tagExhibitionist & VoyeurHalloween Cross-Dressing Bash Ch. 03

Halloween Cross-Dressing Bash Ch. 03


She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were for him. Maybe, she'd even try the clothes on to model them for him.

Nah, she'd never do that. It's probably against store policy. Besides, this wasn't Rodeo Drive. This wasn't a high end store where they had models to model the clothes while you lounged in a chair sipping champagne and comfortably waited for your wife or girlfriend or significant other to make her fashion selection and she wasn't Pretty Woman.

"I can try it on for you, if you'd like and model it so that you can see how it would look on your wife."

"Really?" He couldn't believe his ears. Suddenly, he imagined her whipping off her dress and putting on this one right in front of him while he stood behind her with his cock planted between her ass checks helping to hold her big bra covered tits up and out of the way for her to fit in the dress. "You can really do that?"

"Sure, it's part of our personal service and what makes our store better than the competition. We pride ourselves on our customer service."

"You won't get in trouble? I mean it's not against store policy to model the clothes for me, is it? That would be great if you could do that."

"Well, if it is against store policy, it's my policy to break. I own the store," she smiled. "It's one of the benefits of being the boss."

"Oh, okay, sure. Yeah, I'd like to see the dress on you, that way I can tell how it would look on my wife."

"Follow me," she said and headed for the dressing room. "What's your name," she said turning to look at him.


"Pleased to meet you, Bob. I'm Gloria, but everyone calls me Glory," she said turning and stopping to shake hands with him.

"Glory? Why Glory?"

"Glory is the name of my store."

"Oh." Bob was so nervous walking in the women's clothing store that he didn't even notice the name on the store.

He stopped short as he neared the dressing room.

"It's okay, you can come inside. There's a sofa across from the three full sized mirrors where you can sit and wait for me to change."

Bob impatiently sat on the sofa while Gloria went in the dressing room to the right and pulled closed the curtain. Only, she didn't pull the curtain all the way closed and when Bob looked in the first mirror that was conveniently angled to the right and pointed at where she was changing, he could clearly see Gloria's reflection while she unzipped her dress.

She removed it from her shoulders and shimmied it down past her bust, wiggled it past her waist, and pulled it over her hips before stepping out of it and hanging it on a hanger. She stood in the dressing room in her white, full sized panty and big white bra with her back to him. She had a big, full, round and shapely ass. He couldn't believe what he was seeing. Immediately with the sight of her, he started developing an erection. He couldn't believe he was seeing Glory in her bra and panty. She was giving him an unbelievable strip tease show.

When she turned a little to the left, he could see the entire side of her bra and part of the front of her bra covered tits. Her tits were huge and she was wearing the biggest bra he had ever seen. He could only imagine what her tits looked like. Her bra cups were so round and so full with the tops of her breasts squished a bit together to form a long cleavage line. He imagined his cock fitting nicely in there and in between her breasts as she lowered her head down and licked the top of his penis before shooting load of cum in her mouth and all over her big tits. All she needed was a yellow caution sign, as her big, white bra looked like painted white scaffolding to support those big breasts.

He wished she wasn't wearing a bra. He wished he could see her tits, her areolas, and her nipples. He could only imagine what they looked like. No, he couldn't imagine what they looked like because, surely, he had never seen tits this big before. Only, as soon as he thought it, she did it. He couldn't believe his eyes when she reached around behind her, unhooked her bra, pushed the straps from her shoulders, removed her bra, and hung it on the hook. Oh, baby, there they were and they were magnificent.

Are you kidding me? Clearly, he had a good view of the entire side of her boob. If only she would turn a bit to the left, there, he saw her left breast, all of it. She had the biggest tits he had ever seen. For tits that were as big as hers, they didn't sag as much as he thought they would. They were spectacular. He imagined touching them, feeling them, caressing them, fondling them, sucking them, and fucking them before shooting a load of cum all over them.

Her areolas were as big around as saucers and she had these giant nipples that made his lips reflexively move in the shape of a goldfish's mouth when begging for food. Finally, she emerged from the dressing room wearing the dark green dress with the gold buttons. The dress looked a little like a uniform, but he liked it.

"What do you think," she said. She stood up on the platform that they have where the seamstress pins the hem of the dress to hem it. With a wide smile while holding up and out the hem of the dress, she twirled in front of him. From the low angle of the couch and in the relaxed vantage point of how he slouched down while sitting, he was treated to a complete up skirt view of her panty from camel toe to waistband. Was she purposely teasing him or did she just not know what she was doing? Whichever, she was driving him nuts.

"It looks good on you," he said barely able to speak after her sexy show. Unable to remove the vision of her up skirt and of her in her panties and bra and only removing that image to remember her giant naked breasts, he suddenly saw this saleswoman in a whole new light. He imagined calling home while spending the night at Gloria's house.

"Honey, I'm going to spend the night here," he'd say to his wife while Gloria sucked his cock and he felt her enormous tits and fingered her giant sized nipples. "They're having another truck show tomorrow, too, and Willie Nelson is giving a free concert and you know how much I love Wet Willie."

"I just love how this dress fits and falls. It's a real bargain for the money. She'll get years of use out of it." She laughed and a flash of red brightened her cheeks. "I had to remove my bra otherwise I'd never fit myself in the dress. Besides, the way this dress is cut, it squishes my tits so tight that I almost don't need any more support."

"I'll take it," he said. He just wanted to watch her change again. He hoped that she'd forget to close the curtain all the way, again. From where he was sitting, unless she looked at his reflection in the mirror, she couldn't see him.

