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Chapter 1 Skyler was a lucky guy. He had just graduated college with good grades and was set to start his adult life in a way very few can. He was set up for great job prospects, if he cared about that at all. Skyler's parents had died when he was young, and he was raised by his great aunt. Sure, it was rough when he was younger and missed his parents and the normal life his friends all had, but his great aunt was from old money and so Skyler lived quite comfortably without the nagging and judgmental pressures of parents. Skyler's aunt had recently passed away as well and so he was now the proud owner of a college degree and a quite sizeable inheritance. Skyler was your typical, red blooded, American male, and as such had plans to use that inheritance to travel the world before he settled down and started looking for work. He was going play out the adventure that so many dreamt of, but so few achieve. It was going to be his right of passage. His trip would start in about a month, and it was going to be jam packed with adventure and excitement. He had plans to start the trip with a cross country road trip from his home state of New York to California. From there he would fly to Japan and hit the famous Hokkaido slopes and hot springs. The itinerary also included stops in Thailand, India, Italy, France, and the UK. The only thing the trip lacked was a beautiful lady to share it with. Skyler wasn't the sleeping around kind of guy and really hoped to be able to take a girlfriend on the the trip with him. That's where Skyler hoped Karen would come in. Karen and Skyler had been friends since high school and had gone to the same college. Although there was some obvious chemistry between the two, they never got together except the occasional drunk make out session. The stars never quite aligned, either they were dating other people or too focused on school work. But now, things were finally looking up for the would be couple, they were both free from the stresses of school and single. To top it all off, Karen, not being so financially stable as Skyler, was now desperately searching for a place to live after moving out of the college dorms. Skyler invited her to live with him as roommates in his late aunt's small but well furnished home. Skyler was of course hoping to develop their relationship in time to ask Karen to join him on his trip. The day Karen moved in, Skyler was reminded once more of why she always remained out of his reach. Karen was a knockout, with a fairly tall 5'10" frame equipped with the perfect proportions of breasts, to waists, to hips. Karen stood on long, lean, and irresistible smooth legs, covered on this day by only a pair of athletic shorts, that ended in a perfect bubble butt. Her body was the perfect combination of good genetics and diligent exercise. Karen's face was equally well endowed with beauty. Her half Asian, half white heritage resulted in a perfectly shaped face with smooth skin and the most beautiful eyes that hinted at her ambiguous racial mix. Skyler helped her move in but couldn't help but steal glances as Karen moved and flexed with the effort of unloading her many belongings. "Thanks again so much for letting me to stay here Skyler," Karen said as she took her last box into her new room. "No problem at all, glad to help" was Skyler's response. "And I don't want this to be weird for you at all so if you have any questions or concerns at all, please let me know." "As Sweet as always, Huh?" Karen laughed. "But don't worry about me. In fact, I might make things weird for you! I'm used to living in an all girls dorm. I'm rather accustomed to speaking openly when at home. And with a shared bathroom, you're bound to see way more than your fair share of female beauty products. I'll have to remember to put everything away instead of leaving it out for my roommates." Skyler handed Karen a glass of wine as they sat together in the living room for the first time. Skyler knew the wine was a favorite of Karen's and was hoping to start charming her early. With his own beer in hand, Skyler returned to the conversation, "don't worry about it at all. In another month or so I won't even be here anymore." That last line was Skyler's first attempt to hint at inviting Karen along. "Oh yea, your wonderful around the world adventure! I almost forgot about that. How exciting for you! But do you really plan to leave lil' old me home alone?" Karen said, half jokingly. Skyler couldn't believe his luck, it looked like Karen was already open to the idea. The two started into each other's eyes for a moment, neither quite sure what to make of their exchange. Soon enough Karen broke the stare. "Well, I'm exhausted. I think I should get to bed." "Yea, sounds like a good idea," said Skyler as he finished his beer, taking his bottle and Karen's glass into the kitchen. "Good Night..." Said karen as she walked up the stairs towards her room. Skyler couldn't be sure is she was intentionally giving him the perfect view of her ass or not, but he didn't really care. He was lost in the experience and the prospect of possibly traveling the world with such a beauty. Chapter 2 Their first week as roommates went perfectly, Skyler had thought. He has decided that he would try to be a little more flirtatious in attempts to try to gauge Karen's reactions. For Skyler, this mean a little light teasing and initiating little games and challenges whenever he could. He also snuck in a few at home dinner dates with challenges to make the best meals. It was early Saturday night, when Skyler tried this trick again. "That Vietnamese pork you made the other night way pretty killer Karen, but I bet I could do better tonight!" Skyler teased, expected to then move in the kitchen for an impromptu cook off full of nudging each other of the way and playful mini food fights. But Karen didn't bite this time, she just sat on the couch looking worried. Skyler knew there was something she wanted to say. Skyler dropped the playful act, asking with sincerity, "What's wrong Karen?" "I don't want to seem ungrateful for everything you've done for me..." Karen started, pausing to gauge Skyler's reaction. "But, you have been awfully competitive lately, I don't know what's gotten into you. But I'm just not used to it. In the dorms me and the girls always cooperated and worked together, instead of always challenging each other." Skyler couldn't believe it! He thought the flirting had been working but now Karen was genuinely upset! He couldn't let her know that he had been trying to flirt with her. "Oh my gosh, I'm so sorry Karen, I never meant to upset you. I guess I've just been letting my competitive nature get the best of me! I've always tried to keep it in check but I can never quite beat it," Skyler said half truthfully. He indeed had a competitive spirit but not so much that he couldn't dial it back. Skyler looked away, not sure what to say next. After a moment Karen offered a suggestion. "You know, I learned a little bit of hypnosis as part of my psych degree. Maybe instead of cooking dinner, tonight, we could take the time to try a hypnosis session to try to break that overly competitive attitude." Skyler was stuck. He didn't want to pedal back what he said and appear untruthful with Karen. His only option was to go along with the hypnosis. He didn't believe in such nonsense but he was willing to do anything to stay on Karen's good side. He agreed and laid back on the couch. Karen sat for a moment, planing the hypnosis session in her mind. She knew she couldn't make any large changes with just one session but she saw an opportunity to make her life with Skyler a little more like her life in her all female dorm. To do this, she decided that instead of fighting Skyler's competitive nature, she'd use it to her advantage. She guided him into trance, and whether he believed it or not, she