The Robertson's Sissy Ch. 12

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Come here Sweetie. I'll help you," A yawning Jenny offered.

I sat on the bed as she did it for me, fixing everything to perfection.

"You look so pretty. I really like you and wish you'd be mine," she whispered as I spooned her to nap with her.

I wanted to tell her not to say that but instantly turned happy when the plug turned on again. Instead I spooned her and immediately drifted off to sleep. I was so tired that I didn't wake up once to the plug going off which I knew it had to.

I don't know how long we slept for but I woke to someone rubbing my back and shoulders. I slowly woke to find Lela finally in bed and Laura standing at the edge.

"Wake up you two," Lela softly woke Jenny and I.

"Jenny and Laura can go downstairs to the movie room for the rest of the night. No one will be down there and you two can have the rest of the night together. Take whatever toys you want."

Jenny softly protested that she wanted to stay with us but Lela quickly shut that down.

"Sorry ladies, I want some private time with my special little girl," Lela explained as she rubbed my body.

Jenny and Laura gathered up whatever they needed and left the room leaving Lela and I alone finally. They left the door cracked open but Lela didn't care as she went to the closet.

"Now I think my little girl offered that I could do anything I wanted to her all night. I think I want to fuck her all night with this," Lela giggled as she opened the package to the massive 12 inch strap on she bought today.

I instantly protested, "Please Lela I can't. I'm too exhausted and that is way too big. Please don't. I'm sorry if I did anything wrong. Please don't punish me anymore."

Lela giggled as she loaded up the batteries and attached the dildo to the harness, "I'm not gonna punish you babe, I'm not gonna fuck you either. I'm going to make love to you all night. Stop being intimidated by its size. If worked right it will be amazing. This thing is perfect. It vibrates and has a small piece that inserts inside me as well and I know I'm going to love it. It is also safe to use with silicone lube so relax babe."

I asked, "What's so great about silicone lube?"

"It's amazing for anal but we normally use water based lube because of the silicone toys we use. I promise you'll love it."

I believed her but this night was too much already and I was exhausted, "I love you Lela but I'm so tired. I'm not used to all this."

Lela put the large toy down and pulled me to her, "Go to sleep for a bit longer. I'll wake you later. It's never like this but most likely being the last night we had to go out with a bang. It's just us now."

I asked her, "You wanted Laura so badly. Why did you let her go with Jenny?"

"I got all I want right here," Lela whispered as she rubbed my face, "Now sleep my love."

Normally Lela laid on me as we slept but this time I laid on her. Her body was so warm and soft from the extremely long bath that Immediately I passed out. I deeply slept as she held me tight to her. I slept so soundly that I didn't even wake when she slipped from under me.

I woke to the plug vibrating at full intensity in my ass and opened my eyes to Lela between my legs missionary. She kissed me as I slowly woke up. She didn't say anything to me as she grabbed the large toy and hooked up the harness while inserting the small ribbed end inside her pussy.

She told me not to be intimidated by its size but I was and immediately was fully awake and nervous. She noticed and rubbed me as she pulled the small plug from me. I felt so empty and wanted it back in but instead she got the bottle of silicone lube and smeared in on my hole.

She then smeared a bunch on the tip of the dildo and she explained to me, "You're look so perfect and I love fucking you. There is one more thing we need to work on tonight. I want you to act more girlie and like a whiney little sissy as I fuck you. I love pushing you to your limits and comforting you through any discomfort."

I subconsciously knew this as she always comforted me and held me after any punishment she gave me. The night her and Jenna pounded me she ended up holding me all night until I was ok.

Lela rubbed the rubber cock head around my hole, smearing the lube as she told me, "I want you to call me 'Momma' when I fuck you. Not in some weird incestial way but more in submitting to my dominance. Just like you call Chuck 'Daddy'. This is what we've been working you to. I love you and this will be perfect so relax and enjoy it."

I spread my legs for her and laughed as I said, "Yes Momma."

