That's "Em" for "Emma." Dear aunt Em was well-liked by everyone in the family. Never married, but the word was that she was bisexual. She'd been an equally beloved high school teacher. After retirement, she'd moved 50 miles to a large cottage on the Blue Rock River, where she loved to entertain visitors. She could afford the home in that expensive area because of her large inheritance. She last had a roommate there for eight years or so, until the woman departed.
Personality-wise, I can best describe Em as sort of like Julia Child of French cuisine fame, without the accent and upper-class mannerisms. Not quite as forward as Julia. But a very good cook! When we visited as kids we were always treated with the best oatmeal-raisin or chocolate-chip cookies, and smoothies.
I always loved the full-size tree that grew right up through her cottage's large sun room.
Like Julia in her later years, she was overweight, but not overly so. She did her part to stay in shape, though, by jogging, bicycling and so on.
*****
It was in my cards to get to know my aunt much more when I was a couple years out of high school, drifting in and out of part-time jobs while still living at home.
During this period my mom died of a heart attack, which didn't contribute to my stability. After that, my dad, equally sad, took a construction engineering job in Saudi Arabia. I declined his offer to take me along, so he and I had a long talk about my future. Part of my restlessness and lack of direction was due to my nascent desire to be an artist, while lacking in confidence and marketable skills. So we agreed that I would start going to the local community college, where I'd take both bonehead courses and art classes. If that played out well, I could then transfer to a public university or art college.
Since aunt Em now lived only five miles from the community college, dad approached her (his sister-in-law) about the possibility of my staying with her for a year or so until I became more independent. I'm not sure what her actual reaction was, but she okayed the idea, and when dad dropped me and most of my goods off one day, she was her usual humorous and gracious self.
"Stevie," she gushed, "finally we'll get to spend some real time together! You are so grown up and handsome now!"
One worry I had was that I'd been a secret crossdresser for years. I'm sure my mom knew, but she never said anything. At first I'd often felt weird and freakish wearing some of her lingerie and clothing, but prowling the Internet about crossdressing soon revealed I wasn't that unusual.
Before my dad donated my mom's wardrobe and so on to a charity thrift store, I managed to extract my favorite bras, panties and jewelry, along with a good number of dresses, pants, tops, and shoes. My sizes matched hers except for the shoes. So when I arrived at aunt Em's with two suitcases, one contained entirely women's things. My dad still didn't appear to know about my predilection.
I felt a bit eerie when wearing my departed mom's things, but I had such wonderful masturbations when wearing them, or any other woman's, things.
My dad and I hugged goodbye. From then on, I saw and spoke with him only on video chats.
Em led me to her loft bedroom. It was small, brightly lit by a large window, and offered a nicely decorated bed, small dresser and closet. Em left to make lunch while I put things away in the dresser. My secret stash remained in the suitcase, which went into the closet.
I looked out the window at the beautiful river just across her lawn, and loved the maple and birch trees surrounding the house. I figured she must have someone managing her landscaping. She could certainly afford one.
As I came downstairs for her lunch, I was wearing panties underneath my trousers. Ah, the feeling of wearing them.....
"Dear, look what I've prepared for you -- a BLT sandwich plus a nice carrot and raisin salad, and some apple cider..... I remembered you liked those things when you were here before."
"Gee, Em, I don't know how you could remember all that. Yes, you're totally right."
Em was looking nice for her age, which I guessed as 50. She wore a white fitted skirt (not slim enough to be called a pencil skirt) and a dark turtle-neck top filled out with her generous but drooping breasts. Over that was an open, peasant-decorated and thin sweater. Her earrings were small, and her dark brown hair was coiffed into a do closely surrounding her head. Somewhat like a Julia Child.
As we talked, Em herself only had the salad. And a beer.
"I should've asked if you were into beer," she said.
"Just have one once in a while with the guys," I admitted. "Beer and pizza."
Em laughed. "Oh yes, that reminds me of my college days."
We talked about my college plans and how she might help me get to classes. I told her about my artistic inclinations, and my fragile plans to pursue them. We remembered my mom, and how beautiful and talented she was. I said I was finally getting over her demise and hoped to move on.
