Will Bobbi Sue still love Jack when she discovers his “Big Secret”? Definitely a TG story — with an unexpected twist.

Jack’s Big Secret

by Dawn DeWinter

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Last Entry: Bobbi Sue’s Diary, May 2003

I’m a dud diarist. I’ve only made nine entries in mine since May 2000. And when I reread what I wrote, I realize that I’m too thick-headed to keep a diary. I mean: I must be the most naíve girl living in North Texas. It’s embarrassing to look at the entries. I should have cottoned on to Jack’s big secret long before I did.
 
 
First Entry: Bobbi Sue’s Diary, May 2000

Jack is my best guy friend, so I wish knew more about him. But he’s kind of secretive. I think he started keeping secrets from me just after his fourteenth birthday. We’d only known each other for a year — ever since his folks had moved to Lake Roberts from Dallas — but we’d bonded immediately, ‘cause he was the only boy in my class who didn’t play football.

Instead, we’ve been watching old movies on cable. We must have seen “Gone With the Wind” a dozen times. I’ve become fascinated with Rhett Butler; thanks to him, I’ve got a thing for men with mustaches. Jack says that Scarlet O’Hara had “balls twice as big” as Rhett’s, which I somehow doubt. Of course, I know what Jack meant, even when he said he’d also have worn that red dress if he’d been Scarlet, even if did make everyone madder than a rodeo bull.

It wasn’t, mind you, that Jack has ever imagined himself actually wearing a red dress. No sirree, there’s nothing queer about Jack. He’s a real Texan. He doesn’t like anything prissy. He even likes women to wear a black Stetson, a pearl-buttoned shirt, tight Wrangler jeans, and Tony Lama boots. While I’ve never been his “woman” — we’re just friends — I dress that way myself.

Jack is mainly attracted to women with raven-black hair and olive-colored skin. He says opposites attract. You see -- Jack himself is fair-skinned and the blondest boy in the school. He’s always worn his hair long — to flaunt his good fortune, I think — for it looks so luxuriant that none of the other girls can believe he doesn’t fuss with it every night. But I remember Jack saying as how his hair is too tough to have split ends. That’s what he said, yet his hair isn’t tough at all. I’ve never felt softer hair in all my life, save maybe on a baby. I must confess that I’ve taken every opportunity I can to stroke those flaxen locks, just as I do whenever a golden retriever comes within reach of my hand.

Jack’s also got blue eyes like a baby. And a turned-up nose that’s makes him look real young for his age. A lot of the girls in high school say he looks like Leonardo Di Caprio. Last month, however, Derek Davis accused Jack of looking like Cameron Diaz. Those were fighting words, and Jack beat up Derek good and proper — right there on the school campus. It was worth a one-week suspension, Jack later told me, to prove to everyone that he’s a man.

Jack doesn’t talk much about his own dad, who works out of a home studio. I think Jack finds it a mite embarrassing that both of his parents are artists, and that people come from as far away as San Antonio to buy pottery that his dad has hand-painted with Texas wildflowers. “Texas longhorns — I wish he’d paint them instead with black-eyed Susans and Scarlet Sage,” Jack once confided in me. “It would be better for his reputation with the other guys.” That’s what Jack said.

Yet the top of his dresser has been covered with his dad’s pots for as long as I have known him. The pots would be perfect for my room, but they don’t belong in a boy’s room — even if they’re made by his dad. The watercolors by his mom are quite another matter. Someone told me that Jack’s mom’s paintings are “derivative” of Degas. Well, I don’t know whether that’s true or not, since I’ve never met Mr. Degas. But I do know this — no one can draw a young ballerina the way Jack’s mom does; and Jack has four watercolors of five dancers on his wall.

After we’d known each other for nine months, I asked him if he jerked off to them at night. I said they must be mighty arousing to a boy. Jack got as red as salsa, then stammered, “It wouldn’t be proper for me to look at them, least not while I am thinking about sexing it up with girls.”

I thought that was a mighty strange thing to say, so I kept pressing him for an explanation. Finally, he admitted it would be queer to cum while looking at the pictures ‘cause he’d been the model for ‘em. I didn’t believe him until he had me look closer, and then I saw that all of the dancers were blonds, and that the three looking towards me had his blue eyes.

“Gol dang,” I thought. “Those girls do look like Jack, except that they’ve got breasts. I guess it’s easy enough for a painter to add breasts to a guy’s chest. It’s just a couple of brush strokes after all. But what about his rear? How much flesh did Jack’s mom have to add to his butt so that it looks like a pretty girl’s?”

