Going Pro for the Final Time

This is a follow up to

Going Pro

and

Going Pro Again

. It should stand alone but I recommend reading the first two to set the scene. ~BT73.

It's hard to believe that I'm already half-way through my associate degree in financial planning. My earlier financial problems showed me the importance of good financial planning, particularly the value of putting money into a reserve fund in case of problems. It was a major car expense that first taught me this lesson and then when the store where I worked shut down for a couple of weeks, that cemented it.

If I had money put aside, I probably wouldn't have become a part-time escort. But I didn't have an emergency fund and all the alternatives, like asking my parents for money, were worse than having sex with strangers. As it was, I was lucky. I wasn't beaten up by a client and I wasn't arrested. I didn't get any STD and, as far as I know, none of my family, friends, or co-workers found out about my other job.

Some of the experiences, to my great surprise, were no worse than some one night stands I've had. I was amazed to find that there were people who were willing to pay to go down on me. I'll never say no to cunnilingus and being paid for it was sort of crazy. Even when it was a woman who licked me to a climax, I enjoyed myself and I didn't have to lick her back.

The ones in the middle were the GFEs--the girlfriend experiences. Some of these were sad. These guys paid to kiss me and play with my boobs and to fuck me like we were on a date, or like they imagined what a date would be like. A couple of them were upfront about not having time to find a girlfriend but some of them totally lacked social skills and I got the impression they were connecting with me more than they ever had connected with a girl before.

Some of the experiences though were about as disgusting as you can imagine. Going down on a guy I just met, who normally I wouldn't even let buy me a drink, wasn't even the worst. When a guy wanted the GFE, I at least felt like he wanted me as a person even if that person was really someone in his fantasy. But some of the straight fucks made me feel like the guy wasn't even renting my whole body. He was only renting my vagina so he had a place to stick his cock and basically masturbate. Those were the clients who left me feeling the most degraded.

Since the time that my bosses decided to shut down their store and take a vacation, I've been fairly stable financially. I started school that fall and they lived up to their promise to give me the flexibility to work around my classes. About half of the people working there are students so everyone was kind of used to this but I still appreciated it. They even let me cut back during finals week and make up the hours the next week so I didn't lose any money.

This means that I haven't had to repost my ad in our local alternative weekly and I've kept my burner phone turned off. A couple of times, when it looked like I'd have more monthly expenses than monthly pay, I was tempted but the skills I'm learning in school helped me make it through until I got my next pay check.

But now I needed to make a decision. My bosses apparently had such a good time on their vacation that they're going back again this year. I can now survive on half-pay for a couple of weeks but it's going to wipe out a good chunk of my emergency fund. Plus, one of my teachers is trying to convince me to transfer to a four-year school when I finish my two-year program. She showed me the salary I can make with a bachelor's degree and I have to admit that I'm tempted, as long as I can find a way to pay for it.

Well, yeah. I do have a way to pay for it. I can always use the money-maker between my legs if I decide that I want it bad enough. Do I?

I don't think I qualify for any scholarships but there are always student loans. If I do go on in school, I'd rather graduate without a ton of debt if I can pull that off. I'll also have a heavier class load and probably harder classes so I may not be able to work as many hours as I've been doing, even with a flexible boss.

I now know how to make a budget so I opened up my laptop, clicked on the spreadsheet, and started entering my data. I began with my current expenses and then estimated what they'd be if I continue in school. Then I looked at my income--what it is now and what it would be if I worked fewer hours. Then, bottom line, I looked at the gap between my expenses and my income.

Ouch. The gap was a lot bigger than I thought it would be. Maybe a college degree is a dream that's just not going to happen--as much of a fantasy as some of my GFE clients finding a real girlfriend. I closed my computer and picked up one of my textbooks to work on this week's assignment.

I'm distracted though so I went back to the spreadsheet and played what-ifs with a couple of new scenarios. I looked at getting a new job and I thought about getting a roommate. These would help but they wouldn't do as much as the scenario I tried to force out of my head but which kept coming back.

