Kalypso and Odysseus

Please, come sit by my fire and allow this old man to tell his story, a tale of joy and a tale of warning.

No, my name is not Odysseus but like the wayward seaman I too have indeed traveled long and hard, searching for what I consider home.

I have been married now for over thirty years. A statistical anomaly for sure but I will not lie and say they have been happy years. Now don't get me wrong, I have always loved my wife but things have not always been wonderful, nor have I always been faithful.

I'm not going to make excuses. I've been a bad husband. My weakness has always been women, powerful, controlling women. Even before I met my wife, I was even lucky enough to have served as a live-in slave for a wonderful Domme when I was nineteen years old. That however is a story for a different time, tonight I will share my tale of heaven and hell, my bliss and terror and how I am trapped not unlike Odysseus on the island of Kalypso millennia ago.

As I said I crave submission, serving, to be a slave. The wife however has no desire to participate in any such activities, despite years of open dialog on the topic. In fact she deems such desires as maladaptive behavior; some sort of codependency. So I guess at some point I justified, in my mind, stepping out on her...finding a play partner. My search was largely fruitless. I met a few ladies along the way but they were into hard core impact play and such...just not my thing...then add in the desire to be discrete. It just wasn't going to work.

I had almost resigned myself to just giving up and then I saw an ad: A sensual Domme seeking a sub. Nothing serious just two people getting what they need from each other. Oh such a siren song; could I be so lucky? I leapt at the opportunity; the email could not be sent fast enough.

I included my kik screen name in the email along with some photos of myself. I described my desires and experience as well as my physical stats just as instructed.

To my surprise she reached out to me via my kik. She introduced herself as Miss Kalypso. We chatted for a very long time and everything seemed alright except for one nagging issue: she would never provide a picture. I figured one of two things either she thought she was not attractive or this was just a dude hoping to get me horny enough to let him suck me off when we finally decided to meet.

We began playing online with some simple things like instructed tease and denial sessions. She really loved when I would send her videos of my poor cock throbbing, aching to cum and not quite being able to. She enjoyed videos I sent of me playing with my precum and instructed me to eat it. I did everything she asked. She wouldn't let me cum, I had to watch 30 minutes of porn that she would send me each night...basically she did everything she could to arouse me and torment me. Once every two weeks she would instruct me to cum for her. I had to record each time I was allowed to cum and show my face in each recording. She said she liked the expressions I made as I was cumming. She said she would turn the sound off and just watch...it made her chuckle because she wasn't sure if I was in ecstasy or pain. She also said it was the only way to verify I was obeying her when she instructed me to eat my cum. I thought nothing of it other than the physical difficulty of actually masturbating to orgasm and contorting to have both the cumshot and my face in frame on the cell phone camera. It was a lot to manage.

At that point I could have just gotten off this ride at anytime but I was enjoying having someone "paying attention" to my need to be submissive, and I wanted more...much more.

Finally after three months of heavy teasing and instructed orgasms, she told me to meet her at her apartment. I was to stop and buy a list of items from the store along the way. I did as instructed, left out of work midmorning with some lame excuse about not feeling well and went straight to the nearest Kroger to get the items on the list. Then I drove on down the road another two or three miles to her apartment. She had only given me the location of her apartment complex and her phone number. She told me to call her when I was parked and she would give me the apartment number and further instructions.

I parked and called her, she simply said "107 the door is open come in and lock the door behind you." and hung up. Her voice was beautiful but I still had no idea as to who this woman was...in any sense of the word. She had kept herself a mystery but soon all was to be revealed. All I knew for certain was I had to serve her. I truly needed her to utter those two words...those magic words that make me do anything: "Good boy."

I stepped through the door into a totally dark room except for the single light that was shining on me; obscuring my view of anything else in the room. She spoke from the shadows. Such a sweet inviting voice, she instructed me to set the bag of cleaning supplies down and strip all my clothes off.

