Miles's Conundrums

"Paint my nails?" I asked Gretchen in disgust. "I'm a guy...why would I want to do that?"

Gretchen looked down demurely. "I don't know, Miles. I thought you wanted to amuse me...to put me in the mood, you know?"

God, she was so beautiful, I thought. Gretchen's huge, perky breasts were just barely holding up that tube top...I hadn't seen them naked in a while.

There was a knock on the door, and Tom came downstairs, and unlocked it, and in came two of our mutual friends, Cade and Stu.

Stu looked over at us and gaped, and it was understandable. I was standing naked in front of my fully dressed wife, who was relaxed on her couch, poking my rock hard dong occasionally with a heel.

"Jesus, having fun there, Miles?" Cade looked too, and Gretchen turned and grinned at him...and then the little bitch flashed her tits at him!

Just pulled the tube down and waved her tits at my friends! Tom, Stu and Cade clapped.

I was furious that she'd do that, but on the other hand it had been a while since I'd seen her boobs, so I just bent over to look

Really, I—hadn't seen them in a while—and Gretchen reached up and slapped me!

"Stop looking, this is just for the fellows!" And I stood there with my mouth open!

Gretchen primly tucked her boobs back in the tube top. "Little boys don't get to look at women's breasts, Milesey...they're rated R." "What the fuck're you talking about, woman?" Cade asked, shaking his head.

My friends had always thought that Gretchen was a ball breaker. As I said earlier, Gary used to give us an earful of what a bitch she could be.

"Dude, that's the deal here." Tom said, grinning big. "Miles is Gretchen's slave boy now. Mister Dean's List is now ...I don't know."

The three of them laughed uproariously, and they went upstairs. I was burning with shame, but also...I was resentful.

"B-but..I can't look at your breasts now? And..." I had forgotten the issue of being humiliated in front of my friends. What was up with that?

Gretchen was just giggling, and her tits were shaking madly in that damned tube top. This was hilarious to her. "You're just...like, pitiful, dude..." Gretchen put her head in her hand and giggled some more.

For some reason, my dick was even HARDER now. Zowie! But I was furious.

Suddenly Gretchen looked up at me quite seriously. "I asked you a question earlier, Miles."

"Do you want to arouse and amuse me, or don't you?" Gretchen looked straight in my eyes.

"Cause if you don't, then I'm just going to send you to bed and go out with the guys upstairs for some beer."

She-she can't send me to bed! I'm not a SIX YEAR OLD!

And going out with my friends!

I remembered being six and being made to go to bed early and hearing my friends play outside because my parents were Christians.

But more importantly, I thought about amusing and AROUSING her. My baby who hadn't let me touch her in awhile.

"Well, of course I want to um, amuse and a-arouse you." I said.

Gretchen looked up at me and passed a tongue across her lips. There was a noise of laughter and a football game going on upstairs.

Gretchen looked upstairs, somewhat longingly. She wanted to be with the real guys.

I had to do something. I had to entrance her again. Tom had gotten a job in construction after we'd graduated, because his grades were so crappy.

Cade was a bicycle courier, and Stu hadn't even graduated from school, and did drywall work. They were all in good shape from those crappy jobs.

Mister Deans List had the pot belly, and didn't watch sports much. What could I do to compete?

"What-what can I do to arouse you?" I watched her paint her last nail and put the little brush back in the little polish bottle.

"Well, I asked you to do something for me." Gretchen made her eyes real big and looked at me.

"What? You wanted me to, what was it?" I shook my head, trying to remember. Gretchen ran a long tongue across her lower lip and looked at me quite seriously.

Stretching her heel, she stroked the sweating tip of my penis.

I decided to make something up. "I-I'll take you out to dinner...get you jewelry?" Grabbing at straws.

Gretchen shook her head again, and made a motion to get up.

"Where are you going?" I asked in a panic.

"Look, Miles. I asked you to do something to amuse me!" Gretchen looked at me as she half rose.

"You want to screw me and paw me, but I am attracted to men who remember what I ask them for...you can't even do that."

God she was hot. My dick got even bigger. I tried to remember.

"What? You said something about me painting my nails." I laughed nervously.

Gretchen sat back down and beamed at me! "Yes! You remembered!"

"But what--you weren't serious, were you?" I laughed...

I mean, either I paint my nails for her, or she goes out with my friends for beers. What the...?

Gretchen looked at me and smiled. "Miles, it would really turn me on if you let me paint your nails and put some makeup on you."

