I suppose it's rather trite to say your first time with a woman can set the pattern for your whole life. I know it was true for me, but my pattern bears more resemblance to a crazy quilt than some nice, ordinary bedspread.
I suppose the allusion to bedding is apt, as my pattern certainly included sex, but in many unforeseen ways it changed my whole attitude toward women and life.
I was 18 and very green, having grown up in a rather liberal family in the Midwest, which would count as conservative in just about anyplace else. Much to the concern of my parents, I had fled to California and entered the theatre program at a school that shall remain nameless, intending to make my living as an actor. Like I said, I was green, and that did not only apply to women. I just knew that I was destined to be a star.
I had only dated a few times since entering college, too busy studying and dreaming, not to mention trying to prove my small town denizens wrong! Away from home and despite the normal adolescent male longing to find out what was under those feminine clothes I had never even come close to finding out. Then Emma came into my life and it was never to be the same again.
We met in theater classes at school, both of us aspiring actors. She was an "Older Woman" of 19, but we hit it off from the start. We shared a couple of classes and hung out waiting for whatever was going to happen during various productions. I was flattered and excited to be with her in public. Something clicked between us and we began to spend more and more time together, both in class and out.
At first I tried my best to be John Wayne or Clint Eastward, but I have neither the body or the temperament to pull that off. Until I started noticing girls I hadn't been unsatisfied with my beanpole body, but once that switch was thrown I certainly noticed the Jocks and Macho types always seemed to end up with the girl.
Me? I usually ended up with the oddballs and eccentrics of either gender. That's where I felt most comfortable. Flirting through dinner or a movie, trying to impress some woman with my manly demeanor? Sadly, my acting skills weren't up to the task. Emma's response boiled down to 'Don't be an asshole, I like you the way you are.'
So I tried not to be an asshole.
When spring break came along, I was staying over as home was too far away to return for only a week. Emma lived in town and, to my amazement, she suggested I could stay with her with only a very tentative hint from me. I was horny and amazed and readily agreed, especially when I found out her family would be gone. We would be alone and the fantasies flamed in my head.
Hindsight tells me she was gently but firmly leading me to the bedroom with great finesse, but at the time I could hardly believe how forceful and macho I was to seduce this vision. I tried hard to be cool and experienced while undressing her, but the infamous bra hook almost defeated me. My attempt to be suave and manly while not being an asshole ended up as a farce when I got tangled in her bra strap as I tried to remove it. While I attempted this task she was trying to undo my belt, but I sort of tripped as she pulled on the buckle. I tried to steady myself but a tangled bra offered little support. We both ended up in a heap on the floor.
She looked at me. I looked at her. We both started laughing.
"Uh, Nate?"
"What say I take off my panties and you take off your whatever it is you're wearing under those jeans?"
"Uh…"
"It might be safer."
"So it's safe sex you're after?"
"Duh!"
"Just sex, then?"
"I'm on the pill. You don't think you would have ended up on the floor with me with my boobs hanging out if I was worried about getting pregnant."
"I stopped thinking when I started undressing."
"But I know what you were thinking before that."
"I suppose it wasn't too hard to figure that out."
"I beg to differ, it looked plenty hard to me."
"It sure was. Seems to have gone away, though."
"That can be fixed. You're a guy. I'm a girl. We have the house to ourselves. "
"I hope you aren't referring to 'fixed' in a veterinary sense."
"Not until I've had all the kids I want. I just don't want them now!"
"Can we try to get off the floor?"
"The bed would be a lot more comfortable."
"Ladies first?"
"Since I'm on top of you, I suppose that makes sense. Oh, I do intend to be on top at least part of the time, you know."
"Oh…"
Not the most auspicious beginning to an affair, I have to say. I certainly hadn't seen anything like this in the blue videos that were fairly common in the dorms. Well, actually most of those videos dispensed with the undressing and went right to the fucking, so I had no real guidance in the subject. I was getting a hard on, though, so at least that was moving in the right direction.
We made it into bed without further comedy and I tried my best to be cool. She had a devilish smile on her face as she reached for what passed for my manhood - rather diminutive when compared to the guys in the videos, but I wasn't going to complain. When her hand wrapped around me I was almost driven mad. I could see just why most men were so intent on sex, my own hand just didn't produce feelings like this!
I fear I erupted in her hand when she first touched my cock, putting quite a large dent in my attempted image as macho seducer. I didn't realize it then, but that was just about the best thing that could have happened to me. With that intense pressure relieved I was able to think about what Emma was feeling.
More accurately, I was able to listen to what Emma was saying. I knew what went where, but I hadn't a clue as to what would make Emma happy. It doesn't take much to figure out when a guy climaxes, those videos were rife with cum shots. I always did wonder why those girls seemed to be so happy to have their face covered in some guy's goop.
Emma was quite pleased to set me straight about that. Somewhere along the line I forgot to be worried about being a manly man and found myself enjoying the fact that I could give someone else pleasure. It was comic and passionate and a wonderful way to learn about sex. I didn't last as long as those hunks in the videos, but by the time we were through we were both very satisfied.
Well, at least until we heard a car pull up in the driveway and the cheerful whistle of her father walking up the sidewalk.
The stark terror of being caught soon washed away the languid feelings after our mutual pleasure. There was no surreptitious way out of the house, my car in the drive clearly told her parents she had company and the back door was opening before we could remove the bedclothes, let alone get dressed. I have to hand it to Emma, she was cool under fire and quickly grabbed two nightgowns from her dresser, put one on and handed me the other.
