The Gentlemen's Panty Club

Chapter 1

Sunday morning I awoke from a deep sleep, feeling rested, relaxed, rejuvenated, and above all, extremely happy! Yes, it's a glorious day, because last night I passed my initiation, and as a result of my successful efforts I've gained membership into a very exclusive and prestigious private club in the great city of San Francisco, The Gentlemen's Panty Club. The membership of the club includes important men of power and influence, and they all share a common interest, wearing pretty panties.

For some mysterious reason I, Edward Joseph Mason IV (though I prefer the less formal moniker, Joey) have been blessed with incredible good luck all my life. Sometimes I forget how fortunate I am; how blessed I am. I was born into a wealthy family of the upper class. At birth it was preordained that I would have a lifelong career managing my family's very successful business, Mason Industries LLC. With the mentoring of my father and the help of his Executive Assistant, who later was to become my wife, Bridgette O'Brien, I quickly mastered the art of making strategic business decisions. After a few short years my father felt comfortable with my abilities, and passed the leadership of his business to me.

He retired at the fairly young age of fifty-five, as he wished to spend more time with my beautiful mother. They still loved each other deeply, and I had learned that they are quite adventurous when it comes to their sex life.

My first significant encounter with Bridgette happened when I joined my father's business. My father had instructed me to get "intimately acquainted" with his very capable Executive Assistant, as she would show me the ropes. At the end of my first day of work she took me to a cocktail lounge near the office for happy hour. After two badly needed rounds of drinks, I shared my deepest secret with her, that I love wearing panties, and had been enjoying this fetish for two years. Bridgette was not bothered in the least when I shared my secret.

Her response was, "I think it's wonderful that you've found something that gives you pleasure. I also think it's sexy as hell! In fact, I think you're making me juicy!"

That shocked me, but it also excited me. I felt my penis stirring inside my trousers.

When she asked if I was wearing panties, I offered to show her. This seemed to excite her, and then she discretely showed her panties to me. She told me that a lot of women like showing their underwear secretly in public.

"I love thinking about a horny man drooling over my panties, with his cock getting hard inside his trousers!"

As it turned out, Bridgette and I have a strong sexual attraction. The following year, with encouragement from my parents, I asked Bridgette to be my wife, and she honored me by accepting my proposal!

Yes, life was going quite well for Joey Mason, the man with a life long panty fetish, and I was looking forward to many more years of managing my "panty problem."

Chapter 2

The next weekend my parents had planned a small party to celebrate my admission into the Gentlemen's Panty Club. Their neighbors, Judge Harold Chatsworth and his wife Julia were invited, as well as their daughter Edith who is one year older than me.

The judge and my father are close friends and are both long time members of the Gentlemen's Panty Club. Julia was one of the women who participated at my initiation ceremony, and witnessed me masturbating, dressed as a sissy girl and coming on my mother's beautiful face, while Bridgette and Edith captured my actions on video.

Edith and I had been best friends since childhood. She often told me I was a "sweet boy" and that we would marry some day. When I left home to attend college, she was the first woman to give me a "real" kiss, and she was the first woman to suck my cock. I loved Edith with all my heart, but fate was cruel to us. After university she married another man.

Today was a glorious warm summer day. My party was to be held outside on the backyard patio, scheduled to start at three o'clock. Bridgette and I arrived about a half hour early; as I wished to speak with my father privately about a problem at work, and I knew he would give me sound advice as to resolving it.

As I was turning into my parent's driveway I noticed Judge Chatsworth standing next to a brand new Ferrari sports car parked in his driveway. It was a magnificent machine, and I wanted to check it out.

I looked over at Bridgette, "If you don't mind, I'm going to talk to the judge for a bit. I'll be along in a few minutes."

She chortled, "That's fine darling. I know you just want to look at his new baby. As the saying goes, the difference between men and boys is the price of their toys!"

I gave her an exaggerated look, pretending my feelings were hurt, and we both laughed.

"You know me too well Bridge. Tell Mom and Dad I'll be there soon."

