Sex & Relationships

Virgin territory

Expanding your erotic horizon is a lifelong adventure, from your first kiss to your favourite costume. Here, six women share their stories

When it comes to sex, they say you never forget your first—first kiss, first orgasm, first French maid outfit…and how could you? These experiences are not just quick thrills. They’re milestones and they leave deep impressions, both mentally and physically. Our sexual firsts change us and educate us; they make us the women we are.

If only there were an adult version of Girl Guides and we could earn badges for our sexual accomplishments. Our uniforms would proudly proclaim everything from “I used a vibrator” to “He said he loves me—without prodding!” and by wearing our achievements on our sleeves, we would give others the courage to conquer these rites of passage for themselves. For example, a friend’s admission that she is just figuring out how to climax during sex says, “You’re not alone,” and a colleague’s revelation that she has just discovered her elusive G-spot says, “I’ll tell you how you can, too!” It may seem un-Canadian to expose our private lives, but in these post Sex and the City times, really gratifying sex talk goes well beyond whispered confessions. And so, in the interest of higher learning, we’ve found some real-life Carries, Mirandas, Charlottes and Samanthas and asked them about their memorable firsts. Here are their stories, for your reading pleasure and your education.

Kiss and tell

If there’s one thing Alex Dallas knows about, it’s sex. A comedienne and British expat, this saucy lass traipses across Canada, telling stories from her sexual oeuvre that would make a sailor blush…or laugh. Originally part of the feminist comedy trio Sensible Footwear, the vivacious 46-year-old now performs autobiographical one-woman shows such as her crowd-pleaser, Nymphomania. With a mischievous smile and a twinkle in her eye, Alex delves into her bag of sex-capades and pulls out raunchy tidbits—such as the time she had sex in the back of a hearse.

Over the years, Alex’s legions of fans have come to expect these racy tales, but lately she’s been peppering her shows with innocent memories as well. One of Alex’s favourites is the story of her first kiss. As she tells it, she and another 12-year-old, John Pretty, were both lunchtime librarians. One day when they had nothing better to do, the two shy students decided to go into a cupboard and give smooching a try.

“It was quite shocking to kiss somebody for the first time,” she recalls. “I remember the sensation of having another person’s hot breath on my mouth—it was stunningly weird but nice.”

Alex feels that naive firsts can be just as momentous as the bawdy break-the-headboard kind. To this day, she fervently believes that kissing is the most intimate connection you can have with another person. “You know you’ve fallen out of love with someone when you don’t want to kiss him anymore,” she says.

At this moment, Alex is single and willing to kiss a lot of frogs until she finds her prince. “I’ll take a good kisser over someone who’s good in bed any day,” she says. “In bed people can be trained in what you like or don’t like. But if they don’t have something special in the kissing department, that’s it.”

Lost—and found

For years, Parker* dreamt of losing her virginity. After all, she’d read enough about it. As with many adolescents growing up in the ’80s, her sex education came from manuals awkwardly handed over by her parents and well-thumbed copies of Judy Blume’s Forever, furtively passed around the school. She had the mechanics of the act down pat and eagerly anticipated putting her research to the test. So, when the blond blossomed from a pudgy awkward adolescent into a shapely 17-year-old and started dating the captain of the high-school football team, she thought she’d hit the jackpot. It was a modern teenage fairy tale come true. Almost.

The big event seemed inevitable during a particularly heavy petting session in her parents’ rec room. Little did she know, her Romeo and Juliet moment was about to become a comedy of errors.

“We were both pretty uncertain and embarrassed,” recalls Parker, whose first partner was also a virgin. “There was lots of fumbling, and I kept asking, ‘Is it in now? Is it in now?’ The whole thing was intimidating, embarrassing, messy—quite frankly, I wish I’d been drunk my first time.”

To add to the farcical element of it all, the young lovers worried that Parker’s mom would walk in on them. But they knew she wouldn’t disturb them if they were watching a movie, so they threw a tape of Anne of Green Gables into the VCR and turned up the sound. Years later, Parker met one of the Anne actors and couldn’t resist telling him her story. “His smile turned to an expression of horror when I joked that seeing his face made me a bit tingly.”

Making fun of the incident and sharing it helped Parker recover from an embarrassing, potentially traumatizing first.

“Losing your virginity is like playing a board game and realizing you only know half the rules,” she says. “Once you’ve played the game a few times, it gets much better. And when you find somebody you love, it becomes interesting in ways you could never dream of.”

*Names changed to protect the not-so innocent.

O is for…

Melanie* has always been a speak-up take-charge kind of gal. For example, when this smart, sassy 32-year-old realized she wasn’t satisfied with her job, she didn’t hesitate to take charge and change career paths. But being brazen in the bedroom didn’t come quite as naturally.

“I knew how to achieve an orgasm by myself, but whenever I became intimate with a man, I couldn’t do it,” says this single girl. “I would be too wrapped up in how he was feeling. I had a hard time relaxing and just letting it happen for myself.”

