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Barrack Room Betty - Chapter Five

"Transvestite Wrens seduce their sailor tormentors and experience sex as a woman for the first time"

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Chapter Five – Boys Will Be Girls


The three Wrens and three Leading Recruits were sitting engrossed in the movie. Michele rested her head on Jason’s shoulder and they were still holding hands.

Jean was reaching into Mary’s popcorn bucket every few minutes, chewing popcorn around swigs of beer; he was enchanted by her perfume and found her very attractive but he had no idea how to woo her. Then he reached for some popcorn and misjudged and his hand fell in her lap; he looked at her startled and snatched his hand away.

“Oh my god I’m so sorry,” he whispered.

Mary looked at him and smiled. She dropped the popcorn carton on the deck and took his hand in hers and put it back in her lap. Jean beamed at her and leaned into her.

“Thanks,” he murmured.

Mary kissed him chastely on the lips and squeezed his hand.

“Watch the dit; we’ll snog later,” she grinned at him and then turned to face the dit.

Jean sat there holding Mary’s hand, a raging erection in his bell-bottom pants and a beatific smile on his face.

Polly and Jimmy had been exchanging furtive glances on and off since Jean had moved next to Mary; the sexual tension between them was palpable and eventually Jimmy could take it no longer. He leaned over and whispered in her ear.

“Spike and Michele seem taken with each other,” he nodded towards the two lovebirds sitting three rows in front of them.

“Like it was some sort of secret? Really!” Polly replied satirically.

“What do you think?” Jimmy enquired.

“I think it’s disgusting; a transvestite Wren canoodling with a Leading Recruit,” Polly replied.

Jimmy blanched, disappointed with her reply.

“Yeah,” Jimmy sighed.

“Of course, if I was to do this, it would be entirely different and acceptable,” Polly sniggered.

She pulled Jimmy’s face to hers and kissed him passionately and reached down and squeezed his cock through his trousers.

Jimmy gasped with surprise and then responded to her kiss, putting his arms around her.

Polly shrugged him off after a minute or so.

“Okay, enough; let’s watch the movie."

But she left her hand in his lap and tortured him, running her nails along the outside of his cock, squeezing it now and then.

“You teasing bitch!” Jimmy smirked.

“Shh, watch the dit,” Polly sniggered, squeezing him again.

And so the three couples watched the movie, Michele holding hands with Jason, and Mary holding hands with Jean. Polly was idly stroking Jimmy’s cock through his bell-bottomed trousers. They were all content, entertained by the movie but at the same time wondering with anticipation what would happen next.

They had crossed the line just as Michele had predicted. This was no longer the Leading Recruits tormenting their grommets by making them dress as Wrens. The Leading Recruits had become infatuated with their creations and were now carnally involved. The Wrens had been feminised to the extent that they actually liked being dressed as women, and not only that, they appreciated the attentions of the four men left in charge of them.

They were all a little nervous about what had transpired but they were all content with the consequences; the only question was, how far were they willing to go?

The six newly acquainted lovers sat watching the movie, holding hands and canoodling, sipping beer and munching popcorn, just like sweethearts out on a date. Then all of sudden the reel ended and the screen was bathed in bright light. They all let go of each other and sat up straight, the cruel light putting an end to their intimacy.

“What the fuck?” Spike growled.

“Billy was supposed to have the second reel cued so it just cut right in seamlessly.”

“Never mind, folks; let’s call this intermission. Jimmy, go and get some more beer from the wets. Mary, you make more popcorn, and I’ll find out what the fuck is going on in the projection booth.”

“I’ll go with Jimmy and help with the beer,” Polly volunteered.

“And I’ll help Mary with popcorn,” Jean replied.

“And I might as well help Jason find out what’s going on in the projection booth,” Michele huffed.

“And fucking hurry up, you lot! I wanna see how The Sting ends; it was really getting interesting!” Michele whined.

She grabbed Jason’s hand almost dragged him up the aisle.

“Fuck! She’s got her knickers in a twist!” Jimmy laughed.

“Come on, big boy, let’s get that beer and get back here for the last of the show. I wanna see how it ends too,” Polly took Jimmy’s hand and followed the others.

“Just you and me left,” Jean said to Mary, who was still sitting in her seat.

The cinema suddenly went dark as the projector stopped, only the dim light of the exit signs providing a faint hue.

Jean held out his hand to help Mary out of her seat. She took his hand but surprised him by pulling him down into his seat and then she closed her face to his and kissed him. He was surprised briefly and then he responded, kissing her deeply and passionately. She threw her arms around him and pulled him to her.