I complied as quickly as I physically could placing the bag of cleaning supplies on the floor beside me and stripping myself bare. A virgin getting ready for his first sexual encounter could not have stripped so quickly. She chuckled: "It's been a very long time for you hasn't it?"

A very contrite "Yes ma'am." was the best I could offer.

She replied: "That's good. As the saying goes: 'Eagar beats pretty every time.' not that you aren't pretty...well yet anyway."

I could hear her getting up from a chair and walking in the shadows. "You are eager to actually see me aren't you? I have kept you in the dark about me for so long now. Each night you would ask if you would get to see me, and each night I would encourage you with a simple 'maybe...if you behave'." That was all it took to keep me motivated, she lead me on each night with not a promise of an action but the promise of hope. I felt slightly foolish now that she said it but she continued: "Well now I think you have indeed earned at least the honor of seeing me, I don't feel pictures do me justice and besides how else would I judge a slave's patience and potential to serve if I revealed myself at the first request?"

The bright light turned off and I was left in total darkness for a moment. Then the room lights came on, revealing her stunning beauty. Standing before me was a goddess. She had long flowing black hair, deep dark brown eyes...almost black...the kind that draw you into them. Her skin was alabaster white with just a few freckles indicating that was indeed her true skin tone. Her body was amazing: she stood right at 6ft in high heels, with flawless legs that lead up to a perfect apple ass. Her hip to waist ratio was on point and her breasts matched her well-proportioned ass. She was clad in a red body suit with matching thigh high boots. I fell to my knees, not so much out of respect but simply because my knees grew weak and gave way. On the floor at her feet was the safest place to be.

She gave me a moment to collect myself and began explain the rules. I wasn't to make eye contact unless instructed, follow all commands, and say "yes ma'am" and never say no unless it was the answer to a question. She said she had company coming over in two hours and the entire apartment was to be cleaned before her guest arrived. She instructed me to start in the kitchen. I leapt into action...having worked in commercial kitchens in my youth I knew how to clean a kitchen and bathroom like nobody else.

I flew through the kitchen, had the dishwasher loaded and running in no time. The stove was cleaned and the refrigerator and freezer took very little time. In fact the entire kitchen and bathroom were cleaned before the dishwasher was finished cycling. I moved on to dusting and vacuuming. Miss Kalypso decided I was moving too fast. So while I was on a step stool cleaning the ceiling fan she began to molest me. I was already rock hard she just wanted me in a little more discomfort. She snapped a parachute around my swollen balls and added what felt like fifty pounds of weights but was in reality just a few ounces. The parachute pulled down on my scrotum, squeezing my full balls tightly together. I had experienced this before but never as I was going about my domestic duties. I knew this was going to slow me down quite a bit. She also slid a stainless steel butt plug into my tight ass. It had a leash on it and I was told I was not to let the leash touch the floor.

She sat back and started playing on her phone. I used every opportunity I could to be facing her so I could see her beautiful face or those incredible legs...just quick glances to remind myself that this was not a dream. I moved as quickly and efficiently as possible though, I knew my time was short.

I had just finished and cleaned myself up when the doorbell rang. I looked at the clock; I had managed to clean this entire apartment in exactly two hours. Miss Kalypso motioned me to the door. I opened it and hid behind it. I didn't want anyone to see me naked and in the state I was in. As I opened the door I was surprised by a lady whose beauty rivaled that of Miss Kalypso herself. She had fire red hair; stunning green eyes and a smile that simply made me melt. She was tall and slim and was wearing a sun dress that highlighted her pleasing curves. She acknowledged me as I closed and locked the door: "You must Kalypso's new slave. You may call me Lady T." She gracefully slid past me and kissed Miss Kalypso on the lips.

