Living The High (heel) Life free porn video

Chapter 1 It had all started about two months previously. Chris had been at his part time job, at the show store, and his boss, Amy, had noticed that he was pretty ineffective when it came to dealing with female clients. Amy had thought that maybe a better understanding of woman's footwear would inspire Chris to sell better. So she made him an offer, if he would take home and wear around a pair of heels for the next couple of days, then she would give him an extra hundred dollars, betting that his increased effectiveness would offset the money that she had given him. Chris refused outright at first, but after thinking about the money he said he would consider it. That night at supper, he discussed it with his mother and sister, and they said that they would give him some help. His mother, Diane, was a bit more skeptical. Her husband had left when Chris was born, forcing her to raise Chris and his older sister on her meager hairdresser's salary. Her whole life she had worried about Chris having a lack of male figures in his life, and still at the age of 17, he had never really filled out as a man. He was still pretty short and not very manly. Jessica, his sister, on the other hand, was excited about this little project. Although a year older, she and Chris had been best friends throughout their lives. Although she was pretty enough she hadn't had many boyfriends, and she was presently following in her mother's footsteps. She was finishing off her high school and was planning on studying to become a makeup artist in the coming year. Chris had chosen a different route. His marks in school had always been very high and he was looking forward to going to university in a couple of years. He had been increasingly consumed by his studies so much so that he made little time for other pursuits. He was a nice guy and although not very masculine some of the girls at school had expressed an interest in him and so he had been on a few dates, though never really had a full time girlfriend. He spent the rest of his time studying and trying to make as much money as possible to save for university at his part time job. His only other pursuit was his on-again off-again membership in the school chess club. So Chris had decided that he would take Amy up on her offer. The next day after closing he chose a pair of black matte pumps, with 3 inch heels, and then later on at night he tried them on. His first attempts at balance were pretty ridiculous and he got Jessica to show him how to walk and balance. After showing him for a few minutes Jessica had suggested that he try on a skirt. It would allow him to feel a bit more comfortable and also emphasize the femininity of the movement required. Chris accepted, though not without much deliberation as he didn't like the idea of his increased feminization. Jessica selected a simple black skirt which went down to Chris' knee. Chris felt what she had been talking about, he immediately felt much more feminine and his walking soon became much more rhythmical. In fact he even started to enjoy it a little bit. The next couple of days when he was supposed to wear the heels would not be so bad after all. Maybe he could even make the best of it. When Chris returned home the next day he found that Jessica had had more ideas. Diane was working late, she sometimes augmented her salary by working on movies in the area, doing hair and makeup for the actors and actresses. Diane was going to be working late for the next while and so Jessica and Chris were mostly home alone. Jessica had gone out this day and bought a couple of pairs of panties. She argued that as Chris was wearing just men's underwear under his skirt that the full experience was still being lost. Again Chris was hesitant to the idea but Jessica persuaded him. As she explained panties were not much different than regular men's briefs. Also, she said, this would force him to think of the modesty that women have to always think of. So Chris begrudgingly accepted. When Jessica next brought out a pair of black tights for Chris, explaining he could put them on if he was getting cold sitting around the house, Chris said thanks but had no real intention of wearing them. But as he was sitting around later he noticed that his legs were indeed getting cold and so he thought that trying on the pair of tights would not really bother him, so he decided to give them a try. When he slipped the thick nylon up his leg, he felt shocks go through his system. These were so comfortable and they were so sexy. Chris felt himself getting hard in his panties and immediately went and masturbated. These tights felt absolutely amazing to him. A few minutes later he went to Jessica asking if he could try on different pairs. She agreed that he could, but she said she mostly had pantyhose and that his legs would look much better if he shaved them first. Chris thought about it for a minute, there was no reason that shaving his legs would be bad, it was October and there was no reason to wear shorts outside anymore. No one would notice that his legs were shaved. So with a bit of advice from Jessica on how shaving legs differed from shaving one's face, he went off to take a bath and rid his legs of hairs. The next couple of days after school and work became ones of exploration for Chris. Jessica was very close to the same size as Chris and she didn't mind if he tried on her tights and pantyhose. So Chris experimented with all her different types and colours. He tried the thick wool ones, barely there black shades, ones with funky colours and designs and so on. It was after trying on a pair of white