I arrived in college as an uptight virgin, the closest to sex was a short feel of a fat girls tits at a drive-in, before she pushed me away.
My roommate on the other hand was the anti-me. I can confidently say he had model good looks, because he honestly was a model, having appeared dozens of times in several department store catalogs since he was 13. He was outgoing, and friendly, and one flash of his dimpled smile and perfect teeth had girls in his dorm bed in record time. I swear... he got laid the first the night we arrived, nailing the girl that sat next to him at orientation. I was shy, unsure of myself, and in total awe of Jason. In the first month, he had sex at least 10 times, with at least five different girls... all beautiful. I spent most Friday and Saturday nights in the common room, waiting for him to finish the deed, and come tell me it was okay to come back. I would've have been pissed, but he was so nice, and was going out of his way trying to getting me laid. He would ask girls all the time if their room mates were available, embarrassing the shit out of me.
It was October 6, 1990.... 10:45 pm when my life changed. Jason stuck his head into the common room, and called my name. I looked over, and Jason's face and shirtless torso were leaning around the door, and he was waving for me to come. I went to the door, and he excitedly looked at me and said, 'C'mon, I got a girl in the room, and she will help you with your 'problem!' I looked down, and saw Jason had on only his BVD's, his erection barely concealed by the thin white fabric. We got back to the door to our room, and he whispered for me to just let him take the lead. We entered the room, and Jason slid next to this blonde girl sitting on his bed, illuminated only by the light from the closet. She had his comforter pulled up over her chest. Jason introduced me, and like the dork I was, I put my hand out and said 'nice to meet you'. She giggled, extended her hand, and the comforter fell, revealing the two most perfect breasts I had ever seen in my life. I can state that emphatically, as they were the only two breasts I had ever seen in my life. She made no effort to cover them, and as I stared in total awe at them, she giggled again, and then asked 'you really a virgin?' I just nodded, and she pulled me onto the bed, her now sitting between Jason and myself. Jason reached his arm around her back, and cupped her breast, pulling her back into his chest, and she giggled again. 'Ashley, if you help Brian out, he'll be forever grateful, right Brian?'
I just nodded, watching as Jason stroked her nipple to hardness. Ashley ran her hand up my thigh and on top of my raging hard on, and giggled again. She turned and kissed Jason, still pawing me. She broke off her kiss, ran her hand up to my t-shirt, and told me to take it off. I quickly pulled my shirt off, and she tugged on my shorts, and said these too. As I pulled my shorts and underwear off, she started to rub Jasons erection through his underwear, watching me. Jason slid his underwear down, freeing his dick, and pulled on Ashley's panties. She lifted her hips, and as Jason pulled them off, I saw my first pussy. Jason quickly ran his index finger into her, and Ashley put her fists around both of us. She slowly masturbated us, as Jason leaned over and licked her nipple, furiously rubbing her pussy. Jason looked at me, grabbed my hand, and pushed it onto Ashleys pussy. I froze, my hand just sitting on her crack, feeling the moistness (unexpected.. but I was a dork), when Ashley put her hand behind my head, and pulled my into her breast. Like the instinct of a baby to breast, I latched onto her nipple, gently sucking and flicking it She moved her hand over mine, frozen on her pussy, and guided my index finger to her clit. 'Rub it here' she directed, returning her hand to my dick. Jason was now leaning back eyes closed, enjoying the hand job from Ashley. He tensed up, whispered he was cumming, then shot a spurt into his stomach. Again I was surprised, as I never 'shot' just oozed. But his stomach was coated. He leaned in and took over on Ashleys pussy, and watching him work her pussy, and seeing his cum on his stomach and chest made me cum right away, in the most intense orgasm I have ever had. Ashley giggled again, wiped her hand on my chest and leaned back into Jason. He was furiously rubbing her as she writhed against his chest, then with a little gasp, had her orgasm. Jason reached over and grabbed a towel, wiping Ashley's pussy, then himself, then tossing it to me. I wiped my dick and pubes clean, feeling their juices on the towel. Ashley patted my still erect dick.. and all I could do was mumble 'thank you'. She pulled her pants up, put on her bra and shirt, and said 'you're welcome' with another giggle, and asked Jason to walk her home.
I flopped on my bed, my head still whirling, and promptly jerked off again, reliving the experience. When Jason got back, he closed the door, and laughed saying the room stunk. He peeled off his clothes hopped into bed, and as I thanked him over and over, he informed me that Ashley had said she thought I was cute, and if I kept my mouth shut, she'd take my cherry too, next time.