A Costume Affair
Reluctance/nonconsent Story

A Costume Affair

by Steppingout58 19 min read 4.2 (3,600 views)
best friend blow job cross dressing degradation domination submissive swallowing
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Previously, James lost his bet with Caroline and is now completely beholden to her. He managed to also set himself up to be black mailed by three cab drivers.

The next morning, Caroline made sure I didn't see her naked cunt. She was happy to show off her tits and the rest of her body but not what I most wanted to see. Her only edict was that I would be naked from the waist down whenever I was in the flat. No one would notice from outside but I would always be reminded of who was in charge. I was also ordered not to challenge her in anyway, or discuss my predicament. People, well men from the party, stopped by occasionally for me to provide a "service." Caroline quite liked this as it kept me on my toes whenever the doorbell rang. A pattern was forming, much to my dislike and Caroline's obvious enjoyment. The blow jobs and swallowing never got easy.

Caroline and I were coming back in together one Saturday evening when a chink in the armour appeared. Dan is our neighbour, opened the door. Caroline had humiliated Dan's wife Doris. Dan helped Doris get her's back in spades. He said in a very commanding voice, "Please come in." Caroline's face told me she was not pleased with this.

"James, go on upstairs. I will join you in a bit." Her scowl told me to obey. An hour or so later she returned. When I asked what happened, she told me point blank it was none of my business and I was not to ever ask her about it again.

Well that got me to thinking. The next day I cornered Dan. He was cagey until I started talking about the story Caroline told me how she took advantage of Doris. Dan relented and said that Doris had made Caroline go into our flat to get something precious that they could force her to give them sex for the next six months, while Doris was pregnant. At first Dan was hesitant about this. But after his first blow job and Doris's obvious delight in having Caroline clean out her pussy had convinced him otherwise.

I didn't tell Dan the hold that Caroline had over me but I told him enough for him to entertain the idea of asking Doris to help me. When Doris came home, I had to work hard on convincing them to take more advantage of my wife's compromised position. Eventually I had to part fess-up. I told them that at a costume party Caroline had fixed a party game so that I had to remove everything except my mask. The only way to get my clothes back was to then give a bloke blow job. When I refused, she agreed that they could keep my costume so I was naked for the rest of the party. Though aghast, I could tell that wasn't enough for them. So I had to expand. "I had seen her whispering in the host's ear but didn't think anything of it. As we were leaving I expected to get my costume back. When I asked for my clothes, the host said, with a nod to Caroline: No blow job no clothes! Faced with no choice I had to go down. Fortunately, I pulled away before anything went into my mouth but they made me go home with cum on my face." That did it.

As a first step we agreed that they would invite a couple their friends over for a free blow job. This would help them feel comfortable in taking more control. Dan reported back a few days later that the mission was accomplished. Though Caroline was able to deal with Dan's output, she couldn't swallow everything from the other blokes. And they had a bit of laugh seeing Caroline's consternation. That was music to my ears.

I could now go to the second stage of my plan. I convinced them that I would invite as many of the blokes from my party as I could on the next Friday night. Dan would tell Caroline to come in. They would tell her she didn't have to remove any of her clothes. Then they could drop the bomb that she had to give a blow job to everyone in the room, and to swallow every last drop. Every time she failed to do this she would lose a piece of clothing. If that meant going home naked that's what it meant. I didn't have to be there, in fact probably wouldn't be allowed to. But I'd know from the state of her clothing what had happened.

The fateful night came. Caroline went in expecting the routine and, I knew, was in for the surprise of her life. Several hours later, there was a knock on the door. When I opened it I saw one pissed off wife! Unfortunately, she had the Welcome Matt wrapped around her body. She started to just about scream wanting to know why I had done such a thing to her. I told her it should be bleeding obvious! Also, by now she should have hair growing back, as I had. It was the only way I could think of to see if any hair was growing on her cunt. Boy, was that a mistake.

"So, you want to see my cunt?"

"Well, it's only fair. How else will I know when I am free from my pledge?"

"Okay, let me think about it."