About half an hour later, I was um, a different person.

Gretchen had had a ball. She'd had me shave off my prized Van Dyke beard, and then moisturized my face.

Putting concealer on my moles, she'd put heavy blue cream eye shadow on my lids, highlighting the brows with shimmer.

The false eyelashes were really uncomfortable, but hey, anything to get laid, right?

"Now for the lips. I'm going to highlight your lips and then gloss them to make them real big."

My nails were painted, and she put a big blonde wig on me.

"Now shove your feet in these nice Capezio heels! They're gonna pinch, but don't complain, honey."

And then she gave me earrings!

Though I was still stark naked in the living room, I'd almost forgotten this in all the disturbing new changes.

So then I said, "So are you um, turned on by this...do you want to make love?"

Gretchen looked at me, giggling to the point that she hid her face. I couldn't blame her, I mean, really.

I was standing there with painted face and nails, a wig and high heels! And stark naked to boot.

Gretchen finally looked at me, semi seriously. "Well, I am amused, I must say." That was good, right?

But then, the unthinkable happened. She yelled upstairs. "Fellas, come down here!"

My God, I was paralyzed.

Cade, Tom and Stu stomped downstairs in their construction-worker steel tipped boots. Smoking Marlboros, they came in the hall and looked at me.

"HA HA HA!" Pointing and laughing at their old college friend.

I'd actually known Stu since high school! And they were laughing their asses off.

I ripped off my wig and threw it on the floor and stomped upstairs in my high heels.

Slamming the door to the bedroom, I threw myself on the bed and, Jesus, I began to cry.

As I sobbed angrily, my face a mass of wet, disgusting makeup, I heard the laughter and talking downstairs.

My mind went back to childhood, when Mother would dress me funny in European velvet suits with knee breeches and frilly collar...not cool in the seventies.

The boys would laugh and beat me up as I made my way to my violin recitals...it had been a tough childhood.

Now I cried in my manicured hands, and I just thought, I'll show the bitch! I'll leave her in the lurch!

I'll tell her to support herself with her failure film job, dammit!

But there was a light knock on the door after about twenty minutes, and Gretchen looked in, somewhat penitent.

"Honey...please don't be mad at me. You were just so cute." And I...what I should have done was left her...but she came over and kissed me tenderly.

"Honey, you don't understand, those are my friends." I tried to reason with her. "You've ruined a friendship with them now..."

But Gretchen kissed me again. "I'm your friend, Miles. Forget them."

But then there was a shout from downstairs. "Gretch are you coming?"

Gretchen smiled shamefacedly. "I did promise to go to Cerberus with them for a little while. But I'll be back!"

Cerberus was our old hangout--me and the guys. "But, what about lovemaking?" I was trying not to whine.

"No, I'll be back soon." Gretchen said. "I'd invite you, but--but maybe not. You're not um--" But she was speechless with giggles again. I nodded. I wasn't their type of friend anymore.

"Look--I really want to make love to you tonight!" Gretchen said urgently.

There was a shout from downstairs. "Forget that faggot!"

Gretchen looked out of the bedroom door. "I'm coming in a moment."

She looked back in at me. "I want you to wait for me, okay?"

"Uh, all right." I said. "I can wash all this dreck off. Do you have nail polish remover, by the way? I understand perfume works--"

"No, no!" Gretchen said, laughing. "Keep it all on, you look cute."

"Just--why don't you play with yourself and think of me, and the good time we're going to have when I get home, okay honey?"

Gretchen smiled tenderly at my wounded look.

"But don't cum! I want you to be ready for me when I get back in. Half an hour at the most."

Gretchen smiled again, on the verge of hilarity. "Mommy will be mad at you if you cum."

With a slam of the door, she was gone. I lay back and began massaging my cock, thinking of my beautiful girl. And God, was she beautiful!

Gretchen's short, curly hair, her large breasts, that impudent smile...the way her full butt twitched when she walked ahead of me!

But the more I tried to think about fucking her or her blowing me, the more I remembered standing naked in front of Gretchen and the guys, with the wig and the full makeup on...them laughing at me!

Mysteriously, my cock hardened in my painted fingers. I thought of Gretchen whipping my ass with the wooden paddle we'd bought.

Me crying in the corner, my damaged bottom on display as she laughed and watched "The View." What the hell was I thinking of that for?

Wait, what about when I fucked her in the ass a year ago? Why wasn't I thinking of her magnificent blowjobs?

I kept thinking of the paddle whipping my ass...me cowering naked before my construction-worker friends...

