It’s a trip and a half to sleep with someone who’s read every word you’ve ever posted. This happened last week. Super nice guy, he messaged me via Instagram. We had several direct messages, which included a little about our lives, but mostly about pricing and logistics. He admitted to having never done anything like this. He thanked me for being so open and kind, and said he’d think about it. Not much time passed before I received a DM saying he was ready. We decided to meet for a drink first and if all went well, we’d get a hotel for the next time. Our drink date was set for almost two weeks in the future. Our schedules were hectic. It’s tough when I travel so much. It’s especially time consuming when I need to factor in at least a full day after I get home to decompress from my time with the crazy Texan. He was extremely respectful of my space during this the two weeks—minimal messaging and mostly as a response rather than an unsolicited reach out—which I greatly appreciated. Some men (most men) push my boundaries—looking for free attention—once they feel they have an in. This guy was different.
He’s a self-professed fan. He told me that he’d read every word I’d ever posted on my sites as well as the pieces that have been posted on online publications. During our first time fucking, he made a joke about the girth of the condom—hoping it wasn’t too thin—stemming from a late night anecdote in one of my stories from my first book. We laughed, but it made me slightly nervous knowing that this man had read all of my inner most thoughts about life and hooking, and there we were, doing the thing he’s read about. I countered his joke by saying I wouldn’t fake an orgasm, which I almost instantly regretted. This was going to be tricky. A tightrope walk between the real me, the writer me, and the hooker me. Men always say they want the real me, but let’s face it, the real me wants them to hand me cash and then leave so I can take myself to dinner alone. But that’s not as fun for them.
We met for drinks. He seemed nervous. It was sweet. I could tell we had some things in common and over the course of time we discovered even more. Most notable was our hippy upbringing. I mentioned this sugar free taffy like thing called a yinny that I used to eat and he knew what I was talking about! He’s the first person ever to know what that was. I liked him right away. I remember thinking: this might be the easiest john I’ve ever had. He’s not necessarily my type—although, I’m not sure I have one—he’s short with tight curly hair, but his sense of style was something I could relate to. He wasn’t the classic mid-fifties white guy in a salmon-colored Tommy Bahama shirt. In case you were wondering, there is a common denominator between all men and women I’ve dated: tall with beautiful hands.
This guy was easy to be around. I prayed the sex would go well—assuming he wanted to fuck me of course. He paid me for the meet and greet and we made a date to hook up a few days from then. Apparently he did want in my pants. Our neighborhoods aren’t far from each other, so I called a motel halfway in between us and booked the room—I had to make the reservation because he’s married. He said he’d reimburse me in cash. I wasn’t too worried about it. He was a straight shooter, polite and professional. I trusted him.
We discussed our love of dive bars and dive motels, so while I chose a clean motel, I went with simple and easy. I’d rather benefit from a regular gig and extra cash. I have expensive taste, but when it comes to hooking, I’d rather that money go in my pocket, not the hotel’s. I brought snacks, water, booze, a candle, and a Bluetooth speaker. I was a little tense while I waited for him. This was my first client whom I’d met from Instagram. I toggled between swigs of vodka and cucumber water.
He arrived and we hung out for a bit. I knew he wasn’t going to be a Twenty Minute Man type of john, but also not an all-nighter like The Texan. Most dates in this field last an average of two hours or a little under. This includes chatting—both before and after.
We moved it over to the big bed and kissed. He was a decent kisser, not the sparks like with dude from 2012, but not horrible like some of my other tricks. We started to disrobe. I was curious about his penis. He had big hands, but with his stature, it was tough to say. Although, like I’ve mentioned before, none of that seems to matter much anymore. I’ve been thrown off track in this arena over the last few years: one or two men I would have sworn had swingin’ dicks, and a couple with the opposite read. I’ve given up on looking for clues. The only way to know is to see the damn thing.
