Inevitably Pink

`Inevitably pink'

PART TWO

By

Pink Pantyboy

This is a work of adult fiction. Names, characters, businesses, places, events and incidents either are the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Note: The story is intended for adult reading only. It contains graphic sexual scenes that include rough, intense male/male oral and anal intercourse with domination, humiliation, and punishment of the main character. This story is intended for adult reading pleasure only and contains graphic male on male sexual scenes. Underage reading of this material is strictly forbidden by the author, and by legal status.

PART TWO:

As I worked on my fourth `Mojito' I looked at Malcolm sitting across from me in a booth now, and knew that was the day it all started. I shivered and shook myself, seeing Malcolm smile. He must have known what I was thinking by the look on my face, and just to make things worse I felt his now shoeless foot worm its way between my legs and start rubbing my crotch out of sight under the table. I wanted to tell him to stop and push his foot away but I didn't because it felt so wonderfully dirty to just sit there and let him do it, something I hadn't felt for a long time and didn't even know I wanted until now. Malcolm looked around carefully at the other booth and tables but here wasn't anyone close.

"Does naughty little Bobby feel nice and dirty now?" He laughed. I didn't have to answer, as he knew I did, having answered that question a long time ago when he first asked me. I remember showering that morning and using my Mom's underarm deodorant so I would smell girly when we dressed up. My semi stiff cock gave away just how excited I was as we walked to the woods but Malcolm didn't say anything, just smiled and turns so I could see his semi stiff cock. My curiosity was running wild as we check each way before climbing the fence into the hotel grounds. This was one of those snobby `members only' places for rich people to play, with tennis courts, golf links, a private wood to frolic in and god knows what else. I did wonder who the girl and guy were as from their clothes I thought they were some of those snobby rich people. Why they were fucking in the woods instead of their bedroom was another question.

The security fence was sixteen feet high and almost impossible to climb, but Malcolm and I found a small gap in the fence where it joined a brick wall. A little careful work and we could open and close the gap without anyone knowing we'd climbed inside, certainly not the security guards that drove, rather than walk around the property. On a few occasions when they were due to, we watched and they barely slowed as they drove by, hardly looking at the fence. After one close call, we always hid and waited for them to drive by before getting inside. Once inside we scurried through the woods, giggling and shushing each other when we though the other was laughing to loud, as boys are won't to do when doing something secretive and dirty. We saw a couple of people strolling around the lake but they were too far away to see us and we made it safely to our hideout without anyone seeing us. We stripped naked, and unrolling the towel Malcolm held up and pair of pink lace panties.

"I found these at the back of my sister's panty draw." I sucked in my breath as images of a girl wearing them flashed through my fevered brain. These weren't just ordinary panties like those that you see in the magazines, as they had no middle part. I discovered later they were called crotchless panties and that only naughty girls and sluts wore them.

"Fuck, I didn't even know my sister had anything like this. Finding a girl wearing a pair of these you know what she wants." He giggled, making my ears get red. Before I could say anything, Malcolm pulled on the other pair of panties, black lace ones that looked just like the pictures in the girls' underwear mags. I hesitated, not wasn't sure I wanted to wear the pink ones, but Malcolm pushed me onto my back, and put the panties over my feet.

"Get on your knees." He ordered and when I did, he pulled them all the way up. The feeling I got looking down was at them was almost indescribably, part excitement and part shame with my stiff cock sticking out through the front opening.

"Fuck, they look so good on you." He murmured as he grabbed my cock and started stroking me. "You need to put the other things on so you look like a girl."

"What... no... what things?" Frightened and intrigued at the same time, curiosity getting the better of me. The other things turned out to be a bra and a pink thing they called a teddy. He held the pink bra out.

"Put your arms out."

"You wear it first."

"Oh, going to give me trouble are you." He snapped and before I could react he pulled me down over his knees and started spanking my butt. It didn't really hurt at first, but the longer he spanked my half panty covered bottom it started to sting.

"Ouch! stop... that hurts." But he didn't. I struggled and put my hand back to stop him but he pulled it away and continued spanking me. Then it really hurt and I started to cry.

"Malcolm... stop, please... it hurts."

"You gona to do what I tell you?" He snapped.

"Yes... yes... I will." I sobbed, anything to get him to stop spanking me.

"Say it, say it out loud what you'd going to do." I dawned on me he liked ordering me around and spanking me.

"I... I'll put the pink thing on and the bra." I sobbed, feeling defeated. He sat me up and I used one hand to rub my butt and the other to wipe the tears off my face, hating for him to see me cry.

"Put your hand out." He ordered, smiling at me. I pouted and did what he told me and he slipped the bra up my arms and fastened it at the back. Now I felt really ashamed and shivered as he put the teddy on me. It slithered down my arms and body like water, feeling as if it was molding itself to my figure.

"Oh fuck. That looks so fucking hot." I dropped my eyes in embarrassment, unable to look him in the eye. "Yeah, all you need now is a little lipstick and you'll look like a proper little girl."

"Come on... please, no lipstick... that's for girl's to wear."

"Yeah I know, but I want you to look like a girl. I'll wear it next time, promise." With his fake promise ringing in my ears, I let him put the frosty pink lipstick on me, feeling a little stupid kneeling there like that. While all this was going on my dick went limp until he made me stand and started sucking my cock. Lifting the hem of the teddy, he put his head underneath and took my limp cock in his mouth. I looked down and started panting at how dirty all this was, and just that started making me hard again. It wasn't long before I was holding his head and fucking his mouth, moaning like that girl. I couldn't help think about the pictures of the boys in slutty panties and girl's underwear and wondered if was how they felt when a guy sucked their cocks. Malcolm didn't let me cum, stopping just as I was on the edge and pulled me down.

"Lie on your tummy and spread your legs."

"What... no..."

"I just want to put some Vaseline between your legs is all." I knew what he wanted to do, and for some odd reason wanted him to do it. He spread it between my open legs and some on his stiff cock before climbing on top of me. As I felt his hardness between my legs I closed them, and straddling my legs with his, he started `fucking' me. As much as I protested about not wearing these thing, and him spanking me to make me do it, his cock sliding between my legs felt good. I started humping my hips, more to rub my cock on the blanket than pushing back to meet his thrusts.

