Straight to Sissy Pt. 02

Thank you all, who shared feedback on my last story. My hope is to get better as I write more so any feedback is appreciated.

I sit here bound and dressed like a slut, I look over and see my girlfriend with her new partner. They're holding each other in their arms, I feel a wave of humiliation come over me then my cock starts to grow harder. How can I be turned on by any of this? It's so perverse, yet I eagerly wait to be used again.

***

I hear an alarm go off and start to come to, I slept through most of the night despite being bound and gagged. My girlfriend and the man start to wake up as well, she reaches over to turn the alarm off. I watch them as they start to kiss and greet each other, she glances over at me and smiles. My face turns red as I look down and see just how excited my cock is, my girlfriend points it out to him.

"He's still enjoying this, look!" she points at my erect cock. The man laughs and gets off the bed walking towards me on the chair. He grabs my balls and holds them tightly.

"Did you enjoy sucking my cock last night boy?" I nod my head eagerly. He smiles and continues, "I think we should take this over to my place. I have more toys and devices we can use on him." He squeezes my balls as he says this, and I let out a whimper through my gag.

"Why don't you get things packed up while I have some fun with him this morning?" the man tells my girlfriend. She obeys, getting out of bed and gathering things into bags. The man, still holding a firm grasp on my balls reaches with the other hand to take out my gag. He lets go of my balls and stands up where I face his cock head-on.

Without being told, I get to work and push my head towards his cock taking it in my mouth. I lick it and take it deeper, once I start to gag, I pull off a bit and start to suck him off. I bob my head up and down on it for several minutes. He positions his hands on the back of my head to keep me going. "Look at me boy." I look up at him briefly then shut my eyes again. *SLAP*

He hits my face. "don't look away." I look back up immediately; he stares down at me with a look of anger. I keep sucking him and the humiliation sets in as I stare up at him while he has full control over me. Meanwhile, my girlfriend packs up, she occasionally looks over at me serving this man. He holds me on his cock not allowing me to move, my eyes still locked on him.

I feel his cock start to twitch in my mouth and a warm liquid shoot across hitting the back of my throat. He empties his load into my mouth, and I swallow it without being told. He smiles now, his angry expression is gone. He removes his hands from behind my head and slowly pushes me off his cock. "Lick it clean boy." I do as he commands and clean the rest of the cum off his cock, the humiliation is in full swing as I continue to stare into his eyes.

My girlfriend waits idly by as she's finished packing all our things. As I finish cleaning his cock he moves away, and I'm left with my tongue out. "I'll get the things in the car when I finish getting dressed, please untie him and dress him up in that princess costume you showed me then we will get to my place." The man orders my girlfriend.

She walks over to me and starts to untie my feet and legs. "I love how commanding he is; you seem to like him too..." she chuckles as she sets me free.

"I feel like I belong on my knees serving his cock. I don't understand why I feel this way." I tell her.

She starts to take undress me, "It's because you're a sissy now, what gives you pleasure doesn't matter anymore." She taps my cock then gets up to grab my new outfit. She returns with a blue plaid skirt with white frills on the bottom, a white corset, white heels, and white thigh highs with red bows on top. "Stand up." I do as she says.

I step into the skirt as she pulls it up my body, to no surprise it hardly covers me, next she puts the corset on me ensuring that it's tight which takes a minute or two. The man steps back into the room as she puts the finishing touches on my outfit. I look in the mirror the red bow accents on my thigh highs go nicely with the rest of the outfit. I put on the high heels and then noticed the man coming from behind me. He attaches a white collar and leash to me; he holds the leash in his hand.

"everything's ready to go. I'll drive, but I want him in the passenger seat with me." He tugs my leash, and we walk to his car in the driveaway, he opens my door and gestures for me to sit inside. I take my seat and my girlfriend sits in the backseat. He shuts my door and then makes his way to the driver's seat.

We set off to his place, he still holds my leash in one hand. I feel a slight tug on it and look over at him. He says something, I look back out the window but feel another tug I turn to look at him again this time I look down. I know what he wants without him even asking for it, I reach over and remove his pants then take his cock in my mouth and suck him as he drives us.

***

I have no idea how long we've been in his car, but he holds my leash tightly as I continue to suck him off and switches hands occasionally as one gets tired. Finally, he pulls me away as we bump up into a driveway. He parks the car, "why don't you get things inside while I get him ready?" he says while looking at my girlfriend. She nods in agreement, and we all step out of the car.

