Gordy Gets a Skirt Ch. 02

Story Info
Gordy continues his adventure into forced crossdressing.
3.5k words
4.45
21.3k
13

Part 2 of the 5 part series

Updated 06/09/2023
Created 01/22/2020
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I wish to thank Mike Lair for feedback, discussing ideas with me as my editor.

***

As expected another box arrived before the weekend making him the proud owner of four bras and six panties all free samples from his employer, the lingerie leader, Maidenform. Free in exchange for wearing them daily and giving feedback on fit. He was tricked into the runway program by some mischievous co-workers but mostly his crush and their boss. These bras were two of the same style but one was a dark grey t-back and the other was pink. He sighed opening the package and thinking maybe another plea to his boss would get him out of the runway trials program. Or, not! He'd figured out by now it was a punishment. Same notes as before. Blah, blah, blah. "Wear the stuff, see fitting team." Twelve weeks, huh? This note was different than the previous ones in that it had a little burgundy lipstick kiss signature. He laughed not giving a thought that only his note got this private touch.

Weekend is here. He hung up his sport jacket and watched himself in the mirror remove his shirt-he did get a kick out of seeing the delicate lace bra appear from under the shirt on someone, anyone really. Sexy lingerie always caught his attention and he laughed at himself. These bras were a total nuisance. He didn't have time before work to quick change at the office but on the way home he got into the habit of removing it at the end of the day and stuffing it in his backpack before walking out the door. At 4:55 he could manage to get the bra off without removing his shirt or jacket although the sleeves had to be big enough to allow a hand to skinny up to grab the straps. The panties weren't bad at all. In fact they were very lovely soft, sleek, and yes, sexy! He found himself sneaking a feel down his trousers several times a day and giving his cock a good tease. "Girls were so lucky" he thought to himself, walking around all day in sexy, hugging panties must make them perpetually horny. He wondered why he never caught girls reaching up their skirts and playing with themselves. Oh, well. He decided panties were no inconvenience at all and would perhaps in other circumstances be quite content to wear them all the time.

Monday arrives. "How's that t-back fitting, Gordy?" he heard a voice and looked around. Cammy! He wondered if it showed under his jacket somehow. "You know some girls think the front close bras make the best cleavage, right Gordy dear?" she sniggered and continued. "If you want, I can show you mine but I want to see yours too." She walked away with a smirk taking high steps and planting her pumps down with a distinctive cadence, tossing her shoulders back and forth, letting her curls wave at him. Did she just wiggle her hips at him? He didn't get it. She knows what bra he's wearing and now offered to partially disrobe for him. Plus she turned him into the boss for harassment and now she's flirting again? He scratched his head and went back to work but the conversation wouldn't leave the back of his mind.

After lunch he wandered over to Cammy's desk and without asking permission began to massage her shoulders as he had done so many times before. She moaned in a low, sultry, quiet voice obviously approving his caress. He whispered "I've been thinking" as he moved laterally then pushing his thumbs down her spine he thought he felt the same bra he was wearing-no back clasp, and straps moving diagonally from shoulder to center, joining a couple inches above the chest band. "What did you mean show me yours?" he asked. "Just where?" He continued rubbing her shoulders and she moaned again, more quietly. He began to slip his hand down her torso to her cleavage to confirm but her hand quickly stopped him from getting very far.

She turned looking up but without shooing his hands. He was free to continue massaging her back when she dropped the icy truth "Don't you have a girlfriend, Gordy? I was sure you did?" He froze for a moment face gone pale white and eyes glazed like a deer in headlights. Only a moment had gone by and he started moving fingers again, down her back and shoulders only, mostly not swayed by her insinuation. He meant intuition. That was it-intuition.

He slipped a finger inside her collar and under her bra band "Maybe." He pulled the strap enough to get her attention "I want to see this on you. Only this. Where?" The truth was his girlfriend was on a college expedition for the winter in the outback of Australia-summer down under. He'd hardly heard from her in two months. "Don't worry about Sandy. I'm sure she's still alive."

Cammy detected the sarcasm and loneliness in his lament. It explained his chauvinistic tendencies somewhat but he was still a playboy. "The 5th floor rest area is hardly used. Can you meet me there at 2:00?" It was already past 1:00. She would have just enough time to plan some surprise. "Ladies room of course, sweety" she winked and pushed his hand away. "See you then."

