2 comments/ 30254 views/ 1 favorites Interactive Crossdresser...Dare Me Ch. 02 By: PorscheKaru Hi Porsche I loved your kinky stories and I think its hot how you let strangers tell you what to do. I would like to hear you do something more humiliating though... Are you ready? I dare you... to dress as a hot woman, very high heels, fishnets, tits on, makeup, but with a very short mini skirt and no panties. I want you to get a dog collar and a lead around your neck, I also want you to chain your ankles together so you have to take small steps and cant run. If its possible I want you to tie your own hands behind your back and I want you to go to a public park somewhere and find some sort of pole that you can sit on that will fit in your ass (hopefully its big so it hurts). I want you to fuck yourself on this pole until you cum - BUT YOU ARE NOT ALOUD TO STROKE YOUR COCK - GOT IT! YOU ARE NOT TO MOVE UNTIL YOU ARE FINISHED CUMMING. Find something you can cum on and when done get in the doggy style position with your hands still tied behind your back and lick up every bit of cum. I think you will have to fuck yourself very hard and fast to cum quickly so you don't get caught huh? Imagine someone finding you there and all you can do is fuck yourself on that pole dressed as a slut and then licking up all your cum afterward - wouldn't that be hot? Do you dare to take on this challenge? I am ordering you to and I want to hear all about it. If you succeed then I have another dare for you. Get back to me promptly OK? Master - Jake That was the first email I received from Master Jake. I was so turned on by his dare I wanted to do it right away. It took a little while to plan and gain the confidence to perform but I finally did perform his dare and I will tell you all about it. It was around 9pm Sunday night when I got showered and put on girly body lotion and put on all my make up...lip stick, eye liner, mascara, foundation, blush painted nails etc. I had to change a few of your rules but I hope that's ok. I slipped on a little yellow thong so I could hide my man part and put on a matching yellow bra to cover my big tits. Next i slid on black opaque thigh high stockings and put on a garter belt and attached the garters to the stockings. I then put on my black and blue plaid school girl skirt. Its really short and comes down just to the stocking tops, barely covering my perfectly smooth ass. I put on a stretchy black long sleeve top and pulled my blond wig on. I sat down to put on my leopard print 5" high heels. They have the strap that I wound up my entire calf. The park I was going to was about three blocks away, so i went to the front door with my little purse, gulped a little and walked out the door. It was fairly dark out now and as soon as I got two houses down a car came driving past me and it was my neighbor. I walked down the entire block, got to the end and turned left up a half block to the main road and turned right. I now walked down the main street about a block and a half. I was pretty nervous and jittery as I walked my sexiest walk and cars drove by. I got to the park which was set back a little ways and walked down the path to it. No one was there and it wasn't too much of a park, a few benches and a swing set. I couldn't find any pole or anything so I got scared I couldn't complete the dare. I sat down on the bench and there in a garbage next to where I sat was some corona bottles. Perfect I thought, in my purse I brought some lube and a some condoms, 2 magnums and 2 regular. I bent over and pushing the string of my thong to the side I lubed my little hole, put a magnum over the empty beer bottle, then stood up and holding the bottle between my legs I sat down on the bottle, pushing it into my hole. Nobody around I got the bottle inside me up to the part where it flares out and gets bigger. I bring my feet up onto the bench and squatting on the bottle holding it with one hand and steadying myself on the bench back with my other I fuck myself up and down on the bottle. I'm so scarred, I wonder if anyone can see anything driving by. Then nearby a car pulls up and I see 4 black kids getting out. They are pretty far away from my but I panic a little and sort of leap off the bench but as my heels hit the ground, bottle in my ass I impale myself further, in one quick shot of pain the bottle is forced up further and my hole is quickly filled with the fat part of the bottle as i take it almost all the way inside my. My God I scream inside, almost yelling out loud but not wanting them to see me. Don't know what could happen, I'm so scared inside. They don't seem to be coming over and the pain is turning into pleasure now as I grind on the bottle back and forth, my cock straining against the fabric of the panties. They leave now and I'm riding this condom covered bottle that is almost all the way inside my and feeling ready to come so I grind faster and faster and as I come i stick my hand there to catch all the come, stand up and bring the bottle out of me and rub the cum on the bottle, then lick every drop off the bottle while I suck on it like a cock. Then I straighten up and make the slow walk back on very queasy legs. Could I please have my next dare, I'm so excited for it. Love, Porsche Interactive Crossdresser...Dare Me Ch. 03 Hi again, I'm back to share a