Well, I circled around Jack to his rear, but couldn’t tell a dang thing ‘cause he was wearing cargo pants that were two sizes too big. That was standard for him — Jack never wore tight pants. He said tight was for sissies. That day I decided that Jack’s mom must have added several inches to his butt to make it so wide, round and feminine in the paintings, but two months later, I stumbled on the real truth.

It was strictly an accident, I think. Or maybe curiosity got the better of me. It happened like this: Jack’s mom told me that Jack was having a shower, but I could wait for him in their upstairs den. That’s real close to the bathroom, and I couldn’t help but look into it as walked by it real quiet like. And I saw Jack standing naked as a heifer. From the rear only, mind you; but honestly that’s all I wanted to see.

God, how I envied his butt. And still do. I’m still boyish in the rear. My mom tells me not to fret, that I’ll get a womanly figure soon enough. But I do worry. After all, I’m fourteen and I can still fit into boy’s jeans. I doubt that Jack can — that is, unless he adds two inches to the waist size. He’s got an hourglass figure and the perfect butt — for a teenaged girl. It’s fleshy, plump and ripe. Seen from the rear, with that blond hair flowing down his shoulders, Jack looks more like a woman than half the girls in gym class.

Does Jack know that his mom didn’t have to add a single curve to her model’s physique when painting the backsides of the two ballerinas? I think he does. Leastwise, he’s told me that he doesn’t like the way he looks from the rear, which is why, he said, he’s was mighty grateful that it’s considered stylish for a boy to wear pants that are two or three sizes too big. I’m ambivalent about the baggy look on boys: It’s awfully sloppy but it does allow me to check out their boxers. But for Jack, tight pants aren’t an option — leastwise, not if he wants to avoid having his butt patted every time he turns around.

As for the front of the ballerinas, I just had to ask whether Jack’s breasts were as big as the ballerina’s. “Do you use a sports bra to hide them?” I teased. He got a strange look on his face, but confessed that he’d been wearing two breast forms when the photos got taken. Yes, they were of high quality, he agreed, but NO, they definitely weren’t his. For a cheap thrill I had him pull off his T-shirt to prove he had a normal chest. Actually, it wasn’t that normal. It was better than normal. Possibly to compensate for his big butt, Jack had been working on his pecs. It crossed my mind that he’s have to continue working on them, for if his pecs turned to flab, he’d look quite titty. He wouldn’t tell me who owned the breast forms, but it definitely wasn’t him. He was quite loud about that.

When Jack admitted that he’d been photographed with fake breasts, I knew the answer to the next question, but had to ask it anyway: “Don’t tell me you were dressed just like those ballerinas when your mom photographed you? You didn’t wear pink tights and a tutu, did you? You didn’t stand on your tiptoes in a white dress, did you? Nah, you couldn’t have. No way, right?”

Jack reddened a bit — but a lot less than any other Texas boy who’d been caught wearing pink — when he nodded that he had indeed dressed and posed like that. “But only for a few minutes each time,” he added. “I reckon that I wasn’t dressed like a ballerina for more than half an hour, tops.” That didn’t seem likely to me, considering as how it would take his mom a lot longer than five or ten minutes to do a painting of her son the ballerina; but then Jack informed me that his mom always worked from photographs. So she took about a zillion photographs of him posing in various ballerina outfits, and had then done her painting from the photos she liked best.

It eased my mind that Jack hadn’t dressed like a prissy girl for hours on end. Even so, I openly wondered why he ever agreed to put on tights and a tutu, even for a few minutes at a time. He said he did it to cheer up his mother, an answer I found a mite odd. Indeed, I asked, “I don’t understand. Are you saying that your mother wishes you were a girl? That’s sick.”

Jack flared at that last word. He said his mother wasn’t sick, leastwise not now. But she did need cheering up two years ago, so he did what he could to get her back to painting. “She needed a model, and I was it,” he whispered. “I’m proud that I was able to help her. I’m not embarrassed at all by those paintings. They were life-giving.” And then to prove that he wasn’t embarrassed, he let me see the original photographs. Gosh, did they ever make him look like a girl! For some reason I just had to have one of them, and after much pleading, I took home the picture that showed the most cleavage. It was definitely the picture that made him look the most feminine. It’s now on my dressing table beside the photos of my three best girlfriends.

