“Yes, Holly,” I replied, “did you guys like me?”
“Yes, Tom and I liked you a lot. We’d like you to join us again.”
I visited Tom and Holly for many evenings of play. She gradually ramped up the pain by introducing different floggers, paddles, straps and the most painful of all, the “Sadistick”. Holly also introduced me to predicament bondage. In one session, I was placed in a crouched position and my cock & balls were secured to a spreader bar that my ankles were attached to. My nipples were held with the butterfly clamps; the chain between the clamps was secured to an eyebolt on the ceiling. I could not sit or stand. If I tried to sit, the clamps would pull harder on my nipples. If I stood, the rope would pull on my nuts. Caught between standing and sitting, my muscles began to burn. Eventually extreme pain would shoot through my body. Holly could sense when I had suffered enough; she would then release me and embrace me in her arms.
In other sessions, I was introduced to the never-ending sit-up. My torso is suspended in a 45-degree angle. If I try to lie, the clamps tighten on my nipples. If I try to sit up, my chained collar tugs at my neck, almost choking me. After a half hour my thighs burn in intense agony attempting to hold this position.
The more intense the sessions were, the deeper I felt attracted to Holly. Watching Holly torture Tom also turned me on; she made him endure much more pain than I could. At the end of most of our sessions, we had exhilarating sex. Like most guys, I was at first reluctant to engage in sex with another guy; with Holly and Tom it was different. Somehow sex seemed as a joyous conclusion of our BDSM sessions, a sort of celebration of sensuality.
I soon learned that she was active in a local BDSM club. She encouraged me to join - or at least check it out. She would sponsor and mentor me.
I went to the next munch and met a lot of nice people who were also new to it. I applied for a 1-year membership and was accepted. Holly and I planned to go to the next "party" which would be held a few weeks later. Tom decided to stay home with Holly’s kids.
So I purchased the outfit Holly suggested - nothing fancy - leather cuffs, g-string and a play collar. She also suggested I assemble a toy bag. It contained some rope, a ball gag, clamps, a flogger, lube and condoms. The club was in a nightclub and bar neighborhood with crowds of people standing outside and loud bands playing inside. Holly and I walked up the stairs and signed in at the front desk. The attendant directed us to a changing area. We entered into a hallway lined with lockers. We stripped down to our play outfits and left our street clothes in lockers. Holly was wearing a black corset with fishnet stockings and stilettos. She attached a leather flogger to her belt.
We went into a large dimly lit room that had couches, tables and chairs in one end, and smaller numbered playrooms with curtain doors. Loud music was playing as costumed members wandered around and greeted each other. It was like Halloween, except it was more of a “Sexalloween” - or like the Exotic Erotic Ball. People meet up and drift off into the rooms for play sessions.
Many of the attendees said hello to Holly. She introduced me as her new “student”. She agreed to meet some of the people later.
Two women said hello to Holly and started a conversation. One was tall, slim, wearing horn-rimmed glasses. She was in high heels, fishnets & red corset, long black leather gloves with a red or magenta streak in her long black hair. The other woman was similarly dressed and had short bleach-blond hair. They were introduced as Jane and Mary. Holly chatted with the women while I purchased several bottles of water.
Holly persuaded the two women to "break me in" on my first session at the club. They protested that they had never "done boys".
“Don’t worry,” Holly said, “I will show you how to do a boy".
Mary secures Dave to the wall
Our group found a room. It was dimly lit with a few candles. In the room there was a large frame with a padded table inside and a cross that was mounted on the wall with various eyebolts attached. Holly directed the women to tie me up to the wooden cross. She pulled several lengths of rope from her toy bag and gave them to the women. She gave them instructions on how to wind the rope and how tight knots should be. I felt scared about the dark dungeon-like room we were in and the women I had only just met. I began to tremble. Holly sensed my fear and assured me that everything would be all right.
Holly then pulled a leather flogger out of her toy bag. “I always warm up my slaves with some light flogging”, she explained to the women.