As I watched them embrace, I felt slightly guilty in thinking what fun it would be to have both of them dominating me. They separated briefly and I was instructed to take Lady T's large bag. As I relieved her of her bag I realized it wasn't a crazy large purse or even a gym bag as I had thought when she came through the door. It was a camera bag full of equipment. Someone was going to be recording something today.

Miss Kalypso slid her body suit off over her boots and I could not help myself. I had to look, taking in her soft sexy curves, silky skin. I saw she was completely shaved and her breasts were firm and held their shape. She sat down on the couch and motioned me to become her footstool. I happily complied. She had me kneel down then sit on my feet, lean forward and place my hands on the floor. She placed a leg on each shoulder so I was staring at her pussy.

She reclined and waited for Lady T to set up her camera equipment. As she waited she began to talk with me. Asking me all sorts of random but harmless questions like what I thought of the Texans chances this year and who I thought was the best looking actor. Lady T was a pro, she got her tripod and camera set up fairly quickly and said we could begin.

Once the camera was recording the questions became more specific and probing. Miss Kalypso asked me my full name and birthday. She then went on to discuss hard limits and how much I craved her dominance. I answered all of her questions truthfully. She asked about my wife and why I was cheating on her, what would my kids think if me. She was shaming me. I was embarrassed to answer and thought for sure she was going to send me home never to see her again. She finished her questions.

She leaned forward and judged me: "You are a pathetic excuse for a man. You lie to your wife, your friends, family, coworkers...everyone. You wear a vanilla mask and are ashamed of what you are deep inside." As I sat there listening to her biting commentary I actually began to cry because I knew everything she was saying was true. She continued passing judgement on my body now: "You are incapable of satisfying me, that pathetic cock is too small. You are old and overweight too...how could you possibly hope to keep up with me?" She never gave me the chance to answer she carried on: "Look at you! You are actually crying! What a mess you are! Do you really want to be my slave that badly?"

She paused and I answered "yes ma'am" as I nodded my head.

"What would you do for me to please me? Would you do anything I asked? Would you play with anyone I instructed you to be with?"

I nodded my head and said: "Ma'am I am yours to do with as you please."

She motioned Lady T to come over to us. She repeated herself softly now: "Would you do anything I asked?"

I looked her directly in the eyes, I knew I wasn't supposed to but I needed her to understand my conviction: "Yes ma'am."

"That's good because I want you to suck my pussy while Lady T fucks your ass." I shifted myself to my hands and knees and she guided my hungry mouth to her hot wet pussy. She stopped just short of pressing my face in and told me: "You can show me how well you eat pussy, don't stop no matter what, unless I tell you to. Understood?" I nodded and moved in to pleasure her.

I could smell the sweetness of her pussy as I got closer to her. My tongue just grazed her lips. They were wet with her sweet nectar. She tasted so good. I struggled to control myself, I wanted to dive face first into her pussy but I needed to pleasure her so I had to take my time and let things build. I traced her lips with the tip of my tongue, up and down one side then the other always stopping short of her clit. With each pass I moved closer to her clit and applied just a little more pressure. She moaned a little more each pass.

Lady T spread my cheeks and I rocked my hips giving her full access to my tight hole. She removed my plug and leash then applied a generous amount of lube and began massaging the outer sphincter; slowly working her finger into me. She leaned in and whispered in my ear: "I love a nice tight hole. I'm going to really enjoy this." With that slid her finger deeper into me; pushing lube up inside of me. She knew exactly what she was doing and I relaxed as much as I could.

She pulled her finger out and I could feel her pressing on my ass. I soon realized she wasn't using a strapon. Lady T was filling me with her cock. I did my best to relax and let her in. I soon had her completely inside of me. She was larger than the toys I played with but since it was flesh and blood I could take more of her than I could any silicone toy. She started slow and I matched her rhythm by rocking my body slightly making sure she knew I was taking her all the way.

