I know this is more than overdue but I had been super busy for a while and didn't find myself enjoying writing, so I took an extended break. Thank you so much to the people who have been asking about the story, and I'm sorry for making you wait so long but I appreciate anyone who reads this and enjoys it.
The next several weeks went by in a blur with the chaos of a new routine adding to my sense of well-earned exhaustion. It was now simply a habit to wake in the morning, step into a pair of snug panties and fasten a bra on my chest before dressing in the only men's clothing I left; several pairs of jeans and a small selection of plain colored t-shirts. What used to be comfortable clothing now felt loose and irritating and I often found myself waiting to get home and into my new, proper attire. I was getting quicker at applying makeup, but still an amateur at actually using it properly to accent the features I wanted. Upon my arrival at home, if Derek was there my first order of business was typically to fetch him a beer and get on my knees to suck him off. If he was out, I would spend my time sorting out the apartment before inevitably servicing him when he got in. I would cook all the meals, do almost all the chores, and cater to Derek's every whim. I was quite busy but would take any chance I could to curl up beside him on the couch, tranquilized by his presence. When he fucked me I felt like a volcano was bubbling inside me, ready to fill me with an eruption of warmth and passion as Derek climaxed and emptied himself into me.
Getting dressed one morning, I picked up the first bra I ever owned, the hot pink one Derek had seen me in, and put it on with a smile as I thought back to how I got into this situation. Reluctantly grabbing a white t-shirt and jeans I finished dressing and left for class. It never crossed my mind that wearing a white shirt over a bright pink bra wasn't the best wardrobe choice until I ran into Beth, one of the girls Derek used to call up for a late night booty call.
"Hey Andy!" Beth called out to me with a small wave as she hurried her steps to approach me. "I haven't seen you or Derek in ages, it feels like! How are you?"
"Oh, Beth, um – hi..." I never really talked to this girl when she was around, maybe subconsciously jealous of her having so much of Derek's attention. My words trailed off as Beth got near and I turned to face her.
"Are you okay?" She narrowed her eyes to look me over, pausing for a moment as they lowered past my face. "I don't want to trouble you, it's just that I haven't heard from Derek in a couple of weeks, has he mentioned me at all?"
I told her that both Derek and I had been giving all our time to school lately, and I didn't remember him talking about her but that I would tell him to give her a call when I saw him later.
"Well, OK... thanks Andy" She flashed me a crooked smirk and winked at me as she reached a finger out to run down my shoulder, right along the strap of my bra. The touch of her finger was electric and started my heart pounding before she took it away.
I looked down as Beth turned away to see that as my t-shirt lay against my skin, the bright pink of the bra showed through almost clear as day. There was no way what she did was a coincidence, she'd seen me wearing a bra to school and let me know it. I didn't have time to go home and change before my next class so I spent the rest of the day anxiously hoping Beth would be the only one to discover my secret. I jumped when anybody came close to me and fidgeted my way through my last classes, practically running out of the school when I was finished and hurrying home as fast as possible.
I pulled dark t-shirt on in place of the white one and went to smoke to clear my mind. It took a lot of pot to calm me down, letting the events of the day slip away as I dozed off to the TV and fell back onto the couch. The front door opening and slamming shut pulled me out of my slumber as Derek came rather loudly into the apartment. He looked at me lying on the couch, rubbing my eyes, and gave only a slight frown before he walked away into his bedroom. It didn't occur to me at first that he was unhappy to see me in my old clothes and lazing around but the fear of being outed at school had been like a splash of cold water to my face. That night, I saw Derek only very briefly as he heated up some pizza from the fridge and went back to his bedroom. I told him that Beth had been asking about him but he didn't answer and walked right past me.
Eventually my head started feeling heavier and heavier as tiredness clouded my head. I dragged myself to bed and slept uneasily through the night. I woke up to a quiet room with a fleeting hope that the previous day had just been a surreal dream but this feeling was shattered as the striking pink of the offending bra caught my eye and screamed at me from the floor where I'd left it. Kicking it across the room, I decided to forgo a bra today but as I had only women's underwear I pulled on a pair of dull gray panties and the darkest, baggiest clothes I had.
After a couple hours at school I had forgotten about the scare of the previous day and went about my business free of distraction. I got back home and found Derek sitting on the couch, turning to look at me as I set my things down.
"Hey, bitch, you forget something?" The sudden harshness of his voice startled me, and I flinched before freezing in place. I knew he was angry.
