sex diaries

The 23-Year-Old Temp Playing the Field for the First Time in Four Years

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the 23-Year-Old Temp Playing the Field for the First Time in Four Years, female, temp, East Village, 23, straight, single.


6:10 a.m. Starting a new temp job. I had trouble sleeping because I want to make sure I get there on time. I’ve had to purchase a whole new corporate wardrobe. For the first time, I’m grateful about my breakup two months ago with the guy I’d been dating since sophomore year of college. One of worst things about him was his snoring and I often overslept because of it.
8:15 a.m. Stop for coffee and am extra careful not to spill it on myself, as I’m prone to do. Discover I’m sweating through my blouse. Will have to keep jacket on all day, and find a stronger deodorant.

8:50 a.m. Check in at job in large Midtown office, where I’ll be answering phones for three attorneys. Two are older and not attractive but one looks barely older than me and hot in a preppy kind of way.
10:15 a.m. Already bored. Check e-mail and news but afraid to click on anything that might get me fired.
12:30 p.m. Lunch break; sit outside and people watch; wish I were wearing something sexier.
8 p.m. Meet best friend to see comedian friend of hers. She thinks he’s hilarious, I’m less amused. Guy next to us is texting, which totally annoys me.
8:17 p.m. He is still texting so I lean over and politely ask him to stop or go outside. He looks up and I almost gasp at how much he’s my type … and looks like my ex.
9:35 p.m. Hanging out in hallway after show. Texter comes over to me and apologizes. “You’re right, and it was ballsy of you to call me out. Can I make it up to you by taking you to dinner?” I agree, and we exchange information. First time since breakup I’ve felt genuine attraction for a guy. Up close, I see he’s not exactly like my ex; his eyes are blue, not brown, his lashes are longer, and he’s probably in his early thirties.
11 p.m. Go to sleep early, excited about date possibility.


9:30 a.m. I offer to get the lawyers coffee, even though it’s not technically part of my job. It gives me a chance to walk around a little and scope out Hot Lawyer.
9:37 a.m. I’ve brought them all coffee and done my best to flirt with Hot Lawyer and still be workplace appropriate.
11:24 a.m. E-mail from Texter asking if I’m free tomorrow night. Glad he’s not asking about tonight; I have plans with friends, and last-minute dates aren’t my style. I agree.
11:33 a.m. Start to look up Texter online, stop with his Facebook profile. I’d rather see what he’s like in person. Hard to resist with a whole day ahead of me at the computer, but I think I can manage.
8:30 p.m. Meet friends for drinks. Plan to only have one but have so many I lose track. That often happens with this crowd, and every time I try to set limits but I usually ignore them.
10:52 p.m. Fall into bed, head spinning. Was afraid I might puke. I didn’t, and now afraid that means I’ll be more hungover tomorrow.
1:27 a.m. Text from my ex. Every once in a while he gets drunk and either tries to rekindle our relationship, have a booty call, flirt, or just look for sympathy. Sometimes I reply, sometimes I ignore him. I choose the latter.


5 p.m. Leave at five on the dot, since temp agency told me I can’t get overtime. I peek in at Hot Lawyer but he’s on the phone so I don’t say anything. I’m excited about tonight’s date but it’s just a date and doesn’t mean I can’t look around.
6:25 p.m. Shower and slip into date outfit my best friend made me buy during the week after my breakup. I have worn it out twice to parties but this is the first time I’m putting it to its proper use. It’s a scoop-neck navy blue dress that falls to just above my knees, paired with navy heels. I usually keep my blonde hair back with a barrette, but let it down for tonight.
8 p.m. He’s waiting for me at the bar, looking a little nervous. His phone is on the bar and I walk over, pick it up and hand it to him. “I hope you won’t be needing this during dinner.” I say it so he knows I’m half joking — but only half.
9:15 p.m. Dinner is winding down and I’ve had a good time. He doesn’t mention my age every two seconds, which I’ve found older guys, whether they’re flirting or not, tend to do, like we’re from two different species rather than a decade apart. Still, there are a few times when he seems impatient when I don’t get a reference, and twice I pretend to know what he’s talking about while trying to memorize the reference to look up later. Despite that, I like him and don’t want our date to end.
9:30 p.m. We go outside and I don’t rush to fill the awkward silence. We’re near my place but I don’t want to invite him back. Maybe if he weren’t the first post-breakup date I would. Thankfully, he suggests we go to Veniero’s for dessert.
9:45 p.m. Sit down over coffee and dessert. I love cannoli but they’re one of those foods that are a little too suggestive, at least for a first date. I get cheesecake and he gets tiramisu, and we share them.
11:35 p.m. I think only an hour’s gone by until I check my phone. They’re closing soon and I should go to bed. I’d love to make out with him but barring going to one of our apartments, I don’t really know where we could except outside and that seems too cheesy.
11:40 p.m. We hug and I kiss him on the cheek, then pause there and he takes the lead and gives me a real kiss. It starts out gently but then we are full-on making out and I forget my squeamishness.
11:52 p.m. We finally part and he says he’ll call me. I have two friends who always say that and never call, so I don’t really know how to respond, but I tell him I hope he will, and walk home.


9:30 a.m Didn’t get called today for any jobs, and it is too hot to stay in my apartment all day. A little bummed about the money and not getting to see Hot Lawyer again, but choose to look on the bright side: It’s beautiful out. I take advantage of the weather and head to the park in one of my skimpiest dresses.
10:07 a.m. Cute guy walking golden retriever is checking me out. I don’t know why, but he just looks like he’s in a relationship; I feel like I can spot that and have been known to warn my friends about guys on the make. I still smile back at him.
10:11 a.m. Dog Owner sits on bench next to me and we chat. I tell him I’m off today, he tells me he works from home. We sit there and don’t say much; then he tells me that he thinks I’m really cute but has a girlfriend (score one for my intuition) and doesn’t want to jeopardize their relationship. It’s a little TMI but also sweet. I hope that if I get into a relationship again it’ll be with a guy who knows the boundaries between innocent flirting and unacceptable behavior (let’s just say my ex didn’t).
6:27 p.m. Just when I figure I’m not going to hear from Texter, I get … a text. He asks how my day was and if I want to go out the next night.


