My Wife and the Homeless Man

I live in a large city with my wife. My kids live with us part-time. Thus, every other weekend, my wife and I are alone, and for a two-week period during the summer, my kids are on vacation with their birth mother. This event occurred during one such two-week break.

Living in a large metropolis, I've grown accustomed to many things like traffic, gun violence and other crime, pollution, etc. But one thing that I've never grown used to is homelessness. Every time that I go downtown, I'm overwhelmed by the amount of people living on the streets. And over the past few years, I've begun to notice beggars at the intersections outside of the downtown area, slowly making their way towards my end of the city. In the past few months, I've noticed a small group of homeless men, asking for change a few blocks from my home. They seem to work the stopped traffic from sunrise to sunset and then make their way to the train stop, take their earnings from the day, and ride the train all night. Every time that I see them, I wish that I could do more for them than just hand them some spare change.

But my wife will have none of that kind of thinking. She doesn't even like when I crack the window to give them money.

"Please, they could be dangerous. They could have diseases. They smell so bad," she would whisper before I would open the window. And she would always give me the silent treatment for a bit afterwards.

Don't get me wrong. My wife is normally a kind, caring woman. She always goes above and beyond to help my kids, or family and friends, or anyone at work, but she has a fear of homeless people, thinking that their situation is always their fault. It's an irrational fear, as she has really never had any extended contact with a homeless person.

I have a different mindset, and I try to help when I can. However, I don't feel like my tiny bit of change is really making any difference, and I have long had a desire to help on a grander scale. I've thought about making a lot of food and distributing it, but I really don't have the type of transport for that. I've thought about starting some kind of non-profit, but I wouldn't even know where to begin. I was frustrated by my lack of ability to do more. And when I expressed my feelings, my wife was supportive, but she assured that there was nothing that I could do.

One morning, when I needed something from the grocery store, I decided to walk. It was a nice summer morning. My wife was asleep, and the kids had just gone out of town. The store is about a mile from my house, so too far to walk if I were in need of anything heavy or in mass quantities, but fine for the loaf of bread that I needed that day. At the intersection, I saw one lone homeless guy. He was on the corner instead of in the middle of the street.

He greeted me, "Hey, mister. You give me change sometimes. I know you. Not driving today?"

I responded, "Nah, I thought I'd walk. How's it going out here today? Are you doing ok?"

"Thanks for asking, and God bless. Good as I can be, I suppose. Have anything for me?" he asked.

"Let me catch you after I hit the store." But as I left him and shopped for my bread, I couldn't shake the guilt that I had. I wanted to help. I needed to. So I bought my bread and more items, anything. I can't even remember what. I just had enough that, when I left the store, I was having a hard time walking, and there was no way that I'd make it a mile back home.

As I got across the street, he was waiting there.

"Looks like you got a heavy load," he smiled.

"Uh, yeah, I guess that I got too much. I don't know how I'll get home," I absent-mindedly muttered.

"I could help you, if you need. You've always been so giving to me. I'd like to pay it back a little," he kindly offered.

I accepted, and we divvied the bags and began our march. On the way, he told me his name, Jerry. He was 32. He told me how he ended up homeless, how he had a job and wife, but she divorced him and took the house. He became terribly depressed and lost his job and subsequently his housing. He said that it took over a year of living in shelters until he was over the pain caused by his divorce. But by then, he had been out of work for quite a long time. Since then, it had been difficult to find a place to work, since he had no address for applications. And he had not been able to break the cycle of homelessness.

I felt so sorry for this guy. So I did the only thing that I could think of. I offered him the opportunity to stay in my basement for two weeks, during which I'd help him find a job. He could use my address, and I'd lend him clothes. I told him that my kids would be back in two weeks and that he'd have to be gone by then.

He completely understood and was overjoyed. He wept.

We went inside, and I showed him the basement. It had two couches, a fridge, and a bathroom with shower. It was almost like a studio apartment. He just kept thanking me over and over. As this day was a Sunday, we'd start the job hunt on the very next day.

After he and I ate breakfast, he went straight into the shower. I snuck into my room, where my wife was still sleeping, and got some clothes for our new housemate.

