Met Jack when I was young, and he changed my life in so many ways. I could never repay or thank him enough.

It was the early 70s when I found myself living in my car in Seattle WA. Mom kick me out and all I had was a shit job and nowhere to go. I pulled into a motel on the edge of town. Of course it was raining because it was always raining that time of year. I had no money for the Motel, but it was a good place to park. Not many cops would check a motel parking lot, at least back then.
I had just put on my Jacket that was three sizes too big for me. When I saw the room light come on from the room in front of me. I was thinking that some asshole was about to call and complain about me sleeping outside their room when fate turned in my favor for once.
A man stepped out of the room and lite a cigarette, Blue jeans, white T-shirt hair was a little too long for his age, even back then. He stood there looking at me as I tried to pretend to be asleep. When he was done smoking, he came over to the car.
“Hey, buddy, you need a place to sleep for the night?”
“No, I’m good thanks.” It might have been the 70’s but I wasn’t into men. And I really was just scared to death, that someone else was going to start beating on me besides my mother. I hadn’t had a very good life up until then. And I didn’t trust very many people.
“Okay, well, if you change your mind, I’m right inside. Here’s some money kid, you know; so when you wake up you can have a good breakfast. I don’t want anything from you. I’ve just been where you are right now. Thought I should help you out. You have a good night now.”
He truned around and left without another word. I look at the money he handed me and it was two five dollar bills. Not a lot of money back then. It would be like someone handing a homeless man a $50 bill today. So to say, I was surprised, would have been an understatement.
I kept on looking at those two fives for a long time. I wasn’t exactly stupid, I was in the part of town that people got paid for returning favors for money. I wondered how much I would have to do if I knocked on the door.
Like I said, I wasn’t into men. But the truth was I wasn’t into anyone. I wasn’t that lucky in high school? And the closest thing I ever got to getting laid was feeling my girlfriend’s tits, my junior year. Other than that I really had no experience. With girls or guys. In the in the cold and hunger won me over. I figured if I had to suck a dick for a nice warm bed, it would be worth it.
“So, you decided that it was too cold out there?”
“yeah, the temperature is really dropping out there.”
“hey like I said before, I’m not looking for anything. You don’t have to be nervous around me. Want a drink?”
“Yeah, I could use a drink.”
“my name is Jack. What’s your name kid?”
“Michael.”
“I take it life is not going well for you?”
“You could say that. As soon as I graduated high school, mom kicked me out. I wasn’t a big loss. All she ever did was beat on me anyway. Took me a while to save up the money for that piece of shit car out there. But I’m work at a gas station about 5 miles up the road. It might take a while, but I’ll be on my feet pretty soon.”
“Good, sounds like you got a good plan on how to get things moving in the right direction. I don’t suppose you know anything about carpentry?”
“I’m afraid not, I know how to swing a hammer, but I’ve never hit nails with a hammer. Pretty much swinging it is all I know how to do.” Jack seem to find my answer amusing.
“Listen, Michael I’m a building contractor. I build house, buy land, build more houses. All my guys are Union carpenters. Good money if you can show up sober and want to work.”
“Really, just like that?”
“Yeah, just like that kid. Like I said, I’ve been where you are. I saw you sleeping out in your car, and I thought I should offer a hand up. Somebody did it for me once.”
“God, Jack I don’t know what to say.”
“Well, don’t have to say anything. Don’t have to do anything but accept the job offer. Now I’m not going to lie to you. I find you attractive. But you don’t have to do anything you don’t want to do. The job is yours, I can call the hall in the morning, and you’ll be an apprentice before the end of the week. You don’t have to suck my dick for it. But if you feel like sucking my dick I would appreciate it.”
Jack smiled and pour himself another drink. He turned around and filled up my glass. I didn’t know what to say. I had never been in the situation. I didn’t know if what he was telling me was true. If I turned him down, would he still make the call? Would I still have a job offer?
I drank down the whiskey, he poured in my glass quickly. Trying to build up the courage that I knew would never come to me. “Jack, I think I should be completely honest with you. I know the area of town in. Would make you think that I’ve done something like this before. But the truth is, I’ve never been in this situation. Not that I think anything wrong with you being gay. I’ve just never been with anybody before. Not a man or a woman.”
“Well, If you want I can show what it’s like to be with a man. But really Michael, you’ve already had a couple of drinks. I don’t want make you feel like you have to do anything. Why don’t we call it a night. If you don’t feel comfortable sleeping in the bed, there is a couple of sheets in the bottom drawer. I’ll turn up the heater.”
