Going Pro

$150 for about fifteen minutes' work. Yeah, probably going to do that again.

* * * * *

Another text the next night was also worth returning. He wanted straight sex and when I gave him the price, he texted an address. This time, it was one of the nicer hotels in town and I wondered if walking through the lobby in my tee shirt with my nipples poking through was going to be like a flashing red light telling people what I was there for. I opted for a polo shirt instead and at the last minute, decided I'd wear a bra.

The hotel room was really nice and was bigger but otherwise it felt similar to my first time. One difference was that he really did just want straight sex. He didn't want to kiss or play with my boobs first or anything resembling foreplay. When I came into his room, his only question was if cowgirl would cost more. I hadn't thought about charging different rates for different positions so I told him no extra charge. He handed me the money which I counted and I went into the bathroom to get undressed, admiring the fancy shower there. I left my clothes on the counter but took my bag back with me. While I was getting ready, he had also stripped and was lying on his back, playing with his cock to get it erect. I placed my hands over his and we moved together until he was fully hard. I didn't see a condom around so I reached into my bag to get one and opened it.

"Is that really needed?" he asked.

"Afraid so." He didn't say anything else so I unrolled it on him and then got onto the bed straddling his lower legs. I slid up over his thighs and then up to his pelvis. I lifted one leg up and grabbed his cock to guide it into me. He was medium length but was wider than most guys I'd known and, since I wasn't really wet, there was some resistance even with the lubricated condom. I finally worked my way down slowly until my lips reached the base of his cock then leaned forward placing a hand down on either side of his shoulders. My boobs were hanging down over him so his hands went to them like magnets. I started to move my pelvis up and down as he gently massaged my boobs.

Fortunately, it didn't take much of this before I was fully lubricated and he was able to move in and out easily. He started to lift his pelvis in sync with mine. We'd move up together, with him deep inside me, then he'd lower his hips pulling part way out. I'd then lower myself back onto him pushing him back in. Despite the circumstances, I felt myself getting aroused from this pattern and wondered if I might actually climax when I was being paid for the sex.

Well, maybe sometime I could but I didn't this time. I sensed from his flow in and out of me and the way his hands tightened on my boobs that he was going to cum soon. I sped up my up and down movement until he gasped and stopped moving. I let my pelvis down on him so that he was as deep into me as he could get and sat there watching him. He just stared upward for a while and then moved so that he could pull away from me. Without saying a word, he got up and went to the bathroom. I heard the toilet flush and when he came out, I went in and peed. I checked out the fancy shower again and thought briefly about trying it but instead I just got dressed. When I came out, he was standing there naked and handed me another $50.00. My first tip! I thanked him, kissed him on the lips, and left the room.

My three "dates" had given me almost enough to make up the shortfall on the rent. One or two more should do it.

* * * * *

It wasn't until the next weekend that I turned on my burner phone and checked to see if I got any texts. I had renewed my ad for what I thought would be the last time. There weren't any texts waiting and the phone didn't beep for about an hour.

When it did, the text confused me. "Would you like to join me for dinner?"

For a second, I wondered if I had checked the wrong phone and some guy was asking me on a real date. No, it was the burner. I texted back "Dinner?"

"Yes. I'm in town and I'm just looking for a pretty girl to join me for the evening. Just dinner, nothing else."

Nothing else? Well, why not? Who says that an escort has to only be escorted to the bedroom?

I had to think about what to charge since I didn't know how long our "date" would last. I finally decided I'd ask for $300--the same as for sex. I texted that to him and he texted back with the name of a nice restaurant and told me that we had a reservation for 7:30 tonight in the name of David.

I took a quick shower and, since it was a nice restaurant and since my clothes were (I assumed) going to stay on, I thought carefully about what I'd wear. Instead of something meant to look slutty or that would come off quickly, I decided on a dress that was more formal but still sort of sexy. I put on a low-cut bra and left my top button undone to show a hint of cleavage. I even put on nylons and heels. I spritzed some perfume onto my wrists and between my boobs and left for the restaurant.

I figured that David would be an older guy but other than that, I didn't know what to expect. When the hostess led me to his table, he politely stood up to greet me. He was older, probably late-60s. He was tall and thin and looked distinguished with a full head of silver hair. As I sat down, he reached into his coat pocket and took out an envelope which he slid over to me. I smiled and thanked him, deciding that counting it in the middle of the restaurant would be a really bad idea.

I used a normal first date conversation starter then asked him if he was local or just visiting. I learned that he had lost his wife a few years ago and was visiting his daughter and her family who lived here. He needed a night off from family and repeated that he liked to go to dinner with a pretty girl. Yes, I kind of blushed.

As we ate a nicer dinner than my dates generally went for and a much nicer one than I could afford, David and I chatted. Fortunately, he didn't ask me a lot of questions that I didn't want to answer, like what's a nice girl like you doing working as an escort. Instead, he asked where I had grown up and I told him about my normal job although without any identifying information. He told me what he had done before retiring. We got into a great discussion about movies and books and I wrote down the name of a current author who he recommended.

The time went fast and when the server brought the bill, I thanked him for dinner. He told me that he had enjoyed the evening and hoped I'd be willing to meet him next time he was in town. I told that I would love that and to my own surprise, I really meant it.

* * * * *

Less so for the experience with my client the next night. It was another meet me in my car except he wanted full sex. I wasn't exactly thrilled about the risk of doing it in public but he offered to double my fee. So, for $600, I met him in the far corner of a strip mall parking lot. The stores were all closed but we were close enough to the street that I was afraid someone might pull in to check on what we were doing there.

He didn't say that he would want me to get naked, just that he wanted to fuck me. Based on this, I decided to wear a loose dress that I could pull up instead of slacks that I'd have to take off. In addition to not bothering to wear a bra, I (blush) went commando. My dress turned out to be okay with him. After he paid me, I put the money back in my car and leaned back against the side of his car.

The guy dropped his pants and I carefully watched him put on the condom that I handed him. I pulled my dress up to my waist, spread my legs apart, and added some of the water-based lubricant that I had learned to bring with me. I leaned back against the car and he put his hands on my hips. Then, without a kiss or anything else resembling foreplay, he pushed himself into me. I stood there passively while he pumped in and out. Honestly, it felt like he was just masturbating into my vagina and, while it may not have been the worst sex I'd ever had, it had to be up there. I think I understood why he was paying for sex but doubling my normal charge made it tolerable.

So, I now had enough money to pay the rent and a little bit extra to put into my new emergency fund. I had started to read up on financial planning and I set a target of having at least two months' salary in the bank for emergencies. Yeah, adulting. Please don't tell my mom.

And, if I'm going to be more financially responsible in the future, I guess I'm going to have to keep my second job for a while to get that money.