Jerry was taller than I, but a tiny bit more slender. I'm about 6 feet tall and weigh about 155, but Jerry was maybe 6'2" and probably weighed about the same if not slightly less. I knew that some of my pants might be too short, but it was better than nothing. I got him a pair of shorts, a t shirt, and some underwear and socks. I'd save the formal wear for job hunting.

When Jerry exited the shower, he was wrapped in a towel. I handed him the items.

"No offense," he said, "but I would feel weird wearing your underwear. I'll just do the other items."

"Oh, fine by me," I stated, almost embarrassed.

I left him and went upstairs. When I got there, my wife was making coffee.

"Hey, baby, what's with all of the grocery bags?" she asked.

"I needed something, and I went to the store, but I walked, and I had too many things, and..." I was rambling and speaking much too quickly. My wife, though, was no longer looking at me. She was staring over my shoulder with a shocked look in her eyes.

I turned and saw Jerry, smiling and half waving.

"Honey, this is Jerry. He helped me carry things home," I stated, but knowing how to proceed.

"Why is he wearing your shirt?"

"Oh, I let him borrow it after he took a shower," I realized that my words probably seemed nonsensical to her.

So I sat her down at the kitchen table along with Jerry and relayed the entire story. I could see the concern, anger, fear, confusion pass across her face as I spoke, but she said nothing in front of our guest.

After moments of silence, Jerry was the first to speak: "Miss, I understand how you must feel, so if you would like, I can leave now, no hard feelings. I'm already blessed for what I've received today."

Those words must have broken her heart a bit, because she shook her head no and indicated the he could stay as long as I had promised. But the glare immediately after told me that I needed to speak with her alone. I showed Jerry how to work the tv in the basement and left him to return upstairs. I met my wife in our bedroom. She was upset.

"How could you let a stranger in our house? How do you know he won't kill us?" she asked.

"I couldn't do nothing. We'll lock the door. It's just two weeks or until we can get him a job. If you let me help Jerry, I'll never do anything like this again," I pleaded.

"And I don't mean to sound racist, but what will the neighbors say about a tall black man lurking about the house?"

"Screw the neighbors. They can mind their own business," I stated firmly.

She seemed to acquiesce. We went about our Sunday as normal, doing little things around the house. Only this time, as we were working in the yard or cleaning something, Jerry would always emerge from the basement to ask if he could help. It was very thoughtful and seemed to relax my wife a bit more.

That evening, we ate dinner together and got to know Jerry even better. He really was just a guy beaten down by life's circumstances. Eventually, he went down to bed, and we went to our room. We locked the door to be safe.

I attempted to make a move on my wife to entice her into sex, but she was having none of it. She told me not until Jerry was gone. This was going to be tough, as we had sex regularly, probably three or four times every week, but I understood.

On Monday, I woke and got dressed. I picked out some stuff for Jerry. My wife hated what I picked and designed her own outfit for him. Since she was going to work and I had summers off, she said that she would drop the clothes on the way out.

I kissed her at the top of the stairs. She descended, and after I short pause, I heard a gasp and some talking. She ran up the stairs with a crimson face. Not explaining anything, she left.

Later in the day, Jerry and I were out looking for jobs. We found a few decent prospects, and he filled out applications. Jerry wasn't looking for a high-end career, just something that could get him a work history and make him enough to sustain living in a small apartment. It was a pretty successful start.

That night at dinner, Jerry and my wife were very quiet. They didn't speak or really look at each other. It was a bit odd. Later, in bed, I asked my wife if everything was ok, and she told me to go to sleep.

The next day was similar. My wife picked out clothes, brought them to Jerry, and climbed the stairs with a crimson face but maybe a smirk this time. As I was out with Jerry, I had to ask what the weirdness was all about.

Jerry laughed. "Your wife caught me in a state of undress yesterday, and I think we're both a little embarrassed."

Things proceeded like this until Friday when my wife had off of work. On that day, we'd do some stuff around the house. As on Sunday, Jerry was very helpful. At about noon, we got a call. Jerry had an interview on Monday. Jerry hugged me and my wife, but became worried.

