The Robertson's Sissy Ch. 15

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

I asked, lIs this seat taken?"

I wasn't sure how she would react but her face said it all. When she turned and saw me her face lit up in pure excitement and she couldn't fight back her smile if she wanted to.

"Hi Sweetie! How are you? Oh my god, I can't believe you're here," she excitedly hugged me as I sat down.

She looked around before asking, "I'm sorry to say this, but you look like shit. What's wrong? Where's Lela?"

"Not with me. I got thrown out," I told her.

I proceeded to tell her the entire story about how I got thrown out and basically how fucked up things have been. She listened to everything I had to say before finally talking.

"It's ok. I hate to say this but she wil get you back. That woman is beyond crazy for you," she told me as I looked at her confused.

"Sorry, I didn't mean to say it like it was a bad thing. Just means I can't lock either of you down as my permanent play thing," she laughed as her hand creeped onto my lap.

"Well, I haven't heard from her in a few days so you may have your chance to lock me down for good," I whispered to her.

Jenny just stared at me and seductively bit down on the straw, "Well either way I think we can have some fun while we can."

She was incredibly beautiful and flirty causing any thought of Lela to slip my mind. We sat there and chatted for a while as her drinks allowed her to loosen up a bit. I watched as she would occasionally undo a button on her blouse here and there causing her massive cleavage to stare at me.

She turned to me and leaned forward as her breast squeezed together. The pink lace bra showed as her breasts popped from the top. My hypnotic stare was interrupted as she lifted my chin with her finger in order to bring my gaze to her smiling face.

"Up her Sweetie," she giggled knowing she was teasing the hell out of me.

Her beauty caught a lot more than just my eyes as another guy approached her and offered to buy her a drink. It never ceases to amaze me how cocky some guys are to approach a woman who is clearly involved with someone else.

"Sorry dear, I'm only interested in women. Oh and this young stud's cock," she told him as she gave my crotch a squeeze.

He retreated in shame as I sat surprised. Jenny was never like this; she was always more reserved and proper outside the bedroom.

"Damn Jenny, I have never seen you like this," I told her.

"Well, I know what you like and will be a little dominant whore like Lela for you," she giggled as she sipped her drink.

I was completely turned on by this and played along with her. I joked, "I thought you only enjoyed me as Michelle?"

"Yeah I love my women but you can be my exception. You make me feel alive and I'm happy I ran into you today. Happy isn't the only thing I'm feeling by the way," she seductively whispered as she started to stand up.

"Oh really, what else are you feeling?"

She leaned in and whispered into my ear, "Follow me to the bathroom and I'll show you."

I watched her walk away and towards the hallway with the restrooms. She gave a quick look around before slipping into the men's room before I quickly got up to pursue her. I almost made it to the door when another man walked up and entered the bathroom before me. I was right behind him and was relieved when he took the first urinal by the door. I walked down to the last stall where I found Jenny undoing the last buttons of her blouse. Her large breasts screaming to be freed from the pretty lace bra.

I quickly entered the stall and held my finger to my lips to tell her to stay quiet. I turned to close and lock the door and immediately felt her hands undoing my jeans. She squatted and freed my cock as I turned to her. She stayed quiet and kissed my cock while staring up at me. Giving little teasing kisses to my cock head before giving each one of my balls a kiss. She gave me one last smile before taking me into her mouth.

It had been days since I felt the warmth of a woman's mouth on my cock and I leaned my head back in ecstasy. I held the back of her head and guided her down the length of my cock as she took all of me that she could. She couldn't deepthroat like Lela but damn she did an amazing job.

We heard the toilet flush from the other guy as Jenny changed from sucking to licking me. She stared up as she licked the bottom of my balls, up my shaft and across my sensitive head. Over and over she did this while squeezing her breasts together. Finally we heard the other guy leave and she shot up and turned around.

Slowly she lowered her jean shorts revealing her ass and the fact that she wasn't wearing any panties. Fortunately she was wearing sandals and was able to slip them off quickly and completely before putting them on top of the toilet paper dispenser. With her legs closed together she bent over while looking over her shoulder at me.

"Well what are you waiting for? Lick this pussy bitch," she ordered with a smile.

