A Halloween to Remember

It started as a silly trick or treat fun game for our husbands on Halloween. I am Sandra. My husband, Jeffery and I had been married for three years at that time. I don't work anymore because Jeff makes very good money. He is an inventor and has contracts all over the world with small companies that manufacture some of his simpler products. Jeff is 30. He is just 5'-6" and weighs about 135 pounds. Jeff was sort of a nerd in high school and a bit awkward around women. He did come out of it some as he got into college.

I was working for a major oil company when I first met Jeff. He was proposing to sell one of his inventions to a service company which the oil company owned. I was just twenty at the time and he was 26. It was not your usual courtship. Jeff, by then was quite skilled at public relations and over time seeing him in the office, he asked me out. We hit it off for unusual reasons. I was drawn to his honesty and mental acumen. I think he was drawn to my body. Maybe my wit and personality. I am 5'-7" tall and weigh an athletic 125. I played soccer and ran track in high school.

Since I don't work and have plenty of time on my hands, I have several close girlfriends who I pal around with. We have coffee together, sometimes lunch and go out together with our husbands from time to time. There may be as many as four couples or as few as two at a time. I must say that all these women are very attractive in their own right. Not one to compare, but I probably hold a slight edge in the looks department. Especially in swimwear. My ass is round, and my boobs are a full DD cup. I developed early and was quite popular in high school. To my high school friends, I married down. I don't think of it in that way, but everyone has their own opinion.

The girls and I were a month ahead of Halloween and we were discussing our upcoming adult costume party. I was the youngest at 24, but all were under 30. Over coffee, we planned our costumes. It was the typical stuff. Wonder Woman. Cat Woman. She-Devil. French Maid. Cop.

We were less than enthusiastic about every suggestion and wanted something unique. We tabled the discussion just about every time until we were getting closer to the party. It was a block party for adults, and we were sure that we would be outclassed if we did not come up with something memorable.

We were all young and attractive so needless to say we intended to make the most of our assets and wear sexy costumes. One of the girls, Sharon, suggested that we dress like hookers. Those outfits would be on a theme, but we could still be very different. Another asked if we should dress our husbands as pimps. We all were having a good time laughing about this. The ideas were pouring out until Beth said, "What about us dressing the husbands as hookers and we will be the pimps. We roared hilariously about that. We teased each other about how one husband or the other could dress and so on. There wasn't much happening productively after that. We were all in silly mode talking about what dress size each guy would wear.

The next time we all got together we had mostly forgotten about Beth's joke. We were discussing costumes again when Sonia asked, "What about Beth's suggestion?"

We started the laughter all over again until Sonia said, "I am serious. It would be a great gag on the guys, and it will challenge our imagination to fix our husbands up in hooker garb that will look authentic. The makeup will be up to each girl. That is the real challenge anyway. That and actually getting our husbands to go along."

We all looked at each other to see if she was joking, but she seemed serious. Beth looked a little in between. Just reading her face, I began to get the idea that maybe she was serious to begin with. Now Sonia was on board. At least it appeared that way. I looked over at Sharon. It was beginning to dawn on her also that maybe they were serious.

Sharon was still waiting on the punch line, but not quite sure. I looked at both Beth and Sonia waiting for their next suggestion.

"Well, really girls, it would be very different, "Beth said.

Now, I knew that Beth had put it out for our reaction. If no one had turned serious, she could still laugh it off like we did initially. Sonia had moved the needle and you could see that Beth was beginning to take credit for the idea.

"Beth," I said, "Bart weighs almost two hundred pounds. Plus, he has a mustache. How the heck can you make him look like a girl?"

"He doesn't have to pass as a woman. And he only weighs 180. The dressing up is the novelty and the concept. Getting him to dress will be my main concern, not making him look like my wife," Beth argued.

"Well, he sure can't wear any of your clothes," I reminded her.

Beth is 5'-5" and weighs about 120. She is pretty and has a slim figure with maybe C cup breasts. Sonia is 5'-6" and weighs about 120 also. Her breasts are about a B cup. Sharon is 5'-4" while her husband Ronald is around six feet, weighing about 160. The thing about Sharon is that she appears a little stocky, but it is all because she wears an F cup bra. Being that big on top makes her look a little chubby and she does have a full butt, but she is not fat at all. She has a nice curve at her waist to go along with her spectacular top and bottom assets.

