I've cross-dressed on and off since I was a young boy, sneaking into my sister's underwear drawer trying on her lovely panties and, later, bras and slips. I always loved the feeling of silk and satin and nylon against my body. Over the years, the opportunities to cross dress came and went.
Eventually, I met a sexy, smart girl and we got married, both in our mid-twenties. After I married Julie, I stopped dressing for many years. We loved one another and had great sex but decided not to have kids. I was doing well in my career as an electronics executive as was Julie as a real estate agent. Life was good.
One day, in my mid 30's, I stepped into the bathroom to shower and spotted a pair of Julie's panties on the floor. I picked them up and was turning to place them in the hamper outside the bathroom door when I had an old urge; the urge to feel that glorious fabric against my ass...against my cock. Trembling slightly, I slid them on. The feeling was electric. I immediately became erect. I sat on the toilet seat, eyes closed, caressing my cock through the silky fabric. I slid the panties down and my I began stroking my rock hard cock. I came in no time, spurting cum all over my stomach, legs and on to the panties. I managed to get them cleaned up and when they dried, I put them in the hamper.
From that moment on, I knew I badly wanted to wear women's clothes every chance I got. Of course, I didn't share this desire with Julie, deathly afraid that it would ruin our marriage. I did buy men's silk boxers and briefs. Although they never brought me the excitement of women's panties, I could wear them without arousing suspicion.
We led a busy life and over the years I collected a nice assortment of panties, bras, stockings, slips, blouses, shoes, wigs and makeup. All of it was carefully hidden in the garage. Occasionally, I would wear some of Julie's lingerie, being careful to return it clean and folded. I would dress fully every time Julie visited her family in upstate New York. Those 4 to 5 day periods were heaven, dressing from the minute I returned home from work until I woke up in the morning. I would take many of my feminine things on business trips, rushing back to the hotel after dinner to dress. Each time was wonderful.
After each business trip I would carefully separate my feminine things and put them in a small bag that I kept in the trunk of my car until I had a chance to move it back to its place in the garage. As a habit, Julie would empty my suitcase when I returned home and take care of the laundry.
At the end of one trip, I must have left a pair of blue stretch satin panties in my suitcase. They were Julie's and I had borrowed them. Of course I didn't realize this had happened until the panties appeared in my underwear drawer, washed, neatly folded and placed directly on top of my white jockey shorts. At first I was going to point out to my wife that she had misplaced her underwear in my drawer.
Then I realized what had happened!! She had found them in my suitcase, knew that she hadn't put them there and surmised (correctly) that I liked to wear them. I nearly panicked she never said a word; nor did I. If she hadn't recognized them as her own, she would likely have suspected me of being unfaithful.
Over the next several years, I "borrowed" her panties several times and when I did, she would always leave them in my underwear drawer, making them mine forever. I also started putting some panties that I had purchased in my drawer and she would always wash them and return them for me, never asking me about them. It became a lovely, unspoken arrangement.
As I moved into my late thirties and early forties, I needed to work out several times a week to maintain what was a fairly lean, athletic body. Each Monday, Wednesday and Friday morning I would rise at 5 AM dress in my workout gear and head to the club. Julie would place a shirt and suit on a hanger for me and would pack my gym bag with my dress shoes, socks and underwear.
On Monday, I finished a good workout and showered, shaved and headed back to my locker. After I finished toweling off, I reach into my gym back to remove my underwear. As I pulled out my shorts and T-shirt, I was mortified when I realized that Julie had inadvertently packed a pair of white stretch satin high cut panties instead of my jockey shorts. I looked around to see if anyone was looking. There were only two men in the aisle where my locker was. One of them, a heavy set gentleman, was straddling the bench, facing the other way, deeply engrossed in a cell phone conversation. The second, a tall nice looking dark haired man, was toweling off and apparently not paying any attention to me.
I was certain that I would have enough time to slide the panties on and then quickly slide on my trousers. After I stepped into the panties and started sliding them up my legs and over my butt I looked up and saw the attractive dark haired man looking at me intently. I thought I saw a slight smile, but I was rushing too much get my trousers on to be certain of anything.
