Straight Male / 43
I have been married for 20 years. For 17 of those, I was completely faithful. Somewhere around my 40th birthday, I started to feel like I wanted more. More experience, more women, more sex. This is a confession of the affairs and dalliances I have had in the past three years. I'm done with that lifestyle, so think of this as a final confession of what I did.
In no particular order:
Eva was a sweet little Texan with a great ass. Met her on Craigslist, had dinner and drinks before going back to her apartment. Nice make out session, blowjob and fuck.
Kirsten is a smart, beautiful professional who I have the utmost respect for. I met her on Ashley Madison. We met several times over a few months. Great make out sessions, we went down on each other, played with each other until we came, but no sex.
"Vegas" (I forgot her name) was a flight attendant I met while flying in to town for a dinner. We shared a cab, and just happened to be staying at the same hotel. We met for drinks with her friends, gambled a bit, drank a bit more before we started making out at a bar. We had to leave, and went back to my room. We screwed around for a couple hours. She wanted me to cum on her tits once, and her ass the second time so I obliged.
I met Carrie on Ashley Madison. She lives in a different part of the country, and I met her when I traveled there on business. Very smart, accomplished and married... She knows how to have a good time, though. I was fucking her from behind, in a hotel window, when I came, she turned around, pulled off my condom, and sucked the rest of the cum out of my dick. Saw her a few times, whenever I made it to that part of the country.
Allison was the only woman I met on OK Cupid. We met at a bar in her hometown. We had a few drinks, some appetizers, then shared some gin before heading out. We made it as far as her car. A quick peck on the cheek turned into a full blown make out session in the parking lot. We quickly moved in to her Prius V wagon, where we screwed around some more. She sucked my cock a bit, then told me she wanted me to fuck her. She had a condom, so I obliged.
One night in Washington DC, I was on Ashley Madison when I started chatting with Janet. She's single, 25 years old, and was looking to experiment. We chatted for about 45 minutes before she was on her way over. She had a great smile, looked a bit like Anna Paquin. We made out, fucked a few times, I went down on her, she went down on me. Was a lot of fun.
Sophie was the first to uncover my dominant tendencies. She was beautiful, tight, and kinky in the best way. Met her on Ashley Madison. We got together several times. She was the second woman I ever throat fucked, and she took it like a champ. Amazing.
Donna... Another meet from Ashley Madison, but she was from a bit too far out of town to meet with frequently. Didn't stop us from meeting up once for dinner and having a great make out session in the parking lot.
Marissa was striking. Beautiful smile, smart, funny. Met her on Ashley Madison as well. We clicked, and chatted a lot. Only made out once...
Lisa was a woman that I met while traveling. Met her on AM first, chatted on Yahoo and over web cam a bit before meeting. She met me in my hotel - was there when I got their from the airport. We were supposed to go out to dinner, but instead decided to have a bottle of wine that I brought up with me. We downed that bottle, started on the second bottle, then ordered food. We started making out, and were fucking with her up on the bathroom counter when the food arrived. I threw on a robe, got the door, had the food brought in to the room, then went back to the bathroom to finish. We fucked 7-8 times that night and the next morning. She told me she loved sex, and wasn't kidding!
Aileen was my first Asian. She loved porn, especially kink. We made out a few times - the first time she blew me in the back of my wife's car after I bound her hands behind her back. Very hot. The last time we were together, we spent the day in a hotel. We watched porn together, she gave me her best porn-style BJ, then we fucked around the hotel - including in front of the window. She was an AM find as well, and a flight attendant...
Jess was a freak. Met her on AM. Her husband was just boring in bed, and she wanted it rough and kinky. We chatted for a while on Yahoo! and over the phone before finally setting up a meet at a local hotel. She arrived at about Noon on a very rainy day. We made out on the couch, before she pulled my pants down and wanted my cock in her mouth. We talked about it before - she wanted me to push my cock down her throat until she gagged, and cum in her throat. I held the back of her head, pulled her on to me, and pushed in deep. She gagged, I pulled out a little, then pushed it back in. I did this until I felt the rush up my legs and shot my load in her mouth. She said she had never done it before, but loved it. We fucked a few more times that afternoon. From behind, reverse cowgirl, missionary for good measure. We only met the one time. She had her fantasy and lived it out.
Lynn was the first coworker I fucked. We were on a business trip, it was late, we were both pretty hammered when we started making out at the bar. Before we knew it, she was bent over naked on my balcony with my cock inside her. We got together once more after that, but then called it quits.
Marie was the second coworker I fucked. Similar story - at a business dinner, got a little drunk while celebrating a big win, and ended up back in her room. She is hot, great body. Would fuck her again if I weren't turning over a new leaf with this confession.