It was awkward with both of them sitting side on and Jean lifted Mary out of her seat and put her in his lap and embraced her and kissed her, his tongue exploring her mouth.

“Oh god,” Mary moaned and threw her arms around her suitor and wriggled her buttocks in his lap.

Jean slid his hand along her leg and stroked her thigh.

“Oh, you naughty boy,” she gasped and kissed him again.

Michele led Jason through the lobby and up the stairs to the projection booth; Jason’s eyes were locked on Michele’s taut buttocks, her skirt tight against her cheeks as she climbed the stairs. At the landing he hauled her up and pulled her to him and kissed her; Michele pressed against him and lifted her leg and wrapped it around his as they fell against the wall. Jason’s hand went to her thigh as he kissed her deeply. Michele reached down and squeezed him briefly through the flies of his bell-bottomed trousers.

“We can do this later, honey; I really want to see the end of the movie,” she cooed.

“Jesus you’ve got me so horny, Michele, but yeah, I want to see how it ends too,” Jason capitulated.

They made their way up the last flight of stairs and opened the door to the projection booth and were shocked by what they saw.

Billy was sitting in the projectionist's chair, his bells around his ankles. Doris was sitting astride him, face to face. Her skirt was discarded and he was holding onto her suspender straps as she slowly rode up and down on his erect penis. They were kissing as they fucked, oblivious to the outside world. Doris had her heels planted on the deck and slowly rose and lowered herself on Billy’s engorged member. She still had her knickers on; the gusset had been pulled aside to allow Billy access to her virginal bud. Billy moved his hands to her waist lifting and lowering her in tempo with her gyrations.

Michele yanked Jason out of the doorway and back onto the landing and pulled him to her.

“Let them finish,” she whispered in his ear and then playfully bit his earlobe.

“They won’t be long,” she smiled up at him and drew his face to hers.

“But I wanna see how the movie ends,” Jason whined between kisses.

“It’s intermission; they’ll get the second reel going soon. I can keep you amused until then,” Michele smiled at him and dropped to her knees.

Michele opened the buttons on Jason’s flies and reached in and extracted his semi-erect penis.

“Oh, Michele, I’ve never had a girl do this to me before,” Jason gasped looking down at the pretty transvestite Wren on her knees before him.

Michele looked up into his eyes and smiled and then lowered her lips to his manhood. It quickly became fully erect and Michele slid her lips along his shaft and worked her tongue on his glans.

Jason put his hands on Michele’s head and slowly rocked backwards and forwards as Michele clasped her lips around his shaft and lapped at his fraenulum with the tip of her tongue. She didn’t expect him to last long and he didn’t. He filled her mouth with creamy semen and shuddered as he orgasmed; Michele looked up and was rewarded with the countenance of pure pleasure on Jason’s handsome face as she swallowed his issue. He gazed down at her and looked in her eyes with an expression of gratitude and devotion.

Michele dutifully drained him and licked him clean. She eased his deflating penis back inside his underpants and buttoned his fly. Jason helped her to her feet and drew her to him.

“That was wonderful,” he sighed.

Michele smiled wistfully back at him.

Jason made to kiss Michele but she turned her face aside.

“What?” he looked hurt.

“Well, you just, you know, came in my mouth and…”

Jason silenced her, turning her face to his and he kissed her deeply; his tongue exploring her mouth as they embraced.

“And it was lovely. I’m not ashamed or offended, Michele,” he stroked her hair and then pinched her playfully on the nose.

“Come on, let’s see the end of the dit,” he took her hand and then kicked at the projection room door.

“Hurry up, you two; we want to see the end of the movie!” he yelled.

There was the sound of a chair scraping and the scrambling of heels on the floor from inside the booth.

“Sorry, Spike; I got a bit distracted. I’m just loading up the second reel now. Won’t be long,” Jean’s muffled voice came through the door.

Michele and Jason broke into peals of laughter and made their way down the stairs to the foyer.

Over at the wets, Polly and Jimmy were rolling on the big couch, kissing, groping, fondling and stroking each other. The sexual tension between the two had been palpable for a couple of days now and as soon as their first chance to be alone together presented itself they couldn’t keep their hands off each other.

They started kissing as soon as they entered the wets and Polly had guided Jimmy over towards the big couch and pushed him down and sat astride him kissing him passionately, mussing his hair and squeezing his broad muscular shoulders.

“Is this okay?” Jimmy asked when they broke to get their breath.