could tell that Skyler was under. She began her suggestions. "Skyler, Listen very carefully to my suggestions. From now on you will feel more and more competitive every time you lose a challenge or a bet. As your competitive nature grows stronger, you will begin to fear making bets or challenges for fear of losing. However, when ever you are issued a challenge or a bet, you will not be able to turn it down, your competitive spirit will always accept, no mater what the stakes. When you pay up for your bets, you will feel prideful and happy. You MUST always pay up on your bets. Not doing so will cause you great discomfort and anxiety until you do." Karen repeated the suggestions in a number of ways until she was confident that they stuck. Happy with the results, Karen brought Skyler out of trance, making sure we wouldn't be able to remember the details of the session. Skyler woke up to see that it was now much darker outside. He was confident that the hypnosis didn't work but couldn't figure out how so much time had passed without him noticing. He decided to play along. "Did it work?" he asked. "No way of telling quite yet, we'll have to wait and see," Karen replied. "Well, what should we do now?" Skyler asked as he went to get himself a beer and Karen a glass of wine. "Well," Karent started, "on Saturday nights, my roommates and I always gave each other mani pedis. I don't expect you'd be very good at it but I could do yours..." Skyler laughed at the idea, "no thanks, I think I'll keep my plain old nails, thank you very much" "Aw, come on! I bet our hands and feet would look really cute with painted nails!" Skyler heard this as he finished pouring Karen's wine in the kitchen. "No way would my hands look cute, "he thought to himself. He practically ran out of the kitchen to accept the bet. "You're on!" he yelled. "Great, but let's make it even more fun!" Karen responded. "If I win, and your hands and feet do look cute with painted nails, then you have to practice doing mani pedis all week so that next Saturday you can return the favor. You'll give yourself a mani pedi every day this week, painting your toenails a different color each day and at least painting your finger nails with clear coat." "Sure," was Skyler's almost immediate response. "And if I win?" "Then every Saturday, instead of mani pedis, we'll give each others feet and hand massages." It was too good to be true! When he won the bet, Skyler would get to giver Karen massages every week. His plan to charm her into being his girlfriend was going better than planned. "Deal," he said. Skyler settled into the couch for the second time this evening as Karen worked away for well over an hour. He had no idea how much was involved. He was instructed to pay attention as Karen exfoliated and moisturized his hands and feet. Cut and shaped his nails, and finally started applying polish. "Now, I don't want to you to cut your nails this week when you give yourself a mani, we need them a little longer by next Saturday," Karen said as she finished up the last coat. "Fat chance of that," Skyler joked. But his attitude completely changed once Karen was done and removed his fingers from her portable dryer. He couldn't believe his eyes, his hands and feet were so well moisturized, that they looked just as soft and lean as Karens. Karen had also picked a soft pink polish that was barely darker than his nails were normally but the color combined with their shape, and the soft skin left him speechless. "What do you think?" Karen said with the same excitement and enthusiasm she'd share with her old roommates. "They're... cute," Skyler replied without realizing what he had said. He instantly regretted it. He was too embarrassed to look up at Karen as she went the kitchen to make them some salads for dinner. As she passed him, she reminded him of the bet. "I look forward to my mani pedi next week!" Chapter 3 The next morning Skyler awoke in his bed and was startled once again by his cute hands and feet. They were still soft and feminine and he was eager to remedy that. He went to the bathroom to remove the polish. As soon as it was off, he began to feel really anxious. He knew that he should honor his bet but he just couldn't bring himself to paint his own nails. This lasted until mid afternoon. He wasn't able to focus on planning his trip at all. All he could think about was how he was welching on his bet. Karen could see his discomfort and offered her help. "Hey Skyler," she said as she walked up to him and sat next to him on the couch. "Still upset about losing the bet? I could help." Skyler looked up at her as she continued. "I could put you back under and try to reduce your competitive attitude a little more." Skyler was eager to try anything to ease his anxiety, short of actually painting his nails and quickly agreed. Once Skyler was in trance, Karen went to work. She reminded him that the only way he would feel better was if he paid up on his bet, he had to paint his nails. Karen also saw another opportunity to make sure that she'd always have a mani pedi buddy. "Skyler, listen very carefully. From now on, if you do something every day for a week, it will become part of your regular routine. You might not always do it as frequently as every day but you will always have it be part of your life. Once you do something every day for a week, it will become completely normal to you and you won't remember life without it." Happy with the results, Karen reinforced Skyler's triggers, and brought him back out of trance. "Any better?" she asked. Skyler thought for a moment before responding, "No... I still feel really anxious but I think I know what will help." Skyler went to the bathroom and found a jar of light blue nail polish and clearcoat, as well as exfoliant and moisturizer. He took his tools back to his room and got to work. It took him a lot longer than Karen took and he had to watch several youtube videos to remind himself of proper technique but when he was done had had cute blue toenails and shiny, plain colored finger nails. Even with the clearcoat, Skyler's hands were still undeniably soft and feminine thanks to the moisturizer. Despite the embarrassment of his clearly feminine appendages, skyer was proud with himself for following through with his bet. The rest of the week was relatively uneventful. Skyler took the time every morning to redo his nails and spent the rest of his days planning his trip. Karen spent her time looking for jobs and planning her next hypnosis sessions. She occasionally made little bets over things like taking out the trash or paying bills with Skyler, just to maintain his conditioning. I was Saturday night again and at this point, painting his nails was second nature to Skyler. In fact, it seemed odd to him that he and Karen even had to make a bet like this since he's always painted his nails. He had even returned to his old habit of painting his fingernails with soft pastel colors. Karen and Skyler sat in their living room in shorts and t-shirts as they did each other's nails. They chatted about technique, colors and moisturizing tips. Skyler had seen a french manicure tutorial online but couldn't quite pull it off on himself and decided to ask Karen to do his nails in that manner. As they finished, Karen seemed to be distracted by something on Skyler's arms and legs. "What's wrong?" Skyler asking, inspecting his arms, expecting to find a bug or something. "Oh nothing," Kareen started, "it's just that now that you've gotten back into painting your nails, it's a shame that you have so much body hair. Your hands and feet would look so much nicer with smooth arms and legs attached!" Skyler looked at is nails. Karen had done a wonderful job and since he had let them grow out again, they had a nice length to them. "I don't know Karen.... I've always painted my nails but I've never seen a problem with my body hair." "Really?! I just