The Robertson's Sissy Ch. 18

I woke the next morning to the soft strokes of a finger across my face. I woke startled, not knowing where I was until I saw Jenny leaning over me, I was still in her bed. The night before the asian goddess pounded me to exhaustion and I slept soundly through the night. My balls were constantly hurting which reminded me of the chastity cage and not being able to cum all night.

"I'm going out for my run Sweetie. You can let yourself out when you're ready," Jenny told me as she stroked my face.

She was pantless but had her sports bra on already, her hard little nipples poking through the tight fabric. Normally she would ask me to stay until she got back but I could see the disappointment on her face. With her pants in hand she leaned in and kissed my cheek.

I grabbed her face and immediately started making out with her. I wanted to give her something before I left. As much as she tried to force herself to leave she couldn't resist and kissed me back. Our kisses grew deeper as she finally swung her naked leg over me and straddled my lap. I sat up and kissed her as my hand slid down her flat toned stomach.

I couldn't fuck her with the cage so I decided to use my fingers. My hand wiggled under her and was greeted by her warm soft flesh. I rubbed her pussy hard as she tried to stop me.

"No babe," she whispered until my hand began rubbing her clit.

She let out a soft moan before nodding in approval and locking me into a deep kiss. I gently pushed inside causing her to moan in my mouth, my fingers hugged by the warmth of her soft flesh. Slowly I worked her as she breathed heavily and moaned. Not once did our kiss break until she was finally wet enough for me to get rougher.

I opened my legs, forcing her thighs to spread open. Now at my mercy I began savagely finger fucking her, causing her lips to quiver against mine as she moaned uncontrollably. Our kissing was passionate but my hand underneath was giving her a forceful fucking. Each time I drove inside her my palm would smack against her clit causing her tight body to twitch and shake.

She couldn't last with this intensity and began to cum. Dropping her hips down and trapping my hand between us. She was now in control and grinded hard against my fingers, her swollen pussy lips gliding across my palm. She held me around my neck as her head dropped back, screaming as she rotated her hips.

I allowed her to come down from her blissful state as we kissed some more. I worked my way down her neck and began sliding her bra strap down when she stopped me and suddenly jumped off the bed.

"Stop babe. This isn't going to make it any easier," she said as she grabbed her yoga pants.

I sat on the edge disappointed and she saw it in my face. With a small smirk she walked over to me and lifted her leg up on the bed. Her wet pussy stared me in the face as I felt her hand on the back of my head, pushing me closer. I gave her pussy a couple of long soft licks and savored every second of her taste, I wasn't sure when I would get to again. I finished by giving small soft kisses around her pussy before she finally put her leg down and pulled her pants up.

"Thank you babe," she whispered before giving me one last kiss and turning to leave.

I watched the sexy woman walk away before getting up to get dressed. I stripped off all my lingerie and packed it up before washing my face of all the make up. I found my shorts and shirt and threw them on before heading downstairs and grabbing my shoes. Jenny was already gone so I had no reason to stay and left her house for the last time.

I hoped to get a final glimpse of the magnificent woman running down the road but she was gone by the time I drove down the street. The emotions from this morning distracted me from how sore my ass was from the night before. I laughed to myself about how badly Jenny plowed me as I drove home. It might not have been the best idea considering Lela and Chuck would sure be putting me through a lot later.

I did love being with Jenny but I couldn't wait to see Lela and just be back at the Robertson's. Not going to lie though, I was nervous as hell to see Chuck. I pulled into my driveway and grabbed my bag to go inside. I dropped it on the floor of my bedroom and collapsed on the bed, just lying there thinking. I grabbed my phone see a message from Lela that I missed while driving.

"Hey Matt, Come over at 3pm. XOXO"

I figured it was a good sign the way she ended the message but was surprised by how early she wanted me over. Chuck didn't normally get home until 7 or 8 pm so I knew she had something planned for me. I responded before putting my phone down and going back to thinking about everything. I really wanted to do something but my ass was slightly sore and my balls were killing me. I couln't stop thinking about sex though it made my balls hurt even more.