The more we compared our husbands' body type to our own, we realized that we might switch some clothing between the women to fit another husband, but we might have to actually purchase some clothing. Beth mentioned that we would definitely need to buy them bras and maybe panties.

"What about high heels," Sonia asked.

Damn, you couldn't put the money and effort into dress and makeup and not have them wearing hooker heels.

"And jewelry," Beth suggested.

It was growing by leaps and bounds now. Surely someone would come to her senses and realize that it would take too much time and money to make our husbands look like women. I was not going to be the one to chicken out. I even began to think of what clothing and accessories of mine that I could dress Jeff in.

As the idea took hold, each woman decided to go explore their closets and come up with something our husbands could wear. Sonia seemed very calm. As we went out, I approached her.

"Sonia," I asked, "Keith is not much bigger than you. You probably have some things he can wear. Same with me. Jeffery is a little shorter than I am. I was hoping that even some of my heels would fit him."

Sonia seemed amenable to planning out our husbands' costumes. She asked, "Why don't you come over and we can look at my things, then go to your house. This could turn out to be fun."

When we got to her house, Sonia poured me a drink and we adjourned to her closet. She was pulling some dresses and skirts from the back of her closet and I would comment on it. One in particular was sexy and I had not seen her wear that.

"Special occasion, only?" I asked.

She blushed a little and said, "Well, sort of."

She seemed a little too vague and defensive, so I had to find out why.

"Something I am missing?"

"Uh, well, no, not really. When Beth suggested that we dress our husbands as women, I was really nervous about revealing too much. Uh, you see, Keith and I are a little adventuresome in the bedroom and we play a little with, uh..."

"Go on." I encouraged her.

"Well, several months ago I was teasing Keith sexually and I was doing a little striptease. I would take my clothing off and rub it on his body. I dangled my sexy bra over his face and cock. When I took my panties off, I teased his cock with them. He groaned and reacted very enthusiastically. I wrapped his cock with the panties and started moving my hand around his hardon. I was just teasing and suddenly, he started cumming. I caught his cum in the panties and chastised him for coming so quickly. I assumed that once he came, he would go soft and that would be the end of it. I really chewed him out and told him that he was going to have to bring me off orally for being so insensitive. Then I upped the ante and told him he had to wear my panties while he did it. He did not resist and I slid the cummy panties up his legs and over his limp cock. He still did not fuss, but in two minutes, his cock was fully hard again. I was amazed at this because he can only get it up once usually. I still made him satisfy me orally and he was all too eager to service me. I had two wonderful orgasms and after I came the second time, he pulled the panties aside and fucked me long and hard."

"Oh, wow, Sonia." I said. "That sounds really kinky. So, he was turned on by the striptease or wearing the panties?"

"I think both. Anyway, he was so good that I decided to try it again a few nights later. He had showered and seemed like he was hinting at something. I went in the bathroom and shaved my legs and all my pubic hair. I was as smooth down there as a newborn. Then I put on a sexy bra and panty set with garter belt and stockings. I wore my highest heels and fixed my makeup very slutty. He was watching TV and I strutted out into the den with my outfit on. His eyes just about popped. I asked if her would rather watch TV or come to my boudoir."

"He raced to the bedroom, but I made him strip and lay naked on the bed. I put on a little jazzy music and started my provocative dance again. In a while, I stated to unfasten my sexy bra, but I teased him well before I unsnapped the back. I took it off and twirled it around my finger. I got on the bed and dangled it all over his face, chest and hard cock. I then placed the cups over his chest and let it lie there while I moved back and shook my boobs to the music. My panties were getting wet from the dancing and seeing his hard cock. I teased him with starting to take off my panties and then stopping just to give him a little glimpse of my shaved pussy. His cock was throbbing. I finally took my panties down and dangled them on his face and cock. I placed them over his feet and pulled them up his legs and over his cock. In just my stockings, garters and high heels, I mounted his face and fucked his mouth with my gushing pussy."

"Damn, Sonia, I have never seen you so descriptive."