"Oooo that feels so fucking good." He whispered in my ear. "What a little slut you are."

"Oh god!" Rubbing my cock on the blanker harder.

"You like that? You like me calling you nasty names?" All I could do was nod as I felt so wonderfully humiliated but was too ashamed to say anything.

"You're such a dirty little boy, aren't you? Just a dirty little sissy queerboy." He breathed in my ear. I nodded, wanting him to talk even dirtier to me. I loved the shameful feeling and other feeling I couldn't even describe.

"Yeah, you like me forcing you to wear slutty panties and dress up like a girl... like a little slut..." He moaned. "A swishy little panty wearing sissy boy slut." I wanted to say no, I didn't, but I knew it was a lie. I did like him forcing me to wear girl's clothes but didn't want to admit it.

I don't know how long we lay there with Malcolm `fucking' me, first fast, then slow, whispering dirty things in my ear, but suddenly we heard voices and we both froze looked through the screen of holly leaves and saw two men, not twenty feet from us. We both lay still, not daring to make a sound as both men started fishing. Once Malcolm realized they weren't coming up the slope or looking to find us, he started moving again.

"Spread your legs." He whispered and I did, not sure what he was up too.

I soon found out as he repositioned his cock and it slipped between the cheeks of my butt, pressing against my ring. Suddenly I knew what he was going to do but I was powerless to stop him. As if anticipating I'd make a sound he clamped his hand over my mouth. With him lying on top of me, I couldn't move for fear of making a sound and attracting the attention of the two fishermen. Between the pressure of his cock and the lubrication of the Vaseline, he cock slowly slipped inside me. It hurt, but not a lot, just enough to make me moan through his hand.

"Gona fuck you like that guy." He breathed. I shook my head and tried to buck him off. That only let his cock slip in deeper, and with one last flash of pain, he was inside me. I'm not sure what I felt, shame, humiliation, anger and something else as he wiggled his hips back and forth to settle his cock deeper inside my butt.

"Ummm feels so good inside your boy pussy." I shook my head, dearly wanting to beg him to stop. "Fuck... feels so good." He murmured in my ear as he started fucking me. I felt tears running down my face, but if Malcolm knew, he didn't stop. He lay on top of me, thrusting his cock in and out, as we'd seen the guy doing to the girl. For me, it felt like an eternity before the fishermen moved off to try another spot and Malcolm took his hand away.

"Stop... please stop... it hurts." I moaned.

"Just relax. I promise not to do it hard." He lied. I lied as well as it wasn't hurting anymore, it was starting to feel good. I knew it shouldn't.

I didn't want it and wanted him to stop, or did I. There was something about doing this that felt so wonderfully dirty and I didn't really want him to stop. He speeded up, thrusting into me faster and faster, moaning in my ear, kissing my neck and cheek. I couldn't help myself and turned my head so he could kiss me on the lips, as if to say don't stop. In truth, I was enjoying it, enjoying the whole idea of being forced to dress up in girl's clothes, enjoying feeling him lying on top of me and the feel of his cock moving in and out, fucking my boy `pussy' as he said.

"Oh yeah, you like it, don't you?" I shook my head, not daring to answer.

"Get on your knees." He hissed, pulling out of me.

"What?"

"Get on your knees like that girl."

"What... no!"

"Do it... I'll do it for you next time." I turned my head and looked at him, knowing the lie for what it was, but I believed him and got on my hands and knees.

The moment I did, Malcolm grabbed my hips and pulled me back as he slipped his stiff cock between my cheeks. This time his cock slipped in easy with barely any pain, and I groaned as I felt his cock slid all the way inside me, even deeper.

"Oh fuck yesssss." He moaned and started pounding his cock into my `pussy' I let out a sob, more in shame than pleasure as he was right, it did feel good, but I felt humiliated letting him fuck me like a girl. Malcolm must have remembered what the guy said to the girl as well.

"Oh yeah, nice tight pussy, bitch." I moaned hearing that, and let out a few squeals of my own, now knowing she didn't do it out of pain, like me, she was enjoying it. I too started wiggling my ass just like her and pushing back against him.

"Oh god... fuck me." I whimpered.

"That's a good little whore, work that pussy... what a nasty boy you are letting me fuck you like a girl."

"Ooooo... please... don't cum inside me."

"Shut up sissy queer boy!"

"Ohgod... don't say that." A boy calling another boy a sissy or a queer at school was the worst thing you could do. After that, everyone pick on him and called him names.

"Oh yeah, Bobby is a little sissy queer boy... panty wearing sissy queer." I shuddered in horror and reached down to stoke my cock.

"Ooooo... please... say it again." I moaned, hating myself for saying it.

"Ummm now you're my cock sucking sissy cunt, aren't you, Bobby."

"Yes... yes... yes I am."

"Just a dirty little panty wearing faggot." He said the forbidden word on my ear and I almost shot my load.

"Oh god... no... not that."

"Oh yeah, that's what you are," he panted, fucking me as fast as he could, "you're my dirty little sissy, panty wearing, cock sucking, sissy faggot bitch now, aren't you!"

"Oh fuck... yesssss." Malcolm thrust his cock all the way into my `pussy' and held it there, cumming just before I did, filling my bottom with his cum. That felt so wonderfully, making me shuddered in shame as I shot a long stream of cum across the blanket.

We both collapsed as lay there panting for breath, unable to move for a moment as we floated on a soft pink cloud of sexual satisfaction. Neither of us knew those words at that time as we just lay there with the edge of the blanket pulled over us. How long we slept, I don't know, only coming awake a few hours later. One look at what I was wearing sent a wave of shame and humiliation washing over me, and I quickly stripped of the clothes, swearing to myself that I'd never do that again.

"Arr, you look so good dressed like that." Malcolm sighed, looking at me while I stripped and got dress in my own clothes.

"Shut up! That's not funny." I pouted. "You made me wear them."