My hand rubbed my dick faster and faster. Suddenly the fantasy changed and Stu,Cade and Tom were sodomizing me!

Gretchen was laughing, and pointing as I cowered on the floor!

Lying on the bed now, my dick grew huge as I jacked it faster and faster considering this bizarre scene... I was getting closer and closer...I was about to cum...

Suddenly the phone rang! I picked it up, annoyed. There was a sound of loud music.

"Miles? Honey?" It was Gretchen's voice, she was slightly drunk.

"Y-yes, Gretch." My penis flailed in frustrated misery as I let go.

Strangely, I wanted to continue masturbating to this weird image, instead of talking to my princess!

"Miles, I wanted to make sure you hadn't squirted." I could hear my friends laughing at the table.

Stu's voice came from the side: "Don't jerk your dick too much, Milesy, you faggot!"

Then Gretchen's voice was gently scolding him. I burned in humiliation as I held the phone in one hand and my dick in the other. "Miles, I wanted to tell you something important" Gretchen's voice was urgent.

"What's that, honey?" Jesus, now what?

"I know your face is a mess from crying and all that makeup is smudged--" My friends now roared with laughter.

"But what I want you to do is touch yourself up, you saw how I did it--re-do your lips and your eyes, so you look cute when I get home...make yourself pretty, and you'll get laid!"

After she hung up, I was furious and humiliated...but I thought of her beautiful body, and off I went to put on my face before the mirror!

My pelvic muscles were tensed as I worked on my face quickly. God, women have it hard, I thought as I sloppily outlined my lips. I went back to lie on the bed and touch myself carefully. I had to be really careful not to cum.

I began getting much too close, and holding the tip of my penis. I was getting really really, close to cumming, though.

I began vividly imaging Gretchen in a tight red dress, whipping my naked body, while a group of guys pointed and laughed at my garish makeup.

I pumped my cock and my hips began going up and down. I could feel the semen in my urethra, waiting to spurt.

It was getting damned close... Quickly, I pinched the tip of my cock again, to keep from cumming. God this was difficult. Suddenly, the phone rang again. I sighed and picked it up.

"Hey landlord...Gretch wanted me to make sure you weren't spilling your seed!" Tom was drunk off his ass.

"Look Tom, enough. This was a bad scene tonight but--" I had to be firm with the guy.

Gretchen had really overstepped her boundaries. My friendship with Tom would never be the same.

But I'd try to be manly with him. "Dude, just forget tonight okay? We're still buds--"

But Tom rudely interrupted me.

"Gretchen said if you make a nasty mess with your dick, she's going to let me beat your ass with a belt, so be a good boy!"

Then he hung up. At first I was furious, and embarrassed.

But then I thought about it, and I began jerking my dick really fast...humiliated, angry and horny!

God damn that woman for saying that to Tom, but what would it be like if he beat my ass? What's wrong with me?

But I gritted my teeth and didn't cum, and kept jerking my dick. She would be home any moment now...

But Gretchen didn't get in for five hours.

By the time she got in, quite drunk and disheveled looking, I was ravenous with the desire to cum.

"God, where've you been?" I stuttered.

I tried to hug her, and she shoved me back, staggering.

"What-the hell...your makeup looks like shit!" Gretchen began laughing, but then turned nasty.

"Why should I give you any pussy, when you can't put on lipstick right, you whore?" Gretchen raged.

"I've been jerking myself all night, waiting for you" I pleaded.

"Please don't make me finish off alone." I couldn't believe she was so crass!

"Finish off? Are you kidding?" Gretchen asked incredulously.

Suddenly she gave me a roundhouse slap, and before I could recover, she'd produced handcuffs.

"Shtu--Stu gave these to me." Gretchen slobbered drunkenly.

"He's going into th' police academy." Gretchen forced my hands behind my back. Click!

"I'm going in Tom's room tonight, since you're such a loser!"

Slam!

There I was, alone in the room, with a bad makeup job, and unable to jerk off!

It was an outrage. I should leave her...but I just cried and looked at my rock hard dick 'til dawn. The next morning, I was in terrible shape. The makeup was all smeared over my face, and I had a cramp from lying on the floor.

I kept waiting for Gretchen to come in the room, and apologize and unlock me. What a bitch she is!

Of course it was because she was drunk, but she'd locked me up after promising me sex, AND I'd heard disturbing moans from Tom's room all night.

And of course, I'd tried to get off, to get an orgasm...

