How it started

My high school girlfriend used to finger my asshole whenever she blew me. It started with just rubbing it, then pressing on it, until she eventually slide in. After it had more or less become routine, she started eating my ass and fingering me before she’d even touch my cock to get me hard. Sometimes she’d eat my ass and jerk me off instead of blowing me. One day she brought up the idea of a butt plug, and the next day she slide a plug inside me instead of her fingers and legit fucked my ass nice and slow while she blew me.

Then in college, I was hooking up with a girl who mentioned she was curious about playing with a guys ass. I told her my high school experience and she was very excited if I’d let her try. Started out just touching rubbing and pressing. Eventually she would suck me hard, plug me and we’d fuck. That was sort of as far as it went with her. However I had found out that her one friend, Emily is who got her interested and curious about it. So I met Emily at a party. She knew exactly who I was, and even what my plugged looked like. As the night went on and we drank more. Emily was showing me more and more attention. She whispered in my ear that she wanted to peg me, she wanted my ass. We were both drunk, nothing more happened that night.

I was waiting for my girlfriend outside her dorm, and I ran into Emily. She was a little embarrassed and asked me if I remembered the party. I told her I did, and asked if she remembered. She invited me up. After some small talk, she pulled out a strap-on and asked me what I thought. I told her she’d have to eat my ass if she expected it to fight. Much to my surprise she pulled out a bottle of lube instead. She told me to get on the bed...I wasn’t used to such direct language, I had always controlled things, but I was hard and horny. She rubbed the lube over my Ass hole and her cock. Wasted no time in slipping it right in, and started really fucking my ass. She had reapplied lube, but it still hurt. She spread my ass wide and kept fucking me. Her thrusts started shallow, but were now long and deep. Suddenly she stopped and pulled my hips towards her held it deep. I was so full, I started to move forward off of it, but she collapsed on top of me burying it deep again, grinding her hips hard. I could feel the leather straps rubbing my asshole, like she was trying to push them inside me also. Suddenly she rolled off me...she had been grinding her pussy on her side of the strap on...she had cum, but I didn’t. I told her I didn’t cum yet and motioned for her to finish me off. She unbuckled her belt and told me do get dressed