This is a fantasy, my fantasy and is not real. Please make sure you are of legal age before reading the following graphic story.
My sister knows that I have been dressing in girls clothes for four years now ever since she caught me in her black string bikinis and white patterned tights when I was 14. Needless to say, I freaked out but she was completely cool with it. Ever since, we go shopping for new clothes together whenever she comes into town. For our last trip we went to the mall an hour away and pretended to shop for her since I am still very much in the closet. In one store we found a tiny, cotton stretch black skirt that hugs my ass perfectly, a soft gray and white striped tight tee that gives me amazing boobs with just a bra. I noticed a 6'1 guy, mid-forties, with jet black hair staring at us. My sister didn't bother to look and when I turned back, he was gone. I just put it out of my mind as we paid and left the store. Next, we bought some AE panties and patterned tights, black, white, and blue. After that, we decided it was time to go home and go our separate ways, besides, I couldn't wait to put on the new outfit.
By the time I got home it was dark. I live in the country surrounded by trees with the next neighbor a mile down the road. There is never crime so half the time I don't even lock the door. I ran upstairs to the bathroom, started a scented bubblebath, and looked at my new clothes. I hopped in and shaved my entire body, god I loved the smoothness as I rubbed my hands up and down my legs. Time to get dressed. I start by sliding my new white and black polka dot string bikinis up my newly shaved legs and squeezing my tiny penis into the tight panties. Next is my white bra and new top. Now my favorite part, the tights. I roll the tights up, inserting my toes and savoring the feeling of sliding the silky black pattern up my smooth legs. That part is heaven for me. Lastly I slide my new black skirt up my tights and around my waist. The skirt stretches and lands around my mid thigh. I go to look in the mirror at the smooth blonde hair bombshell looking back at me who is 5'5 140 pounds. I also see that guy I saw at the mall standing behind me.
He reaches around me and covers my mouth while using his body to slam me up against the full length mirror. I try to fight but he takes an arm and pins it behind my back while still hand gagging me. I try to reach out with my other hand but he just squeezes my arm tighter into my back. He whispers into my ear "I like the new outfit my fuck toy just bought." I redouble my effort only to be slammed back against the wall, the wind knocked out of me. He takes the opportunity to tie my hands together using an extra pair of tights he must have grabbed. He warns me not to yell for help as he leads me out of the bathroom and into my bedroom. I can't help but love the feeling of my silk covered feet on the soft carpet. A fleeting thought as he pushes hard on my shoulder and I fall to my knees. He moves in front of me and I'm face to face with my first cock and his is much bigger than mine is, by several inches. "Open wide" he says. I'm too scared and don't move. SLAP. He doesn't have to say it again and I open as wide as possible. At first he places the head just in my mouth and I taste his precum as it lands on my tongue. I can't believe I have a cock in my mouth but there is no time to think as he slides in to the hilt causing me to gag. He holds onto my head as his hard throbbing cock is deep in my mouth and throat. I can't breathe, I can't get away. "Take it deep bitch" he yells as he thrusts in and out of my mouth. I barely get a breath in, drool is dripping down my chin as his balls slap my chin and neck. It seems like forever but within minutes he is shooting a load of semen down my throat and I am ready to throw up.
I hope and pray that that is the end but I know thats not the case as he grabs my arm and forces me to stand. With a shove I land on the bed face first. I begin to panic and try to struggle again but he is on top of my holding me down. "What did I say about struggling fag?" he says as he starts to spank me. I cry out with each smack as I feel the burn spreading across my ass cheeks. "If you want it rough, I can make it rough. If you are a nice girl though, daddy will make it nice for you." He reaches under me and my skirt to find my tiny penis rock hard and dripping precum into my new white and black polka dot panties. While rubbing it he says "I think you are really going to enjoy this, aren't you baby?" "No, please stop" but he didn't and I couldn't help but moan as he ground his now hardening penis into my ass crack through my skirt. He tells me not to move as he gets off me and starts rummaging through my drawers. I'm too scared to move, not like I could do much anyway with my hands tied behind my back. He comes back to the bed, grabs my long hair and pulls making me arch my back and forcing my mouth open. He shoves a pair of my girlfriends used panties into my mouth and ties them in with her worn pantyhose. I can taste and smell her as he ties my ankles together with another pair of tights. I am now completely helpless.
"She said you were a fag but I never knew you'd actually enjoy this." This can't be happening, Becca set me up. My girlfriend set me up. "She thought you only liked to be dressed up but I guess it is much more than that. Are you still a virgin with that lovely pussy you have?" "Y-y-yes daddy." "That's my girl. Daddy is going to make you a woman tonight. You would like that and you better give me the right answer." I know better than to hesitate even though its not what I want. "Yes daddy." With that he slides a pillow under my hips forcing my ass in the air and my face into the mattress. I am panty gagged, hands tied behind my back, ass in the air, and completely helpless. I feel my skirt being flipped onto my back, my panties and pantyhose being pulled down to my knees as he climbs on the bed behind me. I start to cry and whimper as a lubed finger enters my ass, then another one. "I hope you're ready to become a woman" he whispers in my ear as he moves his penis to my hole. "Just stay relaxed and it won't hurt too bad." He starts to push and I whimper into my panties. My ass stretching hurts as his thick and long penis moves in me inch by inch. He takes me gently, making sure I feel everything. Each thrust pushes my face into the tear stained mattress and each thrust starts to spread a warmth throughout my body. "You like that bitch, don't you?" he says as the intruder reaches around to start rubbing my dripping little cock. He picks up the pace, his moans getting louder and deeper as my moans turn into squeals of delight. His hips slap into me, his hand reaching around to jerk me off, my arms tied tight, his penis thrusting deep within me, and I am forced to take it like his little bitch. "I'm going to cum bitch, cum with me." Mmmphyes mmdaddymph I scream into the panties as I feel shot after shot filling my ass as he pulls my panties up in front and I cum into my new white polka dot panties. He rests on top of me until he goes soft, breathing heavily into my ear. He slips out of me and pulls my panties and tights the rest of the way up to catch his warm cum sliding out of my ass. Grabbing another pair of tights, he ties my ankles together and leaves me helpless on the bed with my panties full of our cum. "Don't you dare tell a soul what happened here unless you want Becca to tell everyone about your little secret." he says as he snaps a photo and walks out of the room leaving me tied and helpless on the bed.
I hope you enjoyed the story, feedback is always great. Please email me, Brie, at sissibarbimastr@hotmail.com and thank you for reading!