When he got down to his boxers. I fondled his erection through the thin material and was pleasantly surprised. He was on his knees. I was half on my side. He leaned forward so he could remove his shorts, which put his face near my crotch. He went down on me. Holy crap! His tongue movement and soft lips felt incredible. And his dick was gorgeous. Reminiscent of my ex, the chef, whom we all know has one of my all time favorite dongs. I was having fun.
We sixty-nined like for a bit, it was super hot. I’m not currently fucking anyone besides for work, and I’ve been sexting with my long-distance crushes, and jacking off like a crazy person, my body has been starving for decent sex.
We finally broke out of that position and I grabbed a condom from the nightstand. Since he’s read all of my work, he knows I make fun of men for not putting on their own condoms, so he did the deed. Again, we laughed at this. So far, I was only seeing positives from him knowing all my secret info.
I licked my fingers and rubbed spit on the outside of my puss, and he entered. He felt really good. We kissed and fucked. And then I had a small orgasm...without even touching my clit! That almost never happens. Hearing me come, did it for him and he came too. I felt like I had one of those news banners in my head: this guy’s a fucking dream! I just hoped he could afford to see me on the regular.
Second date with my Instagram client, whom I’ve now christened, The Unicorn. You’ll see why. We met at the same motel. Talked and laughed before the sex. We could talk for hours. In fact, I had to steer us to the sex portion so we wouldn’t be there for a week. Not that he was avoiding having sex, he just likes being in my company. Perhaps a little too much. And see, here’s my conundrum, he’s going to read this, so many bullets and feelings to dodge. Good news is, he’s a grown man. I think he can take it. I mean hell, I’ve coined him the damn Unicorn, his ego should be soring, right?
The usual commenced. I absolutely love his cock. He felt great like before, but I could tell that my body didn’t feeling like coming. As you know, I don’t normally try to climax with clients. But I was enjoying myself nonetheless. This alone was a near first. He came. We washed up, hung out for a bit, and then he left. When I rent rooms in Southern California, I don’t always spend the night, but sometimes I do, tonight was one of those nights.
He text me when he got home. We said some of the usual, “It was great seeing you” stuff, and then it took a sexual turn. I admitted that I wished we didn’t have to use a condom. He agreed. No matter how you slice it, or which condoms you use, sex is simply better without them. That’s the sad truth. There’s just something about skin on skin. The detailed discussion got us both worked up. Again, this has never happened with a client. I don’t sext with them. They don’t usually turn me on. I can only attribute it to him being different, but honestly, I think he also lucked out and got me at a time when I’m getting zero action...my body is missing it.
Anyway, I thought his wife was home, but it turns out she was out of town. We talked about him coming back to the hotel. He asked about money and I told him to skip it. He said he was jumping back in the car. All of this was a first. Not only for a john, but I don’t think I’ve ever even done that with a booty call. Well, maybe one other time, but what you know about my sex life, that makes it practically a first.
I took some swigs of vodka and did a tiny bit of meth. I was beat from my long day. I needed just a tiny kick. Despite the fact that he was turning out to be a unique client, he was still paying me, and I was still performing to some degree.
We laughed and hugged when he arrived. I was already wearing next to nothing. He took his clothes off and we got on the bed (again). He slid my panties off and went down on me. I don’t know what the hell he was doing with his tongue and fingers, but it felt like heaven. Before I knew it, I was coming really fucking hard. Haven’t come like that since Bull Durham. Come to think of it, have I even had sex with a non-paying since Bull Durham? I don’t think so.
He came up and kissed me, I needed him inside me immediately, if not sooner. He was rock hard. He pushed in slowly. We wanted to savor the sensation. It was pretty fucking magical. It didn’t take long before he came. He pulled out and came all over my stomach. I could tell that like mine, his was epic. I’m the first woman he’s been with besides his wife, and then add the non-condom factor. We laid there for a bit and talked about how amazing it felt. He marveled at how strong my pussy muscles were and what they did when I came. It was nearly 3 a.m. by the time he left. He is, by far, the best client I’ve ever had! I’m so happy he came into my life.