He leads me up the stairs to his front door, we step inside his home, and I'm led into a room that looks like a sex dungeon. I try taking it all in but we glide past everything and end up stopping by a pillory. He removes my leash then the collar and opens the pillory, it's connected to a padded bench which I kneel on top of my heels hanging over the edge. I poke my head and arms through. He shuts and locks it into place, I try pushing up but it's no use. The next thing I know I feel a harsh slap on my ass. I turn my head trying to look but can't see, I hear his footsteps leave the room.

My eyes look all over the place, I see dildos, all different types of whips, bondage devices, restraints, and so much more. I hear the two of them talking amongst themselves. About five minutes later they both enter the room completely nude; my girlfriend walks over to a cabinet while the man sits just outside my peripheral vision. My girlfriend pulls out a strapon, this one bigger than the ones we've tried before. She laughs and turns around, "what do you think?" she puts it on and walks over to me.

I notice the man start to jerk off, my girlfriend positions herself behind me, "you ready to put on a show?" she chuckles and starts to tap my hole with the strap on. I tense up and she slaps my ass, "You know it'll only hurt the more you resist it!" I try to let it in but it's so big. She takes her time until I feel it deep inside me. I'm letting out so many groans of agony, but it's obliterated into screams as she pounds me.

"You like it when I fuck you don't you sissy?" I cry out in pain feeling like I'm being torn into two. She doesn't let up and only goes faster, the pillory starts shaking, and start to get aroused as my hole gets used to the size. "Answer me sissy!" I feel her whip my back with a crop whip.

"Yes!" I cry out, she keeps pegging me. Her pace not letting up. I look over in my peripherals and see the man standing while jerking off he's walking over to me. I look up at him while I'm being fucked and open my mouth. He sticks it inside me and then grabs a hold of my hair. He pounds me and face fucks me. I'm being spit-roasted mercilessly for what feels like hours.

My girlfriend's pace starts to slow down but with sudden thrusts out of nowhere, the man keeps using my mouth and my eyes go in. They both pull out, my girlfriend takes off her strap-on and lays on the couch, and the man starts to fuck her in front of me. I stay locked in the pillory humiliated once again. He fucks her doggy style and I watch wishing it was me instead. While I watch them my cock can't take much more and starts to cum. I let out a loud moan.

He turns and sees the mess I'm making. As he finishes, he gets off her, she lays there exhausted and turns to face me out of breath. The man grabs a paddle and walks towards me, he gets behind me. I wait in anticipation as he pulls my skirt up to reveal my ass more.

*WHACK!* "AHH!" I let out a squeal as he violently hits my ass, then again... and again. It continues and I cry out in pain begging him to stop. He comes to the front and holds my head up with the paddle.

"This is what happens when you cum without permission." He pulls the paddle away and my head falls back down. *WHACK, WHACK WHACK!* he hits me three times in a row. I scream in agony but take my punishment. *WHACK!* he hits me again this one with a huge wind-up. I feel my ass sting. He comes back in front of me and lifts my head with the paddle again, tears flowing down my cheeks. "Think you learned a lesson?" I cry and nod my head. He sets the paddle down and then sits on the couch with my girlfriend. "What do you say we invite our guests over?" he asks her. I look at the two of them with a confused expression.

"don't worry, they'll treat you like the sissy you are," my girlfriend says while they both laugh. I start to shake in the pillory, but she reassures me that all the guests they invited have been vetted and tested. I feel a little less worried but continue to shake in anticipation of what will happen. The man gets on a computer and starts informing people to come over when they please.

My girlfriend leaves the couch and walks over and mocks me tapping my ass. It stings and still hurts; I quiver as she teases me and slaps it a few times. "I better get you ready for the rest of the day!" she says leaving a huge slap on my ass causing me to jolt forward.

She leaves the room and I prop my head up looking around. The man is still on his computer, but he looks up at me and smiles. "I hope you know you're doing a great job so far; I'm impressed with how well you're taking everything." He compliments me and keeps typing away.

"I don't understand why I'm getting so much pleasure out of being humiliated and used like this," I tell him and he looks back up at me, shutting his computer, he walks towards me then holds my chin up.

"I think you've always known you've wanted this, you're naturally submissive. A real man wouldn't allow himself to suck the cock that would fuck his girlfriend. Yet, you don't just allow it you eagerly await it. These men that will be stopping though won't be here to use her, she's mine. They're coming to use you." He talks down to me, still holding my chin up.

