One for the Team Ch. 04

Chapter Four -- Wendy Takes Charge

November 1984

Robert wanted Charlotte to stay the night but they both knew it was fanciful and a downright dangerous idea. Robert Fellows may be the housemaster of Bridge House but he was still a student at Chelmsford College and would be subject to expulsion if they were caught.

"Do that thing to me again and then I'll leave, but I'll come back tomorrow night and every night after if you want me to," Charlotte kissed him and stroked his burgeoning erection.

"What thing?" Robert teased.

"The thing that made me cry," Charlotte said wistfully.

The look of shame and disappointment on Robert's face was worth the hyperbole.

"I'm sorry Charlotte I never meant to hurt you. I err... I like you so much; I desire you and I couldn't help myself. I wanted you... I mean I want you... I mean I think about you all the time... Christ I don't know what I mean," Robert stammered.

Charlotte put a finger to his lips to shush him.

"Can I tell you something?" she murmured.

Robert nodded.

"So long ago now that I can hardly remember, when I had my first sexual awakening, I used to fantasise that a handsome young man would seduce me. I would play coy and rebuff his advances. He would become insistent and force himself on me and I would feign abhorrence as he ravished me but I would eventually submit and let him take me and would secretly enjoy it."

"It's a common young woman's fantasy but I actually got to live mine," Charlotte kissed him softly.

"But I hurt you," Robert stroked her cheek softly.

"Yes you did at first but then it was kind of nice and then it became wonderful. You were my first Robert. You will always be my first and I'm glad it was you," she smiled at him.

"Now... can we stop all this sentimental drivel? I want you in me. All the way," she squeezed his dick very hard and rolled over, offering Robert her derriere.

*****

Robert was very satisfied with this new arrangement. Charlotte could come to him every night if she wanted to and she did most nights. But Wayne Jenkins and Steven Belfour-Brown were not. They had been cut off and they were angry about it. They were also determined to do something about it.

Charles had just changed into his rugby kit and had gone to the toilet before running out on the pitch to train, when the door to the cubicle he was using was suddenly kicked in.

"Sitting down to piss like a girl. Appropriate I think," Wayne Jenkins squeezed into the cubicle followed by Steven Belfour-Brown.

"Don't bother screaming. There's no one in the dressing rooms except for us," Wayne Jenkins hissed.

He produced a copy of the photograph of Charlotte holding the newspaper. It had been so long ago that Charles had almost forgotten about it.

"My father might not be a member of Brooks's but he's well-to-do enough to get an audience with Reginald Ward. I'm sure your dad will recognise his youngest son, even through the wig and the makeup," he pushed the photograph into Charles' face.

"What do you want?" Charles asked.

"We want Charlotte back. We want her in the inner sanctum three times a week doing what she does best," Steven Belfour-Brown snatched the picture and shoved his face into Charles'.

"What about Robert?" Charles retorted.

"What about him? He can have Charlotte when we're not using her. She's House property not his personal plaything," Steven replied.

"I don't think he sees it that way," Charles said indignantly.

"I don't care what he thinks. He might be the housemaster but he can't take everything for himself. You tell that slut that she had better get her arse back to the inner sanctum tomorrow night or Reginald and Penelope Ward are likely to find out that their son is still a sissy!"

"You can keep this; we have plenty of other copies," Wayne Jenkins tossed the photograph at Charles.

"Now pull up your shorts and get out on the track Mister Ward; you're late for training," the two thugs left the lavatory, the studs on their football boots clattering on the concrete floor.

Charles immediate reaction was to tell Robert. But what could Robert do? He could confront Wayne and Steven and do what? He couldn't go to the faculty; what would he tell them? 'I moved a young man into the dorm next mine and almost every night he transforms into a pretty woman who sneaks into my room and pleasures me. Oh I forgot to mention, before she became my girlfriend I threatened to expose her to her parents and made her give my friends blowjobs. Now I want to keep her all to myself.'

The whole situation was too bizarre to be true.

This was a situation that Charlotte would need to tend to on her own. There appeared to be only one option which was for Charlotte to give Wayne and Steven what they wanted.

Charles was sitting at the breakfast table, his food untouched, pondering his quandary when William Larkin plonked himself down across from him.

