New York’s Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. This summer, the Sex Diaries will appear on the Cut as a special edition. Check back Tuesday afternoons for your weekly peek behind doors left slightly ajar.
This week, a newly single indie musician who prefers women au naturel and hopes to not hurt anyone: male, 28, Red Hook, straight.
DAY ONE
9 a.m. I wake up in D.C. We had a show there last night, Sunday. Shows are tough on Sundays, they’re always sort of a letdown. This one had a good crowd but not nearly as big as normal. I’m in a moderately successful indie band. We play in clubs, usually selling out about 150–300 seats.
This is my first time being single on the road in three years. My ex and I broke up last month, this time for good. I’m really excited to see what’s ahead. I was always pretty faithful, save a few random make-outs on the road.
There was a cute bartender in D.C., but she mentioned a boyfriend, so I backed out of that scenario fast.
11:30 a.m. We have a radio show in Philly to get to. We are five guys in a van, usually staying at a Best Western, tonight at a friend’s place. It’s all very exhausting and redundant … not the blow-and-models scene people imagine. Being in a band is a workman’s job. It’s a labor of love.
2 p.m. We do the radio show.
3 p.m. A girl I met a year ago in Philly, Claire, is coming to the show tonight. I’m hoping she’s still single. We’ve been in touch a little but no personal details have been revealed.
8 p.m. I meet Claire for a drink before the show. She looks great. She is single! I get excited.
9:30 p.m. I go back to the venue to play.
11:30 p.m. Post-show, I help sell some merch, but I’m anxious to be hanging out with Claire. She was kind enough to stick around.
Midnight We load the van. Claire is being a trooper and meanwhile, I’m fading. She suggests we take off, but I know I have to leave early in the morning to get back to New York. I’m just so tired. I feel bad. I thought about rallying in the name of getting it on, but I’m just too tired. She seems a little upset but … I just can’t.
DAY TWO
9 a.m. The band wakes up at our friend’s place. We shower and grab breakfast at a diner. You try not to eat fast food when you’re on tour. You’re already feeling disgusting enough.
Noon We keep the van at our bassist’s place in Carroll Gardens, and everyone splits up for a few hours. I have the afternoon off.
2 p.m. Jog in Prospect Park.
3 p.m. One of my best female friends, Bethany, wants to set me up with her art-world friend, Tally. Apparently Tally was already a fan of the band — which may or may not be true, but it feels nice to hear. She describes Tally as tall, lean, and glasses-wearing. Sounds hot to me. Also, my friend has incredible taste in people, so I trust her.
5 p.m. A few texts from female “fans” come in. These girls always find us. I think they have little crushes on me, and they’re kind of annoying, and definitely not attractive. But I try to be nice, as I’m appreciative of the support. I tell them I’ll put them on the list, as well as Bethany and Tally.
9 p.m. Bethany, Tally, and I have drinks before the show. Tally is so cute. We hit it off. It feels promising.
10 p.m. NYC is so much fun to play. New Yorkers at a concert are oddly not jaded when it comes to live music. They have the best energy. Much better than L.A. or Nashville.
11:30 p.m. More hang time with Bethany and Tally. I can’t get a read on Tally. Is she looking for a boyfriend or just fun? I am weary of meeting anyone right now who wants a relationship. I know that’s not what I want for a while. And I’d never want to hurt anyone who might have hopes for more.
12:30 a.m. I get Tally’s number before I take off. And then I play nice (for five minutes) to the annoying girls, because they’re still around.
1 a.m. I go home. I’m getting horny. I feel in my bones there is a fun week ahead.
DAY THREE
8 a.m. We’re heading to Boston in a few hours. But first, I beat off. Beating off is a challenge when you’re on tour because you’re always with the other guys and believe it or not, we are not all barbarians.
9 a.m. I do some laundry and a little Tindering. I have no energy to ask anyone out.
10 a.m. I text Tally that I would love to hang out when I’m back in New York in a few days for a Brooklyn show. She doesn’t reply right away so I get nervous.
Noon We leave for Boston in the van.
2 p.m. Tally writes back and seems enthusiastic. I’m relieved. My confidence is a little wobbly these days since I haven’t been in the game for a while.
3:30 p.m. We do a college-radio-station show. There’s a cute girl working there. She’s in college, so that’s a little weird, but she’s a senior, 21 or 22. Her name is Melinda. We flirt a little and I invite her to the show. She says she’ll “try.”
6 p.m. We load in for the show. I hate Boston. It’s impossible to drive and the people are all assholes. We are playing in Cambridge.
9 p.m. Melinda shows up with one friend. The evening just got a little more exciting.
10 p.m. It’s all very repetitive. We play the show, sell some merch, hang out for drinks.
11 p.m. Melinda and I take off for one-on-one drinks. She’s very self-assured and suggests we go to her apartment. We have some beers there. Within a half-hour, she’s kind of seducing me. She’s particularly confident for her age, and obviously very sexually experienced.
