"I...think we should...be open to..." I stammered. I was trying to tell my girlfriend that we should see other people as we went our to our separate colleges but was choking as I looked into her big brown eyes.
Amanda was my first real girlfriend. I had met her just after graduating from high school when we were both taking an advanced mathematics class that would give us credit when we went off to college. We were both 'nerds' in high school...neither of us were sporty or popular and we had focused on getting great great grades vs. socializing. She had got a scholarship at a state college, I was headed out of state for an Engineering degree.
I had awkwardly flirted with her in class, and was surprised she was receptive. I was not a great looking guy, and had never had a lot of luck with the ladies. But it seemed easy with Amanda. We both had enjoyed making fun of the other students, most of whom were college kids who had failed and needed the course to catch up. The course was every weekday morning and we started to hang out during our morning break together and eventually we started having lunch together after class.
Amanda was no beauty queen but she was cute. A petite, skinny girl of Japanese and Mongolian heritage, Amanda wore glasses that somewhat took away from her big brown eyes. She had shoulder length brown hair. Amanda didn't smile a lot but when she did, she had a big, toothy grin that was a bit goofy but made me smile. I had fallen in love with Amanda when I kissed her for the first time.
It's embarrassing but I had really only had a romantic relationship with one other girl, Ashley Jones. Honestly even that wasn't really 'romantic'. Ashley was a popular cheerleader who normally wouldn't have had time for me, but I had agreed to tutor her in calculus. I enjoyed having the chance to be so close to her, but realized quickly that it would be very tough to teach her since she had no aptitude or interest in the subject. Often my tutoring session would be interrupted by her texting with a friend or her boyfriend. I brought up some kind of compensation when I realized it would be very time consuming, but Ashley said there was no way she was 'paying for math'. Ashley could see me trying to talk my way out of continuing the tutoring when she suggested an arrangement. Unwrapping a lollipop and putting in her mouth she said, "Tell you what. If you can get me a C or better in the mid-term, I will let you...jack off while looking at me."
I looked at her with her mouth open and felt myself harden just at the suggestion. I stammered and blushed, but agreed. I spent so much time teaching her simple ways to remember answers to the likely test questions and in the end she managed to scrape by with a C. I had to keep texting her to remind her of our agreement but she conceded and one afternoon after school when her parents were away, she invited me over. I was hard even walking up her driveway. I had been fantasizing about her for months, but especially since she made the offer. She plopped down on the living room couch after she answered the door and I fidgeted wondering where we were going to do this.
"Well", she said looking up as I stood nervously. "You had better get to it."
When I realized she was serious I didn't hesitate long. I had hoped she might take off some clothes, but there was no way I was going to miss this chance. It was embarrassing to take out my cock while she sat there fully clothed. Ashley wore the yoga pants she often dressed in, sexy but not showing any skin other than her bare feet. She wore a simple white t shirt on top but it was evident she was not wearing a bra under it and her big nipples were faintly outlined. Amanda smirked a little when she saw me start stroking, then picked up her phone and started texting. I was a bit pissed at first but somehow her ignoring me felt...hot and feeling less self conscious I started stroking faster. I imagined what it would be like to kiss her, imagined her lifting her shirt and showing me her big tits. I started to breathe heavy and she looked up. "Cum in your hand." she said sternly but with some amusement, "none on the floor." I came quickly and as instructed made sure to capture it all. She let me clean up and that was it. I never got to teach her again. She would give me a little smile in the hall when I passed, but that was it.
So when I kissed innocent Amanda, it was special. When I fucked her fore the first time, after almost two months, it was awkward, but epic. I finished way too quickly but Amanda was patient and let me try again not long after. It turned out Amanda liked to fuck and loved to have me go down on her. I never lasted long, but I would get hard again quickly and was happy to go down on her to please her.
So, at the end of summer, why did I want to...kind of break up with her? Well, we were going to be far apart and I thought it was the mature thing to do. Also...well...Amanda's friend was going to the same school I was and...she was really pretty. Her friend and I got along and I thought...well...I hoped...
It turned out that Amanda had been thinking similarly. I mean, not about her friend, but that it wasn't realistic that we would stay boyfriend and girlfriend when I was going away. We had a pretty hot session that night. She asked me to try spanking her, which I had never done before. I tried a little and asked if that was ok but she told me not to worry about it and had me go down on her instead.
We texted a lot the first few days apart but a lot less as time passed. I made a lame move on her friend, but she politely told me she had a boyfriend and I was firmly in the friend zone. There were so many beautiful girls at the school, but my class was almost all dudes and I was the opposite of a 'player'. I studied hard, played a lot of cards with my roommates, and got no action.
When Thanksgiving approached I was really excited to see Amanda again. I had texted her and made arrangements to see her the night after I got back. I took her to dinner and we caught up but honestly I was really just thinking about was fucking her. When we got to my parents' place and we were alone I kissed her and quickly went to get on top but she directed me to go down on her.
I was so grateful to have my face buried in her pussy, feeling very close to her again. I told her there hadn't been anyone else. I started licking more but realized she was quiet. I looked up and asked her if there had been other boys. She looked a little shy, but then placed her hand on the back of my head and pulled my face into her wet gash.
"There...have been other guys." she said haltingly. "Many...other guys."
I was surprised but she was writhing a little and I kept eating her out. "Actually the second week after school started, I...went to a party and...there were a lot of shots." I was even more surprised now. Amanda didn't drink...we had made fun of kids who had to drink to have fun. "I got pretty drunk and...I guess I was flirting a lot with one guy. Actually he went to your high school. Brad Tanner?"
Now I was really surprised. Tanner was a big dumb jock and a bit of a jerk. He used to bully me when we started high school. Not Amanda's type at all. Why would she be flirting with him? I kept working my tongue though as Amanda seemed to be enjoying what I was doing.
