The Settlement

Story Info
Husband caught cheating is sent to Relationship Rehab.
8.1k words
4.23
53.3k
60

Part 1 of the 2 part series

Updated 06/07/2023
Created 03/08/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

While my wife was away visiting her mother for a week I had a wild fling with Kate, the sexy new secretary at my office. A young tart about 22 yrs. old in tight skirts and spike heels. She drove me crazy and before I knew it we were doing it on my desk with our clothes mostly on. Then, at her place near the beach and then, on the beach at night. Wild times.

The Sunday night before my wife's return the next day, I decided to take Kate out to dinner. It was the last week of August and most all of our friends were on vacation so I didn't fear running into anyone my wife and I knew, and I sensed Kate was getting restless to go out.

As we entered the restaurant and were seated I noticed, off in the distance, a friend of my wife's and another woman exiting the restaurant. She didn't see or acknowledge me and I breathed a sigh of relief. It was that Jill Hitchcock woman who lives around the corner from us, a friend of my wife. She is a divorcee, not remarried, whom I never liked. Word on the street was that she turned lesbian after the divorce and has a bug about men.

Kate and I enjoyed a great meal and after-party at her place.

The next morning I awoke and went to work as usual. My wife, Sue, would arrive at 11 am and taxi in from the airport, so I wouldn't see her until that evening. It was a normal day at work except that Kate was especially sexy all morning but I tried to avert my gaze thinking about Sue's return.

It was late in the day, near 5pm when Kate told me she had been called by Tom Blake's secretary. Tom is the General Manager of our company. She was called to his office and was going down there. About 10 minutes later the phone rang. It was the Mr. Blake's secretary,

" Hello Darrell, can you come down here for a moment the boss wants to see you."

When I got there I said hi to the secretary and took a seat in the waiting room where a smart-looking business woman was already seated. tall, black hair, elegantly dressed in a tailored suit and heels, carrying a briefcase. We exchanged glances, smiled.

Suddenly the door to the boss' office opened and out came running Kate, in tears.

"I've been fired." She said as she ran out.

After a moment the secretary said that the boss would see me. That is when my old life ended and my new one began. He spoke.

"Darrell, you know our company's policy about fraternization with fellow-employees. It has come to my attention and the attention of others that you have been carrying an affair with the new secretary, Kate. We can't have this and, quite frankly, I'm surprised at your indiscretion. As much as we like you here, Darrell, I can't very well fire the secretary and let the supervisor stay on, so, regrettably I'm going to have to let you go too, Darrell."

I interrupted,

"Who are the others whose attention it came to?"

He replied,

"I don't want to make any of the employees uncomfortable but let's just say that even your wife asked me about it. I'm sure you understand the difficult situation you have put me in but my hands are tied. Please gather your affairs and vacate your office by close of business. My secretary has a check for 2 weeks pay as severance for you. Thanks and Good luck, Darrell."

I was dumbfounded as I slowly exited the office and returned to the waiting room. The smart-looking woman who had been waiting since my arrival stood up and looked at me and asked,

"Excuse me sir, are you Darrell Wood?"

When I said yes she said,

"I have this for you." and handed me a paper.

I saw it and read "Wood v. Wood an action for divorce..." I asked the woman who she was. She said her name was Joan Miller attorney at law, and that she represented my wife in a divorce action. I was knocked out.

"What's this all about? What's going on?"

Miss Miller replied,

"I was just retained today. You should speak to your wife. All she said to me was, "Start a divorce and take that s.o.b. for every penny he's got...By the way, call her on the phone because I have an order that you are not to enter that house."

I asked her if this could be worked out, have talk, a settlement, anything. She said she would discuss it with her client and get back to me.

I was fucked. I slept at the Holiday Inn.

Miss Miller called the next day and asked that I come to her office at 10 am. I asked if Sue would be there and she said,

"No, but she has given me detailed instructions as to her wishes and how to perhaps reach some agreement."

I was relieved a bit and told her I would be there. Relief is something I would not be getting much of anymore.

When I arrived at the offices of Cockburn & Miller the receptionist offered me a cup of coffee and shortly thereafter I was invited into Miss Miller's office. After exchanging pleasantries, she began talking.

