2. Our First Playtime Together

Hi there, to all our readers...this is Jeremy. I was instructed to write this part of our back story. My mistress, Wendy, recently conveyed how we reconnected after two decades apart. She chronicled her back story and how initially we interacted via online chat sessions. Ah, the wonders of social media! During these nightly chats, we discovered our shared desires, mine to be submissive and hers to dominate. This is our tale of how our relationship progressed from kinky, hot, online banter into a real liaison. A tryst that exceeded both our expectations (and fulfilled both our needs).

I didn't come to the realization of my inner desires all at once. I was married for several years, and my ex and I would occasionally tie each other up like a lot of couples do and get into light BDSM. I enjoyed both roles and considered myself a switch. My favorite thing was to tie her down and force her to suck my cock (something she would never do otherwise). As time went on, I did find that I also got immense satisfaction from being tied up and left helpless. I think that because at work I was always having to be so in charge all the time, making complex decisions, and running meetings and projects. When I was bound and powerless it gave me an amazing sense of freedom to be able to just let go.

Well, several years ago I got a friend request on Facebook from my first lover, Wendy. As she already related, we began as most old friends do. We caught up on old times and filled in the blanks about how our lives progressed since we were first working at McDonald's lo those many years ago. After several drinks one night I confessed how my marriage had gone sour. She told me her marriage did the same and eventually it had to end. I hadn't gotten to that yet, but I think I was just in denial.

One thing to know about me is that I suffer from Narratophilia. That's to say I get sexually excited by the telling of dirty stories to a partner. Of course, listening to the same gets me just as randy. I'm not sure who began it, but when our conversations turned sexual, I jumped in with both feet not caring where it would lead. Our nightly PM sessions got very hot and graphic, and we often played with ourselves, one hand typing while the other was busy down between our legs.

Would I have changed anything? Easy question and it deserves an easy answer. No. From our first sly dirty innuendos to some full-up kinky BDSM PM sessions to where we are today, I've come to experience so much more of the sexual spectrum. I've been brought to my limits and pushed well beyond them, learning so much more about myself and my sexuality. Plus, Mistress Wendy is one hot lady with an amazingly dirty and creative mind.

After a few months of hot, nightly PM sessions, Wendy asked if I would like her to come to visit. She had a trip already planned for Texas next month, and she could hop on over to Florida afterward. This way we could get together in the flesh. I was thrilled (and a bit nervous) at the idea. It had been over 20 years since we were last together, and I was interested in seeing if she was catfishing me with the photos she had sent me. Could she really look that good after all this time? I have to admit I also had a twinge of consciousness due to still being married. I was sure that sex was going to be had in one fashion or another.

We discussed having a "play" session when she visited. We agreed that after we had gotten to know each other again if we both felt right about it, we'd try having a real-life BDSM session. She would be my Mistress and I'd be her "dildo-whore", submitting to whatever she wanted to do. Safe words and hard limits were agreed on. She told me that unless I gave my safe word, she was going to do things to me that would push me to my boundaries to make her Dark Goddess come alive.

Ok, I know you, the reader, want me to get to the good stuff, and I'm almost there. I wanted to be accurate in the storytelling, so bear with me for a minute. Trust me; the destination will be worth the journey.

So, the day arrived when Wendy flew into northwest Florida. I had taken off work the week in preparation for our reunion. I figured that if it didn't go well, I could go back to work and call it a missed opportunity. The day came and I gave her time to get to her hotel and get settled. I arrived as planned at noon with a dozen red roses (I try to be romantic and classy when I can). My heart was beating in my chest as I waited until the door opened and I was bowled over. Wendy looked even better than her pictures! Smiling she took the roses and we kissed -- and what a kiss it was! It was like the 20-plus years we'd been apart melted away in that passionate embrace.

We spent some time catching up. I had to hold myself back from jumping on her right there and then. I was trying to be a gentleman and restrain myself. I did admirably as I took her out and showed her the magnificent area I live in and where I worked. You know the basic "nickel tour." I felt the old excitement of courtship again -- holding doors for her, holding her hand, sneaking in a kiss and we had a fantastic time reconnecting. It just felt so natural and easy being with her again!

