![]() I hated it because of what was said to me: G et out! Was the nicest version. But I hated using the women’s room and not just because of being a boy. Grunge and androgyny were reasonably widespread, even in the sticks of Maine. And I wore the same t-shirts and jeans and flannel shirts and sneakers that I always wore.ĭown that hallway, I thought, which one? Easy enough to just go in the women’s room, give people a dirty look when they scowled at me. They’d been calling me Al for years, so I didn’t have to tell them that I’d changed my name from Alice to Alex. My short hair hadn’t been mentioned - I’d had it short third grade through seventh grade, after all, only growing it out at my mom’s insistence. Afterwards, debating Denny’s versus Friendly’s, we veered down the hallway toward the movie theater’s bathrooms. We went to the movies, five of us crammed into someone’s mom’s sedan. ![]() And also because now at 17 I was, for the first time in my life, a boy. And, for me, because though I had known these boys since preschool, I had gone away every September for the last four years to a prep school. Second, because none of us owned a car and the nearest movie theater was 40 minutes from our rural Maine town. First, because we all worked odd jobs with odd hours. I’d been back in my hometown for a week or so, and a bunch of us decided to go to the movies together. Home for the summer from boarding school, that awkward and potent summer between high school and college, I was working as a dishwasher. I’d been living as a guy for about a year. The first time I used a men’s room with friends - friends who’d known me from before, friends who’d known me my whole life - I was a few weeks shy of my eighteenth birthday. And maybe they were washing their hands when I was leaving, and that’s why I’m thinking I probably didn’t wash my hands. Both at the urinals, and so their backs were toward me when I entered. I do remember that there were other men in the room. I can’t remember if I washed my hands or not. I made a beeline for the stalls, which were the same as the stalls in every women’s room I’d ever used in my first 17 years of life. In fact, I didn’t see most of it as I walked in, head down and turned slightly away from the line of urinals. I looked about 14, probably, with my hair freshly cut short, my head still feeling light and buoyant after getting rid of the ponytail I’d carried through most of high school. He had a roommate so I guessed at which one it was.The first time I used a men’s room, I was 17 years old. Leaving his dorm the next morning I realized I had no idea what his name was and had to try to find it using the campus directory for that building. We went to his dorm, I got my cherry popped, it was fine, mission accomplished. “I was in college and determined to lose my virginity so I just grabbed a guy at a party and started making out with him. We shall finish, awkwardly and way too soon, with this one: Sometimes, names aren’t as important as losing your virginity ASAP. Neither of us came, and we haven’t spoken since.” ― Lili Michelle, a comedian in New York City ![]() I uncorked myself like a bottle of wine (red, obviously) threw it across the room like I had just drawn a sword and hacked it toward my worst enemy. I said ‘Ew, no.’ He tried again and exclaimed, ‘No, I’m pretty sure you have a tampon in’ so I rolled my eyes and said, ‘There’s literally no way ―’ then felt the tampon. ![]() I laughed in his face because what a crazy thing to ask during my first time. I wish I could remember more about that night but I couldn’t see much.” ― Daniel Tirado, a comedian in New York City “My older cousin let me use his place and left a pair of Ray-Bans on the coffee table with a note that read ‘take them if you do it, leave them if you don’t.’ Being young and stupid I thought he wanted me to wear them while having sex. Huff Post has 11 uncomfortable, hilarious, and worrisome ‘How I Lost My Virginity’ tales, but here are our picks of the more interesting ones. To ease you into the long weekend, we thought it might be nice to giggle and squirm along with these comedians, entertainers, and generally funny people sharing their ‘first-time’ stories. The rest of us are just happy to have the initial challenge and awkwardness out of the way.Įven if it lasted a whole 10 seconds, for some. If you managed that bed of roses, candlelit body bonding kind of session, then good for you. Not many people can brag that their first time having sex was as perfect as it was made out to be in movies from the 2000s.
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