tagTranssexuals & CrossdressersCocksucker: Cum Bucket

Cocksucker: Cum Bucket

bysilkstockingslover©

Summary: Shemale and others gangbang straight crossdressing anal virgin.

You do not need to read the first parts to enjoy this story of a straight man's hotel orgy of gay submission. In case you are curious how this straight married man got into this predicament, here is a brief summary of the first three chapters of "Cocksucker":

Chris, a married straight man, is stuck at the airport when his flight is delayed. While waiting at the bar he is slyly seduced by a younger man. After submitting to him in a washroom stall, he must complete seven humiliating tasks to get his wedding ring back. Task one was to walk around with cum on his face until he got to his hotel room hundreds of miles away, and to tell the woman at the check in why he was late for his flight (Hewas sucking cock in the bathroom).

Task two was to service a very gay hotel clerk and begin his training as a cocksucker. He also gets his first blow job from a man. Disobeying an order from his Master also leads to a punishment that has him sucking an older man's cock.

Task three was to go and purchase lingerie at an adult store and wear it underneath his clothes at all times. This led to a visit to a glory hole and the beginning of cross-dressing. He also ends up learning the older man he sucked last night is his boss's father, which complicates matters greatly.

I hope you enjoy the continuing adventures of a straight married man who discovers everything he thought he knew about his sexuality was a lie.

NOTE: Thanks to Goamz86, Robert and MAB7991 for editing this story.

*****

I got to the restaurant and, of course, James (my boss Kevin's father who I had secretly blown twice) was there, too, and offered me a seat beside him. Besides Kevin and his father, two potential clients were there, too.

Dinner included a lot of whiskey, great food and bullshit sex talk. Once dinner was done, James grabbed my hand under the table and placed it on his cock. I rubbed it slyly under the table for the next few minutes as the conversation shifted to business.

I continued rubbing his cock as I talked business. Eventually, the meeting done, Kevin paid and asked, "Do you want to go to the strip club with us?"

"Oh no, I am supposed to Skype with Laura," I said, seeing it was after eight and I was already late for my next cocksucking session what had already been planned by m Master.

"You are so whipped," he teased me.

James whispered, "I'll be knocking on your door whenever I get home."

"I might be in bed," I said.

"All the better," he replied.

I walked back to the hotel quickly, well, it was more of a run, really, as I worried I would miss Oliver or them (if his promise of bringing a friend, or friends, was true). I shook my head at the silliness that I was worried about missing my chance to suck a twink's cock.

I got to the hotel and saw that Oliver wasn't at the front desk. I got up to my room and opened the door and almost had a heart attack, as I walked in on Oliver getting ass fucked by a hairy Italian looking man while he sucked the cock of another young looking twink.

"Get naked," the Italian looking man ordered, as he slammed into Oliver.

Oliver took the cock out of his mouth and said, "Sorry, cocksucker, we started without you."

"How did you get in here?" I asked.

"I woooork here, silly," he said as he literally squealed from the cock in his ass, before taking the other cock back in his mouth.

The hairy Italian man ordered again, his accent confirming my original assessment of his nationality, "Get naked, cocksucker."

Like I seemed to do all the time lately, I obeyed. Once he saw I was wearing a bra, the Italian looking man laughed, "Shit, we have ourselves an adorable little girl here. Are you wearing panties too?"

"Yes, sir," I nodded, as I began to pull down my pants.

"Sir, I fucking love it," the Italian said, as he continued pounding away hard into Oliver's ass. "Oh shit, he is wearing pantyhose too. This is fucking too rich. Keep on the girlie shit for now, cocksucker and come join me on the bed."

I obeyed again, now only in girl's lingerie.

From the bed, he gestured to me to move beside him. Once I was there, he pulled his cock out of Oliver's ass and shoved it straight into my mouth. Although it wasn't overly long, it was ridiculously thick and it stretched my mouth. He fucked my mouth as if he was fucking a cunt or ass, his whole cock filling my mouth so completely that his abundant pubic hair went up my nose and his balls bounced off my chin.

I should have felt humiliated, but humiliation no longer seemed to be an emotion I could feel. Instead, I just enjoyed the opportunity to be used and to please.

"And you say he never sucked cock before yesterday?" The Italian asked.

"No, he was straight and pure," Oliver said.

"Well, he has a great pair of cocksucking lips," the Italian approved, as he kept fucking my face.

