A Costume Affair

Cross dressing trouble

Husband models dress for friend and is sucked into trouble.

A female friend and I had a great, platonic relationship as they call it. We talked about the troubles we had with the people we dated, the woman I married and her on-off relationships. This lead to an air of trust and familiarity that lead us down an unexpected, exciting and ultimately master-slave relationship that I have yet to recover from.

It started as a bit of a joke. I wore a wonderful rust coloured shirt to one of our evening get togethers. Being in the fashion industry, Grace liked to dress people up in funky costumes. As Halloween was coming up she wanted to test out a costume she had thought up for her latest boyfriend. I naturally agreed. She got out some orange and black tights, bright orange fairy slippers and a crape paper, string dress thing. She told me to take off my trousers which I obligingly did. I bulked when she said the underwear had to go too.

When I asked why, she simply said it would spoil the affect if my underwear was

scrunched up under the tights. I sheepishly and quickly dropped the underwear and pulled up the tights. The rest was easy.

The surprise came when she told me to hold up the dress. This time the question of why was answered with she was trying to see if she could create an autumnal affect. Bewildered, I did as commanded. I then felt her pull the tights, grab my penis and manoeuvre it so it was aiming straight up and then let go the tights. She started laughing at my reddening face. "Don't worry, I've seen loads of penises."

"But not mine," I tried to chuckle. Then I felt something outline my balls. What next, I thought.

"Okay, you can take off the tights." Relieved, I did so and dropped the dress. It felt weird with only the paper dress between me and the world. We chatted while she cut and sewed on the tights. "Here you go." I looked a bit confused. "Try them on again." I did so. "Can you lift the dress again?" To my amazement, I felt her hand around my balls and then them being pulled out. The tights then fitted snugly around them. Once again, my penis was manoeuvred straight up only this time I felt cloth around it and heard a click. I am sure I was bright red. But I did have a raging hard on!

"That's perfect. How does it feel?" We had talked a lot about relationships with the occasional reference to sex. This was the first time it was so direct, and personal!

"Fine, I guess."

"Not too tight on the balls?"

"No, not now."

"And how's the penis holder?"

"Fine now but what on earth is it for?"

"Too ensure the effect is not ruined. So do you mind wearing them for the rest of the evening? I want to dress up Matt in this for a costume party. I need to make sure they are comfortable for the evening."

I again sheepishly agreed as my balls weren't always covered by the stringy dress.

"It's a bit embarrassing as my balls aren't always covered by the dress."

"Well, it's Autumn isn't? That's when the nuts come out!!!"

It was a good joke. I knew she went to risqué parties so assumed that Matt liked them too. The rest of the evening went fine. I became quite used to the costume and stopped noticing my balls were occasionally "out." At the end of the evening I gave her back the costume, got dressed and went home.

When we met a few weeks later, I was wearing the same shirt so asked her how the party went. She was disappointed because Matt wouldn't wear the costume. "And after all the time I had put into it!"

Trying to be a good friend and gentleman, I offered, "If it makes any consolation, as it is Halloween and we are both stay-at-homes so to speak, I'll wear it tonight." She was very pleased by that and quickly got me into the dress and tights. She giggled at my balls this time which gave me a pretty good hard on. "Why didn't Matt like this?" hoping to diffuse the situation a little.

"Well, when I realised nuts don't have hair, he became less enthused." Confused I asked what she meant. "I wanted him to shave his balls."

"That's a lot to ask of a man!"

"It's not that much if you know you are going to please a woman." She started jiggling my balls again. She must have seen the reaction it provoked the first time. "Wouldn't you want to please me? I'd love to see if my idea would have worked." I was melting.

"But how would I ever explain it to Caroline?"

"Would Caroline ever notice?" She had a point. I had always wanted my wife Caroline to give me a blow job or just play with my kit. But she simply wasn't into non-missionary sex. I had told this to Grace and was playing for all it was worth. "Besides, I would do it gently. And I'd want to make sure I got every hair. Do you know the best way to do that?" I shook my head. "Well for someone to lick them ... with their tongue... ever so gently." She was circling my balls with her fingers and I melted some more.

