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Maybe I should have become suspicious when I saw him for the first time in this flowered apron. Or at last when I found the bag of make up and female toiletry in the back of the bathroom cabinet. Back then I had be convinced that it had been from a Caroline or another female friend. Even when it was too much assorted to be just a left behind.
For me the big revelation came the day when the goons of Colonel Oliver had abducted Jim. They had searched our apartment to get a clue about how much Jim knew and the whereabouts of me; more like ransacked would be the better description, and had thrown out all the contents of the drawers and closets. I had returned to the loft under police protection. Devastated about Jim's possible fate and unable to do anything else useful I started to put everything back in its place, and found... a couple of dresses and silk stockings. Even then I still opted naively for the easier explanation that it had been Caroline's.
Until I saw the shoes.
Jim has big feet, pretty, well formed feet, but nevertheless big. As were the shoes. They weren't by any stretch of imagination female shoes. They even didn't fit my feet! A pair of black pumps and another pair of white, high heeled sandals.
After that I was dumbfounded, sitting for a while on my butt in front of the closet holding the shoes trying to wrap my mind around the incriminating find. Suspicious, I then took a closer look at the dresses. They too were his size. Elegant and feminine, no cheap stuff. Bought mostly out of the country, as far as I could tell. A fine smell of expensive perfume lingered on them. I put everything away carefully.
I didn't freak or anything. I know that something like that happens more often than people like to believe. Most men have tried on a woman's dress secretly at least once in their lives to find out what it was all about, but would only admit it under torture. See, women wear men clothes, but not the other way around. Except maybe if you are a member of a British pop band. And Jim, well Jim, was the repressed military type, grew up in an all male household. I assumed that he had the need to balance his machismo. Getting in touch with his female side or something. The big question that was nagging in the back of my head was: did he like only to dress up as a woman, or did he like men too?
Nevertheless my picture of him had changed a lot after this discovery. I had seen him in the beginning of our friendship as this macho, comic style superhero. Man of all men. Tough as nails and it had excited but also intimidated me. Therefore I had looked down at him for it a bit, for being a Neanderthal without hidden depths. And now I really admired him for being special, vulnerable and yet strong and brave. I had thought he was brave because he was too stupid, too one-dimensional to think otherwise. But no! This macho hombre dressed up in his spare time in a Chanel combination to allow himself to be different.
When we got him back I was so glad I hugged him and he smiled shyly and pleased at my outburst of joy to see him alive. On my way home from the police station and a short stop at the hospital I told him everything about our search and all my fears and worries. When we were back at the loft I told him also that they had turned the place upside down. Everything was in his place again now. He stared at me for a moment but I only smiled at him. What could I do else?
When he went up to his bedroom I was sure he would look and find his stuff where it hadn't been before. My smell would probably cling to it too. He didn't say a thing that night. There were only some thoughtful stares. I was relieved. His abduction had been traumatic enough for both of us. This wasn't the time or place for discussing his kinky games right now.
But he must have known I'd seen it, because when I went up a few days later to carry up the laundry I peeked into his closet. The dresses were gone and the boxes with the shoes too. I found them at the back of the closet wall hanging on a new nail and shoes were pushed back. I left the laundry on his bed. When he came home I tried hard not to grin inanely. I didn't want to give him the impression I was amused or something. He gave me a sharp once over, like he had learned in covert ops. The moment he entered the bathroom to shower I knew he had relaxed.
I wasn't also entirely sure how to handle this. I was experienced enough in the fine art of human interaction to understand my limits in this delicate situation. Besides it wasn't really my business.
So I simply waited and Jim came forward with it himself, probably dying out of curiosity what I was thinking about that matter.
We were on a stakeout when Jim began out of nowhere.
"I wanted to ask you something for a while. Did you clean away my room after the break in? Put my stuff away?"
"Yep."
"All of it?"
"All." I confirmed calmly and waited. The silence stretched. "You mean the women's clothing?"
Jim looked down at his hands, kind of embarrassed.
"I did put it away, nobody else saw it." I assured him. It hadn't occurred to me that he might be worried the other cops had seen it.
"Good."
The silence was heavy and I felt the need to make a comment about it.
"Pretty elegant clothes."
"You think?" Jim asked to my surprise, pleased.
"Do you ever wear them?"
"Sometimes." Jim squirmed a bit, unsure what to think about my curiosity.
"One day I'd like to see you dressed up like that," I told him earnestly.
Jim stiffened a bit and threw me a sharp glance as if I was making fun of him.
"I don't think so, Chief. I don't do this for an audience." He growled.
I shrunk back a bit in my coat. "It isn't like that. I ... I want to know what's like. I..." I whispered, shocked about my own audacity and desire to want to be part of this secret.
And Jim recognized in my eyes another fellow pervert. He saw I had fallen hard, wanting it too and it excited him. He grinned, delighted.
"Okay!" He drawled.
There was a promise of forbidden delights in his wicked smile that made my stomach flutter.
Later we drove home and I knew we would do it right now instead of sleeping after a night of watching the docks.
