So I fucked an escort tonight. And that wasn’t even the best part. Ok fine, it was pretty fucking dynamite, actually, but still. Read on.
I went downtown for dinner earlier cause I was in the mood for a steak and I had a little chunk of money in my pocket. I went to a restaurant where I used to bartend a few years ago. Pretty swanky place and I knew I'd be comfortable sitting at the bar by myself and eating a $30 steak. After chatting for a while with the 3 people next to me who I thought were all together, the couple got up and left, leaving behind a single woman. She also knew my friends who were there working and we quickly starting chatting. She was pretty feisty. We stepped outside for a cigarette and she was really digging me. After we went inside, I got up to leave and said I was supposed to go meet some friends, to which she replied, 'I hope I'll see you later on'. Not bad. She texted me her number, I said my goodbyes to everyone at the restaurant and left. $50.
I really did have a commitment to go meet someone. It was a girl I'd met on an online dating site, Tracy. She was also going to be downtown tonight for her friend’s birthday and she invited me to join, as it would be a good opportunity for us to finally meet. I strolled down to the bar she was hanging at and chatted with her for a little while before we headed to the bar where the party for her friend actually was. It was my chance to split. I felt bad though. An exit that early could only mean one thing in her mind and I didn't want to leave her feeling like that. So I downed my drink and joined her and the two guys she was hanging with at the first bar to go across the street to the other place. I spent the whole walk trying to think of a way to ditch before we actually went inside. I failed and ended up going in. The bar area itself was pretty crowded and I managed to wiggle my way up to the bar pretty quickly and caught the eye of the female bartender who was happy to promptly take my order. (I'm finally starting to get used to being as attractive as I've become over the past few years. Others tell me that I've been this way all along, but I guess I haven't met my own standards until recently.) Naturally, as I was the only one who managed to get to the bar itself, I ordered and paid for the drinks of the two people who were still with me. $20.
Tracy and I sat down to talk after getting our drinks on what turned out to be a really low sitting sofa. Neither of us realized it at the time and as we went to sit we both kind of fell into our seats and I almost spilled my drink all over her. She had a bottled beer so I was safe from that. It wasn't very long before I started yawning. Mind you, today was my 8th day without a cigarette (ok, fine, ‘would’ve’ been my 8th day) and I also gave up taking Adderall during this period. I really was tired and felt pretty bad about the yawning. I apologized quite a bit for it and tried to keep the chatter going. The additional challenge was that she wasn’t as attractive as I really prefer. Or require, actually. As a result I was sitting there watching, or trying not to watch, the parade of hot women there, wearing their sexy spring clothes. Living near a beach and a university has its benefits. But at the moment it wasn’t serving me well.
After another minute or two I told Tracy that I was really tired, had been up since 5am and filled her in on the non-smoking week. I let her know that I felt horrible for sitting there yawning and that I was going to hit the road and get some sleep and that she should continue on in to see the birthday girl or whoever it was they were there celebrating. She seemed to understand so I wasn’t feeling like a total piece of shit. A little while after I left the bar and got in the car I sent her a text to thank her again for understanding and said I’d be sure to rest up for next time. I seriously doubt there will be a next time, but why drop the hammer in the middle of her night. Who knows, she probably thought I was a total douche. Actually no, she seemed to like me, but it’s not like I was leaving her beaming after an all day date.
What I haven’t mentioned is that during all of this - dinner, the feisty chick at the bar, and the subsequent visit to meet up with Tracy - I was texting with with Amy. Before I’d left the house tonight, quite possibly before I’d even decided to go out, I’d texted her to say ‘why is it that whenever I get a nice chunk of cash in my pocket, I’m tempted to just go out and give it to strippers?’ The conversation then went like this:
Amy: I’ll be your stripper
Me: You just want the money
Amy: So do they
after some time, when I was eating dinner, I received
Amy: Do you want to go?
Me: Maybe in a bit? I’m having dinner and then need to go pop in on some friends
She called me, I discovered later, when I was outside having a smoke with the feisty chick. Then I called her back as I was walking over to meet Amy. She was out somewhere and we couldn’t really hear each other but said we’d touch base in a little while to see if we were up for the strip club.
