The Deal Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

That caused me to freeze up again for a moment, but I shook myself out of it and tried to turn around and tell Mike "goodnight" and that I had an early morning or something. Instead, when I had turned enough to see his calm expression and his grin, I realized I was starting to cry. I'd never felt so embarrassed in my life, and that made me cry even harder.

"Come on, Keith, let's get you up to your apartment," Mike said as he put his arm around my shoulders and walked with me, holding me up and guiding me along the way. "Relax, everything is going to be okay."

I didn't know what to say at that point, so I said nothing and kept walking nervously towards my apartment. As usual, I was terrified of this man, afraid he might hurt or kill me, even though he wasn't acting threatening in any way. Mike was an imposing figure at over 6'3" with a powerful build, but he spoke calmly and reassuringly as well as being very assertive.

When we got to my apartment door, I dropped my keys twice fumbling to put them in the lock. The first time I had to bend over to pick them up, Mike stood back and said, "Mmm, mmm, that is quite the view." That sent my nervousness through the roof and I quickly dropped the keys again after fumbling a second time to work them in the lock. This time, Mike came up behind me, put his hand on my butt, and said, "You can't keep tempting me like that, sweetie."

Finally able to get the door open, I turned around, shaking like a leaf, and tried to tell Mike "goodnight." As I stammered, Mike put his index finger over my lips and said, "Shh, relax, everything is going to be okay, Keith."

Once inside, I was shaking so much I could barely stand up, turning to Mike and stammering hopelessly out words of protest while he just smiled.

"I bet you have a pair of sexy high heels around here somewhere, don't you?" he said with a calm smile. "I'd love to see you in them."

Swallowing hard, any words I could think of sticking in my throat, I nodded as tears began dripping down my cheeks.

Mike reached up to my face and calmly wiped my tears away. "You are such a meek and willing pussy, aren't you, Keith? Well, tonight you'll start to learn your place in the world. Go put on those heels for me, sweetie."

As I made a meager attempt to tell Mike I couldn't, another voice came out of me, very soft and very feminine, that instead said, "I'll just be a minute." There was no stammer, no stutter, and the words came out so smooth and fluid that they sounded nothing like my usual voice. With that, there was nothing I could do but turn and walk nervously into my bedroom and into my closet where I kept my secret stash of "girl clothes."

It took a while, with my hands trembling so much along with the rest of me, to get on the pair of strappy five-inch heels I'd recently ordered online and only tried on a couple of times. When I finally made it out, having to hold onto the wall as I went out to the living room, I knew I wouldn't able to stand without support. I'd had very little practice wearing heels and as nervous as I was the sight much have been laughable.

"Come here," Mike said with a demanding snap in his voice. "Someone obviously needs a lot more practice walking in heels. Stand up straight. I can't see how sexy those faggot legs of yours look in those heels if you are stumbling all over the place."

I tried to stand and fell over. Mike caught me and stood me back up, putting his finger under my chin, lifting my eyes to look at him, and said, "Maybe we need to cut to the chase. You best practice more walking in those heels. For now, get the fuck on your knees and suck me, fairy boy."

This, much like the men in the laundry room, had so often been a part of my masturbatory fantasies that I'd completely blocked the memory of those times out so I could pursue my non-existent hopes for having a relationship with a woman. Mike was so strong, so commanding, and as I stood there, looking meekly into his eyes with tears rolling down my cheeks, he simply put his hands on my shoulders and helped me to my knees.

"Kneeling in heels is so much easier," Mike said nonchalantly as he unbuckled and dropped his pants. "Aren't you going to even look at it?" he added with a laugh as I tried looking away as I knelt before Mike willingly and admittedly eagerly.

I finally worked up enough courage to look at Mike's cock, hanging there, half-erect in front of me. It was very large, so much bigger than mine or even the men in the laundry room. Tears were flowing down my face as Mike lifted my head up to look at him as he told me, "This is where you've always wanted to be. From now on, you won't be able to think about anything but cock and pleasing men and turning them on so their cock will get nice and hard for you to suck on. Now, stop shaking and put your fucking hand on my cock and stroke it already."

As much as I could try to deny it, I knew that Mike was right. My hands were trembling so much I barely realized when I finally had them on Mike's cock, my fingers coiling around it, starting to stroke that beautiful piece of man meat.

"Oh god..." I gasped out as I looked at his beautiful cock, right there in front of me, begging me to suck it because it was getting so hard in my hand.

"Give a nice little kiss to the tip, Keith," Mike told me, talking down to me like I was a child.

Leaning forward I very lightly touched the tip of his cock with my lips and let out a huge gasp. I couldn't help myself. My lips trembled as I began excitedly kissing all over the head of his cock. After a dozen or so increasingly passionate kisses, I found my mouth right at the tip of his cock again. I couldn't help myself. My lips parted and then completely engulfed the head.

"Someone has been mighty hungry," Mike said, laughing as he watched me clumsily come off the head of his cock, pulling back and panting as I just stared at his stiff cock, the head now wet with my saliva.

"Why do I like this so much... why do I..."

"Because you're a fairy cocksucker, Keith. Stop thinking and suck that cock."

At first, a million thoughts raced through my mind. I remembered all the bullying I'd endured throughout my school years and how I would never fight back or defend myself. All the taunts and the beatings behind the school I took and all I ever did was cower and take the beating or the abuse until I gave them what they wanted, to see me cry so they could laugh at me.

Pathetic would have been a good way to describe myself, and now here I was on my knees sucking a man's cock and enjoying it more than I'd enjoyed anything in my life. It was as it I could not stop, no matter how clumsy and sloppy I was as I tried to do a good job and please Mike.

And then it all became an ecstatic blur as I felt my erection, half the size of Mike's man meat, pop out of my panties and wave wildly in the air, bone white with excitement, harder than I'd ever been in my life, hard to the point of it being painful.

"Don't you dare touch yourself," Mike warned me as he made me look up at him. "This is the only cock you're pleasing," he added as he slapped his cock back and forth across my cheeks.

Once it went back in my mouth, I sucked it with passion and enthusiasm, no longer thinking as I worked for I have no idea how long and Mike pulled out of my mouth, jerked his cock quickly a few times, and ejaculated a huge load all over my face. He'd moaned loudly, yelling out, "Here comes your prize, cocksucker," and then using the head of his cock to smear his semen all over my face.

"Here's my number," Mike said as he got up, put his pants back on, wrote his phone number down on a piece of paper on my desk, and walked out the door saying, "Call me when you want some more dick, sexy legs."

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
TVFrannieTVFrannieabout 5 years ago
Welcome back!

I used to read your work all the time and loved it. You really had a way of making me and my little clit so excited. And now I find you are back and as erotic and exciting as ever! You excite me so much gurl! Nice work!

CarrieQCarrieQover 5 years ago
Wonderful read!

Sissies everywhere will easily relate to this excellent story! Can't wait for more!

panty_ho44panty_ho44over 5 years ago
This took me back to my first apartment

This reminds me so much of my early 20s... when my ex-wife taught me how to be a sissy cuckold cocksucker!

Lovely story!

AnonymousAnonymousover 5 years ago
I love sucking cock too

I started sucking cock when my sister's boyfriend caught me wearing panties. He said blow me or else I'll tell. So I proceeded to give him the world's worst blow job but swallowed his entire load. Ever since then, I'll suck cock whenever I can and always swallow.

sissyjolie4usissyjolie4uover 5 years ago
The love of cock

Great start to this story, hope more in on the way!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
Better as Riley Ch. 01 Ryan discovers everything is more fun as Riley.in Transgender & Crossdressers
More Stories