Crossdressing Charlie Episode 6 The Tennis Uniform
- 3 years ago
- 10
- 0
Crossdressing For Sex free porn video
The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock throbbing with anticipation. I never dress exactly the same each time so in truth they’re never sure exactly what’s going to happen. My transaction today is simple enough. We had been chatting online and I showed him various photos of me doing kinkier and kinkier things. He was inexperienced with a woman like me but had always been turned on by the idea. We had first bonded over a shared fetish for leather so today’s outfit is going to incorporate as much of that as possible. Our initial meeting at the door had been brief and he probably wondered who I was relative to Brooke. Without providing explanation I led him to a room to wait and I could see his eyes open wide. The walls of the room are decorated with images of kinky sex scenes involving Brooke. I like to be photographed in action. After watching him take a seat while trying to get a sense of his surroundings I leave him to it and shut the door behind me. No words.
I get ready in the next room with a large mirror and a table for my makeup. At 6’1 I am a tall woman, towering when I am in my ridiculously high heels. Fortunately I like to spend my time on my hands and knees or on my back. My short brown hair is easy enough to hide under a wig and my thin body fits well enough into women’s clothes. I start by undressing in front of the mirror, removing my masculine clothes. Top first, I play with my nipples which harden quickly. I imagine what they’d be like as large breasts bouncing away as I ride a thick hard cock. My own cock is already hardening at the prospect. Next I undo my pants, dropping them to my ankles. My hard meat protrudes out aching at what is to come. At 7.5” uncut I carry my own although I always hope my lover is bigger. I never bother to tuck or to hide it, anyone who is with me knows who I am and what I have. I encourage my lovers to enjoy all of my body and I get a lot of pleasure out of any attention. Pulling my pants from my feet I am a blank canvas ready to paint.
Staring at my body in the mirror I lightly stroke my shaft. A little glimmer of precum appears at the tip as a reminder that I mustn’t get ahead of myself since there is a lot more to enjoy. I turn around and look at my ass. Small but very spankable, I love feeling hands on it as I am used. I grasp it and spread it apart. After so my years my hole is well fucked and it certainly looks it. Used by countless cocks and more, it almost pulses at the prospect of what’s to come. I’ve never wished to have a pussy and nor do I call it one either. Rather I think of it as something else entirely. I can clench it tight and milk whatever is in me, controlling how much pleasure my lover receives. I like it rough, hard and to be pounded into submission. I like be stretched. I like it to hurt. And I want to be filled with hot cum. Don’t waste it on my face or down my throat, fill me with your seed and then pass me onto the next stud to have their turn. Fill me till I overflow. I take one finger, cover it in my spit and push it into my hole. I feel a shot of pleasure up my cock. I can’t wait to get fucked.
Ready to start getting dressed I begin with my black fishnet stockings which I roll up my legs to my thighs. Sometimes they are torn from another encounter but these are fresh and new. To hold them up I buckle a black leather garter belt around my waist. It is studded with a thin chain running around it. The buckle is thick, the metal clasping sound music to me ears. Already the smell of leather is starting to fill my nose, god it is intoxicating. Six elastic clips run down to the fishnets. Attaching them is not something I’ve ever been particularly good at but I muddle along. This is always a moment I stop to enjoy as the first part of Brooke begins to appear.
I am not putting on panties. I don’t see a point hiding what is between legs and I have never found panties effective at holding back a hard cock anyway. Inevitably mine pops out from behind the flimsy material or I start stroking it furiously and the panties just get in the way. My lovers always want to see how I am enjoying myself anyway so I might as well make it easy for them. My lover today has showed particular interest in my cock and I expect they will play with it. I always wanted to get mine pierced but have never had the confidence. I imagine what it’d look like.
On top of my garter belt I wrap around a black leather pencil skirt. It comes down to around my knees and is a thick material, almost motorcycle leather. It has two silver zips which run the full length down the skirt, one at the front in the middle and one at the back falling between my ass cheeks. Both give my lover the ability to expose what they want to see first and also allow the skirt to stay on as I’m being used in any direction. It is tight around my legs and I won’t be able to move very quickly. Instead I’ll have to waddle slowly. Probably for the best given the heels that I wear. It is also short enough so it won’t cover my knees when I’m on all fours. With it secured tightly my cock is pushing hard against the material but for now at least is a little more under control.