I jumped off the bed and started a cold shower to calm me down. Last night was rough and I had to wash off all the filth to make myself perfect. The cold water eased my discomfort as my blue balls relaxed, I was still beyond horny though.

After showing I cleaned up my room a bit and gathered everything I may need to go away. Lela would tell me where we were going but I figured it was somewhere warm and tropical. Throwing my items in an extra suitcase along with my passport until I knew more about what I may need.

Done cleaning and somewhat packed I laid back down and grew bored. It was just after noon and I didn't know what to do with myself. I reached over and grabbed my phone and decided to ask Lela if I could come by early and she quickly responded.

"Are you that eager to start?" She asked with a playful winking emoji.

I responded, "I'm bored babe and don't know what to do with myself."

"Oh I know a few things you can do. Yes, you may come over whenever but just because we are starting early doesn't mean we are ending early."

I don't know what was going to happen later but I just wanted to see her. I finished getting dressed and cleaning before grabbing my lingerie bag and heading out. I missed this woman so much but was so nervous about how things might go. It was a hot summer day but I felt like most of my sweating was due to my nerves. I took comfort in the fact that she sounded upbeat in her messages.

The drive over felt like an eternity but I finally pulled into the Ronertson's driveway just after 1 PM. I grabbed my bag and slowly walked across the gravel driveway to the front door. Normally I just walk in but after this week I figured I would knock. My heart raced as I waited until her silhouette appeared and the door opened.

"Hi babe!" Lela greated as she pulled me inside.

The mature latina wore a pair of baby blue booty shorts and black spaghetti strap tank. She looked fucking great and I didn't have to wait long to have her as she immeidatley grabbed me after shutting the door. She excitedly pushed me against the door and locked me in an aggressive kiss. Her hard nipples indicated she wasn't wearing a bra and was raring to go though she slowly broke the kiss.

"Welcome home. I missed you," she whispered before grabbing my hand and leading me to the bedroom.

In the bedroom she grabbed my bag and threw it off to the side, "You won't be needing these anymore."

"Wait, that has my stuff."

Lela shushed me and led me to the closet and turned on the light. I stood amazed at everything she had done this week.

"I upgraded your wardrobe and everything else my little Michelle may need."

I walked in and checked out all the clothing. There was all new and sexy lingerie but also a lot of other clothing. Skirts, dresses, blouses and tanks. There were more heels, sneakers and accessories I may need. I stood there kind of shocked when Lela grabbed my waist from behind and held me.

"Will my little girl like all this? Here I got more," she whispered before opening a cupboard door revealing new wigs.

"These are more realistic and no one will ever know the difference. I also got you these," she said while pulling new breast forms from the closet. They were bigger as she held them out for me to feel and I couldn't believe how realistic they felt.

"These are so much better babe. We had to go up a size but they can be held in place better by the suction they create and are the most realistic money can buy. They were expensive but I only want the best for my little girl."

Lela wrapped her arms around me and kissed me before continuing, "Do you like it all?"

"Yes Lela, I am kind of shocked."

"Good, I got one more thing," Lela added as she bent down to open the bottom draw of the cupboard.

My eyes lit up when it opened revealing a draw full of sex toys. I knelt besides her and looked through all the plugs, vibrators and strap ons. One toy piqued my curiosity, a long but thin pink silicone toy that had a tear drop shaped ball at the end. I picked it up to check it out when Lela took it from my hands.

"This one's for me. It works just like your little plug but for my pussy. Maybe I'll show you how amazing it works in a bit. Come though, let's start getting you ready."

I stood up and followed Lela to the bathroom when she began drawing a warm bath. As the water filled the tub she embraced me in a series of long kisses as she undressed me.

"Did Momma do good with her shopping all week?"

"Yes Lela, Holy shit you did good. Thank you," I responded.

"Good, If you're a good girl tonight it's all yours. Bath is ready babe, get in."

Her statement reminded me that I am not out of the woods yet and there is a possibility that I would be asked to leave again. I climbed in the tub and sat down in the warm water as Lela left for a bit. The warm water relaxed me and almost put me to sleep until Lela reappeared with all the new things I would be wearing tonight. She laid them down before I could get a good look and came to tub with me.

