Milking Lessons

Sissy 24 challenge

This is my first attempt at writing a sissy fantasy story. Like 10% of it is based on my personal experience. I hope to continue and complete it someday... but my sissy creative juices are very unpredictable. I'm also working on another hypno video, so stay tuned if you enjoyed the first one. I've learned so much, my next one should be immaculate...

Anyway, enjoy the story:

 

I am awoken in the best way a sissy can imagine. My mistress (Michelle)lies down on top of me, her perfect breasts pressing snuggly against my neck, her gorgeous face inches above mine, our eyes locked despite the almost absolute darkness. "I have a very unique proposal for you today" she says. As I begin to respond she stuffs what I can only assume are dirty panties into my mouth (though I can not tell whether they are mine or hers) and I accept that she wishes my silence. She continues, "I will release you from your chastity device All day today, and if you can go the whole day without cumming, then I will leave it off permanently. But, if you do cum, then the cock cage goes back on, and you will never be able to cum again as long as I'm your mistress." Quite a decision for so early, (I actually don't even know the time, but glance at the clock and see 12:01. Midnight) and Michelle hates when I make her wait for... well pretty much anything. The constant straining of my cock against its prison drives me insane at all times, now not an exception, and with only the positive in mind, I slowly nod to accept her challenge. "I'm so glad you've agreed" she said enthusiastically. Immediately she turned and took the device off, then turned back to me, straddling my body, her wonderfully firm ass pressing down on my newly liberated and (obviously) fully erect cock. "This is going to be so much fun, for everyone!" Something about the way she said that worried me. Who's everyone? What is fun to her? I realize how difficult this day could be, especially considering how twisted a mistress's sense of "fun" can be. I plead for more explanation with my eyes, but she wouldn't say another word. A wicked smile took over her face as she began to slide her ass crack up and down the length of my little dick. Her eyes never left mine, her evil smile remained constant as she continued to tease me in that way. She increased her pace, the lightness of how her ass cheeks hugged my cock began to drive me crazy in hardly no time at all. She began to masturbate on top of me, and occasionally would use a free hand to play with my package or slide a finger into my ass. I know now that I'm not going to last much longer. Soon she stops what she was doing and kisses me passionately on the lips. She hadn't kissed me like that since the times we were dating, back before I was her sissy bitch. The kissing sexier than before, but because she was no longer directly stimulating my cock, I started to feel more in control of that orgasm. She then removes her face from my lips and replaces it with her ass. No place I'd rather be. Grinding her ass into my face, pleasuring herself, and teasing my cock all at the same time I almost shoot my load; but with a laugh, she hops off my face and turns to leave the room. "Don't want you cumming too early do we?" She manages to say through her grin, between the giggles. "We've still got lots of time to play. Get dressed and come downstairs, I've got a big surprise for you! This is going to be the longest day of your life!" I turn to the clock, 1:00, 23 hours remaining. As I get up to dress myself I realize two things: 1.My Mistress can has the power to make me cum at almost any time, she will not let me have a chance at completing my goal. She will break me, and I will be locked in chastity forever, The only question is how much "fun" she wants to have with me first. 2. This really is going to be the longest day of my life.

I opened up my panty drawer and looked inside in an attempt to find my pair of panties for the day. My first thought was my favorite pair, my powder blue thong, but that fabric riding up the crack of my ass would turn me on all day, and I didn't need any extra stimulation today. My pink rhumba panties? No, also too humiliatingly pleasing to wear. Gotta be my white cotton boyshorts; very comfy, very plain. I watch my panties disappear back into the cabinet and I think about my situation. Will my panties disappear, or will my life be nothing but panties from here on out? Either thought scares me. I finish dressing with my mind in a worry flurry and timidly walk downstairs, forcing myself on towards whatever she had in store for me. Chores I supposed. Michelle smiled wide and pounced at me as I reached the foot of the stairs. A hard smack on the ass was my greeting and in one swift motion her perfect hand was pushing my ass out the door. "Get ready for a car ride my brave little sissy, and be prepared, I got a great surprise for you so you don't get bored on the way." In the passenger seat I look down and see a horrifying contraption sticking straight back up at me. Strapped on to the seat and raised 8 inches straight up in the air was a brand new, thick pink vibrator. "Get in." "Or get on I should say" she giggled with a wicked smile, "we don't want to be late for the party." My mouth was agape with all that I had just taken in. Party? At one in the morning? "That's right baby, we're going to a friend of mine's femdom party, and I would just hate to be late with my party favor." I eased down on the pink shaft and went as far down as was comfortable. Before she turned the car on she got out, opened my door, put her face right up next to mine, and said to me "Now don't do a half-assed job tonight honey, you need to do everything 100 percent of the way", she paused, moved even closer and said "for me". She pursed her lips and came even closer as if to kiss me again, I was dying for her lips touch again, I would do anything for her, then... she came down on top of me with all her weight. Driving the full length vibrator all the way into my ass. I had never been penetrated so deeply, it felt like it pushed all the way up into my stomach. Sickening pleasure, and my cock was stiffening rapidly. As she started the vibrations my cock got fully erect. This was the most powerful vibrator I had ever felt, intense ripples of pleasure entirely consumed me. I didn't know how much I could take. "Now just sit there and relax" she said taking her seat and turning the ignition. "It's only about an hour drive."

