Fantasy Island

She put her things in her suit case and we left. I carried three bags, Jo had a small purse. I walked behind her, and watched as men cranked their necks to get a better look at Jo. Repeatedly I told myself, “This IS what you wanted.”

We walked out of the hotel and got in Jo’s car. She drove to a clothing boutique in a strip mall. We parked directly in front. The store was not supposed to be open until 1pm.

“The owner owes me a favor, so I got her to come in a little early. We will have the store to ourselves. Come on. She is waiting for us.” Jo stated.

I looked at Jo and said, “I would rather wait out here.”

Jo looked back at me. “How are you going to try on your new clothes if you wait out here, Dear? Now, put down your phone, open the car door, and get your little ass inside of that store, “Phyllis”. We are meeting Debra for your fitting. This had better go well, or this fucking key will be flung out the window on our way home and your cage will stay on even longer. Am I clear?”

Jo spoke with an authority I had rarely witnessed and it excited me and scared me at the same time.

With that, Jo opened her car door and got out of the car. She walked to the front of the car and stopped before I got my door open.

Jo was peeved at my lack of urgency. As I walked up to her and gritted her teeth and condescendingly said, “Suck one cock and it slows you down to a miserable hag.”

Jo grabbed my arm and said, “THAT was your last warning, Phyllis.”

Debra met us inside the store. Jo greeted her like a long lost friend.

“Debbi, THIS is your client today.” Jo said as she pulled me forward and pushed me towards Debra.

Debra looked at me, “I see. So you want black thong panties, with lace?” she asked.

Before I could answer, Jo answered for me. “Debbi, 8 pair in black, 3 pair in blue, and 3 pair in red, 2 whites, one green and 4 pair in nude if you please.”

Debra looked at Jo and nodded. She smiled and then grabbed me by the elbow and led me to the back of the store. “Come with me Dear, We need to measure your hips and then get you fitted.”

We walked to the back of the store into an office with a platform.

“Jo is something else, isn’t she?” Debra asked as we walked through a doorway.

“Yes she is.” I answered.

Debra looked at me, “Is this your first time buying women’s underwear Dear?”

I nodded.

“I need you to strip down, then I will measure your waist, and then what I do not have in stock will have to be ordered.” Debra said. “You will have to pick it up later on, I do not ship. Is that okay?”

I nodded again, forgetting that I was wearing Jo’s panties.

Debra took a deep sigh. She pointed at a platform. “Take off your shoes and pants and get on the platform so I can measure you. Since its your first time here, lets get ALL your measurements and I will keep them on file. Then we don’t have to make these kinds of early appointments.”

I kicked off my shoes and froze. “Debra, is it common for men to come in here like this and buy women’s undies?”

Debra chuckled, “More than you would think – OR IMAGINE. I have almost as many male customers as I do female customers. I am one of the few stores around here that carry the more popular brands for cross dressers, and I can order anything for the cross dressing line, so I have quite a following.” Debra explained.

I dropped my pants and felt my face turn red. Debra looked at me. “I have seen a few caged dicks before too Hon, you have yet to surprise me.”

Her voice was reassuring in some ways. Almost like the voice of reason.

I nodded again.

I pulled off my shirt moved across the room.

“You are quiet today, but I have a feeling this is just the beginning.” Debra said.

I made my way onto the platform. Debra measured me, then she would write things down on a slip of paper. After a few additional measurements, she disappeared. She came back with one package of blue, one package of red, and two packages of black.

“Which color you want to try on Sweetie?” Debra asked.

I answered, “Black” very sheepishly.

Debra smiled and pointed to the dressing room. I took a single pair from her hands, slipped into the dressing room and pulled them on. They felt REALLY nice against my skin.

“How’s the Fit Sweetie?” Debra asked from right outside of the curtain.

“Perfect.” I replied with some amazement in my tone.

“Hon, since its the first time, I would like to take a look. Once we get the brand and sizing down, then I will trust your judgement.” Debra asked.

I slid the curtain back sheepishly and Debra stepped inside the room. She slipped her finger inside of the waist band moved her finger around. At random, she pulled at the fabric.

“UH – Huh.” she mumbled.

“Turn around Sweetie.” Debra ordered.

“Jo said to let you wear them out of the store.” Debra acknowledged.

Again, I managed a nod.