couple quick dares, I still wish you all would send me more dares. This first one is from Jason. This is from an email he sent me. "You're first dare will be a simple easy one that im sure you can handle ;) I simply want you to wear the shortest skirt you own, next you will go out to a public place and just sit across from either a sexy girl or a guy if you like and give the a peek of whats under there. That's an easy one for you. Hopefully you will let me know how it turns out." This the email I sent back to him describing my completion of his dare. "Hi Jason darling, Sorry I've been meaning to write you back but I've been very busy. I can't add to your yahoo because I don't use that but I would love to keep emailing each other. what turns me on a lot is getting dares from other people and performing them. Its so hot, I get so turned on. I performed your dare Saturday night. I went out kinda late, around midnight. I wore yellow satin thong panties and matching bra, I'm 36d when i dress up. I wore a tight baby blue sweater, a short pleated, plaid schoolgirl skirt, black fishnet stockings, black 4 inch high heels, and all my make up and i wear a long blond wig. I went to a gas station, I saw a couple so I stopped to get gas near them. I drive a big truck so I parked and when getting out i took just a little too long getting down, my panties clearly visible, but my little clitty tucked between my legs hidden. When I got down and straightened my skirt I glanced at them and saw the girl slapping the guy's shoulder so he must of gotten caught looking at my exposed panties. What a turn on!" The next dare is from Trent and here is his email to me. "I want you to get dressed up conservatively, not slutty, but still sexy. Jeans, heels, sweater or blouse. Nails, perfume, breast forms,wig etc. Find a laundromat and bring a load of lingerie and wash and dry them there. Stay there the whole time and take a cell phone cam pic of yourself. Pick a machine away from everyone else and lean your crotch against the washer when it is spinning and cum in your jeans discreetly. Go in the bath room or your car and take off the panties. Lick them clean and bring them back in and very deliberately put them in the running washer, try to let someone see you putting them in." I performed his dare but unfortunately couldn't do part of it because there were no people there but here is my email back to him. "I need another challenge please. I went Sunday night and washed my panties. I wore black Express pants, pink sweater, black high heels, full makeup and wig, red bra and panties underneath, but nobody was there. I was nervous the whole time though." Trent emailed me back a dare that he would like me to put an ad on the internet and meet a man dressed and suck him off. So I did just that, I put an ad on gayuniverse.com on the cruising section. My ad was to meet at my house and that I was a boy and I crossdressed as a girl and I wanted to suck a cock and swallow cum. I had put in the posting that I wanted to meet Sunday night and to text me on my phone. I did not receive any texts so I went to sleep. I woke up to my phone beeping and an incoming text that said he was interested and in the area and what was the address. I got very nervous not expecting a response especially at 10am Monday morning. We text back and forth for a while basically saying I needed time to get dressed up and not to mention I really didn't know if I would go through with it. I decided I would at least start getting dressed up and ready just in case and start drinking some beer to help take the edge off, I was so nervous. The process took me almost 2 hours to get my make-up just right and I drank quite a bit too. I started by putting on a pair of hot pink nylon panties and tucking my little clitty in between my legs. These panties hold it nice and tight. Then I would put on my concealer, drink some and I turned on porn too. I went back and forth between putting on make-up and putting on clothes. Next I put on black thigh high stockings and a little more concealer and made sure I was shaved nice and smooth. Back to the bedroom, drink some more, put on a hot pink lacy bra and put my breasts in them giving me my big tits, then back to the bathroom to put on my foundation. Then I'm drinking some more, watching a little porn and putting on black high heels and back to bathroom to touch up foundation and put on black eyeliner and eye shadow using some pink and black to make my eyes smokey pink and so sexy. Back to the bedroom to drink some more and to put on my little pleated schoolgirl skirt, it's so short it barely covers the stocking tops. I'm also texting Tommy to let him know I'm still getting ready. He teases me that I'm a typical girl taking forever. Back to the bathroom to apply jet black mascara and bright pink lip stick, making me look so sexy. Then back for more beer, I'm getting a little buzzed now and losing some inhibitions too, and to the bedroom to put on a tight black sparkly, long sleeved turtleneck and my blond wig to complete me. I go look in the mirror for a few touch ups on the makeup and to see how amazing I look. Then I find myself texting Tommy my address and he will be here in 5 minutes so I drink another beer. Oh God, I'm actually going through with this. I see him approaching, he is a little