After a few more deep thrusts, he pulled out of my mouth and slid his cock back in Oliver's ass. I watched Oliver take the thick cock in his ass and instantly wondered again what it would be like to have one in mine.

The other guy, whose cock was still in Oliver's mouth, said, "It looks like our new little play toy wants a cock in his ass."

"N-n-no, I don't," I stammered. It was one thing to be curious, but another to actually go through with it.

"You are practically drooling as you watch Oliver get his man pussy pounded," he said.

Oliver took the cock out of his mouth and moaned, "Leave Chris alone, Zeke. He is still coming to grips with who he is."

Truer words had never been spoken. I wanted to suck all their cocks, I wanted to be treated like a cocksucking whore, I wanted to be called names, but I wasn't sure I wanted a cock in my ass...it was intriguing and yet somehow it crossed a line I wasn't ready to cross. Instead, I was hoping the toys I bought would be a good starter to see, at my own pace, if I liked something in my ass.

"What do you say cocksucker? Do you want to become the full service twink you obviously crave to be?" The Italian asked.

The words 'crave to be' fazed me as did being called a twink. Before yesterday they would have been absurd, yet now, after taking a plethora of cocks in my mouth, dressed as a girl, it was becoming confusing. I didn't crave a cock in my ass, but I did crave a cock in my mouth. I answered, "Sir, I am not ready for my ass to be fucked, but I would love to suck all three of your cocks like the hungry cocksucker I am."

Zeke laughed, "Well, I can't resist such an offer. Get on the floor, cocksucker."

I quickly obeyed, giddy with excitement and hungering to have a cock back in my mouth. Zeke quickly shoved his cock in my mouth as Oliver said, still getting reamed from behind, "His Master wants him to practice getting face-fucked today."

"That I can make happen," the twink laughed, as he began pumping his cock in and out of my mouth. It wasn't big, but he was very rough. He held my head, as he fucked my face and said, "Oh, fuck, you have a great cocksucking mouth, faggot."

I just focused on not gagging as he held me firmly and plundered my mouth. My slobbering sounds were loud, and his balls bouncing off my chin turned me on as I began rubbing my cock through my pantyhose and panties.

"Don't you dare touch that cock, cocksucker. Cocksuckers suck cock first and if they are good they may be allowed the privilege of getting to come," The Italian ordered.

I instantly obeyed, moving my hand away from my iron stiff cock and continuing to focus on the cock pounding away at my mouth.

I heard movement on the bed and was instructed, "Take a cock in each hand cocksucker, keep them nice and hard for that pretty mouth of yours."

I again obeyed, stroking the two cocks while sucking a third.

A moment later, Oliver said, "My turn," and the twink let go of my head and pulled his cock out. I looked up and saw I was surrounded by three cocks, three hard, yummy cocks. I leaned forward and took Oliver's long cock in my mouth and, without instruction, began bobbing hungrily back and forth.

"I still can't believe he had no clue he was a cocksucker before yesterday," the Italian said, his tone implying he was in awe of just how big a cocksucker I was.

Oliver laughed, "He seems to be making up for lost time."

"Well, let's help him do that," the Italian said, ordering, "My turn, cocksucker. Come clean Oliver's ass off my cock."

Again, such a task should have been disgusting, but since I had already done it, it was just another perverse moment in the subversion of my old life into my new life as a cocksucker.

Over the next fifteen plus minutes, I just moved from cock to cock, getting face-fucked by three cocks of very different shapes and sizes. Each would slam into my face for a minute or two before giving way to the next cock. My jaw was sore, my knees were burning when the Italian asked, "Ready for the circle jerk boys?"

I didn't know what a circle jerk was but I soon learned as all three men started jerking off, their cockheads aimed directly at my face. I understood instantly that I was going to get covered with cum. Again, it should have been humiliating, but instead I couldn't wait to feel their sticky seed spray my face, although I was disappointed to not be able to feel them shoot their loads in my mouth.

I watched the three men stroke their cocks, unsure which one to be ready for first. Eventually, Zeke, 'what a funny name for a twink' I thought to myself, said, "Look at me twink-in-training." I instantly obeyed even as I processed being called a 'twink-in-training.' Seconds later his cum shot out of his cock covering my forehead, face and chin, I couldn't resist as I leaned forward and devoured his cock, hungry to sample a taste of his cum.