"Look, Derek..." I began to speak feebly, but Derek cut me off.
"Shut up and strip, you pathetic little slut!" He rose from the couch and took a step in my direction.
I slowly took my shoes, socks, and pants off but stalled before pulling off my shirt, knowing I had no bra on underneath it.
"Let's go, we're almost there" the tone in Derek's voice told me I had better listen to him so I pulled the shirt over my head and waited for his reaction. "You seem to be missing something, is it so hard to get properly dressed in the morning?"
"No, it's not that it's just that I was thinking that maybe I should go back to wearing all my old stuff to school. I almost got caught yesterd-"
"What?!" again interrupting me, Derek took another several steps towards me. "What makes you think this is your decision? I'm the one who paid for all that shit and besides, it's clear that you love it. You made a promise which you broke and you have to pay for that. Get on your hand and knees on the couch."
Wordlessly, I moved past Derek and got into position on the couch. He stood at my side, pulling the panties down my legs to bare my ass cheeks. His hand gently slid over my ass and caressed each cheek individually with a firm squeeze and a jiggle. Just as I let my guard down, he pulled his hand back and brought it down hard and sharp against my ass causing me to yelp in pain.
SLAP
SLAP
SLAP Again and again he spanked my now red and stinging ass, reducing me to a whimpering mess before him. I pleaded for him to stop but as my words had no effect, I gave myself up to the involuntary gasps and cries that jumped from my lips. When he finally stopped, I turned my head to look up at him. Derek gazed upon me with a slight look of disgust and turned his back to leave me lying there.
It was almost an hour before I mustered up the willpower to get off the couch and stumble to the bathroom. Derek burst from his room and blocked my path, holding a bag at his side.
"Now that the first part of your punishment is over, time for the real discipline."
I wasn't sure what he meant and would get no more explanation as Derek shoved the bag into my hands and pushed me into the bathroom before disappearing once more into his own bedroom. My mind was racing and the fact that Derek had more punishment in store for me scared me. I gingerly down on the toilet, my ass raw and sensitive but soothed by the coolness of the seat and opened the bag. When I pulled the opaque pink chastity cage from the bag, denial filled my head. I had loved just about every minute of being his personal sex slave, his girl, but finished most nights masturbating furiously in my own room after Derek was done with me and the thought of locking my penis in this device was more than I could handle. The fact that there didn't seem to be a key in the bag didn't help. Sitting there in the bathroom, my ass burning, I convinced myself that this would be for the best, carefully fitted the cage around my dick, and locked it shut, the snap of the lock ringing loud in my head. Derek didn't respond to my soft knocks on his door so I went to sleep, idly playing with the newest pink accessory in my life.
Derek's treatment had worked it purpose to great effect and upon waking, I dressed in my bra and panties without hesitation. Normally I would be slipping the tight panties over my morning wood, but the cage prevented that, leaving only a small bulge in the front of my panties. I smiled at the look of it, from the right angle you wouldn't even have thought I had a dick between my legs at all. It took me a day or two to fully adjust to the cage but I hardly noticed it soon enough. I was worried about using the bathroom but I just had to sit down and let it go. I wasn't getting hard anymore but any time I got aroused I would leak more precum than ever before. And that happened a lot...
Just a few days after Derek gave me the cage he finally broke his recent silence, telling me that Beth was coming over that night and he wanted the place to be clean for her. Him talking to me was enough to make my dick twitch at this point so of course I quickly agreed to everything Derek said, hoping for some approval but he very quickly turned and left for school. He didn't seem cold or angry anymore but simply distant.
I spent my most of my day cleaning up, not knowing what to do or expect for later on when Beth arrived. I nervously thought about if I should leave the apartment for the night, or go hide in my room. It wasn't so much her telling Derek what she'd seen, but what he might tell her that scared me. I didn't know if I could trust Beth and this meant that my secret identity could be revealed to everybody.
Derek and Beth surprised me, entering while I was in the kitchen. I had no choice but to face them and nodded quietly to the pair as I slipped past to my bedroom. I heard them chuckling quietly but didn't care, closing my door against the world for the night.