As I walked to my car after leaving Tracy, I texted Amy with ‘titties?’, to which she replied with a picture of hers. Then she realized and asked if that was my way of seeing if she was ready. It took another 30 minutes or more to hear from her and she said it’d be a little while still before she could get out of where she was. I assumed she was fucking someone or was in some way setting something up. Perhaps someone for the both of us to fuck at a later date. At this point, I was sitting on my patio having a smoke and was fading quickly. ‘You know what?’, I said. ‘Let’s save it for another night. I’m fading and you stay out and have some fun.’
It was almost 1:00 by then and by the time we got there we’d only have time for one drink and wouldn’t even get to see all of the girls cycle through on stage at least once. And really, it just doesn’t leave us enough time to pick out the stripper we want to try to talk into leaving with us, or at least meeting us another time for some fun or possibly a photo session. (more on that below…
So, fading, yet having spent my evening with sexy women near me and on my mind, I thought of cruising over to the strip club on my own. Eh, not really my thing. Unless I have coke in my pocket, in which case you want to go alone cause you’ll probably leave with one. Then I thought of a friend I’d made back when I was bar tending at a different joint than than the nice restaurant. It was a fantastic dive bar in the basement of an old Masonic Temple. Anyway, he, Ted, owned one of the local escort service companies. He’d come into the bar a number of times and would pass out lighters with his company’s info on them. One night I checked out his website and was surprised at the (lack of) quality of the photos of the ‘models’ that he had. The next time I saw him I proposed that he hire me to photograph the next round of new hires and told him it should bring in some more business. I know I’d certainly be more tempted to hire one of his girls if they’d looked better in their photos. Some time after, I got the call. (That whole episode could take a while to write about so I’ll save it for another time, but don’t get too excited, it wasn’t the awesome time it could’ve been, and was about to be, before it got interrupted.)
So with hot women and naked tits and that lovely smell of strippers and their otherworldly skin they have on my brain, I lit another smoke and scooted on over to his website. Then I brought up the site of a different company. Then another. Then I found a site with individual ads for escorts - some were agency girls, some were independent. I was tired, and I’d already jerked off earlier in the day and was really just checking things out killing time. Then I see an ad for a girl who was just ridiculously fucking hot. Then another. Then another. Before I knew it, I was checking out every girl in every ad that was placed during the month of March. And these girls post a new ad virtually every day. But in my mind was‘no dude. don’t spend the money. you’ve already blown enough for a night and there are those other things you wanted to do with some of that cash’. (a faster Mac for better photo and video editing capabilities, for example
But you know, a phone call or two to some of these really hot girls whose rates aren’t listed wouldn’t hurt, right? There was one girl with a rocking body in a little black dress, but you couldn’t see her face. I tried calling her but couldn’t get through. I think her voicemail box was full. Via text, I’d made some progress with another two women, but I lost interest. I called one crazy hot bitch who had a pretty shitty attitude on the phone. I can’t deal with that shit. Granted, she has no idea what I look like or would be like and it was nearly 2am so I couldn’t really blame her, but I certainly wasn’t going to hire her.
Then I hit up the site of the Ted’s main competition in town. 4 out of the 7 girls, oops, I mean ‘models’, were really beautiful. One of them was one of the girls I’d photographed for Ted. She was not one of the 4. I called and none of them were available but the lady taking the calls recommended another girl who isn’t listed on the sitembased on what I told her I like. She told me about ‘Alyssa’ - 5’6”, 110 lbs, long blond hair - and, as I guess anyone would’ve predicted, I went ahead and placed my order. She’ll be there in 45 minutes. $175 for the hour of ‘companionship’. Tips appreciated.
Well shit. Guess who now has to straighten up the place and make the bed; and, not knowing what exactly said tips are all about, grab a little extra cash. Oh, and quick popped one of my magic sex pills that I love, and crushed up an Adderall and blasted a bit of that off the kitchen counter.
45 minutes turned into 60. I didn’t give a shit. I thought about how many assholes must sit there in that situation and get frustrated and irritated and even call the agency to give them a little WTFuck. Me, I just sat here on the patio with my laptop and started pulling up some samples of some of the nude/boudoir/erotic photos I’ve taken in the past - both of the other local escorts, as well as some other models, real models, I’ve worked with. I’m a man with a plan, don’t you know!
