A Costume Affair
Reluctance/nonconsent Story

A Costume Affair

by Steppingout58 20 min read 4.4 (3,800 views)
blow job cross dressing domination submissive swallowing neighbours office sex
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Previously, Caroline had created Jasmine from her husband James. She humiliated her husband by exposing him as a man while he was sucking the cock of his best friend. She further humiliated him by making him give blow jobs to his work colleagues. James then got his own back by having Caroline's work colleagues use her for their orgy. Paybacks between them continue.

The next morning nothing was said about what I had set up. It was as if Caroline had simply gotten drunk last night and didn't want to talk about it. I was happy with that. She brightened when I got a text. It simply said that Jasmine should come to the address given at the appointed time. My heart sank as this was right in the middle of the day. I had to go to work and started to panic.

Caroline just smiled. "I'll pack your athletic bag with what you need to make a fast change into Jasmine. Hopefully you'll have time to change back before work. And if you don't..." An evil smile appeared, "...you can go to work as Jasmine!" That was no big help. The attached picture, though, made that about the only viable option.

So off to work I went with heart pounding. Somehow I managed to actually get things accomplished. I shot off to the toilets on the floor above to do the fast change. The makeup and wig were on top. I was relieved to find a nice, reserved dress and the necessary accessories. I put on everything best I could and headed out the door. What a strange experience it was to be walking as a woman in my builduing. I could tell men were appreciative as well. I got to the appointed place, recognised the person and went over to him. I was relieved that all he wanted was a blow job. I happily complied. He deleted the photo to my great relief. One down and three to go. Back to work I went and back into my comfortable clothing.

When I got home, I was surprised to see Alek and Ginny. I guess they had decided they needed servicing as well. Naturally I said nothing. I was hoping that Caroline would allow me some slack and not require me to up the ante, so to speak. I nodded at them trying to confirm if I could speak.

"You are doing well and are following our instructions by not speaking to us. That's good."

I could tell from Caroline's face that this was not going to be the case. "I think James does have something to say."

"I want your cock so much I'm going for more months." I trailed off to let them do the maths that I was now at 48 months.

Alek didn't object in the least. He just looked at Caroline who then knew she had to disrobe if she wanted to stay. Off came her clothes. Alek set himself up on the couch and I did the business. As they went to leave, Ginny extended a line of hope to me: "I don't think real woman shave their pubic hair. So, if you want to continue to be part of the repayment plan, Caroline, you must grow back your pubic hair." Caroline's face fell as they left.

Well, that was an unexpected bargain. I knew not to ask what Caroline's decision would be. I now had a reason to look forward to the next visit. After they left, Caroline pumped me for information about my day and appointment. She was very pleased by my report. The next few weeks went back to the routine of blokes stopping by for a fuck & suck. However, Caroline was no longer inviting me in to clean out her box.

I received another text for an appointment early Saturday morning as Jasmine. I had mixed feelings as early morning Saturdays were never good but at least I was going as Jasmine. Caroline enjoyed getting me ready and off I went. I was floored when a woman in bathrobe opened the door. "Come in, I've been expecting you." I obeyed but was confused. The bloke appeared also in his bathrobe. "I thought you were kidding but it's true. You've arranged a maid for my birthday morning so we can play!" Shoot, if a bit of cleaning was all that I needed to do I'd be over the moon. They showed me the kitchen, which needed a good going over. They must have had some party last night. "We want coffee with a bit of toast in bed as well. Bring us coffee at 9:30 and we'll let you know what happens after that." So I got started and I can only imagine they got started on each other.

I found the coffee and all the fixings for breakfast as I was cleaning. As the clock struck 9:30 I knocked and took in the coffee. They looked well pleased. The bloke then said, "The maid is here to clean whatever you like." The woman looked a bit confused. "She's from the three C's agency."

"What in the world does that mean?" she asked.

"Citchens, cocks and cunts," he replied. The bloke looked at me and I knew I had to play along.

"All part of the 3C service, ma'm. Do you have a cunt that needs cleaning?"

She sat up with a broad grin. She kept herself covered so I had to crawl under the sheets. It was an odd situation but actually fairly enjoyable. There was plenty of cum but that was quickly out of the way. She made encouraging sounds so I just continued. Her orgasm was the indication that I had done a good job.

When I finished, I decided to ask, "And you sir? Do you have a cock that needs cleaning?" He nodded appreciatively. Down I went. But as at the party, there was nothing coming out. He was certainly enjoying my efforts but I gave up after a bit. "I think that should be it for the visit. Is there anything else you would like?"

