I was back to staring at my watch again. Twelve minutes had passed since the last time I checked. I looked down at my phone. The agency sent me a text earlier in the day, confirming all of the details. Then an hour ago, she called and told me she was on her way. That was the first time I’d heard her voice. She said she’d be here by 9. It was 8:37.
I was still sweating, and I’d already showered twice. Once before I left home, then again, not long after I got to the hotel. It wasn’t the heat. It was my nerves. I kept changing my shirt until I ran out of options. I was down to the last one.
I walked a circuit through the room, pacing from the couch to the door, then from the door to the window and back again. Stopping in front of the mirror was a mistake. The guy looking back at me didn’t look ready to be waiting for a woman like her, in a place like this.
The agency’s website said her name was Londyn. They never use their real names. This one sounded like it was made up by a girl who might have had a more ordinary name like Sarah. I wondered why Londyn. Maybe visiting the city was her fantasy, the way she was mine.
Her profile was different from the other ones. They were all loud and competed for attention. Hers had the confidence to sit quietly and wait for the right kind of person to discover it. She wasn’t advertising sex in a flashy way. There weren’t any pictures of her in lingerie bent over a desk. It seemed like all the other ones had some version of that shot.
What she was presenting was an opportunity to spend time with her, with the suggestion that if the chemistry was right, anything could happen. She wasn’t a sure thing. She laid out what she was looking for and expected anyone interested to agree to her terms. The small print made it even more clear. Quick visits weren’t offered. She had a four-hour minimum. Girlfriend experiences only. First timers welcome. Wine was mandatory.
Her whole profile was set up to discourage the wrong kind of client. She was there for guys like me. Someone who’d never done anything like this before. Not with an escort. Not with anyone. A virgin.
My phone was ringing. It was Londyn. She was as calm as she was professional, and understood exactly where my head was at. She knew I needed something to focus on.
“I’ll be there in twenty minutes,” she said. “Make sure the place is clean. That includes the washroom.”
“Of course,” I said.
“And Greg, if you don’t have a bottle of wine, have one sent to the room.”
I knew I’d forgotten something.
“Most of all, relax,” she said. “You seem like a great guy. I can already tell we’re going to have fun tonight. Don’t spiral.”
“Too late.” I laughed nervously.
“See you in fifteen now.”
I did a quick run through of the place, hoping it was more ready than I was. The sitting area was good, and I’d already taken care of the washroom after showering. I went to the bed, and just stared at it. It was made and had clean sheets. I wasn’t worried about that. I just couldn’t help but think about what I hoped might happen there tonight.
The last thing to check was the envelope. It was right where I left it, on the coffee table, looking like a movie prop. I filled it with cash in the morning. Ten hundreds and fifty twenties. It was the most I’d ever taken out of an ATM before. Now it just sat there, waiting for her as much as I was.
There was a knock at the door. I froze for a split second, but it was too heavy to be her. Room service brought me the wine. I asked for the best they had. A bottle of champagne showed up, delivered in an ice bucket.
“Will Sir be drinking it soon?”
I couldn’t figure out why he was asking, and looked back at him, confused.
“Would you like me to open it and let it breathe?”
“Oh, yes, please.”
A few minutes after he left, my phone lit up with a text.
I’m in the elevator. Room 403, right?
Yes. I texted back with a shaking hand.
My eyes locked on the door, waiting for her, wishing I’d had another shirt to change into. The ice bucket came with a towel. I wiped my sweaty hands on it. I took one last look in the mirror. Nothing changed since the last time. I was still the same guy who looked like he was in over his head.
There was another knock at the door, lighter this time. She’d arrived.
It took everything I had to take the first step towards the door. I had to remind myself that this is what I wanted. I’d spent weeks planning, and months before that thinking about it. It was time. And Londyn was the right choice. I was sure of it.
I took a deep breath and let it out slowly as I opened the door.
“Greg?”
