Home in the Hills Pt. 02

Jonathon had to endure two weeks of waiting until his next session, if it could be called that, with Nora. Nora -- a name that might've once seemed unexciting, now seemed sexually tinged and full of possibilities. Nora began to play a major role in his masturbation fantasies, until what he was imagining departed greatly from the real woman. At some level he knew this, but the thought of her telling him to do this or that thing was just too exciting.

In college classes now, he was increasingly mentally undressing his female classmates. Just seeing the hint of a bra under their clothing -- just a little strap-line or seam -- prodded him to imagine what her bra looked like, and what her breasts looked like as they merged into the bra. Of course, some of the more brazen women would display their bra straps in the open, and Jonathon found that so stimulating that he had to avert his gaze.

Jonathon had to decide what lingerie he would be wearing to Nora's. He possessed three bras but for various reasons he didn't think any would impress her. So he ordered one for quick shipment online, hoping that the mother in his house wouldn't open the package by mistake. It was a dainty white bra with little bows, a 36A, almost like what a still developing girl would wear. He certainly couldn't wear a double D bra to Nora's! When the little confection arrived, it fit perfectly, and he almost instantly pleasured himself with it on.

Then there was the matter of panties. He had to select a pair that contained his bulge well, so he found one in his stash, also white, and stretchy, with lace.

On the day of his next visit, a Friday, he added control-top pantyhose to his ensemble (he loved the tight feel) and took the bus up the hill to Nora's place, getting more nervous by the minute. A shrink session with benefits!

Nora didn't immediately answer his doorbell ring from the building's entry, and he began to wonder if she was home. Maybe he was a nothing to her, he thought, and she forgot about their "appointment." Maybe she was just toying with him, and had dumped him. But eventually that cloud disappeared as he was buzzed in and made his way to her apartment.

Jonathon's diary: "Surprisingly, Nora was wearing about the same outfit as before, with different nylons -- fishnet this time. That was a bit over the top, but who am I to complain? Also, her moist lipstick was a more provocative red. I immediately said I'd been looking forward to this visit A LOT. She was all smiles, but seemed slightly high-strung. She took my coat and told me she could see a hint of my bra under my sweater. To which I replied that I assumed no one could see. She then asked what I wanted to drink: wine, beer, or something she called a Bourbon Lift cocktail which she said was nice and creamy with some coffee liqueur. Well, this sounded intriguing, though I knew I had to be careful not to get drunk, so trying to be funny, I said I wanted a lift.

Nora's diary: "Jonathon rang, and I let him ring a couple times more. I just enjoyed the thought of making him wait and making him more nervous! I really think I can get inside his head well, though sometimes he surprises me, like asking to see my bra. ... I decided to get him a little more inebriated this time with a sweet cocktail, which he went for. And I had turned the heat on in the apartment, assuming we'd get to the point of partially undressing. Like strip poker.

Jonathon's diary: "It only took one drink to get me high. Delicious. I felt like I could drink three of them, but I held the line there. I was sitting on her leather sofa, with her across from me in a comfy upholstered armchair, wearing studious rectangular glasses for the first time. Sipping some bourbon and Coke on the rocks, she asked me how it felt riding the bus, wearing women's things underneath. I admitted enjoying having a secret, and that I was much more attuned to what the women passengers were wearing, like their jewelry and hair. And shoes. Then, without a hint of emotion, she wanted to know if having such a secret sexually excited me. I told her yes."

Nora's diary: "Jonathon was getting a bit inebriated ... Yay! And he was beginning to sit in a much more relaxed manner. ... I asked him, as I went around the living room closing the blinds, how he wanted me to react when I saw what he was wearing. He gave this some thought and said he knew it was outlandish, but he wished it would turn me on. So then I kinda led him on by saying that maybe it would turn me on, or maybe it wouldn't. He nodded. So I told him to go ahead and undress for me. Fortunately, he was inebriated enough to have shed some inhibitions, and he carefully removed his sweater. There was the cutest, loveliest little bra, with tiny bows and sewn-in ribbons, and little AA or A cups. I noticed no hair on his body, and guessed he'd been body shaving."

