Turned into a Slut Ch. 04

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Timmy meets the man that made him a cuckold.
3.4k words
4.52
119.3k
54

Part 4 of the 5 part series

Updated 10/25/2022
Created 07/01/2012
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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.

"Timmy huh, you don't look much like a Timmy," he said, as he looked me up and down.

"I've taken to calling him Tiffany, I think it suits him better, don't you?" Jennifer giggled. Jack laughed, agreeing with her.

"Ya it sure does, Tiffany it is than. Come meet my friends baby doll and bring your bitch too," he told her, smirking at me. I blushed, trying to fight back tears and barely succeeding. We followed him to the living room where he introduced us.

"Hey guys, this is Jennifer and her 'boyfriend' Tiffany. Jennifer, that's my bestfriend Andrew over there, we all call him Andy though. The lovely girl sitting next to him is Nicky.

"Jennifer, sit with me over here," Jack told her, indicating the love seat. They sat down together and I noticed that there wasn't any place near Jennifer for me. Jack noticed this too. "Andy, take Tiffany out to the kitchen and show her where all the drinks are. Help her bring us back a few."

"Alright bud; Tiffany, follow me," he said. I looked back at Jennifer as we went out to the kitchen. She winked at me before grabbing Jack and settling down for some serious necking. In the kitchen Andy showed me where the cold beers were. I grabbed a few and started to return to the kitchen but Andy was blocking the way. He took the beers from my hands and set them on the counter.

"Jack told me you sucked a dick earlier, did you like it?" he asked me. I blushed and shook my head, refusing to meet his gaze. Andy took my chin and lifted my face till I was looking at him. He was a pretty hot looking guy, a hard jaw and the most beautiful green eyes. "You're a bad liar," he said. "Jack didn't mention that I'm gay. You look pretty fem," he said as he reached under my skirt and fondled my caged penis, "but I think I can have some fun with you anyways."

He slid his hand behind my head and, gripping me firmly by the neck, pulled me into a deep kiss. I swooned as soon as his lips found mine and all my hurt feelings gave way to the sissy lust that welled up inside of me. All I wanted at that moment was to feel love in some way and this hot stud was giving me what I needed. That and a hard cock in my mouth and ass. All too soon he broke the kiss.

"I want to suck your cock," I moaned, my tongue darting out to lick his earlobe. Andy laughed at me as he pushed me to my knees and pulled out his dick. It was bigger than the dick I had sucked earlier and beautiful to look at. I pulled it into my mouth immediately and began to worship it. Jennifer was right; I didn't have to walk in my heels for very long.

My tongue made sweet love to it and I gripped his hard ass muscles in my hands, forcing his cock all the way down my throat. His hands were stroking the back of my head. I looked up into his face with wide eyes, a look of lust displayed in them. My cocksucking was interrupted by a shout from the living room.

"What's taking so long," Nicky yelled.

"Ah, nothing, just grabbing the beers is all," Andy, yelled back. He pulled me off his dick, put it away and zipped himself up. I straightened my skirt and grabbed the beers, following him to the living room.

"Tiffany, your lipstick is messed up," Jennifer said when we returned. "Were you being a naughty slut again?" They all laughed when I froze and blushed red.

"It's ok Tiffany, we already know you're a slut," Jack said, taking the beer I offered him. "Go over and sit by Andy now, you two can have some fun while I show your girlfriend what she's missing."

"Ya, Jack's gonna fuck me with his huge cock, little sissy," Jennifer said teasing me. I wanted to say something to stop her from doing it but Andy put an arm around my shoulders, silencing my protests with a passionate kiss. As our lips locked together I saw Jennifer pulling Jack's dick out of his pants. It was by far the largest cock I had ever seen and Jennifer wasted no time swallowing it.

"Way to go girl," cheered Nicky. "Let's see what your boyfriend is hiding under that skirt." I felt a hand reach under me and pull my panties down my legs but I didn't see where they went as my full attention was on Andy's lips. My caged clittie popped out. "Haha, I can't believe any guy would ever let a girl do that with his dick but I have to say, it looks very cute all caged up. It's pretty small too."