I tried to sleep but was woken up by the rhythmic moans of pleasure flowing from Beth's lungs through the walls into my room. I knew the walls were thin, but I didn't remember her being this loud when Derek brought her over before. She sounded breathless and elated and I knew just how she was feeling. I knew how easily Derek could manhandle me and I was picturing him tossing Beth's 5' frame around like a doll. It wasn't long before I slipped a finger into the front of my panties and I felt the now familiar wetness in my crotch when I got turned on. Tasting the sweet precum only excited me more, listening through the wall to hear Beth getting what I was so thirsty for. Derek soon became more vocal and after a few minutes must have come because I heard a growling moan followed by silence until I gave up and crawled back to bed. I dreamed that night that I was the one with Derek in the room next door, him fucking my pussy in every position conceivable. My tits bouncing as he pounded me harder and harder until we came and fell asleep in each other's arms. Waking up to my flat chest and locked cage was disappointing but my panties were soaked and sticky enough to tell me I enjoyed the fantasy enough for now.
This became a near daily habit at the apartment. I would clean while Derek was out and then took shelter in my room to listen to him fucking Beth until I fell asleep. My sexual frustration was hitting a peak and every night I sat by listening to Beth be in what should be my position made it worse. I began to listen while slowly and quietly riding my dildo, my eyes closed and biting my lip. Having no access to my dick, it was extremely overwhelming how I felt the sensation of being fucked so differently now. The focus of pleasure was purely inside my body and every time the dildo touched my prostate, I felt shivers of bliss explode from within me. It was nearly a spiritual moment the first time I 'came' this way, not ejaculating but feeling a definite climax of pleasure that absolutely floored me and yet still left me immediately wanting and ready for more, unlike a normal orgasm.
After the first purely anal orgasm of my life, I was hooked. I learned quickly how to get one after another and have multiple orgasms in a row just like a girl. Derek was still avoiding anything but minimal contact with me and daydreaming about my nighttime sessions was the only thing getting me through the day with any dignity I had left intact. Although the thought crossed my mind, I couldn't bring myself to actually find another guy to give me what I needed.
It wasn't until many days later that, while I was washing dishes in the kitchen, Derek showed up at the apartment alone. I had grown accustomed to Beth being with him every minute of the day and so tried to avoid looking towards the door when I heard Derek enter. Only when I heard his voice behind me did I realize something was different from the routine.
"Having fun?"
I whipped my head around, unused to hearing Derek speak to me at the apartment. I saw that he was alone.
"Um, hah, I guess so? Where's Beth?" I answered him.
"Take your pants off," Derek ignored my question and spoke with authority. "I want to make sure you've been following the rules."
I stripped to my bra and panties, standing meekly before Derek as he looked me over with a smirk.
"I only asked for the pants, but whatever you want. I have to say, the cage was planned to be a punishment and I really expected you to be begging for the key days ago. Seems like you've just forgotten your dick entirely, haven't you?"
Looking down, I knew he was right but still felt humiliated as my mind flashed with images of my recent nights locked up, riding the dildo to orgasm. "I just... didn't want to make you mad again."
"I'll take that as a 'yes'."
I felt my face flush red and couldn't voice a response. Derek laughed at me on his way over to the couch in the living room where he sat and looked back at me expectantly. I followed up and stood before him as he sat until it was obvious he wanted me on my knees. A quick glance between me and his crotch was all I needed to extend a hand to unzip his pants and pull them out from underneath him. Even seeing the barely erect outline of his dick inside his briefs had me salivating, it had been much too long since I had so much as seen Derek's perfect cock that I was about to do anything he asked. While on one hand I wanted to savor this moment and let it last, I couldn't resist reaching into his underwear and fishing out his cock. It had barely touched open air before I dove on it, licking the entire length and tasting the musk of his manhood. It didn't take long before I had a rock hard dick in my hands and mouth, losing myself in the moment and worshiping Derek as best I could. My tongue swirled around the mushroom head and I tasted his precum which only pushed me further. I took him as deep in my throat as I could before kissing his dick all over, working my way to the base. Sucking his balls into my mouth, I flicked my tongue against his sack as I pulled his briefs under his ass and down his legs. I ran my hands up and down his hairy thighs and took a moment to catch my breath while I looked up to see him looking down at me. He smiled at me but grabbed the back of my head and pushed me back to his cock. I continued giving him the full treatment, ignoring the growing ache in my jaw until he stopped me a few minutes later.
"Go back to my balls, keep them in your mouth," Derek instructed me. "I'm going to cum soon."
