SYNOPSIS: When Jack's neighbor discovers his feminine alter ego Jill, it's the worst day of his life. But sometimes bad beginnings have happy endings.

 

Jack And Jill

by Tammy Richards

 

Jack Williams rolled over and hit the snooze button on his alarm clock. It was 6 AM on Saturday morning. He lay in bed planning out his day. Saturday was Jack's favorite day of the week. From Monday through Friday he was the loan officer at a bank. Saturday was reserved for Jill, his feminine alter ego.

The basic routine for the day didn't vary much from week to week, just the details. Jack started every Saturday morning with a hot and soothing bubble bath. As he soaked in the tub, he would shave his entire body, removing the accumulated stubble from the preceding week. He loved the feeling of his lingerie sliding over his smooth skin. After drying himself he would use moisturizer and powder to soften and perfume his body. He would then pull on his white satin ruffle panties. The feel of the satin caressing his manhood always made him as hard as a rock.

Next he would attach his breastforms using medical adhesive. He had spent a lot of money on them and they were very natural. When the adhesive had set he would put on his corset and lace it tightly. The cups of the corset pushed his breasts up and out, giving him a very sexy bosom while the lacing reduced his waist to 28 inches. He would then sit on the bed and slowly work his shear black seamed stockings up his legs and attach them to the garters of his corset. He always stopped to admire himself in the full length mirror. From the neck down he looked very feminine, except for the bulge in his panties.

Jack was very proud of his makeup skills. He had an extensive collection of cosmetics and a professional mirrored vanity. He loved to experiment with different looks. For the morning, he always tried to achieve a natural, feminine appearance with his makeup. It frequently took him 30 minutes or more to get everything just right. When he was satisfied, he would place a wig on his head and attach it with adhesive tabs. He always wore his shoulder length blonde wig for the morning. Once he had brushed out the wig, he would attach a pair of long dangly earrings and check to make sure he now looked feminine from the neck up. Then he would attach a set of glue-on nails and paint them an appropriate color for the day.

He was now ready to get dressed for the morning. Jack spent Saturday mornings cleaning his apartment. That meant dressing in his black satin maid's uniform with a full white petticoat and 5-inch stiletto-heeled shoes. The uniform was trimmed in white lace with a white satin apron that he tied around his waist.

Jack usually started his morning with a light breakfast, perhaps a poached egg and a glass of juice. Then he went to work. As he worked he would fantasize that he was cleaning the apartment of his mistress. It usually took him most of the morning to complete his cleaning chores. When he was done he would change into his afternoon attire. He liked to wear a skirt and blouse or dress for the afternoon. He generally selected an outfit that was pretty and feminine, but not too sexy. He always put on his zippered panty girdle to hide his male bulge. The girdle had padding for his hips and ass, which gave him a beautiful hourglass figure. Depending on his mood he might also change to a different wig (he had four of them).

After he changed his clothes he would make himself a salad for lunch. He liked to spend the afternoon reading his women's magazines and surfing the Internet. He often fantasized about going to the mall dressed as Jill to shop for clothes and shoes. However he never left the apartment. Even though he thought he made a very passable woman, he couldn't take the chance that someone might recognize him.

Late in the afternoon, Jack would prepare a casserole and put it in the oven to bake while he got ready for the evening.

Jack really looked forward to his Saturday evenings when he would dress in his most beautiful and sexy clothes. He would start by cleaning off his day makeup and re-shaving his face. Then he would select his outfit for the evening, usually a cocktail dress or evening gown.

After getting dressed Jack would again sit at his vanity and do his makeup. He used more makeup for the evening to create a dramatic, sexy appearance. He would then put on a wig and his jewelry. A spray of perfume and he would be ready.

Jack always made an effort to create a romantic environment for the evening. He turned the lights down and put on some soft romantic music. He would then set the table for an intimate candlelit dinner. After dinner, Jack would put a disc in the DVD player, pour himself another glass of wine and sit down on the couch to watch a romantic chick flick. He liked to fantasize that he was sharing his evening with a beautiful woman who would love and accept both Jack and Jill.

By the end of the movie Jack was usually starting to become aroused. It was time to get ready for bed. He liked to stand in front of the mirror as he removed his clothes, admiring his shapely feminine body. He would then put on a nightgown or one of his sexy lingerie sets, along with stockings and high heels and return to the living room for a nightcap. As he sipped his drink he would slowly begin to stimulate himself. As the pressure in his groin increased, he would slip a condom over his throbbing cock to hold his juices. When he could stand it no longer, he would lie down on his bed and bring himself to a powerful and satisfying orgasm. As he did this he fantasized that he was being fucked by a woman wearing a matching outfit.

When the pressure in his love nest had subsided and his breathing returned to normal, he would clean himself up, remove his makeup and slip into a sleep filled with wonderful dreams.

For the past two years Jack had spent nearly every Saturday dressed as Jill. Little did he know, as he bounded out of bed, that this Saturday would be different from all the previous ones.

