Home in the Hills Pt. 01

All names and characters in this story are fictional and have no connection with any actual person living or dead.

*****

Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was no money left for him. So he enlisted in the Air Force for four years to earn GI Bill support for college. The support is generous, but the rental situation at his college town is so dire that Jonathon is forced to rent a room in a family home with two kids.

Fortunately, he has privacy, because his room is the only room in the third story of somewhat split-level home. And he needs privacy because he often dresses as a woman when alone and studying. He has accumulated lingerie and clothing through hit-and-miss online ordering.

Jonathon's attracted to the woman of the house, in her 30s, but never thought of acting on his impulses. He sees her lingerie from time to time when using his hosts' washer and drier, and imagines what it might look like on her - or himself.

There are a fair number of women taking art history courses alongside him, but other than one very plain and overweight woman who he's had lunch with, he has not clicked with any of the other women, except one he kissed at a drunken college party. But the next day, she hardly noticed him. He would be uncomfortable, anyway, bringing a woman home to his room. Would be nice, though, he thought, if someone came on to him and had an apartment.

But there is something going on in his head. He wonders if his dressing up is OK, or if it's twisted and perverted. He knows from online surfing that there are a lot of crossdressers out there, but can't escape the feeling that his raptures while dressed as a woman are making him unsocial, withdrawn and making him open to gossip and jokes should people find out. He takes every precaution to keep his women's clothing in several locked suitcases.

It gets to the point where he's becoming mildly depressed, and studying is becoming a little harder. And when he's that way, he dresses even more, and some days can hardly wait to return home and bloom into bras, nylons, panties and dresses.

Finally, he decides to take advantage of the University's counseling service. At first, he just sticks his toe in the water by going in to take occupational aptitude tests. Sure enough, they confirm his artistic bent. They also reveal that he might like teaching, which makes him feel good, because that's what most art majors end up doing. The older woman who goes over the results with him puts him at ease and he leaves the center with good vibes.

That gives Jonathon the confidence to seek psychological input about himself, and he makes an appointment with a counselor. At his first meeting, he learns that all the counselors are grad students getting interning hours toward their psych degrees, and he's assigned a fellow only a few years older than himself.

Unfortunately, their session doesn't go well, and they don't even come close to his reason for coming, because Jonathon finds him a cold fish with no trace of empathy. So Jonathon tells one of the managers of the psych operation that it won't work, and could he be reassigned? That person gives him a hard time, saying he can't go shopping for a counselor, but finally relents, perhaps knowing full well that Jonathon's first counselor isn't cutting it.

Jonathon realizes that he really wants a woman to talk to, and is rewarded when he sees that his next appointment is with a Ms. Jansson.

This story now continues by revealing the dairy entries of these two ...

Jonathon's diary: "Met with the new shrink today, Nora by name. This will work. She's open and friendly enough. Doesn't hurt that she's attractive, with a Swedish look - tall, big boobs, blonde. She asked me what I wanted to talk about, and I just said I wondered why I wasn't having any success with women, etc. Will meet every other week."

Nora's diary: "Second client today, named Jonathon, interesting. Thin, but not terribly so, clothing bland, finely featured face, and measured, soothing voice. I told him he had a radio voice, to boost his ego a little. He mentioned his lack of social success, wants to improve in that area, especially with women. Noticed that he would sometimes look off to the side when talking to me. Hmmm."

A later Nora-diary entry: "I haven't heard anything from boy-doll Arnie for a month. Guess it was a one-night sexcapade - we drank too much. I should know better than to expect anything would come of it ... But he was so goodlooking! Damn. Have restrained myself from texting him."

Jonathon's diary: "Second visit with Nora. She was wearing the sexiest shoes! Could hardly stop looking at them. We talked further about me and women. She wondered if I had made an effort to pal around with them, ask them out. I said I was afraid of rejection - talking to them or asking them out seemed dangerous, except for my plain lunch friend. She suggested that my friend was a good start. She asked if being attracted to a woman scared me. I said that I hadn't given much thought to that; that maybe feeling sexual toward someone was unsettling. And then, I FINALLY got around to saying that the main reason I was coming for counseling was because of my penchant for crossdressing. Like, maybe it was a refuge from mixing with women - that dressing was something I had total control over. Like, my female side would never reject me. She said she appreciated my honesty, because she had clients who never revealed their inner, inner concerns. She said we could talk about this subject next time."