"If you're not going to eat that don't let it go to waste," he leaned across and speared a sausage off Charles' plate and stuffed it into his mouth.

"How do you stay so slim? You eat like a bear about to hibernate," Charles looked at the 'full English' that William was devouring before him.

"Well I train hard for my soccer team, I run cross-country with you, I fag for an upper houseman who won't lift a finger to help himself and I spend all night studying to make my grades. It's tough being a scholarship student," William replied around a mouthful of bacon and eggs.

"Yes I sometimes forget that most of us are privileged," Charles mused.

"Oh don't worry Charlie, I get by. I have my skills," William chuckled.

"Skills?" Charles' mind was drifting back to his own problems.

"Well no one gives an Oxford rub like I do and I'm pretty good at..." William picked up a sausage off his plate and pushed it in and out of his mouth, sucking on it.

"Jesus William!" Charles blushed.

Then he thought about what William had just said.

"You said you get by, using your skills?" Charles was suddenly very interested.

"You toffs take everything for granted but some of us have to work for a living. There are plenty of upper housemen who like us younger pretty boys. They'd never admit it to each other of course, but a hard dick has no conscience," William smiled.

"There are a couple of blokes over at Crozier House who hand out fivers for handjobs," William reached over and took one of Charles' uneaten fried eggs and stuffed it in his mouth.

Charles hardly noticed; he was lost in thought.

"William? Can you skip the lecture on ethics this afternoon and come to my dorm?" Charles asked.

"Wow! It's like being asked to come to the palace," William teased.

"Oh stop it. Can you?" Charles asked earnestly.

"Sure. Of course I can Charlie, I have no ethics anyway. Now can I have the rest of your baked beans?" William asked and Charles pushed his plate across the table.

That afternoon William climbed the stairs to Charles' dormitory. The corridors were silent with most of students in class. He knocked on the door and waited.

"Is that you William?" William didn't recognise the voice that called to him but he responded anyway.

"Yes of course it is? Who do you think it is; the Queen Mother?" he answered sarcastically.

"Come in and lock the door behind you," the voice called.

"Oh intrigue. I like a bit of intrigue. Nothing like a... well fuck me!" William was gobsmacked.

He had entered Charles' dorm and closed and bolted the door behind him fully expecting that Charles' might have some booze or a joint to puff on, hence all the secrecy. What he did not expect was to see was a rather delightful young woman dressed in a French maid's uniform, black stockings and high heels. She sported a black bob hairstyle and full makeup.

"Jesus Christ you look like that waitress in Allo Allo," was all William could bring himself to say.

Charlotte stood dead still in the centre of the room and William circled her looking her up and down.

"If I was at all interested in women I'd have to say I'd give you a good rogering any time," William touched the frilly hem of her dress.

"I'll take that as a compliment I suppose," Charlotte replied.

"I knew it! I guessed you were into crossdressing. Those little ringlets of nailpolish on your cuticles, the eyeliner and mascara that you failed to wipe away. But my god, you're... you're... you're passable. I mean if I saw you on the high street I'd think you were a woman," William gushed.

"The highest compliment a person can give a tranny," Charlotte stopped posing and walked over to the side table and handed William a beer.

She took one herself and sat down, smoothing her skirt under her legs.

"You even move and sound like a girl. Where did you learn to do that? The French maid thing is a bit cliché though isn't it?" William took a seat opposite her and popped the ring-pull off his beer.

"Robert sometimes likes me dressed this way," Charlotte replied bluntly.

"Does he now? I never would have thought you batted for the other team Charles. Congratulations on taking up with the handsomest guy in the College though. I guess that explains why you moved into these quarters," William took a long pull on his beer and looked around Charlotte's rooms.

"My name is Charlotte, William, if you don't mind," Charlotte replied, pouring her beer into a glass and taking a ladylike sip.

"Well Charlotte. Don't leave me guessing. Tell me how this all came about," William took another sip of his beer and reached for his cigarettes.

Charlotte told William her life story, omitting nothing.

"I wondered why you kept sneaking out back of the common room. But you didn't like what those rugby lads were doing to you down in their inner sanctum but now you like being Robert Fellows' girlfriend?" William tried to make sense of recent events.