We agreed that I'd help her out with household chores, and try to keep things neat and orderly (even as I recalled how messy my room had been at home). She showed me how her home alarm system worked and gave me the combination to the front door.
"Stevie, you must tell me about your favorite foods, and I'll do my best to keep you happy that way. And, if you don't mind, once in a while I'll try to introduce you to new foods you may not have tried."
"That's fine," I said. "Maybe you could even give me some cooking pointers that I could use when I'm on my own."
"Stevie," she said, abruptly steering the conversation elsewhere, "do you have a girlfriend you would want to bring here? I mean, we should discuss this."
I laughed a little. "Auntie, you known I'm shy. I've only had a couple dates in my life, like to a dance or a double date to see a movie. There's no girlfriend in my life now."
"Oh good. No need to worry about that, then."
I was thinking: no girlfriend except for the woman in my suitcase! By the way, I had taken to calling my other half "Jamie" when communicating with other neophyte crossdressers online.
*****
So, my relationship with Em began nicely, with both of us very polite and friendly, as I tried not to be a burden.
Now, Em wasn't a homebody by any means. She belonged to a historical society, a gardening club and a municipal seniors club offering bus trips to casinos, apple festivals, and all sorts of things. I always knew when she'd be gone by looking at her desk calendar (she was old fashioned in not wanting to keep a cell phone calendar).
So, one Saturday when I was free for the weekend and she was away on one of her trips, I soon took the opportunity to become Jamie. But just as I was wondering what lingerie I'd wear, I yielded to my curiosity about Em's underthings. To look at them seemed like an exciting, sensual and dangerous thing, because how would she react if she found out?
I began a search through her bedroom, which was much larger than mine. What a large bed!
I planned my foray carefully, looking at the most provocative things last. Like saving dessert for last. Her large closet had some nice things, but they weren't very sexy except for some satiny nightgowns. Only the fabrics her dresses were made from were a turn-on. There were even a couple wigs on foam head forms.
I looked at her jewelry, her perfumes, her shoes (rather utilitarian except for one pointy pair of heels), until I finally found a treasure box of underwear in her chest of drawers. First, I went through her panties, of the plain, granny variety with high waists. Her bras were next, with what turned out to be D cups. She had five of them: Three had pre-formed cups and two were semi-transparent, with sensual lace or embroidery. Handling these gave me a stiff hard-on. I even lifted one of the sexy ones and held its cup against my penis' tip. Jeez, I was in heaven.
In the next lower drawer were the real prizes, for me at least. There was a longline bra, extending down to waist level, then two open-bottom corselettes -- one flesh colored, and one entirely sinful and black. And..... a long, open-bottom white girdle -- the old-fashioned kind with a zipper on the side. Yes!
I couldn't resist trying on the black corselette. Because Em was larger than me, the experience wasn't perfect. It kinda fit me on top, but was too large around my midsection. Seeing myself in the mirror, and getting wet with pre-cum, I began to worry I'd leave a trace on the garment's elastic. So I took a selfie, slipped out of the corselette and grabbed some toilet paper to erase any vestige of pre-cum.
I took every precaution to place the treasures back in their original spots in the drawers, realizing I couldn't get it perfect and hoping she wouldn't notice.
Oh, and I just had to try on one of her wigs. I'd never worn one before. The one I tried, the longer-haired one, was really tight on my scalp and I wondered if it was cutting off my blood flow. I took a another selfie, looking rather ridiculous, I'll admit.
After doing my absolute best to cover my tracks, I returned to my room in a horny state, slipped into my own lingerie, looked at some trans porn on my laptop, beat off, then felt a little guilty as usual. The orgasm, though, was nine on a scale of ten.
Jamie disappeared back into her suitcase.
*****
Em returned with mixed reviews of the casino she'd visited, because the restaurant food hadn't been up to her standards. I noticed she was wearing nylons. Funny, I had missed seeing any in her room (probably because I'd been so captivated with her corselettes). Did she wear pantyhose or the alternative? I imagined how she might look just wearing pantyhose and a bra.
