Ash and All the Girls @darkness
Chapter 27 The Punishment

This takes place the day of and the day after Ash finds out Dawn is working at that Sexamainia place.

Serena was at home while Ash was out with some friends. She knew he was cashing in his once a month. Suddenly there was a knock at the door; when Serena answered it she saw that it was Iris who she didn't care for all that much.

"Oh… hello Iris. How can I help you"? Serena asked.

Iris sighed then spoke. "Last month me and Ash broke your rule. After he had done it with Shauna at the tournament he did it with me".

With that Serena was mad.

"Hugh! I knew he'd go and do something like this. Once a month I said. To give me a break and so he wouldn't have to be bond to me. But now he goes breaks it, I swear I'll-"

"Serena wait"! Iris interrupted. "I came onto him, he tried to resist but I wouldn't let him back out. It's mainly my fault, and I'm sorry".

"Ok" Serena said. "Thank you for telling me the truth. Goodbye".

"Bye" Iris said before the door was closed.

Serena thought to herself "Ash Ketchum, I know it is hard for you to resist girls but you still broke our rule so… I don't know what to do with you".

A few hours later Ash returned home, he hugged and kissed Serena and then she said they needed to talk. They sat down on the couch and Serena spoke.

"Iris came by today".

"Oh, what did she want"? Ash asked.

"Well" Serena said. "She told be a few weeks ago when you were at that tournament, that you guys had sex".

Ash just stared at her with a straight face.

"Is it true"? Serena asked.

"It is" Ash said. "I only didn't tell you because it was a fluke and I didn't want to upset you. In my defense Iris came onto me, but I still did it. I'm sorry Serena".

"Even though she came onto you, you should be punished so your subconscious will always remember not to do it again unless I say so. But, since you came clean I'll go easy on you".

"I suppose that is fair" Ash said. "What are you going to do to me"?

"You'll find out tomorrow" Serena said getting up and walking out of the room.

The next day.

The next day the morning passed by quickly. Ash was in his Kanto outfit and he already ate and fed the pokemon. Later in the day Serena approached him.

"It's time for your punishment" she said.

"Sigh, ok" Ash said.

Serena pull out a can and sprayed some purple mist in Ash's face making him pass out and fall on the chair behind him.

Ash later wakes up in their bed and his arms are tied together and attached to the bed by one rope instead two which he figures Serena will want him to turn on his back at some point. another thing is Ash is wearing Serena's black tank top and red skirt, they are a little tight since Ash is a bit bigger than Serena. Ash's boxers are still there though.

"What in the world" Ash says out loud.

He tries to look up and sees a camera on a tripod pointed directly at the bed.

A minute later Serena walks into the room. She's got Ash's black t-shirt and hat on, she also has on her pink panties and a strap-on dick. In her hand is Ash's belt.

"Serena" Ash asks. "What are you doing"?

"For your punishment I'm going to show you what it is like to be me every time we get it on" Serena says. "And I'm going to record the prosperity" she says turning on the camera.

Serena walks up to the bed and says "Now let's begin".

She starts off by smacking Ash's thighs with his belt. Ash gives tiny groans of pain. Serena continues to smack the thighs until they turn red.

Serna then lifts Ash's shirt, or her shirt that he is wearing above his head. She goes on with smacking his his chest, making it turn red as well. With only 3 minutes in Ash already looks very uncomfortable.

"Turn around on your knees" Serena says.

With a little maneuvering Ash gets on his knees with his butt in the air. Serena flips the skirt over a little and pulls Ash's boxers off. She starts wailing on his ass with the belt, these whips are harder than in the other places.

"Ah, ah, ahhh" Ash moans in pain.

"Who's the boss of this relationship"! Serena demands. "Who"!

"You are" Ash says eyes tightly closed.

"That's right" Serena says. "And don't forget it".

Serena flips back over and jams her tongue into Ash's mouth for just a moment. After pulling it out and whips his stomach as hard as she can making Ash's head go up. She drops the belt and grabs Ash's head. She pushes the strap on penis into his mouth making Ash gag a little.

She starts moving it in and out.

"This is what I do to you all the time" Serena said. "Know you know what it is like".

After a short while serena gives Ash's mouth a break and makes him spread his legs.

Serena lines up the strap-on up with his ass and then plunges into Ash.

"Ahhhhhhh" Ash roars in pain.

Ash feels his muscles pulling trying to make room for the long rod. Tears start to roll down his face, Ash hasn't felt this uncomfortable in a decade.

Serena starts moving in and out, but all Ash can feel is pain. A minute into it Serena looks at Ash's face and sees the distress.

"What am I doing" she thinks to herself. "I'm hurting the boy I love".

Tears start to roll down Serena's face, she pulls out of Ash.

