Married Crossdressing Fun Ch 1 free porn video

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I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover.

I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance.

She was the most beautiful woman I had seen and I thought I had no chance with her. She was the life of any gathering, the centre of attention wherever she went. I, on the other hand, was quiet and shy, preferring to sit back and watch things happen.

One night I was quietly sipping a beer at the bar next to our campus that we frequented. Caz was, as usual, right in the thick of the noisy College crowd, doing shots. She was at the bar ordering more drinks when she tripped and accidently knocked my beer over.

“Oh, my God, I’m so sorry, here let me clean that up for you.”

“No matter, nothing much went on me anyway. There’s no problem.”

“Aren’t you sweet. Thank you for saying that. Most men would go ape shit if I did that to them. Have a good night.”

“Thanks, you too.”

“Maybe I’ll see you again,” she said, as I got up to leave.

I smiled at her as I turned to leave. I didn’t see her to speak to for another week. She was leaving the bar as I was walking past.

“Hey,” she called. “Wait up.”

I looked around and realised she was talking to me. “Oh, hi, how are you going?” I asked.

“Good, hey listen, do you want to have a beer? I still feel awful about the other night.”

“Um, yeah, OK.”

We spent about five hours drinking and talking that night. Caz never once joined her friends, nor was she in the middle of any mayhem that was going on. We went out together again the next night and again two days after that.

We were inseparable for the rest of our time at College. We graduated together and were fortunate enough to find jobs in the same city. It was then that I asked her to marry me. She said yes and we set the date for a year later.

Our engagement was one of huge workloads and a busy working life. But it was also one of plenty of quiet, intimate times. We lived together for about six months before the wedding. It was a wonderful time in our lives.

The wedding went off without a hitch and we spent a great two weeks in Hawaii for our honeymoon. Life was bliss. There was only one time that we had a little spat in Hawaii. Caz asked me one night if I would like to go out to a steakhouse for dinner or get some pizzas delivered to our room. I didn’t particularly care and told her that.

She blew up. “For God’s sake make a decision, please.” And she stormed off.

I found her an hour later in the bar, back in the middle of a group of people dancing, laughing and doing shots. I went up to her and said, “Let’s go to the steakhouse.”

“Well, it’s about fucking time you made a decision. Let’s go. I’m famished.”

It was such a small incident that I took no notice of her reaction, or of what she had said about me not making a decision.

Over the next few months our life together was great. Plenty of good sex and we seemed to understand each other’s needs really well. The only time we argued was when Caz cracked it when I allowed her to make decisions. Whenever there was a decision to be made that affected us both I allowed her to choose. She actually called me a wimp one time because I couldn’t choose between a PlayStation and an Xbox.

It didn’t help that she towered over me. We were the same height, 5-7, but she loved to wear heels, usually 4-inch heels, so she was much taller than me most of the time.

Caz calling me a wimp surprised me but that night our sex was better than ever. Afterwards Caz mentioned it. She said, “Hey, did you like it when I called you a wimp? You’ve never fucked me like that before. For a wimp you fuck me really well.”

I was immediately hard again. Caz kept up her verbal barrage while she played with my cock. “Such a wimp. Can you even fuck me again? Maybe you need to wear my knickers you’re such a wimp.”

That last statement made me cum so hard I nearly passed out.

“Ooh, so wearing my knickers excites you? Maybe I need to find myself a real stud if you are going to be a knickers-wearing wimp.”

“No, Caz, please, I love you so much. Please don’t do that.”

My cock was getting hard again, even though I’d just cum for the second time.

“Seems like you keep saying that but your little fella here is telling me different. I might just have to explore this side of you some more.”

Over the next month or so Caz kept on taunting me in a similar fashion. She would call me a wimp and threaten me with wearing her knickers. At the same time we fucked like rabbits. Only now she would have me go down on her after I came inside her.

“You love it don’t you, wimp, cleaning me of all your sticky cum.”

“No!”

“Yes you do. Don’t deny it.”

“No!”

“You do so. You are just a cum loving wimp.”

“No!”

“Stop saying no. I know you love tasting your cum, don’t you?”

“Yes.”

“What did you say?”

“Yes.”

“Yes, what?”

“Yes, I love it.”

“Yes, you love what?”

“Yes, I love the taste of my cum.”

“Oh, that makes me hot. Maybe you’d like more?”

With that Caz went down on me. She took my cock into her mouth and sucked like a vacuum cleaner. I never stood a chance. I came quickly and with force. She caught it all in her mouth and then, with a twinkle in her eye and a smirk on her face, she raised her face to my level, grabbed my head in both her hands and gave me a sloppy kiss. She kissed me hard and swirled her tongue around in my mouth. In doing so she transferred most of my cum into my mouth.

