This story contains graphic scenes and is not intended for persons under the age eighteen. It is a work of fiction intended for adults only. Please enjoy.
Natalie's Drive
What a Stupid Decision
It was the ultimate closeted cross dresser's nightmare. I had worked up the courage to leave the safe confines of my home fully dressed. I was just going to take a drive.
It had been a desire of mine since the age of ten to go out in public dressed as a girl. It had only taken nineteen more years to finally go through with it. It had started out well, till the ultimate nightmare happened, the car upped and died. I could handle the car breaking down, but I was full on female without a backup plan incase this sort of thing happened.
Back track, work had been stressful all week. I was thankful it was Friday and had caught up with everything by two o'clock that afternoon. I had taken it upon myself to leave work early that day. When I hit the road and on my way home and my mind was racing with what I was going to do with my extra stolen time. First thing that came to mind was I should go for a good run, but then I had recalled today was the day my package from "LuLu's" was to arrive. My mind was made up, and it was going to be a whole weekend as Natalie.
The whole drive home I dreamed of nothing but stockings and heels until I turned the wheel of my car in to the driveway. My eye spotted the package sitting on my porch right beside the front door. Depressing the button for the garage door it slowly opened and the car gently maneuvered through to a stop. Stepping out of the car I headed straight for the package. The anticipation was over whelming, but I held out wanting to tear it open right there. It would be better I thought I should wait till I got inside before opening it.
Cradling the package in one arm I headed straight to the bedroom. I placed the brown plain box on the bed and plopped down next to it. Reaching over I picked up the box and placed in my lap. Try as I may could not get the packing tape to budge. Looking around the room I spotted just what I needed, it was a metal nail file upon the dresser in front of me. Inserting it between the flap and body of the carton, then zip the tape came right off. Like a kid on Christmas morning I tore into the package, ignoring the packing slip and tissue paper, I gripped the dress and held it up admiring it. Placing it up against myself I went to check it out in the full length mirror that was on the back of the bedroom door.
UGGGHH... With all the excitement when I looked in the mirror and had noticed I was still in drab mode. I place the dress back down on the bed and stripped out of the ugly man clothes. All that was needed was to remove my shoes and socks, then black pants and gray shirt. Voilà I was just down to my nude thigh highs, mauve boyshorts panties, and mauve camisole. Oh hell forgets about holding that dress up in front of me, I went straight to putting it on. The black skater dress was so cute with an off the shoulder cut and mid length sleeves, but the best part was the midriff with its two band of see through thin mesh.
Now having been fully cross dressing in the past year and half I went into fem mode and prepared myself properly. Stepping out of the rest of my attire I head straight for the bathroom. I started with an enema; I had installed a stainless steel hose and with a nozzle in the shower, as you may never know who you would meet. I was still a virgin in that department. After making sure I was clean inside; I started with the outside. I ran a bath and touched up on any razor stubble on my body. I lightly dabbed dry, moisturized, and slip on my white satin robe that barely cover my ass. Next I had to do my nails, I have become quite good at it, this was going to be a white French tips weekend. Makeup was expertly applied with dark eye liner and smoky eye shadow with just a hint of green to make my hazel eyes pop. To top my look off look I chose an auburn wig with hint of curl and the length was just shy of touching my shoulders.
Having finished my look next thing was to pick out what to wear under the new skater dress. As being a sissy kind of cross dresser I had many role play outfits and under garments. My choice was a matching set of gold satin with black sheer panels six strap garter belt and demi bra which I stuffed with breast forms to give me a b-cup. To which I added contrasting black seamed and welt light tan color sheer toe stockings. Feeling that I should really whore it up I finished my lingerie with black lacy back door panties. Walked over to my closet in stocking feet to inspected my heel collection, but could not quite see which pair would look good with my new skater dress. I knew it had to be black but which kind. All of my shoes had four or five inch heels either in a platform pump, an open toe pump, and a single toe strap sandal, or the tee strap sandal. I had place them all on the floor in front of the full length mirror and tried each one on. My final decision was the single toe strap sandal as with the painted toes it really looked sexier in the sheer stockings. The final step was to accessorize with white pearl tear drop earrings and an eighteen inch pearl necklace.
As I stood there in front of the full length mirror looking at myself, I was amazed on how good I have become making myself look passable. I wish I just had someone to share this with, but that was not going to happen as I was just too afraid of what people would say. Anyway it felt good, I was more relaxed, just to get away from daily grind and just be Natalie. More I thought about it I really wanted to go out instead of just sitting around the house dressed the way I was right now. Maybe I could find a gay bar or drag show. I sat down at my computer and did a search on transgender friendly places. As I surfed the net I came upon blogs that helped me out to make that first step. I took the advice and started with what they called baby steps. The one that appeal to me was just go for a drive, to which I did that night.