love having nice smooth skin," Karen responded. "I bet you'd love it too." Skyler had to fight back his immediate urge to accept Karen's bet. He had lost so many of their little bets over the past week and was afraid what would happen if he lost this one. But his competitive attitude got the better of him and eventually agreed. "Fine, but if I win this bet, I want to get to feel your smooth legs" Skyler said in an attempt to turn their exchange into a flirtatious one. Karen laughed and gave Skyler a coy smile. "Fine," she said, "but if I win, you have to keep your body smooth for this whole week, that means waxing or shaving every day. No hair other than your head, your eyebrows, and your pubes, if you want to trim them into a cute shape" Karen ended her challenge with a wink that sent Skyler's head spinning. "You have a deal!" Skyler said confidently. "Wonderful, why don't you go take care of that now? You can use any of my nair or razors," Karen responded. Eager to win the bet but embarrassed at the idea of talking about his hiar removal, Skyler moved quicking to the bathroom and began to draw a shower. He could hear Karen downstairs, ordering some pizza. It took about an hour, as well as a mix of nair, shaving cream, and about 3 razors, but Skyler was now completely hairless, save for his head and a trimmed patch of pubes. As Skyler dried off and got dressed, he headed back down to the living room to confront Karen. This time Skyler felt confident, as he could honestly say that he did not love his hairless body. He was cold and his rough cotton clothing made him uncomfortable without the barrier of body hair. He told all of this to Karen who was disappointed but she too decided to honor their bet. "I guess you'd like to claim your prize now?" she asked coyly as she layed down on the couch and struck a pose that left her legs free for the touching. Skyler smiled a mischievous grin as he moved over to claim his prize. He started at Karen's ankles, gently touching the soft skin with his perfectly manicured hand. He shot karen a sly glance as his hand moved up her leg, savoring in the experience. As he approached the top of her thigh, Skyler noticed that Karen had changed into her silk pajama shorts. He stopped to admire the soft shimmering look of the fabric. "Go ahead, feel them," Karen encouraged. Skyler ran his hand slowly further up Karen's thigh and just under the edge of her shorts. As he went a little higher, he could feel the very edge of her soft cotton lace panties. Much to Skyler's disappointment, Karen jumped back with a wicked smile on her face. "Something on your mind?" Skyler played along. "Yea actually.... I think you should try on what i'm wearing, I think they'd just about fit you!" "Oh yea? And why would I do that?" Skyler asked. "Double or nothing!" Karen shot back. Skyler sat a moment confused. "Ugh, do I have to explain everything to you?" Karen joked. "I want you to try on a pair of my soft cotton painties and pair of my silk pajama shorts. If you just LOVE the way they feel on your soft , smooth skin, then you have keep yourself hairless all week. Plus wear a pair of panties every day and silk shorts to bed. If you win, I'll let you see what I've got on under these shorts..." This was going to far for Skyler. Panties every day?! No way. But then again, the payoff if he won would be amazing. After a short internal struggle, Skyler decided that it wasn't worth the chance, that he'd get to see Karen in her lingerie the old fashioned way. As he was about to decline the challenge, he heard himself accept! Before he could realize what he had done, Karen reaching into the couch cushion and brought out a pair of pink cotton panties and pink silk shorts and tossed them to Skyler. "Great, get dressed!" she chirped. Skyler caught the soft fabric and grew worried as he could already tell that he liked the way they felt in his hands. As he wandered into his bedroom, he had to wonder why Karen had a pair of panties and shorts ready and waiting. Safe in the confines of his room, skyler stripped off his own shorts and boxers and started to pull up the soft panties. Skyler knew he was in trouble. His soft hairless skin that was so uncomfortable before was now soothed as the soft fabric caressed his legs. Skyler started to get an erection but knew that would certainly mean a week in panties. He did his best to quell his arousal with thoughts of math and politics. It worked, but just barely. With the panties on, Sykler caught a glimpse of his smooth hairless legs and ass in a pair of pink lace panites in his mirror. From this angle, he looked almost like a real woman getting dressed. He turned so that he now faced the mirror head on and his bulge ruined the illusion. With great embarrassment and more math problems and presidential speeches in mind, he quickly put on the shorts, trying his best to ignore their soft, sensual caress. With all the concentration he could muster, Skyler headed back to the living room to try to win his bet. "Wow! So sexy!" Karened whooped as he descended the stairs. "Why the serious face? Is the soft embrace of silk to much for you you bare? Or are you imagining me paying up and stripping off theses shorts?" With such temptation, Skyler's concentration broke and he was left a large bulge in his feminine attire by the time he reached the bottom of the stairs. He knew he had lost. He felt his competitive spirit surge, ready to take on another challenge to regain his pride. "Well well well, look who enjoys the finer things in life," Karen teased. She walked over and ran her hand up Skyler's thigh. Before Skyler could enjoy the sensations, the doorbell rang. "Oh that must be the pizza guy! Be a dear and let him in while I get some money." Karen said nonchalantly. "No way," Skyler shot back. "I can't be seen like this!" "Stop whining, I bet they'd love to see your smooth legs and cute painted toes!" "I can't..." Skyler started, but stopped as he realized this was his chance to win again. "I'm just kidding anyway, they probably won't even say anything," Karen joked, "but if they do, listen to any tips they might have for you!!" Karen continue her playful laughter as she left to find her purse, not realizing that she had just set another bet. This time Skyler wasn't even offered a possible prize, but with the embarrassment of his recent loss, he had to take the challenge, even if Karen didn't intend to make the bet. He bravely walked over to the door and opened it. On the other side was quite possibly the worst possible choice in Skyler's mind. A burly straight guy would be too embarrassed to say anything, and a woman would probably just laugh at his embarrassment. But on the other side of the door, holding the pizza box, was Jake, the most flamboyantly gay guy from their college. Skyler could see that he toned his exuberance down for work but as soon as he saw Skyler's shorts, he broke into his expected persona. "Ooooh Skyler, I had no idea you enjoyed such things," Jake said as he cocked his head and hips in opposite directions, resting his free hand on his hip. He did an up and down look of Skyler's legs. "Giiirl, those legs are fierce! I guess I should call you Sky from now on, huh, honey? You know I'm digging that bulge but it ruins the look, you need to tuck that man meat!" Skyler could have died of embarrassment. He looked down in shame and walked to the other side of the room as he let Jake into the foyer to wait for Karen. Jake chimed in again, "Now you know that's no way to walk when you've got legs like yours! You got to give us a little sway girl! And put your shoulders back, arch your back, be confident!" As Skyler continued his journey into the living room, his back and hips suddenly became extremely uncomfortable. He adjusted his stride to add some sway to his hips and brought his shoulders back. Instant relief. But as his hips and back relaxed, a discomfort grew