I Helped My 28-Year-Old Friend Have Her First Orgasm

I always like a challenge, especially this time of year as I’m all hopped up on Christmas miracles and philanthropy. So when my sexually awkward and wonderful friend told me she’d never had an orgasm in her 28 years (“Even by herself?!” I hear you cry— even by herself) I decided to put all my anxious holiday energy into helping out a friend in need. Hattie tells me she has never even tried to touch herself and when she told me this I was speechless. What does she do when she can’t sleep?!

As many as one in three women have trouble reaching orgasm when having sex, and it’s suspected that 80 percent of women fake it. But for my friend Hattie—who wishes to remain anonymous so as not to uproot the sexual prowess of her previous partners—faking has been the only ever ending to her sexual exploits since she started having sex ten years ago.

“I’m a wonderful actress,” she says when prompted to show me Harry Met Sally-esque at the table. “Faking depends on the person, with my boyfriend it was more of a show… I think I thought I loved him more than he loved me so it was my way of giving him something.” Hattie confesses that screeching, thrashing and wailing into a mythical climax was her way of ensuring her man didn't stray, but this meant her own sexual development was never realised. Hattie’s amateur dramatics could be responsible for supporting the unfounded sexual mastery of a tiny portion of the males of Vancouver, she could even be responsible for the Tinder date you just went on when a guy asked if you’d come after two brief thrusts and a clumsy tap tap to your clitoris.

Hattie is the first female friend who I’ve met who didn’t spend her formative years with some kind of sexual curiosity; whether that was discovering the well placed jets in swimming pools or partaking in weird sexual play with friends. She’s the only friend I know age 28 who swears she doesn’t touch herself and actually truly doesn’t. “I’m not comfortable with it,” she says. “I’m extremely sexually repressed.”

Hattie tells me she wants to try but doesn’t know where to start. “I obviously would like to, but might need some help,” she says. So we give ourselves a week to rid Hattie of all her pent up sexual repression and get her that happy ending that she so deserves. The orgasm doesn’t even need to be the goal here, just some general fun loving with herself. It is perfectly common for some women to not be able to fully climax, and I’m aware that there are psychological aspects to consider that are better suited to a year of therapy rather than my vague sexpertise; but just by addressing the physical I think we could get somewhere, even if it’s not the big finish. You know what they say—shoot for the moon and even if you miss you’ll be amongst the stars. Well same here I guess, but instead of stars it will be the possibility of saying the word “moist” without having a panic attack.

So what’s our tactic for the sexnaissance? Well first I want her to start feeling more sexually comfortable, certainly enough to stop faking orgasms left right and centre but also comfortable enough to find out how her body works and what she likes. I can’t do this for her however, and as much as friendly cunnilingus would probably be a quick fix here I’m not sure how comfortable I would be having the weight of 28 years of unobtained orgasms on my mere shoulders… Talk about apron strings. Instead I talk to Hattie about going to the only place I can think of that will reassure her that this quest is perfectly normal. Somewhere that will undoubtedly be an invaluable aid for her ultimate goal—a sex shop.

So Hattie and I venture to Womyns’ Ware, a sex positive, women-centred sex shop in Vancouver. Initially Hattie hates it all. There’s too much sex everywhere and even finding a place to lean without accidentally touching something phallic is impossible. Lesley, the owner of the store, and Hattie start to have a chat and I take myself away at this point. I think it only fair that Hattie has the experience of a genuine customer and having your pushy friend smiling at each baby step you make towards sexual freedom probably doesn't scream normal. So I have a walk around.

The store is like an erotically-charged adult candy shop. The brightly coloured toys and aesthetically impressive beads and dicks and vibrators are undeniably attractive—and I find myself kind of wanting everything in a Pokémon “catch em all” kind of way. Who knew sex toys could be so visually appealing?

There are rows of dicks; big ones, small ones, ones with curves, ones with veins, and most unpleasant of all, ones with detailed balls complete with hair. Feeling one I noticed it was quite sticky. “Those are the lifelike ones” said Anne, the co owner. “They’re made to feel like skin.” I couldn't help but grimace at the little bits of fluff clinging to this skin-like plastic. Most of these faux skin toys have a plastic pair of balls to accompany them. “Some people like the ones with balls.” Why? A pair of loose skin simulating plastic balls certainly wasn't for me but just looking at this menagerie of dicks was enough to show me just how diverse everyone’s needs and desires are. I want Hattie to take a nine-inch multicolour monster penis home but I know sadly this isn't my decision, and for the girl who’s currently choking on the other side of the room trying to say "lube" it might be the rainbow, cock shaped, nail in the coffin.

