Punished by Mother, Sister and Wife Ch. 04

I guess it goes without saying that standing naked in my mother's kitchen, wearing nothing but a hard-on and a condom, was not how I expected to spend my Sunday morning. And, coupled with the fact that my mother and my sister were dressed in nothing but their bra and panties, my cock was reacting exactly as it should have been – it was hard and sticking out furiously in front of me.

My little sister snickered smugly as she stood next to my mother, looking at me. Given the fact that it wasn't even mid-morning yet, I was both anxious and semi-terrified about what the day would hold for me if my mother kept her promise to make me live the same punishment I'd written in one of my nasty stores that, apparently, both Cassie and Mom had already read and discussed between the two of them.

After mother gave her little speech about why I was being punished and the rules for the day, I was filled with a multitude of feelings. Making me stand completely naked in front of both of them made me feel utterly shameful. It also excited me to no end. And, there was no way I could hide my arousal – it was plainly evident to the two of them by the way my cock strained out in front of me. And looking in to first Cassie's eyes, and then my mother's eyes, I became keenly aware that they both knew exactly how this was affecting me. Practically as soon as my mother produced the condom and told me to get myself hard, my cock obeyed the order, growing longer and thicker until I was rigid, and it hadn't let up one bit

Being naked in front of my little sister last night in my old bedroom was a blessing the likes of which I thought I would never receive. She patiently walked me through one of the stories I'd written where I detailed how she would order me to undress and masturbate for her, and then how she would dress me for bed in one of her nighties and a pair of her panties. Throughout this unbelievable hour, she was sweet, kind and thoughtful – not at all what I deserved.

And, I would have been happy with what Cassie had done alone, all by itself. But, when my mother came into my room this morning and found me dressed in Cassie's nightie and panties, and asked me to jerk myself off for her, it was like I'd hit the lottery twice in the matter of ten hours.

Then, to add a bit of icing to the proverbial cake, when Mom took me in her room and lay down on her bed, spreading her legs so I could have that long dreamed about look at her pussy – I thought I'd died and gone to heaven.

It was all way too good, and way too unbelievable. The most unbelievable part, though, is that both my little sister and my mom alluded to the fact they'd be willing to help me live out more of my stories if I wanted them to. Of course, hearing their offers tore me up inside for two reasons: 1) I ought to be living these stories out with my wife, and, 2) I wish to hell I'd known they were willing to help me out long before this! Especially my mother, who is a beautiful, sexy and loving woman, and someone whom I'd very willingly suck, fuck, lick and love to whatever extent she'd let me.

This morning, my little sister, Cassie, seemed to be participating in this on a completely different level than my Mom was. Yes, I remember Cassie telling me last night she'd have to act mad and upset with the things I'd done in the past in front of Mom. But, I think my little sister had another agenda in mind, too.

It started this morning when I was standing naked in my room in front of Cassie and my mother. When mother told Cassie to put the condom on me, I assumed Mom told her to help because she didn't want me touching my cock – maybe fearing I might try to pleasure myself. So, when Cassie bent down in front of me to put the condom on my cock, instead of being confused or baffled, my little sister seemed to be enjoying herself. I absolutely knew Mom and Cassie talked about what they were going to do to me ahead of time because their little act seemed rehearsed and because my little sister came into the room wearing only her bra and panties. And, compared to Mom's serious attitude when they gave me the news that I was going to be punished by the two of them, Cassie appeared to be having way too much fun.

It felt absolutely disgraceful and shameful to have an erection in front of my mother and my little sister, and it was humiliating to be told that I'd have to wear a condom for the sole purpose of catching my precum drippings and my ejaculate. Mother did a good job of heightening my shame when she announced I would be milked every two hours, adding she'd personally instruct Cassie on how to milk me. When she said that, I conjured up a vision of me bending over to allow my mother and my little sister to put their fingers up my butt to rub my prostate, and believe me, that vision sent a strong message of what I was going to endure during the next several hours. I know I should have been mortified with what they were planning, but, deep down, I wasn't. I was actually hoping they would do exactly what they said they were going to do.