"I know, but it was so much fun." He giggled. I didn't think so as I felt his cum leaking out of me into my underpants. I blushed, thinking that I might have a wet spot showing at the back when we walked home.

"It's a pity I have to put them back. I have to wash and dry them so my sisters won't know I took them." He grouched. To me that was a good thing as I wouldn't have to wear them again, but I couldn't help glancing at them as he rolled them up in the towel and nibbling my lower lip. What if he found something else? Would he `force' me to wear them again? I shivered at the thought and pushed it out of my mind. I never wanted to wear girl's clothes again, ever.

The trouble was, I couldn't stop thinking about them, and looking at those dirty panty boys in the magazines and playing with myself. As if by mutual agreement, we didn't talk about what had happened, or play with each other for a few days. Of course, it didn't last and we soon ended up in my bedroom naked and playing with each other. Mostly is was a mutual jack of, sucking session, but wearing panties wasn't far from our minds, making references to panty wearing sissy faggots and being dirty little queers. In the end, Malcolm insisted it was my turn to find a pair of panties to wear, but it wasn't until my mother and I went to visit an aunt that I got the chance to get a pair. My aunt had a young daughter and when I got the chance, I snuck into her room and went through her panty draw. Everything was so neatly in place I didn't dare take anything for fear she or her mother would notice. Having been told to go play in the back garden I did, as sitting around listening to my mother and aunt talk about stupid things was boring. Walking through the kitchen, I passed the laundry room where I had a thought. It only took a moment for me to find the laundry basket and a pile of clean clothes. Digging through I found some of her underwear, quickly spotting a pair of pink undies. In a flash, they were in my pocket and I was out the back door, shaking like a leaf.

It wasn't until I got home that I had a chance to examine them, shivering with excitement. They were the sort of panties a young girl wears, puffy so maybe you could wear a diaper under them, with little red bows and pink ribbons around the leg opening and hanging down each side. The material was soft and shiny at the back, and almost transparent at the front. I just hoped they weren't her favorite panties or my mother would be getting a call to ask if I'd stolen them. That would be so embarrassing, so I hid them well just in case my mother went looking for them. I was nervous for a few days, but she didn't call and I didn't get any funny looks from my Mom, so I figures I'd gotten away with it. The moment Malcolm saw them, he stripped and pulled them on and started prancing around, limp wristed and tittering like a little girl. I felt a little jealous seeing him wearing them as I thought he'd make me wear them first. We played for a while, not cumming, but getting close. At last, he pulled them off and held them out to me.

"You're turn." He giggled. "Let's see you prance around in them."

"What... no..." I spluttered, blushing bright red. That was Malcolm's signal to pull me over his knee and spank me until I agreed. Gradually he was getting bossier and I didn't just have to put them on, but swish and prance around for him. He insisted I put my hands out like a limp wristed sissy boy and lisp my words, smacking my bottom if I didn't do it right.

"That's it you little sissy fag, show me what a little bitch you are." That made me get harder, and I didn't have to say anything to make him talk dirty to me. "Oh yes, what a pathetic little sissy queer boy you are, prancing around in those pretty little girl's panties."

"OOOhhhh yeth... I'm such a dirty little sissy fairy." I lisped.

"Get down on your knees and lick my cock, sissy faggot." He grabbed my shoulder and pushed me to the floor, almost forcing his stiff cock into my mouth. Of course, he tried to push it all the way in, and that made me gag, but not as much as before.

"Take it all, sissy bitch. Sucking my dirty cock." I knelt there, stroking my cock, tears running down my face, and taking a deep breath I took his cock all the way into my mouth, hardly gagging as all six inches slipped all the way in. I shuddered, desperate to hold my gag reflex back. I managed to for a few moments and thankfully he pulled his dick back out and let me breath. Once he'd got it all the way in once he expected me to take it all the way from them on. It was difficult, and I gagged a lot but finally I managed to take and hold his cock all the way in my mouth few several seconds. That felt so nasty and dirty and it didn't take long for him to fill my mouth with his cum. I squealed around his cock, and tried to pull away, but he wouldn't let me.

"Swallow it you filthy little faggot, swallow all my dirty cum!" Between his cock fucking my mouth and trying to breath I swallowed, feeling it slid down my throat. It was too much and I shot my load all over the floor. Pulling out he pushed my head to the floor, giggling.

"Lick it all up you dirty little queer." I couldn't help myself, feeling so ashamed, I did. For a while, I just lay on my bed and cried while Malcolm lay beside me stoking my hair.

"That's okay. I know how you feel." He soothed, but that only made me cry harder.

"You promised you wouldn't do that." I sobbed.

"I know. I'm sorry, but it felt so good I couldn't stop." I swallowed again, trying to get the taste of his cum out of my mouth, but it didn't help.

Without ever realizing it, I slowly became his panty bitch with my wearing the panties and pink lipstick more than he did, and ending up on my knees sucking his cock. Of course, he lied and filled my mouth and throat with his cum on more than one occasion. I of course protested, cried, and told him I hated it, but after a while, I knew that was exactly what I wanted. I liked him spanking me, making me cry, forcing me to wear the panties, and sucking him off while kneeling in front of him. I jacked off night after night just thinking about it, thinking about being dressed up all the way like some dirty little faggot in the magazine.

Sadly, that wonderful summer came to an end and school started again, so we didn't have enough time to play a lot. When we did, inevitable I wore the panties and lipstick and forced to my knee to suck him off. After a while, I didn't question it any more. This was my place, on my knees sucking his cock but it scared me. What if I couldn't stop, what then? Maybe I was to the point where I couldn't stop. Either way I never found out as without warning, his Dad got a job in another city and they moved. I did manage to get one last quick meeting with him and as a parting present he sucked me off all the way and I shot my load into his mouth like he always wanted.

I set there in the booth opposite him, thinking about all the things we used to do, coloring slightly under his gaze while he massaged my crotch with his foot. I tried to tell myself that it didn't turn me on, but that would be a lie seeing my cock was hard inside my pants. He could feel that and smiled.

"Still the same old Bobby I knew." He chuckled.

"No, not really. I don't wear panties anymore."

