Accidental Call Girl

I mean, there were a few different reasons why I ended up a sex worker, but the biggest reason was boredom. I was so bored. I was soooo booored, Audrey. I was on vacation with my parents, this was the summer after my sophomore year of college, we were in Italy and they wanted to go to some museum and I was like I'm just gonna go shopping, but I accidentally left my purse in the room and it had my phone and the room key in it and all my money and the front desk pretended like they didn't speak English and I was basically just stranded all day.

So I went to the bar. It was all I could think of to do! I just sort of sat there at the hotel bar, drinking water. And that's when Orlando showed up.

He came over and sat next to me and said, "Would you like a real drink?" He had a light Italian accent and I wondered how he knew to speak English to me. Did I look that American? Probably. I have this sort of all-American look, girl next door, whatever, with the blonde hair and dimples, and I was wearing short shorts that said PINK on the butt and a pink tank top. Okay, I probably looked that American.

Anyway normally I'd brush someone off if they tried to hit on me at a bar, buuuut what was I? That's right: bored. I would talk to anyone at that point. I had literally nothing to do. I looked at the guy and he seemed fine. Like way older than me, middle-aged, but he dressed well and carried himself well. I figured he might not be too bad to kill a few minutes with. So I gave him a friendly little smile, like "oh my God, I would love that." I told him the whole purse story and he nodded sympathetically. Before I knew it he'd sat down next to me and we each had a glass of wine in front of us.

He was actually pretty slick. He just seemed really confident and laid back, so it didn't seem like a big deal. Just a couple of strangers killing some time. He told me he was there on business, he traveled a lot. When he heard I was from New York he said "Ah, I am frequently there as well." He'd never been to Brooklyn, though. I told him he should come and he flashed me a dazzling white smile.

He was definitely flirting with me, at this point. Like, it was clear that he was interested. It was kind of fun. I'd never been seriously hit on by an older man. He seemed sophisticated and important, and I indulged in a quick fantasy of hanging on his arm on some yacht somewhere, his inappropriately young sidepiece. I wasn't seriously going to do any such thing, of course; I didn't think there was any chance I'd actually leave the bar with him. I was just playing. But I did flirt back. Why not? Flirting was fun. Flirting with him was fun.

You can probably see where this is going, because I already told you. We hung out for probably half an hour, just chatting to each other, and then finally he said, "Listen, if I were to suggest we continue this conversation up in my hotel room... how much consideration might I offer you for a little more of your time?"

I squinted at him. It took me a moment to even parse all those words. "How much... in your..." Finally I caught up, and I gave a startled little yelp. "Oh my god!"

Orlando sat back, looking dismayed. "Oh no," he said. "You're not..."

"You thought I was a..." I gaped at him, and then burst out giggling. "You thought I was, like... for money?!"

He bowed slightly. "I'm so sorry. The higher-range girls sometimes work here. You're so beautiful, and you were sitting alone. I'm quite embarrassed."

I was still laughing. "No, it's... it's flattering, honestly. Sort of. You think I'm pretty." I sing-songed the last part, teasing, and kicked him lightly in the shin. He didn't seem dangerous or gross. I saw how he might have made the mistake. It's not like I had a problem with sex workers. This had turned into a funny story, at this point. But I was totally thinking about you, Audrey, I was like oh my god, Audrey's gonna lose her shit when I tell her this.

"Perhaps I should go," said Orlando apologetically, picking up his hat.

"Wait, so... you thought I was a high-class girl, huh? Like not even just a normal girl? You think I'm fancy looking!" I kept the teasing tone in my voice. I sort of didn't want him to leave. I wasn't mad, and chatting with him was still fun. To be honest, the mistake had made me more interested in him. It added a sort of dangerous, grown-up touch to the whole thing. I wanted to talk about it more, or something. I wanted to hear him say I looked like a high-class hooker again.

(And, okay, there was one other thing I was curious about. Wouldn't you be?)

"You are quite beautiful," Orlando said again, hand hovering, still holding his hat, unsure whether to stay or go. "Yes, you look like the kind of girl who would come here to work. Amongst a... more profligate type of client."

