sex diaries

The Portland Woman Masturbating With Clothespins on Her Nipples

Once a week, Daily Intelligencer takes a peek behind doors left slightly ajar. This week, the Portland Woman Masturbating With Clothespins on Her Nipples: Female, 31, Portland, Oregon, hosiery salesgirl/writer, in a polyamorous relationship, bisexual.

DAY ONE

7:20 a.m. My partner, Sidebeards, and I have separate bedrooms because of opposing schedules and sleeping habits. I’m rushed to catch a bus but make time to sneak into his man cave for a kiss good-bye. He smiles and cuddles me briefly; this reassures me last night wasn’t a total disaster. We had an episode of spankus interruptus. Our kinky game and dirty talk went sideways. No one got hurt, but no one got off either. I went to bed horny and confused.

1 p.m. One of our regulars, Heavy Breather, calls. He needs help finding argyle socks for his wife. Her vagina is real loose, so he wants to see her in tight socks. He hangs up without making a purchase. These foot fetishists are mostly harmless, but we don’t get paid enough to provide customer service, spank fodder, and phone sex. This happens about once a week.

7 p.m. Writing isn’t going well, so I procrastinate by e-mailing Focus, a photographer I’ve shot with many times in the past. He’s sexy in that older man with a camera kind of way. We have an intense but unconsummated flirtation, so planning for another shoot quickly becomes dirty talk.

8:30 p.m. The flirting gets me worked up, but just as I reach for my vibrator, Sidebeards comes home. He was recently interviewed about his newly published book, so we get caught up in excitement over his success. I’m happy for him but also understand he’s in writer promotion mode and know better than to expect him to slow down long enough to spend naked time with me.

10:30 p.m. He’s tired and distracted so I settle for some smooching before he puts me to bed.

DAY TWO

11 a.m. Focus and I finalize plans to get together without a camera. This is the first time I’m considering being intimate with anyone other than Sidebeards in the year we’ve been together. I’m nervous. The high of flirting with Focus gets me through the day so that I can momentarily stop obsessing over the failed playtime with Sidebeards the other night.

2 p.m. I’m modeling for photos that will become an advertisement for the legwear company I work for. Fully clothed, posing in the park, I’m chastised several times to cover more leg and keep my hands far away from my lap so that the photos won’t be “suggestive.” Proof that suggestive is awfully subjective.

8:30 p.m. I refuse to go to bed frustrated again. I’m kissing and fondling Sidebeards, glad that he’s getting into it. He goes down on me.

8:40 p.m. His tongue is driving me crazy, but I can’t get off this way. I insist he de-pant and fuck me. Instead, he teases me by going slow, tossing me around through half the Kama Sutra. It’s sweet and a little naughty, just what we need to reconnect.

9 p.m. I say the magic words, and he orgasms inside me. I need my vibrating bullet to get off, which he’s more than happy to assist with. All the crazy from the last few days melts away as I come.

DAY THREE

8 p.m. At the hipsterist venue in town to see Stereo Total with Sidebeards and his work friends. On my way in I run into Mopey, a failed OkCupid date from several months back. After two dates, he was making plans for summer trips together, not understanding why I broke things off. Awkwardly, we work in the same neighborhood, so we see either other regularly but never speak. Tonight is no different.

9 p.m. So many young sweaty bodies rubbing on one another. I’m not in the mood for their shenanigans, so I sit down and watch from afar, happy that Sidebeards is enjoying himself in the thick of it.

11 p.m. Sidebeards’ friends are staying with us for the weekend; they take his room. I was secretly excited to have two nights sharing sleeping space with him. Instead of coming to bed he goes out with Beer Guy, whom he hasn’t seen in a while.

Midnight Can’t sleep, but I can’t jerk off since the boys are in the living room and I’d feel too weird turning on my vibrator.

DAY FOUR

6:30 a.m. Sidebeards is on the couch. They must have been up late drinking; he barely moves when I say good-bye and go to work.

4 p.m. Just barely manage to stay awake through work. Sidebeards has the day off; having opposite schedules is frustrating.

7:30 p.m. On a bus to get tickets to the Black Angels show. Stuck in traffic on the bridge, I glimpse the balcony of a condo; a girl is going down on her man-friend. I smile at the crazy exhibitionists.

9 p.m. I would love to go to sleep or lie in bed naked with Sidebeards, but Beer Guy and his wife lure us into drinking on the lawn. It’s nice to get to know some of Sidebeards’ oldest friends.

2 a.m. We literally crawl into bed and pass out.

DAY FIVE

1 p.m. After a half-day at work I’m out to lunch with a co-worker. She might be the only person with a filthier mouth than me. We end up having a distinctly inappropriate conversation while surrounded by soccer moms by using ridiculous euphemisms to not offend anyone. She’s telling me about a new acquaintance who admitted to only being able to masturbate by humping furniture. Apparently he has a special chair in his apartment for such purposes. I’m impressed with his creativity.