Hattie and her new fairy sexmother Lesley are looking for two toys for Hattie to take home. They focus on the middle section of the room which contains the multi-purpose toys designed to target the clitoris and the g-spot—Lesley thinks this would be a good place for Hattie to start as she’s not sure what she likes yet. Apparently these multi-use toys are quite popular for a variety of different women as they cater for the basic and more middle of the road requirements. Yet even this section includes a plethora of different colours and sizes. They’re all so ergonomically satisfying to look at, and I’m pleased to see in this section there’s not a faux skin hairy ball in sight. It seems Hattie has made her decision on what she would like to take home; a small lighter-sized vibrator and a multi-purpose toy thats pink and non threatening; Lesley approves. Sadly she was less willing to let Hattie try the giant self thrusting dildo that I suggested—too much too soon perhaps.

It’s (se)Xmas eve and Hattie and I sit down for one final discussion before she takes herself away to try her new presents. I get the chance to ask her what she expects her first orgasm might feel like. “Underwhelming,” she suggests. “In three words?” I ask. “Good not great,” she replies. Perhaps, but I feel even the progress she’s made today has make the whole experience worthwhile. “I feel slightly sexually liberated,” she says, “or it’s going that way, it’s made me feel better.” So with $400 worth of sex toys on her person I send her on her merry way. It feels like I’m a parent finally letting go of my child on their bicycle for the first time without training wheels.

I wake up to a text the next morning that just says “Didn’t happen.” It feels like waking up on Christmas morning having been stood up by Santa and I can even feel the disappointment oozing out of the text despite the lack of emoji. I start to feel a little guilty. The pressure I’d put on Hattie can’t have been sexually liberating. In fact it’s playing into the stigma that female pleasure exists for and from other people. This is her experience so I have to stop trying to be so heavily involved. I tell her that it’s perfectly normal and apologize, I must remember that this is her experience and not mine.

We speak on the phone later that day and Hattie tells me she had tried the small vibrator. In fact she had slaved away for an hour and nothing had happened. “Nothing exciting happened, it was fine,” she said. “Felt good but I’ve felt like that before.” Eesh. “Fine” and “good.” This is hardly the earth shattering sexual initiation I had predicted for her. “I think I need to become more dexterous with the toy,” she added “I didn't really know what I was doing.”

“I wasn’t concentrating a lot,” was her response when I asked her what she was thinking about. The idea of Hattie using this baby vibrator and flitting in and out of thinking about food or what she was going to do on the weekend is hardly the image of total sex confident self pleasure. After an hour even the most well-versed self pleasurer would get a little bored. “I also think I just need to get a little more comfortable using them.” OK, so all she needed was practice and some saucy thoughts to get her in the mood. Hattie is a fan of erotic fiction, always has been; so tonight I suggest she gives that a whirl before she tries the other toy. As we end the phone call Hattie says “orgasm” without taking the usual inhale to prepare herself and I can’t help but feel a little proud.

Hattie seems in higher spirits the next time we speak. She doesn't quite have the dilated pupils and look of sheer hedonism of someone who’s just experience their first ever climax, but she seems a little freer. “I’ve used the big one the last two nights and it’s very intense.” By “big one” she means the small pink multi purpose toy that Lesley suggested as option two. This one is more powerful than the small vibrator that essentially feels like someone’s lightly humming into your crotch. “It’s definitely something I haven't felt before and feels like it’s going somewhere.”

No climax has happened yet but I’m apprehensive to bring that up again so as not to spook Hattie back into her shell of sexual discomfort. “I think I just need to figure myself out a little bit,” she says, and I encourage her to take her time. “I haven't put anything inside yet, I think I might do that tonight.” This may be the most comfortable I’ve ever heard her sound, she’s talking about putting things inside herself and she’s not cringing nor sweating profusely—what progress!

