Billie

I've known Billie for about 4 years now. As a scoutmaster I've worked with her, via email and such, coordinating the troops that come out to help clean up her property during the Civil War Weekend at the plantation/ranch she manages.

I've never seen her in anything but period costume...one of those big hoop skirt dresses. Blue...it's beautiful with her tiny waist and perfect sized breasts. The blue dress is so perfect for her. The color really sets off her skin and makes her look like a porcelain doll with alabaster skin, dark brown eyes and long black hair. She keeps her hair up in a bun and wears a matching hat with little blue crystals dangling in a fringe around it. That combination frames her delicate face so beautifully. Every time I go out there I make it a point to see her in person...not that I need to...but because I want to.

A few months ago though things were different. My unit was hosting a large Scouting event and wanted to do it on her property so we had to visit with her to negotiate the costs and help her coordinate things at her end. We had arranged a meeting at the big house during the week and we were not going to be in period dress.

I arrived with my other leaders and met Billie on the porch. She was wearing the tightest blue jeans I had ever seen along with a black tee shirt and a pair of knee high riding boots.

Like I said I had seen her many times before but always with the big hoop skirt. I often wondered what was hiding under those petticoats...now I knew. She was stunning. She had a beautiful hour glass figure and that tiny waist...not an illusion created by that skirt. Her shirt was tight enough that I could tell she wasn't wearing a corset or girdle but I guess the years of doing the reenactment thing had reshaped her body to this ultra feminine form. I was mesmerized.

We managed to agree on prices and locations. Thankfully I was in uniform, and with other adult scouters which puts me in a very filtered frame of mind.

So we come to this weekend...the big event. 250 youths...boys between the ages of 10 and 18...my unit had devised a weekend that was going to either kill them or make them cry for sure...more than they could do...all of it cool stuff that guys that age like. However the local district tossed a wrinkle in our well oiled and perfectly negotiated plans...they booked a leadership class that same weekend and they tagged it into my event. The class was supposed to start at 2pm Friday and run through Sunday morning. I had called Billie and let her know I would be out early to babysit the early arrivals since none of then knew who she was and where we needed them to be. She said give her a call when I got to the gate and she would meet me at the site. So when I pulled up Friday afternoon I called and she said drive on in and get myself set up...she would be right out.

She pulled up in a big pickup truck and climbed down out of it. She was wearing those boots, jeans and that tight black shirt again. She smiled and greeted me. I wanted to run over and give her a hug...one of those big movie hugs where the guy picks his gal up and spins around with her.

I helped her open the tailgate and we sat on it talking until the instructor for the class showed up. I introduced them to each other and Billie said she was running up to the big house for a bit. She needed me to come up once I got him settled in...there were a few things we still needed to cover. I got him set up where he was supposed to be. I also gave him the run down on the events for the weekend and he may have youth running through his camp to various activities...we spread things out when we did the planning. We didn't know this extra class was going to be here.

So once I got him all sorted I headed to meet Billie. My mind was struggling to stay focused and filtered. Sitting on the tailgate with her was so pleasant and relaxing. It was actually kind of romantic in a rustic cowboy sort of way.

We had sat talking about nothing...watching the cattle in the next field, birds flying around. The breeze made her black hair flow and shimmer in the sun light. So my mind was racing, trying to not be obvious that I just wanted to ravage her. She was so damned sexy.

I pulled up to the big house and collected myself before I went in. She met me at the door and said she needed some paperwork signed, but she wondered if she could impose on me for a moment. She said she was alone and there was some heavy furniture she needed help with.

I smiled and said with a big fake southern accent "Ma'am a scout is helpful" and followed her upstairs...keeping my eyes focused on her amazing ass in those painted on jeans.

We got to the top of the steps and she said she lived here alone. The owner only came by on Mondays and the ranch hands never came around the house anymore.

She lead me to a room with a small couch that she needed me to shift from one side of the room to the other. It was very light so it didn't take much effort. I asked if there was anything else she wanted me to take care of while I was here. She smiled and said "follow me..."