I guess she didn't find it as funny as I did as she immediately started pushing. It was thicker than I thought and immediately pushed out against it. Despite its size the new lube pushed it right in as I yelped extremely loud. Lela leaned forward and kissed me as I held her and whimpered.

My loud yelp drew some unwanted attention as I noticed Joe peek into the room. His ass was probably outside the whole night waiting on a second chance to get Lela to be his. I grabbed Lela's face and whispered to her that he was watching. She immediately started slowly fucking me.

"I love you Michelle. No one else can have me but you. I'm yours," Lela loudly spoke to me so Joe could hear.

It hurt as she fucked me. I wasn't ready yet but needed to put on a little show for Joe. I fought through it and whimpered like the sissy she wanted until I saw him disappear in defeat.

"Stop babe stop. It's too big," I immediately begged as soon as I could.

Lela ignored me and continued to slowly thrust inside me. I immediately grabbed her face and stared at her with my best imitation of the innocent look she always gives me.

"Please Momma," I begged in the most submissive voice I could.

She immediately stopped and held it in place as she kissed me. Her hand moved between our legs when I heard a click. Suddenly the large toy buzzed and hummed between us as we both started moaning. I held my legs apart as I held her waist and began grinding my hips on the large toy.

"Fuck me Momma," I begged as I couldn't take it anymore.

Lela leaned in and kissed be before whispering, "I'm not gonna fuck you. I'm going to love you."

She pushed back in and resumed thrusting as she rammed her tongue deep inside my mouth. I latched onto it and began sucking it like I was giving it a blowjob. Her hand reached down between the harness as she rubbed her clit. I kept sucking her tongue as I squeezed both of her firm breasts as she started to cum.

The vibrations of the toy were nothing compared to her body shaking and convulsing like she normally did. It was intense, causing her to fall forward, driving the toy deeper inside me. I yelped again and held her tight as I whimpered like a little girl. Her pussy became too sensitive as she turned the vibrations off which I missed.

We passionately kissed as she recovered and I looked to see Jasmine standing in the doorway biting her lip. I didn't want her to know she was there and ruin her moment so I whispered for her to flip me over and slap my ass as she fucked me.

She didn't hesitate to turn me over and start thrusting inside me. She turned the vibrations on again as her hand cracked down on my bare cheeks.

"Spank me Momma. Fuck me harder and spank me," I screamed.

Lela knew my limit and wouldn't drive in deeper than I could take it though she savagely slapping my ass non-stop. I let out one long loud moan as she pulled my ponytail and head back. I wanted to cum so bad but my balls ached from the long night. Suddenly she pulled out and jumped off the bed.

"Sorry dear this show isn't free," Lela said as she shut the door in Jasmine's face.

She walked back to the bed and she wasn't happy with me. She ordered me on my knees as she scolded me.

"What were you putting on a little show for her?" She yelled at me.

I pleaded, "No Lela, I didn't want her to ruin your moment, our moment."

Lela put me in my place again, "You know she likes it rough like that. If anything you turned her on. You dumb bitch."

"I'm sorry Lela, please don't hurt me," I begged as I hugged her thigh.

Lela calmed and rubbed my face as I looked up at her, "I'm not gonna hurt you or let her ruin what we already started. I love you and though you had good intentions you will still get a mini punishment later. Now back on the bed."

I climbed back up and laid with my legs spread. Lela grabbed my thighs and pulled me to the edge as she reentered me. She swung my legs over her shoulders as she used one hand to hold my wrists pinned across my stomach. As she fucked me I bounced on the bed causing my breasts to bounce as well. Lela gripped them and kneaded them as I closed my eyes and whimpered.

When she had enough she turned me on my side with my ass hanging off the bed. She leaned over me as she turned the vibrations up on the toy. Her right hand slid up my body until she found my neck and gently choked me. This was new and I liked it as she leaned over me and licked my neck and ear.

She started pushing in deeper as she grinded the big toy inside. She was pushing my limits as I whined in discomfort.

"Too much baby, You're so big," I cried.

Lela didn't give in and whispered in my ear, "It's ok baby, Momma's got you."