A sense of humiliation comes over me after he tells me all of this. Before I can reply my girlfriend returns with a new outfit for me to wear, it appears to be a plaid schoolgirl costume. The man lets go of my chin and makes his way behind me; I tighten up waiting for a slap until I feel him messing around my cock. He fits me into a chastity cage locking it and setting the key inside one of the glass cabinets.

My girlfriend frees me from the pillory, and I stretch out a bit trying to limit as much pain as possible. When I finish, she undresses me, so I'm left standing there with nothing on but the chastity cage. I'm handed a black seamless bra and panty which I begin to put on, it feels a little tight, but my girlfriend helps adjust the bra. Next, I put on a pair of black thigh highs, then a brunette wig which fits me nicely and doesn't shift. I reach for the plaid skirt before the man stops me.

"The guests won't be here till a later, let's get some fun photos of you!" my girlfriend agrees, and they motion for me to get in the middle of the room, the man takes a camera and points it at me. My girlfriend strikes a pose and tells me to copy her.

I get on my knees, slightly turning my head. "Pull up on your panties a little." I do so and hear a few snaps from the camera. My girlfriend keeps changing poses and I follow her lead, my ass just above the floor and my hands out past my head keep me up. I kick a leg out revealing more then put my elbows on the ground to support my body. Now I stand with a slight lean, my arms in the arm following the curve my body makes. I feel confidence start to rise in me, I stop following her lead and pose for myself. Ass towards the camera, leaning on one of my hips, then laying my body on the floor holding up my foot with one of my hands in a lateral pose.

I stop myself and look at them, they smile at me. My girlfriend compliments my poses as she hands over the plaid skirt and top. I slide the mini skirt on and then tie the top on, my outfit is finished off as she adds makeup to my face. Once fully dolled up, I look in the mirror and want to get hard so badly. The person looking back can't be me, she's too slutty, smooth, and clear. I admire myself in the mirror for a bit, striking a few different poses until I notice them coming from behind me. He pulls me towards him, and I feel his cock touching my ass foreshadowing what will be happening to me soon.

"I think they'll be here soon; they're expecting you to be tied up and ready, but I think we'll keep you free for now. You can greet them on your knees as they come in once everyone is here and we're ready we'll head off into the bedroom where I'll get you properly tied and ready. Sound good?" I nod my head and immediately get on my knees without being told.

"Good girl." He says while patting my head. My girlfriend returns to the room wearing a pink swimsuit, the man is still nude as she latches on to him. He holds her ass, and they make out until we hear the doorbell ring. My girlfriend rushes over to answer it, she greets the two people instructing them to go ahead and change as soon as they get inside.

They complement her look and step inside, the man greets them as well, and I just look up at them too afraid to say anything, I assume I should speak only when spoken to. The two men that arrive look to be older than the man, my girlfriend, and I. As they start to undress one of them notices me. "No way, that's a man!" the yells, my girlfriend laughs and walks over to me lifting my skirt and moving aside the panties. The man's mouth drops, and I see a look in his eye that says he can't wait to use me.

Let's introduce ourselves another, as we haven't formally met. My girlfriend introduces herself using a fake name, "Ella" The man whom I still don't know his name introduces himself as Smith but he looks down at me, "You call me Mr. Smith." I nod in agreement. The other men introduce themselves but the meet and greet is cut short as the doorbell rings again and my girlfriend rushes to open it.

More people come inside as the doorbell continues ringing and being answered. I remain on my knees and some men come over to me, not talking to me only acknowledging my body. They ask Mr. Smith if they can touch me, and he allows them to, telling me to get on all fours. I do so and start getting groped all over my body.

More people come and go until Mr. Smith announces that we'll be moving to the bedroom. He waves his hand at me, and I crawl on my hands and knees to follow him. The hoard of men follows behind as my girlfriend follows behind them. I get into the bedroom and lay face down ass up. Mr. Smith intentionally left a few pillows on the bed so my ass would be propped up. My legs are spread as Mr. Smith and my girlfriend take one foot and tie it to the bed frame. My head is buried in the sheets until I feel my hair getting tied then pulled back, I see up to six cocks in front of me. Mr. Smith ties a rope around my hair and then to the bedframe keeping my head up.

Last are my arms which get tied to the sides of the bed, I wiggle a bit to see where I'm loose. Mr. Smith ties more rope around my thighs and to the sides of the bed. I wiggle again this time unable to move much at all. "Are you ready?" my girlfriend asks.

"I'm ready."

Mr. Smith gives the rundown, "Alright everyone, just as the message stated, no limit on how many use him at once, but please be respectful of those that want it to be one one-on-one." He points to one of the men in the front. "You were the first to reply to our ad, therefore you will be the first cock he takes in his ass. Once he's acclimated then we will allow another to join, then another.

