The school crossing guard Sex Stories for free – Y2Stories

Back when I was 30 and my two boys were in 3rd and 4th grade, I volunteered in the mornings to be a crossing guard at their school on a busy street. On the first day I got paired up with a 69-year-old lady named Penny. My first thought was, Oh great, I volunteer my time and I get stuck with a crotchety old lady.

Well, I was totally wrong. Penny was an angel. An incredible lady where soon we became friends. Her husband had died about five years prior to this and her kids were grown up and out of the house. My wife and I invited her over several times for dinner and she became like a third Grandma to our boys. She always had a smile on her face and loved to laugh.

I always felt though there might be a little naughty side to Penny. Sometimes while working with her, a handsome dad would walk or drive by and she would make comments like, mmmm I wonder if that hunk is single and then she would laugh her awesome laugh. Or sometimes when a dad walked by, I would just hear her go MMMMMM.

I must admit, I myself sometimes had some naughty thoughts of Penny. One of my wildest fantasies had always been having sex with a beautiful mature woman that still had a strong appetite for sex. Penny had a sweet, almost childlike voice, and for being 69 years old, she was in great shape with a set of tits that would drive a big tit lover insane.

It was a great two years working with Penny, but when my boys moved on to middle school and took the bus, I felt there was no need for me to continue the crossing guard. Penny cried when I told her the news and I have to admit, so did I. But we stayed in touch. I stopped by the school at least once a week in the mornings to say hi and we still invited her over for diner occasionally.

About a year or so later, my wife and I hit a rocky point in our marriage and after some counseling, we decided it was best to get a divorce. One morning when I stopped by to say hi to Penny, I told her about the divorce. She was really bummed at first as she had gotten close to our family and gave me a big hug. At the same time though, I was sensing something when I told her. Almost a hidden smile maybe.

Penny was a nice shoulder to lean on during this divorce process. I have a bunch of guy friends, but you can’t lean on them. They would just tell me to man up. The day after our divorce was final, I stopped by to let Penny know. She gave me her usual hug and told me things will get better. At the same time, she asked me when the last time was that I had a nice home cooked meal. I laughed and said, does frozen pizza count as home cooked. She gave me that wonderful laugh. She then said, I want to return the favor of a wonderful dinner like you have given me over the years. She asked if I had the boys this coming weekend and I said no. She then said great, I will not take no for an answer. This Saturday evening you are coming over to my house for my word famous lasagna and homemade French bread.  I told her that sounded great, and I would bring a bottle of wine. She said wine gets me silly, so jokingly I told her I would bring two then. She gave me that wonderful laugh.

Saturday evening couldn’t get here soon enough. I was really looking forward to this, wondering if that little bit of naughtiness i have seen in her will come out even more. Maybe the two bottles of wine will help. I arrived to her house which I was surprised was in a wooded area away from neighbors. I remembered her saying her boys come over and help maintain the house.

She opened the door, and I was amazed how beautiful she looked. I always thought she was beautiful, but today there was an extra touch to her. She was wearing a black shirt that had some shiny things on her chest. To break the ice, she asked me if I liked how her breasts sparkled. We both laughed.

The smell of lasagna was incredible in her house. She said it wouldn’t be ready for another hour, so we opened a bottle of wine and sat on her couch and talked and laughed and had a good time. I could see pictures of her family. i was the same age as her two boys. That made me feel just a little guilty of the naughty thoughts I had been thinking about Penny. She was 39 years older than me.

Dinner was finally ready and we opened the second bottle. The lasagna was incredible. During dinner we had some more great conversation. One question that she asked me would be the start of where the rest of the night was heading. She asked besides missing my boys, do I miss anything else about being married. I told her the friendship my wife and I had and all the good times we had. The next question took me by complete surprise. She asked, what about your sex life you had with your wife. do you miss that. Was the wine getting to her and she was being silly or was she serious. I told her that we used to have incredible sex life, especially before the boys. But it seemed as they got older, her sexual desire faded and I think that’s a part of our divorce. She then said, I hope you don’t mind me asking but, you wanted more sex than she was willing to give you. I said yes and when we had sex, it was like she just wanted to get it done with.

I noticed kind of a wicked smile on Penny’s face. i then said, since we are getting personal, what do you miss mostly about your husband. She gave me a big smile and said, no doubt, I miss our sex life. She went on to say, we had an incredible sex life. He could not keep his hands off of these, as she cupped her breasts in both hands. I laughed and said, well I can’t really blame him. She laughed and asked, are you a big tit lover like my husband was. I told her the bigger the better. She said, good to know that info. and laughed again. She then went on to say that there was hardly a day that went by that they didn’t have sex. She said many times she would wake up in the middle of the night and he was rubbing her pussy or sucking on her tits. She also said several times I would be in the kitchen making dinner when he got home from work and he would shut off the stove or the oven and said I am horny, dinner can wait. She asked me if all of this was embarrassing me and I told her not at all. I don’t know if it was the wine talking but I told her it’s actually turning me on. She laughed and said, me too. One last thing she told me was a real shock. She said nobody knows this but my husband actually had a heart attack while we were having sex and died. She kind of laughed and said, he left the way he wanted to, doing what he enjoyed the most.

We talked a little more and then she excused herself to go to the kitchen to get dessert. My cock was bulging in my jeans after that conversation. I had a naughty thought and a course of action in my mind. If I took action, it could mean either I get sent home with a hard cock or I end up in Penny’s bed having sex with her. I knew I had to go for it.

