I Never Planned on Mandy


by Tabitha

Chapter 2

On Monday at school, Louise saw Kyle chatting with Mark, one of the football team's linemen.

`Hi Kyle, how did things go?' she asked.

Kyle greeted her affably and told Mark that he would see him later. Walking away with Louise, he told her, `It went very well. You know I think Mandy and I really hit it off.'

`Did he, you know, er…' she trailed off, then added, `Usually he shares details about what happened – or rather what failed to happen – afterwards, but he seemed rather tight-lipped this time. No pun intended.'

Kyle smiled, `I suppose I shouldn't really go around discussing what we did together, but you are his sister, and he's always shared with you before. He felt too nervous and light-headed – I think someone spiked his drink – to really feel ok about doing much. We just kissed and caressed and, well, made out I guess. He said he wanted to leave the next stage until Thursday night.'

`Thursday night?'

`Yes, I'm taking him out for a bite to eat and then on to a movie. Say, do you know what sort of films he likes best, there's that new Julia Roberts one on. Does he go for the romantic comedies, or does he like something a bit more cerebral. There's a foreign language film on that I fancied seeing about the Spanish Civil War.'

Reeling from the twin shocks of hearing that her brother had another date as a girl and that a football player was interested in an intellectual film, Louise was rather lost for words. But finally managed to say that Brian - Mandy she corrected herself - would probably prefer the Julia Roberts film. Afterwards she realized that her mind must have still been working on some level as she knew that Brian would hate a piece of Hollywood fluff, and much prefer some arty piece of foreign cinema.

Confronting Brian at lunchtime, she quizzed him about his Thursday rendezvous. At first he did not want to talk to her, just as he had not talked to her throughout all of Sunday. However, after she pressed him against the wall and pinched the skin of his neck, he was more forthcoming.

`Yes I told Kyle I'd see him again.' he sneered, `If I hadn't he would probably have made me give him fellatio. I don't know what you told him, but I'll get you back for it sometime. Anyhow, do you really think I plan on going along on Thursday? I told him I would meet him underneath the large clock near the train station at eight-fifteen. He may turn up, but I have no intention of going – as `Mandy' or otherwise.' Brian shock off his sister's hold, and, slipping beneath her arm, darted for an exit. Louise was too slow to catch him.

Louise thought long and hard about what to do, feeling (quite correctly) that she was in some way partially to blame for this, and feeling bad about Kyle being left standing forlorn underneath the clock. Feeling that it would be unfair to Kyle to tell him the truth, and mad at her brother for how he had acted, she did not want to tell the catcher that Mandy would not be showing up. Louise was not sure just who knew about Kyle's sexual preference, but guessed that Roger Jordon - the football team's captain and longtime friend of Kyle – would be a good bet.

Approaching him at lunchtime the following day, she asked if she could have a quiet word with him. Louise had known Roger since kindergarten, but even so it was hard for her to address what was on her mind, in case it caused problems for Kyle.

`How well do you know Kyle Hudson?' she asked hesitantly. Roger laughed, `Probably as well as anyone. Heck you should know, we've all grown up through the education system together.'

`Does Kyle have any, er, secrets.'

`Loads I would guess. Why?'

`It is just that I heard, that is…' Louise paused, `Have you ever heard anything about him having, er, different preferences?'

Roger frowned, and did not seem very pleased with Louise. Taking her elbow firmly he steered her into a nearby empty classroom. `What are you getting at?' he demanded.

Louise had known Roger a long time and never been the target of his angry stare, and she baulked a bit. `Is Kyle gay?' she asked.

`What business of yours would that be?' he asked crossly.

`It is just that…' She paused, swallowed hard and then continued, `Do you remember Mandy, my cousin at Nick's party this weekend.' Roger nodded but remained frowning. `Well Kyle and Mandy got on, er, very well.' she went on. `The problem is that Mandy is not actually my cousin.' Another long pause during which she lowered her gaze before completing, `Mandy is my brother Brian.'

Roger's frown disappeared as the look of astonishment crossed his face.