The man wastes no time in getting on the bed right behind me. He grabs his hips and tries pulling my ass towards him. He lifts my skirt and pulls my panties down. I tighten up a bit until I feel him tapping it in, I let out a moan as it goes in deeper, and he slaps my ass telling me to take it like a good girl. I try to relax and let it happen, he starts to go deeper until I feel his balls slap on my ass. I'm moaning and see the men in front of me jerking off. The man inside me starts to fuck me and pound me my head bobbing back and forth.

Mr. Smith looks at another man and nods his head. This man jerking off comes towards me and puts his cock in my mouth and face fucks me. I try to bob my head up and down to the rhythm of being fucked. While being used I feel hands all over my back and someone feeling up my legs and thighs.

My body is at the mercy of these men, just when the cock in my mouth comes out another replaces it this one already twitching. Within seconds it cums down my throat, the man fucking my ass keeps going. He pulls out for a second, then shoves it back in harder. I cry out but gag as another cock goes in my mouth. I feel the cock in my ass start to twitch then the man's whole body weight collapse on top of me as I feel him cum deep inside me.

The men start to get loud telling him to get off as they want a turn. They get off not before slapping my ass. Another man climbs onto the bed this time I feel a finger in my ass, he pushes deeper until he touches my spot. I instantly moan loudly and start to cum, my drive starts to disappear, but it doesn't matter as he shoves his cock in my ass, I feel him grab the rope attached to my hair and pull. The man fucking my mouth goes deeper and I gag on it.

I feel completely helpless, the fucking continues, and two men push their cocks in my mouth as I struggle to take them. My lips are cracking as I try to open wide enough for both, a feel warm cum being shot onto my back from all directions then more right on my ass. The two cocks pull out of my mouth and cum on my face. I feel cum all over my body now, some of it dried up. As I breathe in and out heavily still getting pounded from behind. I look up and see most of the men leaving, except for Mr. Smith. He stands there watching me get fucked while he holds a tablet in his hand.

"Need a break yet?" he chuckles looking past me and at the man using my ass.

He laughs and stops with his cock deep inside me, I let out a groan in pain. "Oh no, I can go for hours." He slaps my ass and leans his body on top of me, I feel disgusted as I feel his sweat on me. Mr. Smith just laughs and starts setting up a pop-up table in front of my face while I endure the fucking for longer. As he finished getting things set up the screen went from black to a live video of the living room I was in earlier.

I see my girlfriend locked in the pillory completely nude. My eyes widen, Mr. Smith notices and smiles down at me. He covers the screen as he stands right in front of me with his cock hard. "Need it nice and lubed up for someone." He says while getting my mouth open and forcing it in. As he pushes in and out of my mouth, I catch glimpses of the screen showing my girlfriend surrounded by men standing by her. I suck on his cock and accidentally bite down as the man fucking me lunges so hard, I feel the pain radiate throughout my body and I let out a cry.

Mr. Smith violently pulls out and slaps my face then grabs a ball gag and tightens it around my face. He gives me another slap before going on into the living room, I watch as the man fucking me starts to let up. Mr. Smith enters the frame and wastes no time mounting my girlfriend, he thrusts into her and the men watching start to jerk off, while others gasp as he starts shaking the pillory while fucking her.

As my focus shifts from the man fucking me to what's on the screen the man gets off me and turns off the tablet, then shits the bedroom door, he takes the gag out my mouth but lets it hang around my neck. "Listen, sissy, I'm the only thing that matters right now. You're gonna enjoy this and participate understood?" he says while pinching my cheek. I nod in agreement, and he returns to top me.

I let out a moan as I feel him insert his cock back inside me, I feel him start to gather a rhythm as he pounds me. I moan in pleasure to please him, he grabs a fistful of my hair, and he keeps going for what feels like hours until I feel his cock finally start to twitch but he pulls out and jumps off me. With the room quiet now, I hear my girlfriend moaning assuming she's still being used. The man walks back over to the table and turns the tablet back on.

The camera has shifted to a new angle pointed where I see the side of my girlfriend instead of behind her where I see her being fucked by a dildo strapped to a fucking machine. Suddenly I feel the rope around my right leg loosen, then my right hand. I see the man untying me and freeing me from my bondage. His cock is significantly less hard but still big, he instructs me to sit up, and I do so. He lays on the bed with his legs spread and points at his cock.

