With My Best Friend's Mom

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Frustration, lust, passion, and nylons.
3k words
4.38
296.7k
65

Part 1 of the 4 part series

Updated 10/29/2022
Created 04/15/2006
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nylondad
nylondad
182 Followers

My name is Danny Maxwell. I just turned nineteen years old. I am the oldest in my high school graduating class. I just started school late as my mother did not think that I was ready to start school at five years of age.

I was told that when I was about two or three years old that I would always touch and run my hands over the nylon legs of relatives or friends that visited my parents. I got away with it when I was young but after a few years my hands were slapped so I stopped.

As I became older this infatuation became more pronounced. I would focus on girls in schools, teachers in schools and sometimes the mothers of kids I knew. I always was on the hunt to look at and fantasize about stockings and legs.

I met Bobby when I was in kindergarten. We became best friends and were inseparable all through grammar and high school. I usually went to his house after school because there was so much to do.

As kids and we would climb the large apple tree in the yard at his home and go into the tree house his father had built. Bobby had a television in his room and had every conceivable toy to play with.

Bobby's mother had her own car and that was unique since in my family there was only one car and that was used by my father. She would drive Bobby and me to the mall and also to and from baseball games.

Bobby was an only child of his parents Lois and Bernard Shaw. Bobby's father was twenty five years older than his mom. He was always hunting in the winter (usually) traveling to New York State to hunt for deer.

In the spring and summer he would go fishing in Canada sometimes for weeks at a time. He was a successful lawyer by trade and met Bobby's mother when she was hired by the firm where he worked. She ended up as his secretary and they married two years later.

Bobby and I were both athletic. He was a star at baseball and I was considered a great dancer. I had taken dance lessons in my aunt's dancing school.

Although I was initially resistant, my parents thought that learning to dance would be an asset socially. At the time I had no idea how true that would be.

When there was a school function such as a dance or a play (where dancing was a part of an act) I always participated. At dances there seemed to be an unending supply of girls wanting to dance with me. I first had sex with a girl shortly after my eighteenth birthday.

I could never get this one girl (Monica) to wear stockings when I had sex with her. She did not like wearing pantyhose either. I wanted to rub my hands up and on a woman's legs and maybe get her to have sex with me while she wore them. Evidently I was asking for the world.

Monica asked me if I had "psychological problems" that made me want her to do that.

Women always seemed to analyze everything. I once heard that women looked for a reason to have sex and men looked for a place.

My frustrations were ongoing.

So were the frustrations of Lois Shaw.

Bobby's father never seemed to be around. His appearances at home were sporadic. He was always away on hunting or fishing trips. He could do so because he was a senior partner in his law firm. As a result Lois Shaw always had time on her hands.

She participated in fund drives for the school. She also volunteered to assist in school functions assisting with decorating ideas for dances and proms. She was a Red Cross Volunteer.

Lois Shaw had time for her son and on occasion for her son's friends but there was never any time for Lois. Although Lois always seemed happy and bubbly, she was a lonely and sad woman.

She saw her life passing by as her son became older. Nothing in her life ever changed. There was never any excitement.

She would look in the mirror and would see a woman who at one time had been young and vibrant. She felt stale and her marriage was stale.

Her husband was a great provider as far as money was concerned, but the age difference and the lack of mutual interests between the two of them had taken its toll. She was a loyal woman who had needs that were not being met.

Her five feet nine inch height and slim figure still received second looks from men on occasion. She thought that she was too tall to wear heels and as a result usually wore flat shoes when she dressed up.

She had soft large blue eyes and auburn hair. She had long slim legs. She always wore a dress or skirt when she left the house. She dressed conservatively.

She would not conform to wearing pantyhose but rather wore a garter belt and stockings. In her subconscious she wanted her husband to notice her legs as he once had. Her skirts were always a conservative length.

The senior prom was being held in the local women's club. Bobby and I had dates for the prom. Since Lois had assisted with the decorations, she was invited.

Lois checked with Bobby to see if he would be uncomfortable with her being there and he said it would be no problem. I was at Bobby's house when this conversation took place.

She asked me, "Would you dance with me just once just once?" My dancing reputation was well known. I said I would.

My parents and Bobby's parents shared the cost of the limousine for the prom. Bobby's mother came alone in her own car as Mr. Shaw was out of town.

One of the senior's fathers had donated the services of a live band for the prom. This band had twelve pieces and three singers and they could and did play anything.

Monica and I had stopped seeing each other months earlier and I needed a date for the prom. My date was a pretty senior named Leslie Johannson and Bobby's date was her younger sister Shawna.