I immediately squatted behind her and dove my face into her. Her pussy was already so moist and I savored every bit of it. As I ate her I felt her grab my wrists and pull forward driving my face firmly into her. She began gently wiggling her ass, grinding her pussy on my tongue a she gently moaned. I was loving this and wanted more but we needed to be quick.

I felt her release my wrists allowing me to stand up and prepare to take her from behind. I pressed against her and easily slid right in. The warmth of her pussy felt amazing and I immeditely began fucking her. As I thrusted I wrapped my arms around and pulled her back against me. Looking over her shoulder she began to kiss me as we made out while fucking.

My hands caressed her chest and found each of her large breasts. I squeezed them hard as I began thrusting with force. Lust over took me as I pulled the cups of her bra down, allowing her soft firm breasts to flop free. I kneaded them as I pounded her causing her to moan in my mouth as we kissed.

Suddenly she pulled off and squatted in front of me. She began sloppily blowing me again causing large globs of saliva to dangle from my cock.

"Your cock taste so much better with my pussy on it," she whispered as she wiped the saliva from my cock to her breasts, "Let's make this quick."

She knew my weakness for a good titfuck and smiled at me as she wrapped her breasts around my cock. Once inside she lowered herself up and down as I fucked her soft cleavage. The sensation of her breasts were amplified by her sheer beauty as she smiled up at me.

"I want to swallow every drop of you," she told me knowing I was getting close.

Suddenly the door to the bathroom opened and another person entered. Jenny stood up quickly and we panicked as we heard the footsteps approach the stall next to us. I grabbed her waist and picked her up as she wrapped her strong legs around me. With my hands under her ass I held her up so only one pair of feet could be seen under the barrier. She wrapped her arms around my neck and silently laughed at our situation before reaching under and guiding my cock inside her.

An expression of relief took over her face as I was again inside her. Slowly she ground her hips against mine as her toned legs held a death grip around my waist. I was in heaven as she worked me and wanted to moan loudly as I started losing it. Jenny pulled my face down between her large breasts as she continued her grinding while I held her. I was trapped between them and wanted to stay like this all night but felt my orgasm coming and knew she wanted it in her mouth.

I pulled my head from her cleavage and mouthed that I was cumming. She didn't stop though, instead she leaned in and whispered in my ear, "Cum inside me."

I squeezed her ass tight as my legs shook with my impending release. I tried squeezing my PC muscles to stop my cum but they weren't strong enough yet. I held her tight as my cock pulsed inside her. Her grinding slowed as I began pumping my load inside her. She just smiled as I filled her velvety soft pussy with every drop I could give her. Now spent I still held her as she silently kissed me as the guy next to us finished and began to wash is hands. Quietly we got dressed and prepared our escape from the men's room.

I slipped out first and made my way to our seats just in time to watch her slip out unnoticed. She joined me at the bar and couldn't get rid of the smile on her face.

"Oh my god, that was amazing. I need to try slutty things like this more often," she quietly told me as she tried settling down.

We sat there and chatted for a while before she put her number into my phone. I had to warn her about Lela getting all my messages and she assured me that we would work our way around it.

She told me, "My husband is home tonight so I can't see you but every morning I go for a run. Maybe I'll look for you around 8am outside the strip mall on Main Street."

"Oh I'll be there waiting for you," I assured her.

"Not unless Lela calls you first," she said in a snippy manner.

This whole time I barely thought of her but now she was on my mind. I wanted to appease Jenny but she was right. As sexy as Jenny was and no matter how much fun I had with her I knew I would go running to Lela as soon as she called. Before I could think of something to say Jenny took my attention.

"Oh what the fuck?" She whispered as she pulled a wet hand from between her legs.

She continued, "How much did you cum you nasty little slut? It's dripping down my leg."

I laughed, "Well it's been a few days, sorry."

She smiled before asking for the check, "You're not gonna find it so funny in a minute. Let's go."

We finished up paying and got up from the bar stools. I caught a glimpse of a small wet spot on her jeans and knew I filled her up good. Outside she hurried to her car and jumped in the driver side before I could catch up. When I got there she already had her shorts to her ankles, turning her body to me before leaning back with her legs up. What a sight to see, her two swollen pussy lips stared at me as a small amount of cum leaked out.

