My Beloved Jenna Goes Bonkers On Me Ch. 02

In the car on the way home from my appointment with my doctor ex-girlfriend, Jenna told me what my punishment would be for my trying to come on to Samantha.

"It's a good thing she stopped you," said Jenna. "If anything had really happened, I would've broken up with you right then and there. As it is, your punishment will be that, for a duration that I haven't decided on yet, I will NOT be inviting men over to fuck your ass. NOR will I fuck you with my strap-on. I will, however, continue to ride your cock with my pussy. I'll lay you on your back and ride your dick every night, as usual. But no ass-fuckings for you."

Hmm. That kind of sounded like the opposite of a punishment!

"I bet you think that sounds like you're getting off easy, but let's just see how you feel when you've gone a few days without anything going up your ass. I bet you'll miss it, and I bet you'll beg me to farm your ass out to anonymous men again! This'll be a fun little experiment!"

The first night was just fine. Jenna sat on my dick with her pussy and rode me good, and I had a thundering orgasm. The second night was similar, though I did notice as Jenna rode my dick that my prostate twitched in an unusual way, as if it was trying to say it needed something bumping up against it. By the third night, I couldn't stop fantasizing about those men who'd fucked me. I wanted it again so bad, but I couldn't bring myself to beg Jenna to fuck me with her strap-on or invite a man over. By the fourth night, I broke down.

"Jenna," I said, "You were right. I need it up the ass. I admit it. Would you please fuck me with your strap-on? Or. . . invite one of those men over again?"

Jenna smiled wickedly. "Well, well, my boyfriend really has sunk to a new low! Let's go down to the kitchen. Why don't you bend over that kitchen table that you like being fucked over so much, and tell me what you'd like to have happen to you."

Downstairs I pulled down my panties, bent over the table, and lifted my skirt up over my back. Jenna stood across the table from me; she had turned on the camcorder that pointed at me from the kitchen counter.

"What was it again that you'd like done to you, Michael?"

"Jenna, I'd like one of those men, one of those men who all had such big cocks, to bend me over this table, just like I'm bent over now, and have his way with me."

"Do you really need it? Do you need it bad?"

"Yes Jenna, I need it bad! I'll do anything if you'll just have me fucked again!"

"Well aren't you just deliciously pathetic!" said Jenna. "But no, you're punishment isn't quite over yet. In two days, on Saturday, we will be going over to Samantha and her husband Jim's house on the lake. Samantha has told Jim all about your appointment with her the other day, and Jim has expressed a desire to fuck your ass in order to show his dominance over your, and to punish you for trying to come on to his wife. Samantha tells me that Jim's dick is enormous. From her description, it sounds bigger than any of the dicks you've taken so far. So, on Saturday your "punishment" will end, in the sense that you'll get fucked up the ass again, though I think you might find that the ass-fucking you'll get from Jim will be its own form of punishment, given that you won't be used to a dick of that size. Between now and then, though, you'll have to just be patient and wait for Saturday afternoon to come around."

"Thank you Jenna!" I said.

"Oh, also," she said, "no more orgasms for you between now and Saturday. I want you to be horny as hell for Jim's big dick."

Later that night, with Jenna asleep, I got out of bed, went down to the kitchen, took a cucumber out of a bowl, and wiped some olive oil on it. I then went out to the backyard and got on my knees, pretending I was at the mercy of some guy about to fuck me roughly. I shoved the cucumber up my ass so that it was half in and half out, and began masturbating furiously.

Then I heard a window open. A flashlight was now shining on me from above.

Jenna called down to me, "Goddamn it, Michael, stop masturbating immediately, and take whatever that thing is out of your ass. When I come downstairs I want you standing in the kitchen with your hands behind your back."

"Yes, ma'am," I said despondently.

In the kitchen, Jenna held a strange-looking metal device in front of my face for me to see and appreciate. At first I didn't know what it was, but then realized it looked like things I'd seen online before. It was a cock cage. A truly wicked looking chastity device.

"No Jenna, no," I said, "I don't want that thing on me. I'll be good, I promise. I won't jerk off."

"It's getting hard to trust you, so this thing is going on you. It will come off on Saturday when we're at Sam and Jim's house, but not before. And I don't care that you say you don't want it on. Our contract says I can do what I want with you, and this is what I'm damn well doing."

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When Jenna and I arrived at Sam and Jim's place on Saturday, Sam greeted us at the door.

