted him with a kiss as well.

Lela grabbed a pair of handbags for us while Chuck stared at me, "Jesus Lela. If I saw her at the bar even I would try to take her home."

"I know. I told you she would be perfect when we scouted her out working at that gross deli," Lela said as she handed me a small back handbag and crossed her arm through mine to escort me outside.

The night was humid but slightly cool as we climbed into the car. I sat alone in the backseat and stayed quiet while they chatted about where they were going. The drive through the scenic and secluded area gave way to a busy city like area full of restaurants, hotels and clubs.

We pulled up to a small upscale steak house and stepped out as the valet worker took the car. Lela and I each took one of Chuck's arms as we walked in with him. He must have looked like a fucking pimp with the two of us. I was still on very thin kce with him but knew I had to play my part perfectly. A waitor escorted us to our table, a small curved both which overlooked the place, almost like a VIP table.

We slid in across the smooth seats with Chuck in the middle of us as the waitor took our order. Lela was talking spanish and I had no idea what the hell she was saying. The waitor left as Lela told me what she had ordered me.

"I got you a wine and small steak and vegtable dinner," she told me.

"Whoa. That's more than you let her eat all week," Chuck joked.

Lela grabbed his hand and told him while staring at me, "We are on vacation. Plus Michelle has been a very good girl. Michelle, what do good girls get?"

"They get rewarded," I replied.

"You're getting this bitch trained well I see," He laughed in amazement, "Do you like being a good girl Michelle."

"Yes Daddy. I love it and I hope you love it too," I answered as I rubbed his thigh in a seductive manner.

"Holy shit Lela, I don't know how you do it," He laughed again in amazement as Lela blew me a kiss across the table.

The waitor returned with our drinks and handed me my wine.