Oliver grunted, "Turn to me, cocksucker." I reluctantly took one cock out of my mouth, getting just enough of his seed to desperately want more. I was just turning my head when the first shot hit me directly on the cheek. The second and third ropes of cum hit my nose, lips and a bit landed in my mouth as I opened wide...wanting as much cum as these men were willing to give me.

The Italian grabbed my head and shoved his cock in my mouth and roughly fucked my face again. I prayed he was going to deposit a load of cum down my throat, but after a few hard deep thrusts he pulled out and added a third load of cum all over me.

All three men spent. The Italian said, "I'm thirsty, cocksucker. Go get me a Coke from the end of the hallway."

I stood up, thankful to be off my knees, as I reached for my jeans. "Go as you are cocksucker. True cocksuckers are not ashamed by who they are."

"Can I at least wash my face?" I asked.

"Of course, not," he laughed. "Cocksuckers swallow or wear the cum they are privileged to have shot on their pretty faces with pride."

"Say cheese," Oliver said, his phone now out.

I smiled like a dirty slut, suddenly curious what I looked like with three loads of cum all over my face.

"Now go get me a fucking Coke," the Italian ordered.

"Get three," Zeke said.

"And ice," Oliver added.

"Yes, sirs," I nodded. Although I thought I couldn't feel humiliation any more...I was wrong. The idea of going out dressed in a bra, panties and pantyhose, my face coated with three loads of cum was definitely humiliating. Yet, I felt compelled to obey.

I grabbed the ice bucket and my wallet, took a deep breath and headed out of the safety of my room and to the hallway praying it would be empty. Thankfully, it was, and I reached the vending machine without incident.

My hands trembled as I tried to quickly put the bills in the machine. I had two sodas done when I heard girls giggling down the hallway. I got the last soda and moved to the ice machine where I quickly got the ice bucket filled as the girls' voices got closer.

Rushing, I dropped all three sodas and was bending down to pick them up when the young women arrived.

"Oh my," one said, as I quickly picked up the cans and stood up, revealing my fully erect cock in my panties.

"Is that cum all over your face?" the other girl asked.

I said, "Excuse me," as I rushed passed them, my face red as the flames of hell, and I scurried to my room.

"Nice ass," one called out from behind laughing. Reaching my door, I realized I didn't leave it open and had to knock...my public humiliation getting extended.

"Hello," Zeke said.

"Please, let me in," I replied, as I heard the elevator door beginning to open.

"What are you?" He asked.

"A cocksucker," I whispered.

"I can't hear you. You better speak up," Zeke said, clearly enjoying my humiliation.

People exited the elevator as I said, "I'm a cocksucker."

"Oh my," said a woman from behind. Her voice appeared to be that of an older woman.

The door opened and I quickly entered my room and slammed the door.

Zeke asked, "Meet any new people?"

"Yes," I said. "A bunch who think I'm a sick, twisted pervert."

"Which you are," the Italian said. "Now bring me my Coke."

I handed out all three Cokes as Oliver said, looking in my bag of toys, "You have made some interesting purchases today."

I couldn't go any redder as I stammered, "M-m-master instructed me to."

"Pull out the wall cock," the Italian said.

"Not now," I said, not comfortable with them watching me experiment.

"I wasn't asking," he said. "It's either the wall cock or my cock, you choose."

I sighed, feeling that I was incapable of saying no, as I went to the bag and pulled it out. I also grabbed the lube knowing I would need a lot of it.

Zeke said, "I would love to watch this faggot sodomize himself, but my shift begins in twenty minutes."

I gasped as I watched him put on a police uniform and I asked, stunned, "You're a cop?"

"Yep," he shrugged.

I always envisioned cops as burly men and to see a clear twink as a cop was just another earth shattering revelation that nothing was as it seemed.

"Oliver, help our little cocksucker," the Italian said.

Oliver grabbed the cock and connected it to the wall across the foot of the bed as Zeke left. "On all fours."

I looked at him and said, "I am not sure I can do this."

"I'm here," he said, all soft and reassuring. "I'll make sure we do it right."

"Okay," I agreed, somehow feeling more relaxed with his help as I dropped onto all fours.

Oliver tugged my panties and pantyhose down enough to get to my asshole and poured an abundance of lube down my ass cheeks.

"Now slowly back up," Oliver instructed.

I wordlessly obeyed, curious to find out what it felt like, yet not liking having an audience.

