Archive of Our Own ^beta

"What the hell are you doing in my room?" I had just gotten home and grabbed a drink before noticing the door to my room was ajar. Jenna was sitting on my bed, a blush on her face like she'd been caught red-handed.

"Is that any way to greet your big sis?" She said, quickly finding her composure after straightening my bed up.
"Hello Jenna, now why the fuck are you in my room?"

"So the thing is, I needed some batteries so Mom said to swing by. She thought you had them in your room."

"Well I don't. Now if you don't mind, I'd like some privacy, I'm beat from practice and just want to lay down."

"Okay, okay, I'll go. But first, there's something we need to talk about."
She was usually annoying but she really was testing my patience today. "Spit it out then," I said, taking a seat on the bed next to her.

"I know I shouldn't have, but I was rummaging around and found this." She pulled a dildo out from beneath my pillow and my eyes went wide with horror.

"I-it's not what you think! I'm holding it for my girlfriend!" I said in a panic.

"Cut the crap Tommy, I checked your laptop too. There was gay porn on there and I know Mom's never met this 'girlfriend' before. Just be honest with me, are you gay?"

I racked my brain trying to think of an excuse, but I was almost on the verge of tears. "Fine! I'm gay, are you happy now? Please... just don't tell mom and dad... They'll be so pissed!"

She could tell I was shaken and she pulled me in for a hug."Hey, calm down, let's talk about this." I sniffed a little and nodded.

"So how long have you thought you might be gay?" she asked. I told her it had been a few years now, ever since junior high. "And you've never done anything with a girl?"

"No, never. I've always felt awkward around them and they never turned me on or anything... One asked me out once, but I turned her down."

"It's normal to feel a bit awkward around girls at first," she comforted. "But how do you know you're gay if you've never been with a woman romantically?"

"Uh, I don't know? Everyone online says it doesn't work that way, that you just know."

"Well who are you going to listen to, randos online or your sister?" She had a point, she's always had my best interests at heart. "I'll tell you a secret. There was a time I thought I was into girls too since a lot of my high school friends were, but turns out I was just confused and wanted to feel accepted by them."

I was shocked, she'd never told me this before. "Really?"

"Yup! But then I got drunk one night and fooled around with a guy and it cleared up in an instant. Have you ever thought about trying to be with a girl?"

"I mean, sure. What gay guy hasn't thought about what it'd be like to be... normal..."

"See? That's what I'm worried about. Life can be harder for gays and lesbians, and you can miss out on some wonderful things in life. And that's not even mentioning the health concerns with that lifestyle. I just want you to be sure."

"Yeah, don't I know it... I've been so nervous trying to hide it for so long. I know it's nothing to be ashamed of, but dad wouldn't approve, so I've just been coasting." Confiding to her felt so freeing in the moment.

"Then do you want to give it a try? Being with a girl, I mean."

"I don't know... I wouldn't even know how to begin. Besides, I'm pretty sure I'm hella gay," I said, lifting up the dildo with a laugh.

She laughed too. "You never know until you do. Tell you what, I have an idea that could help."

I was curious, "What did you have in mind?"

"Well, the 'rents are going on their European vacay all summer, so I'll stay here and put you through a little bootcamp of sorts while they're gone."

"A bootcamp?," I chuckled. "So like training or something?"

"Yeah, something like that. Think of it like straight lessons and exposure therapy. But it might get pretty extreme, so you need to be absolutely sure you want to do this and you'll have to do exactly what I say all summer. Do that and I'll let the whole issue slide."

"Haha, you're kinda scaring me sis..." Whatever she had in mind, it sounded rough.

"I just need you to know how serious a decision it is. If you want to be straight, to be normal, then you're going to have to put in the effort and let me manage every aspect of your life. If you back out after agreeing, you'll have to tell mom and dad too. They deserve to know."

A chance to be normal? Everyone says being gay is normal, but sometimes it's just so hard it makes me wonder... Is it worth giving up how I've come to know myself to not have to deal with the stress anymore? Regardless of that wish, I didn't think anything would change.
"What about your husband? Won't he get mad with you staying gone all summer? And what if it doesn't work and I'm just that gay?"

"Pshh, he's been so obsessed with trying to get a promotion he won't even notice me gone. Worst comes to worst, you're still gay we get to spend another summer together. And if you follow what I say and nothing changes, I won't even mention anything to mom and dad. I'll even back up your fake girlfriend story, haha."

I thought in silence for a few moments before speaking up. "Okay... Do your worst. What could happen, right?"
"Well, I could forcibly drain the gay right out of you," she teased.
"Haha, knock it off, I said alright already."

"Great! Pinky promise me and I'll make you a real man this summer!"
We pinky promised like we used to do as kids, but I didn't know at the time how much of an impact it would have on my life...

-----
A few days later...

"Alright, now strip," my sister commanded.

"Huh? What do you mean?" Our parents had just left a couple hours ago on their way to the airport and I was relaxing in my room when Jenna called me out to the living room.

"You know what strip means. Now get to it, and that includes your boxers." Her tone was harsh and authoritative.

"I'm not stripping in front of my sister! Why would you need me to do that?" She hadn't seen me naked since we were kids, no way that was gonna change now.

She sighed. "Listen, you said you'd follow my instructions to the T. I need to assess your body if I'm going to make a lesson plan for the summer. Don't wimp out on me now, I'm a scientist, it's nothing I haven't seen before."

I begrudgingly grumbled and swore under my breath, but relented and turned around to remove my clothes, covering my junk to save some face before turning around.

"You're pretty fit, could be improved but that'll do nicely. Girls don't like a fully shaved body though. Now hands to the side." I could feel her eyes scanning over every nook and cranny of my body.

"Seriously? You need to see that?"

"Duh, that's the main piece of equipment when it comes to relating with women."

I sighed and removed my hands, my embarrassment rising to my cheeks.
She moved in for a closer inspection of my crotch and I flushed. "Better than I was expecting considering what mom's said about dad."

"Ugh, gross... I didn't need to know that." I almost wanted to vomit hearing that while having a girl closer to my groin than I've ever had before.

"Kind of a waste though and small for your cocky attitude, since you're a bottom I take it? And still a virgin?" she probed.

"Hey it's above average and does what it needs to for me! But yeah, I think I'm a bottom, though I've never had more back there than my dildo and fingers."

"What about kissing or oral? Have you had a boyfriend before?" Why did she need to know all this? It was getting humiliating.

"...I kissed and blew a guy once, but it was a random thing at a party and he had a girlfriend. No boyfriend, though I am chatting up a guy. He's on the east coast checking out colleges this summer though."

"I see.. Very informative," she said giving me one last circle.

She reached into her bag and handed me a cold chunk of metal. "This should fit, but we may have to swap out as time goes on."
"What the fuck, Jenna? A chastity cage?"

"Oh, so you're familiar with it. Good, then I don't need to explain how they work," she grinned mischievously.

"Ain't no way in hell I'm wearing this! You're out of your mind. I never agreed to this!" I was furious, to think my sister would suggest something like this.

"You did actually, we pinky promised and it's for your own safety going forward. But fine, have it your way," she said, pulling out her phone afterward.

"What are you doing?"

"Calling mom. You wanna break your promise then you'll have to take the punishment and tell her you're gay."

"Jenna... wait! Let's talk about this!" I had completely forgotten my nudity at this point.

The call connected. "Hey mom, Tommy has something he wants to tell you," and then she tossed me the phone.

Panicked, I tried to think on my feet. "Uh, hey mom... I just wanted to say I hope you have a good trip and see if you got to the airport okay. Oh, you did? That's good, hope it goes well. Ok, that's all I wanted, I'll let you go now. Mhhm, love you too. Bye."

I sighed in relief. "So you changed your mind?" Jenna asked.

"God you can be a real bitch sometimes... I can't believe you did that."

"That's what big sisters are for. Now get it together or next time I'll tell her myself."

"Fine..." I resigned myself to her control and fumbled my way through locking up my dick. The steel felt cold and the heft tugged on my junk in an odd manner.

"See? That didn't hurt, did it? Good boy, Tommy." I scowled, her remarks almost biting into my skin like the cage did.

"Whatever, just get on with it."

"You really need to learn how to speak to women, boy. But that will come in time. To start with, here are some rules for the summer."