pantyhose that Jessica had pointed out how sexy white pantyhose look when the toenails are painted red. By this point Chris was no longer hesitant about any further feminization when it came to his legs. He let Jessica pick out a deep red colour and then paint his toenails. He rationalized this the same way that he had before. No one would ever see his nail under his shoes and socks at school of at work. The feminization of his legs was done. Over the next few days Amy asked if he was going to bring back the shoes. Chris asked if he could borrow them for a while longer. Amy agreed and told Chris that he could borrow anything else as long as they were not the only pair of shoes left in the store. So after looking around Chris found an extra pair of knee high boots, some red pumps with 3 inch heels, some strappy sandals also with 3 inch heels and some stiletto heels with 5 inch heels. Arriving home that night, still with his mom working late nights, he found that Jessica was a little upset. One of her friends had gotten sick and another couldn't some over. She was supposed to have done a makeover on either one of them for her co-op class the next day, and without them she would fail. Chris told her that it was too bad that he couldn't stand in for them because he would like to help. But as he mentioned it Jessica liked the idea. She assured him that if he let her make him over that he wouldn't look bad, she could use her skills and highlight his natural feminine features and draw away from his masculine ones. Also she said that she wouldn't tell her teachers about who she made over and that these pictures would never get out. After some begging and pleading Chris finally gave in. To get himself in the mood he first put on his skirt, panties, pantyhose and black stilettos. Not good enough Jessica told him. He would need to look more like a girl. So she sent him off to the bathtub to shave the rest of the hair off of his body. She would lend him one of her dresses. Coming out of the bathroom about a half hour later Chris found a dress and bra on his bed. The dress was one which covered his whole top half but was rode fairly high on his leg. He suspected that he was going to have to wear the bra and so put in on without much thought. As he came out of the room Jessica stood there. In her hands she held a pair of ankle high pantyhose, which she had filled up with some rice, to simulate some breasts for Chris. After she positioned them for Chris, he went to sit in the hairdresser's chair in the basement. Diane also sometimes saw her clients at home, but as she was away at her toher work so frequently, this mainly became Jessica's area for praticing. Jessica came in with a dark curly haired wig and some clip-on hoop earrings. After putting them in place she looked at Chris and noted that any need for anonymity was not required. He already looked nothing like a guy and her makeup would only help to hide his secret. Sitting with his legs crossed Chris settled into the chair and after about an hour of careful makeup application Chris finally looked at himself in the mirror. Gone was the gawky teenager. Now in front of him was an attractive young lady, looking like she was ready to go to her prom. Chris was immediately very aroused. He thought of how sexy he looked and wished he could have a woman this amazingly beautiful. But now he was this amazingly beautiful woman. What before had been a passive adventure now became an active one. Chris loved the way he looked and wanted to keep it going. Now it was him who was doing the begging. He begged Jessica to take him out in the car and go to a fast-food restaurant. He wanted to see what guys would think of him. Jessica at this point feared a little bit for his safety and thought that maybe she had gone too far, but Chris reminded her that he had done a favour for her so now she owed him a favour. Jessica agreed and told him that she would need about half an hour to get ready, so that she wouldn't be outshone by her brother. After about 40 minutes Jessica came back with a short skirt and some red tights. Her makeup was immaculate and they both felt like a couple of girls going out on the town. They went to a nearby restaurant and Chris felt immediately more powerful than he ever had. There were a lot of guys looking at his sister, but then there were also a lot of guys looking at him. Chris was now intent on trying out more and more stuff as a woman. Diane continued to be working late and Chris took as much advantage of this as he could. He began experimenting with all of Jessica's clothes, from jeans to miniskirts and sweaters to tube tops. About five hundred dollars spent on the internet returned everything else he needed. Special panties designed to hide any appearance of his penis, a special bra like device designed to simulate cleavage and breast forms all rounded out the physical needs. Jessica and him made a few trips to some second hand stores and picked out some cool clothes for him. Jessica spent all he free time with him trying to teach him small makeup or hair tricks and the two painted each other's nails. Also Chris worked hard to get his voice sounding more feminine. He was not sure where he going with this but for the time being he was happy pretending to be a woman. Chapter 2 This coming weekend for Chris was going to be a special one. He had told Amy everything and asked if he could come into work on Saturday dressed as a woman. After some deliberation, and seeing Chris dressed completely and talking like a girl she agreed, but Chris would need a new name. Without much thought, they had come up with Christine. By now Diane was