"I haven't interviewed for years. What will they even ask me? How should I answer?"

My wife answered, "Don't worry about it today. I'll help you prepare over the weekend."

By the end of the day, Jerry had interviews set up for Monday, Wednesday, and Friday.

The rest of the day was uneventful, save for two things. At one point, my wife was getting something out of a low cabinet. Jerry was next to her, cleaning a high cabinet. I noticed her just staring up at Jerry, as he cleaned, not noticing her. I found it strange. Then, the second eventful thing is that my wife was very frisky with me in bed. I told her that I thought that we were done until Jerry wad gone. She told me that she needed it, and she was gushing wet when I entered her. She normally had an orgasm, but that night, she had three.

After I finished, I asked, "Did that have anything to do with our guest and what you've been seeing?"

She giggled. "What did he tell you?"

"Only that you caught him semi-undressed," I added that I saw her looking up his shorts earlier.

"Semi? There's nothing semi about him. On Monday, he had just gotten out of the shower, so I saw him totally naked on accident. Every day since until this morning, he's been waiting for me naked. On Thursday, he was stroking himself hard."

Her words hung in the air. I was angry, but I noticed that my cock had sprung up to a full erection. I didn't know if I should go kick him out, confront him, do nothing... but my wife distracted me by pulling my erection back into her needy pussy. We hadn't fucked twice in a night in years.

As I was inside her, I asked why she kept going back downstairs.

"The first day," she moaned, "it was so long and thick. I had to see it again to see if I was mistaken. I wasn't. It is so big and veiny and black."

"What about when he was stroking it?" I asked, not knowing if I wanted the answer.

Her pussy clenched around my cock, "It was enormous. It looked heavy and menacing and glorious..." Her words trailed off as she was cumming. I could handle no more, and I unloaded in her.

On Saturday, my wife spent most of the day at the kitchen table, doing mock interviews with Jerry. That night, before coming to bed, she walked to the bedroom door and left it not only unlocked, but also ajar. I had a quizzical look, but she wiped it away when she started to suck me hard, something she rarely did. Once I was erect, she mounted me. After her first orgasm, she spun around, so that she was in reverse cowgirl, facing the door. I lost count of how many times she came in position, which again was a rarity for us.

On Sunday, she said that she would conduct mock interviews with Jerry in our small office. It would seem more professional. About halfway through, she left the office. Upon returning, she was in a formal outfit and had clothes for Jerry. He must have changed in front of her, as he never left the room.

That night, I tried to get her to make love, but she was nervous for Jerry. She kept saying, "He's too worried that he'll do something or say something wrong."

On Monday, my wife gave Jerry a pep talk before heading out to work. I took Jerry to the interview. As we rode home, Jerry looked dejected. He did not think that it went well.

That night and the next day, Jerry wasn't his normal cheery self. He was falling back into the depression. My wife and I tried to encourage him, but he was making himself more nervous.

On Wednesday, he really bombed the interview. He was just too nervous and lacked confidence.

On Thursday, he never left the basement. I was worried about him. When my wife got home, I told her that I didn't know if we could help him anymore.

She asked if I trusted her, which of course I did. Then, she told me something that floored me, "I think the Jerry needs a woman's help to gain confidence and relax his nerves. I'm going to touch him and get him to ejaculate. Are you ok with that?"

I wanted to help Jerry, but this was crazy. Wasn't it? But, again, I was rock hard.

My wife didn't wait for an answer. She just walked downstairs. I followed like a zombie.

Jerry was sitting on the couch, looking down. My wife sat next to him, and I on the other couch. She didn't speak. She just took his right hand and put it on her leg. She took her right hand and started rubbing the front of his shorts.

Jerry started caressing her thigh as the bulge in his pants kept growing and growing. With her left hand, she tried pulling the elastic waistband of the shorts off, but it wouldn't get over his monster cock.

Jerry took that opportunity to pull my wife in for a kiss. He kissed her deeply, tonguing her, and she was reciprocating. Soon, Jerry's hands were at my wife's breasts, kneading them through her shirt. Jerry pulled his own shirt off and then removed my wife's. He took a nipple into his mouth, and my wife arched her back, tossing back her head in ecstacy.