I did as told and opened my mouth to accommodate his heavy balls and went back to giving them full treatment with my tongue. He grabbed hold of his dick and stroked it until he began to grunt with every other stroke. I knew he was about to unload and sure enough he became louder and his balls tightened in my mouth before I felt his warm cum splashing onto my face. I continued sucking his balls until he was finished, his load covering the side of my face and dripping down to my chin and neck. Derek told me to lick him clean, which I did, and then told me to bring him a drink in his room. He tucked his dick away and left me on my knees on the floor.
I fetched him a beer and just about ran to Derek's room. He was sitting naked on the edge of his bed and again pointed between his feet. I handed him the beer and assumed my position. He grabbed his now limp dick at the base and shook it a couple times while taking a drink from the bottle. I began sucking him again, taking his dick into my throat until I was gagging and drooling like a maniac. I was just getting in to the blowjob when he put his hands firmly on my head behind the ears and stood me up. He pulled me close to the bed which elicited a surprised gasp from me which seemed to turn him on. Kneading my ass, he spanked me a couple times before rising to his feet and pushing me down on my stomach on the bed with my ass exposed and my legs hanging down. Was he finally going to fuck me? I needed it so bad I couldn't think of anything else and my dick was throbbing inside the cage, precum gushing out by the second. I heard him go to his closet where his dresser was and when he came back, the snapping lid of the bottle of lube before he stuck a couple fingers into my ass without warning. This was by no means too much for me. At this point my hole was able to accommodate almost everything I shoved in there but the fact that it was finally Derek penetrating me made me jump and gasp loudly. Derek snickered, and slowly worked his fingers in and out, twisting them around and prepping my hole for what I hoped was a great fuck. I closed my eyes and enjoyed myself being stretched out and sighed when he finally pulled his fingers from my ass. I heard him go back to the closet but just lay on the bed in wait for whatever he had in mind.
"You've been waiting for this haven't you?" Derek asked from behind and above me. I felt the head of his cock rubbing around and over my hole, toying with me.
"Yes, please, Derek fuck me!" I grabbed my ass cheeks and pulled them apart, giving him no reason not to shove into me right then and there.
"Well, I'll fuck you but I don't know about calling me Derek..." While the voice I heard was familiar, I was expecting to hear Derek's voice and the high pitched feminine voice caught me off guard.
I whipped my head around to see Beth standing behind me with what looked like my own 8" dildo in a harness around her waist. She was waving it by the base and looking down at me with a twisted, conquering smile on her lips. My heart fluttered as my mind raced over what was happening. Derek must have had her hiding in his closet while he worked me up and had me begging for his dick. Beth had caught me wearing a bra but I was not expecting anybody other than Derek to see me like this and I had no idea what to do. I must have looked nervous as Derek leaning in over Beth's shoulder to comfort me.
"Relax, Brandy. Beth knows everything about you. She thought she freaked you out at school the other day and just wanted to make it up to you with some quality girls' time." Derek reached forward and grabbed the dildo, pushing it towards my asshole.
"Yeah, don't worry babe, I'll give you what you need! I've always wanted to do this!" Beth said excitedly as she slapped Derek's hand away and grabbed hold of the dildo herself.
I had nothing to say and just buried my head in the sheets of Derek's bed. I heard him whispering and encouraging Beth as I felt the dildo poking at my hole. She worked the head in and slowly pushed forward, giggling at whatever Derek was telling her. Suddenly, I heard him tell her to go faster and she rammed the rest of her 'cock' into me. Her hips touched my ass when she bottomed out and let it sit for a moment. I looked back cautiously over my shoulder to see Derek turning on the vibration in the dildo and both Beth and I reacted instantly. I let out a loud moan while Beth bit her lip and let out an adorable squeak as the vibrations hammered on her clit. Derek placed his hands on Beth's waist and started guiding her in and out. It wasn't long before she was all in and began fucking me with an intensity I was not expecting. She placed a hand around the front of my throat and pulled my head up and towards her, making me arch my back as much as I could while she pounded me. Derek, not needed where he was, came around and sat on the bed beside me. Beth let go of my throat and pushed my face to Derek's hard and glistening cock. I was like a machine doing what I was told as these two took complete control of me and swallowed Derek's dick down my throat.
"That's so fucking hot, is he as good at this as he looks?" Beth exclaimed as she watched me going down on Derek.
"Beth, HER name is Brandy," He corrected her. "But yeah, she knows her way around a dick."
"Oh – you're right! Sorry Brandy, I won't forget it again."