All the time I spent getting dolled up and checking the net surprised me as it was already about nine thirty at night. It was becoming more likely I would finally leave the house as my femself. I had gotten very nervous as I grabbed my keys and phone and headed toward my garage. I could hear the clacking sound of my heels on the kitchen tile floor as I become very attentive and nervous for what I was about to do. I turned the knob on the door to the garage took a deep breath and step toward the car. I carefully open the door to the car, so not to chip or break a nail. I entered with my rear end first and slowly place each leg in trying not to snag my nylon clad legs on anything. The adrenaline started racing throughout my body as I place the key in the ignition. I took one last look down at my stocking feet and the heels I had on before I closed the car door with that the dome light slowly dimmed out. Depressing the garage door opener button I waited for the door to climb up which now seemed to take forever. Depressing the brake in heels felt right as painted finger nails dug into my sweaty palm as I pulled the gear shift lever into reverse I had thought. Now in gear I let the brake slowly up ready to move my foot to the gas. Shit, the car lurched forward instead of back I quickly pounded on the brake and slipped the car in the right gear.
As I started out down the road I did nothing but look forward. Thank god no one was out and about in the neighborhood. I was feeling a lot better as I headed out down the main drag. Then a car was coming down the road toward me as I kept both hands steady on the wheel, and I purposely looked straight ahead trying not to make eye contact. The nervousness was slowly going away as I told myself nobody can truly see who I really was, but to be safe I headed toward the country back roads. The more I drove the less frighten I had become, but thoughts started entering my mind, horny thoughts. I started thinking of cock and of me on my knees sucking that cock. Then it turned to be two cocks and more, and then it became me bent over the hood of the car and taken from behind. I always wanted to be in the female role when dressed but could never act on it. Maybe tonight or this weekend as the drive and dress made me feel like I really could finally take that next step.
The Damn Thing Just Stopped
I became little braver I drove on and was close to the park that was infamous for hook ups. Maybe I could just take a look. I spotted the sign that said park next left. I made the turn headed toward the entrance but kept going. I chickened out, but after a mile or so I talked myself into turning around and headed back. The whole time I kept telling myself go for it this is what you always wanted to do. The entrance came up fast and I turned right into the park entrance and found that here were two other cars in the lot next to each other. I parked far away from the two cars and sat there watching and waiting thinking how I should go about this I never done anything like this before; most of all dress as a girl. A few cars came and went past the park entrance to which I became very nervous again. I turn the key in the ignition and decided it was time to get the hell out of there. As I was pulling up to the main road I could see in my rear view two men emerging from the woods of the park. They stopped at the edge of the woods and waited till I had fully exited the park before they moved toward their cars.
This got me all the more horny again thinking what those two guys must have been doing in the woods as I drove on into the night. I began to think about the adult book store down by the expressway. I always knew about the gloryholes there but never truly could get up that much nerve to do something like that, but tonight I just may as I made a turn and headed that way. As I drove in the late autumn night past farm fields ploughed under for the year the car started to hesitate and sputter; I saw gravel rode up ahead as when the car finally died. The car had just enough momentum to make the turn and go down a few car lengths till it came to a complete stop. I cursed and pounded the steering wheel as I tried to restart the car to no avail.
I reached for my cell phone and started to think whom should I call. I started to think who, whom can I call that I could trust with my secret. Fellow workers, friend, family, or neighbors. No, no, no and NO. I have to call someone but whom? I sat there thinking...maybe I could walk home...no damn these heels and the way I am dressed no way...why did I not think this through and have a change of clothes. I decided I had to do something...yes have to call tow truck...they should not care...they do not know me...beside bet they had seen worse. I open the browser for search...damn no 4g hell no 3G...shit not even a cell signal. I put the phone out the window holding up but nothing. I got out walked around the car and damn near twisted an ankle walking in the rocks. I got back in the car as closed my eyes trying to think. As I sat there I heard a loud short WHOOP.
When I had opened my eyes I could see nothing but bright head lights and flashing red and blue lights in my rear view mirror. They were bouncing off trees, shrubs, clouds, hell little fury animals scurrying about. I hung my head in shame as this had to be the ultimate nightmare for a cross dresser. I was startled by a tap of my window, I depress the window down button as this seemed to be the only thing that was working on the car.
Between a Rock and Hard Place
With the window down the officer said. "Hello ma'am what seems to be the problem?"
I returned with small timid voice. "Just won't start."
"O.K. I will call you a tow truck but first may I see you license and registration."
Shit I thought... in my rush I never grab my driver's license. I started to panic but dug through the glove box and produced the registration and handed it to him.
"I am sorry sir but seem to forgot my license tonight."
He put his flash light to the registration and had a quizzical look on his face. "Is this your husband?"
"No"
"Ma'am could step out of the vehicle"
He stepped back and waited for me to open the door and get out of my car. I sighed as I reached for the door handle and accepted my fate. I slowly opened the door and turned slowly in the drives seat while keeping my legs together I placed them on the ground. I reach for the door to help prop myself up on my heels. The officer shone his flash light on my feet. He must have notice that I was in four inch stiletto heels as he held out a hand for me and helped me up the rest of the way.
"Come on Ma'am I will help you to my car."
Oh Thank You I am Not Alone
He was gentlemen as he place a hand on the small of my back and held my hand with his other hand as he lead me to the drives side of his police car. He open the door for me and help me inside. I just sat there with my legs still out and the car door open. As he looked one more time at the registration.
