Relationship with an Ex Freelance

Hi everyone,

Here is a story of how i get into a relationship with an Ex Freelance who and is in a dilemma of what to do.

Brief intro :

I am in my late 40s, Tall, a bit tummy and average looking man. According to the latest CNA survey. I am of median household income because my wife work but she does not contribute to anything at all.

Have been chionging freelance for ~20 years. Initially book only once in a bluemoon. Then become more frequent (like once a week)

My wife is from a foreign country. I know when working oversea. Even after married i still crave for booking for freelance because somehow i still miss the excitement of meeting new pretty young girl and getting laid.

I have 2 kids and both is around teenagers. They are quite independent. Wife is a good mother to the children and take care of the family well. Only problem is her family back home who always need support in term of money to solve their personnel problems.

My wife’s family member and in-law most have story of infidelity. Some become forgive and forget and some ended in separation. Well i think my wife is not the forgiving kind.

Sorry due to this account is new. All post need to be approved by moderator. So even if i posted an update it will not appear immediately.

Maybe you guys can help give me some power up so they allow me to post reply sooner

Quote:

Originally Posted by

Huer

First and foremost, are you and ex fl at the free fuck stage ?

I would not call it a free fuck stage. Currently she is back in thailand and attending school again. As of now i am supporting her with very little money i can spare. I ask her what is the status of our relationship and she said she is my mistress and she does not mind.

I have manage to find ways to travel to Thailand to visit her soon for holiday. So ever since i last booked her. I haven’t fuck her once without booking.

Last year, I had the chance to meet a freelance girl (Name : Gin) who was the most attractive among all the ones I had encountered. Based on my experience, she seemed to have just started working in this line, as her body was still fresh and untouched in many ways. She was stunningly beautiful and knew exactly how to turn a man on. Her natural assets were breathtaking—proudly hanging D-cup breasts that bounced as she walked naked around the apartment. She had a slightly meaty build, but her overall package was simply irresistible. She was the kind of woman who would turn heads wherever she went.

I rarely return to the same freelance girl, and I have never developed any lingering feelings after a session. However, something about her made me go back again. On my second visit, I got her contact details, and we started exchanging messages. I confessed that I had feelings for her but also told her that I was married. I explained that I couldn’t afford to “bao” (keep) her as a mistress because I wasn’t rich enough. Instead, I hoped that once she had earned enough for her school fees and living expenses, she would leave this line of work.

Gin managed to extend her stay in Singapore, and I saw her regularly, never growing tired of making love to her. I would meet her almost twice a week. However, due to an urgent matter, she had to return to Thailand. Unfortunately, immigration issues later prevented her from coming back to Singapore. Her agent then suggested that she work as a freelance escort in Hong Kong or Malaysia instead.

Through my conversations with Gin, I uncovered an ugly truth—the freelance stable owners in Singapore were making an excessive amount of money from these women. Based on my analysis, their strategy was to limit the girls’ earnings, forcing them to continue working to reach their financial goals. It was completely unfair. If the earnings had been split 50/50 from the start, Gin could have easily covered her living expenses for an entire year with just a month of work.

As we continued exchanging messages and video calls, I learned more about Gin’s past and the reasons she had chosen this line of work. She wasn’t in it for luxury or an easy life—she desperately needed money to cover her living expenses, university tuition fees, and her mother’s medical care. I genuinely felt that Gin was a good person who had been pushed into this trade by financial hardship.

I wasn’t sure if my attachment to Gin was driven by lust or real emotions. To test my feelings, I booked another freelance girl. The session was incredible—one of the best I had—but I felt nothing beyond physical satisfaction. With Gin, however, there was something deeper, something I couldn’t quite explain.

Ultimately, I decided to put an end to my days of booking freelancers. Instead of spending my spare cash on these encounters, I chose to support Gin until she completed her university studies. I researched the cost of tuition and living expenses in Bangkok and came up with a rough estimate. When I told Gin about my plan, I made it clear that my only condition was that she must never return to this line of work. She agreed, but to my surprise, she said my estimated amount was far too high—she didn’t need that much. Instead, she requested a sum that was less than half of what I had initially calculated.

As of now, even before meeting Gin, my role in my family has primarily been that of a provider. Emotionally, I feel very little for my wife, and we have been sleeping in separate rooms for years—she sleeps in my daughter’s room instead of ours. In many ways, it feels as if we are already separated.

Since Gin knows all about my secret life of seeking out freelancers, I can be completely open with her. I feel comfortable sharing almost everything, and from what I can tell, she has also shared her past with me. As time went on, we grew closer, and she even motivated me to start exercising and update my wardrobe to look younger. I had hoped that she might eventually settle down in Singapore, but it seems she no longer wants to return.

For now, my plan is to travel to Thailand frequently to spend time with her while keeping it hidden from my wife. It’s not easy, especially during festive seasons, but I will find a way to make it work.

Honestly, I don’t mind her past at all. What truly matters to me is building a future with her. Likewise, she doesn’t judge me for having been with so many women over the years.

However, being realistic, if she were to come to Singapore and we attended a party at a friend’s place, there’s always a risk that someone might recognize her—or worse, that one of the guest could have been her client before. That would be an incredibly awkward situation. This dilemma is difficult to navigate. Do you have any advice? How can she and me tactfully handle this situation?