That eve I took her to a nice restaurant for dinner and afterward we made love for the first time in 23 years. It was phenomenal; her body was thin, trim, and with a fabulous ass. She made me take my time and extended foreplay for the longest time. Necking on the couch first, and then finally allowing me to remove her blouse. I'm not a boob man, but hers were firm, yet supple and enough there to tempt me. Her fabulous nipples got so pert when I suckled on them.

I wanted to show off my oral skills and when she finally allowed me to remove her pants; I performed the best cunnilingus that I could. I went down on her as she reclined back on the couch. I pride myself on being pretty adept at it, and I was happy that I was able to bring her to climax with just my mouth on her sweet cleft. She held my face firmly between her smooth thighs, her fingers wrapped in my hair, as she trembled all over with the first of her many orgasms. Soon after her third orgasm, she pushed me over onto my back on the floor. She yanked off my pants and mounted me, impaling herself on my rock-hard erection, she rode us both to a final mind-blowing orgasm.

(Trying unsuccessfully to condense my story)

Exhausted, we retreated to the couch and basked in the afterglow. We rested, gently stroking each other and remarking how sex between us had only improved with experience. I don't recall it being that amazing when we were teenagers! As I got ready to leave (not being able to spend the night), she saw me to the door and with a kiss pulled me close and whispered in my ear, "Jeremy, tomorrow I want to have our first play session. My Dark Goddess is begging to surface. Bring a sawhorse with you and you better be prepared to get in touch with your submissive side." She then bit my ear and with a smack on my butt, sent me away. I drove home with butterflies in my stomach and a raging erection between my legs.

(Now for the good parts, sorry it took so long, but I'm sure it will be worth the wait.)

The next day I went and saw her just after lunch. It was a warm day, and we spent the afternoon savoring the sunshine out on the beach (something she could never do in Connecticut in March). For dinner, I took her to a local French restaurant. The whole time she kept me distracted by putting her hand between my legs to elicit an erection. She was doing her best to unsettle me, even going so far as to unzip my fly and pull out my dick. I didn't give her the satisfaction of seeing me nonplussed and kept my composure despite my turgid cock sticking straight up and the waiter giving us strange looks.

We didn't stay for dessert, having other things in mind, and went back to her hotel room. She bid me settle in with a drink while she got changed. I poured myself a double bourbon over ice and sat down to watch a movie on TV, both excited and nervous about what was to come. I couldn't concentrate and don't remember what I was watching. This was going to be my first Domme/sub playtime and I was trying to mentally prepare myself.

It seemed like my wait was eternal, but I finally heard the door to the bedroom open. Looking over my shoulder, my breath caught in my chest as I beheld Wendy slowly strut toward the living room. Her dark hair was pulled back into a ponytail and she had on a black and red tight top that hugged her slim figure. Her cleavage was poking out of her bodice, but my attention was caught by her visage. She had taken great care with her makeup and had applied dark red lipstick to her lips which were set in an evil grin. She outlined her eyes with black eyeliner as well as smoky eye shadow. A tight shiny black skirt with a very revealing hemline covered her hips. Black stockings covered her legs held up by a garter and on her feet were back high heels with straps that went up her firm calves.

"Jeremy, are you ready?" she spoke in a low, dark voice entering the room

"I am," I replied standing with a nervous grin.

She looked at me with a scowl, "I am.... What??"

"Mistress," I stammered. "I am ready, Mistress."

"That's better. You are to give me my due respect. You will refer to me that way for the rest of the night. Now, stand up and remove all your clothes, I desire to inspect my property. Be quick about it!"

I stood and hastily unbuttoned my shirt. Removing it I draped it over the back of the couch and pulled off my shoes. My pants were next, and I tossed them next to my shirt along with my socks until I stood before her in my boxers. Looking down I was embarrassed by my dick standing tall, making an obvious tent.

"Really?" she intoned coming up to me and poking a finger into my chest. "You are just going to toss your clothes like that, making a mess of your Mistress' abode? Tidy up my place and I can't believe you left your underwear on. Did your Mistress not command you to remove 'all' your clothes?"

