The Robertson's Sissy Ch. 10

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.**

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This was becoming the best day of my life. After all the crap I had been putting up with things were finally turning around. Lela and I were happy with each other as we relaxed on the bed after our unexpected threesome with Jenny, the busty asian of perfection. Chuck would be home by the morning leaving Lela and I alone for one more night. Not going to lie, I missed his cock and couldn't wait to blow him as soon as he got home. In the meantime, Lela had one more surprise lined up for me tonight and I couldn't wait.

We laid in bed together as the sun began to go down before getting up and eating. I showered as Lela laid out the lingerie set she wanted me to wear this evening.

"Babe, let's try one of the lace nighties I bought you today. Get dressed and join me downstairs in the movie room," she said as she excitedly left the room.

I walked to the bed and checked out the new lingerie. It was cute but simple. Black and teal lace top, black thigh high stockings and a pair of black lace panites. I couldn't wait and threw each piece on. The top was shorter than I thought, stopping just below my waist though blending into my panties perfectly. The panties were different, they were tight up the bottom of my butt but spread across the top of my ass cheeks. I checked them out in the mirror and loved them, the bottom half of my cheeks hung out as the top half was covered in pretty black lace.

I slipped the silky smooth stockings on before stuffing in my large breasts. They were a bit tight but I looked fabulous in the mirror. The tight top hugged my torso and chest making my breasts look huge. I followed my usual routine and did my makeup and wig before walking down the hall to meet Lela. I felt so hot in this outfit and couldn't wait to show her.

I walked downstairs and found Lela in the movie room, snuggled up under a blanket. She was sipping a glass of wine on the couch as she watched me walk in.

"Wow babe! I love it! You look so fucking hot!" She stated as she got up and ran her hands over my body.

She lead me to the couch where she sat behind me, playing with my hair. She pulled it back, securing it in a ponytail with a hair tie. Standing in front of me she fixed it to her liking.

"Babe, you look so cute like this. I'm going to need to put your hair back more often. I don't want to hide your pretty face."

She returned to the couch and cuddled up to me, enjoying every second of my new look. She was so happy and flirty that I wanted her right then. I leaned over and began kissing her and she couldn't help but kiss me back. We began making out as my hands found their way between her legs, rubbing her pussy through her sweatpants. She moaned as I kissed her neck while playing with her but reluctantly stopped me as I tried pulling her pants down.

"Stop, stop, stop babe. Wow, you almost got me," she giggled while fanning her face, "You get me so hot but not yet, it's almost time for your surprise."

I was disappointed to have my advance shot down but knew it was for the best. The kinky cougar most likely had some crazy night planned for me. Instead we cuddled up on the couch and made out while finishing the movie she started. Before the end her phone vibrated and she excitedly bounced up.

"Yay! Your surprise is at the door!" She shouted as she jumped up.

I got up to go upstairs with her but she placed her hands on my chest and pushed me down before jumping on my lap.

"You're not allowed up yet. I need to get ready for you. Relax here until I come get you." She said as she began aggressively kissing me while rubbing my cock through my panties. She moaned as my cock started getting hard before grinding on me. Suddenly she stopped and giggled as she kissed my cheek.

"I love teasing you. I'll be back love," she laughed before jumping off me and excitedly running upstairs.

I sat on the couch, hard as a rock but patiently waited. Based on the look of Lela's face this was going to be a great night. I sat there and waited but she was taking forever. I laid down and started falling asleep though my massive erection was keeping me up. I finally was able to doze off a bit while Lela prepped her surprise.

I woke up to the touch of Lela's lips on my cheek. She hovered over me with a gigantic smile as I came to.

"Wake up sweetheart, it's time!" she happily stated as she straddled my chest.

I laid there and took in the site of the amazing woman. She wore a red satin bra and matching thong that sat high on her hips. I was drawn to her flat toned stomach and leaned up, kissing her around her belly button. I worked my way down before she stopped me and readjusted herself to trap my arms under her.

She reached back and began rubbing my cock through my panties again. As she leaned back her hips pushed closer to my face though staying just out of reach. I couldn't reach her but was able to smell her intoxicating scent. The smell of her warm moist area made my mouth water as I stared up at her.

She was beautiful with her hair up in a bun. She wore bright red lipstick to match her bra and panties and her face glowed in excitement. She released my cock and looked down at me.

