The Gentlemen's Panty Club Pt. 05 - Final

"You have to start slowly dear. Its good to use a finger at first."

Harold's feet were spread two feet apart. She placed her hand at the top of his cheeks and then slowly moved her middle finger inside his crack searching for his opening. When she found it she rotated her fingertip around it in a circle, massaging him, before inserting her finger up to the first knuckle. Harold let out a weak groan of pleasure, but continued thrusting his cock into my mother.

"Harold likes having his prostate massaged before I fuck him. It helps him relax his sphincter muscles."

She moved her finger slowly in and out of his asshole.

"Put your finger inside about two inches and push up towards his belly button, while making the come here motion. As you can see from his expression he likes it."

Bridgette looked up at Harold's face. His eyes were closed and he was grinning. He was still thrusting into my mother, though much faster than before.

The prostate massage lasted another minute before Julia pulled her finger out.

"I'm going to put my cock in him now, but just the head to start."

She positioned her dildo at his opening and used one hand to guide the head inside. She waited a few seconds and then pushed her hips forward. The shaft of the toy slowly disappeared inside the judge's body.

"Ok, that was the tricky part, inserting the whole shaft inside without causing him discomfort. He's relaxed now, so it's ok to really fuck him as hard and as fast as I want to. That's how he knows I'm in control.

That's what I love! "

I watched intently as Julia proceeded to fuck her husband's ass in earnest, ruthlessly pounding away at him with her purple dildo. This was so exciting for me to watch. My own cock was so hard it felt like a hot bar of steel in my hand. At this point I'd lost all self-control and was stroking myself. I desperately wanted to cum!

I closed my eyes and fantasized that Edith's soft hand was stroking my cock. I could almost hear her sweet voice whispering in my ear.

"Joey, what the fuck are you doing!"

I opened my eyes. Edith was standing beside me, and she was pissed! This was bad... really fucking bad! How could I possibly explain myself? I panicked.

"Oh Edith, um... I was just... I mean...oh God!"

"What are you doing here? Why aren't you at the Panty Club meeting?"

She looked at the computer screen and her eyes opened wide.

"Are you spying on us, Joey?"

What could I say? I was busted... big time!

"Um...yes Edith."

"Why Joey? Don't you know that's fucked up; that what you're doing is really creepy? Why would you do that?"

I looked into her eyes, "Edith, please let me explain."

"I'm listening, Joey. You better have a damn good reason for being such a fucking little pervert!"

"I heard Mother talking to Bridgette at the party last Saturday; telling her about pegging and how she could use it to take control of me in the bedroom... so she could make me happy... so we would have a happy marriage."

"So you thought you could spy on us to see if she'd do it?"

"I needed to know if she liked it. I have no experience with pegging. To be honest, Edith, I'm afraid."

I looked into her eyes. She didn't look quite so angry now.

"Afraid of what?"

"I'm afraid that Bridgette will like pegging, but that I won't like it, or even hate it. In that case pegging could destroy my marriage!"

Edith seemed amused by my statement.

"Ha! You really are a pussy sometimes, Joey. There's nothing to be afraid of, but it does take a bit of getting used to before you really enjoy it."

I wasn't convinced and shook my head.

"I don't know, Edith. I'm really worried."

She looked down at my penis. My erection had vanished.

She giggled, "Yeah, I can see that."

She tickled my penis with her index finger, trying to bring it back to life.

"Would you like me to help you Joey?"

"Help me with what, Edith?"

"Pegging silly. If you want I can peg you right now, and then you'll know whether you like it or not."

I thought about her generous offer for a few seconds. Edith continued tickling the underside of my penis.

"You'd do that for me?"

She chuckled, "Sure Joey. I think you worry too much. In fact, I think you'll love pegging, once you try it."

I smiled sheepishly back at her, "Alright Edith. Tell me what to do."

She pulled her hand away from my rapidly growing penis and pointed towards my feet.

"Get down on the floor, on your hands and knees. I'm going to fuck you doggy style. I'm going to make you my bitch!"

I pretended to be frightened, but then she stuck her tongue out at me, which made me grin. I was feeling much more relaxed and comfortable. Edith knows me so well.

"Oh, what the hell!"

I got down on the floor as she'd instructed me. Edith knelt down on the floor behind me.

"Spread your legs apart Joey."

