Disclaimer: This is not the sluttiest thing you’ll read all day, so please lower your expectations beforehand. This takes place in 2016-ish. At the time, I was 20 and my then GF was 19. Names have been changed for privacy purposes.

My ex (Mary) and I dated for about 3 years. She was always a very innocent looking girl. Blonde hair, petite upper body, wide hips with a fat ass, glasses, wore dresses, etc. She had a very “church girl” aesthetic about her, just without actually being religious.

Anyway, that cutesy, innocent, girl next door look she had was, for the most part, pretty accurate. However, behind a closed bedroom door, she was a demon. The sex drive of a porn star. If sleep wasn’t a human necessity, she would’ve gone for 24 hours a day 7 days a week. I unfortunately am not built that way, so most of our arguments would stem from our differing sex drives.

She wasn’t into the freakiest/kinkiest things, but her being my second relationship and sexual partner (the first being the most boring partner I have ever had, which in turn made me very shy inexperienced sexually), she definitely opened my eyes to a lot of new things. She was very spontaneous and I was not used to that at all. She was my first experience with road head, having riskier sex while people were extremely close by or even in the same room, and yes even me sending nudes. My first partner sent me 1 nude within our entire 3 year relationship, so having someone that actually enjoyed sending nudes was a mind-blowing concept to me at the time.

At one point, I joked that I would make a booty pic she send me her contact photo on my phone. It was legitimately a joke on my end, but she seemed very excited about it and told me to do it. I asked what if someone saw and to my surprise, she responded by saying “So what? Let them see it, it’s just a butt.” We laughed and I agreed and set the picture as her contact photo. After a few days, the nervousness of someone seeing had fleeted and I was just happy to stare at her ass at the top of our text conversation all day. She was away at school at the time and we only saw each other every couple weeks, so getting that reminder throughout the day was nice.

A few days later I’m at work just doing my thing. My boss (Brady) calls me up to his office, I don’t specifically remember what about. Probably just to BS because that’s the type of relationship we had. We were at the time (and are still to this day) extremely close friends. Brady is a few years older than me, definitely the “class clown” growing up, and kind of a perv (more so in a joking way and not in a creepy way. I think he’s just always horny so he turns that into making a lot of sexual jokes). Anyway, I go up to his office and we start chatting about whatever. I guess something about Mary had come up, and I went to show him a text conversation between us, definitely not realizing that he would be able to see her new contact photo… He reads the texts, responds accordingly, and then asks about the photo. I immediately get embarrassed and turn red. He laughs and says it’s no big deal, then pulls out his phone to show me a picture of his GFs ass and says “now we’re even.” That definitely put my mind at ease, but I was still extremely embarrassed.

Later that night, I was on the phone with Mary and I told her about what happened (besides the part that he showed me his GFs ass, I didn’t think she’d appreciate that part too much so I left that detail out). I apologized to her and told her how embarrassed I was when it happened. But to my surprise, she was not phased by it at all. She actually laughed a bit and told me that she figured it would happen eventually and that she didn’t mind at all. In fact, she said “It’s actually kind of hot.” I asked what she meant by that and she said something to the effect of “I guess the idea of you showing me off to your friends is kind of flattering. I almost kind of want you to show people how hot your girlfriend is.” She also specifically mentioned showing them to Brady, but I just assumed that was because he was kind of the reason this whole thing started, so I didn’t think much of it. My confusion turned into horniness rather quickly. I was at little taken aback at first because again, this was all brand new to me at the time. But I became more intrigued and understanding as the conversation went on. She told me there was one rule if I showed her pictures to anyone. She wanted to be told what was said. I obviously agreed and was excited to go to work the next day.

That next day goes by and my shift is coming to end. I march up to Brady’s office, enter, and close the door behind me. Usually closed door meetings are serious, so he immediately asks if everything is okay. I say yes everything is fine and I pull a chair up next to him. Confused, he asks what’s going on. I tell him I have a surprise for him. I open my nudes folder and quickly skim through for a good tease picture to start. I find the perfect one and show him. He stares, looks at me again confused, and looks back at the picture again. He tells me she looks amazing, but asks why i’m randomly showing him. I explained to him that I had told Mary about our interaction the day before and that she told me she actually wants me to show her off. He sarcastically responded “well what are you waiting for, let’s see em!” We both laughed and I showed him a few more, each one slightly more revealing than the last until I showed him a full nude. We were both very much enjoying this experience and he even showed me a few more of his GF as a thank you. I secretly had a HUGE crush on his GF (as did many of the people we worked with so it probably wasn’t much of a secret, but it was a win win for me getting to show off my GF and see his).

That night, I talked to Mary on the phone again and told her about Brady and I’s interaction (again, leaving out the detail that she showed me pictures as well). She was so interested in what he had to say and how I felt about it. I told her that Brady said she looked very good and that it was hot that she wanted me to show her off. I said, for me it was kind of weird at first, but that quickly subsided and it was a lot of fun to watch someone gawk at her beautiful body. She was extremely flattered and turned on by the whole thing. We then proceeded to masturbate on the phone together and had incredible sex the next time we saw each other.

Unfortunately, this all happened toward the end of our relationship so this was as far as we had gone with it. I do still occasionally think about how much further that it could’ve went if we stayed together. Would I have kept showing off pictures of her? Would I have shown more friends? Did she specifically want me to show Brady because she was secretly into him? Who knows, it’s some of life’s greatest mysteries. Thanks to Mary, to this day I still have a thing for showing nudes to my friends. Brady has seen multiple nudes from multiple women I’ve dated/slept with (no that does not mean I will show you…) and it continues to be a staple in our friendship!