It’s been a long time since Charly had seen the light of the grid. Almost 2 Years. Back then the last thing I did was working for tips at Cafe CumCum as a sex waitress. 

Charly is a character who resembles an older woman in her early 50ties. The original purpose was to investigate special kinks in Second Life. You know, the weird ones such as ageplay, incest families, and the like.

I retired from all that. Ever since I entered the grid on rare occasions, but didn’t do anything spectacular. Just the usual stuff, hanging out in music clubs and chatting away with people.

Yes, I know a little boring.

That was about to change when I received a call from Candy.

“Charly, you need to do me a favor. I have a guest at the hotel who is asking for some company from an older lady and all my girls are rather young. Can you jump in and serve this guy?”

Wait a minute.

“Candy, I retired from the sex business long ago and my looks are not even close to being good enough to do that kind of job.”

She insisted:

“Come on just this one time, I don’t want to disappoint this guy and he usually tips well .”

I suggested a compromise:

“Look, check me in as a hotel guest, not as one of your girls. I have a chat with him and see where it leads. If he tips me, you can keep the money for the hotel, I am not that often online anyway and don’t need any L$.”

I checked in and went straight to the hotel bar, where this guy Carter was sitting in a bathrobe. They give those out to guests to make undressing for sex easier. It was obvious what he is there for.

“Oh nice, so that is the older woman you have on the house menu, Candy?”

That bitch already sold me to him. How did she dare?

I had a closer look at him.

A black guy. Pretty old school looks, nothing special, but hey I have done worse at Cafe CumCum. It was mandatory back then to let anybody who walked into the Cafe fuck me.

He continued:

“Finally a mature woman in the house, I go for it.”

The situation was strangely arousing and exciting. I decided to go for it, this one time only, and afterward I would have to have a serious talk with that bitch Candy.

We went upstairs into the hotel suite. At first, I was a little reluctant to undress. I was sure that he was very spoiled by all those good-looking, sexy girls at Candy’s. How can I possibly compete with them, with my outdated looks as an elderly woman?

Boy, I was wrong.

He was really into it, When he sat on the bed he had already a boner, a very explicit sign that he liked what he saw.

Of course, I have fucked with every Dick Tom, and Harry at Cafe CumCum (I had lost count of how many fucked me there) and had no inhibitions. Without hesitation, I started to wank his cock to get it on.

It turned into a session of wild and passionate sex. He was really into me (literally) and got very excited.

I was the whole time in control on top of him and in the end was riding him, massaging his cock with my pussy until he finally erupted in said pussy.

It took him a while to recover from that.

A little after he had climaxed and recovered he went on like this:

“I am glad there is now a mature lady in the house, I am myself in my end 50ties and would prefer someone to fuck with in my age group.”

Wait.A.Minute

I was laughing and explained:

“I am not working her. Candy kinda tricked me into this. Look, if I was to work here, I would have to get my avatar up to date, which does cost a lot of money. I’d need to spend at least 20000 L$”

I continued.

“I would have to do this regularly to recover the investment. I doubt I could compete with all those pretty girls here. It would take me ages to make that sort of money.”

Then I had a fun Idea,

“You know what? This is what we can do. What if you finance my upgrade to a decent-looking, up-to-date older woman, and in return you can fuck me as often as you want without having to pay or tip me.”

He thought about the proposal for a bit. Then he said:

“Ok, but are there any limits as to how often or how long and what time frame?”

“Well, it’s subject to availability and we can cap it for a year maybe.”

He agreed. We had a deal.

Take that Candy-Bitch. You just lost a customer.

There is nothing she can do about, it as we both are hotel guests and I am not an employee. After all, it was Candy who paired me up with him.

My revenge for tricking me into sex work.

There was just one thing that did bother me a little. His looks. I mean for an on-off fuck, that is not a problem at all, but if this turns into something regular (maybe a sugar-day-like relationship of sorts, or a friends-with-benefits thing) I’d prefer him to look the part as well.

I asked him:

“What about yourself, would you like to get up to date as well? I think it would be a lot more fun for both of us.”

“I was thinking about that. Would you assist me with that?”

I certainly would!

The next days, I was busy shopping spending the 20k he paid me, and very busy getting my looks right. The result was a cool-looking, sexy woman in her mid to late 50ties.

I’m really happy with the results. What do you guys think? Please leave your views in the comments.

To be continued. 

Read in my next stories if he likes my new look and how we improved his very own look.

There is yet another challenge for us: We shouldn’t use the hotel for our sex encounters for too long, it’s a sex business after all, and it could potentially upset the girls working there.