Cocksucker: Crossdressing

Once I had tits, she said, "I'll take a picture for your master like this and then one with the dress and heels on."

"Um, okay," I replied, overwhelmed by how casual this whole experience was.

"Pose with a finger on your lips, like you're being flirtatiously coy," she said.

I tried what she instructed.

She laughed, "No, like this," as she posed sexily. My cock flinched and I thought to myself at least I still get turned on by a woman.

I tried to replicate her look as she took a couple more photos.

"Since your master likes pink, I brought you a very sexy pink dress and matching pink high heels. You're a size ten, right?"

"Yes," I nodded, impressed she could get my shoe size right with just a look.

She opened the door, quickly grabbed the dress and returned. "Bend down a bit, this needs to go over your head," she ordered.

I again did as I was told and she assisted putting the dress on me. Once on, she said, "A wig, you need a wig. Do you want to be a blonde?"

Not even considering the reality that I was being turned into a cross dresser, I answered, "How about a redhead?"

"Hmmmm, are you flirting with me?" She asked.

"Is it working?" I countered, completely out of character for me.

"Well, it might, but I only eat cunt," she answered, shocking the hell out of me.

"It's okay," I tried to respond casually; "I'm married anyway."

"And you have a master?" She asked.

"It's complicated," I answered.

"It always is," she shrugged. "That said, with your skin color and high cheek bones I think you would look most natural as a blonde."

"Well, they do have more fun," I joked.

"But redheads are better in bed," she quipped back, as she left me alone in my stall, mouth wide open and my cock dying for attention.

While waiting, I put on the heels and almost fell flat on my face, catching myself on the wall. My wife only wore flats and I guessed these were about four inches high and they completely threw off my balance.

She returned and asked, "Fall?"

"Almost," I answered with a soft chuckle.

"It takes practice," she said, pointing to her heels. "Now I can run in these."

"That would be fun to watch," I said, glancing towards her well-endowed chest.

She smiled, as she put the wig on me. "Wow!" She said.

"Wow, what?" I asked, suddenly feeling completely insecure.

"I may reconsider," she said.

"Reconsider what?" I asked, confused.

"With some lipstick and eye liner, you could be a girl," she said.

"Really?" I asked, suddenly feeling sexy.

"Just wait a second," she said, leaving me again. I wished there was a mirror in this room but there wasn't, which I thought strange for a dressing room.

She returned and said, "Pucker up."

"Please, no! I don't want any lipstick on," I said, that somehow seeming to make this go too far.

"Just pucker up, you know you want to," she said, ignoring my words as she moved the lipstick to my lips.

Reluctantly I obeyed, as I always seemed to do now. She proceeded to put make-up on me; lipstick, eyeliner and something on my cheeks. Once done, she said, looking impressed, "Dammit, you're prettier than me."

"I am?" I asked, bewildered by the whole experience.

"Come take a look," she said, grabbing my hand and leading me into the hallway, where I stumbled on the heels again and almost killed myself.

"Sorry, forgot you're new to those," she said.

"Not sure the heels are me," I said, which was silly considering dressing as a girl wasn't me either.

"I disagree," she said, pointing at the mirror behind me. "Look.

I looked at myself in the mirror and stared. I didn't recognize myself. I was a pretty good looking guy, but I was an even prettier woman.

"Pose," she said.

I did, wobbling ever-so-slightly as she quickly texted someone on my phone.

I asked, "What are you doing?"

"Sending the picture to your master. He liked the earlier ones," she said.

"You have been talking to Gary?" I asked, stunned.

"Isn't he Master or Sir Big Cock?" She asked with her eyebrow raised, making me blush.

"Yes, he is," I nodded.

Just then my phone rang. She clicked answer and handed me the phone.

"Hey cocksucker, you look incredibly cute," Gary said.

"Thank you, Master," I replied, somehow not embarrassed to be seen as a submissive bitch around the pretty salesgirl.

"I'm impressed. You went a bit above and beyond today's task, cocksucker. You must really want to be a girl," he said.

"She just kept adding to the outfit, Master," I explained.