I felt the cock head between my cheeks and I paused.

"Keep going, Christina," the Italian said.

Hearing him change my name to feminine was another embarrassing moment and yet it made my already stiff cock flinch.

I obeyed, moving back and feeling the cockhead at my anal entrance.

"Go slow," Oliver suggested, his hand gently rubbing my back.

I continued at a snail's pace as I felt my ass reject the first attempt to be violated. Yet, with an extra push I felt my ass widen and allow the mushroom top to enter me. A slight pain hit me, but nowhere near what I was expecting, as I paused and got used to having something just inside my ass.

"Keep going, Christina," the Italian ordered.

I obeyed again, being called a girl somehow only enhancing the thrill of sexual submission.

I had just begun to move back more, taking in another inch, when there was a knock at the door. I froze.

"Ask who it is," the Italian ordered.

I called out nervously, "Who is it?"

"Management," a female voice answered.

The Italian ordered, "Don't move, Christina," as he got up, still buck naked, his semi erect cock dangling between his legs, and went to the door.

He opened the door, to my dismay, and said, "Hello, boss."

"I should have known it was you two. I had a complaint of a man walking down the hallway in girl's clothing," she said, shaking her head and walking in. Seeing me, she said, "This is new."

Oliver explained, "He is leery of taking a cock in the ass, Debbie."

"Doesn't look like it," she said, looking down at me. She was a very pretty brunette with long legs in black pantyhose.

"It's his first time," Oliver explained.

"Her first time," the Italian corrected.

"How did you hook this one in?" She asked, looking me over.

Oliver recapped the story as I sat there silently with a couple inches of plastic cock in my ass.

"Is that true?" She asked me.

"Yes, ma'am," I admitted, being caught in the act by a woman as pretty as her only compounding my humiliation, which apparently had no limitations.

"Well, keep taking that cock in your ass," she instructed.

I obeyed yet another stranger as she asked, "Is he a good cocksucker?"

The Italian answered, "She has potential."

"I think I will see for myself, Antonio," she replied, pulling down her skirt. I looked up to see a cock outlined in her pantyhose.

My eyes went wide as I stopped backing up on the cock that was unnaturally stretching my ass.

She laughed, "Never met a she-male, cocksucker?"

"No, ma'am," I answered, having only seen them in porn.

"Want to suck my cock?" She asked, tugging her pantyhose down and releasing her cock from the nylon prison.

Staring at the smallish five inch cock, my mouth watering as usual, I didn't hesitate as I answered, "I would love to suck your cock, ma'am."

"He is so adorable," she smiled, kneeling down, her cock aimed directly at my mouth.

"She," Antonio corrected.

"Semantics," she shrugged, as her cock dangled like a carrot right in front of me. "But you really are a cute little cocksucker, boy or girl."

"Thank you," I said, like the twink I was beginning to realize I was.

"Now you can have this cock as soon as that ass of yours is full," she said, tapping her cock on my hungry lips.

"Yes, ma'am," I agreed, willing to do almost anything to feel her yummy cock in my mouth.

Slowly, I continued to move back, a pain appearing that burned my insides. I paused again as Antonio said, "Hurry up, Christina, get that ass nice and ready for cock."

My eyes again went wide at the obvious implication of his words. He wanted to fuck my ass.

Oliver tried to comfort me. "Honey, we won't do anything to you that you don't want to do."

"Oh. he wants cock in his ass," Antonio confidently said.

It was true, as I filled my ass with plastic cock; I wondered constantly what it would be like to have a real one in me. The toy in me felt both good, because it was so naughty and bad, but the simmering pain had yet to go away.

Debbie said, "It will hurt at first, baby, but just slam your ass back and take it all inside that cute man-cunt of yours. It will be like jumping in a cold lake...at first it will paralyze you, but once you get used to it...you will be submerged in it."

"O-o-okay," I stammered, not ready for any more searing pain in my ass.

Her hands went onto my shoulders and she said, "I will push you back on three. One, two, three."

"Fuuuuuuuuuuuuck," I screamed, feeling as if I had been impaled. The excruciating pain coursed through my very being and yet I also felt a rush of pleasure at completing the seemingly impossible task.

"Just get used to the cock in your ass while you soothe yourself with this," Debbie said, offering her cock to me.

I opened wide and took her cock in my mouth.

Oliver explained, "Today is supposed to be about training him to get face-fucked."

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