How far would you go?
Where is your line that you will not cross?
Are there any restriants on you?
At what point do you say stop?
Matt and John were always competitive, they would go to the gym and have to do more distance, time, weight, whatever, than the other, and they would challenge each other over fitness as well as random things, but whatever they did it was never certain who would come out on top. They were also gay and had the stereotypical fit and toned man look, wearing tight vest and trousers to show off their hard won physique, but neither fancied the other as they were both dominants and would not want to be the others bottom, both however did have steady and reliable partners who worshipped them, Jamie and Paul thought they looked great, and though wanting to look toned did not have the frame or body shape to achieve anything masculine, so happily fell into being Matt and John’s submissive partners.
One Saturday night they were out as a four and things were going slowly when a transvestite came into the bar, he was a terrible advert for the cause, matted wig, visible shadow on his face, beer belly and badly put together outfit. They all made fun of the poor unfortunate but it had set a seed in Matt’s mind for a challenge.
Sunday morning found Matt and John running in the park and discussing the previous evenings events. Matt commented on the TV and John agreed he was terrible, then Matt suggested Jamie and Paul would make better cross dressers given half a chance, John agreed but went further suggesting that Paul would be better than Jamie, and so the challenge was set. By their next Sunday run they had to get their partner into something female, without them knowing about the challenge, otherwise it would be too easy.
The week rolled by, and Sunday came on. Matt had managed to get Paul to buy new trainers but not from the men’s section, from the women’s they were light blue with silver detail, very nice said John who had got Jamie into wearing an apron when he was cooking. It was now they realised they needed a referee to decide who had won, as there were no references to judge by. They later rang a friend called Angela a close friend of all four to ask if she would judge who had won.
Over a drink the three of them sat down and discussed what they were doing, Angela reckoned that many men wore ladies trainers especially as they were a slimmer fit, and an apron was just convenient and practical, so judged them equal.
Disappointed they went off sure that by the next weekend they would have got their partners onto something properly feminine.
Once again they needed Angela, John had bought Jamie a short nightie telling him it would turn him on, Matt had persuaded Paul to use lip-gloss. Angela felt lip-gloss though very public, was something many gay men might use, but the nightie was the winner, just a shame it had been a private affair. Matt felt he could top the nightie and said so, saying by next Sunday he would have Paul in something to top the nightie.
The following weekend Matt was confident, he had persuaded Paul to try silk knickers, which Paul apparently loved the feel off. This re ignited the challenge. If Paul would do this then Jamie would surpass it.
By the following Sunday Jamie was wearing knickers and camisole sets as well as his new found nighties, the newest being full length, satin, lace and pink. Paul had been persuaded further and he too was wearing camisoles under his male clothes. Angela judged it a draw, but suggested instead of trying to compare different things she would give them something to achieve, for that week she suggested complete loss of body hair, they agreed.
By the weekend both men had hairless partners, and both said how nice their skin felt to touch and that they would be keeping Jamie and Paul hairless from then on. Next week she said she wanted a night out with them, they had to be wearing the underwear, which both knew was not a problem, but she wanted to see either arms or legs to verify the hairless body challenge, and for that weeks challenge they had to wear a delicate piece of jewellery, not a chunky man’s piece.
They turned up at the appointed bar, Jamie in a t-shirt; Paul in a sleeveless top Matt hoped to show Jamie’s off bare armpits for a bonus. Jamie however won with the jewellery; he had a thin neck chain with a stone hanging from it as well as a delicate chain around his wrist. Paul did have a ring on his thumb and a ruby stud in his one pierced ear, but Angela felt Jamie had it that time.
Their challenge for the next week was to get the boys to have both ears pierced. But this proved quite easy, both relationships easily accommodating this demand.
The following week she wanted them to get Paul and Jamie to have a manicure, not that hard, but to keep a coat of polish on them, she did not say a colour so both ended up with clear polished nails.
For her next idea Angela thought one of them might refuse at a salon, she suggested highlights or a colour change, something she knew some gay boys would do, but at a salon, that she was unsure about.
She had underestimated the willingness of the boys to please their men, Jamie was now a blonde and Paul had silver and gold highlights in his mop of a haircut.