She didn’t say anything, just got up, went into the bathroom and got into the shower. After her shower she climbed back into our bed, hugged me and said, “That was soo hot. “

I silently agreed but didn’t say anything. I was still in shock; not only at what happened, but that I loved it so much.

The next day she sprung a surprise on me. “I think you loved it so much that you would happily clean my pussy of another man’s cum.”

I was stunned. I had never even considered that Caz would even think of cheating, much less talk about it with me. But my little fella downstairs had other ideas. I was immediately as hard as a rock.

“I can see by your reaction that you’d like that,” she said as she stared at my hard-on.

“Caz, I…”

“I know dear, you don’t know, how could I even think it, I’d break your heart. Yes, I know what you will say. But your cock speaks differently. You’d love it. I know it, and you know it, even if you can’t say it.”

I was shocked but deep down I knew she was right. I’d love it.

She went on, “So this is how it’s going to be. There is a guy at work who has made it pretty clear he wants to fuck me. Don’t look at me like that. You’re such a wimp you probably won’t stop me anyway. So I am going to get together with him after work tonight and you’re going to wait up for me to get home. If you’re lucky I’ll have a present for you.”

I watched her, as she got ready. She showered and then walked into our bedroom. She went to her lingerie drawer. She pulled a few things out and threw them onto the bed. They were black and sheer. She grabbed a garter belt, wrapped it around her waist and hooked it on. Then she took picked up a stocking. She sat on the bed and slowly rolled it up her freshly shaved leg. Then she grabbed the other one and repeated the process. I was really hard.

“Are you enjoying this, Michael?”

I nodded, unable to speak, as my mouth was too dry.

She hooked her stockings onto the garter belt. She then picked up her bra. It was very pretty, sheer with flower patterns on it. Caz hooked it on and adjusted it so her beautiful breasts fit snugly. She walked to her wardrobe, opened the door and picked out a black pencil skirt. She put it on. A satiny black shirt was next. It was a snug fit as she did up the bottom three buttons. Her breasts stood out and she was showing as much cleavage as I had ever seen her show. Then she did them all up. “This is the look for work. I’ll undo the buttons afterwards.”

She sat down at her vanity and picked up something. “First, concealer. A little on my fingers and dab it under my eyes and around my nose. This helps cover any dark rings under my eyes.”

Then she picked up a large brush. She opened her foundation and started brushing it onto her face. “Foundation and then highlighter. You see, first you flatten everything out with foundation and then use the highlighter to show depth.”

She contoured under her cheekbones and in the hollows of her cheeks. “Next comes blush, not too much, but enough to look natural.”

“Eyebrows come next, the same colour as my hair. After that I prime my eyelids. Dab it on with my fingers and brush it from my eyelashes to the top of my lids. Now we are ready for eye shadow. I am going with dark and smoky. Not too high on the lids, but darker as we get lower until they are nearly black at my lashes. Black eyeliner is next. This will help my baby blues stand out. Mascara next, two coats on my top lashes and a light coat on my bottom lashes. This makes my lids look darker but really enhances my eyes.”

She looked over at me and saw how hard I was. “You like?”

“Oh, yeah.”

“Now for my lips. I think bubble gum pink tonight. Flirty, sexy, but not screaming, ‘Fuck me.’ A sealer first, then liner, then lipstick.”

She had a quick look, turned to me and said, “And all done. Now I’m ready for anything.”

She wiped the pink lipstick off and went for a dark red for work, as she said. “And the pink is for after work.”

It was almost midnight when she got home. I had spent the day thinking about what she might be doing. My imagination wasn’t even close. She walked into our bedroom and kissed me passionately. Then she pushed me down onto the bed, lifted her skirt and said, “Eat me, baby, make me cum with your tongue.”

With that she smothered my mouth with her pussy. I licked and licked. It didn’t take too long before she was screaming in joy, cumming all over my face.

“How did you like that, babe,” she said?

“It was fantastic. You must have been really horny to cum so quickly.”

“Yeah, well, you know what I’m like just after I’ve been fucked. I can’t get enough. And, yes, I’ve been fucked; so many times I lost count. I’m full of Antwan’s sperm. Well, not now, you just cleaned me up.”

I was already hard but when Caz said that I think I was harder than I’ve ever been. She noticed. “Ohh, so you like that I’ve just been fucked?”

“Um, ah…”

“That’s OK, wimp, you don’t need to say anything. Your little fella tells me all I need to know. It makes me hot knowing that you like me being fucked by Antwan’s big cock. Do you know, when I told him I was going to see him after work, he grabbed my hand and took me to an unused storeroom. He tore my knickers off and fucked me there and then. That was at ten o’clock this morning. He fucked me three more times before we finished work. After work he took me to his apartment and made love to me all night. During the day it was raw fucking but at his place it was tender and loving.”