"Okay..."

"First, when at home, you are to be naked or wearing a jockstrap at all times. I've taken the liberty of replacing all your boxers with them as it'll help support the cage."

"All the time? What's the purpose in that?"

"You need to get comfortable with a woman viewing your body. As a woman myself, that's a huge factor in attraction to men and a man needs to be proud of his body and its ability to turn on a woman."
"Whatever I guess... Just sounds emasculating to me," I scoffed.

"Second, I've confiscated your laptop and locked most features on your phone except for calling select numbers and you'll be tracked with it. I took the liberty of texting your boytoy that you'd be going on the trip with mom and dad and most likely won't be able to respond. We can't have anything interfering with your progress."

"So I'm basically your slave for the summer? Fucking great..."
She tittered, "Basically. By the way, about how often to you usually masturbate?"

"Uhh, once a day I guess?" I was slowly becoming numb to her invasion into my private life.

"Well say goodbye to that. Rule three, you'll be practicing restraint. A cage shall be worn at all times and all ejaculations are to be allowed by me and only me."

"Are you insane? I'm a teenage boy! Jerking off is what we do, you can't take that away from me!"

"Well too bad, you're already locked up nice and tight. A real man can exercise patience and this will help you direct energy outward toward women instead of inward to self-gratification. Besides, you can come to me if you're feeling pent up, but it's up to me if I let you out or not."

"Argh! ...fine, whatever. It's your fault if I die of blue balls though."

"Trust me, you won't, haha. Fourth rule, supplementary tools. Here's a voice recorder. I'll be giving you affirmations for you to record yourself saying that you'll play back at night for subliminal reinforcement. On top of that, you'll be taking these." She fished out a bottle and handed them to me.

"What are these?" I asked rolling the labelless bottle in my hand.

"Something from the pharma department at my work I've been itching to try out in humans, they're still experimental but safe. Dosage may change over time, but you'll start at one in the morning and one before bed. They're to help keep your body primed and receptive to change, in layman's terms."

"So I'm a guinea pig too now? Lucky me..." By now I didn't even care, I just wanted to put the day behind me and go to bed.

"I guess so, you'll be helping me kill two birds with one stone now. Well, that's all the big rules anyway. I'll be adjusting them as I see fit, so just do what I say and follow my lessons and the summer will just fly by. Any questions?"

"No, not that I think it matters if I did." The ramifications of my promise were just starting to hit me. What had I gotten myself into?

She leaned over and hugged my naked body tight. "Trust me, Tommy, this may be hard but it's what's best for you. I love you."

"Sure... I love you too..."

-------
Day 7
Dose: 2 pills
Affirmation: Women are attracted to my body. It's normal to be confident in my body and want to respond to female adoration.

The first few days were fairly normal outside of the nudity. I'd do chores, watch TV, and even eat dinner with Jenna in just a jockstrap. She didn't even mention it so what embarrassment I felt at first was quickly melting away into normality with us bickering like siblings do from time to time. I'd gotten used to the cage for the most part, outside of the pain I'd get when an erection would start to stir but be stymied by the cold steel. Mornings were extra painful. She was right about the jockstraps helping with support, but I was still constantly aware of it.

Jenna and I spent a lot of time together at first, just like the old days laughing and watching whatever movie was on. But I'd noticed that since this started, Jenna has been more physical with me than before. A touch on the shoulder, a lingering hand on my lower back almost grazing my buttocks. Being aware of it now, I realized that girls had done similar things to me in the past as some sort of signal and it didn't even register. Jenna's touch however didn't repulse me, I guess since she's family.
Not jerking off has been the hardest part. The seel made it impossible to get hard let alone stimulate any of it. I tried fingering myself in the shower as it was the only place I didn't have eyes on me, but it just made my dick hurt when it engorged. I don't know how those gay guys get off wearing a cage like I'd seen online. Also, I'm not sure if it's those pills or what, but since starting bootcamp I'd wake up with strings of precum smattered in my jock, something that never usually happened to me before. Thankfully she bought a lot of them so I could change before she could see any tiny stains in the morning.

I managed three or four days without cumming fairly easily, but as the weekend neared, my crotch started thrumming with need. I'd find myself grinding against the bed when I awoke and I blamed it on not having abstained this long in years. I struggled with my pride, but eventually, I broke down and went to Jenna.

That evening, Jenna was reading a book on the couch when I approached her. "Hey, uh, you got a minute?"

"Sure, Tommy, what's up?" She closed her book and took off her glasses.

"This is kinda awkward... I'm not sure how to say it."

"Speak up, if a man wants something he should ask for it." She looked at me expectantly.

"Right... So, uh, you said before that if I was having... trouble, that I should come to you?"

A grin spread across her face. "What kind of trouble?"

"Ugh, don't make me say it..." I could tell she was toying with me.

"Well I have noticed you've been a bit fidgety the past couple of days, but you still need to tell me what you want."

All I could think about was getting some relief, my mind entirely focused on my dick. "Fuck! Fine, please, Jenna... It's been a week, I can't stand it anymore, I need to get off."

"Aw, you poor thing, that wasn't so hard, was it? I suppose it's time for your first lesson then."

"What do you mean? Just let me out of the cage so I can jerk off, please..." I stood there confused, humiliated I had to just ask my sister for permission to beat my meat.

"Don't worry, you'll get your release, but you won't be touching yourself." I watched silently as she undid her blouse and right after, her bra, leaving her pale tits open in the air, the key to my cage dangling over her cleavage.

"What are you-" I was stopped mid-sentence as she grabbed my hand and guided it to her breast. I stayed silent, my mind in a mild fog, as my hand touched the bouncy flesh of a boob for the first time in my life.
"Today you're going to learn about breasts. They're the first thing you notice on a woman and they're very effective erogenous zones as well. Go on, try rubbing them."

Too stunned to realize I was pawing my own sister's tits, I did as she asked, massaging it with my hand.

"Don't be afraid to play with the nipple either. And use both hands."
I did what she asked and started to explore her chest with both my hands. "But what about the cage..."

"Shhh... We'll get there. Just explore for now. Tell me how it feels."

"It's... not as bad as I imagined. They feel squishy and like soft skin."

"So you're not grossed out?" she probed.

"No, not really. I'd always heard gay guys say they're gross, but they just feel.. normal?" I moved to a nipple and tugged it a bit, making her gasp inaudibly.

"That's right. They're just a normal body part, just like guys have. Well, maybe not just like guys, since they're fun in their own way, haha."

"Yeah... I can sorta see why straight guys like them..." Deep in my mind, a part of me was yelling. Here I was doing something I'd swore I'd never do, and with my own sister, but something prevented that voice from crying out louder.

"Do you want to try something else? I'll let your pathetic, gay boyclit out of the cage if you do."

She didn't have to say another word to convince me. "Yes, please."
Jenna guided me into laying down across her lap, my head supported by the armrest. She looked down into my eyes and moved her breast to my face, offering up a nipple.

"You're a big boy, I bet you can figure out what to do," she said, petting my head gently. Without further prodding, I took her nipple into my mouth and started to suckle.

I heard her sigh in delight and a chill ran through me. "Such a good boy. See what pleasure you can get out of woman's breasts?" I nodded gently, continuing to suckle like a baby. She stroked my own chest and tweaked a nipple causing me to bite down gently on hers, eliciting a moan.

I sucked like a baby with a pacifier and started rubbing her free breast of my own volition, the rational gay part of my brain in a haze.

"Yes, just like that baby boy, keep going." She reached down to my jock and tugged it down my thighs. "My, my, look at the mess you've made!"
I glanced down and saw the inside of my jock sticky with precum, more leaking slowly from the tip of the cage. I realized my cock had been in pain, straining against the metal. I must have been leaking for a while now.

She yanked the key off her neck and slowly unlocked the cage, every throb of my cock helping to remove it. Eventually, my cock slipped from its confines and slowly rose into the bracing air, exposed and fully hard for the first time in a week. I moaned around her breast in my mouth.
"Look at that! You should be so proud, getting hard with just a woman's tit in your mouth." Her exclamation stroked my ego somewhere deep inside me. "Little gay boys don't do that, their little boyclits stay soft and useless with a girl, don't they?"

