Bedding the Bag Lady

of
genre
straight

I (32) was new to the city, having just arrived weeks before. Still getting my bearings, as they say. While walking back to my apartment, I came across a woman who was living rough. Down on her luck and nervous about the police cars driving around. It seems there was a no-tolerance rule for vagrants in the city. I expected her to be older than she actually was; she was only 27, I found out later on. She had no family and had lost her job and rental soon after. With no jobs available, she was forced to live on the streets. Average in looks, with a nice figure; I'm also average, at best a little overweight and balding. It started raining, and being somewhat lonely. I made the offer of my spare room; at first she was reluctant to accept, but then a police car came into view she accepted. It was better to risk being with me than wherever the police would send her. I had no expectations of sex with her. But I was raised to help, and so I made the offer. My new job was as acting supervisor while the restructuring happened. Then I would get a higher position; the company I worked for was family-owned and had purchased another business. So while it was merged with the family business, I would just supervise. Then maybe be it, manager. A job which I didn't get; my cousin got instead. She was more qualified than me. I got the regional manager's position, monitoring the smaller sections of the business around the state and reporting to my cousin. But on the bright side, I would get an assistant. By the time I got the regional manager's job, the baglady and I had become friends, then lovers. I hired her as my assistant; she was already known to my cousin by then also. In the months since we married, she is now pregnant also. This means my mother has started visiting us regularly. The best decision I ever made was offering her a room to live in.
written on
2026-09-25
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