in Skyler's crotch. "That's it! Work it!" Jake teased from the foyer. Much to Skyler's relief, Karen returned with money for the pizza. With Jake gone, Skyler could finally relax. He went to the kitchen for another beer. Karen noticed Skyler's feminine gate but had no idea where it came from. She decided to let it be for now. Jake sat uncomfortably as he ate a single slice of pizza and try to discreetly adjust his aching junk. He was too lost in though to pay any attention to the chick flick Karen had put on the TV. This was going to be a tough week for Skyler. Had to shave and wear panties everyday. And on top of that, Skyler noticed that for some reason he could now only walk with a feminine sway to his hips and arched back. He turned in early that night hoping that things would sort them out the next day. He was finally able to sleep after discovering that he could relieve the discomfort in his crotch by sliding his junk back and up between his legs. Chapter 4 The next morning, Skyler woke up early to try to sort out his thoughts. Karen came into the kitchen to find him eating his small breakfast. "You look stressed, buddy," she said as she joined him at the table. Skyler just sat there in his silk shorts and t shirt as he stared into his breakfast. "Let me take you out today," Karen offered. "We could go shopping, get you some panties for the week. And maybe we could go to the new yoga place together." While he didn't like the sound of lingerie shopping, Skyler could already feel the oncoming anxiety associated with welching on a bet. And the yoga class part sounded pretty great, He'd get to watch Karen twist and bend in all sorts of ways. He finally started to cheer up. "That sounds pretty good actually," said Skyler as he finally looked up from his breakfast. "Before we go, why don't we see if some hypnosis will help you relax," suggested Karen. Skyler quickly agreed. Once Skyler was under trance, Karen first asked why he was now moving femininely. She found out that it was the consequences of her unintended bet last night and made a mental note to be more careful. She also decided to inject a few suggestions to make their shopping trip a little more fun. "Skyler, it is now very important to you that when you are shopping that you consider a lot of options. You like to look at things and consider things more like a woman on a shopping trip than a man. Also, if something you're buying has an additional piece to match it, you just have to buy it. You love to have matching sets. Anything you buy, you will love to wear, even if it's not your typical choice of attire." Excited to test the new suggestions, Karen brought Skyler out of trance and drove them to a local mall. Once there, Skyler was clearly uncomfortable as they headed into Aerie. "They'll have everything we need here," assured Karen. Skyler was ready to get in and out with a quick purchase but all that changed as soon as they entered the store. Presented with such a selection, Skyler suddenly found a new thrill in going through all the options. He had no idea there were so many different colors, styles, and materials. After about 30 minutes of sorting through the selection, Skyler and Karen found an assortment of seven pairs of panties in a size that they thought would fit Skyler. Despite the impending embarrassment, Skyler was actually having fun shopping with Karen. With panties in hand, they started to make their way to the pajama section but Skyler stopped dead in his tracks when he saw an assortment of bralettes that looked like they matched some of the panties he had selected. For some reason, he just had to have the matching sets. After another 30 minutes of bra browsing, they finally made their way to the PJs where Skyler was met with even more matching sets. Here, Skyler picked out two of the required silk shorts, one in a light lime green, and one in a peachy pink. But once again, Skyler found himself drawn to their matching tops. He picked up the matching silk camisole tops as well. The pair finally returned home with their purchases and Skyler was surprised to find himself excited to try on his new underwear. So excited, in fact that Skyler issued his own challenge for the first time in nearly two weeks. "I bet these are going to looks so good," Skyler gushed with an excitement that surprised both of them. Karen was shocked but entertained at the thought of whatever challenge he might offer. "What are the stakes?" she asked. "How about I do a little fashion show of my favorite set and if you like what you see, you have to show me the lingerie you're wearing right now too," offered Skyler. "Deal," Karen chuckled as Skyler hopped off to his room to change. Karen took the moment to think about what she was doing. She had been having fun up to this point but began to think about the possibilities. She knew that Skyler was going to ask her to go his trip as his girlfriend eventually. While she did like Skyler, a lot actually, his approach to relationships was far more narrow minded than she prefered. She prefered open relationships and while Skyler didn't know it, she enjoyed the company of both sexes. She thought that although this isn't what Skyler had in mind, she could do them both a favor and help him become her perfect partner. As she resigned herself to her decision, she was interrupted by Skyler entering the room. Skyler's naturally tall and slender frame, now silky smooth and soft, sauntered into the room clad in only a lavender colored halter t-back bralette and matching bikini cut panties with lace trim. Karen saw no sign of a bulge and wondered when he had learned to tuck like that. He had pulled his shoulder length hair into a high ponytail to give a clear view of his pretty lingerie. His hips swayed proudly as he walked to the center of the room and struck a pose. "What do you think?" he finally asked after a long pause. Karen stared, speechless. Skyler already looked better than she could have imagined. She had definitely made the right choice in continuing with his feminization. Without saying a word, she stood up and removed her shorts and blouse to reveal her own matching set of lingerie. Ecstatic that he had actually won a bet, Skyler hopped in place which had the unintended consequences of making him look even more like a girl. Before Skyler had a chance to take in Karen's full beauty, she had pounced on his slight frame, tumbling them both to the couch. Karen's hands were all over Skyler as he got a first hand experience of being the one to be felt up. He instinctively took on a more feminine and coy posture; he was receptive but trying to maintain his modesty by keeping his arms close to his body as his legs closed. As Karen's tongue plunged into Skyler's mouth, her finger also plunged into the nook between his legs. She eventually found what she was looking for, the tip of his cock. Karen continued to invade Skyler's mouth as she massaged his cock through his panties. She was fingering him like a girl and he responded in kind, squirming and bucking beneath her. She stopped just before Skyler came. She looked him right in the eyes and said, "I want to travel the world with you, will you have me?" This was everything Skyler had hoped for. "Oh yes!" he cried out. "Travel the world with me! Be mine! Make me cum!" And with that, he took matters into his own hands, rubbing Karen's soft mound through her panties. They continue to rub each other off. Karen had two ear piercing orgasms before she let Skyler cum, she knew just how to play his panty clad sweet spot. Karen collapsed onto Skyler, her ample breasts pressed against Skyler's own lace covered chest. Skyler stared down into Karen's soft cleavage. "I bet you could never grown big beautiful breasts like these suckers" Karen challenged. This took Skyler out of the moment, how could he even grow breasts to start with? Even if he could grow breasts, they'd never