The Stiletto Pt. 04: Junior is Shy

Gabrielle and I were having Jack and Tina over for dinner. It was formal enough that we used the dining room. Aricely and my wife prepared everything (it was a lot of work for Aricely to do on her own, so Gabrielle had offered to help). Aricely sat down to eat with us, of course.

"So how are the twins?" I asked at one point.

"They're doing very well at school. Beatrice moved out of the dorm to live with her boyfriend, and Junior couldn't stand the dorm food, so he got himself an apartment."

"That must be expensive," I observed.

"Yes, everything is expensive in LA."

Tina seemed worried about something. "I'm actually a little worried about Junior," she finally spoke up.

"Why's that?" I asked

"He just seems very shy; he still doesn't have a girlfriend, and this is his fourth semester at college."

"Is he still a virgin?" asked Gabrielle.

"I'm not sure; he might be."

"Does he say anything?" I asked.

"Not really."

"Maybe he should find a girl here, instead of in LA," offered Jack. "Maybe the girls in LA are too fast for him, or too slow. I don't know." Jack threw up his arms.

"Why don't you bring him to the Stiletto next time he's in town? There's tons of nice girls there. Maybe he'll click with one." Gabrielle tried to help. "Or a few!"

"I don't know whether he'd be into trans girls," said Tina. She fully accepted her husband's love of trans women, but wasn't sure that all men shared the same tastes.

"Everybody's into trans girls, sweetie, some just don't know it yet."

"You've never been to the Stiletto, have you?" it suddenly hit me.

"No, can't say I have," Tina answered slowly.

"Tell you what. Why don't the four of us go this Friday? We can have some drinks, watch the show, and you can meet some of the girls. Make it a fun evening."

"What do you think, honey?" Tina asked her husband.

"I think Jim and Gabrielle are right."

Tina gave in. "Okay, I guess we can go."

"Perfect!" I exclaimed.

"It's a date then!" exclaimed my wife, clapping her hands together.

Gabrielle thought for a moment: "Oh, but we will need to do something about your look."

"What do you mean?" asked Tina, not sure if she should feel offended.

"This suburban-professional-woman-look of yours. It won't cut it at the Stiletto."

Gabrielle added: "The Stiletto is sexy, it's hot, it's avante-garde. You need to exude sexuality, just ooze sexuality. In other words, you need to look slutty. You will stand out like a sore thumb dressed like you normally do."

Jack laughed. "My wife doesn't own any slutty clothes."

Tina glared at her husband. "That's not funny!"

"Not to worry, sweetie. I have tons of slutty clothes. You can wear something of mine."

"Just not too slutty, I hope."

"You can pick something with just the right amount of slutty, dear." Gabrielle laughed.

"We might have a problem with shoes though; what size do you wear?"

She did not wear the right size.

"No problem. We'll go shopping."

"Wait," interrupted Ari. "That's my shoe size, I could lend you some of mine."

"Slutty enough?" asked Gabrielle.

"I think so," laughed Aricely.

"You know who would be perfect for Junior?" Gabrielle suddenly exclaimed.

"Who?" I asked.

"Amber."

"Ah yes, I think you may be right."

To Tina: "She is the sweetest thing. Cute as buttons. Very smart. Very outgoing. Very confident. You will love her!"

"How old is she, again?" I asked.

"Twenty-one or twenty-two, I'm almost sure."

"She goes to City University. Nursing, if I remember correctly. Right up your alley, eh, Tina!"

Tina looked intrigued. Somebody who was studying nursing couldn't be all bad.

"You can meet her on Friday!"

"How do you know she'll be there?" I asked.

"'Cause I'm gonna call her and tell her we'd like her to meet some friends of ours. I'm sure she won't say no. She is so nice, really."

"Silly question," I had to admit.

On Friday evening Jack and Tina arrived at our home at about seven. Gabrielle and Tina spent two hours in our bedroom getting ready.

"What on earth is taking them so long?" asked Jack, as if having to wait for his wife to get ready was a novel thing. Perhaps he was nervous.

"They're women, that's what women do. You know that. Besides, we've got plenty of time, it's still early." I tried to put him at ease.

When Gabrielle and Tina finally emerged, they both looked ravishing.

Gabrielle wore a black mesh, see-through halter top minidress with sparkly silver rhinestones here and there, the dress cut low at the back to show off her thong. Her jeweled nipples poked proudly through the see-thru fabric. Sparkly six-inch strappy sandals, long sparkly tassel earrings, and silver pocketbook completed her outfit.