I felt the grip on my neck tighten as her other hand pressed my thighs tightly closed. The added pressure pushed me close to orgasm and my whining pushed her as well.

"I'm cumming again baby," Lela panted as her body went through the usual spasms causing me to begin another orgasm I didn't think possible.

My entire body clenched down as my anal muscles squeezed. My pelvic floor muscles fluttered as my cock began jumping violently. My muscles uncontrollably contracted so hard that I thought I would squeeze the large toy out. I cried as the most intense pleasure ripped through me.

I laid there light headed as Lela rubbed me in shock, "Did you cum baby?"

I couldn't speak and just nodded my head. Lela gave a huge smile as she rubbed my cock looking for my cum.

"Either we sucked your balls dry or you just had your first Non-ejaculatory orgasm."

"What the fuck is that?" I panted.

"I'm not getting all scientific with this up your ass but you can google it tomorrow. Now if it was then you just opened the door to a whole new world and just made Momma extremely happy. So happy that I will forget about the mini punishment you're supposed to get."

Lela laid down on her back, "Come ride this, I know you don't want to cum anymore but I am going to make you one more time to be sure."

I didn't question her as she wasn't going to punish me. I straddled her and inserted the toy. It was clear that through everything I was barely able to take a bit more than half of it. I tried riding it but it was too long so I leaned forward and allowed Lela to do the work.

She squeezed my ass as she thrusted inside me. It felt so good like this but she got a little carried away and started jack hammering me like I did Laura earlier. I fell forward and whimpered as I held onto her tightly.

Sweat was pouring from our bodies as they slickly rubbed together. We were exhausted but continued as sweat dripped from my face. She pulled the strap of my nighty down and removed my fake breasts. Immediately she started sucking my nipple and I never felt anything like it. She never did this before and I was now going to want this all the time.

"Suck me Momma. Suck me and love me," I begged as I felt an orgasm near.

Lela continued to suck my nipples as she stroked my cock while grinding inside me. I whined louder as my orgasm neared until I couldn't hold back. I sat up and stroked as she gripped my hips and jack hammed shallowly in my ass.

My orgasm started but she wouldn't let up as a quick blast of cum shot across her body on her face. She flinched at the intense force as strong quick spurts pumped across her chest and stomach. It was clear and mostly semen like the others and she slowed her thrusting. She finally pulled from me and leaned up to sucked my sensitive and irritated cock clean.

"You almost took my eye out babe." she giggled as she wiped the cumshot from just below her eye.

I fell off her exhausted as she climbed back to a pillow and laid there. I almost passed out before I heard her hum to grab my attention.

I looked up as she told me, "You know the rules, now be a good girl."

I barely had enough energy to crawl to her but I laid my head on her and worked my way down her body as I licked up all the cum I pumped onto her. It tasted different being mostly semen but it wasnt bad. I almost fell asleep face down on her stomach before she pulled me up to her.

"I love you so much you have no idea. I can't even express how special you are to me. Get some sleep, I feel bad you're so tired. I was going to wake you up and love you again later but we might be done now."

She held me and played with my ponytail as I quickly fell asleep. I must have been sleeping very deeply because she woke me once giggling that I was snoring and had never done that before. While I was awake she didn't miss the opportunity to love me missionary again.

She was so soft this time and just held me and kissed me as she made love to me. It wasn't a long session as the passionate love made her cum quickly. I closed my eyes as she removed the toy and collapsed back on me. Our sweaty bodies tangled with each other as we passed out for the final time that night.

Never once did I experience a night like this and honestly I didn't want to again. My balls ached and I couldn't keep up with these nympho women. Lela promised me this was the last party but we'll see about that. What I do know was the private time we shared at the end was the best sex we've ever had. I couldn't wait to fully recover and do it again with her but after tonight it might be a long recovery. I passed out fully and slept through the night, most likely snoring loudly but neither of us cared at this point.

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Women's Studies Ch. 01 A young man's odyssey trying to attend an all girl college.in Incest/Taboo
April Fool Office Sissy Coworkers prank him into coming to the office crossdressed.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
More Stories