Halloween leads to something new

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Wife's choice of costumes leads to new discoveries for both.
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It was Halloween Eve, Devil's Night, and my loving younger wife was finishing my makeup. She had decided we should go as Bride and Groom with the gender roles reversed. I wasn't real thrilled with the idea, even less so as my wife finished with my lips then said, "Time to get dressed."

"It's bad luck for the Groom to see the Bride before the wedding," I reminded her as she took off my tee shirt.

"It'll be much more bad luck if you don't relax and enjoy the evening," she warned as she picked the bra up off the bed.

Yesterday had been one of the most embarrassing days of my life. My more-than-somewhat kinky wife had decided to help me lingerie shop for the costume. We went to Walmart late in the evening, thank God. My wife had worried over the bra, panties, slip, stockings, and finally shoes as if she were shopping for herself. She had me try on the undergarments much to the amusement of the young woman working the department.

"On with it," she demanded, dangling it from her pointer finger. "No fun no sex for a month."

The warning wasn't lost on me. I took the bra, hooked it, slid it over my head. "That isn't the way you put on a bra," Alandra said in a slightly annoyed tone of voice.

"It's the way I put on a bra," I replied as I grabbed her beautiful ass and kissed her with passion.

"You smeared your lipstick dumbass," she said clearly annoyed. I silently pulled on the panties, the garter belt, the hose, and then stepped into the slip and pulled it up while she fussed with my lipstick between garments. "What're we going to use for tits?" she wondered aloud then took off.

"Way too serious she is," I mumbled.

"Fuck you Yoda," she said, reaching down my slip and under my bra to pull the cups out before dropping in grapefruits. "You're stacked babe!"

Satisfied with her work, she motioned I should step into the wedding dress she had borrowed from someone. "You're a big size 20," she commented as she zipped up the back of the dress before motioning me to sit down.

She slipped the wig on me, shook her head. "How the hell are we supposed to keep this on with your bald head?" she wondered aloud.

"I'm not going to be riding the Harley or anything, it should be fine," I did my best to assure her before she thought of using Superglue. "You better get ready," I chided her.

"You never know what you'll be riding," she replied as she stuck the headpiece over the wig. "You're pretty but you won't ever be a beautiful woman."

"My heart is broken," I said with a sniff.

An hour later she pulled into the driveway of her brother's place. The street was packed with cars; everyone knows my sister-in-law throws fully wicked parties. My wife, er, husband put his arm around my waist as we walked the short distance to the front door.

"Oh! My! God!" my sister-in-law Becka said as we walked in. And yes, she did pause between words. "You two are absolutely adorable! Can I kiss the bride?"

I blushed then she kissed me with more than a hint of tongue. Becka was model material; Junior responded to the affection and poked her a bit. I hoped it didn't show.

"Bit of a lesbian tendency?" Alandra teased her. "She's mine! All mine!"

"Who's the beautiful bride?" my brother-in-law Fred asked. "Do I get a kiss?" he asked and his lips met mine before I could respond. His tongue was pushing hard against my lips, I pulled back aghast.

"What the hell you doing!?!?" I asked, pissed as all her.

"Jesus Jack, I didn't know it was you!" he sputtered before blanching.

The party was fun and more than a few of the woman hit on me in a maybe just kidding manner. Perversely it aroused me to think I was turning them on while dressed as a woman. Then there were a couple guys who didn't know I was one too or their doors swung both ways or the other way.

When we got home my husband pretended to try and carry me over the threshold. Alandra was full tilt into the roll playing as she sometime was in our lovemaking. I let her seduce me and undress me like a proper groom would. I demurely acquiesced to her advances and requests as a blushing bride might on her wedding night. To say the sex was the best we ever had wouldn't be much of a stretch. I learned something new about my wife as we snuggled down and talked in the post-sex aurora of emotions.

The next morning I tossed the soiled lingerie in the wastebasket before heading in to shower. Shortly my wife joined me and we had some soapy fun before toweling each other off. I noticed the lingerie in the laundry basket, asked "Why not just throw them out?"

"Last night was fun," she said. "Much more than fun. I had the most intense orgasm I ever had. I thought we might hang onto the stuff for a while."

What could I say? She indulges my fantasies, usually without too much protest. Could I do less for her? Especially in the light of her sexual arousal and fulfillment?

A couple days later Fred stopped by. While Alandra's older brother wasn't quite my very best friend, we had a comfort level many would envy with their best friend. We feel free to stop by and walk in each other's house, having swapped keys years ago. I was in the garage working on my pet project, restoring a 75 Trans Am.

"Looking like new," Fred said as I hand buffed the paint I'd put on the door a week before. He looked down the panel before saying "You're a master; you can't tell anything was wrong. It's smooth as glass and not wavy like a lot of body work."