“It’s a picture of Jacqui, the new girl at school,” I lied to my mother when she first asked about it. I didn’t have any choice -- did I? -- but to use a girl’s name, as I couldn’t have my mother gossiping about Jack. This is, after all, a small town; there are only three churches. My girlfriends think that Jacqui is a dance student in Dallas. I’ve given her a very interesting biography. Maybe too interesting. Jacqui makes everyone in Lake Roberts seem dull and repressed. Every so often I look at Jack and ask myself, “Why can’t you be more like Jacqui?”

Some people might say that I’m the one with the big secret — you know, that I’m passing off a picture of Jack as a portrait of Jacqui, my talented friend the danseuse from Dallas. They might think that Jack has no secrets at all. How could he have any left if he’s willing to tell me that he modeled tutus for his mother? What’s there left to hide? Oh, I appreciate that some people — those who’ve never watched Jack strip the clothes off women with his eyes — might wonder about his sexual orientation. But take it from me: Jack is as straight as they come.

There are no secrets about Jack’s sexuality. And yet, Jack is keeping an important secret from me. I’m not sure what it is, but I suspect it has something to do with the breast forms he wore for his portraits. If they’re not his — and I’m sure they’re not — why won’t he tell me more about them?
 
 
Third Entry: Bobbi Sue’s Diary, July 2001

Last night I lost my virginity. It wasn’t like I thought it would be. The earth definitely didn’t shake. My body didn’t shiver, and I doubt I experienced the Big O. At least, I hope I didn’t. If that’s all there is to sex, I may devote myself to missionary work in Guatemala. I don’t blame Jack. After all, he seemed to know what he was doing. He had lots of endurance, unlike some of the boys I’ve heard tell about. I think he was in me for half-an-hour before he finally came. He said he was going slowly so I could share in the orgasm, but I got the impression that he found my breasts more arousing than my vagina. He spent so much time sucking on them that they ended up hurting, which may be one reason why I didn’t have a proper orgasm.

But I’m not blaming Jack. He was definitely giving more than he got. Indeed, I can’t figure out why I had so little interest in his cock. My girlfriends all tell me they fantasize about “sucking dick,” but I wonder if they’ve actually seen one up close. It’s not at all attractive. And I definitely didn’t want to touch it with my lips. It looked unclean. Of course, it wasn’t. Jack’s cock was circumcised and he took a long shower before we made love. His body smelled like jasmine -- even his dick.

Even so, Jack’s cock was a turn-off. I’m not sure why. After all, Jack told me that he’d been comparing himself to the other guys in the shower room and that he was, objectively speaking, well hung. Maybe that was the problem. If his cock had been more petite — more like a clitoris — I’m sure I would have found it more pleasing to the eye. I might even have licked it.

Though he praised it, Jack didn’t seem very excited by his cock either. He didn’t pump it with his hand or rub it against me to keep it hard. Anytime it began to soften, Jack would start sucking on my tits and it would get rock solid again. Jack said he’s a “breast man.” I’ll say he is! He even had me suck on his own titties, whose nipples were large for a boy’s. While I was briefly excited to see that his nipples hardened, just like mine, they were too small to keep my interest for long. I couldn’t help myself. As I pulled away from his chest, I blurted out, “I wish your breasts were more like Jacqui’s.”

“Jacqui?” he puzzled. He had of course never heard the name. So I told him that Jacqui is a dance student in Dallas and that she has very sexy breasts. Jack was definitely intrigued: “How do you know her breasts are sexy? Have you ever touched them? Have you ever … kissed them?” He was breathing so heavily that he gasped out the questions. I noticed that he’d gotten harder.

“A typical male,” I thought. “The idea of two women having sex turns him on. What is it about lesbians that arouses so many guys? Well, I’ll give him what he craves.” So I told him that Jacqui and I had spent an afternoon fondling each other’s breasts. “We got into a sixty-nine position,” I purred. “She sucked on mine while I sucked on hers,” I lied. Jack’s body suddenly arched; he cried out; and his jism rocketed out, smacking the wall four feet in front of him.

“He’s more turned on than when he was screwing me,” I realized. It was true for me too. I had gotten a lot moister and my nipples never got harder that night than when I was fantasizing about Jacqui’s mouth on them.

Am I gay? Am I a dyke? I hope not. I don’t think I am. Leastwise, I am not going to let Jack convince me that I’m a lesbian. Maybe he’s not a very good lay. Maybe sex is bound to be bad between friends. And yet, we both said we felt romantic feelings towards each other. That’s why we had sex. It was supposed to seal our love. Instead, it’s pushed us farther apart. I blame myself. I should never have allowed Jacqui into my life. She got in the way last night. I kept comparing Jack with a ghost of himself.