"I haven't done this in a while," Jim murmured
He expertly ran the razor along his shapely legs. I sat on the ledge of the bathtub and watched amazed. His legs looked bare, different, sensual. Then after some thoughtful hesitation he shaved his forearms too. Standing in his black, silken boxers he finally shaved his face with slow carefulness.
I watched with rapt attention as he applied his make up expertly, like he had done this a thousands times before. He transformed in front of my eyes.
"When I'm on vacation I pick my eyebrows to a fine line," He explained.
I nodded. He didn't layer it thick like some drag queens. It was decent, like a make up that didn't look at all like a makeup. Only his very long, thick lashes looked killer. He had awesome beautiful eyes and the light eye shadow made them perfect. A pink lipstick without lining or gloss, only a hint of gold. He added slender ear clips. When he slid into his silk stockings and fastened them on his garters I had to swallow. His legs were incredible.
We walked up to his room and I sat on the bed while he tried his dress out, with shoes and jewelry and all. One after another were presented. All fit perfectly, elegantly. He strutted around and turned so I could see all angles. Every dress had a story behind it, where he had bought it and why. When he finally sat down beside me in a pink, classic Channel costume, with silk blouse and white sandals I was devastated. He was awesome and he reminded me of Annie Lennox of Eurhythmics. It was the short hair and the long angled face.
"So what do you think?" He asked.
"Can I try one too?"
"You want? You look as if you want to try it too."
I nodded. "All the way."
It was true. I had fingered the fine cloth of his dresses and had been fascinated and intrigued by the idea to have something like that at home, as a secret pleasure. Change yourself into a different world, a different feeling and perception of yourself. If I hadn't been so worried about Jim, during his kidnapping, I would have been tempted.
"I do, I mean I want to know what it feels like. It looks great."
"Thanks!" Jim smiled. "Do you want to now?"
He studied me as if to take measure. "How about the little black and the pumps. We can stuff them."
"Okay!"
And then started the weirdest afternoon of my life. Blair Sandburg's transformation into a woman, with the help of his very macho best friend. I felt like being in some of this girly High school comedies, where the girls have a pajama party and try their new make-ups and cloths.
I shaved like he had done, legs, arms and in my case, chest. It was exciting and arousing. A sublime arousal from the strange feeling on my skin and the closeness of another human being I cared about a lot. If Jim noticed something he didn't show it, but I was sure he wasn't entirely oblivious to the implications of the situation.
My heart hammered in the anticipation of doing something forbidden and crazy. Jim felt it too. We both felt crazy. I could see he got a kick out of it to work me over and I felt languid under his hands like under a spell. His hands touched my face delicately when he applied the make up. His face was very close to mine and I was almost panting and getting aroused in earnest.
"You have such beautiful hair, you could do so much with it. I wished I had some like that. I could play all day with it." Jim admitted.
My obvious nervousness and excitement was catching and Jim let himself go and touched me more and more intimately, giving in into the draw that was building between us due to sharing what was a wonderful taboo.
He helped me into my stockings, running his hands over my legs smoothing out the folds. When his fingers touched the back of my tights to close the lock of the string from the garter my cock leaped to attention. That touch was too intimate
I ran my hands up the inside of my legs. The sensual feeling was overwhelming. The skin was tingling and hot. I could fuck myself, I was so hot. The air was thick and smelled of heavy perfumes mingling with our musky male scents. The artificial light in the small bathroom gave us a demi-world look. Wicked, dangerous, erotic.
Staring in the mirror and cupping my chest, I realized that I wanted a bra to fill my breasts. Jim didn't use one with his hard pecs it didn't work. He filled his dresses anyway. Or better a corset. Black satin. I knew I wanted one, restricting myself, changing my male form. Jim rested his hand at the small of my back and ran it up my spine until it rested possessively at the nape of my neck. I shivered. There was some promise in that gesture. That this could be come more than just a dress up.
Jim chose a perfume from a row of expensive flacons. He opened Poison and carefully wetted his fingertips. Then he rubbed it slowly, gently along my jugular on both sides. More drops landed on my wrist and inside my elbow. His face questioned me and he bent down and run his finger down inside my stockings, along the main artery feeling the rapid pulse. I gasped for air when the smell emanated from my heated skin.
"You okay?" he murmured.
"Yeah. All okay." I sighed.
He smiled at me seductively and gave me the stuffed pump. The silken lining of the dress glided sensually over my heated skin when I peeled it over my head and down my body. Jim turned me around, holding onto my hips while he closed the long zipper. I shimmied around, trying to find the right fit in the tight garment. Then I turned around towards the mirror.
I didn't know myself, nor the woman behind me. We were someone else. Some other secret part of us let out for a rainy afternoon in the secluded walls of the loft. My dick was pushing at the front.
Suddenly awkward, I asked: "And what do we now?"
"Drink champagne," Jim declared, frivolous.
He walked out for a bottle form the fridge and two fluted glasses. He handed them to me and easily opened the bottle. The bubbling liquid filled our glasses and we went over to the couch, sat down and grinned and toasted each other.
"To Blair and his new life!" Jim laughed.