This time I couldn't have answered her even if I wanted to, with Derek shoving himself in and out of my throat while Beth did the same to my ass. I was in heaven and felt almost numb to anything but the two cocks thrusting into me from either end in alternating rhythm. Every time one of them pushed into me I felt an electrifying burst of pleasure inside me which only got more and more intense the longer they kept going. I had no idea how much time passed but it didn't feel like long until I felt the warmth spreading from my prostate before my little limp dick twitched in it's cage and let out an almost unending gush of cum. I was involuntarily moaning around Derek's cock as the orgasm washed over me and it must have felt good for him since he started shoving me down until my nose was pressed against his bristly short pubic hair. Just when I was expecting him to cum from me sucking him off for the second time that day, he pulled me back and I was suddenly only connected to him by the gooey strands of saliva and precum that stretched between my lips and his dick. I looked up to him but he was busy watching Beth who was as engrossed in fucking my ass as I was in sucking Derek. He pushed my head to the side and stood up, grabbing Beth around the stomach with both arms and pulling her off me. She first gasped, then giggled, and finally whistled at me when Derek set her down on her feet.
"My turn. Brandy already finished me with her mouth like a good slut before I came in here and I think we both want me to finish in her ass." Derek announced authoritatively.
Beth sat on the bed where Derek had been sitting and similarly took a hold of my head and shoved it into her sopping wet pussy. I only had a couple seconds to process the fact that I was now eating pussy before Derek rocked my world by thrusting balls-deep into me in one thrust. While Beth had enthusiasm when she fucked me, Derek had the experience and strength to put me over the edge. I came for a second time almost instantly after he entered me and must have annoyed Beth with my lack of focus on her as she grabbed my ears and pulled me into her, my face being pushed into her crotch every time Derek pounded into me. I did my best but she quickly took over and ground her pussy over my mouth and nose, adding her own juices to the cocktail of bodily fluids coating my face.
Derek's pace slowed and I knew he was close to busting his load in me. The excitement I felt at that thought felt nearly as good as when I had cum with his dick in my ass. He grunted loudly and I could feel his cock pumping into me and knew that he was breeding my hole. Beth was entranced as I sucked her clit like a tiny cock in hopes of making her cum at the same time. I didn't quite succeed but not long after Derek pulled out of my well-used hole Beth started breathing fast and shallow while pushing my face into her harder than ever. She finally squealed and yelled as she came, and we both collapsed onto Derek's bed in a post-coitus haze. I looked to Derek standing over us and gazing on his two little sluts lying before him. He grinned widely, not saying anything to us before he left the room and we heard the shower turn on.
"So baby, did I rock your world?" Beth asked, pinching my ass with a giggle.
"You... were pretty damn good at that, I have to say." I rolled my head to look into her face and started giggling alongside her.
"It's something I've wanted to do for a long time. I'm happy Derek found me a girl to play with. And I have more in mind for you than just fucking you. We're going to have a lot of fun."
"What more?" I was beyond the point of being nervous and simply resigned myself to whatever Beth or Derek wanted of me.
"Now don't get me wrong, you're a sexy little cumslut when you've got dick on the brain, but you've only been a girl for what, a couple months?"
I nodded, thinking I knew what she was getting at but not quite sure.
"Right. So I'm going to try and jam my years of experience into some lessons for you. Makeup, clothes, and keeping your cute little body fuckable at all times are going to be our top priorities but you need to learn so much more. You might make a good little slut for Derek, but when I'm done with you you'll be as close to a girl as you can be with that tiny excuse for a penis between your legs."
"Please, Beth, I want nothing more than that!" I pleaded, my eyes nearly tearing up with anticipation and gratitude as I imagined the work Beth could do with a malleable lump of clay like myself.
Beth laughed and lay beside me, raking her nails lightly through my hair as we cuddled and waited for Derek to come back. He was pleased to find us getting along so well and sat himself down at the foot of the bed. After a few wordless minutes, he pulled Beth up beside him.
"Thanks for your help with this, Beth. Brandy and I are both thankful for it – even if she can't express it right now" Derek said candidly.
"Oh, stop. You say that like I got nothing out of this. She's a great fuck and I'm going to have just as much fun dolling her up and making her into a real girl for us to play with."
They kept talking romantically about the plans they envisioned for me while I lay subdued on the bed listening and wishing it would all come true. Eventually they both lay beside me and we all succumbed to sleep in a warm tangle of bodies, me in the middle of the two people who were going to transform my life.