Cripes, I must be gay: I do prefer Jacqui to Jack.

And what about Jack? Did he wish I was someone else? I don’t think so. He certainly liked my breasts. It was almost like a fetish. He seemed to like my breasts more than he liked me — as though he wanted them for himself. After the sex was over for the night (we had another disappointing round this morning), and as we lay in bed talking, I asked him about his breast fetish — though I didn’t use that word. It’s too judgmental. So I asked, “What’s this weird fascination you have with breasts? Do you wish you had some of your own?”

Jack flushed. He was clearly flustered, for he stammered, “D...d…do I wish had br…br…breasts like a g...g…girl? Of course not! It’s your breasts I love. I wish I could suck on them forever.” Then, just as I was thinking that he might be a normal boy after all, he added, “You girls don’t realize how lucky you are to have breasts. You’ve even got milk.”

“Is that what you were doing?” I asked. “You were suckling, weren’t you? You were acting like a baby, you know. You were sucking on my nipple like a real baby. You can’t deny it.”

Sheepishly he nodded: “I was hoping to get some milk. If you gave me some of yours, I’d be your loving slave for life.”

Boys are so stupid! Jack should know that a virgin doesn’t have any milk in her. And how about that statement! — that he’d be mine for life if I nursed him like a baby! Where did he ever get the idea that girls wanted to nurse him? After all, he’s going on sixteen. Then it struck me: Jack must have been breastfed as a baby and for some reason — which only a shrink could figure out — he’s still got the sexual cravings of an infant. No wonder he sucked as a lover! So I asked: “Jack, did your mother breastfeed you?”

He nodded quickly, then looked bashfully away.

I persevered: “I bet you liked that — your first opportunity to get close to a woman’s breast. So how long did it last? Six months? A year?”

He mumbled an answer. He had to give it three times before it registered: He had nursed for more than five years! Twice a day until he’d entered Kindergarten! And for the next two years she’d nursed him whenever he demanded comfort or calming, which he made sure was fairly often. That hadn’t been the end of the nursing. It hadn’t stopped entirely until he was nine.

I was upset. A nine-year-old boy shouldn’t have his lips on his mother’s nipples! That’s incest! Poor Jack! His mother had really messed him up! I reckoned that it was up to me, and me alone, to save him. Now that I knew his big secret, I was in a position to help him sort out his real feelings towards his mother. I intended to make him realize how much she’d betrayed her child.

I let Jack suckle on my left nipple between answers to my leading questions. I didn’t want him to know how much I disapproved of his mother’s behavior, so I feigned some sympathy towards her: “Gosh, Jack, your mother must have had nipples made of steel to nurse you twice a day for five years. You must have had some sharp teeth towards the end, especially when you were (I shuddered) … nine years old. Is that why she stopped nursing you? Because you were biting her?”

“No,” he muttered, his eyes cast downward. “She stopped because it wasn’t possible any longer.”

“I reckon your mom got a job outside the house. The modern, career woman has no time for nursing. I’m amazed that she didn’t end it years before. After all, it must have put a big crimp into her life to always be with you at feeding time. But I suppose she put her breast milk in bottles for you to drink.”

Jack nodded, and then added. “And she had help. She didn’t have to do it alone.”

As I didn’t think he’d had a wet nurse — did they still exist? -- I replied, “Of course, your father must have helped with the bottle-feeding.” I wondered if it was any healthier for a nine-year-old boy to be bottle-fed by his father than to be breast-fed by his mother. What ever would Simon Freud say?

Once again, Jack visibly flushed, as he whispered in the dark: “My dad did more than give me bottles. He helped out in every way conceivable. I’ve always been as close to him as to my mom.”

Whatever did Jack mean by that? I decided that Jack was slyly changing the subject. He no longer wanted to talk about breastfeeding. Who could blame him? His big secret finally uncovered, he just wanted to forget the sins of his mother. As I reckoned that he needed my breasts more than my advice, I let him suckle till my left nipple was raw.
 
 
Fourth Entry: Bobbi Sue’s Diary, December 2001

It’s been three months since Jack and I last had sex. I know he misses it, but I sure don’t. He never did learn how to use his cock to please me. That may not be entirely his fault, for I suspect that I’m simply not into dick. However, Jack became quite skillful with his tongue. He became an expert at — I do love this word! — Cunnilingus. He could even bring me to orgasm. I’ve definitely gotten familiar with the Big O. I miss it now.