We drank delicately, not wanting to ruin our lipsticks. I found that looking that good involved a lot of strenuous behavior. But it felt completely different. I could understand why Jim did this. You felt like being someone else. Someone aristocratic, beautiful, special. Humans have painted their bodies for ages to become someone else.
It is the opposite to sit around unshaved, unwashed in your dirty underwear with a beer watching a game and throwing popcorn at the TV. It had its moments too, no doubt about it. But that you could have all the time and nobody would look down at you for it.
I thought next time we should have caviar and salmon sandwiches going with the champagne and watch an opera or maybe Ed Wood. Too bad that we couldn't go out like this to an exhibition of contemporary art down at the upscale wharf promenade. I had to giggle at that thought.
"What is it?" Jim asked, grinning.
"I just thought what we could do next time."
"I see, you like it? Got you hooked?"
"Yeah!" I looked down at myself. "Very much. I could get used to this. And I want my own dress and shoes."
Jim raised an eyebrow in amusement. "I think I have corrupted you."
"Totally!" I agreed. "You showed me the pink side of life. The only drawback is when they would find us like that it would be sooooo embarrassing."
I had calmed down a bit from the drunken arousal in the daylight of the living room.
"Who? I mean, when was your first time?"
The champagne was starting to make me lightheaded. Jim leaned back into the couch and smiled secretly folding his long legs elegantly.
"As a kid," He studied his rosy polished nails, " I raided mom's wardrobe."
"Me too." I admitted. "I dressed up in Naomi's clothes. Of course she knew about it."
Jim grinned as if he didn't expect it otherwise.
"I had a girlfriend who liked to dress me up."
"Really?"
"She got off from it. We had always wild sex afterwards."
"It became a habit then?"
"Kind of." Jim admitted.
"Did you?" I coughed, I wasn't sure I could ask this.
"What? Spill it, chief!"
"Have you ever been with a guy?"
"In female clothes?"
And I thought he meant he dressed up together with another man in female clothes like we had done.
"No, I mean had sex with another guy?"
"I know what you mean, Sandburg."
I held my breath, watching him expectantly, hopefully. He avoided my gaze as if not sure how to answer this. As if the answer would change everything. Jim put his glass down and studied me for a moment and then he leaned forward and kissed me gently. I kissed him back fiercely and he groaned. Pressing against me closely he ran a hand up the silky dark heat between my legs. When his finger touched my dick I thought my heart would stand still. The last coherent thought I had was that we would smear our make up. After that we were all squirming bodies and tangled limbs.
Jim drew back and tore off his jacket. He kneeled on the couch and tried to shove my dress up my tights. He got a hold on my panties and pushed them down. There was something fierce in his face and I though 'oh my god' with my legs up in the air.
He grabbed my ankles hard and stared between them down at me.
"I'm gonna fuck you, Sandburg," he growled.
"Go ahead!" Was all I could manage.
He scrambled up and disappeared into the bathroom. He returned immediately. His skirt was gone and he was opening his blouse. I got up when I saw the package of condoms and the lube. He leaned me forward over the back of couch and I got a good view of his CD collection when a slick finger entered me. I couldn't suppress my jerking when one after another pushed in.
"Hold still!"
"Ungh," gritting my teeth.
Jim kneeled behind me on the couch, holding one arm firmly around my middle while his other hand guided his dick in. I felt split open and gasped in pain and pleasure trapped between the couch the heavy muscled body behind me. Growling and grunting Jim pressed his arms against my ribs until it became almost painful. When his balls finally rested against my ass, we both were breathing heavily. He nuzzled my hair and ear.
"Gonna fuck you so good, Blair. You'll never want anybody else," He promised.
I pushed back against him in invitation. His instant natural reaction was to nail me into the couch. My dick was worked against the stuffing and I had this monster on my back that tried to break me in two. The moment I was ready to come Jim drew out and I cried in disappointment. Jim flipped me over onto my back wordlessly and shoved in again. Hanging my legs over his shoulders, I could watch him. Beautiful, so beautiful, so powerful, over me.
Coming he arched and shouted my name. I bent upwards, clutching at him coming too like mad.
We tumbled from the couch together without hurting each other. Exhausted we simply lay there and his hand ran restlessly over my body, caressing me until he fell asleep half on top of me.
I lay there for a while staring up at the high ceiling. Dust was dancing in the golden rays of the evening light that shone through the high windows. Ever since I had found that shoe I knew I had opened a door to another life. And it had been far more than I had expected.
Later when Jim woke up and we got up from the floor we had to laugh about our smeared make up and how silly we looked. Debauched, sluttish. Jim looks great - sluttish in silk stockings and garter and nothing else except a few outstanding hickeys.
We made grilled sandwiches and tomato soup. Munching his sandwich Jim explained to me where I could buy pumps, lingerie and a dress of my own.
There was one question left that was burning inside me.
"Is it the clothes, or would you have sex with me anyway?"
Jim tilted his head and smiled gently.
"Sandburg, you are sweet piece of ass. I would fuck you anyway you are."
Such a sweet talker!