Intro

I'm planning on this being a series of short stories detailing interactions I've actually enjoyed with my mother-in-law over the 20 years that I've known her. We still play a little bit today but each of these chapters have been an experience I've thoroughly enjoyed and cum thinking about over and over.

My name is Brian. For most of my life, I've always been turned on by women's legs. Stockings, nylons, garter-belts and high heels have always made my cock rock hard. For years my desires were fed by movies, magazines, and porn sites. My head has always turned for an attractive older woman in a bar or even at a grocery store. Looking to catch a peek and determine if she was wearing thigh highs or pantyhose. I got married in 2001 at the age of 26, and my wife would occasionally wear them for me but thought my fetish was pretty ridiculous. It was around this time that I noticed my mother-in-law, Diane, wore stockings almost every day.

Let me describe her for you. They say a woman grows up to look like her mother and if that's the case, I was in for a treat. Diane was curvy, not thick but not rail thin either. She had a pretty dark complexion from trips to the tanning bed or laying out by a pool. Her eyes were very seductive and her lips looked like you could kiss them for hours. Perhaps by design, but she always dressed in a way to show off her large breasts and firm sexy legs.

I never really looked at her in this light until we had our first child a year after we were married. Diane came to stay with us and help my wife take care of our newborn son since I had to go back to work. She stayed in the bedroom for over a month and I took every opportunity I had to look through her lingerie and run her silky smooth nylons and underwear along my cock. I remember following her up the stairs one night, stopping myself from running my hands up the backs of her legs while wondering if those were the same nude stockings my cock was inside earlier that week.

While I really wanted to take action on these feelings during this time, nothing eventful happened with my mother-in-law. I often look at this as a "missed opportunity" but also chalk this up to the beginnings of my feelings for this woman and the need for me to feel her legs wrapped around me with my cock buried deep inside her.

The first opportunity I got to make this a reality was several years down the road. Our son was old enough to stay with a babysitter and we were going to spend the weekend partying at a Ski Carnival about an hour away. Being an annual event, the whole family was meeting up there and secretly I was very excited about seeing Diane and the outfits I'd get to see her in. I have never been skiing but to set the stage, this was more about the party. Skiing was an hour or so activity in the middle of the day but most of the fun was at the lodge. Girls wearing sexy outfits, live music, tons of alcohol and always some dirty dancing.

I spent most of the day with a beverage in hand and hanging out on the back deck watching the skiers flying down the hill. There were some talented people but most were just out having fun until the real party started. By this time, I was feeling pretty buzzed and lit up when I saw my mother-in-law walking towards me and the bar. I won't pretend she was in some super sexy outfit but it was funny seeing her walking in ski boots and bundled up to her scarf and ski goggles on top of her head.

"Brian" she called out to me. "I need your help!". Turns out the bartender still required ID and she wasn't able to get another drink without showing her driver's license. Gloves and arms in the air, she asked me to fish her ID out of her pocket. To this day, I blame the alcohol but I'm not sure what came over me. My hands went straight into her side pockets first. Feeling her hips and curves of her body more than looking for any form of ID. "Up here, in this pocket" she pointed. I slid my hand inside her chest pocket, immediately feeling the card she was looking for. Instead of pulling it out, I took the opportunity to grope my mother-in-laws breast through her jacket and sweater. In an effort to be as "helpful" as possible, my other hand slid around her back into her back pocket so I could feel her ass as well.

Here I was, groping Diane right out in public. One hand on her ass, the other squeezing as much of her breast as I could. Instead of getting smacked though, I looked right at her. Eyes closed and a little smile on her face as she bit her lip ever so slightly. Realizing the truth of what I was doing, along with where I was doing it, I quickly pulled the ID out of her pocket and handed it to her. She gave me a quick peck on the cheek then turned and walked back inside to the bar. Not before giving me a brief look back and naughty smile.

The rest of the afternoon was pretty uneventful. More drinking, more skiing until we eventually all went back to our rooms to get ready for the evening party at the lodge. My wife and I walked into loud music and tons of people right around 8pm. The dance floor was crowded and she started spinning as I worked my way to the bar to get us more drinks.

I was happily surprised to see Diane with a stool at the crowded bar so I worked my way down to where she was sitting. I wished she was showing more leg but she still looked stunning in tight blue jeans, a black form fitting sweater and some calf high black boots. Had to admit, it had my cock stirring. I was hoping she wasn't upset from my groping of her body earlier and my fears were put to rest when I realized how far ahead of us she was in the drinking department.

Over the loud music, I ordered three drinks and then leaned down to get closer to her ear and told her how sexy she looked. I always go back to this being the moment that changed our relationship forever. Looking straight into my eyes with a look of desire, I felt her hand work its way from my thigh straight to my hardening cock over the top of my jeans. I could tell she was pretty buzzed as she stared at me but didn't object as her hand started to run up and down the length of my cock.

She was staring right at me completely full of lust as the bartender walked over with my three drinks. I slid one to her as she continued her hand-job under the bar. Her touch was so purposeful as I could feel her fingers gripping and sliding over my hardness. "Don't stop" was all I could muster as she stroked me.

After a couple minutes, the only thing that stopped me from cumming right there in my pants was my wife. She found us a booth and there were other friends already sitting there enjoying some simple bar food. I slid in the side opposite my wife but was surprised when my mother-in-law squeezed in right next to me and dropped her hand right back to my lap. Looking at my wife, I declined a dance as her mom still had my cock at attention between her fingers. Perhaps a good thing at that moment for all but she grabbed her mom's free hand and dragged her out onto the crowded dance floor.

