The Robertson's Sissy Ch. 06

**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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I woke a few hours later, my eyes swollen from crying, irritated by a mix of tears and last night's make up. I was alone, Lela must have slipped out of bed without me knowing. I wanted to eat something but was afraid of seeing her, she was unpredictable. One moment ruining my life while the next cuddling and caring for me. One thing was certain, I would be punished today.

I got up and washed my face before returning to bed. Lela must have heard me up as I heard her down the hallway.

"La la la laaaaaaaa la, la la la laaaaaaaa la," she sang as she skipped down the hall into the room.

She was excited about what she did last night. Not only to me, but the raunchy night she had with Jenna would put anyone in a good mood. I could tell she couldn't wait to tell me all the fine details of how she abused Jenna all night. She jumped on the bed laying inches from me as I laid frozen.

"Good morning my love, oh wait, your not my love anymore," she said poking me in the chest.

"What a night I had with your little girlfriend! I thought she was a little prude at first but let me tell you, deep down she is a filthy whore. Just need to learn how to release her inner slut, just like I did ALL night long!" She laughed as my face turned red in anger.

"Don't be mad that you weren't man enough to do it. Don't worry, she wouldn't even allow me to put more than a few fingers in her ass," I was relieved Jenna didn't let her do it but my relief was short lived.

Lela continued, "She was a little follower doing everything I wanted, except anal of course. But when I gave her a chance to take control she released her inner slut demon. My god! She fucked me so hard last night, I had to beg her to stop!"

My cock began to stiffen at the thought of Jenna plowing the shit out of Lela in every position. My balls hurt so much from the night before. Lela didn't allow me to cum at all and blue balls were killing me. My discomfort made worse as Lela grabbed them hard.

"Ouch, Stop Lela. That hurts!" I jumped in reaction.

"Oh poor baby, that's what happens when your a bad girl. I can help you out but you need to help me first," she stated while pulling off her shorts

Lela got up and straddled me in the 69 position, her pussy right above my face. She didn't lean forward towards my cock, instead she lowered herself, sitting on my face.

"Jenna fucked my tight little twat so hard last night, it's so sore baby. Please be gentle and take care of me. Do a good job and I'll return the favor," Lela offered as she freed my engorged cock.

Her pussy stunk like stale sex and I knew she didn't shower on purpose. She wasn't kidding about Jenna plowing her. He pussy was red and looked abused. I opened my mouth, sticking my tongue out as I gave her one long stiff lick from front to back.

"Oh! Gentle baby, it's so sore," Lela giggled as she jumped at my first touch.

Her pussy wasn't just sore, it was sticky with a nights worth of cum. I continued to softly lick her, soothing her irritated pussy with my tongue. Lela softly moaned with relief as she lowered herself completely, sitting on my face. Her ass was so big it smothered me. I loved her ass, it was the best part of her perfect little body and it swallowed my face.

"You feel so good babe. I hope you enjoy the taste of you little girlfriend on me. Might be the last time you ever taste her, if I decide to keep you around, I don't know after last night," she moaned making sure I knew she was still pissed.

I stuck my tongue out flat and held it in place as Lela began grinding on my face. Her big ass suffocating me as she ground her pussy against my tongue. Even with all of last nights filth, she tasted and smelled amazing. I felt so dirty cleaning up her abused and sticky pussy.

I finally was able to breathe again as Lela leaned forward, her big ass cheeks freeing my face as I licked her still. I felt the warmth of her mouth as she began returning the favor, blowing me slowly, my balls hurt more than I have ever felt. I almost couldn't enjoy it as I brought my focus back to her tender red pussy.

Spreading her ass cheeks apart I exposed both her holes as I began licking her harder. I wrapped my entire mouth around her dirty pussy, latching on with gentle suction, Carefully I inserted my tongue and gently massaged her sore insides.

"Fuck Matt, Your going to make me cum soon," Lela whispered before blowing me harder.

With my cock down her throat and tongue inside her pussy, I moved in on her remaining hole. My finger caressed her dirty little asshole as she moaned on my dick. Her moans grew more intense and felt great on my cock as I slowly pushed into her. Using my saliva and last night's cum as lube I gently fingered her ass, focusing more on her sensitive entrance more than anything.