I was almost bursting at this stage. Caz began stroking my cock. We were lying on the bed together while she gave me a hand job. She rolled me onto my back and suddenly, without much warning, I came. She pointed my cock towards my head. I didn’t quite cum on my face but Caz made sure she wiped it all off my stomach and chest and fed it to me with her fingers.

“We’re going to do this again, wimp.”

This went on every couple of days for a few weeks. Caz would arrive home really late, usually around midnight. She would sit on my face and get me to clean her up. Then she would make me cum and clean up again. Sometimes I fucked her but mostly she gave me a hand job. Once she gave me a blowjob and kissed me with a mouthful of cum. It was a strange time but we were both happy.

One day Caz decided that I was such a wimp that I should wear her knickers. “I never wear any since Antwan ripped mine that first time. I just thought it would be a waste of money. He likes it like that. So you get to wear them while you wait for me to get home. Tonight I want you to wait laying on the bed with these on.” With that she pulled out a pair of frilly red knickers.

I showed surprise to Caz but secretly I couldn’t wait. That night when I got home I stripped and put them on. I wore them while I ate dinner and kept them on as I lay down on the bed. When Caz came home at about ten o’clock I was waiting on the bed for her, as she wanted.

“Good little wimp. Don’t you look sweet?” She walked over to the bed, took off her skirt and proceeded to get me to clean her up. I was tenting my knickers with my hard on. She grabbed me through the material and wanked me until I came. She rolled the knickers off me and stuffed them in my mouth. “Clean your knickers like a good little wimp.”

When this had been going on for a few months, Caz came home from work one evening, “Hey, wimp, got something new to try tonight. Are you wearing the black knickers I bought for you?”

I took off my trousers to reveal a pair of sheer black knickers.

“OK, good little wimp. Go to the bedroom and lie on the bed. Then I want you to grab the rail at the top of the bedhead for me.”

I did as she asked. She came into the room carrying a bag. “Close your eyes”

I did as she asked and felt her putting a blindfold on. It was a good one, too. I couldn’t see a thing. Then I heard the bag rustling and a funny clinking sound. Then Caz Grabbed one of my wrists and I felt something furry around it. She grabbed the other wrist and I felt the same thing. I realised she had handcuffed me to the bed.

“Tonight, my little wimp, Antwan has invited a few of his friends around. He wanted you to know that they were all going to fuck me and was worried that you might not cope so he suggested I cuff you to the bed. Don’t worry; I’ve put the key on the bedside table so I don’t leave it at his place by mistake. See ya later, wimp”

I was hard while she was talking to me and I remained hard while she was gone. The sensory deprivation was extreme. My mind was imagining all sorts of things. How many men were going to fuck my beautiful wife tonight?

Just after midnight the front door opened and I heard Caz’s heels clicking their way to the bedroom. She grabbed my face and kissed me. Her mouth was full of cum. “Antwan drove me home and I sucked his dick in our driveway. This cum is fresh from his cock.”

I just about burst my knickers. “You like, huh?” she asked.

“Uh, huh,” I replied.

She planted her pussy over my mouth. She was full of cum.

“How would you like it straight from the source?”

“I, uh, I don’t know, Caz, that seems a pretty big step.”

“Well, after tonight, Antwan and his friends want to meet you and we thought that you like cum so much you might like to get some straight from the source.”

“Honey, I don’t know…”

She shifted positions so her little pink anus was over my mouth. She dropped down and said, “Can you clean me here too tonight? There are a few loads there too.”

I stuck my tongue into her ass and licked like my life depended on it. It was amazing. Caz leant forward and began sucking my cock. “It would be really hot to see you with a big, black cock in your mouth. I think you’d love it as much as I do. Maybe they would like your ass too.”

“What? My ass?” I cried.

“Don’t worry, wimp. Antwan gave me a present so you can practice.”

With that she whipped out a huge black dildo in a harness. She strapped it on and made me go down on her.

“Oh, that looks so hot. Look up at me.”

I looked up at her with my mouth wrapped around the rubber dick.

“Oh, yeah, you look like a natural. Make sure you get it plenty wet.”

I wasn’t game to ask why. Somehow the idea of Caz fucking me with that monster was really hot. I couldn’t wait. She made me stop sucking and get on my hands and knees.

“Now, honey, just relax. It’s just like taking a huge dump, just it reverse. If you push while I do it’ll be much easier.”

I felt the head of the cock at my hole. I clenched in anticipation.

“Relax,” she said. “I’m not stopping so it’s gonna hurt like hell if you don’t relax.”

So I tried to relax. As the head entered my ass the pain was like nothing I’d ever felt before. I had tears running down my cheeks. “Honey, it hurts. Please stop, please.”

