My first anal

This was a couple years ago, but I still remember it very well.

I was insanely horny one night so i signed up for a sex dating/chat site. I'm siting around, rejecting chat invites from guys, thinking I'd never want a cock. After a while, I decided to try chatting up a guy, see what kind of stuff he would be into. I started to watch some gay porn too, to see what i was getting into, and I found myself pretty horny.

I started to chat up guys all over the site, but then I got a chat invite from a self-proclaimed tranny. She told me her name was Jade. She said she could pick me up, bring me to her place and she'd fuck the hell out of me. I nervously said yes, and snuck out (I lived with my parents at the time). I waited where we agreed to meet, and soon a van pulled up and a large black woman stepped out. She was wearing the bright yellow shirt and red pants so i knew it was her. I walked up and she kissed me and we got grabby right there in the dark.

I was super hard just from her grabbing my ass and kissing me, and I started to feel her ass too. She whispered "I'm so ready to fuck your ass, baby." I said "please take it easy, I'm new." She chuckled and told me to relax, and this was just some fun.

After a ten minute drive we arrived, and she said her friend would be there, but not getting involved. We went in, and another black woman was siting inside, smoking and watching tv. "Is that your bitch tonite, Jade?" She replied, "Yeah come watch when you hear him moan." She laughed and pulled my loose fitting jeans down right there in the living room, for her friend to see. My cock stood at attention, and her friend just stared and said "hope you don't plan on using that, baby."

I figured she was teasing me because my dick wasn't too big, but I figured it out soon enough. We went into a small bedroom where there was some porn going on. "Jack off until i'm ready." Jade left the room, and i sat there lazily stroking my dick, in a stranger's bedroom, second thoughts racing through my head. She returned soon, holding rubbers, tissues and some lube. She told me to stand up and bend over. Soon I felt something stroking my asshole.