Please excuse the chaoticness of this story
Im trying to convey the memory/details of something that happened many years ago and be forewarned that unfortunately these all end in a way that is probably not going to be the way you/I would have liked them to...
When i was 20, before I had ever heard the term cuckold or knew that I was one, i was dating this girl katie. Sometimes she would dress sexier than normal and i loved when she did.
It wasn't right away, but i realized that not only did I like seeing her dress sexy for me to see, but it was also a turn on that strangers were am getting the view i was.
Though we never discussed it, it was obvious that she also liked the extra attention, so I started buying her very short skirts and bustier like tops.
A group of us used to play a weekly poker game and a few days before poker night i jokingly said that she should wear the new skirt that i had gotten for her.
It was the shortest one yet, the back didnt even completely cover her butt, i definitely didnt think she would go for it but she did, asking me if i really wanted to her. After a few seconds i said yes, yes i really would like that.
Once before poker night, we somehow got on the thought topic of her being in bed before poker was over, still wearing the skirt, but having the door open a little bit so anyone going for the bathroom would get a very nice view.
This progressed to the questions of how she should handle it if kyle (the resident guy who would have zero problem fucking a friends girlfriend) were to enter the room, we agreed that she wouldn't instigate anything but wouldnt stop anything either. While she did wear the miniskirt to poker, nothing beyond that happened.
Another night, we were fooling around and somehow got on the subject of her going into our friends room across the hall and climbing into bed with him.
At the last minute before she went, she stopped and asked me "panties or no panties?" I definitely chose no panties and off she went completely naked to climb into his bed.
That night, I didn't even know it was possible, I got myself off, stayed completely hard, and got myself off again.
Unfortunately, nothing happened, which made sense since our friend came out as gay a few years later lol
There were times on the highway that we would start going back and forth on her removing clothing items, letting truckers get a eyeful.
Overall, it was unfortunate. She was my first real girlfriend for any length of time and due to my own insecurity, despite being turned on by some instances of being cuckolded, i was also very jealous and overbearing towards her when we could have had alot of fun had i known what a cuckold was and that i was one.
The two instances that now get me very aroused thinking about but hurt me a ton when they happened were her getting drunk and giving a pussy job (no penetration) to a friend she grew up with and had dated in the past.
The second was when a small group of our friends played strip pool on a night that i was working. Now, i like to embellish the memory and think of things they could have done,but didn't tell me about.
FUCK MY WIFE!
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