She had only had sex four times and wanted more experience before going back to uni. She contacted me through Reddit and we talked for a bit, going over our likes and desires. Once we’d decided we were a good fit for each other, we swapped numbers and started chatting on WhatsApp. She was due to head back to uni soon, so we moved quick and arranged a date to meet.

She lived a short train journey from London, so we arranged to meet in Paddington. Her train was delayed, which only added to the tension, and she was very nervous when we met. She hugged me, told me how nervous she was, and I suggested getting a coffee first, which she agreed. We spent an hour talking, and had a coffee and some food, although she didn’t finish her food, which she told me later was due to nerves.

After the coffee, I asked if she was ready, and she said yes. We went back to the hotel. She hardly said a word in the lift, it became very real. When we got in the room, I gave her the remote and asked her to find something while I jumped in the shower. I came out wearing just my boxers and told her to have a quick shower and freshen-up, and not to get dressed before she comes back in. She obliged, showered, and came back in the room naked apart from her socks - she said her feet were cold. She shyly covered herself with her hands as she walked in.

I kissed her and told her to lie on the bed with her bum on the edge. I spread her legs and she had the cutest looking pussy - it was tiny! I went down on her, and spent a lot of time and attention down there, I needed her to relax and enjoy the moment, and then I felt her cum, she was doing fine!

She went down on me next but wasn’t confident, as she’d told me previously, so I guided her. She did lots of oral, worked my perineum, did deepthroat for the first time, and was face fucked for the first time. She got real sloppy, which was a first for her!

Next, I put her in doggy position, applied some lube to her pussy, and slowly went inside her. She was tight! I slowly increased the pace and intensity until I’m thrusting fully and pulling her hips towards me. We had sex in multiple positions as I tried different angles, tempos, and depths, to see which she preferred. Things got exciting in flatiron though, as I put a little lube on my thumb and slipped it up her ass while fucking her. She had told me prior that she wanted to try anal, but there’s a big difference between wanting to, and actually doing. I could tell as soon as my thumb went in that she liked it. I verbally confirmed, and then checked if she wanted to try more, which she did.

The success of anal relies heavily on preparation work… and her being relaxed! Lots of lube, outside and in, and I worked from one to two fingers, stimulating her ass until she came again. I then asked if she was ready to properly try anal, and she said yes, so I put some lube on my penis, and slowly pushed into her ass, reminding her to relax and constantly checking it was ok, as I could feel her tensing and tightening. Once I was fully in, she relaxed a little, as same as earlier, I begun to build up pace and tempo, checking with her as I did. We had anal in multiple positions, she took it really quite rough, and she came twice during it!

I was ready to cum now, and we’d already discussed that she wanted a facial (her first) and some swallow (which she’d done before), so I told her to drop to her knees, mouth open, eyes closed, and I wanked until I came all over her face, putting my penis in her mouth for her to finish me off and suck out every last drop.

Afterwards, we grabbed a shower together and lay under the duvet naked together, watching Big Bang and eating snacks. Aftercare is important. I walked her back to Paddington and we said goodbye at the station. She got the experience she wanted, did anal for the first time, and had three orgasms from anal stimulation (four in total)!

TLDR: Student wanting experience. She had only had sex 4 times. Very nervous. Lots of oral, deepthroat and face fucking for the first time, lots of sex, anal for the first time, 4 orgasms total, first time facial and finished with a swallow.