My cross-dressing journey started when I happened upon a pair of my then girlfriend's panties that she had mistakenly left in my college dorm room. They were pink nylon bikini-style panties with pretty white lace accents. She had worn them a few nights previously when we had gone out on a date, returning to my room afterward for some wild, passionate sex. I remembered with a smile how she had looked so incredibly sexy wearing them. I don't know what came over me, but as soon as I picked them up, I had an intense urge to try them on. Before I had a chance to change my mind, I quickly dropped my pants and boxers and slid the silky panties up my legs and into place. The feeling was indescribable. They looked and felt amazing on, and I quickly brought myself to an explosive orgasm just by sliding my hand over the nylon fabric covering my rock-hard cock.
From that point on, I was hopelessly hooked on purchasing and wearing women's panties. Over time, I expanded my enjoyment to wearing other types of lingerie by adding bras, slips, camisoles, garter belts, and stockings to my feminine wardrobe. I couldn't get enough.
All of this did not come without its own set of problems, though. There were many instances over the years when I amassed a nice stash of women's lingerie, only to do my best to suppress my dressing habit when the feelings of guilt and embarrassment would inevitably set in. I entered an endless loop where I would purge my entire stash of women's clothing only to start the cycle over and over again.
I had always hidden these urges from my girlfriends and made sure to only partake in my dressing away from prying eyes.
Eventually, I found someone special. Julie was all I ever wanted in a woman. We dated for over a year and eventually were married. Those first years were amazing as our love grew. I did my best to try to push my cross-dressing out of my mind, as difficult as that was. I had hidden my entire cross-dressing past from her in all the time we had been together. Soon I realized I had made the biggest mistake of my life in not telling her of my desires for wearing women's clothing. Of course, I had stupidly thought, once again, that I could push that all away and bury my urges to wear pretty things.
That, of course, was a fallacy, and within a few months, I was secretly purchasing and wearing pretty lingerie again. I carefully hid everything in a trunk in the attic, where Julie rarely ventured. I only wore my silken treasures when she was out of the house for long periods at a time.
This continued until the inevitable happened. Julie had decided to do a little spring cleaning while I was out of the house. The attic was the first on her list to clean, as we had started to collect quite a lot of boxes filled with things we rarely, if ever, used. She figured this was a good time to donate anything we no longer needed to the Goodwill. Of course, that meant she eventually discovered my stash of sexy lingerie in the trunk.
When I got home from work later that day, I was shocked to see my wife sitting in the living room with my trunk in front of her and my stash of clothing piled all around her. She looked at me with anger in her eyes and asked what I was doing with all of this women's lingerie.
With nowhere to turn, I spilled my guts, explaining my lifelong love of wearing sexy women's lingerie. How I had tried multiple times to stop over the years to no avail. I apologized profusely with all of my heart for never telling her about this side of me before now.
She asked all the standard questions that cross-dressing men hear when their secret is finally exposed. Have you ever cheated on me? Do you want to be a woman? Do you want to be with men?
I answered all with a no, again trying to express how it was just the wonderful feeling I received from wearing such pretty and feminine clothing. How it made me feel whole as a person. We talked for over an hour about how I had started my cross-dressing journey, along with my history of wearing, purging, and then starting the cycle all over again.
Her anger started to subside a little as her mind tried valiantly to absorb all of this information and come to terms with all I had told her. Julie said she needed some time to unpack everything we had discussed, and we left it at that for the time being.
After a few days, Julie broached the subject with me once more. She asked again if I wished to be a woman and if I wanted to be with a man. Again, I reiterated that it was just the look and feel of wearing the women's lingerie that I loved so much. She looked into my eyes and struggled to see if I was being honest with her.
To tell the truth, I had often fantasized about exactly those scenarios many times. What would it have actually been like if I had been born a woman? What would it be like to be with a man wearing just my most feminine lingerie? What would it be like to pleasure a man with my mouth? I had brought myself to many powerful orgasms over the years, my mind picturing those fantasies as I slid my hand over my cock while wearing my silky treasures.
Of course, I did not admit any of that to Julie.
