The Settlement Pt. 02

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Complying with the settlement Darlene becomes sissy maid.
3.1k words
4.48
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Part 2 of the 2 part series

Updated 06/07/2023
Created 03/08/2016
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I went to my room and sat down at the vanity to remove my make-up, remove my clothes, and hang them up in the closet. Saw a glimpse of myself standing in front of a full length mirror wearing bra, panties, garterbelt, stockings, and heels and began to realize my predicament. When I got to bed I spent the night lying awake, tossing and turning. It was dawn before I fell asleep.

The next thing I remember is waking up in a most delightful way. I was hard and aroused and cumming...cumming, as it were, into Sue's mouth. She made eye contact smiled and swallowed. She was already dressed in a most sexy way-fuzzy tight sweater dress dark hose, pumps.

"It's about time you woke up, sleepy-head. It's almost noon. Here, put on this peignoir and some shoes and come into the kitchen and have some coffee," she said.

I took the sheer nylon, boa-trimmed black peignoir and put on the only shoes I had, my high heeled pumps, and went into the kitchen, still astounded by the morning's events.

Sue said,

"I know you must be a bit confused. Drink your coffee and I'll explain. You must think that I agreed to take you back to be our sissy maid and occasional bitchboy for Tom. I'll admit that was my original idea but since I watched the video of your rehab with Ms. Ann Drist I think that you have much more potential. You could be a team member. You see, since I've been with Tom it has been a complete sexual reawakening for me. He is very experienced and kinky. He's a swinger and he and I have swung several times with other couples and I even did it with women which I also liked a lot. We have lots of playmates as a male and a female couple but if we were a male, female, and t girl trio we would have endless possibilities. Maybe you prefer to return to what's left of Darrell's life rather than to have fun as Darlene. I don't know. But I do have the video. Let's review it, shall we? I wont play the whole thing, just a few parts."

Sue slipped in the disc and forwarded the video to the part when I was being dressed by Bev and Kim. She stopped the tape and said,

"Do you see?" You're in a bra, garterbelt, stockings, heels, and panties. Look at the panties. See that dark spot? That is cum. Your pre-cum from being so excited dressed as you were. Also, the boner protruding from your panties tells me how much you were enjoying it ."

Sue, then advanced the video to the part when I was sucking Randy's cock.

"Do you see how lovely you look with a man's cock in your mouth? I think it's so cute. Notice your enthusiasm as you suck. How about that expression with cum all over your face. Priceless. Let's move forward. Here you are being fucked up the ass like a whore. Notice how you are wrapping your legs around him? How you chase his cock with your ass... that's hot, girl."

Then she advanced again to the part where I say, "I am a cock-sucking sissy faggot." She asked me,

"Shall I continue?"

"No," I replied. "What's your point?"

She answered,

"If you listen to me and do as I say, you can have an easy, nice, stay here. Tom is rich and buys me whatever I want and you too could have a gorgeous wardrobe and be treated like a princess if you play ball. Let's give it a try for a week and see then. If you still want to leave, you can. But I'd rather you stayed with us of your own free will because I know you would enjoy it."

"Sure," I said, "What's to lose? I don't have much choice anyway."

"Glad you could see it my way," she smiled.

Sue continued,

"You know, sweetie, it's indeed very curious, all of this. I found that when I was watching the video of your rehab with you all dressed up as a woman and dolled up in make-up, that I was getting aroused. You are quite attractive en femme and also very sexy. It got me excited in a strange and decadent way. You turned me on far more as Darlene than you ever did when you were Darrell pretending to be a man. I found myself getting moist and wet and couldn't resist coming into your room to suck your cock. Tom had already left for work and so he doesn't know about my idea of having you joining the team with us. As far as he's concerned you are here to be our sissy maid and bitch boy. So, don't say anything to him about it until I have had the chance to float the idea and convince him. Therefore you will be our sissy maid for a day or two until I have his agreement. OK?

I nodded yes.

Sue continued, "So, we have lots to do today. Go to the bathroom, shave real close, shower and then wash out the panties and nylons that you wore yesterday. I'll be in to check on you.

A little while later she came into the bathroom and said that I could hang up my nylons and panties on the towel bar. She handed me a package of pantyhose and said,

"You can wear these today. Also, put on your bra while I go get you something different to wear."

She returned with a jogging suit and sneakers, obviously Tom's, and said,

"You are going out with me as a guy today to do some shopping but I want you in a bra and pantyhose underneath to remind you of who is boss. Nobody will know what you're wearing except us."

She called a taxi which brought us to a little shop downtown called Pleasures. It was a fetish, sex shop with all kinds of toys and costumes. We were greeted by an attractive 40ish woman dressed smartly in business attire. Sue started the conversation,

"Hi, Gloria, this is my new maid, Darlene, and she needs a uniform."

Gloria replied,

"Oh we have lots of girly maid's uniforms for you to try."

Sue responded,

"I'm not looking for one of those ridiculous uniforms. We want something a little more modern. How about a simple straight, black pencil skirt, sheer white blouse, and white apron?"