The day started like every other Saturday. After breakfast Jack went to work cleaning his apartment. A few minutes after 11, as Jack was using his feather duster to dust the lamps and pictures, he heard a loud disturbance in the hallway outside his door. He looked through the peephole and saw his neighbor Cindy running down the hall screaming for someone to help her. Cindy was one of the most attractive women he had ever met. Her long auburn hair framed her beautiful face. She had a spectacular figure with a generous bosom and a small waist. She often wore short skirts that showed off her long shapely legs. Whenever Jack saw her around the apartment building, she was always very pleasant and talkative, perhaps even a little flirtatious. Jack would have loved to ask her out on a date, except for one very large problem: her boyfriend Ed. Ed was 6'2" tall and built like a football player. Jack had no doubt that Ed could beat him to a pulp if he got mad.

Cindy headed straight for Jack's door. She screamed as loud as she could: "JACK, ARE YOU HOME? OPEN THE DOOR!" She reached the door, pounded on it and moaned: "Oh God! Please be home, Jack."

It was clear that Cindy was scared to death. Jack knew he had to do something. He pulled the door open wide enough for Cindy to enter and then slammed it closed and turned the deadbolt. As he closed the door, he saw Ed enter the hallway with anger etched on his face.

He turned toward Cindy and found her staring at him with her mouth hanging open. "Who the hell are you? Where's Jack?"

Jack could feel his face turning red. In his most feminine voice he said: "Jack's not here right now. My name is Jill."

Cindy was speechless as she continued to stare at him. The moment was broken by the sound of Ed pounding on the door. "Cindy, I know you're in there. Open the door. I need to talk to you."

"Get out of here, you bastard," Cindy screamed. "I don't want to talk to you. I'm calling the police right now so you better leave." As she said this, she picked up Jack's phone and hit 9-1-1.

"Please don't call the police. I just want to talk to you."

The 9-1-1 operator answered the phone. "Police. What's your emergency?"

Cindy spoke loudly into the phone. "Send a police car to the Dearborn Avenue apartments, Building 6, Apt 1A. My ex-boyfriend is outside the door and I think he might hurt me."

When Ed heard her, he pounded his fists against the door in frustration. "Damn it Cindy. I'm not going to hurt you. I just wanted to talk." When she didn't respond he slowly began trudging back down the hall.

Jack watched him go through the peephole and then turned to Cindy. "It looks like he's leaving."

Cindy relayed this information to the operator. As she talked to the operator Jack was conscious that she was still staring at him, taking in everything from his blonde wig to his satin maid's uniform to his stiletto-heeled shoes to the feather duster that he was still holding. Finally she hung up. "They're sending a police car. It should be here in about 10 or 15 minutes." For the first time since she entered the apartment, she smiled at Jack. "Do you have something else to wear? It might be tough explaining that outfit to the cops.

Jack knew that there was no way to transform himself before the police arrived. He would have to stay as Jill for a while longer. "I've got a dress in the bedroom that I could put on."

Cindy giggled. "You better get that cute little ass of yours moving then. I'll watch for the police."

Jack hustled into the bedroom. He quickly stepped out of his shoes and stripped off his uniform. He then removed his stockings, panties and corset and threw everything onto the floor of his closet. He raced to his dresser and pulled out a bra, panty girdle and a pair of nude pantyhose. After putting them on he went back to the closet where he pulled out a short-sleeved navy sweater dress. He pulled it over his head, being careful not to mess up his hair or makeup, and smoothed it down his body. The dress molded to every curve, ending about 4-inches above his knees. He then slipped on a pair of navy blue sandals with 3-inch heels. They were the lowest heeled shoes that he owned. He checked himself in the mirror to make sure there was no male bulge in the front of his dress. Satisfied he sat at the vanity and quickly brushed his hair and touched up his lipstick.

He was just finishing when he heard Cindy yell from the living room: "I see them coming. Hurry up."

Jack took a deep breath, fixed a smile on his face and walked back into the living room. Cindy turned when she heard him. Her eyes opened wide in amazement. "My God! You're really beautiful. I love your dress."

"Thank you. It's one of my favorites."

They heard a knock on the door. "Open up. This is the police."

Jack checked the peephole and then opened the door. "Come in officers," he said to the two cops standing in the hall. "I'm Jill Washington. This is my boyfriend's apartment." He motioned toward Cindy. "This is Cindy Carter. She's the one who called you."

One of the officers turned to Cindy while the other one continued to stare lustfully at Jill. "The caller ID system lists this apartment as belonging to Jack Williams. Is Mr. Williams here?"

"Jack left early this morning with a couple of his friends to go fishing. He won't be back until tomorrow night. I was just getting ready to meet some girls for lunch and shopping when Cindy showed up."

Cindy chimed in: "Thank God Jill was here to let me in."

The second officer spoke up: "It sounds like you are lucky she was here. Who was chasing you?"

"It's my ex-boyfriend Ed Rodgers. I broke up with him a couple of weeks ago. Since then he keeps calling me. He even showed up at my work last week. This morning when I was leaving to go to the mall, he drove up and got out of his car. When I told him to get lost because I didn't want to see him anymore, he got mad and started chasing me. I ran back into the building. Fortunately Jill heard me screaming for help and opened the door before Ed could catch me."

Jill spoke up. "Ed is built like a football player. He could have really hurt Cindy if he had caught her."

"Has he ever hit you?" asked one of the cops.