For what she said would be her last idea because no one seemed to be winning, she asked if they could meet up the following weekend when the boys should be wearing something that screamed female and for all to see, nothing like underwear this time. This time she felt sure one of the men might give in, or one of the boys might refuse to wear whatever it was they were being persuaded to wear.
Jamie was bought a lemon angora top with an unusually deep V that on a woman would display some cleavage; he liked the gift and needed no persuading to wear it out that Saturday. Paul was less obvious he had on white cotton trousers that hung from his hips and flared out to unbelievable hem lengths, Angela’s response was to declare it a draw, both men could get their partners to do whatever they wanted and both looked comfortable in their feminine styles. But this last challenge sparked something between the boys, seeing each others new clothes and realising how they had both got piercing together, been and had their hair coloured, worn jewellery, and when they talked found out what the other was wearing underneath, it was obvious they had been used as a challenge, Matt and John both admitted to what they had done, but insisted they had only improved their looks by doing these challenges, there was nothing detrimental, and the boys agreed because they loved the soft underwear and nighties as well as the changes the challenges had made to their appearance.
The following morning while the men were out running, Jamie was round at Paul’s discussing what the other had actually done, Jamie liked the cotton trousers Paul was wearing and offered him the lemon top to see how they combined for a look, and both loved it. Then they got around to the nighties; Paul got his long satin one out and Jamie immediately announced he was getting one also. They knew the challenge had come from the sight of the ugly TV, but now they were cross-dressing themselves they wondered how far they might take it themselves. They choose not to push it too hard because they were gay men and going to feminine might put off their partners, so they would give it a week as things were, basically the underwear and nighties to judge how Matt and John would react to them staying ultra camp. This went so well, neither Matt nor John objected to Jamie and Paul still wearing the knickers and nighties, even making it clear they were staying in one evening to clear their body hair and do their nails created no complaints. This meant that Saturday morning the boys would be out shopping. The men had been able to say the purchases were for a girlfriend as a gift, but two camp men buying first a long satin nightie, then a cream roll neck top from a woman’s boutique was causing them to get embarrassed and have fits of giggles. But by the time they had bought trousers for Jamie they had got used to the awkward feelings and were just going for it. So much so that as they passed a make up counter they bought lip-gloss and mascara knowing that they had seen boys wearing these already so should be fine for them.
That evening they were out as a four as they always seemed to recently, only this time the boys wore their female clothes, jewellery and make up, loving it. Feeling completely at ease with their partners who were the clearly dominant men while they fulfilled their role as the sissy in the relationship. After a few drinks they plucked up courage to ask what Matt and John thought of their look, John just kissed Jamie very powerfully, while Matt asked if the long nightie was still available. A positive result.
On the Sunday, the boys were chatting on the phone seeing how it had gone the previous evening, and when they both realised how well their purchases had been received they were left with the dilemma of what to do next in this cross dressing adventure. They could go straight for skirts but felt their men would baulk at this so wondered what they could do without going full on.
It was now their turn to contact Angela, they knew her part in the challenge and thought she might like to continue it but in a reversed way, what could they get away with before comment was made. She told them not to get their haircut, to let it grow, but to maintain the new colour they had got. Also to file their nails not clip them, and let them grow a little. All a bit long term they felt but definites for the future. For a more immediate challenge Angela suggested wearing some of their new clothes daytime, maybe even try out the make up daytime in the week as well.
The following week found both ringing the other to tell what they had done, Paul did the weekly shop in his trousers, Jamie went to work with mascara on one day, which inspired Paul to try the same. By the weekend they were so excited they wanted to shop for more things. Paul bought himself a matching nightie and wrap saying how this would work magic on Matt. Jamie bought another top, this time a soft cotton kaftan but did think it might be too much.
He need not have worried the top was a hit with Matt, while John suggested Jamie be a little more adventurous in his clothes selection. For their Sunday chat they could only say wow that went well. Jamie was going to try out the nightie and wrap that evening and would let Paul know how it went. But by the Tuesday both had decided to see how mascara would go fulltime, upping it to lip-gloss in the evening by Thursday.
They kept it at this level for about six weeks, the mascara became fulltime, Paul was able to wear his trousers more often, but that was just because he worked in a call centre and Jamie worked in an office that was a bit more conservative, but he did try out his tops on several occasions without comment. They did shop and increase the number of tops, Paul bought a kaftan style top and enjoyed the girlyness of the look as well as the attention Matt gave him.
