I was 19 years old and I had just arrived at my first BDSM party. A popular leather/BDSM store put on a party every month and I finally found the courage to attend. Looking back I must admit I was still a callow young man. I sat by myself at the bar, having a few drinks, and taking it all in. After an hour or so, when I was beginning to feel a bit like an outsider, a beautiful young woman dressed in an amazing leather outfit approached me. She asked me if this was my first BDSM party. I smiled and confessed that it was. She smiled back at me and said, “Let me introduce you to someone. I’ve noticed a woman over by the tables that have had her eye on you.”. She led me across the bar to a woman sitting at one of the high tables near the wall. She was a bit overweight and seemed fairly reserved, but I could tell by the way she held herself she was clearly Dominant. I was excited, but at my young age, I found myself thinking, “Why couldn’t it be the hot young Mistress that was interested in me?”. In any case, I sat down and we began to talk. We talked for the majority of the night and towards the end of the night, I found myself becoming slightly smitten with Her. She was strong, confident, and clearly unabashed in her kinky sexual desires. Somehow during our conversation, she got me to reveal that I had never had a butt plug (or anything really) in my ass and how I was really a bit hesitant about the whole thing. She smiled at me and asked if I would be willing to come home with Her. Earlier in the night, she had given me a playful spanking with the crop she was carrying, and she told me she wanted to take me home and give me a proper spanking. I was a bit nervous, but my penis spoke up and convinced me.
When we arrived at her house, she wasted no time escorting me to her ‘playroom’. I was nervous as I followed her down the hallway, but I also found myself terribly excited. She had been very calm and relaxed the entire evening and now was no different. I could feel her drawing me in, and I suddenly got the sense she’d been guiding the conversation all night towards this moment. As I stepped into her dungeon playroom, I saw a room full of bondage furniture, paddles, rope, dildos and BDSM equipment of all types. My heart raced and I began to question whether this was the best idea, but when she calmly asked me to undress, I felt strangely compelled. She watched as I undressed, and smiled when my cock popped out of my underwear and pointed straight towards the ceiling. She guided me to a pair of wooden sticks in the center of the room and directed me to place my head and wrists into the half-moon cut-outs so she could swing the top bar into place and lock me firmly into position. I did as she instructed and remember the mixture of excitement and nervousness as the top bar swung into place and she locked it shut. She circled me, admiring my naked body locked in position and fully at her disposal. I felt her hand trace a line down my back and come to rest on my ass. She rubbed my ass cheeks for a few moments and then pulled them wide apart. The cool air on my butt hole scared me and I arched my back, pulling away slightly. She moved with me keeping them apart. She held them apart for several minutes and then pressed a finger against my butt hole. She didn’t penetrate me, but I could feel her finger pressing against my butt hole. It felt good, but I was nervous… nervous about what she had planned for me. Finally, she removed her finger and stepped around to my side, running one hand up my back and the other reaching down and finding my cock.
I could hear a smile in her voice as she said, “A handsome young man like yourself out at your first bondage party… and now you’re locked up in my dungeon”. She began to stroke my cock and continued, “Will you be a good boy or do I need to give you a good hard spanking?”. “I’ll be good”, I responded expecting a spanking anyway but enjoying what I considered to be a bit of role-playing. Her hand stopped stroking my cock and she left me for a moment. It sounded like she had gone across the room to a table of equipment. When she returned she stepped in front of me, squatted down and looked directly into my eyes. I could see she was holding a butt plug in one hand and a bottle of lube in the other. “I want to take that virgin ass of yours sweetie.”, she said with a clear glint of desire in Her eye. I told Her, “I’m not too sure about that. Maybe some other time. This was just our first time together.”. I was very nervous. “I’ll make you a deal. I’ll only stick it in if you beg me to stick it in”, she told me. I envisioned never-ending spankings until I agreed and I began to protest when she continued, “and I won’t use any spankings or pain to coerce you.”. I was amazed… and I paused for a moment. “OK”, I agreed.
