The Robertson's Sissy Ch. 04

**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 the next morning almost forgetting where I was before realizing I was still at the Robertson's. I layed there in bed, still dressed in the baby blue lingerie, sticky from the raw sex the night before. Lela's head rest on my chest, using my fake breast as a pillow. My ass was on fire, hurting to move the slightest bit. There I laid, contemplating the events that brought me here, thoughts that were interrupted as Lela began stirring.

"Good morning sunshine," She said with a smile before kissing my lips, still sticky with last night's cum. "Today is a new day love, let's start it off right."

I didn't say a word, I just laid there with her snuggling me, running her hand up and down my now smooth body until reaching my flaccid cock.

"Please Lela, I'm not in the mood, not after last night," I groaned.

"Normally I don't take no for an answer, your lucky I like you so much," she said bringing her hand back up to my chest. "Last night was rough I know. It hurt me just as much seeing you in such pain. Today I'll let you rest but never let that happen again."

We just laid there in silence for a while until I became concerned about work. I grabbed my phone and checked the time.

Pushing my phone away Lela started in, "Put your phone down my love, your not going to work today. Call out sick and then call back later and quit."

I got pissed, "What! I'll call out sick but I can't quit! I have bills to pay like my phone, car insurance, gas and food."

Calmly Lela laid there, running her fingers up and down my stomach. "You will quit later today, Chuck and I will take care of every financial obligation you have as well as giving you a weekly allowance."

Angrily I got up from bed, pulling off the lingerie and grabbing my clothes, "What am I supposed to tell everyone Lela? I just decided to quit for no reason?"

Lela sat up in bed. Even after a rough night she looked so damn good, but I was fuming at her.

"You will tell everyone that you were offered a job by us, taking care of our estate, mowing, cleaning, whatever the fuck you want to say. It will also give you an excuse to sleep here most nights of the week. Face it, you'll make more money from us anyways," she explained as she approached me. "Plus, Chuck and I are extremely generous to those who are extra good to us," she finished by slapping my sore ass with a devious look on her face.

I raced to get my clothes on and get the hell out so I could think clearly. I threw my shirt over my head while walking out of the bedroom.

"I think you should wash your face sweetie," Lela laughed.

I almost forgot about all the makeup she put on me the night before. I ran to the bathroom sink and started scrubbing it off. In the mirror I saw Lela follow me in, grabbing me from behind.

She stared at me in the mirror, rubbing clean the makeup I missed, "Today you have two tasks, one being to quit your job like we discussed. Second is to rest, your training starts tomorrow." She kissed my cheek before walking away.

I ran out the door and drove home as fast as I could. On the way home, I called into work sick as it would buy me the day to figure out what the hell to do.

At home I laid in bed and thought about everything that happened, searching for a way out. I couldn't find a way around it. Lela had been planning this for some time and she always had an answer for something. Unless I wanted my slutty video to go viral, I had no choice.

I thought about packing my shit and leaving town but I had nowhere to go and no money to do so.

I thought about the worse case scenario. I quit my job and spend most of my nights at the Robertson's house. Ok, that wasn't so bad, they would take care of me financially. Ok, another plus, but I would have to submit to being their sexual slave.

I thought about Lela dressing me in slutty lingerie every day, fucking her brains out at her will. But then there was Chuck. I'd have to suck him off and let him fuck me whenever he wanted. My sore ass reminded me how that turned out as I replayed the previous night's events in my head.

Me on all fours, dressed like a high priced hooker, being plowed from behind. Lela's face appeared in my mind as I hovered over her, begging for Chuck to fuck me as I came deep inside her. I found myself becoming aroused, my dick starting to stiffen.

"Did I enjoy it? Did I want it?" I thought before rolling over. Neither questions were clear, though the fact that I had no choice was. I called up the deli and quit, explaining my new job offer by the Robertson's. They understood but I felt like shit.

It wasn't long before I got a text from Dave, "What the fuck bro? Just up and quit like that?"

Dave was a good friend of mine for years so I had to say something, "Sorry Dave, I unexpectedly got offered a job taking care of the Robertson's estate. I had to jump on it quick. They are paying me a ton."