"My folks know I'm no virgin, but I really don't want them to know I'm screwing someone in my own bedroom. You've just become a girlfriend from college that I invited home since you were all alone over the break. Just get under the covers and fake it!"
Yeah right!
I quickly hid my clothes and put on the nightgown, which we stuffed strategically with my shirt and pulled the covers over us. My inability to raise a beard and my long hair were unexpected assets, but could we get away with this? We had barely hidden my clothes when her mother knocked at the door
"Oh good, you're still awake."
"Just a little girl talk, Mom. What happened?"
"Our plans got discombobulated. There was a landslide on the road to the lodge and we couldn't get there. I'm afraid you and your friend will have to put up with us for the week."
Emma coolly introduced me as Jan and lied six ways from Sunday. Feigning sleepiness I mumbled something in a high voice, hoping Emma's mother would take the hint.
Nope! Emma had to get all the details while I lay there quivering. Those quivers were nowhere near as much fun as the ones I had experienced a short while before.
After far too long we were alone again. Then the realization set in, Emma had just committed me to being her girlfriend for the entire spring break!
There I was, having just had sex with a woman for the first time in my life and she had just tossed my masculinity into the dustbin for the next week!
"Emma! What were you thinking?"
She rolled over and gave me a hearty squeeze. "I was thinking that you are now going to share this bed with me for the entire week and my parents will not be annoyed."
"But… but…"
"You have a very nice butt."
She illustrated the fact by grabbing my ass and doing… things…"
"But they'll never believe I'm your girlfriend!"
"Are you or are you not an actor?"
"I am but a poor, benighted student clinging desperately to a scholarship in the hopes of becoming an actor."
"Hey! Not bad for improv. Remember two weeks ago when the Prof had us doing Shakespeare with gender roles exchanged?"
"Oy vey!"
"So you remembered I was Shylock!"
"Mainly I wondered where anyone could find a pound of flesh on your body without a mastectomy."
"Hush your mouth! The point is - you made a wonderful Portia. You nailed the part."
"Sure, in a classroom with everybody laughing their asses off at our outrageous overacting."
"By the second read-through your voice was downright perfect."
"And my -uh-hum - slight stature…"
"Gives you a real shot at being my girlfriend for a week, Portia."
"I thought I was Jan."
"Portia. Jan. A rose by any other name would smell as sweet."
"So now I'm Rose? I'm confused."
"Quit struggling. I have you in my power. By the way, I wouldn't describe your endowments as slight."
"Which is not something your girlfriend would possess, remember?"
"Two pairs of panties and a full skirt should take care of that."
"I don't have a skirt."
"But I do. A nice wraparound that will fit anyone."
"I'll get hoarse talking like Portia for an entire week."
"Says the woman who's hung like a horse. Details! Consider it a challenge. Consider that we get to spend the next week together in bed."
"Consider that even if that is a very tempting invitation I haven't a thing to wear."
"See! You already know just how a woman would answer. I have a closet full of clothes."
"Won't your parents get suspicious if I wear your clothes all week - that is if I can fit in them?"
"So we can go shopping!"
"Jeez, a couple of hours ago removing your bra utterly defeated me? How the hell am I going to figure out how to put one on?"
"Portia didn't wear bras, they hadn't been invented back then."
"And I don't wear bras, either."
"Not until now."
"You're crazy!"
"Nope, but you drive me crazy - as long as we're sharing a bed."
"Can't we…"
"Nope. My parents may be liberal, but I don't want to test their limits, girlfriend. But I would love the chance to test your limits."
"By making them think I'm a girl for an entire week?"
"Only out of the bedroom, lover."
"And what happens when your sexy body turns me on and I get a hard on while your father is watching?"
"I can keep the sexiness under control if he's around. Don't want to spoil his illusions."
"Or my illusion…"
"So you'll do it?"
"If you'll help."
"Goody! I can hardly wait for tomorrow!"
"Funny, I'm not so much in a hurry."
"All the better when I have you in bed, lover."
We did get to sleep, but I'm not saying when.
We woke late in the morning to the sounds of the rest of her family moving about. In the light of day Emma's ruse began to fray a bit. How was I going to get out of the house when her family thought I was a girl? I didn't want to get either one of us in trouble, not after last night, but I couldn't live in her bedroom forever, could I?
Then again…
We were both thankful her room had an en suite bathroom, a luxury not to be found in an old, rambling farmhouse in a Midwest town. So after a shower and a shave - a shave that didn't stop with the few hairs on my chin but included my legs - I was pronounced ready.
Ready for what, you ask?
With a curious grin she she dug in her bureau and handed me a bra and panties, telling me to put them on while she found something for me to wear. My bruised macho tried to rear up, but as I was standing there naked at the time I was pleading a rather weak case, even to myself.
So I donned her rather too small underclothes (she had to help me with the bra hooks), stuffed the cups with stockings and socks, then reluctantly put on Emma's wraparound denim skirt and a baggy sweatshirt. I looked longingly at my bluejeans, but they were too darn tight to allow me to impersonate a woman.
A pair of frilly socks on my feet with my own sneakers, a little makeup and nail polish and the result was far better than I had feared. I stared into the mirror and saw a casually dressed college girl staring back. Granted her breasts were somehow a little odd and she looked rather uncomfortable, but a gentleman wouldn't be staring at a woman's breasts. (Sorry, that's the Midwest upbringing in me, I know that's bullshit!)
