Did you date your friends sister? What was the spark of your story?

I always enjoyed talking with my best friends little sister and making her laugh. I think that her being “off-limits” helped me be friends with her.

I came over to see my best friend one Saturday. She had a t-shirt and underwear on, and I noticed her incredibly attractive thighs. I hope that I was not staring like that looney toons wolf. Her mother told her to go get dressed. She went from the little sister of a friend to an over the top, made me want to cry, gorgeous girl.

Some time later I was looking for a date to prom, and my best friend said “why don’t you take my sister.” I was so confused and exited. She agreed to go with me because her friend was going. She wore a little black dress that showed off her hourglass figure. The image of her in that little black dress haunts my dreams.

One day extremely early in our courtship I went to her house. She was wearing a bikini that made me want to cry. She came up really close, super close, and asked me “what do you want from me?” My mind went into panic mode. I knew that what my teenaged hormones wanted was not the correct answer. I was smitten hard. I let her know that “I wanted to go steady” like we were in was some 1950’s television show. My teenage mind replayed her, in that bikini, asking me that question over and over again. It was torture.

Somehow I ended up dating a girl that I feel is soundly out of my league. We have been together about 26 years, and have been married about 20 years. I really need to see if she was testing me with that bikini move, or if it was just hot outside.

Not a single day goes by that I do not think that I am the luckiest man alive.

TL;DR: dating your friends sister can work out well.



Submitted April 12, 2020 at 12:09AM

I always enjoyed talking with my best friends little sister and making her laugh. I think that her being “off-limits” helped me be friends with her.I came over to see my best friend one Saturday. She had a t-shirt and underwear on, and I noticed her incredibly attractive thighs. I hope that I was not staring like that looney toons wolf. Her mother told her to go get dressed. She went from the little sister of a friend to an over the top, made me want to cry, gorgeous girl.Some time later I was looking for a date to prom, and my best friend said “why don’t you take my sister.” I was so confused and exited. She agreed to go with me because her friend was going. She wore a little black dress that showed off her hourglass figure. The image of her in that little black dress haunts my dreams.One day extremely early in our courtship I went to her house. She was wearing a bikini that made me want to cry. She came up really close, super close, and asked me “what do you want from me?” My mind went into panic mode. I knew that what my teenaged hormones wanted was not the correct answer. I was smitten hard. I let her know that “I wanted to go steady” like we were in was some 1950’s television show. My teenage mind replayed her, in that bikini, asking me that question over and over again. It was torture.Somehow I ended up dating a girl that I feel is soundly out of my league. We have been together about 26 years, and have been married about 20 years. I really need to see if she was testing me with that bikini move, or if it was just hot outside.Not a single day goes by that I do not think that I am the luckiest man alive.TL;DR: dating your friends sister can work out well.
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