I continued to focus on the incredible pussy in front of me and pressed in now, licking her clit. I locked my lips to her and sucked her clit out from under its hood, flicking my tongue back and forth over it. Her hands gripped the back of my head and she began grinding into my face. I pressed in harder and brought one of my hands up from the floor. I slid two of my fingers into her. She was flowing with juices and very tight. Her pussy clamped tight on my fingers as I slid them in and out of her. Soon her body was trembling. I sucked harder, curled my fingers and picked up the pace. She pressed my face harder into her crotch.

I could taste blood, it was mine. My lips were being cut by my own teeth as my face and her pussy were grinding together. She tensed up, shuddered and let out a loud scream and soon I was being showered with hot wet juices. They were amazingly sweet. I kept sucking and licking her clit while my fingers kept fucking her she kept cumming. I thought I was going to drown but what a way to die. Her grip relaxed as her orgasm began to fade. She pushed me gently away.

She asked Lady T: "How about it Lady T? Is he any good?"

She replied: "He is very tight may I cum now ma'am?"

Miss Kalypso said "Yes fill him up, breed him!" and I almost instantly felt Lady T stiffen and explode inside of me. I could feel her cock pumping and throbbing with a massive orgasm. I could feel her load filling me and begin leaking from my ass when she pulled out and pressed back in; each time pumping more cum into me. Soon Lady T was finished, she grew limp and withdrew from me. A large amount of her cum ran down from my ass and onto my balls.

Lady T asked if she could make me cum. She then slid her hand over my balls pushing her cum onto my throbbing shaft. She stroked me firmly. Miss Kalypso began questioning me again. "Did I enjoy pleasuring her? Did I like getting fucked by a beautiful tranny? Did I enjoy being bred?"

To each of these I focused and answered "Yes ma'am it is an honor to serve!"

I wasn't sure if I was allowed to cum, fighting it was very difficult soon I gave in. My body convulsed and my load shot onto the floor. Lady T kept stroking, mixing my cum and hers on my cock. Each time she got to the head I felt the raw nerves firing causing me to writhe. Miss Kalypso laughed: "Oh the joys of post orgasm torture!"

I was told to get up, clean up the mess and go shower. I did so as quickly as my weak trembling legs could manage. When I returned from the shower I found Miss Kalypso and Lady T sitting on the couch, my clothes were on the coffee table and they had my wallet out. My heart sunk as I thought to myself: "I was being robbed?!" They had my driver's license out and took a picture of it. In fact they had taken pictures of everything in my wallet.

Miss Kalypso looked up at me and saw the look of protest in my eyes. She stood up, crossed the floor, looked me directly in the eyes and delivered her ultimatum in a very stern and serious voice: "You are now my bitch! I have every credit card, every bit of identification you own. I've researched you already online. I know everything. I can destroy you if you don't fucking do exactly as I wish! Do you understand this? Your wife, job, kids...I have all of it. They will know what a piece of shit you are, how perverted you are! All of the videos you have sent are on my laptop, the videos from today will be there soon after you walk out the door. I own you."

I stood speechless. My mind was racing. I hadn't thought about any of the things going on as material for blackmail. I tried my best to collect myself. Out of my mouth came the words "What must I do?" I had no idea I was speaking. It was a total fog.

Miss Kalypso was very stern: "You will arrive here at my door every Friday afternoon at 430pm and serve me and whoever I decide will join us. You will learn to suck cocks. Lady T is an excellent teacher. After each session you will take us all out for a few drinks then to the local club where we will play in front of others. This will go on until I bore of you and release you. You are mine! Understood!?"

That was five years ago. I am still under her control, five years of fear and ecstasy, pleasure and pain, bliss and terror. Each Friday she reminds me that the evening will be recorded. Each Friday I dig myself deeper into the pit. It's hard to believe that much time has passed now that I say it out loud. I see no way to escape I am not certain I want to either.

So you see I am indeed like Odysseus trapped on the island of Kalypso; bound by her sweet seductive spell and my fears and desires.