Loving Aunt Sarah : Chapter 2

Note : This story is completely fictional!

The following day, which was a Saturday, had been very uneventful. Then again, welcome to every Saturday of my natural born life. For the past few weeks, I had been trying diligently to get some over time at work over the weekends, to remedy this problem. My efforts, however, have been unsuccessful.

Hence this Saturday was turning out as boring as any other. With nothing to do, I had spent the better part of my morning sitting on my couch playing video games. I had an Xbox 360 and a Playstation 3 hooked up to the TV, as well as an ass-load of games for each one. But for some reason, I was in the mood for the older systems. Sad as it was, my morning was spent playing Super Mario Bros. 3 for the original Nintendo system.

Why it took me so long on this particular Saturday to realize that I actually had an answer besides Mario to my boredom, I have yet to figure out. But somewhere around noon, the answer hit me. With a smile, I turned off the Nintendo and grabbed my cell phone, dialing my Aunt Sarah’s home number. With each ring, my tension grew stronger. By the fourth ring, I was nearly ready to hang up, but Aunt Sarah answered the phone just before I had the chance.

“Hello?” came my Aunt’s sweet voice.

No one makes a phone call without expecting an answer, especially when calling a family member. But actually hearing her voice only made me more nervous than before, even speechless. I found myself unable to say anything until she said hello a second time, sounding slightly annoyed. “Hi,” I finally said. “It’s me.”

“Oh, hey Val,” she said, a bit less irritated now. “What’s on your mind?”

“I just wanted to thank you, you know, for listening last night.”

“No problem. Whenever you need to talk about anything, just give me a call, or come on over. I’m hear for you.”

“Well, that’s actually why I called you. I was wondering if you had any plans tonight?”

Aunt Sarah took a moment before answering, undoubtedly thinking about the day ahead. She never did write anything down, insisting that she could keep everything clear in her head. “Nothing I can think of off-hand. Why, you have an idea?”

Now it was my turn to pause before answering. I knew now that I had my Aunt’s support, but I was still new to being out, even if to a single person. “I was thinking… now that she has some outside support, Valerie would like to go have some fun. You game?”

“Do you even have to ask? Just tell Valerie to be at my house no later than 9:30 tonight so we can get ready. Think she’d like to go for some late night bowling?”

“I think she’d love it. See you tonight.”
*****
As the day had drawn closer to the night, I was becoming more and more excited. With my Aunt’s help, I was finally going to be able to go out in public as Valerie! What’s more was that I knew this would draw my Aunt and I closer together. Perhaps my attraction to her would become more than physical through future bonding, and I certainly hoped it would. The question was, when do I open up to her about it? Timing was everything, but I couldn’t wait too long. The woman was amazingly perceptive, making hiding things from her almost impossible. Beyond that, she had this unique ability to observe others so subtly that the person would never knew someone was making mental notes. No way did I want my Aunt to simply figure out that I had a thing for her; she would have to hear it straight from my mouth.

When I pulled up in her drive way, there was a black Honda Pilot there that I didn’t recognize. My tension suddenly changed from positive to negative as I realized what this meant. I began to understand now that once you come out of the closet, you start moving further away from it at high speeds that you can’t control. It’s a leap in which you have to know what taking it entails before committing to the act, because once you hit the accelerator, the brakes go out.

Eventually I was able to turn off my own engine before taking a deep breath, and walking up to the front door. I moved my hand up to the doorbell, but paused momentarily before actually ringing it. Inside, an unfamiliar, female voice called out that she would answer the door. No doubt she was the owner of the also unfamiliar vehicle in the driveway.

When the door opened, my eyes were greeted by the sight of a middle-aged woman who, like my Aunt, was extremely gorgeous despite her age. A friend, I figured. “Val?” the woman asked me.

“Yea, that’s me,” I replied.

The woman stepped aside to allow me in from the cold as she offered a handshake. “I’m Jennifer Holland, a friend of your Aunt. Nice to meet you.”

I accepted the handshake as I wiped the snow from my boots. “Likewise.”

“I’ll go let her know you’re here.”

“Oh geez,” I muttered to myself.

By the time I unlaced my wet boots and removed them, Aunt Sarah had come back downstairs with Jennifer. My Aunt took a close look at my face and sighed with disappointment. “You couldn’t get a closer shave?” she said.

“Talk to me dad about that, he’s the one who gave me the thick facial hair. I did the best I could.”

“Well, you have a mask. It’s very light, very subtle. I doubt anyone would notice, with you looking the way you do now. But dress up like a woman, and that’s gonna stick out sore thumb.”

I turned my gaze to Jennifer. “I take it she’s told you already?” I asked, though it was more of a statement.

“You’re not the first drag queen I’ve ever known,” she said with a reassuring smile.

“Jennifer’s going to help you get ready,” Aunt Sarah explained. “So you two can head on upstairs and come down when you’re ready.”

Jennifer nodded to me, and I followed her upstairs to the master bedroom. It came as no surprise to me, to find that I’d be wearing my Aunt’s clothes again. After all, we were the same size. I didn’t mind. In fact, I preferred it. I know this night wasn’t about nailing her (not yet anyway), but wearing things that had been on her body previously would do just fine for tonight.

The first thing Jennifer had me do was strip completely naked. She assured me that she’d done this sort of thing before, and it was nothing sexual for her. Nonetheless, I was still reluctant to do it. Eventually I did, as Jennifer was picking out a few clothing articles. “Lay on the bed,” she instructed me. I laid down, and she knelt beside me on the bed, placing a pair of satin, white-lace panties at my feet.

“Now, before I do anything else, I’m gonna have to ask you not to get a hard-on,” she said, trying not to laugh. I shrugged, giving her the go-ahead to do what she needed to do. “To put it bluntly, I’m gonna tuck your dick in so you don’t have a bulge beneath the tight jeans you’ll be wearing. And about that hard-on I don’t want you to get, you may wanna remember that the entire night, ‘cause it’ll hurt if you get one while it’s tucked.”

“Gotcha,” I said. What I never knew before was that there were two open spaced just above the scrotum where one’s balls could be tucked. Jennifer was careful as she moved them, knowing what a sensitive part of the male body this was. As she handled me, I considered fantasizing that these were my Aunt Sarah’s hands, then decided against it. Thinking about that would get me rock hard almost instantly.

“Okay, hold your shaft down between your legs please,” said Jennifer. I held my dick down with two fingers and Jennifer pulled the panties up my legs. They were a snug fit, nay, a perfect fit. There was no way my dick would fall back down with these on. “You know, it’s a good thing you shave your body. You’d have a hard time feeling feminine with all that hair.”

“Having my own restroom helps,” I told her. Matching the panties was a white lace wonder bra. Clever really, because I wouldn’t have to stuff that. The jeans I wore were indeed tight, almost skin tight, and had a line of buttons in the front rather than a zipper. Finally I wore a black, long-sleeve turtle neck sweater (to cover my Adam’s Apple and short arm hair).

We then moved to the master bathroom, where Jennifer helped me put on the wig (same one from the Halloween party) and make-up. Amazing how she knew how to cover my mask with just the right amount of foundation. I also found it amazing just how long my eyelashes were. I’d never noticed them until Jennifer straightened them out, putting in some black mascara. Last but not least, she applied lip gloss to my lips, giving them a gently shine.

When I looked into the mirror one last time before returning downstairs, I no longer saw any traces of Valerian. That night, there was only Valerie. We rejoined my Aunt in the living room, and I knew with one simple glance at her lovely face how difficult it would be to not become aroused.