After shooting the girls for Ted, I’d got to thinking about all of the strippers and escorts in this town. In any town really. What woman who relies on her sexuality and her body for her income wouldn’t want to have really well done nude/erotic/boudoir images of herself? How many of them could use it for marketing material? How many of them are gonna end up all fucking beat looking by the time they’re 35 and would love to have some great shots of themselves in their prime? How much money do these chicks make in a night and wouldn’t they just jump at the chance to get this work done? And finally, how do I get these women to hire me? To feel comfortable with a guy they met at their strip club, or his house? How do I show them I’m not just a GWC (guy-with-camera for those of you who aren’t familiar with the mildly derogatory term) and that I know what the fuck I’m doing and that I’ll make them look amazingly beautiful and that while I’m working, I’m working and not just ogling them with a hard-on in my pants? And sure, how do I recognize eventually the ones that will dig the hard-on in my pants? While this is primarily a money making venture and opportunity, I’m certainly not going to pass up on any potential trade situations either. (don’t judge me perverts! you know i watched that video of you putting that giant thing in your ass/getting peed on/licking his asshole, right?
So at about the 60 minute mark, I was sitting outside having a smoke with my laptop and her car pulled up right in front of me. I was somewhat expecting her to get of the car with, uh, an escort of her own who’d check to make sure I wasn’t going to slice her up or that there really weren’t 6 dudes inside waiting to circle jerk around her. As she started walking towards me I waved and she waved back, and I couldn’t help but think that her body looked just like the chick in the black dress. Remember? The one with the rocking body? But I’d never seen her face. We said hello and stepped inside so she could call the office and let them know everything was on the up and up. Then we sat outside for a smoke and shot the shit. I told her how it was funny that I’d seen two of my images on their website. ‘Probably the really nice ones, right?’. Fuckin A right! ‘I have a few pictures on
whateveritscalled.com from my ad on Wednesday - pop it open’. So I did. And what do you know? Rockin body babe!
‘Wow, I’d love to have some really good ones taken of me. What do you charge?….I know a few girls who’d probably love to do it too….Why don’t I even talk to my boss cause I know he’s getting ready to totally revamp the website’. Bingo.
‘Oh here, take a look…’ and I pulled open the laptop and showed her some of the photos that I had wisely selected prior to her arrival. She was psyched. Blown away, even. She loved my work. Can’t wait to do it. Probably this week she said. ‘Here, let me text you my number and I’ll call you in a day or two.’ In under 5 minutes I’d proven myself as charming, talented and trustworthy.
As we sat I asked her to tell me about what to expect for our encounter. I said I’d done it once before (a girl from Ted’s place) and at the time didn’t realize that the $175 for the hour was really just for a dance/massage or some other vague bullshit. She asked what I got for that and I told her…I was bar tending one night at the place I had dinner tonight, was closing up late, had gotten some blow with some of the staff and had it on me. The escort came to the restaurant and we had some drinks and smokes and did some coke off of the bar. She told me she didn’t fuck or give head though (fucking seriously?) and for some extra amount of money that I don’t remember anymore she had me jerk off on her tits while sitting at one of the tables in the restaurant. Alyssa then said, ‘well I certainly do more than that! and I work for tips’. Somewhat vague, but whatever. We went inside and I have her $180 and said I’m sure I’ll be giving you more so just keep it.
Now had she asked me right then what I wanted or was into, I probably would have blanked and not really had any sort of good answer. At the same time, I was a little disappointed right then that she kicked off her heels and started taking her dress off. I had a moment where I wanted to tell her to keep it on and we’d figure out a way for a more sensual undressing. But then I saw her body and her lovely bra and panties and decided to keep my mouth shut. What more could I want? She lied back on the bed and pulled me towards her. We lay there face to face on our sides making small talk for a minute or two.
I’m always curious about the real lives of strippers and escorts, so I ask a few questions. She told me that if the client isn’t attractive or has a shitty personality, she’ll just dance for him and hit the road.
We started kissing and after a quick minute she stopped to tell me that she wished they were all like me. Lip service from a hooker? Quite possibly. At the same time, I know the effect I can have on a woman. I know that I know what I’m doing. Way more than most men. I’ve heard this from a number of women who weren’t taking money from me. At least not directly.
