The Spy who Fucked Me

I can't tell you my name, but if you'd probably recognize me if you've picked up a copy of The Wall Street Journal in the past three years. I'm the CEO of a large Midwestern company. Thousands depend on me for their paychecks. Millions rely on me to stock grocery stores with toilet paper and 10 brands of breakfast cereal. A few words from me to the right people can send stocks soaring or plunging for days.

I'm also a sex-addicted cross-dresser.

Nothing gets me off like public humiliation. I love strapping on a bra and then rushing to an adult bookstore to meet strangers for sex. We usually don't even make it to a hotel. I suck them off out in the parking lot.

I recently went out in full drag in Portland, Oregon. I wore a red, low-cut, dress over a lacy black bra and panties. I wasn't even close to passable as a woman, so I drew some attention, even in a porn shop. But I quickly found a couple of guys who were looking for a third. We went back to their house. They introduced me to "finger cuffs." I got in the doggy-style position so one could fuck me up the ass, while the other jammed his cock in my face. One guy's girlfriend watched while fucking herself with a vibrator.

I know powerful men need to be careful with their sexual appetites. No one needs to remind me of what happened to Eliot Spitzer or Larry Craig. No doubt my competition would love a few snapshots of me in a cute miniskirt. But I can't help myself. When the urge to cross-dress hits, I'm driven by forces beyond reason. It doesn't yield until my cock explodes.

I always knew getting caught was a risk, but it never sunk in until the nightmare came true. Nothing could've had a more profound affect on my sex life.

It all started when my secretary, Lois, rang my phone on the Monday morning after the Portland trip. I was in my penthouse office overlooking the park. My desk was covered with legal documents as I struggled to make sense of a hostile takeover I was considering.

Lois called from her desk in the outer office.

"Hello, sir," she said. "A Ms. Julia Hunter is here and says she'd like to see you."

"Never heard of her," I said. "Does she have an appointment?"

"No," Lois said.

"Ask her what she wants," I said, "and have her make an appointment with one of the department heads."

"Yes, sir," Lois said.

I hung up the phone. Not a minute later, it rang again.

"Yes, Lois. What is it?" I asked.

"Sorry to bother you, sir," she said. "But Ms. Hunter insisted that I call you back. She said she knows about the Portland bookstore."

My stomach leaped into my throat. I dropped the folder I'd been perusing. My mind searched for an explanation. Who could've known? Certainly, the two guys I fucked. But who would they tell? The answers wouldn't come.

"Sir? Are you there?" Lois asked.

My mind snapped back into action.

"Yes, yes," I said. "Did she say anything else?"

"She wouldn't elaborate," Lois said.

"That's fine, Lois," I said. "Go ahead and show her in."

When Lois opened my door, the most amazing red-head came swaying in. Never have I seen a woman make a plain, gray business suit look so sexy. She had huge tits that bounced as she walked with a black brief case in her hand. Her eyes locked onto mine. This woman was all business.

I did my best to play it cool. If there's one thing I've learned in my years climbing the corporate ladder, it's that you can never let the opposition see you sweat.

"What can I do for your, Ms. Hunter?" I said, while leaning back in my fat, leather chair.

Without invitation, she took a seat in a chair on the other side of my desk. Her skirt slid up her leg as she sat, revealing the lacy top of her white, thigh high stocking.

"Tell your secretary to leave," Ms. Hunter said. "You're going to want to discuss this in private."

I nodded at Lois.

"It's OK," I said.

Lois closed the door.

"OK," I said. "You've got my attention. Who are you? And what's this about?"

Ms. Hunter flipped open the latches on her brief case. She opened it and pulled a business card out of a side pocket.

"Julia Hunter, private investigator," she said, while handing me the card. "One of your competitors hired me to learn what you do in your spare time."

"You've been spying on me?" I asked.

"That's right," she said.

I slammed my open palm on my desk. The crack echoed through the office.

"I demand to know who hired you!" I yelled.

Ms. Hunter didn't flinch.

"Demands don't get anywhere with me," Ms. Hunter said. "I suggest you calm down and take a look at what I've come to show you."

Ms. Hunter pulled out a laptop and flipped it open. She hit a few buttons and the set the computer on my desk with the screen facing me.

"This is what I gathered last Saturday night after you closed the deal out in Portland," she said. "By the way, congratulations on that. You personally made $13 million. Not bad for a week's work."

I gritted my teeth.

"No one was supposed to know about that," I said.

Ms. Hunter smiled.

"I know," she said. "But I do."

