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Caught en Femme

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx

*****

"I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out with some coworkers after work."

"Alright hon, I'll hold down the fort." I said from my spot at the kitchen table where I read the newspaper. I was still in my underwear and t-shirt that I had worn to sleep. One of the few perks of being a freelance writer was not having to change into something more business appropriate. Annie, however, had to change into her dress slacks and blazer for her IT job. She was lucky enough to gain a job out of college, and when we got married 3 years ago when I graduated we were able to make it on her salary.

"Bye babe, I love you." she said as she closed the door. I waited to hear the garage door close before I put down my newspaper and made my way to the attic of our two story house. Now that I knew for sure that Annie would be out for the house for at least the next 8 hours, plus the time she would be out with her coworkers. This gave me more time to indulge in my usual Friday activity.

Ever since I was a kid I have indulged in crossdressing, and over the years I have acquired quite a wardrobe in a trunk that I now keep in the attic. I climbed the stairs leading to the attic and found the trunk. I brought it downstairs to the bedroom and I turned on the shower. I went to work immediately: I grabbed a razor and went into the shower. I didn't have much hair on my body, but whatever hair I did have on my legs, arms, chest, and pubic area I completely shaved off. After toweling myself off I went to the trunk. I sifted through it for a few minutes before finding a pair of panties I liked. They were bikini style, white and trimmed with black lace. I had purchased it with a matching bra online awhile back. I retrieved the white and black lace bra and took out my falsies. They were C-cup size and matched my fair skin tone. I pulled the panties up my legs and a chill went up my spine as the lace rubbed against my hairless legs. I fastened the bra and inserted the falsies into the cups.

I sat down at my wife's vanity and took out the makeup kit from the trunk. After putting on some foundation and concealer, I did my eye makeup, putting on a good amount of eyeliner, mascara, and eyeshadow to give a bit of a smoky eye effect. I put on a little blush before finally finishing it off with a light coat of pink lipstick. I went back to my trunk and retrieved my long straight haired blonde wig that was very close to my natural blonde hair. I fixed the wig onto my normal short hair with some bobby pins and let the hair fall down my back. I looked at myself in the mirror. Even after all these years of dressing I still amazed myself at how sexy I was when in girl mode. I was never a really big man, topping out at about 5'8 in terms of height.

I put on a garter belt over my panties, and then took out a pair of black stockings and rolled them up my long legs. I didn't feel like putting on a full outfit, so I put on a pair of 5" stiletto heels and walked over to my home office, where I would normally write. After taking a seat in my chair and firing up my computer, I took some pictures of myself with my webcam. First, I took one standing up, then one bending forward, showing off my falsies. Then I sat in my chair, legs open, my cock slightly visible through my panties, before finally taking one last one bent over, ass in full frame. I went to my favorite crossdressing site and uploaded the pictures to a profile I had on a website I spent much of my time on under the name "Tiffany", finally bringing my picture total to 700.

In addition to my crossdressing, I also had a fantasy about getting fucked by a man while dressed en femme: not only that, but I also imagine my wife being there, egging on the man fucking me. The website I frequented helped people out with that. Of course, I had never gone through with it, but I had spent countless hours having dirty chats with men on the site who were more than willing to be "the other guy" in my fantasy. I went to go check my private messages and found only one new message from one of the regular guys I chatted with, Reggie. Oddly enough, there wasn't any text in the message or the subject: just a link. I clicked the link and found myself on a porn site, under the shemale section. I pressed play and found a white woman pulling down the pants of a tall, muscular black man. As the woman was giving head, the man reached into the woman's panties and found a rock-hard cock. Before long, the black man had pulled his cock out of her (or his) mouth and pulled her panties down. He started to fuck her in the ass, first slowly and then in rapid motions. I was so turned on by my fantasy being fulfilled on screen that I plugged in my headphones to continue watching and stroked my cock through my panties

I continued stroking as the video kept playing. I closed my eyes and enjoyed hearing the sounds of the moaning through my headphones as I reached my climax. I was about to let loose, but I was startled by my chair suddenly doing a complete 180.

"GOTCHA" I heard a female voice say. I opened my eyes as I came in my panties and was immediately blinded by a bright flash. I repeatedly blinked my eyes as I tried to regain my vision, but a set of hands grabbed hold of my wrist and attached something cold and metal to it. When I heard the click of the metal against the armrest of the chair, I started to panic. I looked down at the handcuff that my right wrist was now locked in to and tried to free myself using my other arm. This was met with a slap to my face, and before long my left wrist was cuffed to the other armchair. I looked up at my attacker and I couldn't believe my eyes.

In front of me was my wife, Annie. Around her neck was a very professional looking camera, which she was now looking through.

"Smile bitch." she said with an evil smile, and the flashbulb went off again.

