Going Pro Again

This is a follow up to Going Pro. It should stand alone but I recommend reading the first one to set the scene. When I wrote Going Pro, I planned for it to be a one and done story but some of the comments that I got from readers suggested additional adventures so I decided to do this sequel. I'm not currently planning a third part but if there are suggestions, I won't rule it out either. ~BT73

Every time I responded to a text on my burner phone, I did it with some regret. I never would have imagined myself reaching in a point in my life where having sex for money was my best option. It made me look back at earlier decisions from skipping classes in high school to skipping a chance to go to college. I have a job at a small, family owned store that, while it's not exciting, is at least steady. It pays enough that I can live okay as long as nothing goes wrong.

Of course, something had gone badly wrong. My car decided to stop working and it wiped out my small saving account, including the money waiting to pay the next month's rent on my apartment. None of the options for finding a quick loan were going to work and there was no way I was going to ask my parents for money again.

So, I carefully studied the ads in our on-line alternative weekly, bought a burner phone and posted an ad. I dreaded actually meeting a strange guy and having sex with him but I did. Actually, I did it several times over two weekends. A couple of times were not as bad as I figured, and a couple of times were pretty disgusting. One time, it was actually kind of nice in a weird way.

Those two weekends gave me enough to pay my rent and get me out of my crisis mode. I read some stuff about financial planning for people in their 20s and I swore that I would build an emergency fund so I'd never be in that situation again. That meant that I'd probably do some "dates" for a while to collect some cash and then I'd never have to do it again.

My best intentions kind of went out the window. Once I paid my landlord, I decided that two weekends of working should entitle me to a couple of weekends of fun. I went out with friends who, thank God, didn't ask where I had been and what I had been doing. I hooked up with a guy I met at one of the bars and had sex with him for free. Yes, I did think about that but when he went down on me and made me climax, I realized the big difference was that when I wasn't charging the guy, I was entitled to enjoy myself too.

I may have never renewed my ad and added minutes to the burner if nothing else bad happened. At least nothing until my emergency fund had reached the point where it could cover me if something bad did happen. Nope, on both. The fund wasn't anywhere close to what the financial planning sites told me I needed when my bosses, the owners of the store, decided they needed a family vacation. Nice for them but I learned from someone who had worked there for a couple of years that every few years, they'd close the place for two weeks during what they figured would be a slow time anyway. When they took off, the staff got a vacation too. Unfortunately, they put us on half-pay for that time.

Okay, I know that they could have just not paid us at all so in a way we did get a paid vacation. But realistically, I didn't have the money that I could go somewhere for a vacation and losing the rest of my salary for two weeks was going to put me back in the hole.

I still didn't have any reasonable alternatives. Unemployment if you're laid off only kicked in after two weeks. I didn't see any kind of temp job around that would make up the difference. I wasn't thrilled but having done sex for money before, I didn't hesitate as much as I had the first time. I reposted my ad and added some minutes to my burner phone. Maybe having two weeks before the store opened up again would give me a chance to put some money away.

Our bosses closed the store and left for their vacation on Saturday morning so my last shift before the layoff ended on Friday afternoon. I posted my ad Thursday night and when I got home on Friday, I dug out the burner from the drawer where I had buried it and I turned it on. I made a quick dinner and waited both wanting and dreading a text that would lead me back selling my body. It was good timing since I was doing the dishes when the phone beeped.

"Sup?"

"Not much just waiting for you." Yeah, I know. Corny.

"Same. Hoping for a blowjob"

"Hoping to give one"

"How much?"

"$150"

"K." He gave me an address. It didn't ring a bell so I had to look up where it was. It was in a residential area that I had driven through before. Houses that seemed like they'd be nice.

I had decided that I'd wear a sundress that I could take off quickly. Time is money. Oral sex meant I didn't have to get undressed but I figured that taking off the dress would be the same as pulling off a t-shirt. I'd show him my boobs and I wouldn't have to worry about getting any cum on it. I didn't bother with a bra but the dress had a double layer there so I wasn't worried about my nipples showing if I had to go through a hotel lobby or something. I double checked that I had condoms, some body wipes, and some breath mints in my bag and I headed out.

