Sex Gets Better After 60 – Mary

Literotic asexstories – Sex Gets Better After 60 – Mary by Doug2024,Doug2024
Everyone involved in sex is over 18. The story is based on events that happened in my life. I have changed the names and some things to make the story flow. This will be part of a series. I guess I will call this story a prequel. The future stories start in 2015 and go to the present. My wife and I have a special friend. This series is about our relationship with her. I hope you enjoy my stories. I am open to suggested changes though.

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I had a best friend with a pool that lived a few blocks from me when I was in high school. Mary and I met my first day at a new grade school which was about a week after my family moved a couple states north. My father was offered a promotion and accepted. Mom loved it, because she missed snow and hated the heat down south.

Mary and I sat next to each other in 4th grade and we just clicked that first day. We decided to walk home together when we noticed we were headed the same direction anyway. We were surprised to find we lived four doors apart. We instantly became good friends.

Mary was intelligent (the first thing I liked about her), funny and just plain fun. She put the boy in tomboy. We loved to mentally spar with each other. She was as pretty. Her hair was closer to strawberry blond than red. By the end of 9th grade, she was close to her eventual height of 5′ 2″ with a thin athletic body. At 18, she had large D cup tits. For years I had a thing for large tits. She was likely part of the reason.

Her family moved the summer before 9th grade for better schools. We were disappointed, because we were best friends since 4th grade. We promised to stay in touch, but it did not happen. My family moved to the same small town in the suburbs for the same reason late in the school year when I was in 9th grade. I got on the bus for the first time the second Monday in March. I was hoping to run into Mary at school, but imagine my surprise to find her on the bus.

We were two of the first students on the bus and talked all the way to school. We found out we lived a little over two blocks apart. Mary said, “Let’s we eat lunch together and talk some more.” as we got off the bus at school.

I got to know a couple guys I sat next to the class before lunch, Algebra, my best subject. They asked me to eat lunch with them. I was watching and spotted Mary come in the door, so I waved at her. She spotted me and waved. You should have seen the look on their faces when she walked over and put her arms around me from behind. She then gave me a little peck on the cheek and said, “I am going to get something to eat.”

After she left, one of the guys asked, “Is that your girlfriend? I have her in a couple classes. She is really hot.”

“No, just my best friend since grade school. We were surprised when we ended up on the same bus to school this morning.”

Mary helped ease the transition to a new school again. I should mention I was average looking at best, 5′ 8″ and thin. Light brown hair in the spring that was basically blond by the end of summer, because I was outside as much as possible. Mary was already part of the in crowd. I was accepted as part of the group initially only, because I was Mary’s best friend.

They quickly figured out I was a nice guy who was polite, courteous, funny, a bit of a class clown at times, very intelligent and the first to help anyone in need of help. I became known for my occasional practical jokes which were normally pretty creative.

Six of my friends and I removed the divider between the walkout basement double doors and carried one of my favorite teacher’s Volkswagen bug into the hallway about a month before my family moved. The janitor removed the divider, so she could drive it out when she was shocked to see it in the basement on the way to the teacher’s parking lot. She told me she knew it was me the next day in class, but she could not prove it. She said it was a good joke though and was going to let it slid this time. The whole class laughed as I had turned red with embarrassment and she said “I will accept that as a confession and an apology.”

Mary heard what I did from a friend in the class. Soon I had people I did not even know ask me if the story was true at my new school. I always denied it, but nobody believed my denial. I was told it was because of the smile on my face when I denied it. I was still a nerd, but a likeable nerd.

I really got along well with the ladies, because I respected them, so they felt safe with me. Several said I was the perfect example of how a gentleman should act. It helped that I believed in equal rights, so I saw them as equals. Most likely my mother’s influence. My dad travelled for work, so mom was mother and father Monday through Friday. I did not participate in extra-curricular activities at school, because I was devoted to Boy Scouts where I attained the rank of Eagle.

Mary loved to tease that she would change into her bikini with me in her room knowing I would never even think about sneaking a peek. Actually true. Of course, she would giggle after I always blushed. One jerk said it was because I was a homosexual. Mary defended me saying, no, he is not homosexual. He likes girls, but he is a gentleman that would never take advantage of a lady.