be the full D cups Karen had. Despite the obvious hurdles, Skyler found himself agreeing to the bet. "Great,"said Karen. "Let's not put a time limit on this. We'll compare whenever yours stop growing. If they're not as big as mine at the point, you'll get breast implants." As Karen got up to get dressed again, Skyler just lay there, unable to believe what he just agreed to. He was going to have breasts, no way around it. Chapter 5 The next week went by in a blur. Skyler had starting taking extra strength hormones in order to win his boob bet. He and Karen were also now regular members of the new yoga club, going every day. Skyler also had a standing bet every day to come up with a new way to style his hair otherwise Karen said she'd die it neon pink. By the end of the week, Skyler was convinced that he had always worn his hair in a feminine manner and decided to get a trendy new hair cut. He had it cut into an asymmetrical bob with side bangs. He had a dark red under layer added to his rich brown hair. Around this time, Skyler noticed that he had somehow accumulated a large collection of boxers. This was particularly strange because he only wore panties. He got rid of the boxers and and he and Karen made another shopping trip to Aerie. His drawers were now full panties, thongs, and boy shorts. He had almost as many bras. He was frustrated because he had been trying to grow boobs for as long as he could remember and still had nothing to show for it. He'd favored heavily padded bras lately to at least create the illusion of a bust. Skyler's relationship with Karen was going great. They spent their time cuddling, shopping, and doing each other's nails. They had even gone for a full body waxing together. They were perfectly smooth, save for matching heart shaped pubic hair patches. The sex, however had not yet evolved beyond handjobs. It was Saturday afternoon when the topic came up again. As Karen was filing Skyler's nails, he suggested taking things further. "So... I was thinking that tonight maybe we could try taking the sex to the next stop" Skyler offered tentatively. "I'm not that kind of girl Skyler!" Karen joked. "I want our relationship to be unlike any either of us has ever had before. I want us to understand each other completely before we start sleeping together. I really like you but I don't think you're there yet." "What can I do to better understand you?" Skyler asked nervously. "We tell each other everything, what else is there?" "Your beautiful Sky, but you don't really know what it's like to be a woman in this world, how everybody treats women is different. To really understand me, you have to fully understand women. You'd have to convince the world that you are a woman. And there's no way you could do that." Skyler's conditioning reacted to the challenge. "I absolutely could! How hard could it be?" "Fine, let's make a bet then. We'll go out tonight and you have to try to pass as a woman. If no one calls you out, then you pass and I'll rock your world tonight. But if anybody calls you out tonight, you have to ask them what you should do to be more passable and follow their instructions for a week." Skyler eagerly accepted the conditions and asked for bright red nail polish. "I've got to go all out." Once they were done with their nails, Skyler and Karen spent the rest of the day at the mall, preparing for tonight. Their first stop was Sephora where they both got sultry night time make overs. This was Skyler's first times wearing makeup but the beautician was very reassuring, "If your practice makeup techniques for even just a week, I bet you'd be an expert!" Karen smiled as she imagined the results of that unintended bet. Sure enough, Skyler took it seriously and left with a stunning makeup job, and several hundred dollars worth of supplies. As Karen's makeover was being finished up, Skyler disappeared. Karen started to worry when he suddenly showed up with percy D cup breasts poking through his t shirt. "Holy cow Sky, did you find the boob fairy in the food court or something?" Karen joked. "I wish!" replied Skyler. "I had these attached at the special effects makeup place. They're super lifelike and semi permanent. Here, feel." Skyler thruster his chest forward for Karen to get a handful. If Karen didn't know any better, she would have said they were real. "Let's hit Victoria Secret next," exclaimed Skyler. "I need a sexy new set of lingerie for tonight and none of my current bras will hold these cans." Karen couldn't help laughing to herself at how femininely Skyler was already acting. It was all too good to be true. Skyler wore his new lingerie out of the store so as to support his new assets. They next hit the boutique shops. This was the first time Skyler went shopping for actual women's clothing and he had a blast. The existing conditioning meant the he reveled in the options and loved trying on all different fashions. He ended up buying way more than what was necessary for tonight's outing. He got several skirts of various lengths, sun dresses, shorts, all sorts of tops, and a little black dress for tonight. He also found the perfect 3 inch heels to match his dress and several pairs of more casual shoes as well. With his new semi permanent breasts attached, he also needed a few sports bras and the matching yoga pants so that he could continue with yoga class. He was of course dying to wear it all, thanks to his conditioning. All through out the shopping trip, the sales ladies treated him wonderfully. No a single one made a comment about him being male, even when he was practicing a female voice. His confidence was growing. Happy with their purchases, the couple headed home and got ready to go out. The two of them were stunning. They looked like two tall models, ready to hit the town and land some studs. The yoga plus hormones gave Skyler a great ass and thin waist that helped create the illusion of curves. And they both sported short dresses that showed off their killer legs. As they parked the car and approached a local club Karen reviewed the bet, "Remember, if anybody calls you out, you have to follow their advice on passing as a woman. If you make it to closing and nobody calls you out then we go home and make crazy love. We can leave anytime you want but remember that I want you to understand what it's like to be a woman in this world so the longer we stay the better." Karen leaned in for a kiss and a slap on Skyler's ass as they walked into the club. Chapter 6 That night at the club had pushed Skyler further into femininity than anything had up to that point. The night had started out well. Skyler and Karen hung out together by the bar for about half an hour before things took their first bad turn for Skyler. At that time two young attractive men approached them. The shorter Latin one started flirting with Karen and the tall white guy was trying to talk to Skyler. But all Skyler cared about was getting the the Latin guy away from Karen. "Hey, she's taken, so you can keep on moving." Skyler yelled at the Latin guy. He turned to face Skyler, clearly angry, "What are you, her boyfriend or something?" He spat. Skyler could see that Karen was disappointed, he had no idea what was going on. After a moment and a long hard look at Skyler's face the Latin guy spat back, "Oh my God you ARE her boyfriend, aren't you? Damn, good thing you both look fine as hell otherwise you'd get your ass kicked." He leaned in close to Skyler's faces and said, "you had better stop worrying about your girl and start flirting with some dudes otherwise they gonna kill you, bitch." With that the first two men left and Skyler sat in shock as he processed his first "tip" of the night. He'd have to flirt with guys all week. "Well that wasn't very lady like," Karen yelled with anger. "I know, I know, I'm sorry. I'll do better," Skyler promised. "Well you had better, I'm going to go apologize to that