He spoke again quizzically. "My I ask are you this person on the registration?"
I sighed and answered. "Yes that is me." As I lowered my head into my chest.
"Damn you could have fooled me Tim."
"And you know me how?"
"I am Ryan from high school."
"Ryan?" "Ryan Manns"
"Yes the very one."
"Shit...god...I...I...I am so embarrassed...I can explain..."
"No...no...need to explain. I glad it was me that found you instead of someone else; they might not so understand."
"What do you mean?"
"Well some of the others are...well kind of homophobic."
"That is sad, that people are still like that today."
"Well they are just frightened and little minded people I guess. Wait here I will get your keys and lock your vehicle up and will take you home. You can call a tow truck in the morning."
"Thank you, god, and thank you."
Ryan did as he said as he came back handed me the keys and closed the door for me. He got in his side of the squad car and proceeded to call in on the radio. He then turned to me and said he was now off his shift and would take me home. He shut down all the flashing lights then turned to me.
"Hey you do not mind if I say that you had me fooled there...I really had no idea you were really a guy? How long have you be doing this if you do not mind me ask'in."
"Well I really started out when I was about eight years old...use to take my older sister's and mother's stuff and try them on."
"Yeah I can understand that, but I heard you had gotten married and stuff. So does your wife know you are out doing this?"
"No, she left me about two years ago."
"Was it over this kind of stuff?"
"No, we just could not get along and the married life was just not for her. I got kind of depressed afterward and started dressing up again as kind of a day to day relief thing. Well this really is the first time I ever left the house like this. Really."
"I understand I have had it hard myself after high school."
"What do you mean?"
"Well...hum...hey I am off shift and would you like to go out and get a drink and I will tell you all about it."
"I do not know...I possible cannot go out like this."
"Hell yes you can, you fooled me, and beside where we are go `in people do not give a shit."
It's All Out on the Table
Ryan put the car in gear and we were off. We ended up on the old side of town at a hole in wall kind off bar I never visited before. He pulled around back of the place a told me to wait right where I was at. He got out and went to the back of the squad car and opened the trunk. It was dark and secluded back behind the bar. I heard him rummaging around back in the back of the trunk of the car till I heard him slam it shut and he walked up and opened the car door for me and gave me a hand out. Wow he change out of his uniform quickly and was into some khaki pants and nice button down dress shirt. He led me to the side door of the place and even opened the door for me.
The place was dark and everything was brown and orange motif. It smelled of stale cigarettes and alcohol. He led me to an empty booth near a blacked out window across from the bar with an empty set of tables between them. Soon as we sat down a skinny young girl with pig tails, white blouse tied in front at the tails over a tank top, cut off gene shorts over black tights, and wearing black leather combat boots asked us what we would like to drink. We both order a beer and she was off. Ryan and I started small talked about few people we knew in school till our drinks arrived.
He commented on how good I looked as a women and all I could do was blush. I changed the conversation to him and wanted to know what he was up to after high school. He came right out and said he had started working here cleaning the place up during off hours till he was old enough to join the sheriff department. Then it was quid quo pro for a while. I told him about going to college while he talked about the academy. He asked me about how I met Jenny my ex-wife till I asked what about him and why he was not married as he always was with the hot girls in high school.
After along stare into the ceiling he came out and said he was gay. Not just gay but full on leather and BDSM and the dominate one. That got my panties in a bunch right away, and I just about spit my beer in his face as I was tipping my beer back that very moment when he was telling me all about it. I then asked him why he was so gentlemanly like to me tonight as from what I heard gay me are just not into transsexuals let alone transvestites. That being said he told his story about not too much like me he was also hurt by his lover a few months ago and he too had left him. He said he was thinking about maybe he would try women again like back in high school till I fell in his lap.
I was almost flattered and did not know what to think. I excused myself and said I had to use the ladies room. As I headed toward the restroom I stop and looked at both doors one mens other womens and paused on which one till a man bumped into to me a said excuse me hun. That decided it I step into the ladies. I headed for the first stall and it was just as bad as the mens. I took hand full of toilet paper to clean the seat as I thought I should really sit as a lady to pee. Next to me the other stall was occupied, it was the bar matron. We finished about the same time doing our business.
We met at the sinks. She asks how I met Ryan I explain how my car broke down and we knew each other from high school. She complimented me on how sexy I looked for a dude "her words" and how good Ryan I looked together. In fact she wished her girlfriend would dress up like me. I took her words to heart after she left and thought about what the worst could happen if I gave whatever I was feeling a try. I looked at myself in the mirror and turned on my heels straight out of the womens restroom right up to Ryan sitting there in the booth.
I came at a standstill right in front of Ryan placing one foot perpendicular to the other, as my wife did when she was mad or horny for me, both hands on my hips I stood there and looked at him. When he turned to look up at me I placed booth hands on the side of his face and leaned down and gave him a deep kiss right on the lips. His response was delayed at first but a hand behind my neck knew what I needed to know. He threw a twenty on the table and stood up put an arm around my waist and asks me if I wanted get out of here. I turn back to see the bar matron smile and wave good bye to me.
