Doctor's Orders
Chapter 1
by willtann
I've never been very attractive to women. At 30 years old, I'm tall, yes, but I'm also overweight, prematurely losing my hair, and I need strong prescription glasses to see beyond the end of my nose (contact lenses just won't cut it). The few times I've tried to date, they leave as soon as possible, usually with a line about not feeling a "spark" even though I "seem very nice." Well, I'm sick of being the poster boy for "Nice guys finish last."
Fortunately, my brain didn't fail me the way my looks did. I am almost always the smartest person in the room. And here is a little secret you may not know: most people are so afraid of being seen as stupid that they won't contradict you if you speak with any kind of authority. I didn't use this technique for purely selfish purposes until I was in medical school.
For most of my undergraduate years, I was in love with one particular girl: Jessica. She was tall, only a few inches shorter than me, but she didn't have an extra ounce on her except for her breasts. I was amazed that such a slender girl (she had the body of a dancer) could have breasts that substantial. Her wavy, dark brown hair reached to the middle of her back when she wasn't wearing it in a ponytail. She tended to wear loose jeans and flannel. And she wore reading glasses, which countered her intimidating beauty enough for me to relax around her.
I only confided my feelings for Jessica to my roommate, Pete. He was just as unappealing to women as I was, though he was shorter and skinnier. He kept encouraging me to make a move and tell Jess how I felt about her. However, I didn't want to risk losing the low-stress friendship we shared; high school had taught me that confessions of attraction only created discomfort if the feelings weren't reciprocated.
The summer before the three of us started at Harvard Medical School, Pete and Jess started dating. They did their best to make me not feel like a third wheel, but it was inevitable that I would feel jealous and hurt. If Pete was able to pull it off, I should have been able to as well. I did my best to act normally around them, but my gut started to feel hollow whenever I watched them together.
We were coming up on final exams when I finally gave into temptation and tricked Jess into sleeping with me. I was the smartest of the three of us, so I was in charge of preparing the hours-long study sessions. Pete had left exhausted two hours earlier and Jess was starting to nod off, catching herself just before her face smacked onto the table. She looked at me with a pleading expression in her tired eyes. "I don't think I can manage any more studying tonight."
"We have to try to make it through this next chapter. If we don't, there's no way we'll be able to cover everything, especially with Pete slacking off."
"He's not slacking off! He's tired from...well..."
I had a suspicion she was going to mention sex. Despite the pit in my stomach, some masochistic part of me needed to know. "What? Sex?"
"Yes."
Part of my heart burst. I knew with the stress of exams, they wouldn't have as many chances to be intimate. I hoped they would grow apart and I would finally get an opening to be with Jess. But since they were still close, I needed to do more than wait. "When did you two find the time?"
"Is that really any of your business?"
"Orgasms are stimulants to women and depressants to men. Basic neuroscience. If he crashed a few hours before you, when you two had intercourse could be a factor."
"I just don't want to weird you out..."
"I'm an adult. I also need to know in order to adjust the study plans."
She seemed extremely uncomfortable when she finally answered. "We snuck off during dinner."
"Right before Pete called it a night."
"Yes. I'm sorry."
"Jess..."
How should I try to convince her to have sex with me?
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