I've always really enjoyed reading people's stories on this website about how they got into this lifestyle, and I've been meaning to write my own for a while now. I plan to start with some background and add to this thread when I can. I used to write quite a bit for fun, but it's been 15 years since then, so hopefully I'll get better at this as I go along. Hopefully some of you will enjoy hearing about this as much as I've enjoyed living it!
I've changed the names of my wive(s) and myself obviously to provide some anonymity, but this is really my story to the best of my recollection...
A little background
I'm in my early 40's, from the midwest. Raised in a small town and married my first wife at the ripe age of 20. We were both virgins and fairly religious as we attended the same church together and went to high school together as well. I had always had a rebellious streak, and was a typical 'Pastor's Kid' since my dad was the pastor of our church. I was popular, 6' tall, sociable, and pretty successful in school as well, so had my pick of girls in the church.
Holly was tall and statuesque, about 5'10 and 135 lb with long light brown hair and some great DD tits, plus a decent ass for the time (asses weren't as big of a thing for white girls then...). I pursued her throughout high school and after graduation we finally started going steady.
When we were 17 (while we were flirting with the idea of dating) we watched the movie "Any Given Sunday" together. Anyone that is familiar with that movie knows about the infamous locker room scene, but we had no idea. After it played, Holly was bright red and insisted that it was fake! For some reason the entire exchange turned me on, I remember being hard and we went back and watched the scene several times to 'see if it was real'. This was before HD was really a thing, so a somewhat grainy scene on a 24" CRT TV made things uncertain (circa 2000 or so). Holly asked me if that was a normal size. Being a typical 17 year old, I said it was. I went home and jerked off thinking about it, and this manifested in my first interest in interracial/cuckold porn, which became somewhat habitual over the next few years. I kept this habit a secret from Holly, of course given our conservative upbringings.
Fast forward 4 years, we were together and got married at 21. I took her virginity. We left our church and attended an in-state public university. We started drinking, going to bars, and exploring the world that we had previously been sheltered from. We became somewhat adventurous sexually but I don't think I was very skilled in bed at all. We got on well enough, though looking back I'm sure the sex was pretty unsatisfying for her. We eventually took a vacation to Miami, Florida and while we were there I talked her into going to Haulover Beach, as I'd always wanted to go to a nude beach.
When we got there I went nude, but Holly kept her bottoms on, which was fine. We spent the afternoon in a state of perpetual titillation discussing the bodies of those around us, but as we were going to leave, a very muscular hung black man walked by. Watching Holly out of the corner of my eye, she didn't take her eyes off of him for the entire time he was near us. I had to roll over on my beach towel to hide my obvious erection. I teased her about it a little, and she acted appropriately embarrassed. When we got back to our hotel that night, I brought it up in bed. She took the TV remote and held it up to my dick. "I think he really was literally the size of this remote and he wasn't even hard. That's crazy!" I reached down and her pussy was soaked...we had some of the best sex of our marriage. I was hooked. This was around 2007.
Eventually my cuckolding obsession culminated in Holly and I fooling around with a (white) friend who was a marine who lived in our spare room as a roommate during a time when we needed a little extra money. While I was initially involved, it turned into a months long affair and he was much more sexually experienced than me. When I found out they had been sleeping together, it broke our marriage up. She took off and joined the army, leaving me with the house we owned together. I had gotten fat and had dropped out of college, (probably had something to do with her cheating on me...) working a somewhat menial job, and was basically house poor in 2009 during the housing crisis. I had pretty much become a loser, and I was newly single living in a college town.
Over the course of the next six years I got in the best shape of my life, went back to school, sold the house and got my own place. I landed a great job at a tech startup out of college. I stayed single, and after an initial struggle of re-learning how to talk to women, I had the time of my life and became somewhat of a ladies man. Numbers are hazy but I definitely passed 50 women sometime before I turned 32. It got to the point where I was ready to seriously date again as sex had become meaningless. I had lots of kinky sexual moments with randoms - threesomes and other situations, too much to detail here, but through it all I had a cuckolding/interracial hotwife kink. I was hoping that when I did find someone she would be what I fantasized about, but didn't want to make it a 'must' have as I thought actually being in that kind of relationship was pretty unrealistic.
