Category: gonewildstories

Remind me not to earn another punishment from Mr. Envelope.
I knew it would be bad- the man gets under my skin like no other before or since him. The mental gymnastics that he puts me through surpass the physical; when I play with him, I know that I am going to be challenged and broken. I had never been punished by him until tonight- and I am not eager for a repeat performance.
He started by reviewing the agenda; he enjoys watching my face as he walks me through his plan, and it also serves as a way of gaining consent and assessing limits. “As you know, tonight is about punishment,” he began in his low, even tone. “You will not orgasm tonight. This is not going to be fun for you. I, on the other hand, will be having an orgasm, and I will be using your mouth to do it. You will be hooded and wearing a ring gag for the duration of the night. I will use you as I please, and you will make me cum using your mouth. I will cum directly into your mouth, and you will swallow as much as you can. Anything that leaks onto the floor, you will lick.” I nodded along, making an effort to quell the butterflies, knowing that they were wholly inappropriate for the situation. “I may write on you, I may spit on you. I will hurt you. I will degrade you. You are little more than an object to me tonight, and I will make you feel that way. You will not hear me call you a good girl. When I am done with you, you will remain an object while I drink my coffee. You will remain still and silent until I free you. Do you understand?”
I made an effort to keep my witty quips to a minimum. As excited as I was by much of what he said, I am experienced with him enough to know he meant it when he said that this wasn’t going to be fun for me. I nodded, steeling myself for what was to come- if I had only known, I might have run for the hills.
I stood in my living room fully clothed while he secured the ring gag and hood. I was plunged into complete darkness, my mouth the only part of me exposed. My tongue and jaw tested the ring gag, finding it fairly rigid and unforgiving. I could already feel the spit in my mouth pooling. Gulp (literally).
“Strip,” he said simply. Even though I couldn’t see him, I could feel his gaze burning through me. I removed my shirt, bra, and pants (of course I wasn’t wearing panties). I found myself feeling disoriented, even though I have spent countless hours in my living room. My spatial awareness was flawed, and as he moved silently around me, I lost perspective. When he finally stopped in front of me, he had my full attention.
I felt the tip of a marker on my breast, and briefly tried to guess what he was writing (I still don’t know- the drool and bruising made the writing disappear before my hood came off- I’ll have to check the photos). The moment was intimate, a symbol of his control over me and my surrender to him.
I took a deep steadying breath as he wrote, embracing my submissive role. I squared my shoulders, dropping them and focusing my weight into my feet and through the floor. I placed my hands behind my back, sinking deeper into my favoured submissive stance. I felt grounded and serene- ready- until the first blow landed.
I forgot to mention- he got a brand new riding crop, made of the smoothest and softest leather. It transformed to a biting flash as it made contact with my soft breast. I yelped, more in surprise than in pain, though the sting of the crop lingered. I adjusted my posture, mentally preparing for additional impact. As a practiced sub, I could already feel myself sinking deeper into the moment.
I was therefore quite surprised to feel tears sting the corners of my hooded eyes after the third blow. He was just getting warmed up, and so was I- tears were decidedly unexpected at this stage. I mentally chalked them up to irritation from the hood, and refocused my attention on absorbing the intensifying sting of the crop on the tops of my breasts. The leather made a wicked sound each time it made contact, and the resounding sensation was becoming more painful. He struck my left breast, and then my right, and I felt the first string of drool in between them. The yelp I swallowed became a sob in my throat.
I could feel the tears coming before they arrived, seemingly from deep within some unexplored part of my soul. I choked out a sob as the next blow landed, my mind racing to try to understand what was happening. I have endured some pretty impressive impact play in my years exploring BDSM, and I have truly sobbed only twice. The shock of the tears was just as jarring as the continued assault on my breasts. I breathed deeply in an effort to get myself under control, but the tears were already flowing. I finally moved my hands to my breasts, an effort to protect my body while I sorted out my mind.