"Mmhmm" was all I could respond in agreement, my hand leaving her breast to instinctively grasp my cock. But before I could reach it, she slapped it away with a smack.

"What did I say? You don't get to touch that filthy, gay cocklet by yourself. I'm in charge of your orgasms from now on." My hand stung, but I knew better than to stop sucking and brought my hand back to her breast.
"That's more like it. Real men have to learn to focus on a woman's needs before they can take charge on their own. But you've still got a long way until you're a real man."

I pried myself from her breast, taking a breath just long enough to beg, "Jenna, please... It hurts so much..."

"See? That proves it, right now you're just a shameful little homo sucking on his sister's tits begging for your little faggot cock to get milked, always thinking of yourself."

I started to tear up. Why was she being so mean to me? I did everything she asked, so why? ...But she was right. If someone was watching us right now, they'd think I was pathetic, even I could see that. I had to do something, real men don't act like this.

My tears stopped and I dove back into her breasts, sucking like my life depended on it now. I rubbed her breasts, pushing them together and changing pressure, gently bit at her nipple and listened to her moans to see what she responded to. Now that I was paying attention, I could tell what worked and what didn't, how it felt to focus on another person and give them pleasure before myself, something I'd never done before.
"Oh god, yes! That's the right spot! Good boy, now you can get a reward." She reached down to my dick, gathering the precum that had dripped down its side and grasped it firmly in her palm. I moaned through nibbles as my dick felt the first touch of another human. Not only that, a woman, and my sister.

She stroked me quickly but gently, the sensation building faster than I'd ever experienced before. I started panting into her breasts, their size muffling my breath, but still never letting go of them.

"Yes, baby, you're doing so good! How does a girl's hand feel around your little gay cocklet?"

I mumbled, "Good... And it's a cock..."

"Aw, poor baby thinks he deserves to have it called that. Well, you will by the time I'm done with you." She squeezed my dick harder in response and I could hear the wet shlicking sounds echo through the living room with every moist stroke.

I grunted, "I'm... getting close..."

"Oh? Then keep sucking, show me deserve to cum. You want it, don't you? To empty that faggot load all over my tits?" I sucked harder in response, finding the more I played with her tits the closer to the edge I got. I was so close, moaning my pleasure louder and louder, but unfortunately, she stopped stroking right before I could cum.

"Jenna... Please! I'm right there..." I pleaded.

"Tell me what you want Tommy, you must be so pent up," she almost whispered.

"I want to cum...!" I could hear the desperation in my own voice.

"No, say it exactly how I did."

"I... want to shoot my... faggot load all over your tits..." I started to tear up again, the pleasure and shame mixing into a crescendo I hadn't ever felt before.

"Such a smart boy! Fine, but you can't cum until I tell you to. Get yourself to the point of no return on your own. I know you're falling in love with these tits, they're all you need to get off.

I whimpered, but desperate for release I went back to servicing her tits. By now they were wet with my saliva and I wouldn't doubt the neighbors could hear my suckling. She was right again though. The more I focused on her tits, the more worked up I became, my cock twitching in the air on its own as my hips started to thrust involuntarily.

It took a few more minutes, but I could feel my balls tighten as the semen rose up inside me. "Please..." was all I could manage to sputter in my teary, tit-crazed daze.

"Cum for me, Tommy! Shoot all that filthy faggot cum and don't stop until your balls are empty! Do it now!"

Her words were like popping a cork and I could feel my load rush out of my cock, unassisted by her hand. I moaned and grunted, my hips trusting as each shot left it, arcing upwards. The first rope hit me in my already tear-stained eye, another few splattered onto her tits with the rest leaving streaks across my abdomen. The short orgasm felt like minutes though, my body rapt in this totally new experience.

Eventually I caught my breath and stopped sucking, Jenna petting my head and wiping the cum and tears from my eye with a nearby tissue. "You did so well for your first lesson, Tommy. I'm so proud of you." Her words felt like a balm to the shame I'd felt, what just happened not having fully caught up to me.

"Now I need you to clean me up too." She guided me to her breast and without thinking, I started to lap up my still-warm cum from her breast. My head still muddled, I didn't stop until her breasts were spotless. When I was done, she cuddled me warmly, petting my head and whispering into my ear.

"You're such a good boy, Tommy. I love you so much. Just do what I say and we'll keep emptying all that filthy, wrong, faggot cum out of your balls, over and over again, until all the gay is gone. You'd like that, wouldn't you? To be a real, straight man?"

I didn't respond. Her warmth and love having already rocked me to sleep in her arms left Jenna to clean me up and take me to bed, but not before re-locking my cage.

------------
Day 19
Dose: 4 pills
Affirmation: Nothing is more beautiful than the female body. I enjoy the sight, touch, smell, and taste of a woman.

The day after my first experience with Jenna, I didn't leave my room. Reconciling what I knew about myself till now and the immense pleasure I had felt would take time. A part of me regretted agreeing to this inane bootcamp idea of hers. A part that wanted to run away, but I couldn't hurt my sister like that.

Eventually I came out of my room. She was putting a lot on the line to try and help me, and while I still didn't think it would work, I didn't want to disappoint her. Surely it had just been a fluke, a moment of weakness in desperation. I would be stronger going forward. I relayed my troubles to Jenna and she hugged me before increasing my pill dosage, saying that would help keep my mind off things.

It didn't though. If anything I was getting hornier even faster. Now a few days was an immense struggle to get through and I spent more time in the gym trying to vent my frustration. Good for my gains, but it did little to ease my mind. Every night I'd listen to my aspirations and sometimes toss in my sleep while every morning my jock was soaked through staining my sheets, and sometimes I had to change throughout the day as I'd start leaking out of nowhere. I had promised myself I'd gather my willpower, but I failed miserably.

Every few days, I'd swallow my pride and come to Jenna begging for release. She'd tease me about how painful my balls must feel and how only a weak homo would let his faggot dick control him. Then she might stroke me slowly while I suckled her breasts, or make me thrust against them like a horny goat in a rut, goading me to shoot all the gay away, my mind having already accepted I was fooling around with my sister.
As a gay man, I should have been repulsed by her body, let alone the verbal onslaught she'd give me, deriding my sexuality. Oddly, though, it started to turn me on, almost like I really believed with every load I might somehow get less and less gay. Preposterous.

Today I was informed I'd be getting another lesson and that we'd be going on a date. Shopping for clothes actually, since she noticed I was building muscle rapidly that I might not fit my current wardrobe soon. I was excited to leave the house for a bit and got dressed up for a day on the town, but my hopes were dashed as she placed a remote-controlled vibe onto my cage. All it took was a button press to send vibrations reverberating through my cage in an attempt to pleasure my locked cock. It stopped as soon as it started but that's all that was needed to make me tense up momentarily as I felt a drop of precum fall into my jock. Jenna laughed leaving for the car while I still gathered myself.

After we reached the mall and made our way to the entrance. Jenna grabbed my hand in hers. "What are you doing?"

"Duh, silly. This is a date, we need to look the part."

I hadn't thought she meant it literally, but we held hands as kids before so this wasn't a big deal. Somehow I still felt nervous though.

We stopped for a bite in the food court, which was fine enough. Except for Jenna taking the chance to randomly activate the vibe and almost making me choke once. I called her an ass as my knees grew weak, but she just laughed it off as usual.

Next stop was a clothing store and a female clerk stopped to ask if we needed help as Jenna thumbed through the racks. "Hi there ma'am, can I help you find something? Maybe something special for you and your boyfriend here?"

I coughed out loud. "Oh, we're not dating actually."

"Really? But you make such a cute couple! Okay then, let me know if I can help you find anything!" she responded cheerfully, before wandering off to another customer.

"Oh my god, I can't believe she thought we were a couple!" I groaned in disdain.

"Really? I thought this was a date. Besides, you should be happy a woman thought you were good enough for me," she jabbed playfully.
I blushed. "I guess it is kind of flattering..." But before I could continue Jenna had picked an outfit out for me and pushed me into a changing room.

"Uh, I don't know about this, it really isn't my style usually," I shouted from inside the changing room.

"Quit stalling and just try it on. I went to the trouble of picking it out for you."

I rolled my eyes and started to strip. It wasn't long before I felt the familiar buzz around my cock cage though. "Stop it! Do you want me to ruin these clothes? I'm messy enough as it is with you teasing me all day!"
"Fine, fine, you win. Now hurry up and show me."