We arrived at a nice house with about 10 cars parked outside and my asshole still ringing. That was the longest car ride of my life, I had passed my mistress's test, and I'd never been so afraid of speed bumps. "Dismount sissy" sang Michelle playfully. As we got out I thought my nervousness had reached its peak, but I was wrong. Mistress made me strip entirely and handed me a bag saying "sissies have a special dress code at this house." The first thing I pulled out was a gorgeous new pair of silky ultra frilly pink panties. I slid them on, almost surprised at how good they felt on my cock without the cage. These were my new favorite pair of panties without a doubt, I was so horny I half wanted to masturbate right then and end it, and I had barely even started my day. My eyes welled up a little just thinking about my predicament. I put on the tiny skirt and the small white tank top with pink glittery letters spelling out sissy slut. Michelle wiped the tear from my eye and put a thick coat of pink glossy lipstick on me. God I loved her. She led me up to the door in her regular fashion, gently pushing the palm of her hand against my pantied bottom. On the front porch I felt Michelle's sweet breath close on my neck and she whispered in my ear "Relax baby, just have fun with it." With that she rang the bell and slipped a blindfold over my eyes. Great, now I faced whatever was behind those doors blinded. I heard the door open and Michelle guided me in, it sounded very crowded in there, full of women conversing and laughing. I was led further into the room and left alone, Michelle's hand no longer anchored to my ass, no more courage provided from her touch. Just a sissy, all alone, surrounded by what I assumed was a house full of mistresses. The laughter and chatter continued for a minute then slowly died down. Shuffling on the floors. At first it sounded like people leaving but I wasn't sure, maybe some people went upstairs. I could still feel their presence, wondering what they were doing, was I all alone? Doubtful. I could feel them closing in around me, or was that my imagination? SMACK! One hard hit to the back of my panties brought me to my knees. I was forcibly moved around and positioned over one of the mistresses knees, I couldn't tell whether or not it was Michelle. My ass was sticking straight up in the air and as I felt my skirt being lifted up to my back I knew what was coming. The hand sounded like a gunshot coming down on my frilly panty ass. This was not Michelle. I had never been spanked so hard by a bare hand. It lasted only a few minutes and I thought I was spared, but then I was being repositioned again and found myself over another set of knees. A dainty feminine hand ran over the frills on my favorite panties mixing a tickle of pleasure in with the pain I already felt. My cock was rock hard still and she was rubbing against it with her legs as I dangled helplessly in her lap. I felt my panties sliding down and then the spankings started again. But this was no hand, it was a large wooden paddle that felt like a sledgehammer. I gasped in painful surprise and the mistress stroked my hair and cooed: "That's right bitch, moan for me, there's a lot more coming." After that it was a furious assault on my bottom, I lost count of the strokes through the pain and before she was done with me the tears were back in my eyes. I was picked up and moved around and found myself draped across another woman's lap. Placed now so that my cock was sandwiched by her soft thighs. My panties were pulled back up and I received 100 spanks from another bare hand, all the while she was bouncing up and down, jerking off my cock with her thighs. I was passed around again, wound up with my panties down and then felt the sting of a whip. On the next mistress it felt like a hairbrush, then another wooden paddle, then a Singapore cane. I was being passed around by who knows how many Mistresses and spanked hard by each one in her favorite style. The cane hurt so bad I was openly crying the whole time she spanked me, which felt like forever. Tear stained face, gasping for breath, and ass on fire, I was passed around for what would be the last spanking. And they saved the worst for last. I heard an incredibly sexy female Russian voice come from the last Mistress as I straddle her powerful thighs. "Aww this sissy is crying. I don't think she likes getting spanked. Well you are going to learn to love it sissy. I don't stop spanking until you stop crying, got it?" I nodded my head and tried to choke the tears back (not easy for a sissy). I felt freezing cold metal pressed against my bare burning ass. A shiver ran through my body, and then was replaced by blistering pain. She hit harder than I thought was possible and I have no idea what exactly she was hitting me with. Every time I got close to controlling my tears another couple of devastating smacks and they were streaming down my face again. Conversations between the idle mistresses began again, I could hear insults I assumed were aimed at me (pathetic, sissy, pussy, cry-baby) and laughter at me as well, but all sound was drowned out by the thwacking on my ass. The mistresses would walk by and twist and pinch my nipples and slap my face all while making fun of me. I heard one say between giggles "She's gonna spank the cum right out of you, then you'll never get to cum again." So they knew about my bet with Michelle. They all knew and they all wanted me to fail. Surely I would. So embarrassed, so worried about losing the bet, and in so much pain from the continual beating of my ass I broke down. I sobbed uncontrollably, blubbering like a little girl. Now surrounded by laughing mistresses feeling the worst pain and shame of my life I continued bawling harder and harder. They were all touching me now, reaching in to slap, spank, tickle and torment me every part of me at any available opportunity. They were all giggling and teasing me, it seemed to last an eternity. I was crying so hard I couldn't breathe. I couldn't take any more. The last thing I heard before I blacked out was a mistress calling out: "I don't know how much longer this will take, but let's go set up the next room." I heard Michelle call back "Ok, but don't forget the lube."

