Under a Napa Moon

My name is Maryanne. I'm a 28-year-old single woman living in the guest house on an old wine estate in the hills above the Napa Valley. It's purely a rental (I'm not a guest!), and I've lived there for around four years. It's very quiet, and the drive to work in my old jeep (I work as a social services psychologist) isn't too long. After a long day with patients, I can return home to relax, cook, walk and watch as the hillside grapevines are tended and harvested.

On the other hand, I miss some socializing because of this living choice, and a girl has her needs. So, I opted to try online matchups -- seemed like it could be fun if I choose the right website and diligently vetted the guys I might meet. I signed up at a professional's meetup site, used one of my better photos (I'm short, lean, with decent Germanic features, but with small breasts), and hinted at my profession and living arrangement.

The first guy I met, Brian, was a carpenter living down in the valley. He was outgoing, strong and pretty good-looking, but his tastes were so contrary to mine: country/western music, beer joints, and probably hadn't read a book in 10 years. So, bye-bye Brian, after only a hug and a kiss. Next was Johns, very much the opposite. As one might guess by his name, he came from an affluent family, was a successful real estate agent (in this area, some big deals are consummated), and yet had an erudite side: he liked classical music, was into Russian literature, and loved Masterpiece Theater. But something didn't click between us. Even though he seemed interested in me, he always seemed on the go, and constantly had to stake out times we could get together. So, after many phone calls to set up three get-togethers, and after a little fondling and some deep kissing, I said my adieus.

"Sorry it didn't work out," he said sheepishly.

I had entertained some hopes of sharing in his wealth. A girl likes to dream.

I could tell both guys wanted to jump in bed with me, but I didn't flirt in that direction or invite them up to my lair.

The third entry in my sweepstakes (am I really a "catch"?) was an oddity. By the name of Dave, he advertised himself as an IT professional. His photo showed an attractive, sensitive-looking guy. When I contacted him, he soon confessed that he wasn't that at all -- he'd lied just to get on the dating site. "So what do you do?" I asked.

"I work part-time for the post office in San Francisco, and am getting my master's degree in film-making at SF State."

Hmmm. No job status like the other two, and yet I was intrigued. Because he didn't live nearby, we communicated for a while by email, and then graduated to talking on the phone. I learned he was 23, tall, and really liked the outdoors, which endeared him to me. He also liked to experiment with cooking and eating out. Sometimes he seemed a little clueless about girl-boy dating and the social niceties that one usually observes, and he wasn't in the least pushy about actually meeting. This let me lower my guard a bit. I suggested he come up to Napa some weekend for lunch.

"Wonderful," he said. We arranged to meet at the Napa bus station the following Saturday (he didn't even own a car!).

So I drive down the winding road into Napa and meet this Dave. True to form, he has his knapsack with him and looks like he could start hiking at any moment. He's a bit lanky and is wearing a plaid flannel shirt. After scanning the people around the bus looking for me, he comes over with a nice smile and gives me a hug. He smells OK, in fact, kinda nice. And he didn't overdo the hug like some opportunists do. I'd say he seemed enthusiastic and upbeat -- qualities I like, especially after dealing with so many downbeat patients on the job.

I usher him into my jeep and we trundle on over to Zinfandeli, my favorite casual place on the edge of downtown. We have sandwiches and chips, and he insists on going Dutch, even though I know I'm a lot better off financially than he is.

We do hit it off. I can't explain exactly why, except that he seems kind of like a very good friend, or brother, and I relax with him. Of course, there has to be something beyond being friends! I confess to liking his lips, the chest hair peeking out of the V of his shirt, and his veined hands. Details, details. Something about his voice, too. Soothing, yet every word clearly enunciated in a lovely male voice -- a Canadian voice. No pothead here.

At one point after I turn the conversation toward him, he gets exciting talking about a film he's editing with some buddies at school and he briefly reaches over and puts his hand over mine. It is so totally natural and friendly I practically melt. Me, Maryanne, the psychologist.

It's not in my master plan for the day, but Dave shows so much interest in the wine estate and my living arrangement that I volunteer to take him up there.

"Last bus is at 11 p.m., so we should have plenty of time," Dave says. Good that he apparently has no hopes of spending the night with me.

