The next morning my alarm starts buzzing already at 4:30. I want to have plenty of time to get through my morning routine. I'm usually very tired in the morning, but today I wake up easily with lots of energy. I try to stop myself considering why that is.
I look at the floor beside the bed where the gift box from Mike lies. The row of butt plugs looks like an exclusive set of cutlery. I see the step up in size from the Monday plug that I had to remove overnight to the Tuesday plug and get simultaneously scared and excited. I know the week's supply of enemas lies below the layer of plugs and realize that it's time to move.
I pick up the box carefully and walk to the bathroom where I proceed with taking the Tuesday enema, which is much easier now after the training yesterday. I then proceed to shower before it's time for the inevitable. I remove the Tuesday plug from the box and hold it in front of me. It's almost looks twice as large as the Monday one and thicker as well. Aside from that, they are similar in color, the penis shape with a head at the top, a shaft below and then drastically thinner size closest to the large pink colored silverish plate base, ensuring it will remain tight in my ass once it's in.
Although I desperately want to do this degrading procedure in private, I know that Emma and Jessica are expecting to see it in the morning video that I am forced to send to our What's app group that also includes Amy and Lisa. Reluctantly I set up my phone for video mode and press record.
"Dear wife, dear daughter," I start. "Dear Lisa and dear Amy. Thank you for allowing me to be your cuckold. Please enjoy as I try to fit this cock into my tight little asshole."
I hold up the pink, penis shaped plug to the camera as I contemplate how easily and emotionally those words rolls off my tongue these days. I proceed lubing the toy before getting on my hands and knees and put a similar large glob of lube on my needy hole. With my ass turned to the phone, I proceed to push the plug as hard as I can but after a few tries, I must give up. My sphincter is simply not flexible enough in this position.
Thinking about what I've seen in porn films, I conclude that maybe it will be better to crouch over the plug. So, I get up on my feet and as I crouch, I push it again as hard as I can but to no avail. It feels impossible to make it fit. Even if I open a little bit, it's not nearly close enough to swallow the round, pink head. Knowing failure is not an option, I get down on my back and put my legs up in the air. I apply another generous click of lube around my asshole and proceed to push the plug. This time I can feel myself open up more and more.
"Aaahh, aaaahh, aaaaouuu," I pant before having to admit defeat once again as the pain gets overwhelming. I give it another go. This time my sphincter is already more relaxed so I get even further. It's so close, and so frustrating. In the end, I must remove the pressure once again. Instead, I start pumping the plug with just a little bit of force. After fifteen pumps I shove it in as hard as I can. I feel my inner walls give way as the plastic, pink head enters my ass with a "plop".
"Aaaarrrgghhhh," I scream from the pain. Once my ass opens up for the head, the rest of the plug slid right in at the same time. The thin ending next to the base plate ensures my sphincter closes tight behind it, keeping it in place.
"Ah.. ah.. ah.. ah..," I pant as I breathe heavily, trying to encompass the huge intrusion in my ass. I can't imagine how pathetic I must look on the video with my shaved pubic area, legs spread in the air and panting like crazy from a plastic cock in my ass.
After a good five minutes, I got more used to the size and decide to make an attempt to fulfill the final part in the video. My daughter instructed me to jerk off every morning, just to the point before I cum. I get up and take a seat on the edge of the bathtub to comply with the request. It feels so strange to move around with such a big thing in my ass. To my surprise, I notice that I have a full erection, harder than I've ever experienced before. It's like the plug in my ass shoots straight up to my penis, filling it with a completely new level of stiffness. I touch the head and it jolts from the sensation. I can't help to let out a moan.
I slowly wrap my fingers around my stiff shaft and move my hand upward slowly. The sensation is extreme and as I move my hand downwards again, I feel the rush of a bursting orgasm building. I instantly remove my hands but the nerves in my body make my sphincter twitch against the plug planted in my ass. The sensation feeds back to my penis that jerks up and down without me even touching it. In a last attempt to keep from climaxing I breath heavily and try to focus on things turning me off. I finally feel the impending rush of cum settling down after ten seconds when I allow myself to relax a few drops of pre-cum, or maybe it's cum, appear from my cock head.
"Thank you, Emma," I state in normal fashion. "For allowing me to be your cuckold. Thank you, Jessica, thank you Lisa, thank you Amy. Thank you for training me," I go on. I don't really want to, but I'm so horny now that the words just roll off my tongue. "Thank you for making me understand I'm just a useless cock slut, orgasming from having a plastic cock in my virgin ass. Now I'm off to suck Nick's cock. I thought I would hate it, but I'm excited. I can't wait for his cum to coat my pathetic cuck face. Thank you," I state one final time before stopping the video and uploading it in our chat group. Immediately after pressing send, I regret my words, feeling embarrassed. Looking at the time, I realize I need to get moving if I'm to make Nick's 6 AM wake up time.