nearing the end of her film work, but she was still going to be working for the next weekend. Jessica had also made plans with her friends for Friday night. After spending almost all her time with Chris in the past two months her friends felt as though she had been ignoring them and so she agreed to go out. And so Chris was left alone that night. Diane was adamant that her children not have tattoos and the two of them respected this, but the previous night they had painted some henna tattoos on each other's lower back and a floral pattern around each other's ankles. Jessica also pierced Chris' belly button. He was looking more and more feminine every day. So it came that on Friday Chris was home alone. He figured that other that studying and acting like a girl in the past couple of months that he had not had chance for any of his other pastimes. So after getting completely made up he settled in front of his video game player and put in one of his usual favourites. He had chosen to sit around in some racey clothes. He had just bought a little black dress that he was eager to wear around. Underneath were some thong panties with a black garter belt and some thigh high stockings. His toenails were painted red and so were his fake acrylic fingernails. Again he was wearing hoop earrings, though these ones were regular earrings. He had gotten his ears pierced a couple of weeks previously and he was still getting used to the feel of them. He wore some sexy makeup, red lips and smokey eyes with some fake eyelashes. Although he lacked real breasts the device he bought allowed him to make a fairly convincing allusion. Really he looked like a girl ready to go out for cocktails and not someone that wanted to play video games on a Friday night. At first he realized the game play would be a bit more difficult. He was not yet used to using nails, and the game controls were such that even with no nails it was hard to master. So he decided to give up on gaming and instead put in a movie. It was not long until he fell asleep. He had been very busy recently and not noticed how fatigued he had been. Without noticing that he had gone to sleep, he did notice when he woke up, to the sound of a male voice -Chris is that you? Chris bolted upright. It was his friend Dave. He had met him a couple of years ago in the chess club when Dave was a senior in high school and he was still a sophomore. They had become friends and Dave came over regularly to play video games and hang out. Dave was not a very attractive guy. He was fairly big and awkward and had not been very good with women as Chris had remembered. He hadn't stopped by in over a couple of months. He was usually off at university in a nearby town, but apparently he was home for the weekend. Chris knew that no matter how he tried to explain this, that it would be impossible to explain it except with the truth. So instead he chose to modify the truth. -Yeah, hey Dave. -What are you doing dressed like that? Chris explained it very logically and told Dave exactly the circumstances leading up to the transformation. But instead of happening a couple of months ago, it happened last night and this night. Rather than liking it, Chris explained that he was being heavily reimbursed, by Jessica, who he said would be back soon, though really she wasn't -Well whatever I guess. I mean it is pretty strange but as long as you are getting something back for it. When is Jess going to be back? -I don't know she just went out to give something to mom. She will probably be back any minute. -Well that's all right, this can just be our little secret. I decided to come home at the last minute for the weekend but found out that my parents had already made plans to be out-of-town. So I figured I would swing by here and see if you were up to anything. -I just fell asleep after watching a movie -Any new video games? -No just the old ones. Chris was a little surprised that Dave was not very disturbed by the way he was dressed. It had the effect of putting him a bit more at ease. -Well do you mind if I stick around and play some? You want to play a fighting game? -I can't really because of my nails, I tried earlier, but couldn't quite master it. But if you want, you can play, I will jut watch. -OK sure thing. Dave put in their regular fighting game and chose one of the female characters. -If you are going to be a woman tonight so then maybe I can too Chris laughed a small laugh and starting watching Dave play. After a few rounds Dave started to get a bit exasperated. -Man it has been a while since I played I'm rusty. -Maybe we should just watch some tv. -Sure Chris got up and switched on the TV -I guess you know, seeing as you are a guy underneath there, that you look very hot tonight. The compliment touched Chris, but he pretended that it hadn't -Thanks I guess. They started watching some random action movie that was on the television. -That's a pretty cool tattoo on your leg, is it real? -No its temporary. -Do you mind of I have a closer look? -Uh sure I guess Chris lifted up his leg for Dave to see. He was surprised when Dave grabbed onto it. He could feel impulses run up his leg like shocks of electricity. He got as hard as his underwear would allow. -That's pretty cool. Shocked and embarrassed, Chris replied thanks. They continued to watch television for a few more awkward moments. When the commercial break came on, Chris got up and went to the bathroom. He didn't know what he wanted, but he knew what he needed, and that was to orgasm right away. He was so excited it did not take long to cum. His body shuddered with pleasure and he got himself ready to go back out. When he