You Know, I’ve Been Thinking…I Always Get Asked About Long-term Male Chastity, And I’ve Always

You know, I’ve been thinking…I always get asked about long-term male chastity, and I’ve always felt like a month is the longest period of having a guy locked up without orgasm that I would be able to stand, mainly because I love having sex and would want to have my holes penetrated, etc. But, upon further thought on the matter, I think I could probably push the max chastity time to 3 months, under a few conditions. He would be giving me lots of oral sex. For his health and safety, as well as my personal enjoyment, he would agree to periodic prostate milkings, either by my fingers or a toy. He would need to present himself to me on all fours, nude, on our bed for nightly inspections of both his caged cock and his ass. And, most importantly, he would need to learn how to use a strap-on very well, as he would need to fuck me whenever I needed to be filled and still be able to maintain his chastity. As long as I’m having orgasms and having my holes filled, several months of having my sub locked up actually sounds rather…enticing.

More Posts from Dangerousangleofadream and Others

7 months ago

I’m so hungry for a shy boy in bed… I want to tie his hands to my bed posts, strip him off his pants and see him turn crimson red in the face when I look at his body like it’s the most delicious meal I’ve ever seen. I want him to moan and squirm when I touch his hard cock the first time… begging me to stop but his body language will tell me otherwise.. slight thrust against my palm and later in my mouth. I want him to whimper and sigh, be noisy and desperate. I’m hungry for the look on his face when I slide his throbbing cock inside my pussy and feel him all the way in. When he tries to hide his face or bites his lips to muffle the moans I just part his lips with two fingers and force his mouth open, make him unable to suppress all the sweet sounds he makes while I ride him. What I want is a boy stripped off all the worries and thoughts that make him think he has to act cool. Act ‘manly’. I want him to lose a fight against boundaries and give in to the pleasure I cause. And I want to hear him cry my name as he cums.

The Diapered Banana Challenge

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While I was being changed in the bathroom, I looked over to see a bowl of peeled bananas. These ripe fruits were cut in half and glistening with an unknown liquid. Being the innocent babyboy I was, I meekly asked my Mommy what the bananas were for and she declined to respond. Having no diaper secured around me, I grew anxious as my feverish chilled body demanded warmth. Mommy had me crawl to her on all fours and turn around. I did not know what to expect as I waited for something to happen.

Only moments later, I felt something circling at my rear entrance and then plunging in, I turned around and yelped to find that Mommy was fingering me to ensure I was well lubricated. In a split second, the finger was replaced by a thermometer to measure my fever. Mommy pushed down on my back so my ass was facing up and commented on the excitement between my legs, “Someone is enjoying this, isn’t he?” I couldn’t muster up a response… She quickly picked up a paddle and swatted my ass several times before saying that I would be forced to use my diaper appropriately.

I felt a nudge behind me once again, but this time it was noticeably larger. Looking back, I saw that there was a banana half missing from the bowl, and before I could say no, a felt the fruit slip inside of me as my butt pulled it past my tight hole. I sobbed in protest, “Mommy, I’m a big boy! You can’t make me use diapers!” To which she responded, “You don’t have much of a choice, babyboy. These glycerin coated bananas are going to ensure that you won’t be able to hold your bottom. You’ll prove to Mommy that her babyboy needs to be diapered!” I continued sobbing as I sank deeper into subspace, becoming silent and relaxing my butt to make the process easier. Before I knew it, the process was over, and I knew I had seven banana halves packed into my sore butt. My mommy restrained my ankles and left the room, allowing me some time to process what had just happened.

Upon her return, I felt more pressure… “Baby, you are going to take this plug for me so that I can control when you lose control. We can’t have you give up too quickly or you won’t be able to savor how truly helpless you are!” She pushed the plug home with the palm of her hand and rolled me over and quickly diapered me to ensure that the plug would be held in place. She pulled me up guided me to bed, setting me atop a pile of pillows so that I could indulge myself, gently rubbing myself against it.

I began to lose myself in space again, then a cramp stopped me immediately. Mommy noticed and commented, “Awe baby, that’s the glycerin doing its work in your bottom. It will make you start to push soon enough!” In an incoherent protest, I mumbled into the pillow under my head and resumed humping the stack of pillows as cramp after cramp began to debilitate me. I rolled to my side in defeat and curled into a little ball as I found myself on the edge of releasing, only to be reminded that the plug was holding everything in. I begged, “Mommy please I need to go potty!” The pleads fell on deaf ears as she stared into my eyes, conveying the message that I already knew: I was going to use those diapers…

She reached behind me, her hand caressing my clenched butt before grabbing the base of the plug, pulling it out, and watching my eyes immediately widen in anticipation of what was going to happen. In a kind voice, she cooed, “Use it honey. It will make you feel better.” I told myself I couldn’t give in to my body’s demands and help for what seemed was hours… and then it happened.

In seconds I transformed from an adult wearing a diaper to her babyboy. I tried to hold even as the first half left my bottom, but the rest of the tightly packed bananas filled my diaper as if I were incontinent. The warm mass caressed me and calmed me in a way I wouldn’t have expected. I froze once again before gently humping the pillows again. Mommy let me continue, knowing that having cummies would enforce the events leading up to this moment. I climaxed, immediately became drowsy, and drifted into sleep.

I was Mommy’s babyboy.

7 months ago
DATE 💯

DATE 💯

7 months ago

"Puppy boy, this"... "puppy boy, that"

Totally valid, and very adorable... But what about the slightly cranky, solitary and often, incredibly smart black cat boys?!

Coaxing them out of their moody little shell until they're practically nuzzling against your palm for attention...

10 months ago
Mistress??

Mistress??

8 months ago
@myheartinherhands

@myheartinherhands

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