"Oooh, this is a nice one." she said, turning the camera around so I can see the picture. I had to admit: it did look pretty nice, except for the handcuffs. Without them, it'd just be a picture of a hot looking blonde woman in her underwear with a wet spot in the front of her panties.

"Annie...I thought you were at work..." I muttered.

"And you thought I was going out afterwards too, huh? So away I go and out come the panties. I knew you were doing this crap. I just had to catch you in the act." she said. She left the room for a moment. I struggled to wheel myself towards the doorway in the chair, but eventually she came back in with a briefcase.

"No, no, no. Why leave now? Your fantasy might finally be fulfilled." she said, "in fact, Reggie is on his way right now. Yeah, he may have been farther away than most of your other little suitors, but he seemed like the most worthy candidate."

I looked at her with a shocked expression in my eyes. "How do you know about that?" I asked.

"Oh come on now, you think you can hide something on a computer from me? The goddamn COMPUTER SCIENCE MAJOR? Yeah, I know all about your little fantasy of being fucked by a real man. Well, now's your chance. But I say that we warm you up a little bit, and while you're at it, you could recreate one of Reggie's favorite photos." she said, holding up a printout of a photo of me in a sexy nurse's costume that I had gotten years ago.

"I'm going to uncuff you now. I suggest you don't try any funny business. Lets face it here, you're not all that strong of a 'man', now are you? Hell, you're not much a 'man' at all." she said with a laugh. She was right: we were both the same height, and she was a rower in college, so she had some muscle on her. I nodded my head meekly in obedience. She pulled out a small key and undid the first cuff.

"Don't act so scared babe, I'm just trying to help fulfill a fantasy for you. I'll make sure everything goes well, okay?" she said, trying to reassure me. I nodded my head yes, yet again. She undid my second cuff. I got up and went back to the bedroom and stripped. I went back to the trunk and took out my white lacy bra and my white thong. After putting them on, I put on my white thigh high fishnet stockings. I put on the white mini-dress, which barely covered my ass and didn't come close to reaching my stocking tops. I put on the 4 inch red heels and fixed up my makeup, for the most part reapplying the makeup I had on, except now adding in a slutty red lipstick. As I fixed my wig back to my head with bobby pins, I heard the doorbell ring.

"Ah yes Reggie, hello. I'm Annie. Tiffany's upstairs, let me go introduce you to her." she said faintly. I heard them coming up the stairs. "Shit," I thought, "here it comes." The doorknob turned and I saw Annie standing in the doorway with a man I can only describe as a big black hunk. He must have been at least 6'4 and his arms were very muscular.

"Tiffany! You look sexier in person." Reggie said with a smile. I blushed at the compliment.

"Aww, the sissy is blushing because a real man called her sexy. How pathetic." she said. "Have a seat in that chair in the corner Reggie. Make yourself comfortable. Slut, sit on the bed. Don't get too excited now that your man is here." Annie took a shopping bag from the hallway and took it with her into the bathroom. I nervously sat on the bed, sometimes glancing at Reggie, who continued to smile the whole way through. After what seemed like forever, Annie opened up the bathroom door and stepped out. She had strpped down to her bra and panties. What really shocked me was what she had between her legs: attached to a harness was a gigantic dildo. It looked almost 10 inches long.

"Get on your knees, bitch." she said. I couldn't take my eyes off of the dildo.

"ON YOUR FUCKING KNEES RIGHT NOW." she ordered. I broke out of my trance and got onto my knees. She walked behind me and cuffed my wrists together behind my back.

"Now, if you're going to suck a real man's cock, you need to suck a fake one first." Annie said, walking in front of me and holding the positioning the dildo right at my face.

"Well. What are you waiting for? Start sucking sissy." she ordered. I kissed the head of the plastic cock and ran my tongue down the length of it. I took the massive head between my lips and starting working it farther down my mouth.

"Are you ready bitch?" she said. I uttered out a sound in confusion, but with the gigantic rubber cock in my mouth it sounded like a moan of pleasure.

"That's right, you like this don't you. I bet you'll like this too whore." she said, grabbing my head with both of her hands. She rammed the cock down my throat, pulling my head into her crotch. I shrieked out, but again it sounded like a moan of pleasure.

"Haha I knew it Annie, she likes to be facefucked." Reggie called from his chair. I glanced over and saw that he was now naked. Annie continued jamming her plastic cock down my throat, going faster and faster by the minute. After what felt like forever, she'd had enough, and she took the cock out of my mouth.

"Reggie, get on the bed. Stay on your knees for now, Tiffany." Annie said. Annie went to get her camera again.

"Alright Tiffany, this is a video now. I want you to crawl on your knees to the edge of the bed. . Take off your heels if you want." she said, holding the camera up to me. I kicked off my heels and started crawling on my knees. I reached the end of the bed where Reggie was sitting, naked. I stood up and bent over his cock. His cock was out and at full mast. My God, that's bigger than the dildo. It looked at least a foot long and was as thick as a coke can.