Even though I was less stressed than I had been the first times I had done this, it didn't mean I wasn't nervous at all. I didn't like the idea of going to someone's house and I hoped that the police weren't doing any kind of crackdown that would get me arrested. This guy had directly asked me for a blowjob and I don't think that cops can do that. At least I hoped so.

GPS led me right to his house but I drove back and forth a couple of times looking for any red flags. It was a one-story house and the front yard looked like it was well taken care of if that meant anything. There was a big window showing a front room and the light was on but I didn't see anyone. Finally, I took a big breath, parked my car on the street and walked up to the front door, my hand in my bag holding onto my pepper spray.

The door opened before I had a chance to ring the bell. The guy who opened it was maybe mid-40s. Nothing special about him and no alarm bells. He smiled like I was a friend visiting and I wondered if that was for me or in case his neighbors were watching. I smiled back and glancing around went into the house.

He actually thanked me for coming and asked if I wanted a drink or anything. I suspect that he might have been nervous too or maybe he wanted something closer to a girlfriend than admitting to himself that he was going to pay for it.

I smiled again and told him no thank you. Thinking of a possible tip, I decided I wouldn't rush him yet and I'd play along with him. We went into the living room. He motioned for me to sit down on the sofa and sat down next to me but with some space between us.

I went to what may become my go to line for getting things started. "What can I do to make you happy tonight?"

"I want a blowjob but can I lick you first?"

Damn. Really? I've never hesitated to let a guy lick me first, during, or afterwards. But it means I'm going to have to get completely undressed and since I'm selling my time, should I charge for it?

"That would be great but it will be another $100." I grabbed that number out of thin air since I hadn't pictured a guy wanting to pay me for that.

"Can we do it sixty-nine?"

I smiled like he was offering my favorite position. It actually isn't since I have trouble concentrating on what I'm supposed to be doing when someone is licking my clitoris. But for $250, I'm certainly willing to try. "Of course. We can do it that way if that would make you happy."

He got up and picked up his wallet which was sitting on a table. He took out some cash and counted out $250. I kept track as he did this so I could just stick it in my bag without counting it again. Instead of sitting back on the sofa, he moved toward a hall so I followed him into a bedroom.

He had a full-sized bed with the cover pulled down and the sheets looked like they had just changed recently. When I'm having regular sex (that is, free sex), sometimes we tear each other's close off but some guys make a big deal of us undressing each other slowly. There are guys who just get undressed on their own which is a hint to me that I should too. I figure that any of these could happen having paid sex so I watch for a hint from him of what he is looking for. He sat on the bed and took off his shoes and socks then stood and pulled his shorts off. I took that as him wanting me to undress myself so I reached down to pull the bottom part of my dress up to my hips then slowly pulled it past my chest and over my head, tossing it onto a chair. I kicked off my sandals and I'm now only wearing my thong. He stood across from me wearing only his shorts so I knelt down in front of him and pulled them down. He evidently liked this move since, when his cock appeared, it was already starting to come erect.

I pushed him toward the bed and pulled off my thong. Reaching into my bag, I grabbed a condom and asked him if he wanted to put it on or if he wanted me to. He asked me to do it so I sat down on the bed next to him, jerked his cock up and down a few times to make sure he was fully erect and then opened the package and unrolled it down his shaft.

He moved over to the center of the bed but before he lay back, I took one of his pillows and placed it behind where he'd be laying. He was still being pretty passive and hadn't reached for me at all so I figured I'd be able to drive what was going to happen next. I lay next to him and kissed him then I swiveled around and rolled on top.

I positioned my pelvis so my pussy would be within reach of his tongue. He put his hands over my butt cheeks holding me in and I felt his tongue on my labial lips. I'd love to just let him do that but the main event wasn't him licking me--it was going to be me licking him.