And that was it, Jack stripped down to his boxers and crawled in bed. I sat there with the light off for a long time. Then I pulled off my clothes and got in bed beside him. I didn’t wear any underwear at the time. When I said, I was poor, I was really poor.
In the very early hours of the morning, Jack rolled over and put his arm around me. It scared me.. but I heard him storing. His warm body feel good. I started thinking about what Jack said. I knew I didn’t have to. But I wanted to help him. It wasn’t every day that someone came up to you and offered you a future. I would’ve been sitting in that gas station for the next 10 years at the very least trying to pay my way through college. I had no future. And this Man just offered me a ticket to make something out of myself.
So I slowly pushed him on his back and started kissing his nipples. I didn’t know what else to do. But I figured that was a good place to start. When Jack woke up and saw me kissing and sucking on his nipples. He smiled at me.
“I know I don’t have to Jack, I want to. If you show me what to do I’ll try my best.”
Jack told me to roll over on my back. He kissed me, a long and passionate kiss. I felt him taking down his underwear. He moved down and took my cock in his mouth. God it felt so warm and wet. I had dreamed so many night that some girl would be doing this to me. I was lost in the sensation. It lasted for a while, and I was about to cum, when Jack stopped. I thought I might’ve done something wrong, but he was still smiling. He told me to roll over.
I was such a virgin I didn’t even realize what Jack was planning on doing. I felt his tongue licking my asshole. It was a Little weird but, I thought if he was into it, I would just go ahead and let him do it. It wasn’t long before he added some lube to his finger. That too felt good, and on and on it went, until Jack was sliding his cock between my ass cheeks.
“Just push out like you’re going to take a shit, then hold on while I change your life. After tonight you’ll be begging for this again kid.”
I was so sleepy and so relaxed, it felt like I was being hypnotized by his words. I would have done anything he told me by then.
I felt the tip of his cock open me up, and my eye grew wide. I was staring at that white wall, and feeling the most wonderful full feeling come over me. Jack was a Master in bed. He knew just how to handle me. Slow and easy he kept a nice slow pace until I was pushing back on him and asking for more. My dick was so hard, and I just knew if He could hit that spot just hard enough I was going to cum.
Jack pulled out, and I was empty, searching for that full feeling again. He grabbed my hips and pulled me back until I was on my hands and knees. He pushed my head down until I was touching the pillow again. Then he drove into me hard and fast.
I bit into the pillow and moan like a whore. I didn’t stop Jack. He kept right on fucking me. It was like I was in the ocean with the waves of pleasure washing over me again and again. I looked back between my legs and saw my hard dick bouncing back-and-forth. I was so close to cuming, Then it happen, I started leaking cum drip after drip, then blast after blast shot out of me. I thought I was going to lose my mind.
Jack rolled me over again and took my leg over his arms and started driving down into me. He went on and on. I never wanted it to stop. He flipped me all over that bed. He took me from the side. He had me ride him. He put me on the corner of the bed. While he stood over me holding my feet up as he pounded on my ass. Long after my balls were empty. I still felt like I was cuming.
I’m still not sure if it was the whiskey, or if it was just how tired I was. But all that night I felt nothing but pleasure. But in the morning, it was a whole another story. I woke up with every muscle in my body aching. Especially my ass. Visions of the night before danced in my mind. I looked over at Jack sleeping peacefully.
I looked down his body and couldn’t believe what I was seeing. His cock wasn’t that long, but god was it thick. It looked like a two inch pipe covered with skin. The head of his cock was about the only thing normal about it. From the head down was just ungodly thick, except for maybe the last half inch which started to narrow just a hair.
No wonder I felt like I had gotten fucked. Jack should have gone into porno.
“Good morning kid, you sleep well?”
“Yeah, that was something. I never thought it could be like that.” Jack laughed and ran his fingers through my hair. Then they pulled me to him.
“Are you going to be my little bottom bitch now?”
“I’ll be whatever you need me to be Jack.”
“Good, get your mouth on my cock and show me how much you enjoyed last night.”
This new side of Jack was almost scary. But after the pleasure he had given me that night, how could I say no. I grow down between his legs open my mouth. And wrap my lips around that beautiful cock love his. It didn’t fit very well. But I tried my best. I did what I wanted all those girls to do to me. Jack seemed to like it. So I kept at. I kept going until my tongue ached. My jaws hurt. But I didn’t stop until I had a mouthful of cum.
