My First Time With a Woman Was During a Threesome With My Boyfriend and a Sex Worker

“Okay, but I’m definitely not going to eat her pussy,” is a text I sent my then-boyfriend the night before our first threesome.

As you might imagine, the whole threesome thing was his idea—and, yes, pretty much any sex expert will tell you that having a threesome you don’t really want to have just to please your boyfriend is literally one of the worst possible reasons to have one. But since I, like our lord and savior Samantha Jones, will try pretty much anything once, I was down to give it a whirl. Not to mention, I had a growing feeling monogamy wasn’t really my bag and thought a threesome might be a convenient, boyfriend-sanctioned way of exercising my non-monogamous tendencies—one that might even become a gateway to the open relationship we both knew I secretly wanted.

There was just one problem: I had never been with a woman before and was pretty sure I had no desire to. The closest I’d come to hooking up with another girl was a New Year’s Eve kiss with a college friend. I was definitely in no position to be going down on anyone with a vulva—especially not a professional.

Of course, that part—the hiring a pro part—was my idea. Because it would be my first time with a woman and my boyfriend’s first threesome (I’d dabbled in MFM threesomes before, by which I mean I had literally one threesome with two Tinder randos when I was 19, which went about as smoothly as you might imagine sex between three college kids would), I insisted my boyfriend hire a pro. I mean, I figured at least one of us should have some clue what they were doing. But even knowing I would be in the hands of an experienced professional, I still wasn’t fully on board with the idea of going all the way downtown with another woman. That is, until Alison* walked into our hotel room in black leather pants and Louboutin stilettos.

Okay, so did I take one look at Alison and her red-bottomed heels and think, “Wow, I definitely want to eat her pussy”? No, not exactly. But she did radiate a warm confidence that pretty immediately put me at ease. Like any woman having a threesome for maybe not quite the right reasons, I had been worried about feeling intimidated by a beautiful, sexually experienced woman entering the chat. But Alison’s beauty—combined with her warmth and friendliness—somehow only made me feel more confident in my own.

A woman in her early- to mid-thirties, Alison was about ten years older than me, and I found myself in awe of her the way you might admire a friend’s older sister or a mentor at work—someone who’s so beautiful and smart and objectively enviable, but doesn’t actually make you feel insecure. Like, “Wow, I want to be her,” but in a way that makes you feel like you actually could, a way that makes you proud and excited to be a woman, because, damn, look how gorgeous and amazing women are.

Of course, it helped that she was a professional. She knew exactly how to hype me up while putting me at ease, all without making me feel like the total novice I absolutely was. She deftly positioned me on the couch between herself and my boyfriend, making me feel like the star of the little show we were putting on even though she was really the guest of honor. We sipped Prosecco and chatted about Louboutins and Louis Vuitton bags and my relationship with my boyfriend. In other words, we chatted like girls—like friends of a mutual friend who happen to hit it off at a bachelorette party, or drunk girls in line for the bathroom at a club. (I would later describe the pre-threesome chatting period to my roommate as, “Like making friends with a drunk girl in the bathroom, except then you eat each other’s pussies after,” but we’re not there yet.)

After a few glasses of bubbly and a solid thirty minutes of girl talk, any pussy-eating anxieties I may have brought with me into the room that night had completely dissolved—in part because I was having such a good time hanging out with Alison that I had almost forgotten the real reason she was there, i.e., to have sex with me and my boyfriend. Fortunately, Alison hadn’t forgotten. And, ever the professional, she knew exactly how to break the ice and transition from girl talk to, uh, girl action.

“Can I kiss you now?” she asked.

Not to brag, but I’ve had my share of kisses in the decade or so since I exchanged my first awkward smooch with a boy in a high school gym. In all those years of kissing, however, I’ve had very few—even among the really, really good ones—that I remember with the specificity with which I can recall my first kiss with Alison. For months afterward, I could remember exactly how her lips felt against mine—soft and full—as if the kiss were happening all over again in real time.

More importantly, I could remember exactly how she smelled. I’ve always been a big believer in the sex sniff test, which is a very unsexy way of phrasing what I think is actually one of the most erotic sensory experiences we have access to as human beings. If you like how someone smells—and I’m not talking about their perfume or shampoo, but their natural, human smell, the one you can only pick up on when you’re close enough to kiss them—you know there’s sexual chemistry. It’s the surest sign that there’s at least some level of chemical or spiritual attraction at play, and that’s something you can’t fake. Alison may have been a literal pro whose job was to turn me on, but there’s no way even the most experienced professional could have faked that level of sensual connection. I may not have been into women—as far as I knew, anyway—but I was definitely into Alison.

As soon as I kissed her, I knew not only that I could do this, but that I genuinely wanted to. Not just for my boyfriend, who was watching us kiss with a giant grin splashed across his face like a giddy schoolboy, but for me. Alison took the lead, naturally, guiding me to the bed and undressing me before going down on me. She was obviously phenomenal at it, BTW, but within just a few minutes, I was ready for my turn. Practically vibrating with nervous energy, I took a breath and dove in head-first.

This is probably going to offend vulva-havers everywhere, but honestly, the experience wasn’t entirely unlike that of going down on a guy. In part because, yeah, it all tastes the same in the dark, but also in that I seemed to know instinctively what to do. Going down on Alison, I was reminded of giving my very first blow job back in high school—how after weeks of anxious Googling, (and, yes, poring over every blow job tip Cosmo had to offer) my body just took over in the moment, as if I’d already done it hundreds of times before.

Much to my relief, going down on Alison was a similarly intuitive experience, one that came as an exciting reminder that my sexuality is, at least on some level, instinctive—that I myself am an inherently sexual being whose body instinctively knows how to give and receive pleasure. Realizing that my body was wired for pleasure the way I did with my mouth between Alison’s legs helped me embrace and inhabit it more fully than I maybe ever had before, in a way that is often hard to do as a woman in a world of diet culture and Photoshop—a world that usually sees and treats our bodies as objects of men’s pleasure, rather than agents of our own.

Going down on Alison and feeling more in tune with myself as a sexual being than I had in a very long time (maybe ever), I suddenly understood how sexuality can be fluid—how there’s an extent to which it maybe isn’t about dick or pussy or gender, but some raw form of desire and attraction that transcends all of that. I mean, yes, I knew that “sexuality is fluid” the way I know all squares are rectangles but not all rectangles are squares, or that matter can be neither created nor destroyed, it just changes shape. But before Alison, I had never experienced my own sexuality as fluid. I didn’t know my rectangles could be squares, so to speak.

Suffice to say, it was a pretty eye-opening experience, one that also happened to end with three orgasms and left my boyfriend and me so turned on we ended up having sex again that night after our guest left. Naturally, my boyfriend had fully caught the threesome bug after that first experience, and I was obviously a lot more comfortable with the idea now too, thanks to Alison.

Unfortunately, I was never quite as into any of the other women we had sex with as I was Alison. And yeah, maybe that’s just because Alison was a pro who’s good at her job, or maybe it really was a matter of chemistry. Most likely it’s some combination of the two, but ultimately, it doesn’t really matter. What matters is that I got to have an amazing, enlightening, and sexually satisfying first threesome experience, and I’ll always be grateful to Alison for her role in creating that moment we shared.

Now, am I saying you should have a threesome with your boyfriend even if you’re not sure you want to because you might just surprise yourself? No, that would be bad advice. All I’m saying is, you really never know.

*Name has been changed.

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