When I got into Yale, back in 2009, everyone at my high school was shocked. Not because it’s expensive, we were all the rich kids in Indianapolis (and I’ll admit, that’s not exactly Gossip Girl territory, but we weren’t too far off from, say, Dallas, for money and power). Not even because they thought I was dumb, though I’m sure a few of them did. It was because it wasn’t Oberlin – where the kids who did well in languages went – or Northwestern – where pretty much everyone else went. I was going back East to a different type of rich, a different culture, and there was no way I would fit in at an Ivy.
Well, that’s what everyone thought. I was a good Lutheran boy who lit the candles on the altar one Sunday a month and sang in the junior choir until his voice broke. I lettered in track and field, crew, and golf. I did well in my studies and had two steady girlfriends – sophomore and senior years – and played the field, no pun intended, my junior year.
Let me tell you, that first semester at Yale, everyone was right. I didn’t fit in. The money helped a bit, especially since it was old money, but I had a Jag at a school where all the East coast preps rode bikes or Vespas. I didn’t make the varsity crew, and I barely ended up on the varsity track and field thanks to radical long jump skills. I’d never been to Europe or South America or even Canada (though we’d had a sweet senior spring break in Acapulco). I had to figure out who I was, and where I fit in. Turned out it was my residential college.
After three years, I have a good life here. I’m a freshman counselor at Silliman, working hard on my senior project for my major in Economics and my minor in Chinese. I still go home to Indianapolis for the summers and help at the Vacation Bible School, but everyone I knew and went to school with stayed in the Midwest. They’re doing well. They’ll continue to do well, but, other than Mary Lou Eisenbach who got pregnant her sophomore year at Northwestern and transferred to Berkeley after her son was born, they’re all on the path they started on when they were born to moderately wealthy parents in a moderately wealthy mid-western city.
And I’m on the other trajectory – the “gets out of town and has a different life for some number of years” trajectory. They all expect I’ll be back after my stint as, well, whatever I end up doing with Economics and Chinese. I’m going to take the Foreign Service exam, just for a back up. What gets me is the expectation that I’ll be back. One day, maybe a decade from now when I want to bring up my kids a particular way or thirty years from now when I can retire with a series of good investments to finance it, they think they’ll see me again in Indianapolis. They could be right.
Between track and field, crew beginning my sophomore year, and just generally participating after I got over my first semester funk, I’m doing pretty well -- academically and socially. Plus, I’ve found more people are impressed by the Jag than admit it.
So freshman advisors get assigned to a court at Silliman. We have our suite and among us look after the incoming students in our section. That’s how I met Andrew Ashkirk, helping him carry his luggage into the residence on the first day. Unlike every other freshman I met that day, his parents weren’t around to help him. And unlike every other freshman, he knew exactly who he was and why he was at Yale.
Theater was his passion. He already planned to try out for every play on campus. He begged to make a Broadway play (“a serious one, not a musical,” he said) one of our freshman expeditions. He played guitar well enough, piano better than average, and sang like a teenaged girl’s wet-dream. The only acapella groups on campus who weren’t chasing him were all female. He finally decided to go with the Duke’s Men. He liked their sense of humor, and they needed a baritone who could hit some clear tenor notes.
In the meantime, he threw himself into his studies. I noticed that most of his study buddies were girls and said something to Kath, my fellow freshman counselor on the distaff side.
“He’s playing the field, Greg.”
“Andrew? I mean he’s paler than milk, freckles if someone uses flash to take a picture, and dresses like an unmade bed.”
Kath rolled her eyes. “Those of us who don’t iron our jeans,” she peered at me severely, “all dress like unmade beds. We’re college students. And let me tell you, a straight, red-haired, intellectual, theater major, who doesn’t have acne and will dedicate his latest songwriting effort to you, is going to be popular with all sorts of female type people.”
Since the first “forgot to put the signal out so I could have sex without my roommate walking in” incident of the semester went to Andrew, I figured that Kath was right. Other than that incident, he and his roommate caused me less grief than any other pair in our section.
Andrew participated. Every freshman mixer idea we came up with, he joined whether it was a hockey game, an art exhibit, or a taffy pull. He didn’t even complain when the Broadway play, we organized as an activity was a musical. He and some of the other theatrical types came up with an arrangement for “Coffee Break” on the way home.
I didn’t have to do much for him, but I ended up doing quite a bit with him. We even studied together for the one freshman requirement I’d been putting off for three years -- my intro science class. Andrew was my lab partner and explained stuff better than the prof. I was going to end up with a solid B thanks to him, and I was pretty sure without him, I’d have been lucky to scrape a C.
Exams came. Sick freshmen, mostly the ones who weren’t used to New England winters, were dosed with Nyquil. All nighters were pulled. Concerts were given. I was invited by several people I knew to an acapella competition, so I shrugged and went. Every group on campus did a song or two, and Andrew got a to sing a line on “We Three Kings” that got a few sighs from some of the Silliman girls -- and one of the guys, now that I think about it -- who’d attended.
I took the Silliman performers out for hot chocolate afterwards, and we just all generally had a great night talking about our holiday plans and reveling in the fact that exams would be over in two days.
