My Favorite Boss

It was that next Wednesday night when my boss-turned-boyfriend said something that bothered me for the first time.

We were laying in bed, cuddling after a nice date and romantic love making. I had changed back into my pajamas, a pair of boxer shorts and a regular t-shirt, and he had slipped his briefs back on.

I was asking him about his rugby team. It was a team for gay men in Charlotte, and I was surprised to find out there were multiple gay rugby teams across the country. They had formed a little league for fun, and this past Sunday was a scrimmage tournament, as they were in their off season. "It's a great thing for a lot of us guys, really," Carson said. "We stay active, we get to travel on weekends, and we get to build community with other gay men."

"That's really cool," I said. I'll admit, when I came to college and got involved with our LGBT club at school, it was the first time I'd ever belonged to a queer community. Growing up, the only exposure I really got to that was what they show on the media, with rainbows and loud parades. I was never really drawn to that, though -- while I respected how people celebrated their identities, I thought it wasn't right for me. "So, are you friends with the guys on the team? Have you ever, like, dated any of them?"

"I've dated a couple, yeah," Carson explained. "But not while we were on the team. A handful of guys hook up after, but most of us just do it for the friendship."

As much as queer communities seem to be sexualized, I've learned that in practice they're actually much more friendly and normal than that. "So, do y'all hang out outside of practice?"

"Yeah," Carson said. "Every Sunday we go to The Cave, a bar in town, and grab a beer."

"So you went last Sunday? Do you think I could come some time?"

Carson hesitated for a moment. "Yeah, uh, I don't know if you would like it. It's not really your scene."

"What does that mean?" I asked, confused.

"Well, it's a gay bar," Carson said. "I don't know, you don't seem like you'd be that into that."

I was a little offended. "I would totally be down to go to a gay bar," I said, defending myself. "If you didn't know, I'm gay."

"Yeah," he said, laughing a bit. "Let's talk about it tomorrow, okay?"

"No, what else?" I pushed.

"You know that I think that you're sexy and sweet and awesome, right?"

"Yeah."

"Well," he started, "the thing is, you dress like a frat boy, and I think the guys on the team would totally make fun of you if you came."

I was a little surprised. "Do you have a problem with how I dress?"

He laughed nervously. "Look, I think you're sexy and dress fine. Sometimes I wish you dressed, I don't know, less like a frat boy and more like a gay frat boy."

"What do you not like?"

"Babe, it's not that I don't like it," he started, but he could see I wouldn't stop until I got an answer. "Okay, for example, you wear boxers, like, super straight dude boxers. I don't know a single other gay man who wears those."

I crossed my arms, though he wasn't the first person in my life to point out that I should update my wardrobe. Danny, my ex, had brought it up countless times. "They're good to sleep in!"

"Okay, okay, I said I didn't want to talk about this," he said. "Look, we had a great night, we had great sex, and now let's just relax. You leave on your trip tomorrow, let's just enjoy this last night, okay?"

I settled down, but as I lay in bed that night, I was still bothered a bit by what Carson said. Was he embarrassed by me? For a second, I wondered if he'd even actually wanted me to come to his rugby game. Was he embarrassed by the way I dressed? Really, I was at a time where I was wrestling with some internalized homophobia. It wasn't something my mom or family believed, they were always supportive. But for some reason I never wanted to be perceived as flamboyant in any way, didn't want to stand out. What parts of me were just a more subtle, subdued person, who didn't see myself in skimpy or flashy clothes, and which parts of me were ashamed of myself? This is something I still struggle with today, sometimes, but this was the beginning of a journey for me and my identity.

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The next day at work was a little tense, as Carson and I hadn't fully resolved what we talked about the night before. That evening, Carson drove me to the airport. My ex-boyfriend and good friend, Danny, had invited me to stay with him in Miami for the weekend, along with two of our other friends, Skylar and Kas. Danny knew I was exclusive with Carson now, though, so it was purely a social vacation.

Carson was sweet, and walked me to security. "Don't worry about that stuff last night," Carson said. "I think you're cool, and don't want you to change. Got it?"