Three days later, in the evening after dinner (which was sole with Brussel's sprouts and small potatoes), we were making conversation when out of the blue, she mentioned she thought someone had been through her lingerie -- because, for one thing, one of her corselettes had been poorly refolded.
"I wonder who could've done that?" I ventured. "You think someone broke in?"
"Not without the alarm system going off," she answered.
That left the intrusion up in the air.
"Do you have any idea who might've done this? Someone who likes lingerie, maybe?" she asked.
I just shrugged my shoulders, feeling my face redden a little.
"Stevie."
"Yes?"
"You?"
OMG. Me? Why, why would young innocent Stevie do such an unnatural thing?
"I think you did it, Stevie, didn't you? But why? You have a thing for women's underwear?"
Silence.
Then, "OK, me." I looked away. "I apologize. I know I invaded your privacy. I did it just like I used to go through my mom's things when she was alive. I don't know, it was like, maybe, they were magically sexy, like my mother was. I know this sounds insane."
Silence again.
"Not really," said Em. I wasn't born yesterday. I knew of several young men in my long experience who had a fetish for lingerie, bras, panties, shoes, you name it... And you, Stevie, I think you have very good insights into yourself. Your attraction to your mom..... yes, that could explain it."
I remained quiet, still extremely embarrassed.
"So, Stevie, are you one of those crossdressers? You brought women's things with you? Do you ever dress fully as a woman?"
"I brought things of my mom's that my dad was about to throw away. I dress partway, kind of. I really can't make myself look like a woman.:
"And then," Em speculated, "do you have sex with yourself?"
That was the hardest to respond to. Going down into my deepest secrets. But there was the question, right out in the open.
"Yes. I suppose it makes up for not having a girlfriend."
"Thank you for telling me all these things. Usually guys are so reluctant to admit anything like this. Like they want to keep up the manly image."
"Well, you're absolutely the first person I've ever mentioned any of this to."
"Look, Stevie. I understand and I won't tell you you're a deviate or something. But you must stay out of my things..... I was thinking about this before tonight and thought if you were into what I thought you were into, I'd be supportive. I decided that if you wanted to dress female here, well, I'd just make it possible for you to do so, just as long as it's kept entirely between the two of us, and the neighbors and my friends didn't know. They're not as liberal as me."
I thought I'd been spared an execution and had been sent to girlie-land. I imagined dressing fully as Jamie when around the cottage, and being female-friendly with Em. Could I be so lucky?
REP
It went beyond just allowing me to dress. Em took me on several shopping expeditions to malls in the big city with her buying everything I wanted, and even more of what she herself thought was nice, feminine and appropriate. She bought and had delivered a dresser just for my womanly things, and a stand-alone wardrobe cabinet with extra room for dresses and so on.
My grades improved in college, and I was more happy and balanced. But my Jamie was entirely contained within our little cottage. No trips out into the world, even though Em had taught me about makeup, dressing and femininity to the point where I could pass as a young, nubile young woman. It helped that I was slender, with a face that could easily pass as female when enhanced with a wig and makeup.
With her acceptance of me, we became closer. Fortunately, all the trees and brush around her cottage kept neighbors from peering into the house as "Jamie" walked around. When someone unexpectedly dropped by, Jamie retired to her room temporarily. When guests came for dinner, they had dinner with Steve and Em.
I became quite comfortable wearing bras, panties, dresses, feminine tops and wigs (we'd bought two that fit comfortably). I loved the feeling of my faux hair falling down around my face, my breasts jutting forward, my earrings dangling, wearing sexy shoes, and more. Before, dressing had inevitably led to orgasms; now, it fit more into my feminine lifestyle. I always sat down to pee, even when presenting as Steve. My voice uncannily went up in pitch, naturally (no, she secretly wasn't feeding me hormones). My ways of speaking with Em became more woman-to-woman and we talked more about feminine things and concerns.
Em even joked that I should introduce tampons to my routine!
We touched each other more and hugged once in a while. She developed a habit of coming up the stairs into my bedroom to kiss me goodnight as though I were a child. But I liked it because it brought me back the days when my mom did the same. I think I began to fill a need in Em just as she helped me meet my needs.