My final semester at Yale started well. My advisor liked the work I’d done on my final project. I’d already fulfilled all the requirements for my minor, so other than an Econ Seminar and an advance International Relations course, everything else on my schedule was something I was taking for fun. I even shared a course with Andrew again; this time it was Versions of The Tempest. I don’t know how he got the instructor’s permission to take an advanced seminar but it was nice not to be the only person in the room who wasn’t majoring in English. We ended up working on the first project together and got a decent grade.
Other than that class, I saw Andrew around the hall -- usually in a group or with his arm around a girl -- and I continued to pursue Gina, a junior I’d met at the Safety Dance. She was cute and funny and called me on my bullshit, and, really, what more could anyone ask from a relationship.
Everything was good. Andrew posted flyers for the Duke’s Men’s spring concert on every available bulletin board in the College. I got an invitation over a double espresso while we were putting together our presentation. I told him Gina and I wouldn’t miss it and went to grab a couple of cookies to go with our coffee.
I knew what to expect from the concert. In the first act, there’d be skits and bad dancing and worse drag -- there were always at least a couple of pieces of comedy around gender identity (as I’d learned to call it since moving east. I wouldn’t dare repeat what most of my friends in Indianapolis would have called it, and I went to a liberal school.). The second act they’d be in white tie and tails. There’d be at least one soloist who was slightly off-key due to nerves, but overall, there’d be some good music by a bunch of really talented guys.
Gina convinced me not to wear jeans and to put on a blazer over my sweater for the concert. We’d been dating for nearly six months, and, yeah, I thought she might be it for me. We got seats on the center aisle, not too many rows back, and settled in for the show.
The first act was pretty much going as I expected. The skits were a step above awful and filled with in-jokes; the music was fantastic. There was another skit for the alumni, and then two songs with returning members of the group. The freshman members were brought out for an introductory song, and there she was. He was.
One of the girls in our court had sent Andrew a copy of the terrible poem from Harry Potter about “eyes as green as a toad” or whatever as a Halloween joke. Now the impression was greenness -- huge green eyes, a bottle green dress with matching shoes, and legs that went all the way up. I could just barely see a tremor in Andrew’s hand from nerves as he reached for the microphone. His eyes locked with mine, and he visibly relaxed.
They found their pitch and went into a perfect doo-wop version of “Come Rain or Come Shine.” Andrew’s voice was lush and rich and felt like every word was for me alone.
The blood had slammed down to my cock. This was the sexiest woman I’d ever seen. It wasn’t just lust; it felt like... love? I wanted to get on my knees and slide my hands under his skirt. I didn’t care that I’d find a cock there. Really. All I wanted was to give her/him pleasure.
The rest of the group was doing some simple choreography, and the other freshmen were doing a close harmony bridge. When Andrew started the last verse, he found me again and smiled as he started to sing. My cock twitched, and I had to bite my lip to try to quell my responses.
I barely heard the rest of the first act. I couldn’t take my eyes off of Andrew. Six feet of lanky redhead was wearing a dress that didn’t pad him out in any way, and it was all I could do to stay in my seat rather than try to sweep him off the stage and ravish him in a dressing room -- or the most expensive hotel in Venice, if that’s what he wanted.
Gina nudged me into applauding at the end of the act, and I laughed that I’d fallen into a trance. Well, it wasn’t too far wrong.
I told her I needed the men’s room and rushed toward the backstage area. They wouldn’t let me in, of course, but Andrew came out for a moment and clapped me on the back.
“I hit the high note and the low note. I’ve been messing up one or the other in rehearsal all week,” he said.
I stopped staring at his lips, looking lush in a shimmery lipstick, and found my voice. “You sounded great. Really stunning, man. I was shocked. I mean, I figured you’d have to be good to get in, but nerves and all...”
“Yeah. Especially wearing heels. Thank God I’ll never have to do that again.”
“What?” I nearly panicked. I managed to calm down and say, “Aren’t you going to sing that song in other concerts?”
“Damn straight. But the dress and make-up were just for this performance. Hazing. A bit of a gag. I’m happy about that. I’m sure I have lipstick on my teeth.”
I managed to keep myself from saying, “Your lips look perfect and kissable,” and instead said, “I’ll let you get ready for the next act. Do you get another solo?”
He grinned. “I have a couple of lines here and there, but my big accomplishment for the second act is that I arranged ‘Mama Says’ by Jason Mraz. If it’s popular, it might go on the next album.”
“That’s great. I’ll keep an ear out for it. I’d better get back to Gina. You sounded great.” I kept talking so I could keep on looking at the most perfectly beautiful woman I’d ever seen before she disappeared for good. “Join us for coffee afterward?”
“No. But I’ll put you and Gina on the list for the after party.”
“Cool.” I took out my phone and grabbed a picture of him before we both went back where we were supposed to be.
I found Gina and we finished the concert. They got a standing ovation, and I was right about Andrew’s sense of humor fitting well with the Duke’s Men. His arrangement of the song was made funnier by the way the lines went around the circle. He had all kinds of talent.
We made it to the party. I walked Gina back to her college and kissed her goodnight. Then I went back to my room, looked at his picture on my phone, and jerked off to the idea of kissing my way up Andrew’s thighs while he sang torch songs.
Well, a man can dream.
I do all the time -- about Andrew in drag.