Jerry went to take off my wife's bottoms, but she said that she just wanted to jerk him off.

With that, Jerry removed his shorts. He was very large. He was 9-10 inches long and as thick as a water bottle. My wife's hands immediately went to work. Jerry kept kissing my wife and whispering in her ear. Sometimes, she would smile, sometimes giggle and shake her head no, and sometimes just moan.

After several minutes, Jerry whispered to her again, and she began to move her head down. She was going to suck him off!

She was millimeters away from the head, which was gushing precum. It was like she was considering the impossibility of this giant phallus fitting into her tiny mouth. Then, she closed her eyes and took in the bulbous mushroom head. Jerry groaned, which paired perfectly in time to the slurping noises coming from my wife's mouth. When she came up for air, with two hands both still on his cock, a long string of precum connected her to him still.

Jerry pulled her back and kissed her deeply again. He went to remove her bottoms, and she did not resist this time.

He pealed them off my wife and tossed them to me. He began sliding his long tool over her dripping slit in order to coat it in her juices.

"I need this, baby. Watching you watch me touch myself wasn't enough. Watching you fuck your husband wasn't enough. Having you suck me was close to enough, but to become a man again, I need to feel your cunt quiver around my cock. Are you ready to be fucked like never before?" Jerry asked my tiny wife.

She couldn't speak. With her hands still lovingly stroking him, she just nodded. With that, he pressed the head against her opening.

She gasped loudly, like she had gotten the wind knocked out of her. "Fuck, it's already stretching me out!"

Jerry withdrew all but the tip and pressed in further, this time rotating his hips to help ease the passage.

"Jerry, you are splitting me open. It feels so good."

Jerry responded in two ways. "Yeah, baby, keep telling me how it feels," and by withdrawing the three inches that he had inside of her and pushing back in five.

"Jerry, are you all the way in? I'm not sure will fit."

Jerry laughed, "About halway. Don't be nervous. Be confident that you can handle it. Isn't that what you're always telling me," and with that he pulled out the five and reinserted seven.

"I'm cumming, Jerry. I'm fucking cumming on your big, black, marvelous, giant, dick."

Jerry was smiling ear to ear. After rotating his hips some more, he withdrew the seven and replaced it with nine.

"Jerry, it's like one constant orgasm. I've never been fucked like this," my wife was speaking as if I wasn't even there.

"I've not begun to fuck you yet, darling." With those words and thrusts, Jerry pulled out his nine and didn't stop pushing until his pubic bone met my wife's. I knew that they were fully couples by my wife's scream.

Jerry began to plunge his massive rod in and out of her like a piston. He kept this up through at least four of my wife's orgasms. Then, he flipped her onto all fours before he started hammering away at her stretched hole. With his left hand, he grabbed a fistful of her hair and pulled her head back so that he could keep talking into her ear. With his right, he rolled her right nipple. I was amazed at how rapidly he was sawing in and out of her, how her tight pussy hadn't made him cum yet, how she could handle all that meat inside of her.

After whispering something in her ear, my wife declared, "Yes, Jerry, this is your pussy whenever you want it."

With that Jerry slammed her one final time and bellowed. His massive balls contracted several times, and my wife was still cumming as she was being filled with a homeless man's seed.

Jerry withdrew eventually. His softened cock was still bigger than mine could ever be hard. He walked past me so that I could get a look of it with his cum and my wife's cunt juice all over it. As he went into the bathroom, my wife stood, and a flood of semen hit the floor. She giggled and went upstairs.

I cleaned the floor and followed my wife, who was now sure that Jerry would do better on the interview.

She was right. Jerry got the job. We helped him secure an apartment on the Saturday before my kids returned. He now lives in a somewhat sketchy but very affordable part of town. He is happy with his job and lives simply but comfortably. My wife tells me that he has a regular girlfriend, but Jerry tells me wife that he prefers her every time they fuck, which is still once a week or so.

My wife says that if Jerry gets married that she'll stop fucking him, and at the point, maybe me can help another homeless man find a job.