It was her. The woman from the internet, standing in front of me— a real, live person. Londyn’s profile pics showed me what to expect, but nothing could prepare me for what it felt like to be in her presence. I already knew she was beautiful. The agency called her ‘elite’ and charged a premium, but it wasn’t her figure that hit me. It was how she looked at a man full of doubt, too nervous to speak, and smiled patiently without judgment.
She gave me a few moments, then leaned in a little and whispered a suggestion. “You should probably invite me in.”
“Right. Of course, sorry I—”
“It’s okay,” she assured me.
I stepped aside and motioned her in. I caught her perfume as she walked past me. It was familiar. Some of the girls on campus wore it. The kind of girls who usually didn’t talk to me.
“Listen,” she said as she made her way deeper into the room. “I know you’re probably freaking out a little bit, but it’s going to be fine. I promise.”
“It’s just—”
“Let’s slow down and not get ahead of ourselves,” she said calmly. “We’ll start with the basics, yeah?”
“Okay.”
“You are Greg, right?”
“Yes.”
“Good. Imagine if you weren’t,” she said. “Try explaining that one to the wife. I don’t know who she is, she just showed up, I swear!”
That made me laugh.
“See, we’re already starting to loosen up a little.”
“I’m sorry, it’s just that I’ve never…”
“I know.” She said it like it wasn’t a problem, just something she understood. “You’re in good hands.”
She gave me a second, then her tone turned more serious.
“We’re going to go over some rules,” she said. “You don’t have to say anything, just listen.”
I nodded.
“The first thing is: you’re paying for my time. That’s it. Nothing is owed. Whatever happens, happens because we both want it. Understand?”
“I do, yeah.”
“Good. Second, no means no. It doesn’t mean ask again. It doesn’t mean pressure or try to charm your way around it. No’s are final.”
“Of course.”
She smiled at that. “I figured you were a sweetheart,” she said. “But I still have to say it. It’s part of the job.”
“Makes sense,” I said.
“Now, if our date gets to a point where we’re both comfortable, and things escalate, you have to wear a condom. No exceptions.”
I got hit by a sinking feeling. For all the work I’d put into this, condoms never occurred to me. Everything was about to be ruined because I left a trip to CVS out of my planning.
“Oh… I… umm…” I looked at my watch, trying to think how long it would take me to get to a drug store.
“You’re okay, sweetie,” Londyn said, patting her bag. “I’ve got you covered.”
“I’m really sorry… I’ve had a lot to think about and—”
“Say no more,” she said with a smile.
Londyn looked behind her and took a seat on the room’s couch, placing her bag on the coffee table as she did.
“Just one last thing,” she said, as her eyes drifted to the envelope on the table.
I reached for it. My hand was shaking. She didn’t say anything, just opened her bag and left it there for me to drop the envelope inside.
“I’m not going to count it in front of you,” she said. “But just so you know, there’s a guy from the agency downstairs in the bar. And he really hates it when someone thinks eighteen hundred or nineteen hundred is close enough to two thousand.”
“It’s all there.”
“I believe you,” she said. “You’ve got an honest face.”
She put her bag on the floor, then sat up straight, clapping her hands against her lap. “Okay,” she said, “That’s the business part done. Now let’s get to know each other.”
I stood up and went for the champagne. “I forgot about this too,” I admitted. “But when you called, I had it sent up. It’s been chilling here… in the ice.”
“Well, I’m impressed, Greg. Wine is part of the deal, but champagne is a thoughtful touch.”
Londyn pulled her legs up onto the couch and looked at me with a warm and excited expression. She looked like she actually wanted to get to know me. I couldn’t help but think of it as an interview. Nothing is owed. That was rule number one. I felt like I had to make a good impression.
“Why don’t you tell me a little about yourself. Whatever you’re comfortable with,” she said, then leaned in and fake-whispered, “You can even lie. I’ll never know.” She smiled and gave me an exaggerated wink.
“Well, uh… I’m a student. Last year of college. Business Admin degree, just a few months away now.”
She nodded slowly, like she was genuinely listening.
“And what comes after college?”
“New York, hopefully,” I said. “That’s the plan.”
“A smart guy like you? You’re going to crush it in the big city.”