As I slowly regained consciousness I could gradually begin to comprehend my situation. I couldn't move head an inch, actually I found that my entire body was immobile. I was lying on my back with my legs thrown way back behind my head, and tied tight to an anchor behind me. My cock was mostly soft by now (I had no idea how long I'd been out) but it was pointing directly at my face. My ass was the highest part of my body and I knew what was coming next, I just didn't know when. I thought I might have heard some movement in the room but couldn't be sure. The anticipation combined with the tight bondage was driving me wild and my cock began to grow again. Minutes passed, try as I might I still couldn't move at all. There was rustling to my right, I was sure someone was in there now.... maybe. All I could see was my cock and legs and a fixed spot on the ceiling. Was that a tickle I felt running up my back and ass? I could feel a gentle and pleasurable twirl of my hair. My ass now felt a cold, wet cream being gingerly applied and spread getting ever closer to my asshole. I knew they were messing with me now. A slippery finger penetrated me sharply, causing me to gasp in surprise. How were they doing this? I hadn't even seen anyone yet. Without warning a medium sized pink strap on (about 8 inches I guessed) bobbed into my field of vision to my right. "This is Jessie" I heard a mistresses voice call out. A larger purple strap on appeared right above me "This is Tom" (maybe 9inches). A huge black strapon appeared to my left, "This is Bruce" (maybe 12 inches and as thick as a soup can). Another one materialized, flesh colored, introduced as peter was a very realistic looking 10 incher. "This is Steven"- Another 8 incher with a wide head and tapered shaft. The final one was called Jimmy which was bright sparkly pink, 8 or 9 inches, and had bumps and ridges all along the shaft. "Six distinctly different strapons we have for this game sissy. We've told you their names, now look at each one and repeat the name." "Umm..." I stammered "Jessie, Tom.... Bruce (the big one I told myself, trying to take mental notes) um... Peter." I paused for too long on the next one and watched it smack me in the face. "St-Steven and uh... Jimmy." I couldn't believe how well I did. "Very good, what a smart little sissy we have here, Now pay attention cause here's the game." I'd noticed I'd never heard Michelle's voice and I was wondering where she was, wishing she was at least here with me."We are going to blindfold you", this happened as soon as she said it. "And now we will take turns fucking you with our different strapons until you are able to identify them just by the feeling in your ass. Have Fun!" And with that the first shaft penetrated me. I let it fuck me for a while before I ventured my first guess. Smooth shaft, not too big , felt real nice... "umm.. Jessie!?" I cried out. "Correct" I heard from the voice fucking me and Jessie was quickly removed, and then replaced. It squeezed in so easily and I could feel the ridges right at first. I'd never been fucked by a ridged dildo before and I was enjoying it supremely. I could picture the dildo in my mind but couldn't remember the name, not that I wanted this to stop right now anyway. "umm... uh..." thinking while getting pounded was tough, she was really slamming into me now. "uh..ohhho... Jimmy!" I squealed. "Correct again." Jimmy was removed and followed by a great pushing force on my hole, I knew it was the big one cause it wouldn't fit but right as I was about to yell out Bruce, the giant tool impaled me all at once knocking the wind out of me. I'd never been stretched on all sides like that before. "Bruce, Bruce oh god it's Bruce" I was able to eek out. "Good girl" Bruce was removed and emptiness wallowed inside me, but not for long. The next one slid in effortlessly and was hard to feel, not very distinctive... "ummm... peter"?