With all three hole being worked Lela began to cum. Her mouth never left my cock as her anal muscles clentched down on my finger. She blew me faster, moaning like a whore in heat as she came in my mouth. The sticky stale cum from last night was replaced by a fresh flow of fluid as she ground her ass in my face.

I licked her clean and continued giving little licks and kisses as she worked my cock hard. She was trying to bring me to orgasm but my balls hurt so much. Lela never quits though, she gently grabbed my balls as I twitched in discomfort. She very slowly and gently massaged them as they suddenly began to feel less painful.

That was all I needed as I felt myself ready to cum. Being suffocated by her big ass again I tapped her a few times trying to signal I was about to cum. She held my balls, stroking me as she sucked hard on my head. My muscles tightened and I lost all control over my body as I came. What should have felt great instead was extremely painful as my cum engorged balls released.

I began filling her mouth as my screams were muffled by her ass on top of me. The pain finally eased into pleasure as my pelvic floor muscles rhythmically contracted with intensity. I wouldn't stop cumming as the longest and most intense orgasm of my life ripped through me. The sheer strength of it became clear as Lela struggled to contain it.

She moaned in surprise and panic as her mouth reached full capacity. Too much to handle she slipped my cock from her mouth, stroking me until my organsm calmed. I was lightheaded and laid there as Lela got off me and moved to my face. Her cheeks full as her wet glossy lips quivered to hold back the flood behind them. I knew what she wanted and opened my mouth accepting a large portion of my built up load.

It didn't taste like it normally did, stale from sitting in my aroused balls all night. I quickly swallowed before Lela added another large wad in my mouth. We both swallowed the remainder together as my body went numb, my balls warm and fuzzy from their release of pressure.

"What the fuck babe! Your poor balls," she laughed before continuing, "I did plan on swallowing it all myself but it never stopped! I guess our little show last night was that good."

I laid there, paralyzed from my core shattering orgasm as Lela noticed all her fluids on my face and lips. She leaned over a licked the whole side of my face.

"You taste so much better with my cum all over you," she giggled with a smile while hovering over me.

This woman was so hot and dirty, she was nothing like any woman I had ever been with. I was convinced more than ever that she was bipolar, almost like a real-life Jekyll and Hyde. She could be so loving one minute then pure evil the next. As much as she fucked with me, deep down she had me.

Lela got up and got dressed while I laid paralyzed in my post orgasmic state. "I'm going out for most of the day to run errands, normally I'd take you with me and have some fun along the way but your still punished. I need some time to think about if I want to keep you around or replace your ass with your little girlfriend."

I was relieved that she was going to be gone most of the day. She couldn't do much to me if she wasn't here. Her last statement scared me though. If she didn't want me anymore she would throw me out, with no job and most likely release my video. I had to tread lightly with her.

She chimed in before leaving, "You have one task today. Lay out at the pool and get some sun. I like my bitches with a little tan."

I got up to retrieve my swim trunks from the bathroom before she stopped me, "No no no, I don't like tan lines, lay out there naked. Make sure you don't burn either. It will cause the punishment I have planned for you to hurt that much more."

She walked over to me as I stripped naked and got in my face, "After tonight we will see if your still worth loving."

She leaned in to kiss me and I moved in to meet her. Before contact she pulled away, denying me before turning to leave. I grabbed a towel and headed out towards their pool. The patio floor was hot from the sun on my bare feet but their pool was awesome. It wasn't large but crystal clear and lined with stone. Small BBQ area sat off to the side as the area overlooked their large back yard.

I grabbed a lounge chair, setting my towel down before laying. The sun was bright and warm against my naked smooth skin. I laid there and thought about Lela and Jenna the night before. They were so hot to watch, the two beauties erotically going at it. I found myself becoming jealous of Jenna. When Lela liked you and was in a good mood she was amazing.

I rolled over so I didn't burn then thought about Lela denying me a kiss. It hurt, deep down I knew I loved this woman, though she scared me. I wanted to be good to her, I wanted to be back on her good side. I realized I had to take my punishment without any issues tonight, no matter what she had planned. Then tomorrow I would tell her how I truly felt about her in an attempt to win her back.