Gloria answered,

"No problem. May I also suggest this sexy black, lace-trimmed bra. It will look so alluring worn underneath that sheer white blouse?"

Sue answered,

"That's perfect."

"Ooh, let's see those open-toed red pumps in Darlene's size."

Gloria brought them over for me to try on and said,

"Let me get him some knee-high hose to try them on with."

Sue interrupted her,

"No need to, Gloria, he is wearing pantyhose already."

I tried on the red pumps and they were fabulous.

Gloria asked, "Shall I wrap them up?"

Sue answered,

"No, but put them aside and perhaps we'll be back for them. If Darlene is a good sissy maid maybe I'll buy them for her as a reward next week."

We hailed a taxi and returned home.

That evening I was wearing my new uniform and after dinner Tom and Sue went into the living room while I was doing the dishes. Sue walked in while I was at the sink with my hands in the water and came up behind me and began caressing my ass. With my hands busy in the sink I just let her continue and soon she had lifted my skirt and put her hand inside my panties probing my boy pussy. Before I knew it she was fingering me from behind and said,

"I love to fingerfuck the maid."

Then she stopped and said,

"When you finish washing the dishes please come into the living room.

When I came into the living room the Sue and Tom were locked in an embrace. Sue was fondling Tom's cock which was now protruding from his trousers. Tom was feeling her breast. Sue looked up and said,

"Darlene, will you please bring us two glasses of Cognac?"

I turned and returned to the kitchen and prepared two glasses, put them on a tray and returned to the living room. Both were now naked on the couch and smiling. Tom spoke first,

"Thank you for the Cognac, Darlene. Would you mind doing me a favor? I'll be fucking Sue shortly but when I fuck a woman I like her to be aroused, hot and moist. Since I am drinking this cognac I hope you wouldn't mind getting Sue ready for me. I'd do it myself but I am so enjoying this Cognac that I'd like you to do the honors."

So, I knelt in front of Sue, put my head between her legs and began licking her pussy. After a short while Sue said,

"Thanks Darlene, I'm getting so hot. I think I'm ready for my fucking but before you go I need you to do me a favor. When a man fucks me I like him to be excited, enthusiastic, and very hard. Would you please suck on Tom's cock a bit while I finish my Cognac?"

So I knelt in front of Tom and began kissing, licking, and sucking his cock until it was hard as a rock. Sue provided commentary,

"Oh Darlene, you are so cute with Tom's cock in your mouth. You are sucking like a real pro, girl. Suck that cock. Mmmm you are really a hot little cocksucker now."

Sue interrupted me saying,

"I think that's enough, Darlene. Why don't you sit down in that chair and watch the way a real man fucks woman. I'd like you to masturbate while you watch so you don't get bored and so that you associate my pleasure with your own. You don't have to ask permission to come. Just come right in your pantyhose."

So, I sat there jerking off while watching my wife get fucked by the guy whose cock I had just sucked. Soon thereafter I came in my pantyhose.

When they were finished. Sue said,

"Such a good girl, Darlene! I just love seeing a sissy come in her panties. You had better go wash them now. We don't want any sissies prancing around here with cum-stained panties."

Tom added,

"Darlene, why don't you lick my cock a little, just for old times sake. You got Sue so wet that her juices are all over it. It may remind you of how her pussy tastes."

I licked it, and, yes, I remembered that taste.

It was a completely humiliating experience yet I found it extremely exciting. I pondered that for a moment before I realized that I had truly become a total sissy.

As I stood there at the bathroom sink intently focused on washing my pantyhose there was a knock and Sue entered. She had a big smile on her face as she looked me over. Then, suddenly she screamed,

"Look at yourself. Look in the mirror. Do you see that lipstick all over your face? Smeared! You are telling everyone what you have just been doing. Didn't they teach you that at the Relationship Rehabilitation? Girls always check their makeup after giving a blowjob. You look like a cheap slut! No maid of mine is going to walk around this house looking like a slut."

With that, she slapped my face and said, "Now fix that makeup. Right now." and left.

I was so startled that I immediately began fixing my makeup. A few minutes later there was another knock on the door. It was Tom. He seemed relaxed and said,

"I'm sorry Sue yelled at you. Just forget it. I stopped by to say that I was very impressed with your performance this evening and I know Sue was too, despite her anger. I want to let you know that Monday we are having guests-a swinger couple we know. They'll be here for dinner and playtime. I will ask Sue to have you serve and help entertain our guests. I know you'll do just fine."

The next morning Sue approached me after I had served them breakfast in bed. (One of my duties was to serve breakfast on a tray each morning. I must dress in a bra, sheer to the waist pantyhose and pumps...and nothing else. I asked Sue,

"Why no skirt or uniform?"

She only said,

"Because in the morning I like to see the penis I own.")