Sometimes she even asked me what I thought about her outfits when she was preparing to go out.
Of course I still masturbated frequently. To get me to that place, I usually fantasized about making it with other crossdressers or trans women, or about a guy roughly forcing sex on me and kissing me. I even fantasized about Em several times, wondering what she looked like wearing her black corselette. Other times, I looked at erotic photos of sexy women in girdles and corsets on my laptop.
Eventually the issue of my being asexual came up. Em and I were in a more talkative mood than usual after some wine with dinner. This particular evening, I wore loose tan slacks along with a loosely draped, longish and soft top with long sleeves. My breasts made nice dents in it. I felt so comfortably female.
Em complimented me, saying I was becoming more and more feminine, and she was seeing me more and more as a daughter or young female friend.
Afterwards, we went to watch her favorite English PBS TV series, sitting comfortably next to each other on her couch. After it was over, she turned to me.
"Oh Jamie, I've wanted to ask you this for so long, but I hate to be intrusive. Can I ask you something quite personal?"
"Of course."
"Well, I know you masturbate, for sex. And I think that's what young men oftentimes need to do.
"So," she continued, "what do you fantasize about when you're doing 'it,' for lack of a better word. I've never seen a man masturbate, never."
Had she apparently never looked at online porn to satisfy her curiosity?
I responded: "All sorts of things. Other crossdressers, women with penises, you know. Sometimes I just look at the sexy lingerie I'm wearing. I might imagine a powerful man taking me, fucking me -- or me giving him oral sex. Actually though, more often I just look at these things online rather than fantasize."
I wondered how the work "fucking" resonated with her. She didn't mention it.
"I'm going to ask something that's way out in left field," she said quietly but intently. "This is really odd coming from an older woman to a young man -- maybe it's even illegal!"
Where was this going? Jesus.
"Would you let me watch you have sex with yourself? I've always wanted to watch a man masturbate while he's lying in bed, but it would be equally vivid to watch you masturbate while being Jamie."
The way she talked about it, it all seemed so rational and neat; how could I turn her down? In fact, there was an undeniable turn-on about her request.
"This is all so new," I managed to say. "I don't have any experience involving sex with real women. ..... I'm a virgin, after all. But you want to watch? ..... I would probably be nervous, you know, but I guess we could do it. When?"
"This weekend, when we have lots of time."
"In the evening?"
"No, I was thinking afternoon."
"Like me to wear anything in particular?"
"Hmmm. A nightie, maybe. With wig and makeup. Jamie with her penis!"
*****
As was our habit, sort of, we didn't talk any more about our rendezvous until Saturday rolled around. We had been a little more high strung and tentative leading up to that day. I was more aware of being a girl with sex in the offing, whatever it would be. I wondered if she actually wanted more than just watching. The prospect actually excited me.
At our appointed time, I donned my sexiest nightgown, applied makeup exactly as she'd taught me, including a sexy shade of lipstick, and I eased into my nicest wig. A tiny spritz of expensive perfume completed the prep.
I called for Em, and she soon appeared up the stairs, ebullient as ever, in a long, red-velvet skirt and a burgundy-colored satin top, filled out with her generous boobs. Her hair was pulled up more neatly than usual, and she was wearing large silver hoop earrings.
"Oh dear," she managed. "What have I gotten us into with this unusual request? Jamie, only do this if you're totally comfortable with it. Really."
I knew she was just being polite, as was her habit. I had pulled the blinds mostly shut, so my bedroom was quite light-subdued. I lay down. Em sat on other side of my bed, smiling.
"Em, I'm going to dwell on my own fantasies, because I think you're not that comfortable seeing porn."
"You are so perceptive. It's true. I think pornography isn't quite right. I just have that feeling. Like, it's not real enough, if that makes any sense. It's people acting. Now, fantasies -- they come from within."