guy" Karen's yelled over the crowd as show ran after the Latin guy. Skyler thought to go after her but the guy had told him not to worry about Karen, and doing so caused him great anxiety. He tried his best to forget about her for now and finish his drink. As he did, a tall, well muscled man walked right up to him. "Buy you another drink?" He offered. Skyler was going to send him away but the the anxiety started to hit and he knew what he had to do. He looked the man right in the eye, gave his best coy smile, and accepted his offer. Doing so filled Skyler with pride and happiness as he was completing his bet. He was actually enjoying this man's company. "The name's Mike." "Sky," Skyler replied as he sipped on his drink. "What brings you out tonight, Sky?" "Oh, you know, just looking to have a good time." Skyler realized the implications of what he had said too late but figured he must have been doing a good job of flirting as the man leaned in even closer. They were now talking with their faces practically touching. "I'm looking for a good time too," Mike whispered as his hand found Skyler's exposed thigh. Skyler was so proud of being a good flirt that he actually moaned a little at his touch. He figured the flirtatious thing to do would be to return the touch and so he found his hand wandering over Mike's muscular abs. "Is that a six pack.... No feels more like an eight pack," Skyler cooed. Even though he didn't really enjoy the feel of Mike's muscles or find them appealing, he really just enjoyed egging Mike on. As Mike's hands wandered up, Skyler's went down, matching the flirtatious advances. Mike leaned in for a kiss but Skyler managed to avoid it without anxiety by convincing himself that being coy would be the flirtatious thing to do. As Skyler's hand felt the tip of Mike's bulge, he snapped out his flirtatious trance and jumped back. Mike leaned in real close to Skyler and said, "I know you're one of those special girls, Sky. I can tell that this is for first time in public with a man. But you can relax with me," he reassured Skyler. Skyler was filled with embarrassment for having flirted with a man and being call out for being a man himself. He also knew what this meant. "What could I do to be more convincing?" Skyler asked. Mike was surprised by the straightforwardness of the question. He thought for a minute and continued, "The way you flirt is pretty stereotypical, like your just emulating what you've seen in movies. You have to really want to impress an attractive man such as myself. You have to want his attention and approval, his body, and most of all, his..." Mike's lips were now right next to Skyler's ears as he whispered the last word "cock." It was all too much for Skyler. He had to get out of there. He excused himself to use the restroom, with no intention of returning to Mike. Skyler entered the women's room, knowing that the men's room would be a minefield. He entered a stall and closed the door. As he stood to relieve himself, he was horrified to find that he was taking great joy in thinking about Mike's hard abs and his powerful member that Skyler's only got to barely feel. He needed Mike's attention again. He decided that he needed to go back to Mike to ease his anxiety. As he washed his hands, the woman next to him began talking. "You know, if you want everybody to believe you're a woman, you can't stand to pee!" The woman was being playful and non judgmental but Skyler turned to her, speechless and staring. "And don't be so quiet!" She continued, "women gossip to each other, tell each other what's on their minds." Skyler suddenly became very anxious about keeping his concerns to himself. He opened up to the woman, "I was flirting with a guy out there... But I think I offended him. I just want him to be happy with me again. He was so muscular too! And I almost got to feel his cock. None of this should matter to me but for some reason it's really important to me now!" Skyler looked down at the sink, holding back tears. "Let it out honey," the woman cooed. "Women wear their emotions on their sleeves, there's nothing to be ashamed of." With that Skyler began to sob. Despite his fear and confusion, it felt good to confide in another woman. The woman gave him a tight hug and he began to feel better. He knew what he had to do, he had to go find Mike. He composed himself and fixed his makeup. "The names April, by the way" she said as she left Skyler alone in the bathroom. " I hope we get to hang out again sometime soon." Skyler headed back to bar with a renewed confidence. He was still confused but he knew that Mike's attention would make him happy again. Upon returning to his spot, Skyler was filled with disappointment, Mike was gone. His disappointment was soon replaced with excitement as he spotted Karen near by. As he approached her, he could see that she was talking to April, the girl from the bathroom! "Sky!" Karen yelled as she noticed him. "Come over here and meet one of my old roommates, April!" "Oh my god!" April gushed. "YOU'RE Sky? Karen's new roommate?! That Sky?" Skyler nodded sheepishly as Karen watched their exchange with confusion. "Have you two met before?" Karen asked "Just now, in the bathroom," replied April. "In fact, Sky was telling me about her night. Why don't you fill in Karen?" she said as she handed Skyler a Cosmo. Skyler didn't want to tell Karen about his feelings for another man but it had felt so good to open up to April before. He grew more anxious until he decided to bite the bullet and told Karen all about his exchange with Mike. It felt so good to talk to other women like this, that he got really excited as he told the story. "But now he's gone, and I don't know what to do..." concluded Skyler. Karen couldn't believe it, the night wasn't even over and Skyler was already on his way to appreciating her version of sexuality. She wondered what kind of tips and suggestions he had gotten so far. She decided to take a moment to ensure that he stayed as open minded about relationships as she did. "It's ok babe, why don't we find a quiet place and I can try to ease your concerns with hypnosis?" Skyler was so happy at the thought of Karen removing these strange thoughts that he practically ran to one of the private booths with the two ladies. April watched in awe as Karen put him under. She began her suggestions. "Skyler, you are beautiful and confident. There is no need to worry yourself over just one person. You and I will grow to love each other but we both need to continue to experience other people. Never worry yourself over just one person again. There are so many people in this world and you're open to experiencing so many of them. Don't forget the other things you learn here tonight, but always be open minded" As Skyler came out of trance he was relieved to find himself no longer so worried about Mike. It was Mike's loss, not his. He thought that his strange gay thoughts had passed until another group of men approached their booth. They were all handsome but one was definitely more fit than the other two, Skyler admired the way his biceps strained against his rolled up sleeves. They introduced themselves as Chris, Murphy, and Lee. Lee was the muscular one and he tended to speak for the group. Skyler was enthralled by Lee's presence and quickly accepted their request to join them. Karen and April had to hide their mix of amused disappointment as Skyler claimed Lee by sliding right up next to him and resting him hand on his thigh as he flirted with him. Skyler could feel Lee's strong thigh through his jeans and wanted to desperately to move his hand up to feel his crotch. But he also desperately wanted Lee's approval and tried to keep his advances in check. Skyler and Lee were lost in their own little world as the exchanged playful banter. Skyler wanted Lee to make the first move so as not to offend him and so was constantly trying to lure him in. He pressed