"I had a long talk with your wife, Sue and I think we may be able to work something out but it won't be easy. In my many years of practice I have known many female clients in divorce cases and I have seen some pretty irate women but your wife is absolutely furious with you. She kept on talking about betrayal, treachery, and what a double-crossing sneak and liar you are. Not only did you betray her trust but were you so uncaring and arrogant to do so in your home town where you could be, and were, seen by people who know you two. Her shame and embarassment is probably even more devastating to her than your infidelity. She insists that you suffer punishment for your behavior so that it is never repeated and that you check in to rehab to change your ways. She doesn't even want to see or talk to you until that is completed. She also insists that all marital assets be placed in a trust and be administered under her control until she is satisfied that you have mended your ways. If you agree to these terms, I will be the settlement administrator and I will assure your compliance with the terms of the settlement until your responsibilities are completed."

I agreed, seeing no other alternative, and signed the document she handed me.

"Good, then," she said

"That concludes your business here with me for now. We may as well begin today since you are free and are no longer employed at your former job. I have contracted with a marriage counseling firm called Relationship Rehabilitation Associates and set up an appointment for you at 1p.m. today. So, go to your hotel, check out, and go there. You are booked for the one week course which will be paid for through the new trust fund. Don't be late. Ask for Ms. Ann Drist when you arrive at this address. I must caution you--you must comply with all the terms of this deal in all respects and pass the course. If for any reason you fail or do not cooperate, then the deal is rescinded and she will proceed with the divorce."

We shook hands and I left. I checked out of the hotel and went to the address that Miss Miller had given me.

Ms. Miller handed me their brochure and I went outside and hailed a taxi. While in the taxi I read over the brochure which was a one page card about 3 inches wide and six inches long with printing on only one side. It read:

Relationship Rehabilitation Associates.

Four Step Rehabilitation Program

Patient Edition

Step One--Orientation and Commitment to program. Patient is welcomed and given an overview of goals and steps to achievement. Patient is encouraged to adopt the goals and accept the commitment to the program.

Step Two--Sensitivity Training. The patient, through the use of all the senses, will learn to become more sensitive to daily life. By heightening his awareness of the sight, sound, smell, and feel of things around him, the patient will learn to be more diligent and caring about his own behavior and its effect on others.

Step Three--Discarding male pride and macho behaviors which can be hurtful to others and replacing those traits with the virtues of cooperation and humility. This step includes punishment for past transgressions which is tailored to the individual patient in consultation with the patient's sponsor.

Step Four--Teamwork. Team building. The responsibilities of a team member. Performing as a member of the team for the good of the team.

I groaned as I read it. It sounded like so many corporate training programs which I had attended over the years which had always bored me to tears. But in my situation with the settlement agreement, I decided to simply resign myself to this exercise and suck it up to get it over with.

When I arrived at the address it was a 2 story building with a Martial Arts academy on the ground floor. As I entered I could see through the plate glass window a class being conducted by a female instructor with 4 female and 2 male students. Nobody was in the reception area but shortly one of the men in the class came in.

"Hi, I'm Randy. You must be here to sign up for our new class."

I asked, "What class?"

Randy said, "Self Defense for Gay Men. I'm teaching it."

I replied,

"No, I'm not here for that and I am not gay. I am looking for Rehab Associates."

Randy said,

"Not gay. Well that certainly is a disappointment. Ms. Drist, our judo instructor also owns Rehab Associates which is on the second floor. You can go upstairs and wait and she will be there shortly."

About five minutes later Ms. Drist arrived still dressed in her Karate costume, and was accompanied by two of the women from the class, whose names were Bev and Kim.

"You must be Darrell Wood. I have spoken to your wife and to Ms. Miller and our program has been customized for you. As you know you must pass all phases of the course and I must certify to Ms. Miller that you have learned the lessons. Any failure on your part to follow instructions or to fail to cooperate will result in your expulsion from here and the settlement manager will be informed, and your divorce will proceed. We start of with a routine physical examination to be sure you are in good health, so remove your clothes and kneel here on the floor in front of me."

I was stunned by her candor and stood there agape snickering that she must be kidding me. Just then she leapt up in the air, spun around and delivered a strong karate lick to my midsection which knocked the wind out of me. Temporarily blacked-out I found myself crumpled on the floor looking up at Ms. Drist.