"No, I have a right to see if I'm free of prancing around with no bottoms and sucking the occasional dick. I've got hair. So should you!"

"Okay, I'm far too mad now to do anything. I will show you my cunt tomorrow."

When I came home the next day the kitchen was full of food and drinks. There was a large sheet of paper on the table saying I was to get dressed in my best woman's clothing and be the hostess for the evening. She was having an inspection party but didn't say what was being inspected. That sounded a bit worrying but did as I was told. Soon after I finished, there was buzzer. A bloke said he had been invited to Caroline's party. I let him in. He was followed by several others. I served and made decent conversation with a group of men I didn't know and dreading that I may come to know them more intimately than I wanted.

The food and drinks were getting low and I was wondering what to do if Caroline didn't show soon. Fortunately, she arrived at this time in quite good spirits. "So Jasmine, before we start the inspection you want, it looks like we are at the dessert stage. Which would you prefer: that these lovely gentlemen fill up my cunt with their cream or that they fill your mouth directly?"

I was confused by the choice and couldn't figure out if this was a trap. I certainly didn't see how this fit in with an inspection of her cunt. Others in the room also appeared unsure of what was happening. She was laying it on pretty thick as to what she needed and could cope with. Things were moving too fast for me to know the best strategy. There were a goodly amount of men there so I decided to see if she really could take them all. Besides, cum in her cunt meant less cum in my mouth.

"It does sound exciting what you are proposing. But, I'm not sure you can take all these blokes as you're saying. I might have to finish them off for you. And that would be quite a let-down for them, I'm sure."

"Oh no, I wouldn't do that to them. I'm sure I can do it."

"Well if you are so sure, how about I tie you down so that you have no choice. If you call out UNCLE, then our previous agreement is off and you take responsibility for sucking and swallowing anyone you can't take in your cunt. If you take them all then our agreement stands and, as I expect you will want, I will dive into your cum filled cunt." There were some confused looks. Caroline was looking worried. This wasn't quite what she expected. "After all you are the one who has gotten all of these hunks excited about screwing you. I wouldn't want them to be the ones screwed!" She was realising that she had backer herself into a corner. There certainly weren't any objections from the blokes. Caroline had to comply.

So I happily went into the bedroom followed by the first few men. Caroline started to take off her clothes and I got some belts ready for her. She could tell I was going to be enjoying this far too much. "No, wait this night should be about what the guys want. So you can help tie me down but then I think you should leave the room. I'm sure they'd have more fun without another woman to make them inhibited. They can take off my clothes any way they want. I am absolutely sure I can then take them all on. UNCLE or no I want them to keep driving their pricks into my cunt. I'm happy to let the men decide when they've had enough."

That was a disappointment as I had planned to get things set up so that I had a free view of her, hopefully, hairy cunt. I was sure she was bluffing to make sure I couldn't do this. "Okay, well, let's get you tied up then." She laid herself on the bed allowing me to tie her up. I had a sudden brain wave and switched to her nylons. I had her first hand down before she could object or figure out what I was doing. I continued: "Okay guys I've made the knots just as tight as they can be. She won't be able to get herself free. In fact, I've made them so tight that we'll need scissors to free her. Us girls should stick together but if you don't want me to be part of this and want them to decide when they are satisfied, I guess we might as well give up all control. I'll leave you entirely in their hands. I won't bring in any scissors to free you until they tell me to."

I could tell I had gotten another one up on her. She was stunned into silence. "Okay guys, silence is her approval. And just to show that we are in agreement," I took out a pair of her knickers, "and to maintain silence," I stuffed them into her mouth. The look on her face was priceless. "You can remove her clothes anyway you want," and out I went out. The head dick motioned for most of the guests to leave with me. The moans and groans said someone was having a great time. Those with me had mixed looks of confusion, anticipation and embarrassment. A couple of guys came out with big smiles and motioned for others to go in. Eventually, one of the guys came out.

"Well everyone, a bit of a change of plan. As we can't free Caroline, I want Jasmine to come back in."

I naturally assented while he motioned for everyone else to follow us in.