"Shame, you should, you always did look good in them." He withdrew his foot and looked at his watch. "It's getting late and we both have to be at work early." Shifting my cock into a more comfortable position, I finished my drink, hoping no one would see my boner as we left. I wasn't sure how I felt about meeting my old friend, half-scared, half-excited. The next week went by in a whirl as each of the interns/associates vied for a converted full associate position. Gradually each fell by the wayside, the group grew smaller, and smaller until there was only three of remained.

"Bill Woodcock," my supervisor made me jump as he walked up behind me and clapped me on the shoulder, I cringed, thinking the worst, "congratulations, you made it." I gulped, feeling myself shake in relief.

"I did?"

"Yup, you did, in fact one of the partner want you on his design team. He liked your work."

"Wow, that's great."

"He'd pretty tough, but fair. You turn in good work like you've been doing and you'll get along find."

"No problem." I stuttered feeling a sense of relief wash over me.

"You'll be moving to a new office on the eighth floor and work directly under his supervision from now on."

"Oh, okay. Who will I be working for?"

"Mr. Elliot. Get your things together and I'll take you up to meet him. For a moment, the name didn't click. Then I did, Malcolm. I swallowed carefully and simply nodded. Gathering my things, I followed him to the eighth floor and we went through the awkward introductions as if we didn't know each other at all.

"I'm glad you'll be working for us as an associate, Bill. We work long hours here but you'll be well compensated. I hope you have a long and successful career with us." It sounded like the normal company BS speech for the new comers, and after shaking hands all round, he showed me to a small office next to his. He didn't say anything until we were alone, and then only to smile and welcome me abroad.

I took the rest of the day to settle in and get my stuff sported out, but just as I was about to leave, Malcolm stuck his head into my office.

"Hey, I'm going to the gym, want to come?" I didn't know what to say and just nodded. The gym turned out to be the company gym on the top floor and there were a number of people using the work out equipment.

"Um... I don't have any shorts or sweat shirts with me." I said as a way of bugging out.

"No problem. I have a spare set in my bag you can use those for now." We changed and headed into the gym, spending the next hour working up a sweat on the machines. I did think that the shorts and muscle shirt I was wearing were a little small and not really something, he could fit into. I did wonder why he insisted on wearing a baggy tracksuit top, but shrugged it off. At no time did he give any indication that we were anything more than work associates as he rambled on about the engineering project on his plate, and how I'd be an asset to the design team. After we showered and dress again, he invited me to dinner, and I was hardly in a position to refuse, but again, he kelp the conversation on work. Just as we were about to go our separate ways, he took my upper arm and turn me to face him.

"You want to come over to dinner at my place tomorrow night?" There is was the invitation to dinner, and maybe something else. I looked him in the eye to see if I could discern what he was thinking but other than a slight smile, there was nothing. I hesitated, torn between two conflicting desires. Say yes and maybe start our relationship all over again, and what that might entail, or say no. My no, was more out of fear of what might happen, and the secret disappointment if it didn't.

"Yeah, okay." I said at last, and I had the impression that Malcolm was holding his breath waiting for my answer.

"Great. I'll give you the address tomorrow and you can come around after work." I swallowed carefully and nodded, wondering what I'd let myself in for.

The day went well and he kept me busy and running for department to department to gather the latest data and information on several projects. I didn't even have time for a real lunch, just a quick sandwich, and a cup of coffee. As it was a Friday, we worked late and by the time we finished most of the people in the office were gone. Malcolm gave me the address and told me to be there by eight o'clock, which just gave me time to get back to my apartment and change. I did, slapping on some deodorant and after-shave lotion after shaving, but not enough time to shower. Fresh underwear, a pair of tan slacks, and a loose white shirt, loafers and a light jacket and I was out the door and on my way. Why I was rushing, I didn't know, as I doubt he'd mind me being late. Even so, what with the traffic in Hollywood on a Friday night I was still fifteen minutes late. I lost an additional ten minutes trying to find his place off Laurel Canyon, at last finding a nice two-story house set back from the road in some trees.

"You're a little late, but no matter. I thought you'd changed your mind."

I detected a definite note of relief in his voice, but other than a smile and standing back for me to enter, he gave no indication he was mad at me. Malcolm was wearing a lose, pinkish silk shirt, white slacks and no shoes, and that indicated I should kick my loafer off as I entered. As he closed and locked the door behind me, a slight shiver ran down my body that I put down to the cool breeze blowing down from the overhead fan. Dinner was great, light and not to filling along with several glasses of red wine, and other than a few glances he kept the conversation light and free from sexual overtones, until we ended up side by side on the huge couch. I felt very relaxed after three glasses of wine and sipping on my fourth.

"You looked good in the gym the other night."

"Thanks, you didn't look to bad yourself from what I could see. Weren't you hot in that tracksuit top?"

"A little." He smiled as if he had a secret. "How come you don't wear panties anymore?" That caught me by surprise and I blushed. I shrugged, as I didn't know what to say.

I... I didn't want to after you and your family moved." I finally managed to get out. This wasn't how I imagined the conversation would go, but as usual, Malcolm was direct and to the point.

"I was a bit surprised you don't have more hair on your body, but I like it, it suits you, especially if you were wearing panties." Malcolm shifted closer and started stroking my hair. "I like the long hair as well, but you should be blonder."

"Malcolm... I... I..." I didn't have a clue what I wanted to say.

"Poor little Bobby, still scared and reluctant to tell me what he wants."

"N... no I'm not." I blurted out.

"Oh I think you are. Finish your wine." I obediently swallowed the last mouthful and he took the glass from me and put in on the coffee table.

"I think that you want someone to spank you to tears and force you to put them on, just like before."

"N...no, it's not that." I stammered, feeling a little light headed as he put his hand on my thigh and gently squeezed.

"Yes it is, you haven't found anyone to do that to you, have you, and that's what you want."

"No... no it isn't... I haven't... I mean." I wasn't even sure what I was saying.

"Oh I think that's what you want and need." His hand moved up and started to undo my pants and I was powerless to stop him. I felt my eyes get wet as he unzipping the fly, his hand moved down my head to the back of my neck, gently pulling me towards him. As if drawn by a magnet I leaned forward and over his lap.

