The Robertson's Sissy Ch. 07

**A quick note. The chapters of this story can fall into mutiple 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 the worst night ever. Lela, my little devil ruined me. Jenna probably hated me and even if she didn’t she wasn’t allowed to see me.

On the bench I waited, now cold and broken. The pain I felt from the hard ass fucking was intense but I tried to stay strong and not cry. I laid there with my body in shock, quivering and weak. Most of the night passed before I saw the girls. I watched as Lela and Jenna came out from the bedroom and walked to the front door. Jenna was now calm though I could tell from her face that she had been hysterically crying for hours.

The women calmly parted ways as Jenna left to drive her new and desperately needed car home. Lela locked up and made her way down the glass corridor, she was coming for me. Normally, I would have been nervous but I was too in shock to feel anything.

Lela entered the room holding a blanket and pillow, before laying them down on the bed. The same bed where, a few hours earlier, Jenna received the fucking of a lifetime. Lela changed from the devilish red bikini, now wearing a white tank top and sweatpants. In my mind I hoped that the devil who ruined me would now be my angel.

She didn’t say a word as she walked over to me, stopping to look me in my eyes. I wanted to break down crying as I shivered uncontrollably, but fought to stay strong. She went to remove the ball gag but stopped herself deciding to leave it in.

“I don’t want to hear you speak. Not a fucking word from you,” she told me.

I don’t think I could have spoken if I wanted. Her voice sounded angry but the expression on her face showed pure sadness. Her eyes teared before she untied my wrists and ankles. Though free my body couldn’t move, I was paralyzed in shock. Lela tried helping me up but I fell to the floor, the pain too much. She pulled me to the bed and assisted me as I crawled up on it. I collapsed on the pillow in the middle as Lela covered me with the blanket.

She crawled under the covers with me as we laid face to face. Not a word was spoken as she stared at me and caressed my face. I stared back as my body shivered. Lela’s face was full of pain as tears formed in her eyes. It gave me hope that she still loved me enough to keep me around.

She didn’t want me to see her like that, so she helped me roll over. She held me tight to her warm body as I uncontrollably shook for hours. Through the rest of the night she never loosened her grip and she never once left me. My angel came to save me though my fate with her was still unclear. I fell asleep with her as the sun began to rise.

I woke in the early afternoon, alone and in pain. I was finally able to remove the ball gag from my mouth. My jaw was stiff and hurt but not nearly as much as my torn ass. In bed I laid there contemplating my next steps.

I didn’t have a lot of money but could have found a way to disappear, somewhere far away. Even if I didn’t do it on my own Lela was most likely done with me and would kick me out before releasing the video of me sucking Chuck’s dick. Common sense would have been to get the hell out but deep down I didn’t want to go. The release of the tape would have been every guy’s nightmare but for me it was losing Lela.

I’ll admit it, I loved her. Most people would think I was crazy, hell I think I’m crazy. Despite everything, I couldn’t keep myself from wanting her more. She was beautiful, smart, funny and in charge. She scared the shit out of me but I never felt more excited with any other woman. Her bipolar tendencies kept me on my toes at all times. Would I get the soft and passionate Lela I loved or the angrily rough Lela that would put me in my place?

I wasn’t a fan of the pain but even the rough Lela I started to enjoy. Last night being the perfect example. I never felt so much pain but eventually it turned to pleasure before she finally let me cum. After each punishment her soft side would always come out and care for me.

The one thing that was certain was my love for womens lingerie, I never felt so sexy. The worst part of all this was what happened with Jenna. I felt horrible for her and she didn’t deserve any of this.

After all my thinking I decided I couldn’t go and had to stop her from kicking me out. I loved both sides of her and even the thought of sucking Chuck’s cock made my mouth water. Even If I left and moved on, I don’t think I could find someone who could excite me like they did. Just after one night with them, I got bored fucking Jenna in the back of my car during my failed anal adventure. The envy of every guy who I graduated with would have been to bang Jenna but after meeting the Robertson’s, my sexual desires would never be the same. I had to keep what I had with them, especially with Lela.