Ms. Hunter came around to my side of the desk to narrate her presentation. She put her hand on my chair and leaned in toward the computer. My cock jumped as one tit brushed my face. I wondered if it were intentional. I looked up at her. She ignored me and focused on the screen.

"These first few shots are screen-grabs from your computer," Ms. Hunter said. "They show a few of the porno sites you were looking at in your hotel room. You start off with straight porn at 8:03 p.m. Just naked chicks, Playboy pics. Nothing weird. You move to cum shots by 8:47. And by 9:02, you start looking at transsexuals.

"You log off at 9:17 and leave the hotel. Here's a security camera shot of you exiting the lobby with a duffle bag in your hand. And here's a different video of you pulling into a Burger King parking lot 15 minutes later. You walk in the front door, still dressed like a guy, and head in the direction of the bathroom.

"You emerge 12 minutes later in this sexy, little outfit."

The surveillance video showed me in full drag click-clacking in heels through the Burger King lobby and out the door. There was no denying it was me. My face was plainly visible, even behind the make-up. I remembered all too clearly. I'd gone to the Burger King to change because several of my associates were staying in the hotel. The memory made me pop a woody, even though I knew this all meant I was in big trouble.

Ms. Hunter continued.

"You leave the Burger King and arrive at Big Dick's Porn Palace 23 minutes later. Here's some video of you walking in the front door and browsing through the dildos. This is my favorite part. If you watch closely, you'll see this shopper notice you and then snicker."

I remembered her. Some soccer mom shopping for dildos was none too discrete about giggling at me. It was humiliating.

And I loved it.

Ms. Hunter hit fast-forward. The figures on the screen raced around the store.

"I'll spare you some of the details," she said. "'I'm sure you'll remember meeting Nick and Joe."

"Actually, I don't," I said.

"Maybe you don't remember their names," she said. "But you'll remember what you did with them."

Ms. Hunter punched a button on the keyboard. A raunchy porno film filled the screen. Two guys worked over a chick in a red dress. Her skirt was over her hips, as one guy violently pounded her ass while the other fucked her face. Just behind them, a blond woman sat on a couch with her legs spread wide. She fucked herself with a silver dildo while watching the sex show in front of her.

I took a closer look. The person in the red dress was no chick. It was me.

"I bet you didn't know you were being taped," Ms. Hunter said.

"Enough," I said. "Turn it off."

Ms. Hunter shut down the computer and put it in her bag.

"If that gets out," I said, "I'll sue the shit out of you. And I'll make sure you're brought up on charges. I have friends in high places, believe me."

"I'm sure you do," Ms. Hunter said.

She sat down and draped one leg over the other. They were beautiful legs that made it hard to concentrate.

"But here's the thing," she said. "I'm ex-CIA. I know things about all those powerful friends you keep in your back pocket. Embarrassing and costly things that will keep their mouths shut."

"Excuse me for asking," I said, "but you look a little young to be ex-CIA."

"I do, don't I?" she said. "Truth is, I was the fastest-rising agent in history. Could have been the first female director. But then I got too close to a certain foreign dignitary. A Russian. They sent spies after me. A few pictures got to the president. He thought my relationship with the Russian showed poor judgment. The president himself told me I could either step aside or be forced out like Valerie Plame. So, I went into private practice."

I had no doubt she was telling the truth.

"Fine," I said. "So you're ex-CIA. What do you want?"

Ms. Hunter dug into the pocket of her jacket and pulled out two lollipops. She offered me one. I waved it off. She put it back into her pocket and peeled the wrapper off the other.

"Are you familiar with fem dom?" she asked, while holding the red candy near her lips.

I knew exactly what it was, but I wasn't going to let on, at least not all the way.

"It sounds like a sex thing," I said.

"Right," Ms. Hunter said, while pulling the sucker out of her mouth. "Some women like to sexually humiliate men. They make their man-slaves dress up like girls and then humiliate them. What do you think of that?"

Her tongue played on the candy like the head of a cock. A full-blown hard-on raged in my pants.

"That's fine," I said. "But it doesn't answer my question. What do you want?"

Ms. Hunter giggled.

"You're a good actor," she said. "I bet you're great in the board room. Poker-face the whole time."

This woman was seeing right through me. My back was sweating.

"I'll just get right to it then," she said. "I want two million in cash delivered to me tonight."

"Fine," I said. "What do I get?"

"All copies of the video presentation you just saw," she said. "And just to show how nice I am, I'll give you some dirt on the person who ordered up this investigation."