"Well since you find it so funny you can clean me up. Do it quick so no one sees."

I leaned through the open door and began licking her cum cover pussy clean as she squeezed out more of the cum I filled her with. She was right, I came a lot but I loved it. Before I could finish I felt her hand on the back of my head pulling me in.

"Mmmm I know how much you love to lick your cum out of a tight little twat."

I finished licking her clean and thought about how much of a turn this woman was taking. She was obviously doing all this to imitate how Lela treats me but it was working. She had me wanting more but I was going to have to wait. She sat up and kissed my cum covered lips before saying goodbye.

"Can't wait to see you bright and early tomorrow morning," she giggled before closing the door and starting her car.

I stood there and watched in amazement as the asian goddess drove away. She left me in awe but reality set in when I checked my phone with no messages yet from Lela. This sucked, alone again I felt my depression begin to push its way out again. I got into my car and drove back home for the night.

At home I laid on the couch and thought of my amazing time with Jenny. She was dirty tonight and I loved it. She was definitely trying to compete with Lela but I was going to play along and enjoy every moment of her dirty and dominant transformation. She was so gorgeous that her huge breasts and amazing body were just an added bonus. Looks-wise she was the perfect woman and every man's dream but I still couldn't shake Lela from my mind.

I wondered what she was doing or how things were going with Chuck. I missed her touch and waking up next to her every morning. It was getting late and I had to get this woman out of my head. Staggering to my room I crawled into bed. I wanted to sleep but I was now so horny after thinking about both women.

Rolling out of bed I retrieved some lingerie packed by Lela. I decided on a o blue lace bra and panty set before putting some thigh high stockings on and jumping under the covers. I laid there and rubbed my cock through my panties as I replayed the events from earlier in my mind.

My cock couldn't take it anymore as I pulled my panties to the side and began stroking. I thought of Jenny squatting in the bathroom and innocently kissing my cock, her titfuck and licking her pussy clean in the car. I was so hard and I needed to cum. My hand traced my smooth body and cupped my fake breasts as I tried pushing myself over the edge.

My thoughts suddenly shifted to Lela riding me in her hot tub and the thought of her brought me close. I thought about being all dolled up as Michelle with Lela fucking me hard from behind, slapping my ass and pushing my face down into a pillow while calling me slutty names. That image immediately brought me to orgasm as I came all over my panties and stomach.

I cleaned up a bit but didn't bother changing, rolling over and closing my eyes. I drifted off to sleep thinking of seeing Jenny in the morning and I couldn't wait to get a taste of her again.

I woke early the next morning, still in my slutty lingerie. I quickly changed in case I saw my mother but laid in bed for a bit. I drifted in and out of sleep while exercising my PC muscles. I really wanted to conquer this nonejaculatory orgasm. The one time I had done it was the most body shuddering experience. Though I haven't had one since I have noticed my orgasms becoming more intense and forceful. At least I was seeing some change.

I finally got up and made something to eat and had some coffee. Lela still dominated my mind as I kept checking my phone but I tried focusing on seeing Jenny shortly. Though I was excited to see her I found myself wanting a cock. Real or fake I wanted to get fucked. Again I was hard as a rock and decided to take a cold shower to calm myself down.

Afterwards I got dressed in a pair of mess shorts and t-shirt though I decided to wear my soiled blue lace panites underneath. I love wearing panties, even under my usual street clothes. I left my house and drove down to Main Street and parked at the strip mall. Most of the stores opened in an hour so the parking lot was fairly empty. I was a bit early so I sat there waiting.

I grew excited as my cock stiffened in my tight panties. I looked around to make sure I was alone before pulling my shorts and panties down. I waited as I gently played with myself in the car when I noticed Jenny running up the street. It seemed like she took forever to get to me but she finally got close enough so I could make out the huge smile on her face.

She wore tight black yoga pants and a white spandex shorts bra as she jogged up the street. Her hair was in a ponytail which bounced with each step along with her large breasts. Her jog slowed as she got close to the car as she walked the rest of the way. I sat there holding my cock for her as she opened the door and jumped in.