How I managed to make it through breakfast that morning is beyond my recall, but I summoned all my acting skills to pull it off. I tried to keep conversation to a minimum, but her family kept asking questions and I had to answer. Emma just grinned and winked at me, enjoying my discomfort at this performance. I got a small taste of her audacity and impulsiveness when she asked her folks if it was all right for Jan to spend the break week with her - as if it hadn't already been decided.
As soon as we finished eating she excused us to go shopping and I eagerly escaped to my car. She was serious, though. She actually did take me shopping for clothes. For me.
Now this was a truly new experience. I was a college student, fer cryin' out loud! I had a bunch of jeans, a pile of T-shirts, a bunch of (mostly mismatched) socks and the usual tighty-whities. There was one hardly used suit in the back of the closet and a couple of reasonably presentable golf shirts and one pair of gray slacks for the few times jeans and a T-shirt were out of place but a suit would have been too much.
My shopping expertise was minimal; how hard is it to grab a pair of jeans or a package of underpants? It took longer to get the credit card approval than to pick out my clothes.
This, my friends, is not how a girl shops. I was in blissful ignorance of this fact up until Emma furthered my education in something outside of sex.
Not having any sisters, I was unaware of the agony a young woman goes through in selecting a wardrobe. I hadn't even accompanied my mother shopping since I was a tiny little tot.
They say ignorance is bliss - I'm here to tell you just how true that is. I had no idea what I was in for. We started out simply looking for a properly fitting bra. I was just enough bigger than Emma that her bra was getting to be a pain. Up until that fateful day I had never given bras any real consideration unless they were plainly visible through a girl's blouse; I was far more interested in what the bra contained.
Buying a bra turned out to be a far cry from getting a package of tighty-whities. I had a peripheral awareness that there were a lot of different kinds of bras, after all I had seen the racks in passing when shopping in a big box store. Now I found myself expected to choose a bra for myself?
Good freakin' luck!
OK, band size first. I had just learned what a band size was when Emma fastened me into her bra that morning, so I put this knowledge to good use. Emma wore a 34 and it was a little tight on me, so I guess a 36 was a good choice. But wait! Emma tells me you have to add three inches to your chest size to find your bra size. If the number comes out odd, then add an inch. Since the shirt I wore when I had to wear my suit was a 32 it seemed to be correct. Sure…
Emma says women's sizes don't make any sense, you just have to try things on to be sure they'll fit. That's how I found myself in the changing room with Emma helping me to put on my bra.
My bra…
Speaking of my bra, when I took off my T-shirt I found that the darn thing had ridden up so the band was about to slice off my nipples. No wonder it was feeling uncomfortable. When Emma stopped laughing, she removed the stuffing and I removed the bra. Unhooking those little hooks turns out to be a lot easier than getting them hooked.
I don't want to boast or anything, but I actually got the first hook of my new bra hooked behind my back after only a little squirming. Sounds cool, huh? It was the top hook I got on the middle eye. Hey! I was very new at anything involving bras, on me or anyone else.
Looking at me, Emma said "I think we're going to have to find something better than socks and pantyhose to fill those cups."
"And what do you suggest?"
"Falsies, of course."
"Oh, of course. Do we go out and ask the lady where they keep their falsies and can we try a pair if I'm buying my first bra?"
"This is a big box store, not a big boob store."
"How… disappointing."
"Have you learned nothing in your theatre studies?"
"I don't remember any of the professors talking about boobs - at least not openly."
"Think costuming, think aging someone to look like an old man. Think…"
"Emma, I haven't done the Special FX class yet."
"Oops, sorry. Good thing I have. We make a trip to Supergel in Riverside. You wouldn't believe the variety of fake breasts they offer. They cater to all the drag queens."
"Somehow the idea of having to choose the right variety of breast is something that never occurred to me."
"And that's what education is for - to solve problems you never thought of having."
"Don't think I'm complaining, but isn't this getting kind of complicated and expensive so we can sleep together for a week?"
"One - think of all the improv experience you'll be getting. Two - by the time we're done you're going to look very cute. Three - I have been known to swing both ways and this way I don't have to choose. Four - after last night I think its worth a lot of effort to have you in my bed. Five - putting one over on my folks has a certain attraction and six - who says it's only going to last a week. Summer's coming and I just might have some ideas about gainful employment for two pretty girls."
I didn't have an answer to that rapid-fire recitation. In fact, I couldn't speak. The words got all jumbled up and stuck somewhere inside. So much for training to be an actor when I couldn't cope with the unexpected when it happened.
"So how does it feel?" Emmy queried as I stood there silent.
"Much better than yours, I guess."
"Good. Put your shirt back on and we can choose a few more for you. Something sexy, maybe?"
"You're kidding!"
"You want to see me in just a sexy bra, don't you?"
"Just…?"
"I suppose I could wear some sexy panties, too."
"You're just fine with nothing on."
I had recovered my ability to speak and knew I was heading into a trap. I hoped that was an acceptable answer.
"But you'd like it?"
"Of course…"
"So why wouldn't I like to see you in a sexy bra and panties?"
"Uh, 'cause most guys don't wear bras."
"But you're wearing a bra right now, aren't you?"
"True…"
"And my panties?"
"Uh…"
"And I think you're very sexy."
"Jeez…"
"So why not be even sexier for me?"
"If you put it that way…"
"I saw something in lavender lace that might do. Come on!"