I guessed cautiously. "Incorrect." I let out a sob of frustration and heard a familiar giggle come from off to the side. So Michelle was here, she just wasn't actively participating. Another voice said "You will now be penalized for your incorrect guess and we will start over." I had barely a chance to think about what the penalty might be before I felt it. Soft dainty fingers began to massage my cock and then jerk it off faster and faster, stopping about 20 seconds after she started. My little clitty was raging now, I had almost forgotten that the game I was playing now was but a part of the larger game for me not to cum. I felt the great pushing on my hole again, and then the air was once more pumped out of me as the big black dildo ravaged me again. "Bruce" I screamed "Bruce! Bruce!" but Bruce would not yield. I was screaming and crying out in pain from the relentless jackhammering I was receiving. All the way out, and all the way back in HARD! Finally it ceased and I felt one of the smaller ones again. She was barely fucking me, making it impossible for me to identify the dildo, after having been destroyed by Bruce. "umm.. Tom" ...... "Wrong!" she exclaimed triumphantly. The cock massage started again for a bit longer this time but I still managed to hold back my cum. I continued to do well on every dildo except for the one that came right after Bruce. The mistresses were all audibly enjoying my frustrations. I thought I was about to cum but the stimulation always stopped right before the point of no return. Finally I got all six correct in a row and I felt my legs being untied. Finally I thought, I took a deep breath i was exhausted and ready to go back home. My legs now in a normal position the blindfold slipped off just enough for me to see Michelle's beautiful face right over mine. She looked me right in the eyes and smiled and said in a teasing voice: "I'm so proud of you baby", before stepping back to reveal her own large baby blue strap on. "This is Michael" she said while replacing my blindfold and i felt my legs being tied down again. "One of seven distinctly different strapons you must be able to identify by feel alone, in your mouth... I was so shocked my mouth opened wide to scream and cry, but my sissy struggles were silenced by hard plastic ramming down my throat.

Plastic and rubber cocks surround my face. Poking me, slapping me, being thrust into my mouth. I gagged and choked out some names… Tried to remember which dick was which. It was all a blur. Instinctively every muscle in my body surged for escape but I was too well restrained. This made all the women shriek with laughter. I could barely breathe, was gasping for air, my gag reflex getting hit and bypassed. I was fading away. Cocks…. Cocks…. Blackness.

I woke up on a couch downstairs naked; no longer bound or blindfolded. My asshole was sore as hell. My Throat burned like hell’s asshole. I could see the mistresses were leaving, lining up single file by the door. Michelle came over me on the couch, smiled wide and said “Hello my slutty sissy, It’s 6:00 in the morning, I’m pleased you’ve made it this far.” She gently rubbed my cock which was already hard but sprung to full attention with the contact. “We’re leaving now. You will crawl on your hands and knees down the line of ladies and kiss their feet, then look them in the eyes and thank them for everything they have done, and then go wait in the back seat of the car.” My face quickly flushed red, but I of course obeyed. The fierce eyes of these ultra powerful women tore right through me as I pathetically expressed my gratitude for the spankings and the fuckings. I was always forced to go into details. My sissy eyes began to water, that twirling swirly feeling of a billion pink butterflies grew and grew in my sissy stomach. By the time I got to the end of the line tears were streaming down my red puffy face. That sweet sublime sissy shame. I crawled out of the doorway, ass high in the air and heard the mistresses let out a chorus of mocking cheers. My cock was mostly hard, felt great rubbing between my thighs and stomach as I crawled into the back seat of the car. What a pain this thing can cause me. I was exhausted and sore and scared of what my next test might be, but was looking forward to going home. Michelle came out towards the car and told me to sit in the middle and spread my legs wide. She then tied my feet to the two front seats. My hands were tied behind my back and fastened to the seat so I could not move forwards or sideways. Michelle patted my cock playfully and without a word turned back towards the house. I had expected to be going home and didn’t know what she was doing. I stared at the houses front door anxiously awaiting her return. When she did come back I was surprised to see her guiding what appeared to be a very drunk, very short girl. When they arrived at the car door I could tell that the girl was wearing a super frilly pink and white skirt and was incredibly inebriated. She was quite pretty and had a huge contented smile on her face. This girl got in the back with me while Michelle got in front and drove off.

