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:
