sex diaries

The 18-Year-Old Extensively Cheating on Her Boyfriend

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week: the 18-Year Old Extensively Cheating on Her Boyfriend, 18, female, Upper East Side, straight, cheating.

7:45 a.m.: Make eyes with man running at my pace around the Reservoir. When we finish our laps we sit down and chat. As soon as he hears “18 years old” he looks freaked out and stumbles away.
12:15 p.m.: Get out of class and meet up with “boyfriend.” Quotation marks because he thinks we are much more serious than we are. Beginning to see that not discussing relationship guidelines was a mistake. I do want to get serious with someone, but not as quickly as he does.

12:45 p.m.: Lunch at Ollie’s results in cheesy noodle-sharing and I become so embarrassed that I force him to get the check immediately.
1 p.m.: Quickie with Boyfriend.
5 p.m.: Find wristband from when Boyfriend and I went to All Points West. We met when we were both interning in the Hamptons the summer after high school and spent the entire summer doing fun things.
10 p.m.: Meet up with high-school friends for dinner at JG Melon’s, our go-to high-school eatery. They mourn the lack of sex in their lives. I sit quietly.
10:45 p.m.: Get text from a boarding-school guy, whom we’ll call Prep School Boy, that I knew in high school. We agree to meet up with him and his friends.
12:30 a.m.: Meet up with Prep School Boy and friends at Tenjune. They are hotter than I remember, confirming my theory that boarding-school boys are always cuter than city boys. Remember hooking up with him in my junior year and swooning over him for months. Now I seem to be in the power position, as he texted me.
1 a.m.: Making out with Prep School Boy on a corner couch at Tenjune. I grab his cute, Waspy ass and consider transferring to Dartmouth.
2 a.m.: In Prep School Boy’s parents’ apartment. Having flashbacks of being here in seventh grade. We have sex on his bed. He’s amazing, and afterward, I go down on him, giving him what he calls “the best blow job, seriously.”

9 a.m.: No running today. Wake up hung-over with a text from Prep School Boy saying he had fun last night. He adds a smiley-face emoticon, which makes me regret ever touching him.
Noon: Blow off Boyfriend for lunch. Feeling guilty about last night. Who am I?!
7 p.m.: Order in sushi and thank the Lord I have my own apartment.
8 p.m.: Watch Jersey Shore and think about having sex with Vinny in the hot tub. On second thought, gross. Vinny?

9:45 a.m.: Running the Bridal Path as a licentious old man watches me.
11 a.m.: Showering, envisioning Prep School Boy’s strong hands washing me clean. Decide that, with 30 minutes to be at brunch with my mother, this is the wrong time for this fantasy.
3 p.m.: Get text from Connecticut Boy, an old friend of mine. He’s coming into town for one night tonight and wants to spend it with me. My heart begins to pound, as I was in love with this boy for two years.
9:30 p.m.: Meet up with Connecticut Boy at Pegu and discuss college life. We both agree that we don’t want to turn 19 and bid our youth farewell.
11 p.m.: In a cab home with Connecticut Boy. We begin to kiss and he kisses me in the exact opposite way that Prep School Boy did. Connecticut Boy is soft and loving. Prep School Boy is hot, but I begin to envision a future with Connecticut Boy.
1:30 a.m.: At apartment with Connecticut Boy. Receive a text from Boyfriend saying, “I know you’re out with your friend. Just wanted to say I love you.” I swoon and feel guilty. Connecticut Boy and I make out, but I don’t let it go any further.
2:15 a.m.: Laying in bed while Connecticut Boy snores on the couch. I think about how open and mature Boyfriend is for a 19-year-old. He openly tells me that he loves me and is happy to be with me. He doesn’t play games like I do.

7:15 a.m.: Shrill alarm goes off. Connecticut Boy, who has slept over, groans, asking why I’m getting up so early. I tell him about my running plans and he remembers that he has to be on the train in an hour. We kiss, a friend kiss, and part ways.
2 p.m.: In class fantasizing about my professor doing me on his desk. He is 40-ish with salt-and-pepper hair and a great body. I can’t help it that I like older men.
7 p.m.: Meet up with Boyfriend for an early dinner. We agree that we feel like we never see each other. We sit for three hours talking. I have always dreamed of marrying young. But I think my desire for marriage has put too much pressure on my relationships and instead I have remained overly casual so as to not choose “the wrong one.”
11 p.m.: In Boyfriend’s dorm room, making out on his bed. His kisses are right in between Connecticut Boy’s and Prep School boy’s. We have passionate, in-love sex. I feel connected to him and consider removing quotation marks.
2 a.m.: Cuddling with Boyfriend in his bed, celebrating the fact that he doesn’t have a roommate. I confess to him that I have never watched porn. He looks at me and laughs, “I know. You’re too sweet.”

10:45 a.m.: Having breakfast with college friend. We agree that the boys at our school are almost all too artsy. She is from the land of the Wasps, while I might as well be. We decide to seek out the preppiest spots in Manhattan. We then become aware of how obnoxious this sounds and hold off.
5 p.m.: Meet Hot Professor at Starbucks to discuss my paper. He seems so secure and grounded.
9 p.m.: Get call from Prep School boy. Why are these kids always home? He wants to come to my place. I decide a public environment will be safer. We meet at Bar & Books and chat. He’s gorgeous but pretty boring.
10:30 p.m.: After a few drinks I look past his vacuousness and we make out for a while. He comes to my apartment. I go down on him but politely decline full intercourse. He’s content either way and passes out on my couch after. Lovely.

7:15 a.m.: Wake up and decide to leave Prep School boy where he is. No matter how beautiful someone is, when you cheat, even quasi-cheat, you feel dirty.
12:15 p.m.: Boyfriend is waiting outside my class holding two cups of coffee and two sandwiches. He moves higher on my potential marriage list.
8 p.m.: The homebodies in us come out. We order in Indian food, watch Whip It, and fall asleep early.
1 a.m.: I am awoken from my blissful slumber by a text from Connecticut Boy. I scan it quickly and delete it. I am perfectly content with Boyfriend right now.
1:15 a.m.: Begin to think about my relationship with Boyfriend. I feel that swell of emotion you get when you’re really happy with someone and don’t want to let go.

7:15 a.m.: Alarm goes off. Boyfriend and I wake up and decide I should burn my morning calories a different way. We have hot morning sex. With me on top, straddling him, I can look down at his beautiful face and scruffy beard.
9:30 a.m.: Boyfriend walks me to class. We share a long, loving kiss and part ways. I am in bliss for the next two and a half hours.
2 p.m.: Hot Professor makes comment about running. Suddenly I am turned off by his age and creepy vibe.
8 p.m.: Boyfriend and I meet up at Beyoglu for a yummy dinner. I love that he knows what to order for me.
8:30 p.m.: Looking at him across the table, I realize why I have let Boyfriend in: He is one of the most genuine people I know and I feel he’ll always protect me. I keep smiling at him to the point where he asks me if I’ve had too much to drink.
11 p.m.: Boyfriend and I walk back to my apartment, enjoying our blissful time together. I feel genuinely happy and can’t wait to go home and have a little fun with him.

TOTALS: Four acts of intercourse with two partners; two acts of making out with two partners; two acts of fellatio with two partners.

The 18-Year-Old Extensively Cheating on Her Boyfriend