van_delay
Literotica Guru
- Joined
- Aug 17, 2022
- Posts
- 2,260
Love thisI have shared a little bit of my true experiences regarding this. However after my mom passed, I always wanted to have that thrill in my life, so I ended up dating much older women in my 20's (most in their 50's) I still enjoy it as I am older now, however my fantasies of the M/S relationship have revolved around me embracing a bit of a sissy side to myself, thanks to my ex who also embraced it, (though she wasn't an older woman). I dream of a Mom who tells me what panties to wear if any for the day, keep her updated on how sexy I am feeling through the day, even having me wearing tights, or pantyhose under my masculine exterior. One of my favorite videos to watch that I immerse myself into is Magdalene St Michaels and Nina Lawless, (Magdalene reminds me of my mom quite a bit)