"No... please... this isn't what I want." I pleaded, but he didn't listen and pulled me all the over his lap. I couldn't believe this was happening, shivering, and blushing with embarrassment as he gradually worked my pants down over my butt.

"Yes, that's much better, but you can't wear these underpants, they are men's underpants and you know you aren't really a man, don't you, Bobbie."

"Oh god... please... don't... don't say that."

"Let's get these underpants down and see if you still have that nice tight sissy ass." My body shuddered as he slowly worked my underpants down and his hand stroking and needing the cheeks of my bottom.

"Oh god... please... don't." I begged.

"Oh no, what Bobbie need is a good spanking to make him behave, isn't it."

His hand landed with a stinging slap, first on one cheek, then the other. I winced feeling the sting and determined not to cry. Smack -- smack -- smack -- smack. Hard stinging slaps that brought tears to my eyes, but more from embarrassment than actual pain. Smack -- smack -- smack -- smack as four more landed, even harder. My breath hissed in and out through my clenched teeth as I tried desperately not to give him the satisfaction of hearing and seeing me cry.

"Ummm I think dirty little Bobbie needs something a little harder."

"God, no... please." I sobbed as I felt something cold and hard pressed against my sore cheeks. Oh, fuck... he had a paddle. He knew he was going to spank me and had it hidden. "Whack! -- whack! -- whack! -- whack! God that hurt and I still refused to cry, stifling a sob as best I could.

"Let it go, Bobbie. Tell me you're going to be an obedient little boy." "Whack! -- whack! -- whack! -- whack! God the words hurt more than the paddle and I felt as if I was back in our secret hiding place or my bedroom getting a spanking from him all over again.

"Please Malcolm... stop."

"Tell me what you're going to do?" Whack! -- whack! -- whack! -- whack! It was too much and I let go and cried.

"Please... I'll do it!" I sobbed.

"Do what, Bobbie?"

"I'll... I put the panties on."

"And do as you're told?"

"Yes... yes, yes... don't spank me anymore." I blubbered, unable to control myself.

"You're going to go into the spare bedroom and take a nice shower and then put the pretty panties and the other things on, aren't you." Whack! -- whack! -- whack! -- whack!

"Y...yes... I promise... I'll be good." I sobbed, kicking my legs in pain.

"Good." He slipped me off his lap to kneel on the floor, lifting my head to look me in the eyes while I desperately tried to relieve the pain in my butt. "You go and have the shower and put the things I'll leave on the bed. You be good and do what you're told and I'll give you a nice surprise, understand?"

"Y...yes, I understand." Why I hadn't fought and tried to get away I didn't know, nor why I was agreeing to do what he told me, only that I did. Stumbling to my feet, he led me to a bedroom and pushed me inside.

"Make sure you shampoo your hair and use the conditioner, or else." I nodded and sniffed back another tear seeing him smiles and blow me a kiss.

After stripping, I stood there for a moment wondering what I was doing. Is this what I really wanted? It was a stupid question really, having gone this far I couldn't turn back. I showered and did as he said and shampooed my hair and used the fragrant conditioner as the flowing water cooled my burning bottom. After drying off I used the blow dryer to dry my hair and comb it out, but without a rubber band or scrunchy I had to let it hand lose instead of the ponytail I usually kept it in. Walking back into the bedroom, I sucked in my breath seeing what was now lying on the single bed. Not only was there a pair of bright pink, boy's short crotchless panties, but a pair of white stocking and a white lace garter belt along with a matching bra. The frosty pink lipstick, eye shadow, and eyeliner told me what he wanted me to do. Again, he wanted me to dress up as a girl, evident by the sheer pink nylon teddy hanging on the wardrobe door and the strappy black shoes beneath them.

"Oh fuck!" I shivered, knowing Malcolm was going to make me his bitch again. It took me all of five second for me to make up my mind and I started dressing.

Buckling the ankle straps of the shoes I stood there looking at myself in the mirror, feeling the delicious, wonderful feeling of shame wash over me. I looked like a total slut and so far from the normal straight man, I pretended to be as possible. It dawned on me then that this was what I'd wanted for a long time and didn't know it. Walking carefully I made my way back to the living room and stood there waiting, fully aware of how exposed I was with my semi hard cock sticking out from between the folds of the pink satin panties, unsure what to do next, or what was going to happen.

"Malcolm?" I called.

"Kneel down and close your eye." He called and I slowly sank to my knees and did what he said.

The first thing I heard was the sound of high heel on the floor and the swish of nylon stocking rubbing against each other. Whatever else he was wearing, Malcolm was wearing stocking and high heels. My cock stiffened at the thought wondering what else he was wearing. He came up behind me and stroked my hair, flipping it forward to frame my face more. I shivered at the touch but kept my eyes closed as he walked around to stand in front of me.

"I told you I had a nice surprise for you, Bobbie." He murmured, making my name sound like a girl's name. "Open your eyes." I did and sucked in my breath in shock. "You see, I didn't stop wearing panties, Bobbie."

The Malcolm I knew was gone and in his place was a panty boy's wet dream. His figure was pulled into an hourglass shape by a tight, black, and red satin and lace, open bottom corset. The six attached garter straps held up a pair of jet-black, lace topped stocking the look as if they were sprayed on his long shapely legs. The strappy, spiked heels firmed his calf and thighs muscles in a way that any women would give her life for. My eyes traveled up, seeing the swell of his breast above the top of the corset, and they were real breasts, no sticks-ons. How he came to have real breast I didn't know, only that I wanted to kiss them. He now wore a long black wig over his short hair and his face was made up in such a way I couldn't see any maleness anywhere. His lips were colored `cock sucking' red as the guys used to say and coated with gloss, giving them a pouty look. In the end, I couldn't help looking down at his crotch having skipped it the first time I looked at him, half expecting to see a pussy. Instead, I saw his cock through the sheer black skimpy panties he was wearing, and it looked a lot bigger than I remembered. I swallowed hard, my mouth as dry as a bone. Not that I had to say anything, just the look on my face told him everything he wanted to know.