On the way up, when shifting the manual shifter in my small vehicle, a couple times I happen to contact his leg. I wonder if he's feeling what I'm feeling ...

He shows a proper reverence for the appearance of the estate -- buildings made from large blocks of stone -- with a European flavor. Large oak shade trees. Patterned brick drive- and walkways. We enter my place, which has more room than I need, but the ambiance is just right. He is so impressed with everything, and I hope with me ...

We naturally have to have some of the red wine made from grapes grown on the estate as I show him around the small house. As we end up back in the living room, I show him some artwork I've been doing lately -- just watercolors. The wine has me feeling really pleasant and happy.

"You're a very good artist. You are. You should have a show somewhere," he says.

"Oh well, maybe sometime down the road," I say.

Then, for the life of me, and I've never said this to anyone before, I come up with, "And I really like sex, too." OMG, where did that voice pop up from? But I just look at Dave as though saying it was the most natural thing in the world, like saying, "And oh yes, I like mushrooms in my salad, too."

Blame it on the wine.

Dave's eyes (a psychologist can tell so much by looking at people's eyes) widen for a millisecond, and then there's a brief silence, and he says, "That's great." No more, no less. He could've said, "Now or later?" or "I do too" or "What kind of sex do you like?" or "Would you like to get down and dirty?" -- or he could have slowly and seductively begun to undress me, right there.

But, "That's great." It's like what I said just hangs there in the open air, and he chooses to pretend I never said it, I guess. So now I feel embarrassed, like I'm some cheapo drunk in a bar ready to open my legs to the nearest horny dude.

So what does he think of me now? Like all I want is sex. Well, maybe I do. But it ain't happenin', girl. Maybe this dude is going in that direction but wants to take the slow route there?

I look at his levis ever so briefly, looking at the male bulge there, and fantasize grabbing the zipper, pulling out his dong, and consuming it on the spot. Yeah, right.

But we continue on being ever so nice to each other, me smiling a lot, and listening to him. And I take him to meet his bus in the evening, after I cook a nice dinner. For this, I earn a friendly kiss, another hug, this one fortunately tighter than the first one, and we promise to meet again.

I go home and masturbate to a nice climax.

Here am I the very self-possessed and educated psychologist and for the life of me, I don't know why I'm allowing myself to be involved with this man, which may bring major frustration and disappointment down the road. It's, yes, the Love Trap, isn't it, you idiot!

I tell a friend at work what happened, and she says, "He could be a loser of a lover."

I say, "Maybe, or maybe not. I've got to see."

So, Dave comes to visit a couple more times. There's a hug and a kiss. We go for long walks. I cook more dinners for him. I don't bring up the subject of sex again, though I know that my statement about liking sex hasn't been forgotten. I detect that he gradually moves physically closer to me, but he makes no overt moves. I masturbate thinking about him. I fantasize grabbing and kissing him passionately, but that never materializes. I guess that we're best friends, and there's nothing wrong with that.

Is there?

On the third and fourth visits, he stays over, sleeping in the guest bedroom. I really do think he wants to sleep with me, but the move is up to him.

On his fifth (yes, the fifth!) visit, I bring up something.

We're eating my healthy repast, and I say, "Dave ... got something to ask you. When you were here for your third visit, I went to get dressed for work the next day and I noticed -- I think! -- that it looked like someone had gone through my lingerie and clothes."

"Really?" He looks to the side as he responds.

"Yes. And so before your next visit I put little pieces of paper on the edges of my lingerie drawers, and after you left they were disturbed. So that kinda makes you the culprit."

Dave is without words, obviously embarrassed, and I feel a bit sorry for putting him on the spot.

"So, Dave, what is it about my stuff?"

"OK, Maryanne, I violated your space, I guess you could say. If you want me to leave, I will. I would understand."

"Don't worry about that. But as a psychologist, I want to know exactly why you were looking at my stuff. You didn't take anything, I made sure about that, but you were looking and handling."

"I'm embarrassed. Really embarrassed ... I guess I'm totally fascinated with women's clothing. It's powerful, like magic. I've done it before, and nearly got caught a couple times, but got away with it."

He continues, "So to go back in time, when I was an undergrad, once I was doing my laundry in a our co-ed dorm, and someone had forgotten her bra and panties. I stole them, and later wore them and it was like earthshaking. Then I felt real guilty and trashed them. I figured something was wrong with me and it was unmanly. So something similar to that happened a couple times since then."

