Halloween Cross-Dressing Bash Ch. 06


Gloria left the store in the capable hands of her store manager, Sharon. After paying for his purchases, with Gloria giving Bob a very generous and unexpected 20% discount, Bob followed her car home in his pickup truck. He was just as excited to maybe have a sexual affair with her as he was with the thoughts of trying on the clothes he just bought.

They stopped at a nice house set back away from the others at the end of a long, winding tree lined cul-de-sac. The trees afforded the property plenty of privacy and it couldn’t be seen from the road. When driving up to it, Bob was more than a bit nervous. What if this woman had something against cross-dressers? What if she tied them up, tortured them, and had her way with them before murdering them? What if she was the one who threw the rock at her brother and murdered him? What if that wasn’t her brother at all, but just some customer she invited home in the way that she invited him? What if her Glory Hole story wasn’t a sexual story at all, but how she murdered her victims.

He had never been with another woman other than his wife. Yeah, sure, he’d looked at plenty of women, but he never touched another woman since he’s been married. He’s been a faithful husband. Only, he and his wife hadn’t had sex in nearly three years. He was more than horny. Besides, he wasn’t as interested in being with women, other than his wife, as he was with dressing as one. Cross-dressing and masturbating took the edge off not having sex with a woman. Still, nervous after allowing his imagination to run wild, he calmed down when she opened her front door and invited him inside.

“Come inside, Bob, and make yourself comfortable. What will you have to drink?”

“I’ll have a beer if you have one.”

“One cold beer coming right up.”

She handed him a cold Bud and a glass.

“That’s okay,” he said waving off the glass. “I drink it out of the bottle.”

He was a real man, a man who drank his beer out of the bottle, albeit a man how enjoyed wearing women’s clothes. Besides, drinking from the bottle added to the pleasurable experience of drinking beer and the only better ways to drink a beer was to belly up to the bar for the bartender to pour a cold, frosty one right from the tap.

She sat across from him drinking some girly type of drink, no doubt. She was a lady, after all. He couldn’t believe he was here sitting across from her. He couldn’t believe how pretty she was. Sure, she was a full figure woman and much larger than his wife, but he enjoyed her for who she was inside. She was very personable and he liked that about her. She made him feel comfortable and it was obvious that she liked him for who he was. It didn’t matter that he was a cross-dresser. To her, cross-dressing wasn’t an end all issue, as it would be for his wife, if only his wife knew that he loved to dress as a woman.

“I needed a drink after being on my feet all day and this taste so good,” she said holding the cool glass to her cheek and closing her eyes for a second.

“What are you drinking?”

“A double scotch with a splash of water.”

Wow, he thought she was drinking a girlie drink to find out that she was drinking a real drink, the hard stuff, and she was drinking it like a man without watering it down with ice. He liked this woman. No doubt, after drinking two of those double scotches, her lips, all four of them would not only be loose enough to have sex with him but also to tell him the story about how her husband took advantage of her. He couldn’t wait to hear that story. He wondered what it was. He could only imagine. Surely, it had to be something really despicable and maybe even perverted.

“This is a nice place,” Bob said looking around the ranch style home. “You have a very beautiful home. You live here alone?”

“Yeah, I never had kids. My husband never wanted them. He was tight with a dollar and kids cost money. I was pregnant once, but had a miscarriage. It was just as well because, as it turned out, he was more than a bit weird.”

Bob thought she would get into the story from that statement, but when she didn’t he said nothing to encourage her to say more. He didn’t want to ruin any opportunity he may have with her by pressuring to talk about something that she wasn’t yet ready to share with a stranger and with him. Only, he hoped for the opportunity to bring it up again in conversation.

He took a sip of his beer before peering in the bag of clothes he bought from her little dress shop, the Glory Hole. He loved touching the undergarments he bought. They felt so soft and so silky. He couldn’t wait to feel them against his skin. He felt the bra and fingered the panty before pulling out the dress to look at it, again.

“I really like this dress,” he said. “As soon as I saw it, I fell in love with it as soon as I saw it. I think my mother had a similar dress so long ago,” he said with a satisfied smile. “It’s the gold buttons that make the dress, I think. It looks a little like a uniform, mardin escort only more dressy. Do you know what I mean?”