We went down stairs and to a door off the main hallway. I had seen the door during the tours but it was always closed and marked private. She said this was her suite in the house. It was a section that was completely modernized and meant for the live-in manager. Nobody ever went in except her...even the owner.

I followed her through the door and saw a wonderful modern apartment...very chic furniture, modern art on the wall...some of it very risqué.

She lead me through her apartment to her bedroom...it was completely anachronistic...in this modern apartment she had a giant four post-canopy bed. She said it was a modern reproduction. After living in this place for as many years as she has she just kind of fell in love with that style bed.

I was puzzled why she was showing me this. She could tell I was confused but not uncomfortable...

She pointed to a chair and said have a seat. She would be right back with the paperwork. I complied and waited.

She took a few minutes and returned with a thick stack of papers and said I needed to read it before I signed it and she slipped out of the room.

As I read it was obvious this had nothing to do with anything related to the event. It read more like a temporary employment contract.

I waded through the thing and got to the end of it...now I was really confused. There was no mention of compensation...but the last line said something about other duties as required.

I sat and waited for her to come back. When she returned, I was going back through the document trying to make sense of it...I didn't look up at her. She asked if I was ready to get to work. I looked up and was completely shocked. I was speechless.

She had changed into a period costume..red and black...and was holding a riding crop. I quickly flipped to the last page and said "ink or blood?"

She said "Ink was fine...no souls will be stolen today" and smiled in a rather evil way.

She sat on the edge of her bed and instructed me to come kneel at her feet. As I settled at her feet I could see her boots...pointed toe, high heels but the boot was just above the ankle and had brass buttons on the sides. Very pretty.

She looked down at me and said with a smile: "I know you want me. I've known it for a few years now. You go out of your way to meet me...use any excuse to endear yourself to me. You laugh and say you are a...what is it you keep saying? Oh yes a pathological flirt. Well I am not drinking that koolaid. I know you want what you see. You will get it but maybe not the way you want it. However given your obedience so far I think it's exactly how you want it. Is that right slave?"

Had I been that obvious? I was ready to cry...both from the embarrassment and the joy that I was going to be her slave...even if for only a little while. I looked up and answered simply "yes."

She looked at me with those deep dark eyes and said "It's ok...nothing to be embarrassed about. I have wanted you as my slave for quite some time now and have been trying to figure out a way to make you mine...obviously I have found it."

She told me to stand up, completely undress, put my clothes on the chair and return to my spot.

She never told me what my spot was but I figured she meant back on my knees at her feet, so that's exactly what I did.

She said those magic two words...good boy...and smiled. She had me and she knew it.

She told me to take her shoes off. As I did I noticed she was wearing toeless hose...they looked like lace hose but left the toes exposed. I had never seen them before. She noticed me admiring them and said she got then in Germany while on vacation. I complimented her on her good taste and how beautiful they were.

As I was taking her second boot off she used her foot to play with my body. She ran her toe along my inner thigh. Pressed the ball of her tiny foot against my nuts crushing them slightly. She then stroked my already hard cock with her toes. I managed to focus enough to get those little brass buttons undone and the boot off.

She put her other foot right in my face and moved it to my mouth. I gently supported her heel and began kissing her toes.

She slid her big toe into my mouth. I sucked on it. Twirling my tongue around it like I was giving it a blow job and wanting it to cum in my mouth.

All the while she kept stroking my cock with her toes and when she would get the the base she would crush my balls with her foot.

I kneeled there pleasuring her toes and enduring her torments. She said I was a good boy indeed and asked if I had done this before. I nodded yes. She said: "Oh I didn't realize so there is no reason to start at the beginning...let's see what you know..." And pulled her succulent toes from my mouth and lifted her dress to toss it over my head. I kissed my way up her legs.

Using my tongue, I tickled her soft skin through the holes in her lace hose, as I worked my way up her lovely legs.

I got to her mid thigh and discovered she was wearing hose and garter combination.

I had miles of soft, silky thigh to worship. I was going to take my time. I had fantasized for years about getting up under her hoop skirt and I was finally there. I was not going to rush this moment.

