Emma Humiliates and Feminizes Her Boss, Chapter 6

Posted on April 28, 2012 by admin

Once my eyebrows were perfectly shaped to Emma’s exacting standards, she surprised me by pulling out a little camera and smiling devilishly at me. “I’m going to be documenting my progress here. I’m sure you wouldn’t mind that, would you? ” I numbly shook my head.

After she snapped a picture, she began to make me up. She started out by rubbing a creamy liquid across my face with a little wedge shaped sponge. “Your pores are huge, such a turn-off. How on earth are you going to look like a real woman like that?” The feel of her body so close to mine, the sensual purr of her voice, the smell of her perfume, all combined to make my tiny dicklet begin to throb in pleasure. I knew if I so much as touched my little cock right then, it would explode in orgasm.

As she continued by powdering my face, I began to wonder if she were being honest. A real woman? She wanted me to look like a real woman? For whom? Surely not her; she had already seen me as a man, so she would never be fooled by even the most expert of make-up jobs. Maybe she intended to show me off and humiliate me in front of some of her girlfriends. Yes, that was probably it. She couldn’t possibly be thinking of anything else.

She grabbed my chin in a surprisingly strong hand and held my head still while she penciled in my eyebrows. I wanted to look in the mirror to watch my transformation, but she kept me still. “You’re going to have to wait until the end to see, little man,” She chuckled. With an equally deft hand, she applied eyeliner, mascara, and eyeshadow. I began to appreciate the amount of time and effort women put into making themselves beautiful to the world. All of this seemed like an incredible amount of work to do every day. As I contemplated the act of daily applying make-up, my small penis started to throb again.

Emma applies cock-sucking pink lipstick to her boss

Emma paused for a moment, rummaging in her vanity. I was tempted to sneak a peek in the mirror while she was distracted, but I knew I wouldn’t get away with it. “Aah, there we are.” She grabbed a tube of lipstick and instructed me to pucker my lips. As she applied it, she snickered at me quietly. “Yes, that’s the perfect shade for you, I call it ‘cock sucker pink’.”

Emma Humiliates and Feminizes Her Boss, Chapter 5

Posted on April 9, 2012 by admin

Continued from Chapter 4

Once I was shaved to Emma’s liking, she sat me down at her vanity table. I was still nude, and without any body hair below my neck, I felt more naked and exposed than I had in my entire life. And without its concealing coverage, it was obvious that my tiny dick was not in proportion to the rest of me. It was still standing at attention, rock hard and rigid.

Emma does not want you to look like a clown

“I don’t trust you to do this for yourself, you’d probably end up looking like a bad clown,” Emma said. She spun me away from the mirror and gathered her instruments of sissification; lipstick, mascara, eyeliner, and an assortment of tools that looked more like medieval torture devices than beauty products. “Now close your eyes.”

I closed my eyes while Emma did her work, occasionally tsking over my dry skin, clogged pores, and overgrown eyebrows. I didn’t realize how she was going to fix the latter until I felt something hot and sticky being spread over my brow ridge. And then… RIIIP!

“Ouch!”

“Oh shut up, you little sissy. Quit being such a wimp, women do this all the time.” She moved on to my other eyebrow and I conceded defeat. I had promised myself I would let her do whatever she wanted, even feminize me, just to have a chance with her. But what would the guys at the office say when they saw my newly feminized eyebrows?

Even through the pain and humiliation, my small penis stayed rock hard. How could I be this horny after all this? I thought that it was the presence of such a beautiful woman, and the chance that I might finally get to have her in bed, but what if I was wrong?

Emma Humiliates and Feminizes her boss, Chapter 4

Posted on March 29, 2012 by admin

Continued from Chapter 3

Emma looked over my nude body critically. My rock hard little dicklet seemed to shrink under her disapproving gaze. “Ha! It’s even smaller than I thought! You really must be a worthless loser.”

