sex diaries

The Oakland Lesbian Sleeping With Her Submissive Male Neighbor

Once a week, Daily Intelligencer takes a peek behind doors left slightly ajar. This week, the Oakland Lesbian Sleeping With Her Submissive Male Neighbor: Female, 26, Oakland, California, massage therapist in training, single, lesbian.


1 p.m. Meet up with the Binder to rock-climb. This is our first date, and she’s cuter than her pictures on her OkCupid profile, so it’s a pleasant surprise. It’s not that I felt she was unattractive in her photos — it’s just nice to see that they didn’t do her much justice.

3 p.m. After climbing for a couple of hours, we grab some nonalcoholic drinks before parting ways. We agree we’ll do it again sometime soon when her schedule is freer.

5 p.m. My friend Big Red comes over so I can give her a massage. This is my first full-body massage, and once the nerves wear off, it goes well.

7:30 p.m. Big Red and I get dinner nearby, and she entertains me until I have to meet up with the Nomadic Chemist for date two of the day.

9:45 p.m. I meet the Nomadic Chemist at a new bar I’ve wanted to check out for a few weeks. Not many people know about it yet, so it doesn’t get very crowded — just the way I like my bars. The Nomadic Chemist looks just like her pictures on OkCupid, and that is not disappointing.

10 p.m. We grab some bourbon and talk.

10:46 p.m. More bourbon as we continue to get to know each other. We’re both loosening up a bit and decide to play pinball. We each take a flipper and end up playing for quite some time.

12:30 a.m. We’re not ready to part ways or end our night just yet, so we walk over to a bar that has better music for dancing. It’s crowded with a random assortment of Oakland folk. I’m not surprised.

1:30 a.m. As we’re dancing, I can tell she’s into me. I’m not sure how into her I really am. She’s attractive, but she’s not really my type. I go with it, though, because I am horny and could use a body instead of just my vibrator for a change. The last chick I slept with was a real-life never-nude. She made me feel like I was in middle school having to rub her clit over her pants. It wasn’t until the third time we had sex that she finally let me underneath her underwear, and even then she wouldn’t take off her pants. It’s too bad she was so weirdly self-conscious, because she was also incredibly beautiful.

2:30 a.m. I take the Nomadic Chemist back to my place.

3:37 a.m. After watching a couple of episodes of Girls and some making out on the couch, we move to my bedroom. Finally.

4 a.m. She fucks me hard. Just the way I like it. She has the biggest nipples I have ever seen, like large cylindrical marbles. Her boobs aren’t that big, so the contrast is noticeable. I like them and make sure she knows it by sucking on and flicking them with my tongue. I love playing with nipples. After fucking me with her tongue, she rubs her finger up and down my crack. I love having my ass played with, so I moan to let her know to continue. She inserts her finger and it brings me over the edge. My whole body tenses up and then releases with intense pleasure. I’ve needed this.

4:30 a.m. I’m doing her now and I can feel how wet she’s getting. This further turns me on so I continue even harder. I love my sex rough, so it’s nice being with someone significantly less delicate than the Never-Nude.

4:45 a.m. She asks me if I have a strap-on. I got rid of my last one because my ex had bought it and I went through this phase of rage after the breakup, throwing out everything she bought me. Instead, I use more fingers to fill her up. She likes it and orgasms hard.

5:30 a.m. I’m spent. Need sleep. We pass out.


10:30 a.m. I’m awake, but I don’t want to be. The Nomadic Chemist is up, too. We cuddle and she tries for some morning sex, but I’m too tired and sore from last night. Her nails are long and she scratched me (inside) a bit. The sex was worth the blood. I find that it usually is.

11:15 a.m. Finally get out of bed and make us breakfast.

Noon I drive the Nomadic Chemist home and we agree to hang out again for some baking and wrestling. I head back to my place to set up for my next massage.

9 p.m. I’m lying in bed ready to go to sleep. I pull out my bullet and give my clit the TLC it desires on a daily basis. I find that even when I’m having regular sex I still need or want (not sure which one it is — probably both) to masturbate. I don’t feel like getting up to get my laptop for porn, so I just lie in bed and use the images in my head.