She said it like she was certain, like she’d taken a peek into my future and knew that it all worked out for me.
“Is it okay if I ask about you?”
“Yes,” she said, with a bit of reluctance. “Just none of those ‘how did a girl like you end up in a job like this’ kinds of questions.” She took a sip of her champagne, then added, “But if you want my take on the Kendrick vs Drake beef, then yeah, let’s talk about it.”
I didn’t want to push, but I really wanted to know what it was like to be someone like her. I didn’t mean an escort, just someone who was so confident and comfortable in their own skin.
“Were you always like this?” I asked. “Like, so… sure of yourself?”
She looked past me for a second, over to the window, then came back to me. “No one is always like this,” she said. “But I set boundaries. I don’t let disruptive things get into my life.”
“Do they ever not work?” I wasn’t even sure what I meant by that. I just heard a hesitation in her voice.
“So far, so good,” she said. “But life has a way of humbling us when we least expect it.”
Londyn leaned back into the couch. Her expression changed again. Whatever shimmer of doubt I’d just seen was gone. “Kendrick,” she said, changing the topic. “Final answer. If you say Drake, the date ends here,” she added with mock warning.
Over the next hour, we talked like we actually knew each other, not like two people meeting for the first time. Londyn made it easy for me to get out of my own head, and I was finally starting to feel like my normal self. Which wasn’t exactly a high point when it came to women.
I was far from smooth. I had no experience with flirting or even having a conversation with a woman with the expectation that it might lead to more. She pretended not to notice when my nerves showed, and let me think it was part of my charm. Maybe it was, because I was beginning to think she might actually like me.
I don’t remember what we were talking about when she leaned in.
“Do you want to kiss me?” she asked.
My mouth went dry. “I do, yeah.”
“Then do it,” she whispered, already closing her eyes.
I hadn’t kissed anyone since high school. It had been that long. The second our lips met, I was reminded of everything that was missing from my life and what led me to tonight. Her kiss was soft, not forced or rushed. She wasn’t checking an item off a list. She was making me feel wanted, like I was worthy of her attention.
She pulled back, slowly opening her eyes. “That was really nice,” she said, almost looking surprised, like she might have been caught off guard by something.
“I’m going to freshen up,” she said. “Go make yourself comfortable on the bed.”
No words had ever terrified and excited me as much as those ones did. I passed her interview, and all the calm feelings I’d built up over the last hour vanished in an instant.
When the door closed behind her, I made my way to the bed on shaky legs. I sat down on the edge, not sure what I was supposed to do. Was she expecting me to strip down? Under the covers? On top? In the end, I undid a few buttons of my shirt, just to feel like I’d done something.
When the washroom door opened, I was stunned. Londyn’s dress was gone. She came out looking like a Victoria’s Secret model. High heels, lace stockings, silk bra and panties. All black. She was smiling, knowing exactly what she was doing to me.
“Oh my god.”
“I was hoping you’d like it,” she said. “If you don’t, I have some other—”
“No, that.” The words shot out of my mouth faster than I expected. “I like that,” I said more slowly.
She smiled and raised her hand to her mouth, subtly covering up a laugh. That’s when I noticed that she was holding a condom.
When she stood in front of me, my hands moved on their own and found her waist, then slid lower. I wanted to reach for her ass, but I wasn’t sure what I was allowed to do.
Londyn tossed the condom onto the bed beside me. Her intentions were clear. This was happening. “Let’s get you out of those clothes,” she said, reaching for my hands, guiding me to stand.
“You’re still good?” she asked, once I was up.
“A lot better than good.” It came out as a nervous laugh.
She undid the rest of my shirt. Her eyes moved between mine and each button as she went. When she got to the last one, she pulled the shirt off my shoulders and let it fall to the bed, before it slumped to the floor.
“If this is too fast, we can slow down,” she said, reaching for my belt.
“No,” I said, again too quickly.
With my belt undone and my pants hanging open, she tilted her head up and kissed me again, then went down on her knees. She hooked her fingers into the waistband of both my pants and underwear, and tugged them down in one motion. I stepped out of them awkwardly. As I raised each foot, she pulled my socks off, too.