In spite of her looks, Mary was a tomboy at heart. She loved playing baseball, basketball, and particularly football with the guys. We played football in the park near us starting in grade school until she moved. We normally played on opposite teams, but always played on opposite teams when it was football, because we were huge football rivals.

The guys in the new neighborhood would not let her play, because she was just not a girl, but a small girl. Girls after all were no good at football. I convinced them to let her try to prove she could play. I was not surprised when she insisted, we not be on the same team.

I was unconcerned when she pointed at me the first play and said I get to rush the quarterback. She with her speed, she was good at pass defense. With her size it was fairly easy to block her. I knew she took great pride in her tackling ability and that she wanted to impress the guys. Many of the doubts about her ability to play football disappeared after the first play.

We allowed one pass rusher and one blocker. The big guy assigned to block her did not take her seriously in spite of my warnings. She put him on his ass instantly. She then hit me hard in the ribs just as I released the ball. It was a perfect hit that knocked the wind out of me. Once I caught my breath, I said, “Damn it, Mary, that fucking hurt.”

She smirked at me. “I am only a little bitty girl. How could I hit that hard? Get up you little pussy and let’s play.”

The guys had a laugh at my expense. After that the guy did a much better job blocking Mary the next play. I completed a long pass. Mary decided to let someone else be the designated pass rusher.

Any lingering doubts disappeared the third play. I knew she was fast, but she was even faster than I remembered. Maybe her taking up track had something to do with it. I threw what I thought was a very safe short pass. She managed to break in front of the receiver and intercepted it. None of the guys could catch her. I tried to tackle her. She stepped left and then cut right. I was off balance, so I just lunged at her. My right hand barely touched her back, and my left hand landed on her right tit accidentally. I was not going to grab there, so my hand slipped off and she got by me.

Three plays and Mary got the best of me on two of them. Not a good start to the game. After she scored, she walked back to me. She grinned. “Next time, Leon, maybe you should think about tackling me instead of trying to grabbing my tit.”

I blushed and the guys started laughing at me again. “Leave him alone. Leon and I have trash talked and teased each other for years. He is my best friend and a nice guy. I know he would never actually grab me inappropriately on purpose.”

She gave me a hug and a peck on the cheek. She then added, “I expect all of you to treat me like one of the guys. I will not get upset if you happen to grab the wrong place unless I think it was not an accident. In that case, I will kick your goddamn ass.”

I quickly added, “I believe she will get the ass kicking done, but it will not matter. If I think you have taken advantage of her, my brothers and I will give you the worst ass kicking you have ever gotten.” My three brothers all nodded yes. Mary gave all four of us a hug and “Thank you.” After that, she was just one of the guys.

My brothers and I were at her house swimming quite often. Mary and I continued to grow closer. Not as close as the Wilson girls I will mention later, but close. We could talk about anything. We had just turned 18, because we both had January birthdays. I would tease her that I was into older women, because her birthday was a little over two weeks before mine. Her comeback was always well at least one of us is an adult. We were hanging out Washington’s Day our senior year in high school.

She surprised me by saying, “So, I heard you slept with Jean, Saturday. You know she is a big slut.”

“How do you know that?”

“Oh, come on, you know we’re friends. One day about a week ago, she asked ‘Have you and Leon had sex yet?’ I told her, ‘No, I am still a virgin and I know he is also.’ She said, ‘Maybe I should make a man out of him.’ I thought she was kidding, but yesterday she told me, ‘Leon, turned out to be good lover in spite of his inexperience. Even though it was his first time, he picked up pussy licking quite well. He kept licking when I ask him not to stop.’ She loves sex and has fucked quite a number of guys.”

I never cover my time with Jean. Except for educating me some while I gave her oral sex, it was nothing special. I am still a little ashamed to admit my first time was with such a complete slut.

Back to the story, I blushed and Mary laughed. “Well, that is embarrassing. I knew the guys talked about her, but I thought it was just talk. You would not believe a few rumors I have heard about you. Maybe you should not hang out with her anymore. I guess I will cancel the date we have Friday.”

“Jean is a nice person even if she is very promiscuous. You know I do not worry about rumors. She got me thinking though. I want to stay a virgin, but I would like to try oral sex.”

“Why are you telling me this?”