Tina's outfit was barely less revealing: a red bodycon minidress with multiple cutouts, including an underboob cutout that showed off her breasts to just below her nipples. She wore matching tall red pointy pumps. Her earrings were almost identical to Gabrielle's. I wondered how my wife had convinced her to wear this dress.

"My nipples are poking through," pouted Tina. "And you can see all the bottom of my boobs."

"That's the whole idea, sweetie. You're not going to church. You're going to a nightclub. And you do look delicious, if I may say so!"

Tina smiled sheepishly.

The four of us chatted for a while, and left for the Stiletto shortly before ten.

As we were approaching our destination, I asked Jack: "By the way, when was the last time you came here?"

"Four or five weeks ago, I guess, maybe longer."

"You're in for a surprise, then."

"Why, what happened?"

"We've made some major improvements to the joint."

"I think I heard something, yes."

"I think you'll be impressed."

We parked in the Stiletto's parking lot, and walked toward the entrance.

"Boy, this looks different!" exclaimed Jack the moment he walked through the door.

After years of pleading with Jason, he had finally agreed to let me invest in his nightclub. He had done wonders with the place after he took it over from his father. Jason had turned the Stiletto from a virtually unknown and sleazy hooker bar into THE transsexual-friendly venue in the city. But there was room for improvement, and that would take money. We made lots of improvements. We changed the furnishings, lighting, and décor, but the largest one was purchasing the lot adjacent to the club, on the side opposite the parking lot, and built on it an extension to the nightclub's main room, duplicating its usable floor space. We furnished the new area with sofas and chairs, upholstered in the same plush velvet fabric that we used elsewhere. We arranged these into small circles to create intimate spaces for couples and small groups. We called these booths. We also added in this private area two small dancing stages with a dancing pole in the middle. Surrounding the stages we placed chairs and loveseats in the same style. Here the girls could give private dances, or shows, or whatever. Everything was done in purple and hot pink, including the carpet. We thought it looked very upscale.

"Are we doing strip bars now too?" one of my top people had asked me half-jokingly at the start of the project.

Jason greeted us warmly as we walked in, and led us to our table. I had called him earlier to ask him to reserve us a good table; close, but not too close to the main stage. I didn't want Tina to feel too exposed. With the stage straight ahead, but still about twenty feet away, we would have a great view of the show, but still not be too near to it. Jack introduced Jason to his wife. He had arranged the four chairs like a half circle facing the stage.

My wife asked Jason whether he had seen Amber.

He looked around, looking for her. "She's around here somewhere; maybe in the little girls' room. I saw her come in just a few minutes ago."

"Ah, there she is." Jason exclaimed. Amber had just come out of the ladies' room and was looking around, as if searching for somebody.

"She hasn't seen us, love, go get her." Gabrielle instructed me.

And to Jason, "can you bring us a chair for her, sweetheart?"

I went up to Amber and she greeted me with a kiss on the lips. Holding hands, we walked back to our table. Amber was indeed the cutest thing. If Tina did not fall in love with her instantly, I would be shocked. About 5'5, thin, with C-cup breasts, perhaps a little large for her body, straight black hair that reached almost to her waist, and big brown Bambi eyes framed by the longest natural eyelashes, she could have been a professional model. She smiled at Tina and Jack when I introduced her, a smile that would melt any person's heart. Her outfit was very sexy: a very short low cut strappy light blue minidress with matching blue pumps. The dress had a drawstring running down her left thigh, which allowed her to adjust the length of the dress as short or as long as she wanted, and she had chosen very short, to barely below her crotch. The drawstring was tied into a bow at the bottom. Her long nails were a matching blue enamel. Large, perky nipples poked through the stretchy light blue material.

She sat down between Tina and me, and as she did, her dress rode up and a bulging cock and balls were plainly visible under the silky black and white polka dot material of her thong. Crossing her legs did little to conceal her treasure.

Gabrielle got the conversation going, and told Amber that this was Tina's first time at the Stiletto, and that she worked as a nurse at University Hospital.

"That's awesome!" exclaimed Amber. "I'm majoring in nursing at City University, and this semester we're doing some practical training at the hospital. I would love to meet with you sometime there and maybe have a cup of coffee or lunch! I'm sure I could learn a lot from you!"

Amber couldn't be more authentically charming. She asked Jack and Tina interesting questions, and listened attentively to their answers.

Tina wanted to know more about her.