"I guess that would be fine. You'll never tell Caroline?" She looked at me with surprise. "Sorry, I know I don't have to ask. Forget I said it."

Grace was quick and gentle with the hair remover. Or as gentle as one can be when pulling hair out by the roots! However, she was good as her word. "Now for the inspection." And what an inspection it was. I was putty in her hands, or at least the tip of her tongue. My penis rock hard

The tension rally began after dinner when Matt arrived. This was unexpected and wound up being a rather fraught after Grace and I had our after-dinner drinks. At first Matt didn't see the pumpkin costume because it was hidden by the table. When I finally got up he let out quite the laugh. He became derogatory about Grace's abilities and the design she came up with. I did felt for Grace and could see why she wanted to drop him.

"Before you, go I just want to see if there are some nuts available." Before I knew it, he had pulled the pumpkin dress off me. "Yeah, I thought so. Looks like some damned homo get up if you ask me."

"I think it's a dammed brilliant idea to me and worthy of a good laugh to someone who has a sense of humour." I took off the tights right there and with the most dignity I could muster put my trousers back on and said good-bye.

Grace was right, Caroline didn't even notice. Over the next few weeks I thought about what Matt had said and felt bad for Grace. I decided to propose a bit of an outlandish idea the next time we met: Would she design something that made me look like a woman to see if we could fool Matt? Maybe get him to give me a "homo" kiss on the lips. Grace immediately warmed to the idea. We had a good chuckle as we made plans. We selected a weekend that Caroline was supposed to be away on a hen doo.

We spent the Saturday getting me clothes and make-up and practicing to be a woman. We chose flat shoes to make this a bit easier. Grace was a good teacher helping me change my walk and adjust my voice.

The Sunday morning was spent making me look a woman. She did a bloody good job. I didn't recognise myself. Matt arrived for lunch and seemed to not to recognise me either. He certainly liked what he saw because he flirted endlessly when Grace was not around. This of course was part of the plan. For dessert, Grace made the excuse that she had forgotten cream and just needed to pop out for a minute. This gave me the opportunity to really lay it on. It wasn't long before Matt was trying to put his hand up my skirt. I was wearing the tights used for the pumpkin costume. I kept my groin under tight control. However, I didn't want to take any chances. I told him I wanted a kiss first, and then I would grant him access. He quickly obliged. When he put his tongue almost down my throat, I quickly pulled back.

"Do you want to put something else down my throat?" He almost nodded his head off in excitement. "Well, let's see what you have to offer." As his trousers hit the floor we heard the door open. The look on his face was worth the tongue! However, as I got up to head towards the door, it was my turn to be shocked. Caroline came in with Grace.

"Caroline, this is Juliet, a good friend of mine." Grace was trying to indicate something to me but I couldn't' figure out what. I was too much in shock and did my best to keep my composure. "I ran into Caroline at the shop."

"Yes, I was looking for my husband."

"So I invited her to have dessert with us. Where's Matt?"

"Oh, he's just getting himself sorted out," I giggled. Matt arrived a bit red faced. He had put his trousers back on presumably when he heard the voices. Grace very graciously guided us all to the table for dessert while I led Caroline in a discussion of her "lost" husband.

"I was supposed to be at hen party all weekend but it got a bit too raunchy for me." She tried to change the subject but I couldn't let her stop there! "Well," she finally continued, "We had a great time hounding around on Saturday and tucked into a wonderful dinner. The lead bridesmaid had arranged a five-man strip show to top things off. It was a super show. Then a discussion started about payment. Something went wrong and apparently the bridesmaid didn't have the money. She explained the men wanted the bridesmaid to give them a full blow job. Several of us thought that was outrageous. To our surprise, the bride said she couldn't possibly allow this. Certainly everyone could contribute something. As everything was all inclusive none of us had brought any real money. The senior bridesmaid started looking rather worried. Finally the bride decided to rescue her. "You have been too nice to organise all this and help with the wedding arrangements. This is the least I can do. I accepted the debt and will do whatever you say to clear it. Hell, it's my last night of being free to do such an outrageous thing!"

