Cross Road Blues

Earlier in the night, their long time friendship had taken an unexpected turn. They were having one of their normal, high energy conversations in the living room of Troy's townhouse when the topic turned to sex, fooling around, and other relationship issues. There was never any kind of sexual tension between Troy and Jessica in their lives. They had always dated other people and supported one another as best they knew how. Tonight, though, something changed. After thirty minutes of talking about their past sexual experiences and how their mutual friends used to tease them about the possibility of hooking up one day, Jessica jokingly asked Troy if he wanted to make out with her. Troy, for once in his life, missed the joke, leaned over and kissed Jessica. They would kiss on their couch for twenty minutes before Troy asked Jessica to join her in his room.

The next ninety minutes were spent on Troy's bed, and things went no further than just fooling around. Troy took off just his T-shirt, and Jessica ended up shedding her bra and socks. Five minutes after stopping, Jessica suddenly turned her face towards the wall. Troy tried to gently get her attention a couple of times, but was unsuccessful. He instead turned away from Jessica, and his mind began to race.

Oh god, I think I just fucked up here, he thought.

While Jessica lie silently behind him, Troy wondered exactly where things had gone wrong. He never expected to end up in bed with his best friend, who had done nothing more intimate in their lives than hug whenever they saw each other, or whenever they said good night. Occasionally, Troy would put a hand on Jessica's knee while spending time together, or she would playfully tossle his hair, but nothing more. Perhaps it was their mutual realization earlier that their little makeout session was fun, but there were no fireworks. No chemistry, or nothing that might have seen them take off all of their clothes. Maybe they really weren't meant to be anything more than just friends.

Troy also wondered if he had gone too far earlier after he had enticed Jessica to remove her bra so he could kiss and lick her breasts, followed by him rolling her over on her back and sliding his hand down between her legs for a five minute handjob. She seemed to be into it, Troy reasoned, but was she really? His mind filled up with all sorts of worst-case scenarios. It was now after midnight, his condo was dark, and there was a feeling of impending doom.

But Troy could not just allow fifteen years of friendship end like this. He had to break the silence, or awkwardly wait for Jessica to do or say something, anything.

1. Before Troy can say anything, he feels Jessica's fingers gently draw down his back.
2. Jessica rolls back over and decides to take matters into her own hands.
3. Suddenly, Jessica bolts out of bed. "Look, I've gotta go. Right now. I can't stay here anymore."
4. Troy rolls over and gently shakes Jessica. "We need to talk," he says.
5. Nothing else happens tonight. Troy and Jessica never bring up the events of this evening ever again.

Add New Option

Go Back

View Forward Story Tree
View Back Story Tree