"How old are you, sweetheart?"

"Just turned twenty-one last month."

"Do you live with your parents?"

"Yes, I do. My dad is a Master Sergeant. Works at the base. My mom is a dental hygienist."

"Do you play any sports?"

"Tennis, and I love to go hiking; love the mountains around here. I love nature and animals."

"Our son, Jack Jr. plays tennis too, and loves hiking, and he loves animals too. I'm sure he would love to meet you."

"I'd love that, too!"

Her large breasts jiggled under her dress every time she laughed or spoke excitedly about something, the fabric frequently slipping to expose one or another of her dark perky nipples.

Totally comfortable with her body, this appeared to concern her not at all.

"We'll have to work something out, then," said Tina, the gears working full steam in her mind.

"Do you work as well, or just study?"

"I work to pay for college. I have a younger brother and sister, and my parents have a hard time making ends meet."

"Sorry to hear that."

"Thank you, but that's okay. I love my work."

"What do you do for work?"

"I escort."

"Is that a good way to make money?"

"You have no idea!" laughed Amber, her left nipple popping out of her dress. She didn't bother pulling on her dress to cover it.

Motioning to my wife, Tina observed: "Gabrielle escorts too, but I'm sure you know that already."

"Yes, of course. We are good friends."

I felt a hand on my shoulder, and turned my head to see Dr. Gerifakas, or Dr. G, as everybody called him. He and his young wife, a gorgeous twenty-five-year-old black girl named Keyishia, had just come in. They greeted us warmly; Jack introduced them to his wife. Dr. G and Keyishia had met Jack several times before. My wife and I knew them very well, of course. Not only were we good friends, but Dr. G was the artist responsible for Gabrielle's gorgeous tits, and Keyishia was Dr. G's office manager.

"Lovely to meet you, Tina; your first time here, I assume?"

"Yes, it is."

"How do you like it so far?"

"It's different, but I must say I do like it very much!" Any reservations Tina may have felt when she came in, had completely disappeared after her chat with Amber.

"I'm glad you feel that way! We all love the Stiletto. It's a great place to make friends! We're all here to help each other, in case you need anything."

"Thank you."

"I need to go get ready, honey," Keyishia interrupted her husband.

"Of course, my love."

"It was lovely to meet you!" Keyishia gave Tina a huge smile and sauntered off.

"Keyishia is dancing tonight," Dr. G explained.

"That's awesome," I said. "Always a major turn-on to watch Keyishia dance."

Dr. G agreed wholeheartedly. "She is a pistol, that one." Dr. G's wife could get really wild on stage, and it was always fun to watch her perform. I quietly hoped it would not upset Tina.

"Won't you join us for a glass of champagne?" I asked Dr. G.

"Thank you, but I need to go. Just came in to drop off my wife. I'll be back later to pick her up."

The music faded and Hector, the DJ announced over the PA that the show was about to begin. It was nearly midnight. By this time there were between two hundred and two hundred and fifty patrons in the club, some sitting at the tables, others standing around. There were twice as many girls as men, but that's the way it usually was at the Stiletto.

The patrons clapped and cheered the girls as they came on stage. Venus danced first, then Channel, and finally Keyishia. These girls knew how to put on a show, dancing sexily, and even performing some ambitious acrobatics, to the music. They would slowly remove their clothing as they danced, and end up only in thong and heels. As they danced, patrons, men, and women alike, would approach the stage and slip ones, and sometimes tens in the girls' thongs. The show at the Stiletto never disappointed. It was a very sexy and fun show.

I turned to look at Tina, and she appeared noticeably aroused, judging from her heaving chest and by the way she kept biting her lip. "Give her some money," I motioned to jack. Jack pulled out a bunch of tens and gave them to Tina.

Tina looked confused.

Jack explained: "Show Venus that you appreciate her art."

A little nervous, Tima got up, and walked to the edge of the stage. Venus squatted in front of Tina to allow her to insert a ten in the string of her thong. Then she gave Tina a thank you kiss.

After that first time, Tina started getting really into it. She showed her appreciation to Venus, Channel and Keyishia several times.

During her third song, Keyishia pulled on the side strings of her thong, and as it fell away, she kicked it toward the audience. A lucky patron caught it. As she gyrated her hips to the music, her freed cock danced around wildly, quickly hardening. Keyishia was horny.

A man in his fifties approached the stage and offered what looked like a hundred. Keyishia bent her knees just enough so her cock was level with his face, and allowed him to take it in his mouth.