I am rather fascinated, since I had never had a patient who admitted to this sort of behavior. Sure, I had read a couple case histories of crossdressers or transvestites or drag queens, but they didn't interest me terribly.

"If you had the chance, would you dress all the way up as a woman?"

"I'd be pretty conflicted, I think. Like it was unnatural. And it would feel funny, doing it in front of someone like you. I mean, this has been such a private thing."

Generosity is one of my faults. "Tell you what, Dave. Next time you come, I'm going to obtain for you a simple dress and panties and I want you to wear them the whole time. It's very private here as you know and only I will see. Now if all of this is too threatening to you, then we should just kiss each other goodby for good. 'Cuz I want to see where this will go."

Dave's face reddens a little. I can't tell if he's threatened by this or excited.

But he does return -- his usual all-natural, good-vibe self, but with just a touch of embarrassment.

When we enter my stone-house abode, we first talk, over wine, about everything under the sun for a half hour. I wonder if he'll bring up our arrangement, but he seems to have forgotten about it. That can't be!

"Dave, come on upstairs. I have something to show you."

"Oh, really?"

"Oh, come on, don't act like you don't know."

In my bedroom, hanging from my antique four-poster bed, is a simple, country-style print dress with little puffs on the shoulders. And on the bed is the cutest pair of white lace panties and a pair of modest clip-on earrings.

Dave's eyes widen as he says, "You really did it. I mean, this is a little like a dream. I always figured women would be turned off if they knew what I liked. Like they would say, 'You like my lingerie, not me!'"

"Well, Dave, allow me to be your partner in crime." We both laugh. I leave him alone to change.

Fifteen minutes later, he makes his way down the stairs as I'm preparing dinner. The dress fits him pretty well, with the hem just below his knees. Instead of being gangly and uncomfortable, he, with his naturally long hair, seems to have acquired a new sense of grace and even hints at a previously undisclosed femininity. I wish I'd gotten him some shoes, because his large male feet don't quite match the rest of him. However, I have to confess, I like him even more this way.

"Ta-ta!" he says, as he does a 360, twirling the skirt.

"I love it," I say. "Honestly."

"Now all I need are boobs," says Dave. "Boobs and shoes, or whatever."

"We can do that, yes, we can. But I enjoy you just like this too." What I don't say is that he obviously has an erection under the dress because it makes a small dent in the fabric. So, there's the erotic element at work here too. Love it.

After dinner, in which he was a little more talkative than usual, and, for lack of a better word, lighter, we sit down to watch some PBS TV. We're sitting so close we're almost touching.

My impishness come to the fore again; can't help myself. I unbutton my shirt and show my little-tits-in-bra. Like bras? Like this one?"

"Well, yeah."

Next time you come, we'll go shopping and buy a couple more things.

"Oh I don't want you spending all this money on me. I'll order them online myself."

It's a warm summer evening in the hills above Napa, and like a couple impulsive young kids, we step out into a full-moon semi-darkness, and holding Diana's hand (yes, I have begun to call him Diana) I lead him up a trail through some woods to an overlook with a resting bench. The twinkling lights of the broad Napa Valley stretch out below us, and the scene is very romantic, indeed.

And once more, I smell his wonderful natural fragrance.

"I have something to tell you," I announce, breaking the silence.

"Yes?"

"Well, first of all, are you happy this way, Diana?"

"Very much so. You can't imagine."

"Good. Now I'm going to tell you something more about me. I've been in several relationships with women. Well, actually, the first one was more like a two-night stand. But the second one, with Marcia, lasted about four months. That was just last year."

"So, you're bi then?"

"Oddly enough, I wouldn't call myself that. I think I just wanted to try women out, to compare them to men -- something like that."

"How did they compare?"

"Oh, I don't want to get into that. ... But something else I want to mention is that I really didn't get along at all with my dad. Now you're seeing the shrink side of me come out! I mean, my dad was an SOB, a real cheapskate, and was so petty. When we stayed in hotels, even though we weren't poor, he'd steal silverware and towels. He'd forget my mom's and my birthdays. So I guess that colors my relationships."