Immediately this girl was straddling one of my legs, touching and rubbing all over my body, and kissing up and down my neck. Michelle said, “This is Tina, a chaste little sissy who had too much to drink. We have to give her a ride”. The sly tone she spoke in tipped me off to the true severity of my situation. Bound and helpless, Completely at the mercy of an intoxicated, sex starved, cock craving sissy. I didn’t have a chance… The sissy was making barely distinguishable high pitched whisper sounds; I couldn’t tell if they were words or little sissy moans of contentment. Her soft lips felt indescribably good on my face, neck…chest….stomach…… I knew where she was going. She softly kissed the head of my cock, licked around the tip; sent ripples through my body. She licked the shaft, licked my balls, put the head in the mouth and ran her tongue around it in endless circles. The feeling was great but I fought against embracing it. Now she was really sucking, deep throating to the extent that my little cock allowed. I could see how amused Michelle was, her eyes constantly checking on my predicament in the rear view mirror. The BJ went on and on and during the long drive I didn’t know if I’d be able to make it. She finally stopped sucking when Michelle stopped at a red light and sissy tina fell off me onto the floor board. She staggered her way back up to the seat next to me. She fumbled around with her frilly skirt until she finally managed to slide off her panties. Adorable, white and pink with hearts and a fluffy layer of ruffle on top and bottom. I was terrified because I didn’t think I last in her tight sissy ass, but I couldn’t help but think how much I would love a pair of those panties. I chuckled to myself, even in dire situations you can’t take the sissy out of a sissy. Tina had a precious tiny sissy clitty locked in a chastity cage; my attention was drawn to it. It looked shriveled, almost as though it had given up from lack of use. I feared almost for certain that my cock would soon be doomed to the same fate. Michelle kindly handed tina some lube which she fumbled around with, but was finally able to open and apply. She kissed me deep and meaningful; I could feel all of her sissy love transferred through our lips. With eyes of great passion and longing she turned around, and dropped right down on my cock and began to work it in to her sissy pussy. I popped in easy, she was pretty tight, but had obviously been fucked in the ass before. She was gently riding me, moaning softly, getting all the way down to the base before gliding back up right to the tip. We hit a bump and her ass fell hard, completely swallowing my cock. I moaned. She Squealed. Michelle laughed out loud. This seemed to give tina an idea. She began bouncing on me hard. Virtually jumping up and down onto my cock wild and recklessly. She was yelling loudly in pleasure now, her head rolling around her neck like a rag doll, her delicious smelling hair flying in my face. My cock tightened extremely. I could feel the pulsing from my balls getting ready to burst through. “Argggghhh!!!!” I exclaimed through clenched teeth, my eyes shut tight, tensing every muscle in my body trying to hold off just a few more seconds. I knew at this point I would not make it.

But suddenly I felt the tempo slow. The sissy’s wild moans of pleasure subsided into soft grunts. The hands she was using as leverage slipped off of my thighs and the dead weight of her body slumped back on my lap and on my chest, my cock still buried as deep as it could be in her ass. This sissy had too much to drink alright, so much in fact that she passed out mid-fucking. My cock was still pulsing away inside of her, as hard as it had ever been. Her warm hole served as the perfect prison to keep me constantly on the absolute edge. Mistress had a smile like a Cheshire cat as she looked back and saw my face. She let out a bone chilling, ball shrinking cackle as she sped off for the speed bumps.

As the car came to a complete stop in the driveway, my cum was still safely inside of me. I never knew about that long gravel road that Michelle took to get home. Michelle exited the car and caught my eye while walking straight towards the house, laughing. She’d been laughing for hours. She wiggled her fingers in a mocking wave before disappearing behind the door, into the house. Great. Left alone again, well if you don’t count sissy tina as company. Every now and then she would shift ever so slightly assuring my constant desperate struggle not to climax. Minutes passed…. S.l.o.w.l.y…

Any attempt to move the sissy off me brought me too close to going over the edge.

