This is a print version of story first time web hook up crossdressing dominatrix by lillolly from

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 shopping and get some new outfits. I love going out in public dressed like a slutty girl im very passable when im all done up and I even have the guts to use the ladies restroom.
when I got to my apartment I dashed inside heading straight for the shower to shave and get cleaned up. I then went to the bedroom and got out my supplies, applying makeup used to be a difficult task but now I have the technique down. once finished with my makeup I started to put my outfit together, black seamed thigh highs, a black satin garter belt, some black lace panties the hardly cover my cute little ass and a black corset. over top of the lingerie I slid on a black knee length skirt with a slit up the back, a white button up shirt and black vest covers the corset, and my shiny black strappy shoes finish the outfit. I sit on the dresser and get the wig in position and do some styling untill im pleased with my look I stand back and inspect myself.
sliding down into the seat of my car the warm soft leather caresses the back of my thighs. I hike my skirt up a little so that the top of my stockings are exposed giving guys in trucks something to look down on in traffic, if only they knew a few inches higher there was a cock tucked into my panties. arriving at the lingerie boutique I step out of the car and straighten my skirt out and go inside. I like the lingerie here better than the stuff you get at the porn shops its more expensive but much better quality none of that one size fits most stuff. browsing through the store I find a few cute things to add to my collection a pair of tall white over the knee socks with black and pink stripes at the top a pair of white panties with black trimming a white sheer nylon turtle neck and a very hot corset panty and stocking set made of black latex. excited about my new purchases I decided to go home and try on my new sexy things and chat with some guys online. on the way back I stop by the d**gstore and pick up some makeup and some new eyelashes, standing in front of the lipstick rack I notice a cute younger guy checking me out. he looks somehow fimilar and I hope he doesnt notice me from somewhere, he looks like hes checking me out tho not like hes looking at a guy in drag. I get turned on from knowing hes checking me out so I bend down slightly to show off my ass and legs. glancing back I catch him looking at me still so I shoot him a quick smile and go back to picking out new lipstick. I decide on a lush dark red with a even darker red lip liner, I finish the rest of my shopping quickly and head to my car. getting home im so turned on that my cock is tugging at my panties making a large lump in the front of my tight black skirt. retreating to the bedroom I sit on the bed and inspect my new purchases I was simply in love with the latex set it was clingy and tight ill look like ive been dipped in black paint. lighting a cigarette I open my laptop and log on to a crossdresser networking site im a member on you can chat video post pics and meet guys to hook up with even couples and women were on here. I used the site to cam chat and post pics it was fun and everyone seemed to like me a lot, camming was probably my favortie thing to do on here. sometimes it was private watching someone and being watched other times I would just open my cam up and let anyone watch while I got wild and kinky for them. I read several messages from my fans and checked my comments, after a while I decide to see whos online chatting. about a half hour passes making chit chat smoking and catching up with some of my online friends I get a message from one of my friends. 'did I just see you at the d**gstore or am I dreaming?' my heart skipped a beat when I read it. now I know where I had seen the cute guy before I added him because he was from the same city as me but I figured I wouldnt run into him the city is too big.
it took me some time to type a reply to him 'why didnt you come pinch me to see...I bent over for you and everything'. our conversation went on for a few minutes mostly him telling me how sexy I looked, I asked if he wanted to cam and he agreed quickly. when we started our cameras both of us smiled as soon as the other popped onto screen. I stepped back from the computer so my whole body was in clear veiw and did a slow spin to show off my girlish appearance. I was met with applause from my cute veiwer I stopped spinning and faced the camera again "do you want to see more my handsome young man". with a big smile he said yes, I slowly unbutton my shirt smiling into the camera I let the shirt fall open exposing my corset hugging me tightly. the sleeves slide down my shoulders and off my arms onto the floor, I do a slow spin again this time pausing sideways to the camera and bending down to adjust ankle strap of my shoe giving him a nice view of my long thin legs and cute perky ass. standing again I go to the screen and I see hes stripped down to just a pair of tiny black shorts almost like the ones volleyball players wear hes rubbing his cock through the tight black fabric. I ask him if he wanted more and he says please so I feel obliged to show him more steping back from the screen again I turn my back to him. reaching behind me with both hands I slowly unzip the back of my skirt first exposing the back of my satin garter belt then the lacy top of my panties then I let go and the skirt falls down around my ankles. I look over my shoulder and see him on the screen hes got his cock out stroking it I turned around to give him the full view of my body and so I could watch him stroke his hard cock. sitting back in front of the computer I light up a cigarette taking a long slow drag he stops stroking his cock and pulls the shorts back over it. he leans into the camera to ask the question "so do you want to hook up tonight maybe?" I had never dressed for a guy before and was nervous but Im not gonna lie I have always had the fantasy of hooking up with a hot guy. so why not I think maybe I should do this but its gonna happen my way so I lean in and say "ok baby but you have to play by my rules and rule one is your my slave...ok cutie pie". he takes a moment to think it over "no real pain or any gross stuff right" he asks. "no my pet I wont leave a mark on you and I dont like getting dirty so dont worry no gross stuff," I purrr. "ok mistress" he says with a chuckle.
