The Gentlemen's Panty Club Pt. 05 - Final

I tiptoed back outside and took a position behind the back of the brick barbeque. The chimney is six feet high and three feet wide, so it was a good hiding place. From there I could hear the ladies, who were ten feet away, but they couldn't see me.

The four women had rearranged their chairs so they were sitting in a small close group facing each other. I heard my mother's voice first.

"Bridgette dear, did you mean what you said about doing whatever you can to make Joey happy?"

"Of course I did Beverly, I love Joey more than anything."

"Well, that's nice to hear dear. I want to share something with you that I believe will make Joey very happy."

"Really Bev, and what's that?"

"In everyday life it's good to let the man be in charge. It's feeds his male ego, but in your bedroom you need to be the person in charge, and I mean totally in control. That's how I am with Edward, and he adores me. In our bedroom I call him Edwina! We fantasy role play with him acting as a young helpless girl whom I dominate sexually."

"Doesn't that make him feel humiliated?"

"Yes it does dear, and that's the point of it, he actually likes it. The embarrassment excites him sexually. The pleasurable feelings are much more intense for him."

"Wow, I had no idea men could get off like that!"

"Not all men want to be controlled, but in my experience men who wear panties love being controlled by the women they care about. Believe me Bridgette, Joey will adore you too, if you do what I tell you."

Julia Chatsworth spoke next.

"My situation with the judge is similar but different in one detail, in that Edith and I both have control over him. It's brought us all much closer together as a family. Isn't that right, Edith?"

"It's true Bridgette. Men who have a fetish for women's underwear want to submit to the women who care about them. When you control your husband you're showing him that you care about him... that you really love him as he is, as a sissy panty girl."

For the next few seconds the conversation stopped, so I peeked at the ladies from my hiding spot. Mother was refilling their champagne glasses.

"Let's drink to strong women who know how to make their men happy!"

I heard their glasses clink. Then they chanted together, "To strong women!"

I heard them giggle for a bit and then my fiancé spoke, "Ok, I'll try being in charge Beverly, but I don't know what to do!"

Mother chuckled, "Oh, don't you worry about that dear. We'll teach you, isn't that right ladies?"

Edith giggled, "Fuck yeah, Bridgette! The best way to show a man you're in charge is to fuck his ass, it's even nicer for him if he's tied up and feels helpless. That really shows him that you're in charge of him, and his pleasure!"

Bridgette looked doubtful.

"You know what pegging is, don't you Bridge?"

"Well Edith, I've heard of it, but I've never tried it. It's when a woman wearing a strap on harness penetrates a man's anus with a dildo."

Edith chuckled, "That's right sweetie. Once you train him to like it, he'll be begging you to peg him all the time, and the next day he'll be so grateful he'll treat you like a fucking queen, and do absolutely anything you ask."

Edith's mother interjected, "Or give you anything you want!"

Now it was my mother who added, "And one other thing, Bridgette... he'll never cheat on you, and he'll never leave you for another woman!"

Bridgette took a few seconds to make eye contact with each of her three companions.

"Ok, I'm convinced. I'll do it! Will you teach me Beverly?"

"We all will, dear."

My mother and Bridgette hugged each other.

"Ok dear, we'll meet here next Saturday evening at eight o'clock, and we'll teach you everything you need to know about pegging. You can watch us peg Edward and Harold, and then if you're up to it you can peg them too. Believe me dear, they won't mind helping out. By the way, be sure to wear some sexy underwear... and a matching bra if you have one. If not, you can go to Victoria's Secret and buy what you need. Have them charge it to my account."

Bridgette smiled at my mother, "I'll do that, Beverly. Should I buy something skimpy?"

"Get something that will please a man. The idea is to make my husband and Harold as excited as possible. Edward likes the raunchy stuff. I'm sure Melanie can help you find something."

Bridgette chuckled, "Ok, I'll tell her I want the slutty look!"

When I heard my fiancé say that I almost laughed out loud, but I was able to control myself. Instead I just grinned like a fool.

"Joey will be at his Panty Club meeting. Julia and I will ask Harold and Edward to devise some convenient excuses for missing the meeting. We'll meet in the pool house for your pegging lesson."

"Wow I can't believe it, my future mother in law is going to teach me how to fuck her son in the ass with a dildo! Holy shit!"