So why did we stop having sex? ‘Cause I was feeling so guilty about Jacqui. Jack still didn’t know anything about her, but she entered my mind every time my body tingled with desire. I’d always be fantasizing about Jacqui when I had my orgasm. In fact, I couldn’t get myself off until I blanked out Jack’s presence. It was always her tongue roaming inside me, her nipple between my lips, whenever I climaxed. I was cheating on Jack with his alter ego. It wasn’t fair to him, and so I told him we’d have to go back to being “just friends.”

Ever since then I’ve agonized over the question — am I a dyke? I still don’t have the answer. All I know is that I haven’t looked for another boyfriend. I think it worries me that Jacqui might insist on joining him and me in bed. If I couldn’t have sex with Billy Bob, the school quarterback, or with Pete Jackson, the class president, without thinking about Jacqui, then I’d know not only that I was probably gay, but even worse, that I was obsessed with a girl who existed only in a photograph. Yikes, I may be even more messed-up than Jack. I may never have sex again. Do Pentecostal churches have convents to join?

Jack and I continued to talk about anything and everything — or almost everything, for I’d reckoned that he was still keeping a big secret from me. I was determined to learn it so that I could help him get over his mom, that incestuous tart. I still couldn’t abide the notion that she breast-fed him when he was nine.

That was until yesterday. I’ve just learned something about Jack’s mom — it may well be Jack’s big secret — that’s confused me a heap. The facts simply don’t add up, leastwise they don’t add up to a rational number. It was shortly after school let out that Jack began to give up his biggest secret yet. I found him next to my house, slumped against the wall crying. No, he was actually sobbing. I reckoned that someone had died. But no one had — leastwise, not yet.

“Her cancer’s back,” he sobbed. “My mom’s got lung cancer this time. That’s got to be the worst. And she never even smoked!”

Lung cancer this time? So his mom had cancer before?

“Which type did she have the first time?” I asked. Well, it turned out that this was her third bout with cancer, but the worst, so far, had occurred when Jack was seven. She’d nearly died of breast cancer. Only radical surgery had saved her.

“Did she lose a breast,” I asked.

“Two,” he sobbed. “She lost both of ‘em to mastectomies.”

“But she’s still got great breasts,” I rejoindered. And she really does. I’ve always admired the shape of her bosom. Jack wasn’t making sense. But then I thought about the ballet photos. He’d been sporting some very expensive breast forms. Hers? But of course!

Jack confirmed that his mother had indeed been wearing prostheses ever since her operations. Her breasts were almost as phony as a drag queen’s. Like most women, Jack said, his mom was devastated by her loss. She felt that she no longer looked like a real woman. It didn’t help, Jack added, that his father was such a “breast man.” Breasts had always been what his father admired most, Jack glumly said, and so it had been devastating to both of his parents when his mother lost them.

Humiliated and depressed, his mother had stopped painting. Jack and his father had feared for her life. “It was to get her back to drawing what she did best — ballerinas — that I agreed to dress up like one,” Jack said. She laughed and laughed — really for the first time since the second operation — and she chased after me with her camera as I flitted like Tinker Bell around the room. I would have died if anyone had seen me then, but I’ve known ever since that day that I danced my mom back to health. She sold two dozen watercolors of the “blond ballerina” but gave me four of ‘em. As your inheritance, she said. That’s not something I want to collect anytime soon, but it’s cool that two dozen guys thought I was good-enough looking to hang on their wall.”

“Even if they thought you was a girl?” I asked.

“Especially if they thought I was a girl,” Jack replied. “I wouldn’t want my portrait to be owned by someone who pervs after thirteen-year-old boys!”

It suddenly occurred to me to ask: “Did your mother give a name to the blond ballerina? Buyers must have wondered about it. I imagine they wanted to know your — the girl’s — name.”

Jack blushed. “Yeh, they wanted a name; so mom told them that the model for her ballerina studies was a French dance student named Jacqui. I objected that the name was too much like my own. It might give me away, I protested. But mom said it would be easier to remember if the name were close to mine. So Jacqui it was.”

I was speechless. The coincidence was mind-blowing. Was Jacqui really a figment of my imagination? Or was she as real as the photograph?

I was silent long enough for Jack to reckon that there wasn’t much else to say. He started to say good evening: “I’ve got to go in for dinner. My dad and I, we’re eating real early so that we can make visiting hours at the hospital. What I told you about my mother — you know, that she wears prosthetic breasts — that’s got to remain a big secret, right? It would kill my mom,” Jack added, “if anyone hereabouts learned that she don’t have breasts of her own. In fact, that’s why we moved to Lake Roberts — to get away from people who knew about her surgery. She resented their pity.”