"He hit me a couple of weeks ago. That's what lead to our breakup."

"Do you want to prefer charges against him?"

"Not really. I just want him to leave me alone and quit bothering me."

One of the officers asked: "Did you ever give him a key to your apartment?"

"I did but I got it back when I broke up with him."

The second officer frowned. "Unfortunately he may have made a copy of the key. I'd strongly suggest that you get your locks changed. Do you have anyone you can stay with until they're changed?

Cindy looked at Jill who smiled and said: "You're welcome to stay here with me. Jack's gone for the weekend and we have a spare bedroom."

The officer nodded. "That should solve your problem. Now if you can give us Mr. Rodgers address, we'll go talk to him." Cindy gave the officers Ed's address and phone number, as well as a description of his car. "I'd recommend that you two ladies stay here with your door locked until we've had a chance to talk to him. We'll check back with you later."

"Thanks very much for your help," Cindy said as she shook their hands. Jill opened the door to let them out. She noticed that one of the officers was staring at her tits as he walked out the door.

Jack closed and locked the door, then turned to find Cindy standing right next to him. Before he could say a word, Cindy put her arms around his neck, pulled him down to meet her lips and gave him a passionate kiss. Her mouth opened and her tongue pushed deep into Jack's mouth. He felt his penis straining inside its elastic prison. She looked into his eyes. "Thank you so much for helping me. You were incredibly brave to open the door for me, given how you were dressed."

Jack blushed. "I couldn't very well leave you out in the hall to face that brute by yourself. I still find it hard to believe that he would hurt someone as nice as you."

"Ed turned out to be a real jerk. I actually thought I was in love with him." She shook her head. "I was really stupid."

Jack smiled at her. "Don't think about him anymore. Would you like a little lunch? I could make us a salad."

"That would be wonderful. Let me help you." They went into the kitchen where Jack made the salad while Cindy set the table and poured each of them a glass of iced tea. They chatted as they worked. Jack couldn't believe what was happening. The most beautiful woman he knew was treating him like one of her girlfriends.

They sat down to lunch. As they ate Jack looked across the table. "I don't want to be nosy but it always seemed like you and Ed were very happy together. Was I wrong or did things change?"

"When I first met Ed I thought he was a wonderful guy. He was kind and considerate, and treated me like a lady. Unfortunately another side of his personality began to emerge after we'd been dating for a couple of months. He started trying to control my entire life. I couldn't do anything without checking with him first. He also became very jealous of any other man who paid attention to me."

"Things came to a head a couple of weeks ago. I decided to go out for a drink after work with some of my friends from the office. I called Ed's apartment and left him a message. He showed up at the bar and told me we needed to leave immediately because he had made other plans. I told him I was busy and he would have to go without me. That made him mad. He grabbed my arm and pulled me out of my chair. I told him to take his hands off me because I wasn't going anywhere with him. Then he accused me of flirting with the guy who happened to be sitting next to me at the table. It was really dumb. The guy sitting next to me is gay. He lives with his boyfriend in one of the buildings here in the apartment complex. I told him to grow up and start acting like a man instead of an animal. That's when he hit me. It was the last straw. I told him we were through. I didn't want to ever see him again. I then told him to get his stuff out of my apartment and leave my key. Then I turned my back to him and sat down with my friends. He had no choice but to leave."

"I stayed at the bar and had dinner with three of my girlfriends. They came home with me after dinner. Ed was in my apartment waiting for me. He tried to apologize for his actions but I told him I didn't want to discuss it. I got a trash bag and put his stuff into it and then told him to leave immediately. Ever since that night he keeps trying to get me to forgive him, but I have no interest in dating him anymore."

Jack smiled at her. "Some men are real animals. I think you were lucky to find out what he was really like before you got too serious."

They ate in silence for a couple of minutes. Jack was conscious that Cindy was watching him as he ate his salad. Finally she said: "It's my turn to be nosy. How often do you dress up like this?"

Jack blushed. "Once a week, usually on Saturday. I spend the morning cleaning, dressed as you saw me earlier. I change to a dress or skirt and blouse for the afternoon and then put on something fancy like a cocktail dress or evening gown at night."

"Do you ever go out as Jill?"

"Heaven's no. I'd be scared that somebody would recognize me."

"You certainly don't have to worry about that. Anyone seeing you in public would never suspect you were anything other than a beautiful woman. I watched the two cops checking you out earlier. I'll bet they both were hot for you."

"It didn't take you long to figure out that I wasn't a woman."

Cindy laughed. "That had nothing to do with your appearance. It was your outfit. There are no real women who would do their cleaning in a satin maid's uniform and high heels."

Jack nodded. "I'm sure you're right about that."

When they had finished their lunch, Jack turned to Cindy. "I guess I better go and get out of these clothes."

Cindy stopped him. "Please don't. I think that dress looks very nice on you. Besides if the police come back, they'll expect to see Jill, not Jack."

"Are you sure you don't mind seeing me like this? I don't want to make you uncomfortable."

"I'm sure. It's nice to discover that I have a new girlfriend right across the hall." Cindy paused. "I hope you were serious about me staying here until I can get my locks changed. I'd be afraid to stay in my apartment by myself."