I worked my way up her silky thigh. Kissing and nibbling as I went. I caressed her lovely legs as I moved up, running my hands as high as I could along her thighs.

Finally I was at the top of her inner thigh. That sensitive and very ticklish fold where the thigh meets the pelvic floor. I love that spot. I could feel how worked up she was her pussy was incredibly hot and wet on my cheek. I could smell the sweet scent of her arousal as well. I began to explore with my tongue and suddenly Billie grabbed my head and said: "Enough teasing! I'm in charge here I'm the one that does the teasing! You are very good at it but enough...you will give me what I want...NOW!" and shoved my face into her pussy.

I wasted no more effort trying to arouse her. With her hands pressing my face into her pussy I pushed my tongue up into her as far as I could. She tasted wonderful. My nose was pressed against her clit. I could feel how hard and swollen it was. I was amazed at how large it was...I was going to enjoy sucking on it!

I tongue fucked her for all I was worth. My mouth was opened as wide as I could so I could get as deep into her sweet pussy. My tongue worked on the spongy spot and the tip could get just past it if we both moved just right. It was magical when it hit there. She would hold herself there letting me work her then rock back and I couldn't reach it. When I was deep in her the moans she let out were so arousing for me. I knew I was giving her what she wanted. She would not let me bring her to orgasm...she was teasing me...she knew I wanted her to cum.

She kept herself there on edge for quite a while. My tongue was getting tired from trying to reach deep into her. I was determined to make her cum.

She relaxed her grip but I kept pressing into her. Her hips were grinding on my face. I could feel she was getting close. She pushed me away before I could make her cum.

She then gently guided my mouth to her clit. It was rock hard and sticking out from its hood. I gently kissed it then drew it into my mouth and started sucking on it. My tongue gently flicked back and forth as I sucked harder and harder.

She gripped the back of my head and forced my face into her crotch. She began grinding herself on me as hard as she could.

My teeth cut into the insides of my lips from the pressure. I gripped her thighs so I could hang on and keep my lips locked on her clit.

She let out a scream of passion: "Oh Fuck! Don't you dare fucking stop! Fuck! fuck! fuck!"

Her thighs squeezed against my head. All I wanted at that moment was her pleasure. I was getting what I wanted and so was she.

She was trembling like a leaf in the breeze and let out one more "Fuck!" Then the flood began. She was having a massive orgasm. Her cum tasted even sweeter. She relaxed her grip on my head and I began gently cleaning her with my tongue. Every time I touched her she would twitch like she was being shocked.

Once I licked her clean she invited me to lay beside her and hold her for a bit. I crawled out from under her skirt and onto the bed beside her. We spooned for a while. I gently brushed her hair from her neck, exposing it so I could kiss it. She fell asleep like that and took a short nap. I stayed with her watching over her while she slept. She was so beautiful...even more so now in the afterglow of an amazing orgasm.

When she awoke she told me I was not going to get to cum today. There just wasn't time to do it properly.

She told me to stand facing her with my legs spread. She slid a stainless steel hook into my ass then attached it to the base ring of a cock cage she was fitting me with. The final attachment was a urethral insert that threaded into the tip of the cock cage. It was hollow so I could urinate. She left me with enough play in the anal hook that I could remove it for using the bathroom but it was bulky enough that I couldn't leave it out and be dressed.

She locked the cage as she explained the rules: I was free to go about my business for the weekend. I had to keep everything in place as much as possible...obviously the anal hook would have to come out from time to time. She said I was to return to the big house at 1am both Friday and Saturday night to service her again.

I simply said: "Yes ma'am."

She told me to get dressed and back out the the campsite before people started showing up. She would join me after she got changed.

I went back to the gate and sat in my big chair to check people into the event and my phone vibrated. I looked and I had a multimedia message from a number I didn't recognize. I opened it and was greeted with a full body nude of Billie and a note: "see you in a few minutes..."