Mary shocked me. “I know you have a thing for my tits. I will make a deal with you. I will let you play with them all you want provided you lick my pussy all I want after you are done playing with them. We will not fuck, but I will play with you or maybe try sucking you. I trust you, so I know you will not push me to fuck. Some guys would not take no for an answer, but I know I am safe with you.”

“Very funny, Mary. I cannot believe you are teasing me about sex, but this is one of your better jokes.”

She started unbuttoning her blouse. “I am dead serious. Do we have a deal or do I stop?”

I just stared in shock as she removed her blouse. She started to remove her bra, paused and asked, “Is it a deal or do I stop and put my blouse back on?”

“Deal, deal, deal.”

That is a day I found the power of giving good oral sex. After I licked her for a while, Mary asked “Will you fuck me now, please?”

“Are you sure? You told me we would not fuck, because you want to stay a virgin. I do not want to take advantage of you.”

“Oral sex was even better than I ever dreamed it would be. I can’t believe you got me to climax several times. I want to try intercourse now. One older girlfriend told me her first experience was terrible. The guy just shoved it in her hard and it hurt like hell. I know you will be gentle and stop if I change my mind, right?”

“I do not have much experience, but I will can try. Of course, I will stop if you ask me too.”

“I would prefer my first time to be with someone I love and trust.”

I started slowly entering her. She winced a little, so I stopped. “Are you okay?”

“It is fine, just a little discomfort. Keep going.”

I very slowly worked in and out until all of me was in her. I stopped again. “Are you still, okay?”

“Keep going. It is starting to feel nice and the discomfort is passing.”

I did not last long, so after several minutes I came inside her. “Oh shit, did you just cum in me?”

“Yes, was that not, okay?”

“I guess I did not warn you to pull out. We should have used a condom. Did you have one?”

“Of course not. This is only the second time I have done this. Jean mentioned she was on the pill, so we did not need one. Sorry, but I just assumed you were on the pill also.”

“It’s fine if I do not get pregnant. At least I had another orgasm just before you came in me. That felt amazing. Thank you for being so gentle and caring. It is nice I will have good memories of my first time.”

“Next time we will use a condom.”

“Sorry, I guess I was not clear on that. This was a one-time thing to try oral sex. I had no plans to try intercourse. It just happened. I am glad it was with a special friend like you. I love you, but not in the boyfriend girlfriend kind of way. I will not say we will never have sex again, but I doubt it.”

I was hurt and a felt a little guilty, so I did not go to her house after work and dinner the rest of the week. We ate lunch together, but did not talk much. I drove her to school like normal. I was the stock boy at a bank after school, so she took the bus home. Not much was said on the drive to school either.

On Friday evening, she called just after I got home from work and asked me to come over. Her parents were out with friends and she wanted to talk. When I got there, she said, “I am sorry if I hurt you. Do you want me to leave you alone?”

“No, it was just as much my fault for making assumptions. I also feel guilty, because I believe I took advantage of you. I knew you wanted to stay a virgin. I should have apologized for taking your virginity.”

“Leon, I have no regrets. In fact, to prove it, you can fuck me again now if you really want too.” She chuckled. “Of course, you have to earn that privilege by giving me a good licking again. It felt amazing when you licked me last time.”

“I guess that means you are not upset with me?”

“Hell no.”

“I think it is best we return to best friends. I am good, how about you?”

“Are you kidding? I am fine.” She tickled me. “Are you sure you don’t want another sample?”

“I am okay unless you insist.”

“Good, I have missed my best friend.”

About a week later she called and asked me to come over. We had both eaten dinner with our families already. When I got there, she took me to her bedroom and closed the door. She got a serious look on her face. “Leon, I am late. My mother and I normally start our periods the same day or a day apart. Hers started two days ago. I think I may be pregnant.”

“Do you want to get married?”

“Are you kidding me? No, you know I do not think of you like that.”

“I am not kidding. I am not expecting happily ever after. I just thought you might not want to have a child out of wedlock. We do not have to sleep in the same bed, room or even the same house. You can even date while we are married if you want too. After a respectable period of time, we can get divorced when you are ready for it. We will then move on with our lives. I will pay child support, but I want to be involved in our baby’s life.”