After I had zipped up my trousers, I looked up and the sandy haired man was busy dressing, apparently paying no attention to me. Perhaps he hadn't noticed the silky material! But then I remembered the scalloped waistband, a dead feminine giveaway. Maybe he just wasn't paying attention.
On Wednesday, I went to the gym as usual. I spotted the gentleman from Monday while we were both in the bike room, sweating like crazy. He never seemed to notice me. I was safe! After completing the workout, I showered and was back in front of my locker, toweling off when I notice my "friend" at his normal locker, with his back to me, sliding on a pair of blue satin bikini panties. I couldn't keep from staring. He turned around quickly and his eyes met mine. He smiled and quickly slid on his trousers before anyone else could see his sexy panties.
I was shaken. I couldn't decide what to make of what I had just seen. Had the man always worn panties and I hadn't noticed? Did he wear them especially for me to see after seeing me in panties? More importantly, why was I getting an erection as I pondered these questions?
Like most cross dressers, I spend time online, chatting with other "girls". Often these chats develop into bisexual cybersex. But that was only online fun. I wasn't really gay or bisexual....was I?
I decided to skip the workout on Friday, still confused about what I had seen and how I felt about it. After spending most of the weekend thinking about what had happened, I decided to force the issue. I took with me a pair of dark blue bikini panties with a lace patch in front. I was taking a chance, but I thought I could manage it. I would insure that my "friend" was the only person in the aisle when I put them on. (Plus, I had a backup pair of white Jockey shorts, just in case).
I wanted to send a message to Mr. X. I didn't know exactly what the message was supposed to mean, but I felt an irresistible desire to send it. After toweling off I waited until he was looking in my direction and I slowly slid my panties on, looking at him as I did so. He smiled and slid on a pair of white satin panties, similar to the ones I had worn the previous week. I quickly finished dressing, as did he. As I walked from the locker room, he walked beside me.
He spoke quietly, and said, "My name is Mark Evans", and extended his hand.
I nervously responded, "Jim Tonesh here, nice to meet you".
We continued walking side by side until we reached the small coffee shop that the club had.
Mark said, "Can I buy you a cup of their lousy coffee Jim".
I didn't know whether I was hoping for this or fearing it, but I said, "Sure Mark, sounds good".
We drank our coffee and chatted about mundane items when suddenly Mark asked, "How long have you been dressing Jim"? I knew that he knew and I was both relieved and excited. I told him my story and he told me his. It was so wonderful to speak freely with another person about the secret that I had been carrying for so many years. Our stories weren't much different, except that Mark had never gotten married. This of course, permitted him to dress whenever he chose.
Then the conversation took a more intense turn. Mark looked at me and softly said, "You panties looked wonderful on you Jim".
I was stunned. A man was talking to me about my panties. I felt my panties become strained as I had an immediate erection. I was speechless.
Mark was sweet. He sensed my discomfort and we changed the subject for a little while.
As we were preparing to leave, Mark gave me his business card and said, "I'd like you to come to my place sometime for a drink. We could both dress and see how we look to one another". It turns out that Mark had never been out in public either. I took the card. We shook hands and I said that I would be in touch. I knew at that moment that I was going to do it. I was going to go to the home of another cross-dresser and we would dress together, be girls together. It was something that I had always wanted to do, but thought that it would never happen because the risks were too great. But I felt safe about Mark. In most ways he was a neophyte just like I was. I was excited.
Friday came and I was almost too excited to work. I had decided that today was the day when I would call Mark and accept his invitation to go to his home, to dress as women together, to be girls with one another. I had worn panties to work many times before, but on that day I found myself fighting off and erection all day long. Finally, around three PM I had to go into a bathroom stall and masturbate, just to calm down.
Funny thing: as I masturbated, I just kept visualizing Mark's tight ass in those white panties. I returned to my office and dialed Mark's number. As his phone rang, my heart raced in anticipation and I wondered if I would be able to control my voice when he answered.