As I reflect on it now, I still don’t know what the trigger was for the tears. I have been feeling vaguely unsettled in my personal life, the unnamed root cause still just out of my grasp. Maybe the hood provided a layer of safety- a mask to cover my vulnerability. Maybe it was the degradation- seeing myself as a hooded figure: helpless, marked, drooling, and in pain. Maybe I just needed a good cry. What I do know is that it got much worse.
As I covered my breasts and tried to quiet my sobs, he gave me a moment of reprieve. “Get on your knees,” he said. His voice remained deep and even, without an ounce of warmth in the face of my fraying edges. I did as I was told, grateful for what I hoped was a change of pace. I heard him unzip his pants, glad that his hands were otherwise occupied. I took advantage of the opportunity to collect myself, and found myself feeling more in control as he sat on the couch.
“Come toward me,” he said, and took my hands as I crawled to the edge of the couch. He placed my hand on his cock, allowing me to stroke him. “Use only your mouth,” he said easily, and I lowered my open mouth to his cock.
Without the luxury of sight, and with the ring gag firmly in place, I was decidedly out of my element. Sucking his cock while gagged was like re-learning how to ride a bike. My usual practiced, fluid motions were clumsy and delayed as I worked to ensure that his cock was inside the ring, and then figure out where my tongue goes. I couldn’t close my lips around him, so I couldn’t suck, swirl, and swallow with my usual flair. My teeth were outside the ring, so that was one less consideration, but it took a fair amount of focus to get his cock back into my throat with the added obstruction of the ring- not to mention the drool. There was spit absolutely everywhere, freely falling down my chin and onto his cock. Thick spit pooled at the sides of my mouth as I tried to swallow him, each effort to get him in my throat rewarded with another gush of spit. I gargled his cock and my spit, choking and drooling as I tried to please him.
He let me get my bearings and find.my own rhythm before he put his hands on either side of my hooded face. He bobbed my head up and down on his cock, my tongue teasing the head of his cock through the ring gag before he forced himself back into my throat. The longer he held my head on his cock, the more I felt like I might drown in my own spit. I could already tell that I was a mess.
When he tired of face fucking me, he ordered me to kneel again. I stood tall on my knees again, placing my hands behind my back obediently. I was still shaky from the surprise tears and clumsy blow job, but now that I had figured out how to suck his cock with a ring gag I felt a little more solid.
When he hit me with the crop again I wasn’t ready for it, but I adjusted quickly. I lowered my shoulders, doing my best to quiet the panic building up inside of me. The tears were far closer to the surface than I had thought, and I could feel them falling as he hit me a second time. Before I realized what was happening I had covered my breasts again, falling back on my heels and curling into myself as the sobs took over. I felt frantic and scared, completely out of control.
I am not a dainty crier, especially with a ring gag in my mouth.
“Get back up…you will present them to me,” he said evenly. All I wanted in that moment was to be comforted, and instead he demanded more. I stood back up on my knees, shaky and sobbing, and placed my hands gently under my breasts. I raised them, pressing them together- presenting them to him against all of my better judgement.
My body and mind screamed in protest, drool falling onto my throbbing skin while tears soaked my hood. I squeezed my eyes shut, swallowing a sob as he landed the crop on my breast with a sharp snap. I began freely crying, and he didn’t let up. I tried with every fibre of my being to surrender to him- to the pain- as blow after blow landed on my tender skin. My fingers dug into the underside of my breasts, my teeth biting down as much as the ring gag would permit. Guttural sounds escaped my throat as I sobbed, the pain and fear finally getting the best of me as I turned into myself and covered my breasts.
“Present,” he ordered. I took a few deep breaths, reluctantly straightening myself in front of him. I could feel drool between my legs, down my stomach, even on the floor. I gently cupped my breasts, begging my body for forgiveness as I steadied myself for more torment. He was relentless, his crop demanding tears and screams (and later, I found out, bruises) from me in equal measure.
My body and mind flooded with relief when he grabbed my hair and thrust his cock into my drooling mouth. I was still crying, but it was easier to find my footing when the crop was resting.
