I would like to play these games in order, preferably with the same person playing the various roles (2) mentioned below. Think of this as a 'chronicle' of the life of my specific character.
The First Kiss
Richard had always been a shy boy, well, around girls mostly, and had thus far managed to survive those first awkward years as a teenager without getting involved in the drama known as a 'girl'. But he had a crush on Sarah, a cute girl in one of his classes, and under pressure from some of their mutual friends, had finally drummed up the balls to ask her out on a date. Both are shy, but are attracted to each other, and as bumbling as he is, Richard finally has his first kiss with her.
(Looking for the love interest here...to experience the 'first everything' with Richard in an awkward, first time way. Not sure about losing virginity together, though - see next idea.)
The First Time
Richard has grown confidant since he started dating Sarah, and a confidant guy is an attractive guy. But he is having problems with Sarah, as all young couples do, and she was still reluctant to go all the way. Richard had certain needs and desires he wanted to fulfill but it didn't look like they would if he stayed with Sarah.
Sophie was Richards neighbor and fellow student. She was a year older and something of a slut, with no inhibitions. She had certainly found Richard cute and now that he was dating, he was certainly a target for her. Unlike his prude of a girlfriend, she was willing to put out for Richard - whenever and wherever he wanted it. Are her temptations enough to make Richard cheat on his current girlfriend?