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Dating Disasters
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Straight Male / 25
Finally Got It Right
My wife Ashleigh and I met several years ago when we were both teens. Problem was, I was infatuated with her older sister, Carolyn a frigging beautiful blonde who happened to be on the school's swim team. At 5' 11" and slender, she could have dated anyone in her school. They lived with their Mom on the affluent side of town and although Carolyn was a few months older than me, we started seeing each other.
I guess I was the bad boy type to her and by graduation we ( at least I was) were getting a little serious. The issue was as inexperienced as I was, she was downright prudish. Makeout in the car or basement, maybe some dry humping, but she wasn't giving in. I had met her Mom, but the first time I met Ash, she was in their pool around 8pm. I came around back and she introduced herself and told me Carolyn wasn't going to be home from work until late, there was an issue. So, I sat in one of the pool chairs to wait. I was surprised that Ashleigh, although very pretty, was nothing like her sister. Maybe 5'4", she was definitely " curvy". A Redhead ( she said strawberry blonde) with piercing greenish gray eyes , she was swimming in a Tshirt and bathing suit bottoms, cranking some vintage heavy metal. As I lit up a cigarette ( trying to be the tough guy) she told me that it was bad for me and to put it out. Then, she started splashing water at me. I told her a few times to stop, but she was giggling and kept at it. Finally, I put my wallet and phone next to my cigarettes' and lighter and jumped in to dunk her.
As you might expect, we struggled and splashed and tried to drown each other until we were tired. Then, as we were just floating around, we ended up kind of hugging as we bobbed up and down. I could feel her boobs floating and bouncing against me and I knew I was getting hard, so I swam to the side to get away, afraid to get out because she'd see my bulge. She swam over, and asked why I didn't get out and before I could answer she kissed me. I don't think I fought too hard, although I thought I did. So, I popped of the pool and let my legs dangle in. While I was taking my t shirt off, Ash grabbed my junk. I told her to stop and she just laughed and said that I wasn't getting anything of Carolyn. She undid my button and started stroking me and told me to lie back. Ash took me in her mouth, still stroking with her hand and I was in heaven. It only took a minute or two and I told her to stop. She asked why, and I swear, when I started nutting, she kind of jumped a little, then her eyes kind of rolled and she started swallowing each shot. When I was done, she climbed out of the pool and threw me her towel and headed to the poolhouse.
Over the next few weeks, Ash and I hooked up a lot. I was delivering auto parts for my fathers store, and anytime I was in the area, I'd stop over. We'd fuck, or go down on each other and never told anyone. At night, I'd go out with Carolyn and get frustrated, but knew Ashleigh was willing.
College came, and I left town, Carolyn went to University in the next state, and I'd leave my Community college and drive to see her. After a while, I found out she was getting nailed by some Frat guy and everything ended.
Well, my Dad passed just before I was set to graduate. Ashleigh showed up at the service, and she lost some weight and looked great, we chatted and I promised to call her. We met one night for drinks, and she was wearing her favorite Pantera shirt, we went back to my place and yeah, we hooked up. I felt like I was home. All I remember was her stopping me from pushing, telling me " Deep and slow". Then she took the top and I just stared at those huge jugs as she ground on me until she was there. She whispered, " now, with me. Now!" And I came. Oh, did I cum. Ash rolled off me, had her head sort of in my armpit as we hugged, and I felt wetness. As tears rolled out, I asked if I had hurt her. Then it just exploded. She slapped my chest and started. " You asshole, I loved you. You were my first everything. I did anything you wanted, you never took me out, anywhere. You'd screw me 3 times in a day and I couldn't walk. I had to dispose of all the rubbers you left in the garbage can. I even let you do butt stuff before you left for school, but all you did was follow Carolyn like a puppy!"
Well, I felt like shit. I didn't know what to say, I thought she knew more than me. So, I asked " What now?"