"You're more than welcome to stay here. I have plenty of room." Jack laughed. "I even promise to behave like a perfect lady."

Cindy giggled. "Perhaps we could have a pajama party later. Speaking of pajamas, I'm going to need to go over to my apartment and pack a few things for tonight."

"I'll go with you, in case Ed shows up again." Jack checked the peephole before opening the door. Then he waited until Cindy opened the door to her apartment before he hustled across the hall.

"Make yourself comfortable," said Cindy pointing to the couch. "It shouldn't take me too long." Cindy returned to the living room 15 minutes later carrying an overnight bag and a very sexy black dress on a hanger. She held up the dress for Jack's inspection. "What do you think?"

"It's beautiful. I'm sure you'd look great in it."

"You mentioned that you like dressing up in something fancy at night. I thought it would be fun to dress up with you. I hope you don't mind."

"I don't mind at all. I think it's a great idea."

Just then they heard a knock on the door. "Wait here," said Jack as he walked to the door and looked out the peephole. "There are two men out there. I don't recognize either of them."

There was another knock and one of the men called out: "Cindy, are you in there? It's Kevin and Darryl. We heard you had some trouble this morning."

Cindy turned to Jack. "Kevin is my friend from work that I told you about. He and Darryl live together. I need to talk to them."

Before Jack could react, Cindy had opened the door. Kevin and Darryl rushed in and hugged her. "Are you OK?" asked Kevin. "We just got home from playing golf and one of the neighbors told us that there was a police car here this morning.

"I'm fine, thanks to Jill," Cindy said. The two men turned to look at Jack, standing by the door in his dress and heels. "Kevin and Darryl, this is Jill Washington. She lives across the hall. Fortunately she was home this morning and let me into her apartment when Ed started chasing me."

Each man took one of Jill's hands to bring her closer and then brought her hands to their lips and kissed them. "It's very nice to meet you," said Kevin. Turning to Cindy he continued: "You have the cutest friends of anyone I know. So tell us what happened."

"I will, but let's go back over to Jill's apartment first. We just came over to pick up a few things so I could stay with Jill until my locks are changed. We're waiting to hear from the police that they've caught up with Ed and talked to him."

They went back to Jack's apartment and settled themselves in the living room. As Cindy recounted the events of the morning, Jack tried to figure out how to extricate himself from the situation. There were now five people who had seen him dressed at Jill. He didn't think that Kevin or Darryl suspected his true identity, but he wasn't sure.

When Cindy finished her story Darryl spoke. "You girls have had a very trying morning. I think Kevin and I need to do something special to help you put the ordeal behind you. We'd like to take you out for a real nice dinner tonight. How does that sound?"

Jack could feel his palms getting sweaty as he thought of the potential consequences. "I'm not sure we could do that. We're supposed to stay inside with the door locked until we hear from the police."

"That's OK. Give us your phone number and we'll call you later." Jack was backed into a corner. He had no choice but to give them the number.

They rose and Kevin said: "You girls relax this afternoon. We'll talk to you in a little while." They both kissed Cindy on the cheek and then turned and did the same to Jack.

They were barely out of the apartment before Cindy started giggling. She put her arms around Jack's waist and pulled him toward her. "Were you a little nervous, Jill?"

"I was more than a little nervous. I was scared to death. Cindy, there's no way we can go out to dinner with those guys. If we have to spend the whole evening with them, they're bound to figure out that I'm not really a Jill."

"Don't worry. Kevin and Darryl are great guys who are just trying to be nice. They have absolutely no romantic interest in us. They love each other. Besides if they were to figure out that you were a man, they would never give away your secret. I happen to know that Kevin also likes dressing up in women's clothes. He came to the Halloween party at the office last year wearing a black leather miniskirt and high-heeled boots."

"Well let's wait and see what we hear from the police. Now let me show you where you can put your stuff for tonight." Jack let Cindy into the guest bedroom. It was decorated in a very feminine style. There was a pink flowered bedspread on the bed with dainty ruffled throw pillows.

"What a beautiful room!" exclaimed Cindy. "Is this Jill's room?"

"It is. I keep my feminine wardrobe in here and I usually sleep here on Saturday nights. Don't worry though. This is your room for tonight, I'll sleep in my other bedroom." Jack pointed to the closet. "You can hang your dress on the left side. Jill's clothes are on the right."

After hanging up her dress, Cindy pointed to the other side of the closet. "May I see?"

"Sure, if you want to," said Jack, opening the closet door.

"Wow, you've got quite a collection," Cindy said as she stared at the array of skirts, blouses and dresses hanging neatly in front of her. She bent over and picked up Jack's maid uniform and handed it to him with a smile. "You better hang this up before it gets all wrinkled." As Jack hung up the uniform and put the rest of his morning clothes away, Cindy examined his clothes more carefully. She pulled out a long red strapless evening gown and held it up. "I'll bet you look really sexy in this dress. It's fancier than anything that I own."

"I'd be happy to model it for you sometime." They continued to chat like two girlfriends as they finished putting the rest of their things away.

They were just returning to the living room when they heard a knock on the door. Jack quickly walked to the door and checked the peephole. "It's the two policemen from this morning. I wonder if they've caught up with Ed." Jack opened the door.