"Don't get used to special treatment every night. Tomorrow you're back to being my sissy bitch and being a slave to this pussy," she told me before running her smooth satin covered pussy across my face as she stood up.

With her off me I sat up and took a minute to finish shaking off my sleepiness as she grabbed my hand and playfully stomped her feet.

"Come on! Come on! Get up!" she pulled at my arm.

Now awake I got up and followed her to the stairs. I thought I had seen her really happy before but not like this. She bounced around like a little kid on christmas morning excited to show me whatever she had planned. Up the stairs we walked, passing through the glass corridor, past the pool towards the bedroom. Lela stopped at the door before excitedly turning to me.

"Close your eyes!"

I wasn't going to ruin her moment and closed them as she lead me into the bedroom.

"Stay right here but keep your eyes closed."

She let go of my hand after leading me towards the bed. I heard her climb up and position herself, she was way too excited, what the hell did this woman have planned?

"Open! Open! Open!," she shouted.

I opened my eyes in shock at what I saw. Fucking Jenna bent over doggystyle, her big pale ass staring at me. She was dressed in similar lingerie that I had been wearing all week, all black. Stockings, garter belt, g-string and all with her hair up in a ponytail. She had her wrists tied, a blindfold and the ball gag that I once wore in her mouth.

"Surprise!" Lela shouted as she knelt behind Jenna while holding her hands in the air.

I got pissed, "Lela! What the fuck is this!"

I thought we were done with Jenna, I wanted to move past this. Even though I wanted to be with Lela I felt horrible about what happened with Jenna and just wanted her left alone.

"Well, Jenna did embarrassingly deny you anal. What better present than to make sure you get to conquer the hole you were denied," Lela laughed as she spread Jenna's big ass cheeks.

"What the fuck Lela? No!" I shouted as I walked out the door.

Lela wasn't far behind and ran me down before grabbing my arm and stopping me.

"What the fuck Lela? I thought we were done with her."

"Well we were. But Miss Jenna broke our little rules last night after you passed out from the cop. She messaged you saying she "wanted to talk". Sneaky little bitch sent a message through facebook and not text. Good thing I got it though, she could have gotten you in trouble again. Oh by the way, we are facebook friends now," Lela innocently laughed like it was all a game.

I snapped, "I'm not doing this! I'm not gonna punish her or do anything she doesn't want. This is all you!"

"Wait, wait, wait! I promise she wants it!" Lela explained as she dragged me back to the bedroom to Jenna before continuing.

"Jenna wants it I swear! I made her a new little agreement! If she does this then I'll leave her alone completely and never mess with her again. She also needs all this new school stuff like books, clothes and money on her food card that I promised to take care of! I get to keep her slutty little film though to make sure she keeps her mouth shut and she's still not allowed to talk to you or the deal is off."

Figures Lela would bribe the poor girl again. Lela and Chuck had more money than she could possibly spend so why not bribe the shit out of everyone to get everything you want. Of course the money strapped girl was susceptible to Lela's financial generosity.

"Great Lela, just bribe and blackmail the girl. What the fuck."

Lela threw on her little innocent face while pretending to think, "Yeah, you're right. But it works. See!"

She walked over to Jenna and removed the ball gag from her mouth allowing Jenna to talk.

"It's fine Matt. Just do it. I want to do this. Honestly, It's ok Matt," Jenna stated before Lela stuffed the ball back in her mouth.

"Nope, not happening Lela. I wanted to move on from this."

I walked out the door before Lela ran me down a second time, this time she wasn't as cheerful.

"Now listen up bitch. I worked very hard to set this up so your ungrateful ass better get the fuck back in there and do it. She wants it and needs it, I promise it's done after this. Regardless of what you want to do, I'm not letting her little deed last night go unpunished so If you don't do it then I will. I promise I will make it much worse too."

I stood there not saying a word, I didn't know what to say. Lela got right in my face and held me close, kissing my neck and whispering in my ear.

"I love you Matt. Things have been so great sweetheart and I want things to stay great, Don't let your emotions fuck this up. Remember what happens when we don't listen. I really don't want to have to put my little sissy in her place again. It hurts me so much to see you in such pain."

I looked in her face, she spoke calmly but her eyes were pure fire. The same fire I extinguished a few days ago and I wasn't going back to that.