I understood. I wasn’t about to spread the bad news. I don’t even intend to tell the kids at school about the lung cancer. I’ll leave that up to Jack, when he’s ready. I was curious, however, about Jacqui’s breasts. They looked so real I reckoned the forms had belonged to his mother. “Were they hers?” I asked him.

“Are you kidding? Hers are glued to her body. She never takes them off — at least not in front of me or my dad. At least, I don’t think she takes them off in front of my dad, given that he’s a ‘breast man’. She don’t want to dispel the illusion that she’s got the real thing.”

“So whose breast forms was beautiful Jacqui wearing?” I asked. As expected, Jack winced when I called him beautiful. But what can he expect? Even as a boy, he’s prettier than most of the girls in our class — as he’s been told more than once — and dressed as Jacqui, he, she, he — Jacqui’s so strikingly beautiful that she’d turn virtually any girl into a drooling lesbian.

“The breasts were lying about the house,” Jack shyly replied. “They weren’t my mom’s, and my dad ever wore such a thing. Why would he want to? Or even need to? So I don’t know who owned them. They were just there.”

How odd. I still can’t figure out who owned them. Did some fairy queen conjure them from thin air in order to give birth to Jacqui? Were they pumpkins until the moment she waved her magic wand? There IS something magical about Jacqui. And so, I like to think that Jacqui’s the only person who ever wore those breasts. Only she could find them. Only she could wear them. I must find out if Jack still has the breast forms, and if he does, maybe I can persuade him to bring Jacqui back to life for one enchanted evening.

Ever since Jack revealed his great secret to me — that his mother’s been wearing two breast prostheses since he was seven — I’ve been troubled by something he told me, something that doesn’t add up. How is it that he continued to breastfeed for another two years? He’s never talked about a nanny or a female relation.

I guess there’s still a secret he’s been keeping from me. But I’ll worm it out of him. After all, there should be no secrets between friends. One day I’ll even have to tell him that I’m hopelessly, passionately, desperately in love with Jacqui. But that secret will have to stay buried until Jack is mature enough to handle the truth.
 
 
Fifth Entry, Bobbi Sue’s Diary, May 2002

I finally know Jack’s big secret. I had to pry it out of him, and he never would have ‘fessed up if I hadn’t caught his father in the act.

It all started, dear diary, on a beautiful day in April. It was a delightfully sunny day, with only wispy clouds in the sky. It was only ninety degrees and the breeze kept me so fresh and cool that I even turned down my mom’s iced tea. I was keen on roaming. The fields, still green and lush, were sprinkled with wildflowers. There were patches of white where the egrets were minding the cattle.

I got it into my head to visit Jack’s house — something I rarely do because of its location, about a mile from anywhere and surrounded by dense bush. The first time I met Jack, he advised me against calling on him unannounced, because, he said, there were rattlers and scorpions always lurking in the bush. He alone knew the safe path through it. So if I wanted to go to Jack’s house — which weren’t very often — I always phoned him first, and he’d meet me just outside the thicket. As he led me hand-in-hand down his secret path through the bush, I used to admire his manliness.

I’m less impressed by the he-man now. I reckon he was lying to me about them rattlers and scorpions. I don’t think there ever was any of ‘em. Leastwise, I never saw any in the bush around Jack’s house. Those snakes and scorpions weren’t any more real than Jacqui. They were a concoction of Jack’s to keep me from coming over unexpectedly. Jack — or maybe his dad — wanted me always to phone first.

And why is that? ‘Cause Jack’s dad is a transvestite! That’s the big secret that Jack’s been keeping from me. He didn’t want to discover, accidental-like, that his dad prances around their house in a dress. Whenever I called, I reckon Jack pushed his dad back into the closet. Come to think of it, I don’t recollect ever meeting Jack’s dad. He was always somewhere else — in town buying hardware, or mending their fence line, or shooting varmints. Now I reckon he was probably hiding out in his bedroom painting his nails or curling his wig until I left.

I discovered the truth about Jack’s dad when I snuck up to their house. I don’t know why I was doing the sneaking. It’s possible I was hoping to find Jack dressed up like Jacqui and pirouetting around the living room. That would have been cool. Heck, it would have been downright erotic! But instead I spied a fifty-year old man standing by a stove sipping wine or champagne with one hand and stirring a stewpot with t’other.