`You see I know that Mandy, that is Brian, and Kyle made out and I think they sort of made a date to see each other again, only I don't know if Kyle knows Mandy isn't. Isn't Mandy that is.' Whilst the last of this was a lie, Louise felt it at least offered Kyle an escape route from accusations of homosexuality if his secret preferences were not know to Roger. However Roger soon confirmed that they were.

`Kyle came out to me and the guys about two years ago.' he explained, `We all accepted it. After all it was not as if he was going to suddenly start hitting on us or something. We thought it best not to go blabbing our mouths off. Some people can be jerks about such stuff.'

Louise was rather amazed by the football team solidarity and open- mindedness. `Didn't any of the players get work up about it?'

Roger paused and reflected. `Not really,' he said. `a couple were a bit freaked at first and took some getting used to it, but the guy's a great catcher, a good laugh and, at the end of the day, he's still our pal Kyle, even if he does have different tastes in bed partners. You've got to remember that Coach Melengoff was gay, even if he couldn't officially come out and expect to keep his job. He was straight with us, admitted that he was gay, but said that the only time he would want to be watching our ass was when we were bending over to score a touchdown. Not only that, but Mark's uncle is the most raving queen you ever met, and he's the guy that taught Mark to throw; his own dad throws like a girl - no offence.'

`But I thought all you jocks were real macho, hetro tough guys.'

`My, aren't we the prejudiced one!' exclaimed Roger with mock surprise. `Seriously though, it's hard to be a bigot when it comes to a pal who you've always been able to depend upon and stand alongside. As I said, we didn't make a fuss or go around telling people – that's Kyle's decision. A couple of the cheerleaders know, but apart from that, it's just the team.'

They paused for a while, and Louise realized that the atmosphere had lightened up considerably now that Roger didn't think that she was going to cause trouble for Kyle. She began to relate how Brian was planning to stand Kyle up on Thursday. She neglected to explain all of the facts behind her brother's masquerade, leaving Roger to merely think that either Brian was in two minds about his alter ego, or else that he was some little tease.

`Don't worry.' smiled Roger, `I'll make sure he sees how unfair it would be to stand up Kyle.'

On Thursday morning Brian was walking to History class when he felt a hefty pat on the back, and an arm encircled his shoulders in a friendly but forceful hug. Startled he looked over and saw Mark Nailor from the football team on his left, then became aware of Randy Granger – the team's most brutal and sadistic looking player - on his right.

`How's it going, Brian?' asked Mark, who had never spoken to the younger teenager before.

`Em, good, thanks.' he managed to reply. `What about you?

`I'm doing great.' continued Mark, `everything is going good. Only one thing that worries me.'

`W-what's that.' stammered Brian.

`It's our pal, Kyle.' explained Randy, who despite looking like a violent troglodyte was actually the most softest hearted player on the team, a fact that he worked hard to keep from becoming general knowledge throughout the school. `You see Kyle's got a date with a young lass who I've heard is a bit of a tease. You know the sort, lead `em on, then leave `em standing.'

`Terrible sort.' said Mark.

`Aye.' agreed Randy.

There was an awkward moment for Brian as the three of them continued on in silence, other students moving carefully aside to let them pass. Some people seemed to be nervously looking at him, no doubt assuming he was in some sort of trouble with the two beefy football players and wanting to know who's face to look out for on the news story when they came to report that amangled body had been found.

`You know,' said Mark eventually, `if that little minx breaks Kyle's heart, someone ought to teach her how nasty that is. Nothing major, just enough to leave her in traction for a couple of months.'

`Nah,' disagreed Randy, `I know some bikers who would make her realize that she should cherish the tender embraces of someone like Kyle. I'd turn her over to them for some fun.'

`Of course,' went on Mark, `There's always Tony's pet husky, that bugger is the horniest animal I know, why it would…say Brian, you're not looking too good.'

When they laughed about the act they had put on later, Mark and Randy were sorry that they never saw which of the imaginary fates that awaited Mandy if she failed to show had actually drained the color from Brian's face. As they left him outside his classroom, Randy told Brian in parting, `You know you really are pale, Brian. What you should do is get more fresh air. Why don't you go out somewhere tonight.'