"I'm sorry Mistress," was my only possible answer as I quickly folder my pants and shirt and set them out of the way on a table. My boxers were then removed and set and top of the pile. I made my way back to her feeling self-conscious as I was buck naked while she was fully clothed, watching me with a critical eye, arms crossed.

We had been naked around each other yesterday (for quite some time), but something about standing there in the nude while she remained clothed and in control enhanced her dominance. I don't know why but I felt like I had something to be ashamed of. My erection was now fully grown, poking out in front of me, throbbing away to the trip-hammered beating of my heart.

She slowly walked around my frame and I felt like a piece of meat on inspection. She studied me with eyes flashing, "I don't think you're sorry yet, but you will be. That was slow, sub. You aren't starting off very well serving your mistress, are you?"

I was crestfallen and cast my gaze downward, "No, I apologize and will do better." I was abashed feeling like I needed to cover up.

"Yes, I expect you will learn to do better. Now, what is your safe word, my sub?"

"Pineapple, Ma'am" I answered.

"First of all, I will not be addressed as "ma'am". Do I look like an old lady? Second, you better keep your safe word in mind if I push you too hard, which I might just do. If you voice that our session is done. There will be no going back and restarting, we'll be done for tonight. I hope you won't have to use it too soon and end my fun."

She pointed at the ground saying, "Now get down on your hands and knees and kiss your Mistress' feet. Abase yourself and maybe, just maybe, I'll begin your training."

I lowered myself to the floor and bent to kiss her toes, nails covered in dark blood-red nail polish. She stood, judging me, as I gently kissed each one in turn. When I was done, I remained down on all fours since she hadn't given me any further instructions.

She placed her foot on my head and pushed it down to the floor, "Ok, dildo-whore, I guess I will be gracious and give you a chance. I will endeavor to train you to be a proper sub. I picked up some items before I left Connecticut in the pet department with you in mind," I heard her say. She encircled my neck with a simple dog collar. Fastening it tightly, she then clicked a long black leash to it and tugged my neck. She mused, "I expect in the future we'll have to buy you something a bit better, but I guess this will do for our first play session. Follow your Mistress Jeremy, crawl like the dog you are."

She walked slowly in front of me with me in tow, and I did my best to follow her. I didn't think it'd be as difficult as it was, trying to keep up with her. You observe babies crawling all the time, but damn it hurt my knees and wrists. She led me on my leash throughout the condo. Down the hallway, to the bedroom, I was led. She didn't end there but continued to the kitchen, around the table, and back to the living room.

She brought me over to the couch and with a tug on my leash commanded, "Lean over the arm of the couch, I have a craving to discipline my sub."

I did as instructed with my feet on the floor, face in the couch cushion, and my ass up. I couldn't see what she was doing but she went away for a minute and returned standing behind me. I felt her hands caress my backside as she remarked, "Oh dildo-whore, your ass is so nice and firm and yet so unmarked. I can think of so many things I'd like to do with it, but first, let's give it some color, shall we?"

I turned my head and observed her go over to the pile of my clothes and came back with my belt. I then heard a *swish* noise and felt a sting on my backside as she swung my leather belt through the air to connect directly across my ass cheeks. I was startled by the force of her blow and how much it hurt, so yelped and pushed myself up from the couch.

Wendy grabbed my hair, pushed me back down, and scolded, "Did I say you could get up? Back down and accept your discipline. Otherwise, that's all you might get tonight until you are able to take it like a proper sub!" She pulled my hands back behind my back and fastened small dog collars around each wrist. They were then connected by a simple carabineer effectively pinning my hands behind my back.

"I figured you'd need to be collared and cuffed for our session, I'm glad I brought those down with me," Wendy said as she smacked my ass again with my belt. "You know, dildo-whore, I'm feeling my Dark Goddess starting to awaken. It's been so long that she's had to lie dormant, but like a bear coming out of hibernation she's starting to rouse, and boy is she hungry! We're going to do this nice and slow. All I want from you is your surrender... Beyond that, you don't have to think about a thing."

