Cheaper than therapy

Age 41

I am, unabashedly, an exceptionally privileged, overly-educated, urban snob. From what I can tell I am the third generation of such and so it is well-earned (even if my grandmother was quite plainly, a cunt) and I’m very good at it. I like to think I temper it with 1 - therapy for all that generational trauma and 2 - being generally well-meaning, enjoying a good insult about it, and very occasionally being fun to have a beer with. This was put to the test when I accidentally matched with a guy based 50km west of my city centre flat, deep into the heart of bogan-ville. I wasn't going to bother chatting but then I was drawn in by, sadly, the fact that he actually put in some effort. A smooth compliment and the ability to hold a conversation, let alone the ability to make plans on his own had me following along. The bar for modern dating is truly in hell. I was also going past the year point of a dry spell and had just wasted six weeks on a guy who “needed to take it slow” before I gave him the flick when he never developed any snap in his turtle (I will eventually quit “I can fix him” I promise). The blue balls were real. But enough excuses - I had an itch to scratch so I put my cougar hat back on and went to play in the burbs. I was in the mood for an easy win, and tradies seem to froth over a bossy alternative girl - I’m sure there’s some sort of manic pixie dream girl analogy I could make here if I were smarter.

He was a carpenter (good with hands) and covered in tattoos (good with trauma) so we had our first date in the city. The next I felt Canadian about and offered to meet him “halfway” for some mini golf. Over an hour later on the train I was reconsidering the cost-benefit ratio. Luckily I’m a narcissist who’s easily won over by someone being enthralled by my hotness, helped along by several drinks. He was also the first good (male) kisser I’ve come across in probably years? So I ignored an offhand comment on pronouns, smiled pleasantly at multiple pictures of his renovation work, and invited him to mine next for “video games” and sushi.

so beige

During my last video conference I drank a stiff beverage from a coffee mug in preparation for his arrival but even that was nearly thwarted when his outfit of choice was some basketball shorts and some sort of motorcycle t-shirt. Luckily I had more booze and he had extra gumption. Unfortunately I got the feeling it had been a while since testing his stamina as his excitement quickly outpaced what his cuddly body was up for. I’ll give him credit, he was putting in 110%, not just on the cardio side but he was also working his angles, because he had other shortcomings. This was most apparent when I hopped on top to help a guy out but couldn’t move too much for fear of it slipping out. I appreciate whatever former girlfriend was constructive during her reign, he had some decent tricks for maximising his offering before he collapsed into a snoring post coital nap. I poked him and reminded him about his long drive home and crack of dawn worktime and sent him on his way.

I think it’s safe to say I haven’t been won over to the blue collar fantasy just yet, but it achieved what was necessary. Buying cats and moving to the woods has been postponed... for now.

Age 39

What’s a single woman fast approaching 40 supposed to do? the movies say go to India. Now did I opt for the 18-39 year old backpacker group since I was less looking to acquire enlightenment and more hoping for some drinks and some ass? Obviously. 

Unfortunately my hopes were shattered when I arrived in Delhi to a group of 12 women and 3 men, one of which was half of a couple. On the bright side half the girls were Scandinavian med students that looked like a Viking volleyball team and made for good scenery. The summer camp effect hit with full force as we had barely made it to the Taj Mahal before the troll-like Englishman had managed to canoodle with not one but two of the girls on tour and the gossip and drama was delicious.

for a giant tomb it is very romantic

I got to hear the inside scoop after one night of late night drinks when I disclosed my bisexuality and the German gal who had been part of said canoodling suddenly decided we should be besties. While I was happy to suddenly have a confidant and chai partner, after another night of beers German Lila confessed that she’s always wanted to try the female side and maybe this “could be a special trip.” 

This was not the first, or third bi curious girl that had sidled up to me and my non threatening subtly queer ways, but still I was left speechless for a sec. Now obviously if a pretty lady wants me to be her rainbow bridge I am not going to complain, but I still try not to be a predatory creep about it. I save that for my flirtations with men. So I left it alone for a couple of days. Apparently, the nightlife of Mumbai was inspiring as we had a lot of strong cocktails, and when returning to the hotel, she promptly declared I was coming to her room. I love a bossy femme. Not so excited about a pillow princess though, but what did I expect from a straight girl? Me not having an orgasm is tradition at this point. It was also 3am and we had a 7am start in the morning so I didn’t put too much effort in to be honest. The last couple days of the tour continued like nothing had happened and we went back to being friends aside from a sneaky make out as she was leaving for her 6am flight. I guess some people go to India to find themselves, others help them along the way by fucking them. 