"Good afternoon ladies," they said as they entered the apartment. One of the officers turned to Cindy. "Miss Carter, we wanted you to know that we caught up with your ex-boyfriend. He assured us that he wasn't going to hurt you. He just wanted to talk to you. We told him that you didn't want to have anything to do with him and that he needed to stay away from you or he would be arrested. I don't think you'll have any more problems with him."

The second officer chimed in: "He claims he doesn't have a key to your apartment. However to be safe, I'd still recommend changing your locks."

Cindy thanked the cops for their help and walked them to the door. She was standing in the doorway watching them leave when two of her girlfriends from the office walked into the hallway. They rushed up and hugged her. "We just heard about your problems with Ed this morning. Is everything OK?"

"It is now. The police just left. They've talked to Ed and he assured them that he wouldn't bother me any more. Come in and I'll fill you in on the details." The two women followed Cindy into Jack's apartment. "Jill, this is Jennifer and Marsha. They're two of my friends from work. They helped me the night that I broke up with Ed. This is my neighbor, Jill Washington. Jill was a lifesaver this morning when Ed was chasing me."

Cindy and her two friends sat down in the living room. Jack had no choice but to join them. "So tell us what happened," said Jennifer. As Cindy launched into her story of the day's events, Jack thought about what was happening to him. The list of people who had seen him dressed as Jill was growing rapidly. As far as he could tell, only Cindy knew his true identity. But he also knew that the more time he spent with other people, the more likely that someone would see through his disguise. For the short term however, he had no choice but to continue the charade.

As Cindy talked she and her friends drew Jack into their conversation. They made him feel like one of the girls. Soon he was talking and laughing with them like long-time friends. The ringing of the phone temporarily halted their conversation.

Jack answered and a voice on the other end said: "Hi Jill, this is Kevin. We saw the police car outside your building. What did they say?"

"They talked to Ed. Everything should be OK. He promised that he wouldn't bother Cindy any more."

"That's great. We've made dinner reservations for 7:30 at Antonio's. You girls get yourselves all dolled up and we'll pick you up at 7."

"Hang on Kevin, let me ask Cindy." Jack turned to Cindy and her friends and relayed Kevin's message.

"Wow, that sounds great," said Marsha. "Antonio's is the fanciest restaurant in the city. You two deserve it after the day you've had."

Jack looked helplessly at Cindy who smiled at him and said: "It's up to you Jill. I think it sounds wonderful. I need something to take my mind off that jerk Ed."

Jack knew that he had again been boxed into a corner. Turning back to the phone he said: "We'd love to go, Kevin. We'll see you at 7."

Jennifer and Marsha stood up. Jennifer said: "We better get going so you two have time to get ready for your evening. You'll have a lot of fun with Kevin and Darryl."

After they were gone, Jack stood in the living room looking very forlorn. Cindy put her arms around him and kissed him tenderly. "Cheer up Jill. We're going to have a wonderful evening and you're going to have the chance to enjoy it all as a beautiful woman." She gave him a smile and another kiss. "Come on, I'll help you pick out something pretty to wear tonight."

Jack followed Cindy into the bedroom and opened the closet door. He stood next to her as she pulled out various dresses and held them up in front of him to see how they would look. Suddenly she exclaimed: "This is the one," as she held up a black satin sheath dress. It was sleeveless with a high neckline and V-back. It had a wide satin belt and a straight skirt that ended just above Jack's knees. "We'll look great together in our little black dresses."

Jack took the dress from her and held it against his body. "This is one of my favorites. I'm just not sure about wearing it out in public. I'm really scared that someone will make me as a man."

"After spending all afternoon with Jill, I'm confident that you'll do just fine. Besides I'll be with you to help you." Cindy stretched. "It's been a long day. I'd really like to relax in a nice hot bath for a while before we get ready. Is that OK?

"Everything is in the guest bathroom for you to have a nice bubble bath. I'll take what I need into the other bathroom to get ready for tonight."

"You don't have to do that. I have no problem sharing Jill's room with you. It will be fun helping you get ready for your night out on the town."

Cindy headed for her bath while Jack removed his dress and shoes and slipped on his pink silk robe. Then he gathered his lingerie for the evening and went into the other bathroom to take a quick shower. After his shower he powdered his body and then shaved twice to remove all traces of his beard. Then he pulled on his tightest high waist zippered panty girdle and hooked up a black strapless merrywidow. The garments gave him a very feminine figure. After donning his robe he returned to the bedroom and put on a pair of sheer black stockings, which he hooked to the garters of his girdle.

He sat down at his vanity and began the process of making himself beautiful. First came beard cover followed by his liquid foundation, which he set with powder. This gave him a perfect creamy complexion. He added blusher to bring out the color in his cheeks and then went to work on his eyes. He plucked his eyebrows and then used his eyebrow pencil to fill and shape them. He used his eyeliner and shadow to shape and color his lids and finished it off with three coats of mascara, which made his lashes long and thick.

He was sitting at the vanity admiring his handiwork when Cindy came back into the room. She was dressed in nothing but a very sexy black bustier and bikini thong panties. Jack watched her out of the corner of his eye as she sat on the bed and slid a pair of black stockings up her beautiful legs and attached them to the garters of her bustier. Then she walked over and stood directly behind Jack watching him as he worked on his lips. Her tits rubbed gently against the back of Jack's head as he worked.

