My pricey escort ad (which put me out a hundred and thirty bucks to place) was a dud, but a guy emailed me from the lessor, more down home site, and I met him last night. I got a good feeling from our email exchange. He asked not a single question. A first, I think. He said he liked my unique pictures, and mentioned that he shoots film. I told him that I was too was a photographer. He seemed to like the fact that I was an artist. We made a date in a week’s time. Something I also appreciated. That he wasn’t beating down my door—wanting to meet me in an hour. Which never works for me. I’m a planner. He also didn’t ask for more pictures. Amazing. And almost unprecedented. He lives outside of LA, my ad says I live in Hollywood, so he offered to get a hotel in downtown LA. Huge points. So easy. He made a reservation at the O Hotel, which was perfect. Great bar. Not too flashy. I think I love this guy. The only unfortunate factor was that I had met him through my discounted ad. Ah well, something is better than nothing.
The date: I didn’t have a clue as to what he looked like. No race, size, age, nothin’. I told him what I’d be wearing (he also described his outfit...both on the day before, signaling that he’s a planner too), and I said that he could send me a photo if he wanted so I would know who to look for—but I made it clear that it was no big deal. We’d find each other. The bar isn’t that big, and we were set to meet at 7:30 p.m. on a Saturday. Early by city standards. He didn’t seem keen on a photo, which was fine. I was nervous. It’s been a long, long time since I’ve met a john like this. Years. I’ve met most of my john’s at the club. So there was already a rapport, a warm-up, and they knew exactly what I looked like. Another fact adding to my apprehension: I was a lot skinnier the last time I placed an ad and met someone cold like this. My pictures were current (but I know how to hide/accentuate the good, bad and ugly in photos), I put my weight at ten pounds under the real thing and my age at thirty-five. Luckily, I was having a good face day. You know how one day your face can look super pretty, and the next, like something stuck to the bottom of your shoe?
I had timed my day out well. I wasn’t rushed getting ready. Which is what I always prefer. I listen to music, sip on a cocktail, and apply make-up while I mentally prepare. I was anxious, but I have balls the size of grapefruits, so I knew it would be OK. I found street parking two blocks away. One drawback is that the hotel doesn’t have a valet. I walked to the hotel in my uber short dress, patent leather heels, sparkly eyes and big hair. Well, as big as my baby fine hair can get. I felt like super-hooker! I opened the door to the hotel, and a slight Asian man was sitting just to the left, the way he looked at me, I knew it was him. Even easier than I thought. I gave him instant points for being smart and waiting like that, rather than making me walk up to strange men at the bar. His nervousness was apparent. I said let’s get a drink. I was thinking we would sit at the bar, which is small and dark (the sun hadn’t gone down yet), but he made a gesture for a table. Not only did it put us by the two story windows, but also the table was on the long side, so he was sitting sort of far from me. Not great for a meet and greet. Tough to flirt like that. Also, the music was barely audible and there was another couple sitting just to the right of us. I didn’t want them to hear our how-we-met conversation. But whatever, this was just a preliminary cocktail anyway. Just to make sure he wasn’t the violent or murder type. I just prayed that my wrinkles weren’t making a liar out of me. I’m only nine years older than my lie. I could have gone younger, but I’d rather look good for my age than ragged. He asked how recent my photos were. Uh oh. I told him the truth, which was that most of them were taken within a few months, and one was from last year. Not too bad. I could have used my pictures from twenty-five pounds ago, but would rather a guy know what he’s getting than deal with disappointment. Then he asked if I had done something to my hair. I was dumbfounded. My hair has basically been the same for twenty years. He said that it looked thicker in my pictures. I laughed. “Oh right, I was wearing a hair piece in that one shot. I was going for a retro look and needed bigger hair. Wow, you notice small stuff, huh?”
“I notice everything.”
