Sex Diary: Road Trip To See A Friend (With Benefits)

Welcome to the Frisky “Sex Diary,” in which an anonymous person shares the details of her sex life over the course of a few days. Sometimes these entries are filled with revealing romps, while other times there is nary a naked moment in sight. Some of these diarists are frequent contributors. Want to share a page from your sex diary? Email [email protected] All entries will be anonymous. Diarist: Female college student, 21, living in the Southeast.


3 pm: I leave my college town for another one six hours away. The whole drive, a mantra repeats in my head: I’m going to see an old friend. I’m not driving six hours to have sex. I’m not driving six hours to have sex. Who am I kidding? I feel like a slut. Three weeks earlier I broke up with a short-term boyfriend who was two years my junior. I was bored and sexually starved enough to convince myself he wasn’t immature or bad in bed. I was wrong on both counts. I feel stupid for wasting my time with such a silly little boy. And with the hum of the highway in my head, I realize I am driving six hours to get laid.

I’m going to see a guy I met five years earlier in high school, William*. We’ve always lived far apart and have been having random crazy drunk sex (sans commitment) whenever we get a chance to see each other — a couple times a year — since I was 17. Sex on a raft in the lake with friends 20 feet away, on a boat, in an outdoor shower, in my parents’ bed, on the floor in the spare room, in a car in a parking lot … Am I an empowered woman who has mastered the friends-with-benefits relationship or a pathetic girl who is lacking in self-respect? The truth is he is everything I look for in a guy and I’ve been crazy about him since the day we met. I am driving six hours to have sex and to satisfy a delusional high school crush? As I near my exit with all this in my head, I’m thinking, Yes, I’m pathetic.

9:15 pm: I finally arrive at his apartment, where he lives by himself. I walk up to the door and before I can knock William opens it and we hug. It’s an awkward hug. We haven’t seen one another in five months and there is a tension in the air. We sit in the living room at an odd distance — it feels weird. Questions were running through my head. Do I act like a friend or something more? Was this a mistake? Are we going to sleep together?

William suggests we go to dinner. We do — he pays for it and everything else that weekend. The beer with dinner puts me somewhat at ease but just like when I was 17 he gives me that excited nervous feeling. Our eyes meeting sends my heart a flutter and a tingling in my skin. I’m a confident woman, but for some reason the slightest contact with him and I’m giddy. You know like when you’re 15, insecure, and blush because you feel like they can hear your heart speed up?

11:30 pm: Two hours have passed and things finally begin to feel normal (I might owe that to the drinks). We are at the bar with his friends, most of which I have met. Some girls I haven’t met before ask if I am William’s girlfriend. I quickly and politely respond that we are just friends. I’m glad he didn’t hear this conversation.


1 am: We have moved on to another bar. This entire time William hasn’t offered any attention that suggests we’ll be getting frisky later. He has to be doing it on purpose and knows it drives me crazy. Because I am not usually one for PDA, I ask him if he knows anyone around us in the bar, and when he replies “no,” I grab the collar of his shirt and pull his lips down to mine. It’s a soft, slightly open mouth kiss. When I pull away he laughs, “You didn’t have to ask that; I’d kiss you in front of anyone. And if you had any patience I would’ve done it first.” I feel silly, but triumphant and satisfied. The rest of the bar-hopping goes more smoothly with that first kiss out of the way.

2:30 am: We get back to William’s apartment, but his friend Ryan* is with us. As soon as he crashes on the couch William and I hit the sheets and shut the door behind us. I go down on him — he’s even bigger than I remembered. We have uninhibited sex, short but just what I needed. It feels like his body was made to match mine, he effortlessly stumbles upon all the right spots. Sex with everyone else has never been as good.

9 am: My eyes shoot open and I have an embarrassingly big smile when I remember where I am. I roll over and nudge William with my nose. “I know you’re sleeping but do you think you could wake up and play with me for a little while?” He smiles and answers with a kiss. I go down on him while he wakes up and then have sex that’s too good to have that early in the morning. Keeping quiet so I don’t wake Ryan, I push my face into his chest and claw into his back. I get what I didn’t the night before and it’s well worth the wait. William squeezes me tightly and says, “We finally did it. That was the first time we have had sober sex and it was so good.” We laugh and I hate how much I like him. After a minimal morning snuggle, we wake Ryan and go for breakfast. William and I return to the apartment and drift in and out of sleep, watching ESPN and waiting for his school’s football game to begin.

2:30 pm: We watch the football game at his friend’s house with a bunch of guys we both know. The boys cook an amazing meal on the grill and eventually their moods pick back up after their team suffers a loss.

9:30 pm: After a shower and a wardrobe change, we drive around town spending time with different friends at different bars but can never find a party. With the football game being away and the team losing, the town is dead.


12:30 am: Defeated in trying to find a good time, William, Wes*, and I go to grab a bite to eat and call it a night. While we’re eating, Wes says he has a hotel room booked for him and his girlfriend in the city on New Year’s Eve and they are looking for another couple to come. Shocked at the word “couple,” I turn and look at William wide-eyed but he just smiles reassuringly. “Couple?” I ask anyway. “Yeah, what do you think?” says Wes. “Can you make it?” In the five years that I’ve known William nothing like this has ever happened — we’ve never even planned when we are going to see one another more than three days in advance, much less been called a couple. Of course I want to go, but not knowing if William was really in on this, I don’t know how to respond. Luckily our food gets delivered just in time and I quickly change the subject.

1:30 am: Back at William’s apartment, we snuggle up on the couch and watch a movie on demand, “Rendition.” It doesn’t matter that the movie is about terrorism, I feel blissful. The movie is so action-packed, we still aren’t tired when it’s over, so we get into bed and talk about everything under the sun. After a few hours of talking he rolls over and kisses me hard. William says that he would be content if we just talked the rest of the night away, but because we don’t see one another very often, he might be disappointed if we don’t take advantage of being together. That’s just what I’m thinking! I was getting antsy at the idea that we might not sleep together again and I melt when he vocalizes the same thoughts. The sex is seriously unbelievable. No matter what position we move to, he finds where to go and at just the right speed. With no one else there I don’t hold back and am as loud as I need. We collapse next to one another panting. “That was amazing,” William says.

That’s when we begin to talk about us. I tell him that I thought this might be a friends-with-benefits situation, but he says, “We have never been just friends,” and tells me how he has always had feelings for me. I tell him how I have feelings for him too and I hate that he is always in my head. I can’t even pretend to have minimal interest when it comes to him and play the usual games. William laughs and says he wants whatever we have going on to continue as long as it can.

12 pm: I wake up far from well-rested and gather my things to go home. Just as I’m getting in my car to leave, William tells me how glad he is that I came to visit and that he really wants to spend New Year’s with me. “There’s no one else I’d rather kiss at midnight,” he says. I grab the back of his neck and give him a quick kiss goodbye. Alone in my car, I can’t stop grinning. There probably isn’t any commitment in our future and I am OK with that. It doesn’t mean I am lacking self-respect. I was feeling kind of slutty, but now that he has validated our emotional connection I don’t feel that way at all. I don’t care if I drove six hours to have sex. I don’t care if I’m chasing a stupid high school crush. I just hope our sexcapades continue.

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