One of my best friends from high school had gone off to Kansas to play football in college. While there, he began using d**gs and got arrested. I would stop by and see his parents from time to time, but when his mom called and said he had gotten arrested, I went right over. I had plans on playing college football at Ohio State but injured my knee, so I went to a local college. I also continued to weight train so I could stay in good shape.
When I arrived at my friend’s parents’ house, his mom was sitting at the kitchen table drinking a beer and I could tell she had been crying. I gave her a hug and asked her what happened. She gave me a beer and told me the story. While she was telling me the story, I realized she had been drinking for some time, as she was slurring her words and not making sense from time to time. She drank three more beers while we were talking; I had two.
Now, she is not a beauty queen, but she is attractive and has a nice body. She has great tits!!! She is the type of woman who has great sex appeal. There is something about her that you can’t put your finger on that makes you want to fuck her. I remember having fantasies about her seducing me in high school and masturbating many nights after being at their and seeing her.
She actually walked in the bathroom one time when was I masturbating at her house—she had been laying out and I could not help myself. I was so embarrassed when she walked in and caught me. I had lubed my cock with Vaseline and was stroking it like a madman. I had just started to come, and when I opened my eyes, she was standing there. I did not know what to say. She smiled and said, “Looks like you are having fun!” I turned red! She said, “Don’t be embarrassed—we all do it!” Then she walked out.
The night of her son’s arrest, she was very worried. I tried to comfort her and we started talking about some of the funny things that had happened over the years. She asked me for another beer; she was pretty d***k. I said there was no more, and she sent me to the basement to get another 12-pack from the fridge. When I came back up, I gave her another beer and she said, “Remember the time I caught you jerking off in my bathroom?” I instantly blushed. She smiled and said, “Don’t be embarrassed. You have a very nice cock. She stood up and walked over to me and said, “You have really put on some muscle this summer. You look great.”
I said, “You look really good, too!”
She ran her hands over my chest and my cock got hard. I was trying to move so she would not see it, as I was wearing gym shorts and it was very obvious. She asked what I was thinking about when she walked in on me playing with myself. I began to stammer. She said that she had had fantasies that it was about her, and that she had fantasized that we had had sex right in bathroom.
Then she sat on my lap and my stiff cock poked her in the leg. She said, “So, it was about me.”
I said, “Yes, I have had many fantasies about you.”
She began to stroke my cock and I asked about her husband. She said, “He is out of town on business. Don’t worry about him.” Then she leaned over and kissed me. Her hand felt so good on my cock, I could not believe this was happening. She stood up and removed her shirt.
I said, “Are sure you want to do this? Your son is one of my best friends and you have been drinking. I don’t want to take advantage of you.”
She said, “I have wanted to fuck you for years!” Her tits popped out and they were beautiful—40D with the most perfect nipples. Her nipples are large, almost double the size of a pencil eraser, round and about one and a half inches long. I grabbed her and started playing with her tits, sucking them and biting at her nipples. She moaned and said, “Harder.” I was sucking like I was breast-feeding. I pulled her shorts off to find she was not wearing any panties. My cock strained against my shorts as she stroked it. She finally freed it and started stroking it. Her hand felt so good I almost came right then.
I pushed her back against the table and helped her up on it. She spread her legs wide and guided me into her pussy. I had to have her. I apologized for lack of foreplay but promised to make it up to her. She laughed and said, “This is just like my fantasies—you can’t stop yourself, you have to take me.”
As I slid my cock in, she let out a deep, throaty moan, which really turned me on. I started with long, slow strokes, letting her feel the entire length of my cock. I told her that her pussy felt good and was really tight and wet. She said, “I have not had sex in nine months.”
I was shocked and said, “I will satisfy you tonight.”
She wrapped her legs around me and pulled me in. I started fucking her hard and fast. She moaned loudly and dug her nails into my back. I pulled out and turned her around so I could see her hot ass. I fucked her doggie-style, as she was bent over the kitchen table. Her tits bounced wildly as I hammered her from behind. Then she started to come!
When she was done, she asked me to stop. She dropped to her knees to suck my cock. Her mouth was better than her pussy. She sucked me for a few minutes, then got up and led me to her bedroom. We started to 69 each other. Her pussy was dripping—the more she sucked the wetter she got. She had another orgasm. She kept sucking my cock. I begged her to stop so I could fuck her some more, but she would not. I shot a huge load in her mouth. She took it all and kept on sucking. I asked her to stop because it was too intense right after coming. She did not stop, but kept on sucking. My cock went limp and she kept on sucking. Then, after about 10 minutes, my cock got stiff again.
She stopped sucking it and rolled over on her stomach. She said, “Take what you want! Use me, I am yours!!!” I paused, trying to figure out what that meant, and then guided myself into her tight, wet slit. She moaned and said, “Fuck me hard.” I jackhammered her pussy. I slipped out and when she was helping me back in, I felt her adjust under me. As I slid in, I felt a lot of resistance. I pushed harder and she let out a deep groan as the head of my cock entered her. She panted, “Slow, slow, please go slowly. Be gentle.”
I slowly kept pushing, fighting the urge to jam my cock in her. Then I realized she had guided me into her ass. I whispered to her, “Thank you, I love your ass and have dreamed of fucking you in it.” She smiled and grimaced as the full length of my cock entered her ass. Her ass was so tight, I was having trouble getting in. It felt like it was trying to keep my cock out. I told her, “Breathe and bear down,” and she did and my cock went deep in her.
She groaned and I asked if she was OK, and she replied, “It hurts and feels good. Just go slow. The only thing I have ever had in my ass is a finger.”
I grabbed some lube and slowly pulled out; her ass gripped my cock like it was trying to hold on to it. She asked what I was doing. I said, “You are so tight I need some lube. It will be better for us both. I lubed her tight, pink rosebud and my cock, and reinserted it, this time a bit faster than the first time. She reared up and yelped and begged me to go slow. I said, “Breathe and bear down, trust me.” I fucked her ass slowly with long, deep strokes, listening as she gasped on the in-stroke and moaned deep in her throat. I whispered in her ear that her ass felt so good and tight. It was like heaven. I told her that it was a dream come true to fuck her ass.
I started stroking faster and harder. She squealed at first and pulled away. I said, “Relax and enjoy. You have to embrace the feeling and the pain will turn to pleasure.” Fucking her ass was euphoric. I was lost in the sensation. The only sounds were her moans and gasps, which turned to sounds of a woman in deep pleasure. I was getting close to coming and started fucking her harder and harder. I tried to control myself, but the feeling was too intense.
She bucked wildly under me. She said, “Fuck me! Come in my ass!”
That took me over the edge. I started drilling her virgin ass. She moaned loudly, yelling, “Fuck me, oh please come, please come in my tight ass. I can’t take much more.” Her begging made me come very fast. I came so much it hurt. I collapsed on her and started to apologize for being too rough. She said no, it was good, that she was just new to this, and the more we did it, the more she’d like it. I asked why she let me fuck her ass and she said, “Your ex-girlfriend was over with Tera, Tom’s girl, and I overheard them talking about how much you like anal sex and how much fun it was.” She had been fingering her ass ever since and fantasizing about me taking her ass.
We continued our affair for the next three years. She got divorced, and her son moved home, which made the affair tougher to hide. He almost caught us several times. Once, he came in just as she had taken a load of cum in the mouth from me, but that is another a story for another time.