So this is like really embarrassing to admit, but I'm freaking out a little. I HATE typing this, but I don't trust myself on this and need advice
So, about me. I'm a chef who works at a reasonably nice hotel restaurant (4 star place). I'm pretty good at that, I think. I'm a big guy - very physically fit, who participates in body building competitions sometimes. Had some decent success there, but not like I'm a professional. I'm single, in my early thirties.
I've been dating this woman for about 3 months - her name is Ashlee. Now me and Ashlee have been friends since high school. Kind of lost touch when she went away to college, but reconnected shortly after she graduated. I've had a huge crush on her for like...as long as I can remember. I mean, don't get me wrong - I haven't been pining away for her this whole time. I've been in relationships, etc. But I've always had feelings for her. Never told her. We were just good friends, but recently decided to take things to the next step
We're pretty different. She's SOOOO smart! Like she's a forensic accountant - super good with numbers! And investigating - she's basically amazing. Like she could be a baddass character on one of those police procedural shows lol. Plus she's pretty and funny and just the best. I'm in love. Like...a lot
We haven't had sex yet - taking it slow. To be blunt, one of the reasons why things haven't progressed is because I sort of have a really small penis and I'm embarrassed about it.
It's dumb I know - I'm an adult here, but listen...she's like a million times smarter than I am. She's not dating me for my mind (such as it is, LOL). Like, I think physical attraction is one of my main strengths here. And I totally know that she's not a perfect physical specimen either - she's very overweight for (only getting heavier over the years) and has confessed to being very self-conscious about it. Personally, I think she's gorgeous. Always have. Actually one of the reasons we got closer and ended up dating was because she asked me to help her with exercising, trying to lose weight. But anyways, I know that we both have our own body issues, but like...what am I going to do???
I just don't want her to be disappointed is all. I've had issues with sex in the past - I'm such a big person everywhere else (built up muscles, etc), that it's a bit jarring when the clothes come off, and it's revealed how small I really am. Prior to Ashlee, I wasn't really dating much. And on her end, I'm sure Ashlee has probably imagined how I look, right? How could she not be disappointed?
So where I need advice is, like...should I talk about it to her prior to having sex? It just seems like a creepy and weird conversation to me? Or do I not tell her, and let things progress naturally? I'm just REALLY nervous about this, because more than any person I've dated in the past, this is a relationship that I don't want to screw up. I just wish I wasn't so psyched out on this