"He's not much of a guy if you hadn't noticed," Jack said.

"I was getting so tired of his tiny dick. He never made me cum with in. I had to find something bigger," Jennifer said between licks.

"I'm so horny right now Andy, let me fuck the slut," Nicky whispered in Andy's ear. He murmured an agreement and pushed me to my knees in front of him. I dug his dick out of his pants. It was still rock hard and covered in my spit. I sank my mouth down onto him, one hand pumping his shaft, dark purple nail polish in dark contrast to his light skin.

Nicky kneel behind me and pushed my skirt up over my waist. With one hand she fondled my balls, lightly dragging her nails over them. I tried to squirm away but she pinched them lightly to let me know who was boss and I whimpered into Andy's dick. She poured lube onto my ass, spread it around my hole and slid a finger in, then another when she found me loose and willing.

"This slut isn't very tight," she announced to my shame.

"Jennifer said she has taken a few things up her ass today," Jack chuckled. Jennifer was crouched between his legs just like I was, her clothes in a pile off to the side and she had a hand buried in her pussy. I could see her pussy juice dripping down her leg from where I knelt. I went back to sucking Andy's dick, groaning as Nicky filled my ass with her fingers. I could feel precum dripping from my cock as she massaged my prostate.

Nicky pulled her fingers out and I felt the head of a dildo take their place. I looked back at her and found her shirtless with a thick strapon attached to her waist. Her large boobs stood out proudly on her chest and swayed seductively as she thrust slowly into me. Behind her, Jennifer was now bent over the sofa as Jack thrust his thick cock into her tight cunt.

"Oh fuck me fuck me fuck me, fuck me you big dicked bastard," Jennifer babbled in ecstasy.

"Oh fuck that feels so good," I moaned and reached back with one hand to help Nicky into my ass. Andy seized my hair and forced my mouth back down onto his cock. As Nicky picked up speed I could feel what seemed like an endless stream of precum dripping to the floor. I must have been making quite a mess.

Andy took hold of me with both hands and started to face fuck me. I relaxed my throat and let him slide all the way in, swallowing his precum and my saliva. My throat must have been massaging his cock nicely for he groaned and pushed his cock as far in as it would go before releasing his load into my stomach. I was a little disappointed I wasn't able to taste it but made do with licking his beautiful dick clean while he came down from the orgasm. My eyes never left his face the whole time and I hoped he could tell how much I loved sucking his dick.

While Andy rested I used the time to enjoy the ass pounding Nicky was giving me. Her cock was long but smaller in width than Andy and it touched places nothing had before today. I let the pleasure my prostate gave off wash over me. There was a dull throbbing in my gut and I knew my balls were becoming full of cum and ready to explode. I lay my head on Andy's lap and enjoyed the sensations.

"Ohhhh, you make me feel so full Jack," Jennifer wailed.

"Yeah you sexy bitch, take my dick," Jack grunted as he pounded her from behind.

"Switch!" Nicky shouted and pulled out of my ass as Andy got up off the couch. She pulled off the strapon and sat down in his place as he squatted behind me. She grabbed my hair and a moment later I was licking my third pussy of the day. Andy spread some lube on his cock and slid right into me.

I lifted my head enough to say, "Oh fuck me you sexy stud."

They all laughed at me. "Your girlfriend is over there getting fucked," Nicky said to me as I licked her clit. "She's riding Jack now and she looks so hot spread wide on that big dick. God Jack has such a big fucking cock. I bet she never wants to fuck you anymore." She looked over me at Andy. "Spank that slut's ass," she said.

Andy started to spank my ass as he fucked me. I wiggled in encouragement to let him know I loved it. His cock felt wonderful in my ass. It brushed against my prostate on every stroke in and a little precum would ooze out through the cage.