“Get dressed, you can wear these out of the store. I will meet you up front with Jo.” Debra announced.

I stepped out of the dressing room, put on my pants and put Jo’s panties in my pocket.

Debra met me up front where her and Jo had been discussing a few things.

“Is there anything else today?” Debra asked.

Jo stepped forward with a catalog of high end Halloween costumes. She told Debra, “Add on that one item we were just talking about. In his size. We will just trust your judgement rather than keep things tied up for you today. We are running a little late.”

Debra nodded. She rang everything up and I paid for it all.

Debra told me, “The rest of the panties and your uniform should be in by Thursday or Friday of next week, we close a 7:00pm. You can try it on before you leave to make sure it fits, but once it leaves, its yours Sweetie.”

I looked at Jo with a confused look.

“Halloween is coming. I want you to dress up this year.” she replied without me asking.

We left and walked back out to the car. Jo walked behind me, working her phone. “How do they feel Sweetie?” Jo asked.

I started to answer but said nothing. Then I thought about her promises.

“They are very comfortable and feel nice against my skin.” I replied.

Jo said nothing. We got in the car and she drove to a nail spa. I assumed I was waiting in the car for this appointment too.

NOPE.

Jo shut off the car and said, “This is YOUR appointment too, so get out and quit moving slower than me.”

Jo reached down between her cleavage. “If you don’t, This key will end up in a trucker’s tire on the way home.”

We walked in to the spa. Jo entered first, and I followed. As I let the door close behind me, they called my name out.

“See you in a bit love.” Jo teased.

I was led to the back of the spa by a small Korean woman. She scrubbed my feet, removed the dead skin, cut away the excess, then then rubbed them down with oil.

She trimmed my nails and then let my feet soaked in a hot tub while my hands were given the same treatment.

At the end of the treatment, she soaked my hands in wax after she trimmed my fingernails.

She moved back to my feet where she shaped the nails, then painted them a light pink color. The small woman looked at her paper before she made every move. She hardly spoke to me. After the pink polish dried, she applied a shiny clear over the top.

Then she trimmed my finger nails, shaped them, and then painted them the same pink color.

It was hardly noticeable, but I did notice a lot of snickers in the salon waiting area.

After the pink dried, she applied the same clear.

I was left in the chair for 10 minutes so everything could dry completely.

“Well, I can stick my hands in my pockets and I am wearing close towed shoes, so this isn’t so bad.” I thought to myself.

Just before the timer went off, Jo walked in with a pair of flip flops. A pair of yellow flip flops with daisies on the straps.

“Put these on so we can go to the store.” Jo ordered.

ALL I could think about was getting out of my cage later tonight. I slipped the flip flops on and carried my shoes and socks.

Jo paid for the “mani – pedi”, the polish, and the clear. At the same time, she made an appointment for me to come back in a month.

The small woman said something to me in Korean as we left. I smiled and said “Thank you” really slowly.

We walked back out to the car and got in before Jo said anything else to me.

“Let me see your pretty nails.” Jo teased.

I held them out in front of me.

“That Gee does amazing work.” Jo said.

I assumed this was Jo’s way of poking fun at me for taking Robert’s cock in my mouth, so I played along. My freedom hung in the balance, and if this is what it took to get OUT of my cage, then I would do whatever it took to make Jo unlock my cage.

I figured I would be able to take it off with nail polish remover in the future, so I did not see the gain (for me) to fight this.

We drove across town, moving further away from the house and ended up at an Adult Book Store / Sex Toy Shop. I KNEW I was not going to be allowed to wait in the car here. Anything Jo could do to further humiliate me today seemed to be ALL we were doing.

“I have been looking forward to this stop all day.” Jo said.

We walked in, Jo to my front, and me lagging a little behind.

When we walked in, EVERY man’s head turned and looked at Jo. I don’t mean they looked, they “eye fucked” her really hard. The cashier saw the key around Jo’s neck. She smiled really big at Jo. She managed a look aimed at me.

Jo walked around and browsed a few items. She handed me a butt plug. “Hold this.” she ordered. Then she saw a pink chastity device, similar to the one I had on right now. “I want one of these in black. I really want to color coordinate your costume.” Jo said.

As she finished speaking, the clerk walked up. “Those are on sale.” the clerk told Jo.

Alexia smiled when she spoke to Jo, but she looked directly at me when she said it. “Buy this one, its 20% off.”

