This story is a work of fiction; I own this story. You are welcome to use it for your own enjoyment or send it to your friends. Please do not share it with another website or claim you are the author. Please make a donation to nifty, so they will continue to publish our stories. Please be sociable and write me at: alternativereality783@gmail.com This story is dedicated to all my alternative friends who love to dress up.
The Thanksgiving Holiday was over and everyone was getting ready for fun at The Purple Palace. Jackie Hollingsworth was excited to be partying at The Purple Palace. Jackie was the only son born to a single mother. Although she did not try to make a girl out of him, she really did not understand how to be masculine. His birthname is Jack, but everyone calls him Jackie. His sexual orientation is difficult to understand. He has a dress fetish and will only have sex with someone who is attired in female clothing.
The Purple Palace is a club for those with an alternative preference. They have many stage performers with different sexual preferences. One of their performers is a transgender who was born a male, but has artificial breasts. He is not gay; he will only sleep with a female. One of the performers is straight, but a female impersonator. Some of the other performers are crossdressing gays. The patrons are unique also; some are lesbians, some are masculine gays and some are feminine gays. Then of course there are male and female bisexuals and then there is Jackie Hollingsworth.
Most patrons know how Jackie Hollingsworth swings: Nothing turns him on more than if someone wearing a dress, sits down on his lap. The other night when Jackie was at The Purple Palace, some beauty walked in wearing a minidress and high heels. He asked this gorgeous creature to dance. After they danced to a couple of songs he invited "her" to his table for a drink. After they had drank a couple of drinks, they danced some more. They returned to their table, Jackie patted his knee and this beautiful creature sat down. The Purple Palace is a unique place: There are rooms upstairs that are available for rent. The girl who said her name was Sally sat down on Jackie's knee. As Jackie ran his hand up Sally's knee, he discovered a pleasant surprise. She either had a large clit or a small penis. Jackie later found out that Sally was a nickname, and this creature was really Sal. That did not bother Jackie; the dick was an added bonus to the dress. Oh, how Jackie loved the feel of a dress and naked legs against his body.
After a few more drinks , Jackie and Sally headed to the second floor. Although there was a set of steps to the second floor, most people took the elevator. This was for safety reasons: Having consumed a fair amount of alcohol, they may have been a little bit tipsy. While in the elevator, Jackie kissed Sally with lots of tongue. As was his custom, the first time he entered a hotel room with someone that was dressed in a feminine manner, he would carry him or her across the threshold. For the next few minutes they talked, what time they were not kissing. After really warming up to each other, Jackie began to undress. He then began to undress Sal: he took Sal's dress off and then his bra. That was enough for the moment; he laid Sal across the bed and began to kiss and lick his nipples. Then, he began to run his tongue down Sal's body, eventually removing his panties. He then began sucking Sal's dick, giving him the best blowjob he had ever experienced. After cumming in Jackie's mouth, the two licked each other's tongues so they could share Sal's love juices. Sal began to suck Jackie's dick, while Jackie began to prepare Sal's ass. After Jackie's dick was erect and Sal's ass was lubed, Jackie lubed his dick before inserting it in Sal's ass. Oh, Sal really loved all eight inches and Jackie really loved Sal's ass. After several minutes of fucking, Jackie came in Sal's ass. Oh, Sal exclaimed, you just fucked up your eating. Not really, Jackie replied: I am going to eat my fucking. Jackie proceeded to rim Sal's asshole, driving him over the edge of emotions.
Meanwhile, downstairs at The Purple Palace things were heating up. There was a well built, masculine lesbian in her mid-twenties named Casey who introduced herself to a bisexual, heavier female in her early fifties. As she sat down, the two exchanged their stories. Casey said she liked older women, while Virginia said although she was bisexual, the last twenty years she was with an older lady who identified as a male. Virginia ordered a couple of beers and they began to dance. While out on the dance floor, Virginia pulled Casey close to her and began to kiss her. Casey pulled away and this surprised Virginia. Was Casey a little bashful? She asked Casey if she would like another drink and Casey nodded yes. Virginia asked Casey if she came there very often. Casey replied, no this is my first time. Virginia asked Casey if she was looking for something in particular. She said she had never been to an alternative club; this was her first time. Perhaps this was her first time for other things as well. Virginia then asked Casey if she would like to go somewhere more private. Casey nodded yes; Virginia asked Casey if she would like to go to her house and Casey said yes. Casey said I will follow you in my car.