“Not gonna happen. Relax and push like you’re taking a dump.”

It couldn’t have been any worse so I tried. As I strained Caz pushed. The next thing I knew she was balls deep in my ass. I could feel her plastic balls against my real ones.

“See, I knew you could do it,” Caz said. “Now, you’d better get used to this because we’ll be practicing all week.”

“Oh, babe, I’m so full. It feels amazing. Why haven’t we done this earlier? Now I know why you like it so much. Fuck me, please.”

She pounded me for all she was worth. Her little grunting sounds got louder and louder.

“Oh, babe, I’m cumming, I’m cumming, butt fucking you. Ooohhhh, yeah, oohhh, oohhh, oohhh, yes, I’m cumming, aarghhh.”

With that, she orgasmed and collapsed onto my back. The rubber cock plopped out of me as she collapsed. I looked her in the eye and said, “We’ve gotta do that again.”

“We sure do, babe. Oh, look, you came too.”

There was a pool of cum beneath where I had been on my knees.

“Lick it all up, wimp. I don’t want a wet patch on the bed.”

Caz went out with Antwan again the next night. When she came home, after I had cleaned her out she sat me down and looked at me seriously.

“There’s something we need to discuss. Antwan is all man, so are all of his friends. None of them are gay. So if you want to get cum from the source, and I know you do, you’re gonna have to dress like a girl. No arguments, no crying. Either you dress like me or the whole thing isn’t gonna happen.”

I know she was expecting an argument from me but I was secretly really happy. I had long admired my beautiful wife and the way she dressed. She was beautiful and she had great dress sense. Her business dress was attractive; sexy without being slutty. Usually she wore a skirt and jacket. The skirt generally reached down to mid thigh, although she had some shorter ones. Her evening wear was something else. She always looked as if she wanted every man in the venue to desire her. She always wore heels, usually 4-inch. She had heaps of pairs; I’d lost count of how many she had. There were at least as many shoes as she had outfits.

She also had a great sense of make-up. She rarely looked as if she was wearing any, but I know it took her a long time to achieve this look. It was always well worth it. In business mode, she looked professional, but all woman. In her job in international finance she was not averse to using her sexuality to close a deal. She mainly dealt with middle-aged men. They didn’t stand a chance. Once again she stepped it up a notch whenever we went out. She always looked ready for sex.

These thoughts flew through my mind. “If I can look half as good as you, dear, I’ll be happy,” I said.

“So you’ll do it?”

I nodded.

“Oh, thank you, thank you, thank you. I knew I could count on you. I love you so much. Thank you.”

She went into business mode. “Now, we’re gonna have to practice so you will be perfect. We can start now.”

“Caz, it’s past midnight. We’ll start tomorrow.”

“OK but you can wear one of my sexy négligées to sleep in.”

She went to her cupboard and found a sexy black number, with pink ribbon under the bust. It was sheer, and it was beautiful. I hardly slept that night I was so excited for what would happen the next day.

Saturday arrived and I woke with a huge erection. I knew what was going to happen today and I couldn’t wait. My beautiful wife had some distinctly sexy clothes and hopefully I would get to try them all on.

I thought I knew what agony was but until that day I was deluding myself. We started after breakfast. Caz laid out some of her lingerie on the bed. She picked up each item and showed me how she put it on. Then she explained what it was called. Obviously bras and knickers were easy. I knew stockings and suspender belts too. I had seen her in a corset on more than one occasion. But things like bustiers, basques and torsolettes I had only vague notions of. She had teddies, slips and babydolls. She had demi bras, shelf bras, half cup, front opening and many more. She had bikinis, briefs, shorties and hip huggers, thongs and v-strings as well as cheekies and cheekinis. She explained them all and said that I would try them all.

She threatened that if I stained anything I would be in trouble. That’s what I meant by agony – all day I tried these beautiful things on but wasn’t allowed any relief. Absolute agony!!

That night Caz got me naked in the bathroom. She had some hair removal cream in her hand. “Now, spread this all over, wherever there is hair. I don’t want to see any hair below your head by the time you finish.”

Fortunately I wasn’t too hairy anyway. Whatever hair I had on my arms, legs and chest was quite light coloured and very fine. It wasn’t long before I could shower the cream off. Caz had gotten dressed up while I was covered in cream. She inspected me closely, especially around my cock and balls.

“Completely hairless,” she exclaimed! “According to the packet you won’t need to worry about anything growing for at least a month. Now, you just put your negligee on and hop into bed. I’m off to see Antwan. Goodnight, honey. I’ll see you in a few hours.”

She arrived home just after midnight. Again she got me to clean her freshly fucked cunt. It was full. “Not just Antwan tonight but three of his friends too.”

