Sissy's First Time

This story contains rough bdsm, non-con, and forced content. If you aren't comfortable reading that please do not continue. All characters are 18+

I recently moved to a new state and have been having a hard time meeting people. Since I live far away from most of my family and friends, I think it's the perfect opportunity to meet people on the kinky side. No one knows but I've secretly dreamed of being dominated by a mistress, I wanna have my cock caged, get pegged, and be humiliated. This night in particular the desire keeps growing to the point where I locate the nearest adult store to me. There's one only 3 miles away, I can't believe I haven't seen it before, it closes at 10:00 pm. It's only 9:00 pm so I decided to make my way over there before my drive goes away.

When I arrive there's a decent number of people coming and going. Some are wearing sexy clothes like latex, others short miniskirts. I start getting hard imagining myself like them, I try calming down but only get harder. I step out of the car and make my way inside. There's an area to purchase sex toys, lingerie, costumes, and more. But on the other side is a wall and a black curtain. I make my way over there and peek my head through. I see large signs reading, "glory holes" "R4R board" "theatre" "private room" and more. The R4R board caught my eye first so I make my way over there and see a few people writing. A woman wearing a black latex mini skirt, and a sleeveless top approaches me.

"How old are you?" She asks in a demanding voice

"Oh, I'm 20... is that okay?" I ask with my voice quivering.

"Hm, younger, I'm assuming you're looking to be dominated?" She asks.

"Ye-yes, I am," I answer stuttering.

"Well, you're in luck a lot of people will be interested in you mainly for your age. I'd recommend making a post for male and female. You'll have better luck finding someone. Why don't you go over there and fill out the form?" She tells me while pointing to the M4A section. I nod my head and make my way over even though I know I'd prefer to be dominated by a mistress I decided I wouldn't answer any males who messaged me. I begin filling out the form.

I skim most of it, checking off things and acknowledging that I consent to both males and females. I write my age and sign it off not reading the full document.

"Finished?" She asks. I nod my head again. "Okay, if you want people to notice you, I recommend adding a photo as it will increase your chances of being contacted." She tells me.

"Oh, I don't have anything with me right now, I should've thought of that. That's okay though, thank you for the suggestion." I tell her.

"Not a problem, we have a photo studio here free of charge your first time. I'll personally help you get dressed properly. Are you interested?" She asks me.

My cock is growing hard, and I immediately agree. "Okay, please remove all your clothes now." She says without hesitation. My heart drops to my stomach there are a few people around. "Can't I change in the photo studio?" I ask her.

"If you're serious about this I'm sure you won't mind these people getting a look at you. Also, you're only allowed to be in the photo studio if you're nude. So, if I don't see you in the next five minutes, I'll assume you're not serious and take your post down." She says while walking away.

I'm shaking with anticipation; I don't want this feeling to go away. I justify it in my head that I won't see any of these people and that I'll do it quickly. I start stripping and a few people lock eyes on me, I try to ignore it and once I am fully nude, I hurriedly make my way to where she went and step inside the photo studio room.

"I won't lie, I didn't think you were for real... put your clothes down I have two outfits picked out for you." She speaks. I drop my clothes and she makes her way towards me holding things in her hands. "We'll start with just the chastity cage." She says and shows me a pink cage. As I look at it, I suddenly feel ice on my cock and my erection shrivels away. Before I can even react, she's attaching the cage to my balls, then locking the cage in place. It all happens so quickly; I feel a slap on my ass. She holds a crop whip.

"Get over there boy, on your knees, hands behind your head, spread your legs, tongue out, and look into the camera." She commands me. And I quickly get in front of the camera. Getting on my knees and spreading my legs, I put my hands on the back of my head and stick my tongue out. Already my cock is begging to get hard. As I stay still the woman looks down at me with a smile on her face, taking her time getting to the camera. During this, I look around and notice a few more cameras in the corners of the room with a red dot flashing. I assume it's just for security purposes, so I look back into the camera.

