So I finally had the courage to take the leap! I prepared all day. Took a bath, shaved, prepped my ass with a buttplug, put on my cute pink chastity and pulled on some sexy panties. I made sure I was all clean and ready to go. In the evening I grabbed my stockings and bra and pulled them on. I was ready and full of anticipation. I've had things up my ass before but never had a full blown fuck session. I pulled out my buttplug, put a good amount of lube on my dildo and I was ready. I slowly slipped it in and man did that feel good! I felt so full! It was a bit awkward sometimes because I had find out which position worked for me. But once I got in the rhythm it felt soooo good! Couldn't achieve a sissygasm yet (duh), but the orgasm I had was sooooo good!! I think I never came so much!! Just thought I'd share! 😅