Jackie Ventures Out free porn video

Jackie Ventures Out The bar was dimly lit. It had a long bar along one wall with bottles of all shapes and sizes sitting on glass shelves in front of a huge mirror surface. Many stools lined the bar. The opposite side of the bar had many tables and some booths. At the opposite end to the entrance was a small dance floor and the service area. The Blue Oyster was a high end nightclub. Two elegant ladies sat at the bar. One had dark hair in a page boy style. The other had blonde hair piled high on her head. Their dresses were short, with low bust lines showing the rather large globes hidden underneath. The blonde lady had a narrow waist and somewhat larger bust. They both had cocktails in front of them. "Is he here yet?" The blonde lady appeared nervous constantly moving and shifting on her stool. She wore a red dress with spaghetti straps. Her earrings had some matching red stones that jingled as she moved. Her fingers had long nails in a matching color. "Relax, Jackie," the other lady said. "He'll be here soon. He promised." She patted Jackie's knee. "You look beautiful. Stop moving around. I know that the plug may be a little uncomfortable. But you'll be grateful for it later. Here, have a ciggy to calm you down." "Casey, I didn't know you smoked and I don't smoke," Jackie replied surprised. Even before she could protest further, Casey had lit up and after a deep drag placed it in Jackie's mouth. Casey lit another and inhaled deeply and blew out a cloud of smoke upwards. She was clearly a practiced smoker. Jackie continued to inhale in short puffs. "I smoke when I meet Rob. He likes his ladies to smoke. Says they are sexy." "Hello ladies," the deep voice behind them said as if on cue. The man was over 6 ft. tall, slim, with an open neck silk shirt under a black jacket. He kissed both ladies on the cheek even though he didn't know Jackie. "Hi Rob. Jackie here thought you wouldn't show. Rob meet Jackie." "Why would I stand up a beautiful lady like Jackie?" Rob replied smoothly. "Casey told me she had a beautiful girlfriend I needed to meet." Jackie was surprised at Rob's comments and took a few quick puffs on her cigarette. "She was nervous so I gave her a cigarette to calm her down." "No reason to be nervous Jackie although I do admire beautiful ladies who smoke." Rob took out a cigar, bit off the end and lit up. Fragrant smoke drifted up. "Drinks ladies? Hey Julio, the same again for the ladies. JD on the rocks for me. Put their drinks on my tab." Rob didn't wait for a response. As soon as they had their drinks, Rob asked if they had eaten dinner. "We had some snacks earlier. I'm not hungry. Jackie?" Casey replied. "No," she said quietly. She had eaten a small dinner earlier at Casey's apartment but the tight corset had totally crushed her appetite. She had to stop drinking or she would be drunk. "Ok. Maybe we can get something later. Jackie, would you like to dance?" Rob was trying hard to be sociable. It was a Saturday night and just 9 pm. The night was young. Jackie had never danced in heels and hesitated. "Go on," encouraged Casey. "Rob's a great dancer and will guide you." Rob held out his hand and Jackie got up. He put an arm around her waist and guided her onto the dance floor. It was soft jazz and the few couples were dancing close together in slow movements. Jackie was glad Casey had forced her to wear heels every night for the last week to be able to walk confidently on those 4" spikes. Casey had made sure they were a comfortable fit. Rob pulled Jackie closer to him. She didn't know where to put her arms and raised them around his neck like the other ladies on the dance floor. They were moving slowly cheek to cheek. Jackie could feel the growing bulge at her crotch as Rob whispered how beautiful she was. She didn't believe it but it was nice to hear. Casey lit another cigarette and watched them, Jackie in particular. She hoped the night would end well. Rob was following Casey's instructions and pulling Jackie close, bodies touching, then kissing her ear. Jackie had her arms around his neck and seemed to be enjoying it. Rob held Jackie's hand as he led her back to the booth. "Casey, your turn to dance," Rob offered. "No thanks. I just thought Jackie here would enjoy the experience." Casey smiled at Jackie who looked embarrassed. "Well, I certainly enjoyed the dance. I hope Jackie did too. So what is next? I have champagne cooling and a few snacks in the apartment. Would you ladies be happy with that?" Casey looked at Jackie standing there nervously. "I would like to finish my drink, have another cigarette and then take you up on your offer. But Jackie and I will follow you. We have a car here." "That's great. Perhaps I can invite Peter over too so we have a foursome. He's cruising somewhere but would be glad to meet, I think." Casey smiled at Rob. "That's not at all like you, Rob. You normally wouldn't want to share two beautiful ladies. What's the matter? Not up to it?" "I don't think you have found me lacking before, Casey. I would be delighted to be the center of attention for both you ladies tonight. Why don't I go ahead and set it up? I'll see you both there shortly." Rob smiled, leaned down and kissed Casey on the lips. He turned to Jackie and kissed her also on the lips. "I'll be waiting," he said to her and left. Casey smiled. Things were going as planned. She reached into her purse for a cigarette. Jackie looked very uncomfortable after that kiss. Casey smiled and lit one and gave it to her. Jackie inhaled nervously. "See? I told you that Jackie would get a lot of attention and more sex than she can handle tonight. Don't let me down. We have prepared for this for weeks. Right?" Jackie puffed nervously and nodded. This is what she had wanted. She had followed Casey's tutelage and now stood at the edge. Jackie continued to puff nervously and nodded her head. So far Casey had delivered on her promises. She was nervous about the next steps She was also excited. They exited the club and Casey drove them to Rob's apartment. This was not too far away in a fashionable part of the city. "Now Jackie, you are not going to back out now. You are going to have a fabulous night, as am I. I know Rob and he has great stamina. He will make you happy." Casey was smiling at the thought. "What does he expect? Does he know about me?" Jackie asked softly. "He expects you to have sex with him as a female. I told him you were a special 'gurl' and could only offer him your back passage. So he'll want to use your mouth and arse. You will be glad you have that plug in with the lubrication." Jackie was deep in thought. She had wanted this and had let Casey guide her so far. From the practice in high heels, the tight corset and the glued on breasts Casey had transformed Jack over the weekends into Jackie. She had forced Jackie to suck on her 7" strap on and also had penetrated her daily over the last few days. Jackie had prepped well. She had not yet had to swallow anything and Casey made sure she understood her lips needed to firmly surround the cock and she had to swallow all. Today, Casey had made an appointment for her with Salina, a beautician. She had pierced her ears, trimmed her eyebrows but later decided to cover them and draw eyebrows. Salina had attached and painted her finger nails. Casey had chosen a blonde wig which was pinned firmly to the cap on her head. Prior to the evening, before Salina had come to the apartment, Casey had given Jackie several enemas and cleaned her back passage thoroughly. Her breasts had been glued down last night. The dress had been bought at a discount store together with matching heels under Casey's supervision. Jackie was ready to face the world. She could not understand the emotions in her brain: nervous tension, uncertainty if she could perform and the excitement of a sexual