"Carol tells me that tomorrow night is amateur night at Divas, a Crossdressing bar," he said.

I already knew where this was going, as my erect cock twitched in my panties.

"Anyways. Carol has offered to come to your hotel room and get you ready for your grand entrance into the world of being a drag queen," he continued.

"Oh," was all I could muster.

"So, I have a couple more small tasks for you now," he said, my heart racing with anticipation of the humiliation that was bound to go with the task.

"Okay, sir," I said, looking at Carol who was grinning from ear to ear.

"One, you will not change out of this outfit until you fulfill all the tasks given," he started.

"Of course," I nodded, even though he couldn't see me.

"Two, you will go into a ladies washroom in a nearby mall to check your make-up or take a piss if you need to," he began. "Then task three you will offer your oral services to men until one takes you up on the offer."

"Oh God," I groaned at the task.

"I'm your God now," he replied firmly, "your savior from yourself and your denial of who you really are."

"Yes, sir," I agreed, to the ludicrous suggestion.

"Give Carol your hotel room number and make arrangements for tomorrow. Task 5 will be performing at amateur hour tomorrow," he revealed, before adding, "of course you will probably suck a cock or three while there."

"I imagine so," I said, thinking being in disguise would make me way more comfortable in sucking a stranger's cock, even as I thought don't all these small tasks count as tasks? I then realized he had called that task number 5, which meant a task still awaited me before tomorrow night's drag queen expectation.

"Let me talk to Carol, cocksucker," he ordered.

"Yes, Master," I said, handing the phone back to Carol.

"Hi, Master," Carol said taking the phone, which was a curious greeting. "Of course...no...no problem...sure, give me a call when you are in town...I would love to see that in person...okay, bye." Hanging up, she texted him something else and said, "I'll meet you at the register."

"Okay," I said, walking slowly to the dressing room to get my clothes and the rest of my purchases. It took over a minute, another near fall, and dropping the pantyhose packages before I finally had everything in my hands and awkwardly made my way to the register.

Two customers paid for items, neither really paying much attention to me, before I handed Carol my purchases. She put the items and my clothes in a large bag and said, "I'll keep these here until you complete your tasks."

"Oh, okay," I said, kind of embarrassed.

"That will be four hundred and eight dollars," she said.

I almost shit myself. How would I explain this credit card purchase to my wife? Yet, I handed the card over and signed the receipt.

"The mall is two blocks to your right," she said, turning and walking away to help another customer.

I slowly walked out of the store and into the city. Walking in the heels was a struggle, but as long as I focused I didn't wobble or fall. Every person I passed I felt was judging me, yet, in reality, I was just another woman walking the street. The five minute walk to the mall took me ten as I cautiously made my perilous way to fulfill the next of the seemingly never-ending tasks.

Once in the mall, I was thankful that the restrooms were just across the hallway. I went to the restroom, head down and walked into the women's restroom. One woman was at the counter fixing her hair and I joined her praying she wouldn't speak to me. Thankfully, she didn't, and after checking myself out, I quickly exited the washroom...task two accomplished.

Looking around the food court, I wondered how I would possibly fulfill the next task. Even if I found a taker, where would we go to do it? But deciding first things first, I walked over to a nerdy looking chubby guy reading a book at a table alone and said, "Excuse me, this may sound strange, but I was wondering, could I suck your cock?"

"What?" He asked, looking up at me. His facial expression told me he was trying to connect the girlish look with the manly voice.

"I am really hungry and would love to suck your cock," I said.

"Get lost," he said, returning to his book.

After seemingly having had every guy I met wanting me to suck their cock, the first rejection stung. I quickly walked away and out of the mall, cheeks burning red yet again. Walking down the street, I saw an adult store and thought 'perfect' as I made my way there and entered.

A couple men were looking at videos, a middle aged couple were looking at bondage items (which I thought was cool), a girl was looking at vibrators and I, seeing anal toys, instantly wondered what it would feel like to have something in my ass...remembering how Oliver's finger had me shoot a rocket of cum. I went there and looked around. I saw a set of three butt plugs for beginners and decided I would buy it. I was just about to move to the men when I saw a cock on a wall. I looked at it and immediately imagined what it would be like to fuck myself with a cock. But this one was way too big, and just as I was beginning to look for smaller ones like it, a man's voice behind me asked, "Can I help you, pretty lady?"