Apparently my love of being fucked to within an inch of my life proves to be too much for the bed frame supporting it all.

Age 40

Nothing like turning 40 and a dry spell to make one download Tinder for the first time in years. It did it’s job and led me to find a 37 year old tradie who used to play lock for the Noosa Dolphins, where he had acquired the colourful nickname Meat Tray. Game on. We went for a beer just down the street since it turned out he lived four blocks away, even better. Unfortunately it was very quickly evident all his skill points went to pretty and fit and zero to intelligence. Of course since he could bench press two of me who am I to get in the way of myself. Having someone that can toss my Amazonian frame around and fuck me to within an inch of my life is not a common gift to come across. Especially at my age. I wouldn’t say he had the skilled hands of a carpenter but I was only looking to get bent over and banged like a screen door in a hurricane. Our first date was on a school night so I resisted and settled for a very uncouth makeout on my front lawn and invited him back on a Friday.

That was perhaps a mistake.

This man could both drink and babble. He got blackout drunk, told me his life story while we played Mario Kart, then, surprisingly, proceeded to fuck me rather well, if getting over excited and leaving me with several purple bite marks, before passing out and cuddling me almost right off my king size bed. Apparently being pretty hasn’t stopped him from a suffocating anxious attachment style. That man was a needy mess. When his alarm went off at 5am for no reason and as I angrily tried to get back to sleep he kept trying to get up in my business. And I’m sorry but morning sex is for after 7am and after several attempts I had to kick him out about 6:30. He was still blind drunk and stumbled out while moaning about liking me more than I liked him like a toddler having a tantrum. He texted at 2pm after just waking up and having no memory of leaving my flat.

The next week I opted for an early feed him and fuck him arrangement, sober, on a Tuesday. It did still involve a fair amount of having to talk to this himbo, but at least it wasn’t drunk blather and I quickly ushered him out of his pants after dinner. One spirited punishing of my cervix later, we were laying on my couch, his head on my chest, while he continued an impressive stream of consciousness and I admired his gorgeous shoulders, tanned and freckled from surfing, and occasionally acknowledged his speaking. When he yawned I suggested he head home before he passed out at mine.

“You know you don’t have to stay for a second round, that was a very good fucking. Gold star. You can wander down the hill before you pass out. Honestly, that was proper.”

I helped him find all his clothes and ever the polite small town boy he turned to me

“Thank you for cooking the lovely dinner and thank you for letting me cum on your tits.”

Fantastic. No notes. And all before 9pm.

Shame he’s an idiot.

When trying to make plans later he briefly made me feel bad with “I got the impression you didn’t want to be seen out with me” and so I made proper dinner reservations, but then the very next text was “I want to fold you like a pretzel” and I was reminded to feel just fine. This is a grown man who said “tig ol bitties” to my face, or more accurately my tits, multiple times. After our very first date, he requested I wear lingerie and heels for the next one.

(still trying to figure out where one gets the audacity)

I maybe have to stop letting an impressive set of pecs buy my silence on a thousand red flags.

Age 38

While at a particularly messy and fun pride parade after party I briefly chatted with one Dean, a programmer with long black hair pulled into a ponytail. I didn’t put much thought into it as that evening ended with a delightful and well executed threesome with the couple that was hosting. But in the morning, while still covered in sweat and glitter, the wife enquired if they could give my number to Dean as he had asked for it. Always handy when one can plan out the next romp while still in bed with the current one.

By date number two, even after hearing that he used to have waist length dreadlocks (which he missed…oh god) from his days playing in a metal band (I seem to have a type), I took his somewhat shy nerdy self back to mine. 

no thankyou

He’d also mentioned power lifting so I was interested to get his shirt off. 

I should not have been. 

I’ll never understand how people can spend ages in the gym and still look rubbish naked. More so when one looks… cuddly? at best, maybe don't bring up all the time spent throwing steel around. Manage those expectations people! Also too many weights and not enough speed work certainly shows in the bedroom. Don’t skip cardio day. 

Anyway, after a night of drinking it was some lengthy and low grade sex. But he was not a douchebag and even a bit funny so I opted for a 3rd date to see if another round might go better. 

