Sure, there were nights we’d stayed up late talking about boys, but all those chats had to do with their dimples or their hair or why a kid asked Liv to dance one Friday night and then called her fat to his friends the following Monday.
I couldn’t think of a time she’d told me about any of her sexual partners—except for her first time—and she seemed to have more experience than I did if she’d had sex with two guys in a matter of a few months.
“I’m not sure I’ll have many stories,” I said, thinking how much I wished I would.
GRAYSON
Wednesdays at the Bean had become an event I looked forward to, like the good old days before DVRs and streaming services, when I had to settle into a special seat on the sofa and tune in at a specific time to see the show I’d been waiting for. Except this entertainment was live, and most times it was funnier than any episode of The Office.
Except for tonight.
I tried to focus on something other than Isla’s face, but I found it exceptionally difficult. Not because she was too beautiful to look away—though she was—or because I was trying to read her lips as she talked—though she wasn’t. I couldn’t look away because Isla’s expression looked weary. She didn’t exactly seem annoyed. Discouraged maybe. Or emotionally worn out.
She scrolled through her phone as she sipped on a cup of hot tea. About ten minutes ago, I’d begun wondering whether the guy was going to show, because it was about twenty minutes past her standing appointment time.
Too distracted by whatever she was doing on her phone, she didn’t seem to notice when I approached her. It was only when I took the seat across from her and suggested she stop swiping right that she took note of me.
Laughing, she tossed her phone on the table carelessly, like she wouldn’t have been upset if it broke. “I’m not on Tinder.”
“I’m not judging,” I replied.
“I guess I’m the one judging,” she said. “I feel ridiculous doing this.”
I paused for a second. None of it was really any of my business, but she’d brought it up, so… “What is it exactly that you’re doing?”
She sighed heavily, as if she realized her comment had been a mistake and she’d have to explain it.
“You don’t have to tell me if it’s weird,” I said.
“Oh, it’s definitely weird.”
“Well, now I’m intrigued.” I folded my hands in front of me and leaned toward her like she was about to share the meaning of life with me. I obviously had some guesses as to what was happening. I just didn’t know the why of it.
“It’s actually not that exciting. Judging by your face, it might be a letdown.”
“Try me,” I said, thinking of how my life the past few months had been anything but thrilling. “Actually, hold that thought. Do you mind if I grab my things first?” I asked, pointing to the table I’d left that had all my belongings still on it. “The place is pretty crowded. I don’t want to take up another table if I don’t have to.”
She gestured toward the other table. “By all means. It doesn’t look like this Gage person is showing up anytime soon.”
“It’s just as well,” I assured her. “Anyone named Gage is bad news. He’ll probably have his cheeks pierced and be in a motorcycle jacket even though he doesn’t own a motorcycle.” Then I whispered, “What you don’t know is, he had to Uber here because he lost his license after too much moonshine.”
I headed over to get my things, and when I came back with my laptop bag, sketchbook, and coffee, she seemed more relaxed than she’d been when I’d sat down a few minutes ago.
Her arms were crossed, and she had an amused smirk on her face. “He makes it in his bathtub.”
It took me a second to remember we’d just been talking about moonshine. I shook my head. “His toilet.”
“That’s so gross.”
“So is Gage. He wears natural deodorant, so he has perpetual pit stains and smells like onions.”
She stared at me for a moment before bursting out into a loud laugh. I laughed with her too, and when we both calmed down, she said, “I’m glad it’s you here then instead of Gage.”
“Me too,” I said, trying not to think about how attracted I was to this woman. Not in a way that made me want to date her—because I didn’t want to date anyone—but in a way that made me happy she was simply talking to me. “So what is it you’re doing here exactly?”
“Opening myself up to ridicule and disappointment.”
Cocking my head to the side sympathetically, I said, “Seriously.”
“I blame my sister.”
She then told me about how she’d spent most of her adult life raising Olivia after their parents died in a car accident, and then she focused on her law career. So her sister had made her a dating profile, insisting she do something for herself.
“Your career’s for yourself, though. I definitely get pouring your heart and soul into your work if you’re passionate about it.” However, I had to admit, at least to myself, that it hadn’t been the wisest decision for my love life.
She rested her elbow on the table and plopped her head down onto one palm. “My job’s…difficult emotionally, to say the least. I’m a lawyer. Even though it’s rewarding and fulfilling and everything a career you love should be, it’s exhausting.”
“I can’t even imagine. It’s also way more impressive than taking photos for a small-time paper and running their Instagram account that barely anyone follows.” I’d hoped the comment would lighten the mood, and I was thankful when it seemed to.
“That’s impressive.”
“You’re a horrible liar,” I told her. “My goal is really to draw cartoons because apparently I’m a middle-schooler trapped in a grown man’s body.”
That made her laugh. “So why don’t you?”
“My boss won’t let me even try it until our social media following increases. Apparently that’s where the money is these days.” I raised an eyebrow like she might know better than me.