"Beg to suck his cock, Tiffany. And call him Master Reggie." Annie said.

"P-please let me suck your cock, Master Reggie." I stuttered out in my most feminine voice.

"Well of course you little sissy, you can suck my cock if you'd like." he said. I ran my tongue around the bulbous head and tasted his precum. I swiped my tongue over my lips, enjoying the taste. I looked Reggie in the eye as I lowered my head onto the throbbing head of his cock. I put about half of it into my head before slowly moving my lips back to the head, running my tongue up the bottom of the shaft. Reggie moaned in delight. I lowered my head down again, taking his entire cock in my mouth and letting his balls hit my chin. I continued sucking away, flicking my tongue away at his cock. Before long he was slowly thrusting his hips upward to meet my mouth. I was lost in my own fantasy.

I was finally snapped out of it when I felt a pair of hands find the skirt of my nurse's uniform and lift it up. I felt that same pair of hands pull my thong down my legs before finally getting it off.

"You want to get fucked by a man right? You need to get broken in first." Annie said. I heard a squirt and felt a cold liquid start to get applied in and around my asshole.

"You want to get fucked in your sissy pussy, don't you Tiffany? Don't you?" she asked. I was about to answer when Reggie really jammed his cock in my mouth, and a soft moan escaped my mouth.

"Oh, you do. Reggie, lets lay into this little whore." Annie said. Annie positioned herself behind me while Reggie grabbed my head and started fucking my mouth with his cock. I felt Annie's plastic cock start to press against the entrance to my sissy pussy. At first I thought she'd put it into me slowly: but then she all of a sudden rammed the plastic cock into my sissy pussy. Tears began to form in my eyes: I felt like I was being ripped in half by the cock. I tried to scream but I couldn't with Reggie's cock in my mouth, so another moan came out.

"Oooh, does my sissy like being fucked? She's moaning, look at that. What a little whore." Annie said. Annie began to take the cock out of my sissy pussy, only to ram it back in, harder than before. Reggie kept ramming his cock down my throat. Eventually, he started to slow down and he closed his eyes. I felt his cock start to twitch in my mouth. Reggie groaned and I felt him shoot load after load of hot salty cum to the back of my throat. He slowly withdrew his cock from my mouth, leaving a trail of my lipstick on it. He collapsed onto the bed.

"Keep fucking her Annie, I want that bitch ready to take it from me." Reggie said. Annie kept fucking my sissy pussy. Tears were still coming down my face. I felt the head of the dildo graze my prostate, and a wave of pleasure went all across my body. I felt my own cock stirring, and with each dildo pump I got harder and harder. With one last mighty pump, my prostate was hit again and I let out a long moan as my cock shot my load all over my dress, the bed, and my thong.

"Oh wow, we made the sissy cum. She really must have liked this." Reggie called, laughing.

"CLEAN IT UP BITCH." Annie said, spanking my ass. "I SAID CLEAN IT." I went to work licking up my own cum from the bed. Annie went back and got the video camera.

"Alright Tiffany, are you ready to lose your virginity to a real man with a real cock?" she asked, pointing the camera at my face.

"Yes, yes I am." I said.

"Get into the position Tiffany." Annie said. I got on all fours on the bed, ass sticking in the air. Reggie got up from his chair, his cock now back to full mast. He got behind me on the bed. My ass was still lubed from that pounding I received from Annie. I felt his hands caress my ass and then wrap around my waist.

"Get ready Tiffany." he said. I felt the bulbous head of his cock pressing against my sissy pussy, begging for entrance. He gave me a squeeze on my cock and I opened up for him.

"HERE WE GO!" he shouted as he rammed his entire foot long cock into me at once. I screamed out in a mix of pain and pleasure. My fantasy was finally being fulfilled. Reggie kept pounding into me, and before long I was moving my hips back to me his thrusts. I moaned every time his cock went in, and he moaned in response to my moans. He grabbed my tightly secured wig and pulled my hair as he kept fucking me. My cock was getting harder and harder again, and I felt him start to slow down, signifying that he was getting close. I puckered my sissy pussy up really good to help him get even closer. He pulled out one last time, and with a final hump, let his load loose in my ass. As he came in my ass, my cock started shooting onto the bedsheets. I fell down onto my stomach, overwhelmed with emotion.

"Great job sissy slut." Annie said as she shut off the camera. "This will do just fine."

"What do you mean?" I asked, rubbing my ass.

"Well, you're clearly not fit to be my husband. You'll be living here as my new sissy slave. You will sleep in the guest bedroom, and Master Reggie will sleep in here. This video is now an...insurance policy. To make sure you don't pull any funny business. We need to keep our sissy in line." Annie said, looking at Reggie. "Finally, I'll have a real man around here."

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