"They're gonna love you I know it." She snaps a few photos of me zooming in and out then walks over to the table and returns over to me holding other pink objects. "Open wide," she commands, and I do as I'm told. She shoves a ball gag in my mouth tightening it around my face. "Hands out in front of you," she orders, and I do as I'm told. She starts putting pink rubbery sleeves up both my arms. "Sit on your butt," she tells me, and I obey. I see her reaching for pink high heels which she straps onto my feet. "Hands behind your back." I listen to her and obey once again. I hear the click of handcuffs and feel my wrists tightening. Next thing I know she's attaching a pink collar around my neck then a leash.

"Follow me on your knees boy." She tugs on my leash, and I'm led to a new room where I see other people scantly clothed like me. A chill runs up my spine and I look up at the woman shaking my head. She smiles down at me, "You signed your name on the form honey, welcome to your new life." She laughs and tugs me over to an empty stall where she puts me in. Tying the leash to the wall and then putting the photo she took of me in a folder. She puts the folder next to my stall, then stoops down to my level and smiles at me some more.

"Don't worry, anyone that decides to purchase you will take very good care of you. All our clients are vetted, tested, and clean. You'll be in good hands. Now, you did sign off on agreeing to be purchased by a male or female, I'm not sure who will be showing up tonight but most of our clientele are males." She warns me and frowns a little. "You won't be here long, once the store closes the real party starts and our clientele will arrive. While you wait go ahead and enjoy it here while it lasts. Soon you'll have men touching you all over your body." She gets up and walks away.

The reality of my situation hits me, I can't believe this is all happening to me. I'm unable to move and my eyes are racing around the room. I see a woman in front of me. She's very attractive but she also has a worried look on her face. I start to hear voices piling up in the other room. The woman returns and starts speaking loudly, more women come and stand by each stall. "Attention everyone, the evening is about to begin. Our clientele is arriving as we speak and expect everyone on their best behavior. Your chaperone will be holding your leash until you are bought. Once you are purchased your leash will be handed off to your new owner and you will be going home with them." She finishes and motions for the other women to grab our leashes and folders and bring us to the main room. I start following on my knees behind my chaperone trying to keep up.

As soon as I enter the room, I see only men in professional attire. The other chaperones lead the other subs to the clientele. Mine leads me to three men talking amongst themselves. She hands them my folder and I see one of the men pulling out my photo, he passes it around his group. I notice his eyes widen as he reads a sheet of paper. "20 years old huh?" He speaks. He looks down at me, specifically my caged cock. He puts his foot on it and lifts it. "These types are so pathetic; they'll do anything for cock." He speaks. One of the other men makes his way behind me. I feel his hand grabbing my ass and groping me. The third man watches and I see him getting hard, he touches himself. The man touching my caged cock goes down to my level and holds my cage in his hand. Humiliated I look away from him until, "Look at me." He commands and I do as I'm told. He squeezes a little and I gasp but it's covered by the gag. The other man continues to touch and grope my ass eventually getting around to fingering it.

I want to cum so bad during this and they know it. The man rubbing himself starts taking his pants off and reveals his cock. He starts jerking off to me getting violated by these two men. The one holding my caged cock uses his other hand to grab my hair. I look into his eyes and see an evil look on his face. He squeezes as hard as he can, my knees buckle, and I start to go limp. My chaperone holds my leach tightly keeping me up as well as the man holding my hair. The other one fingering my ass goes faster. Everything starts to heat the two men violating me look at the third man jerking off. He nods his head; I assume indicating he's close.

The man removes his finger from my ass, the other lets go of my cock and hair. He stands and pushes me to the ground holding me in place. The other man grabs my legs and I realize what's about to happen to me, I squirm trying to get free and yell, but the gag holds my screams to a muffle. It's useless, I'm helpless, about to be used against my will. My protesting becomes very noticeable to the whole room. I start to cry knowing it will happen at any minute. I notice the man jerking off move behind me. I try turning my head, but the man holds me in place.

I feel the other man touching my ass, then sticking his finger in my hole. I turn my head just enough to see the woman who started all of this. She notices me and says, "Remember you signed off on this." She says and walks away. I feel the man press deeper into my ass with his finger then pull out. He spreads my cheeks and I feel both men holding me down tightly. I try to beg them not to but it's too late.

I feel the man's cock press up against my hole I cry out in my pain as he goes deeper. The gag fails to cover my screams. The man goes deeper into me and starts fucking me in and out with a rhythm. It goes on for several minutes like this. He grabs my hair and bobs me back and forth. I can't take it much longer until I feel him pull out some. Right when I think it's all over, he shoves it back in harshly and I squeal in pain. He repeats this process over and over. Until he pulls out entirely and both men let go of me. I stay on the ground in pain.