bigger in size and older, maybe in his 50's. Oh God, panic and nervousness as he knocks on the door. I let him in and close the door as he checks me out and starts rubbing me up and down telling me how beautiful I am. I lead him upstairs, he can see my pink panties up my skirt. Upstairs he continues to fondle me, I tell him how nervous I am and he says its ok. He lays down on the bed after he takes off his pants and pulls me down and positions me so my ass is by his head and I gently take his cock in my hands as he rubs his hands all over my ass and legs. I gulp, look at his flaccid little dick and I take it into my mouth. I'm actually doing this! I suck up and down over and over and over hoping he starts to get hard. I take it out and then back in, it's starting to get a littler harder, a little bigger, he asks me where to cum and I tell him I want his cum in my face. I go back down and suck his cock in and out but it's just not that big. As he starts to fill up my mouth with his expanding cock I feel his cum in the back of my mouth, I gag a little at the unexpected cum filling my mouth and it dribbles out of my mouth and down his cock. He gets up and puts on his pants and leaves. I just wish he would have gotten super hard. I put another ad on the site so maybe I will get another cock to suck soon. Please send me more dares. Love, Porsche Interactive Crossdresser...Dare Me Ch. 04 So just to give a small amount of background, besides taking dares from people and performing them, although I don't write about a lot of them, I post ads online using this name, Porsche Karu, seeking men who are looking for a cross-dresser. I get some reply's but they never work out into an encounter. Until one guy, when he first emailed me he was staying at a hotel in town but I couldn't get time for what he wanted but he told me he would be back in town in a few weeks and told me where he was staying and what room number even. The hotel was on my side of town and we emailed back and forth during the following weeks; I told him I had fantasies of being used as a prostitute and he loved it and told me there would be $1000 in it for me to meet up with him but I had to follow his rules, and his rules exactly. So the day arrives that I'm supposed to meet him at his hotel, he told me 8:30 to 9:00pm to be there at, and he would send me a first email earlier in the day, before noon. I'm still very nervous and reluctant to meet him so I begin around 11 in the morning to get ready, and when I mean get ready I mean to start the margaritas, tequila will take the edge off for sure. So at 11, after showering, and shaving my body perfectly hairless, I started the blender and started tipping back the margaritas, awaiting his email to start this adventure into prostitution I suppose. It would really be nice to get $1000, I'm just very skeptical of what I have to do, but after emailing back and forth for weeks he seems legitimate. I'm walking around, naked, well into my second margarita and I still hadn't heard from him, so I thought that I would at least go start applying all my makeup so I can get it perfect. Well before I get a chance to start, I hear a ding from my computer for an email. I run to the computer to check and sure enough there it is from Gus, the email I'm waiting for. I pull it up, the subject line says, "your challenge." That subject is intriguing, so I start to read and realize I won't be getting ready now, I will just tell what the email says, then what happens next. The Email Hi Porsche, So the day finally arrives and I'm so excited, I hope you are too and I hope you're ready for my challenge, it's not going to be easy but I think you will have a lot of fun and enjoyment today and tonight if you go through with everything. Remember, to win the $1000 you must go through with everything the way I say. So here is a list of the rules. 1.You must wear jeans, boxers, a t-shirt, and sandals when you leave the house and you can't get "dressed" or ready at your house, the only items you can take are your wig and your breast forms. 2.You will go shopping for each women's item that you will be wearing today, your outfit needs to be a sexy skirt and sexy top. 3.Once you buy an item you have to wear it and not take it off. 4.Only one item per store, bra and panties are considered a single item as they need to be a matching set. 5.Garter belt and stockings are required and can be considered one item. 6.Every item you wish to buy has to be tried on in the store. 7.At least one item has to be bought in a women's only store. i.e. Victoria's Secret, Fredricks, Charlotte Russe, Tiger Lily, you get the idea, and yes it has to be tried on there. 8.When you try something on, you must take a picture of yourself and send it to me on your phone, then wait for me to reply. 9.You will also email me on your phone what store you are going into before you go into it. 10.All receipts have to be saved and presented to me for repayment, that will not be part of the $1000. 11.Once you buy an item, you then have to wear it, and not take it back off, before putting on your bra, you must affix your breasts, your wig must not go on until immediately after your make-up is applied. 12.Your nails, hands and feet must be professionally done at one store, your make-up must be professionally done at another store. 