I felt helpless, bent over the couch's arm as my Mistress thoroughly whipped my ass. Each time she struck me it hurt like hell, and I couldn't help but cry out with each blow. This went on for some time and I began to fear that this might be all that she had planned for our first play session. Not that I was in any position to complain, but this wasn't what I had expected -- to just be bent over and whipped until I wasn't able to sit down.

I figured the constant blows were causing welts to form on my ass, and the idea of using my safe word popped into my head. "No, I'll not give in that easy." I thought to myself, "I wanted to give up control to my dominatrix and that's what I've done. I have to release my urge to be in control and just accept what she does to me if I am going to find the true release I long for."

A few minutes later, she gave me a particularly hard spank. I let out a cry which elicited from Wendy, "I just find the sound of male erotic anguish SO exciting!" as she continued trying to make my ass red and raw.

At last, the beating ended and she pressed herself up against my raw ass. Leaning over my bent frame she leaned close and purred into my ear, "My Dark Goddess has needed that for some time. Time to explore what other nasty fantasies I have, shall we?"

She left me there, bent over the couch, and went back to the bedroom. I couldn't see what she returned with, but I heard her say, "I think I need a drink, don't go anywhere." She smacked my ass and went into the kitchen and returned soon after. Turning my head I saw her sipping a full glass of wine.

Coming up behind me she held the glass in her left hand and reaching out with her right reached between my legs and found my dick. I separated my legs to give her easier access, and she yanked it backward between my legs. "I have read that with a sub, tease, and denial are both needed. Without the tease, it's just denial and the man will soon lose interest," she mused as her thumb began to rub the sensitive spot just under the head of my cock. I had grown soft during my spankings, but quickly I grew hard with her long fingers caressing my manhood.

She continued masturbating me, and it felt weird being yanked backward like that, but also really good. Without volition, my hips began to undulate trying to increase the pressure between my legs, but she had complete control now of my cock keeping me from doing any thrusting. All I could do was moan as I felt her thumb slowly rubbing my dick driving me mad with lust. "The sexuality part of domination and submission makes you open to change your character, but it's the discipline that drives home the lesson and makes it stick!" she informed me.

She stopped rubbing, leaving me panting with lust and wanting more. Setting down her now empty wine glass she went out of sight for a moment and returned with a small black but plug. Bringing it over to my face she leered, "open up Jeremy. You knew it was only a matter of time before we explored my anal fixation. Get my plug wet so it won't hurt so much the first time I take your ass."

I opened my mouth and she inserted her toy. If I thought she was going to take it slow, I was mistaken as she shoved it all the way hitting the back of my throat, making me gag. With me coughing and sputtering she began to fuck my mouth covering the plug with my slobber.

"Your suffering makes my pussy wet!" she informed me and removed the dildo only to go around my body to separate my ass cheeks. Pushing the small rubber plug against my anus I felt her apply pressure and tried to relax. With a smack on my ass, she pushed more firmly and I felt it penetrate my sphincter making me gasp as I was suddenly filled. I stopped thinking and focused on the feeling of being helplessly tied and fucked in my ass -- and it felt strangely wonderful. I really was starting to lose myself in the feelings my Mistress was creating in me.

"That's much more like it," she chuckled. With a final push, it went all the way into me as my asshole closed around the flared base. She unclipped the two wrist cuffs and yanking on my still attached leash said, "I have the desire to see you crawl again, Jeremy. Let's take you for another walk. Don't you dare let the butt plug fall out."

I climbed off the couch and knelt by her feet on my hands and knees. She again led me across the living room but this time she went to the door to the condo. Unlocking the door I suddenly realized what she planned to do, and it scared me. I heard her say, "it's such a nice night, let's get some fresh air." I made a sound, not unlike a low growl in my throat, she must have heard my reticence because she just yanked on my leash saying, "This is my desire, sub. You will comply!"

Her condo was on the third floor, and the walkway to the center elevator was open to the parking lot. Anyone down there could easily see me naked, being walked on a leash by my Mistress. I figured I could always run back into the room if anyone came by, so swallowing my pride, I crawled after her onto the walkway.