"FUCK!" Nicky cried out. "Jack looks so hot fucking your girlfriend and I love making little sissies eat my cunt. Oh Fuck, LICK ME YOU SISSY COCKSUCKING FAGGOT," she shouted as she started to cum. Her whole body lifted off the couch and she clamped her legs around my head, holding me to her and riding my face with wild abandon.

I heard Jennifer shrieking at the same time and a deeper grunt from Jack as he came inside her. "Oh god, Jack just fuckin' came in your girlfriend," Nicky said, laughing at me.

"Here, make the sissy clean her out," Jack said from behind me. Andy pulled out and I murmured in disappointment. I wanted him to cum in my hot ass. Jennifer lay on her back on the low table in the middle of the room, her pussy spread wide. It was red and gaping, with cum covering it. Jack grabbed me by the hair and thrust his softening dick into my mouth. I could taste Jennifer's pussy and his cum mingled on his cock.

"Clean your girlfriend off my dick sissy," he told me. My cock leaked more precum at his words and I swirled my tongue around his dick, cleaning all the juices off it. He pulled out of my mouth and pushed me towards Jennifer. "Eat her now."

My dick dripped precum across the floor as I crawled over to her and dove into her pussy. I love the taste of her juices mixed with sperm and I hungrily ate up all I could find. My little penis tried to harden in its cage. Andy knelt behind me again and slid his cock back inside my ass once more. He took hold of my hips and started to thrust savagely into my ass. Jennifer had her fingers locked in my hair and was screaming out another orgasm as I thrust my tongue deep inside her pussy, trying to suck out all the cum. With her orgasm came a flood of cum and I swallowed it all, my tongue searching for more.

Andy groaned out at the same time and plunged deep into my asshole. The fire that had slowly been growing in my gut came bursting out as his cum splashed shot after shot into my quivering asshole. My little penis lurched inside its cage and spat a torrent of cum onto the floor.

"Oh my god, the little sissy just came without getting hard or touching herself," laughed Nicky. I let loose a scream of pleasure and blacked out as my orgasm overtook me and all my senses failed.

When I came to I was lying on a bed with a warm body behind me. A stiff penis rubbed against my ass. In the distance I could hear Jennifer and Nicky's screaming and moaning as they were fucked. I rolled over to see Andy looking at me. He arched an eyebrow.

"Wanna go again?" he asked. I looked at him for a moment, a feeling of warmth spread through me. Did I really want to have my ass pounded again without my girlfriend around to force me to do it?

"Sure," I said with a smile and leaned over to kiss him. My ass quivered in anticipation. Of course I did.

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GrrrreatImaginationGrrrreatImaginationabout 2 years ago

"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." This turned the story up for me. It would have been too easy to hold on to the betrayal without her/him choosing to embrace the parts of his life he could influence (of course, not including his ex-girlfriend-now-mistress). When authors show their characters enjoyment of events, its easy for me to connect. Thx.

AnonymousAnonymousover 6 years ago
yes

you should glue mine on me

LUSTYWHEELSLUSTYWHEELSalmost 7 years ago
great

she should make him glue his cage closed

Tootight1Tootight1over 9 years ago
good story

sexually, this has gone great, I wish it happened to me, but a person has to think about doing what's right for the future they want. out in public, a record of what occurred, could kill his future.

devilspy2001devilspy2001over 10 years ago
Loved it.

I have fucked a number of chastity sissy boys and I love how you describe how they leak and even cum. All that goo on the floor. I like to make them lick it up and swallow it. I had one sissy husband who's wife gave him Viagra before I used him. I had not unloaded in days. He was in pain in his cage as his cock responded to me and her playing with his balls and licking his balls and the outside of his cage. He was filling it so he could feel the wet touches, and was moaning and groaning so loud as he sucked my cock. After unloading into his belly, he sucked my hard and then as he was dripping and leaking I fucked his tight pussy for 20 min's till I unloaded again and bred his pussy. He was whimpering and moaning. Then after he cleaned up the floor and my cock. An hour later after playing with his wife, I was hard again and fucked his stretched pussy and gave him a second breeding. Damn that was a good time.

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