As I said, sixty-nine is distracting. I tried my best to ignore the feeling coming from downstairs as I played with his cock. I licked it and played with it for a while. I held it and licked the underside up and down then finally took it in my mouth and moved up and down on it. I played with his balls and then added my hands to his shaft moving them up and down along with my mouth.

I was able to get into a decent rhythm of moving my mouth and hands but as I did that, I became more aware that his tongue which was now licking right on my clitoris was making my arousal level soar. In my experience, there are two types of cunnilingus--really good and incredible and even a guy who is going through the motions can make me feel pretty good there at least for a while. To my surprise, this guy was in the second category and I almost felt guilty charging him for what he was doing to me. Almost. I wasn't going to give it back no matter how good he was. He was licking back and forth over the button then teasing by licking around it. Besides the licking, he was moving his hands around, massaging my butt cheeks and sliding up and down my back and torso which added to how I was feeling.

I pulled my mind back from what he was doing to me so I could concentrate on what I was supposed to be doing to him. I moved my mouth off of him and went all in on my licking moves--underside, tip--then took him back in again. My hands played with his balls and teased the area below them. I returned my hands to his shaft and jerked him up and down with my mouth. I was giving him a pretty good blowjob if I say so myself.

His cock was twitching and I figured he'd cum soon. Even though he was paying and this was for him, I felt disappointed that I'd be brought so close to an orgasm that wasn't going to happen. I wondered if I could get away with finishing myself in his bathroom before I left.

He started moving his hips up and down along with my movement on him and I found he was one of those rare guys whose noises told me that he was going to cum. I sped up and he came loudly.

But, as I started to move away from him his hands crossed over my lower back and held my pelvis over his mouth. I ran my hands up and down his legs as he kept licking me. I heard my moans and recognized the pulsing in my vagina and knew that I'd come soon too. When I did, the tension exploded from my body and I collapsed onto him, my mouth over his cock and my hands holding his legs.

I lay there for a while and thankfully, he let me luxuriate in my post-orgasm feeling. Finally, I swiveled back around putting my head to his and kissed him, tasting myself on his lips. "Wow" I told him and meant it.

"Yeah, wow. Thanks for letting me do that. I've never done that with a girl before."

"Really? You're a natural then." It sounded like something I'd say playing my escort role but I hoped that he knew that I really meant this.

I know that time is money but I didn't feel like leaving so we lay there together cuddling and chatting about nothing. I learned that he was an engineer but was shy so he had trouble meeting girls.

Finally, I had to leave so I got dressed still feeling the effect of my climax. He handed me another fifty dollars and I kissed him and thanked him. If all my clients were like that, I'd do this full time. But they aren't and I know that what just happened was incredibly rare.

* * * * *

It wasn't late when I finished with him but I didn't want to bother with another one. It had been unexpectedly satisfying sex and I would have enjoyed it even without being paid. Being paid to have a guy licking me to orgasm was surreal. Thinking about it as I drove him brought my arousal back up so when I got home, I grabbed my vibrator from my bedtable and thinking of how his tongue felt, I brought myself to another orgasm. I slept really well.

I checked my burner phone during the afternoon and there were some messages. Only one made me want to return it but he must have found someone else since he didn't text me back.

In the middle of the afternoon, I got a text asking if I was around and when I texted back that I was he asked for my price for plain sex. I gave him my price and he sent me that address. This time, it was an apartment in an area that wasn't exactly sketchy but wasn't upscale either.

Again, I held onto my pepper spray as I went in and decided that, for safety, I should check the place out before doing anything. I asked if I could use his bathroom and used that to wander around. I didn't see any red flags so I went back to him. He paid me and I fucked him. Nothing exciting, at least for me. The guy last night had spoiled me!

I grabbed something for dinner and went home.

* * * * *

Remember David? He was the older widower who I went to dinner with. He wasn't looking for sex or anything but was willing to pay "for a pretty girl to join me for the evening." He was a really interesting guy and I sort of felt bad that he was paying me. He said that he would call me the next time he was in town but I decided that I didn't want to take money just to have dinner.

