A Costume Affair Ch. 06

Previously, James was humiliated in front of his best friend and setup to give him blow jobs for the next three years by his wife, Caroline. As well as anything else the best friend's wife may want him to do. Caroline cornered James into agreeing to a night of "practice" blow jobs. She also forced him to ask two colleagues from work to the eventful night.

Caroline took me into the bedroom to be dressed up as a woman. Normally I would have been thankful for this. But with Mark having prior knowledge of who I was only increased the fear factor. She got me well prettified which helped to put me at ease. Caroline re-introduced me as Jasmine. Mark and Tim were dead impress by the transformation. Their

playing along helped to put me further at ease, though I was still on warry side. As guests arrived Caroline explained how Doubles Night was going to work. Being in costume gave me the freedom to help and take some enjoyment in the process. Caroline gave me the option of doing everything in the bedroom but I was happy to do things in the open, hoping it would speed up the process.

Caroline explained that she would give out number cards to everyone as they arrived. Once I had all of them, all would be offered a "second shot" for the night. The goal was for me to have no numbers.

Many of the guys I recognised from the first party as they presented themselves. They had presumably brought friends to make up the numbers. A few looked vaguely familiar but I couldn't place them. I was very glad Caroline had dressed me suitably. So off I started. It was a good thing that Caroline had given the cards. I lost count of the cocks and swallows. Some were an absolute delight to play with and I suspect this showed. Others were hard work and resulted in a cum full I could barely swallow. Tim and Mark stick in the memory, of course. I didn't know if I should do my best with Mark, just do an average job or make it as fast as I could. I opted for the last option hoping that he would not want any more after tonight. Tim, on the other hand, I was happy to give my all. I was thankful for his support so made an extra special effort. So I was surprised, but happy to oblige, when he asked me to stick a finger up his arse. I would have put my whole head up his hole if had asked. He had one cracker of an orgasm. It was an odd sensation to feel is sphincter muscles squeeze my fingers in unison with his ejaculation. He went away a very happy man.

There was an encouraging cheer as the last person left their number. The stack of 18 looked impressive. "Okay, you can start coming around for the second shot," I said. There were naturally no objections. It was a bit harder the second time getting them hard and to cum. Then I came up against the unexpected: Someone I couldn't get to cum. This was worrying. I did all the tricks I knew, though he was enjoying it I could not make him cum. Others were getting restless.

"Maybe you need a bit more rest. Would you like to come back after I have done a few more?"

"Sure no problem."

Then I heard Caroline pipe up, "But I think you give them a piece of your clothing for anyone you can't get to cum. You can only redeem it when you've been suck-susful" There was a round of laughter. "Make it a bit more interesting for the others who are having to wait for their turn." This was not sounding good. "Might give you a bit of an incentive to work harder."

Someone piped up that they were having to leave soon. Either I speeded up or he would have to miss his second.

Caroline was sure playing this for what it was worth. There was no time to argue so I had to agree. Off came a shoe. I continued on and seemed to be only having a 50% success rate. I wasn't keeping count but I had all too soon given away four pieces of clothing. The room had thinned a bit and the pile of numbers was getting smaller. I was down to just my dress. It would be coming off with the next "failure" I had. I would once again be utterly humiliated and shown to be a man. My heart was pounding away. I become wonderfully thrilled when warm cum entered my mouth. I even became pleased as it passed down my throat.

Mark and Tim came up. I think they were the last two. My heart pounded again but had to trust for the best. I did everything I could but there was no success. I was trying to figure out the best strategy for this. I was confident most of the people remaining knew I was a man. But some of the less familiar faces I wasn't sure. And naturally they seemed to be some of the ones I had failed at. I got up slowly and kept close to Mark. "Will you help me to keep this dress on, I beg of you. I'll do whatever you want after this. Just please help me."

"Actually, you'll already do whatever I want I'm sure. What you would do if this got out around the office?" He had an evil smile on his face.

"No, Mark, I really don't think you should do this. He's in such a deep hole throw him a lifeline for God's sake." I was so relieved to have Tim there.

