Mistress Bree gets her way

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Crossdressers in Lust and bondage.
4k words
4.49
15.7k
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Part 1 of the 2 part series

Updated 06/12/2023
Created 05/24/2020
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Some background..This experience is continuing...

It was June 25th; I had not seen Mistress Bree since August. The more time passes the more surreal our relationship seems. It started with me answering an ad in Craig's List "Married Bi seeking same".

Well I had always wondered and no one lives forever so...

My mind drifted back to the first ad in Craig's list that I answered before Mistress Bree found me. This Dom was not a cross dresser but he was definitely into bondage and said he wanted to have sex with me. After several weeks it became evident that he wanted to fuck with my head more so than my body. I had to call it off before we even met. I was depressed for some time, wondering if I could ever fulfil my forbidden fantasies but my attitude changed when Mistress Bree and I met for the first time.

We had several meetings- all but one at Bree's place in a small town nearby. The odd one was at my place while my wife was away.

We always planned on spending a few hours indulging in our cross dressing and sex fetishes, but it always seemed to be over in an hour because we were both so horny that our sessions did not last long.

I also liked bondage and Mistress Bree had said she was comfortable with that and indeed we did include some sessions but again, our hormones got the better of us so my bondage usually did not last very long.

I always thought that I had a good sized cock (or Clit as Mistress demands if be called) but hers was half again as large as mine- not a whole lot longer but significantly bigger around.

That meant when it came time for Mistress to breed her bitch (me) it was problematic. Not only had I never had a male member in my boi pussy but due to the infrequency of our meetings, Mistress's attempts to gape and enlarge me did not last until our next session. Therefore I did my best to do this on my own as time permitted, but Mistress directed me to purchase a strap-on for her to use until my pussy was able to take her big clit.

Because of our extended hiatus, I had kept my cream in the freezer as I had been directed and there were several ounces saved for Mistress.

I had spent many hours and some funds over the past few months while fantasizing about our next encounter.

On the appointed date and time I arrived at her house and knocked on the back door. I heard the click of high heels and a whispered inquiry "Jana"? That was the name that Mistress had given me. I answered in the affirmative and the lock clicked and the door swung open. Mistress was standing behind the door in a slinky black dress with thin straps and a slit to the top of her thigh. She had on lots of jewelry, 4 inch heels and very red lipstick. She grabbed my ass and I did the same as we kissed and our tongues explored each others mouths.

Funny I had had little initial interest in kissing until we actually did and I liked it very much, especially when she tries to fuck my mouth with her tongue. She pulled back a bit and grabbed my crotch- feeling my steel cage. I did the same and felt her grow underneath her panty hose. I knew from experience that there was no other underwear.

"Take off those pants" she demanded and I stepped free from my shoes and dropped the jeans- leaving her a full view of my tiny black lace panties and shaved legs and pubes..

"Yummy" she said "now get upstairs and change we haven't got all day. I intend to use you like you've never been used before slut". She gave me a swat on the ass with a riding crop as I headed toward the stairs but not before I dropped a plastic bag on her table. It contained a bottle of desensitizing anal lube, a strap on dildo (smaller than her clit), camera and a number of vibrators.

I had been thinking of this meeting for so long that I had developed a special wardrobe which I hoped Mistress would like. I had already thoroughly cleansed myself 3 times before I left home. Upstairs I went to the bathroom one more time and put on crotch less panty hose. On top of that I wore a bikini that I had made of small chromed chain- but it was just the outline of a bikini so everything was available. It matched my chastity cage. I then laced up my black silk corset and put on my thigh high pointy black boots with 2 inch heels. I put on my ankle and wrist straps, put the stretchy black hood over my head, checked out my look in the mirror and started downstairs. I used the handrail on the way down the stairs. It would not be good to take a tumble. She loved the taste of my come and always wanted to drink me. She had also come on my face and my clit and and in my mouth but I knew it was only a matter of time before she wanted to fuck me. I have fantasized about the same thing for a long time and just hoped that it could someday happen.

