Somehow this isn’t how I thought it was going to be even though it was exactly what we had talked about. Well there wasn’t much talking just telling, I’d gotten myself in a bit of a bind and was offered a way out so I jumped on it. Literally.
My mind was going in 20 directions trying to process what was going on as I sit, tied to a chair, lube running out my loose asshole, my cock throbbing in a cock cage, gagging on a pair of panties. She was in front of me on her bed, spread out, pleasing herself telling me I wasn’t good enough to ever get her.
I’d started becoming late on some of my bill payments, but Ms had been eyeing me for a while and had came up with a way to atleast do away with some of the late fees. She’d found I was a bit of a sub and thought there was a possibility of some trading.
“How’d you know?” I asked.
“Sometimes things are way more obvious than you would think,” she replied.
We discussed secrecy and how our arrangement would remain between us and we must stay discreet no matter the circumstances. I had an idea of what would be going on in our arrangement but nothing specific was stated. “Keep in contact,” she said, ” there will be some training, don’t bail on me, this will be good for us both!”
Over the next few weeks we chatted, she found out what toys I had and my experience. We’d began to develop a good friendship. I wasnt sure what to think as there had been no power exchange, no tasks, nothing, but I wasn’t in a hurry, I was shy and embarrassed about the whole thing. I kept wondering who all knew and who all would know, but was assured it would be private.
Suddenly our chats became more serious. I’d be asked to do things like, go to the store with a butt plug in or wear your chastity cage and watch some of your favorite porn. I tried not to show how much I liked this. One day I got a message saying, : “Go to a store, pick out some panties for yourself, make sure they are cute!” I was apprehensive as this was something we hadn’t really talked about. I had to grab some other things while in town so I went shopping. My face was red as a beet. Not because I’d never bought panties before, just never for myself.
There was no contact for a while, possibly even weeks. Then on a Friday night, ” you need to get out tonight, wear your small chastity cage, largest butt plug and the pink lace thong you bought, go to the bar in town. Send me pictures as you get ready and after you get to the bar.”
My heart jumped. It was real again. I did as instructed. When I showed up there I saw her in the corner with some of her friends. My mind went crazy, did they know? Not big info bars myself I just kind of hung around, chatted with some of the regulars and burnt the time.
My phone buzzed. “Where are my pictures? This place closes soon!” I didn’t even reply I got up and went to the bathroom. Her eyes glued on me the whole time. I snapped a couple pictures and hit reply. As I walked out her whole table was laughing hysterically. Was it at me? I threw my money on the bar and left.
“You sure left in a hurry!” Was my next message.
“Did you tell them?” I asked.
“Sweetie this is our secret. Promise!”
“Alright, I guess Miss.” I replied.
“Ok boy, come to my house tomorrow night. For doubting me I may have to up our first in person punishment.”
I couldn’t sleep that night and hardly did anything the following day. She texted me around 4 with a list of items to bring. They included many of my toys as well as things she’d told me to purchase over time. I put the things in a back pack and gave myself an enema and took a shower as I was instructed to be clean for our meeting. I was nervous the whole time.
“Be here at 6, sharp,” was her next message.
I gathered my things and begin to walk across town to her house. When I got there I was greeted like a friend or family member and was swiftly brought inside.
“Hello my pet,” as she led me into her bedroom. “Put all your items on the table next to the bed, make sure your wearing nothing but a thong.” I was still speechless.
“Yes mistress,” is what I barely stammered out and she said, ” save your oxygen and energy, you will need it.”
I got things ready and sat on the bed waiting for her to come in. Instead of the sweet lady next door whom greeted me I was faced with a lady whom was all business. She was wearing a long black robe, carrying a flogger in the other hand. She walked towards me and my cock sprung to life.
“Awww he’s got a little bulge in his panties. We need to take care of that right away,” she said.
“But miss..” I was cut off,”did I say you could speak? The only time your allowed to talk is when I say you can, or if you need to use your safe word, but don’t let it come to that.”
“I wanted to have a little more fun, but lets just cut to the chase, hope your ass is streched out!” She said as she grabbed my cock cage. She slid my thong down and put the cage on. “He’s such a cute little guy, no way he could ever satisfy me, ” she stated while locking the device. “I’ll keep the key safe for you,” as she put It on her necklace.
She dropped her robe off and she was wearing a black lingerie set, fishnets and about a 10″ strapon.
“The the one with the bigger cock does the fucking right?” As she caught my stare.
“Yes ma’m” I said
” well I want to fuck you but I don’t want to do any work right away,” as she laid down on the bed, her large cock protruding, ” mm maybe you should suck it a little for me boy.” As she grabs my head and forces it down on the large dildo. I choke and gag. ” Just take it, you want it I know, mmm that’s a good boy.”
She floggs my back as I preform oral on her strapon.
“That’s enough, lube it up and ride me bitch!”
I grab the lube from the table and lube the shaft.
“Good boy, now get on, I’d planned on working you up to this but I’m too horny to waste time! I hope your ass is ready!”
I began to straddle her but was stopped, “No back to me, I don’t need to see that thing you call a cock bouncing around in its cage!”
I turn around and lower my ass on her cock, it slides in with little effort.
“Good boy, I’m glad you can take it so good,” she encourages.
I begin to ride her cock and without warning she begins to flog my back.
“Mm yea take it good you little bitch!” I moan in pleasure as I ride the strapon. She pushes me off into doggy position and thrusts her cock deep into me. I’ve lost all control at this point. Cum dribbling out of my throbbing cock, the bed covered in my drool where she is holding my head.
“Mm I’m impressed, you can take my cock like a good little whore!, Go get on that chair!”
I sat down and she handcuffed my hands behind my back and tied my ankles to the legs.
She slowly removes her strapon revealing her soaked panties, she pulled them down and shoved them in my mouth. “No comments just watch!” Her smell and taste had me high, She laid back down and began to fuck herself with her vibrator, moaning other guys names. “How’d I get here?” I ask myself Now I remember, how long will it last? I feel used and degraded, but I hope it never ends