Dressing For Halloween

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Copyright Oggbashan September 2019

The author asserts the moral right to be identified as the author of this work.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.


Sandra is my wife June’s best friend and was Matron of Honour at our wedding. June knows I like Sandra and more than that I am attracted to her. If Sandra hadn’t been already married when I met her and June, Sandra might have been a potential girlfriend. I would have had a hard time choosing between her and June. But Sandra was already married. I didn’t see June as second best, and was very happily married to her, but both of them knew I had more than just friendly thoughts for Sandra, and they teased me about it.

Sandra flirted with me with June’s consent and encouragement. June knew that Sandra’s mild flirtation aroused me and our love making that evening was likely to be more impassioned because of my frustration at not being able to get anywhere with Sandra.

Sandra is a tall, well-developed blonde with a pink and white complexion. She looks spectacular, dresses well and knows she is attractive. But Sandra is far more than her looks. She is intelligent, articulate and a great organiser. She, and June, know exactly how to play me to get me to do things I wouldn’t necessarily do for myself.

The forthcoming Halloween party had them both manipulating me. I hadn’t known, but should have guessed, that Sandra’s marriage was in trouble. Sandra had been spending more time with June than usual and they were often talking in whispers so I couldn’t hear. I didn’t mind. Having Sandra around was pleasant. Her frequent hugs and kisses were more than pleasant. One evening she sat down on my lap, wound her arms around my head and pulled me into a long kiss. I was embarrassed because June was in the room watching us, but Sandra’s kissing was so effective that I was lost in the passion of her kiss.

“Do you think I have softened Stuart up enough for us to ask, June?” Sandra said. Her head was still pressed against my cheek.

“Yes, I think so, Sandra. Much more and he wouldn’t be able to think at all.” June replied.

“Well?” I asked.

“The two of us want to make a bet with you, Stuart, about the Halloween Party.” June said.

My heart sank. I was not keen on the Halloween Party which was being organised by one of our mutual friends. It would be a costume party, but cross-dressed — the men dressed as women, the women as men. I had been reluctant to go and had said so to June. We hadn’t argued about it but she was disappointed and I knew it. I might have agreed eventually, just to please her, but I doubted I would enjoy it.

“We want to bet that you should go, dressed in my wedding dress, as Dracula’s bride.” Sandra said. “I would be Dracula wearing your evening suit, June as Van Helsing in what you call your country suit.”

“And if you agree and go, you would win the bet,” June said. “You might like the winnings.”

“Which are?” I asked.

“A night, sharing a bed with both of us,” Sandra said.

I was startled. I turned my head to look straight at Sandra. Her expression showed she was serious.

“Won’t Thomas object?” I asked.

Sandra’s face fell. She seemed on the point of tears. I kissed her forehead gently.

“What June knows, and you don’t, Stuart, is that Thomas and I are over. We are separated and the divorce is proceeding. He had a lover at work who is now pregnant by him. He has asked for a divorce so he can marry her.”

“Is he mad?” I asked.

“No. He doesn’t love me as much as you do, Stuart. He never loved me as much as you love June.”

“I’m sorry,” I said, kissing Sandra’s forehead again.

“I know you are, and that you love me nearly as much as your June. Your love, and June’s, is helping me. But will you take the bet? It would help me to face our friends with you two beside me. By the time of the party the divorce will be common güvenilir bahis knowledge.”

I looked across at June. She also looked sad.

“Yes, Sandra, if it will help you, I’ll be there as Dracula’s bride, wearing your dress. Will it fit?”

“We think so, but now you have accepted the bet, I’d like to try it on you. It’s in my car. Shall I get it?”

“OK. But what if I had lost the bet?”

Sandra laughed.

“You will still get a night in bed with both of us, but we would all be fully dressed.”

She went out to her car.

“I’m going upstairs to get the other things,” June said.

‘The other things?’ It seems that they had planned this between them and expected me to accept the bet. The idea of a night with June and Sandra was irresistible and they knew I couldn’t refuse. I had been set up, again.

June was back first with a large carrier bag. Sandra arrived next with a large suitcase.

“Strip to your boxers, please, Stuart,” June asked.

She produced a large bra with padding sewn in. I stood up as the two of them hooked it around me and adjusted the shoulder straps so the padded shapes were at the right height. They were bigger than June’s breasts and similar to Sandra’s.

June helped me into a long corselet that ended below the bra. Once she had adjusted the shoulder straps and pulled up the front zip my stomach was compressed and my erection squeezed.

