Chapter 34: Roommate Fun (based on Bride’s Diary No. 8 cover, Ajax/Farrell, February 1956)

It’s not easy date someone who has a roommate, especially if this roommate is a female one. There is always that feeling that she is trying to hit on you, or even you end up feeling something for her. Not forgetting to mention, of course, the millions of fantasies one man can have about two girls that live together under the same roof.

Judy Cooper is testament for that. She was my girlfriend for a year or so and our relationship was fine until Anne Curbishley became her roommate. They were best friends and, once Anne decided to leave her family for an acting career, she went to Judy, which also tried a life at the show business.

Anne was what Judy sometimes wasn’t. She was a girl full of life, always shining, dreaming about her future, not quitting on her dream to be a start, while Judy seemed at times be not to adventurous as her friend was. Near to Anne, Judy was one of those “average” girls.

I was still with Judy, but Anne got me attracted to her every time I saw her. I didn’t knew how to react when I was with her, because I couldn’t just give her a kiss and throw her on bed because I was still dating her friend, and I was still in love with Judy. Can you picture the situation I was being forced to handle?

Anyway, I needed to work out a way so I could have Anne and still keep Judy, but I didn’t knew how. Or I had to give up one of them to get the other or work out a threesome, but I didn’t knew if Judy could accept that idea. So, I decided to work the toughest way possibly: try to have them together at the same time.

But how I could do that? Well, keeping Judy wasn’t hard, but I had to avoid much fanfare if I had to get into Judy’s pants. Then, at a Sunday, when Judy went to meet her parents, Anne dropped by home to practice for a test she would have the next day and asked some tips to me.

“It’s a romantic movie, Joe, and I am not quite sure if I can handle the love scenes”

“You are very beautiful, Anne. Why a girl like you would worry about romantic scenes?”

“It’s because I never had a steady boyfriend. My relationships weren’t too meaningful to be like the ones in the movies”

“But at the movies you can lie. It’s not real, you know that...”

“I know, but I am still a newbie at these situations. Please, could you help me?”

I played the ‘boyfriend’ side to help Anne to have her play. First of all, she is a gifted actress. No bull! From the first line, I could sense she could have a big success in Hollywood.

But the scene asked for a kiss, and when we had it, I don’t know if it was because I wished that so much or the scene really needed a kiss like that, because the kiss was like ones you give to the love of your life. After a while, we really got kissing like we were husband and wife.

“It’s sure we really must do this?”

“I don’t know, and I don’t want to stop either!”

For a moment that day, I just forgot Judy and embraced myself into that situation. We just kissed and kissed and even rolled on the floor, feeling each other’s lips having the party of their lives.

“Should we go to your room?”

“Well ... Judy will not come back until Tuesday, so ... why not?”

I am not that kind of cheating guy, but, yes, you can call me whatever of a cheater because I was taking my girlfriend’s roommate to my bedroom in order to have sex with her. And I had no regrets on every second I spend taking off my clothes and showing my semi-erect penis to Anne.