"Ok Lela," I reluctantly gave in, "I'm not purposefully hurting her though."

Lela switched back to her happy self before kissing me cheek, "Yes! I'm so excited! I love you!"

I didn't say anything. Just stared at her unhappy. She wasn't very happy at my silence and grabbed my balls through my panties giving them a firm squeeze. My balls are normally sensitive so it didn't take much to get me to squirm.

"Fuck! I love you too!" I squeal before she laughed, dragging me back to the room.

I had let my guard down with this woman and it was a stark reminder. No matter how I felt for her and how great things were between us, she could easily flip and be my worst nightmare. I felt I was already on thin ice with her so no matter what happened in this room tonight, I was going to do everything I was told.

I followed her in and to the bed, Jenna's pale round ass staring at me. Jenna was hot and deep down I wanted to plow her but not like this. Lela crawled on the bed while I knelt at the bedside. Lela was excited as she slowly lowered Jenna's g-string while spreading her big cheeks. There it was, her pretty little pussy and puckered little hole she denied me.

"Lick her babe, get her ready," Lela ordered.

I wasn't testing her anymore and leaned in and gave her pussy the first lick. Jenna jumped at my first touch but quickly settled down. She tasted great, she always did. I got lost mentally as I continued working her with my tongue before Lela interrupted.

"Wrong hole babe," she giggled.

I leaned up and ran my tongue over her puckered little hole. Jenna tensed up but began to relax as I worked her. Darting my tongue up and down, poking her with increasing pressure when I heard her first moan. She started to like it and I wanted her to. This was going to happen either way and I wanted to make sure I made it as pleasant as possible for her. Her moans grew louder through the ball gag which encouraged Lela to join in. She leaned over the top and and began licking her hole with me.

Our tongues lashing around, wrapping around each others as we prodded and twirled around Jenna's ass. Lela's hand reached underneath and began rubbing Jenna's pink little pussy. Jenna's moans intensified and I stood up ready to keep this moving along. Lela sat with her head resting on Jenna's lower back with an evil little smile. I reached up and stuck my fingers in her mouth as she seductively moaned and sucked on them.

No matter how sick and crazy this woman was she was fucking hot and sexy. She didn't want me to remove my fingers from her mouth, she was having too much fun. I pulled them from her and ran them down Jenna's crack before massaging her hole. The more I worked her, the more her muscles relaxed as I pressed in with the first finger. The warm sensation never ceases to amaze me as she moaned while I pushed in knuckle deep.

Lela smiled as she watched me begin pushing inside with a second finger. Jenna jumped but relaxed again once I pushed passed her sphincter. Lela now satisfied with the job I was doing crawled off the bed and onto her knees. I felt her pull the front of my panties down freeing my limp cock. She immediately took me into her mouth and sucked me as I inserted a third finger inside Jenna. Jenna didn't take this one as easy and grunted a bit but Lela's mouth was doing wonders and had me rock hard.

Lust started taking over and I began finger fucking Jenna's ass faster as Lela spit all over my cock. Jenna needed a bit more time but Lela wasn't waiting any longer. She retrieved a bottle of lube and placed a few drops on Jenna's ass, forcing me to remove my fingers. I watched as the seductive cougar poured more out in her hand, stroking my cock while sucking on my balls. Once fully covered she popped to her feet, wiping her hands clean on a rag before allowing me to clean mine.

"Showtime babe," she whispered a she crawled back onto the bed, spreading Jenna's big cheeks.

I mounted Jenna from behind as she put her head down, she knew it was coming. Lela laid her head on Jenna's lower back, getting a front row seat at her first anal penetration. I rubbed my cock head up and down her hole, massaging her and spreading the lube before beginning to push. I heard Jenna moan in discomfort as her muscles pushed apart. They finally gave in as my cock head popped past them into her ass. Through the ball gag Jenna squealed as I allowed her time to adjust. Lela got up from the bed and kissed me on the cheek while patting my head.

"Good girl, now have some fun."

I felt Lela's hands on my lower back as she pushed me foward slightly, forcing my cock deeper into the anal virgin. Jenna let out another yelp of discomfort.

"What the fuck Lela?" I shouted.

"Oops!" She giggled as she crawled back onto the bed up to Jenna's face.