encounter with another human. So far she had only experienced self-pleasure. Casey had teased and taunted her during these sessions, even touched her parts but had never gone further. "You've gone too far to back out now," Casey reminded her. "Look at you with those thin eyebrows and glued breasts. You made quite an investment in Jackie and today is when you get a return on your investment." Jackie had not thought of how he would face his colleagues as Jack. They would see the pierced ears and thinned eyebrows. But Casey had a point. She had not given much thought to the events past tonight. This was the culmination of a dream. She looked forward tonight with nervous anticipation. Casey parked the car and they rode the elevator to the 4th Floor which was Rob's floor. Casey knew her way around and so Jackie assumed she had been with Rob quite often. Rob greeted them warmly, each lady receiving a small kiss on the lips. The apartment was quite large and well appointed. Rob obviously was doing well. "Champagne is cold and I have a few appetizers in the oven." Rob had removed his jacket and now just wore a silk shirt in a pale yellow with beige pants. He was dressed quite fashionably. "We need to freshen up a little," Casey said and steered Jackie to the bathroom. She checked their makeup, repaired the lipstick and added more blush. Casey had Jackie bend over the sink and made sure the plug was firmly embedded. "I think we're ready," Casey said and led them back to the large living area. Rob had dimmed the lights and poured out three glasses of Champagne. Soft music was playing in the background. He was seated on the couch and obviously wanted a lady at each side. "To a fun night," Rob toasted and clinked glasses. They took a sip. Rob placed an arm around each lady's waist. "So Rob, what have been up to?" Casey asked slipping her hand inside his shirt. Jackie looked on and wondered where she fit into this. Rob turned to her and gave her a deep kiss. Jackie watched as it lasted a long time. Was she going to be just an observer tonight? They broke the kiss. Casey reached for her glass and noticed that Rob's hands were occupied. She lifted his glass to his mouth and offered him a drink. Rob turned to Jackie and moved his head closer. With both hands occupied he couldn't pull her head in for a kiss. Casey leaned forward and pulled Jackie's face to Rob and made sure there was firm lip contact. She gently took Jackie's arm and moved it to Rob's neck. Jackie got the idea fast and let Rob's tongue explore her mouth. She had never been kissed like this before as. She had to break off contact in order to get her breath. Casey was smiling as she saw Jackie's smeared lipstick and bemused look. Rob removed his hands from the ladies' waists and took a sip. "Wow," he said enthusiastically. "That was a great start. Appetizers?" he asked. "I'm not hungry yet," Casey replied. "You Jackie?" Jackie shook her head 'no' and reached for her glass. She was processing the kiss. She had kissed a man who had tried to push his tongue down her throat. It was exciting. Casey was feeling the growing bulge at Rob's crotch and started rubbing it. She moved down and knelt between his legs. Whilst Rob looked down with a wide grin, Casey began to remove his shoes and moved up to his belt. With very little resistance, Rob lifted himself up and allowed her pull down his pants and briefs. Soon these lay in a pile to one side. Jackie looked in wonder at the length and girth of Rob's tool. It appeared very large, almost double the size of the little cockette tucked away tightly in Jackie's panties. Casey looked up at Jackie and ran her tongue across her lips. She pointed to the floor beside her. Jackie stared at the massive appendage and then slowly slid down. Rob had to spread his legs to accommodate both ladies. Casey and Jackie kneeled side by side in a tight huddle. Rob's legs were hooked around them. Casey lifted the cock in one hand, smiled at Jackie and kissed her hard. Jackie nearly fainted. This was the first time that Casey had kissed her. It didn't last long but Casey's free hand moved Jackie's head down. It was an invitation to suck Rob's balls. Jackie had not practiced this. It didn't take long for her to get the idea and took a nut into her mouth bathing it in saliva. Then she moved to the other nut. She tried to load both into her mouth but gave up. Casey's mouth was dangerously close to Jackie's as she sucked slowly on Rob's cock. Up and down and almost kissing Jackie on the downward stroke. After a few minutes Casey stopped and licked the cock from root to tip. It was time for Jackie to demonstrate she had learned to do this correctly. Casey still held the cock as Jackie prepared to kiss the tip and continue to suck. Casey moved aside a little and Jackie looked at the hard piece of meat in her hand poised to enter her mouth. She gave it a sloppy kiss on the head, With Casey's encouragement she began to take in the cock ever deeper into her mouth. She did it slowly wanting to taste it and to let it go to her throat slowly. Her practice on the dildo helped her avoiding a gag. Casey's hand moved to the back of her head and indicated she needed to move up and down faster. Casey's hands were massaging the sac with intermittent kisses to the base of the cock so that Jackie's lips met hers. Rob started to lift his hips and thrust faster and this heralded his imminent release into Jackie's mouth. "Don't lose a drop," Casey whispered into her ear as Jackie began to feel Rob's thrusting. He erupted deep in her throat and Jackie kept her lips tightly around the cock, sucking and slowly extracting every drop. Rob gently pushed her face up off his now soft penis and leaned forward and kissed her deeply. "That was incredible," he said. "You were able to take it all in." "She's been practicing," Casey said like a proud teacher rising and helping Jackie up. She hugged Jackie. "See, I told you would get everything you wanted." She kissed Jackie hard on the mouth. "For being a good girl. Let's go clean up. We need to give Rob a little rest. Rob maybe we could use some of those tidbits to eat and more champagne." The two ladies walked to the bathroom. They used the facilities and Casey had to help Jackie pull down her tight panties and gaff. "You won't need this later," Casey said pulling down the gaff. "Just wear the panties." She inspected the plug and drew it out quickly. Jackie could feel the void. A moment later something cool entered her passage and Casey's fingers pushed it in deep and a moment later the plug was back in. "No reason for more pain than necessary," Casey said with a grin. Their faces in parallel looked into the large well-lit wall mirror. Lipstick was repaired and Casey darkened Jackie's shadow. They walked back to the living room. Jackie was still savoring the taste in her mouth. She had crossed a threshold tonight and the next stage for Jackie lay ahead. Very few words had been spoken. But as per the promise, Casey had kissed her and she had been also kissed by Rob and then had sucked his cock. The simple truth was that she had enjoyed all that had happened and she had done. She was looking forward to the next step. Rob had a big grin on his face as he placed small plates of appetizers on the low table. Glasses of champagne were full as they toasted. Rob looked a little less than his immaculate self. His shirt was undone and hanging over his pants on one side. He had attached the clasp of his pant but not pulled up the zipper. He knew he would be shedding them soon. "So ladies, that was fabulous." His smile was wide. Casey looked at Jackie. "I think Jackie enjoyed herself very much." "Great," Rob replied. "We should continue the fun as soon as you are ready." He was looking at Casey. "Now, I think we ladies need to have our fun too. After all, it is a Saturday and