They had done a good job. Her clothes had been ripped off so all her bits open to the world. I had never seen so much cum in one cunt, or in one place for that matter. The remains of the knickers she was wearing covered much of her soaking cunt. From what I could see it appeared she had hair growing back. I was relieved. I couldn't read Caroline's face but could tell from the nervousness of the others this wasn't going quite as planned. I was pleased as this meant Caroline wasn't in full control. Then one of the blokes started to explain the next step. "Caroline has mentioned that you have been dying to know if she has pubic hair or not. Is that really the case?"

I was a bit confused by this as the knickers were still in her mouth but I naturally agreed. "That's great. So we have a proposal for you then. We will clean up her cunt so you can have a good view of what she has to display." I nodded my appreciation of this. "But you have to suck us all off until we're good and hard." I was less pleased by this.

"So want everyone here to cum into my mouth just to see if she has a bare cunt?" I certainly didn't like the idea of this.

"No, no. Not that far. We want to have a bit more fun than just a straight, every day blow job." I had no idea if this was good or bad. "We will give you have five minutes to get cum out of us. If you can't do this, then it shows your blow jobs aren't very good. You'll need to make up for this by giving us a piece of what you are wearing." I started to object. "It's either cum or clothing; otherwise, nothing further happens and no viewing of a clean cunt. It is as simple as that."

"That's not very simple for me," I exclaimed. "You're asking an awful lot of me for fairly little in return."

"There is no requirement to do this. It all depends on how much you want to see Caroline clean."

"That's not fair. You're taking advantage of me."

"Yup. As you said: You have put us blokes in full control. We plan to take full advantage of the situation." From Caroline's look I could see they were doing just that.

"What, you're not happy with making me give you blow jobs. You want to strip me of my clothing as well!" I was close to pleading

"Well that will only happen if you give substandard blow jobs!"

"What's wrong with three minutes of sucking cock - cum or no cum? Surely that would be a suitable reward for revealing her cunt?" I was doing my best to get out of this. There were signs of shaking heads that this was not acceptable. "Okay, how about five minutes of me sucking you off? If I get cum I move on. If not, five minutes of loving would be a suitable treat!"

"You don't seem to get this. There is no bargaining, or at least not on your side! So now it is two minutes of sucking, not three." Some else said "Let's make her swallow."

"Good idea. If Jasmine complains again, we will add that to the requirements." There was nervous laughing and come clapping.

That was a spur to get me to accept the two minutes without any thought. Only having to get them to cum was much better than swallowing. And to be free of Caroline's hold over me would be worth sucking a room full of cocks. I didn't want anyone to up the stakes so I immediately agreed.

"Okay, as you said we've given you control. I submit." I'm sure they could tell from my face that swallowing was not on for me. So down I went and asked for the first bloke. I took him in my mouth and expected him to harden quickly and cum almost immediately. This is what had happened in the past. But he was staying steadfastly soft. I just kept tweaking his soft member in my mouth as I had always done but there was no response. Two minutes came too fast. Off came a shoe. Number two was the same. Off came the other shoe. I started to put some thought into it. I engulfed number three's member and then let it drop out of my mouth. I then used the tip of my tongue to outline is penis. I then went down to his balls. I was relieved when he became hard. From the experience I now had thanks to Caroline, I could tell he was getting ready. I was feeling relieved but didn't know what to do when he exploded. Fortunately, a glass appeared and I was able to catch his cum when he exploded. I felt relieved and moved onto number four. Relief came again as he came. I assumed number five would be the same but again nothing happened. Two minutes again went faster than I expected and off came my tights. I did this slowly to gather my thoughts.

"I think she's trying to waste time. Come on get on with it," someone piped up.

"Nothing was said about how long between cocks. I can take as long as I need." Boy was that a mistake.

"No, I say when time starts and stops. Your two minutes after the cum stops flowing starts or you give up on the cock."

"Wait that's..." But I didn't need to finish to realise I was on the losing end.

"You're wasting your two minutes."