She turned to play with my cock. I came before she did.

She got me hard again. I ate her to orgasm then she sat on my cock and rode me until she came again.

The next morning I spent trying on her dresses and skirts. She had a terrific variety. Most were work clothes, what I called ‘professional dress.’ They were sexy but in an understated way. It was more about how she carried herself as to whether some outfits were sexy or not. At work she was all professional, but outside she was a man-eater!

We found that I was almost exactly the same size as her. She was bigger in the bust (surprise, surprise) so some of her dresses didn’t suit me. She had plenty of skirts and tops that would be fine.

I was really horny trying on all of her beautiful clothes. We stopped with the clothes after an hour or so and fucked like rabbits for the rest of the morning.

After lunch Caz said it was time to try on make-up. “Do you remember me telling you about how to apply make-up, Michael?”

“Yeah, I do.”

“Cool. I’ll start and you can help at any stage.”

I sat at her vanity and we went through the process she had described to me that time she first went out with Antwan.

“Face first. Concealer, foundation, highlighter and blush.”

She applied all of these.

“Now, eyes. Eyebrows, eyelids, eyelashes. We’ll go with the smoky, dark look I like. So sexy.”

I had to agree. She was as sexy as hell when she was all made up.

“Now, lips. We’ll go all out with the ‘my lips were made to suck cock’ red. I think it will suit you.”

I had my back to the mirror on her vanity. She told me to turn around. I was stunned. I looked gorgeous.

“Caz, you are a miracle worker. I look beautiful.”

“I got you a present, too,” she added, as she dashed out to her car.

“Close your eyes, honey,” she called.

“OK they’re closed.”

I heard her come back into the bedroom and open what sounded like a box.

“OK you can open them, babe.”

I opened my eyes. Caz was holding a beautiful, honey-blonde coloured wig. It looked like the hair would go down to the middle of my back, just like hers. In fact it looked to be styled like her hair. We would have the same hairstyle, me as a honey-blonde and Caz with her almost black hair.

Caz brought out a hair net. “This is a wig fastener. You wear it beneath your wig,” she explained. She put it on and then followed with the wig itself. She fastened it to my head. I looked in the mirror again. I really looked like a woman.

“Wow, just wow,” I said. “I can’t believe how beautiful you’ve made me. Do you think Antwan will be impressed?”

“You little cock-slut. You’ve been thinking of him all day, haven’t you?”

“Not all day. Just most of it,” I replied with a grin.

“Well, I think he’ll be happy. Now, the best part is that I’ve organised for him and a few friends to come to our place on Friday night. I think you might need to take the day off. I will too, so we can get you ready for your big night as a sissy, girly cock sucking cumslut. I’ve decided that I will call you Mikki.”

“Ooh, I like that, thank you,” I said.

We found that we were almost the same shoe size, too. In fact I was half a size smaller than her. She said that I would need to put some tissues into the toes of her shoes so I wouldn’t slip around too much. “It’s gonna be hard enough for you walking around in 4 inch heels without slipping around inside the shoes.”

She instructed me to practice putting her lingerie on, which was no great hardship. She also got me to choose some outfits to wear around the house each night. She helped me with the make-up. Each night that week, I was transformed into Mikki. When I was transformed, she got her dildo out and proceeded to fuck me like the slut I was. She really pounded me. I loved it!

The week seemed to go forever but finally Friday arrived. We woke up and made beautiful love before we did anything else.

“I love you, Michael, I really do love you.”

“I love you too, Caz.”

We spent the day getting ready. I think I changed my mind every five minutes about what I was going to wear. I just couldn’t decide.

“Hey, wimp, make a decision,” Caz said finally. So I did.

All black lingerie; black bra, garter belt, sheer stockings and full knickers to keep my cock in. Then a red pencil skirt with a black shirt. We did my make up and put on my wig and I was Mikki.

Caz went for the same lingerie but in red although she wore a thong instead of full knickers like me. She also put on a short red dress that looked like it was painted on. With her make-up she looked stunning. We both put on 4-inch heels, black for me and red for Caz.

When I told her so she said, “No less stunning than you.”

I think I blushed.

We opened a bottle of wine to calm the nerves. I felt like a teenager again, waiting for my first date.

Finally, the doorbell chimed. Caz got up to answer it and I followed behind her. She opened the door and there stood an absolute mountain of a man.

“Antwan,” was all Caz said, but there were a few statements in that one word.

He leaned down and kissed her with real passion. When they came up for air, she grabbed his hand, turned to me and said, “Antwan, this is Mikki, who I’ve been telling you about.”

“Well, aren’t you gorgeous, Mikki,” Antwan said in a deep, bass voice. “I’m very pleased to finally meet you, I’ve heard so much about you.”