I hobbled down the hall to Lela’s bedroom to shower and change out of last nights lingerie. Lela laid there in bed, looking at me as I walked in. She didn’t greet me the way I had hoped.

She softly told me, “I don’t want to see you right now.” She rolled over and turned away as I made my way to the bathroom. Before I made it I heard as she added, “Pack your bags up, I don’t think I want you here anymore.”

My worst nightmare was coming true, she was letting me go. I went into the shower, not bothering to take my lingerie off. For an hour the warm water pelted me as I sat on the floor broken. I pulled myself together, dried and went to get dressed. I stumbled out of the bathroom door to find she was no longer in bed.

“I couldn’t lose this woman,” I thought to myself.

I had to make sure I looked perfect for her. I tore through the closet for something to wear before settling on a purple lingerie set with white stockings. It looked cute and innocent and I couldn’t wait to get it on. I followed my similar routine, loving the way each piece felt against my skin as I put them on. I took extra time with my makeup and wig, they both had to be perfect.

I finished with a pair of white heels to complete my look before standing in the mirror, fixing any blemishes I found. I fumbled with my breasts, trying to make them look as big as possible. Lela was a sex driven woman and I had to appeal to it.

“Time to go find her,” I nervously thought.

I was scared to see her but I knew I had to make things right. I walked around until I found her relaxing after the long night in the hot tub. She wore her devilish red bikini again which reminded me of the horrors of last night. I didn’t care though, I painfully made my way into the pool area, struggling to walk to her. I tried to be as sexy as I could as I made my way to her, ready to appease any sexual desire she had. I wanted the nympho cougar to know that I’d be her little sex slave. I was ready to accept my role if she kept me but it didn’t go as planned.

She looked over to me as I opened my mouth but shot me down before I could speak.

She yelled, “Don’t you fucking dare say a word to me! I told you I didn’t want to see you right now! Now go pack your fucking bag! I’ll come find you later when I want to talk to you!”

My devil was back and she was pissed. She looked so damn good though, the red against her tan curvy body made her the hottest devil one could imagine. I retreated from the pool area in defeat and down to Chuck’s room. He was away for a few days so I could lay in his bed while I gathered myself.

Alone with my thoughts I began piecing together everything. How could I get her back? I thought about who they were and what they wanted. Chuck was easy to figure out. He was an extremely wealthy business man with a big ass house. He had Lela as a trophy wife who he used to complete his powerful image. He loved fucking young guys like myself though he wasn’t looking for any type of emotional connection. He was too busy for that and always away. He wanted to dominate men sexually and then continue on his own.

Lela was tougher to crack but I figured she was the exact opposite. She married Chuck because she loved him and was destroyed when she found out his secret. For the money, his image and their friendship they decided to stay together though Lela was ruined emotionally. She sat alone in this big house all day while Chuck worked.

She was an honest wife but yearned for affection and love which she never got from him anymore. She pushed them to join a swingers club, not only the sexual adventure but for a connection with someone. The swingers club was good for the night but she wanted that one steady person.

She didn’t care if it was a man or another woman, she needed somebody. They looked for someone to satisfy both of their very different needs, and they found me. After meeting me she knew deep down I was a little sissy and would give into her every demand but more importantly I would love her.

I always thought the nympho cougar was all sex driven but it was more clear now. She could have sex with anyone she wanted but she really desired someone to love. There was nothing I wanted more than to be that person. Sexually she was sick and twisted but she was right, I learned to love it as I learned to love her.

I had to find her and give her what she wanted. I didn’t care if she didn’t want to talk. I was going to let her know. I figured my ass was out anyway so if I pissed her off so be it. I had nothing to lose and decided to pack my bags incase she immediately threw me out. I made sure I packed a few lingerie sets to enjoy at home before removing the one I was wearing. If she snapped I couldn’t get thrown out in women’s lingerie. I put my shorts and t-shirt on before washing the makeup from my face.

I sat on the bed to mentally prepare myself before I painfully got up and looked for her.

She wasn’t in the kitchen, her bedroom or the pool area but her car was outside.

“Fuck me,” I thought, “It hurts so damn much to walk and now I have to search the biggest house in town. Just my luck.”