So I ended up with a several bras in several colors, not to mention a bargain pack of panties before we left the place. And yes, one was lavender and lacy.
Sheesh!
So now I found myself with a bra but no breasts, a situation I never had contemplated. According to Emma, most girls find themselves having a bra but not enough breasts. In our capitalist and acquisitive culture where there's a need there will be someone to fill that need - or my bra - for a price.
If you look on the net for the word 'supergel' you get quite a few answers.
Theatre people know the word as a supplier of color filters for stage lighting. The clear colored plastic you slip in front of a stage light is called a gel, which is why the name rang a bell for me. Then there's the Supergel that offers refrigerated storage and meat packing in Europe. That's meat packing as in chicken or pork, not the kind of meat packing I saw in the dorm room videos.
Then there's Supergel carpet and upholstery cleaner, Supergel Dewy Highlighter makeup (Sephora.com), Supergel odor remover (Walmart), Supergel transparent epoxy (Amazon), Gorilla Glue's Supergel (True Value), Facetheory Supergel Oil-free Moisturizer (also Walmart), Supergel Cling window decorations (Instacart from a whole bunch of places), Airplus Super Gel Cushion Insoles (Walmart still again), Relax-a-Lot Super Gel Seat Cushions (Amazon again) and Supergel Alginate Impression Material that dentists use to take an impression of your mouth.
Pretty versatile stuff, that Supergel, but the Supergel that I was introduced to on that Saturday morning was the Supergel Breast Forms.
As Emma promised, the place was drag queen heaven, or so the advertising claimed. I mentioned a while back that I was driving my own car when I went over to Emma's house. From that you can figure I wasn't from a poor family. Not particularly rich, but I had no complaints about money. In fact, I had managed to save a few hundred bucks so I didn't faint on the spot when I saw how much the really good ones cost. I did get a little more woozy, though. I was already more than a little off kilter with the events of the last few hours.
Fortunately, a pair of the low-end forms didn't cost too much more than a medium-fancy date with Emma, a price I was willing to part with to please her. What I didn't anticipate was how pleased I was when I removed the stockings stuffing my bra and slipped in a pair of Supergel TRS3s.
Suddenly wearing a bra felt right! It didn't try to ride up, the faint lumpiness in the cups was gone and the lines under my T-shirt were smooth and inviting. The straps, that had been trying to slip off my shoulders now stayed put with the weight of my new breasts.
Damn it, I liked it! Midwest conservatism be damned!
With my new assets firmly in place we went out to my car and I buckled in, the shoulder belt settled nicely between my new breasts, giving me a small thrill. Driving over potholes was a new experience as well. By the time we left the Supergel place it was time for lunch, which proved yet another new experience. With a full day of shopping ahead of us, Emma suggested a quick stop at the nearest burger joint for lunch to fortify us for the afternoon.
I was getting used to wearing a bra and panties by that time - amazing how quickly this happened - but eating a burger with all the fixings proved to be an insurmountable challenge. The first bite saw ketchup and mustard dripping on my new breasts. Do you have any idea how weird it felt to be wiping the stuff off my own breasts? Do you have any idea how ineffectual it was? I soon had red and yellow stains accented by white shreds of paper napkin all over my shirt.
Emma just sat there laughing. I suddenly froze, realizing I was playing with my breasts in public. That's when I realized there were a couple of guys watching me as I dabbed at my boobs. I suspect I turned red, but since I couldn't see myself I couldn't tell you for sure.
"C'mon girlfriend, let's get you cleaned up. I was summarily hauled into the ladies room, which fortunately was a one-holer and I didn't have to worry about being carted off to the funny farm or the lockup as a pervert. Some soap and water, applied to my shirt as I stood there in only my bra, soon had the stains mostly removed. It didn't help that I now had a big wet spot on my T-shirt to call attention to my boobs.
Could life get any weirder?
Of course it could! I took another bite from my now tepid burger and this time the mayonnaise landed on my left breast. Just to rub it in, the mayo was joined by half a bitten-through pickle.
"Shit!"
"No, mayo. The health department would get very upset about shit on a burger."
"I'm upset about this… mayo… on my boob. How do you manage to eat and not get dripped on?"
"Many years of experience. Besides, mine took ages to grow up so I got used to them. You sort of waved a magic wand and poof! There they were."
"I need a magic wand to get this goop off me."
"Perhaps a bib?"
"If I'm going to be wearing a bib in a restaurant I'd rather be eating lobster."
"Hmmm… Maybe I can convince Daddy to take us all out for seafood while you're here."
"If I can so this much damage with burger I'd probably need a Sou'wester for lobster."
"You'd look really cute with one of those yellow hats that fisherman guy wears on the Gorton's ads."
"The dude with the beard hanging on to the steering wheel in the boat? No thanks!"
"They don't call it a steering wheel in a boat. Besides, a boat is small enough to be taken aboard a ship. In a ship they just call it a wheel."
"Well, shiver me timbers."
"I intend to do so tonight."
"If my shirt gets any wetter I'm going to start shivering right here."
"Finish your burger and we can get you a new blouse."
We haunted the second hand stores that afternoon. At first I felt downright stupid trying on this blouse or that skirt and then coming out to have Emmy vet what I was wearing, especially because there were other people watching. I just knew they were going to start screaming 'that's a man' sometime soon. I did my damnedest to summon all my acting experience to get myself into a feminine headspace, but fear is hard to overcome.