It was clear, though, that both Mom and Cassie had read my punishment story thoroughly. In that story, I wrote in detail how both of them paraded around in front of me in their bra and panties, and, used every trick they could think of entice, excite and arouse me. They would touch me, stroke me, flaunt them selves in front of me and do everything they possibly could to encourage my cock to stay hard, and keep me turned on and frustrated. The whole idea of the condom was that over time, I'd leak precum due to the way they were arousing me, and the condom would capture every drip that escaped from my hardened cock.

Then, when they milked me, the condom would catch my semen, too, and these two things would eventually cause my condom to fill with my own sexual fluids. In the punishment story I'd written, they milked me every two hours, removed the condom, saved the contents and then put me in a fresh condom. This process continued throughout the day as they said and did different things to keep me aroused. They asked me embarrassing and humiliating questions and made me do things to keep me hard. They were relentless in the way they tortured me, and through it all, my mother acted very stern – adamant about punishing me, and my sister openly enjoyed it, taking great joy in my predicament and doing everything she could to make it even more embarrassing, more humiliating and more torturous.

At the end of the story, I was spanked by my sister while my mother kept me still by holding my cock and balls in her hands. When I'd move, Mom's grip would tighten around my balls until I settled down. And, when the spanking was over, Mom produced a shot glass filled with the juices they gathered from the condoms during the day, and then as a final humiliation, they made me masturbate standing right in front of them while I took sips from the shot glass containing my sperm.

Now, you have to remember this was all detailed down to the letter in the story I wrote. Obviously, it was written as a nasty, erotic vehicle for my own personal pleasure and I had no earthly idea it would be read by anyone else, much less ever lived out like I was going to do. So, when mother said I'd be milked and eluded to the fact that I'd be made to 'take care' of the contents of the condoms, you can understand the panic that went through my mind. I wasn't sure if she would really go as far as to make me drink my own cum in front of them, but, part of me prayed that she wouldn't, and part of me prayed that she would.

Since I began writing these stories years ago, I've learned that my sensations, feelings and excitement are highest when I'm forced to do the most outlandish things, such as, masturbate in front of my mother, or my little sister. Or, be forced to let someone dress me in bra and panties – or even worse, dress me up like a little girl. And there are very few, if any, taboos in my list of favorite story themes. I've written about me being on the receiving end of strap-on while my wife, mother and little sister took turns and watched each other fuck my butt. I've written about being stripped and spanked. I've even written about being made to suck a cock and letting a guy fuck my ass. The things I haven't written about are very few – I don't write about inflicting or receiving real pain, and I've never written anything that demeans women in any way.

But, I think it's important to note that in each and every one of my stories, the main female character is either my wife, my little sister or my mother. Sometimes it's two of them, together, and sometimes it's all three. Granted, my wife didn't appear as a character in my stories until after we met and started getting serious, but, since we've been together, it's been a fair mix of all three of them in the female starring role.

One of hardest stories to write, but, which turned out to be one of my favorites, was a story where I repeatedly begged my wife, Beth, to let me watch another man fuck her. And I'm not talking about a quickie fuck, either. I wanted to see some serious, get down sucking and fucking. I wanted her to be a total slut..... I wanted to see her suck cock like a street whore and then scream and moan as the guy drilled her pussy until she was sloppy and thoroughly used. But it didn't stop there. I wanted much more from her.

I wanted my darling wife to cuckold me that night. Not in a harsh, cruel way, but, I wanted her to take complete control of the evening, leaving me helpless to do nothing more than watch her being a slut with someone else – and I wanted Beth to use my fetishes as leverage to make it nasty and memorable for me. I'd begged her for this many times, and then one day, out of the blue, my wife came home from work and told me she would do it as long as I agreed to four conditions:

1)She would do it one time only, and I would agree to never ask this again.

2)She would pick the guy and I would have absolutely no say in anything.

3)I would be under her complete control and I would obey her to the letter.

4)I would grant her complete forgiveness and it would never be held against her.

