The Agreement Ch. 04

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A man's wife accepts his crossdressing.
2.7k words
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Part 4 of the 7 part series

Updated 11/01/2022
Created 11/18/2013
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komrad1156
komrad1156
3,765 Followers

The rest of the week dragged on and I found myself uninterested in work for the first time ever. The only break I had from the seemingly endless routine was my Thursday session with Dr. Turner and planning for Saturday night.

I asked Sarah if she minded my dressing up again for the voice therapy and she eagerly agreed. In fact, she was having a long rest of the week herself. She'd spoken with Dr. Conley or "Kevin" as she now referred to him and he'd agreed to meet her, as well. Sarah couldn't stop babbling about how good looking he was, how slow the week was going, and how she had to get out and buy something really sexy but not too revealing to wear. Like a dog in a Far Side strip, all I really heard was "sure" to my request to go to therapy en femme as she rambled on about her own issues.

The weather had turned colder and the forecast for Saturday included a daytime high of just 40 degrees. That meant it would be even colder by the time we met our dates. While I was a bit disappointed not to be able to wear something slinky, I was really a sweater girl at heart. I'd always loved them—especially with the ribbed knit look. I'd be happy to wear a pretty skirt and sweater and the weather gave me an excuse to go shopping on Saturday morning. Of course, I had other things to take care of, not the least of which was a full body wax so I'd have to plan carefully. As if I didn't already plan things as meticulously as humanly possible!

I'd put together a modest collection of women's clothes and jewelry since "the deal" and now found myself torn trying to decide what to wear to my therapy session. I finally settled on a very pretty white blouse with a scalloped collar and short black skirt with matching three-inch heels and barely black stockings. I choose a string of white pearls and matching clip-on earrings with a silver watch and large silver cubic zirconia diamond ring to complete the look. It was chilly but not too cold so I also wore a nice-looking black cardigan.

I took one last look in our full-length mirror before heading out to the car and I was pleased as I could be. Once I was fully in drag, the look almost made me dizzy. I'd never experienced anything quite like that feeling in my life and even now it still "does it" for me. I've heard crossdressers are narcissists at heart and didn't know (or care) if that was true. All I knew is seeing myself look like a beautiful woman was the most amazing feeling in life. I couldn't help but think that being treated like one by a handsome man might be even better. The thought made me smile—and swoon with anticipation.

I had another very fruitful session with Lisa who was duly impressed with my rapid progress. She told me I was welcome to come back as often and for as long as I felt I needed her help but she let me know there was precious little more she could offer. I just needed to practice what I'd learned until it became second nature. The one remaining area I'd had trouble with was laughing like a woman without sounding unnatural so we spent the entire time working on that. Both of us ended up genuinely laughing—a lot—at my various attempts to get it right. A little over half way through I hit on a technique that made Lisa say, "Oh! Just like that, Callie. Do that again for me." I did and it worked rather well. Practice did indeed make perfect (or at least good enough!)

Learning to laugh well seems silly, but it's critically important. Women smile a lot and they laugh often. Men do much less of both. It was really important to me to be able to carry on a natural conversation and to be able to react the way any real woman would. I'd spent countless hours since "the deal" working on mannerisms and gestures when I was alone and felt very comfortable with myself. Talking and laughing were the last things I felt had to be conquered for me to present as a woman and pull it off in public. By the time I got home, I'd never felt more confident.

As Saturday finally arrived, I was up early for a five-mile run. Keeping my figure lithe and slim was almost as essential as good makeup and hair. Sure, larger women were everywhere and many were beautiful, but it was just a lot easier for a man to pass as a woman if he were small as it attracted less attention than being say 6'2" and 200lbs. I used to hate being "short" which wasn't really short but maybe an inch below average. Now I was very thankful I wasn't even one inch taller!

After a quick shower I headed out to the mall to try and find just the right outfit and I most definitely had to buy a high-quality coat and some gloves. I arrived at 10am as the doors opened and had almost three hours before my body wax appointment at 1pm. That would take around an hour and get me home by 3 o'clock or so leaving with time for a short nap before starting the long process of transforming into Callie.