I quickly suited up in the button-up dress shirt and fitted black slacks with black leather shoes then opened the door to show her. "Well? What do you think?"

"Wow, very nice! I have good taste. Could use a few adjustments though." Before I could ask her what, she pushed herself into the changing room with me and locked the door.

She started to manhandle me before I could protest. "Ok, loosen a couple of buttons, stretch the pleats, and tuck your hair behind your ears... and voila!" She then turned me to face the mirror.

"Wow... That's me?" I was shocked at how good I looked, not being one to dress up usually.

"Yup! I told you to have confidence in yourself, the clothes just bring out the man who was already there." Her compliments made my cheeks warm.

I stood there admiring myself in the mirror a few seconds before she spoke up again. "Now I think it's time for your next lesson."

"Wha- Here!?" I didn't have time to say more before the vibe started buzzing again, the feelings penetrating deep into my cock and balls, eyes rolling back into my head.

She unzipped my slacks, slid my jock to the side, and pulled my caged cock out through the fly. I wanted to worry that people outside could hear the buzzing on metal but I couldn't concentrate hard enough to.

"Lesson number two: going down on a woman," she proclaimed matter of factly.

"Jenna... please... We can't do this here, people will find out... Plus I've never done that before."

"All the more reason to hurry then. Look, you're already making a mess of the floor." I looked down and saw she was right, several drops of precum already littered the floor of the changing room. "If you get to it quickly, I'll take the cage off and you can vent some of that naughty cum in your balls that's clouding your thoughts."

"Fuck... fine! Just tell me what to do!" My sanity was reaching its limit.
"Get down on your knees and lift up my skirt. I'm all ready for you." I did as she asked and she was right. She hadn't been wearing panties this whole time. For the first time in my life, I was a breath away from an honest-to-goodness pussy, her pink lips looking rosy and inviting. Was I really going to go through with this? At least she was shaved, I guess...
She guided my hand to her pussy and without ceremony, slipped one of my fingers inside of her. I recoiled in shock but once it wore off I could feel she was already wet, the thrill of getting caught must have turned her on. "Come on, Tommy, you know how to finger yourself. It's not that different with a woman."

At her urging I curled my finger up and felt around inside her. I was surprised to feel the complex texture of her folds, completely different than how my ass felt. "Ooh, that's pretty good. You're hitting my g-spot already."

"G-spot?" I asked.

"Yeah, it's a feel-good button like the clit, only on the inside. Kinda like the prostate is for you homos. Ahh..." I could tell this spot did wonders for her, but I needed some stimulation myself, so I reluctantly asked her what I should do next.

"Use your lips and tongue, baby. You're a fag who's used them before, besides, you're a quick learner." With that insult she pushed my head into her waiting crotch, my lips touching her own set of lips.

I winced my eyes waiting for a wave of disgust but it never came. Her pussy smelled normal and what liquid I could taste on my lips was as unoffensive as my own precum. Was I lied to? I had always heard pussy smelled like fish and was the foulest thing on the planet, but this was just like her breasts. What other propaganda had I been fed throughout the years?

I pushed the angry thoughts from my mind, choosing to focus on the vibrations on my caged dick and my sister's pussy in front of me. I started to lick and nip at her vulva, my tongue flicking back and forth over her pink warmth.

"Oh god, yesss... You're a natural, Tommy. Such a good boy." Her praise spurred me onward.

"Really?" I asked between lappings.

"Fuck, yes. Now find my clit and suck on it!" I did as she asked, trying to remember from sex ed where it was located. Eventually I honed in on and suckled at it like a little gay piglet.

"Mmph...!" I heard from above as she bit her lips to stifle a squeal. I chuckled inward, clearly having found the target. I continued my assault, my tongue getting covered in her juices as they dripped onto my chin. Suddenly an almost sweet and sour flavor hit my tastebuds, signaling a change.

"Dammit, Tommy... I'm close. You're gonna make me cum!" Her body started shivering in pleasure under my lips. I didn't let up, even as a flood of her love juice soaked my face and the sides of her legs as she came, her knees shaking.

Seconds later I tore myself away from her soaking cunt and got to my feet to help hold her up. Seeing my sister vulnerable and panting, from something I did to her, was a thrill I hadn't expected.

"Jenna... Please..." I needed release or I was going to go insane.
Still speechless, she nodded and took the key from her necklace and unlocked my cage. It fell to the ground with a muffled thud onto my old clothes as my cock sprung to life flinging precum onto her skirt. I stood there, my pained dick bobbing in the cold air as it jutted out from the fly of my new black slacks. A distinct tinge of red colored it and I could still feel remnants of the vibrations running through it even without the cage on.

"Use my thighs, baby, they're slick with the proof of your masculinity." I knew what to do immediately and pushed her against the mirror as she squeezed her thighs together. I nestled my face into her neck at the same time as my burning manhood breached her thighs. The slick juice cooled the heat in my loins and I started fucking back and forth, using my spit and her womanly fluids as lube. "That's it, baby. You need to unload all that faggot cum."

This wouldn't take long at all. I huffed and panted, inhaling the scent of her perfume before grabbing her breasts and squeezing them tight. I thoroughly ravaged her chest and thighs, my overwhelming need to cum the only thing on my mind. My thrusts grew desperate and I slipped out from between her thighs and blindly I tried to realign myself. My hard rod missed the mark though and my tip grazed the entrance to her pussy making me moan, before she reached down and tucked my length back into her thighs, letting her moist lips run across the top of my shaft as I continued my thrusting.

"Ah, ah, ah... You're nowhere near ready for that yet. Now use my thighs like a good little homo and dump that useless gay cum where it belongs. It's not fit for a woman, it belongs in the trash or on the ground, wasted," she whispered into my ear.

"Ah... shit!" Her words struck a nerve and my balls opened the floodgates. I thrust one more time pushing my head past her thighs and bit down onto her neck as I started to unload. I could hear each and every rope hit the mirror behind her even over the tacky pop music playing in the store. We moaned in unison as I feebly thrust a few more times as the last drops of pearly white cum left my shaft.

I caught my breath after a couple minutes had passed and I sank onto the changing room bench, my cock still jutting out from my slacks as it attempted to slowly soften. "Holy shit... Thank god we weren't caught," was all I could manage to say between pants.

"You've got that right... God that was so hot, Tommy. You're such a natural at this I'm starting to think you lied to me. Even my husband can't get me to cum from oral."

She knew exactly what to say to get me flustered and stroke my ego at the same time, but deep down I felt a purer pride I'd never felt before. I didn't know I had this kind of manly ferocity inside me waiting to come out.

"You've been a very good boy today, but you've made a mess of the changing room. I'm gonna take these tags and pay for your new clothes, put your cage back on then use your old ones to clean up your filthy excuse for cum and meet me out there." She didn't even stop for me to answer before she was gone.

I looked around and she was right. There was a puddle of precum and her juices over the floor and what had to be the biggest, thickest load of my life yet was running down the mirror. I sighed then put my cage back on and tucked my package back into my slacks, only now realizing the jock-covered cage was apparent through them. Then I used my clothes to wipe up as best I could, licking my lips at the recent memory of her overflowing juices.

When I finally made my way outside the story, I saw Jenna talking to two other women. One a redhead and the other Asian.

"Hey, sorry to keep you waiting," I offered, not wanting to interrupt.

"No worries! I just ran into a couple of friends and we were catching up. This is Anna and Susan. Guys, this is Tommy."

"It's nice to finally meet you! Jenna has been going on about her little brother for ages but she never said you were this cute," said the redhead.

"Uh, thanks! And yeah, it's a pleasure."

Jenna stepped back in, "So, I was just telling them all the little details about our little date today."

She grinned as she saw the panic in my eyes, "Ohh, did you now? Yeah, we had fun."

"Wasn't it? Well, after hearing all about how much fun we had, they decided they wanted to have some fun too!" My eyes widened in response. She didn't... she couldn't have!

"So I said they should come back home with us and see what other fun we usually get up to with the parents gone."

I didn't respond quickly enough and with a press of the button in her purse, the vibe started going off again. "Nnh... Uh, sure! Sounds fun...!" I said, gritting my teeth to hold my composure.