I nodded and smiled. "Got it," I said, and kissed him on the cheek. I was only gone until Sunday, but as I walked towards my gate, I already started to miss his smile. Carson always made me feel so safe and appreciated and valued, and leaving him felt like I was leaving all of that behind, too.

Basically as soon as I got on the plane, I passed out. I don't know why I always fall asleep on planes, but I'm pretty much asleep as soon as I buckle my seatbelt. Several times, a flight attendant has had to wake me up.

That was the case on this flight, at least. With a little nudge, I got up. My breath smelled awful, and desperately searched my bag for a stick of gum before I saw Danny.

After hopping off the plane, I waited in the passenger area for Danny's car. The Florida night air was even more humid than North Carolina's. I felt my skin get sticky almost as soon as I stepped outside, and I hoped that Danny would arrive before the mosquitoes. After about fifteen minutes, Danny pulled up, and I hopped in.

We hugged over the middle console. In the harsh car light, Danny looked good -- he was tan, from his days at the pool, and seemed to have put on a bit of muscle. But, really, I was just so glad to see a familiar face.

We immediately started talking like normal. The breakup hadn't affected our friendship much -- this was the only relationship where I successfully remained friends with someone after a split. I asked him about his life, and he was still having fun with the dads at the country club. We were both having soiree's with older men that summer.

"How about Carson?" He asked. Though I knew he'd ask, I was dreading telling Danny about what Carson said.

"Well, you're going to say I told you so, but... he said something that bugged me." I told Danny about my conversation with Carson.

"The boxers! I did tell you. I know that's crass to say I told you so, but I did," Danny said.

"I think he's embarrassed of me," I said. "He doesn't want me to meet his friends."

Danny sighed. "Look, can I give you a little therapy right now?" I nodded. "I don't think he's embarrassed of you, but I think you might be embarrassed of yourself. I always thought you didn't present yourself as hot as you are."

"What does that mean?"

"I mean that, you know, confidence is sexy," Danny said. "But I've always felt like you didn't carry a ton of confidence, and you seem to dress that way sometimes? I don't know."

I thought for a minute. "I get that, but I think I have confidence."

"Just, I'll try to advocate for Carson," Danny said. "He knows you're sexy. I'm sure he wants you to feel good about yourself, and wants to show you off to his friends a bit, you know?"

For a moment, I wanted to say that Danny was wrong, but I thought about it for a moment. I'd put a lot of work into my body -- I had nice, puffy pecs, a solid core, and strong legs. I had a nice, big butt, and a great dick. I wasn't ugly, either -- I had light brown hair, full lips, and big, green eyes. I often compared myself to models online, but really, I always wondered if I was hot enough to join them.

"Well, what does he want? For me to wear a thong to bed?"

"No," Danny said, "But if you do wear a thong, please, send me a picture. I don't know what he wants, but I just think you should experiment with your fashion a bit more, maybe try some new underwear. I'm not saying that you have to become a certain type of underwear guy to be gay, but maybe it'll help you build your confidence to try something new."

I thought for a moment. "Okay. Yeah, I'll try something new," I said. I was motivated and looked up stores in Miami on my phone while Danny drove. I found a men's underwear store, called "Underthere." I asked Danny if he'd go with me.

"Sure," Danny said. "I would love to help you shop, I've been wanting to go there myself."

I'd been considering it for years, I guess. None of the guys in porn wore boxers, and though I worked out hard so I could look like them, something inside me made me think I shouldn't dress like them. At the end of the day, back then I didn't ever really think of myself as sexy. It was something I had to learn.

Danny had a small in-law suite behind his grandparent's house all to himself, which is where we stayed. He set me up on the couch, and we were both exhausted from the day, and quickly fell asleep.

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The next day, we woke up at around eleven, and had a slow start to the day. Danny had managed to get the whole weekend off, including Friday, so he was taking the opportunity to sleep in late. He constantly had to be up early to help set up the pool at the country club, so I was glad he could rest. Despite his silliness, Danny was a really hard worker.

Danny took me to his favorite lunch spot. Danny and I never seemed to run out of things to talk about, but especially didn't mind sharing details about our naughty sides. I told him everything I'd done with Carson, and he gave me the details on his hookups. I typically don't kiss and tell, but with Danny there were few secrets between us.

