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  • Halloween Cross-Dressing Bash Ch. 08

Halloween Cross-Dressing Bash Ch. 08

She looked down and saw that he had an erection.

"All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection."

"Sorry."

"Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's four brothers, his father, and his grandfather, now I understand why they all stare at me and giggle like little girls at every family gathering."

"Sorry. I'm ashamed of myself, but it's a guy thing. I can't help it. All guys are insensitive pigs. All guys think with their peckers. All guys get off when imagining their wives or girlfriend or significant other doing another guy."

"I'm just curious," she said giving him another icy look, "which part excites you more? Is it me naked, blindfolded, handcuffed, and on my knees or is it me blowing my four brother-in-laws, my father-in-law, and his father? Or is it me sucking off all my husband's friends? Or did you like the part about me blowing the mailman, the gas station attendant, the grocer, and God only knows who else? Or did you like the part that my husband lied to me that I was blowing him and videotaped me blowing everyone else?"

She didn't realize it, but she was making him hotter with all that dirty talk about her giving blowjobs. She didn't realize that all of it made him hot and horny.

"I'm sorry, but I can't control my erection. It's a hot story and the fact that it is you that I imagine giving all those blowjobs to all those men and not some stranger that I don't even know makes it so much hotter."

"Really," she said cooing while snuggling up to him. Fearing that she was about to bounce him out the door, finally, he said something right to soothe her. "You like to think of me being wicked and erotically adventurous with other men?"

"Yeah, I do."

"Well, my ex-husband was the same way," she said with a wry chuckle. "The difference between you getting off on me giving blowjobs to other men and him wanting me to suck off every man we knew is that he wasn't honest about it with me. At least you're a man and you're upfront with your feelings. He, on the other hand, tricked me and used me. His deception by not being honest showed me that he didn't love me."

"Yes, I'm sorry to say that I agree with you. He couldn't love you and do all those despicable things to you, which is why you two are no longer together. It was obvious to use you for his sexual benefit and monetary gain that he had no respect for you."

"Well, maybe, if he had been upfront about what he wanted, we may have come to some open arrangement that we both could have enjoyed. Although I am a bit naïve and too trusting, I'm certainly not a prude. Maybe, I could have sucked off one of his brothers instead of all of his brothers and/or maybe I could have sucked off some of his friends instead of all of his friends. Maybe, I could have blown the banker or the grocer or the mechanic, but certainly not everyone. He had no compassion for me or respect for my reputation. He's gone now, that bastard, but I still must live here."

"Surely, you must have gotten something out of sucking cock otherwise you wouldn't have agreed to giving your ex-husband a blowjob every day for a year. I can't imagine eating my wife's pussy every day for a year. I mean you must enjoy sucking cock to agree to a daily regimen of blowjobs."

"Yeah, well, there were some days that I was really into sucking cock and whosever cock I sucked that day was the lucky one and really got off. Then there were days that I thought I'd vomit if I sucked another cock," she said with a laugh. "I feel sorry for the bastard that I blew that day because I think I put more teeth into it because my jaw was getting numb. Only," she said looking at him with an expression of appeal, "I thought I was sucking off my husband. I was so trusting and so naïve."

"Well, you are naïve. I couldn't believe you changed out of your dress and removed your bra without realizing I was in the dressing room watching you."

"Well, maybe had I not given you a free show you wouldn't be sitting here now?" She shuddered while making a gross face. "When I think about it, I can't believe how much and whose cum I swallowed. Eww! Sometimes, I pulled out prematurely only to receive a cum bath. My face, hair, and tits were covered with God only knows whose cum. It was okay thinking that it was my husband's cum, but finding out that it was someone else's cum is beyond gross."

"Well, it's over now. You're rid of him. Your ex-husband is gone and gone for good and never to darken your door, again. Now, it's time you got on with your life and put all of this behind you. Just as I'm doing with this cross-dressing, it's time for you to begin a new chapter."

"Of course, you're right, but apparently these men must have like me blowing them while they fondled my tits because they continued to return over and again and they continued to pay my ex-husband money for the pleasure of me attached to their cocks," she said looking at him with an expression of curiosity. "I wonder how much he charged them. I wonder how much money he made from my mouth and my big tits. Well, no matter, all the money he spent on all those entertainment toys downstairs are now mine to keep, should I ever get over my phobia of going downstairs and he did buy me a new car. Here I thought he was a generous husband and it turns out that I prostituted myself to buy my own car. He's such an asshole."

"Gloria?"

"Yes?"

"Uhm, speaking of downstairs...I was just wondering..."

"Yes?"

"Do you still have any tapes of you giving blowjobs or did you destroy them all?"

"Oh, you're just as perverted as the rest of them. You're no better than my ex-husband. You're pathetic. Yes, I still have them." She gave him a look of disdain and put a hand to her hip. "Why? You want to watch them, don't you?"

"Well, yeah, but only if you'd want to show them to me."