The strong, soft voice on the other end spoke clearly to me, "This is Mark Evans".
I gathered myself and said, "This is Jim Tonesh, Mark. We met last week at the club".
There was a slight pause and then Mark said, "I'm really glad you called Jim...really".
From that point forward we relaxed and chatted amiably and we agreed that we would both leave work early the following Wednesday and that I would arrive at Mark's house around one PM. We chatted a bit longer and said our goodbyes.
The weekend at home was uneventful. Julie and I had dinner out on Saturday night and Sunday was mostly taken up by running errands and doing yard work. Julie was a little flirty, but she sensed that I wasn't in an amorous mood and she changed the subject easily.
Over the next few days, I found the moments alone at home that I needed to collect my feminine things in a small bag that I put in the trunk of my car on Tuesday night before going to bed. I had told Julie that I had a call to make on a client in a town that was about two hours away, that I be would driving there and there was a chance that I might need to spend the night at a local hotel. So I packed another small bag for that possibility.
The next morning at work I was next to useless. I could barely concentrate on the simplest items. Somehow I made it through until noon and when I headed for my car in the parking lot I breathed a sigh of relief and began to finally allow myself to let the excitement inside bubble up an wash over me. When I arrived at the nicely maintained ranch style house in a quiet neighborhood I was excited, but calm. Mark opened the door and greeted me before I had even knocked. We shook hands and he offered me a drink. I accepted a glass of Chardonnay and we chatted quietly for fifteen minutes or so.
Finally, I said, "Mark, why don't we get dressed honey"? I was shocked! I had just called Mark "honey"!
He smiled, touched my hand briefly and said, "Good idea, Jim''. As Mark showed me my room and bathroom he asked, "By the way, what is your femme name"?
Slightly embarrassed, I told him that it was Kathy. He smiled and said that his femme name was Emily.
As I entered my bedroom, I turned, smiled and said, "I'll be a little while Emily, I need to bath and pretty myself up". I smiled and tossed my head like a girl.
I closed the door, undressed, unpacked my bag and went into the bathroom. I was struck by how feminine everything was. The décor was soft pastels and the shelves were filled with lovely scented oils and both crystals. I took a warm bubble bath, shaved my legs carefully for the first time in my life. I had decided that this was a chance I needed to take. After all, my body hair was light and fine and that the fact that my legs were shaved wouldn't be overly noticeable.
In any case, it was a glorious feeling. I even trimmed my pubic hair to a tight little bush. I have very little chest hair, so making my chest smooth was a quick job. After I finished bathing and shaving I applied some lotion and dressed in black satin and lace panties, matching bra, silicone breast forms, a black silk camisole, a tight black skirt that was 4" above the knees and a black silk blouse. I saved the nude thigh hi stockings until last, knowing that the feeling of stocking sliding over freshly shaved legs would be exquisite. It was. I was briefly breathless.
I slid on my black strappy pumps and sat down at a lovely dressing table to carefully apply my makeup, paying particular attention to my eyes and my dark red glossy lipstick. I then attached my dark red false nails. Finally, I brushed out my shoulder length auburn wig, carefully placed it and checked myself in the mirror. I smiled and said to myself, "You look pretty good Kathy". I applied a few drops of Giorgio Red to the appropriate places and strode confidently into the living room to meet Emily.
I couldn't believe what I saw. Emily rose from her chair and smiled at me. She was wearing a beautifully fitting long sleeved black cocktail dress with, black stockings, classic black pumps and striking shoulder length black hair.
Emily walked toward me, took both of my hands in hers and kissed me softly on the cheek, whispering, "You look so lovely Kathy". She smiled and turned to get me a fresh glass of wine. As I looked at her from behind, I was still stunned at how feminine and seductive she looked.
We sat together on the sofa and chatted about feminine things, like our clothes, our makeup and the like as romantic music played softly in the background. We both began to get a little silly about girl things. As we laughed we would occasionally touch one another's hands or shoulders.
