Helping the Homeless on Thanksgiving
A world-weary woman finds something she didn’t expect on Thanksgiving Day. A Thanksgiving sex story.
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 maybe, 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 dining 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. A 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 as 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 thought that I look pretty. Whatever psychological problems I might have, have never been based upon my looks. I might not be beautiful as a model, but I’m not overweight 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 picked 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.
Then I began to notice something nudging up against me between my legs. I know that Hal had both arms around me still, so I could guess what it was. I reached down and flipped his big dick against my clit a few times to get my juices flowing and then I pushed him up into me.
It was delicious, he was so big that I truly felt impaled by him. He was taller than me so I was almost lifted on to my toes as he began the slowly thrust in and out of me. From his angle, his long tuber was rubbing against my soapy clit on both the in-thrust and the out-pull, and I was in heaven. I’d never had an experience like this with a man before.
I’d always been disgusted by the men I’d had sex with before. I’d always picked them just because they were disgusting, at least to look at. But Hal wasn’t disgusting, although he was quite hairy, he had a nice strong body and good strong legs and a huge penis, so huge in fact that my body began to quiver as small multiple orgasms began to blast through me.
I began to gasp and moan, holding him adjusting my body so his slow rhythmic thrusting would cause the most pleasure, making my body throbbing. Hal kept on thrusting, then pulling out and rubbing his swollen head against my soapy clit and then thrusting into me again. He was magnificent. I was quickly becoming a quivering mass of nerve endings, totally his to do with what he wanted.
Then he thrust into me to the hilt and hugged me tightly, even lifting me off the shower floor and roared as he came in me, holding me impaled on his massive shaft as he spurts his life-giving load deep inside my body.
By the time he was done cumming in me I was gasping from the most intense orgasm I’d ever experienced in my life. When he lifted me off the floor and began shooting his seed into me I went totally wide and writhed about shooting pleasurable twinges deep within until the light dimmed and my mind went totally blank as blast after blast of incredible sensations swamped my senses.
Finally, after what seemed a lifetime Hal lowered me, still hugging me to him, and pushed me up against the shower stall wall. Leaning over me with his lips to my ear, he rasped out, “God Margaret, you’re exquisite.” And then he kissed me on the lips. A long lingering kiss, one that turned me inside out, tongues exchanged, saliva was as one, a kiss so intimate that it was like sex all over again.
I could go one to tell you what we did, again and again, that night. I could tell you all the wonderful first experiences I had with Hal after 41 years of life, but I think I’ll keep it to myself. Actually, I should say, to ourselves. Because Hal ended up moving in with me and after a few months we got married. (I wanted to secure him to me as soon as possible; I was the one who proposed.)
We’re only a few weeks away from our first Thanksgiving together and I find that I love this time of year now. Thanksgiving is my favorite time of year since I met Hal. We’re going to both work at the homeless shelter this Thanksgiving Day and afterward, we’re coming home and we’re taking a shower together.
Helping the Homeless on Thanksgiving is a Thanksgiving sex story presented by eroticprose.com. The home of sexy stories and Literotica.