He was wearing a black evening dress — with a pearl necklace — can you believe it! — and a star-shaped broach that sparkled like diamonds. The dress was so tight that you could see every one of his phony curves, including his gigantic breasts. They were at least a 40-D. His “breasts” were shaped like grapefruits. Heck, they probably were grapefruits. He had long legs covered with black fishnet stockings, a big butt (I saw where Jack got his inheritance!), and was teetering about on four-inch spikes. I don’t know why he didn’t fall into the stew when he stood on one leg to reach the cupboard where he was keeping his cooking oil. Good balance, I guess.

Jack’s dad was a shocking sight. His make-up wasn’t bad — leastwise, for a guy in drag. But his wig made me want to laugh out loud. It was a blond beehive! Talk about Texas women and their “big” hair-do’s! Jack’s dad had a wig as big as the state of Texas.

No wonder Jack normally kept me as far away from his house as possible. He didn’t want me to know that his dad was a transvestite, and an overdressed one at that! At least that’s what I was thinking as a slunk away, preferring to take my chances with the rattlers — if there actually are any -- rather than have Jack know that I seen his father in an evening gown.

As I finally left the bush, I suddenly realized that I didn’t know whether Jack was even at home. Maybe he weren’t. Maybe Jack had no idea that his father was a transvestite. Maybe the big secret I’d uncovered wasn’t Jack’s at all, just his dad’s.

I have to know the true story. Wouldn’t anyone? I’m going to ask him about his dad the next time we meet, but I don’t want to upset Jack. So I’ll have to be real subtle-like. He shouldn’t even realize that I’m trying to get the goods on his dad.
 
 
Sixth Entry, Bobbi Sue’s Diary, June 2002

“So is your dad a fairy?” I don’t know why it came out that way. Maybe the heat made me cranky — it had been 98 degrees or more every day since I’d last seen Jack. I confess that my greeting wasn’t the ideal way to get information out of Jack, but it sort of worked. His hands dropped to his side. His big smile turned into a small frown. But he looked more confused than angry.

“A fairy? Why would you think he’s one of them?” Jack asked. “You got to be kidding, right? How do you think I got born?”

“I don’t know. Maybe he’s only your stepfather.”

That comment made Jack angry: his lips curled down. It was clear he didn’t want me to challenge his dad’s masculinity. As I’ve said, Jack is all Texan. So I hurriedly explained: “Of course, he must love women — just like you. But he also dresses like one, right?”

Jack thought for a moment, biting his lip: “Who told you that? Are folks talking about my dad?”

I smelt fear. The boy was looking about for danger like a frightened faun. Jack had never looked so vulnerable, so delicate, so feminine. My heart reached out to him as my fingers caressed his golden locks: “No one else knows about your dad, hon. Just me.”

Jack looked confused — “So how do you know, Bobbi Sue?”

“I went over to your house t’other day. I was looking for you, of course. But all I seen was your dad. He was wearing a black dress and cooking stew.”

“Was he dressed up, all in black with pearls?”

“Uh, uh. Does he dress like that often?”

Jack laughed: “Of course not, silly. We were both rushing around trying to get ourselves and dinner simmering before the ambulance arrived from the hospital with my mom. We wanted to celebrate her return with a party, so my dad was wearing his best dress. Even I was dressed up, but you didn’t see me, right?” When I shook my head, he continued, “I was wearing a … tux. It was, uhm, powder blue. You should have seen me; I looked real fine.”

It was hard to imagine Jack wearing a tux. Where would he ever find one that fitted his pear-shaped body? He’d look much better in a dress. Then he’d look like Jacqui, my blond-haired beauty.

Jack broke into my reverie: “You promise not to tell anyone about my dad? He doesn’t want word getting around that he’s a cross-dresser. At least not around here. The local folks aren’t very understanding when it comes to people acting a little different from the norm.”

“You’ve got that right. If your father wants to wear a dress, why doesn’t he live in Hollywood, San Francisco, or Austin? There folks would take no notice of him.”

“My dad doesn’t like cities. He says they interfere with his muse. He likes country ways. Since he never goes outside dressed en femme, why shouldn’t he live in rural Texas? Our house is secluded, out of the way, my dad’s privacy easy to protect. Folks have to make an appointment if they want to buy art. We can hear a car coming down the road ten-fifteen minutes before it gets to our house, and you’re the only one I’ve ever led through the thicket. Everyone else is rightly feared of accidentally treading on one of the varmints. Gosh” — he suddenly realized — “you must have gone through the thicket alone. That’s how you were able to sneak up on the house. Why did you take such a risk? Whatever got into you?”