"I like your skirt and blouse, Michael," she said.

"Thank you ma'am," I replied meekly.

"Jenna," said Sam, "please sit down, and I'll bring you some iced tea. Michael, please go upstairs to the bathroom; it's on the left at the top of the stairs. Jim is taking a bath. He would like to look you over. Just let yourself in and introduce yourself."

I was so humiliated that my heart was racing and I had butterflies in my stomach.

When I entered the bathroom, I saw quite a sight: A rugged, large, muscular man relaxing in his bath, with his ENORMOUS dick - obscenely large, in fact - sticking up past the surface of the water, crowned with a bulbous, angry-looking mushroom head.

"Come here, girl," he said. "Let me take a look."

Terrified, I walked up to the edge of the bathtub. He lifted the front of my skirt with one hand and pulled down my panties a bit with the other, exposing my dick in its metal confinement.

"That is so funny," he said. "Your girlfriend is completely dominating you! Now turn around."

Now he lifted my skirt again, pulled down my panties some more so that they were completely below my buttocks, and shoved a big soapy finger hard up my ass.

"Ow!" I said and reflexively bent over in pain at the knees, causing his big finger to slide even further up my ass.

"You'll say more than just 'ow' before the day is over," he said, withdrawing his finger from my anus and giving me a hard swat on the buttocks. "Do you believe me when I say it's going to hurt?"

"Yes sir I do," I said, now scared and beginning to cry like a little girl.

"There's another thing that's going to hurt you quite a lot," he said. "Did Jenna tell you about this other thing?"

"No sir."

"That was probably wise of her; you would've freaked out too much. The other thing is that, before I fuck you, I'm going to cane you. I'm an expert and have taught classes on it in the past, but haven't done it in a couple of years now. I'm interested in keeping up my skills by practicing on someone, and Jenna has volunteered you for this purpose."

I gulped, and the butterflies in my stomach fluttered even more furiously.

Jim continued: "If you are wondering how many strokes of the cane you'll get, the answer is indeterminate. I will cane you until, in my judgment, just one more stroke would draw blood. We do not want a bleeding ass here. But I won't stop until your ass has gotten right up to that threshold. What do you think about that?"

"Sir, please, I can't take that!"

"You WILL take it, and you'll thank me for it when I'm through. If you thank me and I feel that you spoke genuinely, then I might not fuck your ass as hard as I can. But if you whine and complain or don't thank me, then I will, indeed, fuck your ass as hard as I can. Now, you can see here - take a look - that my cock will be hard to take. So, will you thank me after I've caned you?"

"Sir yes sir!" I said, and he lightly swatted my caged penis.

"Good. Now, go downstairs and tell Sam and Jenna that I'll be ready for you in ten minutes. Tell Sam that I need her to tie you up in the sun room for your caning, and ask Jenna to take off your chastity device. Go, now," he said, slapping my butt once more as I turned away.

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I won't go into the details of the caning, other than to say that it was the most excruciatingly painful, and humiliating, experience of my life. Most people probably live their whole lives without experiencing even half of that amount of sheer physical torment.

Jenna and Sam, of course, giggled and commented profanely the whole time. For example, "Look at how his butt is trembling and shaking in between strokes!" or, "Jim, this is so hot, could you hit him even harder!"

I did thank Jim after the fortieth and final stroke, though, and cleverly threw in a request for a forty-first stroke, just to prove that my thanks were legitimate. Jim turned down my request for a forty-first stroke, since he thought it would cause the skin to break, but he did seem impressed that I had asked.

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After the caning, the girls untied me and put me down on my back on a yoga mat on the floor of the sun room. The yoga mat was pretty soft, but still it was painful for my buttocks to be touching anything at all. Jenna applied lube to my anus, and also used a squeeze bottle to shoot some more lube into my rectum. Then I saw that Jim was stripping off his shorts and boxers, letting his giant erection spring up.

He knelt down and put my legs up over his shoulders. The head of his cock was so big that it took some pushing for him to even get it through my ass-crack to where it was pressed up against my asshole. He was trying to go in gently, because, I guess, he'd appreciated my thanks for the caning, but it wasn't working.

"Buddy," he said, "I know I said I'd go easy on your asshole if you thanked me for the caning, but we've got a problem here. I can't get my dick to slide in gently; there's too much resistance. So, the only way to do this is to shove it into you in one hard stroke. I'm sorry buddy, I did want to take it easy on you. But obviously I do have to fuck you, and this is the only way. It'll hurt very badly for several minutes, but then the pain will subside and maybe you'll start to enjoy it. Sam, please go get something for Michael to bite down on."