I looked around in about a dozen stores and saw so many things I liked I knew I was going to have a hard time settling on just one outfit. I decided to go buy the coat and gloves first. I found the perfect items at Nordstroms and ended up choosing a gorgeous coat in black along with a pair of beautiful matching gloves. The sales clerk was an older woman and she told me how wonderful it was to see a man out shopping for his wife. She never even questioned my trying the coat on as I let her know Sarah was just about my size. I was in and out in 20 minutes and was now faced with a decision.

I'd seen perhaps ten things I liked, five of which I loved, and two I just had to have. My favorite was a stunning long-sleeved cashmere sweater in winter white. It was luxurious and sported a jeweled neckline. Over time, I'd learned to perfect the illusion of breast cleavage using makeup to create shadows that looked exactly like the real thing. This top would be perfect for that. I also chose a knee-length black skirt that was slit up to my thigh on one side and a pair of three-and-a-half-inch black pumps to go with.

On the way out, I stopped at the jewelry counter and bought the most beautiful black onyx necklace, bracelet, and matching earrings I'd ever seen along with a petite silver watch that had a black wristband. Although money wasn't an issue for us I couldn't help but mentally ring up the total cost as I made my way to the car. I'd spent just under a thousand dollars not counting the body wax. Adding that in put the total at just over a grand. "Who cares?" I thought to myself. I'd have spent another thousand if that's what it took to get ready for my first date with Michael. And I most definitely would have.

I was far too jazzed to nap when I got home so I watched some college football to kill time. I found it impossible to concentrate though, as my mind kept running through my checklist of things to do. Being a planner and a linear thinking has its advantages and disadvantages. The upside was I rarely ever missed a detail. The downside was my inability to stop obsessing about missing something. All in all, it worked for me and I accepted it as the way things are. Still, it would have been wonderful to be able to lay down for an hour or two. Maybe next time. Yeah, right.

Michael had made reservations for four at an upscale sushi place in Springfield because it was near the Hilton Hotel which was where "The Blue Parrot" lounge was located. It was one of the nicer places to dance and always featured a live, local band on the weekends. This week's group would be playing a mix of 70's and 80's stuff and all of us were looking forward to both the food and the music and well, the....

I needed to be ready to leave by 7:30 as it would take about half an hour to head south down I-95 and get there on time (we'd settled on an 8 o'clock meeting for dinner as the band started playing at 9pm) or maybe fashionably late. Learning not to be early was something I really had to work on. I knew it was perfectly okay for a woman to run late but as a man, that would make my skin crawl! I was early to everything and people often joked I'd be early for my own funeral! Then again, I wasn't going to look anything like a man tonight so late would be just fine. Maybe.

I had to start getting ready around 4:30 while Sarah could wait until 6 o'clock or so. She'd settled on a very sexy crimson-colored sweater dress she'd bought from Victoria's Secret on-line. It fit her like a glove and had a plunging neckline that was perfect for a long pendant that could hang between her ample breasts. It would be both warm and fashionable and show off her hot body in all the right places. I knew she'd look spectacular for Kevin and I set out to look every bit as good for Michael.

I used one of our other bathrooms so Sarah could have the master. I loved seeing all of my pretty new clothes laid out on the bed waiting for me to slip into them once my hair and makeup were perfect. I showered again and marveled at how smooth my entire was after the waxing. I spent the first half hour just blow drying and styling my hair which I wore with a side part tonight on the left with just a wispy set of bangs falling down over one eye from the middle toward the right side. I spent an inordinate amount of time on my eyes and eyebrows after applying a sheer liquid foundation. Once everything was as perfect as I could get, I applied blush to the apples of my cheeks and blended everything in and set it with loose powder. The last step was adding some false eyelashes to give me that extra length I really didn't need but so desperately wanted.

I was hard as rock when I finished prepping. My hair and face were as perfect as I'd ever gotten them. I thought about masturbating to get rid of my raging hard on but I didn't want to take the edge of off this wonderful feeling of growing anticipation so I forced myself to think about something—anything—else to make things more manageable. Finally, Mr. Happy was ready to be taped down and hidden under my silky black laced panties and CAD-designed padded undergarment. I wore the one in black tonight to match the thigh-high off-black stockings and black skirt and heels while I chose a sheer off-white bra to wear under my beautiful, soft cashmere sweater. I dared not look in the mirror again until I was done for fear I might cum in my panties so I carefully got into my new outfit making very sure I didn't touch my $200 sweater with any makeup—especially as I created the illusion of cleavage. Once I was dressed, I was ready to apply the expensive French nails I'd bought from a salon and glue them in place. I did my own because salons always glued them on so hard it was a bitch getting them off without tearing the nail itself. I knew how much was too much and how much was just enough so this was definitely a do-it-yourself project for me. I left them unpainted but did give them two coats of shiny gloss. I loved seeing the white lines in the tips almost as much as I liked seeing them a dark red. It was a difficult choice but I knew my very full lips would be a luscious, deep red and the nails looked beautiful clear so that was that.