"I know. It was a huge turn-on for both of us. When I saw how this excited him, I began having him in panties each time we made love. He loves it. Eventually, I had him shave his legs and pubic hair. Over time, I introduced him to stockings and sometimes pantyhose with the crotch cut out. I just love lying with him and our legs wrapped around each other feeling the sheer elegance of the pantyhose rubbing together."

"You had him shave his legs and pubes?"

"Oh, yes. And when Beth suggested we dress our guys as women, I thought this would be the perfect opportunity to take the next step with Keith. I have dressed him in some of my clothes before sex and it is fun stripping him down to his panties and stockings and have him satisfy me orally. I have not made up his face so far, but the party would be a slow move for us and I think he would go along with it. I don't know about the rest of the guys. How do you think Jeff will take our plan?"

"I hadn't made a plan until now. What you just told me sounds like a great idea, but you guys have been having a good time with this for a while. I might tell him about the party first and then use your method to excite him. Hopefully with that persuasion and the promise that the other husbands will go along, I can get him in the mood. I might have him call Keith and verify that he is willing. Do you think that he will open up to Jeff?"

"Well, just don't tell Jeff about our little game. Make up your own version. I don't want Keith to think that I have told you these details. I think it would ruin it for him if anyone knew. If we can get the guys to go along with this for the party, it will be up to each girl to see how far each husband will go in the bedroom, if you know what I mean. Starting is the main thing. I was thrilled when I accidentally happened onto this fetish. I am sure that most guys would not want anyone to know that they enjoyed this. You know the macho mystique. I don't think any differently about my husband or his masculinity. I just know that he loves it when it is my idea to take the lead. It is a sign of submission to the feminine power with just an exciting twist. I absolutely love that he is so receptive to this form of foreplay and I tell you for certain our sex life has never been better."

When I left Sonia's house, I had a curious warm feeling between my legs. I had never seen anything in Jeff's behavior that made me feel that he was at all feminine. Then again, I could never have imagined that Keith and Sonia had such fun in the bedroom. She was all giddy about her new sex life and according to her, Keith was just as happy. He still did manly things. I had to hear more from Sonia on this topic. Since Halloween was the event on the table, I had to turn my attention to Jeff. Sonia had said that starting was the main thing. She had discovered this by accident while teasing her husband. I had to get going and convince Jeff to dress up for Halloween. The other bedroom activities would take second place to the party... At least for now... I mused.

That evening I approached Jeff.

"Honey, you know the Halloween block party is coming up?"

"Again?" he asked.

"Yes, you know what a good time you had last year. Remember we dressed as Raggedy Ann and Raggedy Andy. It was fun. You had a blast. But it might have been Sharon's big tits falling out of her Playboy Bunny costume all night."

"Uh, I don't remember."

"Don't even try that line, Buster. Even the women had the hots for her."

He smiled and seemed to drop his pretense. "Yeah, it was a sight to behold. I don't see how Ron would let her out of the house like that. But he seemed to enjoy it more than all the rest of the guys. Did you think that was odd?"

"Oh, I don't know. None of the girls were offended and we knew our husbands were infatuated. To us, it was just Sharon using her god given assets to have a good time."

"Okay by me." He grinned as he made that remark.

"So, anyway, Jeff, have you even thought of our costumes this year?"

"Of course not. You picked up our costumes last year and I just put mine on."

"Yeah, does it matter to you what we wear this year?"

"Not in the least. Just pick something out and I will wear it."

"Promise?"

"Yeah, I guess. I am busy right now. It doesn't matter to me."

I hated to do it this way, but he had given the green light. I went into full speed mode the next day. I looked at his shoe size. It would be too tight if he wore a pair of my heels. I had a brainstorm and decided to go to an adult boutique. They sold stripper clothing. When I looked, they had some reasonably priced high heels that just shouted 'SLUT'. They were perfect. They were red sparkly with a platform and outrageously high heel. Great, I thought. Jeff is not very tall anyway. He can pull this off. The sales girl asked my size and I allowed two sizes up for his foot. When she brought them out, I tried them on. She said, "Let me go back and get the correct size. I thought you might be a seven." I told her that they were not for me and I was just guessing. A look came over her face that made me wonder if this happened quite often. Could there be other male customers that shopped here?

