The Robertson's Sissy Ch. 01

*Being a long time reader I finally decided to try writing my first story. I plan to make this a longer series so this part is a build up of what is to come.*

Summer was finally here and school was out! For me it wasn't just out for the summer, but it was out for good! Through all the years of working my way through the public education system I finally graduated.

Though it was an exciting time in my life it also came with some tough moments. First, my girlfriend for the past year and a half of high school decided it was time to split up. It was going to happen eventually as she was going to be leaving for college at the end of the summer. Though I completely understood, It still stung quite a bit as we really did get along with each other.

This brings up the second downside of the summer, everyone would be leaving soon for college while I was stuck around town. I lived in a very nice suburb where many upper class and wealthy people lived. They would always send their kids off to the biggest and best schools, while those who didn't have the luxury of a ton of money stuck around and worked. Unfortunately for me, I was one to be left behind. I decided to stay home and work until I decided what I wanted to do with my life.

Despite the downside of being newly single, I decided I was going to enjoy the most of this summer. I was almost 19 years old, good looking and got along with almost everyone I met so I was ready for some fun.

The first two weeks flew by as it was an endless barrage of graduation parties. The long nights of music, friends and drinking games quickly took their toll on my wallet so I decided to slow it down and put some hours in at my local job.

For the past year I worked at a local deli. It wasn't much but it was easy work and put a few bucks in my pocket. We were never particularly busy, so between making sandwiches and running the register I would hang out and chat with everyone. All my coworkers were friends of mine from school so we always had some fun when we found a little downtime.

One evening, I was hanging out at the register when my friend Dave came out from the back. Thinking we had the store to ourselves we began slacking and talking about some of the parties we went to during the previous nights.

Dave struck up the topic when he abruptly asked, "Hey Matt, what did you think of Vicky's party the other night?"

I didn't have to think hard about this one and replied, "It was a great time, definitely one of the better parties this year."

He sort of just stood there silently staring at me with a big ass grin on his face. He was obviously up to something.

So I asked him, "Why should it have been bad or something?"

He replied, "No no no, it really was a fun party." But quickly added, "Maybe I should have asked how was your time with Jenna after Vicky's party?"

He kept looking at me with that big ass grin as my face turned red. I should have known in such a small town any rumor or gossip would make its way around in no time.

Jenna was a girl from our graduating class that all the guys would drool over. The 18 year old was tall, blonde and had a body that put most women to shame. Jenna and I would always flirt with each other but because I was already dating someone it never went past that.

Now since I was single I didn't hesitate to offer her a ride home from Vicky's party. She also didn't hesitate and quickly went down on me in the car. Not going to lie, it was the best blowjob I had ever received at this point in my life.

But Dave had no business knowing all the fine details so I replied, "She was definitely more fun than the party but we'll leave it at that!"

"Oh come on!" Dave exclaimed, "She is smoking hot! You need to keep getting with her and lock that up for the summer."

I thought about it for a moment and replied, "Smoking hot is an understatement but she's leaving soon for college. I rather keep my options open for someone more my style."

"Bullshit!" Dave said with a puzzled look on his face. "If she's not your type than what kind of girl is?"

I thought back to my ex-girlfriend and explained to him, "Man, I can't say no to a curvy brunette especially if her skin is tan. I have always been weak for an italian or latina girl with an amazing body."

Dave agreed but the expression on his face quickly changed and he turned to walk to the back. I knew right away that we weren't alone in the store and that someone was most likely standing right behind me at the counter. Before I could look I heard a man's voice chime in.

"Sounds like Matt and I have the same taste in women."

I quickly turned to see Chuck Robertson, one of our regular customers putting a red bull and some chips on the counter. I was relieved that it was him and not some stuck up rich woman because he was definitely cool with our conversation. Him and his wife would always come into the shop for things and we would always have small talk.

He's not joking about his taste in women though. His wife Lela Robertson is the definition of a cougar and in my book is a perfect 10. She's a bit shorter than me, curly brunette hair that flows past her shoulders and large perky breasts that stand out against her small frame. I don't know what her nationality was, maybe columbian, I don't know.