The first Louise knew of the two footballers' success was when she went into her room after school or rather after a trip to the mall after school. It is a strange phenomenon, but the average teenage girl is capable of leaving half a dozen articles of clothing, magazines strewn on the floor, an empty cup from two days before on her nightstand and assorted books in assorted locations around the room. However if a couple of items are missing from her vast array of cosmetics she will instantly notice their disappearance. Checking in Brian's room she found a panicked brother looking rather more like Coco the clown than the attractive young girl of five days before.

`Changed your mind?' she asked with amusement.

`Louise,' her brother responded, `you've got to help me. How do you make this stuff work?'

Louise smiled again. `Tell me truly.' she said, `Do you really want my help with getting ready for tonight, or do you plan on standing Kyle up like you said.'

`No, no,' replied Brian, `I really do intend going. Please help me.'

Still smiling, Louise led her brother into her room. Louise had rescued the wig and breastforms from Brian's floor on Sunday morning whilst he was flossing his teeth in the bathroom. With a little brushing, and the rather better application of the make up, Mandy was again reborn at her vanity table. Brian was sitting looking rather miserable, clad only in his socks, briefs and a dressing gown. Leaving him glazing forlornly at his female alter ego, Louise went and selected some appropriate attire.

Because this might be Mandy's final appearance (though Louise rather hoped not), she decided that the fake female deserved to go out in style, and selected her favorite three piece underwear set. It comprised of a pair of silk panties, a bra and a suspender belt in a deep plum with white lace trim. The set had been a present from an aunt whom she had always liked but who her parents vaguely disapproved of for reasons that were never mentioned. She added to this a pair of black stockings with a fancy pattern at the top, and on her brother's insistence left the room whilst he changed into them.

Returning a few minutes later, having heard her drawer opening, she confronted her now naked brother as he looked for something less `seductive'. Slapping his bare buttock, she told him that the deep plum set was all that was on offer, and that he should be grateful to be offered something so nice. He hesitated at first, but when she pointed out that his only other options were no underwear, his own underwear (either of which would at best leave him flat-chested and at worse leave him over-exposed) or going out to buy some more (rather hard with his face made up but no female clothes to wear), he acquiesced sulkily.

He did bemoan wearing stockings instead of pantyhose, as the latter had proved useful for keeping his genitalia in place on the previous Saturday. Louise told him that he never really had enough down there to need worry about it, and besides, it might be handy to have easy access to his willy, as when he had finished sucking off Kyle, the older youth might offer to return the favor. Brian blanched at this suggestion.

Louise decide to finish off Mandy's outfit with a demure but still sexy cocktail dress she had. The neck plunged quite dramatically at the front and suggested that a glimpse of breast would be forthcoming; its soft folds however ensured that this would not be the case. The dress had a small fabric belt at the waist and came down with only a small flare to just above the knee, a small slit at the back allowing the wearer to walk confidently. The shoes were in a similar hue; they were open-toed sandals with two straps across the foot, another tying around the ankle, and a two-inch heel.

When Brian was fully dressed as Mandy, Louise stood him in front of her full-length mirror. Even though he had no desire to be so attired, Brian had to admit that he looked good.

At a little before eight, Louise and `Mandy' left the house, shouting goodbye to her parents. Both of the adult Greens were well used to a procession of young ladies going up and down to their daughter's bedroom, and did not notice that their daughter had actually come home alone from the mall earlier that evening. Similarly, they failed to notice the absence of their son, who they assumed was busy working on some project in his room. Their mother was watching a program on teenage delinquency whilst their father, who was half watching the same program over the top of his newspaper, bemoaned the slip in social standards and blamed neglectful parents for most of the social ills that blight the nation.

Louise dropped her brother off, and he nervously made his way towards the clock tower near the station. The wind was blowing quite briskly, and he could feel the breeze climbing up the skirt to the exposed skin at the top of the stockings. It also seemed to play around his penis and make him desperate to pee (he had been too worked up to remember to go just before he left the house). The clock said 8:13 when he arrived, and Kyle was already there waiting for him.