Virginia unlocked the door to her house and let Casey go in first. Casey admitted that she was still a virgin; she had been raised very strict and had recently moved out on her own. The only dating she had done was a couple of Christmas dances and her Senior Prom. She had never been touched by a boy and did not relish the thought of having a penis in her vagina. Are you nervous around me, Virginia asked Casey. Ido not know what to expect, declared Casey. I will not hurt you, promised Virginia. I can teach you how to make love to a woman. Are you interested, asked Virginia. We will take it slow, said Virginia as she put her arms around Casey. Casey loved Virginia's breasts squeezed against her own breasts. Virginia then placed her hand on Casey's left breast and lightly squeezed it. That feels good, Casey said. Why don't you remove your shirt and bra so I can make you feel better, Virginia said. Virginia looked at Casey's naked breasts and said, your titties are beautiful. Virginia said, I want to nibble on them and suck; Are you okay with that? Casey shyly nodded her head . Virginia sucked on her breasts for a couple of minutes and then suggested that Casey remove the rest of her clothes and get comfortable. When Casey did, Virginia went back to sucking Casey's breasts and began rubbing Casey's clit. Casey went wild with excitement. She experienced her first female to female orgasm. Did that feel good Virginia asked Casey. Casey said, that was wonderful. It sure felt good to Virginia. Virginia then undressed and said to Casey: Stick your finger in my pussy; when she did, Virginia told her to stick two in and move them back and forth. Casey did and soon she had sticky fingers. Oh, Virginia loved her young student. Casey, I think we had better rest now. I do not want to wear you out.
Back at The Purple Palace, there was another unique situation. Do people just show up there for hookup and sex? There was a transgender named Adrian or was it Adrienne? Either way that person was there. Incidentally, that person would go either way and sometimes both ways at the same time. He walked into The Purple Palace and saw a couple sitting at a table.There was a man who happened to be gay called Erin and a lesbian named Denny; yes, that is their correct spellings. He introduced himself and asked if he could sit down. After sitting down he mentioned that he occasionally came there, had seen them before, but did not know who they were. Incidentally, Adrienne was wearing a dress. When was dressed as a girl, he introduced himself as Adrienne and when he dressed more masculine, he was Adrian. He ordered a round of drinks and the three of them began to talk. Denny admitted she was a lesbian, Erin admitted he was gay, so Adrienne followed suit and told the couple he/she was a transgender. I was born a male, but I love breasts. I was always envious of large breasted women; These are real said Adrienne, as he was looking at Denny. Would you like to touch them, he asked Denny. Denny did not say anything, but rather she reached over and cupped his right breast. Oh, that felt good, cooed Adrienne. He then looked at Erin and said, Don't feel left out. Here reach under the table and feel my dick. Erin did so and was thrilled. Adrienne decided it was time to order another round. After a few more more drinks they all liked what they saw and decided to act on it. The three of them staggered up the stairs.
Casey left Virginia's house around midnight; she had to go to work in a few hours and did not bring any extra clothing: what a silly, naive little girl. She made arrangement to see Virginia around 9:00 at her house. This time she brought an extra set of clothes, but left them out in her car. Virginia knew she was dealing with an innocent girl and she would need to move cautiously. That meant that she might not have an orgasm every night, but she was teaching Casey about true love. One aspect of true love is putting other's needs first. Virginia had prepared a meal for Casey and it was ready by the time they got there. After they had eaten and Virginia had done the dishes, they settled in to talk and do girl stuff. Virginia removed her top and bra and asked Casey to suck her breasts. Amazingly, she did a pretty good job, sucking her titties and licking her nipples. Virginia then removed Casey's clothes and began to kiss her with an incredible amount of tongue. Oh, Casey's pussy was getting wet. Virginia told Casey she was going to teach her the art of cunnilungis. This is an essential part of being a lesbian, declared Virginia. Casey had an orgasm and then Virginia finger fucked Casey to another orgasm By this time it was getting late, so Virginia asked Casey to spend the night. Virginia told Casey she would like to take a shower with her. While they were in the shower, Virginia asked Casey to finger fuck her like she did the night before. Casey did and then she showed Casey how to get her asshole extra clean. Virginia explained that this was known as the double finger fuck method. Virginia put a good amount of body gel on two fingers and inserted in Casey's ass; with her other hand, she massaged Casey's breasts. Virginia kept running her fingers in an out of Casey's ass until the girl's pussy was sopping wet. She then removed her fingers, cleaned them off and rubbed Casey's pussy until she had another orgasm.
After Jackie and Sally's first encounter, they decide to try dating. Sally understands that Jackie has a strong fetish for female clothing. For Sally, this is not a real issue since he(Sal) likes to wear them. He has also accepted the fact that Jackie will not sleep with him unless he has at least a girly nightgown on when lounging around the house. On their second date, Sally wore a red sweater with a green skirt. Oh, how Jackie loved the way Sally looked. Those feminine legs; it made Jackie's dick erect just looking at them. Jackie took Sally to a regular club where they had a really nice dinner. Jackie asked Sally if she would like to spend the night at his place. Of course she agreed; she could not wait to feel the thrill of his dick in her. They had no more than got inside the door and Jackie removed Sally's sweater and bra. The two began to french kiss and Jackie eased Sally down to the couch. He then removed his clothes and placed his ass next to Sally's face and began to suck her dick and Sally began to rim Jackie's asshole. After Sally climaxed and shot cum all over Jackie's face, he held his face close to Sally's and the cute dog licked all the cum off. Jackie then rimmed Sally's ass before fucking her till she screamed with ecstasy. Later that night, Sally wore a sexy negligee to bed. More on this lovely couple in a day or two.