Londyn looked up at me, knowing she was the first woman to see me like this. She didn’t say anything. She just let me get used to being seen, like a silent witness.
She went for my cock, and curled her fingers around the shaft. I recoiled from her touch.
“It’s okay,” she said. “It’s going to feel really good.”
“I know,” I said, nervously clenching my hands.
She smiled and started to stroke me, still looking me in the eyes. “It’s different, right? Having someone else touch your cock.”
I was already breathing hard and could barely speak. “It’s good,” I managed to blurt out.
“I’m going to put it in my mouth now,” she said. “Try not to pull away.”
She didn’t give me time to react. She just opened her mouth wide and then closed her lips around me. I felt the heat of her mouth and the softness of her tongue at the same time. It hit me so hard my knees gave out, and I fell back onto the bed.
It didn’t slow Londyn down at all. When I dropped, her head came with me. In the same motion, she moved her hands to my knees and guided them apart, giving herself more room to work.
Every few seconds, she lifted her eyes, holding them with mine while she sucked. For the first time in my life, I felt like a man.
“You’re doing great,” she said, before returning her mouth to my cock. I was about to realize that she’d been taking it easy on me up until then. Now her hand and mouth were moving in sync as her tongue twirled the head. Her grip tightened, and she added a twist to her wrist with each stroke.
“I want you to cum” she said, pulling off just long enough to speak. “Cum in my mouth.”
Her hand kept moving faster. “You can do it,” she encouraged. “Cum for me.”
My whole body bucked beneath her as I emptied into her, grunting the whole time. She didn’t stop or pull back. She stayed with me, her lips still wrapped around me, her tongue still coaxing the head, as she drained everything I had to give.
When she finally pulled away, Londyn wiped the corner of her mouth with her thumb. “How was your first blowjob?”
I couldn’t speak. I just nodded, still breathing hard.
She gave my cock a kiss, then climbed onto the bed beside me. Londyn looked around for the condom and handed it to me once she found it. “Put it on the nightstand,” she said. “For now.”
I took it with trembling fingers and placed it beside the lamp.
She tucked herself into me, putting her hand on my chest, letting it move up and down with my heavy breathing. Neither one of us said anything for a bit. It was going to take a few minutes for what just happened to sink in.
“Put your arm around me,” she said.
I did, and she cuddled up closer. Her hand went to my hip, and brushed my skin with her fingertips in a way that made me shiver. I hadn’t been touched enough to get over being ticklish yet.
“I wish I knew what to say,” I told her.
“You don’t have to say anything,” she said. “I’m just glad you liked it.”
“Liked it,” I laughed, this time without nerves. “That’s one way of putting it.”
Londyn promised a girlfriend experience, and this really felt like it. I didn’t think it was love or anything close to it, but I’d never felt more connected to anyone in my life. She made it easy for me to forget that I was paying for it.
“You’re better at this than you think, you know.”
“What do you mean?”
“Think about it. You were a wreck when I walked in,” she said, laughing slightly. “I was honestly worried about you.”
She wasn’t wrong to be worried. I was a mess.
“Look at you now,” she said. “You’re in bed with a woman, naked, and just got your dick sucked.”
“When you put it like that…”
“Seriously. An hour ago, I had to pretend that I wasn’t watching you forget how to say hello.”
“Was it that obvious?” I asked.
“Yeah,” she said. “But charming, in your own way.”
I held Londyn a little tighter, and she let herself sink into me. I don’t know how long we lay like that. I almost wished it could’ve lasted all night, but I hadn’t spent weeks psyching myself up for a cuddle session.
“I think I’m ready,” I said, looking over at the condom.
“You’re sure? We have plenty of time.”
“I’m sure.”
She sat up and took my hand, placing it on her waist, holding it with hers before letting go. I kept it there for a minute longer, then let it move behind her, following the curve of her body until I felt the shape of her ass through the silk of her panties.