I had gone too far to stop this close to my goal of seeing Caroline trussed up, naked and clean. So I quickly decided to treat every cock as though it needed my full attention. As I went down and indicated I understood. Number six, seven and eight were all a relief. Number nine, though, was real work. Again I went down his flaccid penis and tickled his balls. I flicked them around in my mouth and then back out to lick around the base of his shaft. I had to do this twice before achieving a hard dick. I moved to the purple helmet and circled that with my tongue. I could tell he was on the verge but time was called just as he filled the glass. I wanted to argue but knew the clock would be ticking. Off came the knickers as fast as I could. I could feel my manhood going free but had no time to get worried as number ten appeared in front of my face. I repeated what I had done before. Hardness was again achieved but that was it. Because it was taking so long to get them hard I little time to lick up and down his shaft and around his purple head. All to no avail. I was really beginning to wonder what was going on. I redoubled my efforts and had never been so loving to a cock in my life. There were approving groans when time was called.

I stood up and slowly undid my bra. Terror was now coursing through my veins. They were padded subtly to enhance what was stuck to my skin. I shuttered to think what would happen if they found out I was a bloke. "Sorry, guys. I'm going to have to call it quits at this. Here is my bra and the last piece of clothing I want to give up. I would love to do more but going naked is not on the cards, I'm afraid."

"Well if that's the case, then I guess that's the end of it. You won't know the state of her cunt. You were so close. There's only one of us left. And look he's almost got a full hard on!" There was some chuckling. They kept piling it on and it was starting to work on me. They were complimenting me on how good my blow jobs were and reminding me how close I was. Surely given the quality it was worth the risk for so much gain. The worst that would happen is that I would be naked for a bit. And that certainly wouldn't be so bad compared to the reward.

I was so sure that she is bare I started to think of what I could offer to entice them to let me lick her out. I also didn't want to spark any suspicions as to why I didn't want to be naked. "Look, instead of you cleaning her up, what do you say I do it? You guys can certainly watch. Surely that would be entertaining?" As they started to agree Caroline started to shake her head. They started to back off and this made me more determined.

"Okay, well I don't have much to offer you in the way of enticements. Is there anything you'd like?"

"Well, we wouldn't want to force you do anything," the seeming leader said. "But if you thought of something that we might like we would happily consider it." Caroline was starting to frown. I got the sense that this is not what she had planned. The leader was going off script, I suspect, so I redoubled my efforts on thinking what I could possibly offer.

"You guys obviously like to know you're in control." They nodded and I threw caution to the wind. "How about you tie me up like Caroline. If I find she has some hair while I'm cleaning her up, you free me and leave the scissors for me to deal with Caroline. If she doesn't have hair, then you can free her and do as you please with me for the night."

"Interesting. But either way we have control of just one of you. While we can't force you to do anything, you guys have given us control of Caroline. Why should we give that up to help you?" At this point Caroline was well livid. This was definitely not as planned. That only fuelled me to offer a few more ideas. Even I knew my suggestions were all limp; that I wasn't recognising the strength of their position. They wanted reassurance about not losing the advantage they had. I decided I had to push to the edge.

"Okay, I'll offer double or nothing. I will clean up Caroline. If she has hair, then the night is over for you but I can have all the fun I want with her. If she doesn't have hair, then you can tie me up. You will have scissors so can do as you please with both of us until you've had your fill."

There was a bit of silence. "And to show my willingness, you can tie up my feet and hands now so I can't go anywhere."

"And how will you get to her," asked someone with a smile.

Good thought that! I was too busy trying to get one up on Caroline to consider the details of what I was doing. "Well, I guess that's for me to figure out and you to enjoy while I do it." They happily agreed. My heart started beating faster as they tied my hands and feet as securely to the bed.

"Before you go to Caroline, you need to finish off Hank. Otherwise he would be left in the lurch."

What was one more cock. Down I went. He did quickly get heard and cum. They held the glass to catch his copious amounts of cum.

They then held the glass of cum in front of me. "Before we let you work on Caroline, drink this."

I'm sure all of the blood drained from my face. "Why? I don't understand. Surely you've gotten everything you want, and on a platter!"

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