sex diaries

The Bisexual Who Can’t Get It Up for Someone Half His Age

Once a week, Daily Intelligencer takes a peek behind doors left slightly ajar. This week, the Bisexual Who Can’t Get It Up for Someone Half His Age: Male, 48, Austin, performer, bisexual, in a non-monogamous relationship.


2:37 p.m. Just short of eight hours away from my date with my new pal Half Pint. I’m nervous, because we’re due for our first full go at it — not counting two previous make-out sessions ending in orgasms and messy sheets — and also because she’s nearly half my age. The gap in years is no big deal in the scheme of things, but my preoccupation with doing us “old guys” proud for the little polyamory-friendly, hard-working, loving, and horny girls just has me overthinking it. Usually ends limply. Thank heavens she’s a good communicator, and relatively easy to please … and hasn’t introduced me to her mom.

8:28 p.m. Down two tacos from Papalote; hope it doesn’t upset my stomach. Need to straighten my place up quick before Half Pint arrives. Molé don’t fail me now.

10 p.m. Half Pint arrives with a bottle of St. Germaine. I make us gin and St. Germaine cocktails. I have one and can definitely feel an edge being softened. She has three and smokes two bowls and is relatively the same. We dance in the living room, make out on the chaise lounge.

Midnight We move things to the bedroom. I’m entranced with her body. I go down on her. Sensing the moment arising, I slip a condom on, but no sooner is it on and I’m trying to purposefully rearrange our bodies than I get soft.

12:05 a.m. A few minutes and another condom later, I’m good to go, confident, and enter her with authority. Her excitement overwhelms her command of her body. She writhes around, in blunt contradiction to whatever I’m trying to achieve. I plead with her sotto voce, “Hold still a minute,” but that minute is reduced to the few seconds it takes to realize I’m no good inside her. It felt great while it lasted.

12:30 a.m. I tell Half Pint I’m nervous. She takes it personally. “Just getting to know you,” I explain. Just getting to know myself is more like it. Take your time, Casanova … what has it been, like, three decades of this?

1 a.m. We get up to fix one last drink. Half Pint takes the cocktail shaker from me and insists on shaking it herself. I must say she looks hilarious and divine bouncing her little curvy body all over the kitchen as the drink rattles to completion. It’s the best cocktail yet, perfected with a “naked shake.”

1:08 a.m. Half Pint has me gripping the kitchen counter and adjacent wall as she spanks me. She delights in it; I grimace in pain as I accommodate her. Afterward, it’s my turn, and I discover (no surprise) she’s far more resilient and tougher than I. We discuss how it’s cool we can explore this stuff. She probably needs to more than I, but I’d like to get back into it, somehow.


6 a.m. Dream of mental patients, self-fellatio, and outbreaks of genital warts. Make. It. Stop.

10:30 a.m. We happily snuggle awake, which culminates in Half Pint masturbating as I assist with fingers and mouth. She comes hard. Then it’s off to brunch at Austin Java, which is less intimate and far less appetizing.

7 p.m. I invite Half Pint to a show I’m playing, though I know she has plans with girlfriends. She texts me photos of herself as she’s getting made-up for the night. They are rather tasteful, as in fully clothed, which surprises me. “How do I look?” she asks. “100% edible,” I answer. “Even after a night eating me?” she replies.

1 a.m. I give Half Pint a ride home from a gig of mine she was dropped off at. She fixes me a gin and St. Germaine cocktail (hers are way better) and takes me up to her room. We hear “Psycho Killer” and “Let’s Dance” on her Pandora station, as she disrobes and acts out her rock and roll fantasies in front of me. I’m “tense and nervous and I can’t relax.” She’s content with dancing about, kissing, and walking me back to my car.

1:25 a.m. Text from Half Pint reads, “U just made my last 24 hours.” I fall asleep soundly under the serious moonlight.


10:30 a.m. I can sense I’ll be lazing around all day (it is the weekend) thinking about Second Chance. I can’t believe it’s been almost two years since we randomly met in an art class and she showed me what a smart, compassionate mom with a brilliant wit, unstoppable body, and insatiable sex drive can almost do to a guy with a so-called “primary partner.” Not take her home to meet the family, unfortunately. My New Year’s resolution is to get over her, as she allegedly has with me. But what a run we had.  And we’re hanging later tonight! (Sigh.)

4 p.m. My undetermined evening plans with Second Chance get started early, if only to visit her and her daughters selling Girl Scout cookies down the road from my place. It’s the end of their shift, so I follow them home.

4:30 p.m. Entertaining myself half-heartedly, as Second Chance stays busy making meals and organizing the girls’ rooms.

5:20 p.m. I leave Second Chance and the girls, hoping to return later, as per the original plan.

