One day I was surfing around the dating site Plenty Of Fish (POF) when I came upon the profile of a skinny woman in her late 40’s. Under the intent section it listed that she “isn’t seeking a relationship or any kind of commitment” which more often than not means she’s looking for hook ups. Based on her profile it looked like she was likely uneducated and lower class. I shot her a message asking how things were going in her world.

I pretty quickly got a reply. It consisted of a ramble about how none of the guys on the site would help her. Her life was falling apart, was badly in need of some help and the guys wanted sex in return for helping her. “so you need help, for what” I asked. She tells me she and her 14 year old daughter got kicked out of the weekly motel they were staying in because she ran out of money. Worse still, the motel kept all of their stuff and it would cost $150 to get it back. They only had the clothes on their backs. She had no way of getting to work, her daughter was staying with a friend for now and she was on the street. She asked if I could help? I got her number and we started to text instead of messaging on POF.

She was about 30 minutes away from me on the other side of town. She hadn’t eaten in 2 days, was on the street and her daughter could only stay at her friends for another night or two and would then be on the street with her. I said I couldn’t do much and only had about 2 hours before I had to get to work but I could meet her and give her a few bucks so she could eat. She was thrilled and told me to meet her at a McDonalds.

About 45 minutes later I walk into McDonalds and see her sitting in a quiet corner. She was happy and relieved I actually showed up. She gets up to greet me and I discreetly check her out. She’s plain but certainly not ugly. Dark hair, what look to be C-cup breasts, a slender body with skinny legs. I sat down across from her and she begins to tell me how desperate things are looking for her and her daughter, but for now would simply be thankful if she had enough to get something to eat. I was originally going to give her $20 but was feeling generous and gave her $40. She was thrilled. I told her I had to get to work but perhaps I could help her more in a day or two if she didn’t have any luck finding help. She hugged me and I left. The entire time simply being a benevolent guy willing to help.

The next day she sends me a text. She’s still on the street, hasn’t found anyone to help and could I please do something to help her. I asked how much she needed and she said at least $200 to get the room back for a week because tonight would be the last night her daughter could stay with at her friend and they would both be on the street the next day. And to make things worse for her the next day was the girls birthday. She was hoping for a little extra from me to get the girl a present. I told her I could possibly do that, but, I would want her to do something for me in return. She said she understood and expected that and asked what I wanted.

I told her I wanted a full 2 hours of her sucking me, fucking her and anal and cuming as many times as I could in the 2 hours. Without any reluctance she agreed. I told her I’d contact her in the morning and arrange to pick her up.
The next morning she hits me up around 8:30 asking if I was still going to meet her. I assured her I would pick her up around 11. She mentions that the $200 will get her the room back for week but she still won’t be able to get her stuff back or be able to eat. “So now you’d like almost $500 between everything?” “If you could, we need our clothes and to be able to eat”. I told her I’d see what we can work out.

“Also, my daughter is with me, she has no place to go can I bring her with me?” I ask “And what will she do while we are alone?” “She’ll behave and be fine on the couch watching TV.” I’m not so convinced saying “Are you sure? For a full 2 hours?” She tries to sound convincing saying “she’ll do what I say, especially if it means not being on the street”.

I pull up to pick her up and see this adorable young girl with her. Sweet face, glasses, skinny and her short shorts and tiny tee show that she is just beginning to bud. They hop in and I wish the girl a happy birthday. She thanks me for being nice and helping them. We get to my place and I ask if they’d like the chance to shower. Mom says yes since she’s been on the street and they go to the bathroom together. The idea of them naked and showering together gets my mind going.

When they’re finished we hang out on the couch for a bit and I whisper to her Mom if she’s ready. She tells me to hang on a minute. I got to the kitchen and here them talking. Mom comes over and asks if I’m going to be able to give her the full $500 she needs.