I give him my phone number and tell him to meet me outside the bar down from my house. when he arrives im already there in my car waiting for him I pull up as he walks from his car. "get in" I say through the open window. when he gets in the car I look him over I can see hes bulging in his pants already "very nice my pet now take your cock out your mistress wants to see her new toy". without hesitation he pulls his pants down and frees his big uncut cock from the tight shorts it looks even bigger in real life long and thick with kind of a curve downward. "arent you just the obedient little pet" I say taking his cock in my hand giving the shaft a firm squeeze. driving to my place takes only minutes and I keep stroking his hard shaft untill we are in the parking garage. "ok put it away my pet the real fun is upstairs" I instruct while opening the door to get out. stepping into the elevator I press the button for my floor ten, we're alone as the doors close hes standing against the back wall. I face him pressing him against the wall and grabbing him by the chin "are you going to be a good boy tonight or am I going to need to punish you". before he can answer I lick his lips with my long tongue and then going in for a deep kiss my tongue filling his mouth as I hold him against the wall. when I free him from my kiss his mouth is marked with my bright red lipstick he goes to wipe it off and I stop him "leave it, so people know your mine".
we step out of the elevator and walk down the hall to my apartment and go inside. "come my pet lets retire to the bedroom and get more comfortable" he follows my every command without question. "now my pet im going to change into something more appropriate for you I want you to strip down to nothing but those tiny black shorts and kneel at the foot of the bed for me and ill be right back shortly" I excuse myself to the bathroom. I change into my latex outfit and fix my makeup putting on the lush dark red lipstick and outlining my lips in the maroon lip liner. im wrapped in skin tight black latex and wearing my tall white platform heels that make me well over six feet tall, I return to the bedroom where my pet waits obediently at the foot of the bed. "do you like my outfit my pet" he obediently nods yes "get down on your hands and knees for your mistress". looking down at this cute young guy on his hands and knees was a huge turn on especially since I knew he would do as I ordered him. "I want you to kiss my feet my pet make my latex stockings wet with your spit" I tell him. he begins licking and kissing my feet slowly working his way up my long legs he makes it to the top of the latex and kisses my bare white flesh. he moves in to kiss the front of my panties and I grab him by the chin waving my finger in his face to scold him "now now my pet dont get ahead of yourself I told you to kiss my legs, now back down on your hands I want to look at you." he bows down in front of me keeping his ass up, I walk around to the bed and sit down his ass is right infront of me I can see the outline of his twitching hard on straining against the tight fabric. I reach down and cup his balls in my hand "we're going to drain these tonight I want your cum...all of it". squeezing and rubbing his swollen sack in my hand stroking him slowly trying to tease him. I release his balls and slide his shorts down to his knees exposing his clean shaven balls and ass. his pink little assshole shines with smoothness, I lick my finger and rub slowly around his tight pink hole. "have you ever been fucked my pet" I ask. "only once" he says. "only once what" I snap back. "only once mistress" he comes back with. I raise my hand and bring it down with a crack against his ass causing him to squirm and moan, a bright red outline of my hand appears on his copper skin. "are we going to remember how to adress me" I snarl. "yes mistress" he says shyly. I return my finger to his ass rubbing and lightly pressing against his hole "I think I have just the thing for you my pet wait here". I go to the dresser and pull out a small pink butt plug returning to the bed I lick and suck the little plug to lube it up, I spit on his asshole and rub it around with the head of the plug. slowly I work the little plug into his tight pink ass untill it slips in, he lets out a moan. I gently tug on the base to watch his little ass stretch open my cock is rock hard and has come out of the crotch of my panties. "turn around and face me my little pet " I instruct. he turn and faces me I motion him between my open legs, when hes within reach I take him by the back of the head. "now open your mouth baby ive got something for you" I chuckle. he opens his mouth and looks up at me, I guide his head forward into my crotch his lips graze the head of my cock and I pull him into me plunging my cock deep into his mouth. his lips wrap around my hard shaft as I pump his head back and fourth hes moaning staring up at me with my cock buried in his mouth. after several minutes of using his mouth I order him to lay on the bed I go to the nightstand drawer and pull out fout pieces of rope. I secure the first around his wrist then tightly down to the leg of the bed repeating the process on his other arm and legs untill hes retrained to the bed spread eagle. I stand over my helpless pet "there we go my pet now its time to have some fun". crawling on the bed bewteen his legs I take his thick throbbing prick in my hand stroking him slowly watching the foreskin