Billie drove up and sat in the chair next to me at the check in booth. She was back in those tight ass jeans but wearing open toed shoes and a more conservative top.

Every time we were alone she would toss her hair to the side away from me, exposing her graceful neck with its creamy skin. I knew I was in for a long hard evening of subtle teasing.

It seemed to take forever to get everyone checked in and to their camp sites. Once we got them all checked in Billie kissed me and said see you at 1. My heart nearly stopped from the excitement.

The hours ticked by; all I could do was wait with anticipation for all of these youth and other adults to go to bed so I could slip away quietly and serve my Mistress.

Finally the last propane lantern went out...midnight...I was going to be able to do this.

I gave myself 15 minutes to walk down the long drive to the big house. I managed it in 10. I went to the side door as instructed and found it unlocked. I went in and the house was lit with candles. I took a seat in the parlor and waited.

At 1am sharp the door to her apartment opened and her hand beckoned me in.

By this point in time my cock and balls were killing me. My ass was raw from the rubbing of the hook between my cheeks.

I entered the room and was blinded by a flashlight directly in my eyes. Then she put a blindfold on me and lead me back to her bedroom.

She helped me undress and then pushed me forward onto her bed. I made no effort to catch myself. I wanted her to see I trusted her.

She rolled me over and began releasing the hook from my cage. She asked how many times I had pulled it out..."not once" I replied.

"Mmmm...good boy! We should clean you out then huh?" And with that she lead me to her bathroom, had me empty myself and then began a nice comfortable enema. The warm water trickled in at first and as she saw I was relaxing she opened the nozzle a click or two. Soon I had taken the entire bag. She had me hold it for a bit.

She removed the nozzle and told me to relieve myself. When I was finished she started a second enema saying she loved a squeaky clean ass and she wanted to make sure I was well hydrated.

Once she had me all cleaned out she lead me back to the bed and had me lay so I was bent over the edge with my feet on the floor and spread apart, exposing my ass and balls. She started smacking my ass. It stung at first then the warming sensation began.

She grabbed and tugged down on my balls. I whimpered and tensed up but did not move.

She asked if she would ever have to restrain me. I said: "No ma'am, I was trained better than that."

She said she was very happy for that because a true sub will restrain himself out of devotion to his Mistress

She dug her fingernails into my back and scratched me hard...the entire length of my spine. My back arched lifting my shoulders from the bed but I didn't try to get up.

Billie then began lubing my ass. She said something about it being medicinal as well to take the sting out of having the hook in so long. Then she slid her slender fingers into my tight ass, probing me to see what I will take. One finger at first...then two. She found I was tight but very receptive as I relaxed more and more. She asked if it had been a while since someone played with my ass; I responded yes...too long.

She slid a third finger in and then a fourth. She asked if I had ever been fisted. I said I hadn't she said that was going to change.

She slowly removed her fingers from my ass and added more lube. She said she wanted me to see something and told me to remove my blindfold. I did so quickly...if for no other reason than to see what she was wearing. I smiled as my eyes focused on her totally naked body...well almost totally naked. She was wearing a harness and strap-on. She showed me that it had a total of three dildos: the one I could obviously see, one in her tight pussy and the other in her perfect ass. She said she was going to fuck me until she had an orgasm.

She stepped back around behind me and soon I felt her pressing the head of the strap-on against my hole. I arched my back, rotated my hips a little and relaxed. It slid right in and she began to fuck me. Slowly at first then gradually building up speed as she thought I could handle it.

Soon she was moaning and I could feel her hands begin to tremble slightly on my hips.

She pulled out and said I was going to ride her. She lay down on the bed and had me impale myself on her dildo while facing her.

I rode her cowboy style(?) fucking my ass for all I was worth. I watched her beautiful face as the first waves of ecstasy came over her. She dug her fingernails deep into my chest and let out an amazing stream of "Oh Fuck!" repeated over and over.

All of this had my poor cock worked into a painful situation. My entire body was in full arousal and my cock couldn't come along because of the cage. It had swollen to completely fill the cage but could not get completely hard and was extremely painful.