Found

Story Info
Story of a crossdresser being found and used.
2.8k words
4.3
64.4k
34

Part 1 of the 2 part series

Updated 06/08/2023
Created 11/11/2016
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This is a work of fiction, any resemblance is all in your head. Please leave feedback if you like it and even if you don't I would appreciate it.

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I still don't know why I didn't checks the door lock beforehand, but there I was standing in front of the mirror wearing a pink satin slip, stroking my hard cock. I must have been wrapped up with what I was doing as I didn't hear anything until I heard the click of the camera followed by the giggles.

The next thing I heard was my neighbor Sally saying "don't let me stop you, by all means finish." This was a lightning bolt that erased my hard on instantly. "Aww, did I scare it?" Sally said with a laugh.

Panic washed over me as I thought this was it. This was going to ruin me. Sally slowly walked over to me and told me "don't panic sweetie, everything is going to be fine. Well as long as you do exactly what I say."

I told her I would do anything as long as she would not tell anyone about me. She then told me to be at her place at 6 and I'd better be shaved from the eyebrows down. She also told me that I should come dressed in something sexy.

I didn't know what to do. I thought that it might all just blow over until my phone chirped. I looked at it and there on the screen was a message from Sally. It read "in case you are having second thoughts, here is what is ready to send out to everyone you know". On the screen was the pictures of me with the slip on and my cock in my hand. I was screwed. The only thing I could do at this point was to comply.

Hopping in the shower I proceeded to shave my body. Some parts, like my arms and chest were easy, but my groin area was difficult. The last thing I wanted was a cut down there. I carefully finished, making sure to get in between my ass cheeks and my legs. After I used some lavender lotion that was laying around I was soft and smooth. The feel and smell was intoxicating.

Next I took to the task of getting dressed. I started with my favorite garter belt. Black lace with a red rose design on the front. I slowly rolled up my black stockings, being careful to keep the seams straight and not get a run in them. After attaching them to the garter hooks, I ran my hands slowly down each leg. It felt like electricity was flowing through me and my cock sprang to life. I knew that wasn't going to help my situation so I ignored it for now and went to put on the matching bra for the set, also black scalloped with 32C cups. I connected the clasps and swung it around like I've see many a woman do before.

I dug further into my special bag where I kept all my stuff and found my lifelike breast forms that I have, but have never used. After applying the special adhesive tape, I slid them individually into the cups of the bra. Holding them against my chest for a few minutes allowed the tape to stick. With the breast forms in place, the last piece was my panties. My cock was still rock hard and I dared not wank as in didn't know what the night would hold. I decided that they would have to wait and perhaps focusing on makeup would help.

I started with the foundation, making sure that any beard stubble gets blended over a bit darker. Then highlighted my cheekbones with some rogue. Next I attempted my eye makeup, trying to follow all the videos I've watched. I went with a two tone approach blending some green and white shadow to compliment my hazel eyes. I glued on the fake eyelashes, liberally coating them with some extend lash black mascara. Lucky for me my eyebrows have never been very think so I was able to draw some light ones in. I fished the look with my favorite lipstick, fire engine red.

My cock had reached a tipping point. If I didn't do something about it soon I would blow my load everywhere. I slipped on my favorite pair of black patent leather 4" heels, and walked into the kitchen. I needed to cool off and fast. I filled a small bucket with ice and water and held it up to my cock and balls. Finally my hard on stared to go down. I pulled up my black satin gaff, pushing my testicles up and into my body and pulling my now flaccid cock back. The gaff flattens out any bulge and hugs me tight.

Now what to wear. Most of my outfits stop at lingerie or 'club wear' that you would buy at a lingerie store. I settled on a tight red faux leather skirt that came to just above the knees. Then a tight black satin button up blouse on top. I still never get used to the buttons being on the opposite side of the top. I leave the top few undone so my 'cleavage' will be on full display with the help of the push up 'add a size' bra.

Now the final touches. I rummage around to the back of my closet an pull out the Styrofoam head that my shoulder length wavy wig sits on. I put my stocking cap on over my existing hair and with a few bobbin pins, I set the wig in place on my head and go over to the mirror to make any additional adjustments. I tug the skirt down a bit, checking my stocking seams to make sure they are straight, and make sure my hair is hanging right. I add another coat of lipstick, some gloss, and apply some finishing powder. Just as I am spraying a bit of perfume on and clipping on my dangle rhinestone earrings, the phone rings.