"Like this?"

"Perfect. Now just relax your body. I'm going to stick my finger in you first."

"Ok Edith."

A few seconds later I felt something wet dripping down in my crack, and I remembered the bottle of lube that I saw earlier in the living room. She rubbed the tip of her finger around my anus a few times, and then I felt some pressure as she penetrated me.

" Wow, that feels interesting... but kind of nice too."

"I'm going to put a second finger in. Tell me if it hurts, Joey."

There was a bit more pressure, but it felt quite pleasant.

"That doesn't hurt at all."

The sensations were quite new for me, but to my surprise I really enjoyed it.

"Can you put another finger in, Edith?"

She laughed, "Wow Joey! You're a butt slut!"

Edith fingered me for about five minutes, and I was really enjoying the sensations, but then she abruptly stopped. I looked down at my cock and was pleased to see my erection had returned! Welcome back buddy!

We both heard a scream coming from the computer speaker. I looked over at the screen. Mother's back was on the pool table and her feet were on top of the judge's shoulders. She was looking directly at my father's face with a fire in her eyes. My father returned her stare. He had a smile on his lips and a twinkle in his eyes.

Harold's closed his eyes and yelled out, "I'm cumming Edward! I'm spurting my jizz into your wife's hot wet cunt!"

Then my mother yelled at the top of her lungs, "Oh fuck yes, Harold. Give it to me! Give me your spunk!"

Both of their bodies began to shake. I was mesmerized by what I saw.

A few seconds later, Edith tapped me on the shoulder with her fingers to get my attention.

"Ok Joey, just relax while I stick my dildo inside of you."

I felt a sharp pain as my anus was stretched open by the head of Edith's rubber cock. I felt it descending slowly into my body, deeper and deeper. The pain was intense, but thankfully, it wasn't getting any worse. Edith stopped pushing when her black dildo was fully inside of me.

"Breath, Joey. Take slow deep breaths and the pain will go away in a few seconds."

She was right. About twenty seconds later the pain was gone! I turned my head around and smiled at her.

"It feels a lot better now Edith."

She smiled back at me.

"That's good Joey. Ok I'm going to start fucking you now. I'll start slowly. You tell me when you want me to go faster."

"Its exciting Edith."

"Why don't you watch the screen? I think you might be interested in what's happening right now."

I looked up at the monitor. My mother, Julia, and Judge Chatsworth were seated on the couch. My father was on top of the pool table, lying on his stomach with his ass in the air. There were two pillows under his tummy and one pillow supported his head. His hands were tied behind his back with nylon rope. Bridgette was standing behind him, and her flesh colored dildo was buried, balls deep in my father's ass! Holy fucking shit! His eyes were closed and he was calling out.

"That's it, Mommy. I've been a bad girl and I need to be punished. Harder Mommy! Please Mommy!"

Now it was Bridgette who yelled out.

"Take it Edwina! Take your punishment like a good little sissy!"

Bridgette's hands were on my father's hips and she was pulling him backwards, while at the same time she was thrusting her hips forward, impaling his asshole on her rubber cock.

"Edith, do you see what Bridgette is doing to my father?"

"Fuck yeah Joey, she's pegging him doggy style, just like I'm pegging you!"

I felt Edith's dildo invade my rectum. She pulled it out slowly, and then abruptly and forcefully rammed it back inside of me. I was at her mercy, and I loved it. I was totally under Edith's control, and that's exactly what I wanted!

I closed my eyes, savoring the pleasurable sensations pulsing through my body.

"Do you want to cum now, Joey?"

"Oh God Edith... yess!!"

She abruptly pulled the dildo out and barked, "Turn over on your back."

I flipped over and pulled my knees up to my chest. Edith had fire in her eyes as she rammed her rubber cock back inside me. When it was buried to the hilt she dripped some lube onto the head of my cock. She interlaced her fingers from both hands together, and wrapped them around my shaft. She totally took control by pushing the dildo into my ass while at the same time, firmly stroking down the length of my shaft. This felt so surreal to me. She repeated this motion, starting slowly and then gradually increasing the pace. I knew my orgasm was coming soon; it was unavoidable. It happened on the tenth stroke.

I looked into Edith's eyes and blurted, "I love you, Edith!"

She laughed, "Oh, that's what all you men say before they cum."

