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Snowbound With A Fun Cougar

"This happened many years ago..."

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I was working as a software technician and was often making service calls around the state to different offices. There was a customer that I usually serviced in Princeton, about an hour south of where I lived. The company did medical billing; there were eight employees, all women. Sheila, the woman who owned the company, was in her mid to late fifties, and she always wore loose clothing, as she was a bigger woman. She definitely had a BBW type of body and it was obvious that she had big tits. She was probably pretty when she was younger. I assumed she was married and she had pictures of her kids and grandkids in her office. I was in my late twenties at the time and I didn't really pay much attention to any of the women there, other than to speak to them about their software. Most of the women there were kind of frumpy and no-one gave off any kind of sexual vibe, which was fine with me. I could do my work and go.

All this changed one Friday in February, when I had to go there to do an upgrade to all the computers in the office. My dispatcher had me making two calls near our office and my last call of the day was to the office in Princeton. I was a little concerned because snow was predicted for that afternoon and with Friday traffic and snow, I was concerned about being able to get home safely. Fortunately, I always kept a bag with a change of clothes and some toiletries in my truck. I figured if worse came to worse, I'd find a cheap hotel and wait out the storm.

I got to my Princeton customer around two that afternoon, just as the snow started to fall. The predictions were eight to ten inches of snow and I wanted to get in and out of there as quickly as possible.

Since I needed to restart the server and all the computers, Sheila told her staff to go home early before the snow got bad. As everyone started to leave, Sheila went to her office and I went to work. I started on the server, which took a bit of time. By three pm I started on the office machines and about an hour later, I went into Sheila's office to perform the upgrade on her computer. She moved to a chair opposite her desk as I sat in her lush chair. I noticed the heat from her ass on the chair as I sat and it felt really nice. Sheila wasn't paying attention to me as she was reading a magazine while I worked.

After I installed the new software on her computer I had to reboot it. I asked her for her login password and she said, "I'll enter it."

As she leaned over me, I felt the warmth of her breasts as she pressed up against me and she smelled really nice. I watched as she typed and I could see her password was "Luvtolick". I smiled to myself as she went back to her magazine. As her computer came back up, Yahoo messenger popped up (this was years ago!) and I noticed her username was something along the lines of "OralQueenForOralKing". I didn't say anything and closed the messenger window. About ten minutes later, I told her I was finished and she asked me to turn off the computer as she wanted to get home.

When we went to the door the snow was coming down really hard. I asked if she knew a hotel nearby as I knew the roads would be terrible. She paused for a few seconds and said that if I wanted to, I could sleep at her house. Her kids were grown and out and she had guest rooms and it would be nice to have some company for a change.

I told her that I didn't want to be a burden and she said, "It's not a problem. You're always so helpful here, it's the least I can do."

She got in her Cadillac, and I followed her on the short drive to her house. She lived in a nice house, not huge, but it looked nice. I grabbed my bag and followed her inside the house. She showed me one of the guest rooms and told me to put my stuff away. She asked me if I liked wine, which I let her know I did, and then she asked me to open a bottle and if I wanted I could put on the TV in the living room. She wanted to change out of her work clothes and then she would make something for dinner for us.

As I went to the living room, I heard a shower running and I went downstairs. I opened a bottle of Malbec and poured two glasses and put on the weather channel. The predictions for the snow were getting worse, with more than a foot now predicted to fall. The local news proved my decision to be right as there was major traffic all over the state, especially in the area where I live.

A short while later, Sheila came downstairs, took the glass of wine and thanked me for taking her up on her offer. She said that since her divorce eleven years earlier she hated being alone during storms. For the first time, Sheila had a warmth about her that I never noticed before. Her face looked softer and she seemed relaxed. She had changed into what looked like silk pajamas, not lingerie, but silk pants and a silk blouse. The black fabric contrasted with her pale skin and blond hair. After another sip of wine, she went into the kitchen to make us some dinner.

Sheila was a great cook and whipped up a nice salad and chicken dinner for us. We talked a bit over dinner and finished off the bottle of Malbec. It turns out that since her divorce she'd devoted most of her time to her company and while she had dated a bit, she was just not looking for a relationship at this time in her life. She opened a second bottle of wine as I cleared the table and helped her with the dishes.

It might have been the wine talking, but I said to her I noticed a kind of suggestive username on her Yahoo Messenger. She quickly retorted, "I like to talk, and would enjoy finding a guy who does too." Trying to change the subject, she suggested we relax with a movie. I didn't want to push her, so I let it drop.

She asked if I had seen "The Secretary", which I hadn't. She let me know that it was one of her favorite movies and she popped the DVD into the player. I settled onto the couch and Sheila set next to me. I was a little buzzed from the wine as the movie came on. If you've never seen the movie, you should watch it; it's a very hot story about a woman falling into a BDSM relationship. I hadn't seen the movie and was surprised at the content. Every now and then I would glance over at Sheila and would notice her crossing or uncrossing her legs. Once I saw her rubbing her nipple over her silky blouse.