As I obtained some fragrant hand cream from a nearby dispenser, I felt the nice tug of my bra straps, and the taste of lipstick. As I pulled up the hem of my nightie, I took a last look at Em before I closed my eyes. She was aptly bent forward, holding her chin with her hand as her arm was balanced on her thigh. She was no longer trying to be casual or funny.
I made sure both my hands were smoothly coated with the cream, and then clasped my halfway erect cock, just holding it still for a while. It quickly attained a full erection.
I needed to select a potent fantasy, for sure. I began to dream away about sucking a trans woman's wonderful erect dick, seeing its perfect cut head inches from my face, and watching pre-cum issue from it. I imagined grasping the shaft, and then planting my lips around its rosy head and tasting it. Such a perfect fit.
Back in the reality of my bedroom, my erection was now very hard. Things were beginning well. I began to stroke with both hands. One thing, though, was that I had masturbated that very morning, so I worried I didn't have a full compliment of jizz. But things were building.
Suddenly my attention drifted involuntarily to auntie Em watching me and expecting me to perform (and titillate her?). At that point my sexual buildup began to waver a bit. I thought that just stroking faster would bring me back toward an orgasm, but embarrassingly, I began to lose my hard-on.
"Oh, jeez," I said, I lost my fantasy. I guess having someone watch distracted me. I had looked forward to sharing this with you."
Em smiled. "Oh, Jamie. Don't feel any pressure; don't get down on yourself. Here ... can I touch you?"
I nodded.
She moved over so as to be next to me.
"I've had male lovers, you know; I'm not a spinster," she said as she lay her hand over my penis. It quickly began to rise again. "There, it just wants some female attention."
Yes, that was very nice. Very helpful. Very sexy, even from an older woman.
She then cradled my balls and lightly handled them before grasping the end of my member.
"I so enjoy feeling your pre-cum, Jamie. .....Close your eyes again," she directed gently.
"Now imagine, dear, that you're Jamie at an outdoors party at night feeling tipsy, when this handsome, muscled young man leads you down to a lake. You begin kissing him, and he soon has you up against a rough tree, feeling your breasts and cunt. You initially protest, but your passion takes over and you want him in you so bad.
"Now, Jamie, lube your hands again and stroke."
I did just that while I had the mightiest erection I'd ever had, I'd swear.
"You begin to unbuckle his wide western belt, unbutton his levis, and pull the zipper down. He pulls out his upward-arching cock, pulls up your dress, and lifts you up to insert himself into you. He's strong, and he moves you up and down on his shaft. Meanwhile, he's kissing you passionately. You reach down to play with your clitty. He cums; you cum."
About this time, I actually came myself, big time. Spurting to high heaven. Getting my nightie all covered with jizz. I was relieved that my earlier masturbation hadn't reduced my pool of semen. I was young.
I finally opened my eyes. Em was looking so pleased and happy.
"Oh good, so good, dear! I'm glad you told me your fantasies; I just went with one of them!"
She left to get me a towel and I then took a shower, and eventually returned to her as the fully dressed Jamie.
*****
So, that was my introduction to sex with a woman! So unconventional, but I was pleased that we'd pulled this off. I now felt so much more comfortable with her -- in every way.
When we talked now, we could talk about sex like anything else -- to a point. I wondered what was in our sexual future, since she'd so deliberately stepped into my sexual sphere. Not surprisingly, she began showing up in my masturbation fantasies, along with women with penises and studs.
One evening she mentioned, "We have a little sharing and trust thing between us now, right? I'd really like to watch you again, sometime."
That happened. The next time, she led the fantasy from the get-go. When my eyes closed, she led me into a fantasy where I was in her bedroom trying on her black corselette. This time, it fit perfectly ..... my dick was erect under it. She had me visualizing the cups jutting out, and noting the way my womanly hips filled out its bottom. I myself fantasized looking into a mirror and kissing myself on it.
As I stroked myself vigorously in the bedroom, I came mightily once more. This sex was really getting quite heavy .....
Again, we talked casually at length about the fantasy, and she needed to know if it was good for me? Yes!
*****
She promised a surprise for our next encounter, so I was one horny Jamie as the week progressed. Now, progress in my classes was taking a dip because of my preoccupation with our adventures -- and this next one was to be on her bed. What did she have in mind? I kept fantasizing.
