Sexy Boy Takes All
He calls me in the morning in order to see me that very afternoon. Justin is very business-like and courteous on the phone, getting straight to the point, no tire-kicking. He says he really likes to dirty talk and asks me if I minded if he was queer/bi-sexual. I grin.”Not at all,” I say. As a queer girl myself, I love getting it on with guys who are open-minded and open-assed. Plus I just love calling a boy a dirty little cocksucker – but only when he deserves it. As an escort, its rare for my clients to be queer…or at least, it is rare that they tell me about it. I am pleased when, by late morning, Justin forwards me a few photos of his beautiful smooth ass all filled up by another guy’s lovely cock… and I wondered who exactly had taken the photo!
Justin shows up to my apartment right on time. He is personable, well-mannered and clean-cut, not particularly a stunner, but has a wide grin and tells me right away that he was pretty horny and worked up. He is wearing blue jeans and a button-up shirt. He peels the 20s off his billfold straight off (love love love that) and sits down in my little wooden kitchen chair to kick off his boots, then leans back, spreads his legs a bit wider open, and I see the outline of his lovely hard cock tipping off to the left. Ready, indeed.
I am wearing my usual clothes: short pencil skirt, transparent frilly secretarial blouse with leopard print push up bra clearly visible underneath, no panties, and red stilettos. He looks me over, up and down, and I perform a saucy turn so he can see everything. He smiles and rests his hands on my ass cheeks, cupping them through the stretchy black fabric. I back up onto his lap, pulling his legs together with mine and sitting down, pulling his hands up onto my tits and squeezing. Wiggling my butt around over his hard-on, I ask if he is ready to get undressed. He says yes, but then pauses, and says he had a little surprise for me. I turn and stand. “Show me,” I say.
Justin starts wriggling down his tight jeans to reveal the prettiest pair of pink panties and garter belt, attached to long beautiful white stockings expertly concealed under his jeans and white athletic socks. I’m breathless. How lovely and kinky! I find femininity so beautiful in unexpected places. But this boy does need some stripping lessons. “Stand up and turn around,” I say. He does so and leans over the chair, sticking out his tight little behind and rubbing it hard on my pubic bone. I push him away and scoop the pink g-string under my finger, sliding it side to side and watching his asshole peek in and out of view, his balls cupped in the lace. He moans and tries to push his ass onto me again. Since Justin is so eager to be such a little sissy girl, I push him back and make him wait. There’s no way that I am letting an opportunity like this go by. “Sit back down and put your arms down by your sides, my little faggot, or your ass is staying empty this afternoon,” I instruct him. He obeys.
I grab some lovely purple hemp rope from my trunk of tricks and loop it over and around his wrists, securing him to the chair. Once he is immobile, I pull off his jeans and socks completely and run my nails up and down the insides of his legs, which I now notice are also clean shaven. I only wish he’d brought some heels – his feet must be twice the size of mine so I can’t exactly lend him any. Instead I tell Justin to arch his feet on his tippy-toes and simply pretend he is wearing a pair of shiny kitten heels with great big bows on the open toes. He obeys and his legs transform into all pointy knees and firm calves. I take a seat on his lap while he strains to keep his imaginary shoes on.
Hooking my heels on the bottom rungs of the chair in order to make Justin take all my weight, I zip open my little black and white gingham vinyl makeup bag and instruct Justin to close his eyes. He flutters his long eyelashes down and my heart skips and prances. What a beauty! Since we only have a hour, I work quickly, applying silver glitter to his temples and eyelids and primp his already curved lashes with clumpy blue mascara. His eyes quiver with excitement and I can see sweat dripping down from his armpits as he struggles to sit still with his toes perched on his imaginary pumps. I jiggle myself up and down on his lap while I pump the mascara brush back into the tube, working my pencil skirt up over my thighs, feeling his silky stockings rub against my bare ass. Justin opens his eyes and he looks so pretty with his makeup on. I pinch his nipples and delight in the way he is catching his breath, looking down at my shaven pussy just a few inches from his lacy dick.
Since he is playing so nicely I decide it is time to treat him a little bit. I slide my body onto the floor and arrange myself cat-like on my hands and knees, back arched. My skirt is still around my waist and I know that he can see all of my back end in the mirrors I have expertly placed around the room. I peel back his panties from his cock and take it in my hand, grasping it at the very base. It’s quite beautiful and of course I want to taste it, so I slip the head into my mouth, delighting in the knob pressing against the front of my mouth. I work up a good spit on it, and start slipping it further and further into my mouth. Justin moans under the stress of the ropes. I play with the idea of leaving him there for a few minutes while I go into the kitchen, but the truth is that I just can’t leave this kinky boy and his willingness to play games with me. So I keep going, letting his cock touch the very back of my throat, until it’s all covered in shiny spit. Then I rub it all over my face, over my cheeks and then over my nipples. I can see his legs quivering and I remember that he is still holding his pretty legs up in his imaginary shoes. “Slip your shoes off,” I say. Of course he does it, and then I lift his legs up and slide his underwear down over his legs. His balls hang down and his cock bounces side to side, the only impatient part of him. I leave the stockings and belt because his smooth legs look so hot.
Justin looks down at me with the sexiest mascara’d fuck me eyes and so I position his legs wide open and reach between his ass cheeks. After covering my fingers in lube, I resume sucking his hard dick and slowly introduce my fingers into his lovely tight asshole. Now he starts talking. “Fuck me, baby,” he says breathlessly. “Treat me like your little whore.” Mmmm! I push in a little deeper until I can feel the pulsing knot of his prostate. The hot little button is all swollen and ready to be pressed. I start rocking my fingers in and out his ass just the smallest amount, of course I am gentle with him. (I always am with the boys.) He starts wriggling around on his little wooden seat and soon there is a wet pool of my spit and lube dripping down onto the floor between us. I perform that tricky balancing act of one hand propped between his ass cheeks and the other on his cock, stroking the bottom half of his shaft while my mouth works the top half. “Oh, don’t stop,” he begs. I try to smile and say something in return but it’s hard to talk with a dick in your mouth.
Instead I focus on synching the rhythm of my two hands and rock him back on the chair with the effort of it. His eyes widen in a bit of fear since his hands are still bound to the chair – if it topples we will have a problem on our hands! But I’m careful and we move slowly backwards with the force of the fucking until the chair is wedged against the wall of my bedroom.
Feeling safe again, Justin again closes his eyes and leans his head back against the wall and I keep up the cocksucking, feeling his body, inside and out… he is getting closer and closer to orgasm. Finally I feel the familiar spasms start deep in his body and his cum rockets upwards through to his cock. I pull my mouth away just in time and soon there are spurting ropes of cum showering his belly and my face.
Justin moans and shakes and I slowly take my hands away from his body and untie his binds as quickly as I can. I then lead him to the bed where he stretches out and falls into a light sleep for about 10 minutes, then he is up, showered, and out the door, promising to come back soon. I certainly hope so. I love my sissy boys. Next time, he can do the same to me!