“I just feel so feminine with you, Jimmy; ever since we started crossdressing I’ve sort of had a thing for you,” Polly admitted.

“I’ve heard the ABs and kellicks talk about going with Kai Tais and Beanie Boys during their deployments to South East Asia; the way I see it, this is no different,” Jimmy said.

“And I’ve had the hots for you ever since the first time I saw you dressed. I mean, I have the hots for Wren Polly, if you know what I mean,” Jimmy blushed.

“Let’s not make it complicated; you like it, I like it, let’s leave it at that."

Polly lowered her face to his and they kissed and then rolled onto the couch. They tentatively explored each other, Jimmy sliding his hands along Polly stockinged legs and Polly squeezing his hard penis through his bell-bottomed trousers. Jimmy loved the feel of her smooth legs and his hand went further up her skirt past the welt and bare skin until he found her nylon panties.

This would be the moment of truth! He slid his hand along the front of her panties and found Polly erect and leaking pre-seminal fluid. He was not disgusted and in fact, he found it very titillating and he kissed her harder and stroked her cock through her knickers.

The moment of truth came for Polly when she released Jimmy’s engorged manhood from his flies but as soon as her hand found his smooth hard flesh she was in heaven. She felt so feminine lying underneath him with his hand up her skirt while she stroked his turgid phallus and they kissed and caressed.

“Oh god, this feels so naughty, but also so delicious,” Polly sighed.

“What about this then?” Jimmy grunted and moved Polly’s hand away from his penis and rested it against hers.

He rubbed his penis against Polly’s through the diaphanous panty material.

“Oh my god, that is so good!” Polly crushed her lips against his and raised her legs and pulled him closer to her; arching herself and thrusting against him.

They were happy to frot for a while, then Polly whimpered in Jimmy’s ear.

“I want to feel it in me.”

Jimmy’s cock strained and pulsed at the thought and he quickly lifted her so that her buttocks were propped up off the couch. He took a pillow and stuffed it underneath her. Jimmy lifted Polly’s legs up in the air, her thighs parted and he pulled the gusset of her panties to one side.

“Be gentle, Jimmy,” Polly whispered her voice full of trepidation but also lust.

Jimmy was kneeling on the couch, Polly’s spread legs open wide as he attempted to guide his penis into her anus.

Polly grunted with pain.

"Sorry, babe!" Jimmy apologised

Jimmy spat on his penis and rubbed it all over, then he spat and rubbed it on her puckered bud.

“How romantic,” Polly giggled.

“Shut up,” Jimmy laughed along with her.

Jimmy pushed forward and the head of his penis pierced her sphincter. Polly moaned and bucked but Jimmy rode with her, not trying to push himself any further inside her but not letting her eject his cock.

"Honey, relax and it will be okay," Jimmy whispered, trying to soothe her.

"Okay, babe, but take it nice and slow," Polly moaned.

Polly knew that she needed to relax her sphincter and fight the instinct to push against the object invading her anus.

"That's it, sweetheart," said Jimmy as he felt Polly's sphincter spasm as she tried to relax it.

Polly forced her inner muscles to relax and the twinges of pain began to subside. Jimmy slowly pushed himself inside her; he took his time and whenever Polly flinched he stopped and soothed her. He took more spit and put it on his penis.

Jimmy continued to press slowly forward cooing and encouraging Polly to stay calm and relax her anal constrictor muscles. Then, when he had about three-quarters of his shaft inside her, he sensed her internal muscles respond and she gasped. His glans had found her prostate gland. Her reaction was pleasure, not pain.

Jimmy knew better than to rush; he took his time pushing the remaining few inches of his shaft inside Polly until eventually he was buried inside her with his scrotum resting snugly against her. He lowered his upper body down and as he slowly wriggled his penis inside her to stimulate her prostate he kissed her. She began to respond and kissed him back.

Polly felt Jimmy's glans rub against an area inside her that suddenly caused waves of intense pleasure to course through her body. As his penis stimulated her prostate, rings of pleasure ran up and down her insides; her sphincter responded and loosened and began to emit its own tingling ripples of pleasure. She gasped with extreme pleasure.

When Jimmy lowered his mouth to hers she kissed him back, deeply, passionately. She drove her tongue into his mouth and lifted her buttocks up off the couch and pushed herself up against him; her legs moved around his waist; she locked her ankles together and held him against her. She felt totally feminine lying here underneath this sailor, wantonly giving herself to him.