With that he grasped my hand, brought it to his lips and kissed it. What a gentleman!

“Pleased to finally meet you too, Antwan. Caz never told me how handsome you are.”

He was possibly the most handsome black man I had ever seen.

We moved away from the door and Antwan was followed by a number of his friends, all huge and mostly quite handsome. I sidled over to Caz. “Do you know all of these guys?

“Of course, Mikki. I’ve fucked them all,” she said with a smile.

I lost count of how many there were but there was about a dozen. Caz said to them to help themselves to a beer from the refrigerator if they wanted one.

With that, Antwan came over to me, put his arms around my waist and said, “I’ve been waiting a while to fuck you Mikki. This is going to be fun tonight. He pushed me by my shoulders so I was kneeling in front of his crotch. I fumbled for his zipper, pulled it down and reached in for his cock. It was huge. While I marvelled at its size, he got rid of the rest of his clothes. I didn’t even notice. I was mesmerised by its size and how it felt.

Then, just as I was thinking that I was about to suck my first real cock, he thrust forward. I opened my mouth and welcomed it happily. He kept thrusting. I gagged a little but then remembered all that practice with Caz and her dildo. I swallowed a few times and this magnificent black cock slid down my throat.

I felt my knickers being pulled down and fingers exploring my ass. Then I felt the coldness of the lube as it was squeezed into me. Fingers kept massaging my sphincter. Then a cock head was pressing on my hole. It split me open and I was being fucked up the ass. It felt amazing. I remember the joy coursing through me.

I hadn’t noticed but one of the other men lay on the floor next to me. Caz had mounted him and was moaning in ecstasy. Then another began fucking her ass too. She was being double-teamed! And another cock lined up at her mouth. She opened wide and accepted it with glee. Caz had three cocks in her while I had two in me.

The thrusting became more urgent and suddenly I felt Antwan tense up and then shoot his load deep into my rectum. He groaned as he came and then pulled out. Straight away he was replaced with another cock. Then the cock in my mouth started spewing cum down my throat. I accepted it happily and then kept on sucking to make sure I got it all.

Another cock presented itself to my mouth. I opened up and took it in. Caz was doing the same next to me. As one would finish the next would begin.

The cock in my mouth took less time to cum. He withdrew his cock from my mouth and aimed it at my face. I copped a face full of cum, which dripped down onto my chest. I put the cockhead back into my mouth to make sure no cum was wasted.

This went on until all of the men had cum at least once. Caz suggested we take a break. She was covered in cum too. We looked at each other. I leaned over and kissed her passionately. I proceeded to clean up the cum from her face and then onto her tits. She did the same.

“I love you, Mikki,” she said.

“And I love you, Caz. Thank you soo much for organising tonight. I think we’re gonna have some more fun before it’s over.”

The night went by in a bit of a blur after that. All of the men had cum more than once and all had fucked both Caz and me, or been blown by us. What a night.

After they left, at about one in the morning, Caz and I showered together. We didn’t say much but just made sure we were as clean as we could be. Caz helped me clean up what was left of my make up. We went to bed and both fell to sleep almost straight away.

The next morning we had a leisurely brunch at our local café. After that we went home again. Caz said, “How are you feeling?”

“Great. I loved every minute of it. What about you?”

“Fantastic. I loved it too.”

She seemed to hesitate for a bit. Then she looked at me and said, “It’s all happened really quickly, hasn’t it? I mean, it was only a couple of months ago that we were a happily married, monogamous couple. Now we’re fucking guys by the dozen.”

“Yeah,” I replied. “I thought about that too. Honestly,” I said as I gazed into her eyes, “if we hadn’t done it this quickly I may never have agreed. But I’m glad we did. I love being Mikki, and I love fucking and sucking.”

Caz took me by the hand and led me to our bedroom. She undressed me and then took her clothes off too. Then she lay down on the bed.

“Love me, Michael, slowly and tenderly, love me.”

I was happy to oblige. I kissed and caressed her all over, paying special attention to her nipples. Then I kissed my way down to her pussy and licked, bit and sucked that until she was on the verge of orgasm. Then I stopped.

“Don’t stop, you bastard, I’m so close.”

I kissed my way back to her mouth. As we kissed I guided my cock into her dripping pussy and made sweet love to her. She came like a train and so did I. As we lay there she started to weep.

“Don’t cry baby. Everything’s fine.”

“I’m so happy, Michael. You love me like that and all I do is go out and fuck other men. I don’t deserve you.”

“Hey, don’t say that. If I didn’t like what you are doing I would have said something. But there’s something inside me that needs you to do the things you do. And there’s something inside me that makes me want to be Mikki, for you, but for me too.”