Susan spoke for the first time, "As much as we'd love to, we're actually on a date ourselves today. Raincheck for sure, Jenna."

"Oh, darn. Anytime girls, Tommy would just love to entertain some guests. Call me later!"

I grabbed her arm and started walking toward the car. "What the hell did you tell them?"

"Gosh, don't be a stick in the mud. I didn't say anything about what we're doing. I mean, unless you want me to."

"...Thank god. You almost gave me a heart attack. And no, the less people who know about this the better."

"I did let it slip that apparently you give really good head. But don't worry, they're lesbians, surely nobody in their right mind tries to go straight, right?" she said running off to the car.

"God dammit, Jenna!" I chased after her intensely fearful of what she might end up doing one day. That night I could barely sleep from dreams of eating out Anna and Susan.

------------
Day 42
Dose: 6 pills
Affirmation: Nature made cock and pussy to fit in perfect union. Using them incorrectly goes in the face of nature.

Jenna's bootcamp went on as planned and so did her life instructions meant to sculpt the real man hiding beneath my skin. Or so she said, but I could tell her advice was paying off as when we went grocery shopping I could feel the eyes of both men and women on me. I've been eating and working out like crazy now, my body slowly growing to that of a wrestler's now. My chest and back feel broader and my biceps bigger, my stamina increasing almost threefold over such a short period of time. While my energy and aggressiveness seemed to be peaking, so did my acquiescence to do whatever she asked of me.

She also instructed me to stop shaving my beard and body so my naturally hairy pelt I always loathed had started to rear its head again. I didn't seem to mind it anymore, it was less time manscaping to act like a twink and I actually found myself admiring it in the mirror now. Jenna also had taken to absentmindedly running her fingers through it when we were chilling on the couch.

Once again she increased my dose again. I assumed it was to blame for my rapid hair and muscle growth, but I was more concerned about the other effects it was having. I woke up one day with my balls visibly swollen and my dick an unhealthy shade, forcing her to buy a new chastity cage for me. I must be losing my mind, but I swear my junk is getting bigger. When it's off my dick gets so hard it hurts and the veins were starting to stand out. Worried for my health, I had her measure it one day, and sure enough, I'd grown almost an entire inch in length and half an inch in width. I thought that was impossible but I was going to look a gift horse in the mouth.

Unfortunately, my libido has skyrocketed again too. Every morning I wake up my jock is drenched in gooey whitish-clear fluid, almost as if I'd had a wet dream. I leak pre off and on throughout the day having to double up on my jock or risk leaking through my clothes when I'm out and about. More than once I've had to get on my hands and knees to wipe up a mess I'd made on the floor after she'd been teasing me.

Jenna doesn't wait for me to come to her anymore and she usually initiates things since I'm basically perpetually ready for her. She has me eat her out and finger her almost daily, saying with me around there's no need for her to masturbate. And I don't mind, I'm more than happy to help out the sister that I love dearly. Despite my overwhelming desire to bust a nut though, she lets me out of my cage even less now. She tried to relieve me more often but it wasn't enough and she said if I had my way, she'd get nothing done during the day and I can't really blame her honestly. Though I'm kinda starting to miss the touch of her hand on my shaft.
Instead, she took a page from her workplace's experiments with animals and found a new way for me to vent the pressure from that pesky gay seed. Every three days like clockwork, when my balls feel swollen and start to ache, I wander into the den which she converted into an office while she's staying here. She has me get onto a table on all fours and straps me into supports and positions a beaker beneath my caged cock letting precum drip into it. She attaches a device to my cock cage and very carefully inserts a probe into my anus, nestling it against my full prostate. I really haven't gotten much pleasure from insertion of any kind recently, so I just treat it as a medical procedure now like she's so keen to call it.

When I'm all set up, she flips a switch and a current runs through my groin. The muscles inside pulse and relax and a long, throaty groan escapes my lips. Steadily, in an agonizingly slow drip, thick, pearly cum starts to fill the beaker. The feeling is hard to describe, but mostly I feel a steady, minute lessening of pressure inside me. I groan a little and she strokes my back and pets my head, calling me her good little gay breeding bull. Eventually she leaves me to myself and for the next hour or two, drop by drop, all the useless cum I'd made the past three days is milked into the beaker against my will.

By the end of the milking session, it starts to hurt as the flow of cum drops runs dry, the muscles having been fatigued from working nonstop. Soon she comes to check on me and every time I'm amazed by how much cum has been milked out of me. About half a beaker full of thick, sticky cum and all of it extracted without getting hard once. She pets and praises me for my hard work providing samples for her job and as they've never had a human test subject, she wants to monitor my changes closely. Groggy and in a daze, I kneel under her desk and eat her warm, pink pussy while she logs her data. It's the rare time I feel relief as I relish the empty feeling in my groin and balls before they start to fill again that night. I listen to her moans as she cums into my awaiting mouth, thinking she was right. This was the best way to relieve me of my worthless faggot seed until I was a real man.

This cycle continued until tonight, when she asked me to spend the evening in her old bedroom with her, the first time I'd been allowed in there since our bootcamp began.

"Don't be shy, Tommy. I won't bite, come snuggle with me."

I did as she asked, slipping under the covers and wrapping my arm around her. "Mmm, this is nice. You're so big and warm. You're shaping up to be such a perfectly handsome boy."

"Thanks, I really love this too." I was being honest. This summer we were bonding in a way we hadn't before. I was grateful that, the gay issue aside.

"Tommy?" she asked, looking into my eyes.

"Yeah?"

"Have you been thinking about boys at all lately? I think you're almost ready for the next step. But it's a big one and I need to make sure you're ready to commit to seeing this through. If you have any reservations at all, now's the time to say so. We can still call it quits and you can go back to how you were before."

I thought about it for a moment. About how I was before. If you'd asked me then I'd have said I was insane for trying to do this. But now I liked seeing how my body was changing, the new experiences I got to have as we took each step, and she was right, I've barely thought about a boy at all lately with all my needs being satisfied. "No, I think I can do this. I want to try."

"Are you sure? Prolonged use of those pills is starting to induce permanent modifications like your sudden growth in size, and I can't guarantee what will happen. And I know you seem to enjoy eating me out and stuff, I do too, but what's coming you can't just handwave away. You'll remember it forever even if you still decide to be gay at the end of this."

I squeezed her hand. "I know, but I trust you. You're always looking out for me and if you think this is right for me, then I want to try."

She chuckled, "Good answer. I'm proud of you baby boy." She reached down and slid off my jock to unlock my cage. I immediately sprang to life and you could feel the heat coming off my loins and see the hunger in her eyes. Without so much as another word, she started licking my shaft from base to tip, a moan escaping my lips as my toes curled. "Fuck... Jenna..."
I'd never had oral before and the prolonged neglect of my cock the past few weeks had made it extra sensitive. She tried fitting my plum-sized head in her mouth but struggled with the newly increased size of the flare. Eventually it cooperated and she was able to smoothly suck up and down half my length while stroking the rest with her spit.

I grabbed at the sheets. "Seriously... I don't know how long I can last... This feels way too fucking good!"

She left my cock lonely as it slid with a pop from her lips. "That's okay. We can practice more later. Grab the box from my nightstand, will you?"
I opened the drawer trying to keep myself from cumming and rifled through it blindly until I found the box. I noticed it was a pack of Magnum condoms before I tossed it to her.

She ceased her ministrations on my wanting member once again, making me whimper. "I know you probably just want to grab my head and face fuck me before you dump your degenerate cum down my throat right now, but sorry, you'd make a huge mess and I can't let a perfectly good sample go to waste."

She ripped open a packet and rolled the condom down my shaft until it reached the base. It fit almost perfectly to my growing size. "Only real men get to dump their loads in a girl, and you're on your way, but you're still just a disgusting homo with a worthless cock," she chided me as she stroked my gloved dick letting me writhe on the bed.

Fuck, I needed to cum. It'd been so long and here she was teasing me on the edge, I had to do whatever I needed to finally get some release that wasn't from an electrode. Whether through instinct or training, I'm still not sure which, I pleaded to her. "Yes, you're right! I'm a disgusting, degenerate faggot who only wants to waste his filthy, impotent seed spraying it in places a real man never would. Please, I don't want to be like this!"