"I get it. The money is good. You also have the added benefit of seeing that sexy MILF Lela everyday. God that woman is sexy and perfect in everyway," Dave responded as I flipped up thinking about what she was doing to me.

In a fit of rage I fired back," She's not perfect at all! She's a psychotic bitch!"

Dave was confused at that response but I couldn't say anything else. I could do nothing but roll over and sleep, recovering from my assault.

I spent the entire day in bed sleeping only waking a few times. One time I woke to a message on my phone.

It was from Jenna, "Hey, I dropped by the deli to see you but they said you were sick. I hope you feel better. I really wanna see you."

I was relieved it wasn't Lela demanding some crazy shit from me but at the same time I felt bad. Jenna really liked me and I've been neglecting her. I knew I shouldn't respond after what happened last night but I had to keep up some sort of personal life before people started asking questions. As long as I don't make it sexual, Lela might understand if I got caught.

"Thanks Jenna, haven't been well all day, hope it's over soon," I replied.

I rolled over and drifted to sleep for the last time that evening. I woke the next morning, had breakfast and showered. My ass wasn't as sore and I began feeling a little better about myself before returning to see a message on my phone.

Of course it was Lela, "Good morning my love! Your new job starts today at noon. Pack a bag for a night or two. There is a lot of work to do! xoxo"

I packed a bag with everything I needed and nervously waited until I had to leave. The drive felt like hours but I arrived right on time. Lela answered the door wearing the short white bathrobe that got me into this mess.

"Come inside baby! I missed you!" She greeted me with a kiss as she lead me to the bedroom, "We need to get you ready my love. First step is looking the part."

Laid out on the bed was a new lingerie set in black and red, though this one was different. There was no bra, instead this one had a corset like top.

Lela was the happiest I've seen her, skipping around the bed in a flirty manner, "While you rested yesterday I look the liberty of purchasing you a brand new wardrobe. Strip down and try this one on, I'll help you with the top"

I didn't protest and did as instructed. Panties, garter belt and stockings were easy to get on. I squeezed myself into the tight corset style top as Lela clipped the garter belt to my stockings. Her focus shifted to the top as she pulled on the laces in the back. It got so tight I struggled to breath and it got even tighter as she stuffed in the large breast forms.

"You'll get used to the tight fit over time as your shape starts changing. You look so fuckable already and I'm not even done yet. To the bathroom babe!" She happily pointed.

I took a seat like last time and struggled to breath as Lela began teaching me how she wants my makeup done. It wasn't difficult, more degrading than anything.

After the makeup came the wig, pinning and weaving it with my own hair before straightening it out.

"Always secure it good. We don't want it falling off when things get rough," she laughed as she stood me up, displaying me in the mirror.

My god Lela can do wonders. I looked like a perfect woman. If I didn't know it was me I would have fooled myself. The corset style top squeezed my waist in giving me curves where none previously existed. I won't lie, I was hot.

"Come babe, training time starts now," Lela said as she dragged me back to the bedroom.

I thought to myself, "That wasn't the training? What does she have planned now?"

I nervously followed her to the bed where she embraced me in a long kiss. Here we stood kissing, her hands exploring my newly shaped body. I thought back to the other night, our passionate time together as my lust for her took over. I slowly opened the top of her robe and kissed her neck down to her cleavage.

"God, you're getting me wet already. Kneel down baby," Lela demanded as she sat on the edge of the bed.

She slowly opened her robe from the top down. Showing the black satin bra which cupped her firm breasts. The breasts I so desperately needed to fondle. She ran her finger through her cleavage, down her flat toned stomach as she opened the robe little by little. I was ready to eat her sweet tender pussy until she opened the robe fully, exposing the large strapon underneath.

"Surprise!" she said with a laugh. "I had this specially made for you, It's modeled exactly to match Chuck's cock."

I was in shock. Here I was ready to eat this woman all day and now I'm staring at this enormous dildo. One modeled exactly after Chuck, massive bulbous head and all.

"Well, don't just sit there. Be a good girl and suck it. Lesson one for today, how to deepthroat Daddy," Lela said while pulling my head down to it.

I took the big head in my mouth, the rubber giving it a weird and awful taste. Never thought I'd say this, but I'd prefer the taste of the real thing over the rubber.