"Okay, the store is about 20 minutes away," Danny said. "You sure you want to go?"

I smiled at him. "Yeah, it's time to grow up," I said.

We drove to the store, and I admit I was nervous. It was in a small strip mall and had a banner for a sign. "Underthere: Men's Underwear Emporium" the banner said. Next door was a Greek restaurant. The windows had signs and merchandise in the way, and were deeply tinted, so I could hardly see inside.

Danny went in first, with me close behind. The inside of the store was lit with fluorescent lights, with a couple of rainbow siren lights illuminated the store in corners. The speakers played dance music, like you'd hear at a club, a little too loudly over the speakers. The walls were covered with different clothes, mostly underwear, separated into style and color. It was literally wall to wall rainbows. Some areas had some other kinkwear, like leather harnesses, and some displays had regular clothes, like shirts or shorts. I was instantly overwhelmed.

Danny, checking the terrified look I had on my face, put his hand on my shoulder. "Dude, you look like a deer in headlights. Come on, let's just go look at the briefs."

He took my hand, and lead me back to the underwear wall. The wall was unbelievably organized: the underwear was hung on hangers (which I still find crazy to this day. Do people not just ball up their underwear and throw it in a drawer?), sorted first by waist size, then by color.

"Can I help you two?" A man said, walking up to us. He was short, around 5'5", but lean and handsome. He had light, buzzed hair and a cute, short nose. In both of his earlobes were empty holes for earrings. He wore a black tank-top that had "Underthere Pride" printed in rainbow letters and short athletic shorts on, which helped to accentuate his large legs.

"I'm taking my friend shopping, because he's finally graduating from boxers," Danny teased.

"I feel like I just got thrown into the deep end of the pool," I admitted, blushing. I realized I really didn't know how to talk to other gay guys about gay culture.

"Well, that's no problem," the man said. "If I were you, just start out with something you know you're going to wear and be comfortable in. Some of this stuff is fancy and sexy, but if it's too extreme, you probably will be hesitant to wear them. My name is Percy, let me know if you need anything." Percy returned to his position behind the counter.

Danny tried to help me search by pulling a few pairs down to get a sense for my taste. "I think I can handle this," I told him, partly because I thought I could, and partly because what Danny was grabbing was way outside my comfort zone.

I spent a long time flipping through all the pairs on the wall. I probably pulled out and looked at everything my size. Every time, I wondered to myself, "could I ever see myself in these?" At the time, most of them were no's. Finally, I settled on two pairs of low-rise briefs. The first was a neutral navy, which I was certain I would wear, and the other was the same brand but a sky blue, to represent my college. The store had a policy against trying on underwear, but they matched my waist size perfectly. "I like them," Danny said as I showed them to him. "Conservative, but cute."

"I feel like there's absolutely nothing conservative about them, but thanks," I said, laughing a bit.

"Cool, that didn't take long," Danny said. "You ready to check out?"

"There's one more thing," I said, and walked over to the other wall. It had been something that had piqued my interest ever since my day with Carson at the rugby tournament.

I silently perused the wall, and finally found what I was looking for -- a simple, black, athletic jockstrap. I had been so turned on fucking Carson in one, and I knew I had the ass for one. I wasn't sure about it, but I decided to go for it.

Danny saw me grab it, and he chuckled, "Oh, I'll definitely want to see you in that sometime."

"In your dreams," I said. I walked to the counter, and Percy rung me up.

"Good choices," Percy said. "These will look great on you."

"Thanks," I responded.

"Don't let your friend tease you, I know it isn't easy," Percy said. "Sometimes, when you try something new, it's hard to get comfortable in your own skin. Just take it easy."

"I will," I said. He was genuine and sweet to me the whole time. I couldn't tell if he was flirting with me, or just doing his customer service job, or both. I'm sure he doesn't remember me against all the other guys that shopped there, but I hope he knows that his words of encouragement helped me that day.