"Well," the bloke said slyly, "have you met the terms of the agreement?"

"Oh, you can let her go. I've never had such a good birthday morning in my life." I was getting encouraged.

"She will stay and follow our instructions until the terms are met."

"Oh, what is that?"

The bloke looked at me again. With heart beating I got up the courage to say: "My contract is to obtain a load of cum from sir's cock for my payment. Failing that, I would naturally stay until successful and follow his instructions until then."

"Oh what a wonderful arrangement!" She exclaimed, and my heart fell.

"So," the bloke offered, "what do you say we inspect the kitchen. If it is clean enough, she can cook us a full breakfast to have in bed. If not, then she must give us a piece of clothing for every item missed."

"Oh, that's a bit cruel, isn't it? Getting oral sex is great but not sure you should make her naked while doing it." I could have kissed her!

"Okay, I'll let you decide." So off we all went to the kitchen. I was sure I would pass with flying colours, until she went to the oven. I was filthy on the inside. I simply had done what I could see and didn't think of opening it.

"Goodness, that is a pretty big omission," the woman said. "So I still want that cleaned. But," she smiled, "I wouldn't want you to ruin your clothes. So if you can rustle up some eggs and toast for us, a bit of jam and juice, you can come back in here to clean the oven..." I was relieved that is all she wanted. I was floored when she followed with "...in the nude. Wouldn't want your lovely clothes to get dirty," she purred.

"No, no, that's really not necessary." I was blushing.

"Oh, yes it is," she said with a wicked smile. "Put them all in here once you've served us." She handed me a case. "To keep them clean." She was having a grand time. "When you're finished cleaning, come get us. I'll have a look. If it is clean enough you can get your payment and have your clothes back." I blanched but had no choice.

I made the items they wanted, put them on trays and left them in the bedroom for them to enjoy. I then took off my clothes, put them neatly into the case and got to work. Being naked but with Jasmine's wig and make-up made me incredibly self-conscious. But I did my best. The appointed time came and to the bedroom I went. I had the case in front of me, knocked and held my breath. I prayed only the bloke would come out but knew better.

The look on her face was priceless. I just wish I hadn't paid the price. "She's a bloke!" Was the most intelligible thing to come out. I turned bright red, I'm sure. As she gathered her composure I could see her starting to think. "I don't need to see the oven. But I do need to see you give my husband a blow job!" She started giggling as I went down. "Oh this is absolutely precious." To work I went. If I was going to be humiliated, at least I would be efficient about it. I shouldn't have been too surprised that nothing came out. "It's all in here," as she pointed to her vagina. "And you know what you have to do." I crawled over on my knees and buried my head once again into her cum soaked pussy. Drinking out what should have been my freedom was crushing.

When I finished and gave her another orgasm, I begged. "Look, you have gotten the best of me. I can't offer you much more so why don't we call it quits. Surely, you've gotten the pleasure you want out of me."

The woman seemed sympathetic. The bloke, though, said, "Well, the deal is you are in my service until you empty my cum directly. So when you do you go!"

I did as commanded, much to the woman's surprise but pleasure. Needless to say, I got nothing out after several minutes. Well, I did get many comments out of her about my technique. "Never thought a bloke could give me lessons in how to pleasure a dick. Okay, my bestest husband, whatever "service" are you going to have my present provide?"

The smile on the blokes a face indicated I had quite the afternoon coming. "We have Jim and Emile coming over. How about having a catered lunch?" She was obviously happy about that. They gave me all the instructions about what to cook, how to serve and what was expected of me. To top it off, they gave me the skimpiest of maid's uniforms. The tights were so sheer, well they may not have even been tights, as you could clearly see my butt and cock. The one-piece top covered only from my breasts to just below the tip of my dick. She did give me back my falsies to push out my chest. It would be a real struggle to hide my true sex.

The appointed time came and Jim and Emile arrived. My heart beat throughout the lunch. Talk about being attentive! I only paid attention to what they wanted to ensure I was protected. The bloke and his wife made sure my butt was exposed as often as possible. After dessert, the bloke ordered, "Jasmine, Jim and I have been having an argument that we need you to solve. Will you give Jim here a blow job?"

I had been expecting this. Emily looked aghast. "There's no way you can ask a hired maid for the afternoon to do such a thing. That's so degrading."