M..I..N..U..T..E..S.. Michelle came back out of the house and headed for the car. She began to release me from my bonds as she spoke, “you are going to carry your new friend tina upstairs to the guest bedroom and lie her down.” That sounded like good news. At first. But I could tell from the way she paused, the way her face looked, the way she peeked at me through the corner of her eye…Something sinister was afoot. There will be a catch. She noticed me noticing. When she finished releasing all my limbs she sat down beside me and we shared a knowing glance. “Care to guess?” she said teasingly. “I have to stay inside her don’t I?” She chuckled and replied “You know me too well baby.” That I did. She stood outside the car and anxiously anticipated her amusement. I began to slowly shimmy out the car door as I pondered the best way to pick her up without accidentally withdrawing. I had to bear hug her around the middle and lean way backwards, but she was so light it wasn’t near as difficult as I first imagined. But then walking with her… oh, such exquisite torture. I wasn’t sure if I should go fast or slow. Michelle kindly opened the front door for me, teasing “sissies first” and playfully tickled my ass as I entered the house before her. The stairs were obviously my main obstacle. One at a time, Up and Stop….Rest…. Up and Stop….Rest…. Up and Stop…. Rest… Each step was a thrust into her tight pussy. Each step I thought I might blow my load. Each step I was relieved to find that I didn’t. I finally managed to get to the top, finally managed to get her on the bed. I pulled out ever so gently, terrified not to explode as I withdrew. I breathed a half sigh of relief. Mission accomplished. For now. I turned to leave and saw Michelle in delightfully skin tight pastel yellow Bra and Panties, sexily blocking the door. She smiled and I shivered. How could I be more aroused now, After I pulled out? In an instant she was gone, leaving only a single finger in the doorway motioning me to follow. And follow I did, right into her bedroom where she laid down on the bed and got under the covers. “I know we woke up so early, and you look like you could use a rest in more ways than one, so come take a nap with me.” I couldn’t get into bed fast enough and Michelle giggled at my haste. I found my pink rumba Panties on the pillow laid out for me and I knew what to do without a word from my mistress. The frilly fabric felt (of course) divine on my rock hard cock. It felt more like a sissy clitty again now that I was back in my Panties. I laid down, tucked myself in, and turned to face her. I found that she was already looking back at me, beautiful eyes piercing mine. Nothing could have moved my eyes from where they were fixated. I could tell she was enthralled in my eyes as well. Time passed and meant nothing. We shared an entire wordless conversation, doing nothing but gazing through each others eyes. Gazing into her soul and she into mine we were one. It is the most perfect and rare moment when both Mistress and sissy realize that their love is being reciprocated in full. She loved me just as much as I loved her. She needed to be my Mistress just as much as I needed to be her sissy. Eventually I drifted off into a surprisingly restful sleep, as Michelle continued very gently to rub the ruffles of my Panties. Pleasantly teasing my clitty and balls.

I woke up and reached out for my mistress still lost in a haze of sissy love bliss. What I found instead was sissy tina sharing Michelle’s bed with me and staring intently into my freshly opened eyes. I tried to sit up and find my mistress but found that I had been restrained by the wrists and ankles during my slumber. I heard my Mistress’s voice from the direction of the foot of the bed. “Good Morning sissies. The time is 10:30AM; Don’t want to sleep the day away, besides it’s time for another test. Sissy tina has not cum in over 2 months; I have just released her from her chastity cage.” As my Mistress spoke tina turned herself around, swung a leg over my head, and with her little dickie pushing down towards my mouth, she pulled down my panties and began licking and sucking on my cock. “First one to blow loses” Michelle chuckled. I’d never had a real flesh cock in my mouth before but with tina attempting to milk my ever-stiffening prick I didn’t have time to hesitate. I took the head in my mouth and swirled my tongue. I sucked the length of the shaft and back again. Lick the balls… Deep throat… Gargle… Now I was aggressively fucking my own mouth and throat with her cock. It actually seemed to swell to a very respectable size when stimulated. I choked and gagged. Tina was a great cocksucker, and at the instant I didn’t think I could last another 15 seconds, I felt her pulse in my mouth. I heard her squeal like the little sissy she was (like we both were). And I tasted her warm spunk flowing over my tongue and down my throat splashing up against the insides of my cheeks, nearly filling my mouth. She continued to cum on my lips and chin as we both stopped sucking and she collapsed next to me. Michelle rushed up to my face and leaned down close over me. The former obvious love had faded from her face and was replaced with that all too familiar wicked smile. “Hold that cum in your mouth baby just hold on.” I felt disgusting with that mouthful of jizz in my mouth and Michelle knew it, savoring every moment of my humiliation as she wiped the stray cum from my face and slipped it into my mouth. She pulled my panties back up and lightly played with the ruffles over my clitty, her face no more than 9 inches over mine. She grinned even more devilishly and commanded “Gargle it! Gargle it like you gargled tina’s cock.” Shock and repulsion shown on my face, but Michelle’s face turned to stone and I knew I had no choice but to obey. The thick warm goo in my mouth bubbled and churned, coated my teeth, and bathed my tongue. I gagged but kept gargling. Gagged but kept gargling. Gagged. Gagged. Gargled. Minutes passed... I could actually hear sissy tina giggling at me. Michelle could barely contain her laughter. I could barely contain my tears. “Ok baby enough swishing, swallow it now.” And so I did, feeling more humiliated and nauseous than before. I was untied and told to quickly put on a tee shirt and sweatpants and then meet them down by the car. We had to get sissy tina back to her owner and then progress to my next “sissy test”. I shuffled back to my room trying to compose myself. I put on some of my few remaining drab male clothes over my ruffly panties and returned downstairs and out to the car. There I found all the doors closed and locked, with my Mistress in the driver’s seat talking on her cell phone and laughing. Sissy tina was standing behind the car and motioned for me to come over. When I got there she jumped up and kissed me full on the lips, shoving her delicate tongue deep into my mouth. And as my sissy clitty twitched with lust I heard the trunk latch open. My heart fluttered. Tina climbed off me and crawled into the trunk, then turned to welcome me in. My Mistress’s steely gaze in the driver’s side mirror confirmed what I already knew I had to do. I took a deep breath and timidly began to climb into the trunk, when I heard Michelle call out laughingly “tina is a really sore loser!” Dainty hands grabbed my hips and pulled me in while the trunk closed on top of us. She was fondling my rapidly growing cock before we even got out of the driveway.