"Oh how exciting!" I had always wanted Caroline to do this but she steadfastly refused to. I couldn't help but take advantage of this to provide some encouragement.

"Not to me or any woman in her right mind. And how many blow jobs have you given? Of men you haven't even met!" exclaimed Caroline.

"Well not five in a row, certainly. But enough to know that it would be quite fun. I certainly would have been up for it. I like going all the way!" I was trying not to be overly enthusiastic.

"Well," frowned Caroline, "she obviously agreed. Down she went on the first one and quickly had him hard. She pulled away as he exploded onto the floor. This started another discussion. The bridesmaid said that she had agreed that a "full blow job" which meant swallowing, and if she failed she would have to give the guys a piece of her clothing to make up for it. If that had been me I would have stopped right then and there."

"Oh, that's a bit prudish. A full blow sends a bloke into seventh heaven. I'm sure they put themselves out for her. A bit of clothing is a small compensation for being let down."

"To the amazement of many of the hens, she again agreed. I suspect more due to alcohol than common sense. 'Look, I'm going to get married so this is the last time I will be able practice my technique, shall we say.' So off came her top and she lined up again. I will admit she appeared to be having a good time. Then one of the bridesmaids started tickling the bride just when the bloke started exploding in her mouth. It's bloody hard to swallow when you're laughing! She scowled at the bridesmaid but she pulled off her bra. A great roar when up, or should I say cackle as it was a hen party? She then said no more tickling her sides; she had serious work to do. Well, the lead bridesmaid didn't know if she could enforce this from her existing position. She said the only way to do this was for the bride to do the 'payment' from the top of a table on the stage. That way no one could reach her sides without being seen. She started to complain but gave in as the lead bridesmaid said the bride had said she would do what was necessary and this is what was necessary. I was floored when she mounted the table and got to work. Her, shall we say, full bosom swayed in rhyme with her movement."

I interrupted again in hopes of softening up Caroline. "She sounds as though she was thoroughly comfortable exhibiting her skills. The more you do it the easier it becomes." This time Matt chimed in with encouraging agreement.

"That may be so but she failed to swallow again. This time, unbeknownst to the bride, the lead bridesmaid directed another of the other bridesmaids to start playing with her swinging tits with a long duster type thing. The distraction was too much. She once again pulled back and cum went flying all over her body as she tried to stop them messing with her tits by standing up. The room exploded in laughter. Before the bride could react, the lead bridesmaid pulled down her skirt. There was a gasp as she didn't have any knickers on! I guess she was expecting some action but her reaction said this wasn't it!"

"Yes, that must have been quite the shock." We all looked at Grace in surprised because she had been silent up to this point.

"I think she wanted to stop at this point but the lead bridesmaid was truly in control and loving it. The bride was now trying to cover herself up as best she could, which wasn't very good I must admit. The lead bridesmaid asked the assembled hens - vultures more accurately - if they should allow the proceedings to stop. All sorts of chants and sayings came forth. The clincher was the lead bridesmaid saying this deal was a deal just like marriage. You got to find a way through it no matter what! The bride fully exposed herself as she repositioned herself on the tabled for number four. But before she started she made everyone promise that no hands would touch any part of her body and on one would tickle her. She made everyone promise no one would do this. She was going a pretty good job when again the lead bridesmaid motioned to a bridesmaid to come over to her. She held up a double-end dildo. There was a gasp. The bride had positioned her knees nicely far apart so the bridesmaid had easy access. The poor bride didn't see it coming and must not have felt it."

"I bet it slipped in easily. Sucking cock can make a woman really hot." I smiled at Caroline.

Caroline just scowled at me as she continued: "Well either that or it was well oiled. Or maybe she was well oiled. Regardless, she didn't stop the bridesmaid from moving the dildo in rhythm with the blow job. This only proved you can't swallow while you have an orgasm. The hens were eating this up!"

"I'm not at all surprised," I interjected. "It's not just men who like sex you know. Women can enjoy it too."

"On a table in front of all your friends!!! Just before you are to get married!!! Really?"

"Well, have you heard some of the stories from bachelor parties? Why shouldn't women be able to do the same?"