Jonathon's diary: "So there I was, right out in the open, for better or worse, and Nora seemed to delight in seeing the bra on me. My nervousness melted right then and there. She had to come over and look at all its little details, saying she'd worn a bra like that once. Like, it brought back memories. She said she liked it on me ... . And then she sat back down and told me to take off my trousers. She didn't comment about the little bulge under my pantyhose and panties, but told me I had a nice boyish figure. She wanted to know where I obtained all my lingerie, and so on. I kept wishing she'd come over and touch me."

Nora's diary: "I confess I've had mixed feelings about his fixation on women's clothing, but told him how pretty he looked, and that I thought pantyhose looked sexy on him. ... I said I wanted to see how he looked in women's shoes, so I found some two-inch heels and let him wear them. He seemed in heaven, and now I was a co-conspirator! So, after a little awkward silence, he finally got around to asking to see ... me. I told him to come over and unbutton my blouse, which he did a bit clumsily, while blushing. There were my neatly cupped boobs in my favorite black, semi-transparent, demi bra with white embroidery. It even turns me on to wear it. He seemed completely entranced, like he'd just stepped into the Sistine Chapel or something. He helped me slip out of my blouse and there I was, open to his male gaze. He tentatively traced the lines of the straps with his fingers, all around, which I found stimulating, to say the least. He unhooked the back, then re-hooked, as though he didn't want to spring nature's jugs free. Then his fingers were on a cup, exploring the stitchery and seams. When his finger reached the area of my nipple, I shivered just a little with excitement, because my nipples are soooo sensitive, especially when touched by someone else. He looked into my eyes directly for the very first time today and smiled a little."

Jonathon's diary: "Unbuttoning her blouse was like living a wet dream. Undoing each button was increasingly erotic, and there she was, adorned in a most beautiful, skimpy black bra. Immediately, I wished I was wearing it. I found myself exploring every nook and cranny of this totally sexy garment. Touching her skin was almost as thrilling. Dear god. I couldn't tell if she was just indulging me or if she enjoyed showing herself off. When my fingers finally reached the tips of the cups (and the bra fit her PERFECTLY) she reacted a little. I couldn't tell if I had just tickled her, or she was having a sexual reaction, or WHAT. So I just said that she and the bra were absolutely perfect."

Nora's diary: "I told Jonathon I was a 38C and mentioned he was a little wet under his pantyhose and panties. That got him a little embarrassed, and he sat down again and sighed. I rather liked this charged encounter where he wasn't clawing at my tits or trying to rape me. I was in the catbird seat. At this point I served him another cocktail, since the other one had begun to wear off. I asked him how it felt to be exploring me. He fessed up, admitting he never could've imagined doing this with a woman, that it was like living a fantasy, and that he liked my body as well as my lingerie ... that touching my skin was electric. Well, that was a little breakthrough -- liking me as much as my gift wrapping. Or at least I hoped that was the case. ... I again led him on by asking if there was anything else he wanted to do with me. And, like he was executing a prenuptial agreement or something (!), said now it was my turn to show him my whole body. I expected as much. But I didn't want to be seen as easy, so I informed him that it might happen next time we got together -- but that also, he must dress completely as a woman then. I told him I wanted to hear how he felt when he looked more like a woman. His face betrayed his disappointment, but he went along with the idea. So I added with a laugh that how he could go home and beat off. He laughed a little, too. Immediately after he left, I confess I fingered myself to orgasm. All this in the name of helping a college student cope with his idiosyncrasies."

Jonathon's diary: "My assignment is to dress as a woman for Nora, so we can find out how I feel when I look more womanly. Well, this is one assignment where I'll earn an A++. I have two weeks to get my act together, to look like a Jenna. I know I sound melodramatic."

So, Jonathon deliberated about his wardrobe and what he would wear for Nora. He decided upon a country-girlish blue-checked gingham dress, which sort of matched the theme of his innocent little bra with bows. It was duly delivered, and surprise! -- it actually fit him well. He splurged and also received a new blonde wig with braided pigtails, some new clip-on earrings, white pantyhose, and more. A truly artistic confection.

