The Robertson's Sissy Ch. 02

A few days have passed since I spent the night at the Robertson's house and I can't seem to shake Lela out of my mind. Everything about this woman gets me going and I'm finding it difficult to focus on much of my work. I'm even getting distracted in my personal life.

Last night I went out to a party with some friends. It was a great time especially when Jenna showed up. For those of you who forgot, Jenna is the blonde bombshell who gave me some after party road head less than a week ago.

As usual Jenna was looking damn fine and after a few drinks and some flirting she was back in my car. This time I wanted a little more than road head, so we pulled over down a quiet back road, parked and hopped in the back. Before I knew it she was riding me like there was no tomorrow. Any other guy in town would have been elated, but after my night with Lela Robertson, it just wasn't exciting enough.

I decided to push the envelope a bit, as she rode me like a horse jockey my hands explored her pale round ass. I slowly slid one hand little by little into her crack, reaching her puckered little asshole, when she abruptly stopped.

"Ummmm what are you doing?" she asked with a puzzled look.

I replied, "Just trying something a bit different. Relax sweetheart, if you don't like it we can stop."

The puzzled look on her face remained as she continued rolling her hips on my cock. Again, I ran my finger over her puckered little hole and softly massaged it with the pad of my middle finger. Surprisingly, she softly moaned in my ear with approval. I pushed my luck, rubbing harder and increasing the pressure, causing her moans to intensify.

My heart raced as I grew more excited, thinking I was finally about to have anal sex for the first time. A deed I wanted to do desperately with my ex, but would never happen. Giving the intensity of her moans I figured I was in the clear, giving the final push, popping the tip of my finger past her sphincter into her ass.

"Oh fuck no!" she yelped as she hit me in the chest, "No fucking way is that happening!"

"Relax, relax, relax!" I assured her, "I'm sorry, I thought it was ok. We don't have to do anything you don't want to do."

She stared at me still pissed but cautiously continued to ride my cock. Not pushing my luck any further I settled for the dick riding I was already receiving. Though I tried enjoying, I couldn't stop thinking about Lela Robertson riding my cock. The image alone brought my balls to a boil as my cock began to pulse and jerk.

"I'm cumming Jenna, pull out!" I warned as I was about to blow my load.

She lifted herself off and stroked me as I spurted wad after wad of cum. A very small amount landed on her thigh but most ended up back on my cock and lap.

"Wow, that was a lot more than last time," she said in shock.

I laughed and waited so see if she would suck and lick me clean. I heard Lela's voice in my head as she told me a few nights earlier, "Remember rule #1, good girls always clean up their mess."

Instead Jenna laughed back as she got dressed, leaving me with a mess of cum all over me.

The next day at work was a particularly slow day. As usual, Dave would come up front and we would bullshit about life, parties and girls. He brought up Jenna and I reluctantly told him about my failed anal sex adventure.

"Dude, that shit is mad funny. Hey, at least you had the balls to try," he laughed.

I guess it was kind of funny, so I laughed back, "I just wanna try anal once, can't blame me for trying."

The bell rang as a customer entered, forcing Dave to return to his post in the back. It was just a kid wanting some candy. He put a bag of skittles on the counter as I noticed another person off to me side. I looked up to greet the customer and was shocked to see it was none other than Mrs. Lela Robertson. Wearing short white booty shorts and a low cut baby blue shirt, she looked fine as hell.

"Excuse me Matt, when you're done with this young boy can you help me get a case of water?" She asked with a big smile on her face.

"Absolutely Mrs. Robertson," I answered, rushing to get the kid out so I could assist the beautiful Lela.

I jumped around the counter and down the aisle where I found Lela sitting on top of the cases. I wanted to fuck her right there, not caring who would see.

She jumped to her feet in a flirting manner and pointed, "I think this one will do."

I bent over grabbing the case and suddenly felt her pinch my ass. My body jolted up as she leaned into my ear.

She whispered, "How's my sexy little stud doing? I've missed you."

My heart fluttered as I began to nervously sweat. This woman had me melting and she knew it. I struggled to answer, "I've been doing really well, though I'd love to see you again."

Her hand left my ass as she whispered again, "Really, your doing well?" She gave me a kiss on the cheek before finishing, "That's not what it sounded like from the story you told your friend there."

