All Pretense Aside...                   by: Diane                © January, 2001

 

Prologue from Part 1 - Our main character grew up wearing his sisters’ clothing. Not as punishment or even as a result of being found out. After his first summer in panties and skirts, Jan had adopted the name Janice, as had been suggested by his siblings, as they teased him about his play pretending as Supergirl while wearing their outgrown tights and leotards.

By the time he graduated from high school and was considering which college to attend, Jan had continues to periodically dress as a girl, although his family kept the secret of his feminine side in the family, up until his younger sister found out that the young woman who had captured Jan’s heart had a family secret of the same nature-her father was a crossdresser! Then Sally had been told of Janice, and came to his house to convince him to attend the college where she had been attending classes Do you think having a woman tempt you into skirts could lend a hand?

 

Part 2 - A Dream of a Summer

Sally lifted her leg and released his member. "There, that should hold you for a while. Now let me clean up a little and change panties. Then we’ll get you dressed while you finish explaining your penchant for wearing panties to me."

Sally disappeared into the bath, carrying a fresh pair of panties to replace the ones soaked by my semen. In a short while, she reappeared wearing bright red underpants and a smile. "Okay, now, can you explain how you went from becoming Supergirl to a swim hero that likes to wear panties? Or is that too much to ask right now?"

I continued to explain as I proceded to slip into fresh red undergarments to match hers. "Well, as a young boy, I did dress as Supergirl. At first, it was a means of entertaining myself since my older sisters refused to let me play with them. Then, after they had noticed my garb that I was playing in, by the end of the vaction time that year, I was spending the full time dressed as a girl, with the full understanding of my whole family. That seemed to be the start of the periods when I felt contented only when dressed in feminine things. All the way through high school, I’ve secretly continued to wear panties and other girl things under my male clothing when possible. But it has always been kept as a family secret, until now."

Smiling, Sally asked, "Okay, did you find cross dressing to be sexually exciting, or was it because you secretly want to be a real female?"

"Oh, by puberty I began to associate wearing feminine things with masterbation. Not that I couldn’t be satisfied without getting dressed in my sister’s things first. But it seemed to be more exciting. But I also came to appreciate the sheer body comfort I got from wearing the clothing that seems so much smoother and softer than my male clothing. I can’t imagine why any woman would want to wear anything that is stiff and rough, unless they’re needed for protection. Like a cowboy wears chaps to protect the legs from mesquite or cactus thorns, for instance."

"But do you want to be a woman? To be attrctive to men? Even to seduce men sexually? Or is your appearance as a woman just so you can get away with dressing as a woman?"

"First of all, I suppose the thought of being able to appear totally feminine in my appearance is to be able to freely dress in a woman’s things. Oh, there have been thoughts about whether I would be able to attract men who saw me as a woman. However, my forays out in public while dressed have been limited to those times when I was with my family. I’ve really had no real desire to attract men to myself as a woman. Making sure that my appearance projects the look of being feminine is therefore just a means to accomodate my being able to wear the clothes, I suspect. Why did you ask if I try to attract men?"

"I asked that to see if men are your thing. Maybe I should have asked in a more polite manner, like, do you like women or men best? There are transvestites or crossdressing men who do so to draw other men to themselves as their sexual partners, you know."

I laughed. "Hah, the closest I’ve ever been to having sex with another person was when you made me come a little while ago!" I exclaimed. "I had never touched a grown woman’s breasts before that either. Except perhaps my mother’s breasts when I was a baby."

A look of surprise came to Sally’s face. She gasped, then asked, "You mean that you’re still a virgin?" as her eye brows raised. "Yep, that’s me. Little ole never been screwed, male virgin. The modern day Cinderfella who never got to go to the ball to meet the Princess...."

"A baseball and swimming sports hero in high school that has never had sex? I find that hard to believe, Jan!"

I blushed. First my face turned red, then the coloration spread down to my shoulders and chest until I was red all the way down to the bra I had fastened about my chest. What could I say to the woman I had wanted so badly for at least two years, but who had rejected all attempts on my part to even be able to hold a conversation with before today?

Perhaps my silence spoke loudly. Or perhaps the blushing convinced Sally that I spoke the truth about never having had sex with another person. In any case, Sally blurted out, "My God! I’ve got an innocent child here. Me who comes barging in and undressing myself in front of you. No wonder you thingy got hard!"

My blush deepened. This embarrassing moment was getting tough to take, maybe even more than being discovered to be a crossdressing male by some one other than my family members who had known about that particular situation for years. I just couldn’t explain why, to her or even to myself.

Sally came up to me and wrapped her arms around me and hugged me close. "My poor innocent baby. You embarrassed to admit being a virgin? Don’t be. I think it’s wonderful. That’s why I avoided getting close to you during high school. You see, I’m still a virgin too, even if I came on like gangbusters today. I’ve been waiting to find some one equal to my Dad before I lose my cherry. Now, shall we get dressed to kill and go to a movie or something? Otherwise, I’m going to start crying." She lifted her lips to mine and kissed me hard, sliding her tongue out and into my lips while hugging me closer. My arms wrapped her in embrace as we kissed for a long time.

We broke apart finally and continued to don matching clothing. From the clothing bag she had bought with her, Sally pulled out two dresses which also matched, except one was for a taller woman. "These are from my folks’ closet. My Dad wears the taller version, and Mom the shorter one. Try on this one" she said, as she handed me the longer dress.

In short order we finished our dressing, except for shoes. Sally had me set down while she applied make up to our faces, again making our appearances similar, which was fairly easy, given our matching colors, both in eye and hair.

Sliding on heels and grabbing the two matching purses, we were ready to leave. But first we stood in front of a full length mirror, side by side. Would you believe it, we looked just like twins! I found myself reveling in the aspect of having a woman I desired who accepted the idea of a man dressing in skirts like she did. The two of us walked out the front door and went to her car and left for the movie theater in a nearby city where no one would know us. After the movie, we two women went shopping, selecting a number of matching outfits. All with skirts, naturally. Then we drove back to see her parents so I could meet them.

Believe me when I tell you that was the most terrific summer I had ever had. Until then at least.. Oh, by the way, I’m no longer a virgin. And neither is Sally! Perhaps that could be the subject of the next story I write. All pretense aside.

 

 

© 2001
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