tagTranssexuals & CrossdressersPenny Learns Julie's Secret

Penny Learns Julie's Secret


Julie and I go way back, to my first moving here. She lives next door and was so shy at first that I wasn't even sure I had a neighbor. As I moved in I caught a fleeting glimpse of a tall blonde, but never got a good look. It was over a month before we formally met and I learned that it was because she is a very, very private person. Eventually my winsome personality brought her a little out of her shell.

I'm a small girl and Julie is the exact opposite, I normally would be seriously attracted to anyone so perfectly built, and so delightfully statuesque, but I couldn't seem to get Julie's attention. She's stunning, dresses extremely well, and is one of the most feminine women I have ever met. She was perfect. I pretty well gave up any romantic notions, but I got something very special in return. We became friends, which isn't as simple as it sounds where Julie is concerned.

She's incredibly reserved and doesn't open up readily. We started interacting over the backyard fence and I discovered a sharp mind, a subtle sense of humor, and a very honorable person. Over time we became close, as long as no one else was around. If any of my other friends or partners was there, Julie did an imitation of a clam and beat a retreat as soon as decorum would allow. My friend Lily calls her Pygmalion's Model, as in her being only alive when she and I are alone.

All in all Julie became a close and welcome friend for a side of my personality that never gets enough exercise, my need for peace, reflection, and quiet meaningful company. I cherish her as much as I cherish my other dear, but much wilder friends. We've shared many confidences and she's one of the few people who accept my life choices as if they were my choices to make. Almost everyone else seems to think they have an opinion about my life. Julie accepted me with a surprising equanimity that I later learn characterizes her approach to the world. Calm, cool, thoughtful, and insightful -- that's Julie, my friend!

"OMG, Julie has a PENIS!"

I just discovered her secret, and it's trying to eat me alive! Julie is . . . a guy, well sort of a guy! Those of you, who know me, know I am bisexual, but when I am in a relationship -- I am as monogamous as most married women (notice I didn't say married men). There I was putting up a new shade in my bathroom window when I glanced next door and see beautiful Julie in all her glory, and I see something totally unexpected jutting out a good 5 or 6 inches from between her legs. She was in her tub and had the window open more than I had noticed before. Not only that, her penis was hard and she was masturbating. I tell you I nearly fell out of my window, and like most bathroom windows, it doesn't open. I don't think she noticed me, she seemed pretty preoccupied -- beautifully preoccupied if I say so myself.

My problem is I love Julie! She's a great friend and a wonderful neighbor. When it's just the two of us we open up to each other and can talk about tons of stuff. She saw me though my last break up and I helped her put her dog to sleep. I mean she's a Friend, with a big capital 'F'! I'll be the first to admit I have thought about her in sexual ways before, I mean doesn't everyone think about someone special when you masturbate? In the years we've known each other she's never made one move in my direction and I always thought she would rebuff me if I made a pass at her. Now I was just so damned confused.

I lay there in my own tub with the shade lying with me while I think about what I just saw. My second story bathroom is directly across from her first story bathroom, and as I replayed it in my mind, yes I saw one where I never thought I would see one. OK, so maybe I wouldn't have complained about seeing a penis penetrating her, I know, it's a bit voyeuristic of me, but to see one as original equipment? Is she gay, is she a lesbian, what is she?

I got up, but when I gathered up the nerve to look down, the tub was empty. My silly imagination could see her cumming straight up in the air and for the first time in a long time, the idea of a living cock made me breath heavy. I finished hanging the screen and went downstairs to take on a little caffeine and also to think about the change in my preconceptions that just happened.

My reaction showed me that no matter how open-minded we like to think of ourselves, we don't always react to surprises in an open-minded way. I hope the real test of being open-minded is how you react after you had a chance to think about things. So I needed to think!

Julie was incredibly shy when I first moved in. I doubt I ever saw her less than fully dressed and made up until that summer when she shocked me with that great bathing suit. Even then she would only wear it on her deck, which has a privacy screen from everyone but my taller deck. How in the world did she hide that package in that sexy suit?

I giggled like a silly girl and thought about a TV show I once loved, Highlander, and how they could pull four foot swords from damn near any kind of jacket imaginable. Just where did she hide it? Hell, stupid thought, it's not like she could remove it.

