tagTranssexuals & CrossdressersHalloween leads to something new

Halloween leads to something new


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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by Anonymous

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by Anonymous04/19/18

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 wifemore...

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