"You look so sweet dressed like that, Bobbie, so fuckable." I gulped and shivered, glancing at his slowly stiffening cock. He stepped closer and pulled my head towards him and he didn't have to tell me, I immediately started kissing his cock through the panties.

"Ooooo yes... you are still a naughty little boy, aren't you, Bobbie." I nodded, stifling a sob. "Such a dirty little boy kissing my cock like that. Are you still a little sissy queerboy, Bobbie?"

"Yes." I sobbed as he stroked my hair.

"That's yes, Mistress." I sucked my breath in.

"Y...yes Mistress." Shivering as I said it.

"I've come a long way since we played together, but poor little sissy Bobbie has been trapped into pretending he's a real man for so long. Isn't that true, Bobbie?"

"Yes, Mistress." I sobbed, unable to lie to him.

"No one to spank and punish him for being a bad little boy, no one to make him wear panties and girl's clothes like a pathetic little sissy fag. No cocks for him to suck or fuck his tight boy pussy." He was deliberately making me cry I shame, whispering dirty things to me as he stroked my hair and made up face.

"I've thought about you since then, and one day I went out and brought you a special present, never thinking I'd ever had the pleasure of actually giving it to you, now I can."

"Please... I don't... I'm not anymore."

"Not what anymore? A panty-wearing sissy queer? What are you so afeard of, Bobbie?" I shook my head, not daring to answer at first. "Come on tell me, what are you afraid of?"

"T...that I won't be able to stop." I blubbered at last.

"Ohhh you're afraid you'll be hooked, unable to stop wearing slutty sissy panties."

"Yes."

"Say yes, Mistress."

"Yes, Mistress."

"When you see what I brought you, you won't have to worry anymore." Saying that he held out his hand, the nails now bright red. I looked and started crying, knowing what he meant. He held out a wide, silver studded pink collar and waved it in my face.

"Oh god!"

"I wanted to put something like this on you're a long time ago, but never could. I wanted to make you my sissy bitch boy and force you to dress up in girl's clothes when I wanted. Put you on your knees where you belonged sucking my cock, or bend you over when I pleased and fuck your tight boy pussy like a dirty little slut." All I could do was cry, party in shame, partly in excitement and humiliation, knowing he knew exactly that I wanted, and what turned me on.

"Please Malcolm... Mistress. I don't..." My voice trailed off as he brushed the pink collar across my shoulders and the back of my neck.

"You want to wear this don't you? Be turned into my bitch. My property."

"Oh god."

"Do you want me to be your Mistress, Bobbie, make you do all the nasty, dirty things you're so afraid to do?" All I could do was nod and cry. "Good, here, put the collar on to show me this is what you want. Once you have I'll add this." He held up a small silver colored padlock, turning it so it winked in the light.

I shuddered, knowing that once I put the collar on, Malcolm... now my Mistress would lock it on me and I'd be trapped. My hands shook as I took the collar and fitted it around my throat, hardly daring to breath, already feeling tight even before I buckled the ends together. I looked up and saw my Mistress take his stiff cock out of his panties, now pointing straight at me.

"That's a good boy, Bobbie. Now suck your Mistresses beautiful cock while I put this padlock on." It was pure humiliation, making me suck him off while he took my manhood away and turned me into his cock sucking, sissy fag bitch boy. I only hesitated for a moment before letting the head of his stiff cock slip between my now wet lips. I whimpered and took a deep breath before sucking his hard cock into my mouth and holding it there. His cock was definitely a lot bigger than I remembered, forcing myself not to gag as the head hit the back of my throat. I cried them, hot tears of shame running down my face as I knelt there. He took his time, enjoying the feeling of power he had over me before he snapped the lock shut. I heard it click and shivered. I was his now to do with whatever he wanted. I knew the punishment I'd get for refusing, hating it at the same time as wanting it. Malcolm pulled his cock out of my mouth and walked over to a side table, coming back with an addition to add to my humiliation. It was a chain leash and it only took a moment for him to snap it onto my collar.

"Up, bitch. Time to go to the bedroom."

I stood, and it only took a slight tug on the leash and I followed him like an obedient little puppy to his bedroom, head hanging, tears rolling down my face, tears of pleasure rather than shame, knowing that this was exactly what I wanted but too scared to admit it. Now I wouldn't be able to.

"From now on you will always kneel in my presents unless I tell you otherwise."

"Yes, Mistress." Malcolm waited until I knelt down before continuing.

"Good. You will be perfectly clean and available to me at all times, day or night from now on."

"But... but what about work... Mistress?"

"Did I give you permission to speak?" He snapped, and I shook my head and remained silent.

"What about day or night didn't you understand?"

"Nothing Mistress." I answered, hanging my head.

"Was it something I said, or did you think this was a debating society? Or that you had a choice or any say so in the matter?" I shook my head. "Good, I'm so glad we cleared up that little misunderstanding. Your position is simple. You are here to please me all the time, not the other way round, understood?"

"Yes, Mistress."

"Unless you want to turn up for work on Monday morning wearing your cute pink collar?"

"Oh god... no."

"I thought so, and don't think you can cut the collar off. You can't. There is a thick stainless steel band running through the center what would take a blow torch to cut off, and the lock is pick proof." Not that I wanted to take the collar off except maybe to go to work.

"Yes, Mistress." I sighed as Malcolm came over and stroked my hair.

"One of the first things I'll have to do is something about your hair."

"My hair, Mistress?"

"Yes, removing it all from your body and having the rest trimmed and colored into a better shape. I want my sissy bitch boy looking sweet and smooth in private." He smiled down at me as he moved closer. A sight push of his hand and I was kissing and licking his cock, making it hard again. "Ummm yes, you haven't forgotten everything I taught you." Visions of me doing this before flashed through my brain, remembering how he loved to tease and humiliate me.

"You always were a good little cock sucker. Now, let's not have any nonsense about you not being able to take it down your throat. Holding my head, he started fucking my mouth, groaning as he did, gradually thrusting it deeper and deeper. The head hit the back of my throat and I desperately held off my gag reflex, whimpering as he pushed it all the way in.

