r/MensSexAdvice

Female here. I’m 31, and my bf is 32. I am in a predicament and I want only genuine advice please. I don’t have anyone else I can turn to about this, because I feel it’s disrespectful to ask anyone I know irl, as it would divulge personal information that my bf may not want my female friends to know. So here I’ve come to the strangers of reddit. Hear me out and don’t judge me.

I have been dating my bf (let’s say Caleb), for about a month and a half now. We met online and met up in person after speaking for a week over phone/text. I was digging his personality because are both nerds and share a lot of niche hobbies. He is successful in his job and is a very sweet kind person. Also a hallmark guy, cringily romantic in an endearing way. Is extremely thoughtful. One thing about him, though, is that he seems very insecure and is easily made insecure.

For example: I am a goofy person and love to roast my partner in a non mean-spirited way. Very light. So he wears this motorcycle chain on the side of his pants, for fashion. And ofcourse I made a joke about “Does it make you go faster? Vroom vroooommmm” Lol. Something playful and banter-esque where he could have easily came back with something to me as a roasty banter contribution and I would have loved it, but instead he gets a sad puppy look on his face;;; and says “Well….I like it :/ >:(“

So he can miss the vibe check sometimes when it comes to flirting. The confidence issue is something that’s hard to bring up to a man.

I can look past that part, of not being able to be fully sarcastic with someone. Some people just aren’t like that, and that’s okay. I can be sarcastic with my friends. Him and I can joke around and stuff but not sarcastic. He’s had a rough childhood upbringing and rough 20’s to say the least in terms of abuse, and started going to therapy for the first time recently. Which I was stoked about; I respected the heck out of that and support it all the way. I do the same.

That was a little background knowledge for my situation.

So being 31, I have always sent partners I was with intimate photos. After a few weeks of being in a committed relationship with him, I wanted a picture of him, because I had sent a few of myself to him already. And he said he wasn’t comfortable sending pictures and never has. So I said okay no problem. I still sent mine, it didn’t bother me. I asked what his size was, and he said 6.

So after a month or so of being together, we had been doing foreplay, and when the “reveal” moment happened, internally I was shocked. It was 3. And narrow. I pretended I didn’t notice the size difference in what he stated versus what it actually was, and I went to town on that puppy and really gave him a good time. He deserved it. He’s a good man. I was very vocal giving him head and made him feel wanted. We did have sex. Afterwards he told me he wanted to cry because he never felt so loved before. As he’s struggled with morbid obesity, abuse, etc. He made a comment one time that broke my heart and it was something of the sort of “Sometimes I have nightmares that you’re not actually into me, because girls that look like you never looked twice at me”.

Here’s the part that makes me want to just bawl my eyes out, because he asked me the next day like how he measured up and how it was. I took it to ChatGPT and asked how I should approach this issue, because that size is just not right for me, and doesn’t do what I need it to do no matter what position we do, it falls out. It’s awkward. And I’m just used to average size and that’s what I prefer…and chat gpt gave me some answers on how to approach the subject but I thought hey let me ask the men of Reddit to see what yall think the most respectful way to say things or not say things from a male perspective. Thank you in advance for reading and responding thoughtfully with no judgement 🙏🏼