I turned around and asked, "Do you have one of those but smaller?"

"Are you new to anal play?" He asked, again not showing any reaction to the reality that I was obviously a man.

"A complete virgin," I admitted.

Taking the package in my hand, he grabbed another one and said, "This one is a few bucks cheaper, comes in five sizes and vibrates."

"Oh, okay," I said.

"As for wall bangers," he said, "we have a few choices in size and colour."

I ended up grabbing a six inch pink one, keeping with the theme.

He asked, "Do you have anal lube?"

"No," I realized, thankful he had mentioned it, as I glanced over at the two men still in the store.

Grabbing a bottle, he said, "This is the best one available although it is a bit more money."

"I'll take it," I said, taking another quick look.

"Anything else?" He asked.

"Um...well...I..." I Struggled to say it.

"Are you looking for a gloryhole?" He asked.

"Yes," I nodded, figuring now that it was out there. "My master wants me to suck someone before I can get out of this outfit."

"You should stay in it, you look pretty natural," he said.

"Thanks," I said, flattered by the compliment.

"Second door on your right," he said.

"Thanks," I said.

"You can pay for these after," he said, taking my anal toys.

I walked down the hallway and to the second door on the right. Opening it, I walked in to a small eight by eight room. There was a small table with a water jug on it and a stool in the middle of one wall in front of a hole.

I walked to the hole and looked at it. I wondered how long it would take to have a cock pop through the hole. I waited a couple of minutes before I heard someone on the other side, followed by the sound of pants unzipping and then, staring me in my face, was a big black cock.

I stared at it. It was long and thick and it wasn't even hard yet. Based on my first experience with a black cock, I had to say the rumours of black cock size are true.

"Stop admiring it, cocksucker, and get to work," the man said firmly.

"Yes, sir," I said.

"Sir, that is rich," he chuckled.

This was a cock I would have loved to savour, to suck on his balls and tease him. But obviously that wasn't possible. Instead, I started by licking the bottom of his shaft and slowly slithering up to his wide cock head. His cock had a natural sweatiness which was salty and addictive.

"Hmmmm, we have a cocksucker who likes to worship," he said. "Do you love black cock, cocksucker?"

As I reached the top and licked his pee hole I purred, "You're my first black cock, sir."

"A black cocksucking virgin," he said. "Once you suck on this you will be dreaming of it all the time."

I believed him as I opened my mouth and took his mushroom top in and swirled my tongue around it.

"That's it, cocksucker. Take your time. Worship my black snake," he said. "Get it nice and hard for that cocksucking mouth of yours."

"Yes, sir," I again said, taking it in my mouth and allowing it to grow iron stiff. The feeling of a cock growing in my mouth was an exhilarating feeling. Knowing it was hard because of me was a major turn-on, and my cock was again ready to burst out of my pink panties.

He talked throughout the blow job which only enhanced my eagerness to please. The more degrading the names, the more it turned me on. I rubbed my cock through the pantyhose and panties as I bobbed back and forth on his glorious chocolate stick, eventually getting over eight of this ten plus inches in my mouth.

He called me a plethora of names: cocksucker, bitch, slut, faggot, queer and more, each word getting me hornier and hornier. When he called me a nigger lover I moaned on his cock and when he said I would be a great bitch at the construction site, I actually came in my panties.

A few seconds later, he followed suit, as he ordered, "Swallow every drop of my cum, cocksucker. Don't you dare stop worshipping my cock until I pull it out." As he came in my mouth, shooting much more than the others had, I almost gagged, but caught myself as I continued to truly worship his cock. I kept sucking hungrily for a couple of minutes after his cum had been deposited in me before he pulled out.

I waited for a compliment or something, but he just left. I was about to get up, my task completed, when another cock, a smaller completely erect white one, popped through the hole.

I considered leaving, but the cock was right there and, well, I am a cocksucker.