"Thanks," I said, meaning it. I dropped the rag and opened the mini-fridge and tossed him a beer.

"Um, you know at the party I didn't know it was you," he stammered.

I fumbled around in my brain for what he was talking about before remembering the tongue filled kiss. "Not a problem," I assured him. "But I noticed you tenting your pants after you found out," I joked with him. "Getting hard now thinking of it?" I asked, messing with him shamelessly.

"I didn't have wood!" he about yelled. "I don't have wood now!" he said while turning away.

"Pull it out and let me see!" I challenged, pushing the button I had just found. "I'll bet you have a big boner."

He turned around, opened his belt, and revealed his engorged manhood. "Happy?" he asked.

I was shocked into silence. What the hell was going on? I was just kidding with him and he pulls out his hard-on. A hard-on about kissing me! "Put that fucking thing away!" I croaked, mouth suddenly drier than the Arizona desert.

"Well you asked," he reminded me with a grin. "Remember that."

There was an awkward silence while we each sipped our beers not knowing what to say next. The growing silence was broken by the sound of my wife's car in the driveway. I headed out to help her with the groceries; her brother followed and lent a hand. He stayed for dinner, Beca was at her mother's for the evening and Fred was a typical guy, helpless in the kitchen.

When he left, I was about to ask my wife if her brother was a bit strange when she said "Come and see what I got you," while taking my hand to pull me toward the bedroom.

"Why don't you slip into something more comfortable while I get us some drinks?" she suggested while handing me two Walmart bags.

I opened a bag as she left the room. There were a couple packages of panties. The other bag held a couple nightgowns. I was about to protest when I remembered the outstanding sex we had after the Halloween party. I looked at the panties, thinking what I would like to see Alandra wearing. I stepped out of jeans and briefs in one motion, stepped into the black satin hip hugger panties. Out of the other bag I took the longest nightgown, a satin affair with sleeves down just past the elbows. I was laying on the bed when she walked in carrying the drinks.

"Wow!" she said, blushing as I had gotten her wig and put it on too.

She put in a DVD, laid on the bed beside me. It was a porn DVD. She was fully into the male role and I fell into the female role of secretly being aroused by the porn but acting as if I was repulsed. Alandra seduced me roughly like a guy would take his girl after being aroused by porn. Very little foreplay, just straight into shoving my head down into her crotch. Like the lady I was, I protested and tried feebly to pull away. The evening was filled with raunchy toe curling sex...

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GrrrreatImaginationGrrrreatImagination3 months ago

Wait, what? I mean, this was a great beginning. Surely you have a chapter 2?