“You are a great best friend and very special guy. I surprise you with this and you immediately step up. I am touched by your kind offer, but I will have to think about it. Let’s just wait and see what happens first.”

Two mornings later she hopped in my car for the ride to school with a big smile and said “I finally got my period this morning.”

“Thank goodness. I am relieved you are not pregnant. We are both too young to be having a baby. You want to go to college and I want to go in the Air Force for electronics and radio technician training.”

She frowned. “I know, but part of me is a little disappointed. I was going to accept your offer. It reminded me just how truly special you are. I wanted to see if we could make it as a couple. I did not know if the marriage would have lasted, but I was going to put everything I had into trying to make it success. Should we try dating and see where it goes?”

“That idea sounds interesting, but we need to take some time to think about it. With all that just happened, we should not rush into anything. Rushing almost got us in big trouble.”

After about a week, we decided to just stay best friends. We drifted apart some, but stayed close through the summer after we graduated. After the near miss, I became extremely diligent about making sure a lady was on the pill or I used a condom. If I suspected a lady was lying to me about being on the pill, I would wear a condom as a precaution.

Although I was outgoing, I was shy about asking a girl out on ‘a date’. It took me some time to work up the courage to ask a girl out on ‘a date’ even when we were good friends. It is funny looking back on it now. I went out with girls all the time one-on-one who were my high school friends. Many of the tellers at the bank were working their way through college kind of adopted me like I was their little brother. During the summer I rarely went to lunch by myself. Lunch was normally with one or several hot young ladies that worked at the bank who were just a few years older than me. Of course, all these outings were not ‘a date’. First dates were just easier when the lady made the first move.

Mary went to college in Texas in August. I went in the Air Force in October. We lost track of each other then. I was gone for 8 months with basic and technical training. I hoped to see her during the Christmas break along with other friends like the Wilson’s. My family instead picked me up in Mississippi and we visited my grandparents in Florida for Christmas.

She met a guy from Texas her freshman year. It was love at first sight. She ended up marrying him after her freshman year. With Mary and her brother out of the house, her parents sold it and moved somewhere else. Her dad was tired of taking care of the pool I heard. I did not know where they moved.

We did reconnect when I was in my late 30’s. I was selected to fill a network engineer opening at work. I would normally visit her and her husband when I took a training classes in Dallas which is where they happened to live. A mutual friend I ran into, gave me her contact information just days before flew to Dallas for my first training class. We enjoyed our visits very much, but we did not redevelop that special bond we had before. Her husband did love hearing our stories.

After our near miss, Mary guided me and another lady together shortly before we graduated. Joyce had dated Mary’s brother, but they had broken up recently. Mary and Joyce had become good friends in spite of her jerk of a brother. I despised him, because he did not treat his sister very nicely. I had seen Joyce in passing a couple times, but did not pay much attention to her.

The first time I got a good look at Joyce and got to know her was when I went swimming at Mary’s. Her dad always opened the pool as early as he could. The pool was heated and it was the first warm weekend of early spring. Joyce was in a small bikini. Her tits were ridiculous and just bounced all over the place. They were even larger than Mary’s. She was just barely under 5 feet and thinner than Mary. She could have passed for 12 or 13 if it were not for her double D tits.

Mary noticed I was mesmerized by Joyce’s tits. Actually, every guy was mesmerized by Joyce’s tits at one point or another. They were huge and in a small bikini top. Mary caught me checking out her own tits in her small bikini also. Mary was having immense fun whispering her teases in my ear about my obsession with big tits. I blushed each time and she loved to make me blush. People would ask why I was blushing and Mary would always say it was a private joke. Mary kept telling us how nice the other one was. She played matchmaker and talked us into going on our first date. The only thing Mary did not do was let us know about our age difference as Joyce was 4 and half years older than me. I was 18, she was nearly 23. Joyce was a big influence on me I will cover in future stories.

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I include the story of Mary as a prequel, because she does not get covered much in the other stories. My wife’s sister and my brother and their families live in Dallas. My wife trusts me and does not have a jealous bone in her body. We went to Mary’s twice. For some reason Mary and my wife do not get along at all, so I have not seen Mary in over ten maybe fifteen years. Needless to say, I do not say much about Mary in the stories I shared with my wife’s and my special friend.

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