This was too much for Tina. Panting hard, she hissed at Jack, "I need a hundred."

Keyishia grinned, and squatting low for Tina, allowed her to suck her cock for what seemed like almost a minute. Then she pulled away and gave Tina a thank you kiss. A young man was next in line to worship Keyishia's cock.

Tina was flustered and panting hard when she returned to our table.

Jack kissed her approvingly. We all congratulated her on her courage.

Tina was besides herself with excitement.

Done with her dance, Keyishia came to our table. I had asked Jason to send her over when she became available. I whispered in her ear: "Why don't you take Tina to one of the booths and give her a good time?"

"Of course, I'd love to."

Without saying a word, Keyishia took Tina's hand, and as if in a trance, Jack's wife walked back with her to the booths.

Jack had a confused look.

"I told Keyishia to take Tina to a booth and fuck her."

Jack smiled.

Jack looked at my wife and said: "I want to fuck you, come with me."

Not sure whether I had heard Jack over the sound of the music, my wife looked at me and said: "Jack says he wants to fuck me, honey."

"Excellent!" I exclaimed

"Wait, I need to pee. Why don't you come with me, sweetie?" Gabrielle and Amber excused themselves to go to the ladies' room. "We'll be right back, don't you two go anywhere."

Gabrielle came back alone. "Amber will be back in a sec. You and Amber come join us as soon as she gets back, okay? She's going to fuck you."

"Thank you, my love," I answered.

Jack took my wife's hand and led her away.

Amber returned shortly and held out her hand: "come with me, I'm going to fuck your ass." I took her hand and followed her to the booths. About half the booths had people in them, on one of the stages a girl was dancing before a group of five admiring young men, totally naked except for her heels, her penis dangling between her legs as she moved around the pole. A bachelor party, I assumed.

Although the area was dimly lit, we easily located the rest of our group. Gabrielle was on a sofa, her knees on the seat cushion, elbows resting on the back, as Jack pounded her ass from behind.

Smack up to them, Tina was riding Keyishia, the two women holding hands, fingers intertwined. I could see Keyishia's black cock pumping in and out Tina's pussy

There was barely enough space on the sofa for Amber and me.

Amber pushed me down on the sofa, stood in front of me, lifted her dress, pulled her thong to one side, and ordered me to suck her cock.

"Suck my balls too," she commanded. I took her smooth balls into my mouth, one at a time, and gently sucked on them.

"Take your clothes off, and raise your legs for me. I want your asshole."

I did as she ordered. Amber slipped off her panties and shed her dress, and from her handbag took out a small tube of lube. She coated her beautiful cock and applied some to my asshole, and then she slid into me. Amber leaned forward and we kissed passionately as she tenderly fucked my ass.

I ejaculated on my belly after a while. "Should I pull out," Amber asked?

"No, I'm fine. Please don't stop. Please fuck me."

Amber smiled sweetly and continued to fuck me.

"I'm going to cum." She slid out of my ass and stood up. "Get on your knees, I'm going to cum in your mouth."

I did as I was told; Amber's beautiful cock was shiny with lube and my ass juices.

Turning to my left for a moment, I noticed that Tina and my wife were also on their knees sucking cock.

Amber stroked her cock a few times, and moaned loudly as her cock exploded, spraying jet after jet of semen into my mouth and on my face.

"Swallow my load, sweetie."

She knelt before me, and cupping my face in both hands, noisily slurped up all her cum from my face. Then she kissed me, feeding me her cum. "You missed some," she smiled.

Then she stood up, her cock still hard: "clean my cock." I licked my ass juices, the lube and her cum off her cock, and then she gave me a long, tender kiss. "Did you enjoy my fucking you?"

"Oh yes, sweetie, I loved it!"

"I'm so glad you liked it, love." Amber smiled warmly. "I loved fucking you, too. I came so, so much! Did you notice?"

"Oh yes! That was a full meal, you fed me."

Amber laughed heartily, and kissed me again.

"Did you have fun, love?" my wife asked me as we walked toward my car.

"Oh, yes, I loved it!"

"Did you give Amber a tip?"

"Yes, I gave her two thousand dollars. She wouldn't accept it, said we're practically family, but I insisted. I told her I know she could do with the money. I also told her that, if she ever needs anything, no matter what it is, we're here for her."

"I'm sure she appreciated it."

My wife kissed me, and I tasted Jack's cum in her mouth.

"Did you have fun too?" I asked her.