Lela chimed in as I sucked the head, "Your blowjob skills impressed both of us, so today we focus more on deepthroating. Get it extra wet, you'll need it."

Lela grabbed hold of my wig and pulled me deeper on her rubber cock. The head was so massive that it didn't get far before I gagged. Lela gave me a moment before pushing me back down, eliciting another gag.

"Keep trying babe, we need to push through it. The more you fight it, the more your body will learn to accept it," Lela instructed as I repeatedly gagged on the massive head.

My saliva glands went into overdrive coating her cock as long strings of saliva dripped from my chin and her balls.

Lela's instructions continued, "Relax your throat and allow it to enter."

My throat began to take more of her cock, sliding deeper each time before my gag reflex kicked in. I felt the head push into my throat as it stretched to accommodate the foreign intruder. I gagged again but Lela wouldn't let me up, gripping my hair and holding the enormous head in my throat. It burned and I couldn't breath, tears formed in my eyes as I finally choked before being released.

I tried catching my breath as Lela praised me, "Good Girl! You did so well! We still have a ways to go though, this doesn't happen overnight but I'm impressed! Come here and take a break with me."

I climbed on the bed with her as she held me tight, passionately kissing me. I grabbed her large firm breasts, loving the feel of the satin bra that encased them.

"I see you love the feel of the satin. Looks like I need to pick you up some," she laughed.

Lela drew her attention to mine as she grouped them before running her hands down my newly shaped waist.

"Your such a hot little slut, I knew you would be but didn't expect you to be so perfect. I can't wait anymore. Time for the next lesson, bend over doggystyle, time to teach you how to take this," she said with a huge smile while wiggling her fat rubber cock.

I grew scared and froze, I remembered the painful assault two nights earlier.

"Relax my love, this will be gentle. I want to teach you, not hurt you," her voice was calming and eased my nerves a bit.

I did as instructed and got on all fours, ass in the air. I reached down and started pulling my pretty panties off before Lela stopped me.

"Leave those on, your getting fucked like a dirty whore," she order as she pulled them to the side, letting go as they snapped across my left cheek, exposing my tight little hole.

She mounted me from behind, causing me to jump as a drop of cold lube landed on my warm hole. She rubbed it in as she smeared the rest of her cock with extra lube. She placed the cock head at my entrance, rubbing the lube in. It felt good, my ass enjoyed the massage her cock head gave, but it didn't last.

"Relax now babe, the key is to stay relax and breath. The more you fight the more it hurts. As I push in slowly, I want you to push out," Lela barely finished before her pushing began.

I stayed relaxed and focused on her instructions, breathing and pushing out. I felt her sliding in, I was doing well, but it was too big. Pain suddenly shot through my ass as her cock began to split me.

I screamed, "Ah! Lela stop! It hurts!"

She withdrew and rubbed my lower back, "It's ok, relax my love, I've got you."

Her cock returned, pushing against me as I again pushed back, focusing to stay relaxed. I felt as if I was being split in half. I almost gave in, begging for her to retreat, when suddenly the head popped in.

"Good girl, hard parts done baby. Stay relaxed for me now," Lela comforted, rubbing my back as she continued pushing forward.

The deeper she went the more discomfort I felt though not as bad as the other night. I buried my face in the sheets as she pushed deeper until I felt her hips contact me.

She held in place giving me time to adjust to her massive size. "We're in baby! Now the fun beings!"

She rubbed my back, holding her cock in place as I adjusted to its full size. Slowly she withdrew until the massive head reached my anus before pushing back in. Her cock was huge but she was gentle, easing it in and out, slowly fucking me. The discomfort dissipated as she sped up her rhythm, adding more force with each thrust.

I closed my eyes and felt the pleasure of her work kick in, I moaned to her, "Lela baby, you feel so big, yet so good. Don't stop fucking me like this."

I was enjoying this more than I could have ever imagined. My cock was so hard it begged to be released from the pretty tight panties. I reached down and freed it, jerking myself as she fucked me.

"I knew you would love this, just need to open your mind to it. Daddy likes it rough so get ready. I'm going to fuck you harder," Lela warned before smacking my ass.