They fucked slowly but passionately, taking their time, Jimmy easing his penis in and out Polly's anus with long slow thrusts as she raised herself up to meet him. The firm, slow deep thrusts provided the maximum stimulation for both of them. They said little to each other; the fucking was accompanied by one long passionate kiss.

Polly felt him orgasm; his cock was fully embedded in her, his scrotum tickling her buttocks when he shuddered and wriggled his member inside her as it pulsed and throbbed. She felt the jets of sperm pulsing from his penis into her anus. He was kissing her wildly now, their tongues entwined, lips mashed, their teeth occasionally cracking against each other with the passion of the kiss.

Polly moaned as her own orgasm shook her body and she felt her semi-erect penis begin to pulse and expel her issue. Jimmy slid a hand between their bodies and milked her as she ejaculated into her panties.

Jimmy lay on top of her, supporting his weight on his elbows as they both slowly came down from their orgasms. He placed little soft kisses on her lips and kissed her on the eyelids and stroked her hair. Polly felt feminine and fully sated.

Jimmy extracted himself from Polly and lowered her legs. Some of his issue dribbled from her anus and Polly pulled off her semen-soaked knickers and wiped herself clean.

“Now I’ll be knicker-less for the rest of the night!” she grumbled as she smoothed her skirt.

Jimmy was pulling up his bells.

“I’ll fix my makeup and brush my hair while you get the beer. We’d better get back or they’re going to be suspicious,” Polly said straightening her blouse and her jacket.

Meanwhile back at the cinema, Mary was taking Jean’s load in her mouth; she was on her knees before him in the darkened cinema. As Jean exploded in her mouth, Mary spent her own seed on the carpet; squeezing the last of it out as she drained Jean; sucking the last globules of semen from his glans.

They adjusted their clothing and Jean went to make the popcorn while Mary went to the heads and fixed her makeup.

Five minutes later they rendezvoused in the foyer, Jean and Mary with the popcorn, Jimmy and Polly with the beer, and Jason and Michele down from the projection room.

“Okay, we’ve sorted the issue with our projectionist; we’ve replenished popcorn and beer, let's watch the end of the movie,” Jason said, rubbing his hands together.

“Okay,” said Jean.

“Okay,” said Jimmy.

The three Wrens looked at each other and rolled their eyes.

“Sure, guys. It’s like just we took an intermission and nothing happened,” Michele quipped sardonically and then broke into peals of laughter.

The two other Wrens joined her, pissing themselves laughing while the boys looked at each other knowingly, conceding that men would never understand women.

Jason smacked Michele firmly on the bum, albeit playfully.

“Come on, wench; let’s see the dit!” He took her hand and dragged her, still giggling, into the cinema.

The others paired off and followed them in.

They divvied up the popcorn and beer and sat in separate rows this time. There was no more sex; they were sated, but there was lots of playful caressing and kissing.

After the movie, they cleaned up the cinema and went back to the block and paired off and held hands. There were long goodnight kisses outside of the block and then they went inside to their respective cabins.

“Well! What a night!” said Jimmy Lovejoy contentedly.

“Yeah, I’ll say,” said Jean Burgess.

“Yeah, but does this make us poofs?" Billy Marron opined.

“Fuck off, idiot!” Jason threw a boot at him.

They all laughed and went to bed.

In the Wrens' cabin, the girls sat around chattering and giggling.

“Oh my god, Michele! I can see why you loved doing this before you joined the Navy,” Polly gushed.

Mary and Doris looked at Michele incredulously.

“What?” they both remonstrated

Michele gave Polly a snarky look and deflected the conversation.

“So, Doris, why the sudden change of heart? What happened to turn you from recalcitrant crossdresser to transvestite slut?” Michele grinned smugly.

“And why did Billy expect to meet you in the cinema before we all got there?” Polly joined in.

Doris smiled mischievously and replied.

“Well, it turns out Billy came over to the galley this morning while I was preparing lunch,” she explained. “Seems he has quite a thing for fuller-figured women,” she looked sheepishly at the others.

“Oh my god! He shagged you in the galley!” Polly squealed.

“Of course not, Polly! I’m a lady; I saved my virginity for the second date. I only gave him a blowjob!”

The Wrens all laughed.

Eventually, they quietened down and got ready for bed. It had been a long day.

They were all in their bunks and the lights were out and they were nearly asleep when Doris called out.

“Michele, tomorrow do you think we can find some nice nightdresses? I don’t wanna sleep in these pajamas anymore.”

“Go to sleep!” Michele replied.

She was smiling and about to fall asleep when she heard Polly grumble.

“And get some fucking KY jelly from the canteen!”


To be continued.

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