The prom was okay. Leslie was a pretty girl .She had long blond hair and brown eyes. She had celebrated her eighteenth birthday on the day before the prom. We had befriended each other in chemistry class as we were lab partners. She and I both needed a date and as a result we ended up together.

There was no electricity between us.

Leslie had her hair up and she wore makeup the night of the prom. I had never seen her look like that. She had a nice figure. She wore heels but was not wearing pantyhose or stockings. I was disappointed from the viewpoint of just looking but it was not to be.

All I remember was that I seemed to be on the dance floor for most of the prom. I danced with Leslie and Shawna as well as a few girls who went to the prom without dates.

There was a point in time Bobby and I snuck out for some "refreshment". We had mixed some vodka (that we had smuggled in) with the punch at the prom and we went for a quick taste.

I had seen Bobby's mom at the prom when we first arrived. She was sitting down at a table talking to one of the teachers who was there. She was dressed in a blue dress that was knee length. She had on what looked like gray or pale black stockings that I noticed would shine when light would hit them from certain angles.

She had on three inch dress heels that were two tones (black and blue).She had her legs crossed so that the hem of her skirt was a few inches above her knee. I took this all in before I spoke to her. I had not been aware that she had noticed me staring at her legs before we spoke. She asked me for a dance I had promised her.

She wanted to jitterbug and we did.

It was a long dance and I was sweating in my tuxedo. She surprised me with her ability on the dance floor. I loved how she moved her hips. For such a conservative looking woman she really could move. After the music ended for the jitterbug we were still on the dance floor when a slow song was being played. She thanked me and I thanked her as well.

She had started to walk off because a slow dance was starting. I asked her for the dance. She accepted. Here I was aged nineteen on the dance floor with a woman nearly the age of my mother. I remember how she felt in my arms. She had a backless dress on and her skin was surprisingly smooth. I smelled the scent of her perfume.

I tried not to dance too closely and to carry on a conversation with her. I felt awkward because she was my best friend's mother.

I suddenly remember looking in her eyes and not seeing someone's mother but rather a woman.

She said she had not danced slow with anyone in several years and wanted to capture the moment with me. We got closer on the dance floor.

There were flashing lights on the dance floor and as a result it would not have been easy for anyone to see how close we were to each other. Yet here I was on the dance floor with Bobby's mother. I remember looking for Bobby but he was nowhere to be seen. I found out later that he had gone out for some more "refreshment."

The dance lasted several minutes. I became excited for a variety of reasons on of which was Lois Shaw was an attractive woman and also that she was so close to me. One other key reason was that she had heels on and stockings.

I became hard. I tried to think it away. I thought she did not notice but she did. We had twirled on the dance floor and she got closer to me than she had been when our hips met and my cock probably bruised her it was so hard.

When I realized that she had become aware of it I tried to create some space between each other. She would have none of it. She kept very close to me until the dance ended.

Her cheeks were flushed and her eyes were wide and unblinking. Her mouth was slightly open.

When the music ended she thanked me again and again. She told me that not only had I made her day but I had made her year.

I told her the pleasure was mine and I tried to hide my erection. She looked at my crotch and giggled. After that comment I did not see her. She evidently left the prom.

After the prom Bobby and I as well as our dates went to a party. I was hoping to get some type of action from Leslie but she ended up throwing up several times at the party after ingesting some "refreshment".

Bobby and I ended up at his house at about 4:00 A.M. The house was quiet. I assumed his mother was in bed.

After Bobby washed up I used the bathroom to wash my face and brush my teeth. Since Bobby had only a twin bed in his room, he had given me a spare pillow and a blanket and I went down to the living room and lay down on the large sofa.

I took off my pants and got under the covers in my underwear.

There was a light outside on the garage that cast a glow into the living room. I started to drift off when I heard someone walking down the stairs from the second floor. It was Lois. She whispered "Danny, are you awake?" I said I was.

I moved on the couch so that she could sit. She said she had not gone to sleep. She had what appeared to be a nightgown and slippers.

After she sat down I could see her legs crossed and I could see and hear the telltale sign of nylons on her legs as there was a shine from the garage light that reflected off of them. I could hear them swish as she crossed them. She must have left them on from when she had gone out. I asked her why she was up.

She responded that she had arrived home after the prom and then went out for a drive. After driving around for over four hours and listening to music in her car did she return. She said she did so because she did not feel like coming home to an empty house. She said she only had arrived home about hour earlier.

She said she was in the process of changing her clothes when Bobby and I arrived.