Cathy was the third coworker I fucked. We have wanted each other for a while, and the tension was palpable. One night, after a late night text, she invited me to her room. We chatted a bit, beat around the bush a little, then got down to business. It was sloppy, we were drunk, but it was fun. The next time we were together was a lot more fun. We got in a room, and my pants were off and her mouth was on my cock in seconds. She gives one hell of a blowjob. Almost made me cum right there, but I held off. We went to her bed, fucked some more, then I pulled out and put my cock back in her mouth. Felt awesome, but I took it out, and put it back inside her until I came. We fucked three more times that night.
Cindy was the fourth coworker I fucked. We almost did once a couple years ago on a business trip, but didn't. Later that year, though, we couldn't help ourselves. She was fun, funny, smart. Maybe a little chunky, but great in bed. She had a full muff, but it was nice and soft - kind of reminded me of Janet, but older.
Beatrice is beautiful, smart and horny. Met her on Ashley Madison. She likes to hike, and we went hiking, kissed a little at the end, but that was it. I think about her a lot...
Emily was the fifth coworker I fucked. The first time was on a trip, and we were drunk, but not that drunk. She is freaky, and I like that. Loves her nipples pinched, ass spanked, and gives an epically good blowjob.
Candice was beautiful, 24, funny. I miss her. Met her on Ashley Madison, she was married at the time. We were together a few times, and she is by far one of my favorites. The sex was incredible, and she knew how to work a cock. Pussy was nicely shaved, and sweet...
Brazil... There is a club in Sao Paulo called Cafe Foto. It's packed with the most beautiful women you will ever see, and for about $300, you can take one home with you for the night. I picked out a beautiful blonde to take back. She was fit, firm, all natural, and fucked like a maniac. I got my money's worth, but got no sleep and was dragging the next day.
Shannon was a flight attendant that I met on Ashley Madison. Notice the trend?? That's three! We fooled around a couple times, including a blowjob in my car, but there was no real chemistry. She was dirty, and a great chatter, but in real life... not so much.
Tammy loves fast cars. I mean, she loves them. I met her on Ashley Madison, and we met up for a couple drinks. I took her for a ride in my Mercedes C63 on some twisty roads around here, and I thought she was going to cum from the g forces alone. After the drive, I took her back to a restaurant where we shared a couple glasses of wine before she had to leave. I walked her outside, and she pulled me close, looked in my eyes and started kissing me. We made our way quickly to my car, and made out more. She pulled my pants down and started to blow me, so I shoved my hand down her pants and started teasing her pussy from behind. It was soaking wet. She worked me over with her mouth, and I had her spun up - my hand was soaked, her panties were soaked. She told me to slow down, because she was a squirter and didn't want to get it all over my seat. Hot... She licked my balls, and stroked my cock until I knew I was going to cum. I told her what was coming, and she shoved my cock down her throat and swallowed my whole load.
Maria was another Ashley Madison find. She had a great smile, and these amazing lips. Mmmm.... Great kisser. The first time we met was at a bar at a cheesy chain restaurant. We had a couple drinks, then I walked her to her car. We made out in the parking lot for 20 minutes at least. The next time we met was in a dark parking lot. The kissing got hot and heavy. Her pussy was in my hand, and I knew I was doing her right, I could feel the twitching. She gave me a hand job, but I held off from cumming... Didn't want to make a mess. We chatted a few times after that, but I never saw her again.
Rebecca... Another one from Ashley Madison. She's smart, funny, sexy. We met several times, and still chat from time to time, but just friendly chat. The first time we were together was at a local hotel. She wore a nice little dress, with nothing underneath. We made out standing up, across from the mirror, and I slowly lifted her dress up, revealing her clean shaven pussy. we made out for a while, before I moved her to the bed. We fucked three times that day. We met again, on a hike in a secluded parkland. We found a nice area, set out a blanket, and fucked all day out in nature. Amazing.
Christina is a real go getter. Met her on Ashley Madison, she is in a different state. She ran her own start-up insurance business, and was in the middle of a nasty divorce. We met for dinner and drinks, then went back to my room for a little make out session. It might have turned in to something more, but there was a lot of baggage with her.
One night, in the city, I met this woman at a bar. I thought she was a friend of a friend, but as it turns out, she was just a bar patron. We hit it off. She was beautiful, smart, and worked at a prestigious law firm (I stalked her on LinkedIn). We had several drinks, but when the bar closed down, we wanted a couple more. We went back to her place - a nice apartment - had a little whiskey, a little making out, then lots of steamy sex. She gave a good blowjob, had a nice, tight pussy. Shaved around the lips, but a nice triangle of soft hair above it. Tasted great. At one point she gave me a hand job, and I showered her in cum. She loved it.