"Oh fuck yes, dirty little Bobbie has a cock all the way down his throat like a good little sissy faggot!" He pulled out so I could breath and started fucking my mouth, long hard strokes, but even as much as I tried, I could stop myself chocking.

That didn't stop Malcolm, he just waited for the spasm to pass and continued fucking my mouth. The lack of air, the wine, excitement or a combination of all three sent me into an erotic daze to the point where I didn't gag anymore, and I started sucking as he pumped his cock all the way in and out of my mouth. I no longer tried to push him away, but held onto him, wrapping my arms around his butt, and pulling him towards me. I didn't even think about touching myself, knowing I was here for his pleasure, not mine. Even so, my cock was as stiff as a bar sticking out of the front of my sissy faggot panties, painfully hard. I'd never felt like this or got so hard with any of my dates, always thinking how much I'd like to be wearing their panties instead. How long he fucked my mouth I don't know, having lost track of time somewhere, but at last he stopped and pulled his cock out of my eager mouth with a popping sound, as I was reluctant to let go.

"What on earth is that sticking out of your panties, Bobbie?" He asked, tapping me under the chin. "Stand up!" I did, now looking down at the top of his breasts. They were real. Somewhere, somehow Malcolm had grown real titties and for some reason that made me shiver. I jumped as he reached down and fingered my stiff cock and laughed.

"Do you think just because you have a silly little cock and a pair of balls that makes you a man?"

"I... um... no Mistress." I stuttered, wincing as he dragged his long nails across the sensitive skin.

"That's right, Bobbie. Having a little cock clitty and a pair of little balls doesn't make a swishy little sissy fairy like you a man at all. But, we'll have to do something about this. We don't want you tenting your panties and dress every time you get excited, do we." I knew it was a rhetorical question and didn't answer, knowing it was true.

"Yes, I think we should do something about that right now and put you into chastity for your own good."

"Oh god... no... please... not that... mistress."

"Did you just give me attitude? He hissed, and grabbing me by the hair, he pulled me over to the bed and over his lap as he sat. All I could do was moan, knowing what he was going to do. My panties came down and he started spanking my sore butt again, hard stinging slaps he kept it up until I was kicking and crying, begging him to stop, and at last, he did.

"Go stand in the corner until I tell you to move." I did, stumbling across the room on my high heels with my panties hobbling me around my thighs. I heard him opening draws as if looking for something.

"Are yes, here it is. Come here Bobbie." I shuffled over and stood in front of him, tearing up again when I saw what was in his hands. By now, my cock had shrunk to a quarter of its normal size, now no more than three inches long. Malcolm sat on the bed, slipping a plastic loop through a pink plastic tube. Reaching out he slipped the loop over the head of my cock and pulled it straight out. I winced in pain and said nothing as he worked the lubricated curved tube over my circumcised cock. I stood there and whimpered as the head appeared out the end of the tube, but he wasn't finished yet. Pulling the loop and pushing the tube, he worked it all the way on, already painfully tight. I doubted I could get any sort of a hard on wearing this. He then pulled the attached plastic ring tight behind my ball sack and locked it in place with a key.

"There, that's much better. Oh, by the way, this is the only key that will unlock the device. If you don't behave yourself, I'll throw it away or destroy it. Then you'll have to wear it permanently." He smiled up at me. "You are going to be an obedience little slut from now on, aren't you, Bobbie." I gulped and nodded my head. As an added humiliation, Malcolm tied a pink bow around the head of my cock that had a small bell on the end on the end of the hanging ribbon. Pulling my panties back up, he pulled my limp cock and the ribbon out so it hung between my legs.

"Thought so. Now prance back out into the living room and get me another glass of wine, and make sure you swish properly like a taught you."

I nodded, remembering how we'd swished and pranced around my bedroom, all limp wristed and swishy like a sissy fairy. It was hard, and I felt so stupid and humiliated prancing out of the bedroom holding my hands out and my wrists limp. I knew that if I didn't, or didn't please him I'd be over his lap again for another spanking. As I swished across the living room to the bar, I caught a glimpse of myself in the wall mirror and almost started crying again. There was nothing left of the young man who'd walked into his house just a few hours ago. All I saw was a limp wristed little sissy faggot in slutty lingerie, even sluttier makeup and a pink studded collar prancing his way across the room, the little bell on the end of the pink ribbon around my cock tinkling as I walked. A wave of shame washed over me, not so much because of what I was wearing, or how I looked, but because I'd let it happen. It was my fault I was dressed and made up like this and I had no one to blame but myself. I tried to ignore the discomfort between my legs but it was hard. That horrible little bell kept tinkling every time my cock twitched, and it was twitching a lot just to remind me of my position.

Tripping back to the bedroom, I made sure my hand was out, palm up and hand limp, seeing Malcolm smile as I pranced in and knelt at her feet as she'd ordered me to. I didn't want to get spanked for forgetting that. Just then, the phone rang, and picking it up he stroked my hair and cheek while to talked.

"Yes, this is Malcolm." I closed my eyes, liking the feeling of him touching me. "Oh hi Dennis, how are you."

I didn't listen to the conversation really, but did hear something about a cocktail party tomorrow night. I shivered hoping she'd hide me away while the people were here. My other thought was that she might dress me up and make me walk around where people could see me. I gulped at that thought. Other than Malcolm, no one knew I was a panty boy. What if people from the office were there?

"Now then, where were we? Oh, yes, about next week. I'll make some appointment and take you in for your tramp stamp, get your ears pierced a full facial and have your body hair removed permanently. It's a shame you won't be able to have your nails and makeup done professional. We don't want people at the office to think you are a total slut, at least not yet." I looked at her with growing horror. This wasn't just some kinky game to her. She... Malcolm was forcing me down a road I was always afraid to take. "I'll also need to take you to the Doctor for a check up and get a prescription for you hormones."

"Hormones... Mistress?"

"Yes of course. In a few months you'll have a nice pair of little girl titties for me to play with, and once they get bigger I'll have the nipples and your cock pierced for the rings." Malcolm looked at me and smiled. "You didn't think you were ever going to go back to being a boy again, did you?" She could see from the expression on my face that I did.