"It seemed to me you really enjoyed his performance with you. Would you want that again?" Tim looked at him blankly. "And again?" Tim was melting. "And again?" A smile started to appear. "And as often as you want me to tell him to do it? Any way you want it done?"

"Is this what you mean by taking advantage of someone when they're down?" Mark nodded. "Then count me in!"

Mark had a grand smile on his face. My mouth dropped to my stomach. I couldn't think of what would be worse than this situation but I am sure he could. "Dear all. Our host has failed and will soon give me her dress. Only my colleague is left but she has nothing to give him should she fail. Nor does she have anything to give should she fail on those of us she has already failed on. So I'd like your approval of the following arrangement. I take her dress now and she moves onto my colleague Tim. We take a photo of the operation. If she is successful, then the photo is deleted. If not, then Tim gets the photo for him to redeem at the time of his choosing. For those of us who were missed the second time, the same applies."

"Can I at least keep my dress on," I pleaded. Various 'boos' and discouraging words followed.

Caroline was happy to go with the crowd and put the kibosh on that, with a broad grin. "If you want to keep your dress on we stop now but that means you will have failed. You've got to give six doubles." She had obviously had done the counting. I had to think fast. Was continuing worth avoiding six more months with Alek. And if Mark was the outlier I would only be in hock to him, which I already was. So I decided to press on. There were no objections.

I reached down and pulled my dress over my head. I had gotten used to the gasps and exclamations, but the humiliation was not lessened, particularly for those who I fleeting recognised. I should have anticipated it, but I failed on every single one. I guess not all blokes can muster enough oomph to enjoy twice in a night. I was distraught but there was nothing to do. Well, the six remaining had lots to do!! They got some great photos of my mouth wrapped around rock hard cocks with my own dick swinging away. It was bloody obvious who I was and what I was.

Caroline made the arrangements which simply heaped it on. "Here is his telephone number. You can just send him a text with the photo, date, time, dress and place when you want your redemption." One asked what was meant by "dress." "Women's or men's clothing without any clothing."

"No, that's not reasonable. I started the night dressed properly. My redemption should be as I started." I was all but begging.

"Yeah, I can go with that," said someone.

I was floored when Tim countered. "That's fine for you. But why restrict others the freedom to choose?"

"Well, let's not take too much advantage of the situation."

"He's lost a bet from my understanding. He shouldn't be deciding the rules," continued Tim. "My motto is to take advantage of the situation to the fullest."

"That's right," added Caroline. "It is up to the individual to decide how the redemption is done. Let's keep it simple."

"Are you sure about that, man?" One of them asked hesitantly. I nodded in defeat. "Well if that's the case..." The details were exchanged.

The four left leaving Mark and Tim behind. "That was brilliant. I've not had so much fun in a night. And so much to look forward to," exclaimed Mark. "And that was wonderfully set up. He fell for it completely."

"What do you mean?" I asked in horror.

"Well, I had a chance to talk to Caroline while you were busy about what was happening. She filled me in on the details. We devised a plan to wank off as many as we could while you were working on the second round. Very few men can produce cum three times in a couple of hours. We got to five of the six. Tim was a bonus as you had done such a good job on him."

"No, I won't do it. I want you to call them and get my photo back. This is simply not fair, reasonable, neighbourly, anything. How could you do this to a fellow man!" I had a mixture of fear and anger.

Tim looked a bit sheepish, but also with a big smile. "You give such a good blow job. And then sticking your fingers up my arse. On my command. Well that sealed it. I was happy to join Mark in taking advantage of a man when he is down if that is the advantage you get." I just stood in silence. "So, um, I think you best keep that mouth in good shape!"

With that they left very happy men. Caroline then started to rub it in more. "So, let's see, you were successful with 12 of the guys but failed 6. So that is four times 6 less 12 for Alex. That means you add another year to your debt!" I hadn't even thought of that. She went back to our bedroom with a huge smile on her face before I could say anything. I made up my mind then and there that I would contact Head Dick (I realised he had only given me his phone number) and Dan to set up one hell of party for Caroline. I set things up for a weekend I knew we had very little planned. That would give them loads of time to take advantage of her. It took a bit of doing to convince Dan and Doris that Caroline was up for 24hrs of unlimited sex. I told them that she had become enamoured by Head Dick and his friends. We had had a session of some sex but I could tell that she wanted more without me around. I said they didn't need to be present for it all. I just wanted to use their flat for the period. They eventually agreed much to my delight. The only downside was that Doris said this was the last time if I went forward with the night. I gathered they'd had enough fun and couldn't really ask any more from them. So I agreed. It was not hard to sign up Head Dick.

