After grabbing some quick sandwiches, Jennifer and I returned to her home. We found a note on the kitchen table from her parents letting us know that they would once again be out of the house for dinner. They didn't expect to be back until ten o'clock, it was seven right now. Once in her room, Jennifer commanded me to strip out of my jeans and bend over the bed.
"It's time for your punishment," she announced. Jennifer ran her hands over my ass. A shiver went up my spine as she touched my sensitive skin. A low moan of delight escaped my lips as she caressed my balls and lazily ran a finger across my abused asshole. I bit my lip in an attempt to hold in my desire but Jennifer could see it anyways.
"Does my little sissy like having his ass and clit played with? Too bad it's punishment time. You are being punished for calling me Jennifer when you should have addressed me as Mistress as well as for begging to cum. Your orgasms are now mine to choose when you get to have them. Now push that cute little ass out." I spread my legs and arched my back, pushing my ass out nicely. She brought her hand down sharply on my ass and I shrieked. "That's it sissy, let the neighbors know you are getting spanked like a naughty boy. Do you think you can keep it down or should I gag you?
"I'll be quieter Mistress," I whimpered.
"Of course you will," she smirked. I heard the intake of her breath as she brought her hand down again and barely managed to hold back another scream as it connected. Jennifer caressed my reddening ass and I moaned again, my mind tormented by the pain and pleasure she was giving me. The next spank was just as hard as the first but Jennifer again caressed me afterwards.
"Hmm, I think we need to use something else," she rummaged through her closet, bringing out a leather cat o' nine tails. "This should do nicely!"
"Please Mistress, be gentle," I begged.
"Of course baby, I wouldn't want to hurt you too much, I love you," she said, kissing me deeply. She pulled away and brought the cat o' nine down sharply on my ass. I groaned in pain and jerked upright. "Back down onto the bed," she commanded, pushing me forwards. I meekly obeyed her, laying back down on the bed and grabbing the other side to brace myself. My ass lit on fire as she started to rain blows down on it. I pushed my face into the sheets to muffle my cries of pain but the torture stopped abruptly as Jennifer's phone rang.
"Hello baby, what's up?" she spoke into the phone. She traced the cat o' nine up and down my back, bringing it down lazily every now and then, as she listened to the voice at the other end of the line. "Oh sure that sounds like fun but my boyfriend is over right now, can he come too? Yeah, invite them too and then he won't feel all left out. Alright, see you soon, bye," she closed the phone, set it back down, and looked at me.
"That was my big dicked lover, Jack. You haven't met him yet but I've been fucking him for a few months behind your back. Your tiny penis just couldn't please me anymore," she sneered. "I just agreed to come hang out with him and I'm bringing you with me."
"You've been cheating on me? Wi... With another guy?" I asked in shock. Despite all that had happened today I still thought Jennifer was my woman.
"Oh don't be so shocked honey. Why do you think we have been spending less time together? Don't worry, I'm still gonna date you. Jack doesn't eat my pussy or pay for all my dinners.
Anyways, there isn't anything you can do about it and considering you are dressed in a wig and women's clothes, bent over a bed getting your ass spanked, I don't think you can really tell me what to do. Now get into the bathroom and take a shower, we have to get ready."
I walked dejectedly to the bathroom. How could she do this to me? I felt as if she had yanked out my heart and stepped all over it. All I could do was follow her commands listlessly; I no longer had any will of my own. She made me bend over in the bathroom while she filled me up with an enema. I got into the shower afterwards and scrubbed myself pink. Once clean I returned to the bedroom to search for my clothes.
"Not those clothes silly," Jennifer said when I picked up my boxers and pants. She was holding the blue pleated miniskirt we had bought today in one hand and some panties in the other. "When I told Jack how much of a sissy you were he said I should dress you in women's clothes. I figured you could wear some of the clothes we bought you today for him."
I was past caring at this point and simply put on the clothes she handed me. I chose to concentrate instead on the wonderful feelings they were giving me. The panties were tight on my butt and pulled my chastity belt in nicely, constantly reminding me how pathetic my little dick was. The mini skirt came down to well above mid thigh and let a cool breeze blow across my tender ass, which it barely covered.
My shirt was another goth looking one, this time in a dark purple that went with the blue of the skirt. I pulled thigh high stockings up my legs and marveled at how they felt on my newly shaved legs. The heels took a little getting used to but Jennifer assured me I wouldn't have to walk around in them much.
After straightening my wig, we reattached it and Jennifer made sure it framed my face perfectly. Before we headed out, Jennifer helped me with my makeup, once again applying everything to make sure I looked as absolutely gorgeous as possible. This time we added a stylish dark blue nail polish to my fingers and toes.
Jack's house wasn't far away and we arrive there in about fifteen minutes. The entire way over Jennifer was telling me about him and, while I still felt dejected that she had cheated on me, I had to admit he sounded pretty hot and my little dick was straining in its cage.
We could hear voices inside the house when Jennifer knocked on the door. A second later it opened and I stood face to face with the man who had taken my woman from me. I guess face to chest was more appropriate though since Jack towered over me. I was immediately intimidated by him and stammered out a hello.
"H...hi, you must be Jack," I said offering my hand. Jack ignored me though and instead grabbed Jennifer, pulling her into a passionate kiss. His hands ran down her sides to cup her ass as he thrust himself hard against her. Jennifer came up flushed and gasping. I figured she was already dripping wet with lust.