The older youth smiled when he saw his date approach and came and gave him a gentle hug and kiss. `You look wonderful, Mandy.' Kyle said.

`Er, thanks. You look very nice too.' was all that Brian could think of to say. They elected to eat before going to the Julia Roberts movie (which did not start until nine-fifteen). As they sat in the local pizza house waiting for their order to come, Brian excused himself and made for the toilets, remembering to go through the ladies' door. After peeing, and straightening himself up, he washed and dried his hands before checking his make up in the mirror. Louise had given him a small purse to match the outfit, containing an assortment of items that he might need (he was annoyed to see a condom included).

As he took a lipstick from the purse, he suddenly realized that he had not the slightest idea of how to apply the make up anyhow and quickly replaced it. In case either of the other two females in the room (a pert bottomed blonde in her early thirties and a rather overweight middle-aged woman in a tasteless floral dress) became suspicious.

Returning to the table, Brian saw that the pizza had been served, but that Kyle had patiently waited for his date to return before commencing with either of his two slices. At first they sat mostly in silence, a few vague comments about the weather and the food being the only dialogue.

`I half-expected you not to come.' said Kyle finally. `I thought you would get cold-feet.'

`I did have second thoughts.' admitted Brian, and they both smiled.

`It's understandable,' went on Kyle, `I remember when I first took a guy on a double date with Roger and Tiffany. I was incredibly anxious, but they were both so cool about it.'

`Roger and Tiffany from school?' Brian's eyes were wide as he thought of the football captain and head cheerleader being relaxed at double- dating with a pair of homosexuals.

`Yeah,' continued Kyle, `We went to a restaurant in Mason City where Trevor – that was my date – lived. I was more uptight about being seen by anyone we knew than they were. Tiffany suggested that if we were seen, then she would answer in that innocent voice she does that we had promised to take her for a gang-bang, and that she was looking forward to it as she liked band music.'

They laughed at this, and Brian asked, with what he realized was a touch of jealousy in his tone, `So what happened with Trevor.'

Kyle gave a half-smile. `I guess that breaks the correct code of conduct for a date. Trevor was a friend I met at a group for young homosexuals just coming to terms with their sexuality. We were close for a while in the sense that we supported each other with understanding our desires, but we were never `an item', if that is what you mean.'

Brian lowered his eyes, aware that he had rather meant that. `But why me?' Kyle looked taken aback by this question.

'What do you mean?' he asked.

`Well I assume you didn't go for me just because I was the only boy dressed as a girl at the party. Or did you' Kyle was quiet for a while.

`I suppose to a degree I did. I guess part of me wants to have the best of both worlds – a girl on my arm to show off to the world, and a man in my bed to share my nights. Also, I guess I saw something in you that I identified with. I was about your age when I first started realizing that I was different, though it took me longer to take my preferences out in public.'

Brian quietly ate his pizza for a while. He had never had any sexual encounters (he was after all underage), nor a girlfriend for that matter (he would wait until after university for that sort of thing). Kyle was the first one to show any such interest in him, but Brian knew he was not gay. Besides, a homosexual lover at school would almost certainly be discovered and would count against him when he applied to universities or merchant banks (his chosen career field). Even if it did not, then being found out as a cross-dresser was hardly a good move for anyone at any stage in their life. Even if Brian had been interested in going further with this relationship – and he most certainly was not – then the repercussions would be disastrous for his future.

The only real question was how to turn Kyle down gently enough for there to be a similar lack of repercussions from the other football players. He doubted Kyle knew about Mark and Randy's intimidation tactics, the catcher seemed too decent for that, but just the thought of the deranged visage of Randy was enough to make Brian shudder.

`Anyhow,' went on Kyle cutting through Brian's thoughts, `we are young and dating is what is expected of us. We see how we get on, and if it leads to something long-term that's great, if not, well, we kiss, say goodbye and move on as friends. You have to let life take its own course.'

Privately disagreeing with this simplistic view of life, Brian agreed and took a mouthful of pizza. The rest of the meal went on in a lighter vein than it had started, and Brian felt able to relax more. The fact was that everyone seemed to accept Mandy was a real girl, and providing the truth never came out, he should be able to minimize the problem.