I had pretty much subdued little Tina by the time Michelle stopped the car. She was still grinding wildly, occasionally brushing my cock with her ass, but I was ok. Mistress came and took Tina and ordered me to stay in the trunk, which I did for a few minutes until she came back and let me into the passenger seat. We strapped up and took off without a word. A few minutes pass and she tells me that I'm going to spend a few hours getting ready for the night's tasks with some friends of hers, while she is off making arrangements. She says she's got "Big Plans" and I shiver. We pull up to a housing unit at the local college and she orders me out and drives off without a second glance. Alone and confused, I didn't even know where to go, but that problem was soon solved as two attractive young college girls gently seized my elbows and led me to the front door of the building. They tell me amidst huge grins and stifled giggles that they know about my wager with Michelle and have received special instructions to help get me ready. I was brought upstairs and into the large living room of their dorm where 3 more girls were waiting. Their eyes lit up upon seeing me and they got to work, setting chairs and equipment in the middle of the room. The two girls I was with led me past the living room, past a bathroom and into a very girly bedroom. The taller and prettier of the two said her name was Chloe. She was sweet and gentle and looked at me with loving eyes when she told me to strip off my "boy" clothes. When I hesitated the other girl named Melinda slapped my face, grabbed my balls and growled "Now Bitch!". I did as I was told and thought about how much I liked Chloe. And how much I loved Melinda. Something about a women calling me "bitch", it just turns me on so hard. Both girls snickered a little when they saw my mostly hairless body and small but obviously aroused package. Chloe started the shower and Melinda ushered me in with her hand pushing my bare backside. I got in the shower and was soon joined by the two of them. They rubbed me with all sorts of perfumey smelling soaps and lotions and in no time my sissy stick was raging at full attention. They teased me and rubbed their naked wet bodies against mine, even started making out with me helplessly pinned between them. We made sure I was as girlishly smooth as could be, removing even the slightest trace of left behind hair. Melinda even slipped her finger in my ass when I bent down to make sure all the hair was gone from my feet. The shower ended and both girls continued working on my appearance by plucking eyebrows, nosehairs, and picking out blackheads. Before I knew it both girls had slipped on some comfy P.J. type clothes and were leading me back out to the living room, still stark naked. When I turned the corner I saw 7 unfamiliar girls standing in the living room, drinking from martini glasses and staring at me. As I was accustomed to every single one of them smiled and giggled when they saw my naked body. I was ripped out of the shower heaven I was just in and forced back into the cruel embrace of shame. Such soul sucking sissy shame. Chairs were set up in the middle of the room, candles were burning, "John Tucker Must Die" was playing muted on the T.V. and I could hear Fergie singing "My Humps" out of the stereo. I thought about the dozens of times I must have jacked off to that video and cum in my panties. I was sat down in the very center and instantly girls were surrounding me, rubbing up on me, talking high pitched and excitedly. They all wanted to ask the sissy crossdresser some questions. "How old are you?" "How long have you been a crossdresser?" "He's not a crossdresser, he's a transexual, isn't that right?" "No, no I heard Michelle say he was just a sissy." I barely noticed that my hands and feet had been seized and that I was undergoing a manicure and pedicure. "So how long have you been a sissy?" "Yeah, have you always known?" "Do you want to be a girl?" The questions came faster and faster, everyone talking at once. I tried my best to answer everyone but it was getting to be too much. "Have you ever had sex with a woman?" All sound stopped with that question. Everyone froze, eager to hear my response. I was blushing as furiously as could be. "I mean like real sex" Melinda clarified "with you penetrating her." I hung my head and whimpered "no". The girls responded loudly. Half with pity, half with mockery. I was so embarrassed, Chloe could see the tears welling up in my eyes. She calmed the girls down, and set them back to work, the questions continued but in a calmer, less invasive manner. Chloe returned with a fruity martini drink and told me to relax a little. The drink was delicious and soon I could feel the calming effects the alcohol was having on me. Deep Breath.... Just relax... Breathe in the