The Agreement

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A small number of people know me as Callie. Who I am depends on well, who I am when they meet me. 

Lastly, I mean no offense, but I personally don't care for the (very) short stories where the horny crossdresser ends up on "her" knees on page one. If that's your thing, this may not be your cup of tea. Otherwise, I hope you enjoy!

I paused for a moment to reflect on the changes the last year had brought. Yesterday was our fifth anniversary in which my wife surprised me with a complete shift in attitude we came to call "the agreement." It was preceded by an arrangement we'd come to one year previously. We simply called it "the deal."

I'm now 32 and my former wife Sarah (not her real name for obvious reasons) is 30. We divorced a year ago partly because of crossdressing but most for other reasons. This story takes place five years ago when we were 27 and 25, respectively.

We married the day I graduated from college while she was still a senior in the University of Virginia's nursing program. I've worked as an aeronautical engineer on a nearby Navy base since, and between the two of us we make an excellent income.

Like most men who crossdress, I didn't tell Sarah my most deeply-held secret until after we were married. Like those other men, I too believed getting married would "cure" me; that I'd lose interest in it once I had a wife. The fact that she preferred wearing the kind of clothes I preferred to wear when dressed up allowed me to superficially convince myself that would serve as an adequate substitute and keep me on "the straight and narrow." For the six months before the wedding until about six months after, it had.

Just over a year ago, on a Saturday evening when she was working swing shift, "the urge" returned with a vengeance. I'd gotten rid of all my female things, something known as "purging" in the crossdressing community "knowing" I'd never need them again. As I looked through Sarah's things to select my outfit, I was as careful as I could be not to either stretch out any of her clothes or to get makeup on them. I knew I was taking a risk, but I couldn't stop myself from spending the evening as Callie. I'm a small man. I stand 5'8" and at the time weighed 150lbs. Sarah is an inch shorter than me and there's no chance I'll give her weight—now or ever. (Suffice it to say she weighed considerably less than me.) 

Even without a wig and with hairy arms, legs, and chest (mine was light but noticeable as I hadn't shaved them in years), I found myself flooded with the endorphin rush that always came from dressing up like a woman. I reveled in every aspect of the experience the way I always had from choosing what to wear to the careful application of my makeup to accessorizing. I preferred a classy, semi-professional look and I have what might be termed a fetish for certain kinds of sweaters paired with shorter skirts, heels, and expensive jewelry. While the sweater thing may seem odd, it's actually pretty logical as I grew up in northern Virginia where it's cold much of the year. Girls and women wore sweaters a lot and I have always liked the dressier, more form fitting type. The thicker, baggier, "granny" variety does nothing for me. Don't get me wrong. I also love nice dresses, blouses, lingerie, and even jeans. It's just that a sexy sweater is my all-time favorite.

My "first" session ended all too soon with a call to a phone-sex line that specialized in crossdressing men and very near wardrobe miss as I came with a ferocity I hadn't experienced in a very long time. Callie was back and I was sure Sarah would never understand. I had no idea how to address this with her, but I knew Callie wasn't going to be able to stay in the closet any longer.

I could tell something was bothering Sarah as she got dressed for work the next day. She seemed puzzled after looking at her neatly-stacked sweaters in the closet. I'd put things back as carefully as I could, but women can just sense when things are out of place. Even worse, she was visibly upset after grabbing her bra and panties from the dresser door. She didn't say a word, however, and I didn't ask as I knew she suspected something. I was grateful for what was likely only a reprieve no matter how short-lived it might be.

Less than two weeks later, I was enjoying another evening as Callie when Sarah came home unexpectedly from work. I was in the master bathroom and had just finished removing all of my makeup. I was toweling off when looked up and saw her. Her favorite white sweater and black skirt were on the bed and a pair of three-inch black heels were on the floor by the bed.

"Who is she!?" Sarah demanded. "Who are you sleeping with, Cal?"

I saw tears fall from her eyes and I sat down on the bed and said quietly without looking at her, "No one, honey. There's no one else."