Sue told me that Monday night I would be attending the soiree as the maid...unless, of course, I decided to join the team. She explained that the maid's duties were to serve and obey and in general to fluff the swinging couples. On the other hand if I were the t girl in the swinging trio with Sue and Tom I would be able to choose partners, date freely, and be financially secure. She said,

"You will need to decide by Monday-maid, tgirl partner, or back to the life of the ruined Darrell. Up to you, Sugar."

The next morning Sue was up early and when I met her in the kitchen she began.

"About time you woke up. You have lots of work to do. Tom goes golfing on weekends with his friend Jack I am going to the beauty salon and when I return I want this house spotless. When you're done cleaning the house I want you to hand-launder my lingerie and stockings and change the color of the nail polish you're wearing. If there's one thing I can't stand it's seeing the maid with the same nail color two days in a row.Now get busy, sissy."

With that she left and began my assignments.

Sue returned around 2 p.m. with a new hairdo inspected my work and said,

"Get busy making lunch, princess. Tom and Jack will be home any minute."

As I prepared sandwiches, Sue continued.

"I love it when Tom and Jack play golf. They always come home relaxed and bring me a present.

Soon the men returned from golf. Sue introduced me to Jack who remarked to Tom.

"Nice maid you've got, naughty boy."

When they finished lunch and I was washing dishes, Sue, as is her habit came up behind me and began caressing my ass and said,

"Join us in the living room when you have finished the dishes. We'll have need of you."

When I entered the living room I was shocked to see both men naked sitting on the couch.

Sue said,

"Darlene, I want you to kneel here and fluff my men while I undress.".

As she removed her dress I knelt where directed and the two men stood in front of me. Tom slapped the left check of my face with his cock as Jack slapped my right cheek with his. I knew what was expected and began sucking. First Tom and then Jack alternatively as each grabbed my head. Sue was removing her bra and said,

"Darlene, that's enough for now. Step aside."

Sue got on the floor on all fours. Tom knelt in front of her and she began sucking his cock. Jack moved behind her and began fucking her doggie style. Sue was moaning. I was astonished standing there watching all this. When they were done, Sue smiled and said.

"I just love it when you guys play golf on the weekends. You always return so attentive to me."

On Sunday the men played golf again. They returned for lunch as they did the previous day. After lunch Sue took me aside and said,

"Darlene. I'll need you to help me out today. The men always expect some fun when they return from golf. Unfortunately I am having my period. So, today we are going to change the agenda. I will fluff the men and when they are good and hard you will take over. Dry those dishes and join us in the living room."

I did as I was told. When I arrived in the living room the men were standing in front of Sue who was sucking their cocks.

Sue told me to remove my skirt get down on all fours. Tom grabbed my head and inserted his cock into my mouth. Jack moved behind me.

Jack said,

"Tom, I hate pantyhose. You should buy your maid some stockings so she is more easily accessible."

With that remark, he ripped open my pantyhose and plunged his big dick into my tranny pussy. I was being double-teamed. Sue exclaimed,

"How memorable for Darlene. This is her first spit roast."

The two men continued fucking me at both ends until they came and I collapsed on the floor. I was in dreamland. I couldn't believe what just happened. I was both ashamed...and completely satisfied.

I didn't say anything but I really had enjoyed the experience. The look of contentment on my face didn't go unnoticed by Sue who stood there smiling down on me.

"Go get dressed and fix that make-up," was all she said.

The next day when I first saw Sue she got right to the point.

"Just remember that if you return to the life of the ruined Darrell with no job and no money and no prospects you won't be able to have panties or nylons or heels or any of the pretty things that I know you like so very much.

Sue started walking away and added,

"We're going out at 10 so get ready quickly. You can wear guy clothes if you want to pretend to be a man."

That last remark hit hard. I was speechless. In fact I was now sucking cock, getting fucked up the ass, and was a transvestite princess undeniably. She was right.

I began thinking.

"No real man would do what I am doing. I'm not a real man. But...I am a real t girl."

That's when I decided to forget the guy clothes and to put on my pantyhose and bra and my black pencil skirt and pumps.

Sue returned near my door and said,

"Let's go."

When I emerged all dressed pretty as a girl. Sue asked,

"Why so girly? I said you could dress in guy clothes."

I replied,

"I don't want to pretend to be a man. I'm a t girl...and I want to join the team."

Sue kissed me long, wet, and passionately.

I grabbed my purse and took out the mirror and checked my lipstick and said, "Shall we go?"

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GrrrreatImaginationGrrrreatImaginationabout 6 years ago
I really like this series.

I liked it all, verrrry much. The intro, the setup, the training/rehabilitation, the trial period living with Sue & Tom, and the eventual acceptance and embrace of his new persona.

There were times that I wondered about his thoughts & emotional reactions to what was being done to him, and especially about what he was doing. At the rehab, I used my own ideas, based upon what you'd told us -he was trying to salvage his marriage or his life. In Chapter 2 I really wanted to know, because the divorce was withdrawn. I love it when a writer reveals a character's inner struggle.

Thanks for sharing your imagination and storytelling. I hope you keep writing. I'm off to see if you have more!

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