She turned away, walking to the front counter, leaving me to watch as her round ass jiggled with every step. Like a puppy dog I followed her to the register.

"Would you be a dear and help carry this to my car," Lela asked with a wink.

"Absolutely," I eagerly responded, knowing she was up to something.

I followed her out, placing the case of water in her trunk when she chimed in, "Anal sex isn't for everyone. It takes a special and experienced partner as it needs to be done right." She then leaned in and whispered, "It always helps if your partner is a dirty little whore who's begging for it too."

The thought of anal sex with this incredible cougar was instantly arrousing.

"And where does a magnificent woman like you fall?" I asked.

Lela smiled as she played with her hair, "Well, I am very special, experienced and I know how to do it right. I can also be a dirty little whore when I want. . . but. . . I'm also not begging for it. Maybe if your a good boy and prove how badly you want it, I'll beg you for it all night."

I should have known that nothing came easy with this woman but I didn't hesitate to jump at the opportunity, "Name it! What do I have to do?"

She took my phone from my hand and started typing.

"Wait for me to text you. I need some time to think about it," She handed back my phone and blew me a kiss before sitting in her car.

Before closing the door she looked back and said, "I am going to have so much fun with you. Your going to beg me for more."

She had a seductive yet sinister smirk on her face knowing she had me ready to do anything she demanded.

For the next two days I kept checking my phone waiting for her text. I even blew off going to Jenna's house for some alone time because I was afraid of not being available in case Lela messaged. Finally, my phone rang and I knew exactly who it was.

The message read, "Hey stud, I've been thinking of you a lot and I really want to see you. I also thought about our little talk and what you can do to prove you deserve it. What you have to do is simple. Be at our house tonight at 10PM and do EVERYTHING you are asked. I'm going out with the ladies but Chuck will be there. xoxo"

I smiled and thought to myself. I don't care what this woman asks of me, it's getting done! Little did I know, that by doing so, my life would change forever.

I rolled up the Robertson's driveway at 9:50 PM that evening. I couldn't tell if Lela was home as her car could have been parked in their massive garage. I parked and approached the door like I did almost a week earlier, though this time I was the least bit nervous and beyond excited. Chuck must have seen me pull up as he greeted me at the door.

"Hey Matt! I'm glad you had enough fun with us to come back. Please come inside," he greeted.

We went inside and made our way to the kitchen. Their house never ceases to amaze me. Massive kitchen with dining hall and just outside a large patio with outdoor pool. Just past the kitchen was a glass corridor which allowed access to their indoor pool and hot tub.

"Lela is still out with the girls," Chuck stated as he grabbed two glasses and a bottle of what looked like scotch.

"She's going to have a head start on us so we need to catch up!" Chuck joked as he held up the bottle.

I followed him down the glass corridor to the indoor pool area. I had never seen anything like it before. Large pool in the middle with a decent sized hot tub connected to the side. Everything was made from stone, just like the outside of the house.

Chuck offered, "Let's wait her out in the hot tub. There is an extra pair of trunks in the closet of the bathroom there."

I made my way to the bathroom and found the trunks he was talking about. Luckily they were a perfect fit. I couldn't stop thinking how awesome of a life this guy had. He had all the money in the world, a smoking hot and kinky wife as well as an amazing house.

I made my way back to find Chuck already in the hot tub filling up our glasses. I took a seat across from him as he offered me a drink. There we sat drinking fairly heavily and having small talk. His phone went off and he smirked at the message.

"Oh boy, I almost forgot. Lela wanted you to take something. She's almost home," He claimed as he left the hot tub.

He made his way to the mini bar and came back holding something small.

"Here take this," he said handing me a little blue pill before climbing back into to hot tub.

"Ummmm what's this?" I asked making sure it wasn't anything illicit and crazy.

Chuck explained, "It's Viagra. Lela told me she wanted you going all night so she asked that you take one. I'm sure it's weird being asked at your age but it's completely normal when your about to have a crazy night like we are."

I was hesitant, but I remembered Lela telling me to do everything I was told. This night was going to be more crazy than I originally thought, but it shouldn't have been a surprise. I should have known by the sexy yet devious look Lela gave me the other day. Reluctantly, I popped the pill and continued downing scotch with Chuck.