Not wanting to do anything that would threaten my clothes I did my best to sooth her. "That is one of the specialities of our agency, ma'am. Chitchens, Cocks and Cunts. Really. Many would consider degrading. But it's all part of our service." I turned to Jim. "Would you like me to drop your trousers?"

Jim wasted no time in providing me access. I gave a long, loving service to him. As I felt him getting close, I decided to add to the experience. "Would sir like me to continue?" He looked a bit confused. "Would you like me to swallow?" I smiled at him.

"Oh, that's not necessary," he said a bit sheepishly.

"It is all the part of the service if you so please."

"Well, do you want to? I mean, sucking a man you don't know is one thing. Swallowing..."

"Oh don't worry about that, sir. To me a man's cum is as tasty as the cream I put in on top of your dessert. I love to the feel a man's muscles as they fill my mouth. I then enjoy the taste as it rests in my mouth and the silky warmth as it goes down my throat. My payment is seeing a smile on a man's face saying I have provided the ultimate in service."

The bloke had a smile and relief spread around my body. Jim approved and back I went. It wasn't long before I was filling my mouth. I gather from the amount of cum he hadn't had sex for a while. I did my first swallow and let him fill me up a second time. I clamped my lips around his softening dick so that I got every last bit of cum out of him. I then stood up and swallowed as slowly as I could. "I can tell from your smile that I have met your expectations?"

Jim agreed. "Yes, that will do and I will accept the bet. Jasmine could not possibly be a bloke. Any bloke who can do that must be, well, an emasculated cock sucking whore not worthy of the name." I looked confused and then my world collapsed.

The woman told me to turn around and take off my uniform. When all was off, I was to turn around. I could feel the blood drain from my body. But I had no choice. It was the most traumatic de-robing I had done. Jim and Emile gasped, clapped and exclaimed.

The bloke then ordered me to get on my knees so he could present his cock. Down I went to the amazement of Jim and Emile. I did as with Jim and finally cum came out. I was both relieved and broken. I stood up with my dignity is shreds once more but put on as brave a face as I could. "I think that is everything sir. Can I go now?"

"You are welcome to stay for any other activities we may want to do," the woman offered.

"No, as you are aware, I have provided the service I am here for. If you can give me my clothes I will leave."

As she got up, she said, "That's a shame. Jim here lost his bet. The payment was to swallow your cum if you swallowed his."

That just rubbed salt in the wound. But I had made my bed so I had to lie in it. I didn't want to take any chances of making it worse. The woman gave me back my clothes and I left as fast as I could. Caroline, needless to say, had a hoot as made me I recalled the visit.

She was even happier when Alex texted he wanted to see me first thing the next morning. Boy this was going to be a busy week.

Caroline naturally tagged along. When we got their both of us took off our clothes. The only solace was that her bush was growing back nicely. I kept absolutely quiet and did the business with Alex. The unexpected solace was that Ginny finished me off. I could see that Caroline was rather put out by this. She was even more put out when they told us we could go and she couldn't find her clothes. She looked confused but, as I was getting dressed, she finally had to ask: "My clothes?"

"Oh, you want them back?"

She started to lose her rag. "Of course I do! This wasn't part of the deal!"

"Oh, okay then. Happy to discuss it with you. But every word you use with us reduces James's debit. We are down to 36 months."

I could see the fury building in Caroline's face. Either she accepted they decided when to give her back her clothes or I get set free. Eventually, she nodded her agreement. I was relieved and Caroline was boiling, but quietly! I left for work fully clothed. Caroline didn't say what happened after I left.

A few days later, I received another text. The appointed time was a Sunday night at a pub. Caroline liked this as it gave her all day to doll me up. She spent a lot of time ensuring my arms and legs were hairless and smooth. I had mixed feelings that she was leaving my groin alone. I suspected this was to get me back for Ginny but it did make me look more normal. By the time she finished I looked gorgeous. She had upped my breasts and tightened the waist line. I looked a bit the tart but very tastefully so. I arrived at the pub and turned many of the heads as I went to the bar. This did wonders for my courage. I saw the bloke at a table and went over. We were joined by two others and had a delightful time over a rather expensive meal. I found it challenging but tantalising to be a woman at a man's dinner table. Naturally a few advances were made which I gently parried. It was in the back of my mind where this was going. I found out when the bill came. The bloke went to pay but made excuses that he didn't have any money.