After 30-40 minutes Emily rose briefly to adjust the CD player. When she sat down again, her hips were pressed against mine. She was so close. When we looked at each other, our faces were so close. I breathed in her seductive fragrance. I was overcome with Emily's closeness. As we turned to each other, without a word our eyes locked and our lips moved together.
The first kiss was soft and feminine. I caressed her cheek as she did mine. We tasted each other for the first time and as I parted my lips slightly, her tongue tentatively probed between them. Without thinking, my fingers went to her waist and gently pulled her closer. The kisses became more intense. As I turned toward Emily, my skirt rode up, exposing the tops of my stockings. Emily's dress rode up as well and our stocking covered legs became entwined. The feeling of our stocking covered legs sliding together was heavenly.
After a few moments our kisses became softer and we began to explore one another's bodies with gentle caresses. My hands found her breasts and squeezed them softly. I ran my fingernails along her silky stockings as she did mine. I caressed the insides of her soft thighs, finally reaching the tops of her stockings and then caressing the lovely flesh there. Emily responded with similar exciting touches on my body. I trembled slightly when she reached my satin and lace panties. Her fingertips danced across the front of them and I moaned as we continued to kiss.
Finally, we paused and stared deeply into each other's eyes. Somewhat shaken, I said, "This is my first time Emily".
She smiled, took my hand to her lips and kiss the palm and replied, "It's my first time too darling Kathy".
Emily stood before me, took my hand and without a word I stood and we walked, hand-in-hand to the bedroom. My heart was racing. I knew now that this was what I wanted and excitement and anticipation swelled within me. When we entered her bedroom I noticed that the shades had been drawn tightly and the room was darkened. Emily silently went about lighting several candles that cast a romantic glow throughout the room.
Emily came to me and we embraced kissing deeply, her arms around my neck mine around her waist. This kiss was long and passionate. Without a word being spoken, she began to unbutton my silk blouse and removed it. While she did that I unzipped my skirt, let it fall to the floor and stepped out of it. She turned her back to me, I unzipped her cocktail dress and she turned to face me and let it fall as well. She was wearing a black slip over her black thong and lace bra. We embraced again. My hands moved hungrily over her silky lingerie and hers over mine as we kissed again.
Emily the led me to the bed and wordlessly I lied down, staring up at her. She knelt beside me on the bed and began to kiss me everywhere. My head was spinning with desire. I caressed her soft hair as she kissed my neck, my shoulders, my bra, my hips, my panties and down my legs. She stroked and kissed my long legs and slowly removed my heels and then kissed and sucked my toes through the stockings. My legs parted slightly as she moved between them and pressed her entire body against mine. Our silky lingerie rubbed deliciously together and I felt her thong, now bulging and damp, pressed against my panties. It took my breath away.
Emily whispered in my ear as we lay together, "Kathy, I've wanted this since I first saw you watched you slide on your panties in the locker room".
I replied, "Darling, I've wanted this from the moment I saw you in YOUR blue satin panties as well". My hand went between us and I caressed her cock through the thong. I felt her tremble and heard her soft moan.
We kissed and touched one another for several minutes until I said, "Lie on your back darling, please".
She complied willingly and my lips went immediately to her thong. I kissed and licked it hungrily as my hands caressed her warm, smooth ass. As she stroked my hair, I slid the thong down her legs and off. Her erect, slippery cock was now before me. I touched it gently, the first time I had ever touched any cock but my own. Then I wrapped my fingers around it and slowly stroked it. Emily's hips moved involuntarily as I stroked her beautiful cock.
I could wait no longer. I looked into her eyes and lowered my lips to kiss the glistening head. Finally, I slid my lips over the head and took her warm, hard cock into my mouth. It was everything I expected and more. I couldn't get enough of it. I sucked her and licked her, caressed her shaved balls softly. Her moans and breathing excited me even more, although I didn't think that was possible. I tightened my lips and drew her pre-cum into my mouth. It was heaven. While holding her cock, I began to move my head up and down quickly and steadily, feeling her grow in my mouth, I wanted her cum so badly. I moved faster and faster and my lover's moans became louder and more urgent. Then she came. I continued to suck her and felt her body tense and felt her cum explode and spurt into my mouth. I loved the feeling of the warm cum. I never knew it would be like this. I continued to suck her glorious cock until she relaxed. I kissed and licked up the cum that had escaped my lips.