My wife was sexy and I'm sure there were many eyes glued to her cute little ass. Mine however were undressing my sexy mother-in-law. Her legs looked hot as fuck in those tight jeans and her ass was lifted by the sexy black boots. Here large tits were held firmly in place under her sweater but the bouncing teased how large they were. I had to stop staring before someone caught on but it was difficult to not look.

The DJ cranked up the music more and I watched as he started throwing out drink tokens in the direction of the women on the floor. Diane caught one as I wanted in jealousy as she reached under her sweater and placed it in her bra. The drinks kept flowing and the dancing was getting even hotter and more sweaty. I decided it was time for something a little harder and ducked outside to get some fresh air. I had a stash of liquor in the back of my Jeep that I was going to enjoy on my own.

As I was enjoying a shot of Jack Daniels, I heard, "Do I get one of those"? I turn around to see my mother-in-law standing there with her hands on her hips staring at me. I told her it would cost her a token and she walked right up to me, held her arms up to the side, and told me to go ahead and collect. She only stands about 5'5" so was looking up at me as I wrapped my arms around her and groped her ass. I used it to pull her closer to me and then worked my way around her hips before sliding my hands under her sweater.

Every piece of me wanted to kiss Diane as I felt her soft warm skin above the waist of her jeans. Ironically, in my drunken haze I figured that would be cheating as my hands slid up to her lace bra covering the tits I have cum thinking about so many times. Like a kid getting to first base for the first time, I mauled her tits. Feeling how warm and soft they were under the sexy lingerie. Knowing she was turned on too, I felt her nipples hardening under my hands. This was nothing to the feeling of how hard they got as I pulled her bra roughly down exposing to the cold night air.

As my fingers were rolling her nipples, the only thing snapping back to reality was feeling her hands on my hard cock again. Feeling the cold air as she undid my belt and opened the button of my jeans. She looked me straight in the eye as she reached through my boxers and pulled my hard cock out into the open. There was no reality of what was happening. Perhaps the alcohol or the lust but no thought given to the fact we were standing there in a public parking lot. No thought to the fact it was my wife's mom whose hands felt so warm and soft on my cock. No thought as to whose nipples tits I was groping like an animal in heat.

"Please don't stop", she whispered and I now essentially was fucking the palm of her hand. She then took the initiative and pulled me closer to her while reaching up and kissing me on the lips. Surprised by her actions, I likely was unsure until I felt her tongue parting my lips. Once that happened it kicked off the most erotic kiss I think I've ever had.

I was on sensory overload as feeling after feeling hit me at once. Our tongues were exploring each other, the night air was cold on everything that was exposed. At the same time my cock was red hot feeling her soft hands stroking me back and forth. I could hear the loud music still coming from the lodge but at this point I didn't care. I wanted to be with this woman. I wanted to fuck her right there in the parking lot and didn't care who watched. We both tasted like alcohol and she knew she could make me peak as the pre-cum was now in the palm of her hands.

She had other thoughts though as she pushed me aggressively against the side of my Jeep. Looking quickly over both shoulders, Diane slurred, "Fuck it" before dropping to her knees right in front of me on the concrete pad. The thoughts of where my wife was were completely erased as I felt her mom's mouth slide over the head of my cock with no hesitation.

Maybe it was knowing who it was or maybe it was being outdoors, but no mouth has ever felt better on my cock. I couldn't believe my eyes looking down and seeing my prim and proper mother-in-law on her knees sucking my cock like a pro. She was taking it into her throat each time she went down on me. Farther and farther each time. Her hand was alternating between my cock and playing with my balls. Cupping them, squeezing them...it felt incredible.

She looked up and momentarily made eye contact with me. To this day, it is one of the sexiest memories I have. Seeing your mother-in-law with your hard cock sliding between her sexy red lips will do that to you. Instinct took over and I held the back of her head while thrusting to get my cock deeper and deeper into her mouth. She reached around me sliding my hands up the back of my legs to my ass cheeks. Pulling farther into her mouth, she likely knew I wasn't going to last long.

She took just enough of a break to say, "Cum for me...". Between the fact that I was so worked up and that my mother-in-law was giving me a blow job in a parking lot, there was no way I was going to be able to hold back. With my hands now both holding her head, I warned her that I was going to cum. Neither of us missed a beat. She looked up at me just as the first rope of cum shot from my cock filling her mouth. She swallowed every drop as rope after rope followed down her throat in the most intense orgasm I've had to that point.

I felt like I couldn't stop cumming as she continued to work my cock like a professional. She ran her tongue up and down the shaft cleaning up every bit of evidence of our taboo act. She stood back up as we began straightening our clothes. "This token belongs to me". She picked up the free drink token that fell from her bra, kissed me on the cheek and said to join her back in the bar.

There was some more dancing, drinking, and flirting that night but nothing compared to that moment that awoke something in both of us that we wanted to explore. Before turning in for the night, Diane walked up to me in the lobby of the hotel and handed me a small bag. She whispered that she knew all my dirty little secrets before she slipped off into the elevator.

Still in shock at what happened that night, I made sure I was alone before opening the bag. Inside was a small black lacy thong and a hotel key card with a room number in black Sharpie.