9:30 p.m. After bringing myself to three orgasms, my clit is vibrating and I can feel the sleep creeping in.


9:47 p.m. On my way home from class I get a text from Slave Bitch. He wants me to come upstairs. I can tell he’s drunk. He lives a couple of floors above me, and one night a few months ago I had blackout-drunk sex with him. A part of me had some fantasies only someone like him could fulfill. He let me, or more like begged me, to fuck him. I did, with a strap-on, and peed on him in the tub. He’s submissive and desires a mistress. I enjoyed nothing about that night, and even though I still fantasize about straight guys, I know for sure I don’t want to be doing the fucking. I’ve been avoiding him and ignoring his texts since our last encounter, but for some reason I give in this time.

10:12 p.m. He answers the door naked and asks me if I want him to get on his hands and knees and crawl to his bedroom. I honestly don’t care as long as he knows he is not sticking his penis inside of me.

10:30 p.m. He goes down on me for a while and it feels good, but I am so not attracted to him that I know I won’t orgasm, so I just let him do his thing. I try hard to bring my mind out of what’s actually happening so I can get off, but I can barely even get wet, which has never been a problem for me.

10:45 p.m. He keeps insisting on kissing me. I generally like a hard passionate kiss with a beautiful woman after she’s gone down on me, but he has a full beard and I don’t enjoy it. I indulge him just a little. I prefer the soft, smooth features of a woman. I’m still questioning my intentions for coming upstairs. I think boredom and sober curiosity played a big role, plus knowing I can do whatever I want to him and he’ll enjoy it. I should have had a drink beforehand.

10:50 p.m. I have him on all fours and I lube him up, along with my finger. I start off slowly, giving him time to adjust, and then fuck him hard. I milk his dick a bit. I can tell he likes it from the precome dripping all over my hand. He asks me if I like jerking him off, and I don’t answer, but I do get a bit of pleasure from this. I can see him looking in his window at our reflection. Knowing how much he wants this turns me on a bit.

11 p.m. He asks if he can get on his back so he can watch me. I allow him to do so. I keep going and he furiously jerks off. He comes all over his stomach. When he gets up to go to the bathroom to clean off, I wash my hands in the kitchen, get dressed, and leave.

11 p.m. Now that I brought someone to orgasm, I figure it’s my turn. I take my bullet vibrator and think about what a submissive Slave Bitch is. I imagine him getting screwed by multiple guys and sucking their dicks. I orgasm three times before I put the bullet away.


9:45 p.m. I get home from back-to-back yoga classes, ready to lie in bed, masturbate, and pass out hard. I bring my laptop to bed with me. I default to one of my favorite Broke Straight Boys videos in which an ugly-faced surfer-looking dude with a huge cock gets fucked by two guys. I don’t know what it is about gay-for-pay that gets me off so much, but it’s been my masturbation material since I was 14 and played a big role in the delay of me realizing I am a lesbian. It can be confusing when what gets me off when I’m alone and what gets me off with someone else are such starkly contrasting things.

10:15 p.m. After orgasming twice, I decide to give my clit a break and attempt sleep.


7 a.m. I wake up horny and I have just enough time before yoga to get my day going in one of the best ways possible … orgasm. Morning sex with someone else would be the preferable option, but my bullet will do for today.

7:35 a.m. After orgasming four times, I get out of bed, get dressed, and go to yoga.

3:43 p.m. Get a text from the European asking if we’re still on for tonight. I’m not sure if this is a friend thing or a date, but I decide to keep an open mind. Even though she’s way too femme, she’s cute and I found myself somewhat attracted to her when I met her at a trivia night last week.

8:35 p.m. We head downtown for Tourettes Without Regrets, an underground performing-arts show. She’s a lot prettier than I remember.

9:15 p.m. Jamie DeWolf asks who’s there on a date. We both look at each other, unsure if it’s a date or not.

