sex diaries

The ‘Terrible Girlfriend’ Making the Most of Holiday Sex

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the ‘Terrible Girlfriend’ Making the Most of Holiday Sex: Female, 25, Chicago, student, straight, in a relationship.


11 a.m.: Driving back from my parents’ house in the suburbs. Brought boyfriend home for Christmas; after two days at their house, I think he’s had enough. He’s the first boy I’ve brought home, ever. Grandparents were a little uncomfortable that he is a different race and kept referring to him as my “friend,” but my parents seemed to like him. In my mind I always envisioned this scenario being a lot more painful.

Noon: Skip my yoga class and suggest we get naked instead before I head back to my parents’. We’re on the couch. I stand up to pull off my thong, intending to straddle him. He stands up too and proceeds to pick me up and carry me to his bed. I try not to think about the extra cookies I ate this weekend and instead focus on the sex. Just as he finishes, I feel myself climaxing too. I grab onto his headboard and ride through the orgasm.
1:30 p.m.:
We go and grab Chipotle. Then I leave, stopping at the gym on my way back to the suburbs.


11:30 a.m.: Wake up. Wow, holiday weekends are great.
Head out for a quick run. Then pack up all my presents, grab some lunch, and head for home. I can’t wait to get back to the city.
5 p.m.:
Pick boyfriend up for yoga. The best part about doing yoga with him is that I have someone to stare at when I inevitably get super horny halfway through.
7 p.m.:
Puttering around Trader Joe’s together; this level of domesticity scares me. Sometimes I feel like this relationship has gotten way more serious than I ever wanted it to be. I know that I am going to be the one who ultimately ends it and feel guilty. Why do I have this underlying desire to sabotage?
10 p.m.:
Boyfriend pulls down my tank top and starts licking my breasts with the game on in the background. I wrap my legs around him we start to have sex. I beg for more and bite down into his shoulder. He promises to do it all night, but I know this will not happen. Boyfriend hates getting woken up for sex. I went and found the only guy in the whole world who would rather sleep then get woken up for sex. He says he just won’t fall asleep if we stay up getting it on like that. Yeah, right.


8:15 a.m.: Boyfriend is still sleeping. Debate whether or not to go to work at my internship. Rattle off an e-mail to my boss; it ‘s an easy choice. Strip down and jump back in bed.
10:30 a.m.:
Boyfriend calls me a sleepyhead. He starts massaging my breast, then rolls on top of me and we start making out. The guy eats me out like a champ; I don’t understand why he is not a better kisser.
10:40 a.m.:
Boyfriend stands up and pulls down his boxers, showing off. I’ve seen bigger, and smaller, but there is something about his penis that is just so nice. I even dig that he is uncut. Boyfriend kneels on the bed and pulls down my boyshorts. He starts fingering me. Being fingered is so under-rated.
10:55 a.m.:
We’re having sex missionary style when he pulls out and teases me. I hate it when he does that. It’s not fair! He pushes back inside me and pulls my legs up over his shoulders. We go at it for a while then he leans back and I place my feet on his chest. He asks me if I want to ride him. Of course I do! When we first met he did not like the girl-on-top position. I take great pride in having convinced him otherwise. It is now our go-to sex position. I tell him if I come before he does I will let him have anal sex. He gets excited, then quickly tells me he is going to come. Damn — I’m not ready. He comes inside me. I tell him he owes me a boob massage. He happily obliges.
We decide to head downtown. I need a dress for New Year’s Eve and he is buying. Yay! Sometimes having a boyfriend is so great.
1:30 p.m.:
Nordstrom’s dress department is terrible. Find one dress that I like: a slinky black one-sleeved number. Whoops, it is expensive. Smile and try my best to act cute as I steer him toward the register.
5:45 p.m.:
Realize that I have to leave for yoga in fifteen minutes. Ask how quickly he can go at it. We strip down and head to his bed. This time I am determined to orgasm. I climb on top of him and start licking him. He pulls off my shirt and I get on top. I love this position; it really is all in the angle and the hips. I feel the pressure building. I have one of the strongest orgasms ever. Not sure when I became such a screamer. My entire body is shaking. I spent all those years not being able to orgasm and then it turns out I’m a squirter.
5:55 p.m.:
He flips me over. Guess he didn’t forget about the butt promise. He sticks it in. It hurts. Not enough teasing. After a few tries I tell him I am not feeling it. He gets up to wash off his cock. He comes back and I get on my hands and knees, another favorite position.
6:10 p.m.:
I jump up. No time for post-sex snuggling. I’m going to be late for yoga. Give him a kiss on my way out the door.


9 a.m.: Wake up and start cleaning; bestie arrives today from Boston.
7:30 p.m.:
Yoga with the boyfriend. Tonight we have a private class. Love when it’s just us. It’s sort of sexy — minus the twentysomething instructor doing downward dog in front of us. Hate her.
9:30 p.m.:
Dinner with the boyfriend. Wish I could stay and get naked with him but my friend just landed at the airport and I promised to pick her up. We make out on the couch instead.
Gossiping with bestie about boys. Gosh, I missed her. She has a thing for Nigerian guys and apparently they are as girthy as rumored. Ouch. We reminisce about all our past bad decisions. Regular sex just isn’t as hot or illicit as a late-night, unexpected booty call.