Sandra took a large dress bag out of her suitcase and hung it from the picture rail. She pulled a floor length white slip over my head and down to the floor. Its straps covered the straps of the bra and corselet. The slip was flared below the waist so I could walk easily. The two of them knelt on the floor to insert four hoops into a petticoat before tying it around my waist.

I had never seen Sandra’s wedding dress. She had married before I had met her and June. She unzipped the dress bag. The dress had a high neck and long satin sleeves. June and Sandra lifted the dress over my head and spread the skirt over the hooped petticoat. The inside slip, the hooped petticoat and the wedding dress’ skirt splayed over the floor.

“He should really be wearing heels,” Sandra said, “but that doesn’t matter for this fitting.”

I wasn’t sure I could walk in heels high enough to lift the dress off the floor, and certainly not all evening at a party.

They eased my hands down the sleeves and fastened the concealed zips in the sleeve ends. The sleeves were almost skin tight below the elbows.

“His hands look wrong,” Sandra said. “Never mind, he can wear gloves for the party.”

“Would gloves fit under the sleeves?” I asked.

June looked.

“Maybe. If not, they could go over. I have some elbow length white satin gloves somewhere, but not now.”

“And now,” Sandra said, “the final touch. When Thomas bought it I wasn’t pleased. It cost too much for a single use at a costume party but now I can use it again.”

She opened a white box and produced what I thought at first was a blonde wig. She held it up to show me and Judy. Yes, it had blonde hair, styled just like Sandra’s but it wasn’t a wig. It was a full latex head mask with a face very like Sandra’s including her make-up. She fitted it over my head. It had small holes for my eyes and nostrils and a very small opening between the lips. It zipped up at the back, concealed by the blonde hair. The lower part covered my neck and part of my shoulders.

Sandra lifted the bodice of the wedding gown and zipped it up at the back. The lower part of the mask was inside the gown’s neck. She lifted a tiara with an attached veil and fitted that to the blonde hair. The veil was waist length behind. When covering the face it fell in front to the bust line. After Sandra had arranged it, she lifted it back to expose the female mask. I stood still while Sandra and June took pictures on their phones. They showed them to me. I looked like a sister Sandra never had but with a face devoid of expression. I tried moving my lips and jaw. The mask’s expression remained türkçe bahis almost unchanged as if the woman was in a trance.

“Now you look like Sandra, or almost like Sandra, and a beautiful bride,” June said. “It is uncanny. I would never know that it was my Stuart inside that dress. But you aren’t yet Dracula’s captive bride.”

She produced a wide leather belt from her carrier bag and swung it around my waist, buckling it at the back. She took my wrists and fitted them into strapped cuffs on the side of the belt. Without gloves on I might just have been able to undo those buckles after a struggle. With gloves? I would be helplessly restrained.

They stood either side of me, took my arms and lowered me to the settee.

“Stay there while we try your suits on,” June said. “We won’t be long.”

I tried to say ‘OK’. To my horror I found that the mask was a very effective gag. All that came out was a muffled grunt. Sandra laughed at me.

“Stuart, you have found the disadvantage of that mask. You can’t speak. That is why Thomas only wore it once. He didn’t like being gagged.”

They left me on the settee dressed as a bride and looking very like Sandra. I might have been able to stand up, or possibly wriggle my hands around to undo the buckles holding my wrists immobile, but what was the point? I couldn’t get the dress off without help. I sat back on the settee and waited.

Within ten minutes they were back. Sandra was wearing my evening suit, a dress shirt and black bow tie. June was wearing my loudly-checked three piece country suit. Unlike me, who looked just like a woman dressed as a bride, they were still very obviously female with their breasts straining at their male clothing, and their long female hair and make-up contrasting with the way they were dressed.

“I think we’ll do, Stuart,” Sandra said. “We sort of fit your suits but are seen as cross-dressed, unlike you who could be a real woman as a bride.”

“Will you go with us to the party?” June asked. “Just nod. I know you can’t speak.”

I nodded. They sat beside me and hugged me before taking the mask/hood off and kissing me. I couldn’t have resisted even if I had wanted to because my wrists were still secured.

I watched, fascinated, as they stripped off my suits and stood revealed in their bras and panties. Sandra teased me by straddling me and rubbing her bra-covered breasts across my now naked face. She pushed against me, forcing my head back against June’s cleavage who was behind me.

I was disappointed that Sandra dressed herself before they took the wedding gown of me. But June made up for that disappointment by dragging me off to bed for a night of sex. She knew what effect Sandra had on me and was determined to prove that my wife could take all the lovemaking I could do.


