Got a request for a “sexy selfie”...

I (F/30) am in a new relationship (started talking in the summer) with a man (M/39) and we are currently long-distance, seeing each other every 2-3 weeks usually. Even though I’m not all that young, I feel new to dating and navigating a lot of this stuff because my last relationship was a decade-long marriage to my first boyfriend. Also, it left me having some confidence issues which my new guy is aware of, but I try not to make it a big deal. He’s incredibly kind though and has always made me feel good.

Anyways, we typically have nice, long phone calls but don’t text much and thus far, nothing particularly “sexy” has come up. Irl we have amazing chemistry and sex, but so far it just hasn’t translated into anything on the phone. In general, he has a more traditional personality, but I know at the end of the day he’s still a man who probably would enjoy some flirty pics! Well recently we were making some jokes and it morphed into a request for a “sexy selfie”... I said that I’m game, but how sexy exactly was he wanting? Ever the gentleman, he just said he’s already blown away by my regular selfies and anything beyond that would be more than welcome.

So this leaves me excited but also wondering what should I send him? I am really feeling my own lack of experience on this one. I don’t know that a full-on nude is good right off the bat.. maybe just a cute pic of me in bed with a bra on or something? Idk.. I also don’t want to come across as this insecure or innocent girl. Thoughts? Tips?



Submitted December 10, 2020 at 11:59PM

I (F/30) am in a new relationship (started talking in the summer) with a man (M/39) and we are currently long-distance, seeing each other every 2-3 weeks usually. Even though I’m not all that young, I feel new to dating and navigating a lot of this stuff because my last relationship was a decade-long marriage to my first boyfriend. Also, it left me having some confidence issues which my new guy is aware of, but I try not to make it a big deal. He’s incredibly kind though and has always made me feel good.Anyways, we typically have nice, long phone calls but don’t text much and thus far, nothing particularly “sexy” has come up. Irl we have amazing chemistry and sex, but so far it just hasn’t translated into anything on the phone. In general, he has a more traditional personality, but I know at the end of the day he’s still a man who probably would enjoy some flirty pics! Well recently we were making some jokes and it morphed into a request for a “sexy selfie”... I said that I’m game, but how sexy exactly was he wanting? Ever the gentleman, he just said he’s already blown away by my regular selfies and anything beyond that would be more than welcome.So this leaves me excited but also wondering what should I send him? I am really feeling my own lack of experience on this one. I don’t know that a full-on nude is good right off the bat.. maybe just a cute pic of me in bed with a bra on or something? Idk.. I also don’t want to come across as this insecure or innocent girl. Thoughts? Tips?
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