Another scowl and Caroline continued. "Well, now an argument broke out about what type of additional payment the bride could give. The assembled hens asked her to show them what she had to offer to number four for not swallowing. She put herself on display for all to see that she was starkers. One of the hens called out all she could see was an unkempt bush. How about offering the cuttings from a good trim as the additional payment? There was a deep intake of breath. The lead bridesmaid asked if the bloke would accept this offer; which he happily did. The bride looked panicked now but the hens cackled away. 'Don't worry. All we will do is make sure you are presentable to your husband. It's the least we can do!' She looked rather confused as two hens gently set her down on the table top, spread her legs wide, and tied them in place. Another two did the same with her hands. A fifth tied her at the waist. Someone turned up with a can of foam and razors. I was amazed that three or four women could work in such a small area. It wasn't long before she was as clean as the day she was born. The final bloke started to position himself when I heard: 'What happens this time if she doesn't swallow?'

'Good question,' replied the lead bridesmaid. 'Any ideas?' I heard myself say 'What about the dildo? Put it in her. If she doesn't swallow then she can give that away.'

'Good start,' I heard. 'What about swapping it around: She puts it on. If she swallows, off it comes. If not, the last bloke gets the key and the bride will have to negotiate its return!' Because the bride was tied down we couldn't see her expression. I can't imagine it was a smile! I was sorry I had said anything. Her waist was untied so they could strap on the double dildo. The bride was squirming and protesting. The bridesmaids, though were smiling broadly. We all heard the lock snap and the bride went quiet. They released her hands so that the bloke could position himself om front for her mouth. Off she started. This time this time she succeeded. We could all see the relief on her face as the bloke stepped away."

"Relief! She was probably savouring the taste," I pipped in.

"And how much cum have you ever swallowed?" Caroline scowled at me.

"More than you have if you don't think she was pleased," I countered.

"Well after this, I decided to call it a night. I suggested the others do the same but they wanted to keep going. I got up this morning, had breakfast and went for a swim in the pool but none of them had come down. I was worried they may still be going on somewhere. I decided I had enough and headed home."

We all agreed that was quite the hen night! But I wanted to take advantage of this to extol the joys of giving a blow job. I had no idea if what I was saying was true. I just wanted to convince Caroline to try it. "That bride will have a night to really remember. If she wasn't already she is now an expert cock-sucker." Caroline frowned. "That's only a derisive term to those who don't know how much fun it is. Unless she has a very open marriage, that will be the last time she has such choice for chances to enjoy cock sucking."

"One would be enough for me," exclaimed Caroline. "What would you say about that Grace?"

Before Grace could reply I jumped in. I know the number of boyfriends she had had so knew I wasn't too far off the mark when I said it. "I'm sure Grace will agree variety is the spice of life, or at least in penis's. Some are definitely more fun than others but all provide a wonderful toy. Sure the bloke gets the orgasm but the woman sets the pace. No "slam, bang, thank you ma'ma." Rather we get to play how we want." Caroline was softening a bit. "I've not done lots but have no hesitation in saying how wonderfully enjoyable it can be to have a cock grow in your mouth, tickle a set of balls and feel the muscles as cum flows out. And for real experts, you can make a man eat out of your hand, or even pussy if you so desire, particularly if you swallow. The slower you go, the more you use your tongue on different parts of his equipment, engulf his manhood in varying degrees, essentially the more you tease, the weaker he becomes. I have no doubt your husband would be extremely appreciative!"

There was some giggling on their part. "Okay, if that's that case, then how about you give Matt a blow job right now?" My face must have dropped a mile. "I'm sure Grace wouldn't mind. And Matt, well he'd disrobe right now from what you've said!"

I looked to Grace for assistance. "Well, I would have thought that would be more appropriate for Grace to do," I mumbled.

Grace had an evil smile on her face and knew exactly the corner I had backed myself into. "I would agree fully with what Jasmine has just said, especially the variety. Matt's got a great cock that can be a joy to ply with. I'm happy for her to add to him experiences." She did at least help as she saw the panic in my face. "I am also happy for you to have a go as well."

Caroline shot quickly back. "Oh, I've never sucked cock and never thought much of women who do."