we have been looking forward to this for some days." Jackie looked questioningly at Casey who continued. "Let's go to the bedroom for the next part." Rob's grin grew wider as they moved to his large bedroom with a king sized bed. "Now Rob, remember what you have wanted from me all these weeks? You might just get it if you play along." "What do I have to do?" Rob asked eagerly. "First of all, Jackie is going to undress you completely. Right Jackie?" Casey looked at Jackie and indicated what she needed to do. Jackie moved in and kissed Rob and began to unbutton his shirt. The shirt fell away and Jackie unclasped his pants that also fell to the floor. Boxers and socks were next. Very soon, Robert was naked. "So Rob, for the next part we will need a little more control. So I'm going to blind fold you and tie your hands behind your back. Agree? Remember the prize." "Sure, I like some light bondage" Rob said enthusiastically. Casey tied a dark scarf around his eyes and used a tie to bind Rob's hands behind his back. She spun him around several times. "Now Rob, Jackie and I are going to do some things to you that you will like. You need to guess which one it is but only when I ask the question. Three correct guesses and you'll win the prize. Ready?" "Oh yes Casey went up to Rob and kissed him, inserting her tongue into his mouth. She indicated for Jackie to kneel down and kiss his cock. Casey kissed him deeply on the mouth. Within minutes they switched positions. Casey tugged at Jackie's dress to indicate they should stop. "So, who's sucking your cock?" Casey asked Rob thought for a minute. "Casey." "Well you got that right. Now our second attempt." Casey asked Jackie to suck on Rob's nipples. Jackie wasn't sure how to accomplish this and bit hard. Rob yelped. "Just wanted to see if you were enjoying this," Casey said winking at Jackie. She pointed to a spot next to her on the carpet and Jackie fell to her knees. Casey had now stopped to suck Rob and indicated Jackie should take over. Jackie took the hard cock into her mouth and went up and down. Casey began to suck his balls. After a few minutes they stopped. "Who was sucking your balls, Rob?" Casey asked Rob thought for a minute and said, "It was Jackie." Casey winked at Jackie. "Damn, right again. Two out of two. One more right and you get your treat. You had better control yourself. We need a good fucking." Casey and Jackie stood up. Casey indicated Jackie go to the back of Rob, wrap her arms around him and slowly stroke his cock. She herself began to give Rob a deep kiss. After a few minutes broke off. "Last question. Who kissed you just now?" Rob didn't think. "It was Jackie." He paused. "Right?" "Damn. Yes, you got it right. I lose so you get to plough my arse. Just to make it easy I need a moment to prepare and we'll keep the blindfold on." "Oh? What about my hands?" Casey thought for a minute. "No, let's keep it like that so I control the action." "Oh." You could hear the disappointment in Rob's voice. "Don't sound so disappointed. You are going to penetrate a virgin arse. How often do you get to do that?" Casey asked. Jackie was looking on confused. Did this mean that Rob was going to fuck Casey? After losing her oral virginity, Jackie was now hyped to also lose her anal virginity. Casey noticed this and came up to Jackie and gave her a kiss. She turned her around and had her step out of her short skirt. She pulled down her panties and carefully removed the plug. She motioned for Jackie to remain quiet as she led her to Rob. "It seems you lost your hardness there," Casey said. "I think Jackie here needs to prepare you." With Jackie looking on Casey knelt down again and began deep throating Rob. It didn't take long for Rob to regain his hardness. Casey stopped and brought Jackie to the foot of the bed and had her bend over and grab the foot-rail. She made sure the skirt was firmly tucked and her anal opening exposed. "Hey Jackie, make sure Rob here finds the opening," Casey said taking Rob's cock and positioning it at Jackie's puckered hole. "Rob push in slowly now. Don't hurt me." Casey held Robs cock as it slowly entered Jackie. "Oh..." Jackie did her best not to cry out. She wiggled her backside allowing Rob entry. It hurt a little but Casey's practice with the strap on made it easier to bear. Rob began to thrust faster. He had been teased enough and felt now that he needed to show his mastery. Jackie moved with him amazed at the feelings coming from the monster thrusting into her. It was truly exciting. Casey was massaging Rob's balls. "I'm close," Rob said thrusting hard. With his hands behind his back he used his full body to push his cock deep into Jackie. "Go on," Casey encouraged, "Fill me up." Rob thrust hard and shuddered. He slowed down as Jackie wiggled her butt trying to extract every drop. She was in heaven experiencing sensations as never before. All this activity had also caused her to explode. Casey had wrapped a set of tissues round Jackie's cock so she wouldn't spoil the bed. Casey pulled Rob back and helped Jackie stand. She smoothed down her skirt and kissed her. She indicated she should go to the bathroom fix herself back up. Casey hiked up her skirt, dropped her panties and grabbed the wad of tissues from Jackie's cock and pushed it between her cheeks. She hobbled around and undid the restraints around Rob's hands and removed the blindfold. "Baby, that was incredible," Rob said looking at Casey. "For me too. I am leaking from the amount you pumped into me. I need to go clean up. Jackie went to repair her face." Casey kissed Rob and walked away awkwardly with a wad of tissues forming a lump in her crack. Rob was smiling at what he had just experienced. Casey knocked on the restroom door. Jackie opened it a wedge and saw Casey and let her in. "Well, did you like that?" Casey asked with a grin. "Incredible," was all Jackie could say. "I promised that as Jackie you would get more sex than you could handle. Jackie is no longer a virgin in any of her holes." Jackie looked at Casey. "Rob thought he was fucking you anally." "I know. He has been wanting that for some time. But I thought he may have more stamina for you. He hasn't done it three time in one evening and I didn't want you to miss out." Casey hugged Jackie. "I told you that the time and practice would be worthwhile." "Yes," Jackie said hesitantly. "That doesn't sound so positive. What's up?" "Does this mean I need to be Jackie to get sex?" "Well, you can choose how and in what guise you can get sex easily. You look so hot you might just turn me lesbian with a gurl like you." Casey kissed Jackie hard. "We better get back. Rob must be wondering what we are up to in here." Jackie looked at Casey. Jack would have loved to have sex with Casey. There were many opportunities but nothing had happened. But as Jackie, it seemed that both Rob and Casey were interested in sex with her. Rob had tucked his shirt in his pants and had a broad grin. "Ladies, some fresh champagne?" Even as he asked the question he handed them filled glasses. "Fantastic. We should do this again soon. Maybe Jackie would enjoy it too." He smiled at Jackie. "Oh yes," Jackie whispered. "I would like that." Casey smiled. It seemed that Rob was quite convinced that it was Casey whom he had fucked anally. "It's getting late and I think you won't be good for some time," Casey said. "Jackie, let's leave Rob here to recover." Rob kissed each of the ladies hard, requiring another lip repair. They left Rob arm in arm. "You know Jackie it's a Saturday night. With all that excitement I recall that I haven't been fucked tonight. I think I might like Jackie to do that." Casey smiled at the thought. "It seems Jackie got a lot of attention tonight. I think you enjoyed it. "Yes. I am in dreamland. Jackie would be more than happy to help. After all, you helped her so