By 7 o'clock, I was ready. I hooked the onyx necklace and bracelet into place and clipped on the dangling black earrings. I slipped on my new watch then took a deep breath as I stood in front of the mirror and opened my eyes. Just as I did, I heard the click of Sarah's heels growing louder. I was breathless as I saw my female image staring back at me and I thought, "God, I want to fuck myself" as Sarah walked in said, "You've got to be kidding me!"

"Sarah! Hi. You look amazing!" I told her as I admired (and envied) her tight-fitting knit dress and matching heels.

"Fuck you," she said with an angry look of bitterness. "I'm about sick of having my husband look better than me. I mean, I've been looking forward to this all week and now this is ruining it for me."

I really didn't know what to say. All I could think of was to say, "But you look freaking amazing, honey." I'd forgotten to use my female voice and Sarah shot back at me.

"Great. Let's hope you don't do that tonight at dinner and blow this whole thing apart." She stormed and said, "We're leaving in 15 minutes."

I made sure I had everything I needed in my small, black clutch as I picked it up along with the new coat and slid it on. I was still excited about tonight, but this outburst had really put a damper on things. I saw Sarah heading for the door and followed her out to the car.

As we both got in and put on our seatbelts Sarah said, "I'm really sorry. That was totally unfair of me. This was mostly my idea and I knew how good you look dressed up. I was just feeling selfish and quite frankly a little jealous. I know that's silly as I have my own date and all. I guess the thought of you stealing the show really pissed me off." She paused for a moment before turning to me and offering, "So again, I'm sorry. Are we okay?"

"We're fine, and thank you," I said remembering to use my feminine voice. "I understand but trust me, you have nothing to worry about. You're gorgeous and if Kevin can't see that, then he's a fool."

"Thank you, Cal. Oh, God. I just did it. I mean 'Callie.' Hey listen. Are you sure you really want to do this? I mean, we're actually going out with two men and the chances are we're going to have sex with them. Will you really be okay with that?"

I now felt much better and smiled as I assured Sarah I not only didn't mind but hoped she got everything she was dreaming of tonight and more. And I knew I was definitely hoping for the same. It hit me that in less than 30 minutes, I would have a handsome man kiss me hello for the first time in my life and I didn't care at all that another man would do the same to my beautiful wife. God I was excited!

"I'll be fine, honey. Absolutely fine. Now let's get going. We have two very good looking men waiting for two very beautiful women!"

Sarah put the car in reverse and as the garage door closed, I closed my eyes and imagined slow dancing with Michael, my arms around his neck, and his hard cock straining through his pants pushing against my body. "Mmmmm," seemed to sum everything up I was both thinking and feeling.

komrad1156
komrad1156
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7 Comments
AnonymousAnonymousover 10 years ago
makes me feel wonderful

Your story makes me feel wonderful because it reminds me of how my wife and I prepare for our double dates. We often go out with 2 men and both of them know my real situation -- and they both always want to fuck both of us. We are such sluts and we always let them fuck us -- of course that's after I suck both their cocks and watch my wife suck them too. Love your stories -- can't wait to read the next chapter.

emilynbemilynbover 10 years ago
Wonderful

i love these series of stories, they are so dreamy and perfect.... it's so wonderful to be desired ones femininity!

AnonymousAnonymousover 10 years ago
great

Love your story (and the humor and travails of dressing), but fact it sounds like VA here makes me want to squirt in my panties! :)

CD Sara

AnonymousAnonymousover 10 years ago
Wow!

Callie's description of this marvelous experience is so sensual and sexy! Good writing! Keep on going

MichelleWhoIsMichelleWhoIsover 10 years ago
Wonderful story

I can imagine the emotional roller coaster presented in this story. It is one that very few ever get to experience in real life. I hope that the continuating chapters show us that life goes on for Callie and Sarah. With the new people around her, a nurse, doctor and a lawyer, all things are possible.

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