The day arrived and utter thrill was running through my veins. Caroline was, naturally, taken by surprise when the call came Saturday mid-morning. She left with nothing but apron on, and a frown, to my great pleasure.

After a bit there was a knock on the door. When I opened the door I could tell immediately that she was not best pleased. I was, though, as she was naked! She flounced on the couch, spread her legs wide and ordered me to clean her up. It became the happiest moment of this whole ordeal. There was the aroma of cum. I didn't know how many men contributed; but that wasn't the point. She was getting it but not the way she wanted. And that was enough for me.

She then went back down dressed a bit more demurely. A few hours later there was another knock on the door. She was no happier this time with cum dribbling down her thighs, and cum in her hair and a gage in her mouth. My face lit up. All she could was point at her cum filled cunt. I took that as an order to clean her up. I would usually object to licking out this much cum. Knowing how it got there and with her unable to say anything, though, meant I had no problems doing it.

She then scowled at me as she left for the bathroom. I could hear her showering. She soon came out dressed more formally. I had no idea what was to happen. But I suspect she didn't either!

Almost at midnight, came the third knock. There was a woman this time on the other side of the door. She asked a bit sheepishly if I could come down with some camera equipment. I think this was one of Caroline's work colleagues. I was naturally a bit surprised but happy to oblige. It looked like Head Dick was taking full advantage of the situation.

"Look," she started to explain, "I know Reece said that Caroline was a bit of a swinger and wanted to have us over for a special night cap. He gave me sufficient hints that anyone I brought from work should be prepared for Caroline being a bit risqué. But many of us are surprised at how, well, extremely risqué the night cap is becoming." This piqued my interest. "There had obviously been some people over for a dinner to get the night going. And she was,,, well, more her clothes were, ummh, gone. I mean right from the start. That was far beyond what any of us expected. She was blinded folded, on her knees, arms and legs tied between two pieces of furniture. She was all there for all to see! You can imagine that we were stunned into silence. Reece motioned for us to be absolutely quiet. Then a bloke walked up to her and stuck his penis in her mouth. She worked on him for all she was worth. We let out a collective gasp. She stopped to call out: 'Yeah, must be quite a sight the first time you see it. You've all had a good dinner I'm sure. As I explained, now it's time for your night cap from the MAC T-Bar (that's Mouth, Arse, Cunt and Tits-bar for those first timers!) before you head home.'" The woman in front of me laughed at that last bit. "One of my colleagues asked the bloke who was now standing next to Caroline (so Caroline couldn't hear him) if she was really sure about this night cap thing. We couldn't believe that this is the type of night cap she had in mind. The bloke standing behind her gave her a nudge. 'As this is a MAC T-bar I can't see or hear so you need to ask the bar tender for the service you want to cap off the night. As I said and you saw after dinner, I've given him full ownership of the bar and he says what's on offer. I've told him to arrange the bar (i.e. me for those who are still a bit unsure) so that it can offer whatever you want at your pleasure (i.e. tie me up like this so I had no control or knowledge of what you wanted to do to me). Don't hold back. I've given myself over to any visitors of the bar to do what they want. The bar's open for your pleasure!' And with that she opened her mouth and spread her legs as best she could. Well we certainly didn't need any more convincing! One of the blokes asked the bar tender if we could have a few photos. He actually offered to film the night. All we had to do was ask you. He said you were her husband. Caroline can't hear or see a thing. I can't believe..."

I cut her off I was so excited. I had no idea what they did to get Caroline to say that or be so willing to give herself over. But I certainly wasn't going to object.

"Yes, I'm her husband. Caroline may be prim and proper at the office but she's been pushing our sexual boundaries for a while now. I am quite shocked she wants to include her work colleagues. But I'm more than happy to act as cameraman."