"Well dear, you did say you'd do whatever you can to make Joey happy."

Strange thoughts began spinning through my brain. My future wife was going to be in control of me in our bedroom, totally and completely! The idea intrigued me, but it also frightened me. What if things went wrong? What if I freaked out? I needed some time in the next few days to think about this.

I decided this would be a good time for me to interrupt the ladies. I tiptoed back to the kitchen door, opened it, and then closed it loudly enough for the ladies to hear it. Then I called out, "I found the chardonnay Mother, but there were two with Hall in the name. Shall I open both?"

"Don't bother Joey. Bring us another bottle of champagne, please. The ladies have one more thing to celebrate!"

Chapter 5, The Pegging Lesson

The following Friday I received an email from Judge Chatsworth. "Unable to attend tomorrow's P Club meeting" was the subject. In the body of the email the judge explained that he was in the final stages of an important court trial, and had to work all weekend.

An hour later my phone pinged. It was a text message from my father that said:

Hi Joey, will miss P Club meeting Saturday. I'm coming down with a cold.

: > (

The email and text message confirmed it; the pegging lesson would take place Saturday evening, as scheduled.

My feelings about this were mixed. I was very curious about what would happen at the lesson, but more importantly, what Bridgette would do and how would she react to it. Would she use a strap on dildo to penetrate Judge Chatsworth's ass... or my father's? That thought excited me, and also terrified me somewhat. What if it repulsed her? Or... what if she liked it? I had never been pegged before, so I no idea how I would react to being penetrated by a woman.

I made a plan to secretly observe the lesson. My parents have a security system to protect their house. My father is very proud of it, and he was very excited to show it to me after the installation was completed. The control center for the system is the iMac in his den. The computer system has a high definition twenty-one inch monitor, and the security software allows him to display live video and audio from any room in the house, including the pool house. My plan was to be in my father's den at fifteen minutes after eight, and watch the video feed from the camera in the pool house, as my mother, Julia and Edith instructed my fiancé on how to properly fuck a man in the ass!

On the day of the Panty Club meeting, I deliberately took my time dressing in front of Bridgette. I looked at her closely, trying to spot anything unusual about her demeanor. She seemed a bit distracted.

As usual, she had chosen the clothes I would wear to the meeting; khaki slacks and a cream colored golf shirt that showed off my sleek torso. It was casual, but also stylish. Underneath I'd be wearing a pink thong panty, a pair of pink thigh high stockings, with a matching garter belt.

When it was time for me to leave for the meeting, I hugged Bridgette and gave her a gentle kiss on the lips.

"Will you be staying home tonight, Bridgette?"

"Yeah Joey, I'm a little tired. I think I'll hop into bed early and read for a bit. Edith gave me a new romance novel that she said is pretty erotic, at least I hope so."

She gave me a mischievous look, "Maybe I'll think about you and masturbate!"

"That sounds interesting, maybe I should skip the Panty Club meeting and stay home with you?"

"Don't be silly, Joey, you know you enjoy the meetings. Besides, I prefer to be alone when I play with myself."

"Don't you mean, when you play with your clit?"

"Oh, that's rude! Get going Joey, or you'll be late!"

I took an indirect route to my parent's house, and arrived a few minutes after eight. Bridgette's car was parked in the driveway. I looked over at the Chatsworth's house across the street, and noticed the lights were off.

I let myself in with my house key and headed towards the den, which is accessed from the living room. I noticed that Bridgette's purse was on the coffee table along side another purse that I didn't recognize. I knew it wasn't my mother's, so I assumed it had to belong to either Edith or her mother. I took a quick peek inside it and spotted a bottle of personal lubricant on top, which made me smile.

I walked into the den, sat down in the office chair at my father's desk, and started the iMac. When prompted for a login, I flipped the keyboard over. My father has his passwords written down on a Post It note, which he keeps under the keyboard. I logged in and clicked on the icon to start the security system application. Twenty small windows were displayed, each one showing video from a different room. I double clicked on the last window, which showed the large family room inside the pool house. The small window instantly expanded to occupy the full screen of the monitor. The security application allows me to control the camera. I can pan to the left or right, up or down, and I can zoom in or out.