got back he realized that he had not even missed any of the show he had been so fast. After sitting for a minute Dave reached out and put his hand on Chris' leg. Chris looked at him and saw that Dave wanted him too. Dave leaned in to kiss Chris and as there tongues met Chris went crazy. He moved over and straddled Dave and started grinding against him. Chris could feel Dave getting hard through his pants. The idea of sex with a man had never even occurred to Chris in his new womanly role, now it was all he wanted. As they were making out Chris stopped for a minute -Do you think you could call me Christine? -Sure So Christine and Dave started becoming hotter for each other. After a couple of minutes Christine reached her hand inside of Dave pants. She felt his warm hardness in her hands and wanted this in her mouth. She undid his zipper and pulled down his pants. Dave was extremely well hung. If he were better looking he would be able to have any girl. As it was Dave's massive hardness was all hers to play with. She licked the head of his penis and then began bobbing up and down, her long red fingernails working his shaft where he mouth had just been. She worked her tongue around the head of his penis and listened to him groan in pleasure. The hair from her wig was being held back by Dave, but her hoop earrings followed her movements back and forth and hit against her neck to give her yet another reminder of what she was doing. She felt Dave's legs and then ass muscles start to clench up and she knew what was next. She tasted a little bit of pre-cum and then seconds later her mouth was full of his semen. She looked up and smiled at him as she swallowed. The taste was nothing like what she expected, it was not a pleasant taste, but she swallowed anyway, eager to please. Dave grabbed her and pulled her back up towards him. He buried his head up her dress and pushed her thong panties aside and started to lick around her asshole. Christine knew what would be coming next and waited impatiently. On the couch Christine got on her hands and knees and prepared for David to enter her. When he pulled his head from her dress he then lifted up her dress around her waist. The initial feeling of his hard penis against her rim felt nice, but the next part, s he pushed in deeper, was not so nice. Christine pulled back in a bit of pain. -Is it OK to go on? -Yes just take it slow -Are you sure? -I just want you to fuck me, get on with it. With this prodding Dave did not take it slow. Instead in one movement he pushed inside Christine. She let out a small whelp, but now that he was all the way inside her she knew his would be as much as she would feel, and while there was some pain, she also enjoyed the feeling very much of having his hardness inside of her. Dave began a rhythmical motion, and Christine ground her hips against his perfectly to maximize the pleasure. Christine looked down her body. She saw and felt her hair hanging and following the swaying of her body, her red nails were on the surface of the couch holding her up. Her eyelashes were just a little weighed down by the feeling of her fake eyelashes and mascara. Underneath her dress appeared to be two perfectly shaped breast, rocking back and forth as well with their every movement. Further down, past where Dave was inside her, she could feel her nylon stockings and she felt her high heels trying to find a place on the couch to push back with. After a few minutes what had seemed like Dave's hardness got much bigger and each thrust carried a bit more pain but a lot more pleasure. As she felt Dave tighten up again, she knew he was almost ready, and he came inside her. She collapsed on the couch, with one of Dave's huge loads in her ass, another one down her throat. Dave collapsed with her and settled in beside her on the couch. He pulled her dress back down and held her in his arms. -Jess wasn't really coming home soon, was she? -No she will be gone for a while still. -You know I wanted to fuck you from the moment I walked in the door? -I didn't know what I wanted before, but I know what I want now. -You took my virginity tonight, Christine. -You took mine too Dave. As the two of them lay there and caressed each other and talked, Dave said that he had always felt something different for Chris, now Christine. Christine was flattered but still a little confused. After some time, she asked if Chris could leave, but she also said that they could meet the next night for some more fun, at Chris' house. Christine got cleaned up. Her ass was still throbbing with pain, but she still felt a sense of euphoria. She decided to leave Dave's cum inside her as she slept. She went to sleep, still wearing her acrylic nails. She would be wearing those the next day at her work. Chapter 3 The next day at work, Christine was in a great mood. She was completely fooling everyone. She had chosen a knee length skirt with some over the knee boots with long heels. Underneath she wore some red tights. On top she wore a black sweater with a plunging neckline, exposing her seemingly real cleavage. Throughout the day she dealt with numerous customers, most of whom, she thought, were a bit surprised at her lower than normal voice, but she was sure she was fooling all of them. More so towards the end of the day a guy had come in looking for shoes and he was flirting with her. Her ass was still sore from the previous night and it affected the way she walked. In fact she seemed to think she walked more like a woman now than before. By mid-day her feet were killing her. Wearing these heels required a high pain tolerance she realized. She all of a sudden had a greater