“You’re getting hard again.” I felt her fingers take hold of my cock. She moved my hand from her ass, further up her back. “Take it off,” she said once I reached the clasp of her bra. It popped open and let my fingers draw the straps down her arms.
She slipped out of it, letting it fall, then shook her shoulders a little bit, making her tits sway.
“Touch them,” she said. “Use your mouth. Lick my nipples.”
I raised my head to meet her breasts and kissed.
“Mmm… that feels nice,” she said. “This is the fastest way to get me wet.”
My cock throbbed when she said it. Londyn felt it pulse in her hand and took it as a sign. She lifted herself and sat upright on the mattress, then leaned back on her hands and parted her legs.
“Take my panties off.”
I swallowed hard. My hands were shaking as I reached for the thin band of the black silk on either side and began to ease them down. She lifted her hips to help me as they slid past her thighs. With no obvious place to put them, I tossed them on the floor. When I looked back at Londyn, her legs were spread wide.
“Have you ever seen a pussy before?”
“No,” I said. “Only on the internet.”
She moved her fingers between her legs and parted her folds open. “See how wet I am? You did that.” She reached over to the side table for the condom. “I can’t wait to fuck you.”
I watched her sit back on her heels and tear the wrapper open. She placed it on the tip of my cock, then rolled it down. She had a different kind of smile on her face now. One that suggested she was both excited and happy for me.
She lifted herself a little and straddled me until her knees hugged either side of my thighs. She put a hand on my chest as she eased herself into position.
“Ready?” she asked.
“Ready,” I said back to her.
Londyn bent forward and gave me a kiss. My last one as a virgin. Then she adjusted her hips, just enough for her to reach between us and guide me into place. My head shot back into the pillow as she began to lower herself on my cock.
The sensation of her tight warmth engulfing my cock felt better than I ever could have imagined. Londyn smiled, knowing what I was going through. First timers welcome.
“Feels good, doesn’t it?”
“Yeah.” It was all I could say.
“Just wait,” she said. “It gets better.”
She planted her hands against my chest, then started to move her hips, gently rocking back and forth, slowly getting me used to being inside her.
“You have a nice cock.” She said it like she meant it.
With that, she lifted herself up, then lowered herself down for the first time. I understood then why she’d given me a blowjob first. Without it, I probably would have cum the second I slid into her. I know I wouldn’t have made it this far.
“I can’t believe how good your pussy feels,” I whispered for some reason, like I wasn’t sure if I was allowed to say it, even though every part of me meant it.
She smiled again, and began riding me, sliding herself up and down the length of my cock. I didn’t know what to do with my hands, so I placed them on her sides. Her pace picked up, and I noticed her biting her lip right before she let out a soft moan.
“This is… good,” she said, breathing harder now. “Put your hands… up here… on my tits. My nipples.” Her voice was breaking up. For the first time tonight, she was letting her control slip away.
When I touched her breasts, she put her hands on mine and moved them along with hers. “Like that,” she said. “Keep doing that.”
She was moving a lot faster now, grinding her hips into me. She lowered my hands back to her waist.
“Push,” she said. “Into me.”
It was awkward at first, but it didn’t take long for our bodies to find a rhythm. She bounced on my cock, and I thrust up each time she came down, making a loud slapping sound each time.
“Just like that,” she said. “You’re fucking me, Greg.”
I never thought that I’d hear a woman say those words.
“That’s it,” she said, breathlessly. “That’s it. You’re doing so fucking good.”
“Greg…” She felt it. I could tell by the way my name thinned out as her voice faded, and how she gasped for air as soon as she said it.
I wasn’t going to last much longer, and it felt like Londyn was close too. It started in her legs, with a small shiver in her thighs. Then I noticed the way her hands were trembling as she moved them between my chest and shoulders. Everything inside her got tight. Her pussy gripped me harder every time she came down on me. Her head went back, and she started to let out a series of loud moans.
“Greg,” she gasped. Her voice was urgent. She pressed her forehead into mine, looking me square in the eyes. “You’re making me cum.”
That did it for me. I bucked up, grunting, over and over again, each time filling the condom more until there was nothing left in me.