Being a fan of erotica I choose to give Hattie advice from my sexually curious 15-year-old self who would read erotic fan fiction alone in her room several nights a week. I direct her to a website where you can find links to all sorts of genres of erotica including, and surprisingly most intriguing for Hattie, supernatural and “non-human” erotic stories. “Oh, I get really into that kind of shit,” she says when I send her the link. Three days ago Hattie was frightened of the word “penis” and now she’s comfortably talking to me about sexy aliens, erotically charged vampires and even “sex angels.” I’m amazed. Perhaps there is something about supernatural erotica that’s unearthly enough to make her detach from the current pressures she lives with everyday. It’s almost as if the sexed up non-humans were a form of escape from the tight ropes of sexual constriction that she has yet to shake off after ten years of being sexually active. Who knows.

I’m sitting opposite Hattie having made a triangle with my index fingers and thumbs. Without any free hands I use my nose to point at the imaginary sweet spots in attempt to give her some more guidance. “I know where everything is,” Hattie says after I reluctantly repeat the word “clitoral hood” at least four times, “it just hasn't happened yet.” Hattie had another long session last night, and I’m extremely impressed by her vigilance. Sadly though it was day five and still no cigar. “When do you decide you’ve had enough?” I ask her. “When the battery runs out” she replies. That must be a good hour, I’m impressed!

“It was good,” she says, “the best so far.” I’m still waiting patiently for words like “earth shattering” or “showstopping” and this lacklustre sexnaissance so far has been, just as Hattie predicted, somewhat underwhelming. But still, she’s talking comfortably about it and I have to remind myself that this at least is something. This girl last week would probably not even have touched herself if she was cramping so this is undeniable progress. Hattie was making slow and steady headway towards her goal and last night she took a couple of extra steps with the help of the sex angels. The sex angels. Having done a little sleuthing myself last night, I can conclude that in no way would a sex angel do anything near to warming my loins but that just shows how delightfully different we all are.

Well it turns out sex angels are an actual thing. The web is bursting with erotica describing winged creatures and their vibrant sexual activities. There’s probably nothing unsexier than reading erotica out of context and there’s only so many times I can read about an angel’s “throbbing member” or “angel juice” before I have to take myself away and try and burn it from my memory. That night I think of Hattie probably beginning another sesh and I hope tonight will be the night. Part of me knows she’s ready, so I cross my fingers and pray, to the sex angels of course.

I receive a text in the morning with six emojis.

It’s a fairly cryptic selection but I don’t struggle to decipher it. She’s only gone and bloody done it. With such an eclectic grouping of emojis though I am left unsure of the general narrative, mainly because theres no angel emoji in sight.

“How do you feel?” I ask her. “Probably the same,” she replies. “I guess happy now I know I can do it.” She’s so blasé! Where are all the erogenous superlatives?! I was hoping for a Jilly Cooper style paragraph from her about the intricate internal details of her experience but she’s reluctant to give it. For Jilly Cooper, literary orgasms always involve something “shuddering” “rippling” or “undulating” and it always sounds so wholesome and uncomfortably mumsy. Hattie’s account was much more simplified. “It felt good” she says, “it felt new—honestly it’s hard to describe it.” Clearly all the erotic fiction she’s been consuming hasn’t inspired her to be any more graphic but I think I would also find it hard to put into words. “It makes sense now because I know what everything is leading up to” she continues “now I just wanna get good at it.” So with her first climax under her belt Hattie has made a new resolution for 2018—get good at orgasms.

So what’s the conclusion? If you try hard enough at something you’ll always achieve it? This certainly is a lesson in perseverance. Hattie spent an hour a night for six days trying to have an orgasm and she succeeded. That’s six hours of self-improvement and self love and she’s honestly a different woman because of it. But even if she hadn’t succeeded she tells me she would have been grateful anyway. “This whole thing opened up a dialogue about my own pleasure that I wasn't comfortable talking about before and now I am comfortable—I wish I had had this moment earlier on,” she tells me as we virtually high five over the phone.

The goal of sex should be to feel good, not necessarily climax because for some people that still isn't possible and I’m super stoked for Hattie that she’s finally starting to figure out what makes her feel good. Hattie is now quite comfortable spending an evening in just with herself, her pink vibrating buddy and the sex angels, and this is quite the departure for the girl who previously described her sexual experience as “mundane.” If walking around Vancouver you see a 28-year-old woman with the weight of an entire life of sexual repression lifted from her shoulders then give her a wave.