I [F] 19 awkwardly had sex with a former teacher [M] 40+

Last year, a few weeks after turning 18 I decided to give casual escorting a go. I mean really casual. Maybe 5-7 a month if that. I’ve always enjoyed sex but I found there was something really powerful about having someone want me enough to pay.

Anyway, a few months after doing it I started getting a call from someone who went by James Michaels. I was a little put off since they sounded familiar but they were nervous so it was hard to tell. At the same time it got me excited at the thought of someone I knew. For obvious reasons they probably wouldn’t tell anyone.

Eventually “James Michael” was all booked for a meet up at a hotel but cancelled his appointment. Thankfully I always get half in advance so it wasn’t a complete waste.

A week later James Michael called on another number (I blocked his old one). He apologized and paid a bit more in advance for the meet up. So I accepted.

A day later I went to a hotel room really curious to see who it was. The door opened and it almost felt like I was on a TV show having a joke played on me. “James Michaels” was none other than one of my old teachers.

I said I had the wrong door but he confirmed he was James Michaels and that he knew it was me and was hoping this wasn’t too weird.

I wanted to get out of the hallway incase anyone spotted us so I went into his room.

My old teacher explained that he knew it was me because of the outfit I wore was the same one and in the same room as on old Instagram post that I had long deleted. That was really really weird because it meant he was following my Instagram for a while and had saved the picture. I assume it happens but I don’t really think about it.

It was also weird because I know he’s married and had seen his wife at the school twice.

After a few minutes of chit chat I calmed down. He offered to pay me more for the hour. Thinking about the whole thing it was weird but also excited. He wasn’t my teacher anymore but it still felt “forbidden” (and it was quite a bit of dosh not gonna lie).

I accepted and took his money. My outfit that he requested was the schoolgirl (I modified my old uniform, which he probably recognized in one of my photos).

I put on some soft background music to avoid dead awkward silences and told him to get undressed. I asked what he wanted but he just told me to take the lead.

I started with a little striptease but he told me to keep the skirt and socks on. I could tell by the way he was looking at me that he had dreamt of this day for a while and that really got me in the mood.

I playfully pushed him back on the bed and sat on him, going in for a long passionate kiss. He was better than I expected at kissing but that’s probably years of experience. I slowly worked my way down and teased his cock. First with a few licks of the tip, then swallow and sucking just the top. This didn’t last long at all and he came in my mouth as I went a little deeper. I was disappointed and he apologised but I played it.

So for the next while I did an erotic massage as we talked. Surprisingly the conversation didn’t feel forced. Once he was ready to go, he asked me to get on top.
I teased his tip again and slowly slid him into me.

I could tell by the hungry look on his face that he probably wasn’t going to last long so I just gave it everything and enjoyed it while I could.

He came about five minutes later and asked if it was good. As far as sex itself went it was less than average but the whole situation brought it up to exciting so I just said yes.

I told him that this was a one time thing and that he shouldn’t contact me. It was fun but still weird. He agreed and so far hasn’t reached out to me.

The whole thing was fun and exciting but it was then that I decided not to do escorting anymore. It was never serious but just for the excitement.

Source: reddit.com/r/gonewildstories/comments/koosvb/i_f_19_awkwardly_had_sex_with_a_former_teacher_m