Now…I’m a giver. I had a very long relationship, over 20 years, with someone who was most definitely not a giver. So by default, probably 15 years ago, I just became the giver. Luckily, I love it. So while we lay there kissing my hands were running lightly all over her body. I don’t rush. I’m not aggressive until it’s right to be. We took our time. Her nipple in my mouth. My hand over her panties for a while before finally pulling them aside to reveal her very wet pussy. Her hand in my shorts, wrapped around my big cock. She’s definitely a clit girl more than a jam-your-fingers-in-my-pussy girl. I pushed her over onto her back and spread her legs and put her hands above her head and held them there under a pillow. I pinched her clit and felt her tense up. Ahh. Challenge accepted. I was going to make this escort cum and she was going to let me. For a moment I thought of her faking it. But why? I could tell the second she realized that I was going to make her. It was still minutes away, but she just changed. She was already comfortable with me. I was making her feel good. It wasn’t lip service. Well…
I pulled her on top of me, straddling me and my hard cock and reached around with the same hand I was using and had just gotten wet with my saliva. I rolled her clit around in between my two fingers, stopping every now and again to flick it back and forth with some force. She was getting close. With each minor gradual increase in her noise and body rocking on top of me I’d switch it up. Pinch. Flick. Again. Switch. Until I knew she was seconds away. Then I flattened my hand and rubbed four fingers back and forth over her whole pussy, making sure each finger noticeably hit her clit until her whole body tightened and bucked and shook and all noise stopped coming from her mouth as her breathing was halted entirely and her hands clenched around my shoulders and then she slowly collapsed on top of me.
She rolled off to the side and looked at me a little bewildered. It was frightening for a moment. I can’t imagine the men she has to deal with in her line of work. The number of men she just has to ‘get through it’ with. And here I am. Attractive. Funny. A good lover. Don’t stalk me psycho! runs through my head for a split second. Then I got a hold of my stupid ego and let her take my shorts off, get a condom out and put it on me after stroking my cock and balls with both of her hands. She climbed back on top of me and put me inside her. Fucking condoms. But, really, it was ok. I could feel it. And it felt good. And she looked fucking hot on top of me with her hair falling over her face and her amazing tits. She asked me how I like it and I shrugged my shoulders. ‘Whatever you want, honey’, I said, as she continued to move up and down on me. I grabbed her ass and just held them on her, not influencing her movements, but syncing mine with hers. As she leaned forward to kiss me we started rocking her harder and harder. She got louder and louder. She said ‘oh fuck’ a lot.
Then I held her ass up, keeping her still while I slammed into her from beneath. Listening to her breath and moans get more intense before I flipped her over onto her back. ‘Oh my god, you’re so deep’, she said to me as she pulled her legs back. I held myself up so I could look down on her and watch my cock pounding in and out of her. I slowed down for a moment before finally unleashing the last of my violent thrusts into her and pulling out, slipping the condom off, and cumming a huge load from her pussy up to her neck. We both said ‘oh my god’ at the same time, looked each other in the eyes and chuckled before I collapsed on the bed next to her. ‘Wow’ was the first review I got. I got the same one a few more times before she left.
We cleaned up and had a cigarette on the patio before she had to go. Duty called. But before she left, she said again how much she was looking forward to the photo shoot. As she grabbed her things she picked up and smelled a cool looking candle that was on the table near the front door and mentioned how much she like the scent. ‘Take it’, I told her. ‘I haven’t lit it in weeks. Enjoy it.’
Then I said, ‘I know you call them tips, but is there like a fixed tip price for what we just did?’. She said just whatever I felt like giving. Not an easy spot to be in! I’d already dropped a bunch of cash tonight and didn’t want to insult her or overpay. I asked her if 100 bucks was good and her reaction was completely positive. I could deal with that. Hopefully it was a $275 investment in what could potentially be seven $150 photo shoots. And with some good PR, there’s no reason why this service couldn’t be brought to the other escorts in town. Wait til (<- I’m tired of getting autocorrected on the spelling of til. FYI, til is correct, till isn’t. It’s the thing in the cash register.)the strippers see the photos. With a friend in my corner who’ll talk me up and provide the confidence in me that these other women need, I’m feeling pretty solid about getting some real business out of this. Then, with a bigger portfolio, I’m hoping to get into the real moneymaker - the boudoir sessions with the rich tennis wives and soccer moms.
In the hours that followed we had a text exchange about the photo shoot, if there was somewhere I could post a positive review for her, that she really likes the way the candle smells in her home and that she’ll be in touch soon. It was a long night. I made my way around town and got to see some old friends. I had a short date that won’t go any further. A delicious meal. Made an escort cum (feather in my cap). And the opportunity to sit and write this first blog entry. I’ve set the bar pretty high I’d say. I guess I’ll see what you guys think. For now, it’s back to Day 1 without smoking.
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