She picked up the shoes and said, "If it was just my skirt and sweater that would be bad enough knowing you let some other woman wear my clothes," she said as she picked up the shoes. "But THESE are someone else's. THESE arenotMY shoes! Don't lie to me. Who was here with you tonight and how could you let her wear MY things???"

I looked up at her, took a deep breath and told her, "Sarah, those are mine. The shoes belong to me."

Stunned, Sarah dropped them on the floor and said, "What are you talking about? How can they by YOUR shoes, Cal? What would you be doing with women's shoes? I might be able to forgive a one-time affair, but if you lie to me, we're done. Now I want the truth. No more lies. No more BS. I want thetruth! Who IS she???"

For the next ten minutes, I explained my lengthy obsession with crossdressing. I told her how much I'd hoped it was over when I met her and that I honestly believed it was all behind me. I explained the sudden, overwhelming return of these urges and that I felt powerless to stop. I felt both a deep sense of shame and relief that this was finally out in the open no matter how Sarah might react. I was shocked by her response.

"That's it? YOU wear my things? Jesus, Cal. I thought you were having an affair. I've been jealous of Erin (an attractive co-worker at my firm) for as long as I can remember and I immediately assumed it was her. I mean, I've seen how she looks at you and the way she laughs at everything you say. Trust me, you're notthatfunny," she said half-jokingly.

Sarah sat silently at the foot of the bed for what seemed like a very long time. Finally, she turned to me and said, "This I can deal with—I think. I mean, I might be able to handle it. I just don't know. I'm just so relieved you're not having an affair that maybe I'm being overly optimistic about this. All I can say is we can try it for a while and see how it goes. I'll need some time to process all of this. Just tell me again there's no other woman, okay?"

I assured her there was not and there never would be. I told her how much I loved her and that she meant everything to me and that no other woman could even compete with her.

Sarah suddenly burst out laughing! "I KNEW something was going on! My bras were stretched out and my sweaters weren't folded right. I thought I was going crazy and then I started to suspect another woman. Then I come home and see my things on the bed and these other shoes on the floor and I was sure you were cheating on me." She laughed some more. "Now I know why you've always been so interested in what I wear and why you buy me so many clothes and so much jewelry. Those are things YOU'D like to be wearing, aren't they, Cal?"

For the first time since I was 14, I blushed. "Yes," was all I could manage to say.

Sarah sat down beside me, leaned her head on my shoulder then took my hand. "I love you, Cal. I don't care what you wear—in private. I don't think I want to see this—at least for now--all that really matters is you love me. You're not much bigger than me which explains why the changes I noticed in my clothes were so subtle. I don't like the idea of you wearing them so really need to get your own things as soon as possible. Deal?"

"Deal," I said as I turned toward to see if she meant what she was saying. I could tell from her eyes she did. "Thank you, honey." I said sincerely as I sat next to her.

Sarah took my hand and kissed me and said, "No, thank you. Thank you for loving me and for being honest enough to tell me this. I can't imagine how difficult that must have been. Now let's put this stuff away and get ready for bed. And no, you may NOT wear one of my nighties to bed," she teased playfully.

That was the "deal." I could buy my own women's clothes and wear them when she wasn't around. I also managed to convince her to let me shave my body hair and grow my hair longer. The "agreement" was still a year away and it came after a seesaw ride of ups and downs with my crossdressing which I'd kept private and away from Sarah as we agreed. She had no problem with me shaving my body hair or growing my own hair longer. After almost a year of nothing but trimming the ends, it was now almost shoulder length and I wore it in a thick pony tail at work. Sarah actually liked my hair long. She simply had no interest in seeing me let alone being with me while en femme. It was a subject we rarely discussed and as my interest in crossdressing drew stronger by the day, avoiding it was becoming the proverbial 800lb gorilla in the room. Other than that tension, everything else seemed pretty much as it had been. Our sex life was good and we had a weekly date night we rarely ever missed. Still, I found myself wanting so much more and those new desires were becoming unbearable. One of those was the need to be seen in public. I desperately wanted to be able to go somewhere as Callie. Anywhere. And yet, another part of me had even more specific desires. Each time I took Sarah out dancing, I found myself wishing I could be there as Callie being asked to dance by the good looking men I could no longer ignore.

