sex diaries

The Woman Whose Roommate Is Her Ex-Boyfriend

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Woman Whose Roommate Is Her Ex-Boyfriend: Female, 22, clerical assistant and retail associate, Salisbury, Maryland, straight, single.


9:45 a.m. I wake up late, cuddling Ginger, the “not boyfriend” of five months. We’re open to dating other people, though it seems more often than not I’m the only one seeing someone else. I hate leaving him in the morning, especially when he is off (which seems like never) and I have errands to run. I give him a peck on the cheek (not the lips, too couple-y), throw clothes on, and head out the door.

10:05 a.m. Spending an hour at Planned Parenthood to change my birth control. Tired of not remembering pills and spending money I don’t have on Plan B. Decide on NuvaRing and begin it that day.

Noon Text roommate/ex-boyfriend to meet for lunch. Spend a ridiculous amount of time waiting for service, during which I get a text from a boy I’ve met on OkCupid confirming plans to hang out tomorrow for an official second date. Discuss current boy problems with Roommate who is more understanding than he should be.

4:15 p.m. Cute text from Ginger telling me he hopes I have a great day at work, which never happens in a big-box retail store.

9 p.m. Finally head home. Shower and hang out with roommate/ex-boyfriend. Decide cuddling with him is better than sleeping alone. I send Ginger a text to wish him a good night and sweet dreams. Fall into the familiar pattern of our old relationship. He asks if he can go down on me. I consent and sleep better than I have in ages.


11 a.m. Slept in for the first time in ages. Roommate texts and asks me to bring him lunch, since he can’t leave work. I agree, hit Taco Bell, and visit him at work briefly. OkCupid calls and tells me he’ll be ready at about three and to come over. Sends me his address and I plug it into my GPS. Hit the mall for a new pair of jeans and lose an hour wandering through stores when I should be getting ready.

2 p.m. Run home and shower. Shoot OkCupid a text saying I’m about an hour away and it will be closer to 3:30 when I get there. I go for comfy over couture, but wear the jeans I bought today that make my legs and butt look fabulous. I hate leaving the house with wet hair, but time is running out.

3:30 p.m. I arrive at OkCupid’s house and we head to the local Halloween store for shenanigans that fall short when we realize how small the store is. We decide to head down to the boardwalk and we walk about a mile in both directions. OkCupid tries to hold my hand, which I subvert by holding my keys in my hand. I realize I have subconsciously friend-zoned him. We eat at this little Mexican restaurant where I end up focused more on the Redskins game playing on the TV than on him. We decide to go back to his place where we watch an episode of The Walking Dead and Cabin in the Woods with his roommate (who I find wickedly attractive and wonder if she’s into girls).

11 p.m. I check my phone and see several missed calls from my mom, so I give him a quick hug and head out the door. Shoot him a text on the road apologizing for running off, but I’m an hour away from home and it may be an emergency.

Midnight Crisis averted. Crawl into bed without changing and sleep.


8 a.m. I arrive at work. Receive a text from Ginger inviting me over tonight to catch up on Sons of Anarchy. I tell him I’ll be over at about seven as I have some things to do.

4:30 p.m. Meet Roommate for dinner at Ruby Tuesday and then meander through the mall until 6:30 p.m. I send a text message to Ginger to make sure he’s home and he tells me he’s heading to the gym for about an hour. I go home with Roommate and play a couple games of Magic the Gathering before leaving for the night.

9 p.m. Ginger and I watch and finish the episode of Sons of Anarchy. He asks me the logistics of my NuvaRing. I decide to stay the night. We go to bed and are cuddling. My hand grazes his erection.

11 p.m. It’s been over a week since we’ve been more intimate than cuddling, so I give him a blow job in hopes of reciprocation. He asks for anal, which I balk at. One unreciprocated blow job it is. I let him come in my mouth and I swallow. I get up immediately after and brush my teeth. He can be so selfish sometimes. I slip back into bed and curl up against his side and fall asleep.


5:50 a.m. Ginger’s alarm is going off and I know that he needs to get up for work. I roll over and gently push his shoulder. He rolls out of bed and gets dressed. Gives me a quick kiss on the forehead and heads out.

6:30 a.m. I still haven’t fallen back to sleep and I don’t have to be up for another hour and a half. I masturbate thinking about the cute boy at the comic book shop who plays Magic with Roommate. Orgasms always make me sleepy and I drift back off.

8 a.m. I arrive at my job and start working on the budget books since the season is almost over for the campground. I get distracted and end up working less on the budget books and more on catching up on Supernatural.

Noon After two episodes of Supernatural, I redirect myself back to work. Roommate sends me a text asking if I want to come to the comic book shop and play Magic tonight, promises me Cute Magic Boy will be there. I’m in.

