boy / girl fantasy ..with a twist

This is my firt time posting a story, so please forgive any flaws in structure spelling and format.

I have always had this fantasy running around in my head and hope to one day make it reality.

I am a thirty something male who has always wished i could be a woman for at least one night. I often crossdress and play with toys. Anyone who has visited my profile knows what i can do with my toys. ...anyway... I have tried to do my own make-up and have failed misserably each time. I end up looking like a clown.

What i fantasize about is having a woman come over to my place one day under the guise of a regular date. We sit and chat for a little while,"getting to know each other". ...guys you know how agravating THAT can be... So after a decent little chat she asks if she can have a tour of the house. ...I happily agree and proceed to show her around. I show her all the normal things, my dvd collection ,stereo .the big screen tv ...which is of course a plasma... I mention, without thinking, that pornos look really good on it. She just grins and says what kind of porns do you have? I built the dvd cabinet so there is a hidden panel that opens up and reviels another set of shelves. she looks through them and notices every genre there is ..from stright and lesbian ..all the way through the bisexual, shemale and gay, all the way to extreme bondage.She tells me that i have quite the collection there. I say "yes i do ..are ther any you would like to watch? She says "there will be time for that later".and asks "which ones do you like"..i tell her "I have always been partial to she-male porn. I love the thought or going down on a beautiful woman and pulling down her panties revieling a cock twice the size of mine" She grins and says "we may have to do something about that"

So we continue the tour, my mind reeling with possabilties. I show her the kitchen, opening the refidgorator and she sees all the sausages, corn cobs, cucubumbers, zuchinis, lemons, apples and oranges, beer and wine bottles. and says "You sure eat heatlhy"...I just grin and say "I sure do" ..again anyone who has seen my page know what i do with them... Back to the story.. I continue the tour showing her the bathroom ...the extra wide shower and the jucuzi tub built for two ..and she notices the make-up table ...fully stocked with make-up and hair brushaes curling irons and hot rollers. she looks puzzled but doesn't say anything.

We continue to the bedroom. I show her the platform bed, which is made, with a nice bedspread and a bunch of pillows and stategicly placed mirrors. i open the door to the walk in closet. One side with all my regular clothes,jeans,t-shirts, work uniforms and shoes belts ..the usual mens stuff and the other side lined with dresses, blouses .womens tops and jeans, lingerie, cubbys filled with stockings and womens shoes ..high heel pumps with three inch heels, ankle boots with four inch heels and knee high boots also with four inch heels as well as a couple thigh highs with five inch heels ...this puts her is a confused state bacause i told her i am single and live alone ...we continue going through my closet and i open a few drawers and cabinets showing her my extensive toy colletion ...all the nornal stuff first. cock rings,penis pumps, the flesh light, and a couple fake vaginas. then with this not freaking her out i open the next drawer revieling the so-called normal sized dildos and vibrators .anal beads. seeing these she begins to get upset and it shows.

I continue to open drawers. The next is my large collection ...several strap-ons, the Bam dildo, the extra long and almost as thick as Bam dildo.the Bella Donna hand, the mans hansd, and the fist. This puts her over the top. She is freaking out and says "you said you were single and obviously a woman lives here" and begins to leave ... not wanting to get invovled with an already involved man... I stop her and ask what she means. She says "I noticed all the make-up, dresses and all the womens things everything built for two ...but when i saw all the dildos and the size of them that was all i needed to know this is a womans house" reluctantly i agreed ...but its not what she thinks ...I tell her that everything in this house is mine and that I have always dreamed of being a woman ...and the woman that does live here is buried deep inside me and i just need the right person to bring her out. All of a sudden she grins and says "really ..i have always wondered what it would be like to be a man and fuck a prety girl...maybe we can help each other out. Can i dress you up do your hair and make-up and fuck you tonight?" Almost needing to pinch myself thinking this is a dream. i say "Hell yes that would make me so happy and you can put on some of my clothes if you want"