In no particular order:
Eva was a sweet little Texan with a great ass. Met her on Craigslist, had dinner and drinks before going back to her apartment. Nice make out session, blowjob and fuck.
Kirsten is a smart, beautiful professional who I have the utmost respect for. I met her on Ashley Madison. We met several times over a few months. Great make out sessions, we went down on each other, played with each other until we came, but no sex.
"Vegas" (I forgot her name) was a flight attendant I met while flying in to town for a dinner. We shared a cab, and just happened to be staying at the same hotel. We met for drinks with her friends, gambled a bit, drank a bit more before we started making out at a bar. We had to leave, and went back to my room. We screwed around for a couple hours. She wanted me to cum on her tits once, and her ass the second time so I obliged.
I met Carrie on Ashley Madison. She lives in a different part of the country, and I met her when I traveled there on business. Very smart, accomplished and married... She knows how to have a good time, though. I was fucking her from behind, in a hotel window, when I came, she turned around, pulled off my condom, and sucked the rest of the cum out of my dick. Saw her a few times, whenever I made it to that part of the country.
Allison was the only woman I met on OK Cupid. We met at a bar in her hometown. We had a few drinks, some appetizers, then shared some gin before heading out. We made it as far as her car. A quick peck on the cheek turned into a full blown make out session in the parking lot. We quickly moved in to her Prius V wagon, where we screwed around some more. She sucked my cock a bit, then told me she wanted me to fuck her. She had a condom, so I obliged.
One night in Washington DC, I was on Ashley Madison when I started chatting with Janet. She's single, 25 years old, and was looking to experiment. We chatted for about 45 minutes before she was on her way over. She had a great smile, looked a bit like Anna Paquin. We made out, fucked a few times, I went down on her, she went down on me. Was a lot of fun.
Sophie was the first to uncover my dominant tendencies. She was beautiful, tight, and kinky in the best way. Met her on Ashley Madison. We got together several times. She was the second woman I ever throat fucked, and she took it like a champ. Amazing.
Donna... Another meet from Ashley Madison, but she was from a bit too far out of town to meet with frequently. Didn't stop us from meeting up once for dinner and having a great make out session in the parking lot.
Marissa was striking. Beautiful smile, smart, funny. Met her on Ashley Madison as well. We clicked, and chatted a lot. Only made out once...
Lisa was a woman that I met while traveling. Met her on AM first, chatted on Yahoo and over web cam a bit before meeting. She met me in my hotel - was there when I got their from the airport. We were supposed to go out to dinner, but instead decided to have a bottle of wine that I brought up with me. We downed that bottle, started on the second bottle, then ordered food. We started making out, and were fucking with her up on the bathroom counter when the food arrived. I threw on a robe, got the door, had the food brought in to the room, then went back to the bathroom to finish. We fucked 7-8 times that night and the next morning. She told me she loved sex, and wasn't kidding!
Aileen was my first Asian. She loved porn, especially kink. We made out a few times - the first time she blew me in the back of my wife's car after I bound her hands behind her back. Very hot. The last time we were together, we spent the day in a hotel. We watched porn together, she gave me her best porn-style BJ, then we fucked around the hotel - including in front of the window. She was an AM find as well, and a flight attendant...
Jess was a freak. Met her on AM. Her husband was just boring in bed, and she wanted it rough and kinky. We chatted for a while on Yahoo! and over the phone before finally setting up a meet at a local hotel. She arrived at about Noon on a very rainy day. We made out on the couch, before she pulled my pants down and wanted my cock in her mouth. We talked about it before - she wanted me to push my cock down her throat until she gagged, and cum in her throat. I held the back of her head, pulled her on to me, and pushed in deep. She gagged, I pulled out a little, then pushed it back in. I did this until I felt the rush up my legs and shot my load in her mouth. She said she had never done it before, but loved it. We fucked a few more times that afternoon. From behind, reverse cowgirl, missionary for good measure. We only met the one time. She had her fantasy and lived it out.
Lynn was the first coworker I fucked. We were on a business trip, it was late, we were both pretty hammered when we started making out at the bar. Before we knew it, she was bent over naked on my balcony with my cock inside her. We got together once more after that, but then called it quits.
Marie was the second coworker I fucked. Similar story - at a business dinner, got a little drunk while celebrating a big win, and ended up back in her room. She is hot, great body. Would fuck her again if I weren't turning over a new leaf with this confession.