That was a thought, was it real? Maybe she was just playing with a double-ender? No, not the way she was tugging on it, that was a real cock, or I would have to get my eyes examined. I think I have seen enough real ones to be mistaken.

After Julie started opening up, we would spend some time together, coffee at either of our places, shopping, or just hanging out. She helped me get a handle on houseplant care and I helped her dig a new garden. Wow, digging that garden, she wore short-shorts and a midriff tee. I remember telling her to be careful or she would pop right on out of there. I was talking about her impressive breastworks, but her blush might show jibe had more than one meaning. I also remember how much I would have loved to see her pop out. I know, I know, I must have been a bottle baby, because I have a thing about beautiful breasts, and Julies were prize winners.

We never got sexual, but I know we've talked about guys and girls. I also remember never having seen her with anyone very often, but considering how private a person she was, I wasn't too surprised. Wracking my brain, I could only remember one time I saw her leaving on a date. The guy wasn't impressive enough to remember, but Julie was! I dreamed about making love with her that night for the first time. She was in a skin-tight skirt, boots, and a dark bustier-style top. Sexy! But I never saw her dressed like that again. She has some wonderful clothes and her taste was exquisite. Her make-up was always perfect and those few times I caught her before her morning shower/make-up ritual, just showed me that she had flawless skin and perfectly colored lips that really required little, if any, make-up.

This isn't fair, a perfect woman turns out to be less, or does this mean she turns out to be more? I am so freaking confused

Calm down, Penny! How do I feel about this? Do I feel differently towards Julie, or should I feel differently towards her?

Obviously this isn't her problem, it's mine. I would hate to lose her as a friend, but I also can't keep the image of her masturbating out of my mind. I have to regain some control, or I run the risk to hurting my friend.

Julie is certainly still my friend! She is still the same wonderful person who takes care of my home when I travel, and helped nurse me though that bout of flu last winter. Oh God, she saw me in my all together, but I guess I wasn't at my best. She acted like a medical professional and dealt with me as the sick person I really was. If she hadn't been there, it could have been so much worse. My Doctor said it could have become pneumonia if Julie hadn't stayed with me, kept me well hydrated and warm. She helped me to the bathroom, and bathed me when I was covered in the sweats. You don't change your tune about such a person because of a lump of flesh! No matter how nice, and hard, that lump was. No wonder I was confused, I was also turned on!

Julie is still Julie and if she wants to be a girl, and act like a girl, then the least I should do is treat her like a girl!

I took my coffee, liberally laced with some high-proof reinforcement, and laid out in the sun on my deck to continue thinking. Do I tell Julie that I know her secret and that it doesn't matter? Oh yea, I see myself -- 'I like transvestites, some of my best friends are transvestites'. Oh sure, that's the kind of words that would be accepted well. I would hate to put up a wall between us, and I know it would be my wall, not hers. This isn't her fault, it was an accident. But I can't get the image of her hand, her beautifully manicured hand wrapped around a lovely cock tugging it in a rapid sequence that always made my boyfriends cum like mad. The idea of seeing her like that again was making me dampen my own panties.

Uh oh, vibrations on my stairs -- someone was coming up to my deck. I refused to open my eyes. 'Please let it not be Julie, please let it not be Julie. Not yet, not until . . .'

"Hi, are you asleep?"

"Oh, hi Jules, no I was just resting my eyes against the sun. What are you up to today?"

Julie took a seat, actually more of claimed part of the railing and sat up on it. She was in shorts and a halter top that almost failed in its mission to halt. She sat with her legs open and even though I know she might take offense, I took a long look from her toes up through her thighs to her face and damn it if this wasn't a perfectly fine woman!

She cocked a perfect eyebrow at me at my glance and took it in stride.

"Oh, nothing special. I have to run to the grocery and was looking for company. You want to go shopping with me?"

"Julie, I would love to, but there is something I need to take care of first."

"Sure I'm not in a rush, come on over when you are ready."

"No, don't leave, this concerns you too."

She looked a little puzzled and just a little defensive. How was I going to talk to her about this and not push her back into her shell?

"How open minded are you really, Julie?"

"That's a strange question after all I've seen you involved in, Pen."

