Jill s JourneysChapter 6 Jill the Gambler
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The Gambler free porn video
Anyway, he was pointing a gun at my face. I would have felt a lot better if his hand was steady. Usually, a steady hand meant that the guy was just trying to look good to his friends not that he was interested in actually killing me.
An unsteady hand meant something else entirely. It meant that he did want to kill me, but was still working up the nerve. It also meant that he could accidently squeeze the trigger thus making the question of how much nerve had could work up irrelevant. So I had to get out of it, but how?
Just then, an angel came to my rescue. “Pa, stop. You can’t do this, Pa,” said the voice of this angel. I looked over my shoulder to see a little slip of a girl coming towards our table. She was about as tall as my chest. Very slender, but with obvious curves, even though her tiny breasts looked like they were small enough to fit in my mouth, they were high and firm. Her hair was long, straight, and blonde. Her skin was slightly tanned. Her lips were small, but plump and cherry red. There was a freshness to her that’s hard to describe, but it was arousing, which was saying something because staring down the barrel of a gun is usually not a situation which encourages arousal.
“Please, Pa, you can’t do this. It’s not right.”
“Sorry, Millie,” the man replied, “But I have to get my money back. We’ll lose the farm if I don’t.”
“Mister,” I say, “I won the money fair and square. If you take it, I’ll go to the Sherrif and have you arrested. Not only will you lose the farm, but you’ll go to jail too. Is that what you want?”
“Shut up! I don’t need you talking.”
I decided that it was time to bluff. After all, he hadn’t caught me bluffing all night. I looked him in the eye and told him, “Mister, talking is the only option you have. Right now, under the table, I have a .45 pointed directly at your guts. Do you really want me to shoot you in front of your daughter? I guareentee that I can pull my trigger before you can pull yours.”
Millie spoke again, very quietly, “Pa, put the gun down. Please come home. We’ll find another way to the money. Come home, please.”
The man hesitated a moment, but then lowered the gun and set it down on the table. Millie took his hand and lead him out the front door. For a moment, I felt sorry for the guy, but like I said. Never gamble if you aren’t willing to accept the risk of losing. But, tonight, I hadn’t lost. I had won and won big. I didn’t just clean out the farmer, but I’d taken a lot from the other men at the table that night. I decided it was time to celebrate. I ordered a round of drinks for everyone and went back to my hotel.
I decided to clean up a bit and then make my way over to the whorehouse. Just then there was knock on the door. I was a little concerned that the guy had changed his mind and decided to try to get his money back again. I opened the door just a little bit and saw Millie standing there. She was alone, so I opened the door and asked her what she was doing there.
“I came to ask for my Pa’s money back. Please, we really need it.”
You’re old enough to understand some basic rules of life. And rule number one is that you don’t gamble if you can’t afford to lose. I’m sorry, but I won that money fair and square.”
“What if I gamble you for it?” she asked.
“Do you have any more money?
“No”
“Then what do you have to offer me?”
She got really quiet and looked at the floor, then said something that I thought for sure I hadn’t heard correctly.
“I didn’t hear you, speak up,” I told her.
She lifter her face and said, “I’ve never been with a man before. You can be with me if I lose.”
“Do you know what it means to be with a man?”
“Kinda. I know that I have to take my clothes off.”
I couldn’t believe it. A virgin. I had a chance at a virgin. I’ve always liked young girls. Whenever I went to a whorehouse, I always picked the youngest one there. But even just a few months in a whorehouse will age a girl years. Now, a real virgin was offering herself to me. All I had to do was win the bet.
“Just to be clear,” she said, “If you win, you get me naked, but if I win, I get your money. Not just the money my Pa lost, but all the money you won.”
I looked her up and down and decided the chance to have her was worth it.
“Agreed. What game do you want to play?
“I don’t know how to play any card games.”
“Perhaps we should just cut cards. You take a card from anywhere in the deck without looking at it and then I try to get a higher card.”
I dug up a deck of cards out of my coat pocket and set it down on the table. She reached out a small, delicate hand and picked up the top half of the deck.
