Switching gears a little bit from where I left off, the relationship between F and I had quite a few complications. We would see each other about 8-10 times a month, but we only got alone time together about once a week. We would try to make the most of it and the days we were together were jam-packed. F and I would talk and correspond regularly, but there wasn't a lot of together time.
I briefly spoke about F having put limits on herself. For years her exploration of dominance had been limited to some mild bedroom play and the occasional whipping sessions with various consenting subs at BDSM gatherings. The events had a start and a finish and there were defined limits. Often being one of the leaders of the events, she believed she couldn't make mistakes (e.g. going to far and really hurting someone).
When we first started meeting privately I realized I was going to have to nudge her forwards a little as well as prove that I could handle it. On a day F was to arrive I woke up several hours early to get prepared. I made some coffee and baked some bread and spent the rest of the time readying the room. By this time I had accumulated quite a bit of BDSM gear as well as a few items specifically for this day. I had some straps set up at the corners of the bed. My collar and wrist and ankle cuffs were out on the table along with a ball gag, blindfold, a collection of locks and chains, and some spanking devices (paddle, slapper, etc.).
F arrived and we performed our collaring ritual. I served her some coffee and bread and we talked for a few minutes. Her eyes kept moving back and forth over the table. I watched her and said, "I wanted to make this special for you." After finishing her coffee, F asked me what I wanted to do.
I replied, "I want you to do whatever you want to do to me."
"Are you sure?"
"Yes. Anything is fine."
"I don't want to hurt you."
"It's okay to hurt me."
"I don't know."
"What's the worst that can happen? You hurt me, I heal, and we dial it back a touch next time?"
I stripped naked for F and put the cuffs on my ankles and wrists. I handed her a lock and allowed her to lock the locking buckles. I took the gag and blindfold in hand and some more chains and locks and moved over to the bed. I had prepped each strap with an unclasped lock beforehand. I took some small sections of chain and locked one to each strap. At that point I handed 4 locks to F. My last words were: "I don't want a safe word. This gag is to make sure of that. Don't worry about me, focus on what will bring you the most pleasure. I love you and I will suffer for you. If you are afraid, just see if I am erect or not and you'll have your answer."
With that I put the gag in my mouth and secured it behind my head. I lied down on the bed, lined up my ankle cuffs with their closest chains, puled the blindfold over my eyes, and placed my wrists as close to where I could remember the chains being. F locked each cuff to the chains and when she was done, I gave a tug to test (and show her) the range of motion I had. I was pretty much secured spread eagle. I couldn't speak, I couldn't see. My penis was erect and my breathing started to get heavy.
I could hear F slowly moving around the bed. She made some small noises but nothing that resembled a word. I felt her climb onto the bed next to me and straddle me. She was still in her jeans but I could feel her heat pressed against my stomach. Her fingers closed around my nipples. First she rubbed them, then gave them some taps and they were soon as perky as my cock. I felt her left hand begin to squeeze, harder and harder. I bucked my hips in pain and she eased up her grip. The nipple was no longer erect. Her lips closed around it. I could feel her teeth gently nibbling and her tongue teasing its tip. She removed her mouth and blew on it several times. The evaporating moisture made this feel very cold, and the nipple was erect again. She gave it a flick with her fingernail and my whole body winced. Her fingers closed around it again and applied firm pressure.
She released my right nipple and I felt her lips there. Suction, tongue, I let out a muffled moan from under the gag... then teeth. I squealed. She removed her mouth and blew again. It was freezing. Tap, tap, tap and the nipple was erect again... F dug her nail in and twisted. I squealed and bucked. This continued for quite a while. When she tired of it, I felt her change position on the bed. I felt her fingers at the base of my cock head. She started to slowly slide them up and down in small motions. It stiffened more under her touch. She added another finger to the grip and widened the motion a little, I took a deep breath and moaned. F then grabbed on and made a fist around it and with a little tug my breath left me.
She finally spoke. "If you dare to cum without permission I'll kill you." Her tone sounded half serious, half joking.
I felt her mouth on my penis. Apparently F was highly skilled at this technique and in about 5 seconds I felt like I was going to burst. I started to lift my hips a little when, SMACK, I felt her hand slap my thigh. I stopped moving. Smack, smack, smack... smack. I tried to shift my body a little and SMACK on my other thigh. F closed her fist around my penis, leaving the head exposed and went back to work with her tongue. Every time I got close to cumming she could feel the muscle contractions in her hand and she would abruptly stop and squeeze. If I moved at all I was met with several hard slaps to the thigh. After a while she released her hand and put her mouth over my cock. I felt her saliva on me. She removed her mouth and blew. The air was freezing and my cock began to shrivel a little. She let out a laugh.
Her hand brought it back to full erection. Mouth. Blow. Shrivel. Giggle. Stroke. My head was starting to ache with this cycle. The last time through she left it partially shriveled and I felt her get off the bed. Some rustling followed from across the room where she left her purse. F then went ninja and I couldn't hear her at all. I felt something foreign touch my nipple and I screamed through the gag. The pain was terrible. F had brought some plastic clothes pins that had grooved teeth. I started to writhe against the restraints and felt her slap me. I was now making plenty of sounds that were audible but muffled by the gag. I started to buck and she slapped me again. My next sounds were a bit like weeping and she responded with a sharp laugh.