Gordy was sporting quite an erection by then, from both the close touching of Cammy and the thought of seeing her partially disrobed in not too many minutes. Hopefully she didn't notice. He went back to his desk but debugging the "AR Cash application" was futile and he couldn't concentrate one whit. 1:55 time to move. He headed for the elevator and punched 5, walked down the empty hallway, and knocked on the ladies room door "Cammy?" No answer. He pushed door open slowly and walked in one step. "Cammy?" Still no answer. He walked in past the entrance. There she was as promised, blouse unbuttoned to her naval and wearing, yes, the exact same bra he was wearing. He could see enough to be sure.

"Take your shirt off mister!" she commanded forcefully. "Show me your stuff." She tapped her foot and the leather of her pump echoed off the restroom tile. He complied almost without hesitation. She unbuttoned her blouse at the same time and there they stood, face to face, looking at each other's chest. "Nice bra!" she chided sarcastically in a giggle taking a step forward then sliding a finger down through his furry chest and pulling the band hard enough to make him lose balance. "But no boobs to put in them, a shame." She fondled the empty cups and waited. He followed her lead and placed his hands on her bosom and to his surprise no objection. No way could she complain to the boss any more about his advances. She stopped fondling him and clasped her hands behind his neck slipping her leg between his and pressing her pelvis against his. She lifted her thigh against him until she was sure she felt his package. Yes, she pushed in radially against his growing member. "I have a secret" she whispered. "Can you guess?" She leaned her head on his shoulder and let all her weight rest on his frame.

Gordy feeling his oats took a gulp and continued to squeeze her breasts, pulse rising, pheromones a pumping "You're in love with me and want to fuck me right now?" he sort of half answered, have asked. Truth was he was ready to lock the door and do her right this minute. They heard footsteps approach the door and keep going past. "I thought you said nobody came up here?" he asked in half a panic with a whisper.

"No!" she hissed back. "I'm not in love with you." She didn't deny the fucking part. His suspicions finally confirmed-she could be charmed. He hadn't lost his touch. He had been fondling her over the bra this whole time and slipped his finger inside the cup to touch more closely and slid across her very erect nipple.

She stepped back and pulled his hand away. "Not now. That's not the secret." While she put her blouse back on she told him the little secret. "I'm in the runway contest, too. So, I'm trying the same products you are!" Then with a giggle "we can be sisters for these twelve weeks. I'll help you." There was more to this secret she didn't tell, but what she said was the truth. He started to put his shirt back on but Cammy stopped him. "Wait, not yet. I have something for you" and with that she produced a pair of chicken cutlets. She slipped one inside each of his cups. "There, much better. Now you have something in there-no substitute for a breast, but it will help fill out the proper shape of that bra."

"Nahhhhh. I have a hard enough time hiding it under my jacket as it is." He handed them back.

She pouted, blinked her eyes and placed hands on her hips. "Listen, maybe I'll think you're hot and you'll get to know me even better sooner" she lied unconvincingly. "How about that? Now, please." She pushed them into his hands pleading with her eyes. "Put them in and be a good girl. I'll make it worth your while." He felt her hand slide across his abdomen and glide across his boner. She squeezed.

Gordy shook his head and wanted to answer "you're so full of bullshit" but he did want her bad and not a good strategy. Feeling like a fish being reeled in on a line "OK, your sweetness" he conceded defeat as he put them back in his bra though with another shake of his head getting dressed. What now? Checking himself in the mirror he could see two unmistakable lumps under his jacket, especially from a side angle. Oh boy.

Gordy's lust for Cammy grew to an intensity the thought of getting a lawyer involved to help get him out of his predicament was just a fleeing thought. He was going to nail that girl and if this was the only path, so be it. Spending about 15 minutes reading the employee manual he was able to confirm the runway trials were spelled out and since a high dollar value of goods were involved he was obligated to finish or have the cost deducted from his paycheck. However, there was no mention of "Pink Blouse Wednesday" whatsoever. What? You're kidding me? Shit, they had him fooled a couple weeks real good. He'd have to pay more attention to subtle rules and enforcements.

Sure enough on Wednesday he wore a very dark, opaque shirt almost hiding the lumps on his chest. "These chicken cutlets have to go as well" he thought to himself. His shirt tented in the middle and a tie did little to hide it. "Boss wants to see you" Sabrina nonchalantly informed him as she sauntered past his desk. Gordy shrugged watching her hips sway as she walked away. Maybe he would do that one too, or maybe he better go see Stormy. With a sigh he did the later.