"Deal," I said.

"Wait," Ms. Hunter said. "You didn't let me finish. There's something else I want."

"What is it?" I asked.

Ms. Hunter slipped the lollipop into her mouth and leaned forward, propping her elbows on my desk. Her tits formed a cleavage that seemed bottomless. She let me stare for a few seconds. Then she pulled the sucker from her lips with a smack. I could smell its sticky sweetness from across my desk.

"You're going to be me fem-dom bitch when you come over to drop off the money," she said. "Your ass is mine for one hour."

I sighed. It was true that I wanted to be her sex slave. But I hated giving in to an extortionist.

"You're a sick woman," I said.

Ms. Hunter smiled and tossed the lollipop into the waste can.

"I know," she said. "But so are you."

I squeezed the bridge of my nose. A headache was coming hard and fast.

"Deal," I said. "Where do we meet?"

Ms. Hunter told me to meet her in room 320 at the Holiday Inn off exit 32 at exactly 8:20 p.m. Then she sashayed out of my office.

Gathering the money wasn't difficult. I keep an emergency fund of $10 million tucked into safes and security deposit boxes around the city. I left the office early and made a couple of bank runs, stashing the money in a black brief case.

At the hotel, I knocked hard three times, precisely as instructed.

Ms. Hunter answered the door almost totally nude. She wore white, fishnet thigh-high stockings and six-inch heels without panties or a bra. A string of pearls hung between her luscious, round tits. Her bush was a neatly trimmed triangle of red hair. She didn't seem to care that the door was wide open and anyone walking by could've seen her.

But Ms. Hunter wasn't wasting any time.

"Get in here," she said.

I stepped into the room. She slammed the door behind me.

"Put the money on the table," Ms. Hunter said. "And strip off those clothes."

She watched from the other side of the bed as I followed the instructions, setting down the brief case and sliding off my tie. Her hands were on her hips, and she was frowing.

"I'm going to enjoy humiliating the shit out of you," she said.

I already had a chubby forming in my silk boxers. When I pulled them down, Ms. Hunter's eyes slid down my body to my prick. Her frown turned into a smile.

"You've got a big cock," she said, "for a sissy bitch."

A ruckus suddenly rose in the neighboring room. Someone banged on the walls. A man yelled, "Allllriiiiight!"

Ms. Hunter banged on the door connecting the two rooms.

"Hey, take it easy in there!" she yelled.

The shrieks and banging quieted.

"What was that all about?" I asked. "Do they think they heard what you said about my cock?"

Ms. Hunter fixed me with a stern look. I froze. She slapped me across the face with her open palm. My cheek stung.

"Shut up, cunt!" she said. "You don't speak unless you're spoken to."

Ms. Hunter grabbed a pink bag sitting on the dresser. She emptied the contents on the bed.

"There's your uniform, bitch," she said. "Put it on."

I started by strapping on the lacy, white bra. The under-wire cups pressed into my chest as I connected the hooks behind my back. I slid the straps up my arms. The cool fabric encased my tits. I was beginning to feel like a woman.

Ms. Hunter could tell, but she didn't say anything. She just smiled and nodded approvingly.

I went for the boyshort panties next, sliding them up my legs. They fit fine. The elastic hugged my thighs and ass. The bottoms of my butt cheeks hung out the bottom. I arranged my stiff cock so that it was pointing straight up at my belly. The sensitive underside brushed against the lace every time I moved.

My outfit came with a pair of white thigh-high stockings exactly like the pair Ms. Hunter was wearing. I sat on the bed and slid them up my legs one at a time, careful not to tear them. I loved how they hugged my legs.

I finished off the outfit by sliding on a pair of six-inch stripper heels.

"Make-up time," Ms. Hunter said. "Come with me."

I followed her to the bathroom, stumbling a couple times in my new heels. Ms. Hunter patted the marble counter by the sink and said, 'Lean here." I settled in.

Ms. Hunter did my make up, making me look like a whore with black eyeliner, red lipstick and gray eyeshadow. Her spearmint-scented breath filled my nostrils as she leaned in to paint my face. Then she slipped an auburn wig onto my head. I looked ready for the streets.

"Now we're ready for some fun," she said. "Go stand in front of the bed."

When she swung open the connecting door, a wall of manhood stood waiting. I never did find out how many guys were there, but it had to be at least a dozen. They looked horny and even a little angry. The horde came rushing at me in an irresistible wave. All of them had hard cocks needing to be serviced.