"I know, but right now this second I really need to know."

"I would like to think I am pretty open, maybe more than you realize."

"So if I ask you to not say anything, and to not run away, will you stay and help me get through this. I can't do this alone!"

"What is it, Pen, you know I'll help you in any way I can. You are starting to scare me."

"Don't be scared, just promise you won't say anything, or even move from that spot until I tell you that you can."

She looked at me, still puzzled, but no longer looking very defensive. I would love to know what's going on under that mane of perfect hair, but I was still having trouble with my own thoughts that I doubt I could have made heads or tails of hers.

"OK, Penny, I promise!" She put down the coke she was drinking; the condensation instantly got soaked up by my wood railing. She put her hands on the rail on each side of her wonderful thighs and waited with the patience of a saint for her perennially screwed up neighbor to let in some light.

I looked at her again, really looked at her and one part of me was amazed that she was my friend; the other part of me was slowly being overwhelmed by her presence.

I can't believe that I never noticed just how hot she always looked! Maybe I was too close and it took this to jar my senses, but she is such a perfect woman, a trusted friend, and absolutely stunning. I couldn't decide how to start the conversation, but my body had other ideas. I dropped my coffee, which made her jump, but then she inhaled deeply as my hand pushed into my shorts and I went immediately to my dripping wet pussy and I pressed my clit hard before rubbing up and down my cunt. My eyes caught hers and I tried to mentally tell her what I was feeling, but I couldn't. I also couldn't stop my hand from bringing me to the edge of an explosive orgasm. Time seemed to slow down as my hand went faster. I saw sweat bead up on her perfect face, and her nipples pushing at her top. She swallowed in slow motion and for the first time I noticed that she had a small Adams apple which bobbed up and down when she swallowed hard, and she was swallowing hard.

I still couldn't see any signs she had a penis, but for the moment I was beyond caring. Jules was watching me with huge eyes, and her breathing told me that I was getting to her at least in a small way.

I couldn't watch any longer, I exploded, sending the lounge chair tilting off to one side and somewhere in the middle of my orgasm; I crashed down to the decking.

When I came around, I was lying in the world's most enviable position, my head was on Julie's thigh, and I was looking up at her concerned face.

"Are you crazy or something, what in the hell were you trying . . ."

My energy returned much faster than usual after an earthquake like that. I reached up and silenced her with a kiss.

She looked like a frightened rabbit and I took her hand to my face. "Shhhh Julie, there is nothing to be afraid of, unless you don't want to love me. I can understand anything but that."

"Pen, you don't understand, you never . . ."

Another kiss, this time she responded as the woman I knew that she truly was. Her kiss was soft, but firm, her tongue exploring, but not trying to overwhelm. I could feel tears but I wasn't sure if they were hers or mine.

We broke apart and took a breath. "Julie, I can understand more than you know. I know that you like me, I also know you care about me, what I need to know is if you love me."

"Pen, I can't . . ."

"Yes, Julie you can! All you have to say is that you love me and nothing else matters, trust me, love, nothing else matters!"

She looked at me, suddenly both fearful and something else. Did I see hope in her expression or was I just hoping? "Penny, I have loved you for months, but you prefer girls and I guess you know . . ."

"I am never going to let you finish a sentence if you don't just give in to the inevitable. Nothing matters but the fact that you love me. And you are also a woman, the most beautiful, and the most perfect woman I have ever known. You became my closet confidant and my best friend before I knew you well enough to know that I have also been in love with you for months, but not understanding it myself."

Julie looked at me with eyes that were finally fully unhooded. They showed me old hurts and betrayals from sources I cannot yet imagine.

I got up slowly, still slightly dizzy from my crushing orgasm and held out my hands to Julie. She got up and stood next to me, unsure of herself, or unsure of me. I took her hand and led her into the bedroom. Over the years quite a few impressive women have shared this bed, but no one as impressive as She. She let me lead her into a place where we have laid together watching television, spoken so many secrets and shared so many confidences. I wonder how many times she imagined herself in here under other circumstances.