I'd tried rubbing my dick against the carpeted floor, pushing it like a dog on the table leg (that nearly worked) everything!

At one point, I know that Tom and Gretchen were joking about it because Tom screamed something about how I should possibly "Suck my own dick"

And I was so frustrated! All this time while listening to Gretchen's screams.

Now my balls were filled with cum, they were huge. Not blue balls, no...purple.

Oh, my cock was sensitive. It just poked out from between my legs, like a metronome, going back and forth.

I kept trying to get the handcuffs off, but indeed they were police handcuffs and quite effective.

Eight o'clock, the door didn't open...ten o'clock...nothing. Finally at eleven-thirty...the door opened!

Was it my princess Gretchen? I was ready to forgive her again...

No, it was Tom, hair tousled from a night of fucking. He looked at me and grinned...

Naked, makeup smeared, dick sticking out, and hands cuffed. On the floor, crying.

"You are such a freak, Miles...Jesus." Laughing, he turned around and walked out of the bedroom.

Later on in the early afternoon, Gretchen came in, nursing a hangover, and unlocked me. She didn't want to talk to me...

What the fuck? I was angry and felt like confronting her, but not really. I showered and jerked off.

Thinking of my haughty Gretchen humiliating me, punishing me and keeping me in bondage! But I was angry at her, right?

I came all over the shower wall...oh, she was so hot.

I thought I would not speak to Gretchen, or curse her out for mistreating me.

She broke her promise about giving me some action after I'd put on that ridiculous makeup. Getting it off, and the nail polish had been awful.

But Gretchen was so sick from her hangover that I ended up waiting on her, bringing her tea and all that stuff.

For the next couple of days, things were really quiet. I didn't speak to Tom any more than I had to.

Of course I no longer went out with Cade, Tom and Stu to bowl or throw darts. I had basically lost my lifelong friends.

It seemed that Gretchen was not very communicative either--when I got home at night she was out with friends or in bed.

I went from being mad at her, to wondering what the hell was going on?

Sometimes I called home from work, and no one answered the phone, and her cell just had an answering machine.

But on Friday night, I got in early, and there Gretchen was...getting ready to go out.

"Hey there, Milesey." she said cheerfully.

"God, I haven't seen you all week, honey." I said tactfully.

"Yeah. Like this dress? I just got it. Like the halter?"

"Uh huh." I said, gazing at her.

"It's cute how these chains criss cross my bust line, isn't it?"

She was putting on the Zesty Red shiny lip gloss she'd had me use the week before...

"I'm going out, babe!"

"Going out?" I looked at her in sad astonishment. "But I didn't even see you all week, honey. I thought tonight might--"

I stopped in mid sentence. Gretchen was looking at me with a kind of pity. Oh Jesus.

Gretchen smiled at me and reached out and rubbed my arm. "Honey, I think I need some space. I don't know about forever, but right now--"

I began panicking. "Honey, don't you want to spend time with me? Isn't there any way we can spend time together tonight?"

"I just need to see other people, though...that scene last week really bothered me." Gretchen said this, shaking her head.

Looking at me as if it had been my decision to dress in makeup and high heels and wear police handcuffs!

"But, on the other hand" Gretchen said, smiling. "I haven't seen you all week, and maybe there is a way I can take you with me. tonight."

"Sure!" I said. "I'll do anything, baby."

In the next twenty minutes, I realized that I had possibly made a mistake. Gretchen pulled out this amazing kit she'd bought.

"What are those pink triangle-shaped rubber things?" I was gaping.

"These are nice transgender breast forms, honey, 42 silicone double D"Gretchen put one around my right nipple.

As I stood numbly, Gretchen strapped the breast forms on my chest, and then had me pull a long girdle slip over my shoulders.

"See I'd love to take you out clubbing with me just as you are, but I'm going with a guy from my gym."

Gretchen snapped a garter belt around my waist. "My trainer, Adonis-Lloyd Baskerville, feels threatened by white men, and so you can be my girlfriend!"

"And don't you love these nice fishnet stockings?"

She put a horrible bone "waist nipper" around my stomach. "Now you'll have a nice hourglass figure."

After she put me in a "genital hiding gaff" that pushed my dick way between my legs, it was time for the dress.

Suddenly I was in full makeup (with beard concealer) and my six foot frame had been stuffed into a black tube dress. Paste-on magenta nails this time...

My Adam's Apple was covered by a rhinestone "choker" and my feet were not as cramped as Gretch had gotten me size fourteen silver pumps!