This is Going to Happen for Real
Ryan was still a gentleman as I placed an arm under his when he led me back to the squad car. Again he opened the squad car door for me and helped me get inside. He asked his place or mine, I came right out and said his place. Soon after I needed to remove my heels and place my stocking feet up upon the dash board. He reach one hand over and placed it on the top of my thigh and said someone needs a spanking tonight. I immediately developed an erection with those words. All I could think of to say was I hope it is a promise. The next word he said to me made me tense up and he knew it when he said that is a promise.
Never in my life would have thought I would meet someone that could deliver on the number fantasy of my life. Since that first playful paddling for my birthday in elementary school from my first grade teacher, I craved it, but I was never able to relive it as I would have desired. Yes, I had self spanked many times, most of all while dressed in my mothers or sisters clothes. From age sixteen on I wanted to be made to dress up fully as a schoolgirl and put in front of a classroom full of students. To which I was made to bend over grabbing my ankles and swatted severely with a big wooden paddle.
I had to shake myself back from my day dream of being swatted in front of class when Ryan announced that we had arrived at his home. I could hear the distinctive pops under the tires of a gravel driveway as I saw the head lights bounce of the front of a classic ranch style house. I reached down and strapped my feet back into my sandals for the walk I was going to have to take to the front door. There was no garage just an old Camaro set off to the side. It looked like a work in progress as we came to stop next to it. Before I could get the last strap buckled around my ankle he was at the passenger door waiting for me. He opened the door offered a hand to me and we proceeded toward the front porch that was dimly light with an old lamp that looked like it belonged on an old stage coach from the nineteenth century. He placed his key into the door handle lock and opened the front door. The interior was dimly lit from a light far off in what look to be the kitchen.
"Welcome to my home." Ryan announced. Then the click of a light switch and a gorgeous lamp on an end table came to life.
"Wow!" I was exclaimed.
A few more clicks and couple more lamps flooded the living room.
"What the hell, you tricked me...you brought me to Martha Steward's house!"
"Funny, but this was all Angle's doing...my ex'es."
"Well I do have to say it is all very nice."
"Thank You." Ryan said as his voice trailed off.
"Hey what does a girl have to do to get a drink?" I said trying to get his mind off of things.
"Well follow me."
I did as instructed to which I was led toward the kitchen. He said take a seat as he headed toward the refrigerator and pulled out a couple of cold beers. I pulled out a chair at the kitchen table and took a seat in it. I gently crossed one leg over the other at the knee, placed an elbow on the table, rested my chin in my hand, then placed other hand on my nylon clad leg and slowly rubbed it up and down my leg. I batted my eyes looking up at him. He placed the beer on the table next to me.
"So, about you being this dom?" I quizzed.
"Yes what would you like to know?" He question back.
"I never was in this kind of situation before?" "Before you ask I truly always wanted to be in this kind of situation since I was sixteen but never or should say never had the chance."
"Well depends on what you want."
"What do you mean?"
"I as a Dom really believe it is a two way street." "I get what I want by being the dominate one and get off by pleasing the submissive with want turns them on."
"O.K. I am totally new to this how does it go."
"We can start with you telling me what you like or I can bring up things you may want to try."
"Well I can tell you I always dreamed of being a school girl and made to bend over and swatted."
"There you go that is a start." "What else would you like to try?"
"Well... not sure but to be caned and oh...oh tied up was always on my list of thing to try."
"Why don't you follow me?"
To Hell With it All
We got up from the table and grabbed our beers then a few short steps we walk to a door which lead to steps that went down to the basement. He led as I carefully placed each four inch heeled foot on each step of the wooden stairs. I placed a hand on the wall as the other held the beer tightly as we descended the creaking steps. As we reached the bottom it looked like any old damp basement with a washer dryer off to the side, old bicycle, dusty treadmill used as a clothes rack, and odds ends strewed about. We had reached the bottom and just to the left was another old door to which he opened.
He reached inside and hit the lights. To my surprise it looked just like a dominatrix dungeon I have seen many time on the internet. It has a leather bound spanking bench lined with silver studs that held the leather to the bench. A large screen television and camera on a tri-pod. The walls were all done in cherry wood that you would see in some CEO's office. Straps and ropes hanging on a peg board along one wall. Paddles, straps, canes, and whips hanging on the other. Off to one side a beautiful cabinet stood proud and erect. He walked up to it and swung the doors open wide thus reviling its contents. It was full of cuffs of all types, bright red ball gage jumper out at me, dildos, plugs, and all other naughty toys I never thought off before.
"Well what do you think?" Ryan said proudly.
"I ... I ... do not what to think." I said wide eyed.
"Sorry." "If it is too much I..."
"Oh, hell no...I LOVE IT!"
"You do?"
"God yes more than you can imagine"
"I glad it did not scare you away as I...I thought it might be a little too much for a first timer."
"Well if you put it that way...yes it is a little much." I said with a laugh.
"It had taken few years to collect all of this stuff."
"Yes I understand...but Wow." "Wow"
"You do not approve?"
"OH, I approve but wow."
"Hey why don't you just look around and finish your beer as I go up stair and clean up." "Then maybe you like to try few things."