Jack used his lip liner to first outline and then enlarge his lips. He then filled them in with a deep red lipstick that matched his fingernails and finally spread on lip gloss to make them shiny. When he was satisfied, he puckered and blew a kiss at Cindy through the mirror. "Do they look OK?"

"They look great. Your makeup skills are better than most of the woman I know."

"I've done a lot of reading and practicing. I really enjoy trying out different looks. I'm always amazed by how much I can change my appearance. I'm almost done and then you can use the vanity."

"There's no hurry. I can get dressed while you're finishing up." Cindy put on her dress and zipped it up. It was a very sexy dress with a deep V-neck in both front and back that showed off her beautiful cleavage. The dress was fitted to the waist and then flared out into a soft full skirt that ended a couple of inches above her knees. She then put on a pair of black patent leather shoes with gold spike heels. While Cindy dressed Jack brushed his wig and put on a pair of long gold earrings. A few spritzes of perfume and he was ready.

Cindy walked back over to the vanity and posed for Jack. "Does this dress look OK on me?"

Jack turned to study her closely. "You look spectacular in it." He looked down at her feet. "I particularly like your shoes."

"I think Ed had a fetish for women's shoes. He was always buying me high heels and wanted me to wear them whenever we went out."

Jack started laughing. "What's so funny?" asked Cindy.

Jack didn't answer but went to the closet and pulled out a shoebox. Opening the box he showed her an identical pair of shoes. "I guess I've got a shoe fetish also."

Cindy burst out laughing. "That's great. You need to wear your spike heels tonight also."

"I'm not sure. They're a little tricky to walk in."

"Come on. Don't be a wimp. If I can wear them, so can you."

Cindy sat down at the vanity and began to work on her face while Jack put on his dress and shoes. He went to his jewelry box and selected a gold heart pendant necklace and gold bracelet to wear. He also put on a couple of rings. When he was done he turned to Cindy: "I'll be back in a few minutes. I think we need something to get the evening started.

Jack had a bottle of champagne in the refrigerator that he had been saving for a special occasion. If this didn't qualify as special, nothing would. Jack opened the champagne and poured a glass for he and Cindy. Then he returned to the bedroom carrying the glasses. Cindy was finishing her makeup when he entered. He handed her a glass. They clinked glasses and Jack said: "Here's to getting Ed out of your life." They each took a sip.

Cindy smiled at him and clinked his glass again. "Here's to my new girlfriend Jill and her first night out on the town." They stood side-by-side in front of Jack's full-length mirror and inspected themselves critically. Cindy said: "I think we look like two very hot and sexy chicks. If we were going out with anyone other than Kevin and Darryl, I'd fear for your virginity."

Jack laughed. "I just hope tonight doesn't turn into a fiasco." They were filling their purses when they heard Kevin and Darryl knocking. "I'll get it," said Jack as he hustled out of the bedroom. He opened the door and smiled. "Come in guys." Both Kevin and Jack were wearing suits and ties. "You both look very handsome tonight."

They both stared at Jack. "Wow, you look gorgeous," said Darryl. "Your dress is very pretty."

Jack blushed. "Thank you." He held up his glass. "Cindy and I were just having a glass of champagne to celebrate her independence from Ed. Would you like one before we leave?"

"That sounds great," said Kevin. "Where is Cindy?"

"She's just finishing getting ready. She'll be out in a minute. Have a seat and I'll get the drinks."

When Jack returned from the kitchen with the drinks, Cindy was standing in the living room talking with the men. Jack handed each of them a glass. Kevin held his glass up. "Here's to a wonderful evening with the two most beautiful women we know. We'll have a great time and forget all about Ed and your trying day."

"Thank you so much for taking us out tonight," said Jill. "It's very nice of you and we're really looking forward to it." She turned. "Isn't that right, Jill?"

Jack smiled weakly. "Cindy's right. It will be a fun evening. We really appreciate you asking us out."

When they finished their champagne, Kevin said: "We'd better get going or we'll be late for our reservation." Cindy and Jack picked up their purses. Kevin held his arm out to Cindy. "I'm afraid you're stuck with me as your escort tonight. Jill is a little too tall for me in her high heels.

Jack took Darryl's offered arm and the four of them left the apartment. As they walked down the hall, Darryl leaned close to Jack and said: "I really like your perfume. What is it?"

"It's called Obsession."

Jack felt a tremendous rush of both fear and excitement as they stepped out the front door of the apartment building. He would be spending the evening out in public as Jill. He needed to make sure that all of his actions looked both feminine and natural. There was no margin for error. He could hear the click of his spike heels on the pavement as they walked down the sidewalk to the car. Darryl held the door for Jack who remembered to sit first and then keep his knees together as he swung his legs into the car. Kevin and Cindy got in the back seat together.

As they drove to the restaurant, Jack made a real effort to participate in the conversation. Gradually he began to relax. When they arrived at the restaurant, the parking attendant opened Jack's door and held out his hand to help Jack out of the car. Jack gave him a smile. It was wonderful being treated like a lady.