The four ladies were seated on the couch. My mother sat on the left end of the couch, and was wearing black knee length leather boots with three inch spiked heels, black string bikini panties and a black translucent camisole top. Her bountiful breasts and nipples were clearly visible underneath it. Ah yes... she looked so sexy! I couldn't help staring at her for a few seconds, and thinking how blessed my father is to be her loving husband.

Seated next to my mother was Bridgette, who was wearing a red g-string panty and matching unlined bra. Wow, she looked amazing in her new lingerie! A thought crossed my mind, how nice it would be if she were to model them for me. I also thought that it was a good thing that I'd shaved her "down there". Fuck yeah!

Julia sat on the other side of Bridgette. She was wearing a flesh colored body suit, and I could see her camel toe through the sheer fabric. She's such a very desirable woman! I thought about her camel toe for a few seconds, and how lovely it would be if she asked me to lick her with my tongue, to taste and smell that cunt! I felt my penis stirring to life!

Edith sat at the other end of the couch. He long brunette hair was tied on top of her head. She was wearing a black leather collar around her neck... and nothing else! Oh fuck! Her body mesmerized me. I openly stared at her, unable to avert my eyes!

The long black leather couch was directly in front of the fireplace but faced the pool table. An oak coffee table was positioned in front of the couch. There were three strapon harnesses on top of the table, and three rubber dildos; a ribbed black one, one flesh colored dildo that looked exactly like a real penis, and a bright purple one. A clear plastic bottle of personal lubricant, and a roll of paper towels sat on top of the coffee table as well. A white bed sheet covered the pool table. I assumed that was to protect it from stains. There were four large pillows on the pool table, and several lengths of nylon rope.

I could barely hear my mother speaking, so I turned the volume up until I could hear her clearly.

"Thank you for coming, Bridgette. I'm here because I love my son, and I've come to love you too, dear. I want your marriage to Joey to be filled with joy, that lasts for many years."

She reached out and squeezed my Bridgette's hand.

"I love him too, Beverly. I'll do anything I can to make Joey happy."

"Well dear, that's why we're here, to show you a fun way to make him very happy."

My mother scanned the women's faces, "So ladies, shall we get started?"

Edith replied first, "Sure Bev, let's show Bridgette how we please our men!"

Julia and Edith stood up, and Bridgette watched them step into their harnesses, adjust the straps and secure them, and insert their dildos. Edith was wearing the black dildo, and Julia wore the purple one. My mother handed Bridgette the remaining harness and helped her put it on, and insert the flesh colored dildo into the harness.

"Do you like your new cock Bridgette?"

She swung it back and forth, and then up and down and laughed, "I love my big fat cock Bev, and I can't wait to use it!"

My mother grinned at her, and then called out towards the back bedrooms.

"Ok boys, you can come in now!"

My father entered first. He was wearing a very short pink summer dress with white lacey fringe around the hem, white girls patent leather slippers, and pink anklets also trimmed in white lace. His lips were colored deep red, there was mascara and pink eye shadow around his eyes, and he wore a long blonde wig. In truth he looked rather foolish, but from previous experience I knew he enjoyed pretending to be this fragile girl named Edwina.

Harold followed behind him. He was wearing a skimpy black thong panty made of leather, and nothing else. I thought that for his age he's in pretty good shape. I knew he regularly took classes at his gym. Julia and Edith have told him he's not allowed to be overweight, and in order to please them, he does whatever his wife and daughter ask of him.

There were two straight back oak chairs on either side of the couch that my father and the judge sat in.

"I especially want to thank Edward and Harold for volunteering to help. I'm sure this will be quite embarrassing for them."

My father addressed the ladies.

"I've only done this with Beverly, but I must admit, I have fantasized about other women pegging me, but the thought of it scares me somewhat. I don't know how I'll handle it."

He looked at Harold, "How do you feel?"

The judge thought for a few seconds before responding.

"The same as you, Edward. I'm ashamed to say, I've thought about your wife pegging me. She's seems so intimidating to me. I hardly know Bridgette at all, so I have no idea how I'll feel if she decides to peg me."

Edith laughed, "Oh Daddy, you know we all care about you and Edward. I promise, we'll be very nice to you, right ladies?"

My mother chuckled, "I don't know if nice is the right word Edith, because I will do whatever I want to your Daddy!"

