Helping the Homeless on Thanksgiving - by Phoebe

by Michael & Phoebe

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Romantic, .

Desc: Sex Story: A world weary woman finds something she didn't expect on Thanksgiving Day.

Author's Note: This story is based upon a true store aired on Dr. Phil three years ago during Thanksgiving week. The names may not be the same but the general facts are pretty accurate.

I hate Thanksgiving. I live all alone and every year on Thanksgiving Day I work at a homeless shelter until I'm about ready to drop from exhaustion, then as I'm leaving the facility I pick one of the men, usually a younger type and invite him home.

I hate Thanksgiving so much that fucking the brains out of some strange grubby homeless guy just seems right to me. My psychologist says that I have a "self loathing" issue and that may be so, but I don't really care what he says. It fills a deep down need in me.

I only have sex once a year, on Thanksgiving Day, and always with some drunken smelly guy who probably won't even remember who he had sex with by morning. He might not even realize that he had sex at all. But I would know, and I always made sure that they orgasmed and I always rubbed their spunk all over my tits and lick it from my fingers.

Self loathing that may be, but it gets me through the coming 12 months until I pluck up the courage to choose another homeless man for my pleasure.

This little scenario has gone on year after year and I knew that it would never change. Then last year I had the surprise of my life. One, I might add, was of my own making.

I was 41 then and I had to admit that this little Thanksgiving thing of mine was becoming a disgusting ritual. I wasn't sure if I could bring myself to do it again. I'd been working since before dawn on that Thanksgiving Day in the homeless shelter, helping to prepare the dinning room and side dishes for the day's handout.

My normal routine was to dish out food all day long and then grab a willing man outside the building and take him home. For some reason, this year I decided that I would try to find someone less disgusting than the dregs that hang around and I'd make a pass at some guy during the day, some guy that was at least attractive to me.

That moment happened around noon. I tall thin guy in grubby clothes came in by himself and walked up to the chow line. I watched him while he moved down the line with his plate. He looked to be in his early 30's and he had good posture. He was dirty, but didn't look as filthy like most of the men I'd had in the past.

As he came down the line and stood in front of me, I said quietly, "My name is Margaret. How would you like to come home with me this afternoon."

To my surprise he smiled at me (no missing teeth.) and said, "Hi Margaret, my name is Hal and I'd like that a lot."

Looking around nervously, hoping that no one was noticing this little conversation, I whispered, "Then wait for me in the park, when I'm done here I'll come across the road and get you."

"Okay Margaret," was all he said and he turned away to take a seat at one of the tables and eat his food.

I watched him while he ate and then as he deposited his plate in the pile and walked out of the dining room without a glance back at me. I was suddenly unsure if he would wait for me. He might have just been playing along so I wouldn't cause him any trouble.

I've always though that I look pretty. Whatever psychological problems I might have, have never been based upon my looks. I might not be beautiful like a model, but I'm not over weight and I have regular features, a smallish nose and a generous mouth and I think I look young for 41 if I say so myself.

But that reflection didn't help me as the day wore on. I finally decided that if Hal wasn't there I'd be no worse off than usual, I'd just have pick up some homeless guy hanging around like I'd done many times before.

As it turned out Hal was waiting in the park and I took him to my car and drove us to my house. Unlike the other guys he wouldn't let me do him as he was. He said that even though he was homeless he had his pride. So finally I stopped trying to dissuade him from a shower and let him take one.

While he was in the shower I suddenly decided that I needed one too. After all I'd been sweating all day too. I hoped that he wouldn't mind if I climbed in with him, I figured most men would look at something like that as a bonus. And I was right about that.

Hal was scrubbing his hairy body and was all soaped up; he had a magnificent hard-on in the making. I just stepped into the shower with him and he reached out and hugged me to his soap-slickened body and we stood like that for a few moments.

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Story tagged with:
Ma/Fa / Romantic /