This time, our sort-of mother-daughter liaison took place later in the day. The sun had set, and her bedroom's lighting was very subdued. We'd just finished drinking glasses of wine when she gifted me what she wanted me to wear: a white corselette she'd ordered online -- which, she said, was a vintage, classic Rago foundation, with all its artful and sexy touches. It fit me nice and tight, and breast forms filled it out quite sexily Adding to it were long with white nylon stockings that attached to its garters (she helped attach them).
All this brought my dick sticking out from under the Rago into full membership
I lay there, feeling warm from the wine, admiring and being very turned on by the curves of my breasts, and seeing my waist pinched in with the corset's insistent pull. This was all so immensely erotic.
I couldn't help but touch the tip of my penis peeking out from under the corselette's bottom. Copious pre-cum there.
While all this was going on, Em had retired to her bathroom to change from her street clothing. Would she emerge wearing a domme's tight and commanding leather, along with a whip, like in so many porn photos? Or holding a cane, to punish me to taking such naughty delight in lingerie?
She was taking too long, so I closed my eyes to imagine more of these things while I touched the end of my cock again.
"Wake up, Jamie!"
After silently creeping up, there she stood, wearing ..... the very sinful black corselette I'd tried on!
She smiled.
I swore she looked even sexier than in my fantasies. Her breasts filled out her cups perfectly, with their sexy shapes and curves. I had always preferred seeing stout women in these foundations.
Her hips jutted out from the sides of the corselette prominently, and all of her was tightly contained by elastic lace. Black nylon stockings were secured with black and chrome garters. Her precious pussy was hidden under the open bottom. Inside her bra cups were the very faint outlines of her nipples.
"This is my gift to you, Jamie, since I know you were taken by it. Like what you see?"
I could barely talk and I couldn't take my eyes off her. Choking a bit, I answered, "It's beyond great. It's like a fantasy come to life."
"Well," said my aunt, "I wanted to give you a little more stimulation for your masturbation, which of course I'm here again to observe, right?"
"Oh, yes," I said, anticipating our event. "And I can't thank you enough, again, for this corselette I'm in."
Now she lay down next to me so we were side by side, and I thought I could feel her body heat. She reached over and found my penis under the bottom of my Rago.
"Oh, yes, Jamie. I love it. There's so much pre-cum. So much! Corselettes do that to you, yes?"
I recoiled in a pleasurable way from her hand's stimulation.
"I'd just love to lay here," she confided, "and keep turning you on and on -- what they call edging -- and somehow collect all your pre-cum in a precious little bottle ..... Like maybe, sometime, you could wear a condom to do that."
I'd never had a condom on before, but could imagine it.
"So, what I'd like you to do now before you masturbate is close your eyes and allow your hand to explore my corset. Just feel it all, while at the same time you're wearing one."
"Mmmmm," I murmured, "And I hope I don't have a wet dream while doing so!"
She laughed a little, so she knew what wet dreams were .....
So, I leaned over on my side, closed my eyes, and began feeling -- her tits first, of course. So big and soft -- filling her sexy elastic lace cups to their brims. I even spent some time on the cups' pointy tips and what had to be her nipples underneath.
"Feels so nice," she responded..
I felt her Rago straps, then let my hands wonder down to her belly and hips, exploring that wonderful spot where a woman's hips spread outward on beautiful curves created by a tight foundation.
Then my hands found her garters and nylons. I was in a Class A erotic heaven, with my ultra-hard cock issuing even more streams of pre-cum, running down my leg.
When I was down in that zone, I felt her body tighten just a little, but she didn't say anything. When my hand, now having a mind of its own, sought to explore the nether region under her Rago's bottom, Em simply said "No."
I lay on my back again, and now it was Em's turn, smiling sweetly. She reached over, undid my garters, rolled up my corselette a little, and totally freed my boi clit.
When she found its head, it was amazingly wet with pre-cum, as was the bottom of the corset and my balls.
