I had a friend who decided to change jobs and went to get her massage therapy license. One of the things that students need to do is get a certain number of hours, so the school offers super cheap massages, about $25, plus whatever you want to tip.
Because of our friendship, she wouldn't practice on me, but she recommended a girl from her class. I got two massage sessions from her. We had a good chat, and then I ran into her one night while out with my friend. I had a few drinks, so I got her phone number and asked her out.
I was 30, she was 24. She was 5'6", blonde, and was the type that was skinny with a little chub. Like a size 8. I would later find out that she was self-conscious about her size, but she was hot as fuck to me.
After the first time we fucked, I asked her if it would be akward if I kept getting appointments with her, and she said it was fine and would actually help her practice techniques she would have been nervous about with a stranger.
So the next time I went, everything was going normally but she seemed to go a little higher when doing my thighs. My brain started racing thinking about it, and my dick started to get hard. When she had me flip on my back, I decided to drop the towel.
"Well, make yourself comfortable, I guess", she said with a giggle. I was convinced she was doing this on purpose because she had a grin on her face when her hands would go right up to my junk and graze it, and my hardening dick would twitch. When I saw that she liked that, I would exaggerate the reaction.
Then she was standing over my head and reaching as far down as possible. Her shirt was lifting up and her belly button was right over my face. I couldn't handle it anymore, so with her next stretch her fingertips were just grazing my dick, so I grabbed her hand and put it on my cock. I moaned to finally have her really touch it, and she laughed and said she wondered how long it would take.
She moved around to stand next to the table and went to grab some more oil when I asked her to take her shirt off. So now she's standing there topless and starts stroking my greased-up cock.
She started doing the two-hand twist, leaning over my cock with her tits hanging. She would slap my cock against her tits, and the whole thing was hot as fuck. Having been edged for the last 20 minutes, I really wanted to cum, and told her I was getting close.
She put her mouth around the head of my cock, one hand continued stroking, and the other cupped my balls. I put a hand on the back of her head and pushed down, and she started bobbing. There were a few gags, and I shot into her throat. She pumped a few more times, pulled up to swallow, and continued stroking until every drop was out.
As I lay there in bliss, she wiped up her hands and mouth, told me to "take my time getting dressed", and that the "receptionist could set up my next appointment." With that, she left the room.
I didn't want to make it weird, so I tipped her the normal amount and set up a follow-up for the next week.
$45 for a blow job happy ending? Yes, please. We saw each other for a few more months and ended up fucking in the room a few times.