So, in the story, I eagerly agreed to her conditions. When the time came for my wish to come true, the whole experience would start early in the day when we checked into a fancy hotel downtown. Once we got in the room, she shaved my cock and balls, and dressed me in a frilly bra and panty set. Then, I spent hours helping her get ready – bathing her, shaving her pussy bare for her lover, washing her hair, helping her dress in the perfect bra and panties and then helping her slip into the sexiest little black dress I'd ever seen my petite wife wear.

As the story went on, I took her down to the classy restaurant in the lobby and we had a quiet dinner of lobster tails and prime rib. We made small talk as we ate, but she never said one thing about her lover, or about what was going to happen that night. Finally, as the waiter brought the check, she simply told me to stay there in the restaurant for thirty minutes and then go into the bar and have a drink. She told me she'd end everything if I didn't keep my end of the agreement and then, she leaned over and kissed me sweetly on the lips, and silently walked away.

I won't go on anymore about that specific story right now, but, suffice it to say that I got everything I asked for, and more. I got to watch him slip his hand up between her legs, take her panties off and fondle her in the hotel bar. When she finally signaled me to follow them, we went upstairs to the room, she stripped me in front of the man and then made me undress her first, and then him. This guy had the biggest and thickest cock I'd ever seen in my life, and when she pushed me down on my knees in front of him, I knew exactly what she wanted me to do. I sucked his cock until he was hard and once he was ready, I guided his cock into my wife and sat in the chair next to the bed and watched this big dicked guy take my wife. By the time it was over, he'd fucked Beth hard and wild, and she had several thunderous orgasms. The evening culminated with him cumming in her pussy while Beth panted and moaned with every stroke. After he left, she made me clean her up and then we spent all night having wonderful sex together.

The story, even now, still makes me seriously hard. And although I know Beth would never do anything like that, it's a good example of the kind of kink I've been writing in my stories.

So, hopefully you can identify with what was going through my mind as I stood naked in my mom's kitchen, along with my mother and my sister, wearing only that condom. I wasn't sure exactly how far they would go with this, how many of my stories they had read and how much they really knew about my kinks, fetishes, and desires. But, there was a possibility I would be run through the ringer by the time they were done with me.

"Oh!" My mother suddenly said, breaking me out of my trance. "I forgot something upstairs we're going to need for the first milking. You guys get started on breakfast and I'll be back in a minute. Cassie," Mom added, "be sure you stay with your brother and watch him closely."

After Mom had left the kitchen, Cassie leaned over to me and quietly asked, "Did you say anything to Mom about what we did last night?"

"No." I answered, shaking my head.

Cassie told me Mom had come into her room this morning and asked about the nightie I was wearing, but, all my sister said was that she'd given me a pretty hard time last night, said some things that made me cry and then she felt sorry for me. So, she ended up giving me the nightie and panties as a way to say she was sorry.

"Well, I didn't even say half that much." I replied. "I just told her we talked for a while and before I went to bed, you gave me the panties and the nightie."

"Good." Cassie sighed. "I think she'd be pretty pissed at me if she knew I let you have my panties and made you jack off for me last night."

Then, Cassie sauntered up to me and put her hand smartly on my ass. "You've got a nice butt, big brother." She said, quietly. "And, by the sounds of it, I'm going to be very acquainted with it by the end of your punishment."

I turned my head to look at Cassie and she was grinning as she spoke, saying, "Mom seems to be pretty adamant about punishing you today. She seems to think it's going to humiliate the crap out of you – maybe even scare you back into Beth's arms." Cassie added. "But, I think she's wrong. I think you're going to be loving this the whole time."

"I can't wait to see this milking thing she's talking about." Cassie whispered to me. "I've heard about it, and if it's what I think it is, it sounds like it going to be more fun for us than it is for you."

Cassie's hand snaked around in front of me and she put her hand on my cock. As she started to rub me, she said, "I've got a surprise planned for you later if I can pull it off. I think you're gonna like it, that's all I can say right now."