"Your fascination with corselettes ..." said Em in a low and husky voice, "I have the same fascination with pre-cum. It's like the nectar of the gods. Not like sperm ejaculate, you know, that's messy and sticky and goey. Pre-cum is my perfect. It's perfection.
"Would you wear a condom sometime so we could collect it? I wouldn't even be surprised that someone, somewhere makes a condom just to collect it. That would be so sexy!"
Not waiting for an answer, she kept swiveling her hand around my penis' head. This time she couldn't even wait for me to do the stroking. She immediately and vigorously stroked me until I came, all over everything.
"You have a big cum, Jamie, you boy-girl, and I just love to make you cum, to take over like this. Or would you rather do it yourself?"
I was still recovering from the massive orgasm. I had to think. "Better with you, when I can look at you in your black Rago. My god. Looking at your breasts in those cups. Perfect cups and breasts. And your hips and face and lips and hair ....."
"Oh, I love to hear what excites you, Jamie. It's so nice that I can bring you pleasure and that you like my appearance. Of course, you're are a lovely and sexy person too, in the feminine sense. With a penis."
And so that was that, as I retired to my bedroom with visions of sex swirling in my head. After an hour I fell asleep. The next morning I was already anticipating our assignation the next weekend. Another surprise?
*****
Is it possible for a twenty-year-old to fall in love with a 50-ish woman? Any thoughts I had about her when I first met her -- frumpish, with wrinkles, extra pounds, and older-generation attitudes -- had been forgotten thanks to our sex and her imagination. Her taking me in hand, so to speak.
I suppose much of my attraction was due to this being my first deep intimacy with a woman. Now those auntie attributes I'd first seen had became imbued with sexuality. Even the memory of having seen her granny panties now made those panties a turn-on for me, as nutty as that sounds. I was taken.
And of course she knew. I asked to draw her portrait for my portraiture drawing class and she consented, "as long as your other studies are done."
Yes, I really had to bear down to complete assignments in English composition and calculus, but with her encouragement (and monitoring!) I was able to do so.
I most wanted to draw her in her Rago, but settled for a head and shoulders. I'm sure she could see my love and attraction in my sketchbook.
*****
The next Friday, we finally ventured out of the house for the first time, with me as Jamie. We went out in her canoe at night, cruising past riverside homes softly lit from within. It's odd to be wearing a wig while in a canoe, but I had to look very much the part. My own hair had been growing longer, but wasn't long enough yet. Nonetheless, I felt very female out there, totally enjoying the night air and the fireflies with their flickering lights. We were an older lady and a younger woman paddling in unison. Em was even singing some obscure song along the way.
The next day might've been our next bedtime adventure, but Em put it off for a day, saying she expected something to be delivered. It was, and Sunday bloomed beautifully, with the promise of more deep fun. Breakfast was eggs and sausage links, with some prosecco.
*****
As had become our new habit, we were in Em's bedroom. She had me wearing one of my sheer nightgowns, with a strapless bra underneath, and frilly panties with ruffles and lace -- looking as thoroughly feminine and Jamie as possible. While deliciously slipping into these delectables, I had already been getting wet. Finally, Em appeared in a dressing robe, holding a small package, the very same one that had been delivered.
"Ah, you look so thoroughly lovely," she said. "Sexy, indeed!"
As i sat on the edge of her bed, she walked up and had me open her robe, which revealed a new black corselette, never revealed before. She waited for my reaction.
This one was more showy, with satin and lace panels, and red embroidery.
To be honest, this creation didn't turn me on as much as her Rago, but I told her it was equally sensational and provocative. It too had an open bottom, and its sexily decorated cups were a turnon.
Something led me to lay my head against her tummy, and circle my arms around her waist. This seemed a bit awkward for both of us, but she began to run her fingers through my hair, and say in a comforting voice, "Oh Jamie, we are such a pair, aren't we? I love you too, and we are having such fun, aren't we? Who'd have thought your interest in my lingerie would take us this far?"
I could feel her body heat once more, and it was comforting. I stood up and placed my face between her boobs.
My hands began to range around her spandex-clad body, giving me a powerful new erection, which I'm sure Em felt.