I turn on all the tvs, which are all connected to the same source so all the tvs play the same thing ...she goes in the dvd selection and pics out some bi-sexual porn with men fucking men while wmen fuck watch and use strap-ons ..we go in the bathroom and get in the shower ,,,she proceeds to wahs my hair and shave my body ...everything from my face and chest both legs then my ass and balls until i am completely smooth the only hair is on my head ...we rinse off and puts me in a silk rob and sits me in the make up chair ..plugs in the hot rollers and lets the heat up while she blow dries my hair ...then puts in the hot rollers and puts the shower cap on me to hold in the heat so the rollers can do their thing while she fixes my face ...plucking my eyebrows and applying the foundation ..doing my eyes ..eyeshadow eyeliner and lipstick .she does my nails ..attatching acryllics and paints them ...now my hair is reary for the final touches ...she gets the curling iron and hair spray not letting me see anything she is doing yet ...we go in the closet and she finds my false breasts and a sexy corsett puts it on me and slips the breasts in so she can sinches it up giving me a nice womanly figure. Then gets my tranny panties ..which is a nice thong with a tuck pouch. put them on push my balls up inside my and tuck my cock in giving me a nice camel toe and they are crotchless so there is easy acsess to my asshole. we both pick out the stockings and knee high boots. tThen she picks out my sexiest mini dress and when i am dressed she walks me to my full length mirror and shows me how good i look. I am shocked and almost cry because i never thought i could look so beautiful.

Now that i am ready its her turn. She leads me to the living room and sits me on the couch to watch the porn while she goes in the bathroom to get maned up. Stopping in the kitchen to get the saran wrap She musses her hair parts it to the side and pulls it back ...uses some black powder to give her a five o'clock shadow look, removes all traces of other make-up and looks like i guy who just got home from a long days work. She goes back in the bedroom and in the closet,gets completely naked and wraps her breasts with the saran wrap to make her ample chest as flat as possible. Going throgh my strap-ons she find my double penitration one ..it has a pussy plug as well as a buttplug with a full panty style harness and inter changable didlo hook-up...she picks out the eight inch white dildo because it matches her skin tone ..gets a pair oof my crew socks and some tighty whities slpis them on and tucks her cock to one side ...she picks out a tight t-shirt and some thight jeans so that she looks like she has a buff chest and a nice bulge in her pants .and she then finds a pair of sneakers and come out to the living room and we are completely role reversed.

Neither of of can believe the transformation and we decide not to waste this in private so we decide to go out on the town for the night. We go to a restaraunt that we both frequent to see if anyone recognizes us. while we are eating dinner i notice a few guy friends that know me really well but have no clue that it is me. so i flirt with them a little ..winking at them and using my tungue to pull the straw to my mouth suductively. while they are not looking i lean to her and say i want to see how far i can go with this and ask her to slip away for a second to go to the restroom ..when she gets up i motion to one of them to come over for a second. I have always wanted to have him fuck me but never had the guts to do anything about it until now ...i talk to him for a second and ask him if he would be interested in a threway later tonight if i can talk my date into it ...he says that he has neve ben in a threeway with another man before but with a woman as hot as i am he would definately do it. I think to myself if he only knew.

She comes back from the bathroom and sees me talking to him and play the jealous date thing to a t. I tell her to relax and that he is just and ex-boyfreind i havn't seen in a long time ..they both play along ..him knowing its not true and her knowing what i am planning.We talk for a while and i get him to slip me his number while she is not looking but I already have it because we are really friends and saw him earlier today before i got transformed. we go our sperate ways ..but the idea is already in his head that i might call him later tonight. It gets him worked up, and he does anything to get some when he is like that.

Later after dinner we go to my other night time hangout and have a few drinks and dance for a cople hours. Knowwing that i will run into my friend again i wait until he shows up because we run in the same circles. when he does he cant believe we ran into each other again and that it is quite a coincidense and that it must be some kind of sign.I tell him that i am getting ready to go back to my dates place and he agreed to let you join us and i want both of you to rock my world tonight. My friend hasn't been to my place in a really long tome and i am sure he won't realize where he is because he has a good buzz going.