his arms together to create alluring cleavage in fake breasts, he played with his hair, laughed at all of Lee's jokes; all in an attempt to get Lee's approval and a sign to go ahead and feel his cock up. After a while, Skyler noticed Lee stealing quick glances at the women who danced by their booth. Skyler was both jealous and relieved as he seemed to have found Lee's weakness, dancing. Skyler squeezed Lee's thing with one hand and rubbed his shoulder with the other as he leaned it and whispered, "Why don't I show you what this body can do on the dance floor." Lee quickly accepted and the two of them excused themselves to the dance floor. Skyler tried his best to emulate the feminine dance moves he saw. It was embarrassing but he wanted Lee's approval so bad. Things were going so well as they started to neck. Such physical contact with another man hadn't been part of any of his suggestions but he wanted so badly to feel Lee's muscles that he quickly overcame his discomfort and ran his hands all overs Lee's strong arms and chest. Kissing was another thing that he been omitted from his suggestions. And unlike physical contact, it didn't even afford him the pleasure of feel up Lee's muscles. So when Lee leaned in and forced his tongue into Skyler's mouth, he didn't know how he should react. The act disgusted him, but he started to participate, if only to make Lee happy. They danced and made out for about 20 minutes until Skyler saw his opportunity for some cock action. A loud song with a strong hip hop beat blared over the sound system. Skyler turned around and seductively bent forward, thrusting his ass into Lee's crotch. Skyler made his best attempt at twerking and although he knew he wasn't very good at it, he finally got to feel a hard cock, albeit against his ass instead of with his hand. Lee responded, playfully slapping Skyler's ass and reaching around to pay some attention to what he thought would be Skyler's clitoris. Lee jumped back in disgust as he realized he had almost given a handy to another dude. "Ugh, you're a freak!" Lee spat, drawing a crowd. "I can't believe I fell for that. A girl should at least know how to dance better than that!" Anger welled in Lee's eyes. Skyler was distraught at the loss of Lee's approval and didn't know what to do. Lee was getting angrier and angrier. Just then Karen and April grabbed Skyler and they hit the road before things turned violent. Karen and Skyler drove April to her apartment, the whole time chatting about their night, the people they danced with, what base they get to. Skyler was getting over Lee by now and was able to look back at the good parts of the night. He gushed about how amazing it was to feel Lee's hard cock against his ass. "I just wish I had gotten my hands on it, I would have gotten a better feel. But his muscles! Oh my God! He was so strong!" They all laughed as their conversation turned raunchy. Skyler hadn't really enjoyed himself but he knew he had to be a good sport and follow through on the be, and that meant playing the part of a flirtatious woman. Skyler should have been upset when he heard that Karen and Chris had exchanged oral sex but he was just happy that they were both experiencing so much of the world. As soon as they were through their door, Karen was all over Skyler. They were making out when the crashed into the couch. They're dresses had long since been abandoned to the foyer floor. As they lay there in their sexy lingerie, sucking face and mashing their breasts together, Skyler noticed a strange taste in Karen's mouth. He soon realized what it was. "Oh my God! I can taste Chris's cum in your mouth. Disgusting!" He got up and started to head to the bathroom to brush his teeth. He felt so dirty. "Oh calm down, you big baby," Karen said. "You'd cum in my mouth too. In fact, I bet you wouldn't even last two minutes!" Skyler stopped in his tracks, turned, and sauntered over to the couch. He seductively removed his panties, freeing his surprisingly large penis. It was a strange sight for Karen. Skyler sat on the couch, with legs spread. He looked every bit a beautiful woman, but with a huge erect penis. Karen kneeled between his legs and ran her hands up his silky thighs towards his cock. She lightly wrapped her hands around his member and looked him right in the eye, "If you do last more than two minutes, I'll swallow." She tightened her grip. "But if I win, you swallow." Karen took Skyler's mischievous grin as acceptance of the bet. Skyler knew that he would regret this if he lost, be he just couldn't decline the opportunity to have Karen suck his dick. He was confident that he could last the full two minutes. Karen kissed the tip and Skyler immediately regretted his decision to take the bet. Karen was clearly an expert, judging by the way he felt after just a kiss on the tip. Karen slowly lowered her mouth down the entire length of Skyler's dick, and then slowly back up. Skyler thought that he might last the full time at this pace but Karen was just toying with him. She stopped with just the tip in her mouth, tongue swirling around the head. She then threw her head back down his shaft in quick well lubricated thrusts. She worked the base and balls with her free hands. At the minute mark, Skyler could feel he was getting close and attempted to distract himself. He thought it had worked because at the 1:45 mark, he still hadn't cum. But Karen knew what she was doing. With a few more quick thrusts and a finger now massaging the spot just behind his balls, Skyler erupted into Karen's mouth at the 1:55 mark. Skyler was lost in bliss. It was the best blow job he had ever had. He had forgotten all about his bet until Karen looked up at him with playful eyes, her mouth open to show Skyler his plentiful load. She closed her mouth and carefully straddled Skyler. She brought her face in for a kiss. Skyler knew what he had to do, and with Karen on top of him like this, there was no escaping it. He parted his lips to allow her entry. A warm, slick, and almost mucus like liquid quickly coated the inside of his mouth. The taste wasn't as bad as he had imagined, in fact he enjoyed the experience, thanks to his conditioning to enjoy paying up on bets. He started to kiss Karen back. Their tongues danced around each other as they swapped his cum back and forth. Karen finally pushed the load back into Skyler's mouth one last time and sat back, looking satisfied. "Show me the load," she said. Skyler opened his mouth, gently rolling his load around his tongue. "Good Girl, now swallow it" Karen instructed. Skyler closed his mouth and took a large gulp. As the gooey spunk slid down his throat, he felt an unbelievable amount of pride. Karen and Skyler fell onto a deep slumber, held tightly in each other's arms. As he drifted off to sleep, Skyler was proud he had been such a good sport tonight but looked forward to things getting back to normal. Chapter 7 The following week saw Skyler fully embracing almost all things feminine. Karen had made a point to always call Skyler "Sky" since their night at the club. After a week of responding to the new name, Skyler now also thought of himself exclusively as Sky. Sky was following all of his instructions and now lived with a number of new habits. He always sat to pee now, his face was always beautifully made up, and after a week of wearing the feminine clothes he had bought, he decided to put all his strange masculine clothing into storage. In preparation for their trip, Karen had been taking Sky out a lot more. They went shopping for all sorts of things, included bathing suites, new casual clothes, and all variety of beauty products and accessories. Thanks to a failed swimming contest, Sky also had to now always wear bikinis when swimming, which had left him with very feminine tan lines. Sky also had cause to celebrate. Almost overnight, the hormones he had been taking suddenly kicked in. By