"I'll take him." The man that used me said. I look up and see him exchanging money with my chaperone. She hands him my leash and he tugs at it. "Come slave, we're just getting started." I try getting to my knees and follow him. He leads me out the door and to his car where he opens the trunk and sticks me inside. He grabs my caged cock and laughs before shutting the door. The engine starts and he drives off.

I shake around in the trunk unable to stay still. My hands have been handcuffed behind my back for hours now. I'm beginning to get sore. I start thinking about what will happen to me from here. Surely, I'll be let go after he's done using me. The denial sinks in my head and I feel the car stop suddenly. I hear his car door open then the trunk unlocks. The trunk opens and I see him looking at me with a big grin on his face. He grabs my leash and yanks me out of the trunk. I fall to my knees on the pavement and grunt in pain, he keeps dragging me by the leash. I try to keep up with my knees in incredible pain.

He brings me up to the door and unlocks it where he pulls me inside harshly. I fall to the ground not wanting to get back up. I look to see him leaving me, he steps into another room. My arms are so sore and hurt, I can't move them. He returns holding a variety of things in his hands. A dildo, rope, clamps, some kind of pink costume, and more. He sets it on a cushion of the couch then reaches for my leash and pulls me up and over to him. He sits down. "Get comfy slave." He orders me. I lay as comfortably as I could on the ground. He comes over to me and takes off handcuffs, I slowly move them in front of me. He sits back down. "If you're a good boy I'll take that gag out too." He tells me with a smile.

This man sickens me, he just raped me and now acts like he cares about me. I take my chance not caring that I'm nude, getting up in pain, and trying to make it to the door. The pink heels I'm in cause me to trip before I even take three steps. I fall to the ground and cry out in pain. The man grabs my leash tightly and pulls me back over to him. The look on his face is one of amusement. "So, it's gonna be like that huh?" He stands up still holding my leash and attaches it to the wall. He walks over to a closet pulling out a folder chair. He sets it in front of the couch and sits me down on it.

He unties my leash and takes off my collar only to attach another collar this one thicker, with some wires poking out. As I sit in the chair, he grabs my hands and puts them on each end of the folding chair starting with my left. He uses the rope to tie it, then the right. He puts rope around my chest and ties it tightly, so my back is pulled to the chair's back. Next, he tied my thighs to the chair and then my legs individually. I can't move and look up at him as he still wears the sick grin on his face. He shows me a remote.

"Step out of line again and this is what you'll get." He pulls the knob slightly and an electric shock radiates throughout my body. I squeal through the gag and look at him with pain in my eyes. The shock continues and I feel like someone is pressing a bunch of needles on my body. I try to beg him to stop but he keeps it on. It feels like five minutes until he stops it. "That was only ten seconds on the lowest setting slave. Disobey me again and it'll only get worse. Nod your head if you understand." He tells me.

I quickly nod and watch as he sits on the couch and starts to rub himself again. "Was that your first time getting fucked slave?" He asks me. I nod my head as he presses and rubs harder. He moans, "Ever suck a cock before?" I shake my head no. He keeps rubbing and smiles at me. "Well, let's change that right now. I'm sure your mouth is dying to be free from that gag." He steps closer to me and slowly pushes my chair back till I'm completely on the ground. He takes off his clothes and positions himself on top of me, his cock right in front of my face, he unties my gag and removes it. Drool spills out my mouth and the man pushes his cock on my face slapping me with it. He gets on all fours, and I see his cock right above me, he wastes so much time and shoves it.

He starts fucking my mouth in and out pausing a few times. "SUCK IT BITCH!" He screams and I start sucking it. He moans loudly going in and out again. I feel completely helpless, it looks like he could do this for hours. My mouth starts getting sore, and he shoves it deeper and deeper down my throat I gag on it, and he pulls out slapping my face with his cock again. "No gagging slut, take the whole thing." He says and shoves it back in my mouth, fucking me again and then going deeper. I feel it in my throat again and he practically lays down on me with all his weight. I can't take it or breathe through my nose because he's blocking it. He stays right on top of me. I gag but he stays still, my gagging becomes impossible to ignore at this point. He slowly gets back up, his cock still in my mouth, then suddenly shoves it back in deeper than before, I feel his cock twitching and I let out a muffled scream in pain when he pulls out. His cock is right in my face as he cums right on my face. It's a huge load that keeps on going. He lets out several moans and gets off me. His cum is still on my face, he pulls the chair back up. The man lies on the couch out of breath.