I took it in my mouth and deep throated it, loving the feeling of being able to take a cock all the way into my mouth. This guy didn't say a word and shot his load in my mouth in just a minute, maybe two.

His cock disappeared and I sat and waited curious if another cock would show up. Of course, one did and so did two more before I finally left the glory hole with five loads of cum in my belly.

I walked out of the booth and over to the cashier, realizing that any of the men in this room could have been the ones who had to cum in my mouth. Suddenly self-conscious, I quickly paid for my items as the man asked, "Did you enjoy yourself?"

"Yes," I said, suddenly ashamed.

"Bart, the big guy you serviced, left me this card for you. Said if you wanted more chocolate meat to give him a call," he said.

"Oh," I said, both proud that I was good enough for him to leave a card and embarrassed by the conversation.

"You must have been pretty good," he said, handing me my cash.

"You didn't find out yourself?" I asked playfully.

"On my own," he shrugged.

I don't know why, other than I was becoming an insatiable cum hungry cocksucking slut, but I said, "I could come back later."

He smiled, "Sorry, my wife would kill me."

"My wife will kill me too," I replied, grabbing my bag and leaving the store.

Outside, I texted Gary:

MASTER G

Sir I sucked five cocks at a glory hole...including my first black cock and purchased some anal toys. I'm going back to retrieve my purchases from Carol.

I returned to the lingerie store and got my packages and gave Carol my room number before going back to the hotel. In the lobby, I saw Kevin and his father walking towards me and panicked, worried about being caught in such an outfit, but neither realized it was me, even though Kevin definitely checked out my voluptuous tits.

I got on the elevator, returned to my room and collapsed on the bed. Had I really just sucked off and swallowed five guys? The lingering aftertaste in my mouth told me yes. I got out of my outfit, which was incredibly difficult alone, and washed up. I was just getting back into my suit and tie when I remembered that I was to wear the girly garments underneath my attire.

I put on a new pair of non-stained panties, the same pantyhose, the pink bra and then my suit.

Gary didn't text me the rest of the afternoon and I actually went to a session and listened. I was just heading to meet Kevin when my phone rang again. It was Laura.

She opened with, "Did you do anything wild, stud?"

Deciding telling her the truth would be the best way to get permission to do more, I said, "I went to a glory hole and sucked on five cocks."

"Only five?" she questioned with a chuckle.

"I thought five was not cheating, but six, well, that might be crossing the line."

She laughed. "When I give you permission to be wild you really go all out."

"You told me to grab the steel rod and ride," I joked. "So I did."

She countered, n her usual playful tone, "Wouldn't that mean you take it up your ass, honey."

"I'm just a cocksucker, honey, not a faggot," I countered back.

"That's good to know. Marrying a cocksucker is one thing, but I draw the line at faggot," she quipped.

"So I can keep sucking every cock I can find?" I asked.

"Suck away," she said, laughing. "Just no eating cunt."

"So cock okay, cunt not okay," I clarified.

"Exactly," she said.

"So have you been living wild since I left?" I asked.

"Just getting fucked by an ex-student," she answered just as playfully.

"Hopefully just in the ass," I protested. "That pussy is mine."

"I don't cheat and tell," she answered, before changing the topic. "But seriously, how is the conference?"

"Riveting," I answered. "Just about to meet Kevin for supper."

"Well, go and have fun. I'm going to go and get fucked again," she quipped.

"Only in the ass," I joked.

"I'll tell him that is what you want," she said.

"If you are talking to him for me tell him to fuck you doggy style in your ass and shoot his load all over your face," I said, then realizing I went too far as soon as I said it.

"Hmmmmm," she moaned softly back. "Where has this authoritative man been all my life?"

"In hiding, but honey he has been released from the chains of propriety," I answered, which had a very clear double meaning.

"Have fun tonight," Laura said.

"I imagine I will," I answered.

"Love you," she said.

"Love you too," I said back.

I shook my head chuckling at the reality that Laura had given me permission, albeit innocently, to suck cock...that said, I had no idea that my day of sucking cock had only just begun.

The end for now....

Coming next month: Cocksucker: Cum Bucket