"I can't say I didn't like it. I just didn't like that they were forcing me to do it. I'll admit to you, but nobody else, that I quite liked being their plaything... but now Robert and I have this arrangement and that's that," Charlotte explained.

"I have to admit I quite fancy those big rugby types but I never would have guessed they were gay," William helped himself to his third can of Carling.

"That's just it. They don't consider themselves to be gay. As long as I'm dressed as Charlotte they rationalise it all away," she explained.

"Just like the lads who give me a fiver for a blowjob and then go home to their girlfriends during the half-term holiday. They rationalise that it's just a public school trope; like house initiations, getting rips for no reason, midnight feasts, pranks between the houses... nothing like a bit of discreet buggery to keep the public school traditions alive," William said sarcastically.

"Well that sort of gets me to where I was going anyway William. Did you say that you charge the upper housemen five pounds for fellatio?" Charlotte mused.

*****

When Charlotte came out of the privy that evening down in the house council's inner sanctum Wayne Jenkins and Steven Belfour-Brown were waiting eagerly for her. It had been some weeks since they had last defiled her and they were both randy as old goats.

She had brushed off her old sperm-stained pencil skirt and mauve satin blouse. She did not intend to give either of the two men the satisfaction of seeing her dressed in better clothes, even her stockings were laddered.

Not that either of the young men cared, they were both sporting erections that they wanted Charlotte to take care of for them.

"I have some good news and some bad news for you chaps," Charlotte strode confidently into the centre of the room.

Wayne and Steven sat in their usual seats eagerly awaiting her return, a porn movie played on the television set providing titillation prior to the main event.

"Get over here and suck my cock Charlotte!" Wayne Jenkins called out.

"There will be plenty of time for idle chit-chat once I've come in your mouth," he sniggered.

"Not happening I'm afraid; at least not with me. That's the bad news. The good news is there is another sexy transvestite who will satisfy your every sordid desire, the only caveat is that it will cost you both a tenner each," Charlotte pulled back the brocaded curtain and a stunning young woman sauntered into the room.

"This is my friend Wendy," Charlotte introduced a very different looking William Larkin

Charlotte had lent William one of her skirt and blouse sets, some lingerie and stockings and one of her wigs. She had sat in her dorm with Wendy and painstakingly instructed her in the application of makeup until she was reasonably proficient. There is a saying amongst crossdressers and transvestites: 'A pretty boy makes a pretty girl' and this was certainly the case with Wendy, the name she had chosen for herself.

Wendy said that she didn't mind dressing enfemme but could take it or leave it.

"Seems like a lot of work for the same results?" Wendy had said as she looked at herself in the mirror whilst Charlotte fussed with her hair.

"What do you mean?" Charlotte asked.

"Well either way you're going to end up on your knees sucking a dick or bent over taking it up the wrong 'un," Wendy smirked.

"That's not what Robert and I do," Charlotte sniped.

"Oh my god it's not 'loorve' is it?" Wendy teased.

"No! It's nothing like that! We just have respect for each other. Our lovemaking is tender," Charlotte quipped.

"Sounds like 'loorve' to me," Wendy couldn't help badgering her friend.

"Hey you want to make twenty quid, three times a week or do you want to keep sneaking around dormitories offering a handie, an Oxford rub or a BJ for a fiver?" Charlotte retorted.

"I suppose you're right. And I have to admit I do look quite pretty. If I wasn't gay I'd shag myself," Wendy snickered.

And that explained Wendy's existence.

"Jesus Charlotte! Where did you find her? She's fucking gorgeous! Who is she?" the two young men spoke over each other in their eagerness.

"All you need to know is that her name is Wendy and she's my surrogate. She'll sneak down here three times a week, go into the lavatory without you ever seeing her and emerge looking just like this," Charlotte explained.

"And we have to give her a tenner every time she does?" Steven frowned.

"Each. But don't you think she's worth it?" the two young men were circling Wendy, touching her and admiring her.

"I guess we will find out. Are you joining in?" Steven Belfour-Brown asked wistfully.

"I'm afraid not. I'll stay long enough for you to get acquainted and then I have other matters to attend to," Charlotte replied.

"Hello my pretty," Wayne Jenkins, stroked Wendy's hair.

