More info to help you decide
My wife is 23 (I'm 26). The women in her family are very beautiful, and she's never gotten too angry at me for "noticing" them (she said she's gotten used to it, and that at least I'm not as bad as her high school boyfriends that would openly gawk at her sisters and mother). She encouraged me to be honest when writing up this info to help you vote, but she admitted that reading it definitely made her less likely to feel sorry for me when I was locked. My wife has told her older sister and her best friend a little about our chastity play, and my wife said she has considered telling her mother. She hasn't told anyone else.
My wife's best friend is 24, they were in the same sorority in college, and they see each other at least once a week. I actually see her more often since I work with her. We mostly work in separate areas, but she is technically over me and likes to jokingly remind me that she's my "boss" despite being a little younger than me. Years ago when they were in college and my wife and I were just dating, some of us were having a party since it was my birthday. my wife gave me the best present: she and her best friend took me aside where nobody else could see, and let me watch them kiss. It was only like 30 seconds, and just kissing, but so hot. Unfortunately they've never repeated this for me, but who am i to complain. She knows a little about our chastity play, and one time surprised me when we were jokingly making fun of each other and she told my wife "you know what, just flush his keys down the toilet." She was just joking of course, but the reminder that she knew and the way she joked casually about getting rid of the keys actually turned me on a lot.
One of my wife's coworkers and work friends is a woman around 28 or 29. She's not as attractive as my wife, but still quite pretty. She is bisexual, and both my wife and I think that she wants my wife. At first my wife took it as harmless flirting, but eventually started to think it was a bit of a crush. I've only been around her a few times and was nice, but immediately it seemed like she didn't like me. Still, my wife knows that the idea of this woman having a crush on her turns me on and leads me to fantasize about them together, so she thought this would be a good addition to the list. She doesn't know about the chastity play.
My wife's mother: I've actually known my wife's mother longer than I've known my wife. My wife's hometown is very close to mine, and her mother is a teacher at the high school I went to. Clarification: she was the teacher all the boys stared at and fantasized about. It's kind of odd admitting this about my mother in law, but my wife knows that all her guys friends used to check out her mother and that surely her mother's students were doing the same. I just happened to be one of those students. I keep my eyes behaved now, but once had an awkward moment with my mother in law when my wife and I went swimming in the pool at her mother's house. I went in to use the bathroom and on my way back out encountered my future mother in law in the hallway. She had decided to join us in the pool, and for the first time I was seeing her in a bikini. There she was, this woman that filled my fantasies throughout high school, standing two feet away in a bikini. She started making small talk, and there i was in my swim trunks starting to get an erection and not knowing how to hide it. All I could think to say was that I needed to go to the bathroom, but she said "didn't you just come out of there?" As I tried desperately to think of something to say, she smirked and said "Just go. I understand," and then walked away. Very embarrassing, but she's always been nice to me and has never mentioned that situation to me (though she eventually told my wife about it; they both thought it was funny). Doesn't know about the chastity stuff, but my wife said she has considered telling her.
My wife's younger sister is 19, has sort of curly red hair, and is in college. We've always gotten along well. She and my wife both have pretty big, very nice boobs. But she tends to wear things that show them off more (tight/low cut) (sometimes my wife jokes with her "put your boobs away" because of how she dresses, but it's all in fun). She doesn't know about the chastity play.
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