The challenge with mid week dates is my rather cockblocking 7am meetings, so I explained to Dean I would have to “get him in and out again” before 10pm which I thought was fairly straightforward but he wholesomely still wanted to make a date of things and we went to a movie before hand. We grabbed a couple of drinks and then I noticed the time and rushed him back to mine. As I shooed him towards my bedroom and suggested he get out of those clothes he stared at me blankly.

“I thought we were just going to watch a movie and then I was going home”

“Oh honey you're so cute. Really??”

I guess I’m not as obvious a creep as I thought.

I hop on his lap and tell him we’re down to 30 minutes and get to fooling around. He was very shy.

“Oh I should warn you that after I’ve had a drink or two it really um, slows things down”

“Ah I gotcha, I’ll see what I can do”

This is what blowjobs are for. I get to work.

“No no really, it can take ages”

I spit his dick out of my mouth and pop my head up “How long exactly?”

“Like, hours”

I remove my hand from his balls and hop off the bed.

“Yeah nah, I gotta get to bed, we’re calling this a night.”

I fetched his pants for him and saw him out the door soon after.

There was, unsurprisingly, no 4th date.

Age 39

After the famous last words of “let’s just pop in to drag karaoke for one on the way home” I ended up at a dive pub filled with a bunch of black out drunk gen z kids. I was not wearing nice underwear and hadn’t planned on pulling, especially not in this spot, but I had a very encouraging wingman, a space brownie and a lot of booze in me. Initially a far too young and handsome boy chatted up my friend and I, but he was so drunk he wandered off to get drinks and when he accidentally wandered back (without drinks) he introduced himself freshly and was genuinely surprised to find his jacket, that’d he’d left with me, in my possession. And so enters Booky, a conventionally attractive guy, who amongst the sea of slurring 21 year olds seemed like a good idea comparatively.

He was not.

Unfortunately as he swung me around the dance floor and called me stunning I decided to ignore that fact. To further my shame, whilst amongst the youths cutting a rug, a girl shimmied up to me and asked for a kiss (which I of course indulged). Now she wasn’t what I’d call a looker and I unfortunately am horrendously shallow whether it be women or men, but it was a she and 2022 is supposed to be the year of more gay. Let’s be honest, men aren’t what I call killing it these days and women are majestic beautiful queens. 

But 

I’m not convinced I’m that great at lady sex and I was tired and not thrilled with the idea of being bad at figuring out someone else’s clitoral preferences. I could so easily just be a pillow princess with haircut over there. I mean I wasn’t planning on doing any kind of exercise or thoughtful sexual exploration at all when I started this night. Also he was doing what drunk boys do and hovering about me touching me and doing all the pick up work and I was gonna have to be brave and go close the deal with the girl all on my own if I chose that route. Look, I’m not proud of my decisions. What I should have done is gone home earlier and alone and just gotten some sleep. 

he also left his vape... I guess it goes in the box with the gangster chains

Instead I took home some eastern suburbs aussie lad who thumbed in a softie and I falsely, and performatively, moaned at him in hopes things might improve but probably just furthered his very incorrect high opinion of himself in bed. I’d like to think the fact that he’ll never be receiving a call from me after kicking him out in the morning without morning sex would deter that, but I highly doubt it. Sorry next girl he shags, I could have been more constructive 😅

This smells like the end of one stands for little old me, I guess this emotional attraction stuff is becoming a thing. Feels like… relationship season 

How appalling!

Age 38

After being driven away from the apps, I’d given IRL pick ups a solid go. Was excited for a wedding which then had no singles, another wedding had so few I ended up with the photographer but a failure to launch left me just as frustrated as ever. Tried speed dating - briefly DM’d a match only to have him disappear but watch my stories until the end of time.

So when I was contacted about a swingers and singles 1:1 party I figured fuck it, I’m overdue to dip my toe back in the lifestyle.