I felt myself flush and reminded myself that she was really into small penis humiliation. This is how she got her kicks, and I had promised myself that I would do anything at all to please her, even humiliate myself like this. I would even let her feminize me as much as she wanted. Strangely enough, I felt my small cock get even harder under her scorn.

Emma is critical of your small penis

“You’re hung like a gerbil but you’re hairy all over. I’m not putting you into my expensive lingerie until we get you shaved.” She turned and walked briskly out of the room, not even looking over her shoulder. As though she knew I would obey her every wish. Which I did, of course.

She led me through the house as though to flaunt her wealth, making me feel lees and less masculine as we went. How on earth could I have hoped to impress this woman with a single expensive meal? There were other men, real men, who could do that and so much more for her. We walked past a number of windows, and I instinctively cringed and cupped my hands around my inadequate manhood, fearing that someone would see how pathetic I really was.

I followed her into the bathroom, all gleaming tiles and polished marble. Her stiletto heels clicked authoritatively on the floor as I meekly entered after her. Wasting no time, she handed me a disposable pink razor and rose scented shaving cream. “I assume you know what to do with this?”

“Yes, ma’am.” I looked down at the bottle and sighed. It was lurid pink and I knew then what other plans she had for me that night.

Emma Humiliates and Feminizes her boss, Chapter 3

Posted on March 13, 2012 by admin

After the extravagant dinner and dancing in the exclusive club, Emma took me back to her house. Her husband was on one of his many business trips, she said, so we would have the entire place to ourselves. I’m glad that she drove, because I was so horny and nervous that I was shaking. I wanted her so bad I could barely stand it.

She let me in and then led me to the bedroom. Once there, she suddenly became very businesslike and started rummaging through drawers and pulling silky lingerie, filmy dresses, and sexy stilettos out and tossing them on the bed. I was astounded. Was she going to dress up for me? I couldn’t believe my luck. My tiny cock began to get even harder and it became difficult to think of anything but her.

She looked at me over her shoulder. “Strip for me.”

I mumbled assent and began unbuttoning my shirt.

“What did you say?” she asked coldly.

“Umm.. yes?” I was terrified of angering her and losing my chance to be with her. I would have cheerfully cut off my right hand if it would have made her happy. I kept undressing as quickly as I could.

“Yes what?”

“Yes ma’am.”

“Good boy. In the office you may be the boss, but here, you’re my bitch.” She looked over my nude body, my pathetically small penis pointed straight up and smiled, wickedly.

She laughed heartily. “Is that as big as that little thing gets?” she said, humiliating my tiny penis.

She thrust a handful of lacy undergarments at me with disdain in her eyes. “Now put these on. You know what forced feminization is, right? Because I’m going to whore you out.”

Emma Humiliates and Feminizes her boss, chapter 2

Posted on February 28, 2012 by admin

I had finally come up with the perfect plan to give me a chance with Emma. The gossip in the office was that she was only with her husband for his money, and she cuckolded him with big black guys because he had a tiny dick. So I would let it slip that I had recently inherited a lot of money and was considering quitting because I no longer needed to work.

After a few days of letting the gossip circulate, I tried again with Emmma. I casually asked her if she’d like to go to dinner with me, at one of the most upscale restaurants in town. I knew my ploy had worked when she agreed. I would be eating into my savings to afford this, but it was worth every penny, just to be near her.. and to have a shot with her.

Emma loves small penis humiliation

After dinner, I took her dancing. I couldn’t help getting hard as I wrapped my arms around her, and I knew she could feel my small penis pushing up against her. By the look on her face, she knew how tiny it was. But even the prospect of her laughing at me later was intoxicating; I had heard she got a kick out of small penis humiliation which is why her husband was such a cuckold. Everyone in the office knew she was a slutty MILF, and that she really preferred to have a big black cock instead of her husband’s small penis. But I still had to try.

