A bit of background to start: She’s a mother of one, had only slept with two guys, had been in a long term relationship for the past five years, was recently single, and her confidence was pretty low.

She had seen my post and sent me a chat. We messaged briefly, she communicated well, and she was very clear about what she wanted - a good fucking for confidence and experience (with an undertone of validation). We discussed and agreed everything, swapped numbers, video verified, and arranged a meet around when she could get a babysitter.

She wasn’t local, so we arranged a hotel roughly halfway between us. I arrived first, had a shower, and got everything out in preparation (camera, tripod, and lube). She arrived about an hour later and we met outside so she could check I was who I said I was, safety first! She was visibly nervous, she’d never had a hookup before, but she was happy to go up to the room.

We had already discussed everything in detail, and I always like to start a meet with the woman stripping naked for me, on command, on camera. It quickly establishes a dynamic where I’m in charge, and also cuts through any nervous awkwardness, we get naked straight away! She was aware of this, and as soon as we were in the room she stripped naked, before I’d even had a chance to turn the camera on, and I was still fully clothed. Never mind, we were off!

I had her drop to her knees and give me a blowjob, something she said she hardly ever did, and her ex rarely got. She was surprisingly good, and with a little guidance, she blew me for a few minutes. I then took over and face fucked and deepthroated her, the latter was completely new for her and she gagged, lots. I then let her continue sucking me at her own pace. She told me after that this was the longest blowjob she’s ever given.

She was ready for a release, and I lay her on the bed, bum near the edge, propped up by a pillow, legs spread wide, and we had sex. Slow and passionate to start with, getting faster and deeper with every one of her groans. We rotated between sex and oral for a bit, and then she tried anal for the first time, which was the thing she was most nervous about. We used lots of lube and went real slow to start, and after a small amount of discomfort at the start, she really got into it. I thought she orgasmed during, but she clarified she was close, but didn’t quite. Either way, she enjoyed it!

We had more sex, more oral both ways, she orgasmed twice in doggy, and when I was about to cum I grabbed her head and she started sucking me, swallowing every drop!

We lay on the bed together, exhausted, and debriefed on the hookup. She really enjoyed it and said she’d never been fucked like that before, both passionately and animalistic. She also admitted that she didn’t think she’d actually ever go through with meeting somebody online, that anal wasn’t as bad as she thought, and that it was the longest blowjob she’d ever given.

We showered, dressed, and went out for some food - Nando’s for those who are interested. She headed back home after, and I stayed the night in the hotel. And if you’ve made it this far, well done! I’ll try to keep up with my write-ups for future meets.