Nora's diary: "I made Jenna (nee Jonathon) wait downstairs again. I am such a sadist. Anyway, he came up all bright-eyed with his backpack filled to the brim, and I told him to go dress in the bedroom -- after another Bourbon Lift, of course. He hadn't hinted about his female wardrobe, so when he emerged, here stood before me a stereotypical Swiss miss! I mean, I think he had gone with the theme of that cute little bra with the bows and stuff. Here he was in this nicely fitted blue-checked dress with a waist drawstring and sleeves gathered at the wrists, and -- of course! -- white pantyhose, and not to forget, blonde pigtails. It was like my 'Jenna' had just returned from milking the cows and yodeling. The only departure from the stereotype was the short dress length, coming just above her knee. All I could do was whistle, saying he had an eye for an ensemble, and that guessed he was wearing the cute bra underneath. To which Jenna gushed that she (I will refer to "he" as "she" now) was wearing an equally cute half slip underneath, and matching white strapped shoes ... in which she was a little unsteady. But she managed to twirl around for me. I was truly seeing the emergence of Jenna."

Jonathon's diary: "It was so strange, changing into 100 percent women's things at somebody else's place. Bra, slip, dress, wig, pantyhose. I didn't know if Nora would laugh, applaud, be astounded or be ho-hum. She did seem to like what I pulled together. I should mention that she herself had changed her look for this visit -- wearing tight leather pants, dark crew-neck sweater, short leather boots, and had her hair in a bun. Very sexy, all of it. ... And then, she decided to do what I couldn't -- she found her makeup kit and made me up with eyeliner and mascara, moist lipstick, and all. I looked in the mirror; she had done such a skilled job. ... And then, naturally, she had to know how I felt."

Nora's diary: "Jenna said she felt so light (lightheaded?) and yet strangely pregnant with womanness, like she felt her breasts were real, her hips were wider, and so on. She said my final-final touch, applying fingernail polish, was wonderful. And, she was candid enough to notice me moving toward the masculine with my leather pants and sweater, and pulled-back hair, and no makeup. Funny, I hadn't really done that deliberately. Jenna admitted that she had always been most attracted to women with muscles who expressed power and weren't very girly. Like, airbrushed Playboy centerfolds had never turned her on. So, while she was slipping into the role I wanted her to try, unconsciously I had slipped toward the kind of person she inwardly desired. Interesting."

Jonathon's diary: "Nora took some photos of me, and then plied me with more creamy bourbon. Love that stuff. ... All dressed as Jenna, I had this insane desire to kiss her and make love. But of course I'm never the forward one, and all I could lean on was our sort-of agreement of tit for tat. So I asked if I could undress her completely. She thought about this a little while I looked at the shape of her boobs under her sweater. She said she had to make absolutely sure I was trustworthy; that if our unorthodox sessions became known, her career would certainly go bust. I assured her that I wouldn't upset the applecart because I liked the apples so much. And so, she beckoned me over and told me to take off her sweater. Underneath was a grayish, rather transparent bra, without much adornment. I immediately felt my prick rising against my panties, and this time my fingers headed straight for her nipples, which were easily seen. But Nora brushed my hand away, saying it was only show and tell and calling me quite naughty. But she did stand up and indicated I could unbuckle her belt, so I did and tugged her pants downward. A black thong came into view, which barely covered her cunt. I mean, I could vividly see the outline of her cunt -- the fabled camel's foot. I had to stop myself from staring."

Nora's diary: "When Jenna began to pull down my pants, I knew I was being a bit of a tease to wear a thong. I just couldn't help myself. The moment was intensely erotic. Also, I'll admit I was a little embarrassed, standing there mostly naked. So I asked, trying to be clinical again, how she felt. Without replying and without even asking, she traced her finger around the edges of the thong, around my cunt, and OK, I lost it. I mean, when Jenna had previously touched my nipple, that had got my engine purring. But now ... well, I told her she could put her fingers underneath. Jenna looked up at me like a child and then looked back again, and timidly, hesitatingly, slipped a finger inside, and then looked up at me again, and I nodded my head -- I was getting hot -- and so she ran the finger between my now-wet labia, slowly exploring, until she contacted my clit. I involuntarily jerked."

Jonathon's diary: "So here I am, deliciously dressed as Jenna, with Nora allowing me to explore. My god. Her cunt was nicely shaved, as far as I could tell. Somehow, running my finger along her privates underneath some sexy lingerie was far more exciting to me than if she had been completely bare! Like when I touched her nipples through her bra. I must've finally reached her clit, because she stiffened and took a really deep breath, and, weird as it sounds, she held my head in her hands and pretty much smashed my face into her cunt. There was my nose stuck against her thong, within her cleft."