By the time of the Halloween Party Sandra and June had dressed me as a bride several times and decided on some adjustments. They had found a pair of black heels in my size but I couldn’t walk in them. They had compromised. I was wearing thick-soled white trainers. They didn’t give me enough height for the dress’ skirt to clear the floor but it hid the trainers. The full length slip wrapped around my feet so they decided to tack it to one of the upper hoops with six stitches. The hem was now splayed enough to allow me to walk freely. No one could see my legs, but they insisted on white pantyhose.

June drove us to the party in our large SUV. I was sitting in the back beside Sandra. June had decided that she was the designated driver and would not drink alcohol. I could only drink with a straw in the small opening of the mask’s lips and since my wrists were restrained by my sides someone would have to hold the drink. June’s elbow length gloves had been covered by the dress’s sleeves. That had been difficult and took nearly as long as the rest of dressing me. Now I was totally unable to release the buckles holding my wrists by my sides, and even if I had, the gloves would have meant I couldn’t get out of the costume.

Sandra had added güvenilir bahis siteleri a large black cloak, lined in red, and had found a white cloak with the hood trimmed in white fur to cover me. June was wearing a large wooden crucifix around her neck and carrying a black doctor’s bag.

As we entered the house we were greeted by our hostess.

“Hello, June and Sandra,” she said. “And this is?”

“My husband Stuart,” June replied.

“It is? I’d never have recognised him. He looks like a beautiful bride, who might be your sister, Sandra. That outfit is stunning.”

It was. I won a bottle of wine for the best costume. The three of us won another bottle for the best group.

My costume confused some of the other guests. The women dressed as men danced with the men dressed as women. Some of the women thought I was actually a woman until Sandra or June told them who I was. I danced with Sandra and June more than with anyone else. Sandra held a gin and tonic for me to drink through a straw. I found it frustrating that I could not talk to anyone because of the mask gagging me. June had to help me to go to the toilet. While my arms were restrained I couldn’t lift the skirt and petticoats, nor slide the pantyhose down and undo the lower end of the corselet.

Several women expressed compliments on the way I was dressed and wished their husbands/partners had been so cooperative or so willing to be transformed. A few appreciated that even without the restrained wrists I was effectively imprisoned in the wedding dress. They praised my tolerance and cooperation with June and Sandra. A couple wished they could do as much to their husbands.

Sandra enjoyed herself, dancing with many men dressed as women. Towards the end of the party she told me that seeing me in her wedding dress had removed the unpleasant associations of wearing it to marry Thomas. She would remember it on me, not on her. Of course I couldn’t respond. I felt her hug but her kiss on my covered face was lost.

Once back home they left me imprisoned in the dress while they changed. They came back downstairs in bra and panties before releasing me. June had to crawl under the hooped petticoat to cut the stitches on the long slip before the petticoats could be taken off me.

It was a relief to be free from the constraints of that costume. It was even better to be kissed and hugged by both women before they put the dress back in its bag and hung it up.

Sandra took my hand to take me up to the bedroom. June pulled off my boxers before all three of us were naked under the duvet.

Sandra and June cuddled me before June impaled herself on my insistent erection. As she did, Sandra’s pussy descended on my face. Sandra and June played with each other’s breasts as they rocked on me until I came into June. Afterwards my head was squashed between two cleavages as I went into a happy and blissful sleep.

Later in the night June rode me again but this time my mouth was filled by one of Sandra’s breasts. In the morning my face was covered again by Sandra’s pussy as the two of them used me to arouse themselves before June squeezed her lower muscles to finish me. I went back to sleep under two women’s bodies,

When I woke again I was surprised that only Sandra was in bed with me.

“Shh, Stuart!” she said. “June has lent you to me. Just relax and enjoy it.”

I wasn’t sure I could. If I had drunk more than a single gin and tonic last night I probably couldn’t have. But being aroused by Sandra was the stuff of my dreams. After she had kissed me frequently and rubbed her sex across mine, I became erect again.

“This one’s mine,” I heard Sandra say as she slid me inside her.

I had to let her do the work but having Sandra arousing me was bliss. She treated me gently and sensuously, bringing me very close before stopping and starting again. Eventually I could hold back no longer and shuddered underneath her. Exhausted, I was aware that Sandra cradled my head against her breasts as I went back to sleep, not believing that I had shared the bed with two demanding women last night, even if I had won a bet. I had never thought they would actually deliver the promised winnings.

They had given me far more than I ever expected for an evening dressed up as a captive bride.

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