13.Any man who attempts contact, or engages you in any way, you give him a note that you write, the note must say, "I lost my voice, but I love to suck cock and would love sucking your cock if you want me to." 14.Your first stop must be a porn shop, buy an anal plug of your choice, it must be one that can stay in your hole all day, leave and put it inside of you out in your vehicle. 15.After you are completely dressed, go shopping as a woman and buy a sexy dress, bra, panties, garter belt and stockings, and another pair of heels if you wish, and don't forget some jewelry and perfume. Don't forget to try on the dress. When you're all done shopping then come to my hotel room, around 8:30 pm, I can't wait to see you. -Mac Interactive Crossdresser...Dare Me Ch. 05 So this is a little story about one night I had with the couple from Australia who were in the original story of this series. They are the ones who gave me my first dare and the idea for this little series, we also continue to chat and recently they got my address because they wanted to send me a gift. We have been chatting for some time now so I felt somewhat comfortable doing this, not to mention they live in Australia so I didn't feel any concern. A few weeks ago I got the package in the mail, even though they told me it was coming I was still surprised when it actually arrived. I sent them a message that it arrived and they asked me to chat that night and to not open it yet. So I did. Later that night after taking a bath and shaving my entire body nice and smooth, and rubbing lotion over my body I logged onto our chat session completely nude. We chatted for a little while first, they told me how excited they were for me to open my present, and I was equally excited. They told me to open it and put it on then come back to the chat session. I opened the bag and inside were a bunch of little bags so I took out one at a time. The package was from Fredrick's Of Hollywood, the first bag I noticed was a bra, so I went and got my fake silicone breasts so I could put it on. It was a sexy, all lacy and embroidered flowers, light purple bra, I put it on and situated the silicone breasts inside. Perfect 36dd fit. Next I took out this rhinestone choker necklace, it was rather wide and a very sparkly purple, I put that on, was a little tight but I'd get used to it, it looked very pretty. There was also matching bracelets so I put those on too. Next was a matching purple lace and embroidered garter belt, I put that around my waist and fastened it nice and tight. Then the matching thong panties, I pulled those up and in place, tucking under my little clitty; they were nice and lacy and so sexy. Lastly was a pair of scallop lace top fishnet black stockings so I slid those up my super smooth legs and attached the garters to them. Wow I looked so sexy, this Fredrick's Of Hollywood lingerie also feels amazing on my body. I didn't do makeup or anything else tonight, so I went back to chat with the Australian couple. They were super excited that I loved it and was wearing it, they told me they wanted a picture when I was 100% dressed up and in their presence but unfortunately something came up and they had to go. So with not much else to do, I watched some porn and masturbated then went to bed. We set up another time to chat a few weeks later. So a few weeks went by and in that time I also got a new computer, it had a built in web cam which I never had before. I was a little late to chat with the Australian couple and just wearing shorts and a t-shirt. I told them right away about the web cam and they got super excited telling me they know exactly what they want to do tonight. They said this will become more of a live dare now, and went on to tell me what I had to do first as long as I accepted their dare which I guess they would explain as it was happening. "Of course", I was excited. To start they said I had about an hour but I had to set up a private web cam page and give them the log on and password, then obviously get naked and take a shower and make sure my body was perfectly shaven, then apply all my make-up, wig, paint my nails, and glue on my breast forms then when all that is finished come back to the computer and let them know I was ready as they will be logged on by then and can hopefully see me. That made me a little nervous, as I've sent them some pics of me but always in either an outfit or in lingerie. A dare's a dare so I got started. First I got the page all set up and the web cam operational and sent them the password and log on. Next I showered and meticulously shaved every inch of my body so nice and smooth, and glued on a set of long finger nails. After some body lotion I quickly painted my toes and finger nails a pretty sparkly purple and let them dry. I had just gotten the breast form glue so this was my first time applying it but it was pretty easy and my big size DD's went on easily and stayed nicely right in place after holding them for a little while so the glue could set. Then I started on my makeup with concealer and foundation, I also applied some foundation around my breast forms which made them look so incredibly natural. I put on my false eye lashes and went with a purple and black smoky eye look, then jet black eye liner and loaded on the mascara. My eyes look so damn sexy! To finish I put