“Yeah, I know exactly what you mean, Bob. Moreover, your mother may have had a similar dress. A dress like that never goes out of style.” She gave him a smile. “I can tell you’re excited about your purchases and can’t wait to try them on. I’m so happy to have helped you find what you wanted. I’m so happy to have met you and made a friend.”

“Me, too,” he said giving her a warm smile. “Yeah, I am excited about trying on my purchases,” he said looking at the inside tag before holding the dress up with outstretched arms. I just hope it fits.”

“Well, go ahead and try on the dress. If it’s too big or two small, we have the same dress and in the same color in other sizes. I’m curious, too. I’d like to see how it fits you, too. I’m dying to see you wearing it.”

“He looked around the room. Where can I try the dress?”

“Try it here, please, Bob,” she said taking another sip of her drink before leering at him, “so that I can see how it fits as you are putting it on over your head.”

“Really? You don’t mind? You want me to get dress in front of you?”

“Well, after you ogled my tits, it’s only fair play that I ogle the bulge in your underwear, don’t you think?”

“Okay, yeah, sure,” he said laughing and standing to unbutton her shirt. He removed his shirt and t-shirt displaying his hairy chest, back, and shoulders and his bulging beer belly.

Before he removed his shirt, she started humming strip tease music while he unbuttoned his shirt and Bob got into the game by slowly stripping and teasing her with his chubby body. Once he removed his shirt, he unbuckled and unzipped his jeans. Intently, she watched him while focusing her concentration on the big bulge that suddenly ballooned out his briefs. He was so horny and so hot for her that he already had a fairly large erection.

“It looks like you have a big cock, Bob.”

“Thank you, I do,” he said looking down at it while rubbing his beer belly. “And with his big gut, it’s a good thing that I do,” he said with a laugh.

She sat on the sofa with her legs slightly spread and enough apart for Bob to see her panty from where he stood across from her while stripping off his clothes. He wondered if she knew she was showing. He wondered if she was flashing him by accident or on purpose. Truly, it didn’t matter which it was, by accident or on purpose, so long as she continued flashing him. Up skirts and down blouses were his favorite views. Definitely, she was giving him a nice up skirt of her white panty. The sight of her panty added to his erection. He imagined walking over to her and her taking his cock in her hand before blowing him.

He wiggled into the dress and walked back and forth in front of her with the dress on. It was obvious that he needed a makeover. His legs from his ankles to his crotch were hairy. He had hair from his fingers to his shoulders with plenty of hair on his back, as well as his chest. She’d be waxing and shaving him for a while.

“Oh, well, I hope you don’t think less of me because I had sex, I mean, comforted my brother during his troubled times while he was going through his divorce,” she said after downing the rest of her drink while hinting at a replay of the conversation that had in the store before they arrived at her house. Obviously, for her to start this sexual conversation, again, the alcohol was already working its magic on her inhibitions.

“Let me fix you another scotch,” he said.

“Thanks, Bob,” she said handing him her glass. This time he poured her a triple with even less of a splash of water. He was hoping to get her high enough that she would enlighten him with her Glory Hole story. Surely, he had heard plenty of glory hole stories, only, he couldn’t imagine that her story would be anything like those that he heard or imagined.

“Why would I think any less of you? I don’t think any less of you just because you showed your brother some sisterly comfort and love. He needed you at that moment and you helped him though a bad time. I’m just as sexually excited by this incestuous story as I am that you’ve volunteered to help me get ready for the Halloween Cross-Dressing Bash.”

“Really, you find my incestuous story of what happened between my brother and I sexually exciting?”

“Oh, yeah, that’s every guy’s fantasy to do his older sister.”

“I’m sure that it is,” she said with a laugh after taking another long sip of her drink.

“I can’t tell you how much I appreciate your help in helping me select my outfit and in helping me do my hair, makeup, and fingernails. Thank you so much. That is really nice of you to volunteer to help me. I can’t tell you what a load off my mind having someone to help me with my hair and makeup and even to do my fingernails. I don’t have the patience to do my nails. My hands start shaking and I get nail polish van escort all over my fingers.”