My heart dropped. Queen of Hearts. “Is that a good card?” she asked. For a moment I was tempted to tell her it was a low card, but for some reason I felt that it was a point of honor that I popped her cherry fair and square.
“Yes,” I told her, “only two cards, a king or ace can beat it.” She smiled for the first time since I had met her and her whole face lit up. Then I reached out and cut the deck again. I turned the card over and couldn’t believe it. Ace of Spades.
“I lost, didn’t I?”
“Yes, Millie. You lost.”
She took a deep breath and then said, “What do I do?”
I took her hand and pulled her to me. I cupped her face in my hands and started kissing her. At first, she didn’t know how to react, but nature took over and she started kissing me back. My tongue pushed against her lips and she parted them, I thrust into her mouth and touched her tongue with mine. They danced for a second and then she pushed hers into my mouth. I started sucking on it for a minute. She broke the kiss and said, “ No one ever kissed me before, but it’s nice. Will everything be like that?”
“I think I can make you cum.”
“Cum?”
“You’ll see. Or rather, you’ll feel it. Now take off your shirt.” She untucked her shirt and unbuttoned it. Before she finished though, I couldn’t help myself. I reached out and kissed her again. I pulled her to me and my hands roamed over her body, grabbing her small boobs. She jumped back when I did that.
“Oh. Are you gonna touch me there?”
“Yes,” I replied. “And not just there.” I then slid her shirt off her and pulled her chemise over her head. There in all their glory was the most perfect set of boobs I had ever seen. They were high and firm and tipped with tiny little red nipples. As I said before, they looked like one would fit in my mouth, so I decided to test that theory. I placed my mouth over her entire left breast, and licked her nipple. I pulled off it very slowly and rolled her nipple between my lips. Then I did the same on her right breast. She sighed, “That felt so good. Do it again.”
No problem. I sucked on her nipples again. Then I reached around and unhooked her skirt, letting it fall to the floor. “Drop your drawers,” I said.
“Don’t look,” she said, turning around. Then, she pulled them down, giving me a good look at her small, but incredibly lovely ass. “Turn around,” I told her. She did so, covering herself with her hands. I reached down and pulled them away to find another surprise. “Wow, no hair.” She was so smooth looking, I thought I was going to cum in my pants, right then.
Instead I picked her up and carried her to the bed. I layed her down and then started kissing her. I moved to her neck and cupped a small breast. Then I moved my mouth down to her breasts and sucked on them, while I was doing that, my hand slid down, lightly across her flat tummy and then to the top of her pussy slit. I used one finger to part her lips and found her clit. She gasped as I started moving my finger in a circle over it. “Do you like that?” I asked her.
“Oh, yes. I’ve never felt anything so good.”
“Well, that’s just the start.” I then moved my head down there. I parted her legs and pushed my face into her pussy, stopping for a moment to smell the sweet scent of her virgin juices. And then I started licking her. I thrust my tongue into her wet hole and then licked her clit rapidly. I could hear her breath getting faster and she tightened her legs around my head. I kept licking and when she came, she screamed. It was incredible. I’d never had a women cum with such abandon before.
When she settled down and her breathing slowed to normal again, she said, “Wow. I guess I can understand why you were willing to bet your money.” “We aren’t done yet, Millie,” I said.
“We aren’t?”
“No,” I replied as I stood up and stripped off my clothes. “It’s my turn now.” I then approached her face with my dick as hard as it’s ever been. Her eyes got big, “What is that?”
“Haven’t you ever seen a dick before?”
“Not sticking up like that.”
“It gets hard, when I get excited, and you excite me, Millie. You excite me like no girl has ever done before. Now I want to feel your mouth on my dick.”
“You want me to kiss it?”
“Kiss it, lick it, suck it. I just know you will be wonderful.”
I slid my dick to her lips, she kissed it softly, then opened her mouth to allow entry. Her lips were so soft. I couldn’t believe how good it felt.
“Don’t stop,” I begged. “Suck me harder.”