For my top I am mixing it up. First, I put on my breast plate. It is massive and heavy with fake DD breasts. They have large areolas and ridiculous pointing out nipples. The nipples are pierced with large rings hanging down from each. Even though I don’t directly feel it I always beg for the nipples to be treated horribly, twisted and pulled, clamped and crushed. The mere act draws out a scream or a cry but also makes me harder still. My lover today wants to explore v******e. They are nervous about hurting me but I have told them that I want it, I want it bad. As I get fucked I also play with nipples and it almost feels like they’re part of me. With how turned on I feel I can’t help myself and play with them while watching my body in the mirror. Over the breasts is a black leather bra, studded of course. It stretches to contain the oversized breasts looking like it is going to break any moment. I struggle to reach behind my back to do it up so I turn around in the mirror. I wish I had a tramp stamp on my back, I’ve always wanted a set of handlebars for my lover to hold. I stop and do a bit of a twirl, Brooke is near. Over top of my bra is a white blouse, fresh, crisp, and tucked into my skirt. Like the bra it barely covers my large chest and the buttons when done up look ready to pop off at any moment. It won’t be difficult to take off, nor should it be. I roll the sleeves a little at my wrists. I choose the blouse purely for how it shows off my breasts. I want my lover to tear it open and throw me to the ground.
With most of my outfit on I can turn my attention to my makeup. I do this towards the end as I am really bad at getting it on my clothes and would almost certainly be covered if I started with it, especially with my white top. A wig liner keeps my own short hair out of my face as I cover myself in foundation. Even with careful application I like the makeup to look thick and almost cheap. I choose a tone separate to my normal skin color to further highlight how much I have own. I want my lover to see I went to effort for them but I’m also a five dollar whore. Too much blush and long thick ridiculous fake eyelashes add to the look. I stop for a moment to enjoy the view, batting my eyes like I’m looking for clients on the street - god I am starting to look hot.
It is at this moment I pull out my favorite piece of makeup. My blood red lipstick. No matter what I wear I always go for this lipstick. The bold color contrasts heavily with the rest of my wardrobe which is usually dark. I apply it liberally to my lips, coating them in the bright red sheen while trying not to get any on my blouse. I need plenty on my lips as I am going to put them to extensive use. My lover’s cock, ass, nipples and armpits at least and then whatever else they want me to lick, suck or eat. I always end up a mess afterwards and I love it.
Looking every cent of the cheap whore I am I now wrap up. For this lover I am going to stick with my look and I choose a long black wig with mostly straight hair and runs down just past my neck. It also covers some of my face but is long enough for me to put behind my ears. It is definitely going to get in the way when I’m sucking cock. Nothing classier than constantly having to get hair out of your mouth as you are desperately worshipping a massive piece of meat. With the hair behind my ears I attach my dangling earrings. They are themed of course, golden hard cocks hanging down with bulbous heads. They were made of metal so should make a nice clanking sound as I am pounded from behind. I am not trying to be subtle nor am I trying to hide what I like. This is about hot hard kinky sex.
At this point I can hear my lover moving around with a little bit with impatience. My body is also aching for his rough alpha touch. But I need to complete my accessories. Around my hands and up both arms go fishnet sleeves which is held into place by a loop around my thumbs. Over these go some black leather spiked wrist cuffs which look like they could take out someone’s eye. They are heavy with a buckle of course which I fasten tightly so to avoid the cuffs shaking too much when I am jerking my hands. I hope my lover requires two hands to pleasure.
Around my neck I put a bondage collar. Thick and black leather as per usual with a buckle at the back. Normally I have one with studs or spikes but this was just plain with a single D-ring at the front. I hold the collar in my hands for a moment. I always wanted a proper collaring ceremony where I become owner by someone. That feeling of being permanently subjugated by a superior. Unfortunately that has never happened instead I am owned fleetingly by countless hungry lovers. With the collar I have a heavy metal leash to attach to the ring that my lover can hold. I like to be treated like a dog, kept on my hands and knees and forced to bark. Then taken from behind like a bitch in heat. For the fastening buckle I pick up a small padlock and clip it shut. No matter what happens the collar won’t come off and I’ll be my lover’s slave for as long as they want.
The last piece. Finally. I feel almost exhausted having been turned on for so long without any relief. My cock is painfully stuck underneath my skirt and I’m desperate to get something in my mouth. All that remains are my boots. My pride and joy, perhaps the items I’ve had the longest. Black leather, of course, platform stiletto ankle boots. They are lace up with an extra zip down the side. Stepping into them is like going up a stair. Where before my face comfortably appears in the mirror now it is just my chest. I slowly zip up each one savoring the sound. I love the look of them on and pause for a moment touching myself through my skirt.