"I would not know where to start." As I giggled.
"O.K. I try to hurry up and be right back down."
Who has Been a Naughty Girl?
Ryan departed leaving me all alone in his dungeon. I heard him scamper up the stairs. I stared at all four walls trying to take it all in. I heard the distinct screech of waters faucets being turned on. Being in the basement I could hear the water running and the squeaking of what had to be Ryan's feet rubbing on the tubs floor. I walked about the room looking at everything. Second time around I started taking things off the wall holding them and then finally picking up an small wooden paddle I smacked against my other hand feeling the sting. I heard the shower stop and like a surprised child being caught touching things I was not supposed to I placed the paddle back and quickly sat on the bench. After a few minutes I decided he was not quite coming yet, so I went over and pick up few dildos and fondled them.
I could then here Ryan descending the stairs as they creaked under his strain. I quickly placed the dildos back where I had found them. My stomach had butterflies as I heard him approach and enter the playroom of pleasure and pain. I had that feeling again as a child would if caught touching things I was not supposed to. I turn to face the door as I heard it creak and close behind him.
"What do think?" "Anything grab your fancy?" Ryan said as he stood in the door way.
"I was really thinking about the paddles." I said as I stop to take a double take of him.
Ryan had on Doc Martin black leather boots, a black leather vest with nothing on underneath it, and then what caught my eye was the very tight, and I mean very tight, leather shorts that left nothing to the imagination. What I saw was a monster of a cock veins and all showed through the dark leather garment. I think my jaw had hit the floor literally as Ryan had stepped up and placed his hand under my chin and lifted it up. With his hand under my chin he looked me in the eye.
"So I see my sissy has been playing with my toys." Ryan said with little forcefulness.
"I was just..." I stammered, as he cut me short.
"I have not been more than fifteen minutes and you hand your hands all over my stuff."
"I was just looking."
"Just looking!" "You did just more than look you touch them, pick them up and were playing with them."
"I was only curious...I ..."
"No more talk!" "I know you were touching my stuff and you know what happens to naughty girls that touch my stuff."
"No." I was getting little nervous.
"Naughty girls that touch things that they are not suppose too get a spanking." "Do you need a spanking, Natalie?"
"Well I was looking and..." I was cut short again.
"Looking and touching!"
"Yes touching." I said with my lower lip pouting, head lowered and eyes wide and trying to flutter my eye lashings like a little girl.
With that Ryan grabbed my arm and pulled me over by a chair that matched the spanking bench. I stumbled on my heels as he dragged me near the chair. Without letting go he sat in the chair and pulled me down to which nearly fell over him, but kept my balance. He let go off my arm and slap me on my back side very hard. I could feel it right through the skater dress and the crouchless panties. I was told to go over his knee. I reached back a rubbed the spot where he just swatted me. As I bent over I placed one hand on his lap and slowly lower the rest over my body over his lap. I adjusted to where I could place my hand on the floor and the tip off my toes could still touch the floor. I crossed my legs at the ankles, placed my other hand around his hairy leg, then lowered my head waiting for the next smack across my raised up bottom. As I laid there across Ryan's lap I could feel everything. I could feel the garter straps holding up my stockings digging into my thighs as my weight feel into his. I felt the slight breeze on the back of my thighs as my dress raised do to the position I was in. I felt every piece of dirt that was on floor where I had placed my hand. Then he landed the first blow, I let out a little sigh, not a sigh of pain but pleasure of the pain. He continued spanking me over the dress I had only just purchased and was wearing for the first time that night.
Without a word the dress was raised and I received many more bare hand spankings across my ass over the knee of Ryan. I never reached back, kick, or scream out loud. I was lost, breathing in rhythm with each stroke, and wanting even more. The spanking suddenly stop and was replaced by his hand gently rubbing my backside.
"Get up and take that dress off." Ryan demanded. "Place it neatly over the chair and go to the wall over there." He point to the one with all the paddles, straps, and cane were hanging.
I unzipped the back or the dress, grabbed the bottom of it, and pulled it up crossing my arms as I did up over my head. It was inside out, I turned back right side out, and hung gently over the back off the chair as I was told. I then step toward the wall that had been directed too.
"Quickly NOW pick out something you are going to be punished with."
I stepped closer to the wall and crossed one high heeled foot over the other, then placed my hands at my side; as I pondered at the wall. My eyes betrayed me they kept looking at a two foot, and three quarter inch thick paddle hanging by the leather strap on a peg in the middle of the wall.
I point and said, "That one."
"You sure?" Ryan said slowly.
"Yes Sir."
"Very well get it and follow me."
I grabbed it at the wide base and lifted till the leather strap relaxed. Lifting further till the strap clear the peg and tilted it so the handle fell to my other hand. I turn with the paddle with handle in one hand and the base in the other. I saw where Ryan was now standing, it was next to the spanking bench in the middle of the room. I could hear click of my high heels on the concrete with the distinct sound of heel first then toe. My hands were moist with sweat and my heart pounding so hard I could feel the pulse on my neck hitting the pearl neckless. When I had reach him I without thought bowed my head and with each hand extended raised the paddle toward Ryan.