roll over his head. while stroking I slide my tongue underneath his sack and draw my tongue up slowly licking untill im at his head. pressing my lips to the tip of his cock makes him moan his cock pulses in my tight grip. I stroke slowly with my lips teasing the head of his cock then I suck his head into my mouth. he gasps and I swirl my tongue around the tip of his cock. he has a big thick cock and the head even does a good job of filling my mouth I slowly start to draw him into my mouth sucking and bobbing on his shaft. he is glistening with my saliva and his cock completely fills my mouth pressing against the back of my mouth. I keep pace sucking him and playing with his balls hes moaning and panting struggling againt the ropes that bind him down. hes trying to thrust into me but is bound much to tightly and can only manage a little push. I press down on his hips "now now lay still I think I know what you wwnt". taking him back in my mouth I wotk him to the back of my mouth then with more than a little effort I swallow his cock letting it slide into my throat I gag a little when my lips meet his balls but keep him in me. I start to fuck his big cock with my throat not sucking anymore just letting the tightness of my throat milk his cock. I can only stay down for so long and have to come up for air, when his cock emerges from my mouth its covered in thick strings of spit connecting us together. I reach up and wipe my mouth gathering up much of the saliva then rubbing it all over his cock and balls stroking him. "is that what you were wanting my pet l" I purrr. "yes mistress thank you mistress" he pants. taking him back into my mouth I slurp and bob on his rock hard cock im moaning like a whore. several more times I take him into my throat milking him just like I always practiced on my big black dildo. im so worked up I need to feel his big thick cock inside me before he cums hes dripping with my saliva as I stroke him. I crawl on top of him sliping the soaking head of his cock between my ass cheeks pressing him against my backdoor. "now my pet im going to take you inside me now I dont want you to come too fast tho so ill start slow" I coo. "ok mistress please go slow" his voice wavers. I ease down sliding his head inside me the thickness of his cock stretches me open pumping. "your so big my pet that big fat cock stretches me open just right, do you like my ass my pet," i feel like a godess riding him. yes mistress your ass is more perfect than I could have imagined you make me feel so good mistress" he replys. slowly im inching him inside me I can feel him spreading my insides open. finally I have him all the way inside me his balls press against my tailbone. I have a trick I want to try on a real cock so I begin to ride slowly. relaxing my hole on the downstroke and squeezing on the up stroke only moving an inch or so keeping him deep inside me. it feels like nothing else exists around me all of my senses are overloaded all that matters is the big cock buried in my asshole. I barely hear him say it but it snaps me back to the bedroom "mistress im going to cum!" I slam down on him as he explodes I can feel him pulsing and the cum rushes into me coating my insides im shaking and baying. I can feel cum leaking out as im pumping him inside me, slowly I let him slide out of my cum filled ass. I collapse on top of him my ass is gaping and cum is leaking out running down my balls and onto his cock. I regain my senses and slide down his body hes covered in his cum I begin licking up the mess slurping our juices up. I sucked his balls into my mouth not freeing them till their squeaky clean then I take his cock back into my mouth sucking him dry. "now my pet its my turn" I smile at him. untieing his ankles I push his legs up to his shoulders "are you ready my pet". I reach down and pull the plug out slowly opening his ass up for my hard cock. I reach behind me and scoop up some cum and spit from my asshole rubbing it on his pink hole. "cum makes the best lube my pet" I purr. I press the head of my cock into his cum slick ass he winces as I push my way into him. "relax my pet im not going to hurt you" I say thrusting into him. by the time im balls deep in him I can feel my balls boiling and know im going to cum soon. I start thrusting harder my balls smack against his ass rhythmically. with one final thrust I fill him with my cum pumping him full of my hot sticky jizz. I release him from his binds and stand up straightening myself up. cum is running down my black latex stocking so I point and order him to lick me clean. he crawls over to me and begins to lick uo his cum starting at my ankle and working his way up. he buries his face between my ass cheeks and drives his tongue into my asshole fucking my hole with his mouth. once im convinced hes done a good job I tell him hes done and he sits on the floor. "well my pet that was fun but now I need to get cleaned up I want you to keep my cum in your ass untill you get home then and only then may you push it out on the condition you will take pictures of your cum filled ass and email them to me, ok" I order. he shakes his head and says "yes mistress anything you like". he left and I got cleaned up putting on some comfy panties and a tee shirt. I checked my email before bed and browsed through the pictures of my pets cum leaking asshole. pleased with my night I slid into my bed and drifted off to sl**p.

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