Lela knelt down and grabbed a luffa to begin washing me down. She started at my shoulders and worked her way down to my legs. The whole time she didn't miss an opportunity to kiss my neck whenever she could. When satisfied I watched as she removed the key to my cock cage from around her neck and went underwater with it. I grew excited as I felt it unlock and be removed. Lela saw my excitement and smiled before leaning over.

"I love seeing my little girl be happy," she whispered before kissing me and stroking my cock.

Immediately my cock awoken from its sleep and was hard as a rock. We kissed as she stroked me and rubbed my balls. My balls hurt and I wanted to cum desperately but she quickly stopped.

"Come out you're done," she said while holding a towel out for me.

I stood up and stepped out of the tub and she wrapped me in the towel and dried me. I sat down on the chair in front of the mirror as Lela grabbed my lingerie. It was red and white with hints of pink. She slid the white and red thong up my legs as I stood to get it all the way up. It had a solid waist band that sat very high on my hips with lace all down the edges. Stockings and garter belt were next before she held the new breast forms up to my chest.

"Watch, these should stay in my place a bit," she said as she pressed them tight to my chest.

The suction held them in place as she grabbed my top and pulled it over my head.

"This is different. I like it," I told her as I saw how it looked in the mirror. I don't know the actual name of it but it was like a combination of an extremely short tank top and a bra. It stopped half way down my ribs and lifted my already huge breasts higher.

"Wow your boobs are bigger but they look amazing," Lela stated as she adjusted them.

Without warning she reached down and pulled my panties to the side and freed my cock. I grew excited as she knelt thinking she might give me head but instead she revealed a new cock cage.

"No Lela. Please no babe," I begged but she wasn't going to listen.

"First it's a new one and will be more comfortable. It's lower profile and will make much less of a bulge down there. Secondly I don't want to hear you say that again. I was going to wait until the bedroom to tell you about tonight but I figure I will tell you one bit now. The word 'no' will no longer be part of your vocabulary. Daddy was extremely clear on that so you better not let that word slip later," Lela explained as she secured the new cage and placed the key around her neck.

"What are you two doing to me later?"

She explained, "It's not what we are going to do to you. It's about what we want from you. We want more of a commitment but we will talk about it soon."

Lela stood up and opened her makeup bag and began pulling everything out. Everything was standard except the extra time she took making it perfect before getting to the lip stick. It was a bright shade of red which matched my lingerie. Lela took her time applying it before standing up and checking me out.

"Perfect!" She stated before grabbing a new wig.

She turned me from the mirror as she placed it on my head and secured it. As she styled it she told me, "These look so much better. It will look 100% like your real hair. Your hair is getting longer though so one day you won't need it."

She styled it before grabbing a red ribbon off the counter which she used to tie my hair back. The chair began to turn as Lela finally revealed me in the mirror. She was right, the wig looked amazing as did everything else. I looked good with all the older stuff but this was a huge upgrade. I really felt like I would have no issue passing as a woman.

I stood up and checked myself out completely. I looked so innocent with the little red bow holding my hair. My waist had gotten thinner and these new breasts were huge though they had just the right jiggle.

"Come on babe, let's go chat," Lela said as she grabbed my hand.

She led me to the bed where she instructed me to sit up against the headboard. She disappeared in the closet and returned with two pairs of cuffs and red heels.

"These are your heels for tonight," she told me as she climbed on the bed and straddled me.

She grabbed each wrist and held it back before cuffing them to the head board.

"Is this necessary?" I asked.

"Yes, get used to it. This isn't a punishment. It's just such a turn on to have complete control over you. This is going to be our new thing."

Luckily I was cuffed in such a way where my arms could rest if I wanted but all my attention was on the latina cougar in front of me. She sported a huge smile as she leaned in and kissed me while running her hands up my body.

"So tell me about Jenny's house last night," she asked.

I laughed a bit, "She was pissed at the cock cage and made me wear a strap on to fuck her. She proceeded to then use it on me and fucked me so hard trying to make me cum."

Lela burst out laughing, "I'm glad to hear of the struggle. I like the idea of having you use the strap on though. I want to try it, at least you got a good fucking.