What I do know is that her best asset was her ass. My god it was perfection. Everytime she took a step her wide hips would cause her perfect ass to sway back and forth, something that stopped every man in their tracks. Worst part was that she knew she was hot and would always wear something tight or low cut. She was always acting flirty, most likely enjoying the effect she had on every man she encountered.

Though I was glad it was Chuck that overheard the conversation, I still nervously rang him up and got him on his way. The rest of the evening was extremely slow and closing time seemed to take forever to come. During our final clean up the phone rang. I am always hesitant to answer the phone so close to closing time, but if my boss was calling and I didn't answer then I would be out of a job.

So I answered the phone and heard Mr. Chuck Robertson on the other end, "Hey Matt! Glad I caught you before you closed. I completely forgot to grab a gallon of milk while I was there and the Mrs. will have my ass for it. Anyways, can either of you deliver it on your way home? I'll make sure to take care of you."

We normally run deliveries for bigger orders but their house was on the way home so I answered, "Sure thing, we'll stop by once we close up."

After hanging up, I quickly asked Dave if he wanted to drop it off. I guess I was still a little embarrassed from Mr. Robertson over hearing us before.

"Hell no!" Dave replied. "Rich people never tip well, your on your own with that one!"

Dave was right. Seems like all the wealthy folks in town always tip like shit. "Whatever, it's on my way home," I thought to myself.

"Hey Dave, finish locking up. I'm going to cut out early and drop this milk off," I yelled as I walked to the door.

I was finally out of work on a day I thought would never end. I got in my car and headed over to the wealthy area of town where the Robertson's lived. I don't know what they did for a living but damn they must have some money. Their street is mansion after mansion, each one bigger than the next, almost as if they were competing with each other. I finally pulled up to their house and was amazed at what I saw. Massive stone house, outdoor pool as well as an indoor pool with retractable roof and a massive garage for their expensive cars. As I walked to the door I couldn't stop noticing how perfectly manicured all their landscaping was. I was so distracted that I didn't notice the door opening as I approached it.

The door opened and their stood Mrs. Lela Robertson. I thought she was going to have to scrape my jaw off the doorstep. I couldn't believe my eyes. She wore nothing but a short white bathrobe and still wore her make up to perfection. Her skin looked so tan and smooth as it glistened in what little sun was left.

She greeted me, "Oh my god, thank you so much for coming by! Chuck forgets everything I ask him to get. Come inside and we'll get you taken care of."

I could barely talk but quickly followed her in and back to the kitchen. The whole time I couldn't stop staring at her legs and how perfect and smooth they were. I noticed Mr. Robertson sitting at the table reading the paper and joined him.

Though I stopped and greeted him my eyes never left his wife as she opened the refrigerator to put the milk away. She bent over to adjust some items at the bottom causing her robe to slide up, giving me a perfect view of the pink lace thong she wore underneath.

My gaze was quickly interrupted by Chuck, "Let me get my wallet and get you taken care of.''

"Take your time," I said as my eyes were drawn back to his wife.

She came over and joined us at the table but while sitting down her robe began to open giving me a glimpse of the ample breasts she was hiding underneath. All wrapped up in a pretty pink lace bra to match her panties. The bra mashed her firm breasts together and her cleavage was starting to get me hard. She talked to me about finishing school but I couldn't focus on anything other than her chest.

Finally Chuck passed over a 20$ bill, "Here you go kid, the rest is yours. We really appreciate you coming by."

I snapped out of my trance like gaze and thanked them both before attempting to get up from the table without my massive bulge showing. Mrs. Robertson followed me to the door and sent me on my way. She gave me one more flirty smile as she closed the door, almost as if she knew exactly what she did to me.

The next day work was going by much faster as we had many more customers in between the rush hours. As I was restocking the shelves I could see a man approaching from my side.

Before I looked up he greeted me, "Hey Matt, I wanted to thank you again for coming by last night. I know Lela really appreciated it."

"No problem," I responded, "You guys were on my way home anyways."

As I responded, he kind of looked around nervously before saying, "Can I ask you something personal?"