She smiled at Bridgette.

"Pay attention dear."

She looked sternly at my father.

"Edwina, last night you told me a secret fantasy of yours. I want you to share it with us."

My father's face turned beet red.

"Oh Bev, no, I can't!"

Julia spoke in a commanding tone, "We're waiting, Edwina."

My father looked down at his feet, too embarrassed to look at anyone while he spoke.

"I want to watch Beverly being mounted by another man, with her legs in the air, while I masturbate. I want him to fuck her hard, until she screams out with pleasure while she climaxes."

My mother smiled back at him.

"Thank you, Edwina."

She turned to Julia, "Do you mind if I borrow Harold for a bit?"

Her girlfriend grinned back at her, "Not at all dear. I'm sure he'll be happy to accommodate you. While Harold is fucking you, Edith and I will be fucking him!"

She looked into Bridgette's eyes.

"You can fuck him too dear, that is... if you want too."

I noticed Bridgette's face flush, but she didn't respond.

My mother stood up and took Harold by the hand.

"Come along Harold."

She led the judge to the pool table.

"Do you think I'm sexy Harold?"

He gulped, "Yes Beverly, very sexy."

"That's good. I'd like you to prove it."

My mother hopped up onto the pool table, with her legs hanging over the side. She spread her knees apart.

"Lick me Harold."

He nodded his head, and without hesitating pulled her panties off.

With a few mouse clicks I made the camera zoom in for a close up view of my mother's slit. Harold used his fingers to open her pussy lips, and began licking the pink area inside of my mother's cunt. The slurping sounds were so very erotic. I felt my penis began to stir inside my panties.

Mother closed her eyes and smiled, "That's feels nice Harold... so fucking nice! Move up a little and do my clit, you naughty man!"

Wow! I couldn't believe my eyes. I felt my penis pressing against my trousers, straining to get out. I pulled my zipper down and levered my cock out.

The judge was furiously licking my mother's clitoris, swirling the tip of his tongue around and around it.

My level of excitement was growing quickly. I stood up, stripped off all of my clothes, and took my seat in front of the monitor.

Mother opened her eyes, "I want your cock inside me Harold...now damn it!"

He stripped off his thong and was about to penetrate my mother when I heard Edith's voice.

"Wait Daddy. Turn around and show Bridgette your cock. She's never seen it."

Slowly he turned to face Bridgette. He looked uncomfortable.

"I hope this doesn't offend you, my dear?"

I zoomed in on Judge Chatsworth's erection. I was impressed with the size and thickness of his cock. My mouth began to water.

My fiancé laughed, "Not at all Harold, you have a very nice looking cock, just like mine."

She gave her flesh colored dildo a shake.

"Show me what you can do with it."

He grinned back at her, turned around to face the pool table, and sank his shaft into my mother's glistening slit. He pulled out slowly and then pushed his hips forward, burying his cock inside of her. Again and again he plunged into her, faster and faster, deeper and deeper he went.

Mother's eyes were closed and she called out, "Yes, that's it Harold. Fuck me like your slut wife!"

She turned her head in the direction of my father. I panned the camera over. My father's pink dress was pulled up past his stomach and his panties were pulled down to his knees. He was gripping his shaft with one hand, stroking up and down the length of it. He was using the palm of his other hand to rub his knob like he was juicing a lemon.

"Stop that Edwina! You are not allowed to cum yet!"

He looked into my mother's eyes and nodded. Then he placed his hands down by his sides.

"You'll have your fun soon enough. I promise. For now you need to be patient while Harold and I have our fun. I like it when you watch me, with this big fat cock in my cunt, being fucked by another man. I want you to see me cum!"

He responded in his girly voice, "Yes Mommy."

Julia stood by Bridgette's side.

"I'm going to fuck him now. Watch carefully and I'll show you how."

Bridgette giggled, "Ok Julia. Wow, I can't believe we're doing this!"

Julia picked up the bottle of lube off the table, shook it, and squirted a generous amount of the slippery liquid onto the head of her purple dildo.

She turned to her daughter, "There's enough lube to get started, but we'll need more later when we fuck Edwina."

Edith nodded her head, "I have more in my purse."

Julia took a position behind her husband. She motioned for Bridgette to kneel on the floor so she had a clear view of Harold's ass.