I don’t know how, but she seemed to know exactly what to do. She reached up and started playing with my balls. Suddenly, before I could do anything, I started cumming. I was shooting into her mouth, but she just kept sucking and swallowing. After a several waves, I was spent. I pulled out of her mouth and layed down beside her.
“I guess I’ve been with a man now,” she said.
“Not quite,” I answered. “You still have to be fucked.”
“Fucked?”
“I’m going to put my dick in your pussy. But, I’ll need a few minutes before I can.”
My hands started roaming over her breasts, I lightly pinched her nipples, and then I slid my hand down to her pussy. I sucked her breasts, while I played with her clit and slid my finer in and out of her. I never got it in very far, I kept hitting her hymen. I could just imagine when I popped it. I knew it would hurt, so I wanted her to be as excited and wet as possible, so I kept sucking her tits and massaging her clit.
Soon, I was hard again. “It’s time,” I told her and knelt between her legs. She looked so beautiful like that. I could clearly see her small boobs, her nipples hard. I placed the tip of my dick against her pussy opening and started to work it in. Slowly, I moved, just a little bit at a time. It’s a good thing I went slow, because I felt ready to cum again already. I just could not believe how tight she was. I didn’t realize it was possible for a girl to be that tight. Soon, though, I hit her cherry.
“This is going to hurt some, I’m sorry,” I told her. Then I grabbed her hips and thrust hard. She screamed like she had been stabbed. I stayed still with my dick inside her until she calmed down. “It gets better,” I said. “It will never hurt like that again”
Then I slowly started pumping in and out of her. She was so tight, I moved faster and faster and despite the fact that I had just cum a few minutes ago, I started cumming again. I shot my load into her as my dick spasmed again and again until I was totally spent.
Then I collapsed on the bed next to her and pulled her close with her head laying on my chest.
“Now,” I told her, “You have been with a man. “ Then we both drifted off to sleep.
The next morning I woke up alone. Just as well, I had a train to catch and I didn’t want any kind of a scene. Plus, I might have talked her father out of shooting me over money, but I doubt I would be so lucky if he knew what his little girl and I had done last night.
As I packed up my stuff, I realized that my money was missing. That little whore. She took it anyway. But as I thought back to last night, I decided it was worth it. -->
An unsteady hand meant something else entirely. It meant that he did want to kill me, but was still working up the nerve. It also meant that he could accidently squeeze the trigger thus making the question of how much nerve had could work up irrelevant. So I had to get out of it, but how?
Just then, an angel came to my rescue. “Pa, stop. You can’t do this, Pa,” said the voice of this angel. I looked over my shoulder to see a little slip of a girl coming towards our table. She was about as tall as my chest. Very slender, but with obvious curves, even though her tiny breasts looked like they were small enough to fit in my mouth, they were high and firm. Her hair was long, straight, and blonde. Her skin was slightly tanned. Her lips were small, but plump and cherry red. There was a freshness to her that’s hard to describe, but it was arousing, which was saying something because staring down the barrel of a gun is usually not a situation which encourages arousal.
“Please, Pa, you can’t do this. It’s not right.”
“Sorry, Millie,” the man replied, “But I have to get my money back. We’ll lose the farm if I don’t.”
“Mister,” I say, “I won the money fair and square. If you take it, I’ll go to the Sherrif and have you arrested. Not only will you lose the farm, but you’ll go to jail too. Is that what you want?”
“Shut up! I don’t need you talking.”
I decided that it was time to bluff. After all, he hadn’t caught me bluffing all night. I looked him in the eye and told him, “Mister, talking is the only option you have. Right now, under the table, I have a .45 pointed directly at your guts. Do you really want me to shoot you in front of your daughter? I guareentee that I can pull my trigger before you can pull yours.”
Millie spoke again, very quietly, “Pa, put the gun down. Please come home. We’ll find another way to the money. Come home, please.”
The man hesitated a moment, but then lowered the gun and set it down on the table. Millie took his hand and lead him out the front door. For a moment, I felt sorry for the guy, but like I said. Never gamble if you aren’t willing to accept the risk of losing. But, tonight, I hadn’t lost. I had won and won big. I didn’t just clean out the farmer, but I’d taken a lot from the other men at the table that night. I decided it was time to celebrate. I ordered a round of drinks for everyone and went back to my hotel.
