I had first met her through a mutual friend at work.  As our paths crossed more and more over the years, we became quite friendly, often seeking each other out at conferences or workshops, frequently being the last ones to close down hotel bars.

Her name was Morgan, and she was the State Policy Director.  She had a reputation as a real hard-ass — always coming out on the better end of any deal in which she got involved.  She was also pretty — dark brunette hair, an ample chest, and she dressed sexy but smart.  She was a little on the short side, so she always wore heels.  Her legs were fantastic.

I loved the flashes being near her afforded me — frequent looks down her blouse, the occasional upskirt.  Her lingerie was always nothing short of amazing, and the occasional tantalizing glimpses of her areola meant my eyes were always on her.

There was never anything between us, but I had lost count of the number of times I had masturbated while thinking about her, usually after a night of bar hopping or staying in at the hotel bar while we were at conferences.  I would normally put on a video of a dark-haired beauty pegging some guy with a big black dildo.  The videos I loved best were when the guys were dressed in lingerie.  You see, I’m a closeted crossdressing sissy.

“Oooh yes, fuck me, Morgan.  Fuck my sissy ass hard!” I would hear myself saying out loud as I watched the dildo pistoning in and out of the man’s boipussy.

Our present conference had brought us to her hometown.  Because she was so close to home, she wasn’t staying in the hotel and had to commute in each day.  We were both disappointed at the prospect of not getting to hang out together this trip.

“Well, why don’t you just come to my house?” she said.

“I really can’t impose,” I began to say.  She held up her right hand, cutting me short.

“I don’t mean to stay over, you mooch!” she teased, punching my arm.  “You can come home with me, and my husband can drive you back later tonight.”

“Are you sure?”

“Absolutely!  Number one, we’re already having a few people over tonight anyway; and number two, he does what I tell him to do.”  My mind immediately jumped to those strap-on fantasies as she spoke.  I pictured her dominating her nameless and faceless husband.

We talked mostly about work as she drove out of the city and into the surrounding suburban area.  I was glad for the simplicity of the conversation because my brain was elsewhere the entire drive.

“I can’t wait for you to meet my husband, Harold,” she said.  “I think you’ll find you have a lot in common.”

Her house was an older home on a large, well-manicured lot with impeccable landscaping.  There were already a number of cars in her driveway, but they had left room for her to get around them to the garage behind the house.

“Looks like Harold started the party without us!”

“Well, then we’ll just have to play catch-up,” I said.

I met Harold, who seemed less than enthusiastic to meet me.  What, I wondered, had she told him about me (or us)?  I wrote it off to knowing that he was tasked with driving me back to the hotel later and maybe resenting me just a little because that meant he couldn’t drink at his own party.

Harold did, however, have a top-shelf bar, and the liquor was flowing freely.  I had a few snifters of some of the rarer whiskies from his impressive collection, which led to him opening up just a little as he bragged about his connections in the world of acquiring rare whiskies.

Morgan introduced me to all of her friends.  I don’t work at her level, so I don’t consider myself “important,” but I am somewhat well-known in certain industry circles, so there were a few of her guests who were excited to meet and talk with me.

As the evening wore on, I found myself looking for some needed relief.  I had just wandered from the living room to the kitchen and ran into Morgan on my way out.

“You lost, dear?”

“Ummm, no, just...,” I started to say.  She cut me short.

“Looking for a snack?  Need a drink?”

“Sorry, is there a bathroom?” I asked sheepishly.

“Oh, sure, right there off the kitchen,” she said brightly.  “There’s a door at the other end that leads to the master, so make sure you close both doors!”

I followed her pointing arm to the door off the kitchen and closed it behind me.  I walked to the opposite end of the bathroom and glanced into the master bedroom as I closed the door.  I noticed a pile of clothes on the floor on the near side of the bed as the door swung shut — a flash of pink fired my imagination.  As I relieved myself, my brain was burning with an intense desire to investigate that pile!

I just can’t, I tried to tell myself.  It would be rude to my friend and hostess to go snooping through her bedroom.  Never mind the professional ramifications if I were to get caught!  As I finished my business, temptation took an unshakable hold.

I avoided flushing the toilet so that it would be assumed I was still using the bathroom.  I slowly opened the door to the master bedroom.  I walked toward the pile of clothes, looking both ways to locate the other bedroom door.  It was also closed.

I reached down and inspected the pile.  It was an athletic dress — one of those Lulu Lemon ones in soft pink with the built-in shorts.  It was a wadded-up mess, and it had been stripped off in an obvious hurry.  A pair of panties was still entangled with the shorts.  I paused, checked both doors, and then brought the whole pile to my nose, panties first.

I inhaled deeply, relishing the intoxicating scent of Morgan’s sex mingled with her workout sweat.  Suddenly, I heard her voice approaching the bedroom door.  I quickly dropped the pile where I had found it and dashed into the bathroom, closing the bathroom door quietly behind me.