Quote:

Originally Posted by

Laolucas

Please carry on your story as you have not mentioned how did you meet the ex-freelance (local or foreigner), the journey to your present day and the complications that you are facing.

Do include all the hot and interesting parts of all the bros here…. heeee

Thank you!

Yes Sex with her is one of the best. On my first booking with her. She does not offer RAW at all on her service offered and she keep asking me to use a condom. However after much teasing and due to her inexperience she eventually allow me to RAW her. I respect her and did not cum inside.

After that session every time we do raw and when she knew its her safe period she allow me to cum inside her.

I did ask her if she allowed other customer to RAW her also and she admit that there are some other guy. But she only allow me to cum inside her and all the other customer need to use condom or cum outside

So thats that for the sex part with her.

Quote:

Originally Posted by

Annoymous

1. I can tell you are living comfortably and has this need and ability to provide security for others.

2. It’s a bonus that “this other” also provides free F and some interest in you.

3. Do cont if you cont to feel comfortable financially. But i advise you not to commit too emotionally.

4. You should know that eventually she will find a BF, get married and move on. For all you know, she already has a bf now.

5. WARNING too. When she said one, do you 100% trust her? Even if it’s one, the risk of sex diseases is already SUPER high. If you feel anything at all for your wife, or even children i advise you to stop doing this.

Currently we txt and video call each other regularly. She is different from other girls i know in this line. They usually carry designer handbags and stick to their phone. She does not use her phone while she is in school or going out with her friends and as far as i know. She does not carry a designer handbag at the moment.

Emotionally there is already a strong connection. Because of the age gap sometime i tend to have nothing to say except look at her and smile. She will automatically talk about her day and sometime tease me with showing her sexy body.

Well i am using ChatGPT as a Consultant regularly to keep myself sane. Because due to her not always looking at her phone. She sometime MIA for 6 to 7 hrs. But when we talk she usually tell me what she was doing. Usually thats check out with what she have told me her plan from the next day. Schooling, activities with friends, Gym, outing, shopping with friend.

Also when she does visit some place that is not previously planned. She will take photo and send me. Well i trust her that she is telling me the truth that she does not have another guy at the moment and if she does goes out dating or have feeling for anyone. She will tell me.

Culturally most thai girls are different from singaporean girls. Especially those that make it to university. She told me most girls that is not from rich family resort to working in massage spa or bar to make money. It is culturally accepted and nothing to be ashamed off. They are not robbing or doing anything evil. But she know i cannot accept sharing her with any other men. So she agreed no more other men even if she is horny. She will wait for me to visit her.

We have just began our journey together. Deep inside i hope it can last as long as possible. But i know its unfair to her to not be able give her any title. She said she is ok with it and i do not need to divorce my wife. She understand it will destroy my family.

My plan is to tell my wife eventually. Maybe after Gin graduate in 1 year time. Then my financial commitment to her have ended. I will let faith decide. Maybe she met someone. Maybe we ended up getting her pregnant. Maybe my wife found out and accepted the fact that she have to share me with Gin.

So far i am lucky to not have catch anything all these years of chonging except one episode of UTI which is cured already. I already schedule for my regular Sexual checkup this year and with me quiting chonging feelance forever. This will be the last one.

I find Gin is genuine to me. I know since she looks good and have a nice body, surely lots of classmate will want to get into her pants. This fact i cannot change or have the ability to prevent. I can only trust her to tell me with anyone express interest in her.

I also asked myself one question. If we are out at a bar in thailand. If i need to go to leave her alone for a moment and some guy get the opportunity to talk to her and try to get her contact details. What would she do. If she give does it mean anything?

Quote:

Originally Posted by

Bigbluebird

You’re a player all the way till your death bed, forever seeking thrill and eating outside, with the assurance of stability at home as long as you are not caught.

What do you seek from us? Compassion? Understanding? Assurance from us fellow Samsters?

For telling my story here. I hope any bro here with same experience to be able to share some insight.

I know everyone is build different. I have been eating outside for ~20 years. Even my wife think i am a decent men who does not fool around. So never judge a person by its cover.

I have seen men who have mistress and the wife accepted it and live in harmony. This guys usually have mistress that can help them in work and the wife is home maker. I do hope my situation will develop into this type.

Quote:

Originally Posted by

corsiar74

I had a similar experience with my FWB too, she’s a Thai with a baby girl at 4 yo.

Got to know her from TF and had been visited her for twice. I do give her some money during meet up, she’s NOT a FL and she’s working in a restaurant.

She also let me RAW her during our 2nd day sex, first day was with condom.

This is what she wrote to me:

I have emergency contraception and I protect myself well. I have never let anyone cum inside me that is not my boyfriend. You are the first.

Read it with a pinch of salt.

Understood and thanks for the sharing. Yes i understand i cannot trust Gin fully yet. Not until i get to know her better and visit her more often.

On the issue of RAW with her. She did say initially she is angry with me for doing it RAW with her. Its a bit of passion and moment that happen and it just went in. She is an Ang Pai and her service is on the high premium side. But for the RAW she does not charge me a single cent. On my subsequent visit. I round up the figure and ask her to keep the balance and not let her boss know.