understanding of what it means to be a woman. Here she was, still sore from last night's pleasure, yet she was expected to be well put together. She was sure that Dave was at his home right now, not looking anywhere as good as she was, and even though she knew she was exerting a lot more effort, she still liked the way he made her feel, warm and protected. She couldn't wait to see him again tonight. She was going to go to his place after stopping by her home and expected a second round of fun. Amy commented half way through the day that Christine seemed to be very happy. Amy was still a little uneasy with the whole situation. She felt as though she had played a large role in turning Chris into Christine, and so Christine didn't mention the real reason she was so happy ? it was because she had lost her virginity the night before, not in a way that she could have ever expected, even yesterday morning. While most guys who lose their virginity feel more like men, she felt more like a woman now. She was eager to experiment more and feel alive again. Amy decided to close for the day and sent Christine home early. Christine swung by her place and didn't expect to be long. She was going to just freshen up her makeup and put on some perfume. Instead when she got home she found Jessica there. -How was it last night Chris? And how was your experiment at work today? Christine debated whether to say everything, nothing or just a little. She thought she would start by addressing her work and hope Jessica forgot the rest. -Work was good, Amy says that I probably fooled everybody -Of course you did, looking like that, you want to me tell me about it? -Well, I can't, really. I am meeting someone. -Oh? -Yeah Dave is in town. -And you are going dressed like that? -Actually he stopped by last night and caught me completely off guard. -Oh so he saw you? Well how did that go? -Seriously? -Yeah of course -You won't get mad? -Why would I? -Well we made out. Jessica stepped back -Really? -Yeah -Wow now you really do have to tell me everything. -Can it wait Jess? -I guess, but don't you think you are rushing things? I mean you are probably pretty confused right now. I just started this with you because I was looking to bond with you in a different way. Now you are making out with guys. I mean I didn't want to turn you gay or anything. -Like you said it was you that helped to put me on this path, and for now I am just enjoying it. I feel more alive as a woman than I ever did as a man. And I think most of all you want me to be happy right? -Well of course, Chris. So what did you do with him? Just kiss him a bit? -We did more than kissing. -Oh, you didn't, like, go all the way, did you? Chris looked away, Jessica could tell he didn't want to answer the question. Jess was immediately taken aback, and knew the truth. -Oh wow! I don't know what to say. -You aren't mad? -No, just shocked. I mean you wouldn't have done this if it weren't for me. -Yes, but that's a good thing Jess. Haven't you had sex with a guy before? Now it was Jessica that didn't want to answer. Chris knew the truth immediately, that despite her lack of boyfriends that she had been with a man. Finally she responded -All right, yes I have. Johnny and I ? uh ? last year after the junior prom. -Was it good? -I was a little drunk. Christine was surprised to hear that Jessica drank at all, let alone was drunk. -But was it good? -It was pretty amazing -So why is it any different for me? -Its just I always imagined my little brother would bring home some girl some day. -Your little brother brings home a girl everyday. She is a part of me now. -OK Chris I can understand that. Are you happy? -I feel more alive than I ever have today, and it has to do with me being a woman, not anything to do with me having sex last night. Jessica moved towards Chris and gave her a deep hug. -OK well you have my blessing then. Just let me know when you get home later we can have a talk -OK will do big sis -OK little sis, have fun tonight. Chapter 4 The previous night had been as amazing for Christine as the first one. While the innocence of the first night had worn off, Christine and Dave made up for it in experimentation. She had been on top, both facing him and facing away, and also let him fuck her from behind and while she lay and he stood. She couldn't believe that Dave could cum four times in one night. By the end, her ass was almost numb from the pain, which really made the experience much more pleasurable. While she was sure that she would be very sore the next day, while he was thrusting inside her toward the end all she could feel was pleasure. When she came home Jess was still waiting up for her. The two talked about making love, about feeling a man's hardness inside them and compared the feeling. While Jess knew her's was much more of the natural biological feeling, she didn't take anything away from Chris'. The opposite in fact, she was jealous that he could feel so amazing in this way and not be a woman. She was also a little jealous that her little brother had had more sex than she had either. Chris was willing to help her out though as much as he could. She was going to try and stay faithful to Dave, who promised to come home as often as he could, which would be about every three weekends. But Chris said with her help that the two of them could go and meet guys and find a nice guy for Jessica. The only ongoing problem would be Diane. They had as far been successful in hiding almost everything from her. She had been a little suspicious upon seeing Chris' pierced ears, but other than that she had no clue what her son was wearing or what he was doing. End part 1