It took about six weeks for the piercings to heal, by which time the roots were beginning to show in their recoloured hair, so Angela suggested they have a trip to a salon to get their hair sorted, but then as a challenge they should buy some earrings and see how girly they would be prepared to go in with the style.
Their next Saturday was now full, a salon visit then shopping, nothing drastic, just getting the roots done and a bit of a trim to tidy up the ends, but Angela had insisted on nothing too much being cut off, they had to wait till the length was better before cutting was a real choice. Then it was off to find some ear decorations, first they looked at small rings with a stone or a fancier stud, but these they knew many men, not just gay men would wear, after much looking and Jamie getting distracted and buying himself some new underwear, Paul bought a pair of hoops and Jamie chains with fine tips that allowed them to be threaded through his holes. They were not allowed to point out to their men what they had bought; rather they had to wait for them to be noticed. Unsurprisingly both earrings went without comment, meaning, according to Angela, they were not feminine enough and they needed to try again.
For the next weekend Paul had bigger hoops and Jamie a red stone dangling from each lobe. This time the jewellery was noticed and for the first time were referred to as girls, well they were in full feminine outfits of cotton trousers, soft short tops and make up, not to mention the jewellery of earrings, as well as necklace and bracelet they had worn before.
Buoyed with the success of the fun they were having, they wanted to try another challenge, yet at the same time their wardrobes would increase and the small collection of jewellery was bound to increase. Paul started with a chain bracelet, Jamie followed with a necklace and an anklet. It took three weeks before they went out fully glittered up, non to discrete earrings, pendant necklaces, bangle style bracelets, a couple of rings and for Jamie his anklet.
The men’s response was very supportive telling them how nice they looked, encouraging them to dress more femininely all week and not just at the weekend. Angela recognised that the jewellery had not found their limit for femininity, and suggested that they get some shoes from the female stands. The boys had a fright when they saw the choice, nearly everything had heels on them or looked just to butch and practical for what they wanted, Paul found himself some suede sandals with a small wedge heel which were not to dissimilar to his beach flip flops, Jamie did not like things between his toes so settled for a beck shoe, but not a boring blue or white his were lemon which would match the angora top. Angela’s response to Paul was that now he should start doing his toe nails as well with them being on show. Matt and John’s reaction was to just call them girls far more often, but still no one was saying, enough it is time to stop this.
Two weeks later Angela challenged them to try proper heels and coloured lip-gloss, she felt this might just make them look like and feel like girls, maybe crossing a line they did not like. But she was wrong, the shoes were conservative, low block heeled courts and the lips were certainly pinker now, but they did look more feminine.
Having failed with that challenge she told them for their next weekend eye liner was a must and new shoes without block heels, they would be allowed the stunted kitten heels if that is what they liked. Paul did get himself some kitten heels but Jamie bought a pair of boots with a low but narrow heel. They had bought them one evening and then had plenty of fun telling each other how odd it was walking in the new footwear, and that combined with eye liner practise, meant by Saturday they were ready for an upping of their look towards the feminine. Matt’s reaction was to call Paul, Paula which gave everyone a laugh, but it stuck, Paul was from then on called Paula by everyone within the four and over time it spread to the wider circle of friends who had not let it go unnoticed the change in style of the two friends.
Angela had a serious eye contact talk with Paula when this happened, wanting to know if he was happy with the new name, and when he did not look away as he said yes she knew it was for real. So she challenged them to learn how to pluck eyebrows and thin theirs to a shape they liked. First they looked at glossy magazines, then on websites to find out how to restyle their own particular brows, Jamie’s were quite fine already but were thinned non the less, but was not that noticeable, Jamie had darker and bushier brows so when he picked a tadpole shape it was Jamie who asked if it was not to far, Paula said no and asked Jamie to get on with it. To be fair neither had a shockingly dramatic shape, but they were clearly different from before.
It was Paula who now suggested they try eye make up, but Angela had a better idea, first go to a salon, get the roots redone and now their hair was well past their ears and in Jamie’s case well down to his shoulders, it was time to get a cut. She took time to show them hair styles asking what they liked and suggesting what might suit them, this took all Friday evening, but by the time they turned up at the salon they had a photo cut out of a magazine and ready to ask if the stylist could do it on them. Paula’s hair was cut so it was long all the way round, needing to be swept back over his head or tucked behind the ears, Jamie came out with a gently waving perm, giving his hair body and lift, and luckily for him enough length so he could tie it back on Monday when he went to work.