I bit my lip and finally blurted out: "Um, can I ask... I'm just curious. I literally have no idea. How much, um... how much do you usually pay the girls here?"

Orlando cocked an eyebrow. He looked amused now. He settled back down; by now he knew I wasn't mad. "For someone like you? I would say eight hundred dollars."

My eyes bugged out of my head. "Eight hundred?! Holy shit!"

It was his turn to laugh. "How much did you think it would be?"

"I don't know, like... a hundred?"

"Oh heavens no. Not for you. You are, what... twenty years old?"

"Nineteen."

"You would be in the very highest tier of consideration, my dear."

It was at this point that... I mean, look, I was still trying to keep it light. It's not like I'd made any decisions or anything yet. But the actual truth is that eight hundred dollars is a ton of money, Audrey. At the end of the day, that's a big deal. It's literally enough money to make me consider something I normally wouldn't.

And the other thing was... I wasn't against this whole idea. I liked Orlando! He was cool! I probably wouldn't have hooked up with him, under normal circumstances, but... not definitely not. It would be weird to hook up with someone that much older, is all. I don't really see myself as that kind of girl. But it wouldn't be anything against him. He was handsome, you know, in an older kind of way. You don't get to judge me, babe; you've told me in graphic detail exactly what you'd do to Pedro Pascal.

So I tried to keep the tone light, like I was just playing around, but I was like, "And what would, um... what would a girl have to do for eight hundred dollars?" I know that sounds like a stupid question, but I wanted to make sure I wasn't misunderstanding him. And also, okay, I wanted him to say more because it was sort of hot.

He grinned, like he knew exactly what I was thinking. "To be honest, in situations like this I usually ask for... ah. I don't want to be crass. With your mouth."

I blushed and clapped my hand over my mouth, only half faking my shocked look. "Like a..." I lowered my voice to a whisper. "Like a blowjob?"

He laughed lightly. "Perhaps I needn't have worried about being crass. Yes. A blowjob."

That definitely made it seem sluttier. Like that's just straight up prostitute stuff, right? It would have been easier to pretend it wasn't sex work if he wanted to have sex. But on the other hand, sex is a bigger deal, pretty much - more intimate and, I don't know, messier - and would I really have agreed to that? I hadn't even had sex with that many guys. I mean, okay, it was three. Luke, Dinesh, Matthias, my three serious boyfriends, that's it. But I'd given six guys blowjobs. Junior year in high school was, like, blowjob year for me. And there was one guy at a frat party when I was just really drunk and I'd just dumped Matthias and I felt like being slutty. Anyway a blowjob didn't seem like that big a deal, in a way. But definitely slutty. But I don't mind blowjobs! I think it's even a little hot, sometimes, with the right guy. And, again, we're talking about eight hundred dollars. To do something I wouldn't have been totally against doing for free just for the hell of it.

It was around this moment that I realized I was actually considering it. Look, I still had like three hours before my parents got back from the museum. They were doing a whole tour thing.

Orlando could tell I was considering it, too. He cocked his head at me, but he didn't say anything. He let me work it out.

Finally - I was too shy to just agree to anything, I couldn't handle it, but I figured maybe I could at least not definitely not agree. "I mean, that's a lot of money," I half mumbled.

Orlando nodded. "It is indeed. A lot of problems can be solved with eight hundred dollars."

I shrugged. It was the best I could do.

He leaned in slightly. "Would you like to come up to my room right now?" He cocked his head towards the elevators. "You can change your mind at any point. No obligation. No expectations."

This was where I almost chickened out. This felt like the moment of no return. Sure, he was giving me a way out, but I felt like if I walked out of the bar with him, it was probably going to happen. And this whole time, obviously, at least half of my brain is telling me this is absolutely not at all what a girl like me does. Of course I'm not going to seriously entertain this. I'm nearing the point where I really need to stop messing around and walk away.

But here it was, getting serious, and I really kind of wanted to do it. I wanted the money - but more than that, I wanted a wild experience in Italy. I wanted to do something exciting. I wanted to be a call girl in a hotel bar for an Italian businessman old enough to be my father. This whole thing was exciting, you know? And again, Orlando himself still seemed cool. He wasn't creepy or icky or poorly groomed. He was hot.

