OAKLYN
I’d never masturbated so much in my entire life as I had in the past two weeks. Each time seemed more intense than the last. Charlotte was right, the first time was the hardest, and it got better from there. She’d laughed and said, “I told you so,” when she saw me filling all three performance slots every night I worked.
A lot of clients had been similar to the first, only wanting the illusion of peering into something hidden, without actually seeing everything. But then there were some that wanted me topless and playing with my nipples, or not wearing any panties, or using a vibrator or dildo.
Sometimes, I lay completely naked, exposed to whoever watched me or under the spray of the shower. Whatever they requested. My heart seemed to beat the fastest when they were completely hidden behind the dark glass in the connecting room.
Tonight felt different though, and feeling brave I’d left the option open to work with Jackson. Not that I was sure I’d take it, but I did it anyway, just to see how it would feel to have the option. So far no one had asked, and I felt both happy and sad about it.
The night had been pretty slow. People were probably still recovering from New Year’s Eve a few days ago, but it
looked to be picking up when I rounded the corner from the back carrying the box of napkins Charlotte had asked me to get for her.
Good. I needed the distraction. The holidays had been hard this year because I couldn’t afford to go home. I loved Christmas with my whole extended family and watching National Lampoon’s Christmas Vacation alone on my couch had been depressing. My parents had called, and everyone wished me a Merry Christmas, but it almost made it worse.
I had to pull back from talking to my parents after that. I didn’t want to resent them for the current situation, but I did, and showing how mad I was wouldn’t help anything. I knew they were sorry. I knew they would take it back if they could. I knew, and it didn’t help calm me at all.
Instead, I’d rather avoid them. At least for now.
And it was the new year. I’d start school soon and that was the biggest positive to focus on. I was achieving my goals, no matter what. That was my silver lining. Reaching the bar with a new resolve to focus on the positive, I set the napkins down with a smile.
Looking up, I noticed a man with a dark head of hair at the far end of the bar. He jerked away when I noticed him.
Intrigued, I wondered if he’d been watching me. Maybe he’d be the one to request me tonight. The idea sent a thrill of excitement zipping through my body. He seemed large under the dim lights. I could see the breadth of his shoulders, straining against his charcoal suit, and how he sat farther above the bar top than the other men sitting around him.
Shadows hid his face, but I could see his long fingers gripping the glass before him. I imagined those fingers gripping his cock, stroking it as he watched. I pushed the napkins off to the side and began to round the bar, wanting a better look at him. Maybe if I would check to see if he needed something, flirt a little. Maybe I could entice him into watching me. I rarely saw the faces of anyone who
watched me, and it didn’t bother me. It made it easier to detach. But something about this man made me need to see his face. Each step closer caused a flutter in my stomach.
The possibilities were making me more excited than I’d been since I started.
When I was just five bar stools away, a body blocked my progress.
“Oaklyn.” The way Jackson said my name, matched with his smile led me to believe he wasn’t about to ask me for the time.
“Yes, Jackson?”
He dragged a hand through his hair. “So, I was requested for a couple’s session, and they specifically mentioned you.”
My heart thumped in my chest. This was it. This was my opportunity to try something out with Jackson. I looked down at my watch and saw that I hadn’t been notified of a request.
“But why didn’t they fill out my form too?”
His smooth smile slipped a little. “Yeah. About that. You, uh, didn’t have the things requested on your availability, so mine was filled out since I’m listed as your partner.”
“What was the request?” I’d opened a partner option up but limited it to kissing and some heavy petting.
“It’s just sex.” When my eyes bugged, he held his hands up trying to stop my panic. “Before you freak out, the note says they’ll pay double the regular cost of the performance.”
My jaw snapped shut and I let those numbers roll through my mind. Just that one performance, at double the price, would cover almost all of my supplies for the semester. Just the thought of having sex with Jackson, who I barely knew, in front of someone made me lightheaded. I knew eventually, I’d make my way to it, but I figured I’d have time to work up to sex.
My skin seemed to be alive with fire the way it heated at the idea, but my heart seemed to be pumping too fast. I didn’t know if it was because of excitement or fear.