Standing up I am now considerably taller than I began. I step back, or at least waddle back, so I can admire myself in the mirror. I turn around and enjoy how the leather wraps my body. God it smells incredible. My breasts have almost popped out already and my ass looks ready to be used hard. I pout my lips and blow a kiss towards the mirror then spank my ass to get it nice and red. I’m so ready.
I grab my leash and open the door to waddle out. My heels click on the floor as I slowly make it to the next room. Attaching the leash to my collar I open the door to my lover and step in.
I get ready in the next room with a large mirror and a table for my makeup. At 6’1 I am a tall woman, towering when I am in my ridiculously high heels. Fortunately I like to spend my time on my hands and knees or on my back. My short brown hair is easy enough to hide under a wig and my thin body fits well enough into women’s clothes. I start by undressing in front of the mirror, removing my masculine clothes. Top first, I play with my nipples which harden quickly. I imagine what they’d be like as large breasts bouncing away as I ride a thick hard cock. My own cock is already hardening at the prospect. Next I undo my pants, dropping them to my ankles. My hard meat protrudes out aching at what is to come. At 7.5” uncut I carry my own although I always hope my lover is bigger. I never bother to tuck or to hide it, anyone who is with me knows who I am and what I have. I encourage my lovers to enjoy all of my body and I get a lot of pleasure out of any attention. Pulling my pants from my feet I am a blank canvas ready to paint.
Staring at my body in the mirror I lightly stroke my shaft. A little glimmer of precum appears at the tip as a reminder that I mustn’t get ahead of myself since there is a lot more to enjoy. I turn around and look at my ass. Small but very spankable, I love feeling hands on it as I am used. I grasp it and spread it apart. After so my years my hole is well fucked and it certainly looks it. Used by countless cocks and more, it almost pulses at the prospect of what’s to come. I’ve never wished to have a pussy and nor do I call it one either. Rather I think of it as something else entirely. I can clench it tight and milk whatever is in me, controlling how much pleasure my lover receives. I like it rough, hard and to be pounded into submission. I like be stretched. I like it to hurt. And I want to be filled with hot cum. Don’t waste it on my face or down my throat, fill me with your seed and then pass me onto the next stud to have their turn. Fill me till I overflow. I take one finger, cover it in my spit and push it into my hole. I feel a shot of pleasure up my cock. I can’t wait to get fucked.
Ready to start getting dressed I begin with my black fishnet stockings which I roll up my legs to my thighs. Sometimes they are torn from another encounter but these are fresh and new. To hold them up I buckle a black leather garter belt around my waist. It is studded with a thin chain running around it. The buckle is thick, the metal clasping sound music to me ears. Already the smell of leather is starting to fill my nose, god it is intoxicating. Six elastic clips run down to the fishnets. Attaching them is not something I’ve ever been particularly good at but I muddle along. This is always a moment I stop to enjoy as the first part of Brooke begins to appear.
I am not putting on panties. I don’t see a point hiding what is between legs and I have never found panties effective at holding back a hard cock anyway. Inevitably mine pops out from behind the flimsy material or I start stroking it furiously and the panties just get in the way. My lovers always want to see how I am enjoying myself anyway so I might as well make it easy for them. My lover today has showed particular interest in my cock and I expect they will play with it. I always wanted to get mine pierced but have never had the confidence. I imagine what it’d look like.
On top of my garter belt I wrap around a black leather pencil skirt. It comes down to around my knees and is a thick material, almost motorcycle leather. It has two silver zips which run the full length down the skirt, one at the front in the middle and one at the back falling between my ass cheeks. Both give my lover the ability to expose what they want to see first and also allow the skirt to stay on as I’m being used in any direction. It is tight around my legs and I won’t be able to move very quickly. Instead I’ll have to waddle slowly. Probably for the best given the heels that I wear. It is also short enough so it won’t cover my knees when I’m on all fours. With it secured tightly my cock is pushing hard against the material but for now at least is a little more under control.
For my top I am mixing it up. First, I put on my breast plate. It is massive and heavy with fake DD breasts. They have large areolas and ridiculous pointing out nipples. The nipples are pierced with large rings hanging down from each. Even though I don’t directly feel it I always beg for the nipples to be treated horribly, twisted and pulled, clamped and crushed. The mere act draws out a scream or a cry but also makes me harder still. My lover today wants to explore v******e. They are nervous about hurting me but I have told them that I want it, I want it bad. As I get fucked I also play with nipples and it almost feels like they’re part of me. With how turned on I feel I can’t help myself and play with them while watching my body in the mirror. Over the breasts is a black leather bra, studded of course. It stretches to contain the oversized breasts looking like it is going to break any moment. I struggle to reach behind my back to do it up so I turn around in the mirror. I wish I had a tramp stamp on my back, I’ve always wanted a set of handlebars for my lover to hold. I stop and do a bit of a twirl, Brooke is near. Over top of my bra is a white blouse, fresh, crisp, and tucked into my skirt. Like the bra it barely covers my large chest and the buttons when done up look ready to pop off at any moment. It won’t be difficult to take off, nor should it be. I roll the sleeves a little at my wrists. I choose the blouse purely for how it shows off my breasts. I want my lover to tear it open and throw me to the ground.
