(There are two separate ideas in this prompt. Both prompts speak to me because I am a nerdy, somewhat unorthodox guy that is shy sexually. I feel as if both prompts subvert cliched attitudes regarding sex and that's a big plus for me. As usual, I am looking for serious writers who want to engage with complex characters and emotions.)

Our First Night of Intimacy- Of course I wanted sex. Every guy does. The thing is, I was not a guy who felt super comfortable with being proactive in getting sex. I was raised the right way by feminist parents who drilled home to me the reality of how nasty men could be towards women. The last thing I ever wanted to do was to make a woman feel uncomfortable. This attitude, combined with a little bit of insecurity on my part, meant that I was never really going to ask you for sex. We had gone out on three or four dates by this point and we got along well. We had romantic strolls in the park and we both enjoyed sharing our favorite restaurants in the city with each other. I told all my friends about you and it was obvious to them that I was quite taken with you.

But you were concerned. You were more experienced than me and you were used to guys making a move on the first or second date. You never had a problem getting intimate on a first or second date so the nature of our dates so far had been quite abnormal for you. On one hand, you knew that I was smarter than your average partner and more considerate than most. You figured I was just being polite. On the other hand, you were concerned that I wasn't physically interested in you. Perhaps you were even frustrated that we hadn't been intimate yet. Regardless, you were determined to be intimate on our next date or you would move on to a guy who would give you what you craved. How will I react to your assertiveness on our next date?

A Couple's Present to Me- We had known each other for as long as I could remember. Over the years, we shared many things with each other. From summer camp cabins to a variety of very inside jokes, you could say that me and you were best friends. Of all the things we've shared, however, I never expected your girlfriend to be one of them.

Despite our common interests, you and I had divergent sex lives. Ever since our high school days, you never had an issue getting laid. In truth, you were probably better looking than me and a lot more confident. On the other hand, I was quite reserved sexually and I famously had "no game" when it came to flirting. That said, your girlfriend really enjoyed my company when the three of us would go out together. As shy as I could be when it came to flirting, I was quite open with the people who I was comfortable with. She liked my offbeat sense of humour and my willingness to be nerdy and "uncool" in a city that seemed increasingly obsessed with appearances and the next big thing.

She felt bad for me as I struggled in my dating life so she decided to come to you with an idea. Unbeknownst to me at the time, she wanted to invite me in for a threesome. She was very curious as to what I would be like sexually and while she was quite happy with her sex life with you, she didn't have any qualms about trying something new. Are you prepared to share your girlfriend with your somewhat nerdy best friend?