Emily said hoarsely, "Please kiss me Kathy, my sweet lesbian lover". I moved up her body and we kissed. She licked her cum from my lips and we kissed lovingly. Then we held each other tight and were silent for several minutes.
Emily stroked my hair as I rested my head on her breasts. She said, "Kathy, you are a wonderful and sensitive lover. I'm so glad you are the first". Then she moved down my body and slid my panties off. She stroked and caressed my cock as I had hers. When she took me in her mouth for the first time, I thought I would faint with pleasure. She made me come with her warm, loving lips and tongue and mouth. I was spent and she continued to hold my cock softly in her mouth for a long, sweet time.
We laid in bed for a long time, holding one another close, our somewhat soft cocks pressed together, both of us in blissful exhaustion. I didn't ever want to move. We drifted off to sleep and slept for some time.
When I awoke, Emily kissed my eyes and cheek and said, "I want you inside me darling". I smiled sleepily, kissed her neck and moved between her legs. "There's some lubricant on the bedside table sweetheart", she whispered.
I got the slippery lubricant and she took some and spread it on my now fully erect cock. I took some on my fingers and gently lubed her pussy as she lay there. My finger penetrated her slowly and she moaned in pleasure. I moved it around and in gently and then a second finger. Emily squirmed and moaned and pressed her pussy against my hand. I loved bring her pleasure like this and softly sucked her cock as my fingers explored her pussy and excited her.
After a few minutes Emily hoarsely said, "Kathy, please fuck me baby. I want to feel your cock deep inside me".
I stood and moved to the edge of the bed, raised her long, silky legs. Pressing my lubed cock gently to her warm, slippery pussy I first leaned down to kiss her soft lips gently. Then I pressed my cock more firmly to her pussy and it popped in so easily that I was a bit surprised. She and I moaned simultaneously in ecstasy. I slid in further and felt her warmth surrounding my engorged cock.
We moved together as though we were long time lovers, in perfect rhythm. She reached with her long arms to dig her mails into my ass and pull me even tighter to her. My cock went in, up to the hilt and once again we both moaned.
"Oh sweetheart", I whispered as we continued to build to a climax.
I stroked her hard cock as we fucked furiously. Our movements became faster, more urgent, aware of nothing but our passion. Then I came powerfully, pouring my cum into her pussy. I felt her cum at the same time, her warm juices spurting against my stomach and running down into my bush. We collapsed into each others arms, kissing caressing, knowing that we would be lovers for a long time.
After a long drowsy period holding one another closely, we slowly showered together, enjoying each others company and kissing periodically.
As we toweled each other off and Emily smiled and said, "Maybe we should shower together at the club darling". We both giggled like school girls and then went to our separate bedrooms to dress.
I decided to slip on fresh lingerie, a short sexy ivory nightie, nude thigh hi's, feminine slippers and a short ivory silk robe that matched my nightie and showed my long legs nicely. I re-did my makeup and touched up my wig and went to see my lover once more.
It was a winter day and it was getting dark early. As I entered the living room there were no lights, but there were candles glowing and a warming fire in the gas log fireplace. Emily was waiting for me, looking even more beautiful than before. She too had decided to dress for bed. She was wearing a black, see-through peignoir through which I could see a sexy nightie with thin shoulder straps, black stockings and a sexy garter belt with a small red rose in the middle.
Silently we came together and kissed softly. "I've never experienced anything like this Emily", I whispered as I nuzzled her neck.
She looked deep into my eyes and said, "Nor have I my sweet lover".
We cuddled and chatted in front of the fire for hours, sipping a nicely chilled chardonnay. Eventually we again walked together to her bedroom, knowing that the night held more exquisite lovemaking in store for us; knowing that this was only the beginning.
But then, what about Julie?