After I say hello, I immediately regret it. On the other end of the line was Frank, one of my teammates from work. "Man, where are you at? You were supposed to be here a half hour ago. Did you forget you were on tonight?"

What the hell was I going to do now I thought. Some how I managed to just sound convincing when I told him "oh hell Frank, yeah it slipped my mind. I've been down and out with a bad stomach bug. There is no way I'm going to be able to make it in. Any chance you'd pick it up for me? I would do anything!"

Frank replied "Man I had plans tonight, but sure and you owe me one. Big time!" "Frank, I owe you." That little escapade would cost me dearly.

It was nearly 10 after 6. I was late. I hurried out side checking briefly to make sure no one was watching and practically ran next door to Sally's house. I rang the doorbell and the light came on. I stood there in all my best, out on her front stoop lights blaring. It felt like an eternity until she finally opened her door and told me to turn around a few time so she could see what I was wearing. As I did she started taking more pictures of me. Finally she said to come inside.

"Not too bad." She said. "You look like a two dollar whore, but not as bad as I had though you would look." I didn't notice at first the riding crop in her hand. I sure noticed it when she swung it firmly at my ass. WHACK, WHACK WHACK, as she smacked me three times with it. I let out a loud yelp as she continued the beating.

In between yelps I asked "what did I do? I'm here and dressed as you asked."

Sally responded in turn, "yes, but you were late. I expect you to be on time when I tell you to be somewhere." I then said "but it wasn't my fault!" That did bode well.

I proceeded to tell her that I was walking out my door when I stopped to answer my phone. She grabbed my small clutch bag and pulled out my phone. Scolding through my contacts and call log she seemed satisfied with my answer.

After one more WHACK, she said "fine, but next time you will face a much worse fate for not complying with me fully."

I responded the only way I knew how by saying "yes Mistress".

To which Sally said "I think I like the sound of that."

"Now, go fix your makeup and wait for me in the den." Sally said with a crooked grin.

I went to the bathroom and touched up my mascara that had run a bit while she was smacking me. I also added a fresh coat of lipstick and another dab of perfume to my cleavage.

All in all, I thought I looks good and my cock was struggling to get hard in its tightly confined panties. I fished up with a quick powder to get rid of any shine and stepped back out.

The den was dimly lit and I dared not change anything. I took a seat gently on the couch. A few moments later Sally was back. She had changed into a tight leather basque that pushed her ample black patent boots that came up to mid thigh, and a tightly wrapped robe around the rest of her. She had the cattle prop still I her hand.

As soon as she walked in she said in a commanding voice "come here to me." I did as I was told and walked over to her at once. Sally then pulled me in close and kissed me deeply. Our lipsticks meshed together as her hands moved around my body. Firmly grabbing my ass in my skirt. She the nuzzled a bit on my neck and moved her hand under my skirt to my pantie covered bottom. Running her fingers around the edge of panties. She then stated to push me down towards my knees. I offered no resistance and dropped down to my knees.

Sally then told me that since I was dressed like a whore, I may as well act like one too. With that she opened up her rode letting it fall to the floor behind her. Starting me now right in my face was huge strap on cock belted to her waist. I looked up at her to ask what she wanted me to do. Sally just say "you dumb slut, open. Your mouth and suck on that cock like you know you want to."

Truth be told, I did. The tool looked so lifelike. It had to be at least nine inches long and was a good handful around. As I reached out for it I heard Sally say "a proper slut doesn't use her hands. Plus you need some color and a manicure. Those man hands look awful."

I didn't respond. I opened my mouth and she rested the phallus right in my mouth.

"Good girl" she cooed. It felt natural, I swirled my tong around the heard and took it fully in my mouth. She told me to lean my head back so I could take more of it in. Soon I had it all the way down my throat. I started to gag as she rocked it in and out if my mouth. Grabbing my head on either side she and started to fuck my face. Fast, slow, fast, slow, soon I was drooling and slurping along with the thrusts.

"Now stand" Sally said. I complied. She held my chin in her had and said "that was good, you'll get better with more practice." "Now strip bitch, I want to see the rest of that body slut." She stepped back and sat on the sofa stroking the hard rubber cock as I stated to strip. I slowly unbuttoned my blouse, letting it drop off my shoulders. Next I reached behind me unzipping my skirt. I wiggled it off my hips, teasing the top of my panties. Then I bent over and let the skirt ride down my legs.