She asked me if I enjoyed the prom. I said that it was "okay". She said, "Just okay?" I said that it would have been more fun had I been there with someone special.

I told her that Leslie was nice but not a girlfriend. She said that Leslie was such a cute girl. I said I knew but that she didn't "trip my trigger."

Lois whispered to me "what would cause me to have my trigger tripped?" I told her that there were a variety of factors.

One was I liked it when girls liked to dance. Another is that I liked it when girls dressed in a feminine way. I told her that Leslie looked good but there was something missing.

I told Lois that I always enjoyed looking at an attractive woman in stockings and heels and Leslie did not seem to like to wear them. I said that I wanted to touch a woman's legs while she wore them but I was never able to do so.

She quietly asked me if I thought she had attractive legs. I said she did. She asked me if dancing with her had excited me. I replied that I did.. She asked me, "Why?"

I answered that, "I am not sure why but that I feel a little ashamed and embarrassed especially that you being my best friend's mom."

She said to me that I was approaching manhood and that she was a woman and that is all that should matter.

She asked me if her wearing stockings were a factor and I said that it probably was.

She asked me if I wanted to touch her legs. I said I did but I was a little scared.

I touched around her crossed legs. Her legs felt so sexy. I had not touched a woman's legs since I was a kid. We whispered to each other as I ran my hands across her legs.

I was getting a major hard on. She kept on asking me if I liked touching her legs.

I told her, "I love touching your legs." This went on for a while.

She moved closer to me on the sofa and asked me if I would kiss her. I thought about it for a moment. She said I did not have to if I did not want to.

I did kiss her. It was a peck. She did not move her face from me. There was another peck.

Her lips were soft. I could see in the dim light that she still had on lipstick.

I kissed her a third time and held the kiss as I still was touching her legs. She opened her mouth slightly.

Out tongues touched for a moment and then touched again.

We continued to kiss and her tongue was making progress in my mouth.

She touched my arm and then held my face as we kissed.

My hands never left her legs. She moved slightly forward causing my hands to drift up her legs and I was now at the top of her garter belt. Her thighs felt warm.

I heard a low groan from her. I leaned back on the sofa and she leaned back with me.

I felt her damp underwear and she started to breathe hard.

One of her hands drifted to my waist then to my underwear and finally found its way to the outside of the underwear. She rubbed my cock.

I knew now that I wanted to fuck her. However there were so many conflicting feelings that I had trouble processing what was going on.

My primal feelings were at hand. I had a willing woman over the age of eighteen who was wearing stockings and liked me rubbing her legs and (I thought) wanted me to do more.

The fact that she was my best friend's mother started to matter less and less

She said, "If you want to stop, I understand."

I did not respond but went back to kissing her and rubbing (now) the outside of her pussy.

She reached under her nightgown and slipped off her panties.

She lay down on her back on the sofa and reached out for me. She opened her legs. I took off my underwear.

I got on top of her. She rubbed her nylons against my back. My cock was against the hair on the outside of her pussy.

I was ready. I started to grind against the outside of her pussy.. She returned the favor. I moved my body down towards her feet and then moved my cock back.

She reached for me with one of her hands and held my cock. She pushed the head against her opening.

I slipped in. She was hot and wet. I moved slowly at first and then much quicker. I could not hold it and I came probably within thirty seconds.

After I came I stayed inside of her. We kissed. My cock had not gotten totally soft. She moved from side to side and I got hard again.

I started to move in and out again. She wrapped her legs around my back and we locked loins for another five minutes before I came again. It was an interesting summer.

nylondad
nylondad
182 Followers
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8 Comments
ingaroberts1ingaroberts1about 1 year ago

Such a wonderful experience for them both. Nicely described and triggered my imagination about times I had as a young man where I had close encounters with older women.

AnonymousAnonymousover 11 years ago
Pee

Could u add a pee fetish chapter please

AnonymousAnonymousabout 13 years ago
Fantastic!

I too love the old school nylons! I got turned on to it by my Mom. She would have me get under her dress, and latch the garter from her girdle to her nylons! It is still hot to this day! More!

MicheleNylonsMicheleNylonsover 15 years ago
What's With The Critique

I have always been a fan of your stories; I too have a raging nylons fetish and penchant for incest (although my current fetish is transvestism).

As for the cockhead who titled his comment in capitals; I wouldn't take advice from an idiot who "SHOUTS" on the Internet.

xxx

Michele

AnonymousAnonymousover 16 years ago
Good but a bit more?

Loved the story but the sex scene was way too short.

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