I was stunned. My heart leaped. I had no choice but to take care of them all.

The first guy through the door was a tall, lean athletic guy with dark hair. He rushed at me.

"On your knees, bitch," he demanded.

Stunned, I dropped to the floor. He grabbed the sides of my head and poked his stiffy at my lips. I opened up. The guy forced his cock down my throat. I gagged as he buried my nose into his pubic hair. I struggled to inhale, but no wind came. The guy's prick was blocking my windpipe. He pulled back quickly, and I took in air. The guy immediately rammed his stick back into my gullet.

"Watch the teeth, motherfucker," he said.

I opened wider and let my throat relax, giving the guy nothing buy soft, wet flesh.

The face-fucking became smooth and rhythmic, as several other guys gathered around me to watch and jerk off. Somewhere on the other side of the room, a guy was saying, "Cum on his face, man! Cum on his face!"

And it suddenly happened.

One of the jerk-off guys let loose on my forehead. A cheer rose in the room as if the Giants had just scored a Super Bowl-winning touchdown. Jizz ran down my cheeks and the bridge of my nose. The athletic guy just kept pumping my lips with his cock.

It didn't take long for the next guy to cum, or the one after him. They all blasted their loads on my face or in my hair. Each time a guy popped, a new guy moved to the front of the crowd.

The dark-haired guy finally gave one last thrust and let his junk fly in my mouth. It was a big load I could barely contain. When he pulled out, I still had the salty love juice between my cheeks.

"Show us," the dark-haired guy said.

I tilted back my head and opened my mouth. I flipped my tongue a few times. Cum spilled out the corners of my mouth. The guys cheered.

A young surfer dude with long, blond hair stepped forward while furiously beating his cock. He took aim and fired. The first shot me hit me right in the eyes. I instinctively shut them. A few guys laughed. Some else shot a load. I felt it splatter between my tits.

All the while I held my mouth open with my head tilted back. Jizz pooled on my tongue Someone yelled, "Swallow it!"

I sealed my lips and let the cum slide down my throat. A roar rose in the room. Another big load splattered across my face.

I swelled with sweet humiliation. I loved it. I was the victim, totally out of control. My cock pulsated.

I never saw the next guy who shoved his cock in my mouth. But I know he smelled like Old Spice and came quick.

After swallowing his load, I wiped the cum out of my eyes with the back of my hand. The crowd had begun to thin. The guys who had shot their loads had moved back into the other room or were watching while slumped along the walls. Two college boys and an older guy beat their cocks while standing in a semi-circle around me. Another guy was up on the bed, fucking Ms. Hunter in the missionary position. She moaned as he glowered at her like a hungry lion. He suddenly threw back his head and gave one last thrust before cumming and rolling off of her.

He looked at me.

"Get up here," he said breathlessly. "Fuck this bitch, sloppy seconds."

I eased between Ms. Hunter's legs as jizz dripped off of my face and onto her chest. The three beat-off guys followed me to Ms. Hunter's side. Her face remained jizz-free. But just as I was easing my prick into her pussy, the older guy popped a shot across her face. He left a trail of sperm from her chin t her lips to an eyebrow. Ms. Hunter gazed up at me and slowly licked the cum off her lips.

I pumped her slowly. Her pussy walls were slick with another guy's cum and her own juices. I could've shot immediately, but then I saw the two beat-off guys move in beside Ms. Hunter's face. I wanted to jizz at the same time they did. One knelt on the bed. The other stood by the bedside. Both had their cocks aimed and were stroking hard.

I tightened my asshole and squeezed my eyes shut. A geyser of cum built inside me. I couldn't hold it much longer.

I didn't have to.

When I opened my eyes, the guys were firing their loads on Ms. Hunter's face. I gave a final thrust and let myself go. My cock exploded into her cunt. Ms. Hunter seemed to love every second of it. She had her mouth open and her eyes closed. Cum covered her face. At least one shot had hit her in the mouth. A line of spunk slowly slid down her tongue.

No one had to tell me what to do next. With my still-stiff cock inside her pussy, I lowered my head and gave Ms. Hunter a long soul kiss. Our tongues played in the sperm like dolphins in the ocean until I pulled away to lick the jizz off her face.

I grabbed my trampled suit off the floor and went to the bathroom to clean up. When I came out, all the guys had gone back to the neighboring room. Sitting on the edge of the bed with her legs crossed was a naked, familiar-looking blond woman. It was the one I'd met in Portland a few days earlier -- the chick who shoved a dildo up her cunt while the two guys fucked me.