Strangely enough, I did overcome it. In fact, after a little while without a screaming mob surrounding me with pitchforks and torches I even started to enjoy it. Being the center of attention is not something that has happened to me often. Actually, being from the Midwest, being the center of attention is something that makes a fella rather queasy.
Good thing I wasn't a fella that morning, I was enjoying my time in the spotlight. Heck, I did want to be an actor. After a while I began to see the logic of Emma's comments. Matching clothes is somewhat akin to the thinking when creating a stage set, you work with color and form and function.
In a few hours we had assembled a wardrobe to get me through the week. Sure, dresses, skirts, a nightgown and such, but also slacks noticeably different in fabric and cut from what I would normally have worn. Not to mention jeans, but jeans with embroidery and fake diamonds on them. And a suitcase to put them all in, as if I had packed my own clothes before coming over.
By the time Emmy was done at the forth thrift store I had a wardrobe far in excess of what I thought I would need for a week. Shows you just how naive I was. The star of the show was a stunning black cocktail dress that somehow managed to hide the fact of my gender. No, it didn't just hide my true gender, it darn well screamed 'female.'
"Are you sure I need something like this? I asked Emmy.
"I'm going to have to order your fries with extra estrogen next time. Of course you'll need that dress when Daddy takes us out for seafood."
"Takes us out?"
"Family tradition, which I was lamenting this year when everybody else wanted to go off to la-la-land in the hills to go skiing one last time. Daddy always takes off spring break week and we celebrate, and on Saturday night he springs for a fancy dinner in a fancy place."
"So why didn't you go with them?"
"Jan, it's Spring Break, as in green and warm and promising. The rest of the family wanted to go skiing one more time, as in cold and white and frozen. Skiing is OK, but I had other plans."
"Oh?"
"Seducing you, sweetie."
"Oh!"
"Yeah. Oh."
"And was all this," I waved at my new blouse bulging with my new breasts, "part of the plan?"
"Well…"
"What?"
"I hadn't planned to let you get dressed at all for days and days!"
"I suppose I'm relieved. But why the whole act?"
"You ever have make a quick decision under pressure?"
"Certainly. Kinda like last night."
"Right. I should have known my folks wouldn't get too bent out of shape with a man in my bed, after all they do know I'm no virgin. But there I was in my little bed in my little room and suddenly Mom pops in the door and catches me doing something naughty. I guess I kinda reverted to a little girl and tried to hide my being naughty."
"The naughty was nice…"
"Wasn't it! But ever since you did Portia I've wondered just what you would be like as a girl. You really did bring out her character quite well. It all came together in a flash, so now we are sort of committed."
"I guess we are. You know, I was a bit scared I might do too well as Portia."
"Really?"
"Really. Being only 5'6," I took a some grief in high school. The whole 'manliness' bit has been sort of a sore point."
"And yet you went along this morning."
"Whatever Lola wants, Lola gets. You wouldn't happen to be the Devil's assistant?"
"I don't think so. My horns occur farther down on my body."
"So they were."
"They regrow pretty fast."
"Nice to know."
"You're not mad at me?"
"Nah. In fact, having breasts is sort of growing on me."
"You need hormones for that sort of thing."
"I understand surgery works, too. Lots of women do it if you can believe the gossip."
"Three in my high school class that I know of."
"You haven't…"
"All natural, sweetie."
"Not grass fed, though?"
"Not unless edibles count."
"I could eat you…"
"Enough! You need shoes before we go home."
"I have shoes."
"Honey, you never have enough shoes!"
I swear, by the time we were done I was almost looking foreword to the week as a female, and not just for the challenge of fooling her family. Not to mention the sex, which we certainly didn't mention to anyone else.
We made it home in time for dinner with the family, smuggling my suitcase upstairs successfully. Emma's Mom politely tossed us out of the kitchen, claiming that guests were guests and shouldn't be working. By that time I was perfectly happy to sit down (remembering to sweep my skirt at the last second) and vegetate. Shopping is hard work for a fashionable woman who doesn't want to spend a fortune to be a fashionable women for a single week.
Fortunately the TV was tuned to a news show and I wasn't called on to make polite conversation until the show ended. After only a few minutes trying to be a good guest we were called to dinner.
So far, so good…
Dinner was a shocking experience, but in order to tell you how shocking it was I need to take a bit of a detour. Remember I said I grew up in a rural town in the Midwest? I hate to say it, but there is a whole lot of Garrison Keillor's Lake Wobegon that holds true of the place where I grew up, but our town wasn't anywhere near as interesting or full of colorful characters. Didn't have a lake, either.
Respect for your Elders, proper behavior, pure thoughts in a pure body, all that stuff was taken for granted. (Please don't ask me about the divorce rate, some things you don't talk about!) Publicly say otherwise and you were taken to the woodshed. Discussions at our dinner table were pretty sparse, and not just because Mom was a great cook.
Sex education was most assuredly not taught in the schools, which means the teen pregnancy rate was pretty high. I lost count of how many girls in our class ended up 'visiting relatives' for six or eight months. Attend school while pregnant? Surely you jest!
As much as most of the town was sure that the Goddam Liberals were just dying to shove the Gay Agenda down our god-fearing throats, we did have a few people in school who came out. It didn't hurt that the captain of the football team came out as gay in his Junior year. That was quite the kerfuffle, as the team was about 70% driven by the very talented quarterback. Ostracize him and the team would suck big time. Accept him and the town morals were headed straight to hell. Being the owner of a body that was first cousin to a landslide and nephew to a grizzly bear, not many people were willing to bully him. Lots of frustrated people trying to reconcile the God of Sports with the Godless Gays.