She hugged me with love. We dozed off and didn’t get back out of bed until mid-afternoon.

This became our life and for about three months everything was perfect. Caz kept going out every couple of days and on the weekends Antwan and his friends would come over and fuck Caz and Mikki.

Mikki was becoming a bigger part of my life. Caz and I discussed it and decided that perhaps I could quit my job and start my own Financial Advisor business from home. Actually, Mikki could start the business. That was I could be Mikki more or less permanently. I needed time to think this one through.

Then we stopped seeing Antwan and his friends each weekend. I knew there was something going on because Caz was coming home from her dates earlier than usual. Most of the time it was well after midnight but for the last few weeks it was ten o’clock or earlier.

She told me that Antwan wanted to take her away for the weekend, next weekend. I asked her if that’s what she wanted.

“Yeah, I guess so.”

“Not exactly a ringing endorsement,” I said.

“I know, but I’m not sure if I want to. Half the fun of going out with him is coming home to you. For two nights I won’t be doing that. I think it’s a really big step.”

She looked to the ground, as if unsure of what to say next.

“Michael, for the last few weeks, Antwan hasn’t invited any of his friends. It’s just been him. I’m not sure if it means anything but I know that he hasn’t seen both of us for a month or more. I’m a bit worried about what this weekend is going to be about.”

“You’ll work it out, Caz. Go with him. If it feels wrong, come home. It’s probably nothing anyway.”

So she went. Her last words were, “You know I love you, both Michael and Mikki, don’t you?”

That left me wondering about what was going on in her head.

I spent an awful weekend alone. I couldn’t sleep and when I was Mikki my hair and make-up was a mess. Sunday finally arrived. I had no idea when Caz would be home so I made myself get dressed as Mikki. I put on sexy lingerie, a short skirt and sheer top and did my make-up with more care than ever before. I was ready for Caz to come home by lunchtime.

Have you ever noticed how slowly time goes when you are waiting for something? I logically knew Caz wouldn’t be home until late afternoon or early evening but I still hoped it might be earlier. By six o’clock I felt that I had spent about three years waiting. Then seven o’clock, then eight. Every hour felt like a month. Finally at about nine thirty I heard a car in the driveway and the front door opened. There she was, my beautiful wife, standing there, looking gorgeous.

“Caz,” I said.

“Babe,” she said. “Let me shower. We need to talk.”

“Fuck,” I thought. That was not what I expected. No hello, no hug, no kiss, not even an invitation to clean her pussy. What the hell was going on?

About half an hour later she came out of the shower.

“Mikki, do you remember the last thing I said when I left on Friday?”

“Yeah, you said you loved both me and Michael.”

She held out her left hand. “Antwan has asked me to marry him.”

My jaw dropped. I looked at her hand. No wedding ring, no engagement ring from me. Only an obscenely large green rock surrounded by about six diamonds. I was speechless, my mouth open wide in shock.

When I finally found my voice I said, “So your statement last Friday was a lie?”

“No Mikki, no. I love you, only you. He made me take off my rings and put this one on. I’ve just spent the last half an hour trying to get this stupid thing off. It’s too small.”

“So what are you saying?”

“I’m saying I love you, and you alone, and we won’t be seeing Antwan again. The stupid prick thought that his cock was enough. I’m not denying it’s good but the man himself? Antwan loves Antwan and there’s no love left for anyone else. There’s no way in the known universe that I’d give up the love I have for you, and I know you have for me, for that self-centred jerk.”

That’s when the tears started. They fell in rivers down my face, my mascara running with them.

“I knew he was up to something. We hardly fucked all weekend. I thought I’d never get out of bed but we had what he called a ‘romantic’ get away. The man has no idea. He took me to places he likes, nightclubs and strip clubs. Nothing that I like and he thought he could woo me and marry me.”

“So how did he react when you said no?”

“Well, that’s the problem. I didn’t. I said I’d need to speak to you about it. You know what he said? He said, ‘Hey babe, we can keep Mikki around as a fuck toy, but Michael can fuck off.’ Can you believe that?”

“When will you tell him?”

“Tomorrow at work when there’s plenty of people around. I don’t think he’d hurt me but I don’t want to take the chance.”

Apparently he wasn’t happy when Caz spoke to him the next day. She told me that because of her position in her company she could make life really difficult for him so he backed off.

The good news? I have started my own business, and Caz has changed jobs too. Her company needed a new General Manager of operations in their head office interstate which she applied for and was given. We moved a short time later and arrived in our new condo (provided by her company) as two women in a loving and committed relationship. Mikki runs her business from home and loves it. The business gets bigger every day. Caz loves her new job. We are both on the lookout for a third party. Mikki hasn’t tasted anyone else’s cum for ages and misses it!