soothing aromas. The polish was tickling my toes. Shania Twain came on the stereo singing "I feel like a woman". Another of my favorites. Just relax... I finish off my drink and I'm feeling much better and I smile as I realize my true situation. Here I am being fawned over and pampered by a room full of cute college girls. This is in fact my dream come true. A living fantasy for any sissy! I began to slip more naturally into my sissy lisping girly voice. I sweetened up my mannerisms and let my wrists go limp. For the first time all day I was able to let go of the stress of this bet. I felt more feminine than I ever had before and noticed that my peenie wasn't even straining anymore... I had transformed into my true girly girl self!! I had another drink and even started to sing along to some songs. When my mani/pedi was done I tried on at least ten pairs of wonderful panties for the girls before we all decided on one. The girls were loving it and their encouragement spurred me on further. In my new panties I danced around to the girly songs and had the best time of my life. I sat back down in my chair as my new best friends gathered around my face and started my sissy makeover! The brushes and fragrances should have sent me further into my deep state of sissy bliss, but I could feel my mind shifting. I could feel that inner girl fading back into the background and could feel my cock start to regain control. My newfound tranquility was gone, I tried desperately to get it back, but the more I tried the further away my inner girl got. And the harder and harder my cock got... Harder.... and Harder... I didn't understand and couldn't control it. I realized that the girls had stopped working on my face and were all now staring at the super stiff cock tenting up in my panties. "Oohh, naughty missy" said one of the girls and tried to flick it back down, almost causing me to blow. I heard a rattling sound to my left and turned to see Melinda shaking a bottle of pills. She put the label close to my face so I could confirm what I already knew.... viagra. "Good Drinks sweety?" mocked Chloe in such a sexy mischievous flirty voice. All the girls laughed. They finished making me over and fully dressing me in soft fluffy material, all the while I was going out of my mind with lust. They stood me up in the middle of the room and down went my skirt and panties, leaving my bobbing throbbing almost purple cock as the center of attention. It felt like I had another heart beating in that thing. Chloe paced around me saying "Michelle will be back for you soon, we just have to do one last thing." I swallowed hard knowing that one last thing could be one too many. Chloe continued: "Michelle wanted you to be pretty all over. We dressed up everything but your sissy clit. Michelle wants your cock covered in lipstick kisses from everyone in the room before you can leave." One at a time they got on their knees before me, applied fresh lipstick, puckered up and left a big fat kissy lipstick mark on my dick. I was as hard as can be and my cock twitched as each girl pressed her lips against it. I knew I could blow at any moment and so did the girls. They started kissing the side and the shaft of it longer and firmer, trying to make me spurt but also trying to avoid a face full of sissy cum. I lost track of how many lips had stained my dick and I really felt that one more kiss would send me over the edge when they finally stopped. I breathed a huge sigh of relief and began to wonder if I would be able to get my panties back up without creaming in them. I could feel myself gently being lowered to my knees and then on my back on the floor. Melinda stooped down to re-apply my lipstick as my legs were lifted back behind my head. My straining cock looked right down in my eye and Chloe sat down on the back of my thighs pushing it right up next to my face. "Just one more big Kissy Sissy Mark, right on the head sweety." I puckered out my lips and stretched my neck but was still about an inch away. I could see all the girls ecstatic faces looking down on me in a circle; giggling, laughing, and chanting something like "sissy kissy cock"... The teasing, the girls, the viagra, and the humiliation were too much to take. In a final effort to make the last mark I stretched out my neck as far as it would go, Chloe pushed down on my cock, my shiny red lips coated the head in a beautiful kiss mark, and semen exploded out onto my face, in my mouth, up my nose, and puddled up around my eyes. For a second the girls were stunned with slight gasps of shock and awe, and then doubled up with humiliating cackling laughter. Chloe fell off me she was laughing so hard. Gagging on my own cumload and choking on my utter embarrassment and defeat, I heard the clicking of a dozen cell phone cameras, and I began to sob...

Makes me go MMMM