9 a.m.: Wake up to a missed text and phone call from ex-f-ck buddy, K. Can’t believe he is still texting me nine freaking months later. He asks if I’m going to marry the boyfriend. Is he serious with this crap? I just feel bad for him at this point … but secretly love that he still texts me.
10 a.m.:
Appointment for fake eyelashes. New Year’s Eve is tomorrow and I am going all out this year. Sitting in the chair, I can’t stop thinking about K; hate that he can still get to me. I totally upgraded with boyfriend; why do I still have a soft spot for K? Oh yeah, because he was my first. And despite his small penis (I don’t discriminate), our sex was really fun and combative. Hate sex is often the best sex. For a long time I thought I would date Boyfriend for a while and then break up and go back to K. Wow, I am a terrible girlfriend.
4 p.m.:
Running on the treadmill. There was a point in my life when I would have chosen working out over sex every single time. These days, sex wins; still, a good workout is hard to beat.
12:30 a.m.:
Back at boyfriend’s. Feeling really sick — stomachache that started a few hours ago has gotten progressively worse. Tell boyfriend I feel terrible and go straight to bed. Feel bad but promise him a show tomorrow. He rubs my stomach as I fall asleep. Find this really weird, but sweet. We fall asleep spooning.


9 a.m.: Still not in the mood for sex. Boyfriend wakes up with a cold. Awesome.
11 a.m.:
We’re making out on the couch. Boyfriend gets hard immediately. I rub his penis while he rubs my nipples. I tell him I need to leave. I have a ton of errands to run before our New Year’s party tonight. Boyfriend pouts. I debate giving him a blow job. We make out some more. He tells me he understands and he’ll just masturbate to the hot girl in the back of his latest Maxim magazine. I pretend to be jealous.
7:30 p.m.:
Running late on way to boyfriend’s. He cleaned his apartment and grabbed dinner for me, bestie, and sister. He really is amazing. He looks so sexy tonight.
8:30 p.m.:
Meet up with friends at their hotel. Other best friend is going through a difficult breakup and has lost weight. She looks fantastic and I am jealous. My stomach is still upset and I am not feeling totally hot in my dress.
11 p.m.:
One drink in and feeling super tipsy. Get another drink and boyfriend takes it away from me. Pretend to pout. I am a total lightweight and I know it. I don’t need him to tell me how much I can and can’t drink.
Boyfriend pushes me into a corner and up against the wall. We make out. I am starting to feel really sick and don’t enjoy it. That one drink is hitting me hard. I don’t know how I could be this tipsy. Heartburn starts to kick in and I have to sit down. This is ruining my night.
12:30 p.m.:
Tell boyfriend I have to go home. I keep telling him I am sorry I ruined his New Year’s Eve. Leave without saying good-bye to any of my friends.
1 a.m.:
Lying on the couch with my head in his lap. He has stripped down to his briefs and is looking super hot. I want him so badly but I’m drifting off. Boyfriend picks me up and carries me to bed. I fall asleep almost immediately. Vaguely remember friends texting me asking me where I am.


9 a.m.: Wake up so angry with myself. Text friends to see about brunch later; turns out they were out until five. Wonder when I got so lame.
10 a.m.:
Boyfriend wakes up. His cold is worse. This makes me feel slightly better for falling asleep on him last night. I am only wearing a T-shirt and keep flashing him “on accident.”
12:30 a.m.:
Rolling around on his bed. He pins me down. Sometimes feeling helpless is such a turn-on. We start sixty-nine-ing. His beard is scratching my inner thighs and can’t help but giggle the entire time.
12:45 p.m.:
I get on top. After two days with no sex, it feels so good to have him inside me again. He starts to come. I am not ready but I don’t mind — it feels fantastic regardless.
1:15 p.m.:
As we’re getting on the bus to brunch I see friend from college who I was in love with for years walking down the street. I didn’t know he was in town for New Year’s. We stopped talking regularly once I started dating boyfriend. Immediately text him and admit that I spotted him. He used to refer to me as his “future wife” and he is still the only guy I can envision myself marrying. We chat back and forth about possibly meeting up later for drinks. That’s okay, right? Maybe I’ll bring Boyfriend.
10 p.m.:
Bestie and I text College Friend to see if he wants to meet for drinks. He says he is too hungover and needs to sleep. Typical. I should know not to get my hopes up.

TOTALS: One trip home to meet the parents; five acts of intercourse; one act of failed anal; one act of sixty-nine; one text by jilted ex; one run-in with old hookup; one failed New Year’s Eve; lots of making out; lots of yoga.

‘Terrible Girlfriend’ Sex Diary