I hobbled around and checked every room before I remembered the basement. I made my way to the stairs and looked at them reluctantly, this wasn’t going to be fun. I slowly took each step one by one, the pain was intense from last nights abuse. I stopped at the bottom to catch my breath and compose myself. As I approached the movie room I caught my first glimpse of the incredible woman.

Lela was laying on the large plush couch napping under a blanket. She must have fallen asleep while watching a movie and I slowly approached her. I cautiously sat on the couch, careful not to wake her, my ass throbbing in pain as I sat.

I took a moment to stare at her, she was beautiful. Her long curly brunette hair was pulled up in a ponytail, leaving an unobstructed view the mature goddess. Her skin was so soft and smooth, not a blemish on her glowing face. Her sweet pink lips were plump and begged to be kissed though I held myself back. She laid there cuddled up in a ball as reached over and gently stroked her cheek, softly calling her name to wake her. She opened her eyes and stared while she came to her senses.

“I told you I don’t want to see you. Now go away,” she mumbled as she pulled the blanket off her half asleep.

“No, I’m not leaving. I’m not going anywhere until I talk,” My words were cut off as she instantly sat up and started hitting me with force.

“I said to leave me the fuck alone! Go pack your shit and get the fuck out!” She screamed while using me as her punching bag.

For a smaller petite girl she sure was feisty and hit hard. She landed a few good blows and in pure reflex I grabbed her and pushed her back down on the couch. I laid on top of her, my weight holding her down with her wrists pinned above her head. She opened her mouth to scream at me but this time I was the one cutting her off.

“I’ve been your punching bag this whole fucking time. Now it’s your turn to shut up and listen,” I screamed.

I was in control for the first time since meeting her and she just stared at me silently with fear and sadness in her face.

“I love you Lela. I fucking love you. You are the most amazing woman I have ever met and I need you. Your mad at me for lying and the few things I said when I was pissed. But take a second to think of all the shit you have put me through. You forced me to dress like a hooker and blow your husband, you blackmailed me, forced me to quit my job, borderline raped me and ruined my relationship with Jenna. After all the fucked up things you did, after all that, I still love you.”

I paused to catch my breath as tears filled her eyes. She began softy crying before I continued.

“I want to be with you and make you happy. I want to be with you every night and to love and satisfy you anyway I can. Even if it means being your submissive little sissy and fucking Chuck. I’m not gonna lie, I love being your little bitch! I’d do anything for you but you’re not giving me a real fucking chance. I’m done with the bullshit your putting me through. I don’t give a fuck about the little video you have of me. What I do care about is losing you. Now, I got my shit already packed and will leave. You can release the video like you threatened, ruin my life and forget about me or you can forgive me like I have already forgiven you. If you call me back I will drop everything and be here in a heartbeat for you. Goodbye.”

It felt liberating to scream out everything I kept bottled up. It felt like the weight of the world was lifted. She laid there sobbing as I slowly began to release her wrists, setting her free so I could go home. I wanted one last look at the woman who ruined me but my stare was interrupted by her hand cracking me across the face.

She slapped me so hard it felt like I got punched. My entire head swung to the side and my cheek immediately burned as blood rushed to it. In shock I slowly turned my head back to her when she grabbed me and kissed me, pulling me back on top of her. Stunned, I kissed her back as she wrapped her legs around me. She wasn’t letting me go anywhere. My ex and I would get into huge fights and make up but this would be the make up sex of all time.

She held me tighter than she ever had before as we aggressively yet passionately kissed. Like teenage virgins we began stripping the clothes off each others body. She pulled my shorts down just enough to free my semi hard cock. Leaning up she immediately took me into her mouth. I pulled her tank top over her head as her large braless breasts dropped free.

She laid back and seductively stared at me, still with tears in her eyes as I removed my shorts. I resumed my position and straddled her chest as she took me back into her mouth. Her mouth was so warm and heavenly, I couldn’t leave it. She held my cock at the base as her mouth worked me to a full erection. The entire time moaning while staring at me. Her eyes which were full of fire and tears before were now soft and full of lust.