I was a bit turned on by the movie and we were both pretty tipsy from the wine. Near the end of the movie there's a scene where Maggie Gyllenhaal has her arms bound on a pole; it's really hot. Sheila had her hand in her lap and I could see her rubbing along the inside of her thigh.

As the movie ended, she asked what I thought. I said it was really good. She then looked me in the eyes and asked, "Did it turn you on?"

I swallowed hard and said, "Yes, it did! I think that it turned you on as well."

She blushed a bit as I leaned into her and her lips met mine. We kissed, very gently at first, then I felt her tongue enter my mouth. Soon our tongues were dancing together as we leaned into each other. Her tits were pressing against my chest and my cock was getting very hard! I kissed her neck and earlobes and whispered to her, asking if she liked being used like the woman in the movie.

She moaned, "Yesss, I do."

As I kissed and nibbled on her neck, she leaned over more so that her ass was off of the couch. I gave her ass a spank, which elicited another moan from her lips. I smacked her ass several more times, and each time she moaned with pleasure.

I suggested that we should go upstairs to her bedroom and she looked into my eyes and said, "Yes, Sir!"

I followed her up the stairs, admiring her shapely ass in her silk pajama bottoms. It was exciting that we had quickly settled into our roles as Dom and sub. When we approached her bedroom she gestured for me to go in first. "After you, Sir," she said as she looked at the ground.

I entered her bedroom and pointed to the king-size bed, telling her, "You're a bad girl and you need to be punished! Get on all fours so I can give you a proper spanking!"

Sheila slowly walked to the bed, got up on all fours and said, "Please punish me, Sir."

I moved next to her and gave her ass a hard smack. 

"Thank you, Sir!" she moaned.

"Tell me about your Yahoo username! Is it really about talking?" Smack!

"No, Sir," she said. "I love oral sex, Sir. Sucking cock is my one true love!" Smack! "And having my pussy eaten, is my favorite way for me to cum." Smack, smack!

"So you lied! You're going to make up for it!" I said as I yanked her silky bottoms down, exposing her pale, fat ass. Slap! Slap! It was such a turn on seeing my hand slapping her ass and watching her fat jiggle with each spank.

"I'm so sorry I lied to you, Sir." She was panting, practically crying, but I could see she was also really turned on.

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"Strip!" I barked at her.

She rose from the bed, and let her bottoms fall to the floor. She then unbuttoned her blouse, letting her big tits flop out. Her tits were really big, about the size of her head, and she had pink nipples that were the size of pencil erasers poking out from each one. I could now see her body. She wasn't really flabby, but had a bit of a belly. Her pussy was covered in light brown hair that was a little unkempt, but I could see her pussy lips poking through her pubes.

"Now undress me!" I ordered her. She unbuttoned and removed my shirt, dropping it on top of her clothes, then dropped to her knees and began undoing my belt. She then unbuttoned my jeans and started to pull the zipper down. I told her to use her teeth to unzip my pants, which she did, very slowly. She then tugged my jeans down, revealing my tented boxers. My hard-on was poking obscenely through the thin cotton fabric. "Use your teeth to remove my boxer, slut!" 

Being obedient, Sheila skillfully pulled my boxers down to my ankles. I stepped out of them, standing in front of her with my throbbing hard cock inches from her face.

I looked into Sheila's eyes and said, "Tell me what you want."

Sheila looked up at me, "I want to suck your cock, Sir."

I grabbed my cock by the base and slapped her cheek with it. I then placed the head at her lips and commanded her to suck me. Sheila wasn't lying when she said that she loved to suck cock. Holy crap, she gave the best head that I had ever gotten up till then. She expertly sucked me into her mouth, using her tongue and lips to caress and pleasure my cock. She got my cock coated with saliva and then she began bobbing up and down on my cock, taking me into her throat with each thrust, never gagging. I grabbed her hair, pulling her head all the way into my groin and holding my cock deep in her throat, enjoying the sensations.

I took my cock out of her mouth and told her to lick my balls. She skillfully licked and sucked on my balls for several minutes. "Look at me, slut!" I ordered.

Sheila looked up at me, and I spit right in her mouth! "Thank you, Sir," she replied.

I moved the bed and lay down, ordering her to "suck my cock and make me cum!" Sheila got between my legs and dutifully began to lick and suck my cock. I was leaking pre-cum and she would moan with enjoyment with each bit that leaked from my cockhead. I put my fingers in her hair and guided the pace, increasing the speed of her bobbing on my cock. I began bucking my hips as I felt my orgasm approaching. With a grunt, I began unloading a huge amount of cum into her greedy cocksucking mouth. Being a good slut, she swallowed every drop and kept gently sucking as my cock began to get soft.

After I rested up from filling Sheila's mouth with cum, she asked me very meekly, "May I show you something, Sir?"