Nora's diary: "Interesting development. This new client, Jonathon, didn't waste any time getting to his core reason for coming. Said he was a crossdresser. Yeah, I can very well see him doing that - he's so gentle and un-macho and into art and all. Funny, I kept looking at his face and wondering how it would look as a woman's. His hair is already long enough to be a woman's. I noticed that after he told me his little secret, his voice slowed and became softer. Very intriguing. I wonder if he wears panties under his trousers! Nora, Nora, stay professional!"

Jonathon's diary: "Third visit. I was able to relax a little more. Nora was wearing a peasant skirt and white, buttoned shirt, through which I could catch just a little glimpse of her white bra underneath. I do so love the size of her boobs and her choice of jewelry. She asked about the history of my crossdressing, and I told her it began at puberty. She asked if I dressed all the way up and pretended to be a woman. I told her pretty much yes, even to the point of wearing a wig when I have the time. She said much of this was new to her, that she'd never met a crossdresser, and if I didn't mind, she wanted to learn as much as she could. Answering another question, I told her that yes, dressing usually led to masturbation, and I usually felt a bit guilty afterwards. She asked how I felt when dressed, like, that was important. I admitted being definitely sexually excited, but also like on a different plane, like life suddenly was heady and full of colors. Then she asked me about my mother. So I thought about that, and told her that I gravitated much more toward her than my dad, and that mother was emotional and rather controlling. I said that in a way, I was glad to get my money from the GI Bill rather than be indebted to my mother and have her use money as a wedge to control me. Nora found that interesting."

Nora's diary: "I'm firming up my picture of Jonathon now. He tells me a lot. Crossdressing is highly important for his stability; he depends on it, almost like a drug. Get the feeling he's both attracted to his mom and yet wants to escape some hold she's had on him. So, I sit there listening to him, and as he tells me more, he gets animated and just slightly effeminate - ever so slightly, but I notice it. I keep looking him over and thinking, that yes, if he were in expert hands, he could be dressed and pass very well as a woman. I don't think he has that skill himself."

Jonathon's diary: "We were getting down deeper into the subject. She wanted to know if I desired to live as a woman; become a woman. I related fantasizing about going out as a woman and passing, and trying to feel what being a woman felt like. But, I had no desire to live as a woman all the time. Just being able to choose when and where! And then I dropped a little bombshell. I told her that I was attracted to her, and wished I could look like her. I said I had fantasized about her. She passed on that that was OK; that it happens with therapists all the time and she felt flattered!"

Nora's diary: "No surprise that Jonathon said he was attracted to me. He'd like to be me, I suppose. Wear my stuff ... . In my current manless state, his being so honest bumped up my self-esteem. However, I'm going to have to be careful when meeting with him and not dress too provocatively. I catch him staring at my shoes and boobs and whatnot. Oh god, I have to confess that I had a dream about him the other night. He was dressed beautifully and I told him that the only thing he lacked was some sexy lipstick, so I applied some, and then passionately kissed him/her and wanted more, but as dreams are wont to do, I woke up. I am a little worried about where this is heading ... ."

Jonathon's diary: "This time, we talked about what I fantasized about when I was masturbating. I said, usually I watch porn on my laptop while dressed, looking at sexy crossdressers and imagining making it with them, and also looking at sexy women in sexy lingerie, especially bras, and sometimes lesbians in lingerie making love, and then laying down, closing my eyes and imagining making it with one of those people. And then of course coming to climax. I admitted that sometimes I had concerns about being more interested in lingerie and stuff rather than the women themselves. She had no comment about this. ... By the way, this time her earrings totally turned me on, and I told her so."

Nora's diary: "Oh, that naughty Jonathon boy. He tells me everything, there's no end to his solitary escapades. This time I led him down the path of his masturbatory fantasies. No big surprises there. He worries that he's fixated too much on lingerie, poor dude. ... What if I told him that I masturbate daily, and maybe twice a day on Saturday and Sunday? And that I often fantasize about making it with women?"

After two more sessions, Jonathon's diary: "We were in the midst of talking about how I might approach women, like becoming more interested in them as people (and not as sex objects), when out of the blue she invited me to have our next session at her place, so we could be more relaxed and have more time. I couldn't believe my ears - I was, like, dumbfounded. I knew, of course, that we'd be crossing a line, and that she trusted me not to tell on her. ... I responded that I'd love to visit, so she scribbled down an address. My heart was beating like crazy just then and I got an erection looking at her boobs. .Now, as the day gets closer, I'm more and more afraid of going to her place. Afraid. Afraid of the unknown, of what we would do. I asked if I should bring some of my female attire, and she said no."