She said,

"Listen Darrell, when I tell you to do something, you do it or it could get very painful for you. Now take off your clothes and kneel here before I have to kick you again. If I do, the next klck will be in your balls."

I stripped and knelt. The two women checked my pulse, listened to my heart with a stethoscope, weighed me and measured my height.

Ms. Drist told Bev, "Measure his equipment, now."

Since I was naked and the room was very cold my cock had experienced some major shrinkage and Bev said,

"I can't Ms. Drist. It's so small. It doesn't measure up."

As the two women giggled, I said,

"It's so damn cold in here, you have taken my clothes away, and that's why it doesn't measure up."

Ms. Drist told Bev to go downstairs and see if there was anything in the Lost and Found that I could wear.

As she left, Ms. Drist added, "Tell Randy to come up here."

When Randy arrived, Ms Drist laughingly told him,

"Our friend Darrell here doesn't measure up. Why don't you see what you can do?"

With that, Randy put his hand on my cock and began to fondle it and my balls. I recoiled at this queer touching me. Soon I had an erection and Randy measured it.

"It's almost 8 inches, Ms Drist."

Ms Drist replied,"Thank you, Randy. Now go see what's taking Bev so long"

After Randy left the room, Ms Drist looked me in the eye and said, "Are you a homosexual?"

I indignantly replied, "No absolutely not."

She laughed and said, " Well, I find it curious that you didn't get hard when a beautiful woman like Bev measured you but you perked right up with Randy's touch."

Bev came back carrying a small bag.

"This bag was left in the Lost and Found but doesn't have much in it. Just a pink spandex sports bra and matching panty, an unopened package of No Nonsense ultra sheer pantyhose, and this pair of black pumps."

Ms. Drist responded,

"I guess that will have to do. Darrell is cold and we don't want him to suffer any more shrinkage embarrassment." "Darrell put these things on. Bev, help him so he doesn't rip the pantyhose or I'll be forced to hit him."

Once I was dressed in this ridiculous outfit, I was told to kneel again in front of Ms. Drist. She spoke as she looked down on me,

"In accordance with our brochure this is your orientation--You are down. I am up. Got it?"

I answered, "Yes."

"Do you accept your commitment to the program?"

Again I answered ,"Yes."

Ms Drist then turned to Bev and Kim and said,

"This concludes Step One. Take him to the training room and prepare him for Step Two."

Bev and Kim helped me out of the room as I was having some difficulty walking in high heels.

On the way to the training room Kim said to me,

"Don't worry, Darrell, you'll do fine. You can get used to walking in heels. I'll teach you. By the way, you have very nice legs for a guy. The heels make them even more shapely and your pantyhose really displays them very well."

Step Two Begins

Kim told me that for the first part of step 2 I would need to be blindfolded because they would be checking my sense of smell. After she covered my eyes she told me to tell her which of the next four smells I found to be the most pleasant. Then she held different things under my nose. The first was obviously gasoline. The second smelled like bleach or ammonia. The third was definitely onion. The last was some kind of cologne. I picked the last one as the most pleasant.

Then, Bev told me that I would remain blindfolded and she would test my sense of touch. The first substance I touched was coarse and scratchy, probably sandpaper I figured. The next was fabric which I thought was wool. The next three substances were all soft and smooth. Bev asked me which two of the five I would discard. I said the sandpaper and the wool. She asked which of the remaining three I liked best. It was hard to decide so I just chose the last one. Just then, someone walked in and Kim removed my blindfold. It was Randy. I was extremely embarrassed with him seeing me dressed in a bra and panties, pantyhose and high heels. He smiled and said,

"Nice legs, dude, and I really like your pumps."

Kim told Randy to shut up and not be a tease. Randy looked at me and handed me a glass of orange juice.

"Ms. Drist thought you might like a drink. It's healthy organic orange juice."

I thanked him and he left.

Ms. Drist entered and asked Kim and Bev how things were going. Kim said that we had completed the smell and touch tests and that I had found the perfume to be the most pleasant. Bev added,

"He chose the silk but had a hard time deciding. He also liked the satin fabric and the nylon."

