sex diaries

The Lovelorn Bisexual Looking For a Way to Gently Break Up With the Boy Toy Who No Longer Does It for Her

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Lovelorn Bisexual Looking For a Way to Gently Break Up With the Boy Toy Who No Longer Does It for Her: female, 22, marketing manager, West Village, bisexual.

10:15 a.m. Wake up to text from Goldilocks, author of a Craigslist posting I responded to. She’s both insufferable and enticing at the same time. “Mmmmm, how would you lick my pussy?” the message reads. Fell asleep mid-sexting the night before. Oops.
12:08 p.m. Receive text from BrooklynBoy, a European grad student I met at a party and have been casually dating. He is completely infatuated with me because I’m “not like American girls” and he’s “so excited” for our dinner date later tonight. When it comes to men I’m rarely interested. But I’m giving him a shot, as he’s nerdy, athletic, accented, and apparently excitable.

3:30 p.m. After heavy internal debate, send happy-birthday text to ex. We were in a relationship for nearly a year until I uncovered she was secretly in a relationship with a man for the last two months. Bitch broke my heart.
3:32 p.m. She responds. Light chatter ensues. She is going to be in town next weekend and despite my residual anger, I know we’ll fuck. We have incredible sexual chemistry. I miss her perfect body.
5:30 p.m. Getting ready for yet another proper hetero-date. I like that I don’t have to get glammed out for this guy.
6:07 p.m. BrooklynBoy texts that he is running late. Glad he’s chivalrous enough to let me know. Eyeing clock, I decide to quickly get myself off.
6:12 p.m. Mission accomplished.
6:45 p.m. Date arrives, wearing zip-up hoodie and fairly messy hair … Strike 1 for presentation.
7:52 p.m. Bill arrives. $27.50. I offer to split it and he accepts. Terribly disappointing. When I take girls out, I generally pay. I was looking forward to being treated … Strike 2.
9:30 p.m. After a walk around my neighborhood, he escorts me back to my building. He kisses like he’s trying to feed a baby bird; I try to making the experience enjoyable. He is such an awkward, smitten boy. I watch his lanky backside as he lopes toward the subway. He turns back and flashes a grin when he spots me checking him out. He waves a little too emphatically and descends the stairs.
11:48 p.m. Sexting with Goldilocks, but not feeling it. Masturbate to erotic story of a MMF (male/male/female) threesome, come really hard. Thank her for inspiring orgasm (blatant lie). Pass out.

2:45 p.m. Get turned on inexplicably at work. Try to dismiss feelings.
2:48 p.m. Retreat to ladies’ room to attend to myself. I’m a classy broad.
5:50 p.m. Meeting with Boss. He’s the perfect male specimen, and bears a striking resemblance to Don Draper. My mind wanders to questioning if he’s a sperm donor.
7:11 p.m. Sexting with Goldilocks on the train. We’ve never kissed, gone on two dates, and she’s describing how she wants to tie me up and lick me from behind. Why am I not turned on?
10:23 p.m. Text from BrooklynBoy asking how my day was and requesting to take me on a date to the Bronx Zoo next weekend. The Zoo? Are we 15? Debate responding. Don’t.

7:50 a.m. Respond to BrooklynBoy offering Sunday evening, casually mention that the Zoo will be closed. He hasn’t earned a Friday- or Saturday-night spot yet. Also, Goldilocks and the Ex will be in town in the next few days, and, as they tend to, the ladies get priority.
8:38 a.m. Get barrage of texts from Goldilocks including sexy picture messages. Good morning to you, too. She describes her dream from the night before. I’m in it. What a surprise.
11:42 a.m. Facebook Ex. No new wall posts or pictures. Disappointed by my own creepiness and inability to get over her. Fondly recall that she was a squirter.
3:44 p.m. Receive text from BrooklynBoy. He’s kind of adorable. Too bad I experience the same amount of sexual tension with my shower curtain. Maybe his facility with foreign tongues will make him amazing in bed? Vow to keep him interested.
9:15 p.m. Dinner with the girls. Discuss BrooklynBoy and Goldilocks. They all agree that Goldilocks is nuts and BrooklynBoy needs to step his game up. So true. They caution me about sleeping with Ex … I assure them I won’t become emotionally invested again. We cheer to group’s collective summary of dysfunctional dating stories.