Just before I got to the bottom I snapped the wrist cuffs on to the sides of my chain bikini bottoms. I could get loose of course but it would take a minute or two. The high boots thankfully gave me some support to walk in.

I then turned the corner at the bottom of the stairs and saw my Mistress sitting on the edge of the table wearing the strap on with her own very well proportioned clit sticking straight out below it.

"Very interesting" she said, "but if you think looking pretty is going to save your ass you are sorely mistaken. Now stand there a minute and while you wonder what is going to happen to you today I am going to take some photos. Then we need to do a little snuggling. She took several digital photos and then said "Come over here while I stick my tongue down your throat."

She did just that and pinched my nipples while grinding against me and licking the inside of my mouth. She took a chair and had me sit on her lap while we kissed hungrily for several minutes. I could feel her hardness under my thighs. Had I not had on the cage I would have been rock hard myself. I could not move my hands so she took advantage of every square inch of my body that she could reach.

Finally she pushed me away and said " Here bitch suck my clit!" What's a tied up gurl to do? I got on my knees and sucked her as deep as I could until she said "That's enough Jana, I want to last a bit longer today. She helped me to my feet and took my caged clit in her mouth and licked the sweet pre-cum off of it. Then she put a heavy leather studded collar on my throat and snapped a leash to it. She turned me around and I could feel her loosening my black corset laces and then tightening them again until I could see that my waist was actually shrinking accentuating my hips and I seemed to be developing cleavage while my breathing became a bit labored. She finished the effect by attaching nipple clips connected by a short chain.

"There, you look much more fuckable now bitch. Follow me my little sex slave, I have a treat for you". Like I had a choice.. I followed her through the kitchen and started down the basement stairs. We proceed to the laundry room where she had tied me in previous sessions. In the ceiling was a new hook screwed solidly into the floor joist over my head in the middle of the room and there was a blanket on the floor below it and a couple of spreader bars standing nearby.

I stood in the middle of the blanket underneath the hook as directed while she unfastened my wrists from my thigh chains and clipped them to the either end of one of the spreader bars behind my back. Grabbing a prepared piece of rope she tied it to the middle of the bar and pulled it through the hook above me forcing my spread arms up and my torso towards the floor.

"We'll try that for a while my pretty and if it begins to hurt too much I might be persuaded to get rid of that bar and cuff your hands together and repeat the process."

Before pulling it too high she got one of the spreader bars and kicked out my legs until the ankle cuffs could be snapped into the rings at either end. My legs were now a good 3 feet apart and I needed to pull on my wrists to keep my balance. She then resumed pulling on the rope until I was bent nearly 90 degrees with my arms above my shoulders behind me and my head and torso parallel to the floor. I had seen this position in books. It was called the strappado. She stood back regarding the scene for a minute and then took my leash still attached to my collar and tied it to the middle of the spreader bar between my ankles. I was going absolutely nowhere. I could not go up or down but my tethers were helping me keep my balance and it didn't actually feel too bad. God was I horny and I could feel the cool air between my ass cheeks. I was in the most vulnerable sexual position I had ever been in. She took a few more photos including one while laying directly under my crotch.

"There, both your holes are fully accessible now just the way I like it. Know what we are going to do now my sexy little slave? Well you are just going to hang out pardon the pun and I am going to make you my slut for real. That means I am going to come in your virgin cunt. And of course I will do anything else I want to do with you. First I need to add some colour to that lovely ass." She then started with the riding crop- several strokes on each side and it was loud and painful. Then she dropped it and started to use her hand. It hurt too but it also felt good to be so helpless in this position. When she thought there was enough colour, she picked up a camera and took several shots from different angles.

She then walked around in front of me and inserted her clit in my mouth and began to slowly fuck my face. She went in deep enough that I could feel the head at the back of my throat and had a bit of trouble breathing while I tried not to gag. I told you she was big,right? She had to hold the strapon dildo out of the way so that it did not poke me in the eye. She held her clit in deep and took short little stokes to push it in further. I felt her pubic hairs under my nose..

"I know what you're trying to do" she said, "but you are not getting off that easily. Today I am going to penetrate you and that is where my come is going to be deposited- the first time anyway. Now lets try out some of these toys that you brought with you.."

