Virgin Boy’s Submissive Journey Continues: Ass Training and His First Punishment

Dear FemdomU Forum,

I’m excited to share more details about Mason’s journey with us. As I wrote before, Mason was 18 and needed somewhere to live for the summer until he started his freshman year of college. We gave him a room in our house, free of charge, and in return, Mason was our sex toy for the summer.

He came to us a virgin, so we decided to really draw out his experiences, slowly introducing one new thing after another. His third week as our sex slave was packed with new and intense experiences, pushing his boundaries and deepening his submission.

We began the week by focusing on training Mason’s ass. Logan and I led Mason into our bedroom, his nervous anticipation palpable. Logan took charge, instructing Mason to kneel on the floor. I watched closely, ready to offer guidance and encouragement.

Logan lubed up his fingers and positioned himself behind Mason. “Relax, buddy,” Logan commanded firmly. “You need to learn to accept this.”

Mason let out a guttural whimper, his entire body tensing up under Logan’s touch. But Logan didn’t back down, his determination evident as he pressed a finger against Mason’s tight entrance. The muscles clenched and resisted at first, but Logan persisted, applying more pressure until finally, with a gasp and a jerk, his finger breached the barrier and slipped inside. Mason’s body shook with surprise and pleasure, his breaths coming in short gasps as Logan’s finger explored deeper.

“Don’t you move, Mason,” I commanded, my eyes blazing with determination. “This is just the beginning of your training.”

Logan’s fingers worked relentlessly, plunging in and out of Mason’s tight hole, stretching it wider with each thrust. Two fingers became three as Logan scissored them inside, eliciting a mix of agonized moans and uncontrollable shivers from Mason. The cutie was so hard at this point, and even blushing a little bit. And when a fourth finger joined the others, Mason’s resistance shattered completely, replaced by an insatiable hunger for more. He pushed back against Logan’s hand, begging for even deeper penetration and giving in to the overwhelming pleasure coursing through his body.

“That’s it, Mason,” I urged. “Let go and feel the pleasure coursing through your body.” Logan’s fingers danced with expert precision, skillfully stroking Mason’s prostate as if playing an instrument. Waves of intense pleasure crashed over Mason, his moans escalating into primal screams that echoed through the room. Finally, after what felt like an eternity of ecstasy, Mason’s climax exploded. Without his cock even being touched, he released a torrent of cum onto Logan’s lap as his body convulsed with pleasure.

The next day, I brought out a massive anal plug that I often used on Logan, determined to push Mason’s limits even further. Logan’s eyes widened in concern as he saw the size of the plug, questioning my decision.

“Are you sure about this, Sara? It’s too much for him,” Logan cautioned.

“It will fit,” I insisted, ignoring his doubts. “I’ll make it fit, and he needs to learn how to take big things, don’t you agree?” I looked down at Logan’s cock, just to be clear where my intentions lie. As I said before, the boy came to us a virgin. We trained him, and by the end of summer, there was nothing virgin about him anymore.

But, back to afternoon, with gentle yet firm hands, Logan positioned Mason for what was to come. “Relax, Mason. I’m here,” he murmured soothingly, trying to calm the trembling boy. Logan was even rubbing Mason’s back as I generously coated the plug with lube and pressed it against Mason’s quivering entrance. Fear and anticipation flickered in his eyes as he braced himself for what was about to happen. With a steady hand, I began to push, meeting resistance with each inch gained. Mason screamed in agony, his body thrashing and struggling to escape the intrusion. But Logan held him down firmly, whispering words of comfort and support.

“Take it, buddy. You can do this good boy,” Logan encouraged him.

As the plug slowly but forcefully entered him, Mason’s screams morphed into whimpers and then moans. His body shook with the effort, tears streaming down his face, but still he pushed through the pain. And finally, with one last push from me, Logan holding him in place, the behemoth plug was fully inside him. “I told you I’d get it in there,” I said, looking Logan in the eyes.

Mason’s cries subsided into gasps of relief mixed with a strange sense of satisfaction. I had him roll over on his back and while Logan praised him with soft kisses and words of admiration, I rewarded Mason with a slow and deliberate handjob, watching as his face twisted in pleasure. Soon Logan couldn’t hold back any longer and stuck his erection in Mason’s mouth. The boy took it like a champ, but didn’t last long himself, shooting his load all over his stomach. I knew Logan would take awhile to cum, and frankly I’d had enough by that point, so I left the boys to do their thing and enjoyed a margarhita on the patio.

His First Ass Fucking

The following day, we told Mason to get ready to be fucked in the ass. Fear flashed in his eyes as he glanced at Logan, but I quickly reassured him. “Not Logan, not yet” I said with a sly smile. “We still want you to remain technically a virgin, for now. That means no dick in your hole, and your dick in no hole. But my cock is a big dildo, so it doesn’t take your virginity. I can fuck you senseless, and you’ll remain our little virgin boy!”