"Very good girl...I like that you are very submissive." "Now place your knees on the two pads that extend out the side there and there and bend over the bench." "Good girl looks you have done this before."
"No sir but it looks right." As I said that I felt a smack across my ass.
"That was not a question...do not speak till you are asked to...got it slut."
I was a quick learner and kept my mouth shut after that. Ryan placed the paddle on the small of my back and left it there while he went to the cabinet. There I was in my bra, garter belt, spank me panties, heels, and stockings kneeling and bent over up in the air on the spanking bench. I looked over and could see him grabbing leather ankle cuffs and leather wrist cuffs with metal rings and hasps. He came back and placed them across my back and then began one at a time to buckle them in place around my ankles and wrists. The wrist straps hasps had neatly reached the two eye bolts that where strategically installed on the spanking bench. The ankle straps need a bit off chain to secure my legs to the bench. After that was done Ryan went back to the cabinet a retrieved a leather strap that was long enough to be wrapped twice around my waist. To which I was then tied securely to the padded bench.
I felt the paddle now lifted from the small of my back. I then felt Ryan's hand on the small off my back to which he uses to keep his balance as he leans down. I felt his breath on the back of my neck.
What is a Safe Word?
"Natalie." Ryan whispers in my eye. "Before I begin we need a safe word." "Something like a color, everyone seems to choose orange, does that work for you."
I nod my head yes and repeat. "Orange."
"Good girl." As he kissed me gently on the side of my check.
"Do you know why you are be punished right now?" "Go ahead it is o.k. to answer."
"Yes sir it is for touching master's stuff, sir."
"Good girl, we will start with thirty with the paddle you had chosen and after that it is master's choice till I feel you learned your lesson."
I nod my head in agreement. Then he began. The first few were hard but nothing I could not take. You could hear each one echo throughout the basement. Soon I made through ten, then twenty, and at that point they had started to really sting. My breathing got heavy to which he adjusted time between each swat. As we reach number twenty seven I began to strain against my bounds. Finally thirty was reached. I was given short break with him gently rubbing my behind. I felt him leave me as he went to the wall and retrieved a leather strap. He returned to me putting his hands in my waist band and pulled my panties down to the middle of my thighs. I was given another thirty hard lashes with the strap. This time I was squirming all over the place but did not need the safe word.
He then gave me a short break after having just taken the strap. I then heard throughout the room the distinct air being cut with a swooshing sound. I looked back over my shoulder to see him flexing and cutting the air with a rattan cane. As I readjusted, I felt the bonds around my wrists, waist, and ankles I could only wonder what painful pleasure the cane could bring. I felt Ryan tap the cane across my full captive bottom measuring it up for the first stroke. Then it landed with new surprise of lustful pain as I struggled against the bounds. He continued with nine more flesh tearing strokes. Then to my surprise I felt the straps of my heels being undone. The cool air hit the bottom of my now exposed nylon clad feet. Just then I began to feel the familiar tap of the cane on the bottom of my left foot, and then he landed a hard stroke on the fleshy part of my foot I almost cried out. Ryan began to alternate each foot fast and hard. I could not keep count as each blow landed.
As quickly as the punishment had all started it ended with Ryan's hand feeling the warmth he created on what I could imagine was a red bruised bottom.
"Was it all you fantasied about?" Ryan asked.
I nodded as loudly as I could as was told not to speak.
"Oh, go ahead do answer me now."
"Yes, god yes I loved everything about it." I said with short breaths.
"I hope it was not too painful, but I guess it was not as you really did not cry out." "I mean...did you like it, as did not get a lot of sounds out of you."
"Hey, no I did love it. In fact I think my face hurts more just from smiling so much." I really could not keep the big grin off my face the whole time it was going on.
"Well let's keep going." He said with few light smacks on my ass.
Well I Could Never Well O.K. if You Insist
As he step away from me I tried to look around a see what was going to be pick off the wall this time. This time he did not go toward the wall. I could not see that far behind me but could hear the noise of something being dragged across the floor. The dragging noise stopped somewhere behind me. The sounds change to something that sounded like metal clanking and winning. I could then hear him step out from behind me just into my peripheral vision. It looked to me he had just plugged something into an outlet in the wall. When he stepped back behind me again, it was a few moments, I began to hear a pulsing hum of something I could not quite make out, and it had soon stopped.
"Are you ready to try something different?" Ryan said as he came back into view.
"Yes, I am so damn horny I willing to do anything right now." I said with a little wine in my voice.
"Great I love to hear that. I think you going to really like this." He said with a hint of evilness in his voice.
"I am all yours right now, as I seem to be little tied up at the moment."
"Good one, like I never heard that before." He said with little chuckle.
Back to the cabinet Ryan went, dove right in, and pulled all sorts of things out. Bringing an arm full stuff he placed them on my back. They felt a little cold as he laid them out one by one. Then the sound of a lid snapped open.
"Hey, before I get started back here did you...ah...you know clean up." Ryan quizzed.
"What do you mean, did I shower? I returned.
"Well back here are you cleaned out?" He said while tapping a finger on my as check.