Ms. Drist said, "OK ladies I think Darrell is ready for more sensitivity, now. Have you finished your orange juice, Darrell? I made it especially for you."

I was feeling a bit dizzy, probably since I hadn't eaten all day but I also felt very sleepy.

I woke up, I don't know how much later, in a dark bedroom. I couldn't see a thing and began stumbling around the room. I was naked. Upon hearing the noise, Bev and Kim entered the room and turned on the light switch. The room was pink with lace curtains and decorated in a very feminine style. There were even two beefcake posters of male models on the wall. Kim stood me in front of a mirror and I was completely shocked at what I saw. First my fingernails and toenails were painted red and my fingernails were long like a woman's. When I looked at my face I didn't recognize myself. I was wearing hoop earrings and my ears had been pierced. My hair had been cut. It was still medium short but the style was definitely not something a man would have. My eyebrows were thin and arched. I looked like a pansy. I knew that this would be a problem when I returned to my normal life. The pierced ears might not be noticed but the eyebrows...

Ms. Drist returned. She began

"Sit down Darrell. I will explain. You see, it is a well-known fact that women are far more sensitive than men are. Since this is an accelerated sensitivity training course I subscribe to the theory that by letting men get in touch with their feelings and their sensitive feminine side they become more gentle and caring. Therefore Kim and Bev will be feminizing you. You will wear the perfume you found pleasant. It is called 'Precious.' Your new outfit will be include all the fabrics you liked--satin, nylon, and silk. They will be grooming you. I suggest you relax and follow their instructions. None of this will kill you and, I assure you, the experience will make you a better person."

Ms. Drist then left the room saying she would return later to check up on me.

Kim and Bev had me lie down on the bed and proceeded to give me a massage which was very enjoyable. Then, they rubbed some cream all over my body. They told me to get in the shower and rinse before they would continue. When I emerged and dried off. Bev dusted me all over with some talcum powder and Kim sprayed me with some "Precious," the smell of which I recognized. The perfume stung a bit and that's when I noticed that I had no more hair on my chest, legs, or armpits. Even my genital area was smooth and hairless.

First Kim said,

"Ms. Drist really admired your legs. They are nicer than most women's. She wants you to wear stockings with a garter belt instead of the cheap pantyhose that you are used to. I will put this one on your left leg. Watch how I do it because you will put the other one on your right leg. Be careful. They are very expensive and 100% nylon. Take care with your nails because they are longer since your manicure. If you ruin these nylons Ms. Drist will spank you."

Once I had carefully put on the stockings Bev helped me with the garterbelt. and showed me the matching satin bra and panties that made up the set. Kim said,

"Don't those nylons feel fabulous on your smooth legs, Darrell? How does the satin feel on you cock and balls? Feeling sensitive yet?"

I was ashamed in front of the two women because my shrinkage problem had disappeared. My dick was hard as a rock...and they noticed. Next, they told me to slip into a very sexy little black dress and zipped me up. They seated me at a table and Bev began to apply some purple eyeshadow , black eyeliner and mascara to my eyes. A finishing touch of blush and lipstick and Kim brought me a pair of 5 inch black stiletto heels to put on. When I looked in the mirror I couldn't believe my eyes. I looked like a woman...a very sexy hottie.

About that time Ms. Drist returned.

"My my" she exclaimed, "what a pretty little princess we have here! She is totally passable, not at all like a man in drag. I like the look. Nice work, girls."

She looked at me and said,

"Now stand up Darrell, let's have a good look at you. Walk over here, twirl and return."

I did as instructed, taking care with every step not to stumble. She kept commenting,

"Those legs look great with sheer black nylons. Don't they feel nice when you walk or cross your legs, Darrell? Girls, we can't keep calling her Darrell now that she looks so girly. What shall we name our new doll?"

Kim said, "Darrell certainly doesn't look like a Darrell. He looks absolutely darling."

Bev suggested calling me "Darling Darrell."

Ms. Drist decided,

"No, let's call her Darlene. It's similar to Darrell and she will remember why she is here. My only two suggestions for improvement--give her some shiny lip gloss on that lipstick. I love the wet look on those pouty lips of hers. Also, Bev, have her work out on the treadmill, slow speed, until she learns to walk in heels. Then, continue with her sissification and comportment."