Julie let me know that she had done some research on her own and was OK with my dressing but would prefer I only did it when she was out of the house. She told me she loved me and would accept my need to dress but could not bring herself to actively participate any more than that. She only wanted the man she had married whenever she was home.
I yearned for her to fully accept my cross-dressing but gratefully accepted all that she could give at that time.
Several months passed. I dressed whenever I had the house to myself for an extended period, but unfortunately, that was a fairly rare occurrence. Julie even got into the habit of calling me to let me know she was on the way home so I could remove my women's clothing and pack it away again before she arrived home.
I was always only in male mode around her. On occasion, I would try to talk with her about my need to dress more frequently and not continue to hide myself from her. She always quickly brushed me off and changed the subject. This led to long periods of time when I grew terribly depressed. It upset me that I could not be my true self around the woman I adored. I believe Julie started to notice this. She could not help but notice how I was frequently moping around the house.
My birthday was coming up soon. Julie was very quiet about what she had planned for my special day. In the past, we had always been so excited to go all out for each other's birthday. We normally made all the plans together. This time Julie was very secretive about it and would not share anything she had planned for me, no matter how much I pried. She just said she had something in the works that she knew I would really enjoy.
When my birthday arrived, I was awakened with Julie's lips wrapped around my morning wood. As I rubbed the sleep from my eyes, she pulled off of my rock-hard shaft and smiled.
"Happy birthday, my love," she said as she took my cock back into her warm, wet mouth again.
She swirled her tongue around my head and then plunged her luscious lips down on it with wanton abandon. Her talented mouth was working wonders. I always loved watching Julie enjoy herself on my cock. It was one of my favorite things to experience. My hands were soon clenching the bedsheets as I got closer to the point of no return. Sensing this, Julie redoubled her efforts. Her cheeks dimpling in as she increased the suction she was applying. I could feel my cock swell in her mouth as I erupted with a groan, shooting rope after rope of my hot cum into her warm and willing mouth. She swallowed greedily, draining me completely before releasing me from her mouth, a string of cum stretching from my tip to her luscious lips.
"That was just the first part of your gift," she said, wiping her mouth with the back of her hand. "I will have breakfast ready for you in a jiffy. Why don't you take a quick shower to clean up? I will put some things out for you to wear when you come down to breakfast."
She kissed me hungrily on my lips. I could detect the faint flavor of my own cum on her lips and in her mouth. With another quick kiss, she was out the door.
I stretched and climbed out of the bed.
"Well, this might end up being a very happy birthday indeed," I thought to myself as I headed for the shower.
I took my time and relaxed as I showered, taking time to shave my legs as I had been doing for several months now. Once finished, I stepped out and dried myself with my towel before wrapping it around my waist. Applying some moisturizing cream to my freshly shaved legs, I luxuriated in the feel of being totally smooth again. I headed back into our bedroom to see what Julie had picked out for me to wear, probably just a new pair of pajamas or a new t-shirt and sweats for my birthday.
I stopped in my tracks when I saw what was laid out on the bed. It was a short pink nylon baby doll nightie and a matching pair of pink nylon panties. There was also a brand-new pair of white lace-top thigh-high stockings placed next to them. I just stood there with my mouth agape.
Julie poked her head in the door dressed in her robe, seeing the deer-in-headlights look on my face, hesitating and not knowing what to do next.
"Go on, my love. Put it all on. You know you want to," she said, smiling. "Hurry now, breakfast is almost ready."
With that, she blew me a kiss and then turned and headed down the hall to the kitchen, quietly humming to herself.
To say I was stunned was a huge understatement.
I picked up the panties, allowing my fingers to slide over the silky material. They had pretty lace edging and a little bow on the center of the waistband. I could feel my cock start to stir with all my senses in overdrive. The thrill of dressing in front of my wife finally broke the stalemate that was holding me frozen in place. I stepped into the panties and slid them up my legs and into place. They fit perfectly.
"Shit, I can't believe this is really happening," I thought to myself.
Before I could talk myself out of it, I picked up the sheer stockings and carefully slid each up my legs as I had done countless times before. In my opinion, there is nothing better than the feel of silky stockings sliding up your freshly shaved legs. The baby doll nightie was next. I slid it over my upstretched arms and over my head and into place. I looked in our mirror and twirled. The nightie rose up, exposing my panties and stockings.