"Nah, my ass is sore which is going to be bad for whatever you two throw at me later tonight."

"Oh babe. Tonight will be much more mental than physical."

Lela paused a bit before continuing, "You know I love you so much,"

"I do and I love you too."

Lela continued, "Chuck and I want more of, let's say a commitment out of you. I'm scared though because I am not sure if you are ready yet. I want you to stay here with me. I've been trying to show you how good I can be to you and how I'll take care of you but in the end it will be all up to you to decide."

"Lela, I want to be here. I don't want to go anywhere."

"I know you do but whether or not you stay depends on tonight and if you agree. Chuck and I want to see some things happen. First we want you to move in permanently. Even if we ever move you are coming with us."

"Deal. That's easy," I stated.

"You have been so good with this transformation with Michelle but it's time to take the final step. It's time for you to be Michelle all of the time instead of just playing Michelle."

"Ok, I'm slightly confused," I questioned.

"It's time for you to embrace Michelle and be her all the time. Even out in public."

"Lela I can't. Not around here."

"If you pass tonight then I will tell you where we are going away and you will be going away as Michelle. Consider it the perfect practice test. You will only be Matt to and from the airport as I don't want issues with security. I know you have friends and family so you will only be allowed to be Matt around town or If I demand my man in the bedroom. Daddy said no to that but I got him to give in. I think it's generous."

I sat there speechless but thought I might be able to do it. Going out in public scared the shit out of me though.

Lela chimed in more, "You know I won't let anything happen to my little girl and I'll protect you. But you need to know that I am not just your lover, I'm your master as well. Anything I say goes. I own you just like you're a piece of property and trust me, there will be no way out once you agree. Just so we don't have issues like with Ralph I will be the only one to control you and make decisions. All Daddy can have is control of you in the bedroom. Remember 'no' doesn't exist in your vocabulary anymore."

I sat silent for a while. The control thing didn't bother me but I knew if I continued that there was no going back. Lela would make sure there was no way out for me. This whole being Michelle full time and practically being owned scared me.

"I love you more than anything Lela but I don't know."

Lela raised her voice, "It's simple, either we go this route or you go back to being boring Matt and never get to see me again. There is no in the middle. Oh and don't think about Jenna or Jenny. I will lock them down so quick they will never see you either"

I sat silent again. It would crush me to lose Lela and she was right that the other girls would choose her over me.

Before I could speak Lela chimed in again, "Well Daddy won't be home for a while so maybe I can help make your decision making easier."

Lela turned herself around and faced her big round ass at me. Seductively she stared over her shoulder and bit her lip before grinding on my lap. Slowly she peeled her blue booty shorts off revealing her tan jiggling cheeks which were swallowing a small black g-string.

"Are you telling me you don't want to fuck this ass anymore?"

Lela resumed her tease and began twerking one cheek at a time on my lap.

"Who's going to pound it if you're not here? This ass needs you so bad baby."

I sat mesmerized as she continued rubbing and giving me a lap dance.

"Please baby, You can have this ass everyday. I need you deep inside it baby. Just like before, only you can have it."

Lela begged as she breathed heavily while grinding on me. She smiled back as she knew she was killing me before turning back around and kissing my neck. Leaning back she pulled her panties to the side revealing her perfectly smooth and wet pussy. She gently rubbed it as she teased me.

"Look how wet you get me. Don't you want this pussy everyday? You know how good Momma's pussy is to you," she giggled as she raised her wet fingers to my mouth.

"Are you gonna tell me you don't want to taste this pussy anymore?" She asked as I licked them clean.

No one tasted like her and now my balls ached more than ever. She paused as she watched me struggle with my aching balls as my stomach started gurgling.

Lela giggled, "Oh is my little girl hungry?"

"Yes babe, I should have eaten lunch before I came."

Lela thought a second, "You know I will always take care of my little princess but you need to skip a meal. I need you a bit thinner for vacation. We are getting your figure the hard way. Other option was to put you on hormones but I didn't want to mess with it. You give the biggest and best cumshots of any man I've had and I don't want hormones to mess with that. See I'm trying to be generous with this transition."