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Obsessions
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Straight Male / 18
Lonely Neighbor
My parents are divorced and I live with my mom. It’s an older neighborhood but most of the homes are well kept. Our next door neighbor here name is Mary. She lost her husband a few years ago in an accident am not sure exactly what happened. All I know is that she is over quite a bit and I have always had a thing for her. I’m tall kind of muscular typical high schooler. Have dated plenty so I am not an ugly guy.
Mary is in her late 50s but she rocks a thick curvy body. He and my mom talk over coffee in the kitchen. I sometimes catch Mary checking me out. I do the same she is around 5foot 6 150lbs. My buddies have been over and they have commented on her body. You can see some age in her face but when she wears large sunglasses you can not tell she is in her 50s.
My mom had her over for dinner a few weeks ago and they had some cocktails and had a good time. It was hot and we were in the back yard and when she got a chance she would flirt. I flirted back. We decided to go swimming she agreed and ran back home to change. My mom in the mean time had another drink. I could tell she was feeling tipsy. She always acts silly and a little loud before passing out. Mary came over in a cover and flip flops. Her and my mom are talking she takes her cover off and she is in a 2 piece bikini. The top is a size too small and the bottoms are like boy shorts but come up high and expose a lot of ass cheek.
At this point I am hard as a rock. We swim around and anytime she come or swims close to me she would rub on me. I know she was feeling the drinks so she swam up next to me and as she did I put my hand on her back and let her swim away and got a good hand full of ass as she swam by. My hand ran down her back as she swallows away. She stood up looked at me and came over to me. She asked me if it felt good. I told her yes but I would have preferred to have something else rest on her ass.
At this point my mom was on the lounge chair falling asleep. We got out of the pool and Mary and I were talking very dirty. She told me that she missed being touched and as she said that I put my hand around her and had it on her lower back. I was rubbing her bare back up by her shoulders and all the was down to her ass cheeks. We looked over to my mom and she was sleeping on the chair. We started to kiss she said we should go inside because she is a little loud when getting fucked. We instantly kissed I closed the slider I pulled her bottoms off and bent her over the couch and started to pump away. I did not last long and blew my load fast. I recovered and started slamming in her again. She was amazingly tight. I am by no means large. I’m only about 7 inches long but I am very thick. I didn’t think she was very loud I mean she did make some louder grunting noises. Well fucked that night we cleaned up. I tried to put in her butt and only got the head in before she said that I would have to come over and practice fucking her butt. She said we could order some plugs that would help her stretch out.
She text me the next day and asked if I would come over and we could order a plug. I did come over we fucked again this time she cleaned me up after we were done. I told get to get dressed I had an idea. I told her were something slutty or a really short skirt. She went through her closet and kept asking what I was going to do. She played tennis so she had the top and skirt. She showered did her makeup and got dressed.
I drove us to the adult store that is right next to the town strip club. She had never been in there and was amazed how many people were actually in the store. There were probably a half dozen people. Almost all men and one butch girl.
We spent some time and did some shopping. We got her some toys and a few different sized butt pluggs. One was smaller and they got bigger so we purchased 3 small medium and giant. Mary looked hot as shit. I asked the clerk if he could recommend how to insert them in her. She was beet red but did ask him how f he could recommend some good lube.
He explained start with the small wear it as much as you can and then go to the medium on a few hours. She asked if we could use the bathroom to insert the small one. He said yes and took us spring the back and asked if she needed help. Mary said yes. That was hot sitting there while some guy spread her cheeks and stuck in her plug. He put the plug in his mouth and used spit.
Mary is in her late 50s but she rocks a thick curvy body. He and my mom talk over coffee in the kitchen. I sometimes catch Mary checking me out. I do the same she is around 5foot 6 150lbs. My buddies have been over and they have commented on her body. You can see some age in her face but when she wears large sunglasses you can not tell she is in her 50s.
My mom had her over for dinner a few weeks ago and they had some cocktails and had a good time. It was hot and we were in the back yard and when she got a chance she would flirt. I flirted back. We decided to go swimming she agreed and ran back home to change. My mom in the mean time had another drink. I could tell she was feeling tipsy. She always acts silly and a little loud before passing out. Mary came over in a cover and flip flops. Her and my mom are talking she takes her cover off and she is in a 2 piece bikini. The top is a size too small and the bottoms are like boy shorts but come up high and expose a lot of ass cheek.
At this point I am hard as a rock. We swim around and anytime she come or swims close to me she would rub on me. I know she was feeling the drinks so she swam up next to me and as she did I put my hand on her back and let her swim away and got a good hand full of ass as she swam by. My hand ran down her back as she swallows away. She stood up looked at me and came over to me. She asked me if it felt good. I told her yes but I would have preferred to have something else rest on her ass.
At this point my mom was on the lounge chair falling asleep. We got out of the pool and Mary and I were talking very dirty. She told me that she missed being touched and as she said that I put my hand around her and had it on her lower back. I was rubbing her bare back up by her shoulders and all the was down to her ass cheeks. We looked over to my mom and she was sleeping on the chair. We started to kiss she said we should go inside because she is a little loud when getting fucked. We instantly kissed I closed the slider I pulled her bottoms off and bent her over the couch and started to pump away. I did not last long and blew my load fast. I recovered and started slamming in her again. She was amazingly tight. I am by no means large. I’m only about 7 inches long but I am very thick. I didn’t think she was very loud I mean she did make some louder grunting noises. Well fucked that night we cleaned up. I tried to put in her butt and only got the head in before she said that I would have to come over and practice fucking her butt. She said we could order some plugs that would help her stretch out.
She text me the next day and asked if I would come over and we could order a plug. I did come over we fucked again this time she cleaned me up after we were done. I told get to get dressed I had an idea. I told her were something slutty or a really short skirt. She went through her closet and kept asking what I was going to do. She played tennis so she had the top and skirt. She showered did her makeup and got dressed.
I drove us to the adult store that is right next to the town strip club. She had never been in there and was amazed how many people were actually in the store. There were probably a half dozen people. Almost all men and one butch girl.
We spent some time and did some shopping. We got her some toys and a few different sized butt pluggs. One was smaller and they got bigger so we purchased 3 small medium and giant. Mary looked hot as shit. I asked the clerk if he could recommend how to insert them in her. She was beet red but did ask him how f he could recommend some good lube.
He explained start with the small wear it as much as you can and then go to the medium on a few hours. She asked if we could use the bathroom to insert the small one. He said yes and took us spring the back and asked if she needed help. Mary said yes. That was hot sitting there while some guy spread her cheeks and stuck in her plug. He put the plug in his mouth and used spit.
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