"You'd want to see me naked, handcuffed, and blindfolded while sucking off some guy?" She turned to face him. "Would that make you all hot for me?"

"I'd just be curious, is all. Actually, who wouldn't want to watch those tapes and I'm already hot for you and watching that would make me more so," he said with a nervous laugh. "It's probably every guy's fantasy to watch his wife on her knees giving a blowjob to someone else while handcuffed and blindfolded.

She put her hand on his cock and felt him through his underwear.

"Do you mean curious or hot enough to get an erection like you have now."

"Okay, I admit it. It would make me hot to see you naked, handcuffed, blindfolded, and on your knees while you were sucking off some guy."

"So, hearing about me sucking off men turns you on?"

"Oh, God yes, only if you were my wife, I might imagine you doing such a scenario, but I would never mistreat you in the way that he disrespected you. I would never do that to you; trick you to give another man a blowjob, if you were my wife. If I wanted to watch you blow another man and if that was my fantasy, I probably would feel you out about it with some hot pillow talk. If you were averse to giving other men blowjobs, well, that would be the last time that I'd mentioned it. I'd never do what your ex-husband did to you. What he did is like those fantasies that you read about online at one of those erotic story web sites."

"Well, if hearing about me sucking off other men gets you all hot and bothered, I can't imagine what you'd be like if you saw me sucking off men." She looked at him and gave him her best sexy smile.

"I'd probably cum in my jeans," he said hoping she'd take the bait and show him a tape of her sucking of other men. There was a long uncomfortable silence before Gloria spoke again.

"Would you like me to suck you off, too, while we watched a tape of me giving other men blowjobs? "She pulled down his briefs enough to expose his erection and then wrapped her hand around it while gently stroking it stiffer. "It would be like watching our own personal porn movies with me as the star."

"Are you serious? Oh, God, yes. I would love for you to suck my cock while I watched you sucking the cocks of other men. That would be so hot."

"Only, I don't know if I can blow you. It's been a while since I've given anyone a blowjob. I'll try, though, if you want me to blow you."

"Oh, yes, try, please try."

Gloria went downstairs and returned with a tape. She loaded it in the video player and waited for the image to appear on her big screen television. At first the tape showed a handful of guys standing around the big room downstairs talking, laughing, and drinking. Then, the lights went out and it showed her ex-husband leading Gloria down the stairs and escorting her down and around the basement.

There was loud music playing in the background. Except for a few night lights, the room was totally dark and it was more difficult to see because everything was so very dark. Still, her figure could be identified by her massive boobs. He had never seen tits so big. They were enormous and they only sagged a little bit. His wife's A cuppers sagged more than Gloria's double D's. He realized that he hadn't even thought about his wife since he's been here with Gloria. He was starting to develop real feelings for her.

He refocused his attention back to the big screen television. There she was walking beside her ex-husband as he led the way to the room behind the bar. Everyone was so quiet. Except for the blaring music, you couldn't even hear a whisper. Then, once she was in the room, there were cameras everywhere capturing the action while she was on her knees. Within a couple of minutes a cock appeared through one of the holes.

"I'm ready, Gloria," said her ex-husband.

Only, it wasn't his cock that was peeking out the hole. It was someone else's cock. Her husband stood off to the front side of her watching her sucking off another while he unzipped himself, pulled out his prick, and started masturbating to the sight of her giving a blowjob to one of his friends or one of his brothers or who knows who she was doing.

It was very hot to watch her skillfully give a blowjob with just her mouth and without using her hands. It was an amazing feat. Within only a few minutes the man shot a load of cum in her mouth. Then, her ex-husband pretended to come around the holed wall by opening and closing the door. He helped her up, gave her something to drink, kissed her, and then whispered something in her ear. Within a few minutes she was back down on her knees again sucking someone else off. The whole process lasted about an hour. It was well orchestrated and Bob could understand how being blindfolded in the dark for a period of time, you wouldn't know where you were after a while.

"What did he say to you?"

"He said that was so great, baby, only I didn't shoot my whole load. I'll give you a few minutes before you can suck me off, again. Normally, he'd wait fifteen minutes or so and tell me that he was ready to go again. It was part of our agreement that I'd suck him off for an hour, no matter how many times he got off. Only, in the dark and wearing a blindfold, I had no sense of time. I could have been on my knees for an hour or for three hours for all that I knew."

"You weren't suspicious that you were sucking off someone else?"

"No, when you love someone, you trust them. I had no idea I was sucking off different men. How would I know that? I thought we were alone in the house. I had no idea there were men downstairs in the basement watching me give blowjobs on the big screen television. I only thought I was blowing my husband. Besides, with it being so dark and not being able to hear anything with the music playing in the background and not being able to feel the cock in my hand because I was handcuffed, I had no way of knowing who the Hell I was blowing. You lose all references of where you are. He never removed the blindfold and/or the handcuffs until I was back upstairs. Most times he kept that door locked and he had the only key, that is, until I threw his ass out and had a locksmith remove the lock from the door."