The first thing I saw in her hand was the black ring gag. I didn't need it of course I would suck her clit any time and any where but she knew it helped to fuel the scene and my excitement. After buckling it tightly behind my head she shoved her clit into my mouth again to make sure it would fit and it did -but just barely. I think she liked the added friction.

She picked up the bright pink electronic vibrator and turned it on experimenting with the speed and intermittent settings on herself before using it on my ass and that sensitive area between my clit and my pussy. It was making me shiver all over. And dance in place. Then she held it directly to my caged clit which made me want to get hard so badly- but that was impossible. She dribbled lube directly on my pussy and tried to shove the head of the vibrator into me. Those vibrations were right at the entrance to my pussy. God that felt good but it would not go in..yet. I heard the camera click a few times.

She picked up the smaller vibrator and inserted it smoothly into me and then she turned it on. Wow! I was squirming for all I was worth but could not move much in any direction. The ring gag did not stop my moans and it made me drool on the floor.

She kept this up until we could both hear the battery begin to fail. I felt her behind me and then felt her lips on me and her tongue in me. It felt amazing. This was followed by a finger and then another with more lube. She stretched her fingers sideways and blew into my pussy and I could feel her hot breath. She withdrew the fingers and I knew what was coming next.

The lubricated head of the strap on cock pressed against my rear entrance and slowly forced its way up into my channel. It did not hurt as much as I thought it might. I had tried it at home so I had an idea of how it would feel. I heard her groan as she watched but she stopped part way in and took some more photos. She then pressed the rest of the false cock deep into me until I could feel her pubic hair against my crack and her hard clit was rubbing against my caged one.

She put her hands on my hips and pushed in and pulled out of me while her hard clit played with my caged clit and clit lips. She held it deep and made a circular motion with her hips. She varied the speed and direction of her fuck. This went on for some minutes and my hole began to get tender. She seemed to sense this and withdrew but stayed behind me watching my pussy twitch.

She came around in front of me and pressed the rubber cock in my mouth. I licked and sucked until she removed it from my gagged open mouth. Another good reason to be thoroughly clean back there. She backed off and removed the fake cock and showed me her real clit in all it's glory. I could not help but compare the size of the two. She took off her black dress and stood in front of me in high heels, panty hose (with a hole in the front of course!) and a black bra. She posed with one knee bent slightly and looked coyly at me over her shoulder. She slowly jerked her clit and added lubrication until it was shiny and looked as hard as a piece of steel. I could see it pulsing.

"Normally I would put this in your mouth to get me ready for you but we can both see that I am ready for you. You better be ready for me but you are getting it regardless. Don't worry you will get to suck it when I am done fucking you. I checked your greedy cunt when I pulled out the dildo and it is nicely gaped and obviously wants to get fucked. Good thing too because I am going to fuck it. Yes I am going to take your cherry and you are going to love it and when I have come in you I am going to take pictures of my come leaking from the cunt of my new slut. This is a turning point for you Jana. After I come in your cunt once you know that it will happen again any time I want.

If I want to do it outside or while you are tied to a bed or in any way I want it that is what will happen. If I want to have someone watch while I fuck you I will. If I message you at 12 and say be here at 1 ready to get fucked that is what you will do. Once I have fucked you, you will be my very own fuck slut to do with as I please. And I have been thinking of the many things I might do with you for some time. I knew she was right. Especially since that is what I wanted too.

With that she strutted behind me on her high heels and I felt the warm and slippery tip of her big clit touch the opening to my boi pussy.

I knew things would never be the same if she could get it into me. While she called it a cunt we both knew that it wasn't. Cunts are made for cocks and tongues and fingers and having babies and this was not made for any of those things but it was as close as I would ever get and I was determined to get my ass fucked- perhaps not as determined as she was to fuck it but that remained to be seen- and felt.

With one hand she spread my cheeks and guided her clit with the other. I tried to relax my muscles and push a bit to open myself up further for her. I felt the head push into me. This is further than we had ever gotten before!