She said, " well, now you're going to make up for it"
To this day, we still fuck every chance we get. We got married a year ago. I run the parts store, Ash makes sure Im happy. Oh, and Carolyn? Her and Ashleigh don't really talk, but she's been sleeping her way to the top of that communications firm.
I guess I was the bad boy type to her and by graduation we ( at least I was) were getting a little serious. The issue was as inexperienced as I was, she was downright prudish. Makeout in the car or basement, maybe some dry humping, but she wasn't giving in. I had met her Mom, but the first time I met Ash, she was in their pool around 8pm. I came around back and she introduced herself and told me Carolyn wasn't going to be home from work until late, there was an issue. So, I sat in one of the pool chairs to wait. I was surprised that Ashleigh, although very pretty, was nothing like her sister. Maybe 5'4", she was definitely " curvy". A Redhead ( she said strawberry blonde) with piercing greenish gray eyes , she was swimming in a Tshirt and bathing suit bottoms, cranking some vintage heavy metal. As I lit up a cigarette ( trying to be the tough guy) she told me that it was bad for me and to put it out. Then, she started splashing water at me. I told her a few times to stop, but she was giggling and kept at it. Finally, I put my wallet and phone next to my cigarettes' and lighter and jumped in to dunk her.
As you might expect, we struggled and splashed and tried to drown each other until we were tired. Then, as we were just floating around, we ended up kind of hugging as we bobbed up and down. I could feel her boobs floating and bouncing against me and I knew I was getting hard, so I swam to the side to get away, afraid to get out because she'd see my bulge. She swam over, and asked why I didn't get out and before I could answer she kissed me. I don't think I fought too hard, although I thought I did. So, I popped of the pool and let my legs dangle in. While I was taking my t shirt off, Ash grabbed my junk. I told her to stop and she just laughed and said that I wasn't getting anything of Carolyn. She undid my button and started stroking me and told me to lie back. Ash took me in her mouth, still stroking with her hand and I was in heaven. It only took a minute or two and I told her to stop. She asked why, and I swear, when I started nutting, she kind of jumped a little, then her eyes kind of rolled and she started swallowing each shot. When I was done, she climbed out of the pool and threw me her towel and headed to the poolhouse.
Over the next few weeks, Ash and I hooked up a lot. I was delivering auto parts for my fathers store, and anytime I was in the area, I'd stop over. We'd fuck, or go down on each other and never told anyone. At night, I'd go out with Carolyn and get frustrated, but knew Ashleigh was willing.
College came, and I left town, Carolyn went to University in the next state, and I'd leave my Community college and drive to see her. After a while, I found out she was getting nailed by some Frat guy and everything ended.
Well, my Dad passed just before I was set to graduate. Ashleigh showed up at the service, and she lost some weight and looked great, we chatted and I promised to call her. We met one night for drinks, and she was wearing her favorite Pantera shirt, we went back to my place and yeah, we hooked up. I felt like I was home. All I remember was her stopping me from pushing, telling me " Deep and slow". Then she took the top and I just stared at those huge jugs as she ground on me until she was there. She whispered, " now, with me. Now!" And I came. Oh, did I cum. Ash rolled off me, had her head sort of in my armpit as we hugged, and I felt wetness. As tears rolled out, I asked if I had hurt her. Then it just exploded. She slapped my chest and started. " You asshole, I loved you. You were my first everything. I did anything you wanted, you never took me out, anywhere. You'd screw me 3 times in a day and I couldn't walk. I had to dispose of all the rubbers you left in the garbage can. I even let you do butt stuff before you left for school, but all you did was follow Carolyn like a puppy!"
Well, I felt like shit. I didn't know what to say, I thought she knew more than me. So, I asked " What now?"
She said, " well, now you're going to make up for it"
To this day, we still fuck every chance we get. We got married a year ago. I run the parts store, Ash makes sure Im happy. Oh, and Carolyn? Her and Ashleigh don't really talk, but she's been sleeping her way to the top of that communications firm.
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