Just as they had promised, Mommy and her friend Mary had done their best to continue their humilation and teasing of me – breaking down my self-esteem until I was a pathetic, always horny slut – willing to degrade myself however it pleased them – all so I could cum again.
These days my mind continually swirled with lust-filled thoughts – and my little sissy-stick was locked up in a chastity tube so all I could do was caress my own nipples. It was such an exquisite sensation – but it made me even hornier and more humiliated each time I did it. It was a vicious, vicious cycle – the horniness from being locked in chastity was driving me out of my mind, a constant, never ending and overwhelming force in my body and mind. My brain burned with thoughts of new humiliations and soft, teasing caresses and words designed to make me feel even more pathetic and worthless, even as they inflamed my desire.
My poor cock strained in it’s curved chastity tube, unable to fully erect, but with blood constantly trying to flood it’s bulging veins. It was yet another delicious agony I suffered for the privilege of serving my Mommy and her friends.
Mommy was a brunette goddess, 5’8” tall with 38GG breasts and the most perfect legs you’d ever seen. She was 38 years old, and devastating in the short skirts and high heels she liked to wear all the time. Her friend Mary, as devious as she, was a stunning blond with smaller breasts, but beautiful wholesome features which betrayed nothing of her wicked nature.
Today Mommy had me dressed in white nylons and v-shaped lace panties. My swollen testes bulged out obscenely on either side of the panties. She had soaked me in a very feminine perfume called Poison. I was wearing one of her brunette wigs, “my” long, lush hair brushing down across my shoulders. She had also made up up like a whore – with wild red lipstick and heavy black mascara and eyeliner on my already naturally long lashes.
Oh, they loved to tease me about that! “With your pretty lashes you make such a nice little girl! In fact, you’re more of a girl than a boy, aren’t you? A real boy wouldn’t let his Mommy put his weenis in a little tube so it couldn’t get hard and then lock it up, would he? No, a real boy wouldn’t let me do that.”
And Mary would chime in and say things like, “Oh, he loves being a femmy little girl-slut. Just look at the way he melts when we softly stroke his nipples. Just like a precious little girl! See how he squirms and sighs – you’d think he was moaning to be fucked like a girl – you want a nice hard cock in your pussy hole, don’t you? Of course you do, you can’t think about anything but sex and humiliating yourself now.” And then they would giggle to themselves and sometimes give each other deep kisses while I watched and squirmed and felt the pressure in my dick that would never stop now.
Today they had something special planned for me. They had made me beg them to keep me in my chastity tube for 3 weeks now. Mommy told me she would kick me out of the house and we wouldn’t be able to play any of our “reindeer games” anymore unless I begged her. She was always like that – she not only made me do things that gave me a sick feeling in my stomach, but she made me beg to do them, betraying myself for the wanton pleasure of cumming (on those rare occasions when she allowed it).
Mommy’s friends (including Mary) were coming over tonight and I was to be the entertainment. Mommy knew how desperate I was to cum and I knew she would exploit my need for her and her guests entertainment.
As the guests started arriving, I wanted more and more to crawl into a hole and just masturbate myself until I forgot what I was being put through. Each of the guests was fully clothed and wearing a light mask, so I couldn’t see their faces, but I was on display for them.
I was almost nude – with only my white nylons, high heels and panties on. Mommy had made me take a Viagra before the party and now my cock was trying to erect in it’s tube again, making me involuntarily groan out loud.
First the men lined up and I was forced to suck their cocks one by one. Mistress Mommy made sure I didn’t give them a quicky, either – I was forced to make love to each cock, licking it tenderly and carefully, prolonging the pleasure and making the orgasm (which I was forced to swallow) that much more intense.
As I acted out the degrading scenario, the women took turns penetrating my pussy hole with strapon dildos. Some of them were coated with a BenGay like substance, which made my hole burn as hot as the shame burning my cheeks.
In between sucking cocks, Mommy would lift my head and kiss me deeply, praising me for being her good little cocksucking whore, and softly play with my nipples, ensuring my submissiveness, lust and continued devotion.
As I finished whoring myself out for her male guests, the females lined up and hiked up their dresses. None were wearing panties and this time I did enjoy my duties as I french kissed their nether lips until they squealed with delight. The bad part was that my hole was still being taken by other women at the party, and both sides kept up a running stream of insulting comments about my sissy make-up and attire and the way I was being used for their amusement and how I deserved to be treated like this.
My jaw and my tongue were aching as badly as my still encased pussy-stick when I finally finished with the women. By now I was almost out of my mind with the need to cum, as a result of the Viagra and all the oral I had just performed.
My hopes raised as Mistress Mommy gently removed my frilly panties and also my chastity tube. At least I was going to get sweet relief – even though I knew that it would be painful because it had been so long for me. But at least it would quell the desperation I was feeling and empty a little of the pressure in my girly marbles, as Mommy called them.