I nodded and she got off of the bed and went to her dresser. She took out an array of dildos, vibrators, cuffs, ropes, clamps, and more. She placed them all on the bed. I grabbed the leather cuffs, both wrist and ankle along with the leather-studded collar and told her to put them on.

While she was putting them on, I gathered up some ropes, nipple clamps, a leather whip, a butt plug and a glass dildo and a Hitachi-style vibrator and put them on the nightstand, pushing the other items onto the floor. Once she had the collar and the cuffs on, I had her lie on the bed as I used the ropes to affix her wrists and ankles to the bedpost, leaving her spread-eagled on the bed. She looked so sexy lying there; her nipples were hard and even through her pussy hair I could see her pussy was wet with excitement.

Grabbing the items I had on the nightstand, I placed them near her feet on the bed. I put the nipple clamps on her nipples and then I got between her legs. The scent of sex and her pussy was strong; it was that lightly musky smell, and it made me horny.

I decided to tease her a bit, taking the end of the whip and dragging it along the inside of her thighs, brushing over her pussy. Each time the leather came in contact with her pussy, she would writhe and moan. As she moved, I held the chain from the nipple clamps and gently tugged and pulled at them at the same time. I kept rubbing the end of the whip around her pussy, giving her pleasure and making the whip a bit wet.

She was really turned on and was gyrating her hips. I leaned over with my face just inches from her pussy and deeply inhaled her scent. It was intoxicating! I leaned forward a few inches and still holding on to the nipple clamp chain, I licked her inner thigh, my cheek brushing against her pussy lips. Using my fingers to spread her pussy hair apart, I thrust my tongue inside her, causing her to moan "fuck yesss" as I licked and pulled on the chain. Her pussy tasted amazing! A bit like the smell, but less pronounced, and she was VERY wet!

Letting go of the chain, I dove into her pussy, my hands holding her hips, as I licked and sucked alternating on her clit and her engorged pussy lips. Her moans were getting louder. Every now and then I would tug on the chain, pulling her nipples, which made her squeal. Increasing the pace of my tongue action, I concentrated on her clit as I slid two fingers inside her. She was moaning and bucking her hips.

Moments later she cried, "I'm cumming!" and flooded my face and mouth with her juices. I didn't stop and just kept fingering her and working her clit until she came two more times.

Sheila was out of breath and looking a bit drained, so I got up and took the glass dildo and slowly inserted it into her cunt until it was deep inside her. My cock was again rock hard and as I walked around the bed untying her for now.

I had her get on all fours and I spread her legs apart. I withdrew the glass dildo and using the juices from her pussy as lube, I began to push it into her ass.

"Stick it my ass, Sir! Please use me!"

This was music to my ears. I worked the dildo slowly in and out of her ass until I was able to get it all the way in with ease. Then I left it deep inside her ass as I placed the head of my cock against her pussy lips, letting it lube my cock. Holding on to her hips, I thrust forward, plunging my cock deep inside her cunt. I could feel the dildo in her ass against my cock as I let her get used to me filling her. For an older lady that had three kids, her pussy was TIGHT!

Grabbing a fistful of her hair, I began to fuck her, slowly at first, then I picked up the pace. As I started fucking her harder, I was also working the glass dildo in and out of her ass. Less than five minutes later she was screaming and cumming on my cock. I don't know how I held back, but I did. Still pulling her hair, I kept fucking her. I pulled the dildo out of her ass and then I pulled my cock out of her dripping wet cunt.

I lay next to her on the bed and told her to ride my cock. She smiled and jumped on me, inserting my cock into her cunt. She leaned forward and kissed me, our tongues passionately dancing as I held her hips and set the pace for her riding me. I broke off the kiss and she sat up and really started to ride me.

I reached up with one hand, grabbed the chain from the nipple clamps and began to tug on them. She looked so sexy riding my cock with the collar around her neck and her tits and belly bouncing as she rode me. She moaning a LOT and the more I pulled the chain, the more turned on she got. Soon she was cumming again, drenching my cock, balls and the bed. I kept thrusting into her as I pulled on the clamps.

"Make me cum, slut!" I ordered her.

"Fill me with your cum, Sir. I want your cum deep in my cunt! Please!" she shrieked.

Holding her hips and increasing the pace, she rode me hard. The room was filled with the scent of our sex and the sounds of wet bodies slapping together, panting and moans and groans. As I felt my orgasm building, I pulled her forward by her tits, our lips meeting and tongues smashing together as we both began to cum. Her cunt seemed to grip my cock even tighter as blast after blast of my cum pumped deep inside of her.

As our orgasms subsided, we just lay there, both breathing heavy. As my cock softened, it slipped out of her pussy and I felt a mixture of our juices leaking out of her, covering both of us and making the bed even wetter. Minutes later, probably because of the wine and exhaustion, we both fell asleep.

I ended up staying until Sunday afternoon. I lost count of how many times and ways we fucked that weekend. It was interesting that after that it seemed like all of my service calls to Sheila's company were always on Friday afternoons. We had a lot of fun weekends together.

 

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Written by oralnjsex
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