AnonymousAnonymousalmost 6 years ago
Smilar Halloween crossdressing experience

Several years ago on my 30th birthday which happens to be Oct. 31 my wife decided that we would go to my sisters Halloween/birthday party as twin sisters dressed in square dance dresses. She as your wife was really into it. So about 3 weeks before the party we went and bought matching red with white ruffles satin square dance dresses. We bought for each dress 3 petticoats. The 2 inner petticoats one in red and one in white and they are made of organza a stiff yet very silky and slippery sheer material made of nylon or silk, ours were nylon, and a white chiffon petticoat to go over it. Actually I am not a large man and she wears a size 5 and I now know I wear a size 9 in a womans dress. They only had one pair of red and white ruffled nylon pettipants in her size (which are ruffled panties that go under the dress so when you twirl they show). They had other colors in my size (my panty size is 5) but she said I would wear full cut white briefs. So we tried on the dresses and knew the petticoats would fit since they are stretch and she knew I ware a size medium. So off to Penny's we went and we bought me a pair of Vanity Fair 100% nylon briefs with lace inserts on the front of the leg openings and a very lacy and pretty Playtex underwire bra . Very silky and a bit sheer but I figured I would not be twirling so who cares. She asked me if I wanted to wear pantyhose or a garter belt and stockings. I thought that a garter belt would be a bit gay as far as I am concerned but liked the idea of not having pantyhose so she suggested thigh high stockings with elastic lace to make them stay up but she said she would wear one of her garterbelts. So off to a wig shop and Payless shoes for size 8 (my womens size) high heeled dance shoes, she had dance heels already. OK you get that it was a bunch of stuff and a lot of work just getting the stuff. Basically I forgot about it until Oct 30th when she brought it up and when we needed to start getting ready. She said I needed about 2 hours to get ready and I was thinking I don't think so but learned just to go along and not argue. So I get home about 4 hours prior to needing to leave for the party and she told me we need to leave about an hour early because she forgot to get stockings, I suggested I give her the thigh highs and I would not wear any but she would not hear of it she said the petticoats would not be that comfortable. So into the shower we went and she took the shaving soap and started to put it on my legs and said she would shave my legs for me, I am like what for and she said I had to shave to wear stockings and that there was nothing more sexy feeling than new Hanes stockings slidding up on freshly shaved legs (later I discovered she was right) so again no argue. I rarely need to shave my face since I have very light blonde hair and just never had much of a beard but I shaved anyway at her demand and we were finished and told me to dry off and in her makeup chair and she began working on me first by plucking some on my eyebrows ouch and went to work on my makeup then false eyelashes eyeliner, shadow to match the dress, of course face makeup cheek blush and finally red lip liner and red lipstick then the long wig and damn I looked at myself and did not even look like me and it was a bit unnerving to be honest. Then she went for the false nails that were having a tough time sticking so she attached them with super glue and it took weeks to get them off. She had laid out all my costume on the bed next to hers and told me to get dressed as she did her makeup. Unfortunately I had no idea how to put on the thigh highs but she came out and showed me then helped with my bra and had some form breasts inserts to put in the bra and said I could put on the panties and said the 2 stiffer organza petticoats first then the chiffon on top and she would help with the dress and zip up the back. WOW is all I could say I mean I slid on the panties and began to feel odd they were so silky kind of turned me on a bit but when I put on the petticoats and then the chiffon petticoat and the high heeled dance shoes and I stood up to walk and felt all that slippery organza sliding between my nylon covered legs and Hanes thigh highs are very silky and the pettis sliding against my nylon covered ass to be honest I was so aroused and gave me an erection that I was very flushed and when my wife saw me she asked if I was OK and then with the satin dress over all of it my legs collapsed together as I pushed through the petticoats to try and get some pressure against my penis so as to not cum in the panties it actually worked the opposite while trying to push against it all the slippery sensations of the petticoats sliding against each other and against my panties was just overwhelming and I had an orgasm in my panties and I will say the most intense orgasm of my life to that point and my wife was just watching in some shock I thought. WOW oh my the single greatest sexual experience of my life to that point. My wife was like damn did you just have an orgasm and if so why. I tried to explain all the slippery sensations of the stockings and the panties and the three silky petticoats and the satin dress and sliding against each other and all around my penis and then looking at this woman staring back at me in the mirror was so sexually arousing it was just too much. She did have a little time understanding but not having a penis and wearing all that silky slippery materials all her life the sensations were the not the same to her. I took off the panties and she cleaned them up the best she could and used a hair dryer to get them dry and sheer nylon dries fast. Actually sitting there with all the sensations of the petticoats around my penis made me cum again but I could not tell her for fear she might get mad but the first inner petticoats had a wet spot but I turned it a bit and when I put the panties back on I mean it was not 5 minutes later and I was hard a rock again and told her I had to use the bathroom and she said like a girl I would have to sit but I did not use the bathroom but had yet another orgasm and yes then another again and by now not much was coming out. Finally we went to the mall so she could get a pair of stockings and she said lets go and I was not sure but she said no one would even now I was a guy being so short an petite and no one did. After she bought them she said lets go into the ladies so I can put them on and I was like I can,t go into the ladies room but she said just go into a stall and I did and yes pulled up my petticoats and pull it out and when I saw the red fingernails grasping it had another extremely intense orgasm and thus was dry and my gosh I was beginning to feel very odd. Finally we got to the party and I could do nothing but focus on what I looked llike and the sensations of what I was wearing. I must of had seriously another 5 orgasms at least the they were getting more intense with each orgasm. we got home and my wife was like, you really like dressing up like a girl I guess and I told her that yes I did. The next day she went to work I took the day off and dress up and had I would say 10 orgasms in a 6 hour period. Now all I want to do is dress and look like a woman and my wife goes along but it is to the point that I cannot get an erection to have sex with her unless dressed completely as a woman makeup long nails the whole thing. She is starting to get pissed cause she says she is not a lesbian and would like to have sex with a man now and again. At this point it will be 2 years in OCTOBER and I quit my job to work from home so I can dress as a female all day. I now shave my legs and underarms all the time and I guess I have ben dressed and livig as a female for about 6 month now without wearing any male clothing.

AnonymousAnonymousabout 8 years ago

You should add on to this story.. It would be hot! Maybe make it where he gets with the brother-in-law.

AnonymousAnonymousabout 10 years ago
No fun no sex for a month?

What a bitch. Any woman that uses that ploy on her husband deserves the divorce she gets. She would have been out the door so fast it would have made her head spin. Disgusting story of abuse and humiliation.

AnonymousAnonymousover 10 years ago
Reboot Please

I know this story is old but I would Love to hear more!

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