It took a few moments, but eventually, we both stopped shaking. Londyn looked down at me, smiling like she couldn’t help it.
“That was…” She stopped herself and quickly regained her composure. It was like she’d almost forgotten who I was, then remembered. “Sorry,” she said. “Are you okay?”
I tried to find my voice. “Better… better than okay.”
“Good,” she said. “Because that was fucking beautiful.”
She pulled herself away, lay down, and curled up next to me.
I let out a long breath. It was more than just relief. It was years of frustration and resentment, maybe even anger, all coming out at once. I let all of it go.
“Greg,” she said, almost hesitantly. There was something different in her voice.
“What just happened… that doesn’t happen. Not like that.”
I turned my head toward her. “What do you mean?”
For the first time, she didn’t seem as sure of herself as she had been since we met. “What you just did to me… when I’m with someone… new. That doesn’t happen.”
“You mean—?”
She nodded. “Never.” She looked away for a second, then found my eyes again. “This isn’t how it’s supposed to go.”
I didn’t know enough to fully understand what she was saying. I just thought to myself that it was good that she enjoyed herself too.
“That was real,” she said. “Every part of it. You should know that.”
She hesitated again, but then, maybe against her better judgment, said what she’d been holding inside. “I won’t forget this,” she said, shaking her head like she still couldn’t believe it. “I won’t forget you.”
As the words left her mouth, I caught a glimpse of something in her eyes. I wasn’t sure what, but she showed me something that I didn’t think I was supposed to see. She let something get away from her.
“I should go,” she said abruptly.
I turned myself toward her, with my hand still on her back, holding her.
“Are you okay?” I asked.
Londyn had been composed all night. But that was starting to come apart. She pulled back and sat upright at the edge of the bed, turning her back to me. She fumbled with her bra, trying to get the clasp to catch. She tried a few times, then gave up and threw it over towards her bag.
“Londyn?” I said, sitting up behind her.
She didn’t turn around.
“I shouldn’t have said what I said,” she replied, quickly. She was anxious, and it was getting stronger now.
“What do you mean?”
She rushed to get her dress from the washroom. Still facing away, avoiding looking at me.
“That thing,” she said from the other room. “About how this was special for me too, how I won’t forget you. I shouldn’t have said that.”
She was unravelling, and I was slowly starting to understand why.
She came back to the bed, gathering a few more of her things. That’s when she angled herself to me, just slightly. Enough for me to see the side of her face. Her eyes were racing. I’d seen panic attacks before, and thought she was having one.
“This is my job, Greg. I’ve been doing it long enough to know what the boundaries are. And this is the biggest one.”
“What?” I asked, knowing I’d regret the answer.
“No connections.” She looked at me and couldn’t hide her fear and vulnerability.
She grabbed her bag and scanned the room like she was trying to make sure that no signs of her ever being there were left behind.
“You didn’t do anything wrong,” she added quickly. “It was me. I let myself feel.”
“You don’t have to go,” I said. “Not yet.” For a second, I thought she might stay. “We can just… sit,” I offered. “Or lie down. No expectations. I don’t want anything, I just… You don’t have to be alone with this.”
Again, I thought maybe, but she shook her head no.
“If I stay, it gets harder,” she said.
She was already at the door, with one hand on the knob, when she stopped. She didn’t turn, just spoke, still facing the door.
“You got through,” she said. “You made me forget my own rules.”
“Please… just stay,” I asked, already knowing she wouldn’t.
“No connections,” she said, not to me, but to herself. A reminder of the importance of boundaries and the line she’d drawn years ago.
She opened the door and took a step out, then stopped again. She looked back over her shoulder.
“Greg?” she said. “My name is Beth.”
It was a parting gift. A final moment of truth. She’d given me her real name.
Beth. Elizabeth. Like the Queen. London.
And then she was gone.
I needed a drink. I got off the bed and poured what was left of the champagne into my glass. The room still smelled like her perfume. I sat on the couch. That’s when I saw it.
The envelope I’d given her was sitting on the coffee table.