I felt a sharp pain on my other nipple and tried to cry out, thrashing about. About 10 slaps got me to stop. I could feel her pressing the clips in various directions. The teeth dug into the tender skin and gave a constant, throbbing, horrible pain. I was now whining and crying beneath the gag. Tears soaked the inside of the blindfold. I felt one release and sighed and she replaced it immediately but at a different spot. I shrieked. She repeated this with the other nipple.
F shifted and spread out next to me. I could feel her breasts press up against me and her crotch hot and wet through her jeans on my thigh. She let me thrash around a little bit in agony.
"Stop moving." I stopped.
Her fingers tapped the side of my cock, which was now almost totally limp. She smirked.
"Does it hurt?" I made a sound and nodded my head.
"What was that? I couldn't hear you." I nodded fiercely.
"Oh, poor baby. I bet those hurt quite a bit." I nodded, still whining/moaning under the gag.
"Well, they couldn't hurt too badly, or you would have said something by now, right?"
I began to sob.
"Poor, poor, baby. slave."
She shifted again. Her I felt her fingers pinch the skin on my scrotum, pulling some of it out. The plastic teeth of another clothes pin touched it. I started to wail and thrash around.
"STOP MOVING!" SMACK.
I was now sobbing and I tilted my head back. I felt the plastic teeth touch my scrotum again. It was the bottom teeth. I felt the top teeth and they stopped and lifted again. Then the teeth again and they stopped and lifted. F was closing the clips just enough to where the other side would touch before opening them again. My penis was completely limp at this point. I was twisting my feet and hands around against the restraints, it was the only struggling I could do without being slapped again. This repeated a couple of more times before finally she allowed the teeth to close, I let out a choked gasp, and the clothes pin was removed after less than a second.
F again shifted on the bed. I felt her remove the blindfold. My eyes were red and swollen. She undid the gag and I closed my eyes.
"Look at me," she said.
I felt her fingers around my chin and I opened my eyes.
Our eyes met. She was straddling me again. I felt completely vulnerable. Her gaze was piercing, almost like it was on fire.
"I love you," I said in an exhausted and hoarse voice.
She leaned forward and kissed me, plunging her tongue into my mouth. F's hand grabbed my hair and pulled my face into hers. My eyes closed again. I could feel her devouring me. The kiss lasted an eternity.
Afterwards, F got up and unlocked the chains. I could barely sit up, so I rolled to the edge of the bed and slid off. When I tried to stand I stumbled back to one knee. My entire body throbbed and I felt like I had run several miles. I didn't know that being restrained in one position for 90 minutes would make me that stiff and sore. I finally made it to my feet after recovering for a couple of minutes.
"slave, get your furs."
I returned with an array of items. F chose my punishment hat and pink fur earmuffs and collar. I presented them to her and knelt in front of her. She pulled the hat on, put the earmuffs on over the top of it, and secured the collar around my neck. She then squeezed my nipples and instructed me to go into the bathroom.
"A slave's seed belongs in the toilet along with the rest of the waste. Now stroke it."
My penis was still limp and a bit sore. My testicles were aching and were so bloated that it looked like they had been replaced by purple tennis balls. I started to rub it. F reached around me from behind and took one nipple in each hand and began to pinch and twist them. She put her chin on my shoulder and watched me.
"Come on sissy, you know you're so pathetic you can only get hard when dressed like this."
I got hard again and my cheeks burned red.
"Hah, see, sissy? You know you like it. These earmuffs are so silly looking! And that hat is so cute on you." F moved one hand and tapped on the fur pom pom on the hat.
"Keep stroking it, I've never seen what it's like for a sissy slave to cum."
I let out a small whimper.
"Aww, what's the matter? Is sissy embarrassed? Should a slave be too embarrassed to follow his Mistresses' orders?"
I whimpered again.
"Answer me," she said as she pinched hard on my nipples.
"Good. Know your place, slave."
"I'm getting close, Mistress." F was breathing heavily and I could feel her hot breath on my shoulder. I kept stroking.
"Mistress, may I cum please?"
"Not yet, sissy. Think about how lucky you are to have a Mistress that dresses you in furs and even permits you to cum."
"Thank you, Mistress," I gasped, trying to hold it back.
"May I cum please, Mistress?"
"Thank you, Mistress."
I let out a moan and violently ejaculated into the toilet across 7 bursts. I felt like I was going to collapse. I was completely spent.
"I love you, Mistress," I whispered.
"Look at me, slave."
Our eyes met. She was tearing up. She grabbed my head and pried my lips apart with her tongue, followed by an intense open mouth kiss. When we separated she was crying. F threw her arms around me and pressed her face to my chest.
"Thank you," she said.
I put my arms around her and she cried into my chest for several minutes.
The next day we chatted about the events through messenger. I let her know that while I was sore, everything had been okay and not to worry about it. This gave her some comfort and from then on, she was able to let go and do what she wanted.
As a side note, it took a good long while for my nipples to toughen up and eventually they got really dry and cracked. During one of our sessions they were too damaged to do much with so F put some lotion on them because she wanted to play with them anyways. Apparently Lubriderm must taste really bad because after sucking on one of them I heard "eeechh" with a little cough and some spitting. I let out a laugh. That was the day I learned what it felt like to have clothes pins on the nipples, and 5 more clothes pins on the skin around each nipple.
To be continued.