11:40 p.m. We talk as we walk back uptown. The conversation has been good all night, and now I am certain this was definitely a date.

11:55 p.m. We get to the BART station where she’s trying to catch the train back to San Francisco. We start saying our good-byes and agree that we should do it again. We’re staring at each other in that way you do when you want so badly to kiss someone. I’m so bad at making a first move, and just as I decide I will, she leans in and kisses me. Her lips are soft, but the kiss is passionate and intense.

12:05 a.m. We’re still making out outside the BART station in downtown Oakland. We acknowledge it’s probably not the safest place for two young women to be grinding their bodies into each other, but it doesn’t stop us. We agree to choose a safer place next time. I’m thinking there should be less clothes next time, too.

12:15 a.m. I am tempted to invite her back to my place, but I have to wake up early, she has to wake up early, and I don’t feel a need to rush this one just yet.

12:22 a.m. I get home. I’m tired but invigorated and incredibly horny. I undress, jump into bed, and touch myself. I decide to leave the bullet in the dresser and use my fingers. I think about all the things I’d like to do to the European. I want to rip the clothes off her body, press her into a wall, hold her down, and do her hard. I orgasm and pass out.


11:39 a.m. I get a text from the Ex asking me if I want to hang with her, her girlfriend, and some queer folks tonight at the Syd the Kyd show at the New Parish. They think they’ve caught a catfish and they invited her to the show. The Ex knows how much I love catfish, so she thought I’d be amused. She knows me well.

9:40 p.m. Get back from a daiquiri happy hour my friend hosted in San Francisco. I’m four drinks in without any dinner.

9:55 p.m. I get to the New Parish, grab a whiskey ginger, and head upstairs to meet them. The Ex’s girlfriend’s friend is the Binder. Typical that everyone knows everyone else in the Oakland lesbian scene. The Catfish is there, and she is not a catfish at all. She looks exactly like her picture, fake nails and all, but it’s tough to believe that she is studying neuroscience at UC Berkeley.

12:12 a.m. I decide to leave since I have to be up early for a baptism. Words I never thought I’d say. Ever.


12:30 p.m. Back at my friends’ house after their son’s baptism. It’s safe to say that I was the only culturally Jewish, atheist lesbian in church this morning.

6 p.m. Connecticut is at Fancy Pants’ birthday dinner, and we awkwardly say hi. I tried to hang with her a couple of months ago when we first met, but she didn’t seem into it and we haven’t spoken or seen each other since. I mostly ignore her at dinner. When she leaves she taps me on the shoulder and asks if she’s going to see me later at Ships, a lesbian dance party. Why are girls so damn complicated?

10:30 p.m. The Catfish spots me and comes over to say hi. She touches my neck and chest while telling me that I dumbfounded her the night before. I only let it continue because I’m hot from dancing and her hands are ice cold. She’s way too feminine for my taste, but she’s not ugly by any means. She tells me she liked my OkCupid profile and that I should hit her up on “The Okay See” whenever.

11 p.m. A little awkward-looking Asian girl who appears to be friends with some of the folks I came with comes up to me and asks me if I am femme or butch. I hate that I seemingly have to choose one or the other. I’m not into those sorts of labels, and I don’t identify with either of them. I tell her neither and ask what she thinks I am. She says she thinks I’m pretty androgynous. I take the compliment and tell her that I do, in fact, identify as androgynous. I can’t tell if she’s trying to flirt with me or not, but either way, I’m not into her, so I move on.

1 a.m. Run into the Never-Nude outside while talking to her co-workers. Somewhat weird experience. She has the emotional maturity of a 13-year-old and very little social awareness.

2 a.m. Go home. Alone. Perhaps not how I was specifically hoping to end my night, but the European is in Tahoe this weekend, and she’s been my most promising date in a while.

TOTALS: 3 dates; 14 orgasms experienced; 2 orgasms given; 1 act of receiving anal sex; 1 act of giving anal sex; 1 passionate make-out session. 

Oakland Lesbian Sleeping With Her Male Neighbor