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My [M27] birthday weekend with my GF [F31] and FWB [M30s][Chastity][Cuckold][Femdom][FM]

Background:

My girlfriend (Harley) and I have explored cuckolding pretty early on in our relationship. She has since slept with about 5 guys. We've only had one guy willing to have me present while I was there, but he couldn't keep it up. About a month ago, we agreed that I could not fuck her until I had lost 20 lbs. for the first week, I wasn't even allowed to sleep in the bed with her. The couch became my new bed. It wasn't bad, considering she let me sleep in the bed while she stayed over and fucked her current fwb.

Day 1:

The Hottest Girl I've Ever Fucked [mf] [pictures] [long]

Disclaimer: I did this whole thing on mobile, please excuse any typos or fucky formatting.

Early Autumn 2015: I had had a somewhat-debilitating crush on Daisy since literally the first moment I met her, a bit over a month prior. I didn't make any romantic moves to avoid alienating her (she had just moved to town and worked for the same employer) but invited her out in a group of friends a few times.

Balcony [f]un with [m]y wife on a family vacation.

My wife and I took a trip last summer with my brother, my mom, and her boyfriend. We are late twenties. She is short and curvy with a great ass and huge tits that are never contained by a bathing suit. I was horny as hell and had my hands all over her every time I could steal a moment.

[MF] Fucked my roommate after letting go multiple opportunities on drunken nights

Last year I was looking for a new place. My current lease was ending in two weeks and I was nowhere close to finding a decent place. Finally I get a mail from this girl and the place sounded perfect. It was 2 bed 2 bath to be shared between two of us and was being subsidized a bit by previous leaseholders who were subleasing it to us. I go and look at the place and it is pretty much perfect.

[MF] In the backseat of her parents' car, with them in the front

I was in my late twenties and my girlfriend at the time was in her early twenties, I'll call her Lyssa.

Lyssa was gorgeous. Perfect body. Natural C breasts, amazing ass. She was 5'5" and had green eyes and shoulder length ombre hair. Probably the best looking woman I've ever been with and maybe the best looking I will ever be with. Once when we were out together a guy watched us walk by, staring at her. He actually said "wow" out loud. I was pissed but I had to get used to it, she received attention like that everywhere we went.

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