much." Jackie leaned forward and kissed Casey, tongues exploring. It was many minutes before Casey started the car. Casey had her hand on Jackie's thigh as she drove home. Her thought went back to how this all started. ******* This had been several weeks in preparation. She thought back to the party that started it all. Jack Kershaw was Casey's neighbor at the company's Christmas party. They had exchanged polite conversation as the drinks from the open bar flowed. Casey had no partner that evening and neither did Jack. Although they worked in the same department Casey had hardly exchanged any words with Jack. When the dancing started, Casey moved to a secluded spot. She didn't want to be groped tonight. Jack followed and they sat together, drinks in hand, in a quiet corner. "So Jack, we sat next to each other all evening and are sitting here together but you haven't made a play for me. Don't you find me attractive?" Jack was dumbfounded. He did find Casey very attractive. She was of medium height, short black hair with a generous bust. She was the envy of all the men in the office. He was sitting next to this beauty and couldnt find anything to say. "Are you gay? Bi? I don't care but I normally get more attention from men." "Sorry, Casey, you are beautiful but I don't know what to say." "Oh, my. A shy boy. Haven't met one if those in a long time." "Sorry," was all Jack could stutter. "I can go and you can go back to the party." Casey touched his arm. "Sorry. Please stay." Jack sat back down again and looked at Casey. He looked confused and uncertain sitting next to this beautiful creature. Casey got another round of drinks and patiently engaged Jack in conversation. It took some time but Jack opened up and disclosed that he was unsure if his sexuality. He liked both girls and boys from a distance. He was too shy to approach them. He had a crush on a boy in college but was too scared to be found out and branded with labels. He needed to keep the job and decided he couldn't afford any risks to his ego or job. It was a longer story and Casey had listened closely. She didn't know that such people existed. They were scared of life and how to express their feelings. Casey was the total opposite and didn't hesitate to approach a guy or girl if she felt an attraction. Casey was now comfortable with Rob, her main boyfriend since Christmas. He was not exclusive but was definitely more entertaining that her other beaus with incredible sexual stamina. She met with him regularly. The sex was amazing and she enjoyed every moment. Whilst Casey was open to most things sexually there was one area where she hesitated: anal sex. Rob really wanted to penetrate her back there. Casey didn't feel the need. That had been the catalyst for her now close friendship with Jackie. "Jack, you need to find out who you are and what you want," she had said after hearing of his confusion. "Today, nobody cares if you like boys or girls. Have you tried to have sex with a girl? I have had sex with boys and girls although I prefer boys." Jack looked at her sadly. After a long silence he said, "In College at a party I was quite drunk on a couple of beers. So was Belinda. I thought I would try and took her to my apartment. We were both quite drunk. She opened my pants and took out my penis but I couldn't get it hard. She tried everything to stroke it, suck it but nothing. She gave up and left disgusted." Casey looked at him and felt sorry. Everybody deserved a partner for sexual release. "Did you ever try with a boy?" Again that same sad look. "I wanted to but was too scared. He was my roommate in college. He always had girls running after him. I wished I was one of them." Casey laughed. "You know Jack, I think I know the answer. Come to my apartment on Saturday and we'll talk. This is not the time." Casey leaned forward and gave Jack a kiss on the mouth. "Happy Holidays." Jack was shocked. Christmas had fallen on a Tuesday. Casey and Jack were back at work on the Thursday. Not much was spoken about the party but Casey did remind Jack that he had promised to see her on Saturday. He was to go there for about noon. Jack was surprised that Casey remembered. He was grateful and thought perhaps she would be willing to try something with him. He looked forward to it. On the Saturday, Jack arrived at Casey's. He brought her a box of chocolates. Casey was delighted. She offered him a drink and he asked for a diet Coke. Casey smiled. He appeared nervous. "Jack, you remember our conversation at the Christmas party?" Casey asked. "Of course. I have to thank you for the time you spent with me. Everybody must have been looking for you." "Yes, well. I enjoyed talking to you and thought I could help." "Help?" Jack asked nervously. "Yes. You know about your sexual orientation. It seems a shame that a nice guy like you doesn't have a partner." "I don't know what to do," Jack admitted. "What can I do?" It was pathetic. "Jack I need you to trust me, ok? This can become quite personal." Jack looked at her. Was she offering sex? He wasn't sure what to do. But walking away now didn't make sense. "OK," he said softly. "As I recall the conversation, you didn't know if you were attracted to boys and girls or both. It seems you had a bad experience with a girl that has shattered your confidence. You had a crush on a boy but never did anything." Jack nodded. He didn't know where this was headed but it seemed that it would end up in humiliation for him. Perhaps Casey would never speak to him again. He had so looked forward to meet her today. "OK. Do you find me attractive, Jack?" "Oh yes," Jack nodded affirmatively. "Are you getting hard?" Jack looked at her sheepishly. He was firm but a long way from hard. "I think so." Casey removed her sweater and skirt and stood there in bra and panties. "How about now?" Casey ran her tongue across her lips. "I think you need to get comfortable and take off your pants. I need to see the reaction as we do things." Jack stood up and dropped his pants. There was a slight bulge in his Y fronts. Casey smiled. It had been some time since she saw a guy wearing Y fronts. Jack look very embarrassed. "I think the underwear too." Casey had to suppress a smile at Jack's discomfort. "Don't be shy. Look I will remove my bra." Casey exposed two magnificent globes that hung down proudly. They looked big for her body size but certainly very inviting. Reluctantly, Jack lowered his Y Fronts. He had a rather small uncut penis. Even with Casey's magnificent body in sight, it was only half tumescent. Jack looked at Casey sheepishly. "I know we need to make allowances for you being nervous, but I can see your problem. Now, let?s see the other side.? Lisa went into her bedroom and came back with a paper. ?I printed this out discreetly,? she said with a smile. She held it out to him. Jack took the picture and stared at it. His eyes widened at the sight. There was a huge African American male with a massive penis in the mouth of a smaller Caucasian male. The Caucasian had difficulty accommodating the girth of the back penis in his mouth. ?Aaaargh,? came the short yell from Jack as his penis erupted all over Casey?s carpet. ?Oh my,? Casey said and went to the kitchen. She brought a roll of kitchen paper and a wet sponge. She knelt down and wiped the carpet clean. She handed a couple of sheets to Jack who looked totally humiliated. He wiped himself and hurriedly pulled up his underpants and trousers. He was blushing red. ?Sorry,? he said dejectedly. He couldn?t understand what happened. He had just erupted at the sight of that huge cock stretching his partner?s mouth. Casey gave him a brief hug. ?Jack, at least we know the problem. Then it is easier to find a solution. Agree? I?ll make some coffee. You can use the bathroom down the corridor if you need to.? Jack went to the bathroom, Casey went to the