Nora's diary: "I lost it when I allowed her fingers under my thong. After I pushed her face into the thong, she seemed a bit embarrassed; didn't know what to do, or actually, didn't know what I wanted her to do. So I managed to ask again, in the heat of the moment, what she was thinking. Jenna looked up, her mascara slightly smudged, and allowed that she felt like fucking. And so I asked, while breathing deeply, if she felt like fucking me as a man or woman. She was very definite about wanting to play the woman's role, like, she would be using a strap-on or something. I told her she'd been seeing too much porn, but, hey, we could play."

And so Nora led Jenna into her bedroom, lifted her guest's dress, pulled down her hose and panty, and grasped her dripping-wet cock. "I like your dick, Jenna," she said, "It's standing at attention!" Jenna stood there, again somewhat unsure, while Nora kissed her neck and nibbled her ears. Nora then undressed Jenna, down to her bra, and led her onto her bed. "I want you to fuck me, Jenna," Nora said simply. "I want to feel your Jenna thing inside me." And so she guided Jenna over her, and helped insert her prick into her cunt. Jenna was then fully inside her counselor and her eyes widened and then slowly closed.

Jonathon's diary: "There I was in just my pretty bra, with my dong kinda dangling there, and I was feeling rather daredevilish all of a sudden. When she guided my missile into her, I began to go into another realm entirely. Here I was thinking of myself as a woman, giving and receiving pleasure, inside her warmth. It was like coming home; that's the only way I can describe it. Finally coming home. I leaned over to suck her nipples -- her breasts were so fine, so perfect. And she began to moan a little. And that got me going, thrusting into her slowly and deliciously, while I was still feeling the erotic tightness of my bra."

Nora's diary: "So here is this kind-of woman sticking it to me, slowly, smiling, and looking into my eyes. And then the angel starts sucking my nipples and it's like I'm swimming with porpoises, and then I head for heaven, the eternal waterfall, the tsunami, and the clouds part and I explode into one great climax. And then Jenna closes her eyes, and after one final big ram, she climaxes too, with a little exclamation. ... After we'd lain there for a while, I had her come over and lay her head between my breasts. I told her that she was good with a woman, very good indeed. And that I loved thinking of her as half-man, half-woman. That I desired her that way, and that other women would surely desire her that way too."

Jonathon's diary: "Well, it was very good sex. Nora has this way of making me feel good about myself, really. She's a saint. Laying there with my head between her perfect breasts, I told her I loved her. Simple as that -- 'I love you.'"

Nora's diary: "Originally, I never intended for us to go this far, but asking him/her to come visit me -- well, what should I have expected? And, I needed a fuck. ... And then he told me he loved me. I think I mumbled something about liking him too. I could see where this was headed: Soon he'd be wanting to move in with me; he was that kind of guy/girl. And he'd want to play out the woman role with me. So I very gently told him that while I had had the hots for him, I had to honestly say that I didn't want a relationship, and that part of my motivation had been to show him that his crossdressing was just fine, and that combining his fetishes with sex with a woman could very well work out. But not just with me, his counselor."

Jonathon's diary: "Well, my dream girl didn't quite work out as I hoped. I got a little moony, and expressed my love. That probably scared her, big time. She pulled back to say that she didn't want a continuing relationship and that she felt I had come to terms with my crossdressing and that it could, well, be part of a good relationship with a woman -- just not with her! I really felt let down, but on the other hand, better about myself."

Jonathon showered, undressed, wiped off his/her makeup, packed up his backpack and gave Nora a kiss goodbye. He figured their counseling sessions had ended, and he returned to becoming Jenna in his little corner of the family home. But now a little flame burned in him that hadn't been there before, and he knew that Jenna was an acceptable part of him.

He didn't initiate any more contact Nora, but one day he received an email from her: "Jenna. I never told you I have a twin sister, Noelle. Identical twins. I told her the other day about you. She lives in Rock Falls, not that far away. She's training as a real estate agent. She was intrigued about you and your alter ego. I showed her one of the photos I took of you. She's currently without boyfriend, and would like to meet you, as Jonathon or Jenna, you take your pick! Good luck; she and I are a lot alike, except she doesn't want to finish college."