She sat doggystyle in the opposite direction, face to face with the blindfolded Jenna. Her big tan ass propped up in the air, her thong splitting her big cheeks, forming a massive cleavage of ass. I began to slowly thrust in and out of Jenna as she moaned. I couldn't tell if it was from pain or pleasure but I kept a steady and gentle pace, my eyes fixed on Lela's massive ass cleavage. Lela caught me fixed on her ass as she wiggled it for me while biting her lower lip.

"Hi," she mouthed as she gave me her innocent stare.

I finally bottomed out inside Jenna's big pale ass as her muscles finally started accepting my size. I picked up the pace slightly as Lela began whispering in Jenna's ear. I couldn't hear her but I knew she was taunting her. I didn't care at this point as Jenna's tight ass gripped and squeezed my cock. She felt so amazing and warm, my eyes rolled back as the pleasure of fucking this anal virgin took over me. Lela caught me in pure pleasure and smiled before talking louder to Jenna.

"He's all mine now Jenna. Matt belong to me. After tonight you better fucking forget about him."

I gave her a pissed look though my cock was in heaven. Lela didn't like the stare I gave her and got off the bed, approaching me from behind. She reached around me and grabbed Jenna's wide hips. I felt a few hard thrusts as Lela began thrusting me into the tight blonde. Jenna moaned louder as Lela kept thrusting and whispering in my ear.

"Fuck her Matt. She wants it. Listen to her moan. Fuck her harder."

Lela pounded me into her as she moaned into my ear. Slowly she allowed me to take over control of the harder thrusts as her hands ran up and down my lingerie covered body. Squeezing and fondling my breasts as she kissed my neck. Jenna's moans increased as I fucked her at a good pace while Lela explored my body.

"These nighties looks so good on you babe. You look so fuckable."

Lela walked away and disappeared in the closet as I pounded away at Jenna's ass. She moaned harder and it was clear these were moans of pleasure and not pain. Lela reappeared wearing the large Chuck sized strap on. Mentally I prepped myself for her to fuck me as I fucked Jenna but instead she moved toward Jenna face. She knelt in front of her and removed the ball gag, ramming the head of the rubber cock in her mouth before she could speak.

I watched as Lela savagely face fucked Jenna as gurgling noises filled the room. Lela smiled at me and threw me a wink before stuffing the gag back in and securing it.

"That enough Sweetie, that's all I needed. Matt pull out for a minute."

I did as I was instructed and watched as Lela laid down on her back. She instructed and guided the blindfolded Jenna to straddle her as she guided the large rubber cock into her wet pink pussy. I watched as Lela fucked her while smearing more lube on my now wanting cock. Lela motioned me to 'come' with a single finger and I followed her order, remounting Jenna's ass. I pressed against her now loosened hole, popping in with ease as Jenna moaned loudly.

Lela and I double penetrated the poor girl as she moaned uncontrollably. Through the walls of her insides I could feel the large rubber cock working her. Occasionally feeling the large rubber balls rub against mine. Jenna began breathing harder as Lela and I began fucking her hard. I watched as Lela removed the blindfold, making sure the first thing Jenna saw was her evil smile.

"Don't ever text my man again. I'll fucking ruin you bitch," Lela taunted.

I had a flashback of the first night Chuck fucked me, I was in the same position, Lela underneath me whispering in my ear. My flashback was interrupted as Jenna started squirming. Lela removed her ball gag as Jenna started shouting.

"Fuck me Matt, Fuck me Lela. I'm gonna cum!"

Lela looked at me quickly and mouthed for me to 'stop', which I did, denying Jenna of her orgasm last minute. Lela began rubbing Jenna's face before explaining to her.

"Seems you like being fucked in the ass like a little whore. Maybe you should have let him do it before. Apologize to him for denying him and then beg him to let you cum."

Jenna had my cock deep in her ass and the large rubber dick in her pussy and couldn't hold back anymore.

"Please! I'm sorry! I'm sorry Matt! Please let me cum. Please fuck me hard!"

Lela threw me a wink though still sporting the evil grin on her face. I gripped Jenna's garter belt and began driving into her with force. Lela quickly followed plowing her from underneath as Jenna screamed in pleasure. I felt her anal muscles clench down on my cock as she began howling in orgasm. A flood of fluid covered the rubber cock as it squished with each thrust. I wasn't used to orgasms like this and stared in amazement as I plowed her while her body convulsed on top of Lela.