“Don’t look at me,” she said. “I can’t even figure out how to use a dating app.”
I chuckled, happy to get back to the topic at hand. “So are you doing this just to appease your sister, or…”
“I was at first, I think. But I’d be lying if I said I didn’t think she was right that I needed to put myself out there and start dating. I’ve only had like two serious boyfriends in my life, and one was when I was a senior in high school. I have like zero point zero experience with…any of this.”
I wondered if she knew she was blushing, and I felt bad that she was sharing all this with me, even though she was obviously doing it willingly.
“So,” she said with another long sigh, “that’s my story. What’s yours?”
I nodded slowly, realizing that I’d need to be honest if only because she had been. “Pretty boring, really. I did the whole college thing, then the career thing. I was a photojournalist in New York before this, but that didn’t work with the whole marriage thing because I was traveling constantly. So she did the cheating-on-me-with-my-best-friend thing, and now I’m doing the recently-divorced-new-job-new-town thing.” I waved Isla off, like telling her all of that had been no big deal. “See? Not at all interesting.”
She was quiet for a few seconds, and the silence made me more uncomfortable than it probably should have. “So you’re happy being single?” she asked.
“Very. I definitely need some time off from the relationship thing.”
She took a sip of her tea before settling back into her chair and staring at me. I could see the wheels turning in her brain, and if I’d been drawing her, I could’ve pinpointed the moment the cartoon lightbulb appeared above her head.
It was right before she said, “What about the sex thing?”
“Excuse me?”
“Sorry,” she apologized. “Sometimes I come off a little forward. I blame my law background, though it probably has more to do with the fact that I’m extremely socially inept. It’s emba
rrassing, really.”
I waited for her to continue, mainly because I had no idea how to respond.
“Okay, this is probably going to sound weird, but hear me out. The other day, I was out with Olivia and she was telling me that she slept with two guys from her art class this semester, and it got me thinking about how I literally have no idea what I’m doing in the bedroom.” She shielded her eyes with her hands and looked at the table as she spoke. “God, I can’t believe I’m telling you this.”
“Are you saying you’re…” I didn’t even want to say the word.
“What? Saying I’m what?” The lightbulb flashed again. “Oh, no! I’m not a virgin!”
“I wasn’t judging you if you were,” I said.
“I know,” she answered quickly. “I’m not, though. I’ve had sex. Plenty of times. But it was like really…vanilla? Is that the right word?”
I shrugged. “Maybe.”
“It wasn’t interesting or really any good, and I was thinking that eventually—hopefully—I’d find someone that I want to take things further with, and I want it to be good when that happens…amazing if it can be.” She was rambling, and I was sure she knew it. But since I found it much too cute, I didn’t rescue her. “Anyway, I’ll just come out with it.” She dropped her hands and made eye contact with me again like the gesture itself might give her the confidence she was lacking. “Would you be my sex guru?”
I wondered how someone might create an artistic representation of my expression right then—eyes bulging out three feet from my face, chin resting on the floor.
“I’m sorry, what?”
Exhaling slowly, she seemed to compose herself. “I told you it was going to sound weird.”
“You did warn me.”
“I figured that since you’ve been married before, you probably have a lot more experience than I do with…”
“Sex,” I finished for her.
“Right. Sex.”
“You realize you have less of it once you’re married, right?” I joked. “And even less than that once she starts sleeping with your friend.”
We both looked at each other for a tense moment, and I allowed myself to imagine what it would be like to be with this woman—to unbutton her sheer shirt and pull her tank top over her head, to suck on her tits, to feel her warmth surround me as I sank deep into her, moving slowly over her until we both exploded.
“Are you considering it?” she asked when I hadn’t spoken.
“I am. I don’t want any type of relationship, and I’m a guy, so…this arrangement could work for both of us.”
Her shoulders fell a bit with an exhalation. “I feel like I should do something for you. Like, in exchange, I mean.”
“Um, Isla, I’m pretty sure the sex itself is the reward for me. Plus, accepting something in exchange for sex makes me a prostitute.”
“I’m being serious. What can I do for you? You’d be helping me, so I want to be able to help you too. I wouldn’t feel right about it if I didn’t reciprocate the favor.”
Her choice of words had my cock jumping in my pants, but I tried to remain calm. I thought for a second, tapping my pen on my sketchbook, but I came up empty.
“What if I let you publish the cartoons of my dates on your Instagram thing? They’re good. Maybe it’ll get you some followers.”
“Really?” The offer was appealing. Maybe it could become something. “I won’t put your name in or draw your face in a way that you could be identified.”
“Sounds good to me,” she said, extending her hand so I could shake it.
We both nearly jumped, pulling our hands away from the other when we heard a deep voice ask, “Are you Isla?”
Neither of us spoke.
“I’m Gage. Sorry I’m so late. My Uber app was all fucked up, and I had to update my credit card or something.”
At his mention of Uber, I saw Isla smirk, but she tried to cover it up by taking a drink.