I decided to clean up a bit and then make my way over to the whorehouse. Just then there was knock on the door. I was a little concerned that the guy had changed his mind and decided to try to get his money back again. I opened the door just a little bit and saw Millie standing there. She was alone, so I opened the door and asked her what she was doing there.
“I came to ask for my Pa’s money back. Please, we really need it.”
You’re old enough to understand some basic rules of life. And rule number one is that you don’t gamble if you can’t afford to lose. I’m sorry, but I won that money fair and square.”
“What if I gamble you for it?” she asked.
“Do you have any more money?
“No”
“Then what do you have to offer me?”
She got really quiet and looked at the floor, then said something that I thought for sure I hadn’t heard correctly.
“I didn’t hear you, speak up,” I told her.
She lifter her face and said, “I’ve never been with a man before. You can be with me if I lose.”
“Do you know what it means to be with a man?”
“Kinda. I know that I have to take my clothes off.”
I couldn’t believe it. A virgin. I had a chance at a virgin. I’ve always liked young girls. Whenever I went to a whorehouse, I always picked the youngest one there. But even just a few months in a whorehouse will age a girl years. Now, a real virgin was offering herself to me. All I had to do was win the bet.
“Just to be clear,” she said, “If you win, you get me naked, but if I win, I get your money. Not just the money my Pa lost, but all the money you won.”
I looked her up and down and decided the chance to have her was worth it.
“Agreed. What game do you want to play?
“I don’t know how to play any card games.”
“Perhaps we should just cut cards. You take a card from anywhere in the deck without looking at it and then I try to get a higher card.”
I dug up a deck of cards out of my coat pocket and set it down on the table. She reached out a small, delicate hand and picked up the top half of the deck.
My heart dropped. Queen of Hearts. “Is that a good card?” she asked. For a moment I was tempted to tell her it was a low card, but for some reason I felt that it was a point of honor that I popped her cherry fair and square.
“Yes,” I told her, “only two cards, a king or ace can beat it.” She smiled for the first time since I had met her and her whole face lit up. Then I reached out and cut the deck again. I turned the card over and couldn’t believe it. Ace of Spades.
“I lost, didn’t I?”
“Yes, Millie. You lost.”
She took a deep breath and then said, “What do I do?”
I took her hand and pulled her to me. I cupped her face in my hands and started kissing her. At first, she didn’t know how to react, but nature took over and she started kissing me back. My tongue pushed against her lips and she parted them, I thrust into her mouth and touched her tongue with mine. They danced for a second and then she pushed hers into my mouth. I started sucking on it for a minute. She broke the kiss and said, “ No one ever kissed me before, but it’s nice. Will everything be like that?”
“I think I can make you cum.”
“Cum?”
“You’ll see. Or rather, you’ll feel it. Now take off your shirt.” She untucked her shirt and unbuttoned it. Before she finished though, I couldn’t help myself. I reached out and kissed her again. I pulled her to me and my hands roamed over her body, grabbing her small boobs. She jumped back when I did that.
“Oh. Are you gonna touch me there?”
“Yes,” I replied. “And not just there.” I then slid her shirt off her and pulled her chemise over her head. There in all their glory was the most perfect set of boobs I had ever seen. They were high and firm and tipped with tiny little red nipples. As I said before, they looked like one would fit in my mouth, so I decided to test that theory. I placed my mouth over her entire left breast, and licked her nipple. I pulled off it very slowly and rolled her nipple between my lips. Then I did the same on her right breast. She sighed, “That felt so good. Do it again.”
No problem. I sucked on her nipples again. Then I reached around and unhooked her skirt, letting it fall to the floor. “Drop your drawers,” I said.
“Don’t look,” she said, turning around. Then, she pulled them down, giving me a good look at her small, but incredibly lovely ass. “Turn around,” I told her. She did so, covering herself with her hands. I reached down and pulled them away to find another surprise. “Wow, no hair.” She was so smooth looking, I thought I was going to cum in my pants, right then.