"Oh no. I hope you enjoyed the last pussy you fucked, because it's the last one you'll ever fuck. You won't be getting pussy anymore, because a sissy bitch like you is pussy. There, there, don't cry, I know this is what you really want but you were just too scared to do it yourself. You'll be so much happier once you're a proper swishy little fuck fairy than you ever were as a pretend man." She laughed hearing me sob.

"Now be a good little boy like you use to be and get on the bed. On your hands and knees, head down and sissy pussy up. It's about time I popped that adult cherry of yours." She smiled and patted the bed beside her. "I'm hoping you are as good a fuck as you use to be, Bobbie."

A slight jerk on the leash got me moving. I climbed onto the bed and got down on my hands and elbows, and like she said, put my face down on the covers, which pushed my boy pussy up for her to use. Malcolm never knew how much I loved being fucked in this position as it made me feel so shamed to be taken like a little bitch. I stopped thinking of Malcolm as a man. She, or he was my Mistress now and I was starting to think of him as a `her' as any semblance to the Malcolm I knew at the office had vanished. Standing, she moved behind me and began stroking my bottom and spreading the opening in my slutty panties, making me shiver.

"First, let's see how tight your boy pussy is, Bobbie." I groaned as she sipped a lubricated finger into my tight rosebud. "Oh yes, you are a little tight ass, aren't you." I tried to relax to make it easier, but she quickly slipped a second finger in beside the first, making me squeal softly into the covers.

"Oh god!" I moaned as she slipped a third finger in.

"Be quite, slut. I know how much you are enjoying this, but you are here to please me, not yourself."

I sobbed and shook my head to try and deny what she was saying, but the truth be told, I was enjoying it, at least the humiliation part. I jumped a little hearing something start to hum and a moment later she placed the tip of a vibrator in my ring and gently pushed. Between the vibration and her working the tip back and forth, the vibrator slipped easily inside me with very little pain. I blushed, wishing I'd thought of doing this myself but I was always too ashamed to ever buy one.

"Noooooo" I moaned as it slipped deeper and deeper inside me.

How much I don't know, eight or nine inches is what it felt like. Malcolm working it in and out, fucking my sissy pussy and making me wiggle with pleasure, but I couldn't help wincing every time my cock twitched and tried to get hard. The tube wouldn't let me and it became very painful. Of course, that was the point. It was designed to stop nasty, dirty sissy pussy boys like me playing with themselves. She was right, if I could, I would have ripped it off so I could play with myself, desperate to cum, but I couldn't, forcing a sob out of me as I started wiggling my butt, wanting more.

"You always were a dirty little boy, weren't you, Bobbie."

"Y...yes... yes Mistress."

"Umm yes. I think the dirty little boy want to feel a real cock in his pussy, don't you slut." I shook my head hard, thinking about the size of Malcolm cock now. "Lying little cunt!" She snapped smacking my bottom hard. "Say it, tell your Mistress what you want." Smacking my bottom again.

"Fuck me Mistress... fuck my sissy pussy." I sobbed, knowing she wasn't going to stop until I said it.

"Whose sissy cunt is this, Bobbie?"

"Yours Mistress."

"And your mouth?"

"Yours Mistress, all yours." I sobbed crying my eyes out as she slowly removed the vibrator.

The next thing I felt was the warm tip of her cock and with a quick push and a flash of pain she slipping the head inside me. I squealed into the bed covers as she began fucking her way inside my, stretching my ring.

"Please Mistress... it hurts."

"I know and it should so you'll remember who took your cherry." The shaft of Malcolm cock was a lot bigger than the head, and a lot longer than it was before.

Gripping my hips tight, she pulled me back as she thrust into me, eliciting more muffled squeals from me, remembering how it felt for him to fuck me when we were boys. I could hear Malcolm panting and moaning as he gradually worked his cock all the way inside, and knew he was enjoying deflowering me all over again. I couldn't help it and started pushing back, wanting him all the way inside me, fucking me like he did before, making me his bitch.

"Look at yourself, Bobbie, see how you look dressed like a dirty little faggot slut and getting fucked like a dirty bitch on your hands and knees.

Lifting my head I looked at myself in the wall mirror, set there just for that purpose and knew I was lost. Delicious waves of shame and humiliation swept over me as I watched, seeing what a dirty little sissy slut I really was, feeling his big hard cock sliding in and out of my tight pussy. Malcolm speeded up and slowed down, working his cock from side to side to help stretch me open until my rosebud was completely relaxed and open. As it did, he started fucking me harder and harder, pounding his cock into me as if he hadn't fucked anything for a very long time.

"Oooo yes... you are as tight as ever and such a wonderful fuck. I think I need to find a really hung stud to open you up properly and breed your sissy ass." He panted, moaning and grunting as he fucked me. "Fuck yes... need to find you some nice rich men to fuck you for money Bobbie, so you can earn your keep like a proper sissy whore."

"Ohhh god... no. Mistress, please... no... don't turn me into a sissy whore." I begged as visions of me fucking and sucking off an endless stream of man who paid Malcolm to use me flowed through my sex soaked brain. The thought of Malcolm turning me into a sissy faggot whore was so wonderfully perverse and horrifying that I shuddered in release, shooting cum all over the bed despite the chastity tube. A moment later, Malcolm pulled me tight against him and he thrust his cock all the way in for the last time. I felt his cock swell for a second just before he filled my sissy pussy with cum. I squealed again, but in pleasure, this time, as my ring gripped his cock as if to hold it in forever.

"God, what a lovely fuck you are, Bobbie, even better than before." He breathed as he sank down over my back. I collapsed under his weight and be both just lay there enjoying the afterglow. After a while, he rolled off me and lay there with a dreamy look on his face.

"Are you going to be my good little obedient sissy slut from now on, Bobbie?"

"Yes, Mistress, I will." I moved closer and kissed his cheek softly. Malcolm turned his head and kissed me on the lips, his tongue flicking into my mouth. This time I didn't resist, accepting that this as his right. He owned me now and I was content.

THE END?