I turned toward her and slipped out of my shirt. My little breasts tight, the nipples stiff and tall. I was still completely aroused. I slipped my hands up from her waist and found the front clasp to her bra. She didn't stop me from unhooking it, but she was starting to get that deer-in-the-headlights look. I wanted to kiss her again, but she was just too tall that I couldn't reach her with her cooperation. Her bra fell open and her breasts dropped just a bit to gravity. I didn't care if they were DuPont's or natural, because they were her breasts. Lifting her shirt I got my first full look and the sheer perfection took my breath away. They were a perfect C, and I think that note was the one I was humming. I tried to pull the shirt all the way off, but she helped me, finally moving. The shirt heading off to parts unknown as I took her bra off her shoulders. She didn't have masculine shoulders, something that defeats other cross-dressers I have seen. Hers were delicate, her frame actually a light frame for all her height. I guess she was 5'10, or maybe even 6', but to me she looked perfect. A runway model couldn't have a more perfect body, and they would be drooling over those breasts that were all mine for the moment.

I slid out on my own shorts; the wet panties went with them. I know Julie had seen me naked before, but she hadn't seen me in my excited prime, I was a bit of an invalid the last time she looked at me nude. Her eyes studied my body, I hope she approved. My skin wasn't as flawless as hers, my breasts smaller, my legs tightly muscled sticks against hers, but in my own way I was like a racehorse being compared to a Clydesdale. We each looked excellent in our own ways!

Her breathing was labored and my heart skipped a beat when I realized that her shorts had been pushing down in the crotch. She was getting turned on and her beautiful cock was tucked back between her legs. I bet it was uncomfortable.

I unhooked her shorts and started to pull them down when her hands caught her panties. I slipped the shorts over her hips and got a good look at an interesting thong panty. Again I would have sworn this was a complete woman in front of me except for one small difference. Any other woman in her position would have been dripping wet and her dark thong would have showed something. Her scent was also missing the overpowering scent of an excited woman, but Julie had a scent all her own. I stood in front of her and pressed my hand to her pussy, feeling the hard cock pointed away from me. "Please Julie."

Her hands released her thong and I knelt down to bring it down slowly. I discovered something unusual, a pocket built for her penis, holding it in position. It was a challenge to get the panties off, because it certainly wasn't designed to hold a 6 inch penis at full extension. By the time her thong hit the ground, we were both fully aroused. I was wrong about one thing, there as a wet spot; it was just a little further back than I was used to.

I lifted the thong to my face and smelled her aroma. Her scent was a mixture of her perfume and whatever soap she used, and somewhere in there was a scent I could still recognize, one I haven't been so very close to in years.

My tender Julie looked like she had been thunderstruck as she watched me do things I hoped she dreamed about. I looked at her cock and I couldn't believe how delightful it looked. It was nicer than any toy I had seen on a woman's body before, and it suited her in a way a toy always looked off. Her public hair was trimmed in a bikini cut which to me just looked like an arrow pointing right at heaven. I placed her cock against my cheek and felt the warmth of her skin against me. Her hands were fluttering slowly around, like she had no idea what to do with them. I kissed the tip of her penis and almost laughed as it jumped in my hand. I looked up at her, watching her looking at me and without breaking eye contact I took her in my mouth.

I haven't done this in so long, not on a real one, but I knew exactly how to be gentle. This was no guy to get off on rough play, this was my Julie and she was as gentle and feminine as any woman in my world. Sucking deeply I took her completely in my mouth and just using my lips I pulled back off until I could see her entire length glistening with my saliva. The tip was expanding into an impressive mushroom; I knew she was so close to exploding. Sucking deep again I could feel the veins throbbing against my tongue as I kept up a sucking feeling that I always loved on my nipples. Just enough to maintain a nice sensation, but not enough to force them to extend to their sharp points. I found her balls with my other hand and cupped then with equal gentleness. I heard her moan, her voice was music to my ears. Pulling out all but the tip I took my hand and wrapped it round the shaft. Pulling, twisting, and pushing on it -- I could see the skin move over the hardness beneath. I teased her glans with the very tip of my tongue and felt her tense up slightly. Her legs tightened and I knew I was about to get my first taste of her. I felt the pressure build from the base and wasn't surprised when my mouth filled up with a slightly salty flavor. Pumping, I felt more of her coming up to fill me. I tried to hold it in my mouth, but there was too much, when a drip threatened to run down my chin I finally swallowed.

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