“I’m sorry, do we know you?” I asked.
Gage looked confused, and he pulled out his phone. “I’m looking for my date. This woman, Isla.” He held out the picture to us. “You’re her, right?”
Isla shook her head.
“She’s already on a date, man,” I said.
He appeared genuinely apologetic. “Oh wow, I feel like an asshole. I’ll let you get back to your coffee.” Then he headed to the door he’d just entered and left.
A long moment of silence hung between us as we stared at each other until I said, “He had tobacco in his lip.”
She dropped her head into her hands. “I know he did.”
Chapter Seven
ISLA
Once Grayson agreed to my offer, I expected him to want to start immediately. I’d been internally panicking that he’d proposition me to meet him in the bathroom or the abandoned alley behind the coffee shop and regret my hasty decision to ask him to be my sex sensei.
But instead, he scribbled his number on a piece of paper and told me to take a few days to be sure I wanted to move forward with what I’d suggested. The consideration he showed made me feel instantly more at ease with the situation.
The fact was, I was hardly ever reckless. Being responsible for keeping my sister alive and off the pole had made impulsivity impossible. But I didn’t want who I always had to be for her to define who I was for myself. I wanted to take this leap, and I wanted to take it with Grayson. Handsome, kind Grayson who sent me home with instructions to Google things I might want to try instead of acting like he knew best what was right for me.
When I got home, I went into my room and launched Google but quickly realized there might be things he wasn’t willing to try either. And there were still other things he might be able to talk me into, because while some things seemed off-putting, they might not be when put into actual practice. I mean, how could I know that nipple clamps weren’t for me? They might sound like a medieval torture device, but what if they were really a path to orgasmic nirvana?
But I also didn’t want to be wholly unprepared. Looking at my laptop critically for a second, I contemplated my next move. He said to research, but not all research had to be read. As Olivia had so graciously reminded me, some could be watched. Before I changed my mind, I went to a porn site and opened the categories.
This was the first time I’d put on porn with the intention of searching for things that involved kinkier elements than a guy pounding away at some perky young girl who could deep throat like she didn’t have an esophagus.
The categories were a little daunting. I could probably rule out the ones that were specific to particular ethnic groups, since I was pretty sure that was something I couldn’t change. Some of the pictures that accompanied the category names weren’t helping matters either. Anal, for example, looked painful. And…painful. I wish I’d asked Grayson how big his dick was, because if he was that big, I was going to need a lot of prep work and possibly a pre-coital training regimen.
After clicking through categories for a bit—and coming to terms with the sheer quantity of fuck videos in the world—I finally found something I was willing to let play for more than thirty seconds. A woman was naked on pink satin sheets, a soft purple blindfold over her eyes and matching ties binding her wrists to a four-post bed. A bare-chested man in leather pants held a cat-o’-nine-tails.
I’d never thought of myself as one to be into masochism. Pain wasn’t my bag—which anyone who’d ever seen me sustain a papercut could attest to. At least I didn’t think it was. But the man wasn’t hitting her with the torture device. Instead, he was letting the tails of it drag sensuously over her skin. The camera zoomed in so I could see goosebumps pebble her flesh. Then he would remove it for a few moments and stand above her silently.
My chest began to heave as I watched hers hitch with anticipation. The longer he waited, the more she would fidget and tremble, no doubt wondering where he was and when his ministrations would resume. The camera focused on her so that the viewer couldn’t be sure when
he would make contact with her again, and it made the internal muscles of my pussy clench in anticipation.
His timing was unpredictable, but eventually the cat would gently descend onto her again. As he worked her up, tickling her mercilessly as well as wordlessly, he began to change tactics. There started to be moments where he would flick the tails against her overly sensitive skin, not hard, but enough that it probably stung—like splashing freezing cold water on someone who’d been overheated.
He mostly reserved this treatment for her erogenous zones: her breasts and the soft skin on the inside of her thighs. The latter location would usually send her arching up, clearly trying to get contact with an even more sensitive part of her body.
As my heart rate sped up and my body zinged with need, there was no denying this scene did it for me. He let the tails drag over her pelvis one last time before he tossed it aside, lowered himself onto the bed between her legs, and began licking her clit. It was clear she hadn’t expected it, because she let out a gasp that turned into a long moan of pleasure.
I couldn’t resist the urge anymore. Pulling up the sundress I’d worn on my date, I rubbed my fingers over where I throbbed. The first touch to my clit caused my spine to stiffen momentarily before I relaxed into the euphoric sensation. While I was no stranger to getting myself off, I hadn’t felt this deep of a need to come in a long time—possibly ever.
I was alive with desire. It was like an out-of-body masturbatory experience, and I was a fan in a big way. Attempting to stay focused on the woman on the screen—who I could see was being fucked now, the man rocking into her without the pounding rhythm that seemed to dominate most heterosexual porn—was like my own version of edging.
Misadventures with a Sexpert Page 4