With most of my outfit on I can turn my attention to my makeup. I do this towards the end as I am really bad at getting it on my clothes and would almost certainly be covered if I started with it, especially with my white top. A wig liner keeps my own short hair out of my face as I cover myself in foundation. Even with careful application I like the makeup to look thick and almost cheap. I choose a tone separate to my normal skin color to further highlight how much I have own. I want my lover to see I went to effort for them but I’m also a five dollar whore. Too much blush and long thick ridiculous fake eyelashes add to the look. I stop for a moment to enjoy the view, batting my eyes like I’m looking for clients on the street - god I am starting to look hot.
It is at this moment I pull out my favorite piece of makeup. My blood red lipstick. No matter what I wear I always go for this lipstick. The bold color contrasts heavily with the rest of my wardrobe which is usually dark. I apply it liberally to my lips, coating them in the bright red sheen while trying not to get any on my blouse. I need plenty on my lips as I am going to put them to extensive use. My lover’s cock, ass, nipples and armpits at least and then whatever else they want me to lick, suck or eat. I always end up a mess afterwards and I love it.
Looking every cent of the cheap whore I am I now wrap up. For this lover I am going to stick with my look and I choose a long black wig with mostly straight hair and runs down just past my neck. It also covers some of my face but is long enough for me to put behind my ears. It is definitely going to get in the way when I’m sucking cock. Nothing classier than constantly having to get hair out of your mouth as you are desperately worshipping a massive piece of meat. With the hair behind my ears I attach my dangling earrings. They are themed of course, golden hard cocks hanging down with bulbous heads. They were made of metal so should make a nice clanking sound as I am pounded from behind. I am not trying to be subtle nor am I trying to hide what I like. This is about hot hard kinky sex.
At this point I can hear my lover moving around with a little bit with impatience. My body is also aching for his rough alpha touch. But I need to complete my accessories. Around my hands and up both arms go fishnet sleeves which is held into place by a loop around my thumbs. Over these go some black leather spiked wrist cuffs which look like they could take out someone’s eye. They are heavy with a buckle of course which I fasten tightly so to avoid the cuffs shaking too much when I am jerking my hands. I hope my lover requires two hands to pleasure.
Around my neck I put a bondage collar. Thick and black leather as per usual with a buckle at the back. Normally I have one with studs or spikes but this was just plain with a single D-ring at the front. I hold the collar in my hands for a moment. I always wanted a proper collaring ceremony where I become owner by someone. That feeling of being permanently subjugated by a superior. Unfortunately that has never happened instead I am owned fleetingly by countless hungry lovers. With the collar I have a heavy metal leash to attach to the ring that my lover can hold. I like to be treated like a dog, kept on my hands and knees and forced to bark. Then taken from behind like a bitch in heat. For the fastening buckle I pick up a small padlock and clip it shut. No matter what happens the collar won’t come off and I’ll be my lover’s slave for as long as they want.
The last piece. Finally. I feel almost exhausted having been turned on for so long without any relief. My cock is painfully stuck underneath my skirt and I’m desperate to get something in my mouth. All that remains are my boots. My pride and joy, perhaps the items I’ve had the longest. Black leather, of course, platform stiletto ankle boots. They are lace up with an extra zip down the side. Stepping into them is like going up a stair. Where before my face comfortably appears in the mirror now it is just my chest. I slowly zip up each one savoring the sound. I love the look of them on and pause for a moment touching myself through my skirt.
Standing up I am now considerably taller than I began. I step back, or at least waddle back, so I can admire myself in the mirror. I turn around and enjoy how the leather wraps my body. God it smells incredible. My breasts have almost popped out already and my ass looks ready to be used hard. I pout my lips and blow a kiss towards the mirror then spank my ass to get it nice and red. I’m so ready.
I grab my leash and open the door to waddle out. My heels click on the floor as I slowly make it to the next room. Attaching the leash to my collar I open the door to my lover and step in.
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