We get back to my place and turn on the porn and i sit on the couch inbetwen the two of them and she plays it up like its her house and turns on the tv and asks if i want to watch some porn and opens the secret compartment and get out some she-male dvds and while the movie is playing i notice that my friends cock is sweeling in his pants and motion to her to look at it but not to obviously.she winks and know what i am goin to do ...i put my hand on her srap-on and start rubbing it making it look hard and he sees thins and motions for me to do the same to his ..i have both hands rubbing their cocks and unbutton his pants and take down his zipper so i can get my hand around his cock and stroke it.and she pulls her strap-on out through her pants and i have both hands full i lean over and kiss her first she grabs one of my faske tits and he grabs the other .They are realistic so its getting him hot and i lean over and kiss him as i go down and take his throbbing cock balls deep down my throat.I get up on my knees between them both and he grabs my head with one hand and my ass with the other and give it a spank as he pulls my head up and down on his cock throat fucking me. She hikes up my dress which is aready so short that it bearly covered my ass anyway. Remember the crotchless tranny panties, she gets bend me and starts eating my ass and i play it up like its my pussy,with my mouth full of cock i say "lick thats pussy baby" taking all his cock down my throat he is so hard i cant wait to feel it inside me.she gets on her knees and slide her strap-on in my ass all the way with on deep strke and i am a human rotisary just like i like it ...with the two plugs inside her and her pumping my ass every stoke brings her closer to orgasm. she cumms so hard that it pushes me off his cock and i turn around and take her cock deep in my throat so i can taste my own ass juice. he takes his turn while i am sucking her. He gets behind me and grabs both my fake tits and drives his cock deep inside me and pumps my ass so hard that i think my cock might pop out ...luckily it doesn't ..but he does cumm just then driving his load deep in my ass and it fills me up so much that it drips down his balls.

He pulls his cock out and i go down and begin to suck it licking his cumm off his cock and i ask her if she want to join me.He still thinks she is a guy so he protests a little but i know he is into it and just tell him to sit back and enjoy. We both suck his cock for a while and tell him that he should return the favor. He says that he has never sucked a cock before but what the hell i'm d***k and probably won'y remember this anyway. She stands up and takes the strap-on in his mouth and notices it tastse like rubber. not sure but enjoying it anyway unbuttons her pants and pulls down her pants accidently taking the star-on off also reveiling her pussy and he is loving this and lays her down and lick her like a champ while i take off his panst and lick his asshole from behind.This gets his cock rock hard and he has to fuck her now .

He get on top of her and fucks her deep and hard while i continue to lick his asshole he says he want to lick my pussy now. i ask him if he is sure and he begs for it ..He says "I want to lick your pussy while i fuck her"so i stand up and pull off my panties leaving my cock tucked back and stand over her he buries his face between my legs and i let my cock pop out. Shocked but also happy he takes my cock all the way down his throat like a champ and i get rock hard. I tell him that his asss is wet from my togue and i want to fuck him. he says go for it and i slpi in behing him and i cant beleive how easy it slide right in like he has been fucked a few times before.I tell him that and he says "yes i love it up my ass and have a friend that fucks me all the time but don't tell anyone.I pump his ass for a while and when i am ready to cumm he tells me to cumm inside him the suck it back out so you can share it with me. and of course i do.and when he feels me fill him up he explodes in her pussy and fills her up ..loving cumm the way i do i ask them both to stand over my mouth and let me suck it all back out ...we all thre snowball and swallow together ...and he still did not know who i was ..i see him the next day and ask him what he did last night and of course he lies and says "I fucked to beautiful women last night"

if anyone liked this story and want to read about some more of my fantasies i would be happy to post them ..i have extreme ass fucked fanasies,gang banged in a biker bar fantasies ..night time break in **** fantasies,bondage,water play, humiliation fantasies ..and many more ..give me a scenerio and i will tell you a story ...i also have some real stories like me inviting a guy over and not letting him say a ting just pull his cock out let me suck him off then told him to leave just a stop drop unlosd and go an ex dressing me up and fucking my with a strap-on ..a first time fist atempt when i was much younger wit an unforunate accident ..like i said if you like this one i will keep posting more ..i just dont know which one i should do first
97% (37/1)
 
Categories: Gay Male
Posted by wilmakucream
4 years ago    Views: 1,682
Comments (10)
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2 years ago
very good story but I want more but hard and perverse
bradleyno...
retired
3 years ago
just came!
4 years ago
interesting
4 years ago
very hot...ive had similar fantasies..i got rock hard and had a great orgasm in lingerie
jackguns
retired
4 years ago
had to jack off to your story thanks
fluffy1
retired
4 years ago
nice story, i'll come and play. i can ride you then you can ride me!!.
loriannth...
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4 years ago
that's a wild one alright

know what you mean about the clown look

it takes a while to find a look that works
bigdick1828
retired
4 years ago
MMM i loved this story you got me rocked hard lol damn wish i could be that lucky guy jaja nd mmmm do another story of getting gang banged nd raped :)
4 years ago
i hope this story gets someone off