What if I reposted my ad so I could increase my income now? I could put what I earned away so that I could get by with lower income until I finished school. I could also earn more money during summer and winter breaks so I'd be able to get by during classes.

I didn't enter it into my spreadsheet, but I did some mental calculations about what I had earned as an escort. It wasn't enough to close the monthly gap I'd have in school but it was close. I hadn't wanted to do it more than a night or two a week but if I increased that slightly?

Another spreadsheet but with codes for the different services in case anyone ever ran across it. Unlikely but I didn't want to explain a spreadsheet with calculations for blowjobs and straight sex.

Under my business plan (see, I'm paying attention in classes) I want to fuck or suck as few clients as possible but still make my target income. Besides volume, I thought about price-points. Like any business, there are some tradeoffs. You can charge more but you might have fewer customers. You can perform easier services but you'd have to do more of them to make the same amount of money.

I'd been giving blowjobs for $150 and straight sex for $300. About a third of guys tipped me, an average of $50. A couple of times, someone asked for an extra so I added that to my price.

Okay, special services. When I first started, I saw these included in some ads without a lot of specifics. I did get $1,500 plus a $500 tip for helping a woman fulfill her girl-on-girl fantasy while her husband watched. I'd do that one again if they called but I suspect that once she crossed it off her bucket list that was it.

I had a guy ask me for anal and I told him no way. Maybe I should have found out how much he was willing to pay.

From a business planning perspective, I knew that these services would pay more but they would probably be more rare so I couldn't depend on them. Plus, there was safety. There is no amount of money that would convince me to let a strange guy tie me up. Boyfriends who I trust? Been there and done that. Strangers? Not a chance in hell.

So, I talked myself into it. It actually scared me how easily I made the decision compared how much I struggled when I posted my first ad. I added some minutes to my phone, rewrote my ad, and added some new nude pictures that didn't show my face. When the store shut down for the owners' vacation, I posted the ad and turned on the phone.

* * * * *

I picked a good weekend to start. There was some kind of convention going on in town and a bunch of horny convention-goers who were evidently taking advantage of being out of town, away from their wives. I had three texts within a half-hour asking if I was available that night. After some texting back and forth about what they wanted and when, I was able to schedule all three of them.

Since I'd be walking through a hotel lobby, I didn't want to be obvious so I checked myself in the mirror to make sure that I was dressed appropriately. My sundress wasn't exactly conservative but it didn't shout out sex worker either. I skipped my bra but the dress had enough material that my nipples weren't obvious. I carried my tote bag with supplies through the lobby to the elevator, rode up to the third floor, and easily found the room he had given me.

I knocked and a middle aged guy opened the door. I looked around the room thinking I might have been there before. He was alone and there weren't any other red flags so I came in and closed the door behind me. Even though his texts had said he just wanted a blowjob, I smiled and gave him my "how can I make you happy tonight?" line. He confirmed what he had told me before and handed me some bills. I counted them and stuck them in my bag then pulled my dress over my head and stood there wearing nothing but my thong.

He got completely naked and sat on the side of the bed. I had assumed he'd slide over so I could lie between his legs but he didn't move. He didn't say anything but I figured out that he must want to do it there so I grabbed a pillow from the bed and put it on the floor to kneel on. No reason to not be comfortable while I work, right?

He separated his legs and I saw that he was starting to get an erection. No smell, discharge, or other red flags there so I tore the wrapping off of the condom I was holding and unrolled it onto him, giving some hand action to make him erect which it immediately did.

I don't want to spend more time than needed but I've learned that at least giving the impression of taking my time increased the chance of a tip. So, I started by slowly licking from the base of his cock to the tip. I went back to the base and licked up again, playing gently with his balls as I did. I gave him a couple of more licks that way and when I heard him whimper, I opened my mouth, put it over his cock, and began to move it up and down.