The wine, the lavish dinner, and the dancing had finally gotten to me. I was more turned on than I had ever been in my life. I leaned in and whispered to her that I loved her, and would do anything for her, just for a chance to be with her. And it was true. Emma owed my heart just as much as she owned my cock right then.

Her sexy, throaty chuckle sent thrills down my spine. “Honey, you know why they call me a ‘trophy wife’, right? If you’re really in love with me, I’m going to make you prove it.”

Emma Humiliates and Feminizes Her Boss

Posted on February 10, 2012 by admin

A fantasy about small penis humiliation, cuckolding, and forced bisexual cocksucking and anal play, told in serial form…

Chapter 1

Emma had been my secretary for a while when I finally had the guts to ask her out the first time. I had heard plenty of the office gossip; that she was a real wild woman who cuckolded her husband with lots of guys. Usually a different guy every night. She’s a beautiful woman, too; long luscious legs, an amazing rack, and a nice round ass. She’s a real Georgia peach. And as a MILF, I just knew that she had plenty of experience in the art of pleasing men, not to mention how kinky she was.

Emma is a Beautiful Kinky Cuckolding MILF

So I finally gathered my courage and asked her out for a drink. She smiled sweetly and said in that soft southern accent of hers, “No, honey, I don’t think so.” I was devastated. But I couldn’t give up. She was just too hot and too tempting to get out of my mind. Every time I saw her my cock would get hard as I imagined everything she did with her lovers… and wishing I could be one of them.The next day she wore a tight little mini dress and stiletto heels to work. I knew she was teasing me, getting my all hot and bothered and knowing I could do nothing about it. So I tried again; I couldn’t help myself. And once again she turned me down. “I’m sorry, honey, you know what I like. I like big black guys with big black cocks. And you just don’t fit the bill.”

She was right, of course. I had seen her leaving work with a multitude of huge black men with (presumably) huge black cocks. And as a short, pasty white, small dicked guy, what was I going to do?

I sat down at my desk and began to think up a plan…

Humiliate yourself with self-bukakke on cam for me, loser

Posted on January 26, 2012 by admin

I want to see you humiliate yourself on cam for me with self bukakke by spraying cum all over your face, loser.

Do you have a tiny little dicklet like my huband? Are you so tiny and pathetic that no self respecing woman will let you fuck her? Then I’ll bet you’re a chronic masturbator, too. I know your type; watching porn, wishing you had a big cock like a real man, masturbating furiously because you know you’ll never be able to fuck a kinky MILF like me. I prefer big cocks, not that teeny peener hanging between your legs.

But you can still amuse me, you know. I get such a kick out of small penis humiliation. I’ve had quite a bit of practice at it, since my own pathetic husband can’t please me either. And I want to do so much more than just phone humiliation, I want to watch you.

That’s right, you’re going to put on a show for me. I want you to get on cam for me and show me that tiny little peener that you can’t keep your hands off of. Give me a good look so I can make fun at it; I love a good laugh at a man’s expense. And I’ll want you to play with it while I’m laughing at you, sneering at you, and humiliating you.

But that’s not all. You’re going to really humiliate yourself for me, loser. I bet you know what bukkake is, don’t you? Well, you’re going to do it to yourself. That’s right, when you finally make that little dick cum, I want you to spray it on your face for me. Show me what a good little cumslut you are.

Spray your own cum on your face for me bitch

Be ready to put on a good show for me, I could use a laugh.

You know you want it

Posted on December 27, 2011 by admin

Hey there, boys. I bet you have some dirty little secrets, don’t you. And I think you need to confess your sins. You’ve been watching lots of porn, haven’t you? Don’t lie, all men do it. But you’ve been doing it for another reason, isn’t that right? You’ve been watching porn not only for the naked women, but to get a glimpse of all of those big hard cocks that the women are getting pounded by. I know you think about those cocks. I know you fantasize about them when you’re playing with that little cock of yours. And you’re going to tell me all of your dirty little perversions.
Confess to me how you’d like to be like those women, sucking on a big hard cock. I know you’ve thought about it. I bet you’ve even borrowed your girlfriend’s dildo and even tried it yourself. It’s not the same, however, since you don’t get rewarded by a face full of cum like a real cock can give you. And what about ass play, hmm? Have you tried that yet? I bet you’ve fantasized about anal with a real man fucking you, haven’t you?