She began stroking my back & butt with the flogger. I felt my skin tingle to the touch of the leather strands. She let the women practice on me and advised them on areas of my back where they could and should not strike.
She then retrieved her leather stinger and directed the women to give me several overlapping strokes on my butt. I began gasping as the stinger cracked on my skin. Jane hit me hard; Mary was somewhat gentler. The three women were sharing jokes. The laughter grew so loud that at one point someone from an adjacent room yelled at us and threatened to get us kicked out of the club if we weren’t “serious”. I actually laughed with them, despite the slowly mounting pain on my back & thighs. This session was becoming a joyous experience for us.
After this Holly said, “I want you two to feel how warm you’ve made his butt. That is the heat you should be going for. While you are rubbing his ass, I want you to grab his cock like this”. She showed the women how to squeeze my cock by its tip, a move she had perfected with me in previous sessions at her home. My erection grew to their touch.
“Its time for a break, ladies”, Holly said. She directed the women to loosen my ropes. We leaned against the edge of the padded table and drank water.
Holly asked me, “how was it, Dave?”
“I liked it very much“, I said.
“Do you prefer Mary or Jane?” she asked.
“I like Jane’s firmness as much as Mary’s light touch, “ I said, trying to be diplomatic, “and your touch is just right, Holly.”
“Good answer, “ Holly said, “shall we show the ladies some NT and CBT?”
Although I was still sore from the beatings I received from the ladies, I mounted the table and lay on my back. The women attached my ankle cuffs to my legs and tied them loosely to the side of the table. They secured my wrist cuffs and tied them together. They connected this to an eyebolt on the bottom brace of the table. Holly retrieved the black ball gag from my toy bag and fastened it on my mouth. She found the cock ring in my bag, lifted my limp cock and fastened it to the base of my shaft.
She found the butterfly nipple clamps and gave one to each of the women. “Now, I’m going to show you how to apply a clamp to a boy’s nipple”, she said. She pulled out a pair of press-style clamps from her bag. “Dave’s got nice pecs, “ she told the women, “but we need to position him before we apply the clamps.” She clutched a large clump of my pectoral muscle with one hand and tightened the press clamp so that my nipple was sticking out like a mountain peak. She did the same with the other pectoral.
“Now,” she told the women, “ attach the clamps to his nipples”. They each fastened a clamp directly on my extended nipple. A jolt of pain shot through my body. “Now, we test the clamps before we release the press, “ she said as she pulled the chain that was attached to the two clamps. The clamps tightened and sent even stronger jolts of pain through my body as she pulled on the chain. I gasped but could not force much of my screams out through the ball gag. The clamps withstood Holly’s stress test; they would not come off by pulling on the chain. She released the press clamps. I felt additional jolts of pain as blood rushed to my clamped nipples; my blood was throbbing through my chest.
Holly then found a pinwheel from her toy bag and handed it to Jane. “I want you to run this over his chest”, she directed her. She told Mary: “start squeezing his cock here” as she pointed to frenulum of my shaft. Holly had sized up the two women as I had: Jane was more sadistic and Mary more into stimulation. Both women assumed their tasks with glee.
Holly then wound a small cotton rope around my cock and balls and tied a slipknot. She tugged on the rope. My hips rose in the pain. She slipped my toy bag under me as she fastened the rope to an eyebolt that was on the frame above me. She pulled the bag from under me. The rope pulling on my cock suspended me. If I relaxed, the rope would tighten and shoot jolts of pain through my cock. I tried to keep my hips thrust high to lessen the pain but after a while my thigh muscles began to burn. I felt the exquisite pain of predicament bondage for almost a half hour until I was writhing in pain, as sweat and tears draining off my face.
Holly sensed that I had enough of her torture. “Lets release him, ladies, “ she told the women. After I was released, we all leaned on the table and drank water.
“Now tell me Dave, “ Holly asked. “How was our play session tonight?”
“It was fantastic, “ I said in a raspy voice.
“Would you like to do this again sometime?” she asked me.
“Yes, “ I answered enthusiastically, “I’d like to do it again with all of you. “