Back in college, I hung out with a group of friends in my last two years. It was a mix of young men and women who like to hang out and party, especially on the weekends. There were some natural attractions among us that led to some casual dating at times but rarely turned into a serious relationship. We were in college, full of life and enjoying being young and wild. I wasn't as big a partier as some of my friends. My first priority was keeping up my grades and my studies came first. A couple of my friends, Ken and Evan, were more the "bad boy" party animals that seemed to attract more women than I could ever hope to. I was more the type that needed to be attracted to my sexual partner rather than trying to make a number of casual conquests every weekend. I would frustrate Ken and Evan when they would try and set me up with a one night stand.
They would tell me, "Come on Joe, I know Cindy over there is horny tonight. Go make your move, bro."
More often than not, I would decline their pressure. Don't get me wrong, I was no angel and there were times when I would sleep with an anonymous stranger I picked up at a party but it wasn't as satisfying as being with someone I cared about. My friends would make fun of me but I didn't care.
There was one girl, in particular, that hung out with our group of friends during our senior year when I shared an apartment with Ken and Evan. Leah was a gorgeous strawberry blonde, with deep blue eyes, average height with full round breasts and a nice tight ass. She had the most wonderful smile that would immediately warm my heart. I could barely keep my eyes off of her, along with most of the guys on campus. She was kind of wild and liked to hang out with our mutual friends.
Every guy wanted to sleep with her and in fact, many of them did. Apparently, she was an excellent student in high school and was receiving a full academic scholarship. She had spent most of her time studying so she could help pay for college and now that she had a taste of freedom, she was making up for lost time. It seemed that when we were hanging out in our favorite local tavern, Leah would end up leaving with a different guy. She would date them for a week or two and then move on to someone else.
Ken and Evan had a small rivalry going on who would have sex with her first and when Evan won their contest, Leah became a regular guest at our apartment. It was at that time that I got to see her in various states of dress and undress. It wasn't unusual for her to be hanging out in the apartment in an old t-shirt of Evan's. I would gaze at her beautiful face with light freckles around her nose, her blue eyes and long reddish/blonde hair. I got peeks at her panties as she sat casually on the sofa or down her top at her full 36c breasts when she wasn't wearing a bra. On several occasions she would be reaching for something in the cupboards or bending over in the fridge in the morning and the shirt would lift up in back exposing her bare ass. It took all of my self-control to not come up and try to fuck her from behind. She became the object of my masturbatory fantasies.
My bedroom was between Ken and Evan's and when she would sleep over, I could hear her having sex with Evan. The walls were paper thin and their grunts and moans along with the squeaking of the bed springs would drive me wild. I would jerk off listening to their sex talk and hearing her begging to get fucked harder or hearing Evan telling her what a good cocksucker she was. I would try to time my orgasm to his so I could pretend I was fucking her rather than my roommate. At times, I think they knew I could hear them and they were extra loud in order to tease, or should I say, torture me.
When I would see Leah in the morning, I could only imagine what it would be like to fuck her. Evan wasn't shy about kissing and fondling her in front of me which only added to the tease. One night I was in my room trying to sleep while they were going at it in the next room again and I had to go to the bathroom. I had to pass Evan's room and I noticed that the door wasn't closed completely and the small nightstand light was on. There isn't a guy alive that wouldn't peek in. I got an immediate erection as I saw Leah with her legs over Evan's shoulders while he pounded away at her as she moaned in pleasure to his repeated thrusts. I got a shadowed view of him penetrating Leah's pussy.
I watched for a few minutes but got scared when I thought Leah saw me as she peered over Evan's shoulder. I made my way to the bathroom and had to wait a minute until I lost my hard on before I could pee. As I made my way back to my bedroom, I noticed the bedroom door was now closed. I was afraid Evan might say something to me the next day. He never said a word but Leah gave me a knowing smile although no words were exchanged. I blushed and quickly left the kitchen to get dressed.
She dated my roommate for almost two months before she moved onto another guy. I never got to see her fucking my roommate again but I listened to them having sex almost every night. During this time, I dated a girl myself but it didn't last long. It was nice to have sex with someone rather than jerking off all the time while my roommate was having a good time. The most difficult part was listening to Evan brag to Ken and me about how great Leah was in bed and how she loved to suck his dick. She even let him fuck her butt a couple of times. Every time I looked at Leah, I imagined her doing various sex acts with me and Evan's stories added to my fantasies.