"No Edith... I do! Oh God, oh God, oh God... I'M CUMMING!!"

My legs began to shake and my prostate began to spasm. I looked down at the head of my cock just as a six inch strand of semen squirted out of my slit and landed on the back of Edith's hands, quickly followed by three smaller spurts of white cream. My head began to spin, and for a second or two I felt dizzy, like I was going to faint.

After a few seconds I started feeling normal again. I opened my eyes. Edith was looking back at me and smiling.

"Well, did you like it Mister Mason?"

I grinned back at her like a fool.

"It was fucking amazing. Thank you, Edith!"

She pulled the dildo out of my ass and then helped me to stand up. She grabbed a box of tissues off my father's desk, and handed me a few. We took some time to clean up, and then I got dressed.

I looked at the monitor. Bridgette was sitting between my mother and Julia on the couch, and my father and the Judge were sitting on the two chairs.

I heard Julia's voice.

"I wonder what's taking Edith so long. She went to fetch a bottle of lube from her purse, but that was ages ago. I better go see what's keeping her."

Edith grabbed my hand and led me towards the door.

"You better get out of here Joey."

I looked into her dark brown eyes. She looked so beautiful, just like that day so many years ago when I first fell in love with her. Without thinking I pulled her into my arms and kissed her on the mouth. I'd wanted to do that for a long time. I felt her hand on the back of my head, forcing my mouth onto her mouth, my lips onto her lips. I opened my mouth and pushed my tongue into her mouth, probing for hers. She enveloped my tongue with her lips and started sucking my tongue, forcing it into her mouth. I didn't resist. I was in heaven for a few more seconds, before she broke our kiss.

"It's time for you to go, Joey. Don't forget, you're going to marry Bridgette in five weeks."

Chapter 6, Good Bye Joey

I called Edith a dozen times the next day, and again the day after, but I only got her voicemail.

I was so confused! For me, pegging had been a very emotional experience, as well as an intensely sexual experience. Being touched like that felt more intimate for me, and sharing that with Edith made me feel connected to her emotionally and spiritually. I was unable to control or understand the feelings I was having for her. But I realized these feelings were not new, that when I first fell in love with her many years ago I had the same feelings.

I wanted her in my life! I wanted her to peg me again!

But deep down I knew those feelings were wrong. I was engaged to Bridgette, and I adored her too! What have I done? Is it possible to be in love with two women at the same time? After all, I wasn't living in biblical times when polygamy was the normal form of marriage. I would have to make a hard decision.

The following Wednesday afternoon I was in a business meeting with an important prospective new client when my cell phone rang. The caller id showed that it was Edith. Immediately I excused myself.

"I'm truly sorry, but I have to take this call."

I ran back to my office, closed the door behind me and locked it.

"Edith... thank God you finally called!"

"Hi Joey, yeah I'm sorry about that. I've been busy."

She sounded more serious than usual.

"With what?"

She hesitated for a bit before answering, like she was deciding what to say. This phone call was starting to feel awkward.

"I didn't know what to say to you after what happened Saturday. I've only pegged one man before, my father, never any other man. Doing it with you changed my feelings for you Joey."

Ok, we're going there, talking about how we feel about each other, which is what I was hoping would happen.

"I meant what I said, Edith."

"What do you mean, Joey?"

"When I said that I love you."

There was another awkward silence that lasted a full ten seconds.

"Are you still there, Edith?"

She still didn't answer me, but I could here her starting to cry in the background.

"I broke your heart once before. I may do it again... I'm so confused... and I don't want that. You're a sweet man and I don't deserve you. You're going to marry Bridgette... she'll make you happy, and that's what I want for you more than anything."

I forced myself to breath.

"Are you sure that's what you really want?"

Now she was sobbing in the background.

"Good bye Joey. I'll see you at the wedding."

Chapter 7, An Indecent Proposition

I knew things would be different from now on. Bridgette had the ability to control me in the bedroom if she wanted to, but there was no sign of her new power. However, our time in the shower did get more interesting, in that she paid a lot more attention when it was time for her to wash my anus. The first time she did it I was taken by surprise and looked at her oddly.

"I just want to make sure you're clean here Joey."

As we both got more comfortable with this, she became more aggressive. She would tell me to bend over, and then stick her middle finger all the way inside of me while making the "come here" motion, applying direct pressure to my prostate and forcing me to moan with pleasure.