Not only that, but the more he tried to keep his normal rational gaze on events and think through what option was most beneficial, the harder it became to stay in character. He considered this and decided that his only concern should be making people believe he was Mandy. That way there would be no possibility of this unhappy episode blighting Brian's life. So relaxing was this thought, Brian was able to watch the rather banal comedy on the screen without too much displeasure. He was able to ignore the plot (such as it was) and think through how best to draw his adventures as Mandy to a close tonight and forever.

Lost in his own thoughts, Brian became aware that Kyle had for a while had his arm around his shoulders, and that he, Brian, had been nuzzling in to the warm jacket of his escort. The awareness crept over him not so much when Kyle started stroking his thigh, but when the older youth's hand reached high enough to run across the fancy pattern at the top of the stockings. Brian started for a second, but as he looked across to Kyle, the footballer just smiled and leaned across and kissed him on the lips, his tongue only pushing a little way in, just enough to brush against Brian's teeth.

At first Brian started to pull away, but he forced himself to be calm. If he were going to break up with Kyle in an amicable way, he would have to give a little and then say it wasn't working out between them. No point in frustrating the footballer when his friends might feel that Mandy had never been sufficiently committed to the relationship. As their lips parted, Brian smiled back, and pushed himself back into the warm pillow of Kyle's shoulder. However relaxed he might have seemed, however, his mind raced as he felt the older boy stroking the top of the stocking, his fingers moving on to the soft, uncovered flesh above, working around the plum strap that came down from the suspender belt.

What if someone sees! screamed Brian's cautious mind, What if they call the manager and the police and we get arrested and they find out I'm a boy and…. Demurely, but firmly, Brian's hand entwined Kyle's fingers, sliding them along his thigh, down to the knee, his hand brushing down his skirt on the way, until it covered the stocking tops.

By the time they left the cinema it was dark, but not especially cold. Brian wrapped his arms around Kyle and snuggled into him, though the older youth had already removed his jacket and draped it around his date's shoulders. It gradually dawned on Brian that they were not going directly to the taxi rank (Kyle's car was currently stuck at a garage with a mechanic who always seemed to be able to find another reason why the vehicle was not yet quite fixed). Instead they had detoured into an alleyway. Kyle turned Brian to face him, and then taking him in his arms, began to kiss him, first on the lips, then on the neck.

Brian was at first shocked to be carrying out such an embrace in a public place, but he stayed calm and thought the matter through rationally. Without a car, they would have to either embrace in a public area or go to one or other of their homes. He did not really wish to face potentially tricky questions from Kyle's parents or even trickier ones from his own.

Therefore the second option was out of the question and he had no choice but to risk smooching in public, even though part of his mind keep seeing the police arresting them for public indecency and himself being unmasked as a boy. Kyle's jacket had fallen from Brian's shoulders, though he barely noticed, concentrating instead on touching Kyle's back and, occasionally to make the pretence seem more real, Kyle's butt.

He first became aware of the jacket's departure when he felt a cool breeze whispering across his back. A few seconds later he realized that the reason he could feel the breeze was not just the jacket falling away, but that Kyle had softly unzipped the back of the dress and was gently caressing his back. For his own part, Kyle was in a bit of a quandary. From what Louise had told him, Brian, in his guise as Mandy, liked to be dominated and drew back from the desires he had inside, despite his own yearning for them. Kyle knew the alleyway was out of the way and that it was highly unlikely that they would be disturbed.

He did not want to force Mandy against her will into going too far, but at the same time he knew that without another's direction, she would hold back. Kyle's right hand came down and pulled at the fabric belt around the waist of the dress. It yielded easily and he felt the dress ease away from the body of his date, hanging more loosely now that the zipper on the back and belt were both undone. This latest release seemed to alarm Brian and instinctively his body jerked forward as his hands came down to fumble for the belt. The dress was only being held up by the material that draped across the younger teenager's shoulders, and the generous opening at the front and now also the back allowed these to easily slip down, the rest of the dress leading the way.

