Shemale Surprise

"Good boy, Robert," she purred, "Now become my cocksucker, just like your wife."

I looked up again surprised, "My wife? You have been with my wife?"

"I'm just kidding," she smiled, relishing the power she had over me. "But she did promise I could fuck her after I fucked you."

"F-f-fucked me?" I stammered as I came to grips with her full intent.

"You're my bitch this weekend," she revealed, as she shoved her cock in my mouth.

I had wondered for months what it would be like to have a cock in my mouth. Writers make it sound so life-changing, and dammit they're right. As she pumped her hard eight inch cock into my mouth, all I could think of was pleasing her. I wanted to be a good cocksucker. I wanted to make her come. I wanted to taste her cum.

Unfortunately, her cock wasn't in my mouth for more than ten seconds when the elevator slowed down and Mia pulled out, pulled her pantyhose back up and quipped, "To be continued."

I looked up at her from my subservient position on my knees in a daze.

She laughed, "Stand up, cocksucker. Don't worry, you will be back on your knees in a couple of minutes."

I stood up just as the door opened at our floor.

"Let's go cocksucker, you need to finish what you barely started," she said, grabbing my hand and leading me out of the elevator and to our hotel room.

I followed like a puppy, my head spinning with shock and excitement. Once in the room, Mia got out of her dress, tugged her pantyhose back down, sat on the edge of the bed, and ordered, "Get over here, cocksucker."

I obeyed, accepting that I was going to do this, accepting that Mary had set up this crazy situation.

I moved between her legs and dropped to my knees, her big cock staring me straight in the face.

"Get sucking, cocksucker," Mia ordered.

I leaned forward and took her cock back in my mouth. I swirled my tongue around her mushroom top, teasing her like Mary usually teased me. It felt so surreal being on my knees servicing Mia, and yet it seemed equally natural.

"That's it, Robert, worship my cock," she moaned.

Hearing my name instead of cocksucker made the submission feel more real as Mary popped into my head. Yet, obviously my wife had planned this moment. So instead I just focused on giving my first ever blow job. Slowly, I began taking more of her cock in my mouth, taking a couple inches in.

"Take more, cocksucker," she ordered, her hands going through my hair.

I obeyed as I began bobbing back and forth, taking a bit more in my mouth with each forward movement. As I continued sucking, I was surprised when I heard Mia talking.

"Eaten any cunt yet?" she asked.

I froze.

"Keep cocksucking, Robert," she ordered.

I did, as I assumed she was talking to my wife while I sucked her.

Mia continued, "Just a minute, I will put you on speakerphone."

My eyes went wide at the reality that my wife was now going to be a listening witness to my first cocksucking experience.

"Can you hear me?" Mia asked.

"Loud and clear," Mary replied.

"So your husband looks really hot with a cock in his mouth," Mia said.

"I bet he does," Mary replied, "Be sure to send me a picture."

"Good idea," Mia agreed. "Just a second."

"Sure," Mary said.

Mia ordered, "Pose, cocksucker."

I looked up, over half her cock in my mouth, as Mia snapped a photo. The moment was utterly humiliating and yet equally exhilarating, knowing it was for my wife.

"Nice," Mia smiled, before ordering, "Now get back to sucking, bitch."

I obeyed, continuing my descent into cocksucking submission, as Mia returned to conversing with my wife.

"Sent, sexy," Mia said sultry.

"Great," Mary said. "Was it as easy as you thought it would be?"

"Like taking candy from a baby," Mia replied, clearly confident in her power over me.

"Oh my," Mary said, "he looks fucking hot with your cock in his mouth."

"He is a natural," Mia commented, as her hand went to the back of my head.

"So it seems," Mary laughed, before speaking to me. "I hope you're enjoying yourself, Sweetie."

Mia tapped my head and I took her cock out of my mouth as I answered, "I can't believe you set this up."

"I can't believe all these years you wanted to suck cock and never told me," Mary countered.

"I-I-I haven't always wanted to suck cock," I stammered.

"Well, you're a cocksucker now," Mary said.

"Are you a cunt-licker yet?" I asked.

"You will have to wait to find out," Mary said, "now get back to sucking Mia."

"Yes, honey," I answered, as I leaned forward and took Mia's cock back between my lips, more determined than ever to take all eight inches in my mouth.

As I hungrily bobbed on Mia's cock, Mia continued her conversation with my wife. "So, this means I get your ass now, right?"

"A promise is a promise," Mary said, her tone implying she was eager to allow that to happen.

"I am going to make you my little slut," Mia promised.

"I can't wait," Mary purred.