I wish I could tell you I came to some kind of epiphany and decided I was going for it, but the truth is that by the time I finished having all those thoughts I was already in the elevator with him.

And by the way, side note, that elevator ride was awkward. It was the most awkward. I thought maybe he'd want to make out or something? But he never did even kiss me, which, I mean, I get it, I've seen Pretty Woman, I guess I just thought that part wasn't for real. I mean, I've also seen The Girlfriend Experience. I think that had kissing in it? I don't know. Anyway he didn't kiss me, he didn't even say anything. I couldn't think of anything to say either. It was a really long ride, too, because he was in this fancy suite at the top of the hotel. Just standing there in silence, both of us wondering if I was really going to suck his dick.

But we finally got to his suite, which was exponentially the nicest hotel room I've ever been in. "Would you like another glass of wine?" he said. I shook my head. I was already tipsy enough.

He took off his blazer. He was wearing what looked like a very expensive suit. I just stood there, feeling underdressed. I was wearing, remember, short shorts and a pink tank top. I looked like I should be at the beach. I felt shy and a little out of my depth, now that I was on his turf. Half my brain was still trying to convince me to run for it. I felt anxious. That was sort of the scariest moment of it, for me: I'd mostly committed, but not totally. I still had doubts.

Orlando came around behind me, and his hands went on my waist, and he lifted my tank top off, and that fixed it. I raised my arms obediently, letting him pull it over my head, exposing my bra. Just a simple pink one, a little lacy. You know my boobs aren't all that, so it wasn't like a big dramatic reveal, but then he slid my shorts down too - matching panties, just briefs, nothing fancy - and once I was in my underwear, it was all definitely happening and I felt like there was no turning back, and that actually felt better.

Orlando stepped a few feet away from me and stared at me. I felt objectified, and it was hot. I'd never been studied so carefully. Usually with guys it's sort of dark or rushed and you're both in bed or something. But Orlando was just taking me in, and it felt good. I like my body! I work out and everything. It's nice to be appreciated. "Do you want me to take off my underwear, or...?" I wanted to do it right, I guess. If he was going to pay me, I wanted to do it just exactly the way he wanted.

He shook his head. "I like you like this. I know I've said this twice already, but you are very beautiful."

I blushed. "Thank you."

He came over to me. He was a few inches taller, so I had to look up at him. "You are certain?" he asked. He stroked my hair gently. It was the first time he'd really touched me, other than taking my clothes off. I mean it was the first thing that felt really affectionate, or intimate. It was startling; I got a little butterfly-stomach thing, reminding me that whether or not he was paying me, I was still hooking up with a man, a real person. It was all real. We'd both been playing it so light, like it was a game, like we were teasing. How funny, this case of mistaken identity. What if we role played it a little. What if... but I was about to get on my knees for this man. We were about to do something really intimate. Well, for me. Mostly intimate for me.

But I was certain. My heart was racing; I was excited. I nodded. "Yeah. I want to. This is... it's kind of fun."

"I agree. It's fun for me too."

I giggled. It was too much tension; I needed to deflate it a little. "Am I doing it right, or am I supposed to act more... like, hookery?"

He snorted back. "What would hookery behavior be, young lady?"

I sort of liked the young lady thing. "I don't know, I could... like, moan more?"

"You have very strange ideas about call girls. No, I don't need you to moan more." He smiled down at me. "But you may get on your knees, if you like."

So I did.

He unbuckled his belt as I went, and then I helped him open his pants, and then his cock was out. He didn't smell bad or anything, and the cock itself was, I don't know, it was nice. Oh shut up. It was maybe a little bigger than average? Or maybe I'd just never had a dick right in my face like that. I'd never even given a blowjob on my knees before! It was always in bed. So even this whole thing of being on my knees felt porny and - well, it felt escort-y. It was weird having it right there pointing at me, like I felt really self-conscious, so I just put it in my mouth.

So that was... I'd really taken the plunge at that point. So to speak. Once his dick was in my mouth, like, I was definitely doing it. Sex work. I'd basically already done it. Even if I called it off right now, first of all it would be sort of mean to go this far and then cancel, but secondly it was too late. He was already my seventh blowjob.