I lost track of time and felt my ass start to burn. I quickly went back inside and jumped in a cold shower to soothe my skin. I dried myself and saw my red ass in the mirror. This wasn't good but it was the least of my problems. I quickly got something to eat from the kitchen. I wasn't hungry but knew I had to get something in me.

I then made my way to Lela's room and into her closet. I picked out a white lingerie set she had for me. I struggled to get the corset style top on myself but I managed to do it. Just like last time I struggled to breath when I stuffed my huge breast in but the fabric felt so good over my smooth skin. I found myself starting to enjoy wearing women's lingerie.

I sat in the bathroom while I did my make up for the first time. It wasn't as easy as Lela made it look but after a few attempts I got it how she liked it. The wig was last as I pinned it and weaved it with my own. I knew tonight would be rough so I made sure it was very secure before styling a bit. I got up and checked myself in the mirror. I looked so good that my dick began to get hard, telling me I did a good job.

I sat on the bed as I put on a new pair of matching white heels. I don't know how women wear these things. They hurt like hell and are tough to walk in.

All set with my looks I walked around the room, practicing how to walk in these heels. It's hard but I got the hang of it though I couldn't walk nearly as seductively as Lela could.

My attention shifted to the driveway as a car pulled up. It was a red jeep, just a few years old, a car I had never seen before. I went to hide myself in case someone came to the door but then realized that Lela was driving it.

"Must be one of their many cars," I thought while watching her walk around checking it out.

I ran to her bedroom and jumped on her bed waiting for her. I had to make sure everything tonight was perfect, I couldn't lose her.

The front door shut as I heard Lela making her way to the bedroom carrying bags of things she bought. She turned the corner and dropped her bags, stunned to see me sitting there all dolled up and waiting for her. She smiled and walked over before sitting next to me on the bed.

"I told you that you weren't welcome in my bed anymore. You look really cute though, white looks good on you," she softy said as she gently fixed some blemishes in my lingerie.

I grabbed her hand and stared intimately at her, "I figured white signifies my surrender. I'm done fighting you Lela. I want to surrender to your every demand. I want to make you happy."

I could tell my words were getting to her. She looked away, not able to look at me as I talked to her.

"I am ready to be punished. I am ready to accept whatever you feel I deserve. I was a bad girl and I am ready to pay for it and learn to never hurt you again. I never want to hurt you anymore Lela," I continued pushing myself down into my submissive role, trying to show Lela I was serious.

She leaned in and kissed me. Her lips were soft and her wet lip gloss tasted so sweet.

I wanted more but she pulled back before saying, "You earned the kiss I denied you earlier. As happy as I am to see this sudden change in you it may be too late. You already hurt me. Your punishment will come later tonight and tomorrow I will decide if you get another chance."

She wiped a tear from her cheek before getting up. "I need to shower and get myself ready. I'll allow you to stay here but get some sleep. It's going to be a very long night for you. Your punishment will start when I wake you," She said before walking into the bathroom and closing the door.

I rolled over and tried to fall asleep. I felt good about how that went. Lela was calm, spoke softly and really seemed touched by me. I closed my eyes and drifted to sleep, I believed her when she said it would be a long night for me.

I slept for what felt like hours before waking to Lela in bed with me. She sat up in bed behind me as I rolled over and rested my head in her lap. I just laid there as she played with my fake hair.

"I'm sorry I was a bad girl. I'm even more sorry I hurt you. I am ready. I am ready to be punished," I quietly mumbled, still waking from my long nap.

"Not yet babe, soon though. I just wanted to sit with you a bit," Lela softly responded as she played with my hair.

We sat there in silence, my head in her lap, her fingers running through my hair.

I broke the silence in a soft sad voice, "What are you going to do to me tonight?"

She didn't respond. "I don't care about what you do to me tonight. I do care about losing you though. I don't want to lose you.

"Why don't you text Jenna, ask her what she's doing tonight, ask her if she wants to see you," Lela finally responded.

I didn't question it. I grabbed my phone and fired off a message to Jenna. I laid my head back on Lela's lap and waited while she continued to play with me. My phone vibrated and I read the message aloud for Lela.