"Funny you should mention that, because I hated my dad when I was growing up. He had a god-awful temper, and I lost count of the times he blistered my backside with a hairbrush. You couldn't argue with him. He did provide for the family by holding down two jobs, but there was something just too militaryish about him. Too much discipline and barking orders."

"OK, OK, OK!" I say. "Enough with the psychology stuff."

With that, in the moonlight, I pull up my long-sleeved T-shirt, and guide his hand over my bra cup and breast. He starts breathing heavily.

After a little while of that, both he and I at about the same time, pull each other close. I detect he's a bit awkward at this new turn of events, but our lips do find each other. I really do want to reach down and handle his dick, but knowing him, I want to proceed slowly.

And so, that's the way the evening ends. We walk back down the hill. He sleeps in the guest bedroom again while I'm in my four-poster bed. I rather want him to slip into my bed later, but he's the perfect gentleman/gentlewoman and doesn't press on.

Three weeks later, Dave/Diana visits once more. I tell you, masturbation is fun, but I really want to try him/her on for size and ring the bell.

As he/she promised, she did buy some extras online. For the shoes, she ordered three different sizes just to make sure she had a proper fit. There's also a bra, several more panties, panty nylons and a necklace.

I'm glad to see that she's continuing to let her hair grow longer.

"Upstairs, Diana. Please get dressed ASAP. I want to be with my girlfiend. My girlfriend with something extra."

She acts a little shy and embarrassed, but doesn't take long to make her transformation. She's even applied lipstick.

"Dear, baby," I say, "the lipstick doesn't look right. Do you mind if I wipe it off? I mean, it looks a little garish, like you selected the wrong shade. In fact, I think I'd like you better without lipstick."

Diana acts humiliated and defeated.

"Just believe me, Diana. And I would expect you to tell me when my fashion sense is screwy, OK?"

So I wipe it off, followed by a quick makeup kiss.

"So what did you use to fill out your bra?" I ask.

"TP, good old TP."

I push in a bra cup and it stays pushed in! "We do have to buy you some silicone breast forms or something," I say. "How does it feel to have boobs? Sorry to say that mine are so small. But you, you get to pick whatever size boobs you want!"

"I love it," says Diana. "I'm so taken with this whole thing that I feel guilty. Feel guilty because I think I don't deserve to be happy."

"I give you permission to thoroughly enjoy yourself, as long as you share some of yourself with me. OK?"

"For sure. As long as I know you really do dig me this way and don't see me as a psych patient."

I laugh. "No, this is genuine. I think I really need someone who's half male and half female. Just let yourself flow this way; enjoy; let you be you. I love what you're becoming."

"What am I becoming?"

"Hmmm. Sixty percent female and forty percent male?"

We both laugh.

We sit down to watch Downton Abbey on PBS. This time we're close, side by side, and Diana has her arm around me. I snuggle closer. I could get to like this ...

We're also drinking some more local wine, and I'm feeling very horny. As the show's credits finally roll by, I nuzzle Diana's neck and nibble at her ear as I feel her long hair drift over my face. Diana puts her hand behind my head and brings my lips to hers. I can feel my breasts against hers, even if they're not exactly the real thing. The longest, most passionate kiss ensues, tongue to tongue and trying to find the most complete seal and tightest contact. Her mouth tastes nice.

From there, we roll onto the thick carpet where we coil together like snakes. I briefly grasp her penis, err, big clit, and it's as hard as hard can get, and big. She runs her muscular thigh against my own clit, and then fingers it. Jezuz fucking god, I've waited a long time for this! Patience has its rewards ...

"Do it, Diana! Do me ... "

Diana chuckles, lifts her dress and exposes her dangling rod, pulls down my hiking shorts and panties, and removes them, and I'm laying there with my legs bent. Diana looks so totally happy and full of fun, and plays her wet cock's head around my welcoming entry and around my clit (driving me batty) before slowly slipping inside. Then she looks at me full of wonderment and curiosity, and I say, "Yes."

And she says, "To the betterment of womankind."

And slowly slips in, and in, and in.

I am penetrated, occupied, solidified, butterfied, and beastified. Until she can go in no further.

"I'm home now," she says.

And we remain that way for a little while. I have her, she has me. Her hair and earrings fall onto my face. Belly to belly ...