kitchen. There was a sly smile on her face. This was good information and would fit her plans well. Jack looked completely dejected. He had blown it with Casey, the only girl who had ever shown interest in him. He didn?t understand what happened. Just the sight of that picture had caused an eruption without even touching. ?Jack, don?t look so sad. At least we know what stimulus you respond to.? Casey had poured out two mugs of coffee and each took a sip. ?You were obviously excited by that picture. It?s OK. I too found it sexy. Not sure even I could get that in my mouth.? Jack looked miserable. ?But I never did anything like that. I never saw any picture like that before either although I know it happens. I am sorry.? ?I?m not sure you should be so down. Having a nice cock in your mouth feels great especially when they grow and get hard in your mouth. I enjoy that.? Casey took a sip of coffee. ?Maybe you should try it sometime.? ?No, I can?t do that. What will people think? They?ll call me all kinds of names.? ?So, you would like to do it if you didn?t think people will call you names? Of course, only your partner will see you like that.? Casey pressed her point. Jack didn?t respond and stared into space. Jack was deep in thought, looking glum and not wanting to look Casey in the eye. ?So, since we are being very honest with each other, what would you say if you saw me with a cock in my mouth?? Jack looked at her aghast. ?You are a woman and doing something like that would be normal, I guess. It would be exciting.? He looked at her as if hoping she was thinking of putting his thing in her mouth. ?See, that?s the answer. Jack needs to become Jackie and then these things won?t be such a big problem. You can pleasure a man and not feel guilty.? ?Jackie?? ?Yes, why not? Then you won?t feel guilty about sucking a cock or getting fucked.? Jack had never heard Casey use such words before. He was not sure what she meant. He looked at her confused. ?So I will turn you into a beautiful girl and introduce you to a great guy who will take very good care of you. You saw the reaction when you saw that image.? ?I don?t know what happened. I saw them and I just exploded.? Jacked looked desperate. ?The point is that when you saw me almost nude it didn?t get any big rise out of you. Agree? You were more stimulated by those guys. I think you wanted to have that big cock in your mouth. You are frightened to do it as Jack. But Jackie won?t have such labels. You said so yourself.? Jack sat there looking totally downcast. ?I can?t become a woman just to have sex. Who would look at me? ? ?OK. We can talk about this all day but I have to get ready for a date tonight. I want to help and think you would look great. Look at your size? Skinny and you probably weigh the same as me. If you want to do this, go to a pharmacy, get some hair remover and then denude your body from the eyebrows down. Follow the instructions carefully. I can see you here tomorrow but after 2 pm. I know it will be a late night and I?ll be very busy tonight.? Jack could imagine her on a date and then coming back here for some frenzied sex. He envied her boyfriend. ?If you choose to do this, you have to do everything I say and be ready to meet the friend I will introduce to you. We will need to buy some stuff so be ready for that. You will get to experience sex as never before but you must dress and act the part. If you don?t come, we will meet in the office Monday and no more discussions.? Casey left Jack sitting there and went into her bedroom, shutting the door. Jack left Casey?s apartment in total confusion. He had hoped to be on a high after having an intimate encounter with Casey. Her test result had shocked him. He couldn?t understand how he didn?t get a rise looking at Casey?s near nude body. Yet he had erupted on seeing those two guys in action. He tried to focus on his feelings at the time. He couldn?t explain it as he wandered the streets trying to gather his thoughts. He couldn?t comprehend Casey?s suggestion: if he dressed as a woman and performed with a man, he wouldn?t feel so guilty. He rationalized that for the male having a warm mouth around his cock and then later a later a tight anal passage to explore was something a male did when the lady had her periods. It also meant that he would have little chance of a sexual encounter with Casey or another woman. He had read that some ladies liked their men dressed like women and wondered if Casey wanted that. She certainly was encouraging him to dress. Perhaps she was one of those ladies. It all boiled down to a simple equation really: dress like a woman and suck and get fucked or stay as Jack and get to beat off. It didn?t seem like a difficult decision. On the way back to his apartment Jack went to the drugstore and bought the depilatory. He didn?t want to disappoint Casey and hoped he would get closer to her. She was his only hope for sexual fulfillment. He thought he had nothing to lose ? except his hair and virginity. Even though it was a Saturday night Jack had nothing going on. He followed the instructions on the depilatory. He thought he was smooth all over. He felt the smoothness of his skin and was aroused as he ran his fingers over his smooth skin. He sat at his computer and researched how men became pretty girls and had wild sexual encounters. By the time he had watched some images and videos he was rock hard. One video in particular where the ?girl? was being pounded in the arse with loud moans whilst at the same time trying to deep throat a large cock caused him to erupt in huge gushes. It took him some time to clean up the mess on his laptop and clothes. He searched for girls with TVs and found some videos where the girl was pounding the TV with a massive strap-on. He fantasized that it was Casey pounding Jackie. By the end of the evening he had erupted twice and his mind was raging with thoughts of being impaled at both ends. Of course he could only visualize this as a female. The thought of Jack penetrating a female disappeared from his mind. He couldn?t wait to meet Casey. The next day Jack appeared promptly at Jackie?s door. She was still in her robe and had apparently just woken up. ?Hi,? she said kissing him on the cheek and giving him a small hug. ?Coffee? I just made some.? Casey came back with two mugs. ?So, what did you decide? Since you are back I assume you agree.? ?Y..Yes,? Jack said hesitantly. ?I would like to try.? ?That?s good. Did you depilate your body?? ?Yes, I did as you asked.? ?Let me get dressed and then we are going shopping for some stuff.? Casey rose and wiggled her butt to the bedroom. Jack watched her go and wondered if this was a prelude to a sex session tonight. Dressed in jeans, T-shirt and sandals Casey appeared some twenty minutes later with a tape in her hand. She measured his chest, waist and hips. ?Size 10 or 12 probably. To practice I think we can use stuff from thrift shops but some don?t let you try before you buy. Then, before the big day, we can get you a nice outfit. We need underwear and clothes, shoes, some makeup, a good wig and of course some big breast forms. We?ll have to buy the underwear new I think.? Jack heard all of this but didn?t take much in. Casey drove to a large Goodwill store in a busy street. Jack followed blithely happy to be in Casey?s company. Within a couple of hours they had bought a fair amount of stuff: two skirts, one dress and shoes. Jack had discreetly tried them on whilst Casey shielded him from other customers. It was not a busy Sunday afternoon. Casey was surprised to see they offered some corsetry and large bras. They also found some large clip on earrings. . For a start this would do. Down the street there was a small salon with many wigs on display. These were all cheap and not very realistic. But they would do for a start. The nice Vietnamese lady