"Oh, yeah that, yes...yes. I do it almost every day now."
"You do! I thought you...were...well...straight and this was your first time."
"Well, a girl need to get herself off just as much as guys do." I said with a laugh.
"I guess I suppose so!"
"I do have a nozzle and hose installed in my shower if you want to know how much I do it."
"You mean you have anal before?"
"No, no I am still a virgin in that sense but I truly love my pink toy if you know what I mean."
"I do, and guess this will not be much of a surprise what I am about to do next. Oh and trust me I still have something I bet you never tried yet."
Just after that conversation cold liquid hit the space between my ass checks and ran done to my hole. Ryan quickly scooped some up by placing his finger between my redden checks and spread it around. His finger then worked its way around the outside of waiting tight opening. My mind tried to use telekinesis on that finger and make it enter me. It must have worked as I was awarded with finger sliding into the gates of my back door. It went in, worked around gently, and removed. More lube was added and the finger inserted again but deeper this time. Next I felt the second finger trying to enter. I relaxed and it slipped right inside with the other one. I was wanting more and deeper. I soon got what I was asking for when the fingers were removed and a cold tip of what would have to be a dildo or plug was making it way inside of me. Ryan could have not been more precise only apply the correct amount of pressure. I closed my eyes and thought of nothing but letting that thing that was being pushed into me do just that. I could not tell you what size it was, but it had seem to have been reading my mine, it would slide in widening me more and more as it went deeper and deeper. I could feel it drop off then go again making me wider, a second drop off the even wider, till it hit bottom.
"Well o.k., I did not expect that." Ryan said.
"Ahha." Was all I wanted get out.
"That is at least one and three quarter inches thick you are taking, you slut you."
"Ahha."
"You hold that there for a few...damn...I did not think you could take that much that quickly."
"Ahha."
With that Ryan was quietly working on something behind me while I enjoyed my new friend back there. It was not long till he returned to my backside. He twisted and pulled on the object in me. Applying more lube he worked it in and out of me getting my whole hole opened and lubed for what was next. When the objected was finally removed I could hear Ryan pushing that thing he was working on up behind me. I then felt that familiar touch of a much larger head of a dildo against my pussy hole. He slowly worked the head into me and said hold on. It jerked just little forward deeper into me and pulled back out. I almost cried, but with a little adjustment it as soon back in but much deeper this time. Boy did it ever go in deeper and it felt great as there was no pain because of the earlier prep work Ryan had done. The speed was slow at first as it went in, and then back out to the point of almost exiting. I tried to push myself back on in but I was too damn well tied up. The machine was ramped up faster and faster till Ryan heard my moans of pleasure. He walked up the side of me dragging his finger tips from the bottom of my feet, up my thigh, over my ass, across my back, over my head, then down my face to my chin. He raise my head and we met eye to eye. He knew I could not say anything as I was lost in the fucking I was getting from a silicone dildo and metal machine.
At some point Ryan had removed those leather shorts that Daisy Duke's to shame. With his other hand he lifted his shinny large thick shaven cock to my lips. There was no thought on my part I let him slid it into my mouth ever so slowly. Ryan was now in control of the best holes I had. The dildo tipped machine fucking my ass and the man's cock entering my mouth. He tested me by pushing it to my mouth ever so till I choked on it. He would pull the shiny, silken, and cut piece of pipe out and try to measure the depth again and again. When depth was just right he fuck my mouth slowly and precisely.
"Oh, my, your mouth feels so good." Ryan cooed.
"Mm mm." I moaned.
"But...cannot do this much longer."
"Mmm...Mmm???"
"I mean it's been awhile and I am going to cum soon."
"Mmm!"
"I really want to take you upstairs and fuck you in my bed."
Hey Just What Happened
The cock suddenly pulled out of my mouth and plopped up right and hit my forehead. It left a wet spot right where it touched me. Ryan walked away and the fucking machine had soon stopped penetrating me from behind. The unmistakable sound of the machine screeching across a concrete floor, and the dildo plopped out and slapped my inner thigh. I felt Ryan's hands around my ankles he was undoing the leather binds. Next came the strap around my waist and finally the wrists were also free. I carefully reach up to the top of the bench to lift my body up. I felt little spent as I must have really used all of my muscles from tensing up the spanking and double penetration that just took place. Ryan was soon at my side helping me. When I was fully up on my knees I place each foot down on the floor feeling how cool the basement floor was. Ryan held out a hand for me to use as I turned and faced him. I slide my hands up around over his shoulders, leaned in, and placed my lips against his. He pressed back I opened my mouth and our tongues met. Taking a deep breath in through my noise a wrapped my arms tighter around the back of his neck. I used this to lift me up a bit and even think raised one foot up in the air like some starlet in a nineteen forties moving. He placed his hands about my hips and pulled us closer together. He broke the kiss and took a deep breath.
"Stop...or...I am...going to lose it right here." Ryan said breathing hard.
"Yes I know what you mean." I panted.
"It has been awhile." Ryan looked into my nodding.
"Same for me." I nodded back.