"Oh my, this must be a dream," I said to myself. "If it is, I don't ever want to wake up."
Noticing my wife had also laid out a pair of pink fuzzy slippers next to the bed, I slid my feet into them.
"Wow, Julie really thought of everything," I whispered to myself.
With that, I headed down the hall to the kitchen. As I walked into the room, I stopped in my tracks as I saw Julie. She was at the stove cooking some scrambled eggs dressed in the very same outfit she had picked out for me. Her pink babydoll nightie exactly matched the one I had on. Her legs were also encased in a pair of sheer white stockings, with her feet in her own pink fuzzy slippers. Seeing that I had entered the room, she turned to me, smiling.
"Well, aren't you the cute one? Have a seat at the table; breakfast is almost ready."
I sat down, my head still spinning from all that had happened so far. Julie brought our breakfast to the table, setting a plate at each of our seats. She sat down, smiled at me again, and started to eat. She made some small talk as we finished our breakfast, completely ignoring the fact that we were sitting at the table in matching pink nighties and stockings.
As we finished eating, she looked at me intently.
"I bet you are wondering about all of this, aren't you?" she said. "I have been doing a lot of research on cross-dressing to try to better wrap my head around this part of you."
"I so appreciate you making this effort for me," I replied, tears starting to well up in my eyes.
She got up, walked over behind me, and wrapped her arms tightly around my shoulders.
"I've noticed you always seem a little depressed ever since I found your stash of women's lingerie. I guessed it was because you have been doing your best to suppress your urges to dress around me. I don't ever want to be the cause of your sadness."
She kissed my neck and nuzzled against my ear.
"I've made the decision to support and help you with this journey. We are in this together. Now that you are here dressed in this cute little nightie, it is actually starting to really turn me on. I think it is going to be fun to have a new girlfriend to play with," she whispered in my ear.
With that, she slid her hand down my chest until her hand found my stiffening cock, sliding her fingers over my new silky panties.
"Oh, Julie, you don't know how long I've dreamed of this," I sighed.
She came around and stepped over my legs, and sat down straddling my lap, her pussy grinding up and down my rock-hard shaft, her silky-smooth panties sliding against mine. The friction felt exquisite.
"Well, my love, what shall I call you when you are in girly mode? I certainly can't call you by your actual name when you are dressed so prettily," she whispered in my ear.
She pulled back and looked deeply into my eyes. I have never felt more loved than at that moment.
"Please call me Emily," I whispered.
She smiled at me.
"You have thought a lot about this, haven't you, my love? OK, all of this is making me so very wet. Emily, I'm going to make love to you now."
With that, she lifted herself off of me, slowly sliding my panties down just enough to free my hardening cock. Pulling her own panties to the side, lining my cockhead with her opening, she slowly dropped her weight back down upon me. My cock parted her warm, wet folds, and I slid into her completely. Julie then started to slowly lift her body up and then back down on my shaft, moaning and grunting with each bounce.
"Oh, Emily, you feel so good in me," she sighed. "I am so going to love having a new girlfriend."
Her lips crashed into mine as she continued to ride my rock-hard cock. Her tongue slipped into my mouth, swirling with mine. I could feel the walls of her tight pussy squeezing my shaft as she chased her own orgasm. Her hand slipped between us as she found her stiff little clit and slowly rubbed circles around it.
"Oh, Emily, your pretty cock feels so perfect inside me. You're going to make me cum so hard."
With that, Julie's entire body seized up. She screamed out loudly as her massive orgasm overtook her. She spasmed uncontrollably. Her pleasure drove me over the edge. I felt my cock swell within her as my own orgasm built and then hit. I grunted as I unleashed a huge load of my hot cum, filling her womb with my copious seed.
We collapsed together as we both continued to ride out the last of our orgasms. Julie giggled to herself. She slowly lifted her head, placing her forehead against mine. We were both still panting, trying to fully grasp what we had both just shared.
Julie looked up. Her eyes locked with mine as she smiled broadly. "Well, my dearest Emily, how did you like my little birthday surprise? I have so much more in mind that we can now explore together."
