The first Sunday after my introduction to cuckolding, we took a break. Our children and their families were over, and we spent the day as we had the Sunday prior. It was a full day of fun for everyone, lots of food, games, and a little alcohol. Prior to their arrival, I made sure all of our new life had been put away. After they had all left, we cleaned things up a bit, and Nancy brought back our new life.
“Harriet,” Nancy began, as she stood by the backdoor. “Once you've finished putting those away, get that leftover bottle of wine from Peter's visit, and join me in the backyard.”
“Yes, ma'am,” I replied, a little surprised as I was not dressed as her.
“No curtsey?' She joked.
“Sorry,” I replied and gave her a curtsey.
She giggled and went out the door. A few minutes later I joined her.
“I think we pulled off today just fine,” Nancy began as I handed her a glass of wine.
“I never expected anything less with you running the show,” I stated, then quickly added, “ma'am.”
“Sit down,” she said with a chuckle.
“Yes, ma'am.”
The dark canopy of the night was broken only by the small garden lights that ran beside where we sat relaxing.
“So, is this how we're going to do things?” Nancy rhetorically asked after a sip of her wine.
“If it pleases you, I'm happy with it.”
“But how do you feel about it?”
Her tone told me that she wanted a straight answer. She wanted to know exactly how I felt and what I wanted.
“Promise not to get upset?” I asked.
“Depends,” she replied. “You say you want me to start pole dancing, you're gonna wear this wine.”
“Well then, thank God I'm not gonna wear wine,” I laughed. “To be honest, I think it's gonna make life a lot of fun.”
“Life wasn't fun before?”
“Yes, but just in more ways,” I quickly added. “I mean, that it'll be more fun, I mean a-”
“I know what you mean,” she said, interrupting my stammer. “I glad you said that.”
“You are?” I answered as I almost choked on my wine.
“I didn't want to sound like a whore, or make you feel inferior, but I really enjoyed myself.”
My heart skipped a beat as a smile came to my face.
“I really and truly enjoyed myself. All four of you.”
“Four?” I questioned.
“Peter, Dan, Greg and you,” she said, as she tapped my leg with her index finger.
Our eyes locked and we smiled at one another.
“So long as you are next to me when all the games are over, anything you want to do will be fine with me,” I stated. I couldn't explain it, I still can't, but the idea of her having sex with other people excited me. The idea that I was a sub, a cuckold, and helpless to do anything excited me.
“I love you,” she said as she raised her glass.
“And I, you,” I replied.
We clicked glasses finished our wine and went to bed. I knew a little bit of age was beginning to get to me, for we again made love, but it was just a little bit of an effort to perform. Keeping a picture in my mind of her with the other men helped to keep me rigid, and the extended time made her happy. After we cleaned each other up, we put on matching nightgowns and slept entwined in each other's arms.
Monday
“Prior to all of this I did a lot of online reading, and if it's okay with you, I want to begin making some changes.”
That was how Nancy began our breakfast conversation that Monday morning.
“What sort of changes?” Talk about your scared excitement.
“For starter, I want to bring out the Harriet in you,” she said, a big smile on her immaculate face.
“The Harriet in me?” I echoed.
“There are several different ways to be a cuckold, and I figure that since you have such a strong feminine side that it'd be best to-”
“Feminized me?”
“Well, yes,” she finally replied after a pause.
My heart began to race with that mixture of fear and excitement.
“Come on,” she began after she'd read my face. “You're probably the only guy who'd come home from fishing and put on a dress before cleaning his catch.”
“What about the time I came home and put on lipstick after I'd bagged Bambi?”
“Do you always have to say 'bagged Bambi'? I like that cartoon,” she countered.
“Sorry, I see your point,” I went on. “I do love to be dressed.”
“So tonight, stop for a couple of bees, and when you get home, leave the car in the driveway, go around to the side door of the garage, and come in there.”
“And what should I be looking for?”
“You'll find out then,” she quipped, as she gave me a peck on my forehead.
----
All day, my mind milled over what it was she might have planned. My biggest concern that morning was seeing Greg. How does someone act after what we had done? Do you ignore the person or just the subject? I was very nervous as I got to work. When I encountered him, our passing left me relieved and confused. He simply spoke my name and nodded as we passed, just as he had done so often. Not a wink or a knowing smile from him, nothing but that same greeting.
My thoughts were a mass of confusion, That's it? I thought. Two days ago you were banging my wife. She sucked your dick. I sucked your dick. I almost fucked your wife, and that's it? A nod? In was, without a doubt, a great relief.
The day was no different than any before it. As my mind went over everything I came to realize that this new lifestyle had many facets, and in a work environment this was the civil facet. Simply put, we know but it isn't anyone else s business. Our lives and pleasures belong to us, and no one else.
After work, I stopped for a couple of beers, which turned into three, but I was still home before six-thirty.
----
When I got home I parked my car beside hers in the driveway. Whatever she had planned, she was using the entire garage. As she had instructed that morning, I entered the garage through the side door, and could immediately see that she had put a lot of work into her plan for my feminization. Using sheets and cardboard, she had partitioned off the garage into a pathway that I had to follow. Upon closing the door, I looked at what she had written on a sign she hung there telling me what to do first.
“Stripe,” I said aloud, puzzled.
After a moment I chuckled as I thought the alcohol must have a grip on me. She had written, “Strip.”
As the excitement began to build in me I took off my clothes. Even the cold concrete did not deter my erection. As I got undressed I an arrow on the floor pointing to my left, and I was naked I started to go in that direction when I saw a sign telling me to go back to the corner. I turned around and went back to the wash area. At the sink was a sign that said, "Douche." I adjusted the water and once I got the water to a comfortable temp, I shoved the hose up my butt and flushed myself out.