I immediately get between his two legs and start sucking, I feel it getting harder the deeper I go. Eventually, I lay on my stomach with my face right in front of his cock while I take it and look up at him. I pull out then jerk him with my right hand then go back to sucking, this process continues, until as I start sucking him again, he grabs hold of the back of my head to keep me on his cock.

By this point I'm used to it and don't gag, I let him control me as he pushes up and down at his own pace occasionally stopping when his cock is deep down my throat. I try to push away but he's too strong and keeps me down. Until I start to choke, he lifts me allowing me to breathe before pushing me down again. He continues this until he lifts my head and flips me, so my back is on the bed, and he sits on top of me with his cock right in my face.

I take it back in my mouth, he puts one hand on top of my head then face fucks me. I feel his cock start to twitch, he uses two hands this time and pushes my head onto his cock, his balls practically in my mouth. My eyes look up at him as he cums inside my mouth, I try to open my mouth to let air in.

He lets go as he finishes his load, and my head falls back, He lightly places his cock over my lips as more cum shoots out and gets on my face.

"Good girl." He says as gets off me and then lays next to me, his hand navigating to my thighs and groping them. I just lay there exhausted breathing in and out trying to catch my breath. He caresses my face and keeps calling me a "good girl." His hands reach under my skirt, and he pulls off my panty that is barely hanging on. I feel him hold my caged cock in his hand while his other one gropes my body.

I start to calm down, feeling very exhausted. But the feeling goes away as I hear the door knock and open, it's Mr. Smith. "Finally finished?" he laughs, entering the room.

"Yes, she took it very well, I know I'll want to come again." The man replies giving my balls a little squeeze. He thanks me for my time gets off the bed and thanks Mr. Smith for the time as well, just as they both exit the room Mr. Smith orders me to crawl behind them. I quickly hop off the bed and crawl behind them as we go down the hallway.

I hear machine noises as we come back to the living room where I see my girlfriend still being pounded by the fucking machine. Mr. Smith walks over and turns off the machine but keeps her in the pillory. The man starts to get dressed as they chat together asking to do this again soon, then leaves.

Mr. Smith locks the door and then unlocks my girlfriend from the pillory, she shakily gets out of it and Mr. Smith helps her lay on the couch as she collects herself.

"Why don't we let her take a rest sissy? I think and I should go out." Mr. Smith says. I look up at the clock it's almost 11:00 pm. He notices I check the time, "Don't worry sissy, I know a place that's open all night. But first, let's get you in a better outfit." He says while going over to a cabinet and pulling out some clothes.

He walks over to me and hands me a navy-blue sailor uniform with a white thong, thigh-highs, and white heels. He instructs me to get strip then dressed, I take off my schoolgirl uniform and transition into the sailor uniform, I put on the thong, pull up the skirt, put on the top, slide on the thigh highs, and finish off by stepping into the high heels. Mr. Smith compliments me and leads me out to the car.

Once inside he unbuckles his pants and I get to work on his cock as he drives. I start to hear loud music outside the car and notice lots of lights shining. The driver's side window opens I move off his cock, but he pushes my head back on it. I hear an unfamiliar voice talking.

"You looking to add another for a threesome?" they ask.

"No no, I'm looking to drop off." Mr. Smith replies pulling me up off his cock. I look up and see a man peering through the window. He starts to grin. Mr. Smith continues, "fully feminized, shaven, clean, 19, and caged." The man smiles and gets an evil look.

"He won't have too much trouble finding someone to please, go ahead and drop him off here... I'll take it from here." He says.

Mr. Smith smiles back, "Alright sissy, I'll come and pick you up later. Your girlfriend--I mean my girlfriend and I are gonna relax this evening. Go ahead and join this man." He unlocks the door and pushes me out. I see flashing lights all around me, so many people walking around wearing revealing clothing. I realize I'm no different from them, the man at the window slaps my ass and a cheek.

"When do you wanna pick up?" he asks.

"I'll come by tomorrow." Mr. Smith replies, he waves at me and wishes me good luck then drives off.

The man holding my ass grabs my chin to make me look at him. "Aren't you a sexy little slut huh?" he pushes me to my knees and reveals his cock. "Suck it!" he shouts, and I take it in my mouth willingly, my head bobs up and down on it. I notice a crowd start to form around us, I feel so turned on and use both hands on his cock. People start gawking and the humiliation sets in, I'm dressed like a slut willingly taking this man's cock while people watch me.

The reality of my situation sets in, I'm no longer a man, I never was. I'm a sissy whose purpose in life is to please real men.