She gave me a quick peck on the lips, turned around and sauntered towards the front door. My fiancé has a shapely round ass that wiggles quite nicely when she walks. For the party she deliberately chose to wear a light party dress, which showed her panties through the thin fabric. She was wearing a white lace thong panty that was one of my favorites. Yes, Bridgette knows what I like, and very well.

I crossed the street and called out, "Hello Judge. Your car is amazing."

"Hi Joey. Thanks for saying that. At my age I think I've earned the right to spend some money on myself for a change."

"I agree Sir. This car suits you."

Just at that moment I heard Julia yell angrily from inside their house.

"Harold, come inside this instant! I need you right now!"

The judge seemed a bit embarrassed by this, and then I heard Edith's voice coming from her upstairs bedroom window.

"Daddy, you heard Mother. Get your sorry ass back inside, and do what you're told, or I'll punish you more severely this time, you silly twit!"

I couldn't believe how rudely his wife and daughter were treating this respectable gentleman. I looked at his face, which had turned bright red with embarrassment and humiliation. He averted his eyes, "I'm needed inside Joey. I'll see you at the party in a little while."

With that he turned around and headed quickly towards his front door. I was puzzled by what I'd just observed. Harold Chatsworth is a very important and respected man in San Francisco, but the women in his family treated him like a little boy. I wanted to know why this was so.

I returned to my parent's house, and found them and Bridgette sitting in the Adirondack chairs on the backyard patio, and sipping martinis. I greeted my father, kissed my mother on the cheek, and poured myself a drink before taking the empty chair next to my father.

I spoke first, "Something odd just happened over at the Chatsworth's."

My father replied. "Oh really, and what was that Joseph?"

"Well, I was complementing the judge on his new car, when Julia and Edith spoke quite rudely to him, and ordered him to come back into the house. He seemed quite flustered by this."

My father took a few seconds to compose his thoughts, but before he could respond my mother joined our conversation, "Joey, Julia and Edith respect the judge, but their relationship is different than what most people would expect. All you need to know is that they're happy, and love each other very much. That's all I will say on the subject."

I considered asking her for more details, but I could see from Mother's demeanor that the subject was closed. I proceeded to have a short conversation with my father about my problem at work, while Bridgette and Mother took care of last minute party preparations in the kitchen.

After a little while I observed Julia and the judge enter our patio area through the side gate. I turned to my father, "Dad, the Chatsworth's are here. I'll go tell Mother."

My father nodded, stood up and waved to the Chatsworth's, while I scurried into the house to fetch the ladies. Our guests took their seats, and Bridgette and I brought out the platters of tasty hors d'oeuvres. I was disappointed that Edith hadn't come with her parents to my party.

"Will Edith be joining us Julia?"

"No, I'm so sorry Joey. She has an awful headache."

I'm sure my disappointment showed plainly on my face. I desperately missed my friendship with Edith. Though she was not destined be my wife, I still considered her my soul mate, and I hoped she would always be part of my life in some way.

Then the judge spoke up, "Joey, after her husband betrayed her, Edith has been depressed, and she's decided she hates all men, and I'm afraid, unfortunately, that includes you too. She only dates women now."

Julia smiled warmly at me, "Joey. I know Edith still cares deeply about you, and I think, over time you'll be friends again."

There was an awkward silence, and then Bridgette gracefully changed the subject of the conversation.

I pondered my relationship with Edith Chatsworth. I couldn't understand Edith's attitude towards me. I had always been very kind to her. I thought, what did I do to deserve this? The answer... nothing at all! I decided right then that I would reconcile with Edith. I couldn't just give up on her!

I stood up and addressed the group, "I'm going to see Edith, and ask her to come to the party."

My mother spoke first, "I do hope you can get her to come dear, but please don't be too upset if she turns you down."

I smiled back at her, "I'll be ok Mother, whatever happens, but I feel like I need to do this."

Bridgette stood up, kissed my cheek, and whispered in my ear, "Would you like me to come with you, Joey?"

I appreciated her offer but I decided I needed to be alone with Edith when I talked to her.

"No thanks Bridge. I'll be ok."

She squeezed my hand, "If you're not back in half an hour I'll come looking for you, Mister Mason."

I gave my fiancé a warm smile, "This shouldn't take long, Miss O'Brien."