Who Cares What People Think we are Adults After All
He dragged me out of the dungeon, and we just about ran up the stairs. The stairs were easier for me now as I was in my stocking feet. Quickly now we were doing the turn off the stairs to the kitchen, around the refrigerator, a quick left down the hall and right into his master bedroom. The room was dimly lit from a light in the attached bathroom. I was grabbed and was turned forcefully facing Ryan as his arm went behind my back and pulled me into him. The other arm reach behind me and slide up to the back of my head. My face was pushed toward his for another quick passionate kiss. My back was facing toward the tall king size bed as Ryan let go and pushed me toward it. When my thighs hit the mattress I put both hand out and down behind me to catch my fall. I could see Ryan tearing at his leather vest trying to get it off quickly, but his body sweat made it difficult. I watched him struggle with the vest as I scooted up fully onto the bed. Once the vest came off he lifted each foot up to his hand and removed the Doc Martin's. I slide even further back into the bed, and know my feet were just off the edge. As the last boot was tossed over to the side he grab an ankle and placed one knee between my legs onto the bed.
As Ryan climbed into the bed I started moving further back and reaching back with one hand I finally found the head board. With his hands using my legs as hand rails, he spread them apart, and climbed in between them. The bed sunk under his weight and could feel myself falling toward him till his thighs met mine. This point my mine was racing with weird thoughts. Why did my car never break down when I was younger? Oh look at his erect cock twitching up and down. Why did try so hard before to stop dressing like a girl? My legs and feet look so go in nylons. Why did I deny myself from wanting to be the fem in a sexual role? Fuck me, fuck me hard.
"Fuck me, fuck me hard!" I said aloud surprising myself as I was thought I was just thinking it to myself.
"Yes, I want you! Ryan breathed.
"Please put it in me!"
Ryan wrapped his hands around the back of my thighs and placed my legs over his shoulders. He moved in closer while grabbing his tool in one hand and placing the other on my knee. He guided the head to my hole and set the tip right there. As he leaned toward me I could feel the pressure of his cock wanting desperately to be inside of me. I reached my hands toward my entry point and pulled my ass checks apart. It was all that was needed for soft fleshy tip of the cock to open the rose bud. He took his hand from his cock then pushed his hips toward me, soon the large head cleared my now relaxed muscle, and he was fully inside of me now. He slowly pulled back and thrust forward again. I removed my hands and placed them upon his arms. As he slow fucked me while I used my hands to tell him how much I enjoyed each time he drove it home. His rhythm picked up in pace and to which started me moaning aloud. I let go with one hand and had to place it palm up across my forehead as I never experienced something that felt as good as this was right now. The fucking I was getting was unbelievable. Ryan's breathing was hard and sharp just like the thrusting was getting at that moment. Then five or six breathy grunts from Ryan announced he was cumming inside of me. I can never explain what hot cum feels like shooting inside of my pussyhole, but the experience of a real cock and hot cum inside of me can never be forgotten. The immense sensation will forever be with me till I die.
Ryan collapsed on top off me. Our sweaty bodies made it hard for him to stay on top of me. As he slid off to the side m hole ached not from fucking, but missing the feeling of having my hole filed with something that was warm and alive. He left one arm across my stomach as we laid there short of breath and our bodies spent. As we cooled down I could feel something wet just were my shirking member was. I put my hand down there and place a finger into the area. To my surprise it was a small pooling of my own seed, I took my finger and grabbed up as much as I could and brought it to my mouth for a taste. Yes I was rewarded with the sent and flavor of our love making. I drifted off knowing I had my first sissy orgasm with a smile on my face.
What do You Mean The Ride is Over
I woke in the morning on my side, Ryan's arm over me, and his erect penis poking me in the back. I reached back behind me and grabbed it holding it in my hand.
"Hey, are we all hard again?" I said turning my head back over my shoulder.
"What...what?" Ryan spoke coming out of his sleep.
"This...this is it ready again?" I said as I shook it.
"Oh...no pee boner." Ryan said as he quickly jumped off the bed toward the bathroom.
The bedroom was lit from the morning sun breaking through the drapes that had not been fully closed. I was still in bra, garter belt and stocking. As I heard Ryan peeing like a race horse, it dawned on me I really needed to go myself. When I joined him in the bathroom he was finishing up himself. When he stepped away I reached for the seat placed it down and sat to pee myself.
"Hey you never had to live with a girl have you?" I said.
"What do you mean?'" He says with a questioned look.
"The seat. My ex-wife always yelled at me about it. I thought it would be funny but guess you never." Saying with a shrug of my shoulders.
"Oh yeah I get it now. How about a shower. As we need to get your car."
He jumped in the shower and got it going. I finished and wiped, and stripped butt naked joining him in the shower. I never thought I would have let a man touch me in shower like he was now. Back when we were in high school this would have never happened, but this was not high school anymore. Well he called the towing company to find out were my car was and it was going to need some work that weekend and could not be possible ready till Monday. Damn it was a shame as it look like we were stuck with other for the rest of the weekend.
Written by Natalie Love, Love to her from persons that read this crap "lol". No love to hear you all as it may encourage me to write more often. Was thinking about something around the line of the apocalypse?
loverhtstockngs@yahoo.com