For one awful moment Brian felt as if he were removed from his body, looking across at himself and Kyle from a few feet away. He was aware that in attempting and failing to grab his belt he has sent the dress tumbling down so that now he stood in Kyle's arms wearing just the deep plum bra, panties and briefs, the seductive stockings and the two-inch high shoes. Panic overrode all over senses. He stood there paralyzed into inaction for a few moments. During this time he felt Kyle hold him in closer, caressing the small of his back, his silk-clad ass, one hand running along the back of Brian's right thigh and pulling it up against him, the crook of the knee resting in the older youth's palm.

This embrace brought Brian back to his senses, and he felt the footballer's strong hands holding him, stroking him. He also felt the bulge that had developed in Kyle's trousers, a bulge that was even now resting against his midriff. Up to this point, Brian's worse fear had been discovery by the police. However, this fear proved to be both well founded and unexpectedly helpful when, in the intimate embrace the young couple suddenly found themselves in the powerful beam of a torch.

Looking past the source of the beam, Brian was able to make out two uniformed figures. Kyle gently patted Brian's ass and told him not to worry. Brian watched as his date walked towards the two men, only realizing after a minute or so that he was standing there wearing just his sister's skimpy underwear. Quickly he grabbed the dress and started putting it on, fumbling at first to get into it. By the time Kyle came back he had it back on and the belt retied, though he was only able to get the zipper half way up.

`Come on.' said Kyle, and picking up his jacket he gently took Brian's arm and led him past the two officers of the law. The two policemen smirked, but wished them a good evening. One even told Brian to hold on a minute and finished zipping up the back of the dress, patting the teenager's butt as he went back to the squad car with his partner. It was a good ten minutes before Brian finished blushing a bright crimson.

Kyle had the taxi drop them off in the next street to the one where Brian lived, and they walked around to the back of the youth's home. Louise had agreed to keep an eye out for her brother's return and make sure he could get in without his parents knowing. When they saw Louise wave to them from the back door, Kyle took Brian in close and kissed him on the lips, his tongue pushing through to seek out its opposite number.

`I want to see you again,' Kyle said, when the broke off the oral embrace. Brian was evasive, citing other activities that would prevent him having the time to set a day for their next date. Finally, realizing that he would not get a firm answer tonight, Kyle said he would talk to Brian about it at school tomorrow, kissed him again, and they parted.

Louise was all abuzz. She wanted to know all the details immediately, but recognizing the wisdom in not having her brother sitting their dressed as a young lady, helped him remove the outfit and makeup. When he was clad only in the panties, she pulled the silk away from his butt and looked into it saying, `Didn't get any KY jelly on my knickers I hope.' Her brother turned and glared at her, but said nothing. Afterwards, as they sat eating cookies and drinking milk (or rather Louise ate cookies as her brother did not believe in eating so close to going to bed), Brian gave her a brief description of his evening, carefully leaving out the events that took place in the alleyway, both before and after the police appeared.

Louise looked a little disappointed. `You know, you should give him a little more than just a kiss and cuddle. After all he is your first boyfriend and you don't know when you might get another as good as him.'

I do not want a boyfriend.' hissed Brian, not wishing to wake his parents by shouting. `I only ended up in this mess because of you.'

`Oh come on, Brian,' retorted Louise, `It could be a lot worse. Besides, perhaps you need a good shagging to loosen up that tight ass of yours.' For the second time that night, Brian went crimson. It was a few moments before he spoke again.

`Look,' he began saiding calmly and softly, `I am not gay, I'm not a transvestite, and I'm not going to start indulging in casual sexual encounters. As soon as I can I'm going to break it off with Kyle, put this whole sordid affair behind me and I never want to hear it spoken of again.' The last of these words were spoken in a cold tone dripping with anger. Louise was rather taken back by the fierceness in her usually dispassionate brother. However she realized that he was aware that she was in a position to use this as a means of tormenting him for years to come, and that did not accord with the carefully planned future he had mapped out for himself.

Louise bit into her last cookie and watched her brother finish the last of his milk. Without another word he left to go and brush and floss his teeth before going to bed.

Continued in Part 3 of I Never Planned on Mandy