4 p.m. I get off work and head home. Roommate has already left the house so I’m free to be a girl and get ready at my own time. Who gets dolled up to play Magic? This girl does.

5:40 p.m. I arrive at the comic book shop and find that Cute Magic Boy is not there. I find Roommate and he tells me Cute Magic Boy doesn’t get there until later some days because of work. I play a couple games of Magic and he shows up.

7 p.m. Cute Magic Boy alternates between tickling me and beating me at Magic. The shop closes at nine, so I head out shortly before and pick up Arby’s on the way home for Roommate and myself.

10:30 p.m. Roommate returns home. Cute Magic Boy talked to him about me tonight. He wanted to make sure it was cool that he talked to me (bro code or something of the sort) and to see if I was exclusively dating Ginger, who had come into the shop with me once. I’m actually kind of excited.


4:30 p.m. I worked all day and my phone was surprisingly silent. No word from OkCupid since our date. I shoot him a “what’s up” text, to no response. No worries.

5:30 p.m. I head to the comic book shop and Cute Magic Boy is there. He waits until everyone leaves and asks me what I’m doing this weekend. We decide on a movie and dinner a few days from today.

9:15 p.m. I check my phone. It’s mysteriously silent. No word from Ginger or OkCupid, and normally they both send text messages several times a day. I start thinking about it and realize I haven’t received my routine “good morning” and “good night” messages from Ginger or any texts from him yesterday either.


8 a.m. I wake up earlier than I wanted to. Roommate is going to help me find a new outfit for tomorrow since my best friend is nine hours away at school. He’s not amused, so I promised him breakfast and a blow job, and with both out of the way before eleven I have plenty of time to shop before I have to work at two.

11:30 a.m. Roommate and I are at the mall and I’ve found the shirt I wanted in the first store I visited. I now have several hours to kill. We pick Target and I buy my luggage for my upcoming trip to South Carolina.

2 p.m. I go to work. Ginger swings by on his way to the rest of the mall. He sends me a text after he leaves asking if we’re still mad at each other. I didn’t realize I was supposed to be mad at him. I tell him we should probably talk about this. He suggests tonight, but I have plans to see Sinister with a few other friends. I can tell he’s miffed that I blew him off, but he’ll have to be okay.

8 p.m. I haven’t heard from Cute Magic Boy to confirm our date for tomorrow. I break my “never text a guy first” rule and shoot him a quick text just saying “hey.”

9:30 p.m. I get off work and Ginger texts me and suggests tomorrow for us to hang out, but my date with Cute Magic Boy is tomorrow. Ginger tells me just not to worry about it then.

11:55 p.m. I talk back and forth with Cute Magic Boy through most of the movie.

12:05 a.m. I get home from the movie and am kind of freaked out. Scary movies do that to me. I talk back and forth with Cute Magic Boy for about an hour until I’m tired enough to fall asleep.


10 a.m. I sleep in and immediately head into town for lunch. I swing by Walmart for new nail polish to match my shirt and laundry detergent.

Noon I do two loads of laundry at the laundromat to get everything ready for my trip to South Carolina and so I can wear my favorite jeans tonight. I run into Roommate’s mom while I’m there and chat with her for a little bit.

2:30 p.m. I finally get home from doing laundry and jump straight in the shower. I get out and there’s a text message from OkCupid. Long story short, he met someone else and he hopes that we can be friends. I can’t hold back the eye roll as I shoot back a quick “sure” and go on about getting ready for tonight.

5:30 p.m. I head to the other end of town to meet Cute Magic Boy for dinner. I always insist on driving myself on the first date. Dinner is good and the conversation flows easier than I thought it would. We only talk about Magic the Gathering once, which is good.

7:20 p.m. We leave from the restaurant to head to the movie. Cute Magic Boy suggests leaving my car at his place and he’ll drive back into town. We get to his place and I switch vehicles. I love his car, but he drives too fast.

7:30 p.m. We get to the movies and immediately remove the armrest from between us and I snuggle into his chest. As the last preview plays, we make out a little bit. I cuddle him and we hold hands throughout the movie.

10:10 p.m. The movie ends and he drives me back to his place. We kiss at a couple stoplights. We pull into the parking lot of his apartment complex and make out for a little bit in the car. He tells me I can come in if I’d like, but I opt for going home. This time.

11 p.m. I get home and call my best friend and give her all the details.

TOTALS: 2 acts of fellatio given; 1 act of cunnilingus received; multiple cuddles; 1 instance of friend-zoning; 2 separate make-out sessions; 1 masturbation session; 1 first date; 1 second date.

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Ex-Boyfriend Roommate Sex Diary