"I still don't understand. How did all these men get downstairs in the basement without you seeing them enter your house?"

"That's easy. There is an outside entrance to the room that leads out to the back of the house. All they had to do was to park their cars a street over, walk through my backyard, and go in through the back way. My husband unlocked the door for them to enter."

While he watched her on video sucking off other men, she fell between his knees, pulled down and off his briefs again, and took his stiff prick in her hand. Slowly she stroked his cock while staring at it before taking it in her mouth, engulfing it with her lips, and sucking it while twirling her experienced tongue around it. Her mouth felt incredible. Never had he received such a blowjob. She sucked him like a vacuum. No wonder why these guys shot their loads so fast. She was an experienced professional at sucking cock.

"You have a big prick, Bob. It's much bigger than my ex-husband's cock," she said removing his cock from her mouth to speak before reinserting it again. "I like sucking your cock better than all of those other men I sucked."

He shot a load of cum in her mouth within three minutes. Never had he cum off so fast from a blowjob before. He calculated if she was this good to get him off within three minutes. She may have blown more than a dozen men in an hour and fifty men within one evening. He extrapolated his imagined totals for the year. She may have given more than 18,000 blowjobs and if her husband had modestly charged $25.00 for a blowjob, no doubt, he charged more, though, but at $25.00, he would have earned $450,000 for having her give 18,000 blowjobs. He wondered how many she did give.

Now, with the Happy Halloween Cross-Dressing Bash tomorrow, Bob kindly accepted Gloria's invitation to stay the night. Since she lived alone, she left her three bedroom home as a one bedroom. She converted the second bedroom to her office and the third bedroom was used to make the media room downstairs. With only the one bedroom and no other bedroom to spare as a guest bedroom, other than the couch, she invited him to share her bed for the night. They had hot sex.

Finally, Bob was able to spend some quality time with her tits. He kissed and kissed her while fucking her. He was all over her big boobs, touching them, feeling them, caressing them, and sucking her nipples. Her tits maintained his erection. Never had he been with a woman who had such big tits. He loved her big knockers.

He ate her pussy. He made her cum with his mouth and made her cum again while fucking her and making sure the length of his cock rubbed against her click every time he humped and pumped her. Then, she blew him again. He didn't think he could cum again. He had already cum twice, but she sucked the cum right out of him. She was so much more sexual than his wife and he loved it. This, by far, was the best sex he had ever had and he wanted a steady diet of this and her.

He already decided to ask his wife for a divorce as soon as he got back home after the Halloween Cross-Dressing Bash. It was different with Gloria than it was with his wife. He didn't have to lie, hide, and sneak around about wanting to dress like a woman. Gloria not only already knew that he was a cross-dresser but also she was okay with it. Further, she owned a woman's clothing store. Moreover, she gave him the best sex and the best blowjobs he ever had. She was his perfect woman.

The next day, she helped him primp for his Halloween Bash. Between helping him comb out his wig, do his makeup, paint his nails, it was a four hour process. He took longer than a woman to get himself ready. It's a good thing they started early and the dance was late.

Of course, he invited her to join him and she was happy to go. It had been a few years since she attended one of these events with her brother. Bob paid for her ticket at the door. As soon as she entered the large hall, she recognized many of the people in attendance as those who attended the couple of times she accompanied her brother. Less than half the men were with their wife, girlfriend or significant other. It was apparent that no everyone had an understanding woman as he did now having Gloria in his life. She pointed out the ones she knew and several cross-dressers gave to her table to give their condolences.

"Gloria! How are you?" A tall man with shapely legs ran up to her, gave her a big kiss on the lips, and hugged her.

"This is my friend Bob. Bob, this is Anthony." The men shook hands.

"I heard what happened to your brother. I'm so sorry," said one man who came up behind Gloria and gave her a hug while she was talking to Anthony. He looked good enough to be a woman.

"Mark, this is Bob." They shook hands.

By nine o'clock dozens of cross-dressers poured in. Many were dressed in outrageous and colorful ensembles. With all the boas, feathers, hats, and high heels, it looked more like a Halloween Masquerade than it did a cross-dressers dance. The cross-dressing men who attended the Halloween bash were not subtle in their fashion taste with some wearing mini-skirts, low cut tops, and even formal gowns. This was their evening to go over the top and they did.

In the beginning, the men separated themselves off in common groups. There were those who looked good enough to be women and had you not known that this was a cross-dressers bash, you would think and mistake them for women. There were those who were gay, those who were post-op transvestites, and others who were pre-op transvestites. Then there was another group who were dressed as women but who looked like men. Many of the men in that group were well over six foot tall, especially with their high heels. Then, there were a group of men who looked much like Bob. They were men with beards and mustaches.

After the music started playing and cross-dressers started drinking and mingling, the groups blurred into one massive scene of cross-dressing men. They all appeared to be enjoying themselves. Everyone looked happy. Bob made a lot of friendships that night while Gloria passed out discount coupons to her store.

*

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.

THE ENDM

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