I found a dress with a reasonable breast coverage and with thin sequined straps. From there it was off to a wig shop. I got him a medium length curly brunette one. It was pricy, but I didn't want to put him in a costume wig. It would ruin the image I was going for.

At the cosmetics counter of a large department store, I picked out some good acrylic press on nails. I had about the same reaction from the sales lady. Why was I buying press on nails since my nails are so long and beautiful? She didn't ask further. I got the most expensive fake eyelashes and some darker eye shadow.

What was next? Ah, yes, lingerie. This was going to be a little tricky, but I had no intention of letting him wear cotton briefs. I went to the lingerie department and bought him some lacy, but well-cut panties. He could have worn mine but I wanted them to be just for him.

My beautiful ass is way fuller than his ass. Although, he did have a pretty good ass for a small man. I was going to let him wear one of my strapless bras. I have plenty of those. They are all DD cups, but I thought we might partially stuff the cups and get by with that.

That evening I was going to go for the gold. When he came home, we had dinner and both showered.

"Oh, Jeff," I said, "We need to try on your Halloween costume."

"Oh, god, what is it?"

"You said for me to pick it out. The theme that the girls came up with this year is 'Hookers and Pimps'.

"Really, Sandra?" he said, "I don't look like a pimp."

"You won't," I giggled.

When I led him to the bedroom, I showed him the clothing and lingerie laid out on our bed.

"Wow," he exclaimed, "You are going to look so hot in this. Where is my Pimp costume?"

"Oh, Honey, Beth suggested that the girls would be the pimps and the guys were be the hookers."

"No way."

"You said you would go along with anything. Besides I was comparing your stuff with Keith's today. Sonia loved your stuff so well that she was going to get Keith a different dress."

"Are you freaking kidding me? Keith is going along with this?"

"Sure, Sonia said that he got a kick out of it when she showed him."

"I can't believe that."

"Call him if you like." I said.

"Keith is doing this, really?"

"Call him."

Just as I had hoped, Jeff speed dialed Keith. He was amazed when Keith told him that yes, Sonia and the girls had convinced him that it would be wild and we would be a shoo-in to win first prize. Jeff kept probing Keith. What he didn't know was that Keith was so excited about this he could hardly get enough of Sonia's pussy. Sonia told me that Keith went wild when she told him he was going to get to go out in public and at Halloween when everyone gets a free pass on costumes.

Jeff was all mine after that. I fitted the dress over his briefs and showed him why he had to wear panties and pantyhose. I had him try on the panties. He was only a little reluctant. When I helped him on with the pantyhose and heels, I made sure to compliment him. "Wow, Baby, great legs. Your legs look as good as mine." It wasn't quite true, but his legs look much better that half the women you see. I had him try on the bra. It would never work so I told him we had to go with a smaller cup. I would take care of that the following day. He tried on the dress and it looked okay. It would be better when I gave him a bust. I had seen some breastforms at the adult novelty store and they would do for now. I didn't show him the wig just then. I did tell him, however that I had purchased him some depilatory crème. I had him undress and go into the bathroom. I lathered him up and told him to wait seven minutes, then get in the shower. When he got out all his hair was gone except for his pubic hair and underarms. We took care of that with a razor and he was ready to go.

With his body hair removed, I had him try the panties and pantyhose on again. I made sure to feel and pull a little paying careful attention to his hardening cock. That was the sign I needed. Sonia had said that Keith went wild when she wrapped his cock in panties. At least I knew that he was not only willing to wear the costume, but that he was enjoying the feel of the panties and pantyhose on his legs and genitals. This was looking like Sonia had discovered a common fetish for some men. The fact that she had been the one who had instigated the sex play allowed her husband to slip easily into the role without having to examine his heterosexuality.

The next day, October 31, I got the bra and breastforms. Everything was ready. When Jeff got home from work, I had him shave his face very closely with a new razor blade. I inspected every inch of his body to make sure that there was no unwanted hair. When I sat him down on my vanity stool, he seemed a little uncertain. I brushed on the foundation to hide his beard stubble. It wasn't quite a concern for me, but I had been watching tutorials on MTF transitions and I was going to make certain I followed the proper protocol. Since it was a costume party, the makeup could be more dramatic without being out of place. Even so, I was reasonable about his cheek rouge and eye makeup.