I wobble downstairs, trying to be as quick as possible with the huge intrusion in my ass making itself known each step I take. When I open the front door and feel the rush of cold morning air hit my body, I realize what I'm about to do. If anyone catches me in this well-off suburban block, a middle-aged man running around naked, with a dildo in my ass, I will become a social outcast a best. Possibly even arrested.
I look over at my closest neighbor on the left and see that they are still sleeping. The situation seems to be the same in most houses. I see one or two lights on but no people. I hear voices in the distance, but my best estimate is that they are far away. I decide to make a run for it. I tippytoe off our porch, over the cold paved driveway and across Nick's lawn where the grass is moist from morning dew. The swift action makes my insides squeeze the plug in my ass. My still rock-hard erection sways from left to right as I make my way over to my tormentor. I run up to Nick's porch and put my hand on his doorknob. As I turn it, I'm happy to notice that he has left the door unlocked. I open it quickly, step inside and close it behind me.
All of a sudden it feels like I'm in a different world. The cold has changed to warmth. The sound of the wind has disappeared and it all feels desperately silent. My mode changes as well, from trying to be as quick as possible to trying to be a quiet as possible to not wake up Nick's sons. I feel even more exposed being naked in someone else's house than I did running in the open. Having been to Nick's for poker night before, I know his bedroom is upstairs. I make my way there being as careful as I can to not make a sound. I push his door open carefully and see Nick sleeping in his huge bed.
"This feels so awkward," I think to myself. But I also know there is no way out. I take a few steps towards the bed and close the door softly behind me. I hesitate a bit on the best way to proceed but decide to crawl under the covers at the foot end. I can see that Nick sleeps in the nude. He lies on his back, tilted slightly to the side. I can tell he showered before going to sleep as he smells fresh.
I make my way up to his soft, clean shaven cock. It hangs from between his legs and the tip rests on the bed. I can't help but feel that this is even more degrading than everything I have experienced before. I've done way worse things, but this is a different level of intimacy, one that I'm forced to have. Somehow, that makes it way worse. Or maybe it's worse because somewhere deep inside I feel myself wanting it.
Regardless, I lift his limp member with my index and middle finger, open my mouth and let it slip inside. It's such a different experience having a soft cock in my mouth. The texture is different along with the smell and size. I let my tongue caress it in my mouth and move my head slightly back and forth. I press my face against Nick's body and can't help but laugh a bit in my head when I realize that I am finally able to fully deep throat his cock again on my own this time. What an achievement.
After a minute or so of work I can feel the shaft coming to life slightly. This makes it easier to stimulate. I remove it from my mouth and jerk it with my hand while kissing the head, making it swell by the second. Nick adjusts himself so he is fully on his back, allowing me even better access. I continue to jerk his cock, but now I'm letting my tongue make its way downwards until I get to his balls. I kiss the wrinkly skin before putting one in my mouth, sucking it while massaging his shaft with my hand. After giving his other ball some attention, I move my head up to the top of his cock, engulfing it again. This time I feel the full size of Nick's white monster and I start bobbing my head up and down as far as I can. Although I can only catch half of his erect length, I can feel the taste of flowing pre-cum as he must get excited from continuously slamming towards the back of my throat.
"Fuck yeah," I can hear him grunt above me.
I continue my frantic pace before removing his cock from my mouth. It's now completely covered in my saliva and his pre-cum. I smear it in my face as I lick and kiss my way up and down his warm and veiny shaft. I can't help but enjoy the messy mixture. I tightly squeeze the base of his cock with my hands, making it stand straight up and pulsate while I use the tip of my tongue to massage the underside of the head. Without thinking I open my mouth again to let him in so that I can taste the alpha ecstasy coming from him.
I instinctively start to bob my head up and down, trying to get as much of him in my mouth as possible. This time I feel Nick's hands grab my head through the duvet. With a powerful grip he keeps my head where it is and start to thrust his hips, force feeding me his cock. It swells with each thrust and the more I struggle, the more excited he seems to get. His pace gets frantic as I hear him pant above me. Then, without announcing it, he slams his cock into my mouth one last time and keeps my head in place. I feel the shaft start to twitch and then the gush of the first cum spurts towards the back of my throat.
"Aaaaaarrrghhh," he grunts like a primate above me.
My emotions are running wild, mixing a sense of pride being such a good cock sucker, with shame, humiliation and resentment. I try to swallow as much as I can, but I can't keep up and start to cough, streams of cum running out of my mouth. Nick removes his hand to allow me to cough. Two spurts hit my face, coating me with his warm semen.