However, my release was not what Mistress Mommy had in mind – at least not yet. I was made to stand in the middle of the room for everyone to see as Mommy’s friend Mary tied my hands together and attached them to a hook hanging from the ceiling. She then attached my ankles to a spreader bar which had little hooks in the bottom which she attached to eyelets in the floor. Now my hands were tethered to the ceiling and my feet tethered to the floor. She iced down my cock until she could fit a cock ring around it and my balls. It caused my balls to stick straight out in front of me, which is just what she wanted.
As I stood there unable to move, Mary took her crop and mercilessly whipped my balls and penis with it. After all I had been through, it was almost more than I could take. I was sobbing and hysterical and all I could feel was the sharp stabbing pain as my poor pussy stick and balls were repeatedly struck. After an eternity, I felt the blows stop but my screams and sobbing continued as Mistress Mommy let me loose and held me in her arms.
Mommy was all tenderness now. “Oh, my precious little baby. It’s all over now, honey. You did such a good job for Mommy. Mommy loves her little girly boy. Shh, shh, baby. It’s all okay now.”
As Mistress Mommy talked to me gently and lovingly, her wicked hand slid down to my penis and began stroking me to arousal again. As all the guests watched, my sobs turned to gasps as Mommy brought me to the brink again and again, only to back off at the last possible moment and snatch my dearly earned orgasm from me.
At last, when I was panting with lust, my face red and with me willing to do anything, anything for release, Mommy asked the guests to step aside from the middle of the room.
I was filled with horror but knew I would do what Mommy asked of me. I couldn’t say no – I was mentally shattered and no longer had a will of my own and also every fiber of my being cried out for relief.
“See, baby” Mommy crooned. “I told you it would be fun to see just how far down you would go to give yourself a cum cum after a little time in your tube.” She giggled and led me to the rubber sex doll she had placed on a mat on the floor.
“You know you will never get a real woman with the little weenis you have, don’t you dear?”
I was crushed. With tears in my eyes I nodded yes.
“But your little thing still wants it’s cum cum, doesn’t it? It wants to squirt its juice just like it was a real cock, doesn’t it honey?”
Again, I nodded my assent through the tears running down my face.
“Well, I think it should be able to, baby,” Mommy said. “So I’m going to tie your hands behind your back and let you have your way with your new girlfriend. Isn’t she pretty, honey? See how big her tits are? And she has a hairy pussy, just like you like, dear! Oh, I can just see you two falling deeply in love!” she said, sarcastically, increasing my shame, if that was even possible.
As Mommy tied my hands behind my back, Mary put a slippery lubrication on my pee pee. The Mary got into place behind me while Mistress Mommy kneeled in front of me and held my new girlfriend in place. Mary’s hands snaked around me and found my nipples, driving waves of sensuous pleasure through my entire body and making me swoon as she kissed and thrust her tongue into my ear.
Meanwhile Mistress Mommy was saying something I could barely make out. “Dear, I’m not sure you’ve entertained our guests enough this evening, do you? I think it would be great fun for the ladies if you asked each of them for permission to put your penis inside your new girlfriend. Now, don’t get shy on me, make your Mommy proud and politely ask the ladies for permission to spill your filthy seed in front of them.”
Each woman in turn stepped in front of me, straddling the love doll as I begged for permission to shoot my boy-juice into the sex doll underneath their shapely legs. Each woman in turn insulted my cock, my balls, my lack of willpower and backbone and slapped me in the face after french kissing me.
Finally every woman had agreed and Mary guided my cock into the love dolls opening. Slowly at first, I began to thrust in and out of my new “girlfriends” hole as I could hear the guests laughing at me. Mary continued to caress my nipples and tongue my ear as Mommy held the doll and, in her most sexy voice, egged me on to completion.
“Baby, I know it’s difficult for you but you want to please Mommy, don’t you? Keep thrusting your little pussy-stick in and out for Mommy. Don’t let the laughter of all my friends keep you from your cum cum. Keep thrusting, baby. That’s a good boy. Mommy’s good little boy! Oh, at least your girlfriend can’t tell how small my baby’s penis is! She doesn’t care if you’re hung like a 5 year old, does she? No, she loves you, baby. She wants your cum burning inside her. Let’s give it to her now, honey – let’s give her your cum. Mommy wants you to cum now, baby – cum for Mommy now – cum for Mommy!”
As I heard those words her training took over and my pent up load from the last several weeks of chastity exploded out of my tiny cock and into the love doll Mommy had purchased to be my fantasy girlfriend.
Drained, exhausted and ashamed, Mommy led me up to her bedroom where she put me into her bed and held me in her gentle embrace all night long. (After sliding my penis back into it’s cruel little tube.)