Once again Matt and John loved the changes, Jamie being rename Jem. They were not yet fully aware how feminine they looked, but now Angela said was a good time to find out more about make up and how it changes and improves the facial features. This was the first time she had accompanied them shopping but felt there was so much to take in they would need help. She was thrilled when a sales assistant came to help, Angela explained how her friends had no idea about make up, with some story about being student drop out types who now wanted to look more normal, the sales girl lapped it up and offered to give them a make up demonstration. An hour later they walked out with perfect foundation, defined cheekbones, sultry eyes and kissing lips, as well as bags of cosmetics they would need if they were to try and recreate the look. Once outside Angela pointed out that at no time did the girl take them for men, which made the boys giggle. Being in charge of the situation she claimed that as they were looking like women then they needed a bra. Walking them into a store where they each bought three b cup bras, then she made them go into the ladies and put one on and fill them with tissues. They came out looking far more self conscious than she had ever seen them, maybe this was where they stopped, but later that evening she bumped into them, both dressed in all their most female attire, faces still made up and most noticeably, their chests sporting breasts, bigger than a b cup was meant to be. She was wrong this had not been a stopper just a pause.
It took them several weeks of private practise and consultation with each other and Angela before they went out again with full make up on, but it was worth it as they felt more finished in their look. They also liked the feel of a bra, but for daytime wore AA cup so it would not show at the front if they wore thick loose tops, but would be felt by them as it wrapped their chests snugly.
Angela was running out of ideas, she could get them to try a skirt but still felt this maybe too much, instead she went for more pronounced shoes, gradually upping the heel height, and once they were happy in 3” courts moved towards 4” sandals, and then onto shoes with no ankle straps, just a strap across the toes to keep them on the feet, meanwhile they had taken to wearing their first female shoes in the daytime and for work on occasion.
Next she persuaded them to try a new top style, they had always picked shorter tops that maybe reminded them of a male counterpart, but this time she wanted them to try a longer top, one that would come well below the hips. Paula took to this easily and bought a black and white geometric pattern which stopped below his crutch, actually looking like a mini dress, with a fitted bust and delicate cap sleeves, Jem at first had trouble finding something he liked, and ended up getting a long white jumper that he easily sat on as it was so long. Angela told them they were beautiful and ready for the last challenge. Next Saturday they would going out in a skirt, tights or stockings, (that choice was up to the men), full make up, new top to go with the shirt and her treat a wash and blow styling at the salon.
At first they were not sure if they could wear a skirt, it meant taking away the last vestige of their male look, but there was nothing left in reality, so they took Friday off and shopped together, they now looked so female they were comfortable browsing the rails and looking at the mannequins for ideas. It was late when they got home, both had chosen full layered skirts that fell to mid calf, Jem a brown, Paula a green, they had cotton blouses with ruffles at the cuffs, neck and down the buttons, they also had a pair of stockings and tights each but would need to ask before opening a packet and trying them on.
Saturday they meet at the salon early afternoon, dressed quite reserved for them now, flat shoes, jeans, and a plain shirt with only a touch of make up, but they still looked like Jem and Paula, not Paul and Jamie. The stylist did wonders on their hair; Jem’s was given loads of volume and curl, Paula’s was swept across his face and lacquered in place. As an extra unknown treat the salon also painted their now trim nails a vibrant pink and given a lipstick to match them. They had left Jem’s clothes at Paula’s and went there to change, the men had been told that it was to be a special night, a meal and a good club possibly, but all they knew was that they had been asked stockings or tights, both said stockings as they reverted to male stereotype.
The cab picked up the girls at 7.30, now fully dressed in their skirts, stockings, 4” sandals, C cup bras, long pendant earrings, obvious rings, matching necklaces and bracelets and small bags to keep those essential girly bits in like a lipstick and tampon. The cab driver knew nothing was amiss, Matt and John at first did not recognise their partners, both of their girls being on them before they could say hello. There were lots of compliments on how good they looked, some pleasant touching. Then it was off for a good restaurant then onto a club and some close dancing, followed by a night of showing these boys what a girls place in bed is, but they knew this already, that was part of the reason they had worn skirts that evening.