When they entered the restaurant, the maitre d' told them it would be a few minutes until their table was ready. "Perhaps you'd like to get something from the bar while you're waiting. We'll call you when your table is ready." The bar was crowded with men in suits and women in beautiful dresses. They worked their way through the crowd. As they approached the bar a couple stood up, vacating their barstools.

"Here you go ladies," said Darryl and he and Kevin held the backs of the barstools. "You can sit right here." Cindy and Jack sat on the barstools, crossed their legs and ordered drinks from the bartender. As they waited for the drinks to arrive, Jack felt like nearly every man in the room was staring at his nylon-covered legs. It made him feel like a real woman.

When their table was ready, the maitre d' led them through the restaurant to a secluded and romantic table. The lighting in the restaurant was low and nobody paid them any attention as they sat eating and talking. After dinner Cindy turned to Jack: "I need to go to the powder room. Would you like to join me?" They made their way to the ladies room where Jack entered a stall. He pulled his dress up around his waist and sat down. Spreading his legs apart, he worked his penis out through the split crotch of his panty girdle so he could pee. When he was done he maneuvered it back up under the girdle. Checking to make sure that there was no male bulge, he pulled his dress back down and exited the stall.

Cindy was standing at the mirror touching up her lipstick. She smiled at him. "Are you having a good time, Jill?"

"It's been a wonderful time so far. Darryl and Kevin are very nice guys. Do you think they have any suspicion of my true identity?"

"I don't think so but I'm not sure. Kevin made a couple of strange comments to me on the way to the restaurant. Don't worry though. If they did suspect you're a man, they would never give away your secret."

When they returned to the table, Darryl and Kevin were paying the bill. Kevin said: "It's still early. We thought it would be fun to get a drink and do a little dancing before we go home.

Cindy looked at Jack who said: "That sounds fine. Where are we going?"

"We're going to take you to one of our favorite night spots. It's called Bunny's Club and it's in the city center. Darryl and I go there a lot. I think you'll find it very interesting."

When they entered the club, they were greeted by the hostess, a tall thin woman in a long slinky evening gown and very high heels. She hugged Darryl and kissed him on the cheek. "Hi Darryl, hi Kevin. Long time no see. What has it been, 24 hours?"

"You're looking beautiful as always Bunny," said Darryl. "Do you have a table for us?"

"For you two, I have a very nice booth near the stage. Follow me please," she said as she led them through the club. As they walked to the table several of the customers greeted Darryl and Kevin. When they were seated, Bunny said: "Your server tonight is Melissa." Looking at Cindy and Jack she said: "Enjoy the evening, ladies."

As they waited for their server, Jack looked around the club. It seemed like a rather unusual clientele. Approximately three quarters of the customers were women. Some of the women were very attractive while others were rather homely, but all were beautifully dressed and made up. Jack didn't see a single woman in the club who was wearing pants. Most of the tables were occupied either by groups of women or groups of men, although there were a few tables with couples. There was also a large group of single men and women milling around the bar. The conversation was very lively and everyone seemed to be having a good time.

Their server, Melissa, walked up to the table and curtsied. She was wearing a very sexy pink dress with a scoop neckline and short skirt over a full pink petticoat. When she bent over Jack could see the tops of her stockings and her garters. "Good evening, gentlemen. It's nice to see you again. And I see you've brought two very lovely ladies with you tonight. What can I get you to drink?"

After Melissa left to get their drinks, Darryl stood up and took Jack's hand. "It's time for a dance, Jill. Come on."

Jack had no choice but to follow Darryl to the dance floor. Nervously he said: "I'm not sure, Darryl. I'm a little unsteady in these spike heels."

"Don't worry, I'll hold you tight," he said as he took Jack in his arms. As first Jack was very tentative, but he started to relax as he gained confidence that he wasn't going to trip and fall. He found that Darryl was excellent dancer. After a couple of minutes, Darryl looked Jack in the eye. "So what do you think of Bunny's Club?"

"It certainly seems like a lively place. What amazes me is the large number of women customers. They far outnumber the men."

Darryl began to laugh. "I'm surprised you haven't figured it out yet. Jill, darling, this is a transvestite club. Most of the women you see here, including Bunny and all the servers, are men in drag. Kevin and I come here all the time. Most of the time, he dresses up and comes as my date, but sometimes we both dress up and occasionally we both come as men. We thought you might feel more comfortable coming here tonight rather than going to a regular bar."

Jack blushed a deep red. "Oh my God! You know, don't you? When? How?"

"You had us completely fooled until we kissed your cheek when we were leaving this afternoon. Kevin thought he felt a hint of your beard underneath your makeup. When we checked the name on your mailbox, we found the apartment belonged to Jack Williams, not Jill Washington. Since neither you nor Cindy had mentioned Jack, we put two and two together and figured Jack and Jill must be the same person. Tonight when I leaned over to smell your perfume, I also detected the faint aroma of shaving cream."

"I'm so embarrassed. I knew this wouldn't work. I didn't want to come but Cindy talked me into it."