“Well, it’s my pleasure to help you get ready for the Happy Halloween Cross-Dressing Bash.” She looked at him and smiled. “Do you know why they call it Happy Halloween Cross-Dressing Bash instead of Halloween Cross-Dressing Bash?”

“No, actually, I never gave that a thought, but now that you mention it, I am a bit more than curious. Why do they call it Happy Halloween Cross-Dressing Bash instead of just Halloween Cross-Dressing Bash?”

“Well, this is my brother’s reasoning and not mine and probably not the officially answer, at least, I don’t think that it is. I don’t have a clue why they named it so, but he said they put the Happy first because they wanted everyone to have a happy time. He said that too many times, too many cross-dressers are torn and tortured and that this bash, one of several that they hold throughout the year, allows men who are so inclined to feel the need to dress as a woman to be happy while dressed as a woman instead of feeling sad before they feel that they must dress, uncomfortable during the time that they are dressed, and guilty after they have dressed in women’s clothes. This happy time removes all of those internal struggles that they have wrestled with all of their lives. This bash really is a place for them to have a happy time. It is their safe haven of acceptance away from the cruel world of ridicule.”

“Well, that explanation makes sense to me. It would take a cross-dresser to come up with that as an explanation.” He smiled at her. “I can’t wait,” said Bob. “I’m so excited.” He looked at her. “Do you think I should shave my mustache?”

“Yes, of course, Bob. How many woman have you ever seen with a bushy mustache like you have?”

“None, but I’ve had this mustache for nearly thirty years. I don’t even remember what I look like without it.”

“Well, there are men who go to the bash with mustaches and full beards, even. The choice is up to you. If you feel the need to look, walk, act, and talk like a woman; then you should shave your mustache. Yet, if you feel that it’s enough of a thrill just to wear woman’s clothes, then I’d keep the mustache.”

“Yeah, I think I’ll keep it. I’m not trying to fool anyone. With my body, the way that I walk, and how I carry myself, there’s no mistaking me for a woman. I look like a guy. Besides, my wife would know something was up if she saw me without my mustache. She’d give me the third degree as soon as I walked in the door asking me if I shaved my mustache because my new girlfriend doesn’t like mustaches.”

Gloria took a couple of quick sips of her drink.

“Don’t look so sad, Bob. You’ll have a good time,” she said with a smile. “Maybe, later, after I’ve finished this drink and had another, you can take some candid photos of my…works of art,” she said looking down at her breasts and then looking up back at him.

“Really? Are you serious?” He stared at the huge impression her tits made in her dress. “You have beautiful breasts.”

“Thank you, Bob. Yeah, sure, why not? What the Hell, you’ve already seen the twin girls anyway; why not photograph them, too,” she said with a laugh.

“Okay, yeah, sure, and maybe later, after a glass of wine or two you’ll feel comfortable enough with me to share your story about the trick your husband played on your regarding the name of your shop.”

“You’ll have to get me drunk to tell you that story, Bob, because if you think what I told you about my brother is hot, you’ll be out of your mind with passion and desire for me when if I tell you the story of how my ex-husband tricked me, but we’ll see. I’d have to feel a bit more comfortable with you to share that story with you.”

“Excuse me while I change into something more comfortable. I’ve been in this dress all day.” She stood and when she did, she flashed him her panties again when getting up from the low sofa. “Would you mind doing me,” she said again, this time turning her back to him and pointing to her zipper.

“I’d love to do you, Gloria. You are a very pretty and sexy woman.”

“Well, thank you, Bob. Maybe if you get me drunk enough, you can take advantage of me,” she said with a sexy laugh. “Only, for now, I meant, would you unzip my dress.”

“Yeah, sure.”

He slowly unzipped her dress all the way down to the top of her hips.

“Thank you that feels better already.”

“Would you like for me to undo your bra?”

“Sure, if you can, it’s very tight. Undoing my bra would be a great relief.”

Bob pulled the elastic material forward and struggled with the hooks, but he undid the four of them. It was a very wide bra. The back of his wife’s bra was very narrow and only had one hook. He had never seen a bra with four hooks before. As soon as he undid her bra, he reached his hand inside her dress and around the front of her and felt her big tit through her bra. It was enormous. ankara escort Never had he felt a tit as big. Then, he lifted her bra cup and her breast fell to meet his hand. He felt the weight of her big tit and briefly fingered her nipple before she pulled away from his hold.