"Hello luv," Wendy replied.

Charlotte poured herself a drink and settled on one of the couches.

She stayed long enough to watch Wayne and Robert paw at Wendy who did not seem to mind the attention at all. Charlotte returned to the privy and transformed back into Charles.

Charles peeked around the curtain before he left.

Wendy was on her knees on the couch sucking on Wayne Jenkins' penis while Steven Belfour-Brown knelt behind, sodomising her. So much for the rules about not kissing or sodomising the transvestite because that would be gay.

Charles went back to his dorm and transformed into Charlotte. Slipping into a negligée she opened the door to Robert's room and found him sitting in an overstuffed armchair moping. He was wearing nothing but his underpants but the room was warm from the fire.

"You're late; I thought you weren't coming," he brooded.

"I had little chore to take care of. Don't sulk, it doesn't suit you," Charlotte sidled over to him and sat in his lap.

His put his arms around her instinctively. She swivelled in his lap so she could kiss him and he returned the kiss. She could feel his growing erection pushing into her buttocks and she liked it. She liked the effect she had on Robert; he was besotted with her and treated her like she was his girlfriend, which she supposed she was, but she wasn't stupid enough to think that it was any more than a contrivance of convenience for them both. She knew that Robert was popular with girls and had plenty of women who gladly gave themselves to him outside of college.

Whatever this was it suited them both for now and she was determined to make the most of the situation. She was in some respects living her fantasy. A handsome, articulate, well-endowed young man was smitten with her and treated her like a lady. That is to say treated her like a lady when he wasn't shagging her senseless as she bucked beneath him coaxing him, whispering obscenities into his ear to spur him on.

Charlotte wriggled her backside appreciatively, pressing her buttocks against Robert's erection, feeling it grow to full tumescence. Normally they would take their time and draw out their love-making but Robert was right; it was getting late.

Charlotte reached behind herself and took Robert's hard cock in her hand. She lifted herself up a little and slipped his cock inside her knickers so that his glans nestled in her sphincter. Charlotte had pre-lubricated in anticipation and she put her heels on the floor and her hands on his knees to steady herself and then slowly lowered herself so that Robert's shaft slid all the way inside her. She was sitting in his lap with her back to him, impaled on his hard throbbing cock.

Robert held her waist and Charlotte rode up and down on his long slender cock, burying it deep inside her and then drawing it nearly all the way out.

Robert tried to encourage her to go faster and rose up out of the chair to meet her but she deliberately kept the pace of their fucking slow and rhythmic. His penis was pressing on her prostate and when Robert's hand slipped under her negligée he found her knickers distended with her erection and soaked with pre-ejaculate. He stroked her and Charlotte purred.

The fullness of his cock buried in her anus and the delectable feel of Robert's fingers rubbing the silky fabric of her knickers against her cock triggered the reaction that Robert so desired. Charlotte began to ride him faster, bucking and writhing in his lap as she worked her buttocks, driving him deep inside her.

Robert put a hand on her shoulder pushed Charlotte down into his lap and pushed himself up out of the chair as he thrust his engorged manhood into her as far as it would go and ejaculated inside her. He squeezed her cock and was rewarded when a sticky puddle of semen flooded through her knickers. They moaned and writhed and extracted every scintilla of pleasure from each other.

Charlotte spun around to face him, still impaled on Robert's cock. She drew herself up so that her knees rested on the seat either side of Robert and she kissed him as she continued to ride his swollen member. As was often the case, Robert didn't lose his erection; it diminished slightly but never became flaccid.

Charlotte kissed him passionately driving her tongue into his mouth and ground her soft buttocks into his groin until she felt him become engorged once again and then she fucked him a second time, Robert held her by the waist and guided her up and down on his throbbing member until she felt he was close to release again.

Charlotte leaned back and threw back her head and moaned as he came inside her. She ripped the hem of her negligée out of the way so she could get to her cock and stroke it, spattering Robert's tight belly with her seed.

They were both exhausted and Charlotte climbed off him and fetched towels so they could clean up and then she snuggled back into his lap content to just kiss and caress.

"So what was this little chore you had to take care of?" Robert asked as he lit a cigarette for them both to share.

She told him.

*****

"So how did it go?" Charles asked William the next day.