I feel his cum on my face as it drips down a little. The man tries to catch his breath as he looks at me. "He looks better with my cum running down your face." He says while I look at him with a look of disgust. He notices, "Listen slave, you can either learn to enjoy this or keep up this attitude. Trust me I don't care if you like this or not. You better get used to it because tomorrow it won't just be my cock inside you, or my cum on you. I'm inviting some guests over that you will entertain. I'd recommend you get some sleep, but you'll also need some practice..." he tells me while getting up. I see him grab a dildo, stick it to the mirror and it hangs there. He pulls my chair over to it until my mouth lines up with the dildo. He forces my mouth open and gets the dildo in.

"Good night slave. I'll see you in the morning." He laughs and leaves a light on in the room so I can see myself in the mirror. I'm tied up to a chair, dildo in my mouth, with cum dripping down my face. I try pulling my head back but fail, the dildo is lodged deep in my mouth. I try shutting my eyes waiting for the night to pass to get ready for my rough day ahead.

**

As I find myself in a half-asleep half-awake state. I can vaguely hear a sound in front of me. My eyes begin to open, and I see a blurry figure in front of me wearing no clothes, as I squint my eyes, I see it's the man jerking off in front of my face. My mouth was still filled with the dildo. The man starts to moan and notice his cock twitching I shut my eyes only to hear him say, "Keep your eyes open slut." I open them and see him holding the remote in his other hand. I try to shake my head no and he chuckles still jerking off faster. His cock is twitching some more, and I see precum dripping. His cock starts spewing out cum right on me again, some getting in my eye. As he keeps cumming he turns the dial and I feel the electric shock throughout my body again. He stops it quickly. My whole body is shaking. The man pulls my chair, and my mouth is free from the dildo The man starts talking to me while untying me.

"We need to get you ready for the day ahead. I have a cute outfit planned out for you."

Once I'm untied from the chair, he lifts me and brings me to a bathroom. The tub has suction restraints on the sides inside of it. He strips off my collar, and everything else off my body except the cage and lays me down and ties my legs and hands to the restraints. He tugs my hands, and the restraints don't even budge. He grabs soap and starts rubbing it all over my body. He lifts my caged cock and gets soap underneath it. My whole body was covered in soap at this point. He starts the water in the shower making sure it's warm. "Enjoy the soak slave, I'll be back soon." He says while leaving. I hear the door lock on the other side.

The water rains down on me from the shower, it's nice and warm. I feel my body getting cleaned off completely. The cum was no longer on my face, I lay there feeling relaxed for about 15 minutes until right in the queue I hear the door unlock and open. The man walks towards me, stopping the shower and then untying my restraints. He pulls me up and starts to dry me off where he hands me a new outfit. It's a white bodysuit with a plaid mini skirt, white thigh highs, and white high heels.

"Getting you dressed up like a schoolgirl for tonight. Go ahead and get changed then meet me back in the living room slave." He orders then leaves. I start getting dressed putting the bodysuit on as I look in the mirror, the skirt hardly covers me and you can easily see underneath. I put the thigh highs on and then the high heels, looking in the mirror at myself I want to get hard, but the chastity stops me from that. I step out of the bathroom and make my way into the living room.

There's a circular display stand in the middle of the room, the man turns to look at me and smiles. "don't you look adorable." He tells me and motions me to come over to him. I step closer to him. "Kneel." He commands and I do so without hesitation. He attaches a new collar around my neck, it's white, and says, "slave" on it. "step on the display stand and pose for me slave." Again I do as I'm told and step onto it, I assume a position you'd see a model do on Instagram. I put my right hand on my hip and rest my left on my thigh leaning to my right. The man sits down behind me, suddenly I feel the platform I'm on start to turn slowly. It moves me in a circle, and I keep my current position.