Cathy was the third coworker I fucked. We have wanted each other for a while, and the tension was palpable. One night, after a late night text, she invited me to her room. We chatted a bit, beat around the bush a little, then got down to business. It was sloppy, we were drunk, but it was fun. The next time we were together was a lot more fun. We got in a room, and my pants were off and her mouth was on my cock in seconds. She gives one hell of a blowjob. Almost made me cum right there, but I held off. We went to her bed, fucked some more, then I pulled out and put my cock back in her mouth. Felt awesome, but I took it out, and put it back inside her until I came. We fucked three more times that night.
Cindy was the fourth coworker I fucked. We almost did once a couple years ago on a business trip, but didn't. Later that year, though, we couldn't help ourselves. She was fun, funny, smart. Maybe a little chunky, but great in bed. She had a full muff, but it was nice and soft - kind of reminded me of Janet, but older.
Beatrice is beautiful, smart and horny. Met her on Ashley Madison. She likes to hike, and we went hiking, kissed a little at the end, but that was it. I think about her a lot...
Emily was the fifth coworker I fucked. The first time was on a trip, and we were drunk, but not that drunk. She is freaky, and I like that. Loves her nipples pinched, ass spanked, and gives an epically good blowjob.
Candice was beautiful, 24, funny. I miss her. Met her on Ashley Madison, she was married at the time. We were together a few times, and she is by far one of my favorites. The sex was incredible, and she knew how to work a cock. Pussy was nicely shaved, and sweet...
Brazil... There is a club in Sao Paulo called Cafe Foto. It's packed with the most beautiful women you will ever see, and for about $300, you can take one home with you for the night. I picked out a beautiful blonde to take back. She was fit, firm, all natural, and fucked like a maniac. I got my money's worth, but got no sleep and was dragging the next day.
Shannon was a flight attendant that I met on Ashley Madison. Notice the trend?? That's three! We fooled around a couple times, including a blowjob in my car, but there was no real chemistry. She was dirty, and a great chatter, but in real life... not so much.
Tammy loves fast cars. I mean, she loves them. I met her on Ashley Madison, and we met up for a couple drinks. I took her for a ride in my Mercedes C63 on some twisty roads around here, and I thought she was going to cum from the g forces alone. After the drive, I took her back to a restaurant where we shared a couple glasses of wine before she had to leave. I walked her outside, and she pulled me close, looked in my eyes and started kissing me. We made our way quickly to my car, and made out more. She pulled my pants down and started to blow me, so I shoved my hand down her pants and started teasing her pussy from behind. It was soaking wet. She worked me over with her mouth, and I had her spun up - my hand was soaked, her panties were soaked. She told me to slow down, because she was a squirter and didn't want to get it all over my seat. Hot... She licked my balls, and stroked my cock until I knew I was going to cum. I told her what was coming, and she shoved my cock down her throat and swallowed my whole load.
Maria was another Ashley Madison find. She had a great smile, and these amazing lips. Mmmm.... Great kisser. The first time we met was at a bar at a cheesy chain restaurant. We had a couple drinks, then I walked her to her car. We made out in the parking lot for 20 minutes at least. The next time we met was in a dark parking lot. The kissing got hot and heavy. Her pussy was in my hand, and I knew I was doing her right, I could feel the twitching. She gave me a hand job, but I held off from cumming... Didn't want to make a mess. We chatted a few times after that, but I never saw her again.
Rebecca... Another one from Ashley Madison. She's smart, funny, sexy. We met several times, and still chat from time to time, but just friendly chat. The first time we were together was at a local hotel. She wore a nice little dress, with nothing underneath. We made out standing up, across from the mirror, and I slowly lifted her dress up, revealing her clean shaven pussy. we made out for a while, before I moved her to the bed. We fucked three times that day. We met again, on a hike in a secluded parkland. We found a nice area, set out a blanket, and fucked all day out in nature. Amazing.
Christina is a real go getter. Met her on Ashley Madison, she is in a different state. She ran her own start-up insurance business, and was in the middle of a nasty divorce. We met for dinner and drinks, then went back to my room for a little make out session. It might have turned in to something more, but there was a lot of baggage with her.
One night, in the city, I met this woman at a bar. I thought she was a friend of a friend, but as it turns out, she was just a bar patron. We hit it off. She was beautiful, smart, and worked at a prestigious law firm (I stalked her on LinkedIn). We had several drinks, but when the bar closed down, we wanted a couple more. We went back to her place - a nice apartment - had a little whiskey, a little making out, then lots of steamy sex. She gave a good blowjob, had a nice, tight pussy. Shaved around the lips, but a nice triangle of soft hair above it. Tasted great. At one point she gave me a hand job, and I showered her in cum. She loved it.
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