Nora's diary: "Well, I did it. Ready to bust your career, are you, Nora? Got the hots for your admirer? Whew! What the hell will I wear? What the hell will we do? Well, he'll be over in a week, insecurities and all. The saving grace is that he's so fucking honest about everything and that's such a turn-on. Should I come on to him or just let him gravitate toward whatever? Sex ed never told me what to do with a cute crossdresser ... ."

Jonathon's diary: "I went over, even though I thought I was getting sick with something. She lived in a so-so apartment building up a hill. Spoke to her on an intercom so she could buzz me through the scratched-up front door. I was wearing cute panties under my clothing, and was nervous as hell as I rode the elevator to the fifth floor. I had the feeling I was entering some kind of institution ... where I would see my shrink! Anyway, she welcomed me and seemed happy to see me. I was pretending we were still in her office on campus. But she was dressed sexier here. Lace-patterned black nylons, leather skirt, and again, a fitted white, buttoned-up shirt. She'd let her hair down and had made her eyes and lips look sexier. And big bangle earrings. We had some wine together. After some nice-talk, she asked me if I were wearing panties, and I said yes. She asked if I always wore them. I said pretty much. The wine was making me feel looser; I don't ordinarily drink much. Told her I wear panties during the day, and nightgowns at night. I speculated about the problem I might have if there was ever a house fire where I live and I had to evacuate in my nightgown. She asked how I felt when wearing panties. I thought about it and admitted that I felt sexy, aroused, feminine, and sinful, like panties have special powers. She called that a fetish, but that it was nothing to feel bad about - that a lot of people have them; like fetishes for cars or money.'"

Nora's diary: "Well, Jonathon showed up, nervous, as I expected. I felt like a spider with prey in my web, and played with him a little. Got him a little tipsy with wine. He fessed up to wearing panties most of the time. I know that he was eyeing the way I was dressed. We were still behaving in our detached psychologist-client mode. I decided to play it slow and easy, and see where things went."

Jonathon's diary: "Nora asked that since I was attracted to her, what did I see in her in the here and now? It was a little hard to be honest, because I'd never talked to a woman about these things, but after fumbling around a little, I told her that her patterned nylons were the big turn-on, along with her black strapped shoes with short heels. And her lipstick and eye makeup, and the way her boobs pushed against her tight shirt. Oh, and that the way her ass looked against her leather skirt was arousing."

Nora's diary: "Turned out that nearly everything I wore and adorned myself with appealed to Jonathon. Well, that made me feel appreciated and sexy, but also a bit guilty about using him as my guinea pig! Funny, we're nearly the same age, but I feel older and more mature than him. In some ways, he's still a babe in the woods. Still trying to figure out how his sexuality fits into the scheme of things."

Jonathon's diary: "Nora seemed to get slightly flustered as I told her what I found attractive. Like she wasn't used to hearing these things. Then she asked what I saw in her as a person, without all the accessories. Well, I was caught a little off balance there, but the wine was helping me along, so I told her I saw her as friendly, curious, smart, very womanly, pretty sure of herself, and someone who likes to control and run things. ... Then I said I guessed she was thinking she was merely a replacement for my mother."

Nora's diary: "Jonathon was one step ahead of me when he had one of these Aha! lightbulb moments, realizing that I was standing in for his controlling mother. Being in control of him would actually make me feel quite erotic ... . I jumped on that realization, asking him that if I were a symbol of his mom - would he be inclined to push back against me, or accede to my control, if that existed? Jonathon was getting animated, and looked around the room. He was obviously losing some equilibrium; entering new territory. Finally, he said he liked it when I told him what to do, because he has fantasized about being a quiet, demure, somewhat submissive schoolgirl."

Jonathon's diary: "Nora said that we'd really broken into some new ground this time around, and that she felt good about our progress. I said I agreed, and that I thought it worked better to be in her apartment. What I didn't say was that I was beginning to have some kind of hope of making it with her. When she asked me if there was anything else I wanted to talk about, I - inebriated now - asked to see her bra. This made her laugh, and she asked if I wanted to see the one she was wearing or one of her other bras. I naturally specified the one she was wearing. She said she was delighted to learn what was going on inside my head. She laughed again and decided that for our next session we could do a show and tell, where I'd show her the lingerie I was wearing underneath and then I could see her wonderful bra. With that, I made my exit along with a firm kiss to my cheek - my facial cheek that is. Oh, and before I left, Nora asked if I had a name for my alter ego, and I said no. So she said she was going to call my creation Jenna. Hmmm, Jenna, I like that. Jenna it will be. ,,, I can hardly wait until the next meeting."

(To be continued.)