6:20 a.m. Loudly get myself off in the shower. I love living by myself!
7:12 a.m. Play straight/gay/bi/closeted with my entire subway car. Focus energy on thin blonde with aquiline features and a masculine watch.
7:15 a.m. Decide for her that she’s bi. Envision subway sex scene where we’re the only ones in the car and it is magically sanitary.
10 a.m. Meeting with some clients. Immediately peg woman as a giant dyke; cropped hair, homo attire, backpack, Sigg bottle, and silly Bandz (seriously).
10:02 a.m. Space out. Start to think about my personal biases regarding gender and sexuality. Vow to never become a stereotype. Being enigmatic is sexy.
10:19 a.m. Dykey client brings me back to attention by mentioning her husband. My mind is blown.
9:03 p.m. BrooklynBoy comes over. He brings me flowers, condoms, and lube as “presents.” Way to cover all the bases. We go out for a late dinner and split the check, as I’ve grown accustomed to doing with him.
10:45 p.m. I invite him up to my apartment and we cuddle on the couch and make out for a while. I feel him get hard and expect him to request sex. He doesn’t. I am now thoroughly confused. Men are nothing if not dependably interested in sex, and he just threw a major curve ball. Does he not want to fuck me? Or is he being chivalrous and taking it exceedingly slow? What about the “presents?” I go to sleep pissed off.

4:50 p.m. Goldilocks lands. Texts me from runway. Debate whether or not I want to fuck her tonight.
7:15 p.m. Get home from work, lay out outfit for the gay bar.
8 p.m. Decide not to get waxed before our date and just trim my nether regions, don’t want her thinking I’m too expectant, eager, and prepared for sex, should we get there.
10:15 p.m. Stop at Starbucks for double espresso. Get eye-fucked by a leggy, dark-skinned woman. Return the favor. I always get so much more attention from women when I adopt more dykey attire. I look femme and dress “straight” most of the time and I frequently wonder how to emit gay vibes without wearing cargo shorts, dreading/chopping my hair off, or leading a unicorn on a leash.
11:25 p.m. Nearly an hour late, Goldilocks shows up. She looks okay. What is it with gay chicks and fedoras? The accessorizing needs to be reined in. Kiss her on the cheek hello. I need a cocktail.

1:30 a.m. Return to the bar solo and dutifully purchase our fifth round of vodka tonics. Extremely attentive redheaded bartendress offers a round on her. And two shots.
1:35 a.m. Think about taking flirty bartendress home, not Goldilocks.
1:50 a.m. Goldilocks is attacking my face, mauling me as I expected she would. I think I’m drunk enough to fuck her.
3:07 a.m. She works me over surprisingly well. Okay, I faked my orgasms; but she got me closer than I had thought, given how drunk, primal, and emotionless the experience was. I would consider making this a more regular thing if her ass weren’t larger than my preference.
6:30 a.m. Alarm blares. I feel exhausted and hung-over. Shake Goldilocks awake.
6:35 a.m. Goldilocks tries to initiate morning sex. She looks a bit rough in the daylight. I decline.
6:35 a.m. Jump out of bed and hop in the shower. Do not extend invitation to join.
7:09 a.m. Admire scratch marks all over my back. And bruises. And bite marks. What an animal.
7:45 a.m. She gets on uptown subway with me and I don’t make eye contact or try to hold a conversation.
7:58 a.m. It’s my stop. She gives me a big hug and a kiss on the cheek. I don’t do PDA. Definitely going to end it.
10:15 a.m. Truly struggling at the office. I’m not as resilient when it comes to weeknight drinking and violent fucking as I was in college.
5:12 p.m. Receive text from Goldilocks asking if she did something to offend me. I decide that I find her generally offensive and don’t know how to respond.
6:30 p.m. Ex arrives at office and picks me up in the rental car. She looks gorgeous, as always. We try to be civil and avoid charged topics (i.e. Goldilocks and BrooklynBoy) in I-95 traffic en route to mutual college friend’s bridal shower.
8:50 p.m. She compliments me, saying I look fitter than the last time we saw each other. I nibble at her earlobe to express my gratitude.
8:51 p.m. She says she’s turned on.
8:52 p.m. She unbuttons her jeans, allowing my hand just enough room to get under her thong.
8:56 p.m. She’s soaking wet and I bring her to a loud orgasm with my fingers. Kids, don’t sex and drive.
9:10 p.m. She pulls over at a rest stop and we jump in the back seat. I go down on her and she comes twice. She gets on top of me and rides me until she squirts and we both come incredibly hard, then collapse in a sweaty heap.
9:55 p.m. We get dressed and get back on the highway, both smugly smiling in endorphin-laced euphoria. Traffic is suddenly far less annoying.