I tend to be obsessive and detail-oriented to the point of being anal. In fact, that's a word I hear rather often at work as I spend inordinate amounts of time ensuring my projects are as close to perfect as possible. I applied this trait to crossdressing and found myself constantly reading and researching areas like hair, makeup, accessorizing, and fashion. Makeup application was clearly the biggest challenge to actually looking like a woman and the progress I'd made was phenomenal.

In addition to growing my hair long, I'd also lost quite a bit of weight. I was down to 135lbs due to careful dieting and the distance running I so enjoyed. As I said, my body hair is light and that's especially true on my face. I'd heard a number of times from women over the years that I had "those eyes" meaning the kind that are framed by long lashes which look like a girl's. It was one of things Sarah most liked about me along with a perfect smile courtesy of the braces I'd once worn and along with my small size, the thing that made it possible for me to actually look like a women in drag.

Other than my increasing dissatisfaction with only being out of the closet, I made time for Callie as often as possible. It's amazing how quickly we take new things for granted and want more. Buy a new car and you think you'll be excited to drive it every day forever. Nope. Just a few months later and it's no big deal. Getting the okay to dress up from my wife was a dream for the first six months. Then I wanted more. Now the frustration was building and I had no idea how to "earn" more privileges without blowing up "the deal." That's when chance or fate or whatever intervened.

A week ago, Sarah and I got our wires crossed. I was under the impression she was working until midnight that Saturday, and I'd made plans to spend the afternoon and evening as Callie. After finishing all of my detailed preparations which took just short of two hours, I was utterly amazed at the beautiful woman looking back at me in the mirror. I'd had my long, dark-brown hair up in rollers for three hours after coming home from a total body wax and a long, warm bubble bath and cleansing shower. My makeup was as good as I'd ever seen it. The eyebrow template I'd designed allowed me to have perfectly shaped brows which framed my green eyes which were highlighted with dark-brown liner and a smoky-grey eye shadow. The false eyelashes were further thickened with just the right amount of mascara and the soft, cinnamon-colored blush sat on top of a perfectly blended liquid foundation which was all covered with loose powder. My long hair cascaded down my face and curled gently around it. I wore it shoulder length and curled it under at the bottom. Soft, wispy bangs fell from one side to just above my right eyebrow.

For my outfit, I'd selected a black, long-sleeved, rib-knit sweater with a jewel neckline and a moderately short goldish-tan skirt with a skinny black belt. I'd long ago ordered a computer-designed undergarment which gave me just the right amount of curves and a nice round tushy. I was wearing an expensive gold and black necklace with matching earrings and bracelet. I applied my own French nails which I'd painted to match my dark red lipstick. Silky suntan stockings and three-inch heels which matched my skirt and purse completed the look.

I was busy making dinner and with some light jazz coming from the stereo, I didn't hear either the garage door or Sarah enter the house around 8 o'clock. I'd poured myself a glass of merlot and as I set the bottle back in its place, I sensed motion behind me and to my left. I looked up and noticed Sarah, still in her scrubs, standing about ten feet away. My heart stopped and I froze in place not knowing what to say. In an instant I realized this was a make or break opportunity. I understood this was the way fate had chosen to present me with the chance to either take my love of crossdressing to the next level or possibly to divorce court. Instinctively, I knew Sarah's reaction would determine the path.

Sarah stood there motionless and just stared. Without saying a single word her eyes moved up and down several times taking in what she saw. "Oh—my—God," she said in a staccato voice. "Sothisis what you look like. Oh—my—God."

I started to speak when she said, "I don't want to discuss this now. I just need time to think. I'm not mad. I'm just confused. And shocked. I got off early and I was so exhausted I didn't think to call and warn you. I should have known but... Oh—my—God, Cal! You're absolutely, unbelievably beautiful." With that, she walked past me, picked up the wine bottle and poured herself a very large glass while I headed to the bathroom to remove all of my carefully applied makeup and turn back into drab old Cal.