"Sure thing Chuck, what's on your mind?"

He started, "Well it's about my wife, I saw the way you were looking at her last night, plus after hearing your and Dave's conversation yesterday. . . "

"Shit!" I thought to myself, "This is going to be so damn embarrassing. He caught me drooling over his wife."

But before I could finish my thought he continued, "Lela and I have a special type of marriage. We enjoy a bit of adventure in the bedroom. I could tell what you thought about her last night and after you left she expressed interest in maybe you joining us one evening, maybe even tonight?"

I stood there in shock. Honestly, I couldn't believe what the hell I was hearing. I looked around to see if we were alone before quietly asking, "You want me to fuck your wife?"

Calmly he stated, "Yes, well I want you to fuck my wife with me. We have explored the thought of a threesome with another man and she thought you were cute and really wanted me to ask you."

My head was racing with a million thoughts. Is this really happening? I've never done anything like this before, especially with another guy in the room. Would it be weird? Finally I snapped out of it and realized I get to bang Lela Robertson the hottest cougar in town. Hell, I am always up to try something once.

Finally I gave my answer, "Sure! As long as your ok with this? Honestly, I've never done anything like this before, so I am sorry if I come off nervous."

He gave a small laugh, "Don't be nervous kid, this is what we do. I get it though, not what someone normally comes and asks you in the middle of a deli. I am perfectly fine with it and I know the Mrs. will be extremely happy to hear. How is 9 pm tonight?"

I almost couldn't answer quick enough, "I'll be there!"

He calmly turned to leave as I was left pondering what the hell just happened. The rest of the day went by slower than it could have possibly gone. I kept watching the clock until finally the day was over and I ran out the door. I had just enough time to run home and shower, change into clean clothes and then head over to the Robertson's. The whole ride over I kept thinking this couldn't be real and the closer I got the more nervous I became.

Finally, I pulled up their driveway and parked my car. "Here goes nothing," I said to myself, "No turning back now."

I rang the doorbell and waited nervously for what felt like an eternity before the door opened and I was greeted by Chuck. He wore a simple pair of sweatpants and a t-shirt as if he had just woken up.

"Hey Matt!" He greeted, "Come inside, make yourself at home. Do you want anything to eat or drink?"

My stomach was so twisted with nerves that food was out of the question but I did take him up on something to drink. I took a seat on the couch in their living room as Chuck quickly returned with a glass for me.

"The Mrs. is in the bedroom getting ready. She'll join us shortly. I know from over hearing your conversations at the store that you guys like to drink. This here is something you might not be used to from your local parties but it's only the best... and damn expensive too," he said with a laugh.

"Thanks," I replied, "What is it?" I took my first sip and it burned more than any other drink I've had before. Being the young inexperienced drinker I am, I almost choked.

"Just a little scotch," he answered, "It's good and gets the job done. It also does a great job settling one's nerves as I can tell your a bit nervous about the offer I gave you earlier."

"Nervous is more of an understatement," I said jokingly. I guess it was very obvious that I was nervous as hell.

He chimed in as an attempt to make me relax, "Hey, don't worry about it. I want this to happen as changing things up in the bedroom always spices up a marriage. I also know that the person who wants it more than us is my wife. She wouldn't stop going on about it last night and I know she is beyond excited you decided to come join us."

Our conversation was interrupted by the noise of someone in the hallway. I turned to see Lela Robertson turn the corner in all her glory. Wearing the same short white bathrobe as the night before, the biggest smile of perfectly white teeth on her face.

"Well there's my two handsome men for this evening," She said before sipping a glass of red wine. She slowly yet seductively walked to the love seat where Chuck was seated and greeted him with a kiss before joining me on the couch.

"How's my young stud doing this evening? You have no idea how happy you made me by coming tonight," She said as she leaned in, closing the distance between us.

Her beauty left me speechless, though I managed to get out how amazing I thought she looked. She responded with a smile before creeping her hand onto my lap. She was so damn hot and the way she stared at me immediately caused my dick to stiffen. She rubbed my thigh, inching her way to the bulge that already began forming.