"You really sure about this? I mean, filming your wife so her office colleagues have a record of her getting, getting..."

I could tell she was still a bit bashful but starting to get caught up in the excitement. "Oh, yes. I'm really sure," I smiled broadly. After all, I was only doing what Caroline had set Mark up to do to me. I told the woman to wait just a minute while I got my camera.

As we entered I had the view of my life. After all she had put me through this was nirvana. There was a mixed crowed of about a dozen around her, including Mark. There was a bloke sticking up it her arse, another in her cunt and a third in her mouth. When they saw me they slowed down and motioned me to set up my camera. Once done, they restarted with gusto. The women seemed to be holding back while the men were getting on with it. Once the woman explained that I was her husband some of them relaxed. One smiled with a mischievous grin, "Can I, um, you know.."

Having been pre-warned I cut her off, "The bar tender is in charge tonight. I'm just the camera man."

The Head Dick smiled. "It might help to remember this a MAC T-bar. It will provide a service from any part of her body you want."

She looked at the other women. "I've never seen a woman shaved and it's so erotic."

As the blokes finished her off, the Head Dick asked if she wanted a drink from the Cunt. She looked a bit surprised by this.

One of the other women came forward. "I've always wanted to do this." Without a thought she sat herself down on the floor and started to tongue away. She obviously didn't mind the cum. It wasn't long before Caroline was having an orgasm. The woman squealed. Another took off her dress and walked up to Caroline. I could tell Caroline wasn't expecting a woman. I found out later that she assumed it was Doris. However, when her tongue encountered hair she knew something was up. But things were far too gone for her to do anything. She just soldiered on. And the woman was obviously pleased.

The hesitant woman came to ask if the bar tender had a cucumber. He looked a bit surprised and went to the kitchen as another bloke put his dick Caroline's cunt. He came back with a nice, long, fat cucumber.

"Sorry, mate, are you finished at the bar," asked the hesitant woman. "I've got something for her as well." The bloke finished himself off inside Caroline and stepped back.

To our surprise, Ms Hesitant stuck the cucumber into Caroline's cunt! She started to use it to give Caroline pleasure. You could see Caroline getting more and more excited. Then the woman slowed down. "Oh, you needn't stop. That was lovely," moaned Caroline.

The woman started again then stopped as Caroline smiled. This happened a couple of times and you could see Caroline getting closer to climax each time. "Oh, you're the tease. I guess you want your night cap to be begging for you bring me off?" The woman twirled the cucumber.

"I'll take that as a yes," purred Caroline. "You are a crafty one. So can you put what you are using into my mouth first? I can tell it's not a man's cock." The woman brought it to Caroline's mouth. She started to suck it like a dick. "Um, cum a la cucumber. One of my favourites. Will you please put it back into my cunt and scoop out all the cum you can?" A cheer went up and the woman happily obliged. This once again brought Caroline to the edge before being taken out.

"Please will you let me bite it? I love mixing the cum with the refreshing taste of cucumber." The woman held it so that Caroline could do this. "If I shape it into more of a penis shape will you then finish me off? You seem to know who to pleasure a woman."

The woman allowed Caroline to do this. In it went and Caroline's face brightened. But again, the woman stopped as Caroline was getting close. "Oh god, no please don't stop. I'll promise to invite you back for a night cap every day of the week." The woman just twirled the cucumber.

"Oh god, don't be so cruel. Haven't I fulfilled your night cap?" More twirling. "Are you saying it is my choice? We stop now with me hanging or I..." There was a pause. "Or I beg even more to show you how much I lust after this fucking?"

This time the woman restarted the fucking. For someone who started out very hesitant, Ms Hesitant was really going for it. "Okay, okay. My Cunt is throwing away all of my reasoning. After all the others have left, the bar tender can take pictures or film me doing anything you want. You can keep the pictures to make me do anything you want. I'll become your whore to fuck or be fucked any way you want. I'll give you not only my cunt but my entire body to you for just one fuck from you tonight. Only a sex obsessed whore would give herself to an unknown stranger so this should to show you how much I've got to have it." With that the woman finished her off. Caroline's face showed she got the fucking she wanted.