She began to rub lube on my ass, massaging it into my butt cheeks. Her fingers occasionally brushing my butt hole. Using more lube she moved her way up onto my lower back and down onto the backs of my legs. It felt incredible and I found myself closing my eyes and thoroughly enjoying it. Her lubed hand found its way to my cock and she stroked it for almost a minute until I moaned softly and begin to thrust slightly against her hand. I was very near orgasm but she clearly had other plans. She moved back to massaging my ass and this time moved quickly to put pressure on my butt hole. It felt good and being a horny young man I was already awash with lust. Before I knew it her finger had slipped inside me and was probing around my ass hole. I found myself beginning to move and squirm a bit, trying to get more of her finger inside me. She pushed in deeper and grabbed my cock from behind with her other hand. She held my cock tightly and slowly inserted a second finger. I moaned as she pushed them in deep and squeezed my cock. My cock was twitching slightly and I was pushing back as far the stocks would allow. She stroked my cock slowly 2 or 3 times as she removed her fingers. I pushed back aching for them not to leave. She stroked my cock a few more times and I could feel the tip of the butt plug as she placed it against my butt hole. She pushed it slightly so the tip just broke the seal and then pulled back. I struggled and pushed back against it. Wanting it inside me, but she would not insert it. She pushed slightly again and held it there while I squirmed against my bonds. She squeezed my cock firmly and I remembered our deal, I had to beg her for it. “Please… PLEASE Mistress push it inside me!”, I nearly blurted out. Still nothing but her tight grip on my cock and the tip pushing slightly against my butt hole. I continued to plead, “PLEASE Mistress I beg You. Please push it inside me!”. I truly wanted it inside me and I was becoming desperate. “Will you take it all?”, she asked me? “Yes, Mistress! PLEASE!”. “Are you sure?”, she asked again. “Yes, Mistress! Please!”, I pleaded again. I felt her let go of my cock and the tip of the plug ease slowly inside me. I was overcome with lust. I pushed back against her and very slowly felt it increase in size as she eased it inside me. Very quickly my butt hole began to feel tight as the size increased. The fullness excited me, but I began to wonder if it was going to fit. She paused for a moment… and as I relaxed she eased it past the hump, allowing it to slip in all the way to the base. I was worried it would be too big, or that it would hurt and now with it deep in my ass I was relieved… and I must admit I was also very excited. She pushed on the base of the plug, making sure it was deep inside me and then began to unfasten the stocks.
I was surprised to find myself blindfolded and tied tightly to a chair, sitting on the plug that was still inside me. She stroked my cock for a few minutes and then told me she was going to take a hot bath and that she would see me in an hour or so. When she left, I immediately began to feel a bit strange, tied to this chair naked with a but plug inside me. After about 20 minutes, I became bored and a little irritated. My butt was starting to go numb against the wooden chair and I wiggled against my bonds to get a bit more comfortable. As I did, the plug pushed and pulled against my butt hole. I was surprised at how good it felt. I squirmed a bit more, enjoying the sensation. And after 10 minutes, I was pushing and sliding, moving anyway I could to get the plug to move around inside me. Lost in my passion I was startled when Mistress touched my leg.
She explained how she had been sitting there watching the whole thing. She didn’t just want to be the first person to put a butt plug in my ass. She wanted to turn me into a slut overcome with lust for that plug. She untied me from the chair and removed my blindfold. Standing there naked in front of her, I remember wanting so badly to have sex with her! She looked down at my throbbing cock and smiled. She had a length of rope in her hands and I savored the feel her body pressed against mine as she reached around behind me and wrapped the rope around my waist. She passed the 2 ends of the rope through the loop on the other end and pulled it tight around my waist. She passed the 2 ropes around my cock, through my legs and over the butt plug still deep inside me. She removed all the slack and fastened it tightly in place creating a rope harness that would keep the butt plug inside me. Then she had me get dressed and sent me home.