Mia said to me, "Play your cards right, cocksucker, and you may get to watch."

Mary laughed, "I want to watch him get your big cock ready for me."

"Hmmmm," Mia purred, "you're a nasty wife."

"That I am," Mary said, before saying, "I need to go. Photos start in ten."

"I expect you to be eating cunt tonight," Mia said demandingly.

"That's the plan," Mary replied.

"Good. Have fun," Mia teased.

"You too," Mary laughed, before adding, "Have fun too, Robert."

I wanted to respond, but Mia held my head on her cock, and responded for me, "Oh, he will."

Their conversation done, Mia returned her focus to me. "That's it cocksucker, I expect all my cock in that pretty mouth of yours."

I moaned in response, now taking six inches with each forward bob.

"I can't wait to tap your ass, Robert," Mia continued. "I plan to fuck you like a cheap little slut."

The naughty trash talk only enhanced my eagerness, as my cock begged to be released from my pants.

"Tell me how much you love my cock, Robert," she ordered.

I reluctantly took her cock out of my mouth, looked up at her to see she was filming my submission, and answered, "I love your big, hard cock."

"And you want my cum?" she asked.

"God, yes," I moaned, curious to discover what it felt like to have cum sprayed in my mouth.

"And how about your ass, cocksucker," Mia continued, tapping her cock on my lips, "Do you want me to fuck that ass of yours?"

Although I had some trepidation about getting ass fucked, I had long resolved that I was Mia's bitch this weekend as I stammered, "I-I-If you want."

She laughed, standing up, "If I want? You are such a cock tease."

She shoved her cock in my mouth, held my head with both hands, and fucked my face. All eight inches were forcefully slammed into me and all I focused on was not gagging as I was roughly face fucked.

Her balls bounced off my chin, which only made my sexual submission hotter.

"I plan to fuck you and your wife whenever I want," Mia informed me, as she continued to pound my face.

The idea of Mia fucking Mary turned me on as I moaned on her cock.

"You want me to fuck your wife, don't you?" she asked, although I couldn't answer with her cock fucking my face.

After a few more strokes in my mouth, Mia grunted and warned, "I'm coming, cocksucker."

Seconds later, I felt her cum shoot in my mouth as she slowed down her deep thrusts. I eagerly swallowed her surprisingly tasty cum as shot after shot of her seed was deposited in my mouth.

Eventually, she pulled out of my mouth and complimented me. "You are a natural cocksucker, Robert."

"Thanks," I absurdly said, still on my knees.

Pulling her pantyhose back up, she said, "We should probably meet your buddies at the bar."

My cock begging for attention, I replied disappointingly, "Oh, I suppose."

She laughed, "Oh don't worry, Robert, I will let you fuck me tonight, but all good things come to those who wait."

"Okay," I nodded, disappointed, yet excited at the promise of sex later.

"Let's go," Mia ordered, "I could use a drink."

I joked, standing up, "Um, could I have a second to let the snake go to slumber."

Mia moved to me, her hand going directly to my crotch, "Is this for me?"

"It is a full scale salute," I quipped, trying to be witty.

"Hmmmmmm, maybe I could have a snack," she said, dropping to her knees.

I held my breath as I looked down at this ravenous beauty, her hand firmly on my stiff cock. After a brief moment, which felt like an eternity, she stood back up, deflating me, as she said, "I think I'll wait."

"You bitch," I quipped.

"That I am," she smiled, giving my cock one more firm squeeze and saying, "Let's go."

"Yes, Mistress," I sarcastically replied.

"Hmmmmm, Mistress, I like that," she smiled, walking out of the room.

In the elevator, Mia dropped to her knees, fished out my cock and said, "Maybe just a quick sample."

She devoured all six inches of my cock in one forward bob.

I groaned, my long neglected cock finally getting the pleasure it had long desired.

Mia bobbed back and forth for a few seconds before standing back up and saying, "Just enough to wet my appetite."

"Just enough to give me blue balls," I countered, reluctantly putting my cock back in my pants.

"What doesn't kill you makes you stronger," she countered back.

"That is what I am afraid of," I shot back, not sure my cock or my heart could handle the sexual roller coaster ride I was currently on.

"Yes, but what a way to go," she smiled.

"Touché," I nodded.

We made our way to the bar and joined the guys. The next hour was full of drinking and the usual bull shit, the only exciting thing being Mia's hand that roamed freely, constantly teasing me.

Frank finally said, "Shit, we're going to be late!"

We downed our drinks, mine being the fourth I had in just over an hour, and made our way back to the hotel ballroom.