Strangely enough, we became friends, both of us being certified oddballs. He looked out for me, I helped him with the subjects he had a hard time with. He was (and is) no dummy, but his first love was football and it was hard to fit academics into his schedule. Speaking of academics, education beyond the statutory limits of state law was vaguely suspect.
Church attendance was mandatory - Protestant, of course, nobody was all that sure Catholics were really Christians - and the mayor and town council were elected for life.
Well, it seemed like that to me, anyway.
I took a lot of flak for wanting to be an actor, the height of the local acting ambition was to be Joseph in the Christmas play at church and you just know what those actresses were really after.
Despite the town's wishes, the outside world was leaking in around the edges. I spent a lot of time in the town library, learning to use the computer. Naturally, I spent a lot of time on celebrity actors and what the entertainment business was doing, not to mention serious theatre. But over the library's Internet connection I was able to access NPR, BBC, AP news, and all kinds of sites that gave me a decent education on the state of the world. I'm still not sure why the filtering software let me read the Washington Post and The New York Times. My cynical side says it was because the people trying to protect us from the Curse of The Liberal Agenda never did figure out how to really use computers.
Oh yeah, the software did a pretty good job of keeping horny kids off the sex sites. I know, I tried.
My folks were seriously concerned for my morals, going off to the Big City all by myself, but they gave in when I scored a full scholarship at my unnamed university. I'm afraid they were right to be worried, after all I had just spent the night in a woman's bed learning about sex and here I was dressed up as her girlfriend and trying to fool her family.
So now you have an idea of where I came from and what my conception of a family dinner would be like. Even after losing my virginity and switching genders I was not prepared for family dinners at Emmy's house.
"So Jan, tell us a little bit about yourself," asked Emma's father.
"Jeez Dad!" At least let the girl take a couple of bites before you start the third degree," Emma said.
"Yeah, Dad," Emma's sister Beth added. "It's not like you're checking out a boyfriend to see if he can be trusted."
"Criminy! That's what I get for having two daughters. Whipsawed for asking a perfectly simple and polite question of a guest. I tell you what, Jan. Sight unseen I'll trade you for both of these hellions. You'd certainly make a better daughter than either of them."
"Now Harry," Emma's mother laughed, "you know what happened the last time you played the stock market. I'd at least hire a broker before agreeing to any trades."
"Mr Schulman, I'm afraid that where I come from daughters trade at least three-for-one against sons, at least sons big enough and strong enough to work on the farm. You'd have to sweeten the deal considerably before my parents would be interested."
"Why do I even bother? Well, at least I now know you come from a farming background."
"Oh goodie!" Beth crowed. "We get to play twenty questions with Jan."
"Nineteen, dear," interjected Mrs Schulman. "You already got your first answer."
"That doesn't count!"
"If you can't count, how will you know how many questions you asked?"
"The ringmaster taps me on the ass and I paw the ground as many times as he taps."
"Where'd you get a ring? You aren't engaged, are you?"
"From the master, of course."
"Is he engaging?"
"Anybody keeping track of how many questions we're asking?"
"They don't count if we aren't asking Jan."
"Emma?" I asked. "Is it always like this at dinner in this house?"
"Sometimes it's worse."
"If you don't ask a question how are you going to get an answer, Jan?"
"There are some things I don't want to know. Besides, sometimes it's more fun to just jump to a conclusion and to hell with the facts."
"You aren't a Republican, are you?"
"I'm from the Midwest."
"Relax everybody. My sister would never sleep with a Republican."
"Just for that, little sister, you can sleep on the couch and Jan can use your bedroom."
"Don't jump to any conclusions, big sister."
"Maybe it's a good thing I don't have any sisters," I said. "All I have is big, hulking brothers."
"At least you don't have to worry about them raiding your clothes closet," smirked Emma.
"I'm the runt of the litter, nothing of mine would fit."
"Not that any big, hulking brother would be interested in wearing your clothes."
"You never can tell, Beth. Some guys get off on that stuff."
"Yeah! A man in a dress. Whoopee!"
"I've known some pretty attractive…"
"This conversation has gotten pretty far afield," cut in Mr Schulman. "In fact, its crossed the field, jumped the fence, fallen in the brook and washed out to sea. We were embarrassing our guest when we should be trying to learn a bit about her."
"Daddy, just sitting at the same table with this family can be embarrassing."
"So it can, pumpkin. How many questions do we have left?"
"Nineteen," I answered.
"So, what did you major in in high school?"
"My school wasn't really set up that way. Since it was so small it didn't have anything much in the way of the Arts so I just got a semi-decent general education."
"The heck with education. Did you have a hunky boyfriend?" asked Beth.
"That's seventeen. I did spend a lot of time with the captain of the football team."
"Cheerleader?"
"Sixteen. Not on your life!"
"Who's your favorite playwright?"
"Fifteen. No way to choose, there are too many of them. I like Wilde, Miller, Checkov and Williams among the classics; Kushner and Shepard among the contemporaries. But there are so many more I hate slighting anyone."
"I like a girl who won't limit herself," Emma's dad approved.
"I believe we're at fourteen?" Emma's mother prefaced.
"Yup!"
"I want to know if you think an actress can combine that career with being a wife and a mother?"