Friday, Sky sported his own natural pair of B-cup breasts. They weren't as big as Karen's yet but he was proud of them. He had the false breasts removed and now reveled in the joys of filling out all his cute bralettes and bikini tops. The blowjob bet continued every night. Each time, Sky failed to reach the two minute mark. He was now totally accustomed to eating cum. Sky also found himself starting to honestly find men attractive. When a man would talk to him while he was out, he couldn't help but flirt back. He had learned that flirting in broad daylight was a different game than flirting in a nightclub. He had to be more conservative, settling for subtly touching men's arms when they talked and always laughing at their jokes. This of course, meant Sky never really got what he wanted out of these encounters, a nice handful of cock. By the end of the week, Sky had to admit to himself what he'd always known, he was bi. Thankfully, Sky's attraction to women also seemed to increase as well. He no longer thought of sexual contact as a monogamous practice, and saw every attractive woman as a potential sexual partner. He was, however, having less success attracting female attention. Very occasionally he'd meet a woman who'd return his interest. Sky no longer saw any of his new habits as strange and thought of himself as a regular male so he never realized that the women hitting on him were likely lesbians. Sky's new gossipy attitude meant he always talked to Karen about his most recent crushes. It was once again Saturday and Sky had just come back from the local pool. He was wearing a pair of tiny denim shorts and a bohemian style cover up over his bikini. He just had to tell karen all about the hunk he had met there. "Oh my god, Karen" Sky started as soon as he walked through the door. "You'll never guess what happened to me today!" Karen had just finished placing an order for pizza and turned her attention to Sky, "Ooooh, Tell me all about it, Sky!" "Well, I was just lounging by the pool working on my tan, when I saw the most beautiful man walk past me. He was tall, tan and had a strong but slight build. I guess he was a swimmer by the tiny speedo he was wearing! Anyway, as I was laying there sneaking glances at the huge bulge in his speedo, he started making his way over to me! Finally, he sat in the lounge right next to me and I decided to play hard to get, so I pretended to ignore him." "Oh, you're such a tease!" Karen interrupted. They both laughed and Sky continued, "So after a while he introduced himself, his name is Josh by the way, and he asked why I wasn't swimming. Well, I don't know what came over me but I told him that I didn't know how to swim!" Sky laughed. "I know what your were thinking, you minx! You wanted him to offer to teach you!" "And that's exactly what he did! I played along, pretending to be scared and held onto him for dear life in the pool. He was so sweet, he held me at the surface of the water as he instructed me how to stroke, I even managed to sneak a few passes a his crotch. It got me all worked up. I had to leave before I made a scene but..." "What is it Sky?" "Promise not to laugh?" "I promise" "Well," Sky started, "he had me so worked up that I couldn't stop thinking about his cock and... well I enjoy eating cum, and I can't stop thinking about cock when I'm around a hot guy.... What I'm trying to say is; what's it like to give a blow job?" Karen couldn't believe it, she thought she'd have to implant that suggestion herself but somehow, Sky had gotten there himself based on the suggestions made at the club last week. "Oh Sky, what an open ended question!" Karen laughed. "It's different every time. Every cock is different and every man's cum tastes different. But it's almost always amazing! I just feel so amazing when I do it. I love the power I have over the man as I control his pleasure with my mouth." Sky was in rapture as he listened to Karen's description. It only made the thought stronger in his mind. "Is it something you'd like to try?" asked Karen. Sky got really embarrassed. "No! No... it was just a thought" he lied. Karen knew exactly what she had to do to push him over the edge. "I bet you'd really like it!" Karen challenged. This bet was almost too much for Sky. Sure, had thought about it, but it was just too much. He knew he was bi but this was a line that he couldn't uncross. He planned to decline the challenge but the best he could do was question it. "How would we even gauge if I enjoy it or not?" Sky asked. "In addition to any physical arousal you might show?" Karen teased. "I know you wouldn't lie to me, I would just ask you." Sky questioned the bet once more, "What are the stakes?" "The stakes are the same, win or lose. If you try sucking cock, I'll know that you'll fully understand what it's like to be a woman, and tonight, we'll make passionate love." Sky couldn't resit, "Deal, all we need now, is a cock!" Sky laughed at his own statement, happy that the lack of another man nearby meant he could at least delay the act. But much to his dismay, he heard the doorbell ring. "That's the pizza guy," stated Karen "maybe it's Jake again, he'd be perfect for your first time! Be a dear and get the door" Sky cautiously opened the door and much to his mix of horror and pleasure, it was indeed Jake who had come to deliver the pizza. He was dressed for the summer heat, wearing a short pair of denim cut offs and a loosely draped tank top. Sky noticed for the first time how attractive Jake was. Sure he was gay, but he was masculine in appearance, with groomed body hair and a well trained body. "My oh my!" Jake exclaimed. "I was hoping you'd answer the door again, Sky" He let himself into the foyer, giving Sky the once over as he did so. "I see that you've decided to embrace your feminine side" Jake said seductively. Unlike their first encounter, Sky returned Jake's playful banter with more banter of his own. "You could say that," he teased. "Do you like what you see?" "Not bad," Jake replied. "But almost a little too feminine for my taste, I like my men with a little more meat on their bones. But overall, not bad." Sky could tell that Jake was teasing him. Sky feigned disappointment at that remark and decided to lay in on thicker. "Sorry to hear that," Sky replied, "because you're just my type." He walked around Jake so that they were close, bodies nearly touching, and looking right into each other's eyes. Sky dragged his manicured hand across Jakes strong chest. Sky had forgotten about the bet and was just enjoying working off his flirtatious energy. Karen walked up to the two and got things rolling. "I'm so sorry Jake," Karen said, "but we don't seem to have any cash! Could we maybe work something out?" Sky was looking into Jake's eyes as he playing with his chest hair. Karen continued, "I know there isn't much I can go for you, but Sky here was just wondering what it was like to give a blow job." Jake was a bit taken back at the forwardness of it all as Karen took the pizza from his hands. Sky worked his hands down to Jake's waist. He felt Jake's wonderful cock grow in his hands and knew it was time to go through with the bet. Sky maintained eye contact as he crouched down and began to undo Jake's fly. He shifted his focus to Jake's crotch just as he freed his massive dick. It flopped out and slapped Sky's face. This was the closest Sky had gotten to another man's junk and savored just rubbing his face along it's length. The smell was something unexpected and not entirely pleasant to Sky but that was out weighed by the sheer pride and joy he felt as he played with Jake's cock. Sky took it in his hand, giving it a few firm strokes. He looked into Jake's eye and felt his cock stiffen to a full erection. He mimicked Karen's technique and maintained eye contact as he kissed and licked the tip. Sky couldn't believe it, he had his mouth on another man's dick. It was all