So this relationship started in high school. I was the typically young, popular jock kid---started dating this girl who was known as "sluttly" by comparison from another school in the area. Come to find out she had been with the same guy for 3 years (we met at 17 mind you)...however the longer things unfolded...there were about 4-5 she had messed around with in high school before me. Nonetheless...high school days will full of crazy weekends after football games, basketball games, etc. We fucked all sorts of ways as you do at that age. What really took the sexual excitement to a whole new level were the college days and the idea of her enjoying two guys at once. So the fantasy had started---mainly with someone just "watching." It was Christmas break of our freshman year of college, I had contacted a good friend from high school. He had an apartment at a different college he had kept the key over break for. After a short-lived Friday night of hanging out at the parents house, we made our way an hour north to the apartment to stay for the evening. Small talk and AIM instant messenger soon led to me on top of her on his bed while he continued at the computer, "acting as if nothing was going on." Soon, the back rub turned to jeans sliding down...then her shirt lifting. I remember vividly her white lace thong clinging to her wet meaty snatch lips as I ran my hand around her legs softly...first around the inside of her knees, then up to her panties. My fingers sunk in her wet hole...and around her slowly-swelling clit. I laid back onto his bed and she looked over at him before unbuttoning my jeans almost teasing him. Her hands rubbed my thighs as my zipper went south. I was telling myself get hard, get hard. My dick remained in a paralyzed, 3" state of flaccid as she took me into her mouth. She knelt on all fours with her pussy half ******* to him. I leaned around her shoulder to spot my friend and gauge his interest. Never until now was there any discussion of a third joining...only to watch. I suprisingly found my friend with his dick out, it must have been a full 8" and as thick as a paper towel roll. I remember the feeling of jealousy..."how was he so hard" and I was soft? Within 5 minutes I was half hard---possibly 4" now...and I felt the sudden twitch in my ball sack. How was I cumming with only a semi-hardon I remember thinking. I think this was likely my first "wimp" cuckold moment...to see my girl sucking me...surely wanting me to be SUPER hard for my friend with my trophy hot girlfriend. But to her suprise, I wasn't rising to the occasion and he was. While the night could have gotten hotter, the fun ended there for the evening. We went into the living room onto the floor for the night; her trying to ride me and unable to get hard a second time. I wonder the thoughts going through her head that evening...