I walked into the kitchen, and she gave me a huge smile, almost like she was reading my mind. She was cutting the apple pie she made. I walked up behind her, reached around her and cupped her large breasts with both hands. She gave a little shiver. Then I whispered in her ear, I am extremely horny. What do you say we hold off on dessert and go to your bedroom for some fun. She quickly turned around, rubbed the front of my jeans and said, I see my plan of talking about mine and my husband’s sex life worked. At that point, our lips met for the first of many kisses and wow, it was incredible.

She took me by the hand and led me to her bedroom. I noticed her bed sheets were turned back like she knew we would end up in here. We kissed again and then she whispered something in my ear that made my cock get even harder. She said, my husband and I made love because we were married. Let’s call what we are about to do fucking. And oh do I want you to fuck me long and hard. Our kiss this time even got more intense.

Before I knew it, she was making the next move. She removed my shirt and then quickly got down on her knees and started unbuckling my jeans. She said, I don’t know if you ever noticed, but when we used to do crossing guard, I used to stare at the huge bulge in your jeans and wanting it so bad. I was in total shock. My cock sprung forward as she pulled down my jeans and underwear. She said, oh my, it’s even bigger than I imagined and have masturbated to. Her mouth immediately wrapped around my cock. It was obvious she had done this before and was very good at it.

She sucked and stroked my cock and balls so incredibly. About 10 minutes into, I could feel the sense that i was soon going to cum. I wasn’t sure how she felt about taking a load of cum in her mouth so I warned her. She released my cock from her mouth and stood up. She kissed me again and said, I love the taste of warm cum down my throat, but I want your first load deep inside my pussy. Once again I felt my cock get harder.

I reached down and touched her pussy with my hand for the first time. I was amazed how wet her pussy was already before I even touched it. I started kissing her and slowly moved her backwards to her bed and laid her down so her pussy was at the edge. I reached over and grabbed a pillow and placed it under her so her hips jutted upwards. I started kissing her legs starting at the ankles and slowly moving up. Once I got to the area of her pussy, Ikissed her inner thighs and barely touched her pussy with my tongue and then away. I did this several times until she begged me to stop teasing her. I continued until she was going crazy and I could tell she couldn’t take any more of it.

My tongue plunged into her wet pussy, and she let out a loud moan. It wasn’t hard to find her clit as it was one of the most swollen clits I have ever experienced on a woman. My first touch with my tongue on it sent major shivers thru her body. I knew right away it was not going to be tough to provide her with her first climax. As I started licking her clit, her body started bouncing on the bed. I then reached up with both hands while my face was buried in her pussy and fondled her huge tits and nipples. This sent even more shivers through her body. I knew all I needed to do was one more thing. I stopped licking her clit and started biting it gently. I was right. She started screaming at the top of her lungs….Oh god, Oh God, Oh God!! She started thrusting her hips and grinding her pussy harder onto my face. She released a river of cum from her pussy. I honestly never met a woman that came so hard and so much.

I let her catch her breath as she rolled over on her back on the bed and gave me that I’m all yours look. I had other plans for her. I was not ready to fuck her yet. I climbed up on the bed and laid on my back. She moved up to straddle me, but instead I told her, not my cock, my face. i want you to sit on my face. Therre was no hesitation from her. She planted that warm wet pussy right on my mouth. I gave her another clit lashing. It was a matter of minutes before her body started shaking and she started screaming even louder this time as another huge river of cum flowed onto my face and in my mouth. She tasted so incredible.

She laughed at me and said I think we need to go take a shower and get both of us cleaned up before we fuck. She took my hand to the bathroom as we started the water and climbed in. I immediately grabbed hold of her luscious tits and soaped them up. I then sucked on her nipples for the first time. They were so large and incredible. the whole time she was stroking my hard cock with her hand.

She was about to shut the water off, when I told her no. I turned her around, so she was facing away from me. I surprised her by bending her over and putting my cock in her for the first time. I figured since it was all soapy, it would be good and slippery, even though her wet pussy really didn’t need it.

My hard cock glided right into her and she had no problem taking my full eight inches. She let out several moans as I started pumping away on her. She got really nasty by telling me to fuck this old ladies pussy and demanding I make her cum. I swear it only took me about twenty thrusts into her pussy before she had another orgasm. This lady was insane. After she came, she started talking dirty again telling me to cum deep inside her old pussy. With talk like that, it didn’t take me long and i came with one of the most thundering orgasms I ever had.

After that we went back to her bed and fucked some more. Finally about midnight we finally had that apple pie. As we talked more, she confided in me with what she called a very dark secret. She said you know my husband died five years ago. If I hadn’t had sex in five years, my pussy would be pretty tight but as you saw it’s not. I told her I just figured i was not the only guy she has invited over for sex in the past five years. She went on to say that there has only been one other guy she has fucked in the five years. I am like ok, why are you telling me this. I asked her how often he comes over to fuck her and she said usually once a week when he comes over to mow the yard, or shovel snow or do other maintenance. My first thought oh she has her own personal handyman for several things and then it hit me. She told me before her sons handle all the maintenance at her house.

She looked at me and said, I bet you think very badly of me now knowing I let one of my boys fuck me. I looked at her and gave her a kiss. I am 30 years old and I just fucked a truly beautiful older lady that has a wild sex drive. There is no way I can think bad of you.

After that we went back to her bed and fucked until the sun came up. Before I left, I told her I would love to do this again and she agreed. And I threw out the idea of maybe having her son join us in an incredible threesome. I asked her if she thought there was a way her son would be willing to do that, and she said all I can do is ask.