It was January and bitter cold. Here I am sitting at work in front on a computer monitor. The clock says 3:45pm, Friday. I am just about finished with work for the day. Its kind of a weird slow day. I decide to hit up craigslist and look at some of the posts for casual encounters. Normally it is just full of men but everyonce and a while you will get a woman that posts a really great pic. As soon as I click on it I notice a MW4M, interesting I think. I click on it but no pic. The description reads; "Looking for a young single male for a no strings attached session this evening. Male will only watch, he is not bi so no contact. She is thin attractive 42 yo." There is no picture. But there is something about the post that gets me a little excited. Maybe its the fact that I have never been with an older woman. I dont really know what promted me to reply but i did.
The time is about 4:30 and I notice my yahoo messenger pop up. It is the couple that I sent the email to. Its the man and he is requesting a picture. The only picture i have is of me on my vacation, I have sunglasses on so i guess its ok. I send it to him. Kind of nervous. He sends me one back of his wife. She is very attractive and she takes care of her body. I am instantly turned on. He asks me a bunch of questions which I happily answer. Then he asks if I have any questions. I really dont know what to ask so I ask a stupid question.... What is her favorite position? He answers doggie. Now I am getting hard, I ask if she likes anal... as I wait for the response my heart starts to beat as if it was going to jump out of my chest. I have never tried anal before. I have always dreamed about it watching porn. He answers.... she loves it. I was rock solid now. He asks to meet for a drink. I agree and get the address. It was about a 40 min drive but I didnt care. I go home take a shower and get dressed making sure I smell and look great. I hop in my car and head out. At this time its about 5:30. I arive at the Bar which is more or less a lounge, very high class. I go in and its kind of dark. I stand at the enterance a bit and look around. I notice a gentelman waving me over. I walk over to a dimmly lit booth. And he is sitting by himself.
"Jason?" he asks
"yea"
"Have a seat"
He has a bottle of Red wine sitting on the table and three glasses. I look around quickly to see if his beautiful wife is there. I couldent find her. He thanks me for meeting so quickly. He asks me some more question... What I do for a living, how long I have been in there area... basic chit chat. Thats when I notice her walking towards our table. She has a pair of black ladies dress pants on a white blouse and a black jacket over it. Her hair is in a bun an she has thick plastic framed glasses on. She is beautiful.
She sits down and introduces herself. I shake her hand and say "nice to meet you" She turns to her husband and says. "What do you think?" he says "lets order some dinner and see what you think." We all order little appitizer things and talk a little bit and drink wine. They are both really really nice people and my cock softened up now and I can carry on a nomal conversation. We order some dessert and she whispers something in her husbands ear. He smiles and says "go for it." she switches sides and sits next to me. She whispers in my ear " your really hot" she puts her hand on my crotch and starts rubbing. I am instantly hard. Dessert arrives. She has about two bites and says to her husband "why dont you pay and meet us in the car" He smiles and says "you got it" As I walk behind her I keep thinking to myself how hot this woman is. She leads me to a silver Chevy tahoe. She opens the back door and climbs in, she says "come on in" I hop in and no faster then when I close the door she has her tounge in my mouth. We start making out and I am really really hard. She has her hand down my pants on my hard cock. Damn she smells so good. What felt like about about 10 seconds goes by and the door opens and her husband jumps in the truck. Not saying a word he starts driving. We are still kissing when she takes my hand and stuffs it down her pants. I feel her pussy and it is steaming hot and dripping wet. I finger her a little bit and she moans. "Wait Wait" we are almost there. I take my hand out of her pants and she takes her hand out of my pants as well. We arive at a very very nice house and pull halfway into a garage. We hop out and they lead me into the bedroom. She says I will be right back, heads into the bathroom. Her husband says "enjoy my friend". He takes his pants off and sits down in a dark corner of the room.
About 5 minutes go by and she walks out of the bathroom in white thigh highs and a matching corset with no panties and high heels shoes. She walks swiftly toward me and unbuttons my pants she grabs both my underware and pants and pull them down. She starts sucking me hard, grabbing my balls at the same time, it felt so good and she was so hot. I said "Im gonna cum" she stops everything. And says not yet. She sits on the bed and spreads her legs open, her shaved pussy just called for me. I was never really good at eating a woman out but I had to eat it. She was so sweet, the more I licked the more of her juice came out. She said "it feels so good." She says I want you to bang my ass... I almost came when she said that. From the corner of the room a condom is flung at me. I put it on, as I get it on she takes some KY and lubes up her ass. She says start slow. I grab her hips and slowly feel my head enter her anus. She says "ok now go all the way in" i slowly push. I start to see white it feels so good. I start pumping. She whispers "harder" I pump her harder. "She says, dont cum in my ass" I pull out and she says are you ready to cum. I say yes. She reaches over and pulls off my condom. "Fuck my pussy now" I stick my raw cock in her pussy, its so wet and hot. I bang her hard missionary. When she says wait. She pulls me out and says Doggie now. I enter her from behind and Start pounding like a mad man. I yell "im gonna cum" she says cum inside of me deep. I keep pounding until I loose control I push one more time really deep and release me seed inside of her. When I do she moans in passion. I pull back and push deep again and cum deep inside of her. I wait there a moment and then pull out. When I do cum drips out of her all over the sheets. She looks over at her husband who has cum all over his hand from jerking off. "How was that?" He looks at her and says "that was really hot."