Evan and Leah's breakup was friendly. I think they both realized they were both looking for a good time and it was never going to last. Leah still hung out within the same group of friends and we saw each other often while out socializing. I tried to talk to her because I really wanted to date her but I was so fascinated by her that I always got tongue tied, not knowing what to say. Some guys are natural players and can talk a good game with women but I never had that ability. As a result, I always watched as other men picked her up and was envious when I saw them leaving with her, knowing she was probably going to have sex with them. It killed me but I eventually gave up hope of ever dating her. I went out with other women but there was never a real connection with them. I liked their companionship but I wasn't in love.
Towards the end of our senior year, Leah started dating Ken which was a little awkward but it didn't bother Ethan. He had moved on to several other women after Leah. Ken's room was on the other side of mine and I got to hear them having sex almost nightly too. The torture of wishing she was sharing my bed had returned and so did the routine of me jerking off to listening to their sexual romps. On a positive side, I got to see her in various states of dress and undress again, stealing glances at her legs, ass and tits whenever I could.
One Sunday morning, I returned to the apartment after spending the night with a girl I was dating and saw Ethan coming out of the bedroom followed by Leah and Ken. Apparently, they just had a threesome and I was pissed that I missed hearing their exploits or even possibly being asked to join in. They were making some veiled comments over breakfast and laughing at some inside jokes between them which only confirmed my suspicions that they both fucked her the previous night.
We all graduated shortly after that incident and went our separate ways. I went to graduate school, became a programmer and got a job with a start-up before I finished my Master's degree. I kept in touch with Ken and Ethan and we still hung out together once in a while but we lost track of Leah.
When I got together one night with the guys, I asked them if they both had sex with Leah that night. They gave me all the gory details of the threesome they had with her. They told me how they were hanging out at the apartment, drinking and smoking some weed. They were teasing her about having had sex with both of them before and it was her idea to fuck them both. They told me what a horny coed she was and acted like a nymphomaniac that night and couldn't get enough cock. They both fucked her a couple of times each in her mouth and pussy and even double penetrated her. Ken and Ethan then went on to describe some of their private adventures with her and how she couldn't get enough sex.
Needless to say, I went home and jerked off that night to the thought of what I would have liked to have done with Leah if only I had the chance. I was kicking myself for not trying harder to date her. The problem was I wanted a girlfriend and she was looking for a much wilder experience with a variety of men, at least that's what I told myself. I went on with my life, dating a few women, looking for the love of my life without much success.
One evening a few years after completing grad school, I was out at Happy Hour with some work colleagues when I heard a familiar voice from behind, "Joe, is that you?"
I turned around with a stunned look on my face, "Leah? Holy shit, how have you been?"
We embraced and I stepped back and scanned her beautiful face with her big, warm smile. My eyes checked out her body and she was still as sexy as ever. I immediately forgot my work colleagues to focus solely on Leah. We began catching up on our lives and telling stories about our college days. She left town to go to grad school and was now working for a company around the corner from the bar which was extremely close to my office. We were talking for a while then decided to have dinner together so we grabbed a table in the corner.
Over the next few hours we talked about our lives, our goals and our dreams. Neither one of us was dating anyone at the time which I found shocking. She told me she got tired of guys just wanting to date her because she was pretty. She wanted something more meaningful and hadn't found "Mr. Right."
She then asked, "Can I ask you a question Joe?"
"Sure Leah."
"I don't want to put you on the spot, but I always wondered why you never asked me out back in college."
She really caught me off guard. I stumbled for a response and finally replied, "I don't know, I guess I thought you were out of my league. I never thought a beautiful woman like you would want to date me."
She replied, "I thought it was because, you know, I was a little wild in my younger days."
"I actually had the biggest crush on you but I was afraid you'd turn me down."
She looked me with her big blue eyes and responded, "That's too bad. You know I would have gone out with you if only you had asked."
I was stunned. I didn't know how to react. At first, I wanted to kick myself in the ass for not asking her out while we were in college. I blew an opportunity to be with the girl of my dreams. The other part of me was now flattered that, maybe, just maybe, I was getting a second chance.
After a few moments of awkward silence because I didn't know what to say, she told me, "Don't look so surprised. You're a great guy."