7:40 a.m. Get a call for possible temp-to-perm job. Was looking forward to another mellow day, but I have to take it. At least it’s Friday so I can sleep in after today.
4:45 p.m. Am grateful this gig is busier than the last one because it makes the day go by much faster. I know I shouldn’t spend money but I decide to try to find a new dress as a little reward for my second date. Also decide that if Texter puts the moves on me, I’ll sleep with him. He’s cute and while I don’t know if I want a relationship, getting laid again would be nice.
5:30 p.m. Find cheap but cute black dress, which I can always wear on nondates too.
7:30 p.m. We were originally planning to see a movie but he wants to go a friend’s party and I’m always up for meeting new people.
9:25 p.m. I’ve met a few people, but mostly listened to Texter talk and observed him. We’ve snuck away a few times to make out, and when he asks me if I want to leave, I say yes.
10:15 p.m. We’d stopped for quick drink and by the time we’re in his bed we’re pawing at each other. He gets on top of me and we do it fast. He comes after only a few minutes and apologizes, but I tell him I don’t mind, and I really don’t. I assume there’ll be a next time.


8:04 a.m. Wake up early out of habit. Texter is sleeping so I get up, use the bathroom, then wander into his kitchen. I’m tempted to look through the stacks of mail on the counter but resist, partly because my ex once almost broke up with me over rifling through his mail, and partly because I barely know this guy. Instead, I make us coffee.
8:35 a.m. Get back in bed and try to fall asleep despite the coffee, but wind up lying there staring at the ceiling. Wonder if I should go home but that seems rude. We didn’t talk about our weekend plans but I was hoping we’d at least have breakfast.
10 a.m. Texter finally wakes up when his alarm blares. I giggle because his hair is standing up all over the place and he looks totally panicked, like he doesn’t know where he is. He turns off the alarm and looks at me first with surprise and then a smile.
10:18 a.m. We cuddle and don’t talk, which is fine with me. I have no idea how often he does this and don’t want to know. For a while we just enjoy each other’s warmth and then I feel him getting hard and slowly start giving him a very quiet hand job. He doesn’t move much and his eyes are closed but I know he’s appreciating it.
10:22 a.m. The hand job is making me horny but I’m not sure of the etiquette here. I have condoms in my purse, but we used one of his last night. Is it presumptuous to pause and go get one? Instead I slow way down until he opens his eyes and eases my hand off of him and gets a condom himself.
10:24 a.m. I’m on top of him, and his eyes are darting from my face to my breasts to where our bodies meet. We were in the dark last night, and I was a little buzzed, so this is very different. I like it but it’s been so long since I’ve been with someone new I’m a little uncertain about how to act. I bite my lip so as not to make too much noise. He touches my clit and asks me if what he’s doing feels good. I appreciate him asking rather than just assuming I like it and I tell him when to press harder. After I come, he moves his hand away and pulls me close, and he comes.
11:20 a.m. We finally get up and take a shower together. I feel a little self-conscious even though he wants to fool around some more. After we’re all soaped up we turn off the shower and make out while we’re soaking wet but we don’t have sex again. Holding off makes me feel like we’re still in the middle of foreplay even when we go outside.
11:48 a.m. Most places we pass have long lines so we grab egg sandwiches at a deli and wind up at the park where I was the other day … and see Dog Owner with his girlfriend. He winks at me and I pretend not to notice.
12:10 p.m. Texter asks what I’m doing next week, which I note is a subtle way of not asking what I’m doing tonight or tomorrow. I wonder if he has a date or other plans; of course my first assumption is a date. I tell him I’m free every night but Thursday and he says he’ll be in touch. Again I have that feeling that now it’s totally up to him whether we see each other again or not.
12:25 p.m. He walks me home and we kiss on my doorstep but it’s more sweet than passionate.
5:30 p.m. Spend rest of day lounging around, filling my friends in about date, trying to puzzle out what it means. Most of them tell me not to overanalyze it, but I can’t help it.


11:30 a.m. Meet friends for brunch and this time I’m the one leading the Bloody Mary ordering. I still feel the afterglow from sleeping with Texter and I must be giving off some sexual energy because the waiter flirts with me, as does a guy while we’re both waiting in line for the unisex bathroom.
12:45 p.m. “So do you want him to call you?” one of my friends asks. My first instinct is to say “Of course,” but I’m not sure if I really like the Texter, or just like the fact that we hooked up and he’s interested in me. “I think so,” I tell her. Part of me wants to start something with him and part of me wants to be the kind of girl who has a few guys in rotation at once. I’ve never done that and it seems exciting, if exhausting.
5:18 p.m. Texter calls, and we wind up talking for two hours. I’m happy to know he’s not just a texter. I admit to him that I pretended to get his references and he laughs. Also get up the courage to ask him what he did this weekend and he tells me he visited his parents. I think I’ll ask him about who else he’s dating the next time we see each other. We make plans for the following night. Our conversation is pretty PG, but when we get off the phone he sends me a dirty text, which leads to some extended masturbation/sexting.

TOTALS: one office crush; three flirtations with strangers; two acts of intercourse; one hand job; one shower petting; one masturbation session.

The 23-Year-Old Temp Playing the Field for the First Time in Four Years