I walked briskly across the street and rang the doorbell. A few seconds later, I saw Edith looking back at me through a window adjacent to the front door. I smiled at her and waved my hand. She looked back at me, and there was no expression on her face. The front door opened about three inches.

"What do you want?"

I peeked at her through the narrow opening, "Well, Edith, I came here to invite you to my party, but you know what? That's not what I really want."

"I don't feel like going to some stupid party and making small talk. So say what you came to say, and then leave me the fuck alone Joey."

"Alright Edith, but I'd prefer you to at least open the door properly so I can see your face."

She opened the door all the way and looked me in the eye. She had a stern look on her face.

"Ok Joey, I'll give you two minutes. Start talking."

I looked into her eyes, trying to find a hint of the Edith Chatsworth I grew up with. The girl who I confided all my secrets to, the girl I trusted more than anyone in the world, the first girl I kissed, and the first girl I loved completely. I thought to myself, "Oh Edith, where did you go? What could have happened to change you so much?"

I started to feel my emotions welling up inside of me, taking control of me. My lower lip started to quiver and my eyes filled with tears. My vision blurred.

"Oh Edith, I miss you so much. I can't stand it! Can't we be friends again? That's what I want more than anything, and that's the reason I'm here. Please Edith, be kind to me again!"

I wiped away my tears with the back of my hand, and looked back at Edith.

Her eyes twinkled and she smiled back at me, "Come inside Joey. Don't be such a fucking pussy!"

She grabbed my hand, led me into the kitchen and gestured for me to sit down at the dining table. She brought down two wine glasses form one of the cabinets, and then retrieved an open bottle of California chardonnay from the refrigerator. She set the glasses down on the table, and then proceeded to fill them to the rim. I carefully picked up my glass, so as not to spill, and Edith did the same. We took sips from our full glasses, and then she held her glass up towards me, so she could give a toast.

"Here's to my best friend, Joey Mason. I'm sorry I've been such a bitch to you Joey. You didn't deserve that. Can you forgive me?"

I just looked back at her and grinned foolishly. I was so happy to have her back. "Thank you Edith. I feel so relieved. Did I do anything to offend you?"

Her eyes began to shine with tears. "Hell no Joey! I really don't want to talk about it. It's just that my asshole ex-husband really fucked me up, and I think it's going to take some time for me to feel better again."

"Edith, tell me please. How can I help you? I'll do anything!"

"You're so sweet Joey. You always were a sweet person."

We sat quietly for a few minutes, sipping our wine and collecting our thoughts. I was feeling much better now. I spied a nice Christmas family portrait on the dining room wall, and I remembered how Edith had spoken so rudely to her father earlier this afternoon.

"May I ask you a question Edith?"

"Of course you can Joey."

"Earlier this afternoon, I was talking to your father outside, and your mother yelled at him, and you were very rude to him as well. I just don't understand. How could you talk to your father like that?"

Edith looked down towards her lap, and I could tell she was thinking about how to respond. After about fifteen seconds she held out her hand to me, "Come with me Joey."

I grabbed her hand and she led me to her father's study. Edith sat down on the black leather couch against the far wall, while I sat in the office chair in front of the judge's desk.

"Do you notice anything unusual Joey?"

My eyes scanned the surface of the desk, and I noticed a framed picture that caught my attention. The picture showed the judge with a look of contentment on his face, and he was standing between his wife and daughter with his arms draped around their shoulders.

But this was not your standard family portrait. Judge Chatsworth was naked from the waist up. Below the waist he was wearing lace topped pink silk stockings held up by a black garter belt, and brightly colored pink bikini panties. I thought he looked lovely. But what really caught my attention was what the women wore. Edith and her mother both wore black leather stiletto boots that came to mid thigh, black leather booty shorts, and black leather vests, which were not buttoned, so their erect nipples were exposed. However, the most unusual thing about their attire was that both women were wearing strap on harnesses. The dildo in Julia's harness was very lifelike. Edith's dildo was a monster, twelve inches long and at least four inches thick! I thought, that's fucking crazy; no way that thing can fit in his ass! I realized Edith and her mother were both pegging her father! Holy shit!