I moaned and as she paused for a moment I could actually feel her throb. She then slowly pushed her massive tool into me and it just kept going and going. There was a sharp pain and when I flinched she stopped her forward motion and withdrew a bit but held it in me.

"Are you OK Slut?" she asked. I nodded my head and she resumed her forward motion until I think she was in.

"Fuck are you ever tight! And hot in there too- like a furnace around my clit"

She began to pull out and when she did she dribbled more lube onto her clit and then pushed it back into me. She repeated this several times until I could feel the slick lube running down the inside of my thighs. Then she put her hands on my hips and began to thrust for real. I could feel every inch of her going in and out. She pulled all the way back until just the head was inside me.

This is the ultimate submission I thought. Willingly dressed like a whore, strung up from the ceiling and getting fucked while my cock was caged and swinging with every motion of my fucker. I could feel pre-cum running from my clit and looking down and back between my legs I could see it dripping off the end of my cage on to the blanket under us. I think I zoned out for a bit.

She stopped her fucking long enough to snap more photos and then resumed.

" I can't take much more of this" she said. "How are you enjoying this, slut? Oh never mind I don't really care. Better get used to it because from now on it is going to happen a lot. I love the thought of having a nice tight cunt to fuck whenever I want."

With that she increased her pace until I felt her tighten and flex fully into me. I think I could actually feel her cum shoot into me. I knew I could feel her throb and spurt. She grunted loudly and leaned over my back and rested for some moments with the odd after shock ripping through her and me.

As she shrank she pulled out of me and grabbed the camera taking several shots of her come leaking out of me. I knew this because I could see it dripping to the floor as I looked back between my nylon covered legs. I also knew what was coming next. She walked in front of me removed the ring gag and fed me her sloppy clit. I licked and sucked as best I could until it became too much stimulation for her and she pulled out. I was in a daze expecting to get untied soon and now that the stimulation was over I began to feel the strain on my thighs and shoulders.

Sensing this she untied the rope above me, lowered my arms and released me from the spreader bar but then immediately re attached the cuffs to each other, ran the rope through them and then pulled my arms straight back up until I was in the same position again.

She walked behind me and squatted down to look inside my rear entrance so recently reamed.

"My My! look at the size of that cunt now! It's still wide open!" she exclaimed. I felt her fingering me and then a smooth slippery bulging pressure and something was shoved into me. She turned on the vibrator and I jumped. She set it to vibrate on slow with intermittent stops. The shoulder of the vibrating bulb at the end kept it in me and I had no chance of expelling it on my own. It was a very strong sensation. I heard the camera click some more.

She returned in front of me and began to peel off her ruined panty hose, shoes and bra until she was naked. She paused a moment and then sat and put her heels back on. She stroked her clit slowly while looking at me. Was it starting to harden again already? She could not resist sticking it in my mouth for a few final sucks. She then strapped a red ball gag in my mouth and picked up her clothes. She looked at me for a moment and then snapped more photos-front and back.

"You know I think I am beginning to like this bondage stuff. I get whatever I want and you get whatever I want to give you. Sounds good, Right? I am thinking of another way to hang you up but I think I need at least 3 hooks for that. I'll think about it some more."

"Well my little cum dump how do you feel now? Oh that's right can't talk can you? Oh well. I am going to go have a shower and perhaps a cup of tea. I'll be back in a bit- don't you go away now! You know, I might be ready to come again when I get back. Just thinking of you helpless and waiting here for my return is starting to turn me on again. Too bad my wife will be home in a couple of hours or I could leave you here all day. Hmm... maybe that doesn't matter anyway, she has a pretty open mind. We once had a threesome you know...maybe she'd like to watch you get fucked."

I watched her ass undulate as her heels clicked until she was out of my sight. Every time the vibrator began again after it's pause I lurched in the ropes and my clit leaked continuously. My legs started to shake. I thought about how I must look trussed up in ladies lingerie with black high heeled boots, a gag in my mouth and a hot pink vibrator sticking out of my butt driving me crazy. I wondered what my wife would think if she saw me now. There it goes again! God I needed to come! I wondered how long could I continue in this way...I guess I was going to find out.

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