Her hand worked its magic as she shared how turned on she was knowing that I was checking her out the previous night. Her hand finally reached its destination and gripped my cock, giving it a tight yet gentle squeeze.

"Oh my!" She gasped, "Looks like someone is as ready as I am!" Lela excitedly announced.

"Here sweetie, hold my drink as I get myself more comfortable," She asked Chuck.

Chuck grabbed her glass and sat down next to me on the couch. Free to now move Lela sat up resting her hands on my shoulders while swinging her leg over me and straddling my lap.

There she was, the woman of my dreams straddling me while I sat frozen, absolutely mesmerized by her beauty. She looked down at me and smiled as I got lost in her beautiful brown eyes. Grabbing both sides of my face she leaned in giving me a kiss that I never wanted to end. Her lips were so soft and tasted even better than I could have imagined. Our kiss continued as she parted her lips to introduce her warm wet tongue. I eagerly greeted it with mine as we locked into a series of long deep kisses.

My heart began to race as my hands slowly slid down her hips until I was able to grab a handful of her perfect ass. The same ass that drove me crazy whenever she came to the store. I gave it a tight squeeze which elicited a soft moan in response. As I continued to massage the world's greatest ass she began to slowly grind her hips, rubbing her panty clad pussy on my already throbbing cock.

My nerves finally settled as I was being taken over from within by naked lust. Our kissing and grinding continued until finally our lips unlocked and parted. I took a moment to look over at Chuck who was just sitting there sipping his scotch and enjoying the show.

Lela turned my head and focus back to her, "Chuck likes to watch the start of the show. Right now it's just you and I," she said as she undid the white bathrobe which I had learned to love seeing her in.

It fell open revealing the same pink lace bra and panties she wore the night before. She smiled before stating, "I could tell how much you loved seeing me in this last night that I couldn't resist wearing it for you tonight."

I couldn't do anything but nod in agreement as she continued her grinding on my cock. I was mesmerized by her dark soft skin, thin waist and flat stomach as well as her breasts that were exploding out the top of her bra.

My hands explored the endless curves of her body as I helped her remove the robe. The grinding intensified as she leaned forward, kissing my neck, working her way up to my ear where she whispered everything I wanted to hear.

"God you are making me so wet Matt. The thought of you and my husband having your way with me makes me feel so dirty. I've never wanted something so bad."

Her grinding on my cock suddenly stopped as she slid down between my legs. Sitting on her knees, guiding her hands down my body until she reached my belt. She wasted no time with the buckle and started tugging at the zipper until it gave way. I lifted my hips in excitement as she gripped the waistband of both my jeans and boxer briefs and pulled, sliding them down in one shot.

As my briefs slid past my cock it sprung forward in freedom and excitement. Her soft hands grabbed me and began skillfully stroking.

I'm not a huge guy down there, about 6 inches cut with average girth. By the look on Lela's face she wasn't disappointed with what I had to offer.

Lela's glossy pink lips started giving small kisses to the head of my cock. Her lips were so soft I thought I was going to explode right there. The kisses turned to small licks until her brown eyes gazed at me one last time before plunging down on my cock, taking me into her mouth.

I was in heaven, her mouth was so warm, so wet, so perfect. She sucked on just the head while working the rest of my shaft with her hand. My legs tingled as she devoured every inch of me, her free hand gently massaging my balls.

She never stopped stroking me as she moved down and began gently nibbling my scrotum. The soft bites continued until she took my left testicle in her mouth, gently rolling her tongue around it. It was clear she was a pro and the sensations I felt shutter through me, I had never felt before.

I almost forgot about Chuck who reassured his presence by whispering to his wife, "mmmm that's right, suck his balls sweetie."

The ecstasy I felt suddenly ended as she removed her mouth from my balls. I wanted to plead for her to continue until I saw her make her next move.

She reached back with one hand and began unhooking her bra while holding it in place with the other. Once unhooked, she slowly slid it down, seductively revealing her perfect firm tits. They were natural yet defied gravity, no tan lines and were the perfect size. They weren't overly enormous yet looked massive against her small frame. The light brown nipples stared at me and screamed to be sucked, but Lela had other plans.