Matt and John had no objections to their partners behaviour that evening, and over the months that followed even encouraging it with presents that might seem more appropriate for a girlfriend, such gifts as scent and jewellery were common over the year. And things seem to settle down after they had worn their first skirts, they were still camp in the daytime, straight men do not often wear mascara and lip gloss, nor do they wear silk underwear but Jem and Paula did, but it was dismissed because they were gay, so camp was to be expected, the full on female look happened in the evenings and all weekend, with the nights being a proper dressing up time, now skirts were included the whole range of women’s clothes were at their disposal, minis, evening dresses and revealing tops became their Saturday night preferences especially if their men were taking them somewhere special and straight.
This part time female life was suiting Jem and Paula when Angela made a reappearance in their lives, she had been away and not out much when she was around so they had not seen her, and besides the odd phone calls for advice, there had been no contact. Then they bumped into each other one weekend when they were in a club dancing, Jem in a crochet top that gave his white satin bra a very visible outline, Paula opting for a tight top instead but with a flared mini as opposed to Jem’s jeans, both on towering 4” heels and with excellent make up, she had to make sure it was them before approaching them. She was thrilled to see they had kept up with the new style, and asked if they were still enjoying it, they told her all about recent shopping trips, salon adventures and the reactions of Matt and John. But it was later in the week when she accidentally met Jem, who was looking very much like Jamie, he was wearing a nice knitted top, jeans and flat shoes he bought from a ladies selection, his hair tied back and no make up. She took him for a coffee and asked why he seemed to be reverting back to boring camp, what did John think, what underwear did he have on, if she saw Paula now would he too be a boy. In short she thought she had left them moving towards full femininity each trying to go one better than the other, but it seems like they have stopped the competition and were actually going backwards. Jem tried to explain he had a job that he thought would not agree to a way-out change of identity, John loved it when he dressed up at the weekend, but close shaves need a few days to recover and after a weekend he needs to let his skin recover.
Angela had some time to herself and pondered her two projects and how they had turned out deciding that she wanted to find out more about the situation, first she contacted Paula to find out if Jem’s experience was duplicated, the answer was, nearly, Paula still wore light make up as his beard was light, but for work his clothes were camp and shoes flat. Next she rang Matt and then John to ask about their partners and find out if they were happy with weekend girls. Matt corrected her when she called Jem Jamie, but was happy for him to do what he likes as long as he was happy, but yes he did like the girl in both Jem’s look and behaviour. John was a little more disappointed she felt, he would like to see more of Paula in skirts but knew how hard it was for him to do it with work and things, so would settle for what he had. This lead Angela to go out and look for fresh challenges for the boys after getting support from the men she invited Jem and Paula to her flat and showed her some websites she had found, it was a mid week evening and they were pretty much in boy dress, so she mocked them for being so conventional saying they should revert back to their old names, being essentially submissive characters they said they were sorry and what should they do. Jem she said should go for beard removal, Paula should wear his bra fulltime again, when he suggested it would be too obvious she allowed him to use AA cup bras, at least to start with. They both had to resume fulltime clear nail polish, she also planned a salon visit, Jem was still blonde and Paula had let the highlights grow out, their hair was certainly longer but the style nothing different from early on really. She would leave a more dramatic style for later, first she had a few other ideas to get on with.
A week passed and the boys were unsure about how things had changed, Jem had been for his first appointment and had a sore face, Paula had gone to work in a bra but felt self conscious in it, but Jem reassured him that they had felt like that before and now look at them enjoying what first had worried them. Angela wanted to know how things were going and was pleased they had done as she suggested, but she was still trying to find the point at which they say no.
A fortnight later, she tells them she has a treat. They already have discovered silicon inserts but Angela wants them to be fixed more permanently, at least Friday evening to Monday morning. And as she is giving the boys their first lesson on how to fix them she realises they never wear tight fitted skirts because they have not worked out how to hid the bulge except with control pants that they don’t like the look off. So having spent time doing research, she explains how all good trannies hide their bits pushing them back inside and taping the remainder up tight. It takes a while but soon she has two boys who at a glance pass as girls even undressed, but for certain in their satin underwear. That Saturday they had to go and buy something either with bare shoulders, i.e. no bra straps showing, our a skirt that was tight across the hips, in a way displaying the fact they have no bulge. That evening saw them out in tube dresses, one gold the other silver and made up to the nines, their men were very impressed with the new look, even more so when they stripped off at night and retained the shape the dresses had indicated before.