Alexia handed the cage to Jo, then whispered in her ear and pointed to the back wall.

Jo smiled and said, “Thank you, we are working our way back there.”

“Let me know if you need any more help.” Alexia said. Then she turned and looked at me and smiled as if Jo had told her everything that happened last night.

Jo browsed a few other items. She had me hold the butt plug, the cage, a bottle of lube, and two realistic dildos with a suction cup on their bases. One was a little bigger than the other.

Jo looked at me, struggling to carry everything. “Don’t chip your nails dear. We have one more stop after this one.”

I walked up front to get a basket. Alexia smiled at me. “Pretty nails you have there Sweetie Pie.”

“Thank you.” I said with some pride.

I turned to walk back to where Jo was and I saw that she was talking to a guy. I decided to let that conversation happen, so I looked at videos for sale.

A few minutes later, Jo came walking up to me with a large brown box that simply said “KIT” on the end of it.

“Lets check out. We have to put this stuff in the car and go next door for a little while.” Jo suggested.

We checked out. Jo made me pay with my credit card.

After we put our stuff in the car, we walked into a different entrance for the book store. Alexia was there talking to the clerk in the book store. She smiled at me the same way she did in the toy shop. She winked at me.

The book store clerk’s name was Brenda. She told us if we had any questions that we should ask rather than browse.

I braced for the worst, as Jo was in rare form today, humiliating me at every stop. It did not take much of an effort, due in part our surrounding, and now, the staff and clerks had joined “Team Jo”.

“Do you have a Glory Hole booth?” Jo asked directly and to the point.

Alexia smiled. “Yes, its in the back. You want to see Sally, she will get you all set up.”

Jo looked at Alexia and laughed, “Oh its not for me.”

A “BOOM” went off in my head. Alexia did all she could NOT to laugh.

“But I would like to go in with him, if that is not a problem.” Jo finished.

“Come with me, we will get you all set up.” Alexia said.

We followed Alexia back to the back of the store. We were led upstairs, and then into an office where Sally made us sign a few documents, scanned our IDs and then sat us down in the waiting room.

A few minutes later, Sally came back and got us. It was very dark. Sally said very little. Jo knew more than I did. I was lost.

As we walked up to a door, Sally looked at Jo and nodded. Sally then looked at me and said, “GO GET SOME Sweet Cheeks.”

We stepped into a dark room about the size of a prison cell. We were locked inside. There were multiple holes in the walls. A black light turned on overhead. It blinked twice, and then a semi erect cock was pushed through one of the holes in the wall.

Jo turned and looked at me, “Here you go Sweet Cheeks. The real deal.”

Jo stood over me, by the cock in the wall. She looked at me with “that look”. The look that ALL predators possess. The look that says, “Enjoy being owned.”

I moved over to area on the floor, closer to the stranger’s cock. I got on my knees and touched it with my fingers. I looked up at Jo. She was smiling with her whole face and her eyes were fixed on my movements. She seemed two feet taller than me at this point. I turned my head back and opened my mouth. I closed my eyes. The head of the cock touched my tongue, and that “switch” went off in side of me.

I pulled the cock in closer, tightened my lips around it and started moving my head up and down.

I slid my mouth over this cock for a few minutes. I made slurping sounds as I moved my head back and forth. I took short breaks and pumped the shaft with my fist.

Jo would put her hand on the back of my head and push my face back into position when I was taking too long.

Again, the sensation of the flesh in my mouth getting harder, longer, and throbbing as I used my mouth to make it more aroused did something to me inside.

I feverishly pumped this cock hard and fast.

I never heard Jo say a word.

I felt the cock inside of my mouth begin to throb. I heard some moaning from beyond the wall.

I sensed things were almost over. I went as fast as I could, bracing for the moment of truth.

On the downward stroke, with the head of this cock in the back of my throat, my mystery lover exploded in my mouth. A stream of heavy thick semen painted the back of my mouth, and I swallowed it hard.

Another spurt shot out and I swirled my tongue under the head as I felt the man on the other end of this cock twitch and spasm. I heard a faint grunt as the third shot rolled out onto my tongue.

I used my thumb and index finger to squeeze and roll any other drops out of the shaft. I loosely moved my mouth up and down the shaft a few times. Then I pulled it completely out of my mouth and held it in my hand. I swallowed some residue that was in my mouth. Then I kissed the head of this cock before he pulled away.