She kept slapping my ass as her thrusts became more intense. I looked up and watched in the dresser mirror as Lela fucked me while smacking me. I looked like a filthy whore, submitting to her sexy master. I kept stroking my cock as I moaned uncontrollably before suddenly she stopped.

Before I could beg for more, Lela looked at me through the mirror, "Lesson 3 today, dirty talk." She rubbed my back as she continued her instruction, "Talking dirty always brings me to the next level, but needs to be done right. It needs to come from your feelings and not what you think should be said."

Lela pulled me up against her, her satin bra and skin felt so soft on my back. Her hand reached around taking over the stroking of my cock as she kissed my neck, whispering to me, "For the rest of this session you will say whatever pops into your mind. No thinking about it, just your pure feelings."

Her thrusts resumed as she bent me back over, letting go of my cock and she gripped my hips tight. She began fucking me harder than before and I became lost in the pure pleasure I felt.

"Fuck me Lela, I've never felt this good before. I feel so dirty, so filthy, but it feels so good. Slap my ass again baby. Slap me like the filthy whore I am," I moaned before her hand cracked back down on my ass. "Oh baby! I can't take it anymore, my cock is aching."

Lela reached underneath grabbing me by one of my breasts and pulling me back. Her other hand reaching my cock where she stroked me as she pounded my ass.

"My dirty little girl looks so hot taking Momma's cock," she whispered while staring in the mirror at me, groping my tits. The site was too much for me as her hand was bringing me to orgasm.

"I want to cum Lela, please finish me off, I'm so close," I begged before suddenly she left go of me before pulling her cock completely from my ass. I felt so empty without her inside me, a depressing feeling took over.

"I'm sorry my love. You can't cum like this, I have plans for your big load. Lie down on your back and spread your legs for me," Lela instructed grabbing a pillow to place under me.

I didn't waste any time getting into position. On my back, my stocking covered legs in the air, I needed her back inside. "Please Lela, I need you so badly, fuck me Momma."

Lela pressed the massive head against my now willing hole and entered. The empty feeling replaced by pure desire. I wrapped my legs around her as she leaned over and began kissing me. This was better than anything. She fucked me with pure passion as I held her sweaty body against mine. I reached down and grabbed her round ass, squeezing it while pulling her deep inside me with each thrust.

"mmmm my little whore likes it deep." she whispered.

All the fear I had was gone and replaced by pure lust. My legs wrapped around her tighter, making sure she couldn't leave me. She fucked me harder as my hands ran up and down my lingerie. The fabrics felt so good, I felt so sexy. I tightly gripped my now bouncing breasts as she pounded me faster. Sweat dripped off her face onto mine as I stared into her beautiful brown eyes.

She was exhausted, panting for air as she made love to me. I didn't want this to end but Lela was spent. My cock sandwiched between us, rubbing against our sweaty bodies, it ached for release.

"Lela my love, finished me up, I can't handle anymore," I begged as I kissed her.

She sat up and fucked me while stroking my cock. I watched as she unclipped the dildo from the harness, holding it in place with her hand for the time being.

"Cum for me baby, cum for momma," she moaned as I felt my orgasm near.

I encouraged her, "Don't stop, I'm so close baby!"

She removed the dildo from the harness, using her hand to thrust it into me. She leaned over taking my cock her mouth sucking me hard while she drove the dildo deep inside.

The warmth of her mouth was too much, "I'm gonna cum Lela!"

I screamed in pleasure as she pumped the dildo as fast as she could. Driving it deep as I began filling her mouth with my load. I felt her moaning on my twitching cock, knowing that I was giving her the massive mouthful she loved.

She slid the dildo out as my orgasm came to an end. My cock slipped from her mouth, though she was careful not to spill any of the cum I rewarded her with. I watched and waited for her to swallow but instead she crawled back up on top of me. Grabbing my face she leaned in and kissed me.

I opened my mouth to accept her tongue and with it came a bunch of the cum I just fed her. We kissed as my cum rolled around our tongues before settling in my mouth. It was sweeter than any of the cum I tasted previously.

Lela then introduced me to the last lesson, "Swallow it babe. I hate giving away a sweet load like yours, but you need to learn to love the taste. Good girls can't clean up their mess if they don't love the taste of a man. I can't get enough of it and soon you won't either. You'll start to crave it and learn to seek it out when you desire."