Same as Married Crossdressing Fun Ch 1 Videos

1 year ago
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My crossdressing fantasies Free Sex Stories and Adult Erotica Stories

I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...

Cross Dresser
4 years ago
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Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

2 years ago
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A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

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4 years ago
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An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

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2 years ago
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First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

3 years ago
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First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

3 years ago
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Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing
2 years ago
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Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

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3 years ago
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Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

3 years ago
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Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

2 years ago
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An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

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3 years ago
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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

Crossdressing
4 years ago
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Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

3 years ago
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Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?This is a real life story of a crossdresser caught in the act!This happened around when I was 15 yrs. old.As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my...

1 year ago
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The Late Crossdressing Husband

THE LATE CROSSDRESSING HUSBAND by enduringshades Edith and I had known each other since we were teenagers. We went shopping together and often met for lunch or coffee. Friday night used to be our Girls Night Out when we dressed to the nines and headed for our favourite bar. Then we got married (not to each other!) and stopped going out together. Edith was still a party girl, but I stayed at home with my wife, Betty. I never told Betty that I was a crossdresser. I missed being...

3 years ago
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Stefanies Crossdressing Memoirs Vol 6

I've decided to switch the category for these over from blog post to sex story, as at this point in my adventures as a gay crossdresser, I had pretty much hit my stride dressing up and finding men and other crossdressers online to have sex with. So I guess you could say my posts moving forward will be a little more "action" oriented. Plus at this point it is hard to remember all of my experiences chronologically, and for the most part that's really kind of irrelevant. If any of you are...

2 years ago
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Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

4 years ago
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An Introduction to Crossdressing Pt 5

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...

Crossdressing
3 years ago
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Girlfriend Catches Me Crossdressing

At this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...

4 years ago
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Duped Into Being a Crossdressing Bull Part I

During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...

3 years ago
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JOANNE SLAM A LIFETIME OF CROSSDRESSINGhellipAlmost

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3 years ago
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First crossdressing experience 3 cocks in1 hr pa

I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...

3 years ago
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The story of how i began crossdressing Part 13

Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...

2 years ago
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first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...

3 years ago
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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...

3 years ago
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Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

2 years ago
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Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

2 years ago
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Crossdressing Fun From A Womans Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...

Crossdressing
3 years ago
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Crossdressing Fun

Hi everyone, Vinnie here from bglr . I am 26 and love cross-dressing and being a slutty girl. Been cross-dressing from college .When my senior made me wear his sisters skirt bra and top and he lip-gloss and makeup. I loved it when he got so hard and he sucked my nipples while i rubbed his cock harder. We are alone at his place so he was biting my nipples on the sofa. We bunked college so he could have fun alone early. Once i sucked him before in wash room in local church. He said i looked very...

Gay Male
2 years ago
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Ashleys Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

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2 years ago
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First time crossdressing with a friend

My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....

Crossdressing
3 years ago
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Sex with a crossdressing in a public toilet

Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...

3 years ago
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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

3 years ago
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Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual
4 years ago
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Crossdressing for sex

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...

3 years ago
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An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

Crossdressing
3 years ago
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An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing
4 years ago
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An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing
2 years ago
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Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing
3 years ago
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Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

3 years ago
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A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

2 years ago
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Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing
2 years ago
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Mother and Crossdressing Son Fantasy

Mother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...

4 years ago
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Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

3 years ago
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Wifes crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing
4 years ago
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Wifes Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing
3 years ago
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Wifes Crossdressing Fantasy

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease. We talked about many things. He told me I was cute and that...

Crossdressing
2 years ago
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Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

3 years ago
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Kissing Crossdressing Cousins

For as long as I can remember, I have always been drawn to wearing women's clothing. When I was 4 years old, my mother would take me shopping and I would throw tantrums if my she didn't take me to look at the girls clothes too. I would try on pants but only on one condition: I got to look at the dresses when we were done!When I was 5 years old, I wanted to be Princess Leia for Halloween. My mother thought it was adorable and was more than happy to buy me the costume. The following year, I...

4 years ago
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Making Scents of Crossdressing

Making Scents of Crossdressing By Ricky I am a hi-tech person. I work and play with some of the latest computers and electronic equipment, have stereo speakers in every room of the house, and can bore you for hours with torrents of jargon on just about any subject you care to name. When I don my feminine attire I have a fondness for synthetics, those modern wonders of the laboratories of some multinational chemical giant. Who else but those hi-tech wizards could turn a barrel...

Humor
2 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

4 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

2 years ago
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Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

2 years ago
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Crossdressing Charlie Episode 3 Relinquishment

CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...

2 years ago
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Crossdressing Charlie Episode 4 Lust

CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...

4 years ago
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Crossdressing Charlie Episode 5 Rachels Date

CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...

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