There wasn't much, as we had cleaned me out just two days prior. Here again, I stayed erect as I enjoyed the pleasure of the enema and the excitement of the unknown that awaited me. After I quit dribbling, I dried off, open the envelope and read her next instructions. They simply said, “Turn around and follow my arrows.”
My mind was filled with thoughts of sex as I walked a slightly zigzag path. As I turned a corner to my right, I found a mirror and lipstick on the floor. The instructions said, “Kneel, apply, then follow the arrow.” Nancy, always concerned for my well being, had a folded towel for me to kneel on while I did my lips. My hand shook while I applied the bright red paste, but I got it on, blotted and moved on.
At the next stop, I was told to jack-off in my coffee cup, and when done to keep the cup with me. I took myself in hand and did as instructed. As I went about the matter, it dawned on me that I would not be having sex tonight. As I stroked and thought I smiled as I had to remember that I was being femmed, and cuckolded. I soon shot my wad, cleaned off, and moved on.
At the next turn was a chair with a lubed dildo attached to the seat. On it was a bottle of nail polish. My toes were still done form the weekend so it was just a matter of doing my fingers. The instructions made me chuckle. It said, “Stuff your pussy and do your nails. While they dry you are to say over-and-over, in your female voice, 'My name is Harriet, and I am a cuckold.'”
I sat down, taking the dildo up my “pussy”, did my nails, turned the little fan on to dry them, and repeated the line. After a couple of minutes of saying it, I started to wonder if anyone could hear me outside the garage door. I began to speak a little softer as my nails dried. I was very happy. The dildo up my butt felt good, and my bright red nails made me smile. Again I was so thankful that life had given me such a fantastic wife.
After my nails had dried, and I cleaned myself off, I moved on to the next station where I again had to jack off into my cup. I was now certain that I wasn't getting any pussy that night. It also took me a little longer to cum and ended with me shooting a slightly smaller wad.
As I made my next turn I found a disposable enema and a sign telling me to douche. After cleaning up, I moved on to a slightly open area with several blankets spread on the floor. In the middle of the blankets was a dildo and a manual timer. On a sheet of paper next to this she had written, “Come fuck yourself.” In small print under that, she told me to set the timer for five minutes. I put the pillow under me to raise my butt, spit on the dildo, set the timer, and began fucking myself.
I have loved anal stimulation as far back as I can remember. The rectal thermometer was my first experience, which was followed by pencils, candles, screwdriver handles, I enjoyed them all. As I tingled I smiled and fucked myself. I thought about the first time I suggested to Nancy that we get a strap-on for her to use on me.
Initially, she was repulsed by the idea, but in time, agreed and found that she enjoyed the role reversal. Before I knew it, the five minutes had elapsed and the bell dinged. I pulled it out and stayed still while the but juices ran out of me. After a minute or so I wiped myself off and got back on my feet.
Going on I found another disposable enema, a clean towel and a sign telling me to douche. Once again I did as instructed.
After again cleaning up, I went on around to the left, where I saw a sign telling me, to go back and get my cup of cum. My wife knows me too well. I had left it back where I had douched. I went back, got it and continued on to another jack-off stop. She had included a vibrator to help, as I was really beyond doing much without some help.
A little further along I came to a tampon lying on the concrete floor. She had written on a card the one-word instruction “insert.” I took it out of its wrapper, squatted and inserted. I then stood back up and walked on.
The next stop really surprised me. There she had set up a posing station. A sign told me to, “stand pretty.” Tacked to the wall she had placed several pictures of women posing. I was to imitate those poses holding each for a count of 100. She had also placed a mirror so I could look at myself. My poses were silly looking, and I laughed at myself, but I also enjoyed the movements.
Once I had done the seven poses I moved on to another bit of instruction. This one told me to, “Walk to the door, and try and do it like a lady.”
I did my best to follow her instructions, and when I got to the door she was standing there waiting for me.
“I'm guessing that you really want all of this.”
I wasn't sure if she was asking or making a statement, but I quickly answered her with a, “yes ma'am,” accompanied with the obligatory curtsy.
“Are you sure?”
She looked beautiful standing there in that lavender gown holding a glass of wine. Excitement had surpassed my nervousness and I quickly answered in the affirmative.
“I have enjoyed the attention and sexual gratification of our adventure,” she said, as she paused to sip her wine. “I have also relished the power.”
“Ye,s ma'am.”
“Are you sure you really want to do this?” She again asked me.
My mind was a mix of worry and lust. I knew my loved me and would not do anything to destroy what he had, so I wasn't worried about what she might have planned. I also know that if thee changes meant that I could dress and act in a way that I was comfortable, and if it put sex at the forefront of our lives, then I could see nothing but happiness.
“I'm waiting for an answer,” she said.
“I want to make you happy,” I said.
“I am happy, but I don't want you to be hurt,” she countered.
As I thought about her words, she went on.
“But you have to remember that this began as your doing. So it is your decision,” her voice had a slightly nervous tone. “If you walk through this door, painted up as you are right now, things will change. If you have doubts on that table is a rag and nail polish remover, and things go back to what they were.”
On the table to my right was two rags and the remover.
“I'm very serious, so you had better be as well” she went on. “If you come through the door as you are, you will be, from now on, Harriet. At the very least, a cross-dresser, and just as much my cuckold. But more than that you will become a slave. A sex slave, or my precise, my girlish-cuckold-slave.”
There was a slight pause.
“I think I have my answer,” she laughed as she pointed to my erection. “Not very hard, but it says 'yes'.”
Once again I put the vibrator to my penis and worked with great effort to an orgasm. The result was the expected pulsations, but the product mere drops.
“So what's it going to be?” Nancy asked after I'd finished. “You going to clean yourself off and come in as Harry my husband, or come in as you are, and forever become Harriet my cuckold?”