My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything.

About one year ago, we were fighting constantly. We didn’t know why, but we were both at our wits end with each other, so we decided to seek couples counseling. During one of the particularly heated sessions, it came out that one of the big sources of our discontent was the boredom we felt with one another in the bedroom. The counselor decided that we go home and each write a letter with a confession of a sexual fantasy, read the other’s, and then find some way to compromise and combine them into one. The goal was to have a new ‘shared experience’ to reignite our passions.

We were quiet on the drive home. I think we both were searching for the fantasy we wanted share and probably both worried about how the other would react. When we arrived home, we opened a bottle of wine, which quickly turned to two, to calm some of the inhibitions we were feeling. Then, we decided to each go to a different room in the house to pen our desires.

My heart was racing as I put my pen to the paper. I knew what I wanted to confess. When I was younger, in my teens, I had experimented with dressing in my sister’s clothes. I would wait until I was home alone, make my way into her room, try on her panties, bras, dresses, and walk around the house feeling feminine and free.

When I had dressed like this, I felt sexy and vibrant. I wanted to feel like that again. So, I wrote down this confession in my letter. I wrote that I wanted to dress up for her so we could make love as two women. My hands shaking, I folded up the letter and made my way back to the kitchen where we would meet.

She was already there and waiting with letter in hand, looking every bit as nervous as I did. We smiled at each other and passed the notes. Excited to see what she had written, I opened her letter. It read as follows:

“When I was in college, I had a girlfriend for three months. I’m still attracted to women now and consider myself bi-sexual. I’ve never told you about this because I didn’t want you to be jealous of me when I spend time with girlfriends, even though I’m not really attracted to any of my friends. My fantasy is for you and me to go to a bar and pick up a gorgeous, sexy woman to bring home for a threesome! ;) xoxo”

My heart began pounding as I read this. The thought of watching my wife with another woman was sending blood rushing through my body and giving me a rock-hard erection. I didn’t even mind not being let in on her “little secret". Obviously, I had never let her in my mind. A sharp anxiety over-took me as I looked up to see her reaction to my letter.

She had the biggest smile on her face.

“Babe! I had no idea you like to crossdress,” she said.

“Oh well, I had no idea you liked women,” I managed to sputter out.

She rushed over to me and buried her tongue in mouth. We made out all the way to our bedroom and proceeded to have the best sex we had had in months! Her five-foot-six slender body rode on top of me while her shoulder-length chestnut hair bounced gracefully. Her C-cup breasts and pink nipples heaved with every lift and crash of her body onto mine while her tight pussy cupped my cock. Despite my drunken state, I was so aroused that I came into her quickly and we passed out for the evening.

When I awoke the next morning, she was in the kitchen making breakfast. I groggily made me way in and sat down at a stool near the island. She turned around from the stove and began pushing scrambled eggs onto my plate.

“So, I’ve been thinking about the compromise,” she said.

I had almost forgot about our letter exchange, given the alcohol fueled romp we had the night prior.

“And?” 

“It’s pretty easy, I think. First, we’ll get you all dolled up, then we can head to Whispers together as girlfriends. We’ll pick up the hottest girl we can and bring her home for a lesbian threeway!”

Whispers was the local gay bar. I was shocked. I had never given thought to leaving our house en-femme. It was equal parts thrilling and terrifying. She noticed the look of terror on my face and started to make her case.

“They have a ‘come-as-you-are’ night where you will fit right in. I can have Andre and some friends come over so we can go as a big group. You will have a blast being able to let loose and free and rock that feminine side of yours!”

Andre was our friend, a local gay DJ legend. He spun at all the local bars and had quite a following. Now she was implying that not only was I to go out in public, but that some of our friends would also be in on my secret.

I was nervous that I would just look like an awkward guy in a dress. I am six-feet-one-inch tall, a hundred and ninety pounds. Not fat, but a little chubby. I have medium length, shaggy brown hair. However, I do have naturally wide hips that could help. I’ve also always secretly practiced a feminine walk and voice just in case this moment ever arose.

“I’m nervous, babe. I don’t want to look some freak show.”

“What? Never. You would be surprised if you knew how the right clothes and makeup can totally change how you look and feel,” she reassured.