Sally was moaning while I performed this strip tease. She then told me to get down on my hands and knees. I sank down and got on my hands and knees. She stood up walking towards me pausing to reach into the end table drawer.

Sally then stood in front of me and told me to open up and get her cock nice and wet. While I was bobbing up and down on the Sally pulled my panties down some, exposing my hole. I heard her open up a cap on a bottle a d felt a cold liquid applied to my hole.

She stood up pulling that strap on from my mouth. "Now, it's time." I knew what was coming and I was scared, but still turned on. I felt her slowly push one finger in, then two. Getting a rhythm going of in and out. hen a third finger stretches mu hole. "Oh so tight. You my sissy, are going to be very popular. At least for a while."

Just as I started to get into the sensation, she removed all three fingers. Before I could turn and look I felt the head of the strap on monster at the entrance to my rose bud. She started to push it in saying "just relax, breathe, and push out."

Then with a pop the head was in me. She leaned forward allowing her body weight to push the remaining cock into my ass. Not having had anything larger than the three fingers she just removed in my ass, I did not know what to expect. At first there was a shooting and burning pain.

I cried out "please stop! Take it out, it's too big!"

Sally was not stopping. She let it sit where it was for a moment and then in one forward motion she drove the remaining shaft deep into me.

I arched my back and let out a squeal. Sally responded by smacking my ass hard while saying "quiet slut! You know you like this. How many times have you whacked off to big cock?"

The truth is, many nights have been spent on the computer beating off to mixtures of sexy CD's and women getting fucked.

The pain started to subside as Sally slowly pulled back and pushed in. After a few pumps a tingling started to build and I started to meet her thrusts with my own.

"Oooh seems like someone like this". Sally Said.

"Yes" I cooed out, "please don't stop." I replied.

Sally's thrusts got faster as she went, driving the hard strap on cock deeply into me. All of a sudden I felt a wave come crashing through me. Streams of cum started shooting from my cock without me touching it. Seeing this must have set Sally over the edge as she shuttered and moaned with orgasm from the other end of the cock tucked into her pussy.

"What a mess you've made. Now, clean it up!" Sally commanded.

I looked around for a towel, but Sally had other ideas. With another shove she buried the strap on in me again and said "silly girl, I wasn't done with you yet and true sluts use their mouths."

Sally then pulled out of my ass, leaving an empty feeling. She immediately told me to get back to cleaning up the mess. I proceeded to lick up the pool of cum that I had left on the floor.

She said "Good girl, now come over here and clean me up."

As I crawled over she removed the cock and harness from her waist exposing her dripping pussy. I eagerly lapped up her juices bringing her to another orgasm.

Sally collapsed back onto the couch and I slumped down at her next to her feet on the ground, spent. After a short time Sally spoke up "well, looks like you had fun. Stand up for me."

I did as requested. She then opened the drawer on the end table again and pulled out a cage looking contraption. She reached over, wrapping the device around my cock and balls. Then with a click she locked it in place.

"Just a chastity device" Sally said. "Can't have my sissy getting all hard. I will have the key and don't worry you can still cum, you will just have to do it like a girl."

I didn't know exactly what she was talking about, but somehow I had a feeling that l soon would.

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6 Comments
AnonymousAnonymousalmost 2 years ago
Used

I never though i would find my self being used as a sex slave.But dressed as a women i guest i asked for it I found my self stripped down to my garter belt stockings heels Down on my knees with a big hard black deep in my mouth.I guess looking like a woman made up head to toe i got what i asked for.As i look up their is a line of men with hard cocks looking for me to suck their cocks.First some just want to fuck me while some make me suck them while i am getting fucked.

cdCindy1cdCindy1over 6 years ago
great start

I too am a sissy CD cocksucking slut bitch -- AND I LOVE IT !!! I would love it if my sexy neighbour caught me dressed up and became my Mistress. I think I'll let it happen soon. Wish me luck.

AnonymousAnonymousover 7 years ago
awesome

I loved the story, I had a similar experience. It was totally embarrassing when I knew I got caught, but when it continued and wasn't aware some guys and women were going to be brought in on the action I really was humiliated. Now I'm a full time mtf CD and have tits and balls casterated

rdoolittlerdoolittleover 7 years ago
Take your time

Your story seemed rushed. Think it through and check spelling. Provide a better description of Sally. Looking for more later.

BrendaNWBrendaNWover 7 years ago
nice story, please continue

yes, I think he needs more practice with cocks.. I would dress for her but wouldn't need to be forced..

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