“Good girl, now go take a shower, you smell like a whore.”
The hot water did me good, I ran my hand between my legs and fell around. My little butt hole at taking quite a beating. I still couldn’t wrap my head around it. How the pain had brought so much pleasure.
When I walked out Jack was dressed.
“Write down the address of that gas station. If I don’t contact you this week, show up here next Friday. Same room same time. Don’t worry, Michael, you’ll have a job by the end of next week. I might even be able to find you a place to live.”
“I don’t know what to say Jack, thank you.”
“here’s 40 bucks, that should pay for a few meals. I only have enough to pay for two more days on the room. But it’s two days you won’t have to spend in your car.”
Jack left and I spent the next week thinking about nothing but the night he had given me. No matter how many times I jacked off, it was nothing compared to the orgasms jacket given me. I couldn’t wait to see him again.
I was working on that Friday, Jack stopped by right before I got off.
“Hey, Something came up, can’t do this weekend at the Motel. But I do have some good news. You start your apprenticeship on Monday, I’ll take you down to the Union hall myself. If you think that’s good news, I have some even better news. I talked to the wife, she said you can move in to the apartment above the garage. We’re going to have to keep our relationship kind of low-key. You understand right?”
“Yeah, I understand. Thanks for this Jack. Thanks for everything.”
On the way to his house Jack pulled into a City Park. I pulled up behind him.
“Why don’t you get in the back sit, And let me have a little fun with that tight little but of yours.”
Jack didn’t have to ask me twice. He didn’t take his time like he had the first time. He just lubed me up and put it in me hard. I was screaming in pain, But Jack seem to be having the time of his life. It felt good, but Man did it hurt. He was fast too. I was so close, to feeling that pleasure again. When Jack emptied his balls into me. He was breeding his bitch once again. And like a good bottom, I was happy to let him do it.
“hey Marie, this is Michael. He’ll be staying up in the apartment.”
Marie, was about two inches shorter than Jack, but she was two inches taller than me. Marie was attractive. I liked her instantly. She had a warm smile. Jack said he had an early meeting in the morning, shook my hand and told me to be ready to work on Monday. And that he would be in and out of the house most of the weekend. Then he went to bed.
Marie smiled at me again, and took me up to the apartment above the garage.
“You have any women’s underwear?”
I wasn’t sure I heard her right. Marie could tell by the surprise look on my face.
“what? Did you think you were the only bitch that he ever brought home? He’s tried this before. Listen I don’t care what my husband does. I have two kids, if I get you looking at them, I’ll chop off your balls. The reason I ask if you have any women’s underwear is because my husband’s cum is leaking out your blowen out ass. We don’t have to look surprised. My ass has been gaping a few times after he had me. I’m sure you know The Man cums like half a gallon up inside you, then kisses your cheek and tells you that you’re a good girl. Yeah, if he hasn’t he will soon. He grows tired of his little bitches quick. If he promised you a job. Work hard at it. The Union will keep you even if Jack decides your ass is tight enough anymore.”
“he told me that he didn’t know anything about it.”
“well we better keep it that way. Women’s underwear is in the bottom drawer of that small trunk over there. Go ahead and drop your pants. I wanna see that little house that my husband likes so much.”
“really I don’t wanna cause any trouble. I didn’t know he was married.”
“it’s no trouble, jack, horny guy. He likes to have lots of sex. Frankly, I’m tired of that big fucking dick tearing a hole in my butt. If you like it, you can have it. There’s just a couple of rules. My pussy comes first. He ever puts you in front of me and you’re going to be out on your ass. And I cannot stress enough about my kids. If you’re one of those sick fucks likes kids. Don’t unpack your bags. Don’t even try to move in. Because I’m not lying. I will go to prison for killing your ass.”
“I’m not like that Marie. Until a week ago I was a virgin.”
Marie laughed so loud. I thought she was going to wake up Jack.
“you mean that big dick motherfucker took your virgin ass?”
I look down on the floor, embarrassed.
Marie walked over to the small trunk on the far wall, opened it up and took out a pair of underwear. She then walked to the bathroom and came back in front of me.
“go ahead and takeoff those pants.” I was embarrassed, but I did it.
“oh no underwear at all.”
“I left home in a hurry. And I don’t have a lot of money.”