“It’ll be fine. Andre and his crew will love the fact that you dress! Plus, we really need this, babe. I was so happy last night when I read your letter. I want to change things up for us. And, I really want to see what you look like as my sexy wife.”

Her last sentence sold me.

“Okay,” I said, “I’ll do it. But promise me that no matter what happens after this night, that it will still be you and me afterword.”

“Promise,” she said with a big gigantic grin.

It being Sunday, we decided to go out the coming Friday. We spent the rest of the afternoon at the shopping mall picking out my outfit. I can honestly say that this was the most fun I had ever had with her. We bounced from store to store like to girlfriends on a shopping trip.

First, we went to the local H & M and looked for a skirt. My inner girl was beaming as I perused through all the ensembles trying to pick out the perfect one for me. I decided on a paisley-patterned bubble skirt with an elastic waist that came to about two inches above the knee.

We then made our way to Dolce & Gabbana where, with the help and counsel of my wife, I picked out a tight, low-cut black tank top. Finally, we picked up a pair of unbelievably adorable black, four inch stiletto heels with point-toes and ankle straps. I still needed some jewelry and a wig, but she told me she wanted to surprise me with that and that she had plenty of jewelry to use. There was only one thing left, the lingerie.

We proceeded to Victoria’s Secret where upon entering the store she whispered in my ear.

“Now, what do I want to see that sexy ass of yours in?”

I flushed with embarrassment as she walked to the rack of panties. She settled on a pair of black lace hipster briefs and a lacy push-up bra.

“Now, this is going to be so sexy on you,” she whispered in my ear as she pinched my ass.

The rest of the week was a blur. Finally, Friday arrived and I rushed home from work knowing our adventure was about to begin.

When I walked through the door, I saw my wife, Andre, and another man sitting around the kitchen island drinking wine.

“There he is!” Andre yelled.

He ran in my direction and wraped his arms around me in a warm embrace.

“We are going to have such a fun night! This is my friend, Michael, also known as Mikayla. He does drag on the weekends, so I thought I would bring him along as an expert in the art feminization. He is going to be the architect of your feminine beauty, my dear! Now, off with you two to the bathroom. I have a feeling this might take a while, so Ally and I are going to hang out here for a minute and then get ourselves ready.”

Ally came over and gave me a passionate kiss.

“Okay, Sam. This is it. I can’t wait to see the finished product,” she said.

And with that, I started walking toward the bathroom with Michael following close behind. When I walked in, I saw a big bottle of Nair sitting on the counter.

“Honey, I’m going to make you into one sexy lady tonight, so just do what I say, and you’ll be in good hands. First step, strip,” said Andre.

I paused not moving.

“Don’t worry, sweetie. You’re not my type. I like a manly-man, not a girly boy like you,” he said with a wink.

I undressed and stood there naked in front of him.

“Okay, you’ve got some nice natural curves we can work with. Step two: put this pink shit on every inch of your body below your neck.”

I did as I was instructed and immediately felt the tingle as my body hair melted away.

“Now we wait for a few minutes while the magic happens. So, let’s get to know each other,” he said.

“Okay, I’m Sam. Nice to meet you.”

I laughed at this being our first introduction, me in the nude covered in pink goop.

“And I’m Mikayla.”

He shook my hand.

“Now tell me about why you dress, sweet-heart.”

I filled him on the details of my youth and on the inner-femininity and desire to dress I’ve always felt.

“And, when you were dressed, did you ever the feel the urge to be taken by a man, sweetie?”

“Oh! I uh, I guess I never, well maybe I did before. I don’t know about know. I mean I love my wife, so no, I think.”

“Mmhmm,” Mikayla hummed, “don’t worry, baby, I won’t tell.”

I’m sure the embarrassed pink flush on my face matched the goo on my body.

“Well, I think it’s about time you got into the shower and wash that shit off. By the time you’re out, I’ll be ready to go and we can focus on your dress and makeup!”

I got into the shower and washed away the Nair. I watched as my body hair ran down the drain. The masculine shell was washed away with it, and the air on my smooth skin gave me the feeling of rebirth. When I stepped out of the shower, Mikayla was there in full drag. She was gorgeous.

“Wow, Mikayla. You look great!”