"Great," she smiled. "Just give me a minute to change." She walked in the dressing room shouldering past the curtain without closing it at all this time. It was nearly halfway open and no matter where she stood in that tiny dressing room, he could clearly see all of her.

This time she took her time undressing and dressing giving him more of a prolonged show. With the curtain open a good two feet, how could she not know the curtain was open? How could she not know he could see her? Intently, he watched as she unzipped her dress. This time, instead of wiggling herself out of it, she lifted it from the hem and up and over her head.

With her dress covering her face, she turned to face him, her tits lifted high up and proud as she struggled to free herself from her dress. As if in slow motion, he watched her big boobs sway and bounce with the movement of her trying to free herself from the tight confines of the dress. It took all the self-control he possessed not to get up and offer to help her.

"Here, let me hold your tits out of the way," he imagined saying to her as he touched, caressed, and felt her tits before falling to his knees and taking them in his mouth.

He couldn't believe it when she faced him topless with her head down while holding her bra and tightening her over the shoulder boulder strap holder.

Both of her breasts were totally exposed to him. She was topless and she was facing him. He saw everything through the mirror. Surely, she was doing this on purpose. Surely, she was flashing him her tits. Surely, she knew that he could see her breasts. How could she not know that he could see her? Hey, if she wanted to show him her big balloons, he was going to look and he did. He stared and he leered while smiling with the thought of spending some quality time alone with her and away from here with those huge knockers.

Only, just as he thought that, she looked up, saw his reflection in the mirror, and caught him staring while smiling. She covered her tits with her hand and arm and snapped shut the curtain with a loud click. Oh, oh, now he was fucked. He was as embarrassed for himself as he was for her. He was such a fool. He just ruined a good thing. There goes his free wet Willie concert. Now what?

Maybe, she didn't know that the curtain was open. Yeah, right? He was certainly grateful for the show, as it had been a while since he had been intimate with his wife, and this saleswoman wasn't a bad looking woman. He couldn't take his eyes of her tits. It had been quite some time since he had been with a woman who had big tits, before he was married when he was dating his first girlfriend Kathy or Linda or Debbie. He couldn't remember her name. He only remembered feeling and sucking her big tits. He imagined Glory sucking his cock with him fondling her massive boobs while dressed in his forest green dress with the gold buttons.

Finally, she emerged again from the dressing room with her dress unzipped in the back.

"I'm so sorry," she said. "I thought that I had closed the curtain all the way. You didn't see my, uhm, anything did you," she asked while biting her lip.

"I did. I'm the one who should apologize. I'm sorry. I was mesmerized. I couldn't take my eyes off your breasts. I've never seen tits so big."

"You saw my breasts?"

"Yes, and I'm sorry."

"I'm so embarrassed," she said turning red and breaking eye contact. "It's a bad habit, I guess. Normally, we don't allow men in the dressing room. Normally, it's just us girls in the dressing room and sometimes we don't even close the curtain.

"Please don't be. Think of it as an artistic display. They truly are beautiful, works of art, actually."

"Really? Do you really think so? Oh, God, I'm so embarrassed. I hardly know you and you've already seen my breasts and are now talking about them." She looked at him and gave him a smile of embarrassment. "Do you really think my breasts are works of art?"

"Oh, yes, I do. They are quite spectacular. If I were an artist, I'd want to paint them. I am an amateur photographer, though. I would love to shoot them."

"Yeah, I bet you would," she said with a smile.

"C'mon, it would be fun."

"Oh, I don't know about that," she said. "Maybe," she said giving him a sexy look. "Let me think about it. In the meantime, would you mind doing me," she said.

All that he could imagine was pushing her down on the rug in the dressing room, stripping off her clothes, stripping off his clothes, struggling to remove that massive bra, and pulling down her white panty before mounting her and doing her. He'd hump her had, really hard, while leaning down to suck on her big nipples.

"I beg your pardon?"

"My dress," she said pointing to the zipper. "Would you mind doing me, I mean zipping me?" She turned her back to him flashing him the back of her wide bra and the top of her panty. He had a sudden urge to reach inside her dress and around her to feel her big breasts through her white bra.

"Oh, yeah, sure."

"Sorry, I don't realize what I say sometimes. Sometimes, my innocence gets me in trouble. Much like my little dress shop?"

"How do you mean?"

"Well, ever since I was a little girl, everyone called me Glory. I figured that'd be a great name for the dress shop. When I started this business, I couldn't afford much to lease, but I found this place, a little hole in the wall, much longer than it is wider. I wanted to call it Glory's Hole In The Wall, but the shop was so narrow, the words wouldn't fit and still maintain the city council's code for sign size. So, I named it Glory's Hole."

"Oh. Oh! I had no idea your shop was named, Glory's Hole," he said laughing.

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on the hanger. "Okay, so we have the dress, what else do you need?"

"Well, now you have me more than curious about the other half of the story. Maybe if I spend more money in your store, you'll tell me the story. Let's see, I need shoes and a handbag. I want to buy her a whole outfit, soup to nuts."

She gave him a look that made him lift up his chin in defiance of her suspicion that he was a cross-dresser. Yet, maybe her look was that she had suddenly taken a sexual interest in him after accidentally on purpose flashing him her boobs and would, perhaps, share the rest of her story that related to the name of the shop and what her ex-husband had tricked her into doing while in the privacy of her bedroom.

In the next chapter Bob jumps at the chance to wet his Willie.


Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...

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