As I did this, he leaned toward me and reached his hands down to my chest. I'm wary when guys do this since some of them aren't exactly gentle. He's okay though. Mostly just touching and petting and a little squeezing but it's not bad so I don't push him away. If boob play helps him get off faster, I'm okay with that.

He played with my boobs while I licked his cock. Every once in a while, I gave my mouth a break from my up and down motion and licked the underside of his cock or the tip. We went on that way until I felt some twitching in his cock. I sped up my mouth motion and added my hand to his shaft until he came loudly into the condom. I let go and stood up. He stood up too and naked, still wearing the condom, he watched me as I pulled my dress on. He opened his wallet and handed me another bill so I kissed him and thanked him. Then I left.

In the hallway, I checked and saw that I got a $20 tip. Oh well. Better than nothing.

I had forty-five minutes until my next appointment. I thought about just hanging around the lobby but I really didn't want to draw attention to myself. I could go to the bar and get a drink but I heard last month about the police arresting someone for prostitution in a hotel bar. Even if I'm just getting a drink, I don't want to chance it. So, I left the hotel and just went for a walk around the area. The hotel is on the edge of downtown and it was busy tonight. I spotted a couple of women standing on a corner. They weren't being obvious or anything but I wondered if they were working girls. I didn't wait to find out and kept walking until it was time to go back to the hotel.

Client #2 for the night had told me that he wanted a half-and-half. That meant that he wanted me to start by going down on him and then at some point we'd move into a straight fuck. It meant that I had to get completely naked and I decided that I'd change condoms too in case the first one got torn or anything. I didn't know if it would take more time or not but decided to tell him it would cost $400 and he had agreed. The fast acceptance of my charges makes me wonder if my rates are too low.

I got to his room and he described what he wanted again. He told me that he'll signal me when he's ready to change positions and then he offered me another $50 if I'll do the second half of the half-and-half with me on top. I think go ahead, make my day but I just nod and tell him that's fine. He pulled his wallet from his pants and counted out $450 on the bed. I put the money in my bag and we both got undressed.

Unlike the first guy, he lay in the middle of the bed with a couple of pillows behind him. I played with his legs, running my fingers up his thighs teasingly, then lay down between them. He was fully erect and I was struck but now beautiful his cock was. It's the perfect size (at least for me), not too big and not too small with a small arch shape. It looked like he'd trimmed his hair since the base of the shaft itself and his balls were smooth and hair free. I put the condom on him and started to lick, actually looking forward to feeling him inside me.

Lying between his legs licking and sucking, I also used my hands to play with him. Besides his balls, I reached up to his nipples and then ran my hand up and down him. At one point, while I had my hands over his chest, he put his hands over mine holding them there. Then, he reached down and pulled on my shoulders, signaling me. I disengaged my mouth and asked if he was ready and he just nodded.

I unrolled the condom from him and tossed it to the side of the bed, then replaced it with a new one. He was still fully erect. I straddled his legs then moved up until my pelvis was over him, then I reached down to hold his cock and guide it to my entrance. Then I lowered myself over him, pulling him into me. As he entered me and I felt my lips separating, I let out a sound that surprised me since it was real--I didn't just doing it for effect.

I like cowgirl since I get more clitoral simulation than with any other position (other than cunnilingus, of course). I didn't expect to cum and that's okay because, as I remind myself, I'm being paid so this is for the client, not for me. But still, there's nothing wrong with me enjoying my work too, is there?

My weight was on my knees and I lifted my hips up and lowered them down. I felt him entering my canal and pulling out as I did this and my breathing got heavier. He held onto my boobs and caressed them as I moved up and down. The tension in my pelvis was growing and, if I was with a boyfriend, I'd probably slow down and edge him so he could last longer. For a minute, I wondered if I could actually climax but then I heard his breathing speeding up and felt some twitching. Remembering my role here, I increased the up and down motion of my hips until he moved his arms behind me and held me tightly to him as he came.