offered them a variety and Casey chose a blonde and brunette wig. Their low prices indicated a low quality. The overall purchases were quite modest. At a pharmacy Casey purchased some stay up stockings and a large pack of cotton wool. Jack just followed Casey with the growing number of bags in his hand. They were back in Casey?s apartment before 5 pm. Casey opened a bottle of wine and poured out two glasses. ?To Jackie,? she said clinking glasses. ?Strip down to your boxers.? Jack slipped out of his loafers, pulled down his pants and took off his shirt. Casey was busy arranging their purchases on the couch. She turned around and inspected Jack for body hair. She ran her hands over his body causing it to shiver. Nobody had done that to Jack before. She briefly touched the growing bulge in his Y Fronts. Casey asked him to hold out his hands and pulled the bra through them, clasping it at the back. She tightened the straps. Opening the large pack of cotton wool, she stuffed the cups until they felt full. They would never substitute for heavy forms but would do for a start. ?We didn?t get any panties so we?ll make do with your Y fronts for now. Why don?t you go to the bathroom and take care of this,? Casey said tapping his bulge. ?Then wear this blouse and skirt. We?ll do the rest when you are done.? Jack walked into the bathroom clothes in hand and mind befuddled. He had hoped Casey might help with the bulge but that was not to be. He stepped out of his pants and took care of business ensuring there was no spillage onto the clothes. It felt different to be wearing a full bra whilst stroking himself. He cleaned up and pulled the pants back up. He stepped into the skirt and closed the zip at the side. He was grateful for the elastic band at the wait. It came a few inches above his knee. He then buttoned up the blouse. It was tight over his large bust and he had to leave the top buttons undone. His last look in the mirror showed an androgynous figure: the body of a female but the face and hair of a male. ?We?ll have to get a bigger blouse but it works for a start. Sit here.? Casey pointed to a straight backed chair. Casey knelt at his feet and rolled the stockings up his legs. She then inserted his stockinged feet into the shoes. These were two inches high. Jack watched in amazement as Jackie appeared. The silk stockings on his legs felt great. Casey went behind him and placed the brunette wig at the front of his head and then pulled it back. Jack could feel the tightness on his head and the hair at the nape of his neck. He wanted to see what he looked like. Finally, Casey applied a bright red lipstick to his mouth. Jack could smell the perfume and the taste. He thought he looked good. ?We?ll have to do a lot better to make you pass, but not bad for a first effort,? Casey said and helped Jack stand. The heels were not high but they certainly felt different to his male shoes. ?Just walk a little with small steps till you find your balance.? Jack was made to walk around the apartment until he felt he had found a balance. ?So, Jackie, can?t call you Jack dressed like that, how do you feel?? ?Good,? Jackie said looking frequently in the mirror. He would never pass as a woman but he was feeling good. ?OK. You should take these clothes back home and practice at home. I?ll see you here Tuesday after work and you can show me how well you can walk. Not that you?ll be doing much of that.? Casey smiled. ?Take your things off carefully and don?t ladder your stockings. Act like a lady. We will have to get some things to improve your shape. You need to be girly when you get fucked.? Casey?s smile gave Jackie goosebumps. She went to the bathroom to become Jack. At work on Monday Casey was her usual self. There were a few exchanges with Jack but otherwise no acknowledgement of the events over the weekend. A knowing smile, a wink and Casey was her usual bubbly self. That evening Jack dressed up again and became Jackie. He enjoyed the transformation. The bright red lipstick changed his whole appearance. He wouldn?t pass as a female but he enjoyed becoming Jackie once again. He walked around his apartment please at the clicks on the wooden floor. The night erupted in a massive spurt into his hand. Tuesday was similar except that Jack found a note saying 6.30 pm at the apartment and he should bring some red wine. Jack went back home, took another shower, shaved closely and left for Casey?s apartment. He bought a nice bottle of wine on the way. Casey greeted him with a kiss on the cheek. ?I hung up the other outfit in the bathroom. I also left out some make up. Take a close shave and change. I want to see Jackie strut out. I?ll put a pizza in the over and open the wine.? Casey was all business, a smile hovering on her lips as she saw Jack disappear into the bathroom. Jack found a complete set of clothes with underwear and shoes. He could manage the underwear and the bra. The dress was a tight fit and he had difficulty in zipping it up the back. After many attempts he gave up and decided to tell Casey it wouldn?t work. He was comfortable in the shoes and stepped confidently. ?That?s not going to work is it?? Casey said looking at an embarrassed Jackie. ?We?ll have to get more stuff and I think a tight corset will be necessary. My stuff won?t fit you. You have got used to the heels so we can try higher ones. We?ll have to go shopping tomorrow lunch and practice seriously tomorrow night. We have a date on Saturday and you need to be ready.? The evening was over within an hour and a disappointed Jack went back to his apartment. Luckily his bag contained the outfit he had worn yesterday. So he dressed quickly, applied the lipstick, pouted in the mirror as if he was inviting a cock into his painted mouth and masturbated. The next day Casey slipped him a note that they should meet for lunch and go shopping. Casey drove to a strip mall not far from the office. Jack looked uncomfortable. He didn?t want to try female garments in a ladies shop. ?What do we need to get?? he asked quietly. ?Look, Jack, if we are going to get this right and not embarrass each other, then we need Jackie looking really good. That means some nice breast forms, perhaps glue ons, a tight corset and higher heels. Don?t forget if this doesn?t work, I will be embarrassed in front of my friend. So are you willing to go all the way or not? I can turn back.? Jack was silent for a moment and said, ?No, I want to see this through.? ?Great,? Casey replied. ?We?ll need to drop some serious cash but I can see that Jackie will be around for more than one night. What do you think?? ?If I don?t do it I will never know. So, I guess I have to do it.? Casey laughed. ?Quite right and good attitude. You?ll see that this will all be worthwhile.? Casey knew where they were headed. It seemed to cater to a broad clientele and had everything from corsetry to wigs. The two very young Asian girls were heavily made up and wore short black dresses and very high heels. Jack wondered how they managed to stay in those heels all day. They were very helpful and didn?t bat an eyelid when Casey explained that Jack needed to dress as a female and needed a corset to give him a female shape. Jack?s cheeks turned a bright red but the girl, named Amy, didn?t bat an eyelid. She had the very thing and also rather good breast forms which could be inserted or glued on. Sensing a big sale, the girl went on to suggest extras in lingerie and even a gaff, a thong like garment. Amy took Jack into a small dressing room. ?My boy-friend, Jing, likes to dress and I help him. So no problem. We have many items for boys who like to dress like girl,? she said cheerfully as she attached the corset around Jack and tightened the straps. She inserted the silicone pads and Jack could now see the shape and fullness of his breasts. ?When you dress, bigger bust is better, like