Shit. Gonna be hard to get over on this one. While we chit chatted, he kept commenting on my dimples and how cute they were. It’s been forever since someone has said anything about my dimples—I used to hear it at the club all the time, but it’s been a few years since I’ve heard a peep about them. I was beginning to think they had disappeared. We had two rounds, and then took it upstairs. The room was extremely small, but no matter, all we needed was a clean bed and bathroom. I took my heels off, and put my Crown Royal bag with lube, pink vibrator and condoms on the bedside table. I couldn’t figure the radio out, so silence would have to do. I made the mental note to bring my iPod net time. Learning from one of the biggest hooker mistakes of my career, I then asked him for the money. He seemed uncomfortable. I get it, I hate the money part too, but no way were we going any further without that cash in my purse. He handed me an envelope. I checked inside. Flipped through, it seemed like the amount. I thanked him. He brought a photography book to show me, so I laid on my stomach with my ankles crossed and up in the air, and flipped through it. He mumbled that it reminded him of my work, but I had only showed him a couple images on my phone during drinks, not but ten minutes previous, so I found this a bit odd. I shrugged it. He was next to me, and wanting to get things moving, I put the book down and kissed him. He was trepidatious. Barely kissing back. No biggie. Better than the alternative. I slipped my dress over my head and told him sweetly to undress as well. He did. To his boxer briefs. I got on top of him and kissed him some more as I lightly touched his hard cock through his boxers. Decent size for a waif Asian with skinnier fingers than mine. He seemed extremely sensitive in that region, so I didn’t go crazy or linger too long. I reached for my condoms (I had two, so I separated them in front of him which I regretted later), and told him to take his boxers off. The fact that I had to tell him was a little strange, but whatever. I kissed him again, and then went down on him just a little, just to get it wet under the condom. He said that it tickled. That’s a first. He seemed really freaked out by my presence down there, so opened the condom wrapper and started gently rolling it down. His energy was peculiar. But he was consistent with the dimple comments. He was obsessed with my dimples!
“Am I hurting you?”
“No, it’s my first time.”
“Your first time....ever?” I tried to keep my eyes from bugging out of my head like that cartoon character. He mumbled, “Well, my first time in twelve years.”
“Oh wow, well don’t worry, you’re in good hands.” It was kind of a dumb thing to say, but it caught me so off guard. I was in unchartered territory, and in real time. No chance to think or edit. I wasn’t convinced that the twelve-year thing was true. He may have only added that after I said “ever”. But I’ve never been with a virgin, so I’m not sure I know the difference.
I climbed on top, but he wasn’t sliding in. He was hard enough. I was wet enough. But no one had been inside me in a couple weeks, which practically makes me a virgin/which is virgin territory for me. Also, he was just lying there. Not helping at all. Not even a hip thrust. Nada. I got him to roll over and get on top of me. It worked. He came very fast. He asked me politely if it was OK before he did. He came hard. I could feel his cock throbbing. It actually felt good. He pulled out a minute or so later, and I went to pee and wash off. Not much sound proofing, and due to the size of the room, I’m not sure why there was a bathroom door at all. But I was happy it was over. I walked out, and he asked if we could do it again. Shit. Why did I show him my two condoms?! Shit. This is not a good precedent to set, and I know better, but he was so sweet and easy, so I said yes. He barely touched me during the first act. And hadn’t made a move or a request to do anything with my pussy, he was more interested in my dimples than my tits or box. I probably didn’t even need to shave. We were well beyond my “hour” as it said in the ad—true, most of it was eaten up during the meet and greet, but again, not a good pattern to set. I managed to tell him (he had inquired as to what I was doing after) that I could stay longer if he wanted, but I would need more money. He visibly balked at this, so I let it go. Not smart on my part, but this is where my big hooker heart gets in the way of my business. Letting him go again without paying more goes against all the prostitute rules, but I’d rather have an easy two-hour than try to find a new club.
I was afraid the second time would be the classic second time nonsense (more work), but was banking on his virgin-like status to make it quick. It was. Although, his dick started to go soft when I tried to put the condom on, so I said that he should probably do it. His dick is so damn sensitive. He wanted me on top. I hate being on top with a john. It’s not even something I like doing in my real sex life. I did the best I could. Bouncing my big natural titties for his visual. Finally I leaned down and kissed him, and he thrust his hips towards me. There you go, buddy. I was making some sexy noises. Nothing that the neighbors could hear, but just enough to give the impression that I was enjoying myself. He shushed me. I couldn’t believe it. I was dying. It was difficult not to laugh. You want quiet, buddy? I can do quiet. No prob. He came. Time to go! I put my hair up and showered quick (just the lower half). Then I got dressed as he peed and removed the condom. When he came out, we talked about our loyalty to others. He said I was the only one he emailed off the site. Said he wasn’t going to look any further. I gave him my phone number, but told him that I did not want to be contacted often (meaning, non-work stuff). He assured me he wouldn’t, but added, “Can we check in one in a while? See how the person is doing?”
“Sure.” I can tell he’s going to be a little needy. What am I saying? He’s a man. He’s like all of my customers. Most of whom are lonely (hence the hooker), and need friends. But he didn’t bug me much in the week before our date, so I felt confident it would be fine.
We did the quick it was so good to meet you. I told him how I’d love to see him on the regular. He said he would like that too. As much as his bank account would allow. He mentioned that he made an OK living, but nothing to write home about. I said the ball was in his court. One last hug, and I walked out of the room, promising myself I’d be stronger next time, and not let the two condom thing happen without more dough. Or just one drink before going upstairs, making the whole thing less time. But the drink section is my favorite part! Ah, the trials and tribulations of sex work.