As I heard her voice in the bedroom, I quickly flushed the toilet and exited into the kitchen.  I breathed a sigh of relief — what a close call!

As other guests slowly took their leave, soon it was just a handful of us.

“I had better get back,” I said to Morgan.  “You know as well as I what time we start tomorrow.”

“Let me get Harold,” she said.  “He’ll drive you back.”

“Are you sure?” I asked.  “Really, I can probably grab an Uber or something.”

“Nonsense!  I won’t hear of it!  Besides, I’ve already told you, Harold always does what I tell him to do.”

“Well, I appreciate it.”

“Maybe we’ll have to find a way for you to make it up to us,” she said with a playful laugh.  That really set the wheels in my head turning.

I waited while Harold pulled the car around front and picked me up.  As we pulled out of the driveway, we chatted about nothing.  Because we had discovered a mutual love of good whiskies during the party, we mostly talked about that.  He wound his way through town and to the highway.

Once we were on the interstate and moving fast, he turned toward me.  I could tell he was done with our small talk, and I wondered what was coming next.

“Why don’t you lean over here and suck my cock,” he said.  I gaped at him.

“Uhh, what?” I said.  I hoped my brief reply conveyed my level of incredulity.

“You heard me,” he said confidently.  “Lean over here and suck my cock while I drive you back to your hotel.”

“What makes you think...,” I started to say.

“My whole house is wired with cameras.  I have them everywhere.  I saw you sniff those panties in our bedroom tonight.  You probably didn’t even realize you were doing it, but I also saw you rubbing your crotch.”

“Look, I don’t know what you think is going on here,” I started to say.

“Let me break it down for you,” he said.  He briefly let his car auto-steer as he pulled his athletic shorts down.  He was wearing the same pair of panties I had sniffed earlier.  His cock was hard and straining against the fabric.

“Morgan has told me all about you.  She told me that she’s pretty sure that you’re a panty-wearing sissy.  She told me that she’s noticed what she is confident are panty lines on you at more than one conference.  Is this true?  Do you wear panties like me? Are you a sissy?”

In answer to his question, I unbuckled my seatbelt and moved to lower my head into his lap.  My right hand reached around to stroke his panty-covered cock as my mouth descended to envelope his hardness.

“Ooohhh, she was right!” he said.  After mouthing his cock through the fabric, I tugged the waistband of the panties down and slipped the head into my mouth.  As my head bobbed up and down on his cock he unleashed their story in a torrent.

“I am a crossdressing sissy, too.  In fact, that pile of clothes in the master bedroom was mine, sort of.  When she comes home from working out, I have to put on her dirty panties and workout clothes and wear them around the house.  If I have done all of my chores well, she rewards me with time out of my chastity cage and a pegging session with one of her dildos.  If I have not done all of my chores to her satisfaction, then I remain caged and get the strap.  Either way, I still get a pegging session.”

I moaned around his cock, slurping on it and sucking it for all I was worth.  I tugged the panties to one side, releasing his entire shaft and balls.  I nuzzled briefly at his balls before I resumed sucking his cock, this time starting to deepthroat it.

“Oh my God, you’re such a good cocksucker,” he said.  He was trying to move his hips in time with my actions — no easy feat in a car hurtling down an interstate freeway.

“Anyway,” he continued, ”because I did such a good job setting you up tonight, my reward is getting to drive you back to your hotel.  She told me that I had to expose my panties to you and that if it turned out that you were a sissy and if you agreed to suck my cock that I was allowed to cum.”

“Mmm hmm,” was the best I could manage.

“Will you tell me your name?” he asked. “Your sissy name?”

“Stacey,” I said, blurting it out in the brief interval I stopped sucking his cock.  I immediately resumed my work.

“Thank you, Stacey,” he said.  “My name is Harriet.”  As he told me his sissy name, I worked my right hand under his balls and past his perinium, seeking his pussy hole.  Unsurprisingly, I found it full of buttplug.  I pushed against the end of the plug, and he clenched, forcing his hips to rise and pushing his cock all the way into my throat.

“Oh, oh, oh,” he moaned.  “I’m cumming, I’m...”  With his hips bucking, he unleashed a flood of cum into my mouth.

I swallowed as much as I could, but some of it still leaked out from the corners of my mouth.  I tried to encourage him with my moans.  I felt the car swerving a bit and felt the bump-bump of the lane reflectors.

“Oh, shit!” he exclaimed.  He regained control of the car without incident.  His cock was now soft and shrinking fast.  I suckled at it like a teat for a few moments before tucking it back inside his panties.

“Thank you, Stacey,” he said.  “That was amazing.”

“Thank you, Harriet,” I responded.  “I’m so glad I got to help you out this evening.”

“You know she’s going to make me tell her everything when I get home.”

“Oh, I rather expected that might be the case.”