Not that I had any intention of calling it off. I didn't regret it at all. I liked it. It was hot, sucking a man's cock for money. It just felt totally different than being with a guy you're in a relationship with, or even that one random frat guy blowjob. To have it so consciously transactional. It was so clear. He thought I was attractive; he wanted a blowjob; he paid me enough to get me to do it. With a regular guy, you know, look, you're probably going to break up eventually. Who knows how it'll end? What if he tells stories about you, tells his friends you're bad at it? Or you do it too easily? It's your real life. But with this older man, in Italy, in his hotel room... it seemed so simple. I was a sexy girl giving a blowjob.

What I'm saying is that I gave that guy the best blowjob I'd ever given. I worked so hard for that eight hundred dollars. I did the spitting thing, I looked up and made eye contact... I even tried to deepthroat him. It didn't go super great. Like I got it down at first, and I was all proud of myself, but after a few seconds it suddenly felt awful and I had to pull off and have a little coughing fit.

"Sorry," I gasped. "I've never tried that before. It's harder than it looks!"

He laughed softly. "You're doing a great job."

I made a weird little shimmy, down on my knees - I was trying to curtsy but obviously that doesn't really work. "Why, thank you."

I wasn't using my hands at all. Everyone knows using your hand is cheating. You do it so it'll be over faster, because just using your mouth it's really hard to get enough action to make him come. So I felt like, for eight hundred dollars, I should give him his money's worth and only use my mouth, even if it took longer. But also I was really getting off on the whole thing. Just feeling slutty and hot. He tilted my chin up and made eye contact with me while I bobbed up and down on his dick, which was embarrassing but also still hot. I had my hands on his hips, sort of using them to help me go faster. I was really trying to fuck him with my lips. He slid across my tongue, hitting the back of my throat a lot; every once in a while I'd try taking him deep, but I'd let him out right away so I didn't choke again. It still made gross gagging noises, but girls do that all the time in porn so maybe guys like that. Maybe it's about knowing how hard a girl is willing to work just to give them pleasure.

It really did take a while. Partly on purpose; at first I was going pretty slow because I was just getting off on it and I wanted to draw it out. It was just really sexy to be Orlando's blowjob girl. But after a while I did start trying to get him to come. My lips were getting sore, and so was my jaw, and my throat, and my thighs were burning because I had to hold myself at sort of a weird position to be at the right height. I was still into it though! It was even hot that I had to work for it. Like a real prostitute. But I was definitely happy when his breath started coming quicker.

He tilted my chin up again, so he could look into my eyes as I gagged on his dick. "Darling," he said. "I want to make you an offer."

"Mm-hm."

"I will pay you another hundred dollars if you take my cum in your mouth and swallow it."

My eyes widened. I wasn't offended, I was psyched. I was going to swallow for him anyway. It hadn't even occurred to me to do something else. First blowjob I ever gave I swallowed just because Ryan didn't warn me and I didn't know what else to do, and it wasn't really that bad so I just kept doing it. I've always swallowed. So this was basically just a free hundred dollars. "Mm-hm," I said, nodding enthusiastically. Yes sir, you can come in my mouth.

It wasn't like I'd tricked him into a hundred dollars. The truth is, I think he liked offering me money. I had this sneaking little suspicion he thought it was hot that a regular college girl had let him whore her out. I figured he didn't just want me to swallow: he literally wanted to pay me to swallow his cum. Maybe I was projecting, though. I thought it was hot too.

He had his hand on my head by now, sort of helping push me up and down on him. If a normal guy did this to me I'd be so mad, but in this context I was into it. I liked feeling like he was in control. So he was pushing me down a little too deep every time, big long strokes, making eye contact. My eyes were all teary from gagging. I knew my mascara was running. Just like porno girls. I had drool down my chin, too... the whole scene was probably super slutty.

And then he came in my mouth.

I was fully in character as he came. Making eye contact, gulping it down. I was glad he was finally coming, that's true, just because I'd been down on my knees for like half an hour, but I felt triumphant that I'd managed to make him come without using my hands, and I felt really slutty and hot down there on my knees in my bra and panties sucking cock, and it was just all, like... it was probably one of the sexiest experience of my life, and he'd barely even touched me. It was all about him, and I loved it. It was wild.