Midnight Amazingly, she does not have a shaved pussy. This is a huge turn-on. She has a nice, mature bush. I find her very hot. And she has these really gorgeous, natural tits, which she concealed really well throughout the night. Big C’s … NICE SURPRISE. I’m so horny, but I try not to come too fast. It’s been a month since I’ve had sex, and that was with my ex. We start fucking on Melinda’s couch, then her bed. Her roommate was asleep.
1 a.m. We fuck. We both come. We fall asleep.
DAY FOUR
8 a.m. I have to meet the band to drive back to NYC. But first, I go into Melinda’s bathroom and squirt some toothpaste into my mouth because I’d like to fuck again. Her hair is messy and her eyes are kind of dreamy. Clearly neither of us has any huge regrets from the night before. We kiss a little then fuck. Then we get a coffee.
9:30 a.m. We both know the fling was a one-off, but we exchange numbers.
10:30 a.m. On the drive back to NYC, Melinda texts me that she had a great night. I write back immediately that I had a great night, too. Meanwhile, Tally texted about the Brooklyn show tonight. I put her on the list right away.
2 p.m. I’m home, relaxing for a bit. No need to jerk off because I came in the morning!
7 p.m. Tally and I get drinks before the show. Then I play the show, sell merch, etc.
11:30 p.m. Tally waits for me to end the show and we get more drinks. As we’re walking to the train, I ask if it’s okay to kiss her. I don’t want to be pushy, but she’s into it. Then she asks if I want to come over for a nightcap. We go to her place in Bed-Stuy.
12:30 a.m. She’s on her period. I’m not opposed to period sex at all, but I know some girls are uncomfortable with that. She keeps her underwear on but we get naked. She looks awesome. Trimmed bush, but not bald at all. Two nights in a row with some actual hairy bush … SCORE. She blows me. I tell her before I come because I don’t want to gross her out. She says to come in her mouth, so I do. She spits it out into the sink … doesn’t bother me at all. I ask if I can at least lick her clit a little bit. She lets me, and comes close to orgasm, but she doesn’t. I wish I had made her come but … oh well. We fall asleep.
DAY FIVE
9 a.m. I wake up with Tally. Our next show is in Cleveland so I have to get home and get ready to take off.
10:30 a.m. The drive to Cleveland is brutal.
2 p.m. Tally is on my mind but there’s another woman on the horizon, too: a woman named Mary, who I met in Chicago when I had a girlfriend. She’s a writer for a weekly newspaper out there. Chicago is tomorrow night …
11 p.m. Cleveland is blah.
1 a.m. I get to our hotel and confirm that Mary is coming tomorrow. Cool. I feel like single life is off to a good start. I know I’ll miss having a girlfriend eventually, but for now, I’m enjoying my freedom.
DAY FIVE
9 a.m. I tug one off in the shower thinking about Melinda and her big, natural, young tits.
10 a.m. We head to Chicago in the van. Lots of driving and diner-eating and complaining. Being in a band is awesome, but you have to want it so bad, it’s just too draining and oftentimes heartbreaking to have this lifestyle unless you really want it.
6 p.m. I meet Mary for dinner. She is really sexy, if not traditionally hot. She’s also a really big drinker. She has a raspy voice, smokes, and swears, and is refreshingly honest and direct. She’s buzzed by the end of dinner.
11 p.m. Chicago is always fun. It’s a great set. I broke a string, but it didn’t matter because the crowd was so great. It’s a sellout.
12:30 a.m. We load the band. Mary and I head to her house. We take some tequila shots and then she opens a bottle of wine. We’re both drunk now. I’m too timid to make the first move. Then she says the greatest thing ever: “Are we gonna fuck or what?!” In the moment, that was the hottest thing in the world. But … I had whiskey-dick and I knew it.
1 a.m. Mary has a great ass. It’s not fat, but plump. I put a condom on, although it’s incredibly difficult to stay hard. I could only fuck for a few seconds at a time. Whiskey-dick sucks. You get really in your head, really defeatist, and it’s just a vicious cycle in which you never can win. I’m embarrassed.
1:30 a.m. I go down on her until she comes. She’s a little sweaty but it doesn’t turn me off at all.
DAY SEVEN
7 a.m. We wake up with terrible hangovers. I’m assuming I can get hard now, so I try fooling around. Yup. We fuck. It’s super-slimy sex, morning-after breath and all. I put a finger in her asshole because I feel like she’s maybe the kind of woman who wouldn’t mind that. And I was right.
11 a.m. I meet the guys to head to St. Louis, a short drive. The hangover is subsiding and mostly I just feel great about all the fun I’ve been having. I definitely want to be single for a while, although I am intrigued by Tally back home. I’m on the road for another three weeks and won’t see her until then. We’ll see what happens when I get home …
7 p.m. The usual grind. I can’t lie and say that getting laid is not a perk of the job, but that’s certainly not why I’m in it. It’s exciting to think about all the possibilities now that I’m single … safe to say, I’m really liking it.
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