It wasn't long later I realized all the scotch Chuck and I were drinking was kicking my ass. Sitting in the hot tub most likely wasn't helping either. I wanted to get up but the Viagra had me hard as a rock. I figured I'd stay put instead of getting up with a massive boner. I leaned my head back for a moment and closed my eyes.

I dozed off but quickly woke to a hand being placed on my shoulder. My eyes opened to find the woman I was waiting for staring down at me. Glass of wine in hand she stood sporting a skimpy yellow bikini which looked amazing against her tan skin. The fabric barely covered her breasts and pubic area, showing tiny bulges in her bottom which indicated how swollen her pussy lips were. The humidity from the indoor pool caused her to slightly sweat, making her glow in the dimly lit area. I would say the look of her got me hard right then but I was still raging from the Viagra I took earlier.

Her soft voice broke the silence, "Mind if I join my sexy little stud?"

I couldn't answer, still waking from my drunken fog. She knew what I wanted and proceeded to sit between my legs, reaching back and feeling the massive hard on I was sporting.

"Good boy, I see you've been listening so far. We still have a long way to go though," She said as she laid back, rubbing my cock with her ass. I was pretty much receiving a lap dance as she sipped her wine while talking about her day with her husband.

Leaning back against me she rested her head on my shoulder. I held her thin waist tightly as she continued her teasing dance. Tilting her head back she kissed me, squeezing her arms together, making sure my only site was of her wet breasts being mashed together.

Lela turned around, straddling my lap like she did the previous time. She kissed me before grabbing my scotch, holding it to my lips.

"I can't drink anymore," I slurred as I turned my head away.

Reaching between my legs she stroked my strained cock while stating "Oh no no no, remember you need to do everything I want or else I won't be begging for it later. Drink up my love."

At this point I wanted it so bad, grabbing the glass and downing whatever was left. She took my glass, placing it down before caressing my face and kissing me. Our kissing was much more aggressive than last time. Our tongues twisted and twirled as we locked lips.

All I could do was hold this woman close and go for the ride she was giving. Our kisses would break only when she wanted to kiss my neck, bite my ear or whisper dirty things, arousing me more than I thought possible.

"I can't wait for you to fuck me in the ass tonight. I've been thinking about it all day," she whispered.

Reaching back she pulled the string on her bikini top causing it to release her large wet tits in my face. I strongly squeezed them together causing her to sigh and moan loudly.

Lela panted as she pulled my face toward her silky smooth cleavage, "Remember to do everything your told, I own you tonight."

I took each erect brown nipple into my mouth and sucked. Her aggressive nature before set the tone as I roughly teased her. Her moans turned to screams as I pinched and gently bit her nipples, causing them to become even harder.

Lela's hands were now down my swim trunks, feverishly stroking my pulsing cock. The aggressive play slowed as all the booze got to me, causing everything to spin. Lela noticed I was struggling.

"Let's slow it down sweetie," she said as she slowly kissed my neck, "We have all night to get crazy".

Though she said to slow down her death grip on my cock remained and I was desperate to cum. Reaching down she slid both our bottoms off before climbing back up. Guiding my aching cock to the entrance of her pussy, she slowly lowered, impaling herself with a loud gasp. The water was warm but Lela's pussy was burning with lust. The riding of my cock never came though, she just sat there, her slightest movements causing my cock to scream for release.

Lela leaned into my ear and whispered, "Chuck and I want to have so much fun with you. Are you ready to prove your willing to give into my every demand?"

All I could do at this point was nod. Her face lit up with an evil yet slutty smile as she turned to Chuck, "Hey Daddy, she's ready for you."

I thought to myself, "Did Lela just refer to me as a girl?"

Before I could question it I was locked into another deep kiss as she slowly rode me. I was aware of movement to my right and figured it was Chuck coming to watch. As our kiss broke I was shocked to see Chuck, no shorts on and his massive 8 inch cock staring me in the face. Lela grabbed and stroked it while whispering in my ear.

"I want to watch you suck Chuck's cock. Nothing will turn me on more and once your done you can have my filthy ass."

Whether it was the booze, Viagra or the fact I was smitten by this woman, she had complete control. Lela knew I was going to do whatever she asked. This was beyond the limit and out of the question but I didn't know how to respond. I opened my mouth to protest but no words came out.