This whole time he was ejaculating in my mouth, huge jets of cum, and I swallowed every time like a good slut. When he finally finished I did a performative clean-up job, licking up any stray spit or sperm; then I sat back on my heels and giggled, wiping my chin. "You came a lot!" I was just being nice. I mean he did, but also I was being nice. I thought a call girl should probably compliment her client. Make him feel special.

He smiled indulgently at me as he put his cock away. "You did an excellent job, darling."

"Why, thank you!"

He walked over to the kitchenette and retrieved his wine glass. "Care to reconsider my offer? A glass of wine?"

I shook my head, smiling, still on my knees. "No thank you. I should get going pretty soon." I was tempted - I wanted him to tell me I was sexy and good at blowjobs - but I had more pressing needs. "Can I use your bathroom to clean myself up?"

"Of course. Take a shower if you like. Anything."

"I just need to fix my makeup." I looked in the mirror. Sure enough, my makeup was a mess. Mascara and lipstick everywhere. I caught him watching me in the mirror and grinned, flirting again. "I got all messy from choking on your big cock."

He snorted at my porn talk. "High-priced escorts do not really talk like that."

"Maybe I'm a low-class escort."

He laughed again. He really was fun to hang out with. I mean, he laughed at my jokes, which is mostly all I want from a guy. I washed my makeup off and borrowed his toothpaste to swish around in my mouth. I was still in my underwear, and he ogled me casually.

Finally I came out. I was in no hurry to put my clothes back on, honestly. It was fun hanging out in my bra and panties, with him fully clothed; I was drawing out my last moments of being a high-class call girl.

Orlando came over and carefully counted ten hundred-dollar bills into my hand. "It is customary to tip for exceptional service," he said calmly. And there I was, a thousand dollars richer, for... what, half an hour's worth of work? Work that I completely got off on? The moment I got back in the hotel room I was getting in the shower and fingering myself silly. I was so turned on.

(For a moment I even considered asking him if he wanted me to do it right there in his room. It would be sort of hot to have him watching me. But then I thought, what if he was like no, I have to get back to business or whatever, and how embarrassing it would be to be turned down for doing a jilling off show, so I didn't. But I would have. For the record. If he'd asked.)

"Thank you sir," I said, pulling my top on and realizing I had nowhere to put the money. I was going to have to tuck it into my shoe. So I leaned down and suddenly it occurred to me: I was wearing sneakers when he came up to me at that bar. I'd been planning on doing a lot of walking that day. There's no way a call girl would be wearing sneakers.

I straightened up. "Hey Orlando... did you really think I was working, when you came up to me at the bar?"

He smiled. "You have busted me. Of course not. A working girl would have been wearing a pretty dress. You were dressed like you got locked out of your hotel room."

"So... why did you come over?"

He shrugged. "You looked bored. And very pretty. I was curious to see what would happen."

"Is that really how much you pay escorts?"

"Oh yes. That part was accurate."

"Damn."

Orlando cocked his head, looking at me, then pulled out a business card. "Listen," he said. "This was probably a one-time thing for you. Boredom, foreign country, feeling wild. I understand. But should you ever want to do this again... I am in New York every month or two, and I would love to see you again. I like your company very much."

"I don't..." I started, but then my voice trailed off.

"Take the card," he said. "Think about it. If you wish, send me a text. If you don't, don't. Simple."

I took the card. "Okay. But I probably won't."

"Probably not."

I gave him a hug goodbye, but I really did figure it would be the last time I ever saw him. Just a funny story to tell you. Oh, but yes, you are so right, Audrey, there is such a but. Such a but. I absolutely texted him. I barely waited until I got back to the States before I was right up in his phone all text me next time you're in ny sir, would love to see you again. And he totally did. Like, a bunch of times. The last time was last week. I'm still a sex worker. Your best friend is a high-class escort. And it's not just blowjobs, either. I mean, it's a lot of blowjobs. But he likes this one other thing... and he pays me double for it.

Nope, not telling! We have to go dance. Next time. Next time I will tell you what else Orlando likes to do to me. I promise you're going to think less of me when you hear it!