Mason looked relieved but still nervous. Logan and I led him to the playroom, where I strapped on my favorite dildo. Logan positioned Mason on all fours again, his hands caressing Mason’s trembling body.

“Relax, Mason. You’re going to enjoy this,” Logan whispered, his voice filled with both lust and reassurance. My cock had been in Logan’s ass countless times, and it was something he could never get enough of.

I lubed up the dildo and pressed it against Mason’s entrance. His body tensed, but Logan was there, once again playing his part of reassuring coach, whispering soothing words and stroking Mason’s back. I pushed in slowly, feeling the tightness of his virgin ass around my dildo. Mason gasped, his body shuddering.

“That’s it, Mason. Take it,” I commanded, pushing deeper.

Logan’s hands roamed Mason’s body, caressing and comforting him as I thrust into him. Mason’s gasps turned to moans, his body starting to respond to the overwhelming sensations. Logan couldn’t help but get turned on, his own erection growing as he watched me fuck the boy.

Logan began to jerk off, his eyes never leaving Mason’s face. The sight of Mason’s submission and pleasure was too much to resist. He moved closer, guiding Mason’s head towards his throbbing cock. Mason took Logan’s cock into his mouth, sucking eagerly as I continued to fuck him.

The room was filled with the sounds of moaning, panting, and the rhythmic slap of skin against skin. Mason was lost in a haze of pleasure and submission, his body completely at our mercy. Logan’s hand tangled in Mason’s hair, guiding his head as he fucked his mouth. I could see the pleasure building in Logan’s eyes, and soon he was close to release.

Logan pulled out of Mason’s mouth, stroking himself furiously. With a loud groan, he came, his hot cum splattering across Mason’s face and chest. I continued to thrust into Mason, pushing him over the edge. Logan started stroking Mason, and in half a minute he came with a loud cry, his body shuddering in ecstasy.

His First Punishment

The final day of that third week was a brutal, relentless barrage of torture for Mason. Mason had a morning routine – he would awake before us, make the coffee, then he’d come into our bedroom and wake me up first, climbing between my legs and pleasing me with his mouth. Once I was done, I’d leave and enjoy my coffee on the patio while he woke up Logan the same way. However, on this particular morning, Mason slept through his alarm, and missed his morning duties. Once he woke up, Mason knew he was in trouble as he faced the wrath of Logan and I with trembling fear. We bound him in the playroom, stripping away any sense of control or protection over his naked body. My fingers curled around Logan’s favorite bullwhip, eager to unleash its cruel power on someone else for a change.

I could see the terror in Mason’s eyes as he watched us prepare. He had never experienced such punishment before – not even a simple spanking as a child. Logan, still seething from the lack of a morning blow job, showed no mercy or reassurance towards Mason. Instead, he coldly ignored him, leaving the boy alone with his racing thoughts and fears of what was about to come.

I bared my teeth in a feral grin as I traced the tip of the whip across Mason’s exposed skin, savoring the fear and anticipation radiating off of his tense body. With a swift snap, leather met flesh with a deafening crack, the sound reverberating through the room as Mason let out a guttural scream.

“Stay still, Mason,” I commanded, relishing in his helpless struggle against the restraints as I continued to rain down lashes on his quivering form.

Mason’s screams echoed off the walls, mixing with his anguished sobs and desperate pleas for mercy. His tears flowed freely as red welts formed on his already battered skin, each strike causing him to convulse in agony. As Logan watched with depraved pleasure, his gaze filled with twisted desire at the sight of Mason’s pain and vulnerability under my control.

“Jerk off on him, Logan,” I growled, my voice laced with sadistic pleasure as I continued to relentlessly whip Mason’s bare back.

Logan eagerly obeyed, his hand moving faster and faster along his cock as he watched Mason squirm in agony. The sound of the whip cracking against Mason’s skin mixed with the wet slapping noises of Logan’s hand on his own flesh. And then, with a final thrust and a loud moan, Logan came, his hot cum splattering across Mason’s now raw and bruised ass.

Mason’s cries subsided into whimpers, his body trembling. I stopped the whipping, running my hand over his marked skin. “You did well, Mason.”

Logan and I untied Mason, comforting him with soft touches and words. We applied first-aid and ointment to his owies, and made sure he had a relaxing afternoon. He’d made a mistake, he’d learned about punishment and he learned his lesson. I was certain he’d not sleep through another alarm.

He had endured so much, and his transformation was remarkable. He was no longer just a virgin boy; he was our obedient, eager sex slave, ready for whatever we had in store for him next.

More to come soon,

Sincerely,

Sara