The Single Guy Getting Over His On-Again, Off-Again Girlfriend

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Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Single Guy Getting Over His On-Again, Off-Again Girlfriend: Male, high school teacher, 39, Astoria, straight, single.

DAY ONE
5:22 a.m.: Wake up next to On-Again/Off-Again girlfriend. I don't consider her my full girlfriend, especially because she essentially moved to L.A. for work six months ago, and is only back maybe one weekend a month. We broke up before she moved but then kept on hooking up, texting, flirting. She's told me she's not seeing anyone else, but she doesn't want to know if I am. I'm pretty sure she knows I have slept with other girls (two, nothing ongoing), but we don't discuss it. I'm not used to her being in my bed anymore. She's more like a fuck buddy these days than a girlfriend and I feel like I'm too old for that.

6:15 a.m.: Both our alarms go off within five minutes of each other. She rolls over and finds me hard, and assumes this means I want to go at it. When she starts jerking me off, I'm not really feeling it. I do something I probably shouldn't and picture this girl I have a crush on going down on me, and soon I'm shooting all over On/Off's hand. She smiles and kisses me and drags me into the shower.
6:30 a.m.: She decides she wants to have sex in the shower, something we've done before, but I'm not ready yet and need to get to work. Instead I give her a quick hand job that I know doesn't satisfy her, but it'll have to do. She's here for two more days and, to be honest, I'm already feeling like I need my space.
5:30 p.m.: She texts me to meet her at a bar. When I arrive she's already a little tipsy and clearly has been flirting with the bartender. She loves to flirt and I was always jealous. That hasn't changed since we broke up. I down a scotch and am grumpy. After an hour, I go home. She has her own set of keys.
8:40 p.m.: On/Off finally gets back and is now officially drunk and wants to fool around. I'm not in the mood but I let her ride me. She comes, and I do too, but I'd still rather be alone. I don't kick her out of bed or sleep on the couch, but I consider it.

DAY TWO
6:02 a.m.: Wake up before my alarm and watch her sleep. I'm hard again but realize I'd rather jerk off. I turn off my alarm, since hers is set to go off too, shower, and jerk off quickly. Glad I didn't drink too much; hard to work with a hangover.
1:15 p.m.: Get a text from a girl I've gone out with twice but have only made out with. I let things die down to see if she'd pursue me. It's been two weeks. She wants to meet up tonight. I tell her I'm busy but we make plans for later in the week. I don't make up an excuse about what my plans are; wonder if it's obvious that I'm seeing someone else, then wonder why I care.
8:00 p.m.: Group dinner with On/Off and mutual friends. Feels like old times. She sits next to me and keeps putting her hand on my leg. I get hard; she notices and ventures just far enough up to let me know she knows I'm hard. Makes it a challenge to focus on the discussion, but I also know none of our friends really care about a little under the table action.
10:20 p.m.: We beg off from the others and she almost takes my cock out as we're making out up against a building. I stop her, even though it would be hot.
10:30 p.m.: She strokes me through my jeans in the cab, but again I stop her from unzipping my pants. For me, that works better in fantasy than real life, whereas On/Off doesn't care what the cab driver sees or doesn't see.
11:10 p.m.: I pin her against the front door and hold my hand over her mouth when she gets too loud. It takes maybe all of five minutes, but feels like some of the hottest sex we've ever had. Is it because she's leaving tomorrow?
3:07 a.m.: Her phone is buzzing and wakes me up. I see a text from a guy I don't know. "Miss you." I read through the rest of their texts and can't tell if they are sleeping together, but they are definitely very close. I have trouble falling asleep.

DAY THREE
7:15 a.m.: We both wake up with the alarm. She wants to fool around one last time before she leaves this afternoon, but I'm unsettled by the text. We settle for an intense make out session.
3:55 p.m. : On/Off texts me from the airport to say goodbye. Not sure how I feel about her going. I thought I'd resolved all that when we split up. I'm partly glad to be back on my own, but don't feel as single as I'd like to.

DAY FOUR
6:00 p.m.: Get ready to meet up with text girl. She's sweet, but she's only 22 and I'm not sure if I can be with someone so young, even for something not serious. I keep looking at her and thinking, "I could be your dad." Yes, that's a little crazy, and gross, maybe, but she's not a mature 22.
7:30 p.m.: Meet her at bar she picked in LES. It's a bit loud for my taste. She's wearing a thin white top and no bra. Again, she's 22. I can see her nipples and so can everyone else, which is probably why there's a guy chatting her up. I swoop in and put my arm around her possessively. We're not together together but I prefer my dates to not flirt with other people.
9:00 p.m. :She's been doing shots while I'm nursing my third beer. She wants to go dancing but I'm not up for it. "Please?" she begs and puts on a little-girl pout that somehow looks cute.
9:20 p.m.: I let her drag me to a club and have a few more beers and halfheartedly dance with her, hoping that my show of effort gets her to come home with me. She's a bartender and, unlike me, doesn't have to be at work at an ungodly hour.
11:00 p.m.: "Ready to get out of here?" I ask her, pulling her close enough so she can feel that I'm hard. "Just a few more songs." I decide "a few" will be three, and when she still doesn't seem into going home with me, I leave her there. Maybe I need to find someone closer to my age.

