I'm a shy nice guy who didn't have a lot of luck with the ladies. That all changed because of my girlfriend. Her name is Jill and she is blonde, 5'5", a tight firm body, small tits, but a great ass. We have been dating for a while and the sex was great. Little did I know she would make me a slut.
One night while watching t.v. she asked me if I masturbated. That question came out of left field, but since I'm an honest guy I answered yes. She then blushed a little and asked if she could watch. I turned bright red and told her I was way to shy to stroke myself in front of her. Jill was not going to take no for an answer.
Later on that night we made our way back to the bedroom. Jill took of all her clothes and got on all fours in my bed. She then looked back at me while slowly running her hands between her legs. A finger slipped into her wet pussy. One of those sexy wicked grins crossed her face and she said "I need something much bigger in my wet cunt." Wow I loved how aggressive and naughty she was being. My clothes were of in a flash. I placed my 7" cock at the entrance and slammed it home. Normally I need to eat her pussy to orgasm before I can get my whole dick inside her, but tonight she was already dripping wet. I fucked her with long fast strokes, my balls slapping her clit. The sounds of our thighs slapping and her moans were getting me close to cumming. That's when she really surprised me.
Jill tossed her hair to the side and gave me another wicked grin. Her hand slowly crept down her back to her ass. Then she slipped the finger inside her asshole. I could feel her finger through her ass on my cock. She had never done this before and it really got my close to cumming. Jill knew I was close so she told me to stop and made me an offer. She said that I could fuck her ass but not cum in her but. I must jerk off for her to cum. Well I always wanted to try anal sex and was so turned on by her dirty talk that my shyness was not going to stop me. She spread her ass cheeks and I slowly worked my dick inside. Cumming twice had loosed her ass up enough for me to get all the way in. Like I said I had never done this before so I was afraid of hurting her. I was slow and let her adjust to my cock. When I finally got all of my dick in she moaned. I started fucking her slow at first while she fingered her clit. Then she started trusting her hips on my dick. I knew she was about to cum again. I fuck her ass hard while she came screaming. I have no idea how I kept from cumming in her butt. Now it was time to make good on the deal.
My cock slowly popped out of her ass. I knew from the length of her last orgasm that this wouldn't be my last time doing anal. I laid down and looked her in the eyes. Anticipation was burning within those brown eyes. She told me to spread my legs and she laid in between my thighs. I grabbed my cock and slowly started rubbing up and down it. She just stared at it. I closed my eyes pretending she wasn't there so I would be relaxed enough to cum. I started stroking faster. I felt something on my ass and my eyes shot open. I couldn't believe it she was giving me a rim job while staring at my jerk off session. I must admit I loved the feeling of her tongue on my asshole. That was too much for me and I shot cum out over my chest, dick, and balls. At the same time I heard her scream. She then licked up all the cum off of me. That was another first time experience for me. We laid together recovering.
Jill turned her head to me and looked me in the eyes. She said she loved everything we had tried, but most of all loved watching me. I couldn't believe it when she said she had cum just from watching. From that night on Jill got me to jerk off in front of her a lot. She would give me rim jobs and watch. I really like when she wanted me to straddle her chest and masturbate while she would talk dirty. More and more her dirty stories centered around Jill watching me fuck another woman. Little did I know that she was going to make the stories come true.
I found out how much she like to watch me a few months later at the club. I loved going to the club with Jill since she always dressed in next to nothing and would pick out my clothes so I would look my best. We were at a table having a couple of drinks when she had to use the restroom. When she came back she was talking to another woman. This woman was about Jill's height, had jet black hair, 34C tits, and a nice ass. Jill sat with the woman at the bar and ignored me. I figured the woman was someone she knew from work and just waited for the conversation to end. My drink was finished so I ordered another. I also notice Jill and the woman were nearly finished with their drinks so I ordered another round for them. When there drinks arrived they looked over at me and mouthed thanks. Then they turned to each other and giggled. Finally they got up and came to my table.