This story is the long overdue second chapter to A Wife's First Date. I want to thank Ken Nitsua for his very helpful editing assistance. It provides the husband's experience at the beginning of his wife's adventure with another man.
"Just landed in Atlanta. I love you!"
My wife's text came though on my phone as I prepared to board my connecting flight to Palm Springs.
"I love you more! About to board."
We play out this loving ritual when we travel separately, which is often. I love it when she comes with me on my frequent convention trips, but she is busy running her own company. This weekend she is headed to St. Louis for a weekend honoring an old mentor of hers.
My wife is a stylish and polished executive with a soft, classy look. For all her business acumen, she still maintains a warm femininity, with an old money refinement. While our texts are a ritual in a long marriage they are sincere and heartfelt. We love each other deeply and are very compatible. Being married to her has been the highlight of my life for the past fifteen years.
Another text from her greeted me when I landed in California and turned on my phone.
"In St. Louis. I will call you later. Let me know when you land. Love you!"
I grabbed my bag and jumped in the rental car for the beautiful drive to Palm Springs. I called her once I hit the open road.
"Glad you caught me! Was about to jump in the shower."
"I'm on the road to Palm Springs. Beautiful here. How was your flight?"
"Long. I am going to get dressed and have a glass of wine in the bar before they pick me up for the reception."
"Great. Text you later before I leave for my reception. I'm not going to stay out too late."
"Have fun. Not sure what my schedule is tonight. I love you. Bye! By the way, I left you a few surprises in your suitcase."
She cut the call. Intrigued, I punched the phone to redial her, but it went to voice mail. She was teasing me.
As I increased my speed, I sensed the tingling in my loins intensifying into a full out buzz, the feeling of delicious desperation caused by more than two months of denial. My wife is particularly indulgent with her surprises and with my quirks, so in my heightened state I was beyond excited to see what she had packed for me.
I arrived at the hotel, threw my keys at the valet, rushed through checkout, and dragged my large roller bag to my room, nervous anticipation growing with every step.
Finally I was there. I slipped in and slammed the door shut behind me before throwing the suitcase on the bed and pulling the zipper open. There was a note from her on top.
Sorry I can't be with you, but I am looking forward to our girls' weekend in a few weeks. I looked in your suitcase, when you left it at the house, and it looked like it had been packed for a real man. Since we both know that is sadly not true, I have taken the liberty of repacking you so you can be the girl you really are. Oh, don't worry, I left you some boy clothes so you can pretend to be a man in public, but, in private and underneath, you are going to live as a girl, feminine and flirty. Here are the rules. Follow them to the letter.
1. The first rule should not be a problem, because you have no choice. I have removed all those ugly boxer shorts and replaced them with pretty panties, perfect for you. You will always wear them under your clothes.
2. In preparation for girls' weekend you must keep your body shaved smooth except for that cute little triangle above your clit. I packed your Venus razor to help you stay smooth and girly.
3. Your room will be a girl only zone, which again should be no problem since you are not a real man anyway. You will not spend more than five minutes in your room pretending to be a man. In the room, you will be fully dressed in panties, leg wear, shape wear, a dress, and heels, except when dressed for bed or for ballet. As you will see, I packed some of your favorites.
4. You will sleep in a night gown, panties, and whatever else I tell you to wear. Tonight, you can start with your white knee socks. So cute and feminine. Don't forget your perfume.
Love, Your Queen.
I love her so much.
As you might have gathered, I have a thing for wearing women's clothing. Like many who enjoy crossdressing, I tried to suppress it, fight it, but could never give it up. Because it was the right thing to do, I managed to work up the courage to tell my wife about my quirk before we were married. I was nervous as hell that she would be repelled and reject me, but I loved her too much to keep a secret like that from her.
She was shocked when I told her. I was afraid she would end our relationship. Her initial reaction was not great. I think she was afraid, maybe embarrassed. She asked if I was gay. I told her that I that I did not think I was. She asked a lot of questions, and I explained about dressing up in my sister's lingerie, pantyhose, ballet leotards and tights. I was not actively dressing up at the time, but I think she knew that it was a part of me that was not going away.
To my delighted surprise, she tolerated my quirks. Although it was not really her thing, she began to indulge me shortly after we were married. It started out with making me wear panties while she gave me a hand job. It evolved into dress up nights and then entire girls' weekends where she would make me stay dressed for an entire weekend twice a year. She loved how much joy dressing up gave me.
I became more submissive to her sexually, and she became more dominant. I was beside myself with joy, but her indulgence only led to a deeper obsession on my part. I could not get enough. I wanted to dress more often and buy more women's clothes and shoes.
While she indulged me out of love and genuine happiness at my excitement and pleasure, she still struggled. It was hard for her.
"I married a strong, confident, masculine man. While I admit to some lesbian fantasies, I like men. I love you."
"You are an incredibly generous and skilled lover, but I am not sure you can be a real man for me anymore. That is why I struggle with your dressing and submissiveness. I don't consider you a real man anymore. How could I after seeing you in panties, tights, stockings, dresses and heels? I can assure you that my romance novel fantasies from my younger days did not include someone who would rather wear a leotard and ballet tights over smoothly shaved legs than a manly suit. I feel like your cock has shrunk and gets less hard since you started wearing panties all the time. I mean you even tinkle sitting down."
"Even if you could go back to being a real man for me, I don't think you would be happy. Knowing that would ruin it for me."
The first time she said this I was worried that she wanted to leave. She assured me, however, that she loved me and would never give up on our relationship. I was also, I must confess, extremely aroused by my beautiful, sexy, and loving wife's blunt acknowledgment of my complete emasculation.