She smiled with glee as she kept cock teetering on the edge, playing me like a fiddle. "Are you sure wanna keep going? Look at how desperate you're acting, I think you might want to stay a miserable little homo who just wants to get his rocks off."

"Yes! I'm sure! Keep helping me drain all the gay out of me until every last drop of faggot cum is gone and I can't make any more!" My mind broke in that instant and I didn't realize what I asked for.

"Ok, but remember you asked for it. From here on out, it's going to be hell before you get to heaven."

"Yes, anything! Please just let me cum!"

She renewed her playful handling of my dick and in less than a minute my moans turned into a loud continuous grunt that resounded through the house. I bucked my hips as a shot of thick cum blasted into the end of the condom. Then another, and another, and another. My eyes rolled back into my head as 12 heavy ropes audibly pelted the inside of the condom, hiding my crimson head in slimy, white goo. Even as the cum stopped flowing, I thought my climax might never end, my body almost giving out before it decided to. I sighed in relief as she carefully extracted the condom from my cock, mindful of the contents she didn't want to spill. I looked through glazed eyes as she admired the nearly 1/4 cup of cum I must have filled the condom with. Sadly, the last thing I heard was "Rest up, baby boy. You're gonna need it," before I passed out into oblivion, my dick still hard and ready for more.

----------
Day 68
Dose: 10 pills
Affirmation: Real men instinctually desire to pass on their genes. Only women can help fulfill this primal need. Make the right choice.

Jenna was right. Hell certainly does come before heaven, but hell isn't all bad. I rarely left the house anymore due to a lack of interest outside of becoming a better man, and when I did it was for a brisk run, wanting to exhaust my extra energy before bed. My life had completely changed since before this summer. While I was moderately athletic before, I now eschewed almost everything outside trying to use my excessive hormonal surges to build more muscle. No more gaming, no more reading, nothing like that. Jenna assured me when this was over, I'd settle into a more normal routine, but right now I couldn't stop.

Now I wasn't starting to look like a bodybuilder or anything, this was too short of a period for that, but I was ripped and brawny rivaling many fitness models out there. It was more than I ever dreamed before and more than anyone could obtain in this span of time normally. My hair was thick and lush, and even without exercise, I had a manly, musky scent about me. If it turned me on just catching a whiff of it, I figured Jenna had to be enjoying it though she'd never admit it.

Jenna was still using me as her personal masturbator and she was slowly letting me into more facets of her life. Sometimes we'd share a shower together and she'd let me wash her while letting me sneak peeks at her curvy body. Perfectly well-intentioned as it was though, it inevitably devolved into something lewd.

Not long after my first night in Jenna's room, her two lesbian friends, Anna and Susan, finally dropped by for a visit. She let me stay clothed as we played a few board games (or as well as I could being unable to focus on higher thinking now) while they had some drinks. It wasn't long before she let the true nature of our relationship slip, and with their inhibitions lowered, demanded to see me in my regular uniform.

The last time we met, I was pissed at the mere thought of it, but now I trusted Jenna so fully and was so confident in myself that I didn't care what others thought of me. I obliged them, stripping down to my double-lined jockstrap, and did a few poses for them to hoot and holler over while acting as a butler to serve them more drinks. Susan then stuffed a dollar down my jock and grazed my bulge just to see if the cage was real. She burst out in laughter, unable to believe Jenna's gay little brother they had heard so much about would submit to wearing such a thing, let alone trying to convert his sexuality. "But hey, as long as you're happy, that's what matters," she said.

"Yeah, normally a man would never do this to himself, but I just trust my sister that much," I responded receiving aws from the girls. I then ripped my jocks off to show them my biggest secret.

"Holy shit!" Anna shouted,"And he's packing too! I bet he's bigger than our dildos. I can't believe you get to mess around with your brother's dick whenever you want..."

"His dick's not even the best thing about him, you should see how good he is with his tongue." She snapped her fingers and spread her legs. "Get to it, slave boy!" She clearly enjoyed showing off her little toy to her friends.

I proceeded to lift her skirt and go to town, now having memorized how to crack her orgasm like my tongue was some sort of key. Soon she was moaning and quivering and out of the corner of my eye, I could see her friends rubbing themselves.

"Shit, Susan... This is hot... Do you wanna, you know?"

Susan replied to Anna, "As long as Jenna's okay with it. Plus, it's only straight if it's a dick, a tongue couldn't hurt just this once."

Jenna, still coming off her ecstasy high, gave a tacit thumbs up and the girls nestled onto the couch beside each other before slipping off their panties. I knelt before them, a brief moment of worry entering my brain as I realized these were totally different women, ones that weren't my sister. I was able to brush it aside quickly though and seeing their kempt pussies on display, I dove in with Jenna's well wishes.

I fingered them both and swapped lapping at their slick cunts until first Anna came with Susan not far behind her. They both praised me for my natural ability as soon as they caught their breath. I thanked them and went back to serving as their faux butler while the three caught up, listening to their stories and enjoying their fawning and stray gropes at my ass until they needed my lip service again. I'm not sure how many times all three of them came, but my mouth was sore by the time they left, making sure to promise to come visit again. Jenna praised me that night over and over, expressing how happy she could share me with her friends and I echoed the sentiment having genuinely enjoyed myself. She let me sleep with her that night after promising me the last phase would start soon. The next day, she upped my dose one last time to 10.

The next few days I was feverish, the higher dose pushing the limits of my body. I stayed in bed most of the time falling in and out of consciousness as my body tried to adjust. By the time I started to stabilize and regain my lucidity, I realized both my jock was matted and my cage was cramped again. I yelled for Jenna to get me a new cage, but apparently she had foreseen this and bought one ahead of time. She removed my cage and an intense musk filled the room. I stared down at my swollen cock, a bruise starting to form at the base. Jenna applied a medicated cream and a numbing agent to my cock to prevent it from hardening and causing any damage while she applied the new cage. The pain quickly died down and she slid on my new cage. Thankfully it fit perfectly and she said it shouldn't cause any further problems, but to treat it carefully so it could heal.

She checked on my cock the next day and let me get hard to take a measurement. Soft it was longer than my erection had been before the bootcamp, and now when I was hard it was unrecognizable. It measured in at around 8.5in and almost 2.5 in width. My whole cock thrummed in time with my heartbeat, the veins rippling beneath the skin, its color healthy and ruddy contrasting against the rest of my pale olive skin.
And my balls! They must have been the size of a large orange now, truly they were bull balls if ever the term fit. Another dose of the numbing agent and my erection subsided, quickly being sheathed away before my new weapon could cause collateral damage. My jocks now strained to cover my package, almost in an obscene caricature, but man was it sexy.
Every morning since I awoke full-on thrusting my bed into submission, my jock having soaked up a fully white load of semen into its fabric the amount rivaling loads I'd made earlier in this experiment. No longer just precum, throughout the night my old jizz had to go somewhere so my body could keep up with the seemingly unending amount my balls and prostate were churning out. I had to take extra care wherever I was for fear a sudden gout of viscous goo might slip out during exercise in addition to the constant leak of precum. Concerned, she ran some imaging tests which confirmed a healthy prostate, although along with enlargement of other glands, it had grown almost double the size of normal in an attempt to store it all. Sad to say it wasn't enough though. My hell truly had begun.

Constantly aroused, I frequently pestered Jenna to let me play with her snatch, just to take the mental edge off. Often she would oblige, but just as often she would turn me away and I'd have to go lift some weights to cool down. Even worse, the news that I no longer was allowed to remove the cage hit me like a brick, and I probably wouldn't be able to for at least the next few weeks. She said it was too dangerous and that every drop was needed for their future testing, so at least my pathetic gay cum could be put to some use. I punched a wall leaving a big hole upon hearing the news, but I quickly calmed down and relented.

Every moment of every day was now dedicated to me managing the urge to stick my dick into something and pound it into submission, so I no longer left the house. The familiar pressure in my balls was now building up every day, and without release, I experienced intense pain in my groin. My milking sessions were now performed daily to provide me even a modicum of relief.