Her door was open and she was on the phone. She motioned for him to sit and he did. Her half of the conversation sounded like a customer conflict, in his estimation it is boring stuff. She placed the phone down and smiled at him with unrepentant evil intent reminding Gordy of a spider approaching a fly. "How's it going, hot stuff?" her countenance softened. "You're doing good work, buster, and possibly up for a promotion to Sr. Software Engineer, but" and after a pregnant pause "it seems you're slumming your way back into non-compliance." He sighed. She continued "Do you know what I'm talking about?"

Gordy shook his head no and shrugged his shoulders. He could even lie with body language. Hoped it passed her women's lie detector intuition.

"I'm talking about Pink Blouse Wednesday" she almost screamed. "You are trying my patience young man. Did you forget? I'm losing confidence here at a critical moment!"

"Uhhhh, no" he stammered slightly intimidated. "I read the company policy manual and there is no mention of 'Pink Blouse Wednesday' nor anything about pink blouses at all. I think it's customary for the women to wear that but not a rule and not for me." There he said it. All laid out nicely and accurately. He smiled.

She giggled "Yes, I know that. But, it's a tradition in this department. If you want to stay in your bosses good graces, and I think you do, you'll go home at lunch and fetch your very pretty pink blouse we know you love to hate." Pointing her finger in the air and lowering it towards him "Did you happen to remember the rule on legs by any chance? Since you read the dress code?"

Truth was he read it but nothing stood out. He shook his head "Not really. Legs?"

"Yes, legs" she confirmed. "It's quite clear, really. And you're part of it." She turned to her computer and clicked a tab which just happened to be on the right page. "All front office personnel" she stopped reading and said directly to him with a wink "that means you" turned back to the page "must wear some kind of hose. Pantyhose, tights, leggings, stockings, or thigh highs are required. No bare legs." She turned back towards him. Pull your trouser leg up and show me.

He pulled his pant leg up past his ankles to his knee. "Stop! Stop right there" she commanded. "This is what I meant. Now over your lunch break you will go home and get your pink blouse and on the way back buy some pantyhose." She added "or one of the other options. I don't care."

"Your silliness, I'm not doing that" he wanted to say. It was on the tip of his tongue. But, instead like a sheep about to be sheared he said nothing.

After a long silence she shooed him away "Dismissed." She gave a hard, cold stare and he returned to his desk.

It was a long commute home and he'd barely make it back in an hour. He considered options while he sulked at his desk for a few minutes and during his daydreams felt a caressing touch. Without turning he was sure who it was. "How'd it go in there? We heard her get excited. Did you get fired?" She slapped his shoulder playfully. "You sure know how to bring out the worst in her." She kissed him discretely on the cheek and rubbed his shoulders hard.

Gordy looked at her saying in a quiet voice. "I need to get pantyhose and a pink blouse over lunch. Not enough time."

After thinking for a moment Cammy came up with an idea "Oh, I'll help with that. Meet me at the 3rd floor at lunch time. The runway area has many discarded outfits and I bet we can find you a pink blouse for this afternoon, then wear your good one next week. And, pantyhose? Goodness, there's a Rite Aid at the corner. Easy Peasy."

This seemed too contrived or was she just kind but little choice did he have. "Can you buy the pantyhose for me?" he pleaded with Cammy.

"Sure, hot stuff" she used Stormy's pet name for him "but, then I help you put it on and fit it with you."

Now that sounded like a fun, kinky time to Gordy. "Sure. Thanks so much."

11:55 he headed to the runway area on the 3rd floor as instructed and it was mostly dark. Some lights were on down a hallway and he went there to find Cammy. "Hi there sweety" she greeted him. "I found some blouses. Go ahead and try them." She pointed to a garment rack with five pink blouses. He looked at the content tags which were missing in two of them. Those were too small anyway. A nice one was too small size M. A sheer and sexy one in XL with a deep V neck fit just fine. "There ya go."

He shook his head. "Not so fast. Not my style." He tried on the last one and it was a bit snug being size L, but it was full, thick, cotton, button down oxford. "Perfect!"

Cammy laughed. "That is way too tight. But, I suppose for just one afternoon." She handed him a new 2-pack of grey tights. "OK. Strip. I'll show you how these work." She made it seem a lot easier than the time he had to put on tights himself only achieving partial success getting a damaging runner on the first wear. "You have to always roll them up, and toes fit first, then roll them out slowly inch by inch. Then after up to your thighs pull firmly to get out wrinkles and slide up your belly as high as they can go. Piece of cake."