Well, he did text me one night and I agreed to meet him for dinner. He had good taste in restaurants and picked another one that I wouldn't have been able to afford on my own. Since his wife died, he had told me that he spent a lot of time reading and I was excited to tell him that I had read a book he recommended. Instead of my normal clothes, I put on my fanciest dress and took extra care with my make-up. I think I looked pretty damn good.

Driving to the restaurant, I thought about the scene in Pretty Woman where he took her to a fancy restaurant. She had told him that she was "a sure thing" but he wasn't just looking for sex. I guess I now have a different perspective on that scene, actually, now that I think about it, on the whole movie.

When the hostess led me to David's table, he stood up to greet me and I kissed him on the cheek. He was a lot taller than me and I reached up to him. We sat and he took an envelope from his coat pocket and slid it over to me. I slid it back.

"David, I love having dinner with you and if that's all you want to do, I don't feel right taking your money" I hold him.

"But I'm taking your time. Don't you deserve something for that?"

"I'm getting something. I get a nice dinner with a real gentlemen who I enjoy talking to. That's plenty for me."

He blushed and nodded his acknowledgement of what I said, then put the envelope back in his pocket. We ordered and it was probably the nicest evening I had had in ages.

I wondered if he had had sex at all since his wife died and if he might want to do more than have dinner some time. I was willing and I don't think I'd want him to pay me for that either. Sorry, Julia Roberts.

* * * * *

I had found a website that was sort of a how-to for escorts. People posted about their own experiences and gave advice. I was glad to get confirmation that a cop would try to get me to make the first offer, so I was probably safe if I didn't say what I was selling. I'd wait for them to ask, then give the price.

I also finally got an idea of what those "special services" that I had seen in ads and was able to say no way to a bunch of them if they came up. I'm open to trying things with a guy I'm dating but that happens only when we've built some trust and it's as much for me as for him. Bondage with a boyfriend, maybe. Letting a total stranger tie me up? No way!

Like a guy who text asking about anal sex. I've done it before but with a boyfriend; it was sort of a special occasion thing for him and I could trust him to take it easy and not hurt me. With a client, who knows and I didn't want to take a chance. The guy asked for my price and I told him I didn't do anal. He kept offering me more and wouldn't drop it so I finally blocked him.

* * * * *

I hoped my bosses were enjoying their vacation but I was actually working harder than when I did my regular shifts at the store. I had a client or two almost every night and probably could have done more if I wanted to. I was making enough money that I didn't have to worry about my pay cut and was able to put the extra cash into my emergency fund.

I got a gigantic contribution to that fund one night from a "special service" I'd have never expected and would never expected to say yes to. I got a text one afternoon asking if I was available that evening and how much I'd want for a three-way.

I've always been a one-guy-at-a-time girl. I know people have sex with more than one person at a time but it's never seemed like something I'd want to do. On the other hand, I was home bored and figured it would be fun to think about. I texted back asking for more details of what he wanted. I wondered he'd want me to give a blow job while I was being fucked or something. No going to do anal was still there for me so if that's what he wanted it wasn't going to happen.

Nope, that wasn't even close. A guy was looking for a girl to fulfill a fantasy for his wife. He said I'd be her birthday present for an evening.

Gulp. Never done that. Never wanted to do it.

We texted back and forth for an hour and I got more details about her fantasy and what they'd want me to do. She wanted us to kiss and we'd both play above the waist. But, he told me that her main fantasy was to go down on a girl and I wouldn't have to do anything back to her. It wasn't really a three-way since he wouldn't get involved, he'd just watch. Hmmm.

I told him maybe but I needed a half-hour to think about it. First, did I want to at all and second, if I did, what would I charge for it?

The two were actually connected. I didn't want to do this but, to be honest, I didn't want to do any of the things I'd been doing as an escort. I was doing it because I needed the money so if all I had to do was to kiss her and play with her boobs and she did everything else, I could probably handle it. No worse than some of the guys I'd fucked or gone down on in the last week, right? And how different would it be to be licked by a woman than by a man?