She took my open mouth as an invitation as she pushed my head down, guiding Chuck's cock in my mouth. I had to open as wide as I could to fit his massive head inside, pausing a moment to feel it with my tongue. His flesh was soft like velvet and throbbed with the beat of his pulse. But my oral exploration didn't last long as Lela kept pushing me down on it.

She instructed, "You can take more sweetie, now use your hand to stroke the rest of him. Since this is your first time, I'll take care of his balls for you."

She reached up and massaged Chuck's massive balls as I began following her instructions, stroking any part of him that didn't fit in my mouth. It felt different but wasn't bad.

"That's a good little slut, now make Daddy proud," Chuck grunted at me.

In all honesty, I started enjoying it, knowing how much it turned Lela on. I wanted to please her, so I decided to go all out sucking Chuck off. My hand would slide up and down his veiny shaft faster and harder all while flicking my tongue around the tip of his dick. Lela was taken by surprise as I let go of any reason, giving into my desire to please.

"That's a good girl. Suck Daddy's dick like you mean it." She encouraged.

The harder I blew him the harder Lela rode my stiff cock. Her soft wet tits pressed against my chest as she cupped her husband's balls.

I knew I was doing a good job when I pulled his cock out and noticed a drop of precum forming at the tip. I didn't have to be told and immediately licked it up. It didn't taste bad, well it didn't taste much like anything, it was kind of sweet.

I hungrily stuffed his cock back into my mouth and tried going deeper and deeper. I began enjoying it so much that I didn't realize I was moaning until Lela joked to Chuck.

"Wow, listen to this little whore moan!" She exclaimed.

Chuck quickly added, "Glad she likes it. This little bitch is going to be getting a lot more of it."

My eagerness turned Lela on so much that she decided to join me. Leaning in she started sucking Chuck's balls while I worked him with my mouth. The two of us were too much for him as he reached the point of no return.

"Here it comes my love, enjoy every drop," Lela whispered as she began stroking his cock in my face. I didn't know what else to do but sit there and watch Lela stroke him.

"Cum on her face Daddy, Feed your new little whore," she finally demanded before it happened.

Chuck's cock jerked forward with the first spasm of his orgasm and with it came a large wad of thick white cum, landing square on my closed mouth. I flinched as another rope of cum hit me in the chin, another on my neck and finally the last bits on my chest. It was so warm and the musky scent overloaded my senses.

"Wow, I'm so proud of my little cum slut! Lela laughed. "Normally I would remind you that good girls clean up their mess, but I'm so impressed that I'll clean this one for you."

She quickly sucked Chuck's dick clean and drew her attention to me. Licking the thick load covering my mouth and chin before kissing and licking my neck. We kissed with our cum coated lips as I got my first hint of how Chuck tasted.

Lela broke our kiss before praising me, "You earned your prize tonight, my ass is yours but remember I still own you." She licked the last bit of cum off my neck before finishing, "Before we shower make sure you thank Daddy for giving you such a big hot load."

"Thank you so much Daddy for giving me such a big load" I helplessly said as I looked up at him.

He wasn't able to respond fast enough before Lela grabbed me, dragging me to the shower of the pool around. Here we made out while cleaning off all the cum we missed. We dried up and headed down to the bedroom where my anal dream would come true. Lela pushed me on the bed and told me to relax while she got ready. I closed my eyes and thanks to all the booze drifted off to sleep.

I woke to Lela on top of me kissing my neck and chest. She let me sleep a bit, wanting me a bit sober as she would be on the receiving end of my built up lust. My cock stood straight up, still hard as a rock but now my balls were starting to get sore. They needed to be released before blue balls set in.

"Get up sweetie it's time," she told me, "While you were sleeping I toyed myself a bit, hopefully making this easier."

She laid down missionary and propped a pillow under her lower back, raising her ass up off the bed. I spread her legs and laid on top of her, kissing her for a while.

"I don't do this often, I'm trusting you to be gentle and follow everything I tell you," she said breaking our kiss.

I assured her, "I would never want to hurt you, you're in charge."

I kissed her down her neck to her chest. Her breasts that I was so aggressive with earlier got gentle treatment this time around. I pushed my way down her stomach, listening to her soft gasps as I moved lower and lower.