But a few summers ago, Melanie hooked up with a guy who took her back to his place—and everything changed. A decor buff, Melanie was impressed with the tranquil setting—leather sofas and floor-to-ceiling windows that looked out onto a landscaped garden. She was also tired from a long day. So, as she and her new friend started to get it on, Melanie found herself relaxing more than usual, particularly during a certain oral event. Naturally, she was jolted out of her lull when, to her great surprise, she found herself having an orgasm.

“I was in shock that it had finally happened and couldn’t speak,” she says. “He didn’t realize I’d already climaxed and so he continued, resulting in three orgasms!”

While her orgasms—and the relationship—were short-lived, the moral of the story endures. “I learned the benefit of relaxing and allowing the focus to be on me instead of my partner,” she says. “I also learned not to be afraid to ask for what I want.”

Three little words

It’s hard not to love Jen*—the adorable 24-year-old has wide blue eyes and is quick to give you a warm smile or tell you what she admires about you. So, when Jen met the man she knew was her soulmate, it was easy for her to say, “I love you.” She just didn’t know what to do when he wouldn’t or couldn’t reciprocate.

“It hurt me when he didn’t say it back,” she says. “I asked him why and he said that he didn’t know if he loved me yet—he knew he liked me, but for him, love was about a deeper connection.”

Jen accepted his explanation, but she kept on saying her favourite phrase. Nevertheless, her professions were greeted with silence. She often filled the void by banging dishes and slamming doors in frustration.

But one day, Jen was stuck on a commuter train for more than an hour. She tried to call her boyfriend, whom she was living with by this time, but the battery in her cellphone was dead. All she could do was wait out the ride. Meanwhile, her beau was getting more and more anxious, not knowing what had happened to the usually punctual Jen. When she finally walked through the door later that night, her boyfriend blurted out the words she’d been waiting to hear.

“He said, ‘I love you and tonight I realized I can’t live without you,'” Jen recalls. “I was overwhelmed. I can’t tell you what a relief it was to hear that.”

Jen feels her man’s declaration was a turning point in their relationship that, four years later, is still strong. “He taught me the true meaning of those words,” she says. “Now when he says ‘I love you’ I know he means it. And now I try to communicate better. If I don’t like something I speak up—I don’t take it out on the dishes.”

*Names changed to protect the not-so innocent.

First position

Sally* could easily be a lost member of the Sex and the City tribe. An urbanite with fiery red hair and a passion for living, she admits to having had “many lusty episodes.” The players changed often, she says, but her position always remained the same—flat on her back, missionary style. “I’d always been afraid to be on top,” she says. “It’s the position where the woman has to take the most control. I wanted to be sexy, not admit that I didn’t know what I was doing.”

As with many women, Sally never experienced orgasm during intercourse and assumed the problem was biological. So, a year ago, when she started dating her current beau, he suggested she take charge by being on top. “At first it was awkward and I was really turned off,” she says. “But then, with some practice, it clicked and I realized this was the best position for me. Now, I want to be on top all the time!”

Experimenting with a new position has helped Sally hit her sexual peak in more ways than one. “I feel as if I’m having more grown-up sex now,” she says. “Before I was brimming with sexuality, but now I’m maturing and coming into my own. I’ve hit the sweet spot, so to speak.”

Dress for success

Mary is the woman you’d want to sit beside on an airplane or stand behind at the grocery store—she’s sweet, considerate and not likely to cause trouble. A sunny blond, this 47-year-old mother of two isn’t the type to ruffle feathers—unless she’s wearing them.

Boas, wigs and costumes have become part of Mary’s erotic repertoire, thanks to a rather unusual first. It happened five years into her marriage, when Mary was working as a cosmetician at Woolco. Her daily uniform consisted of a white lab coat and, sometimes, gloves. One night after Mary’s hubby picked her up from work, he asked her to keep the outfit on and head for the bedroom. A flabbergasted Mary, who’d never had a lover other than her husband, wasn’t sure such a request was “normal.”

Still, she went along for the ride. “We were fairly playful at that point anyway, so I let my husband talk me into it. I realized the lab coat persona was just an extension of my bedroom wardrobe, like lingerie.”

Years later, Mary is still filling her tickle trunk with interesting outfits. Last fall, she took advantage of post-Halloween sales to purchase a Dallas Cowboy cheerleader ensemble and a devil costume. Ever the frugal shopper, she’s also picked up heart-shaped handcuffs at the dollar store.

“Once you get past feeling foolish putting it on, a costume changes your personality,” she says. “A disguise, even a bad one, can make you feel a lot less inhibited.”

Sexual firsts are physical yet emotional, fleeting yet life-altering, unique yet universal. Sometimes successful, sometimes disastrous, they are instructive no matter what. When you’re just discovering the wonders of sex, firsts are easy to come by. But continuing to conquer virgin territory is important, no matter how old you are or how long you’ve been doin’ it. Says Chanelle Gallant, psychotherapist and manager of Good For Her, a female-friendly adult store and workshop centre in Toronto: “Empowering exciting sex is for women of any age, not just the young and hard-bodied.”

So, get out there and try something new. Read a sex manual, talk to a friend or swing from the chandelier if you want to. Because the best thing about firsts is that they lead to seconds, thirds and fourths….

*Names changed to protect the not-so innocent.