“this is a maxi pad, it sticks in your underwear like this. You don’t have to be embarrassed. Well, you don’t have to be embarrassed unless someone sees you wearing this underwear. But it’ll keep my husband’s cum from leaking out on your pants. And I’ll keep the guys at the Union hall from knowing You’re a little sissy freak. Hey, I didn’t mean anything, by it. Those guys down on the job site. They’re gonna eat you alive if you can’t take a little joke like that. Just learned to give it back to them. You start showing that you’re scared of them. And you’ll be like fresh meat in front of sharks. Start acting like a man. Even if you bend over at night.” Marie smiled again, and told me to turn around and bend over.
“damn, probably took you to that park about a mile from here, right.”
“yes ma’am.” Marie slap my ass hard.
“go ahead and put on your panties, get a good night sleep kid, breakfast will be at 8 am sharp. If you’re late, you don’t eat.
“thanks Marie.”
I went to sleep that night in women’s underwear, and my butt hole twitching. I was fine in the morning. Still a little sore but I thought I could pull it off. After spending the weekend watching Jack walk in and out the door. Golfing with a banker, then meeting and land owner in the afternoon, then gone all day Sunday drinking with his guys at the bar. I was starting to feel neglected. And I could see that Marie probably felt the same way. I was young, but I wasn’t stupid. I had a feeling that Jack would be replacing me soon. But he was still my ticket in for a good life. So I wasn’t going to blow it by getting mad about something that meant nothing. Especially when I could see a good life for me so close. All I had to do was reach out and grab it.
Monday morning started early for me.
“Time to get up, Michael. You must be slipping, my husband came in last night fuck the shit out of me.”
“isn’t that a good thing?”
“it can be, anyway, I’m dirty, and he didn’t finish me off. You any good at eating pussy?”
I looked at the door and wonder if Jack was going to walk in on us or if this was some kind of test to see if I follow the directions.
“I don’t know I’ve never done it before. Well you just lay right there and I’ll show you how it’s done.” Marie grabbed my headboard stood up on the bed and put her feet on each side of my head then lower herself down, she picked up her nightgown where she could see my face. Her hairy pussy was inches from my mouth.
“Now, all you have to do is lick me right here, that’s my clit. He just wrapped your lips around it like it’s a little dick. Start sucking and licking on it.”
I must have followed her directions well. Soon her juices were flowing down my face. She was bouncing her hips back-and-forth. And it was over way too fast.
“Damn, that was good. Better hit the shower, wouldn’t want to smell like pussy on your first day. Be sure to empty my husband’s balls before you get home. I took quite a fucking last night. I’m a little sore. You scratched my back and I’ll scratch yours. You understand.”
“yes ma’am.”
I took a shower, and Jack drove me down to the Union hall. A few hours later I was putting on my first tool belt. And learning how to use a handsaw. I was really tired that first day. But that didn’t stop Jack from pulling into the park. And empty in his balls into me.
Got it feel good. That thick piece of meat sliding in and out of me. You didn’t take Jack long and I was dripping in the back of his 1970 blazer. He fucked me so hard, and when he came. It was like he was trying to breed me. I felt his cock twitching in my ass. I was so happy to please him.
“Nice underwear, where did you find those?”
“I was just looking around the room. I thought you might find them exciting.”
“they’re cute. Even got a little maxi pad. Your mom teach you that?”
“well if you didn’t cum so much, and leave me so open after you fuck me I wouldn’t need it.” Jack laughed. And I pulled up my pants, my women’s underwear.
“hey, I can’t go home with my dick smelling like your ass. Put that little mouth to work.”
I went down on that dirty dick of his, and it was clean as fresh snow on a mountain when I got finished.
“Fuck, you’re a natural, born cocksucker. That are not let the guys at work know that.”
And after that we fell into a nice little routine. Jack basically went out and partied on the weekends which Marie and I were sure meant that he was sticking his dick in anything that he could. But on those lonely weekends without him. Marie and I grew close. She taught me how to make love to a woman. And if Jack was ever too rough. I was there to kiss her ass and make it better. And ever so often she would do it for me.
Jack died after another tweeny years of ripping my ass apart, massive heart attack at the job site. I saw his kids graduate. And I took care of Marie. Until she passed away 10 years later. The kids got his business. And sold it as soon as possible. Luckily by then I had saved up a lot of money. I basically paid myself what I would’ve paid in rent, food, and electric. So when the kids sold the business, I retired to the east side of the state. Built me a log cabin, where I sit and write dirty stories. Jack off, and remember the good times I used to have. With that big dick motherfucker. And that dirty mouth wife that he had.

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