Syd's college roommate SeXStoRY

So Syd and I had been fucking regularly for a couple of months. We weren't really dating and certainly LOVE had never been mentioned, but we really got into screwing one another. One night in between fucks she looked at me and started to tell me about something. "I have been with a woman." "Really, interesting." "Yes, she was my roommate in college, Ann, she gave me my first orgasm." "Very interesting" I said She said to me "We were at my house for Thanksgiving day break, because she lived so far away. We were in my room watching one of those softcore porn movies on cable. She said to me that she had to get off, and that she hoped she didn't mind. At that point she pulled off her panties and started masturbating. remember that I was a Preacher's k** and really sheltered. I had never seen that before or done it, so I watched her. When she came I was slightly in shock." Syd looked at me and saw my hard on, "You like this story?" "Absolutely, tell me more." "Well, she looked at me and saw my amazement. So she asked me if I had ever done that. I said no, and she said that I should, that it felt really good and it relaxed you. I wanted to make her happy, so I took of my panties and shirt and started rubbing my pussy, but I wasn't really getting anywhere. So she took over. She fingered me and rubbed my clit, and showed me how to do it. When I came for the first time, I squirted and she was really excited and thought it was cool." "Needless to say we stayed roommates all through college and had sex a lot." "OK, I said, that is really cool, what made you tell me about it now?" "Well, she is coming into town next week for a conference and we are going to get together." "Oh, I see, and you want to get together. Hey, its cool, we are not exclusive or anything feel free, but I may ask you about it." "No, you idiot, that is not it at all. She has never been with a man, and well, she would like to be." "Ummm, me?" "Maybe, you up for it?" "Well, she sounds really sexy, what does she look like?" Syd handed me a picture that I looked at. In it there was a beautiful young woman, chestnut hair, brown eyes, and a wonderful smile that I am sure her parents paid a million dollars for. "Seriously Syd, this girl Ann is seriously hot, she has never been with a man?" "Yeah, weird huh? Seems like she always gets trapped into woman relationships and men get scared away." "Ok, so how is this going to work?" "Here is what we worked out. You will come in, fuck her and then leave." "Seriously? Just like that?" "Yep, I will not be in the room, but I may come in towards the end," "Ok, sounds interesting. I am game" "That's the sport, I knew you would be." and we fucked again very hard that night. The next Friday, Syd called me. "It's time big guy, here is the deal. While she is a virgin she has had plenty of dildos and shit in her pussy, so you don't have to worry about hurting her. Oh, and check this out, she is on the pill to keep her periods regular, so you are good to go. Just come in and go up to my room, I will be in the living room." I went over and entered the house. I looked over into the living room and Syd waved and motioned me up the steps. I climbed the stairs and went into the bedroom. Ann was in bed, under the covers. She was naked. I said "Hello, nice to meet you." She laughed and said hello. I quickly took off my clothes and got under the covers with her. We chatted for a bit, and I started exploring her body with my hands, and she did mine. Finally she grabbed my cock, and said that it felt good. I started fingering her wet pussy and returned the compliment. I pulled back the covers and started sucking on her nipples. I worked my way down her body with my lips and got to her pussy. It was ultra smooth skinned. I mentioned this to her and she said "I have been waxing for ages, it keeps me nice and smooth. At this point I said "You ready?" and she replied that she was. I put my cock at her entrance and entered her slowly. She wrapped her legs around me and let out a low groan. I worked at a moderate speed and she came a nice long slow orgasm. At that point we moved to doggy style. She reached back and played with my shaved ball sack, which drove me nuts. I told her I was going to cum, but she stopped and asked me to hold off. She went to the door and yelled for Syd to come up. "I really have to thank you for this, it has been great. Now I want to jerk him off and watch him cum up close, help me." I laid back and Ann wrapped her hand around my cock. She jerked me slow,and Syd licked my balls. Ann seemed to get the hang of things pretty quick and soon I was ready to blow. I been not jerking off for a couple of days and so I shot a big load which Ann really seemed to like. Syd licked most of it up and and tried to get Ann to try it, but she wasn't into it. She was a hot fuck for sure.