I looked at her face. Edith looked back at me with a calm demeanor. I had to learn more.

"So Edith, I don't know what to say about this picture. It's unusual, don't you think?"

"I know this is hard to comprehend Joey, but as you can see, I fuck my father in the ass with that huge dildo. Mother taught me."

My head was spinning. This seemed so wrong to me, but then I remembered what my mother had said earlier about Julia and Edith respecting the judge, and that their relationship was "different."

My mother's words came back to me, "All you need to know is that they're happy, and love each other very much."

"How did this happen? I don't understand."

"Ok, I'll give you a brief history, but you must promise not to tell anyone. This is a Chatsworth family secret, and I'm trusting you to respect our privacy."

"You can trust me Edith. I would never betray your confidence."

She turned on the judge's computer monitor on the desk and then turned to me.

"I'm going to get us some more wine. You should look at these photos."

She typed a bit on the keyboard, and then a slideshow started playing. The photos had date and timestamps displayed in the corner, and I determined that they were being displayed in chronological order. The first photos were taken twenty years ago. The earliest photos showed Edith's father, standing in his study and posing like a male model but wearing only women's panties. As time progressed the photos became more risqué, some showed the judge with an erection inside his pretty panties. Sometimes the judge could be seen rubbing his rock hard cock. Eventually he exposed his penis, and he could be seen masturbating furiously. There were numerous close up photos of him ejaculating. As time advanced the judge chose to wear additional women's clothing, like garter belts and stockings, high heel shoes, bras of different colors and styles, and very feminine frilly dresses. The judge had gone from being a panty boy to a flaming panty girl!

Edith returned after a few minutes with two full glasses of wine, which she placed on the coffee table in front of the couch. She sat at the end of the couch closest to me, and I turned the desk chair so I was facing her. She looked directly at me, and began to tell me her story.

I was eighteen years old when I first discovered Father's secret. Our housekeeper had the day off, so I offered to help my mother with the laundry. We were sorting a basket of clothing that had just come from the dryer. As I was going through the women's underwear I noticed that there were two different sizes, medium and extra large, and the larger size panties were skimpier and more flamboyant, you know, colored bright pink or red, with lots of lace trim. To me they seemed slutty. This seemed odd to me so I questioned her, "Mother, I've never seen you wearing these bigger panties. Why do you have two sizes of underwear?"

She took a few seconds and then replied, "The larger panties belong to your father. I think you're old enough to understand Edith. Please put the bigger ones in your father's dresser."

I gathered up his folded panties and went into his walk-in closet. I looked into his dresser drawers. One drawer was filled with socks, and the next drawer contained numerous pairs of ladies stockings and a few garter belts of different colors. There was another drawer full of very fancy brassieres and slips. Next to this drawer was his panty drawer, where I deposited his freshly washed laundry. I examined the hang up clothes next, which consisted mainly of his business suits, slacks and dress shirts. On the far right I spotted about a dozen frilly dresses, mostly pink in color, but there was one very chic black cocktail dress. He also possessed many pairs of ladies high heel shoes. It was obvious my father liked to dress as a woman, but I had never seen him dressed that way. I returned to my mother and we continued sorting the laundry.

I spoke first, "Daddy has some really lovely things Mother."

She smiled at me, "Yes he does darling. Do you have any questions?"

I didn't feel comfortable talking about this. It seemed strange to me. I looked directly at her, "No Mother."

She stared back at me for a few seconds, waiting for me to say more, but I just returned her stare. After a few seconds she said, "I can finish the rest of this dear. I'm sure you must have some schoolwork to do?"

I smiled at her, "Yes Mother, it never ends."

After that day I watched my father more carefully. Occasionally I would notice that the contents of my panty drawer looked different. Some of my favorites would change location, and I knew I had not moved them. Also, sometimes I noticed that my dirty panties would disappear out of my laundry hamper for a few days, and then miraculously reappear later. I concluded Daddy had a "thing" for my underwear. I didn't mind at all. He's such a nice man. If such a small thing gave him pleasure, I was happy for him.

The subject of my father's interest in women's underwear was not discussed again until I turned twenty-one. My mother and I had an unspoken agreement about this.