We get cleaned up and she walks me to the truck. We hop in and drive to the Lounge where my car is. Before I get out she says "wait, this ones for you" she unzips my pants, and starts massaging my cock. I get hard again quickly. She then starts sucking harder then before. I yell "o my god, im gonna cum" I then release in her mouth as she keeps sucking. She cums up and swallows it all. She then Thanks me and say "Have a nice ride home".
After that I found out that they where moving and moving too far for me to drive. To this day we still IM each other and talk every once and a while. What a great time we had!
The time is about 4:30 and I notice my yahoo messenger pop up. It is the couple that I sent the email to. Its the man and he is requesting a picture. The only picture i have is of me on my vacation, I have sunglasses on so i guess its ok. I send it to him. Kind of nervous. He sends me one back of his wife. She is very attractive and she takes care of her body. I am instantly turned on. He asks me a bunch of questions which I happily answer. Then he asks if I have any questions. I really dont know what to ask so I ask a stupid question.... What is her favorite position? He answers doggie. Now I am getting hard, I ask if she likes anal... as I wait for the response my heart starts to beat as if it was going to jump out of my chest. I have never tried anal before. I have always dreamed about it watching porn. He answers.... she loves it. I was rock solid now. He asks to meet for a drink. I agree and get the address. It was about a 40 min drive but I didnt care. I go home take a shower and get dressed making sure I smell and look great. I hop in my car and head out. At this time its about 5:30. I arive at the Bar which is more or less a lounge, very high class. I go in and its kind of dark. I stand at the enterance a bit and look around. I notice a gentelman waving me over. I walk over to a dimmly lit booth. And he is sitting by himself.
"Jason?" he asks
"yea"
"Have a seat"
He has a bottle of Red wine sitting on the table and three glasses. I look around quickly to see if his beautiful wife is there. I couldent find her. He thanks me for meeting so quickly. He asks me some more question... What I do for a living, how long I have been in there area... basic chit chat. Thats when I notice her walking towards our table. She has a pair of black ladies dress pants on a white blouse and a black jacket over it. Her hair is in a bun an she has thick plastic framed glasses on. She is beautiful.
She sits down and introduces herself. I shake her hand and say "nice to meet you" She turns to her husband and says. "What do you think?" he says "lets order some dinner and see what you think." We all order little appitizer things and talk a little bit and drink wine. They are both really really nice people and my cock softened up now and I can carry on a nomal conversation. We order some dessert and she whispers something in her husbands ear. He smiles and says "go for it." she switches sides and sits next to me. She whispers in my ear " your really hot" she puts her hand on my crotch and starts rubbing. I am instantly hard. Dessert arrives. She has about two bites and says to her husband "why dont you pay and meet us in the car" He smiles and says "you got it" As I walk behind her I keep thinking to myself how hot this woman is. She leads me to a silver Chevy tahoe. She opens the back door and climbs in, she says "come on in" I hop in and no faster then when I close the door she has her tounge in my mouth. We start making out and I am really really hard. She has her hand down my pants on my hard cock. Damn she smells so good. What felt like about about 10 seconds goes by and the door opens and her husband jumps in the truck. Not saying a word he starts driving. We are still kissing when she takes my hand and stuffs it down her pants. I feel her pussy and it is steaming hot and dripping wet. I finger her a little bit and she moans. "Wait Wait" we are almost there. I take my hand out of her pants and she takes her hand out of my pants as well. We arive at a very very nice house and pull halfway into a garage. We hop out and they lead me into the bedroom. She says I will be right back, heads into the bathroom. Her husband says "enjoy my friend". He takes his pants off and sits down in a dark corner of the room.
About 5 minutes go by and she walks out of the bathroom in white thigh highs and a matching corset with no panties and high heels shoes. She walks swiftly toward me and unbuttons my pants she grabs both my underware and pants and pull them down. She starts sucking me hard, grabbing my balls at the same time, it felt so good and she was so hot. I said "Im gonna cum" she stops everything. And says not yet. She sits on the bed and spreads her legs open, her shaved pussy just called for me. I was never really good at eating a woman out but I had to eat it. She was so sweet, the more I licked the more of her juice came out. She said "it feels so good." She says I want you to bang my ass... I almost came when she said that. From the corner of the room a condom is flung at me. I put it on, as I get it on she takes some KY and lubes up her ass. She says start slow. I grab her hips and slowly feel my head enter her anus. She says "ok now go all the way in" i slowly push. I start to see white it feels so good. I start pumping. She whispers "harder" I pump her harder. "She says, dont cum in my ass" I pull out and she says are you ready to cum. I say yes. She reaches over and pulls off my condom. "Fuck my pussy now" I stick my raw cock in her pussy, its so wet and hot. I bang her hard missionary. When she says wait. She pulls me out and says Doggie now. I enter her from behind and Start pounding like a mad man. I yell "im gonna cum" she says cum inside of me deep. I keep pounding until I loose control I push one more time really deep and release me seed inside of her. When I do she moans in passion. I pull back and push deep again and cum deep inside of her. I wait there a moment and then pull out. When I do cum drips out of her all over the sheets. She looks over at her husband who has cum all over his hand from jerking off. "How was that?" He looks at her and says "that was really hot."
We get cleaned up and she walks me to the truck. We hop in and drive to the Lounge where my car is. Before I get out she says "wait, this ones for you" she unzips my pants, and starts massaging my cock. I get hard again quickly. She then starts sucking harder then before. I yell "o my god, im gonna cum" I then release in her mouth as she keeps sucking. She cums up and swallows it all. She then Thanks me and say "Have a nice ride home".
After that I found out that they where moving and moving too far for me to drive. To this day we still IM each other and talk every once and a while. What a great time we had!