The dinner went without incident, Mia not once touching my cock or making any sexual comments, instead behaving herself with the other couples around us. She even took part in the idle chit chat with the women at the table...all of whom knew that Mia wasn't my wife. Mia, being the polite woman made it clear we were just friends, not wanting to taint my, or Mary's, image in this exclusive, uppity group of women.

When Ken's wife Carrie, a beautiful redhead, excused herself to go to the washroom, Mia whispered, "Time to teach this bitch a lesson."

My mouth dropped open at Mia's intent as she said politely, "I think I'll join you."

I watched as Mia left apparently planning to seduce the vice-President's wife. My cock, which had finally calmed down, instantly jumped to attention at the thought. Carrie was hot, but a complete pretentious bitch. The woman Mary hated the most. I instantly wondered if Mary had anything to do with this.

I texted Mary:

Did you have anything to do with Mia trying to seduce Carrie?

A moment later, Mary replied:

Maybe.

Another text followed:

Want to see what I've been up to since photos?

I quickly texted back:

With a question like that the answer is, of course, yes.

A moment later, which felt like an eternity, a photo came. It was a picture of Mary between a woman's legs, her tongue licking a hairy cunt.

I texted back, my cock again rock hard:

Oh my! Who??????

A text back only enhanced my intrigue:

Someone you know.

I texted back, hating not knowing...a few women I knew all popping into my head:

Stop being so cryptic. Whose cunt are you eating?

I didn't get a response which only fueled my imagination. If it was someone I knew that limited it to only a few people. It was unlikely to be the bride, Jenny, because the thigh highs were tan and the bride assumedly wore white. The other three in the wedding party though I had met. Jenny's younger sister Amber, the maid of honour was very hot. Kimberly and Diane, the other two bridesmaids were friends from high school. It couldn't be Kimberly, as she was larger framed than the legs in the picture. Diane, on the other hand, was a good looking blonde with fake tits. Yet, I couldn't fathom them risking their friendship over sex. Yet, after the past few hours anything was possible.

I texted back:

???

Yet, I didn't get a response, which frustrated me...as I continued staring at my phone, I forgot all about Mia and Carrie...until they came back.

Carrie's face was ruby red and she looked completely humiliated.

I asked, trying to stir the pot and gauge her reaction. "You okay, Carrie? You look flushed."

She stammered, "I-I-I'm fine."

Mia, returning to her seat beside me, added, "More adequate than fine truth be told."

I barely held in a laugh as I knew exactly what she was saying...Carrie was a shitty cocksucker or lay, but her husband gave a perplexed look. Luckily, he had been married long enough to not ask questions to which he didn't want to have to pay attention to the answer.

Carrie's face went redder, as I added, "I hope you're better than fine."

Mia squeezed my cock, as she leaned in and whispered, "She is walking around with my cum leaking out of her cunt." She opened her purse to show me a pair of panties.

I smiled, "Oh my."

"I already sent a picture to Mary," she revealed.

"She isn't responding to my texts," I said.

"Probably eating cunt again," she said nonchalantly.

"How do you know?" I asked.

"She sent me a picture," she shrugged.

"Do you know who?" I asked desperately.

"No," Mia shrugged her shoulders.

I sighed, "She is driving me nuts."

"I think it is almost time for you to play with my nuts," she quipped.

"Didn't you just shoot a load?" I asked.

"True," she said. "Plus, I want you to really want it."

"What?" I asked, even though I knew what she was going to say,

"Me to take your anal cherry," she said.

"I better have a few more drinks," I said, hoping some liquid courage would dull the inevitable pain.

"Don't get too drunk," Mia warned, standing up. "I want you lucid when I pound that tight ass of yours."

Before I could respond, she was gone and I finished my drink.

Over the next two hours, I checked my phone for the reply from Mary that wouldn't come, even though I texted her a dozen times and called her twice; I also had four more drinks, danced with Mia a few times and visited with a few co-workers. The whole time, I kept waiting for Mia to say it was time.

Interestingly enough, the longer Mia waited to make me her bitch, the more I wanted it. I watched her dancing with others, flirting with the younger men and chatting with some women and I was always jealous. I wanted her to myself.

Deciding fuck it, I walked over to her and whispered, "Its time."

"Time for what?" She asked, all innocent.

"You know," I answered, not sure I could say it.

"I might," she said coyly, "but I want to make sure we're both on the same wave length."

I leaned in, even though the music was too loud for anyone to hear me, and whispered, "I want you to take my ass."

"Hmmmmmm," she purred.

"Mens' bathroom in five minutes," she said.