Angela wanted to push them further into being more feminine through the week, which she felt was about the only challenge left. Jem was loosing his beard, and though reluctantly at first now wore a bra full time like Paula. Next she suggested they wore flat sandals full time, which again met resistance but in the end they went to work in sandals that were far too delicate for a man even if the colour was black.
Over the weeks she encouraged them to grow their nails again, nothing long, just neat and rounded, definitely not clipped and short. She had had them on the challenges again for about three months; Jem’s beard hardly showed now and had no excuse for avoiding make up full time though he still would not wear it to work. Paula had been persuaded into wearing light foundation, a lip-gloss and mascara fulltime, and with the other fulltime changes was starting to create gossip at his work, which was starting to worry him a little. Now Angela wanted to see if she could be bold and make a final dramatic change, she checked it out with Matt and John first, and then booked the salon. The boys thought they were just going to have roots and a tidy up. What they got was a complete shock, Jem realised something was up by the amount of hair on the floor, his blond roots had been done but the style was like something Bowie had in the 70s long feathers with a spiky top. Paula faired no better; he was now auburn with lots of tight curls tumbling down to his shoulders. They both loved the new styles and wanted to dress up and go out. They thanked Angela profusely, the look on her face was that of a proud mother, but they all knew that Monday was going to be a hard time. Matt and John loved their boys new look and told them Monday was not a problem, they looked great, and in their dresses dead sexy.
They had a fantastic weekend being totally girlie, but Monday was hard, Jem could not tie his hair back and had to show up with it just a little flatter than when he walked out of the salon, Paula could get a pony tail but the new colour and the curls still showed in the tail. By lunch they had both had trouble, Jem had been into see his manager who told him the hair had brought to head the issue of his appearance and though not inappropriate for a girl it was not good on a man, and though company policy would not stop him, he was asking him to be a little considerate to the company and his colleagues feelings. He was almost in tears when he rang Paula who had not had any company problems but some of his work colleagues were taking the piss with comments about his look. By the end of the day they were glad to get home and escape. It was Matt who had a solution, he loved Paula best at the weekends when he was a full on sexy woman, and his reaction to the comments at work meant that he would probably revert back to a more Paul look, so he called John and Jem inviting them for a meal. This kept Paula occupied preparing the food while Matt made a few calls, by eight he was ready, John and Jem arrived, Jem had been persuaded to be a bit girly and wore a dress, but something rather subdued really. Then as they got past the pleasantries Matt was cornered with questions about what was this all about. He started with a bit of a monologue explaining how Jem and Paula came to be attractive girls, and how he felt responsible for starting this chain of events, and how he loved Paula even more when he was looking female sexy, and knew John felt the same about Jem, which was odd given they were all gay and did not fancy women, but today had caused a problem, and he did not want to go back a couple of years and loose Paula and get Paul back. So he had a suggestion, they pack in at their jobs and work for themselves, doing what? are you mad? they came back with, but he was ready. Everyone knows gays are more careful about being clean than straights, well the urban myth says so, and Jem and Paula are great housekeepers, so he had rung around and there seemed to be a market in the gay community for gay house carers.
They were a bit stunned at Matt’s optimism but he persisted with his idea explaining how it would work and assuring them it would succeed until the boys agreed to give it a try, there was one proviso made by John, there was to be no toning down of the girl in them any more, he wanted his weekend girl to be a week day girl as well, this would not be a problem it seemed.
They advertised in gay papers and amongst friends and soon had enough work to keep them busy, and enough money for clothes, shoes and make up so it was considered a success, being female fulltime was fine. It was some two months later Angela was chatting with them, she was really pleased with how things had worked out for them and how their femininity was blossoming, then she suggested a new challenge, she knew their men liked the fact they were really boys and that they have boy bits, but had they considered breast implants, then they could throw the falsies away, feel with their nipples and enjoy going braless with just a silk camisole on. She could tell from the quick glance between the two that she still had not found something they would not do to be more feminine. Accepting these two boys just revelled in the joy of being able express themselves in a completely feminine way, and with a hug wished them all the best.
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