9:45pm

Get buzzed into a swanky 2 bedroom flat, everyone is still fully clothed. I’m greeted by the host, who, much like the rest of the male portion of 30-40 people at the party, I can best describe as Euro Chad? Not what I’d call my type, but happy to see fit people who are also on the younger side. Not that that's hard considering how ancient I’m getting. I pour myself a drink and quickly befriend two other chicks that had also come on their own. Within 10 minutes I’m down to one as girl #1 has disappeared with a boy. My new friend Sandy has never been to a party like this and is a little nervous so I give the speech on not worrying, not having to do anything if she doesn't want to etc etc and get to people watching and meeting people as they come in or grab drinks. At some point a pale long haired off brand version of 80s Chris Cornell sidles up to me. He’s Russian, works in IT, sings in a metal band and his name is Vlad, because of course it is (*actually!). He unironically makes me watch his music video on his phone and settles into a holding pattern beside me rather than the flitting about the room checking out the talent that is the usual routine at parties such as these. I’m lazy and haven’t seen anyone to tempt away my time so I hang out with Vlad and Sandy and try to avoid blurting out the vampire puns popping into my head.

11:10pm

Half the party is half dressed, the bedrooms now have multiple occupants. Someone is getting a blow job outside the bathroom, there's a stand up threesome up against the kitchen counter and I’m intermittently making out with my dark haired shadow. Sandy has gotten braver (and drunker) and goes on little forays to watch the action and then returns to report to me what she’s seen, often literally sticking her head in between the two of us snogging which I find hilarious. At least she’s not shy anymore.

“Hey remember Jen from before? She’s getting double teamed in the south bedroom now!”

‘Thanks Sandy, I’m glad you're enjoying yourself.’

Each time she returns she’s wearing less clothing and in solidarity I doff my dress. Vlad remains fully dressed.

11:45pm

Most of the party is naked or in lingerie. I feel like I should be making more effort so move our chat and make out into the living room. Sandy ventures to the patio and returns stoned, she finds this thrilling. I briefly peer into the bedrooms and they are BUSY. Several couples are in assorted states of coitus on the couch beside us and I'm beginning to think Vlad needs to up his rather vanilla game or I’m going to have to do some shopping.

12:10am

After more PG rated making out (although some occasional bites which I’m sure will be turning purple in a day or two, he wants my blood) while surrounded by fucking (pretty much everyone is screwing on every surface in the flat at this point) my Russian counterpart asks if I’d like to get out of there. I am easily won over by the idea of sex in the comfort and privacy of my own home - I am obviously less young and fun than I used to be. As we gather our things to go, I look back and see Sandy getting fingered on the couch. This warms my heart.

2:00am

I’ve made Negroni’s, we watched yet another of his band’s music videos on Youtube (a metal cover of a Kiss song… quaint), put on surprise surprise a 90s grunge mix on spotify and at this point I’ve listened to all of Vlad’s hopes and dreams and possibly whatever is on his vision board. Apparently this guy went to a sex party to get free talk therapy? I hopped on his lap in hopes of being inspiring, to which he actually stopped me kissing him so he could keep talking about Arnold Schwarzenegger’s journey to success when he moved to america. It would seem I’ve ended up with Vlad not the Impaler am I right? EH? I remove my dress in a single motion. Still nothing from the Russian.

3:30am

I give up and move things to bed, Im pooped. HE KEEPS TALKING. I tell him I need sleep and suddenly he gets handsy after 5 hours of PG foreplay. “Nope sorry I’m going to sleep, but happy to do this in the morning.” He asks if its okay to wake me up for sex. “Sure, thats always a good way to start the day.”

My king size bed goes to waste as he clings to me like a backpack all night. I guess his sire failed to hug him enough when tucking him into his coffin at night. He tells me he likes the way my skin smells.

8:00am

His alarm goes off. This is earlier than I anticipated when agreeing to this but also its been months and it might just seal up down there so fuck it, literally. I don't even bother cracking a curtain and figured I should (finally) fuck this sinewy pasty character in his native darkness. Half a session of mid tier lazy morning sex commences before he declares he’s still drunk and will need a break before finishing. So glad I woke up for this. But then he gave decent head so I was less upset and fell back asleep.

10:45am

Wake up again, ask him if he’s supposed to be somewhere since he set that alarm. Oh he has rehearsal at 12. THEN WHY DID YOU SET AN ALARM FOR 8. My head hurts too much for any of this or more of his talking so I get up and make coffees. I plonk myself on the couch and make extremely closed off texting on my phone motions and he cozies up to me and kisses my neck repeatedly, this reminds me of how sore my bite marks are and after more talking and more attempts at getting handsy I tell him I have to kick him out, I’m too hungover to deal with him.

12:00pm

Freedom. I order a McMuffin and head to my patio to gingerly put my hand in the sun and see if it burns. I check my teeth for fangs.

So far still human.