She slapped his sexy ass in the grey tights and squeezed him. "I see you're getting excited about this. Are you a sissy?" She leaned into him pressing her breast into his arm and continuing to fondle his cock through the nylon fabric. He leaned down and approached her lips. "Are you a sissy? Do you want to call me mistress?" She pressed her lips to his making it their first kiss. He moved his hand up and caressed her tit, squeezing hard. Wow, a lovely moment. She shivered for a moment and felt a leak in her panties as she became seriously aroused. She put pressure on his hand after a moment to push away, but he held on fast. She moved back down to his groin and continued with the groping. "We have work to do. See you downstairs hot stuff." With a firm push she turned around and walked away.

Gordy was mesmerized by the swaying of her hips and this did nothing for his raging hard on. "Never grow tired of this" he thought to himself. "Thank you" was all he could say as she disappeared down the darkened hallway. He pulled his pants on over the hose, put his crew socks in his pocket, slipped on his loafers and headed to the catering hub to grab a sandwich since he almost missed lunch.

While finishing his sandwich at his desk Stormy stopped by. "I see you listened to me" she praised him. "There is hope for you yet. Did you?" she glanced at his ankles and nodded her head directing with her eyes. "Show me." He dropped a loafer on the floor and pulled up his pant leg exposing the nylon clad leg in opaque grey tights. She whistled "Good girl. Very good. You can take a lesson after all. Maybe I have to start you bringing me coffee in the morning" she giggled.

He scowled at her despite her being the boss. She gave a wry smile as she headed back to her office and he noticed again almost irresistible hips swaying one step at a time. His cock leaped to attention and he had very bad thoughts about Stormy. Very bad indeed. Indescribably bad.

Back home he fished the nice, pink, silk blouse out of the junk pile and read the content tag "Dry clean only." Well, he had a whole week to get it cleaned. No problem. He laid it across the desk chair to remember. As was his new "after work routine" by now he got out of his girlie clothes, hand-washed them and hung them on the back of the bathroom door to dry. Only problem is yesterdays were gone. Next problem was he didn't notice that either. He opened his undies drawer for a nice pair of cotton briefs for clubbing and found a note with the missing bra and panties. He saw the bras were no longer all stuffed into a pile and shoved in without a thought. Now they were all lined up cups inside each other all facing out. Panties all nicely folded and in overlapping piles. He read the note: "I put her undies in here with the rest. I know I've been gone a couple months but didn't expect you find a replacement for me. I'll miss you dear Gordy. Love, Sandra. Muaaahh xoxo"

NO, NO, NO. Sandy has got the wrong idea. He didn't know she was back in town. Of course she probably said that in her letters, but he didn't make note of these things. He could explain. Or could he? What was worse? 1) He got a new girlfriend who moved in or 2) he was crossdressing now and he was the new girlfriend. He sighed and will need to give it some thought.

Just about this time his cellphone rings. It's Cammy. "Hiya, mistress." Gordy jokes around.

"Oh, about time you started calling me by my rightful title, dearie. But, I thought maybe you want to join us for drinks? McNeals at 7:00. Upper West Side. You know the place?"

What a break "I'll find it. Thanks for thinking of me." Fact is he knew the place.

6:30 he heads out for McNeals hoping to score a ride home with Cammy. So far he only made it to first base. Tonight "home run" was the goal.

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AnonymousAnonymousover 2 years ago

His girlfriend figures that he was cross-dressing and today I get him to crossdress at work and how much more did they give him

BrendaNWBrendaNWabout 4 years ago
Loving it

I am enjoying Gordy's story very much please continue .. has he been wearing that grey skirt? I am not sure how he had on pants when he had to put on the tights .. I would think that there would be something about being appropriately shaved, any visible flesh ? Seems like arms, chest and legs need a clipping, not to mention an appropriate hair style, new wig also ? And let's not forget minimum appropriate makeup. :) TG Tiffany

KristaMoraneKristaMoraneabout 4 years agoAuthor
Thanks for Feedback BS

BS,

Good point. However, this is just a cliffhanger moment and I'll weave that idea into chapter 3. You notice it ends just at the moment of discovery and perhaps he doesn't make it to McNeals on time.

- K

AnonymousAnonymousabout 4 years ago
BS

this doesn't make sense, for somebody who just found out his girlfriend back in town and he is not on the phone to her is BS. and since she has a key to his place and all she does is arrange his dresser drawer!!!! after finding lingerie that is not hers I would think she would be lived and waiting for him

I can understand being enthralled with somebody and not thinking strait, but going on a "date " that is not his girlfriend on her first night back is BS . even if he is a player, they don't screw up that bad by not at least calling to say welcome back and when can I see you

need to redo this chapter

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