Jenna wrote, "Hey Matt! I'm so sorry I can't see you tonight. I have a family thing all night and won't be around. I miss you though."

"Good," I thought to myself. Jenna is away for the night. Lela wouldn't be able to use her against me. My relief quickly ended though as Lela chimed in.

"What you don't understand is that when she says a 'family thing' she really means that she will be eating my sweet cunt in about an hour," Lela quietly laughed.

"It sucks when someone you really like lies to you doesn't it? It hurts, that's what you did to me Matt, you lied and hurt me. It's already dark out which means It's time to get ready now," Lela explained as she attached a collar and leash around my neck.

She pulled me off the bed, holding the leash, walking me like a slave. She walked me down the glass hallway, through the gym and into the Shag Pad. I stared at the restraint bench that a night before was my worst enemy. She tugged at the leash pulling me to it. I didn't protest. I laid down as Lela tightened all the restraints. Daddy wasn't home so at least I knew he wouldn't be plowing my slightly sunburnt ass.

Lela adjusted my wig making it less secure so it could easily be removed before putting the ball gag in my mouth. I felt her pull my pretty white panties down before inserting another plug into my ass. This one was much smaller and thankfully she used lube this time. Lela looked at me one last time before turning out the lights, leaving me staring at the pool and hot tub, just like the night before.

I sat there waiting, I was scared of the unknown but was calm. I think accepting this like I was helped calm my nerves a bit. I thought about Jenna lying to me and how it hurt. I had lied to Lela and felt horrible about hurting her.

I sat for about an hour when I saw some movement. Jenna was here just like Lela said. She looked happier than I had ever seen her before. Hugging and touching on Lela while they made drinks and laughed. They disappeared in the bedroom before returning moments later, walking to the pool area.

Jenna wore a dark green bikini which contrasted perfectly against her soft pale skin. Her bottom was small as it got swallowed by her big white ass with every step. Lela lead the way in her usual string bikini. Red was a new color for her and she looked fucking incredible. I wanted to run in there, grab her and tell her I loved her, but I couldn't.

My eyes followed the girls as they got into the pool, swimming around slightly though never leaving each others side. They laughed and had fun as they made their way to the section right in front of me. Here they could stand in the shallow water, holding onto the side while drinking.

Jenna wasn't drunk yet but she was all over Lela. An indicator of how much she loved her night with the seductive cougar. Lela stood there sipping her wine while Jenna wrapped her hands around her, exploring her body while occasionally kissing her neck. Lela looked up at me and stared, not mouthing anything like last night, just staring.

Her stare was broken as Jenna reached around and grabbed a hold of one of Lela's large firm breasts. Lela's head fell back as she moaned before grabbing Jenna and kissing her on the lips. One of the hottest things to me is watching two beautiful women make out and this was no exception. My cock started getting hard but Lela didn't pull my panties down enough and it became strained inside.

Lela broke their kiss though Jenna wanted more. Lela stopped her and held her drink to her lips. It was clear Lela was getting her drunk though I didn't know why. It looked like Jenna was willing to do anything, no alcohol needed. They downed their drinks as Lela pulled herself from the pool, slicking her wet hair back. It looked like a scene from a hot porno as the dripping wet cougar walked seductively from the pool in her tiny red bikini.

Lela refilled their wine glasses before returning to the pool. She sat on the edge, dangling her feet in the water with Jenna in the pool in front of her. Her and Jenna drank more before Jenna moved herself between Lela's legs, rubbing her smooth wet thighs. They kissed as Lela grabbed both their glasses, placing them down. Jenna pulled on the strings of Lela's bottom, causing it to loosen for her. The magnificent cougar leaned back, opening her legs as Jenna leaned in for a taste.

Lela tilted her head back to look towards me, biting her lip before closing her eyes, she knew I was watching. She laid down completely, looking back as she held her legs open. Jenna's hands appeared moving up her lover's body until they found the large wet breasts they were looking for.

She ate Lela out as she squeezed her tits, pulling them out from the red bikini while mashing them together. I watched as my old lover ferociously ate my new one for what felt like forever. Lela just laid there, staring back towards me and screaming in pleasure as she came. Jenna was eating her so hard while teasing her beautiful brown nipples, but Lela's eyes never left where I was.