“Bob, you’re so fresh,” she said turning to face him. He kissed her and she kissed him back, but when he tried to part her lips with his tongue, she pulled back.

“Let me get into something more comfortable, Bob.”

“Sure,” he said allowing her to leave.

He watched where she went hoping she’d go in the bedroom across the way and leave open the door, as she had left the curtain open in the dressing room when she accidentally on purpose showed him her big boobs while she was changing her clothes to model his dress on her. He was hoping she’d give him another show of her big boobs, accidentally, of course, on purpose. Only, she went to the bathroom around the corner and closed the door.

After what seemed an hour but was only twenty minutes, she emerged wearing a low cut black negligee with matching bathrobe. The material was so sheer that even wearing the bathrobe, he could clearly see through both. He saw the outline of her pussy and could see that her pubic hair was trimmed. More importantly for him, being the breast man that he was and being in the constant horny and terribly aroused state that he was, he could see her areolas and nipples. Her areolas were the size of small saucers and her nipples were as big as hard candies and already were erect. He couldn’t wait to feel her breasts. He couldn’t wait to suck her nipples. He couldn’t wait to see her tits, again.

She pulled out a folding table, he imagined like the one she used to give her brother a bikini wax. His mind was filled with her standing over her brother topless while he felt her big tits and while she slowly stroked his cock before leaning down and taking it in her mouth. He imagined the incestuous sight of her blowing her brother.

“Well, Bob. Are you ready?”

“Ready for what?”

“Are you ready to remove your modesty, get naked, and climb up on the table so that I can free you from all that body hair?”

“I’m ready to get naked, but I don’t know about the bikini wax, Gloria. I think it would really hurt.”

“Well, I have an electric shaver I could use on you, if you prefer.”

“Oh, that would be better.”

“Which first? Front or back?”

“Let’s do the back first.”

Bob was quick to change out of the dress and remove his briefs. His cock was semi-erect but grew harder as soon as he saw her staring at it.

As soon as he climbed on the table and got comfortable face down, she giggled and gave his fat ass a slap. He could feel the tickle of the shaver across his shoulder, back, ass, and thighs. Even though it tickled it felt erotic to have a strange woman shave his naked body. Within ten minutes he was ready to turn over. When he did, his cock was pointing straight out.

“Well, Bob, at least with that big boner, I don’t have to hold it out of the way,” she said laughing.

“Sorry, but the sight of you in that sheer, black negligee is enough for any man to get excited. It makes you look so sexy.”

“So, you like my negligee, huh?”

“Oh, yeah, only I like what’s underneath it more,” he said reaching his hand up to feel her tit and fingering her nipples before pulling and twisting them. He remembered she said that she liked it when her brother pulled and twisted her nipples. He remembered her saying that her nipples were sensitive to that kind of play.

“Oh, Bob, that feels good when you touch my nipple. My nipples are very sensitive, but now is not the time. I need to concentrate so that the shaver doesn’t slip and we really make you into a woman.”

She shaved his shoulders, chest, stomach, and legs. Then, she took her time shaving his balls and cock spending quality time holding his stiff prick in her hand.

“I love the feel of your hand around my cock.”

“Do you like it when I do this, Bob,” she said slowly stroking him while staring down at his big prick.

“Yes,” he said while reaching up his hand to feel her massive breasts again.

“What if I did this,” she said leaning down to take his cock in her mouth for a few seconds while sucking it and twirling her tongue around it. “Did you like that, Bob,” she said removing his cock from her mouth to talk.

“Oh, God, yes. That was incredible. It’s been a while since I’ve had a blowjob.”

“It’s been a while since I’ve given a blowjob.

Suddenly, she looked sad.

“What’s wrong?”

“I haven’t been able to orally pleasure a man, since what my ex-husband, the no good, dirty bastard did to me.”

“Tell me what happened. What did he do?”

In the next chapter Gloria tells Bob the Glory Hole story.


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.

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To be continued…

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