5 p.m. My week is finally done, and I’m alone in the house. I should be editing, but instead I’m perving FetLife, looking through the newest photos of friends. Most are rope-bondage-related, and I realize how little of that is in my life recently. I rub myself looking at pretty girls bound, focused on the sexy way their breasts look compressed in rope.

5:15 p.m. I get out my vibrator and some clothespins to torture/tease myself with. Fantasizing about being bound gets me off almost too quickly, so I come a couple of times to extend the experience.

6 p.m. Back to my writing and realize I’m too antsy and horny again to focus.

9 p.m. I’m frustrated, grammatically and sexually, when Sidebeards gets home from his day job. He kisses me deeply and smirks, which means we’re on the same page. I just need to finish writing this story, and he will be all mine.

10:30 p.m. He’s distracted by the time I find him, but I refuse to accept a cuddling-only evening. I go down on him so slowly that he begs me to sit on his face. It’s his turn to wait for what he wants. I enjoy his pleas to let him lick me, which I eventually do allow.

10:50 p.m. I can’t resist any longer; we have sex slowly. I watch him go crazy as I periodically dismount him so he can watch me touch myself before I resume riding him again. He asks nicely, so I do him properly. When I’ve had my fill I pull him out to jerk him off the way he likes.

11 p.m. He’s still hard, so I hop back on before falling asleep on his chest, happy and finally satisfied, still straddling him.

DAY SIX

10 a.m. Two years ago, I, along with several other women, was raped by a local rope-bondage instructor. Today I finally get to give my official statement to the police.

1 p.m. I explain every detail of my sex life while defining words like hand job, sex toy, and BDSM to a detective with a gun strapped to his ankle in a tiny room for three hours. This might be the least sexy thing I’ve ever done.

3 p.m. Sidebeards and I take an accidental nap to shake off our time at the police station.

6 p.m. We wake up just in time to get to our appointment to soak in the clothing-optional communal outdoor hot tubs. The only way this experience could be more Portland was if the tubs were also fair-trade and shade-grown, and yet they are the perfect place to relax. We’re the only ones here at the moment enjoying the treat of being naked in the sun as the water washes away the stress of the day.

Midnight We finish watching a Johnny Depp movie. I’m half asleep spooning with Sidebeards until I feel how hard he is. We have tender, slow sex, all kisses and caresses, until I can’t take it anymore. I use my legs to pull him into me harder; he gets the idea. He comes, then helps me get off with a vibrator.

DAY SEVEN

10 a.m. Kisses and sleepy fondles from Sidebeards before he leaves for work. He gives me a naughty grin and tells me to have fun on my “date” with Focus later. Through his pants I can tell he’s hard and wish I could blow him before he leaves.

Noon Focus is texting me filthy threats, promises, and instructions. I tie a rope harness on myself like he asks. He knows how much I enjoy rope but isn’t comfortable tying it himself; I’m happy to help. I sit tied-up under my clothes, waiting.

1 p.m. We make awkward small talk while Focus shows me his bag of tricks. There are a lot of floggers involved, and yet he asks for a hardcover book to use for a warm-up spanking.

2 p.m. Every inch of me from hip to ankle has been beat repeatedly with his battery of floggers, and yet the damn book is the one that hurts the most. He hits me repeatedly on the front of my thighs with it. I’m restrained in such a way that if I wiggle too much I’ll pull the clamps on my nipples tighter. They already hurt quite enough, thank you, so I hold.

2:15 p.m. He adds a ball gag and blindfold and flogs my nipples with the clamps still in place. He’s as talented at doling out pain as he is at taking photos.

3 p.m. He sits on my belly and Hitachis me into oblivion until I’m a whimpering mess.

3:15 p.m. He’s packing up his goodie bag before I’ve even untied myself. As soon as we say good-bye I feel bad for not reciprocating. He didn’t ask for anything in return, and my brain is too scrambled to offer. I owe him big next time we get together.

4 p.m. I can’t focus on writing; somehow I’m still worked up. I use two dildos to double penetrate myself, coming almost instantly. That’s better!

7 p.m. Sidebeards is home. I show him the bruises already forming and tell him about my day. We end up in my bed, where he torments me by kissing and licking each overly sensitive mark on my legs, telling me how filthy I am for letting another man into my bed.

7:15 p.m. I can’t take it anymore, so I beg him for sex. Everything is swollen and sore, and yet I’m enjoying myself. He’s amused by the ouch/give-me-more conundrum. So amused that just before coming he pulls out and says, “Hold my cock and aim it at your whore cunt,” as he ejaculates on me. I love how dirty and imaginative he is.

9:30 p.m. He goes off to paint. I finally feel satisfied enough to sit down and focus on my writing.

TOTALS: Four acts of intercourse; one blowjob given; two acts of cunnilingus received; two masturbatory sessions; six orgasms.

All good things must come to an end, including the Sex Diaries. After a long run on Daily Intelligencer, this will be the final entry. Next week, we’ll run a greatest-hits post of our most memorable diaries. Let us know in the comments which ones you’d like to see. 

Woman Masturbating With Clothespins on Nipples