“Look, I wouldn’t ask if the money wasn’t so great. Also, it’s been requested as lovemaking, so that usually entails below the covers. Kind of like all the times you’ve been getting off hidden by your underwear. I don’t have to penetrate. I can pull your thigh over mine and hide it.”
“Were there—” I had to clear my throat past the ball of nerves. “Were there any other requests?” I asked staring at this throat, watching his Adam’s apple bob.
“Um, just some oral. For you. I give you oral sex, but I can pretend to do that too,” he rushed to assure me.
The possibilities swirled in my mind, and I calculated the amount of solo performances I’d have to do to make the same amount of money. In the end, agreeing to this was the smart decision to make.
It wasn’t even real sex. I just had to be naked in front of Jackson and, honestly, that didn’t bother me. I wasn’t even sure what did bother me.
That I’d like it, a voice rang out in the back of my head.
Squeezing my eyes closed, I nodded in agreement before I could change my mind. “Yeah. Sure, Jackson. Just let me know when.”
“Now.”
“Now?” I didn’t know why I was shocked like the time made a difference in what was going to happen. I just figured I’d have more time to mentally prepare. Then again, maybe just letting it happen and not mentally preparing was better. Jackson looked like he was holding his breath, and I shook off my nerves and put him out of his misery. “Okay. Now is fine. Okay.”
Two strong arms banded around me and lifted me off my feet. “God. Thank you, Oak. I promise it will be the best pretend sex of your life.”
Once my feet hit the ground again, I gave him my hardest stare. “It better be.”
He laughed and grabbed my hand, leading me toward the back hallway, to hopefully the best pretend sex I’d ever have.
We broke apart to go freshen up before we entered the room, letting the voyeur get settled. Once the light had been switched to green we’d decided to enter making out, like we were a couple coming in from a late night.
“Ready?” Jackson asked once we stood outside the door.
“As I’ll ever be.”
“Remember, it’s just a performance. Not real. Try not to fall in love with me.” He finished with a wink.
I remembered the lack of fire between us, grateful for how much easier this would be. I shook off my nerves and rolled my eyes. “I’ll try not to.”
“Panic button is on the nightstand should you need to use it,” the guard said. “I’ll be out here the whole time.”
Jackson leaned down and pressed a kiss to my lips with his hand on the knob. My lids fell closed as I breathed deep through my nose. Then a strong arm wrapped around my waist and I was being tugged into the room. My hands dug into his hair as I pushed myself close to him. He kicked the door closed and hoisted me up with both palms on my ass.
I opened my lips and tasted the mint on his tongue before he began trailing kisses down my neck. When he’d reached the bed, he gently lay me down and slowed the frantic pace we came in with. It took all I had not to let my gaze flick to the large, dark glass off to my right.
Being with Jackson was more than I’d anticipated for the night. But imagining someone on the other side—a man—
with his cock in his hand as he watched me, sent a spike of adrenaline through my limbs. I wasn’t even sure it was a man. I hadn’t looked at the sheet. It could’ve been a woman or a couple, but the image of a man fueled me, gave me the picture I needed to focus and get amped up.
I was distracted by my white T-shirt being lifted and pulled over my head, leaving me in a barely-there white lace bra. Jackson stripped himself of his own white shirt and then fell to his knees on the floor at my feet lining his face up perfectly with my chest. Holding my gaze, he lifted his hands to my breasts, swiping his thumbs along the hardened tips before hooking them in the cups and tugging them down.
He didn’t immediately look at my bared breasts, but continued to look into my eyes, conveying a comfort that I could trust him. I was thrust back into remembering when he kissed me the first time. It had felt nice, I’d enjoyed it, but nothing about it urged me to demand more. The same stretched between us at that moment.
It was a performance. Like actors in a play. Some nights, when working there felt like too much, I reminded myself of that. Voyeur was a job, and I was an actress.
My body still reacted when his mouth dropped to suck on my nipple. My core still squeezed when he began unbuttoning my jeans and tugging them off my legs. My muscles still trembled as he pushed me back on the bed, hoisting a thigh over his shoulder and planting his mouth at the top of my mound.