Jing? Amy said with a big smile. ?I like Jing with bust bigger than me.? Amy?s bust was probably a B cup whereas she had inserted C cups into Jack?s bra built into the corset. Casey had a big smile as Amy invited her to approve. Amy thought Casey was Jack?s girlfriend. ?We have a big date on Saturday and Jackie here needs to be perfect,? Casey said. ?It?s going to be Jackie?s coming put party.? ?Exciting,? Amy said. ?I am sure she?ll have fun. My friend Salina does great makeovers and could help.? Amy grabbed her purse and showed them a picture of two girls, smiling and in a tight embrace. ?That is Jing ? or June as she is known - and me at a party. She looks great doesn?t she? We have a great time and the sex afterwards is incredible.? Amy?s smile was huge. Casey didn?t need to hear more. ?Jackie needs to be ready by 6 pm Saturday. When can Salina do her? I mean everything.? ?I can call her. She will be meeting Jingi at 6 so before that. May take some time.? Amy took out her cellphone and dialed a number. She spoke in some Asian language. There were lots of smiles. ?Salina says she can meet you at 2 pm. If you want she can come to your apartment.? ?Great. Confirm to her and give me her number. I can send her my address,? Casey said. ?Jackie will be a hit. Amy pack everything up into bags we have to get back to work.? Amy helped Jack with unlacing the corset and put everything neatly back into the packaging. ?Come back tomorrow at lunch and we can get the wig you want. I assume you need one.? ?Oh, yes, what we have now is cheap and was for a trial.? Casey pushed Jack to the checkout. ?We?ll be back. Maybe you keep this stuff and we?ll pick it up tomorrow. Is that OK?? Casey suddenly decided it was time to go. ?Well, let me run your card quickly since these items have been used, I can?t keep them.? Jack handed her his credit card and Amy was quick to run the card. It wasn?t cheap but Jackie would be a definite hit. On the way back to the office Casey suggested Jack come over again as there was still stuff he had to learn. Jack agreed. Precisely at 6 Jack knocked on Casey?s door. He had the bag with the clothes. It was a little boring but he knew they had nothing new. Hopefully Casey would help him buy some new stuff. Casey greeted him with big smiles. The BIG DAY loomed. ?Get changed and we?ll take it a step farther tonight. Take a close shave. I left a razor for you.? Jack hurried to the bathroom. He knew the routine and soon became Jackie. Before he dressed he took a close shave. The wig looked a little worse for wear but they had nothing else. Jackie slipped on the heels and went out to Casey. ?Sit down at the kitchen table. I want to try something.? Jackie went to the kitchen and sat down as instructed. Casey followed with a small case. She removed the wig and inspected his face. She opened her case and Jackie saw a case full of makeup. Casey began to apply foundation, shadow and darkened his brows. She painted a thin line around his eyes. She applied many coats of mascara and finally painted his lips in a bright red color. ?Salina will do a much better job on Saturday. But I want you to feel the part.? Casey pulled the wig over Jackie?s head. She held out a hand mirror for Jackie to see. ?I?ll be right back,? she said and went back into the bedroom. It took some minutes and Casey reappeared. She had a simple robe on. Her breasts appeared bare, no bra. Jackie looked at her. Was she going to get lucky tonight? Casey looked great. ?Jackie, in order to be the woman on a date you have to learn somethings. Most important is that you have to please your man. Agree?? Jackie nodded not knowing exactly what Casey meant. ?Well, if your date has shown you a good time, as I am sure he will, you need to show your gratitude.? Jackie looked at Casey. She wasn?t sure what Casey meant. She knew there would be some kissing and groping. She hoped she would get to erupt through the actions of a partner than her own hands. Casey opened her robe wider. Jackie looked at the beautiful bare breasts. Her eyes wondered lower where Casey?s hands were stroking a big black penis aiming for her mouth. The head touched her painted mouth and she opened her mouth a little sucking in the tip. Within a few seconds, the thrusting got deeper and deeper and Casey made sure Jackie took it all in. ?This is the least you can do for your man, use your tongue and plenty of saliva,? Casey said. ?Sorry I have nothing for you to swallow but you will need to be ready and not lose a drop on the day. Keep your mouth firmly clamped around his cock.? This went on for quite a while. Jackie was getting used to that monster stretching her lips wide. ?You?re a natural but we?ll practice more tomorrow. Then we can take it to the next step.? Jackie saw that monster withdraw from her mouth strands of saliva dripping from it with traces of the red lipstick against the black of the plastic. It was better than she had expected and she believed the real cock would taste much better. On the Wednesday at lunchtime, Casey and Jack went back to the store. Amy had a big smile on her face as she saw them. ?I have chosen two very nice wigs,? she said and pointed to two wig stands. One was blonde with masses of curls. The other a medium-length brunette wig. ?We can try here or in the dressing room.? Jack turned a bright red. Amy understood immediately and took both wigs and led them to the dressing room. She brought a foldable chair and asked Jack to sit. She pulled a stocking like wig cap out of her pocket and pulled it over Jack?s head. She then placed the brunette wig on his head. Jack looked startled at seeing his image in the mirror: without makeup and the clothes, Jack looked like a man with female hair. The blonde wig came next: this gave Jack a totally different and sexy look. There was no contest: the blonde wig was the winner. They paid and left. Casey drove quickly to the Thrift store. Within a few minutes she chose a tartan skirt with red ruffled blouse and a black and red dress in stretchy material as well as matching shoes - a pair of 4: red heels which she had Jack try on discreetly. She shielded him from casual onlookers but the store was not particularly busy. Jackie already had a pair in black albeit in a lower heel. That evening Jackie wore her new tartan skirt, blouse and shoes. The breast forms filled out her top very well. Casey had got her into the corset and tightened it until her waist shrank enough and emphasized the rather large bust. Casey?s make up skills were not great and Jackie appeared more like a hooker than a woman looking for a nice date. There were many layers of bright red lipstick and it seemed that her mouth was much larger. With the blonde wig, Jackie certainly made a striking woman. Jackie couldn?t believe the transformation. She looked in the mirror and admired the result. She was not trying to pass but get sexual excitement. Casey disappeared and re-appeared in her robe. Jackie knew what was coming next as Casey took her to the small living room and had her kneel on the thick carpet. Within seconds Casey had thrown off her robe and placed her cock at Jackie?s mouth. She knew what was expected and opened her mouth. She kissed the head and sucked on it, ever deeper until she felt the hard plastic at the back of her mouth. She sucked on it for several minutes. Unlike a real cock, this one would never tire and go soft. Surprisingly, Casey stopped her and made her stand. Jackie wasn?t sure what she had done wrong but Casey had a big smile on her face. ?Now I just want you to lower your panties and bend over the back of the couch.? Jackie understood Casey?s intention and moved to comply. A couple of fingers entered her back passage with a cooling substance. An instant later Casey?s monster was poised at her back entrance. Jackie thrust back slowly to accommodate the