You shouldn't be embarrassed at all. You're one of the most attractive and passable crossdressers that I've ever seen. Both your appearance and your mannerisms are very feminine. And we should know. One of our favorite pastimes at the club is trying to figure out if the women who come in here are real or imitation." Darryl paused and then continued. "Do you go out as Jill very often?"

"Tonight is the first time that Jill has ever been out of the house. In fact before today, nobody had ever seen me. Unfortunately I was dressed up this morning when Cindy had the trouble with Ed."

"Really. What were you wearing?"

Jack smiled sheepishly. "I was cleaning my apartment in my maid's uniform and high heels."

Darryl roared with laughter. "You poor dear. I'll bet you were really embarrassed. Actually you and Kevin should get together. He also likes wearing his maid's uniform when he cleans."

When the music ended, Darryl put his arm around Jack's waist to guide him back to the table. As they walked he said to Jack: "Just relax and enjoy the rest of the evening, Jill. Your secret is safe with us."

When they got back to the table, they found that their drinks had arrived. The four of them sat sipping their drinks and chatting as they watched the activity around them. The room lights dimmed and the stage lights came up. Pointing to the stage, Kevin said: "It's time for the show."

For the next hour Jack sat fascinated as one female impersonator after another entertained the crowd. The highlight of the show was a very sexy striptease performed by a stunningly beautiful impersonator. As the show came to an end, Darryl whispered in Jack's ear: "I think you're as beautiful as any of them."

After the show, they ordered another round of drinks and danced several more times. It was nearly midnight when they finally left the nightclub. At the door to Jack's apartment, Darryl took Jack in his arms and kissed him tenderly on the lips. It was the first time that Jack had ever been kissed by another man but dressed as he was, it somehow didn't seem strange. Darryl smiled at him. "I hope you two girls had fun tonight."

"It turned out to be a wonderful night. I'll always remember Jill's first date."

Kevin chimed in. "We had a great time also. Let's do it again sometime."

When they entered Jack's apartment, Cindy said: "I don't know about you but I'm not ready to go to sleep yet. Why don't we get out of these dresses and into something more comfortable and have a nightcap."

"That sounds like a great idea."

In the bedroom, Cindy picked up her overnight case. Turning to Jack she said: "I need to use the bathroom. I'll see you in a few minutes."

Jack stripped out of his clothes and opened his lingerie drawer. After a few moments of indecision, he selected his pink babydoll nightie and a pair of pink bikini panties that barely covered his throbbing manhood. He slid a pair of nude thigh-high stockings up his legs and put on his pink patent leather high-heeled pumps. After brushing his hair and fixing his makeup he went out to the living room.

Cindy was sitting on the couch waiting for him. She had turned down the lights, put some music on the stereo and poured them each a glass of champagne. "My, don't you look sexy," she said as she handed him a glass. The sight of her was enough to take Jack's breath away. She was still wearing her bustier with her stockings and spike-heeled shoes. Over top was a black transparent peignoir that was held together by a single tie at the neck. She had removed her panties, leaving her beautiful love nest completely exposed.

Jack sat down next to her, put his arm around her and kissed her passionately. Cindy responded, her tongue flicking into Jack's mouth. They sipped their drinks as their passion began to grow. When she was done, Cindy set her glass down and slipped her hand under Jack's babydoll to fondle his breasts. She giggled. "These feel very realistic."

Jack smiled. "They should. I paid enough for them." He opened the tie on her peignoir and cupped her breast in his hand. Bending over he kissed each one. "Yours on the other hand are real and they're spectacular." He slid his hand down her front. As he reached his target, Cindy spread her knees apart and thrust her hips forward. Jack found her clit and began to gently rub it. Soon she was moaning in ecstasy. As Jack continued to stimulate her, she slid her hand into his panties and began to fondle his cock.

She pulled away from him slightly and said: "We need to continue this in the bedroom where we can be more comfortable." They stood up. As they walked to the bedroom, Cindy slid the peignoir off her shoulders and allowed it to drop to the floor. When they reached the bed, Cindy put her hands under Jack's babydoll and pulled his panties down his legs. Then she gently pushed him down onto the bed and climbed on top of him, positioning her cunt just inches from his face. She took hold of his rock-hard cock and began to kiss its head. Jack could smell the heavenly aroma of her juices. Reaching up he grabbed her ass and pulled her down to his waiting lips. His tongue slid inside her and went to work. He could feel the pressure building in his groin and knew he couldn't hold out much longer. He felt her shudder as her body was gripped by a powerful orgasm. Sliding his penis deeper into her mouth she began sucking on it until Jack also came, sending his cum down her throat.

When their passion had subsided, Cindy rolled off of Jack and cuddled next to him on the bed. "Wow! That was fantastic. I think that's the best orgasm I've ever had." She smiled ruefully. "As long as I serviced Ed's needs he never worried about whether or not I was enjoying it."

Jack smiled at her. "I've often fantasized about making love to a beautiful woman while dressed as Jill. I can tell you that tonight exceeded my wildest fantasies."

"I never realized that my neighbor was such an interesting person." She kissed Jack playfully on the nose. "In fact I have a favor to ask of you. If you're not busy tomorrow, my apartment needs a good cleaning."

Jack kissed her tenderly. "Your wish is my command, Mistress Cindy."

 

THE END

  

  

  

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