My first anal sex experience (with stranger)

I'm a 19 years old boy who loves to dress up like girl and generally act like one (although secretly in my room only). I'm shaving my legs, chests and basically my whole body regularly and living as a girl when no one can see me.

So what happened - About month after my 19h birthday i decided to just have some fun and chat with some older guys who was looking for sex with boys in my age just to turn myself on and dream about sex. I was doing that thing for a week or more, i just offered them to have sex, sent pictures where i was dressed like a girl and just ignored messages that was sent back.

And then what happened. I started to chat with a 57 years old man who was living about 3km from my house, as usual just for fun at the beginning. We just started to chat for 2 days and i felt that he is the man with who i could get my first sex. He sent me his pictures and i was shocked - that was teacher from high school witch i graduated before half a year. When i saw those pictures i was pretty nervous and embarrassed but still decided to meet him (since i was already graduated that school, i didn't really care).

So we agreed to meet at Fridays evening at his place. I took a bag, got my stuff with me (i put in stockings, panties, dress, high heel shoes, bra, wig, makeup and cleaned up my ass with enema , because we agreed that i will be dressed like a girl when we have sex). I told my parents that im going out with my friends and went to his apartment. When we met in person he recognized me as a his old student but we both tried to ignore that fact.

I said him that i need to get ready and he showed my way to bathroom. I locked the door and felt my arms and whole body was shaking i was really scared but I told myself that there is no going back and started to get ready. I undressed and took my enema bulb at first (i didn't want it to be messy) after that i put on my makeup and all the other stuff i had with me. I was really looking like a girl.

When i was ready i went out of bathroom and went to bedroom. He was already sitting in the bed only with his underwear on (he was a bit like a "bear" type of man but without beard). I lied down next. We didn't talk much and he just started to kiss my lips witch i didn't much like at first. To get out of this situation i said that i want to suck his dick. I got down on my knees, pulled his underwear off and then i was my first dick. It was a bit hairy (not like really hairy but like shaved ~2 weeks ago) and the size was about 7-8 inches long. I started to lick it and it was quite enjoyable. He asked if he can cum in my mouth but i didn't allow him at first.

After couple of blowjobs i got in bed and laid down on all four with my ass up. He pulled down my underwear and applied lube on my arse. I was pretty nervous because it was my first anal sex (before that i was only used butt plugs and some household things in my ass. He put on condom and slowly started to massage my arse with his fingers that was quite pleasurable. After that he applied more lube and started to work up his cock in my ass. When he first time put it in, i screamed, that was pretty painful. He said sorry and started to penetrate me more slowly.

It took quite a while until he got his whole cock inside my and started to fuck me for real and it was still a bit painful but the pleasure i got from that was so fucking awesome. He fucked me like that for a while and then was the best part. We changed positions, i layed down on my back and put my legs on his shoulders. He started to fuck me faster and faster till we both cum. After that we lied next to each other for a few minutes to rest, then i gave him another blowjob and gone to bathroom to clean myself up and went home.

That was the most pleasurable experience in my life. And we have another meeting next week. :)