“And I’m going to make you look sexy too, girl. Except, I’m guessing you want a more natural look don’t you. Like your just another girl at the bar?”

“Yeah, I think I would prefer that.”

“Okay, we can do that. Next step: put this softening lotion your skin. You want to be silky and smooth before we get you dressed.”

I rubbed the lotion on my skin and could feel it softening. I was more sensitive to the touch and the sensation on my skin was electric.

“Next step: put on the gaff,” he said as he handed me what looked like a little fabric sling-shot.

“Um, what is this? Why do I need it?”

“Babe, this little device will keep your manhood pushed back. This is just so that, in case you find yourself getting…aroused…you won’t have any embarrassing little bulges. Just step through these hoops, pull it up, tuck in your little clitty there, and the put this back strap in your crack like a thong.”

I took the gaff and put my legs through the straps, lifting it up and pushing my testicles into my groin, tucking my penis back, and using the gaff to secure everything in place. Mikayla then handed me my clothes. I put on my bra first and Mikayla stuffed two silicone breast lifters in to help lift my natural cleavage and push them up and together. I was surprised at how natural they looked!

I put on my lacy panties over the gaff. Next came the tank top which I tucked in to my adorable bubble skirt. Mikayla sat me down in a chair in front of the mirror put on some false nails first, then started with the make-up. I felt like a pampered princess and I loved every second of it.

“Okay, keep your eyes closed, sweetie. I’m going to go get your wig and jewelry to polish you off.”

She ran into the kitchen to get the wig from Ally. I heard my wife’s voice.

“How does she look?”

“Ally, your husband makes for one sexy wife, let me tell you!"

The compliment gave me an immeasurable amount of joy. Mikayla re-entered the bathroom and began clipping the wig in place. She put a necklace around my neck, then lifted my arms and put bracelets and rings on.

“Okay, Sam. Wait, does your inner princess have a name?”

I thought for a minute and answered.

“Call me Sarah.”

“Okay, Sarah. Open your eyes.”

I had to hold back the tears. I was beautiful. The wig was a brilliant chestnut brown, side parted and shoulder length. My lips were pink and glossy, my cheekbones rosy, and my eyes smoky. I was hot. I was sexy. I was happy.

“Stand up and twirl, girl,” said Mikayla.

I stood up a little wobbly in the heels, but regained my balance and gave my best feminine twirl.

“My God, you have fantastic legs, and that’s one cute little butt!”

Mikayla gave my ass a little smack.

“You are going to get a lot of male attention tonight. Are you ready for that?”

My already rosy cheeks flushed.

“Well, I’m going with my wife to pick up another girl. I don’t think there will be much of that going on,” I replied.

“Mmhmm. Let’s go show your lady her new wife.”

Mikayla walked back out to the kitchen and made the announcement.

“Lady and gentlemen. May I introduce, for the first time, the sexy, the gorgeous, the vivacious, girl with the cutest little bubble-butt in town, Sarah!”

I came out giving my best fashion model strut. Ally’s jaw hit the floor. She had a stunned look of shock and lust in her eye. I guess my new look was stirring some of her sapphic desires.

“Oh my God. Sarah, is it?”

My wife giggled.

“Why don’t you come over here and give me a kiss.”

I walked over and Ally reached out and pulled me to her quite aggressively, much more so then ever before, and started to stick her tongue in my mouth. She was usually the one to let me take the lead, but not this time. Her hands reached back and cupped my ass as she kissed me.

Mikayla wasn’t wrong about the gaff. I could feel blood flowing to my groin, but because I was tucked so tight, instead of getting an erection I just felt a warm burning in my belly.

To our onlookers we must have looked like two lesbian lovers in a passionate embrace - me in my cute, girl-next-door club outfit, and my wife in her little black Audrey Hepburn dress, her hands on my ass and my arms on her shoulders.

“This is going to be an amazing evening,” Ally whispered in my ear.

“Let’s get going!” she exclaimed.

Our foursome made our way to our car. Andre and his three girls, our heels clicking on the pavement, piled into the vehicle. Andre and Mikayla got into the front seat. Ally and I sat in the back, our fingers intertwined as the car pulled off into the night. I couldn’t wait to see how this evening unfolded!

...to be continued.