That's when I met Claire (to be continued...)
Attached are some pictures of Holly from back in the day.
I've changed the names of my wive(s) and myself obviously to provide some anonymity, but this is really my story to the best of my recollection...
A little background
I'm in my early 40's, from the midwest. Raised in a small town and married my first wife at the ripe age of 20. We were both virgins and fairly religious as we attended the same church together and went to high school together as well. I had always had a rebellious streak, and was a typical 'Pastor's Kid' since my dad was the pastor of our church. I was popular, 6' tall, sociable, and pretty successful in school as well, so had my pick of girls in the church.
Holly was tall and statuesque, about 5'10 and 135 lb with long light brown hair and some great DD tits, plus a decent ass for the time (asses weren't as big of a thing for white girls then...). I pursued her throughout high school and after graduation we finally started going steady.
When we were 17 (while we were flirting with the idea of dating) we watched the movie "Any Given Sunday" together. Anyone that is familiar with that movie knows about the infamous locker room scene, but we had no idea. After it played, Holly was bright red and insisted that it was fake! For some reason the entire exchange turned me on, I remember being hard and we went back and watched the scene several times to 'see if it was real'. This was before HD was really a thing, so a somewhat grainy scene on a 24" CRT TV made things uncertain (circa 2000 or so). Holly asked me if that was a normal size. Being a typical 17 year old, I said it was. I went home and jerked off thinking about it, and this manifested in my first interest in interracial/cuckold porn, which became somewhat habitual over the next few years. I kept this habit a secret from Holly, of course given our conservative upbringings.
Fast forward 4 years, we were together and got married at 21. I took her virginity. We left our church and attended an in-state public university. We started drinking, going to bars, and exploring the world that we had previously been sheltered from. We became somewhat adventurous sexually but I don't think I was very skilled in bed at all. We got on well enough, though looking back I'm sure the sex was pretty unsatisfying for her. We eventually took a vacation to Miami, Florida and while we were there I talked her into going to Haulover Beach, as I'd always wanted to go to a nude beach.
When we got there I went nude, but Holly kept her bottoms on, which was fine. We spent the afternoon in a state of perpetual titillation discussing the bodies of those around us, but as we were going to leave, a very muscular hung black man walked by. Watching Holly out of the corner of my eye, she didn't take her eyes off of him for the entire time he was near us. I had to roll over on my beach towel to hide my obvious erection. I teased her about it a little, and she acted appropriately embarrassed. When we got back to our hotel that night, I brought it up in bed. She took the TV remote and held it up to my dick. "I think he really was literally the size of this remote and he wasn't even hard. That's crazy!" I reached down and her pussy was soaked...we had some of the best sex of our marriage. I was hooked. This was around 2007.
Eventually my cuckolding obsession culminated in Holly and I fooling around with a (white) friend who was a marine who lived in our spare room as a roommate during a time when we needed a little extra money. While I was initially involved, it turned into a months long affair and he was much more sexually experienced than me. When I found out they had been sleeping together, it broke our marriage up. She took off and joined the army, leaving me with the house we owned together. I had gotten fat and had dropped out of college, (probably had something to do with her cheating on me...) working a somewhat menial job, and was basically house poor in 2009 during the housing crisis. I had pretty much become a loser, and I was newly single living in a college town.
Over the course of the next six years I got in the best shape of my life, went back to school, sold the house and got my own place. I landed a great job at a tech startup out of college. I stayed single, and after an initial struggle of re-learning how to talk to women, I had the time of my life and became somewhat of a ladies man. Numbers are hazy but I definitely passed 50 women sometime before I turned 32. It got to the point where I was ready to seriously date again as sex had become meaningless. I had lots of kinky sexual moments with randoms - threesomes and other situations, too much to detail here, but through it all I had a cuckolding/interracial hotwife kink. I was hoping that when I did find someone she would be what I fantasized about, but didn't want to make it a 'must' have as I thought actually being in that kind of relationship was pretty unrealistic.
That's when I met Claire (to be continued...)
Attached are some pictures of Holly from back in the day.