12:05 p.m. She wakes me up as we’ve finally arrived at the bridal shower after-party, which is still going strong. Our college friends are all drinking and everyone is overjoyed that we finally made it.
3:15 a.m. Ex and I are now drunk and ripping each other’s clothes off in the motel room. She gets on top of me and the headboard is banging against the paper-thin wall as she slides her wet clit against mine. I suggest we move to the floor where we resume activities. I finger-fuck her from behind. She orgasms, then pounces on top of me and rides me to an impressive orgasm for us both.
3:58 a.m. After I come I realize she has terrible rug burn on her knees and feet from friction against the cheap carpeting. She half-jokingly bitches me out as I tend to her injuries with the first-aid kit. We get back in bed and fall asleep instantly. I really missed holding her naked body in my arms.
10:50 a.m. We wake up hung-over and have no time for sex before 11 a.m. checkout. We take a shower together and I let her get ready while I settle the bill.
11:12 a.m. A college friend explains that the session with Ex was abundantly audible throughout the motel complex. I become a little embarrassed yet insist the sounds weren’t coming from me (the Ex can be vocal, and I appreciate it immensely). The college friend relates another friend’s confusion as to how two girls could make the bed frame bang like that. We both laugh at this innocent closed-mindedness.
1:20 p.m. Ex drops me off at train station. We argue about the male suitors in our lives. We both get jealous and defensive, but acknowledge we’re not equipped to be exclusive together. We share a prolonged hug and exchange “I love you”s as it’s true, even though we don’t generally like to admit it. As the train pulls away I realize I don’t know when I’ll see her next. I text her that I already miss her, and we agree to keep in better communication.
3:28 p.m. I wake up from my nap to missed calls and texts from BrooklynBoy. He calls me his “beautiful girlfriend” and I’m feeling a little naughty for my forays with the ladies behind his back …
6:03 p.m. Get back to my apartment and hurriedly get ready for date with BrooklynBoy.
6:55 p.m. BrooklynBoy arrives, we get tea, then Thai, then more tea.
9:40 p.m. While holding me close as we walk to my apartment, he drops the L Bomb. I smile sweetly and say thank-you. He kisses my face and cheeks nearly every other step we take. Am I not into him because I’m too queer? Because I love the thrill of the chase? Or because his five o’clock shadow is irritating my skin? Probably all three. I decide I need either a new girlfriend or a sexy slightly older gentleman to have his way with me.
10:23 p.m. I text message end things with Goldilocks. Halfway through conversation I take a bong rip because this bitch stresses me out. Actually, my whole love life stresses me out. I really am seeking a healthy and happy fully monogamous relationship. Do these even exist in NYC? Where does a young bisexual meet sane, sexually insatiable, open-minded men and women? The pot makes me philosophical and I begin to ponder the courtship rituals of modern urban society. Too bad individual variance makes sweeping generalizations hard to conjure.
11:34 p.m. My musings are interrupted by a text from BrooklynBoy. “I had the most wonderful time with you tonight! I can’t wait to see you again :)” His overuse of emoticons is such a turnoff. I don’t respond.
11:53 p.m. I realize that there is no future with BrooklynBoy, but he’s technically doing nothing wrong. Am I mature enough to cut him loose? Fall asleep thinking of ways to end things, yet know I’m not quite ready to yet.

Totals: Four acts of masturbation, two makeout sessions, four acts of lesbian sex, one act of cunnilingus (giver).

The Lovelorn Bisexual Looking For a Way to Gently Break Up With the Boy Toy Who No Longer Does It for Her