The suction of her blowjob was so great that she pulled me from her mouth with a loud ‘pop’. She repositioned herself, presenting me her firm tan breasts. I laid my hard cock between them as she spit down on it. She smiled as she squeezed them together locking me up inside. It wasn’t a flirty smile like I have gotten from her in the past. No it was the smile of a woman who was truly happy.

I began fucking her soft lucious breasts as she continued smiling at me. I loved tittyfucking her, as much as her ass was her best asset, her titfuck was my favorite. I slowly thrust into them, my cock popping out from the top each time. I thrusted up and held it there as I reached behind, sliding my hand down her sweatpants.

I found her clammy wet pussy and rubbed it while she leaned forward, sucking my cock head as it popped out from her cleavage. I slowly started thrusting as I rubbed her clit. Everytime my cock head appeared from her breasts, Lela would lick it or give it a quick suck before it disappeared again.

“Fuck my tits Matt, fuck them harder,” Lela demanded as she bounced them up and down my cock.

I tried thrusting faster but I was too sore and in pain to do so. With a grimace on my face I tried to fight through it while still rubbing her now wet and ready pussy.

She saw I was struggling and chummed in, “Stop babe and sit down. Relax, I’ll do the work.”

I never wanted to stop fucking her sweet cleavage but was in so much pain that I didn’t protest. I sat down and caught my breath as Lela removed her sweatpants before straddling my lap. This was Lela’s favorite. She could seduce anyone in this position, myself and Jenna were perfect examples. She stared at me while she lowered herself on my cock. Her face squinted as she let out a sigh of relief as I impaled her. Her pussy wasn’t just wet, it was dripping with lust.

I sat back as the experienced and mature cougar did her magic. She slowly fucked me while my attention was drawn to the large luscious breasts bouncing in front of me. I grabbed them, pushing them together and sucking on each brown little nipple. I kept going back and forth sucking and licking each one, getting them as hard and erect as I could. Lela loved this and held my face against her chest as she rode me harder.

Unlike Jenna whose whole body would bounce, Lela’s body was still. The only movement was from her ass and hips as she twerked and bounced on my cock. Her nipples were so hard now as I gently pinched and bit them between my suckling. This was too much for Lela as her twerking turned to long deep grinding. It put her over the edge, releasing a quick but well needed orgasm.

As she came I held her tight, kissing her neck as her grinding began to slow.

“You’re not allowed to go anywhere. God I fucking love you and your cock,” the breathless post orgasmic Lela whispered.

It felt good hearing that from her and I held her close as we passionately kissed. My hands explored her smooth curvy body until I grabbed two handfuls of her big round ass, squeezing it tightly.

Lela happily shrieked as she playfully hit me, “You love my ass don’t you?”

“You know your ass is my favorite part of you,” I laughed.

She gave me an innocent yet slutty smile as she slowly got up, turning around and wiggling her round tan ass before lowering herself on my lap. She held my cock straight before sitting on it. A loud gasp escaped her as she became impaled a second time.

She began bouncing her ass, twerking it again as she fucked me. I tightly held her thin waist as her ass bounced up and down, her pussy swallowing my cock whole. She shifted herself sideways so she could look over her shoulder at me. Using one hand she balanced herself while playing with her breasts with the other.

“Your cock feels so good baby, fuck me,” she said over her shoulder, “There’s so much more this ass can do that you haven’t seen. Your not allowed to leave yet.”

I grabbed her ponytail, pulling her head back and arching her back.

“I’m not going anywhere,” I whispered in her ear as I sucked on her earlobe.

I continued holding her head back as my free hand took over squeezing her firm breasts for her. She placed both her arms behind her, grabbing my hips as she grinded in circles. My cock never felt such pleasure and I wanted her to keep going like this until I came. Her circlular grinding turned back to bouncing as she fucked me more aggressively. Everytime she came down on my cock she drove down with all her weight, causing her big ass cheeks to slap against me.

“Fuck Matt, I’m going to cum again!” Lela screamed as she thumped down harder on my cock.

She was going to beat me to orgasm but I was fine with that. I’d let this magnificent woman cum on me all day. I never let go of her ponytail but my free hand left her breast and slid down her flat stomach, finding her dirty little clit. She was back to grinding me as I rubbed her slippery wet pussy.