Immediately she leaned over and took my stiff cock into her mouth. Jenny let out a loud moan almost as if she was eating her favorite food.

"Well good morning to you too," she laughed as my cock slipped from her mouth, "Drive somewhere else."

I pulled out of the parking lot and drove down the street as Jenny gave me roadhead. Her ass was popped up so I slid my hand down her back and pulled her tight pants down, exposing her tight little ass. I caressed it before slipping my finger over her asshole causing her to slightly jump.

"Sorry, but I just suddenly recalled that you owe me a crack at this ass," I joked.

Jenny stared up at me as she licked my cock, "I was hoping you would forget about that offer. You will get it but not right now. Right now you're cumming in my mouth. I couldn't swallow you yesterday but this morning you're not leaving until you do."

I pulled into a park and drove to the most secluded part of the parking area while rubbing her wet pussy. I took a moment to admire the sight of her head and ponytail bobbing up and down in my lap before she suddenly sat up.

"Get out," she ordered as she opened the door.

I quickly followed her to the back of my car where she seductively bent over the trunk. I grabbed her thin waist and slowly pushed inside her, taking her from behind. I fucked her slow and deep as she spread her arms out across my trunk, lustfully taking it. She turned over her shoulder and stared at me and her beauty did something to me.

I don't know what over took me but I began thrusting with force as she moaned to my aggressive fuck. I gripped her ponytail, pulling her head back as she fought herself from screaming in pleasure. My other hand gripped her hip tight and drove her back as hard as I could with each forceful thrust.

I never fucked someone so hard as she whined and squirmed as I pounded her tight pussy. All that could be heard were the early birds singing in the trees and my balls viciously slapping against her pussy. I released her ponytail in order to get a stronger grip on her hips as I threw her back into each thrust.

"Fuck. Fuck. Fuck. Fuck," was all she could say. Each word coming after each forceful thrust.

Suddenly she squirmed and whined as she began cumming. I didn't stop though and kept pounding her as her orgasm ripped through the silence of the park.

"Stop. Stop. Stop babe. My pussy is too sensitive," she breathlessly begged as she pulled my cock from her.

She squatted and stroked me as she caught her breath with a smile.

"Jesus Matt. My pussy is going to be sore for days. Holy shit," she giggled before giving me a quick suck.

Jenny let my cock slip from her mouth before leaning against my car, leaning back and pushing her chest out. I stepped in front of her as she lifted the bottom of her sports bra up, sliding my cock under and between her breasts.

Tittyfucking was my favorite but this was a whole new ball game. Her tight sports bra squeezed her soft breast tight around my cock as I began thrusting. I watched my cock head appear from her cleavage before disappearing with each thrust. She held her arms against her body causing her cleavage to be extra tight as she stared and smiled at me.

I wanted to cum like this but my eyes caught some movement as I noticed a guy running up the trail with his dog. He didn't see us yet but soon would.

"Shit. Let's go," I whispered as we scurried back into my car.

I put the car in drive and pulled away as Jenny immediately started giving me roadhead again. She told me where she lived and I drove near her street before parking down the road. On the side of the road she kept blowing me but I couldn't seem to cum this morning.

"Come on you sissy bitch. Cum in my mouth. I'm not leaving until you do. Grab my ponytail," she ordered as she took my cock head into her mouth.

She began sucking on it with extreme suction causing more of my cock to slide in her. I pulled her up by her ponytail before releasing and allowing her suction to slide her back down. Over and over we did this until my engorged cock head felt like it was going to explode from the pressure.

Jenny cradled my balls in her hand which finally put me over the edge. I warned her as she stroked my shaft while sucking my tip, ready to receive the prize she worked so hard for. I felt the tip of her tongue tickle the slit of my cock head as I released. I didn't bother to try for a non ejaculatory orgasm, I had to cum.

Jenny moaned louder than ever as the first wave filled her mouth. Uncontrollably she moaned as loud as she could as I unloaded inside her. My cock flexed hard with each pulse as my PC muscles were now stronger than ever.

Finally I was spent as her moans finally softened. She pulled off my cock and stared at me with a mouth full of cum. She happily opened to show me the large load I gave her, proud of her work. All I saw was a white mass of my fluid which started to dribble from the side of her mouth.