Confess your deep dark fantasies to MILF Emma

We’re going to do even more than just fantasize. When you call me, I’m going to cuckold you in only the way a slutty milf like me can. I’ll let you watch while my big black boyfriend fucks me nice and hard while you stroke that little loser cock of yours. I’ll even let you get him ready for me so you get to feel a real live cock pulsing between your lips. And if I get bored with him before he runs out of endurance, well… lets just say that we’ll be using you for backup. He may even make you his bitch while you’re cleaning up my juicy wet cream pie.

So Many Boytoys, So Little Time…

Posted on December 15, 2011 by admin

Cuckolding MILF Emma Has to Farm Out Her Boytoy to Hubby…

What happens when you are such a slut as myself, that you screw up and book more than one date on a given night?

That’s what happened to me last night. I have been working very hard on the phones lately, taking all sorts of humiliation and cuckolding phone sex calls. So I decided to take last night off for a very needed vacation.

The only problem is that I accidentally made a date with 2 different guys!

Now in some cases this would not be a problem. I would just combine the two dates, and introduce the guys to each other, and we could go from there. I date a lot of big bucks that are into watching me cuckold them in a non-humiliating way with another big-cocked boytoy. But both these guys Jim, and Leslie, are into “solo” performance only.

So what to do?

Well I know that Leslie is also into men, especially into topping pathetic little weenied bitches like my hubby. So I called up hubby at work, and told him to come home, that it was an emergency. Naturally he thought he was going to watch his slut wife get fucked by a big cock, and so he found called in the assistant manager, and hurried home.

Instead I was waiting for him alone. I told him to strip for me naked, and then I handcuffed him. I then had him lie on the bed face down. I tied his legs to the foot board of the bed, wide apart.
He was such a site!

Hubby Gets Lucky Tonight

I told him I was going out for several hours, but not to worry, he’d have company soon. Sadly I’d overbooked tonight and so he was going to have to be there for my overflow.

And so I left him like that, squirming and begging me not to leave him. But I am betting anything that tiny penis was rock hard.

When I finally came home in the wee hours this morning, his ass cunt was open and sore and leaking. And he had sperm smeared from his hair to his knees. Leslie must have had a good time.

I’m going to lie down and sleep for a few hours, and then I’ll be back up for more exciting cuckold phone sex.

My Cuckolded Phone Sex Caller in Panties

Posted on December 5, 2011 by admin

So a couple of weeks ago I told y’all about my cuckolded phone sex caller Dave, who started leaving comments on one of my other blog posts.

So Dave has called me several times in the last few weeks and had been telling me about his wife, who is obviously cuckolding him. What’s really funny is that Dave will still ask me from time to time if I think he’s being cuckolded. In fact it makes me laugh so hard, that he would even have any doubts by now.

And so in order to make Dave realize what a tiny little dicklet he has, I’ve ordered him to continue peeing sitting down, and to tie a little pink ribbon on his dicklet, and also to wear girly panties. I think Dave likes my brand of feminization, though

Here is a picture of Dave in girly panties that he stole from his wife.

Dave in cute pink floral panties

Isn’t that just the cutest little thing you ever saw? I mean there’s barely a lump there…

So Dave, yeah keep wearing your panties, and keep looking in the mirror and reminding yourself of the fact that you’re officially now a cuckold. And I and your wife will keep laughing at you…

Are you into small penis humiliation and sissification like Dave? Then you should give me a call.

Cuckold Phone Sex Fantasies

Cuckolding and Humiliation Fantasies with MILF Emma