on shiny pink lip gloss, a little blush and touched everything up a little, I looked so hot like I was ready for a night out. Lastly I affixed my wig in place which is a light blonde with some darker highlights, and a look in the mirror and I couldn't even recognize myself. It had been a little while since I made myself up like this but with the very naturally looking breasts I just look amazing and incredibly sexy! I nervously went to the computer and kneeled in front of it as my computer is only a foot off the floor, I don't have a desk. I looked at the page which had a text section and a screen which showed what the camera was looking at which was a naked hot looking girl with a penis. "Wow" was the first message on the screen. "Now lets have this sexy girl dress in some sexy lingerie for us. " "Put on the present that we sent you a few weeks ago and finish it off with a pair of stilettos." "Make sure you can be seen on camera putting on each item." This was actually really exciting to me, they loved the way I looked and now I was going to dress in front of them, this is hot! So I grabbed all the items they had sent me and my 4 1/2" black stiletto heels and got in front of the camera. "Put on the garter belt," was the first demand. I put the garter belt around my waist then fastened it nice and tight, I also watched the screen to make sure I was centered in the camera. "Now the stockings." Slowly and sensually I slid each thigh high up my smooth leg and attached each garter. "Panties next." I slid the sexy thong up and when in place I tucked my little clitty back behind so I had a smooth feminine appearance. "You can put the bra on now, even though we love looking at those amazing tits!" So I slipped my arms through the bra straps next and clipped into place, adjusting my large breasts in the cups. "Put on heels and jewelry." So I put on my stiletto's, the choker and matching bracelets and stood in front of the camera in this sexy Fredrick's Of Hollywood lingerie waiting for what's next. Not to brag but I was looking at the full picture of me on the screen and I looked so hot and sexy! "God you look hot!" "Go get a martini glass and your big purple dildo." So I took my big purple dildo out of the drawer and walked back to the computer to show it to the camera. It is 9 inches long with a nice 3 inch girth, realistic cock with balls and veins, and also vibrates. Now to get the martini glass, I have to walk down to the kitchen in just lingerie and high heels while all the windows are open and I don't know if my roommate is home, or if he'll walk in the front door. I thought about a cover up, but I wasn't told I could do that not to mention if my roommate sees me it's not like he knows I do this. Nervous as hell I venture down to the kitchen, find a martini glass and back up to my room, phew no roommate but I have no idea if anybody was looking in the windows. Probably not. I show the martini glass and my big purple dildo to the camera. "Start sucking that purple cock." So I hold the base of it below the balls, while i'm on my knees in front of the camera and start licking the big veined shaft up and down, then take the large head in my mouth and start sucking it up and down, trying to give it the best blow job I can. As I'm bobbing up and down on the shaft, trying to take as much in my mouth as I can as I look up and see the next message comes up on the screen. "Fuck that dildo like the slut you are, then while its deep inside you and vibrating, turn and face the camera and stroke your little clitty until you cum, but make sure you cum into the martini glass." I turn so my ass is facing the camera, I spit on my fingers and rub it onto my little hole after I pull my thong to the side. The dildo is well lubed with my spit so I squat over the huge dildo and lower myself onto it. The large head is lined up with my hole and I start to sit down on it, forcing the head to push into me. Gog it's still feels so damn big and it pops into me giving me a quick once of pain until my little hole is used to the head inside me. I start to push down to take more of the big purple cock up inside me. It stretches me nice and wide, feels so good now, slowly sliding inside me. I take more and more of it up inside of me, then I start bouncing up and down on my big purple cock, slowly at first but a little faster and harder. I slam down on it, taking most of the 9 inches inside me, moaning out loud, I spin on it, turning to face the camera, on my knees with my huge dildo buried inside me, I start it vibrating and pull out my little hard penis from my panties and start rubbing it up and down, trying to make myself cum. The vibrations along with this super huge, veined, realistic 9 inch cock up inside me is too much to handle. I stroke myself and moan as the pleasure mounts. My cum spurts out of me as I orgasm, I fill the martini glass with load after load of hot cum. "Now drink all of your cum out of the martini glass." I turn off the vibrator, so I'm kneeling with my huge 9 inch fat purple dildo deep inside me, I pick up the martini glass full of my cum and look into the camera, then I drink the entire glass, swallowing all my cum. Oh my God. Next chapter will be the finish to my story about a man from my town, then this story might continue in the chapter after that. Love, Porsche.