I paid $75 for the three pairs of underwear (which, again, I thought was crazy, but apparently that's pretty standard?) and left. Danny then drove me to a small shopping mall, where he got me to buy a pair of 4" inseam casual shorts and a fitted camo t-shirt. He also convinced me to get a pair of short swim shorts with a 4" inseam to wear to the beach the next day. At that mall, I spent about $150 on new clothes, and another $6 on an Auntie Anne's pretzel. The business student inside me was impressed by how lucrative the gay industry was.

By the time we finished, it was time to drive back to Danny's place and prepare for guests. We ate dinner, pulled out the futon. Kas and Skylar got there around 9, and we went out for ice cream and hung out all night.

Kas and Skylar were both friends from LGBTQ events at school. Kas was a lesbian who was almost a total hick -- she loved racing, though she thought Formula-One was far superior to Nascar. She was my game buddy, who went with me to the football and basketball games when Danny and Skylar were getting their "beauty sleep." Skylar was a trans man and was an absolute total geek. They were super into computer science and gaming, and actually had been practicing their own game development at home, because our school didn't have actual game design classes. Skylar was the only one who would go to McDonald's with me -- Kas was vegetarian and hated McDonald's, and Danny said "fast food messes with my plumbing." We were all juniors, and had formed a little group for ourselves this last year.

Kas slept on the pull-out couch with me, and Skylar slept in the room with Danny.

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The next day was wonderful. Danny convinced me to wear my new, short swimsuit, and we spent the day sunbathing on the beach and getting frozen drinks at the beach bars. After we had one too many drinks, we saw a sandcastle building contest hosted by some hotel. We lied that we were staying there and entered as room 323 (a number chosen by Skylar, who said it was somehow supposed to be related to 69, but I couldn't follow that at all). While most of the people there were families with kids, my group just decided to bury me in the sand and give me a big beer belly. They sculpted my sand body as I lay there. Kas made it a Gulliver's Island theme, and constructed small little people out of sticks and seaweed to be scaling my big belly. Danny sculpted my sand body wearing a pair of ugly, heart-print boxers. Though my fingers were pruning under the wet sand, and at some point my legs started to fall asleep, it was a blast. We didn't win (apparently a kid with a shitty moat is more impressive than our arguable masterpiece of sand sculpture), but we did get a lot of cute pictures with me in the sand. As the sun was going down, I asked my friends to pull me up out of the sand, but they all ran away, and I had to push my way up out of the sand and chase them down, which was a real challenge with my completely asleep legs.

We watched the sunset together. Danny pulled out his ukulele and played music for us, and we sang along as we watched the sun sink into the ocean. We stayed there, talking in the dusk, until the cool night air of the beach was too much for us to take.

We had plans to maybe go out to a club or something that night, but between sitting in the sun all day and the alcohol in our drinks, we were all exhausted. We watched a movie on the couch and ate a delivery pizza. We passed out by 11 PM.

Looking back, at the time I was so embarrassed by my lack of fluency in gay culture. I felt ashamed that I didn't really have any rainbow in my closet, or any Lady Gaga on vinyl, or whatever the hell made someone "gay." But I had gay and queer friends, and we accepted and loved each other, through thick and thin. I had my own little gay culture of my own, and I now realize how special that was and is.

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Skylar and Kas hit the road early that next morning, and I had my flight back to North Carolina at noon. Danny drove me to the airport and kissed my cheek as he said goodbye. "I feel like you've changed, Blake," he said. "You seem more grown up. In a good way."

"I feel more grown up," I said. "Thanks for helping me along the way." I hugged him back. "Talk soon?"

"Definitely," he said.

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I got back to my apartment, and I knew that that evening Carson would be going to the gay bar, The Cave, that afternoon after rugby. I wanted to see him, but also show him that I could fit in with the other gay guys there.

I showered and got ready, and finally tried on my briefs. I slid on the navy ones, and looked at myself in the mirror. As I looked, I thought I looked kind of sexy, a feeling I rarely had about myself before. My side profile was great -- in the front, the briefs pulled my bulge out front and center, as my package filled out the fabric up front, and in the back my round butt made a nice, outward curve from my back to my legs. They felt a little uncomfortable and tight, but really, I was excited to be wearing them.