sex diaries

The Woman Whose Ex Liked Her Better When She Was 300 Pounds Heavier

Once a week, Daily Intelligencer takes a peek behind doors left slightly ajar. This week, the The Woman Whose Ex Liked Her Better When She Was 300 Pounds Heavier: Female, 29, Boston, project manager, heterosexual, single.


4 a.m. I have the sleeping habits of a baby or a meth head. I didn’t fall asleep until one and the alarm clock just went off.

2 p.m. Meet with my shrink, who asks if I’m practicing safe oral sex. When I tell her I let guys finish on my face (“that counts as ‘safe,’ right?”), I know the woman is judging me when I walk out. She looked like an overweight Elle Woods. I bet she makes vision boards while crying every Friday night and binge eating Blue Bunny birthday cake cones. Oh, don’t act like you haven’t been there!

6:30 p.m. Survive the workday without lighting anyone on fire.

2:34 a.m. My favorite cokehead friend from London is drunk and feeling lonely. We’ve had phone sex and regular sex on numerous occasions. If he didn’t live overseas and had his “problem” under control, we’d be together. We’ve both said that. He’s also referred to me as his soul mate a few times, but it was probably the X talking

2:36 a.m. Nice to see his umpteenth rehab stint worked. In honor of his release, he requests some dirty talk, and who am I to say no? Phone sex with friends is always fun, plus he’s gorgeous and I might as well take advantage of the attention when I can get it. And it’s better than listening to him whine about how much money he gave his whore of the month.


1:45 p.m. Getting a safe sex lecture from my doctor. When that happens, you get to leave the office with a goodie bag of condoms, lube, and a scarlet letter to wear on your chest. It’s better than leaving with a heart monitor. No one wants to bang a girl who passes out randomly owing to her blood pressure medication.

3:47 p.m. A guy who is barely a friend starts telling me (via Twitter — classy) his wife left him and how lonely he is. Listen, mister, you’re barking up the wrong tree. (A) I’m five-foot-nine and you’re five-foot-six on a good day, and (B) I’ve done the married-guy thing; it’s fun, but it’s a no-win situation. Plus, having to explain to your co-workers why there’s a random angry woman screaming “If you want him, you can have him and take his baggage too!” in the office isn’t fun. I know. If you think the phone conversation with the man at the center of it all is awkward, try explaining to your boss why you’re babysitting during work hours and why this random broad called you a whore in front of clients. And people say fat girls don’t have fun?


7:30 p.m. Heading off to a date with a guy from my past. A couple years ago, when I was 300 pounds heavier—guess I should have mentioned that before; I used to weigh 448 pounds and now I don’t—he thought I was sexy (or I was just desperate for attention?). He cheated on his girlfriend with me on a pretty regular basis. We haven’t seen each other in a while and decided to catch up (he’s single now).

8 p.m. The look on his face when he sees me walk in isn’t what I expected. He scowls at me. He knew I’d had surgery and knew I had lost weight, but he tells me he thought I was overestimating my weight loss. Evidently, to one man, I looked better when I was cow-like. Just because I’ve lost weight doesn’t mean I lost the ability to have sex or suck dick. I’m still a whore! Doesn’t that count?

8:15 p.m. He tries to get me to eat pasta and fried foods when we’re ordering, which for me is a huge no-no. If I have fried food I’m puking like there’s no tomorrow, and that’s not attractive on a date. 

10:57 p.m. Might as well take care of business myself. I can’t sleep. All I can do is think about how disgusted he was with the new me. I could see him being disgusted if I was still wearing my old fat girl clothes at the size that I’m at now. But I look good! I can’t win. I know he’s not going to change his mind. I’m too drained to find someone else to do it for me right now. Thank God for vibrators and the internet.

11:20 p.m. Life was easier when I was fatter and had no shame. I mean I still don’t, but suddenly I have these things that could be confused with “standards.” For some weird reason I want a guy who likes me for me and not because of my Hoover vacuum sucking skills. Guys may like my oral skills, but I just don’t think their moms would appreciate hearing about my go to moves in the bedroom.