“That was delightful my Dear.” Jo said.

I looked up at Jo who had her phone out and her mouth was wide open. She stood directly under the bulb and I could see her nipples poking through the fabric on her dress.

She stopped the phone video and looked at me with pride. She opened her mouth to say something, but another cock appeared in the hole next to me.

Without any prompting, I moved over to the next hole and took it in my mouth. I did everything just like before. In just a few minutes, that cock exploded on my tongue, and I had to taste every ounce of the semen that shot into my mouth. I heard several grunts which matched the pulsations from this cock, and the load of semen that filled my mouth.

Again, I drained the cock for all it offered to me. Again I managed to swallow all of it and not drip any on my yellow shirt.

Again, I kissed the tip as it was pulled away.

As I finished, I looked up at Jo who was holding her phone in one hand, and rubbing her clit with the other hand. As I moved over to help her, she dropped her phone, threw her head back and let out a heavy whimper as a small orgasm shot through her body. Seconds later, the overhead light flickered and then turned off.

I was still on my knees, and Jo had just gotten her dress pulled down over her ass cheeks as Sally opened the door.

Sally walked in and pushed a button. A dim normal light came on. “This is to help your eyes adjust before we walk out. I have to remind you that if you want to come back into the book store, you have wait outside. Otherwise, I will lead you out, and you can go to your car. The men that participated have to wait in a dark room for 20 minutes and then they are led out. This keeps things safe for everyone.” Sally said.

I stood up and wiped the corners of my mouth. The taste painted my mouth. When we were ready, we were led back downstairs and into the parking lot.

My cock was straining against my cage and I was light headed. wished to go home so I could beat off and then pass out. I was very tired and just wanted this day to be over.

We got in the car. Jo drove home without speeding too much. Every time I used my hands I saw the nail polish on my nails. In the future, I would be reminded of THIS day.

Over the years she had many lovers. After Robert, Jo found that some of their mutual friends were worthy of her body. Robert never remarried. Why would he? He could call Jo and have some of the hottest sex with her with a few days notice. Jo traveled with Robert from time to time. He used Jo to help him get a promotion. Robert had a difficult client and he was going through a divorce. Robert arranged that he and Jo meet at a function. Jo found him interesting, and before the night was over, he took Jo upstairs to his room and fucked her.

Shortly after Robert landed that deal, and got a promotion. That promotion moved Robert closer to us. Shortly after that, Jo lost interest in Robert.

“Welcome to the club Robert.”

Jo met a few men on line, was nearly kidnapped one night, and was offered a few roles in some low budget porn films by one of those contacts. She turned them down. She did have fun fucking the producer and the director for those films, but she had no desire to be in front of the camera.

There were a few duds in her online experiences, but that was expected.

Jo sucked off one of our next door neighbors and he has wanted to get in Jo’s pants ever since.

I had borrowed a ladder from Bill and Jo backed over it with her car. When he came over to get the ladder, Jo met him in the garage with a silk robe on, and NOTHING on underneath. It was one of those short robes that really hid nothing, especially if it was a size too small (like Jo had) and worn by a woman over 5’6″ tall, which Jo was.

Jo apologized for the ladder and when she took her fingertips and traced the outline of robe where her cleavage met the material and asked, “Is there anything I can do to help you move past this unfortunate event Bill?”

He started to stammer a bit, and Jo knew she had him.

She closed the garage door and before the door shut all the way, Jo dropped her robe and turned a 360 degree circle, giving Bill a full body view of her, front and back. Before Bill could say or do anything, Jo dropped down in front of Bill, unbuttoned his cargo shorts and pulled his cock into her mouth.

Bill was already hard and completely speechless.

Jo took his cock inside of her mouth and within a few minutes he started to breathe heavy. Jo worked his cock a little faster, and pumped him with a few fingers and swirled her tongue under the head. She looked up at Bill and Bill looked down at Jo. She (and I) agree that this gave him the best memory he will ever have of her face.

Seconds later, the garage door opener light shut off and Bill shot a load of cum into Jo’s mouth. Jo pumped him empty, and let a little bit slip out of her lips and drip on her breasts. Bill never got completely hard before he came in Jo’s mouth, a true testament to how HE felt about my wife, and what SHE could do to a man with just her appearance.