Did it with my fiancé’s little sister again, we had to get Plan B [M/F]

First Post Here https://www.reddit.com/r/gonewildstories/comments/3qt16b/i_took_my_fianc%C3%A9s_little_sisters_virginity_first/

A week and a half had passed since we returned from the Maine house. A week and a half since Madeline, my fiancé’ Jamie’s younger sister, lost her virginity to me. 10 days after I had sex with a girl other than Jamie for the first time.

It all started with Jamie’s suggestion that we each try sex with one new person before our wedding. The “hall pass” made sense because we had both been exclusive for 10 years (since we were 14 and 16).

Madeline waited almost 11 days after she seduced me to talk about meeting up again. “I was really hoping you would fix the glass on my busted iPhone.” She was cashing in on the favor I drunkenly promised her months ago. Maddie made her visit to Chicago possible by suggesting to Jamie that they dress up as Victoria’s Secret Angels for Halloween. Home run idea.

I was picturing the PG-13 rated costumes that you on TV. Madeline had apparently taken the intensity up a notch. She ordered wings, corsets, thigh highs and (my favorite) cheeky panties with big bows on them. She also added some knock off kimono robes to cover up their asses just enough to get away with the ridiculous getup. Read more »

I took [m]y [f]iancé’s little sister’s virginity [fM] [Str8] [x-post from gonewildstories]

My fiancè Jamie and her little sister Madeline have the same Jewish genes and good girl charm, but they certainly have different body types. Madeline is a taller 19 year old with DDs and a voluptuous figure. Jamie has been training for the Chicago Marathon, so her ass keeps getting smaller and more firm. Her medium perky Cs compliment the small ass quite nicely.

This past weekend the family gathered at their parent's house in Maine for some birthday celebrations. Dinner followed by board games led to a very PG-13 version of 'Never Have I Ever.' As the parents and older folks made their way home and to bed the game continued with more raunchy questions.

Maddie was wearing blue and white checkered pajama bottoms and I noticed about halfway through the game that her teal thong with pink ribbons on it was hanging out. She must have caught me looking because she pulled it out of sight and looked right at me with a wink. Holy shit. Read more »

I took [m]y [F]iancé’s little sister’s virginity… [First post]

My fiancè Jamie and her little sister Madeline have the same Jewish genes and good girl charm, but they certainly have different body types. Madeline is a taller 19 year old with DDs and a voluptuous figure. Jamie has been training for the Chicago Marathon, so her ass keeps getting smaller and more firm. Her medium perky Cs compliment the small ass quite nicely.

This past weekend the family gathered at their parent's house in Maine for some birthday celebrations. Dinner followed by board games led to a very PG-13 version of 'Never Have I Ever.' As the parents and older folks made their way home and to bed the game continued with more raunchy questions.

Maddie was wearing blue and white checkered pajama bottoms and I noticed about halfway through the game that her teal thong with pink ribbons on it was hanging out. She must have caught me looking because she pulled it out of sight and looked right at me with a wink. Holy shit. Read more »