At first they went as usual. I'd get strapped in, have some electrodes applied, and I'd start dripping my useless semen into a beaker for a couple of hours. But over a matter of days, my jizz got thicker and thicker, almost like glue to the point my body struggled to expel it. It took longer and longer to empty myself and at the same time, each beaker was getting fuller and fuller. Each session I got noticeably more frustrated, sometimes fighting my restraints trying to force this stupid cum out of me and it took Jenna longer and longer to calm me down.

She told me she had debated using something similar to a milking device for cattle, but being hard for as long as it would take to make me orgasm enough to empty me might damage me. Plus she had quotas to fill now and this would be drawn out and messy. My spirit sunk having realized I was now basically a bull whose sole purpose was to be milked of my faggot spunk. I begged her, "Please Jenna, I don't want this filthy gay cum in me anymore! Just get it out of me! Use a needle if you have to, I just wanna be normal..." She hugged me tight and cooed in my ear, "Don't worry, I'll think of something to make the rest of summer as painless as possible for you."

She brainstormed and eventually devised a modification to the usual method. I was set up like usual, but this time after the elctrodes were applied. She numbed my penis and inserted a hosee through my urethra, which thankfully grew with the rest of me. She snaked it down to the base of my cock so the semen would have less far to travel, and in theory when the hose detected fluid of a certain density, a light suction would occur to siphon it out the rest of the way and into a metered tank. Mildly horrified of having my innermost reaches plumbed, I just needed relief so I nodded for her to start the session. My muscles tensed and after a little bit of straining, I could feel the gentle suction inside my cock. Soon my thick, almost yellow fluid would snake its way down the tube in bursts, stopping here and there with how sticky it had become.

Eventually I saw and heard a big splat as the first load entered the tank. I sighed in relief, glad something was working now. Hugging my face in joy, she praised me and left me there for a couple of hours. Over time the tank filled and filled, the markings measuring tens of milliliters of my disgusting yellowed homo spunk approached the top, the steady parade of hefty splats slowing to a crawl. While I felt some pressure abate, I could tell something wasn't budging. I wasn't empty yet. I called for Jenna as the suction wasn't turning off and it was starting to feel uncomfortable.
Again worried, she turned off the electrodes and whipped out a portable ultrasound, placing it to my abdomen. Apparently some vesicles were jammed so she needed to perform more direct intervention. Jenna tried to calm me as she inserted the hose further down inside me, monitoring its path with the ultrasound. I felt a pinch as it passed into my prostate and she guided it to the jam. Once in position, she turned the suction back on and slid a gloved finger into my ass to manually apply pressure to the gland. I grunted through gritted teeth and huffed my breath, the firm insistence of her finger almost painful. She adjusted the hose just a few more millimeters and I sighed as the suction started working again. She massaged me over and over, urging the last bit of sludgy, yellow cum into the hose into the tank where it belonged. Another check with both the ultrasound and me, and she withdrew the hose. Soon it was like I was never full to begin with. I was released from my restraints, no worse for the wear and I hugged her tight finally feeling some respite.

"Thank you, Jenna. I love you." I said, tears welling in my eyes again.

"Aw, don't go getting sappy on me, you're fine now. Besides, I should be thanking you and this little milk factory," she playfully remarked, squeezing my oversized balls. With that, she detached the tank to inspect it. It was just more than a beaker's full and the jelly-like seed barely sloshed as she turned it in her hands. "No wonder you're so gummed up, we're getting some stuff from way deep in there. Well, at least we have a solution now."

"Does this mean I'm almost a real man now? Is this the last of it?" I said, hope in my voice.

"Yeah baby, you're almost there. Brace yourself though, it happened once so it will likely happen again." She was right, as usual. Almost every day since then I had to have my insides scraped clean, but it was all worth it if I could finally be normal.

---------
Day 70
Dose: 10 pills
Affirmation: None. There's no turning back now.

Over the past twenty days or so I'd resigned myself to an existence meant solely to be milked daily, sometimes even twice a day. I'd reached an unbalanced equilibrium in my mind which would swap in favor between manliness and emasculation. I could look in the mirror and see evidence of my newfound masculinity, but without the use of my cock, was I even a man anymore? Was I ever anything more than a loser fag destined for degeneracy? I could feel a choice approaching quickly, one that I couldn't ignore. I had to embrace one or the other, and affirm, no demand who I was going to be.

I think Jenna sensed my introspection and let me have my space to think. And think I did, in between moments of mindless lust and harrowing emptiness, until today when Jenna called me to her room.

"Did you need me for something? My session isn't until later..." She was sitting on the bed in just a lac bra and panties, a sight I'd gotten used to recently.

"Sit down, Tommy," she said, patting the bed and I sat down beside her.
"I've reached my quota for work, so you won't be needing the pills anymore."

A weight instantly lifted off my shoulders. "Does this mean I'm done with the milking?"

"Yes it does, baby. You've done so well to hold out this long, lesser boys would have broken. It'll take a week or two for the drugs to get out of your system, so you might need assistance for a little while longer, but your libido and output should revert back to normal. Well at least what will be normal for you, which may still need extra attention and is far more impressive than most men will ever accomplish."

I blushed from a combination of her praise and my happiness.
"Now what I need for you, is to go through with your last lesson. If you want to, I need you to tell me who you want to be and be ready to give up your old life for good. If not, then we're done here."

Did I really need to think? It was all I'd been thinking about the past several days. I was ready to make something of myself. "I... want to be a man. A straight man, Jenna. I never want to touch another boy in my entire life. Please, help me."

She smiled warmly. "Stand up and look in the mirror, Tommy, look at what you made yourself." I stood and peered into our reflection in the mirror, finally seeing my true self. "You're strong, handsome, and learned to care for a woman's needs. My needs. Look at your body, honed through hours of dedication." She reached down and grabbed my cage. "Look at this cock, it's nothing like the pathetic excuse for a dick you had before. It's a real man's cock, all you need to do is learn how to use it right."

I knew what she meant and the mere thought made a steady stream of cum leak from my cock. "See? Your true, virile, manly seed has been fighting against your pathetic, faggot cum all this time. It's always been there struggling, we just had to help it force that filthy gayness out bit by bit. That was some just now, there's only a little left now and only one way to get it out."

"Only a little left... Please, I want it gone, Jenna."

"Then kiss me and we can finish this."

I held her head gingerly in my hands and leaned down to kiss her. My first kiss with a woman in 17 years of life, one I'd never forget. We kept kissing and she sucked on my tongue, neither of us able to get enough, both of us eventually falling onto the bed. We grabbed each other's flesh trying to find purchase until she realized my cage was still on. She hurried to undo my cage and I ripped at her bra and panties until they were shreds, both of us naked, skin to skin, my hard cock leaking against her stomach. We made out a while longer until I'd finally hit my limit. I needed to be inside of her.

I fumbled for the box of Magnums we'd used before, already anticipating a tighter fit than before as I was about to slide it over my cock until she stopped me."No, your first time needs to be the real deal."

"But what if you get pregnant? Are you on the pill?" I asked, never dreaming I'd have to utter that string of words.

"It's okay. We've been trying for a couple of years now, but he's not up to the task anymore and were about to explore donors. I'd be thrilled if it was yours, and with all the changes you've been through, I don't think there would be any doubt of conception."

"You actually want me to knock you up?" She nodded. I couldn't believe what she was saying. We're half-siblings! Was I really going to do this with my sister? Wait, was I really about to sire some offspring into the world and watch her raise it with some other man? Without me? My head was spinning with what-ifs I couldn't handle right now.

"Arrgh, fuck it!" I threw the condom aside and went back to making out with her, tenderly playing with her breasts at the same time. Soon we broke for air and I was losing my mind already.

"I guess that's a yes?" she asked me coyly.

"Yeah, I'm gonna fuck you so hard and fill you so full of seed you won't be able to move. I've been waiting more than two months for this, so you better be ready for it." I slapped my precum-soaked cock against her belly letting her feel the sheer weight of it before rubbing her entrance lightly over and over, coating my member in her juices. I lined up my massive head one last time and started to push forward, her tightness refusing to budge. Instinctually I adjusted the angle of her hips and rubbed her lower abdomen, her lips slowly giving way to my huge girth.
"Holy shit! It's so big..." she moaned through pursed lips as my head finally slipped inside.

"Fuck... that's it. How big am I, baby? Bigger than your husband?" I questioned her as I slowly urged my shaft inside of her.

