This is the story of the best Valentin's day ever!!
My name is Nathan but everyone calls me Nay.
I was only 19 at the time but I was aware of my sexuality enough to understand that I had an attraction to men. Thankfully my girlfriend Jean (also 19) knew I was bi curios and once told me she liked the idea of me with another man. This made things very interesting.
She was the one who started the conversation after fingering my ass while she gave me head one day. The feeling of her fingers inside me made me cum so much and the orgasm felt like the longest one I had ever had until that day.
We talked about it and the next thing I knew we were at the adult toy store. Jean really got into the idea of putting things up my ass, she bought a bullet vibrator, anal beads, anal numbing cream, a 6 inch dildo with straps, and a butt plug.
As soon as we got back to my place Jean wanted to try out some of our new toys. We started with just the vibrator and that felt good but we soon moved on to the anal beads. At first I did not get the point of the beads but I was excited to try new things. I swear I had an orgasm the second she pulled the beads out of my ass but there was no cum and I was not even hard. It was a really fun day and we had only just gotten started.
Next she strapped on the dildo and asked me to suck on it. I was not sure what this was going to accomplish sense I did not think either one of us would get anything out of it but I got on my knees and started sucking. Jean started playing with herself as she watched me suck on the dildo then she grabbed the vibrator and slipped it under the strap on. I could barely feel the vibrations at the tip of the dildo as I sucked on it. Jean grabbed my hair and started pulling and pushing so I would take the dildo deeper and suck it faster. I could see she was really turned on and by this point my cock was hard enough to cut diamonds. I continued to suck on it and even let her jam it all the way down my throat a couple of time but I kept gagging so I stopped.
Jean looked at me and said "Are you ready to take it up the ass babe?"
I just said "Sure why not?" Then I climbed on the bed and got on all four with my ass hanging out in the air. I tried not to show it but I extremely excited about the whole idea. The anticipation of what was about to happen was killing me and I felt like it took Jean a really long time to work her way behind me. Finally I felt the cold touch of her finger covered in numbing cream teasing my ass hole and slowly working its way inside.
She played with my ass for a minute or two pushing and pulling her finger inside me faster and faster. I felt a worm tingly feeling as the cream started to heat up. Next I felt her put one hand on my lower back and then the first touch of the dildo. She rubbed it on my ass hole and butt crack for a little bit then she started slipping it inside me ever so slowly. I could feel it going inside me deeper and deeper as she slowly thrusted back and forth. Then I felt her waist bump against me from behind as she had gotten the full length of the dildo up my ass.