9 p.m. Second Chance invites me over for reals. By the time I get there she’s drowsy, having just fallen asleep. We hang out on her bed and talk, mostly about her path of sobriety, which is part of why we’re not really “dating” anymore. Not because I drink, but because in her journey of being more honest with herself, she realizes she doesn’t want to date someone who dates others and has a primary partner.  I hardly blame her. I want to kiss her and much more, but have to play cool since she recently cut me out of that part of her life, more or less. I run a hand through her hair, squeeze her shoulders, and listen.

11 p.m. Second Chance needs to crash, so I say my farewell. We share a warm, “Aww, wouldn’t this be nice” hug, and kiss tenderly a couple times, but I know this is a closer, not an opener. I want her to be happy, but a little tenacious part of me just wants to make me happy, and that makes me sad. I’ll fix a gin and tonic when I get home.

11:38 p.m. I fix a gin and tonic.

Midnight Screw this. Take a butt plug and a Hitachi Magic Wand to bed. Fantasize about Half Pint. Success!


9 a.m. Text from Second Chance thanking me for hanging out, but bemoaning that I never try to make any moves on her. Dammit, Me! Learn to initiate!

1 p.m. Have lunch with Number One. A casual affair over burgers and beer at Dog and Duck Pub. I think how we’d be in the mellow, if not dreaded, Phase Two of our relationship by now, had it not been defined as non-monogamous. Instead, I live on edge, contemplating what she’s doing, what I’m not doing, what we’re not doing, what I’m overdoing. Thankfully, Number One is as cool as a house cat. She discusses my recent adventures with others with bemused curiosity. Jealousy is not in her vocabulary.

1:30 p.m. Finishing our meals, Number One gives me a tip about getting with other partners, which concerns my oral hygiene. Uh, thanks for telling me now? I feel insulted. She’s apologetic. I’d check my breath with the palm of my hand, but it would be all garlic fries and IPA. Instead I sulk, pay the bill, and whisk us out of there. I drop her off at work, she tries to kiss me good-bye. I tell her, sorry, I haven’t brushed my teeth. She exits the car, remorseful. I peel out, bitter.

10 p.m. Number One comes over. The storm has lifted. After a drink or two and some snacks, I brush the hell out my teeth and we get in bed. I spend a long time with my head between her legs, trying out a new technique she recommended a while ago that I couldn’t quite muster — or believe worked — at the time. It works! Then we do it. It works! It’s been a while, and she claims the soreness she feels confirms that. I’d like to blame my longevity, but I’m really just making up for lost time with Half Pint.


7 p.m. I attend a dinner party at a friend’s. There are a lot of cute women here, all of whom I’m attracted to, especially the one with the ample rack who gives me a welcoming booby hug.  She leaves too soon, and eventually the bevy of beauties winds down to two. They bond with us three remaining men, including the host, over a board game and final drinks.

11 p.m. The party is ending, and we’re saying our good-byes to each other and our host. I hug my friend H, who smiles and tells me, “I’m so making out with you.” When, now? Apparently not. She hangs back with the host, becoming the last guest to leave — or not leave. The other woman I had been getting to know is slowly moving to her car. I try to catch up with her, but I’m cock-blocked at the last second by the remaining male guest. I let it slide, and drive home with the same company I arrived with. 


7 p.m. Half Pint arrives with a bottle of St. Germaine. She makes us gin and St. Germaine cocktails. I make mahi mahi with steamed baby bok choy and roasted potatoes. It is awesome. We enjoy dinner, impressed with each other.

10 p.m. Dessert is served in the bedroom. I indulge in Half Pint, making her very wet. I’m more at ease with her body and her style now, but parts of me are still too at ease to prevent wasting another sad condom. Ever the resourceful when under self-imposed pressure, I manage to get her off with my fingers (the shocker), per her demand. She hits the ceiling before we both hit the hay.


7:30 a.m. Half Pint can’t sleep so she gets up and takes a shower.

8 a.m. I can’t sleep because Half Pint is giving me a morning blow job. She had forewarned me this is one her favorite things to do, and far be it from me to complain at this or any other hour. My only complaint is the days-old, tired beef I have with my tired beef. I decide to let her finish me — or I suppose she makes that decision — on her knees at my bedside, working miracles as I sit up and greet the morning sun like a freaking supernova exploding in my root chakra. Damn, she knows what she’s doing! She gets an extra piece of bacon.

8:48 a.m. I make breakfast for Half Pint and me. She enjoys her extra piece of bacon (the least I can do) and marvels at being taken such good care of. Two to tango, I tell her. Besides, I’m a hopeless romantic like that.  

TOTALS: 1 act of intercourse; 3 wasted condoms; 1 self-pitying over-the-top act of masturbation; 4 acts of oral sex given (cunnilingus); 1 act of oral sex received (fellatio); 1 dirty thumb; 1 naked shaken cocktail; 1 missed opportunity.

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