When I gagged his cock out of my mouth he covered my nose and mouth, causing a new wave of panic to course through me. Breath play demands serenity; panic only makes things worse. I used every grounding technique I know to quiet my screaming body, but the residual sobbing made it much too difficult. I tapped out, and he went back to face fucking me.
When I gagged again, he covered my nose and mouth, this time demanding that I hold on. His encouragement (vague threat?) gave me a bit more stamina, but I tapped out again. I held on longer for the third time, but he still got the better of me. (Side note: that is certainly something I am interested in trying more of, maybe without the tears).
Next, he ordered me to lay down. He rubbed the head of his cock along my pussy. I could feel that I was soaked- with excitement, with spit, who knows- likely a combination of both. He eased inside of me, reminding me that I was not to cum. By this point I had an acute understanding of the depths of his punishment and was absolutely not interested in disobeying. His cock felt exquisite, especially after everything he had put my body through, but I stayed well off the edge.
He sat me back up, thrusting his cock now soaked in my juices back into my ever-awaiting mouth. He used me until he came, filling my mouth with salty cum. I braced myself as he shuddered, feeling his hot load at the back of my throat. I swallowed a few times as best as I could, tilting my head back to get as much of it as I could down my throat. He pulled back, watching me struggle to swallow the rest of him.
I breathed deeply as I came back down to earth, relieved that the torment was over- except it wasn’t, not quite.
He helped me to stand, and then had me sit in a comfortable chair in the corner. I remained naked, fully drenched in spit (more wet than if I had just gotten out of the shower), hooded, and gagged. He told me that I was to sit quietly in the chair- an object for him to admire, but nothing more. He said that he was going to drink his coffee, and that I would sit there for an hour and a half. At the 45 minute mark, I was permitted to ask to be released, but if I asked before 45 minutes had passed, I would endure another round of punishment. If I made it the full hour and a half, I would be released without incident.
You’ll recall that in an earlier session Mr. Envelope had me count ten minutes in my head, and it was an abject failure. I decided early on that I was not about to risk additional punishment by trying to free myself after 45 minutes; I buckled down for the full hour and a half.
I heard him take his seat on the couch across from me and sip his coffee. I could hear the central air kick on and off, making me instantly freezing- especially as I was largely soaked in spit. I could feel acute soreness in my breasts, and my jaw was well past aching. I could feel his eyes on every part of me.
I also knew that this was the home stretch. I had survived (barely) the punishment so far, and all I had to do was sit quietly for an hour and a half, under his gaze. I slowed my breathing, taking deliberate stock of my body and mind. I was still reeling from the surprise tears, so I decided to use the forced reflection time to investigate that. I didn’t get very far with that initially, so instead pivoted to counting- not in an effort to mark 45 minutes, but as a grounding exercise- like counting sheep. By focusing my mind, I was able to relax my jaw, and pull attention away from the self-consciousness he was creating.
The hour and a half passed slowly and quickly, all at once. Each time the central air came on I was sure I would freeze to death, but as it lulled I could feel relief in my skin as it warmed. I remained vaguely aware of his potential gaze, but it became more comforting than intimidating. I thought about our bond, and how incredible it is that he knew to keep pushing me through the tears instead of backing off. I began to feel grateful to him, instead of fearful of him. I felt myself fidget a few times, more in an effort to ease cramps or refocus my thoughts than out of discomfort. I reached a state of serenity, my body and mind finally at peace.
He didn’t say a word until he stood to release me. He undid the gag, and removed my hood. The brightness of the lights was jarring, as was the breaking of the scene- it took me a moment to be able to look him in the eye. I had experienced such intimacy at his hands, and had given him vulnerability and submission- that kind of power exchange takes a moment to recalibrate when the scene is over.
He stayed to talk, ensuring that I was okay and put back together before he left. He photographed my bruising breasts, gently and appreciatively running his fingertips over his handiwork. We brought our dynamic slowly back to neutral, assuming our regular push and pull conversation.
As he was leaving, he took me gingerly in his hands, leaning in to kiss me- and didn’t.
Remind me not to earn another punishment from Mr. Envelope.