He looked at what I assumed were his mates. "Looks like you are in a spot of bother. We are happy to help out if we get some help from your lovely lady." My heart was beating. Naturally I made an excuse as to not having any money.

"Well, there are other things a woman can offer than money," commented one of the mates. I was getting uncomfortable. "Possibly, some under the table payment." He had a big smile on his face. I could tell from the bloke's look what he expected next. I bucked up the courage to offer a blow job on the spot. I figured three swallows was pretty cheap fare. Naturally they agreed and down I went. It was all over fairly quickly and pleasantly. I was well pleased by the events. It hit home, if it were needed, that I didn't mind sucking cock as long as the recipients thought I was a woman. Being found out as a man was an entirely different kettle of fish. One of the blokes asked for my card in case I wanted another dinner. I gently declined as the bloke deleted the photo.

The next week, it was my turn to have a laugh. I had just gotten home from work when Alex and Ginny showed up unannounced. I naturally removed all of my clothing and made to get ready to service Alex. Caroline walked in as I was doing the business.

Ginny was quick off the mark. "Clothes please." Caroline hesitated. "I would like to see if you are becoming a woman again. Once you have, I will arrange for a more active part in our activities." Ginny had a sly smile on her face.

Caroline slowly complied. We were all surprised to see her bra and knacker-less. I had seen her put these on in the morning. I showed enough surprise that Ginny picked up on this. "That's a bit risqué, isn't?" Caroline looked quizzical. "Oh, you can answer direct questions without penalty."

"Yes, well, every now and again I go free, so to speak."

I looked at Ginny for permission to speak. She nodded her approval. "That's news to me. You left wearing them today," I was happy to offer.

"Oh, well, if you are lying then there is a penalty. Now tell us the truth."

This time there was a long pause. "One of my colleagues..." Her hesitation was saying volumes to me. "... asked for them." Ginny wasn't fully convinced.

"Someone just asked for your underwear and you willingly gave it to them. Do you really want me to believe that?" Her voice was heavy with sarcasm. "James, do you believe that?!"

I joyously replied NO. "Neither do I. Do you know people at her work that can verify her story?" I replied that I am sure I could find someone. "Caroline, you best tell the whole truth and nothing but the truth. Otherwise..."

Suddenly a dam burst. "When I came into work there was a note on my desk. It said the most odd thing: We are starting a game of Simon Says with you. Follow our instructions today and we will move on. Fail and there would be punishment. Your first instruction is to leave your knickers in a toilet cubicle by 1000. I thought nothing of it and threw it in the bin. When I came back from lunch, my screen saver floored me. It said I hadn't followed instructions. I would now be subject to their punishment. It said to leave my knickers and bra on the coat racket at the entrance to the toilets within 60 seconds or else the message would be sent around the office. Without thinking I rushed to the toilets. I sat there with heart beating deciding what I should do. Eventually I decided to play safe and took off my knickers and bra. I stuffed them in a pocket as I left the cubicle. As I washed my hands I prayed no one would come in. Looking in the mirror confirmed no one would notice my missing knickers but that I was swaying a bit. My heart sank but I had committed myself. Then a colleague came in. We smiled and my heart started racing. As she went in a cubicle, I quickly whipped them out of my pocket, hung them on the coat hook and left. I was on edge, though, fearful my colleague or someone would come in to the office showing them off.

"I watched everyone's face as I went back to the office. Acting natural was a trial. I could see some were rather puzzled but didn't seem to twig. Needless to say when someone came up close my heart raced. I was convinced the other person could hear it. It was terrifying being so close to humiliation. I couldn't bear it and had an important meeting coming up so went back an hour later to see if they were still there. They were so I decided to take them back and put the bra back on. I was relieved and had a successful meeting. When I got to my desk I went white: Simon didn't say to collect your belongings. I was to put them back immediately or the message would be sent around the office. I headed straight to the toilets, took off the bra and left it and the knickers on the coat hook. The rest of the day was torture. As I got ready to go home, the screen saver said Simon was pleased and said I should collect my bra and knickers to take them home. I was so relieved. As I entered the toilets two male colleagues were looking at my underwear. 'Bit surprising these. Wonder whose they are,' one commented. I tried to make light of it and said I didn't think they belonged to his mate! He chuckled and said they would more likely be mine. I blanched and immediately said no and that they were welcome to do with them as they pleased. With that I headed into the toilet. When I came out they were gone. I just headed home." The story she told was amazing. Surprise was written over our faces.

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