OP here, with the update some folks have been waiting for.
The GF and I broke it off, thinking it mutually beneficial if we go our separate ways but keep in touch and fuck once in a while. It had gotten to where the sex was the only good part of the relationship. We fucked one more good time before I packed up what stuff I had at her place and we parted with a gratified smile. Don't know how I pulled that off.
Haven't gotten my chance with Ally just yet, but our conversations of late had been getting less and less sexual. Tonight she brought it on full fledged though and while I'm not a sexting type person, we are all over some Tango and I'm telling her what to do to herself on Cam. She started off all nervous saying she wasn't the Cam type, but eventually loosened up when I said I would go first. I got three strokes in before she was rubbing her pussy through her pajamas. Less than a minute later I had her naked and propping her phone up so she could spread her lips with one hand and tease her clit with the other.
Eventually I asked if she'd ever tried rusting herself and she said she could never get more than three fingers In before it started hurting. God I can't wait to get in that tight little pussy! Anywho, I told her to try and she immediately said okay. But I told her to take it slow and enjoy it. Five long minutes later she has her entire hand in her pussy pumping in short staccato motions, Cumming on her own fist.