When Adrienne, Denny, and Erin finally made it to their room, they had to rest. They were all dizzy from from the trip up the stairs. They all wanted to have sex, but were not sure how to accomplish it. Adrienne initiated it by taking turns kissing Denny and Erin. Neither one refused her advances. Then, she slowly started undressing. Oh, what marvelous breasts, Denny thought. I can't wait to suck your dick, exclaimed Erin. So there it was; the three of them making plans to enjoy their favorite methods of sex. Luckily for Adrienne, anything was acceptable. They started out on the bed with Denny sucking Adrienne's breasts and Erin kissing Adrienne's neck. Then they changed positions and Adrienne was sucking Denny's pussy while Erin was rimming Adrienne's ass. This continued for a few minutes until Erin stuck his finger in Adrienne's ass. This excited Adrienne and he began to nibble on Denny's clit for a few seconds. He then resumed sucking her pussy while Erin continued to finger his ass. After a few minutes, Denny had an orgasm and Adrienne traded places with Erin. Adrienne then began to suck Erin's dick and he asked Denny to finger Erin's asshole. He continued to suck Erin's dick until he was ready to cum. He then removed his mouth and finished Erin off in his hand. He then rubbed the cum on his dick that was still hard. He told Denny to lube Erin up and gave him the assfucking of a lifetime. If Denny stuck her finger in Erin's ass, does that make her bisexual?
Casey and Virginia had been having some wonderful time; they were taking their sexual activities fairly slow. Virginia realized Casey was new to this environment and decided to take her time with them. But now it was time forcasey to experience the dildoes. After considerable foreplay, Virginia strapped on a medium sized dildo and fucked Casey's pussy with it. She also used a butt plug on Casey, so she would be accustomed to being assfucked. Finally Casey's time had come: Virginia fondled and kissed Casey and lubed her ass. She used a dildo that was larger than the butt plug but smaller than the dildo she was accustomed to. Virginia slowly inserted the dildo and very slowly picked up the rhythm. Casey was squealing and screaming, but she loved it. She was a full fledged lesbian: she even strpped on a dildo and fucked Virginia ass: Virginia was breathing very heavy by the time her pussy was creaming. Oh: Casey had learned very well.
The Purple Palace was having a New Year's Eve Celebration called Gathering of Friends. It was by invitation only; It was slated to be a vaudeville type show where the performers had sex with each other. Obviously, the viewers had to be extreme vetted. The performers scheduled for that evening were Adrienne, Casey, Denny, Erin, Jackie, Sally and Virginia. The script called for sexual contact among those who were not partners. Some gays were going to have female sex and some lesbians were going to have male sex. Oh, what an exciting evening was in store.
It was finally New Year's Eve at The Purple Palace. Annie, one of the regular stage performers who is transgendered, was serving as the Master of Ceremonies. He welcomed everyone to the show and the sound technician hit a button and the song Dancing Queen began playing. All of the performers for the night came out and began dancing. After that song was ended, the next song the crowd heard was Passionate kisses by Mary Chapin Carpenter. After that song ended, Sally, which was in a dress, came over and started giving Denny passionate kisses. Next, they played Mouth by Merril Bainbridge. When the part of the song came to turn me upside down, Sally turned Denny upside down and began rimming her ass and finger fucking her pussy at the same time. After Denny had stadium exploding orgasm, Adrienne came over and gave Sally a blow job. After Sally shot cum all over Adrienne's face, he went over to Denny and motioned her to lick it all off. He then rimmed Denny's ass, and then stuck his big dick in her pussy. Did she ever squeal and scream: she had never been penetrated with a penis. Adrienne kept fucking her and the music kept playing. The song that was playing then was:We Are the Earth. Oh, how the crowd loved this performance. Adrienne kept thrusting and Denny kept squealing. When Adrienne finally shot his load in Denny's pussy, Virginia came up and started tonguing Denny's pussy and licking the all the cum out of her cunt. Then, Jackie came up and began kissing Virginia. He then proceeded to perform cunnilungus on Virginia, rimmed her ass, and then fucked her ass to her heart's content. After he creamed her ass, Erin came up and licked the cum out of her ass and licked Jackie's dick clean. He then sucked Virginia's pussy until she had an orgasm. But what about Casey; who will she be with? Casey walked over and began nibbling on Erin's ear. She then began licking Erin's nipples and slowly started moving down. They got in the 69 position: Casey was sucking Erin's dick and Erin was sucking Casey's pussy. Then they began fingering each other's assholes until they both had stage shaking orgasms. Then the curtains were closed.