dildo. Some pain ensued but Casey kept rubbing her backside and thrusting gently ever deeper into her passage. Jackie nearly stood straight as she felt the Casey?s body at her back indicating all 8? were deep inside of her. It didn?t feel so bad. The thrusts increased and Jackie felt her own cock rising. It didn?t take long for Jackie to erupt against the back of Casey?s couch. ?Lick that up, girl,? Casey said as she pulled out of Jackie. For the first time, Jackie bent down and tasted her own ejaculate. She licked the material clean. ?You?ll love the taste,? Casey said knowingly. ?Since Jackie will have her ?period? on Saturday, your date will have to be happy with this opening. We can practice again.? Casey gave Jackie?s bottom a friendly slap. Thursday was another practice run. Jackie felt comfortable dressing up and also being used at both ends. She was comfortable in heels now. Casey pronounced her ready for Saturday night. She had already set the date up with her friend and she promised Jackie would have a good time. But she insisted that another practice run was necessary before Saturday. Friday was the last practice night. Jack spent the Friday in a daze. His mind was on the weekend and Jackie?s coming out event. He had applied the hair remover again this morning and felt very excited about the weekend plans. He took another shower and went over to Casey?s apartment. He bought her a nice bottle of wine in thanks. He had spent a lot of money on becoming Jackie and it was all due to Casey. Casey opened the door to him with a big smile and took the wine. ?Surprise,? she said as Amy came into view. ?I?ll open the wine.? Amy hugged Jack surprising him. ?Casey thought she needed some help to get you ready tonight. Salina was busy so she asked me.? Amy grabbed Jack?s arm as they went to the kitchen. Casey had poured out wine and they toasted. ?I?ll get Jackie ready,? Amy said and moved to the bedroom with arm hooked into Jack?s. ?It?ll be some time.? Casey waved them off. She was going to relax. It took Amy almost ninety minutes to present a very sexy Jackie. She wore the same outfit as yesterday, but now had blonde hair piled on her head, dangling earrings, a bright red bow shaped mouth and large false eyelashes. The bust was quite large on a very narrow waist. Silk stockings and black 3? heels. Her fingers ended in long red nails. She looked hot. ?She?s beautiful,? Casey shrieked hugging Amy and then Jackie, careful not to smudge her makeup. ?How do you feel?? Casey asked with a big grin. Jackie didn?t answer immediately. ?Incredible,? was all she could say in a low voice. ?I glued on the breasts so Jackie can feel more comfortable by tomorrow. She can wear them for a long time before removing. Even take showers.? Amy was beaming. Casey laughed. ?So Jackie will go to work on Monday instead of Jack?? ?No no no, I can?t do that.? Jackie said although there was a hesitancy. Casey looked at Amy. ?Did you....?? ?Oh yes, Jackie is all plugged up and will have a great wiggle to her walk.? Amy was pleased with the way Jackie looked. ?Almost as good as my June.? Jackie looked at them embarrassed. Amy had lubricated his passage and stuffed a plug in the back under the tight fitting gaff. ?Well, let?s go. Drinks are on me,? Casey said beaming. ?I have a purse for Jackie. Just put cash and ID and what else you might need.? Casey handed Jackie a small purse with a long strap to go over her shoulder. Jackie opened it up and found some Kleenex and two condoms. ?I?ll get the lipstick for her,? Amy said and went to her makeup box. ?You want me to go out like this?? Jackie finally asked in surprise. ?Of course. How are you going to get a man sitting here? Let?s go check out the guys. It?s Friday.? Jackie was uncertain whether she would pass. But Amy and Casey convinced her that she was wrong. Besides, they were with her. Unless she was very lucky to find a guy who wanted to fuck her, she would be safe. Even then there were ways to convince the man: she had her period and could only offer him her other hole. This was the last thing on Jackie?s mind. She feared the humiliation of being read. They all piled into Casey?s car. The bars were lively, two cocktails reduced Jackie?s anxiety and with Amy and Casey constantly chattering, the evening turned out well. Several men made approaches and wanted to buy them all drinks. Casey shooed them away saying Jackie was her partner. They all laughed as the men disappeared. The night ended around 11 pm. ?Do you want to go home and meet tomorrow or come back and spend the night?? Casey asked. ?You can wear the same outfit to come back.? Jackie looked at them confused. She had a great evening. Going back with Casey meant her staying as Jackie. Then she thought that even if she did go back, she couldn?t take her forms off and the nails Amy had attached. Jackie was having a good time and decided she would go back with Casey. ?If it?s Ok I would like to go back with you. I don?t know how to get ready tomorrow to come back.? Jackie looked at her bust and Amy and Casey laughed. ?Great,? Casey said. ?Amy what about you?? There was more in the question than just drinks on the agenda. ?Sure. Why not. I?ve had a great time tonight.? They all linked arms and walked to Casey?s car. Back in the apartment Casey poured out the remainder of the wine, Whilst Amy chatted with Jackie, Casey disappeared into the bedroom. She was back soon wearing her robe and a big smile on her face. ?I told you we need to practice:? she said and let her robe fall exposing that black monster again. ?I think I need the restroom,? Amy said and disappeared. She was back soon fully naked. She too had something hanging at her crotch. It was red and smaller than Casey?s. ?I think Jackie needs to have it at both ends to celebrate her coming out.? Casey and Amy took it in turns to use Jackie?s openings. Jackie came without being touched whilst Casey fucked him. Casey stuffed the plug back in before the night ended with Jackie in a short nightdress sleeping on the couch. Amy promised to bring June back with her sometime for a double date. The big day arrived. Casey went out and made them a substantial brunch. ?You?ll not get much food after we tighten the corset. Drink slowly as going to the bathroom will be quite difficult.? Salina arrived at 2 pm with a roll on and a small case. She took Jackie to the other bedroom. It took almost three hours before Jackie appeared in that new, red dress. She looked perfect. Salina had brought out her eyes, had covered Jackie?s natural eyebrows and drawn on perfectly arched, thin eyebrows and made Jackie?s mouth larger and more inviting. Her waist was small and the short dress showed Jackie?s long nylon covered legs. Salina had applied massive false lashes, bright red lipstick with many layers of gloss. The smoky eyeshadow with hints of red gave her a wide eyed look, Jackie looked every inch the confident lady, dressed to the nines, planning to go out on a special date. She knew that her mouth and anus would be enjoying the real thing. ?Fantastic,? was all Casey said full of smiles. Jackie looked fabulous. ?Salina you?ve done a great job. I know you have to go to get June ready.? Whilst Jackie was getting ready, Casey too had changed into a short black dress. Her makeup was heavy but she had applied mascara and not used false lashes. They both looked hot. Salina wished them happy hunting and left. ?Let?s get some snacks and we?ll leave. I want to be there before Rob.? After they snacked and had a glass of wine, they were ready. Casey took Jackie into the bathroom, lifted her dress and inserted the fat plug with more lubrication. ?You?ll appreciate that later,? she said. They checked their makeup, gathered their purses and left. Casey drove. Both were silent as their thoughts went to what was planned. Jackie was ready for her big date.