She returned with a long wooden serving spoon wrapped with a washcloth. I opened my mouth and she set it back between my teeth.

"Good," said Jim. "Now, Michael," he said as he continued pressing his cockhead against my anus, "I hear you've been taken up the ass by a bunch of men recently. Jenna tells me that my dick is bigger than any of theirs, and has asked me to punish you. So, then, I guess you'll just have to TAKE IT!"

And with that he forcefully shoved his dick up my ass in one fell swoop, all the way to the root.

The sensation as he did this was violent but almost pleasant, but I knew a wave of pain would hit me a second or two later, and it sure did. I bit down on the washcloth-wrapped wooden spoon, in agony, just trying to remember that the worst of the pain should, hopefully, subside within a few minutes.

And after about five minutes, with Jim now having built up a good stroking assault on my ass, the intense pain of that initial thrust had subsided, and I was left with the still significant but now manageable pain of the in-out-in-out, which thankfully now was combined with the nice feelings of prostate-banging and delicious humiliation, as Sam and Jenna cooed at me and made awful, lewd comments.

While still pounding the bejesus out of my poor, obscenely stretched anus, Jim said to Sam and Jenna, "What do you say we all go down to the beach?"

"Don't you want to finish fucking that poor sissy's ass first?" asked Sam.

"I was thinking I'd just pick him up and carry him down to the beach while he's still on my cock," said Jim. "Please, one of you just lay down a towel when we get there, and then I'll put Michael back down and keep fucking him."

"Michael, put your legs around my waist and hold tight. It'll be like a piggy-back ride, except you'll be on my front."

I did as told, and he then reached under my lower back and pulled my torso up against his chest. I put my arms over his shoulders to hold on, and he stood fully up, one leg at a time, with his big dick still up my plowed ass. He then shifted his hands down so that they were now under my sore buttocks, so that he could hold my weight properly in our new position.

He walked through the house and out onto the lawn with me on him like that, with Jenna and Sam close at his heels, commenting on how impressive Jim was.

I was in a state of humiliation so delicious that I'd never dreamed it possible. This man was my ex-girlfriend's husband, he had caned me in front of both her and my girlfriend, and he was carrying me like a ragdoll as I was impaled on his cock with my arms around his shoulders!

At the beach, Sam put a towel down. Jim lowered me down onto it on my back, and resumed fucking me with long, slow strokes.

"I'm sorry about that thrust-in, buddy," he said. "And you were a good sport about it; I respect you for that. But I'm going to have to keep fucking you for a while; I usually last a long time."

"Thank you for fucking me sir, thank you for giving me the punishment I need!" I said, enjoying the buttfucking greatly even though it hurt.

Jenna and Sam had put down another towel next to us, and Jenna was now sitting on Sam's face, making Sam eat her pussy.

"I knew that was going to happen," said Jim. "Sam, you dirty little subbie, didn't I tell you you had a crush on Jenna? I could tell just from hearing your end of the phone conversations. I knew it wouldn't take long before Jenna would be doing something like this to you, and sure enough here we have it."

"Mmmph," said Sam.

"Mmmph is right," replied Jim. "Hey Jenna," he continued, "did you know that Sam has a fantasy about being fucked by a woman with a strap-on?"

"I'd guessed as much," said Jenna, who had Sam's face completely smothered in her shapely, generous ass.

"Well, later on, why don't you - " Jim stopped talking and his body began to tense up. "Jenna, I'm going to come soon, so now's your chance to make Michael lick your asshole while I fuck him, like you said you wanted."

Jenna got up off of Sam's face, patting her cheek affectionately so she wouldn't feel too abandoned, and sat down on me facing Jim, with her sexy butt squashed over my face and her pleasantly earthy-smelling anus pressed squarely against my mouth.

I began licking her asshole, and before long Jim convulsed and shot what seemed like several gallons of hot cum up into my belly. He kept his dick in me, though, even after it had softened.

"Keep licking my ass, Michael," said Jenna. "You've been doing a good job, and I want to reward you."

With that she began stroking my cock as I continued licking her ass. As I came close to orgasm I could feel Jim's dick starting to harden again, and I hoped he'd fuck his ragdoll just as long and hard the second time.