My whole being seemed to be vibrating with nerves of excitement, of fear. What if the customer knew that Jackson wasn’t actually eating me out, but just pretending to? What if they demanded their money back and this was all for nothing? His head dropped lower, skimming my folds and I forced myself to relax. It had to appear natural and I used the tension to arch my back and moan. When his tongue flicked out to slip between my folds and graze my clit on his way back up, I let out a real gasp and one hand shot out to grip the sheet as the other dug into his hair.
I wanted to ask him what the hell he was doing. Remind him that we agreed on pretend and not him actually tasting me. But when he didn’t do it again, just tortured me with
anticipation of the possibility as he moved closer and closer to my slit, I instead focused on acting natural. This needed to appear natural. I picked up my breathing, my writhing, my moans until I tightened my whole body in a fake orgasm.
It wasn’t hard considering I had Jackson’s head between my legs. But my mind wasn’t on him. It was on whoever watched me behind the glass. Add in the soft touches against my folds, and I felt like a live-wire ready to detonate for real.
Soft kisses worked their way up my body to caress my nipples. Jackson’s large hands framed my hips and pushed me further across the bed until my head was almost hanging off the other side. He tugged the cover out from under us, pushing it down and bunching it up at my hip to attempt to block the direct view of us having sex. He crawled between my legs after grabbing a condom, never taking his eyes off of mine.
He didn’t let them rove my body and stare when he didn’t need to. He respected me and the situation, and we performed. We did our job.
When he finally undid his pants just enough to free his cock, he looked down to roll the condom on, and I couldn’t help but look too. Jackson was big. He was long, thick, and perfectly straight. It matched his body perfectly.
Giving him the same respect as he gave me, I quickly averted my eyes, giving him an adoring look as I scanned up from his sculpted abs and defined chest. I stroked my hands up the smooth skin of his arms and gripped his shoulders. He lifted my thigh and then reached to grab his cock to situate it.
Hopefully, to the viewer, it looked as though he was sliding inside me, when in reality, he pressed himself between my folds and began to thrust. The long glide of him brushed against my swollen clit and I knew, despite pretending, I was going to come from the friction alone.
His forehead rested on mine as his thrusts became harder, until he fell into the crook of my neck, picking up the pace. Faster and faster he stroked across me. His hand gripped my thigh tight, holding it in place. All of it swam through me and consumed my body.
But my mind? My mind was focused on the stranger behind the glass. For all I knew it could be an older couple, not even watching as they fucked like bunnies. But in my mind, it was the man from the bar. In my mind, he’d been staring at me and wanting me all night. In my mind, he approached me and took me home and was the man above me. His broad body flexing with each thrust, pushing inside me, filling me up.
I didn’t even know his face, but when I began to come, it didn’t matter. All that mattered was holding on as groans of pleasure vibrated the skin of my chest and my body struggled to ground itself back to the bed. Jackson pressed his head into my neck as he groaned out his own release, pushing hard against my sensitive clit, drawing a few more aftershocks from my orgasm.
“Thank you,” he whispered against my skin once he’d finished, anchoring me to the moment.
I gave him a barely-there smile as he rolled to his side, shedding his pants and tugging off the condom filled with his cum. I forced myself to look away, the picture seeming more intimate than what we’d just done. He leaned back down and shifted us until we laid under the covers, my head resting on his shoulder.
He kissed the crown of my head, but my gaze didn’t leave the light by the window. It was still green, meaning someone was still in there. Was this the part that made them come? The aftermath, the connection? Was this what they liked to watch?
I stared at the light until my eyes burned. I wasn’t even sure how long I’d been watching before it finally switched to red and I blinked, looking away.
“So,” Jackson started. “Best pretend sex you’ve ever had?”
“You weren’t supposed to actually lick me,” I reprimanded with little heat.
“I had to at least have a taste. Your wetness was too alluring.”
“Stop,” I laughed and slapped his arm.
“I won’t do it again. No matter how wet your pussy gets against my chin.”
I laughed.
I laughed at his question.
I laughed at the bizarre situation of lying naked with a man I just pretended to fuck.
I laughed because I enjoyed it. I enjoyed the idea of the man behind the glass coming as he watched me.
I laughed because I didn’t know how to handle these feelings and laughing was easier.