While she was very honest about her struggles, she also became even more indulgent of my femininity. She encouraged me to move away from my initial sluttier looks and dress like her friends would dress. She encouraged me to buy more expensive normal clothing like dresses and quality shoes and to have a complete wardrobe from active wear to cocktail attire, with shoes to match. I was beside myself with feminine joy.
When she continued to express her struggle with, as she laughingly called it, her "manless marriage", I told her one night that I would not have any objection to her satisfying her need for a real man outside of our marriage. That shocked her once again. While she enjoyed talking about the idea as a fantasy, she rejected the reality of this option. She said it was too messy, too risky for our relationship, and too fraught with potential embarrassment in our mid-sized Texas city. While I was initially comforted by her response, I was sad for her. My greatest desire was for her to be fully satisfied sexually. I was naturally scared about the reality just as she was, but I was frankly extremely turned on by the thought of her with another man, a real man who could give her what she needed. While she would not lack for opportunity given her grace and stunning beauty, I recognized it would be extremely difficult for her to find someone who excited her. She is very picky about men, has no tolerance for assholes, and is not the type to fuck the pool boy or other random dude. She like the comfort of our relationship, and she had a tough time imagining that she would ever find the person who would want to be with even if she decided to seek to satisfy her needs outside of her marriage
I continued to encourage her to find a real man whenever she would share her struggles with my emasculation and love of all things feminine, but she would not consider it. She continued to indulge my passion for dressing and expressing my femininity, but I still worried she was missing something. I became more and more intrigued with the thought of her finding other lovers to satisfy her need for a real man. I took a deep dive into cuckold websites and fiction on Literotica. The whole fantasy fit so perfectly with my dressing and craving for emasculation. I mean, what is more emasculating than having your wife take other lovers because you could no longer be a man for her?
When it reached the point of bugging her to death, she let me know in no uncertain terms. I tried to back off, telling her, "Just know that I am good with it if the opportunity arises."
I tried to accept that my fantasies were not going to become reality. In the meantime, she continued to indulge my desires, perhaps even becoming even more dominant and dismissive of any lingering shred of manhood that I might have. Perhaps she was just channeling her frustration into the cruel feminine control I craved.
My present reality was still fantastic. I twitched with excitement as I unpacked the suitcase to see what surprises she'd packed for me.
First, I pulled out a very short baby blue smocked dress with bell sleeves. Next was an ivory lace swing dress, high necked with cap sleeves and scandalously short. Finally, there was a black knit sweater mini-dress with funnel neck and long sleeves.
After I removed the dresses, I uncovered my white Eileen West nightgown, with ribbons and ruffles around the neckline. This was my favorite. She had worn it the night before I left, so it was perfumed with her wonderful femininity.
Under the dresses and nightgown she had rolled up a set of undergarments: a black and a white shaper camisole, black and white Maidenform high-waisted shaper briefs, a pair of black DKNY super opaque high-waisted tights, a pair of white opaque tights, and finally a pair of ivory micro fishnet tights with a pair of Hanes Silk Reflections control top pantyhose to wear as a base layer underneath (a great girl trick she taught me).
Then, much to my delight, I uncovered a black classic ballet leotard, pink ballet tights, and a white ballet shrug sweater with matching stirrup leg warmers. Under those, she had packed my pink leather ballet shoes. I am obsessed with the ultra-feminine look of ballet outfits, a carryover from my childhood adventures in my sister's room. I then found eight pair of Vanity Fair Illumination string bikini panties in a mixture of white and black, one for each day and night. The panties were stuffed between three pairs of shoes, black suede pumps with a bow on the front and 4-inch heels, and a pair of black suede Nine West almond toe platform booties also with 4-inch heels, and a pair of super cute black patent leather Mary Jane ballet flats with a square toe. Peeking out of the shoes were a pair of black opaque thigh high stockings, a pair of white opaque thigh high stockings, and a pair of DKNY white opaque knee socks.
After unloading my male clothes, such that they were, that I had packed, I quickly shaved my body in the shower with the pink Venus razor. This task was easy, since she started making me keep my body and legs always shaved the year before. As instructed, I left only the small, dainty triangle of neatly trimmed hair above my "clit" as she now called it. This cute little triangle really made me look even more girly than nothing at all.
I had about two hours before the 5:30 pm cocktail reception so, in accordance with my wife's instructions, I had to dress.
I pulled on a pair of black bikini panties, rolled up each leg of the black opaque tights, and pulled them over my pointed toes, up my legs and high up my waist. I then pulled on the black shaper brief and pulled it high up my waist, compressing me in its grip. I pulled the shaper camisole up my matte black coated legs and put my arms through the straps before adjusting it to fit. Now encased in a tight black feminine cocoon, I slipped my feet into the suede booties, relishing the cool feel of the leather inside on my feet. I zipped up each of the booties in the back and slipped the black knit sweater dress over my head and straightened it. I admired my feminine dress in the mirror, shivering with delight.
My phone buzzed.
It was a text from my wife. "Dressed and about to head down to the bar."
The accompanying photo was of her tights-covered leg and a black suede almond toe bootie identical to mine. She would often taunt me by buying and wearing the same shoes that I had. She says I have good taste, which is beyond thrilling to hear.
"What are you wearing?" was her next message.
I snapped a quick picture of my legs going down into my booties and sent it to her.
"You are a naughty girl. You need to wear your tights and shaper under your clothes to the cocktail reception. You need to constantly be reminded what it feels like to be a girl stuffed in your tights and control garments like a sausage. I guess you like that in your perverted way."