We heard the toilet flush upstairs and Cassie said we better get busy with breakfast. Mom was just coming into the kitchen as I cracked the first egg and Cassie set the fry pan on the stove to start the bacon. Both my sister and I turned to see what was so important she needed from her room for my milking, and when Mom saw us both looking at her, she sat it all down on the kitchen table and showed us.

She brought three large, fluffy bed pillows, and two clean towels. She also had a few wash cloths, and finally, holding up a small bottle of personal lubricant, looked right at me, saying "You'll thank me later for not forgetting the lube."

Cassie broke out in a fit of laughter which caused Mom to snicker along with her. Then she gathered everything up in her arms and took it all into the living room and walked back into the kitchen.

"I was thinking we'll do his milking in the living room." Mom said casually to Cassie, as I broke the rest of the eggs. "There's plenty of light in there and we can just put your brother on the couch while we do it. Plus, there's enough room to move around so you can see how it's done."

My little sister was giggling as Mom spoke, and as I glanced over at her with a scowl on my face, Cassie just shrugged her shoulders and smiled at me.

"Mom," Cassie replied, "I'm kind of curious about something. How is it that you know so much about this milking stuff?"

Mom was pouring the fresh coffee into cups for the three of us, and without missing a beat, she answered Cassie's question just as if we were talking about the weather.

"Don't forget," Mom answered, "I used to be a nurse, and the milking is purely a physical reaction to stimulation of the male prostate gland." Mom went on to explain, saying, "It's an internal procedure, Dear. You know where the prostate gland is on the male, right?"

"Uh, yeah!" Cassie exclaimed, bursting out in laughter again. "Inside that cute little butt of his!"

"That's awfully crude, but correct." Mom answered. "We'll have to manually palpate the gland using a finger."

"You mean we're going to stick our fingers up his butt?" Cassie howled, laughing so hard I thought she was going to fall down.

"Well, yes." Mom replied. "As you get older, you'll probably discover on your own that many men actually enjoy some degree of anal stimulation, so it's probably a good skill for you to learn, Dear."

I was beating the eggs with a fork as I listened to them talk. My cock was throbbing and my face was red with embarrassment. They were talking about sticking their fingers in my butt and I was right there, in the same room with them, while they were discussing this. After a few seconds, I felt Mom's hand on my shoulder as she peered around my chest to see how I was doing with the eggs.

"You don't need to be concerned about the milking, Sweetheart." Mom said to me, lovingly. "I promise we're not going to hurt you. We'll make sure you're comfortable before we start, and we'll use a lot of lube. I realize this kind of thing can be extremely embarrassing for a man, but, if you want to earn our forgiveness, you'll just have to be brave and deal with it."

As she walked over to see how Cassie was doing with the bacon, Mom turned her head to me and added, "And Tom, you're not the first man to ever be milked, you know."

While we made breakfast, Cassie did little things to tease me – like reaching over to tug on my cock when mother wasn't looking, and, brushing her bra up against my arm or my back. I did manage to get a good look down inside Cassie's bra, though, and that was a pretty sweet treat.

I'm not normally a small tit guy, but Cassie's little pixie boobs were the things dreams were made of. Unlike Mom's much fuller breasts, Cassie's were very petite and firm. They were just little cones sticking out from her chest with cute, perky nipples. She didn't even have enough to have to wear a bra if she didn't want to, and quite honestly, they were beautiful little boobs, and I'd whacked off to the sight of them plenty of times in the past. I'd even tried a couple of her bras on a time or two while I was masturbating with a pair of her panties. And, even though I could get into them, they were way too tight to comfortably enjoy.

After more teasing, we finally sat down to eat. Mom carefully put a towel on my chair before I sat down at the table, casually telling me that while I was naked, I should probably use a towel for the sake of cleanliness. Again, Cassie broke out in laughter, but this time, Mom gave her a definite cautioning look.

As we were eating, Mom told Cassie she wanted her to run an errand as soon as they finished the first milking. "Your brother and I can clean the kitchen up ourselves, but, I'd like you to run over to the outlet mall for me." Mom said, casually. "Go to that underwear outlet store and see if you can find a few things for your brother to wear when I take him out to the grocery store with me later."