“Just so you know, she’s had her eye on you for some time now.  She loves breaking in new “girls” and twisting them to her satisfaction.  She will never allow her games to ruin you professionally, but she will hold that threat over your head to ensure compliance.”

“I would be disappointed if she did otherwise,” I said.

The next morning, I was up bright and early for the conference.  I was just filling my second cup of coffee when she came strolling in.  She walked straight up to me.  We exchanged a collegial side-hug, but before I could even begin to keep it casual, she came out swinging.

“Here,” she said, thrusting a manila envelope in my direction.  “Harold said I should give this to you.”  As I took the puffy envelope, I could tell by touch that it contained some sort of cloth - panties perhaps?

“Very nice of him,” I said.  “Thank you.”  Morgan leaned in and whispered conspiratorially.

“I want you to go upstairs to your room right now and put them on.  Once you are wearing them, text me a picture.”

“Ummm,” was the extent of my brilliant reply.  She leaned back in.

“Do it now, my little panty-freak sissy cocksucker.”

“Let me go get that for you,” I said aloud for the benefit of any onlookers.  She leaned in one more time.

“Oh, and your biggest buttplug, too.  Pictures.  Snap-snap.”

“Oh, absolutely!” I said.  “I’ll be right back.”

My stomach was doing flip-flops as I sped to my room.  I tore open the envelope as soon as the door closed behind me.  As I suspected, it was a pair of sexy panties in a zip-loc bag.  Also enclosed was a short note.

“Stacey.  As expected, she called me last night as soon as I dropped you off.  She asked me to describe in detail our encounter as I drove home.  These are the panties she was wearing, and she wore them while she masturbated with one of her favorite dildos.  When I got home, she put me in chastity, put me in these soaked panties, and then proceeded to fuck my pussy with the dildo she had just used.  I came in my cage from the pegging, so these have multiple loads of our combined juices in them.  She told me to immediately put them in a zip-loc bag to keep them “fresh” for you. — Harriet”

I stripped from the waist down, carefully folding my pants.  When I opened the baggie containing the panties, I was immediately hit with a nose full of their combined scents.  The panties were pink satin.  The front and sides were smooth.  I could see a wide stain in the front of them, clearly where Harriet had cum in them while being fucked.  I held them to my nose and inhaled — the stained front was still damp and musky.  The scent of Harriet’s cum brought memories flooding back of the load I had swallowed last night.

I felt my own sissy clitty rising.

As I held the panties up, my excitement waned.  They were open-back panties, but the wide, smooth sides turned into a large bow tied across the waist in the back.  They were not going to be at all unobtrusive in the back of my pants.  I raised the gusset of the panties to my nose.  That, too, was still slightly damp.  Morgan’s fresh scent in my nostrils drove me wild.

Using my index finger, I scooped the pre-cum from the tip of my clitty and licked it off.  I slid the panties up my legs, adjusting myself in the front of them and revelling in the feel of the damp, smooth satin against my skin.  I went to the bathroom and checked my appearance, smoothing out the bow as flat as I could.

I took a quick picture of myself in the panties and texted it to Morgan.  It was a close-up of the front, and my excited bulge was plainly visible.  I opened the room safe under the sink and removed my largest buttplug — it was metal and had a pink gem end.  I took two pictures, first, of myself lining it up with my pussy hole, and the second, slightly bent over so she could see the flash of the gem.

My phone dinged a return text from Morgan.

“Nice bulge, but I need to see your face, dear.”

“OK,” I sent back.  I had never sent anyone a picture of myself, including my face.

“Try ‘Yes, Mistress’ or ‘Yes, Miss Morgan.”

“Yes, Miss Morgan.”

I sent her the new picture of my whole body in the panties, along with the two pictures of the buttplug.

“Nice.  Thank you.  I saved your seat.”

I dressed and checked out my rear profile in the mirror.  The bow wasn’t quite as obvious as I had thought it might be, and I told myself that someone who wasn’t looking for it would be hard pressed to figure out what they were looking at.  Just to be safe, I added a sport coat to my ensemble before I returned downstairs.

Morgan was in our usual spot.

“Hey, Wilson,” she said.  “I got the files you sent, thank you.”

“Great!” I said, taking the chair next to her.  She leaned in closely.

“Tonight, you'll come home with me again.  This time we’ll have a bit of a private party, yes?”

I nodded.  She gave me a stern look.

“Yes, Miss Morgan,” I said quietly.

“You’ll need to bring an overnight bag,” she added.  “Bring all of Stacey’s things that you brought to the conference.”

“Yes, Miss Morgan.”

“It’s going to be so much fun!” She was smiling broadly.  “I can hardly wait!”

My stomach continued to do flip-flops all day as my sissy clitty — hard inside of Morgan’s dirty panties — betrayed my true feelings.  The end of the day couldn’t come fast enough!