Sarah said she didn't want to discuss this so I gave her her space. Our fifth anniversary was just two days away and my head was spinning with worries over how what Sarah had just seen might affect our marriage. I was also cautiously filled with hope that we might even reach our own version of FDR's "New Deal."

We went to bed a couple of hours later and neither of us spoke. In fact, Sarah barely said two words to me the entire next day which was Sunday. Tomorrow was our anniversary and I'd made reservations at her favorite restaurant. I'd also bought her a beautiful pearl necklace and matching earrings I hoped might soften the blow. I assumed I'd find out soon. That is, if Sarah was ever going to talk to me again.

The Restaurant

Other than asking what time our reservations were for, Sarah still hadn't said much of anything to me (she was off all day and this was also a Monday/federal holiday so I was home, too) and that only increased my level of concern which was now bordering on paranoia. The one thing that served to calm my fears was that Sarah was wearing my favorite outfit—a white, long sleeved sweater, a short black skirt, four-inch black heels, and a beautiful necklace with matching earrings. She had always been good about indulging my clothing fantasies so I didn't readtoomuch into it. My hope was we'd at least have a pleasant dinner and great sex later that night. My fear was hearing Sarah tell me she's not in love with a "woman" and that she wants a divorce. With all those thoughts swirling around in my mind, we arrived at the restaurant right on time after a short, quiet ride through moderate traffic.

An attractive young blonde seated us and told us our server would be with us shortly. In less than 30 seconds, a good-looking young man in a white shirt and black pants told us his name was Ken and asked for our drink order and if we'd like an appetizer. I ordered a bottle of expensive champagne as Ken thanked before leaving to take care of our order. As I turned toward Sarah, she slipped a Hallmark card out her purse and onto the table. She pushed it toward me and said warmly with the first smile I'd seen in days, "Happy anniversary, honey. I love you."

Before opening it, I reached into my jacket pocket and removed her gift and card, slid it closer to her and said equally warmly, "Sarah. I love you, too. Happy anniversary. I just want to apologize for the other...."

"Shhh," she said holding her index finger over her mouth. "It's okay. I'm not upset. Open your card."

"No, you first, honey," I told her.

"No, not this year. I want you to read what I wrote. So you first."

Love and warmth radiated from her eyes and face and yet it did little to quell the mishmash of thoughts in my head which had just turned into a veritable firestorm. She wants me to read what shewrote? What might that be? Is Callie being sent back to the closet? Is this the end of our marriage? Those and a dozen other questions took turns filling my cerebral processing unit as I opened the card and removed the contents. Inside of the card itself was a two-page, hand-written letter.

"Read my note first, okay?" Sarah asked again.

I unfolded it and began reading. "Dearest Cal. The last five years of my life have been the happiest. I love you so, so much. You've always been there for me. You've supported me and my career no matter how many long, crazy hours I've had to work. You've never once gotten upset with me or even raised your voice. In fact, you've spoiled me rotten and I don't take any of this for granted. Thank you and I love you. Now for the hard part." My paranoia gland filled with fresh blood as I glanced up at Sarah to see if her facial expression might reveal any clues. She was still smiling as she nodded to indicate I should keep reading.

"I've tolerated your 'special interest' for over a year now. I told you I didn't want to see you dressed 'that way' and that seemed to working well for both of us until Saturday. Let me just say that when I walked in on you, I was so completely stunned by what I saw, I found myself at a total loss for words. Page 2. The emotion I felt most strongly surprised me. I wasn't angry or even upset. I knew this was what you enjoyed doing. What blew me away was how much you actuallylookedlike a real woman. I kept looking and staring to find some flaw like an Adam's apple or big hands or anything and all I could see was a beautiful woman looking at me. What bothered me the most was all I could think of was that you looked prettier than me. I was so, so—jealous! I was upset. I felt hurt. I kept looking to find some clue you were a man but I couldn't find one. Your hair was beautiful. Your makeup was perfect. Your outfit was amazing and even your "boobs" and butt looked real! I was tired and sad and needed time to think. Well, I've done nothing but think for two days straight. In fact, I was awake all night thinking about what I wanted to say and how to say it. So here goes."