"Ahh! So much bigger! The biggest I've ever had! Nnh..." She groaned as I eventually bottomed out, able to feel her cervix resting squarely against my head. "Fuck I feel so full and you're so deep... You're hitting spots he's never reached before!"

I chuckled, barely holding myself together. "That's what I like to hear, slut. I'm gonna start thrusting now." I pulled back slightly and could feel the flare of my glans dragging her folds with me, refusing to let go. We really were a perfect match. I kept pulling until I was almost out and started pushing back inside, making her gasp. As I deep dicked her over and over she started moaning every time I'd bottom out, grinding against her cervix just to send a tingle down the length of my cock.

I pounded her hard and fast, soft and slow, mixing it up as I lost myself in the beautiful form beneath me quivering with every touch. Never in a million years did I believe I'd be doing something so manly, so feral, so primal. I finally felt right with the world, I just needed one last push to cement it.

"Shit... Jenna, I'm getting close... Your pussy feels way too good..."
"Me too, Thomas. I'm right there with you!" She called me Thomas! She never called me Thomas... Fuck if she didn't know how to rile me up at the perfect time. "Do it baby, flush out that last bit of worthless gay spunk and pump my pussy full of manly, straight seed!"

I pistoned wildly, unable to control myself anymore. "Fuck yeah! You get the honor of savoring the last time I use this pathetic faggot cock, it's finally getting put to good use the right way! By tomorrow there'll be nothing left but a superior, straight male cock in its place!"

"Yessss! Fill me up, I need a real man's cum in my womb! I'm cumming...!"
I felt her convulse around me, her legs wrapping around my back to draw me in. My primal urges kicked in and I pressed my fat cock head flush against her cervix and gave a few, short thrusts nudging it open to accept the huge load churning in my sack.

"Fuck, fuck, shit, I fucking love you Jenna! Here it comes, take my cum, all of it, gay and straight, just have my fucking babyyy!"

My dick throbbed as my abnormally thick and potent load worked its way up the shaft. I grunted and pushed, helping it up and out, not in ropes to paint her insides, but a steady stream that started to pump into her womb directly. My knees shook as seconds turned into a minute, then two, my orgasm rocking me to the core as I slowly filled her womb to the brim.
She was moaning along with me before she spoke. "I love you too, Thomas. I can fill your manhood filling me up, it's so warm, so kind." I couldn't muster a response, but we kissed deeply, locked in an embrace that could never be matched. Soon her womb overflowed and I could feel my cum seeping out around her lips that clutched the base of my cock. We stayed like that until I'd emptied what I could into her without assistance and despite still feeling full inside myself, and I pulled out slowly, a torrent of leftover cum soaking her mattress. I snuggled up next to her as we kissed some more, eventually both of us succumbing to sleep. I rested soundly for the first time in weeks, knowing I'd become a new man.

----------
End of Summer

Over the next few weeks, I steadily grew more comfortable with my newfound self. Like she'd mentioned before, I still needed some help in the milking department, but this grew less and less over time until more bearable methods could be used. I told Jenna I might even miss the ol' electrodes after the last time, but she offered to hook me up if I wanted to relive some good times. I laughed, saying I might take her up on the offer, only half joking.

As my body reacclimated, I found that while I still had a super high libido, I was no longer mindless about it. A great relief that was, as it meant I no longer needed the cage to restrain myself. We did keep it around for when we decided to get a little kinky though.

It seems that all the changes to my body were permanent, which I didn't have a problem with, and soon enough the regression in my semen output and consistency hit a standstill, at about the levels of when I first started needing to be milked, but that was very manageable now that I was a free man and could empty the tanks a few times a day. I still was a bit of a leaky mess though and made sure to wear jocks to sop it up, but not a total negative since it was such a turn-on. Speaking of, I was allowed to wear clothes around the house now, but I usually ended up defaulting to my skivvies anyway since I'd been trained so well. Plus, I liked how handsy sis got with me when I was naked. My confiscated eectronics were returned as well, and the first thing I did was delete any old contacts and gay apps I had. This summer was a new start for me, so I cleaned house and never looked back on that path again.

As for my relationship with Jenna, we kept fooling around the rest of summer with me frequently eating her out while she jerked me off and me bending her over at random times for a creampie at her insistence. Just to make sure she said. I could tell she was pregnant by the new glow she had, but hey, I wasn't going to say no to my big sis.

All good things come to an end though as summer came and went. My parents returned home and they were shocked at my transformation, my father being especially pleased. She packed up her stuff and I helped her move back into her house before hugging her tight with tears in our eyes. We'd bonded so closely this summer and she did me the greatest favor anyone could, helping me find myself. I asked her what I could do to repay her, but she said I already had. I pried myself away before I couldn't leave and promised I'd visit her soon and she did the same.

We kept that promise and regularly met up, but only after she successfully convinced her husband that he'd knocked her up and he was elated. We talked about the future and our child sometimes. I felt mixed about it at first, glad I could give her happiness, but upset I wouldn't be the one raising him. Eventually, I made peace with it after she let me know I'd always be a huge part of their life, both the baby and hers.
One time when I met up with Jenna and was feeling especially bold I told her I loved her, like really loved her, and she offered back the same sentiment albeit with hesitation. She had obligations she couldn't just abandon, and I understood and took a step back.

I tried hooking up and dating other women after that, but I never felt as connected as I did with her and they fizzled out. The most fun I did ever have though was sometime after my 18th birthday when Anna and Susan called me up. They invited me out for a post-birthday celebration out on the town and dropped a bomb in my lap before the night ended. They decided to have a baby and I was the first person they thought of as a donor for Anna and that they would pay me handsomely. I was flattered, but tipsy as I was after making use of my fake ID, I off-handedly joked I was only open for in-person inseminations only.

The two went quiet for a moment before agreeing with my joke terms on the caveat that Susan had to be present. I was dumbstruck, but now I had to put up or shut up, so we agreed to meet at their house the next time Anna was ovulating and I'd stay a long weekend making sure it took. That day soon approached and I'd spent the last few days abstaining to make sure they got the best I had to offer. I settled in, went through the formalities, and signed some contracts and papers waiving my parental rights and that night I took Anna's virginity. It was tough on her but she took my girth like a champ and Susan got so turned on hearing her squeal that she let me eat her out too. I could have kept going but she seemed tired so we all slept in the same bed that night.

I woke up the next morning to Anna tonguing my pre-soaked cock. Seemed like my dick had awoken something in her and she couldn't get enough. Her sloppy blow job eventually roused Susan and feeling jealous and curious she gave it a try too. There's nothing more heavenly than two hot chicks thirsting for your rod, but I had to remind them I was here for a job. Anna got on top of me and shoved my cock into her pussy still wet from last night's creampie. She went to town riding me like I was her personal meat dildo or something, hell if I minded. I filled her up again and the girls went about their day thinking I was some one-and-done guy, but I cut them some slack since they didn't know how I was. I engaged them multiple times during the day in both cunnilingus and raw fucking and by nightfall Susan couldn't take it anymore and she gave up her virginity to my creampie as well. Fascinated by my stamina and the sheer amount of cum, the two of them took turns several times during the weekend milking me however they could, always with my load ending up deep inside of one of them. That was one hell of a weekend and after finding out both of them were pregnant they doubled my fee. They still call me over from time to time and while still lesbians, they make an exception for me. I'm more than happy to help out, I know how randy pregnant women can get.

---------------

Beyond

Fast forwarding some, I tried to give her space, but eventually Jenna's husband got that promotion and got busier and busier, so she relied on me more and more as the pregnancy progressed. Early on she called me over trifling matters, just to have me around. We both played dumb about it, but in no time we succumbed to our desires and ended up fucking in their bed. Recreating that first night between us soon became a regular event that just happened more and more the bigger her belly got. Until one day, her water broke while he was out of town for a convention. I took over for him at the hospital and helped her through the delivery that ended up with our new son Anthony in my hands. He was precious and I'd never felt more blessed than I did right now sharing this moment with them.

Ever since then, I made sure to come by often to help Jenna out, and now Anthony is almost walking. We still mess around from time to time, and I still studded around town for the hell of it, but she knows how deep my affection for her runs and will always be there for her. I know my place right now, but eventually, there will be a chance, and I know we'll both take it. But for now, I'm happier than I've ever been.