2:24 a.m. In the words of Joe Strummer, “London Calling.” The former cokehead is back on the phone. He’s miserable and I needed to get up anyways. He’s weepy and lonely. Great. I know he’s having a hard time coping with being sober and that his doctors are trying to find a new prescription cocktail that works. I know this is probably going to sound incredibly cruel, but I’d rather he be on coke than like this. He used to screw like a champ when he was on blow. Now he’s just depressing. At least when I could drink, I could have a couple shots to deal with him when he was like this. But that’s not an option now. Smaller stomach equals forced sobriety and yes, it sucks. Everything is easier to deal with when you’re drunk. I guess it’s time to put on a show and put a smile on someone’s face.

2:45 a.m. I’m the P.T. Barnum of phone sex.


Noon Wake up and decide to keep sleeping in. That never happens. Day off!

1 p.m. Take care of myself a couple times. Decide against leaving the house. The only downside: My vibrator dies in the middle of masturbating. I’m going for a third round and when I turn it on, sparks fly. That’s never a good sign. Good-bye, old friend. You served me well.


1 p.m. Today is very Larry and Althea Flynt without the coke and paranoid delusions, but I need a quiet day lounging around in bed and shutting out the world. Everything I need is close by and the less interaction with the general pubic, the better. 

4 p.m. Finally decide to enter the land of the living and go to a sex toy store (called Amazing) to replace my old friend.

4:30 p.m. While I’m contemplating my vibrator options, a shockingly attractive guy asks if I’m looking for a playmate. “I could make it worth your while.” Then he flashes a cash roll that for a second makes my mouth water.

4:32 p.m. I turn him down. I don’t know why. Well, I do. I’m assuming if he’s flashing cash to get ladies, he’s either a cop and it’s a sting operation or he’s a serial killer and he wants to use my head as a candy dish. I grab my new Hitachi Magic Wand, condoms, pay, and get out of there quickly. Note to self: find another store or order a backup toy online, just in case this guy is there next time.

4:37 p.m. Guy follows me outside and asks what he can do to change my mind. I’m not that cute; he’s just insanely desperate. An employee who’s taking out the trash asks if I’m okay and want him to call the cops. I should have said I wanted a gift certificate for my next purchase, but instead I rush away.

6 p.m. Home. New toy works and is even better than I remember the old one being. I should have bought a new one a long time ago.


8 p.m. I have a second date tonight. They’re usually painful and I want to stab myself before dinner is served. This guy could be a keeper, though. He let me pick where to eat, since my stomach is so high maintenance, so I chose Red Lantern. I can do vegetarian without being forced to order a salad as always.

9 p.m. I’m attracted to him — appearance-wise, anyway. Other than that, there’s nothing there. It’s like talking to a brick wall. He has no opinions; he says he’s not a music fan. How can someone be that beautiful, but so empty? Still, I decide to sleep with him; I figure second-date sex is better than first-date sex with some random Craigslist hookup.

10 p.m. We chat near my car and kiss and then head up to his place, which is conveniently located a block from my car.

10:15 p.m. Based on past experience, I assume I’m just going to spend time on my knees. I do, but not in the way I’d expected. He gets behind me and wants to have sex doggy-style. Who am I to stop the momentum? The sex is good. I let him finish on my face and in my mouth, and he returns the favor.

11:30 p.m. After resting a bit, we have another go. At my request, he slaps my ads and calls me a “fucking whore.” That’s the best part of the sex. He isn’t at all weirded out by what I like or request. The last two guys I slept with weren’t comfortable with name-calling. I say, if you’re going to treat me like a whore in bed anyway, you might as well call me one and let me enjoy it. Sex post-weight-loss is a lot better. I’m more comfortable with my body now and willing (or at least open) to do more than I used to be.


7:30 a.m. There’s nothing like strolling in your apartment when everyone else is walking out the door for church on a Sunday. Judge all you want and tell me I’m too old to do this stuff.

7:35 a.m. Back to sleep.

1 p.m. Very glad I went home with him last night. I needed someone to get me off like that and prove to myself that I haven’t ruined myself with machinery like the Hitachi.

4 p.m. Give my rundown of the date to friends and am promptly judged by everyone I know. Ugh. If you’re my friend, just let me be me. Don’t just me or my actions. I’m being smart about what I’m doing and I know I probably deserve better, but it’s a learning experience. I’m basically going through puberty again.

TOTALS: 6 orgasms; 3 masturbation sessions; 2 dates; 2 acts of phone sex; 1 vibrator broken, 1 vibrator bought; 2 acts of sexual intercourse.

Weight Loss Sex Diary