"Am I hurting you Joey. I'll stop if it hurts, but you have to let me know."

She knew exactly what she was doing to me, and that it didn't hurt at all.

"Oh God, don't stop Bridgette!"

My cock would get rock hard when she did this to me, and occasionally pre cum would leak out; she seemed quite pleased with herself. But one time I almost made a fatal mistake; I was enjoying myself a little too much and whispered, "Oh God Edith, don't..."

I caught myself in mid sentence.

"Don't stop Bridgette, that feels so fucking nice!"

Talk about dumb luck!

During the next two weeks life became a bit more hectic for Bridgette and me. You see, finalizing the plans for the wedding, the reception and the honeymoon was a more complicated than we'd expected.

I was tasked with planning the honeymoon. I deliberately misled Bridgette about how hard I was working on this. I told her that I was arranging our dream honeymoon in Paris, staying in the penthouse suite of a famous four-star hotel, and how difficult it was to finalize the contract. I told her I was using my influential friends from the Panty Club to act as intermediaries for me. I also told her I was reserving a private jet to fly us to Europe, and I also implied we would be dining every night at the most exclusive haute cuisine restaurants in the City of Lights.

All of this was bullshit! My real plan was to honeymoon at my parent's luxury condominium in Kona town on the romantic island of Hawaii. I'd called the property manager as well as Kimo, the head of our household staff; it took me all of five minutes to complete the arrangements.

Bridgette managed the details for the wedding ceremony and the reception, with a great deal of assistance from my mother and Julia Chatsworth.

Since both of our families were members of the same private country club, we were able to reserve the beautiful outdoor area used specifically for weddings, an open grassy knoll overlooking a pristine blue lake near the eighteenth hole of the golf course. The reception would be held in the Club House dining room, which is more commonly referred to as "The Watering Hole" by the club members.

It was a glorious Friday morning, two weeks after the pegging lesson. I was seated at our dining room table, enjoying my first cup of coffee; Bridgette was standing at the stove making scrambled eggs.

"Do you want toast or a bagel, Joey?"

I pulled my eyes away from my morning Chronicle.

"Wheat toast please, with butter and marmalade."

A few minutes later she placed my breakfast in front of me.

"Remember Joey, I'll be home late tonight."

I gave my fiancé a warm smile.

"Yes, I remember Bridgette."

I gave her my sad puppy dog face.

"I'll be here, all alone, waiting patiently for you to return to me, but please don't hurry home on my account!"

She grinned at me, and I could see the love she felt for me in those beautiful blue eyes of hers.

"I really want you to enjoy your party, dear."

"Thank you, Joey. You're sweet!"

"I know; I hear that a lot."

My fiancé's bachelorette party would take place this evening. Melanie was Bridgette's maid of honor, and had made the party arrangements, with some help from Edith, who had booked the entertainment.

The previous evening Bridgette and Melanie met at our dining room table to go over the party details. The location was my parents' pool house.

Melanie scanned her notes on her iPad.

"I'll be at the pool house around six pm to check on things. I made arrangements to have all the furniture in the family room moved, so we'll have plenty of room to party. I've rented more then enough folding chairs to accommodate the guests. We can get fucking crazy if we want to!"

Melanie gave Bridgette a mischievous smile.

"You'll see why when the entertainment starts."

Bridgette giggled, "You mean the male stripper?"

Her girlfriend responded, "He prefers the title, female friendly adult entertainer."

Bridgette laughed, "Well, who cares? As long as he has a nice dick! Do we get to touch it?"

Melanie laughed, "His web site says that costs two hundred dollars more. I looked at his pictures and I think he's worth it."

Bridgette thought for a few seconds before responding.

"I don't know Mel, that seems like a lot of money just so I can touch it, don't you think?"

Her friend chuckled, "For two hundred, all of us get to touch his dick. I'll pay for it."

Bridgette and Melanie gave each other a high five slap.

"Ok, ten ladies have confirmed they're coming to the party."

"You told them about the dancer?"

"I did. Your sister Kathleen had some questions about it, though. She wanted to know if the entertainment would be too mature for her daughter, Britney."

"What did you say?"

"In my reply I said I assumed her daughter knows that men have genitals, and that nothing weird was going to happen."