I sat on top of him feeling his cock in me as his breathing returned to normal and as, to my disappointment the heaviness in my mid-section eased. Finally, I moved my body off of him and, grabbing my clothes and my bag, went into the bathroom. I cleaned myself up and got dressed. He was still lying in the bed but gestured for me to come to him which I did. He handed me another $50 and thanked me. I kissed him and thanked him back then left.

It may be my paranoia but had a feeling that one of the hotel front desk clerks was watching me. Maybe or maybe not. I walked out of the lobby to my car and drove away. Fortunately, my third client for the night wasn't at that hotel. Including my tips, I had earned $620 so far. I was still pretty aroused from the last guy so I gave some thought to blowing off the third client (no pun intended) and going home for a session with my vibe. My growing financial planner responsibility popped up and reminded me of why I'm doing this and why I need the money so I drove to the spot where he said to meet him.

It was another car sex session. These clients are probably as worried as I am about being caught so they tend to be quicker than in beds. The bad news is that they generally aren't the world's best tippers. I guess I can't have everything.

This guy wanted a blow job. He sat in the backseat, dropped his pants, then slid over. He was going to be my last one for the night and I was doing laundry tomorrow anyway, so I decided that it wouldn't matter if I got anything on my dress and I don't bother taking it off. I lay across him and gave him a quick one. It's not my best performance but he didn't complain. No tip but I headed home, happy with my income for the night. I was still horny from number two so I went I got home; I took care of that myself.

* * * * *

I did some more what-if calculations on my spreadsheet. My question was what if I limit myself to two clients a night? How many days a week would it take to make up for that? What services? Three seemed like a lot last night. Maybe three or four blowjobs wouldn't be a problem but in my pre-professional days, I'd never had sex with more than one guy in a single day before and I realize that it's a lot both physically and mentally. I needed to think about this if I planned to keep working until I finished school.

Fortunately, I got a text the next evening that let me meet my quota for the night with just one guy. It's that trade-off of more money but I have to do more for it.

The text just asks how much for spanking. My first reaction was to ignore it but I decided that I had nothing to lose by asking for more information. If all else fails, as I've done a couple of times, I can always block a number from a guy who doesn't know how to take no for an answer.

I was glad that I didn't ignore him. Like bondage, there's a lot of trust with being spanked and, even though it was a lot safer than being tied to the bed, I still wasn't sure that I'd do it with a stranger. Maybe, but the price would have to be right. Well, I called it wrong. He didn't want to spank me. He wanted to pay me to spank him. I'd never done that before but I'm willing to try it. We agreed on a half-hour session for $750.

Anytime I go into someone's house, I'm cautious. I keep my hand inside my bag holding onto my pepper spray as I go in, I ask to use the bathroom which is really my way to look around for anyone else in the house.

I didn't see any red flags here so I partially relaxed. He and I sat on the couch and he explained his scenario. He'd lie across my lap here on the couch and I'd spank him through his clothes. After about five minutes, I'd tell him to take his pants off and continue the spanking. Finally, after fifteen or twenty minutes, I'd "make him" take down his shorts and spank him directly on his bare butt. I'd use my hand at first and then for the last five minutes, a hair brush. After this, I'd leave and there would be no sex involved unless you think of a spanking as sex. He handed me the money and I warned him that if he came while he was across my lap, it would cost him another $100. He agreed and put five more twenties on the table, just in case.

He brought out an old kitchen timer and we set it for an hour. He lay across my lap and I started to spank him. He was wearing jeans and I'm pretty sure that he wasn't feeling much but I was starting to feel it in my hand. I was glad when we hit the five-minute mark and I gruffly ordered him to stand up and take his pants off. As long as he was standing, I told him to remove his shirt too then, wearing only his shorts, he returned to my lap.

Now, with just his thin jockey shorts, I assumed that he was feeling the spanking more, plus it was easier on my hands. I got into a regular pattern, alternating between his cheeks and moving my target area around. I made some of the spanks harder than others and a few times, I made a fist and slammed that down on his butt getting a flinching and a whimper from him. I assumed that the cumulative spanks had to be getting to him but other than occasional noises, I wasn't really getting much reaction.