DAY FIVE
8:30 p.m.: I could meet friends at a bar but want to just stay home and watch TV. Wind up falling asleep and wake up from a ridiculous fantasy about a fellow teacher. I make it a policy not to even so much as flirt on the job. There's too much room for error. I've trained myself to, as best I can, not even notice the two incredibly hot women who work at my school. This one I'm friendly with but I keep my distance even though I could probably get a date with her. I don't let that stop me from thinking about eating her out. She has that prim and proper sexy-suit thing going on, and it always makes me want to rip her clothes off and send all the buttons flying.

DAY SIX
6:15 a.m.: Wake up and suddenly miss On/Off. For all her faults (and mine), we got along well and out of all the girls I've brought home to my apartment since I moved here two years ago, I've slept the best next to her. I shift my thinking to Hot Teacher, which isn't much better, since I can't have her either, but at least jerking off to her doesn't bring up any mixed emotions.
1:30 p.m.: Feel like one of my students with all their teenage hormones when Hot Teacher passes me in the hall and I get hard.
7:30 p.m.: Friend texts me that his new girlfriend has a friend she wants me to meet. She's 37 and also a teacher. I hate setups for the most part, but I have nothing better to do, and could use some flirting practice.
9:00 p.m. Teacher Setup isn't as hot as Hot Teacher, but she's cute enough and my friend's girlfriend is chill enough not to make it a big deal. Eventually they leave and we stay and keep talking.
1:10 a.m. It's way past my usual bedtime. I know she's not gonna go home with me tonight because she told me that earlier, but I'm actually enjoying talking to her. Neither of us have to be home since it's Saturday, but when I see her yawning, I pull her up and put her in a cab. I get her number from my friend.

DAY SEVEN
1:30 p.m.: I'm trying to be gentlemanly and wait to call her but find myself pressing the buttons of my phone to text Teacher Setup. "Is it too late for brunch?" Not the world's wittiest line, but an attempt.
1:42 p.m. Of course, right after I send that, On/Off emails me a photo of her boobs. Sometimes she does stuff like that, I guess as a way of gauging my interest. I get hard, don't get me wrong, and maybe if she were here and we were trying to have a real relationship I'd retract my brunch offer, but I don't let myself get too deep into thinking about her. I'd rather save that for Teacher Setup.
1:48 p.m.: Teacher Setup asks if I want to do drinks in her neighborhood (Long Island City). I can't tell if this means she wants to hook up too, but I agree. Realize I'm actually nervous about the date.
5:30 p.m.: Meet her at bar wearing favorite date shirt and jeans; I wore this shirt on first date with On/Off and consider it a lucky shirt even though it’s just a somewhat faded dark blue button-down. We get a drink and Teacher Setup is flirtier than she was the night before. I can tell already she's looking for something serious and I'm not sure if I am, but I still make out with her at the bar. All we've eaten are peanuts and beer so we're both a little drunk.
8:15 p.m.: Go back to Teacher Setup's place. It's small but she lives alone; the 22-year-old told me she has two roommates. Teacher Setup seemed kind of quiet and shy before but once our clothes come off she takes charge. She pushes me down, rolls on a condom, gets on top of me, and all sorts of filthy words fly out of her mouth. It's hot but a little disconcerting because unlike Hot Teacher, who exudes sex appeal, TS is cute in a more wholesome way. Less so now as she's thrashing all over and rocking her bed so hard it creaks. She shoves her nipple in my mouth and it takes me a few seconds to figure out what to do with her the piercing running through it. She comes twice, though, and tells me she wants me to come on her tits. I oblige, even though I'd rather have come inside her.
9:05 p.m.: She wants to cuddle and I feel like it would be rude to refuse, even though I want to take a shower. She falls asleep on me.
10:00 p.m. I ease her aside and tiptoe out of bed. Thankfully, she doesn’t wake up. Debate whether to leave a note and head home or set very early alarm and go home in the morning. We both have to work early in the morning and I don't want to start the week off cranky from being tired if I can't sleep, but don't want to be a total ass and just leave. Opt for the alarm. Not sure whether I see me and Teacher Setup together in the long term but she’s the best of my available options at the moment.

TOTALS: One handjob given; one handjob received; one public display of affection; one risque cab ride; one overly drunk 22-year-old; one blind date; three acts of intercourse.


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