"I haven't given much thought to being a wife or a mother, to tell you the truth. I'm not sure if it would be wise to raise children if your career required you to travel as extensively as many actors have to. Besides, there are darn few roles for pregnant women."
It was at that point I realized just how far I had sunk into my role as Jan. That answer just flowed right out.
"So do you plan to get married?"
"Nobody's asked. Thirteen."
"When's your next performance?"
"Twelve. At the end of the semester. I'm a lowly freshman, still learning my craft. I get to mill around in crowds or walk past the leads without saying anything. This year is mostly studying all the history of the theater and doing read-throughs and such. We do do some scenes in class, though."
"A shame. I'd love to see you on stage."
As if that is going to happen!
"How did you decide you'd like to be an actress?"
"Eleven. I never decided to be an actress. I just loved theatre and knew I wanted to be part of it since I was a little kid. School plays in a small town weren't much preparation for acting. They were sort of a side-issue that was expected of the least senior teacher so the school board could claim to be providing a well-rounded education."
"So cynical!"
"You'd better believe it! I have hopes that widespread Internet access will penetrate the small-minded insularity of rural life, but I'm not holding my breath. We actually had several people back home who boasted about never having left the county. If something interesting was happening in the next town over, most people just ignored it. Unless it involved sex, that is. If it wasn't in our town it wasn't worth thinking about."
"Seriously?"
"Seriously. I barely escaped. If anyone from home could see me now they would be utterly scandalized."
"Did anyone give you grief about a girl going to college?" asked Beth.
"Ten. Not about being a girl.There were those who considered higher education a waste of time; all anyone needed was enough education to run a tractor.
"Of course those were the old-timers talking, anyone who runs a successful farm these days needs to know how to use a computer to track prices and markets, order supplies, keep books that the IRS and other government agencies want to see. The also need to be part mechanic, part handyman, part meteorologist, part veterinarian, part accountant, part purchasing agent, part etymologist, labor consultant and part botanist. Farmers don't just walk behind a mule plowing forty acres any more."
"Wow! Were your family farmers?"
"Nine. Nope. My Dad sells farm machinery. Mom doesn't work outside but she's always volunteering for all the stuff people need done around town."
"I take it they aren't so close-minded as some of the people you've been talking about."
"That question won't count since it's not about me. I'd never call them liberal, but they realized that there wasn't much future for me in our town. They knew that I'd need an education to make it in life."
"Cool! None of this 'girls don't need an education' nonsense?" asked Beth.
"Eight. Not something my parents even considered."
"How are you adjusting to the culture shock?"
"Seven. I think…"
"Yeah, that's seven."
"Well, every time I think I'm getting used to this place, something or someone," I gave Emma a look, "comes along and shows me I'm still a hick from the sticks."
"I haven't noticed any hayseeds left behind when you walk across a room."
"It's that cow patty perfume you use," taunted Emma."
"You do realize my sister is all full of bull, don't you Jan?"
"Bulls don't have…" I started before I started thinking.
"No they don't… The other thing bulls usually have comes out the far end and is the exclusive province of my sister." replied Emma.
"NOW GIRLS! You should look to Jan if you want to know how a proper woman behaves in company." growled Mr. Schulman. He didn't growl too convincingly, though.
"So Jan," continued Beth, "If you're such a model of a proper woman, I suppose you had to wear dresses to church, never wear makeup, always have a chaperone when you saw a boy, cook the meals, wash the dishes and all that ancient goodie-goodie stuff."
"I'll do you a favor, Beth. I'll only count that long string of questions as one, which leaves you at six. By the way, it's 2022 now, most of that stuff died a well-deserved death before you were born, even in our little country town.
"So OK, not too many women wore dresses to church unless it was Easter or Christmas. I, personally, don't like wearing makeup. I have never had to be chaperoned if I was alone with a boy, but I think your parents might be wise to insist on it in your case. I'm a lousy cook but I have washed far too many dishes. Satisfied?"
"I guess."
"I have to ask," Mr Schulman said. "How did Trump do in your town?"
"Won hands down. There are many reasons I'm glad to be living here these days. Five questions left."
"Met any hunky boys?"
"Beth!" exclaimed Emma.
"Dozens of them. The campus if crawling with them."
"That's not what I meant!"
"Then you need to learn how to ask more specific questions."
"She has you there," Mrs Schulman gloated.
"Best make the rest of the questions count. Did you have any pets?"
"Two cats that hated each other but both wanted to sit in my lap whenever I was in a chair. I do know something about catfights and have the scars to prove it."
"Where?"
"In places a proper woman doesn't reveal to the morbidly curious. Three more opportunities to learn all about me."
"Are you going to wear a dress when Dad takes us out for dinner?"
"Why do you care?"
"Cuz then I'd have to wear one, too."
"Well, your sister and I just happened to spot this sweet little black number while trolling the thrift shops. It would be a shame to waste it."
"Darn!"
"If your family was conservative and your town was conservative, how did you end up so liberal?" asked Mrs Schulman.
"The town may be conservative, but my parents are more middle-of-the-road. Dad won't discuss politics in public, as a salesman he tries not to alienate any customers. I know he contributes to both sides of most issues. Not to be too cynical, but whoever wins can make a difference in his business.
"That said, he has to keep up with modern technology, so he has a lot more contact with the big cities than most of our neighbors. As far as I can tell, the more you know about the world the more liberal your outlook becomes. One more question left."