Instead I picked her up and carried her to the bed. I layed her down and then started kissing her. I moved to her neck and cupped a small breast. Then I moved my mouth down to her breasts and sucked on them, while I was doing that, my hand slid down, lightly across her flat tummy and then to the top of her pussy slit. I used one finger to part her lips and found her clit. She gasped as I started moving my finger in a circle over it. “Do you like that?” I asked her.
“Oh, yes. I’ve never felt anything so good.”
“Well, that’s just the start.” I then moved my head down there. I parted her legs and pushed my face into her pussy, stopping for a moment to smell the sweet scent of her virgin juices. And then I started licking her. I thrust my tongue into her wet hole and then licked her clit rapidly. I could hear her breath getting faster and she tightened her legs around my head. I kept licking and when she came, she screamed. It was incredible. I’d never had a women cum with such abandon before.
When she settled down and her breathing slowed to normal again, she said, “Wow. I guess I can understand why you were willing to bet your money.” “We aren’t done yet, Millie,” I said.
“We aren’t?”
“No,” I replied as I stood up and stripped off my clothes. “It’s my turn now.” I then approached her face with my dick as hard as it’s ever been. Her eyes got big, “What is that?”
“Haven’t you ever seen a dick before?”
“Not sticking up like that.”
“It gets hard, when I get excited, and you excite me, Millie. You excite me like no girl has ever done before. Now I want to feel your mouth on my dick.”
“You want me to kiss it?”
“Kiss it, lick it, suck it. I just know you will be wonderful.”
I slid my dick to her lips, she kissed it softly, then opened her mouth to allow entry. Her lips were so soft. I couldn’t believe how good it felt.
“Don’t stop,” I begged. “Suck me harder.”
I don’t know how, but she seemed to know exactly what to do. She reached up and started playing with my balls. Suddenly, before I could do anything, I started cumming. I was shooting into her mouth, but she just kept sucking and swallowing. After a several waves, I was spent. I pulled out of her mouth and layed down beside her.
“I guess I’ve been with a man now,” she said.
“Not quite,” I answered. “You still have to be fucked.”
“Fucked?”
“I’m going to put my dick in your pussy. But, I’ll need a few minutes before I can.”
My hands started roaming over her breasts, I lightly pinched her nipples, and then I slid my hand down to her pussy. I sucked her breasts, while I played with her clit and slid my finer in and out of her. I never got it in very far, I kept hitting her hymen. I could just imagine when I popped it. I knew it would hurt, so I wanted her to be as excited and wet as possible, so I kept sucking her tits and massaging her clit.
Soon, I was hard again. “It’s time,” I told her and knelt between her legs. She looked so beautiful like that. I could clearly see her small boobs, her nipples hard. I placed the tip of my dick against her pussy opening and started to work it in. Slowly, I moved, just a little bit at a time. It’s a good thing I went slow, because I felt ready to cum again already. I just could not believe how tight she was. I didn’t realize it was possible for a girl to be that tight. Soon, though, I hit her cherry.
“This is going to hurt some, I’m sorry,” I told her. Then I grabbed her hips and thrust hard. She screamed like she had been stabbed. I stayed still with my dick inside her until she calmed down. “It gets better,” I said. “It will never hurt like that again”
Then I slowly started pumping in and out of her. She was so tight, I moved faster and faster and despite the fact that I had just cum a few minutes ago, I started cumming again. I shot my load into her as my dick spasmed again and again until I was totally spent.
Then I collapsed on the bed next to her and pulled her close with her head laying on my chest.
“Now,” I told her, “You have been with a man. “ Then we both drifted off to sleep.
The next morning I woke up alone. Just as well, I had a train to catch and I didn’t want any kind of a scene. Plus, I might have talked her father out of shooting me over money, but I doubt I would be so lucky if he knew what his little girl and I had done last night.
As I packed up my stuff, I realized that my money was missing. That little whore. She took it anyway. But as I thought back to last night, I decided it was worth it. -->
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- 12.10.2020
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