"Can't we go up to the room?" I asked, not liking the possibility of getting caught being sodomized.

"We could," she nodded, giving me a brief glimmer of hope, before saying, "but we won't."

I knew I was so completely under her spell, I was going to do whatever she told me to, but I pleaded, "Please, I'll do anything."

"I know you will," Mia smiled, before firmly saying, "Men's bathroom, five minutes." She walked away, signalling the conversation was over.

...

Five minutes was an eternity, both because of excitement, I couldn't wait to get fucked by her and trepidation as I was scared shitless (pun intended) to get fucked by her and doubly scared to be caught in the act of anal submission. Yet, again I was completely at the whim of this Shemale goddess...willing to risk my career to obey.

I reached the bathroom and Mia smiled, "Ready to get ass fucked?"

"Yes," I answered sheepishly, the question making my cock flinch.

"I also know who your wife's weekend Mistress is," Mia smiled.

"Who?" I immediately asked.

"Be a good ass slut and I may tell you," she smiled in her usual sultry voice.

"Fuck, you make everything sound so sexy," I said.

"Euthanasia," she said the dark word in the same sexy voice.

"Yep, everything," I nodded, my cock dying for attention.

"Time to take that cherry," she said.

"You know just how to woo a man," I joked, enjoying her bluntness.

"Go check if the bathroom is free, cocksucker," she smiled.

"Yes, Mistress," I nodded, just as Matthew, another colleague, walked past us and into the men's washroom.

"I guess that answers that," she smiled. "It's okay, I just wanted to see how far you were willing to go to become an ass slut."

"I'm completely at your whim," I admitted, thankful that she maybe wasn't going to make my sodomy public.

"Delicious," she smiled, "I have a better place to break in that man cunt of yours."

She grabbed my hand and led me to the elevator as I tried to come to grips with the term 'man cunt'.

In the elevator, she pressed the penthouse floor, which surprised me, before she dropped to her knees, fished out my cock and sucked me furiously. Although Mary was a great cocksucker, Mia did something with her tongue I couldn't explain. After less than thirty seconds, I blame it on all the teasing of the day, I warned, "I'm going to cum."

Her hand went to my ass and as her finger entered my asshole, I shot my load down her throat.

"Oh fuuuuck," I grunted, as she kept her finger lodged in my ass and kept bobbing hungrily on my cock.

After a few more seconds, the elevator began slowing down, Mia stood up, smiled and said, "I expect you to last a long longer now."

"I imagine that is possible," I nodded, putting my cock away. The thought of fucking her ass still enough to get me revved up again.

The elevator door opened and I followed her. We entered a huge suite with a hot tub, wine chilled on ice and a heart shaped bed. This was obviously the honeymoon suite. I protested, "We shouldn't be here."

"Get naked," Mia ordered, ignoring my protest.

"But this is my boss's suite," I pointed out.

"Now, or I go find another bitch to fuck," she ordered impatiently.

Knowing I was indeed her bitch, I silently obeyed.

Once naked, she ordered, as she hiked up her dress and tugged down her pantyhose, "Come get my cock ready for that man cunt of yours."

"Yes, Mistress," I agreed, looking forward to having her cock in my mouth again.

On my knees in front of her, I took her semi-erect cock in her mouth, which had a strange taste to it.

Mia, as if reading my mind, asked, "Can you taste that bitch's cunt on my cock?"

"Yes," I admitted, the taste instantly making sense.

"Although I bet when I make her suck my cock again later tonight the taste of my cock will be even more distinct," Mia quipped.

I asked, taking her cock out of my mouth, "How many times can you come?"

"I'm the energizer fucker," she smiled, shoving her almost completely erect cock in my mouth.

She slowly fucked my mouth as she continued, "I can't wait to fuck Mary. She has resisted my aggressive flirtation for years, but she promised if I took your cunt, I could have hers."

I wanted to speak, to clarify, but her cock sliding in and out of my mouth didn't allow it.

She continued, "Plus, Mary has sent me more pictures and has given me permission to show you photos of her weekend Mistress."

My cock flinched at the thought of Mary having a Mistress.

Pulling out of my mouth, she asked, "Ready to be ass fucked, my cute little cocksucker?"

Her words were absurd, yet so was my answer, as I replied eagerly, "Yes, Mistress."

"Yes, Mistress, what?" She questioned, her fully erect cock pointed right at me.

"Yes, Mistress, I want you to fuck my ass, my man-cunt. I want you to make me your bitch," I admitted, each self-derogatory word getting me hornier...making me feel like a little slut.