"Will you remember us little people when you're a famous actress and living the high life in your mansion in Hollywood?"
"Not a chance!"
"Figures… Hit the heights and poof! They forget their past."
"Not a chance I'll ever become a famous actress."
"Confidence girl! You'll never make the big time without confidence."
"Daddy!" admonished Emma. You're embarrassing my friend."
"Famous actresses don't get embarrassed easily. A winsome smile, a pair of fabulous legs, a big-time agent…"
"A lot you know!"
"Hey! My college roomie is an agent, Jan's got the legs, so all she needs is to get famous."
Alright, I admit I blushed when he said that. All my life my fair skin has let me light up like a beacon when I get embarrassed. Made going through high school quite a challenge, your normal Midwest high school boy isn't supposed to blush.
"Daddy!" Emma repeated. You're embarrassing my friend."
"I think I need to learn how to be an actor before I think about getting famous."
"I'll give you a tip. Just study my daughters when I ask them to do something and you'll see some great method acting. The pain! The put-upon countenance. The quavering voice. I tell you, they're naturals."
"Daddy!" came in stereo.
"Good Lord!" Emma cried as we reached the safety of her bedroom. "You just won the Oscar for Best Actress and also the one for Best Screenwriter! I can't believe it!"
"As long as we're handing out Oscars, you should bet Best Supporting Actress and Best Special Effects," I said as I waved at my nicely filled bra."That was kind of carrying Improv Theatre to a bit of an extreme."
"How did you come up with all that stuff?"
"It was all true, Only the gender has been changed to protect the guilty."
"Really?"
"Really truly. Cross my heart."
"You're really getting into this Jan thing, aren't you?"
"I suppose I am. Something clicked when I got those breast forms. The whole thing seems so darn… natural."
"You have my parents fooled. When they came back I nearly expired on the spot."
"Good thing you didn't. I wouldn't have known what to do with the body."
"Oh? I think I can tell you just what to do with my body…"
I will always remember that golden week together. She was a gentle and loving teacher as she schooled me in feminine ways by day and passionate sex by night. I grew confident with her family, to the point where we all went out to that fancy dinner together and her father escorted me by the arm through the restaurant doors. I was soon able to do my own makeup, minimal as it was, having had some experience in the acting biz. Hiding my mercifully sparse facial hair was no problem.
We explored the town, two girls on a fling and going everywhere together, even into the ladies room. In an amazingly short time I felt I had been wearing a bra and panties all my life; they felt right, somehow. They enhanced our lovemaking, there is nothing quite like sliding stocking clad legs past each other, feeling the tug of a garter belt as we discovered each other in as many ways as we could think of. All the while her family accepted me as a girlfriend and were none the wiser.
Sadly, Sunday evening came at last and I had to return to the real world. The problem was, I had to make my exit as Jan and my subsequent return to my dorm as plain old Nate. Jan's suitcase went into my trunk where Nate's unused rucksack was already hidden. I still hadn't figured that one out, but supposed I could improvise once again.
I settled myself behind the wheel just as Mrs Schulman came out to say goodbye. Putting her arm around Emma, she asked "Jan, have you figured out how to change back before you get back to your dorm?"
"Huh?"
"Please, darlings! When I enter my daughter's bedroom unexpectedly and it smells like pure unadulterated sex, I can't help but realize what had been happening. Jan, you have a great future as an actor - or maybe an actress - if this last week is any indication. I don't think the rest of the family knows, but a mother knows.
Comments
Oh, please tell me
that this is going to continue!
Please
Tell us that this isn’t just a standalone story. It’s very funny !! We want more...
Priceless
The twist at the end is priceless. A great bit of whimsical humor.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Spring Break
Love the story so far. Love the characters and their chemistry. I love stories of guys getting into crossdressing with a loving, supportive girlfriend/wife (as long as she doesn't go all forced fem monster on him). Love the dialog, although your longer dialog sections, especially with more than two people, should have more "he said, she asked, Tom added, Mary retorted" labeling in there. Sometimes it was a bit hard to keep up with who was saying what. You don't need it EVERY paragraph, but at certain strategic spots at least...
Thought it strange...
...that mom hadn't detected they had sex. Had Emma been in on her mother knowing and keeping it from Jan? I do believe this deserves a follow-up story. but I hope it is as good as this one.
Jessie C
Jessica E. Connors
Jessica Connors
Lovely story
This is a lovely story and a wonderful cast of characters. I'd be very pleased to spend more time with all of them. But especially Emma and Jan/Nate. I just love tender romances. Especially ones with that subtle bit of domination and soft coercion. It lets Nate off the hook over having to initiate the transformation. And I love the fantasy of lucking into a relationship with a woman that wants to lead the way.
Wonderful dialog, well written by a consummate practitioner of the craft. As always I will be looking forward to your next work
Crescenda
AKA
Your friend
Crash
Classic Ricky
This is a vintage performance, a wonderful tale of pure Ricky dialogue. It has me part chortling, part sighing at the romance of it all, and part recognising the pitfalls.
It is high praise, but this is one of your absolute best, Ricky. Anyone who can reference Lake Wobegon Days so accurately earns my respect forever .
Bra(vo)
Lucy x
"Lately it occurs to me..
what a long strange trip its been."
Spring break
Definitely begs for a sequel, so I will too. Please more.
Time is the longest distance to your destination.
Love the ending.
Oh God, I love the ending. And I agree - more chapters please.
Dani
SmDani4