Ash looks over at his sniffling girlfriend.

"What's wrong"? Ash asks.

"Ash, I'm sorry" Serena said. "I wasn't even sure I wanted to go through with this. I know you are a good guy, you treat me like an angel. And what you I do to you, this".

Serena unties Ash and turns so she isn't facing him.

Ash sits up and takes off the skirt leaving him nude.

"Serena" Ash says.

"Ash, I'm sorry. I'm sorry" Serena says crying.

Ash hugs her from behind and rests his head on her neck.

"It's ok Serena" Ash says. "I wasn't supposed to break that rule which I did. If you didn't like the stuff I make you do when we have sex you could have just told me.

"No, no" Serena says. "I do like that stuff, it was just the heat of the moment. I never wanted to hurt you".

"Well it pains me when I see you hurt" Ash says. "You know" he says taking his hat off her and tossing it to the side table. 'You actually look really hot in my t-shirt".

Serena smiled and turned to look at him, they shared a long, passionate kiss.

Ash pushes his hand up and under the shirt and feels Serena's breast. They kiss again and fall back onto the bed. They then proceed to make love.

To be continued…

1. Chapter 1 The Boy With the Lust 647 0 0 2. Chapter 2 764 0 0 3. Chapter 3 634 0 0 4. Chapter 4 306 0 0 5. Chapter 5 Only One, Can Be With Him 266 0 0 6. Chapter 6 Date 1 626 0 0 7. Chapter 7 Date 2 530 0 0 8. Chapter 8 Date 3 698 0 0 9. Chapter 9 Date 4 789 0 0 10. Chapter 10 Date 5 729 0 0 11. Chapter 11 418 0 0 12. Chapter 12 738 0 0 13. Chapter 13 1166 0 0 14. Chapter 14 1946 0 0 15. Chapter 15 859 0 0 16. Chapter 16 Captured Part I 1407 0 0 17. Chapter 17 Captured Part II 1164 0 0 18. Chapter 18 Waiting for Greatness Part I 1048 0 0 19. Chapter 19 Waiting for Greatness Part II 1314 0 0 20. Chapter 20 The Best Sex Ever 7247 0 0 21. Chapter 21 New Beginnings 1045 0 0 22. Chapter 22 Once a Month 899 0 0 23. Chapter 23 Tournament 1025 0 0 24. Chapter 24 Female Friends 989 0 0 25. Chapter 25 Who's Gonna Win? 1237 0 0 26. Chapter 26 Fake Love for Money 1091 0 0 27. Chapter 27 The Punishment 1202 0 0 28. Chapter 28 Helping a Friend in Need 886 0 0 29. Chapter 29 The Repayment Part I 1342 0 0 30. Chapter 30 The Repayment Part II 1050 0 0 31. Chapter 31 Mother's Not Buying It 930 0 0 32. Chapter 32 The Truth 875 0 0 33. Chapter 33 The Surprise 1169 0 0 34. Chapter 34 Not Understanding 1006 0 0 35. Chapter 35 Stay in Shape 1080 0 0 36. Chapter 36 Keeping Secrets 1776 0 0 37. Chapter 37 One Last Time? 1487 0 0 38. Chapter 38 New Housemate 1428 0 0 39. Chapter 39 Taken 1104 0 0 40. Chapter 40 Return Home, A New Arc Begins 902 0 0 41. Chapter 41 The Unknown Dangers 1297 0 0 42. Chapter 42 Bachelor Party 1151 0 0 43. Chapter 43 The Final Once a Month 1204 0 0 44. Chapter 44 Serena's Decision 370 0 0 45. Chapter 45 I Love You, Yes I Do 631 0 0 46. Chapter 46 A New Ketchum 1498 0 0 47. Chapter 47 Poker Night 1732 0 0 48. Chapter 48 Recording the Fun 1100 0 0 49. Chapter 49 Things are Getting Worse 807 0 0 50. Chapter 50 Ash and The End 1172 0 0 51. Arc 2 1 0 0 52. Chapter 51 Things Back to Normal? 1115 0 0 53. Chapter 52 Life Always Changes 1342 0 0 54. Chapter 53 The Calm Before the Storm 2547 0 0 55. Chapter 54 Evil Rises, Good Ascends 1834 0 0 56. Chapter 55 The First Of Many Battles 3361 0 0 57. Chapter 56 Gaining an Edge 3471 0 0 58. Chapter 57 Vacation Time Starts 3745 0 0 59. Chapter 58 The Beach Episode 4715 0 0 60. Chapter 59 Forced to Grow Up 4913 0 0 61. Chapter 60 The Tides Shift 3098 0 0 62. Chapter 61 Reservations of the War 5370 0 0