I’d thought the varmints a fiction, and so I shuddered a mite as I struck a heroic pose: “It was affection that led me safely past the rattlers and scorpions. I had to see you.”

“But why?”

As I couldn’t think of a fib, I just shrugged: “I can’t remember. It mustn’t have been very important. You know us girls — we get the queerest notions in our head.”

“I’ll say. Girls are a heap more impulsive than boys. Do you promise to keep my dad’s secret? You’ll not tell anyone about seeing him in a dress?”

“I’ll make that promise, Jack, if you start treating me right.”

“What do you mean — treat you right? Don’t I always treat you proper?”

“No, you don’t. You don’t trust me. You keep secrets from me.”

“Like what?” he asked. “How can you say I keep secrets from you? Didn’t I just tell you that my dad dresses like a woman whenever he’s at home? How about that for sharing secrets?”

“You only shared it with me ‘cause I caught your dad red-handed — you know, with red nail polish!” I was getting a mite steamed ‘cause Jack was dissing me. He hadn’t told me anything I didn’t already know. He wasn’t really sharing with me at all. “If you’re honest about sharing everything with me, you’ll answer me now when I ask, who was it that breastfed you after your mom got breast cancer? Well, who? Or is that a real secret that I’m not friend enough to know?”

“There’s no big secret about it, leastwise not now. It was my dad who was breastfeeding me, just as he had since I was born. I already told you my mom had help.”

“But how? How can a guy give milk? Only a woman can do that. You’re joshing me.”

“I am not. My dad’s started taking female hormones the moment he learnt my mom was pregnant. He took a lot of pills to make him lactate, and once I started suckling, the milk flowed easy-like.”

“Are you saying that your dad’s become a woman?”

“Not exactly. He’s not had the final operation. He won’t have it, he says, as long as my mom likes what he’s got down here” — and Jack pointed to his own crotch before adding, “I reckon the pills have made him smaller, but I know for a fact that he’s still big enough. It wasn’t only his handsome face and brains that I inherited.”

My suspicions seemed to be confirmed. “What do you mean that you know for a fact that your dad’s got a big cock? Has he been waving it at you? No secrets, mind you: have you and your dad been rolling in the hay? Don’t be shamed to tell me the truth; I reckon that most dads learn their boys how to use their cock. That must be a regular part of growing up.”

Jack’s face got an angry red. “It weren’t part of my growing up. My father never touched my privates, leastwise not once he stopped diapering me. And the only time I seen him naked was when he was bathing or stepping out of the shower. You should wash your mind with soap. It’s downright dirty.”

“If your relationship with your dad has always been so pure, how come he stopped nursing you when you was nine? Why then? I wager he was worried ‘cause you were getting turned on by him, right? You was nine and you were beginning to get sexy thoughts about your own dad. I reckon that’s what happened.”

“Why are you so hurtful today? I tell you my secrets, then you accuse me of lusting after my own dad. I’ve never had such thoughts about any man, especially my dad. I’m not queer. It’s females I like. I’m a breast man like my dad.”

“But he’s got br…breasts of his own!” I stammered.

“Of course, so what?” he replied, as if a man with breasts were as natural as a North Texas lake.

“Do you mean that his breasts are real? I thought they was balloons.”

“How could you be so dense?” Jack scoffed. “I already told you he’d been taking female hormones all my life. Of course, he’s got breasts. Big ones. I’ve never known him not to have breasts. My mom would be devastated if he ever lost ‘em.”

“So that’s why you told me that the breast forms couldn’t be your dad’s?”

Jack nodded. “So are you finally satisfied that I’m not keeping secrets from you?”

“Not yet. I want to know why your dad stopped breastfeeding you when you was nine. Did you ask him to stop?”

“No, I reckon I’d still be nursing if he allowed it. I’m only truly happy when I’ve got my mouth around a big, feminine nipple. But you know that already.”

“So why did he stop?” I asked. “If he knew how much it pleasured you to nurse” — and Jack nodded shly— “then why did he deny you his breast? Something must have happened. What was it? Was he the one getting turned on?” As Jack shook his head violently, I asked once again, “So what happened? You have to tell me ‘cause you said there would be no secrets between us.”

Jack crossed his arms. He was defying me. “Well, I was wrong if I said that. Some things ought to remain a secret. And that includes my dad’s cross-dressing. You’re not to tell anyone else about it. Do you swear?”

I nodded and crossed my heart. His dad’s secret will be safe with me. I reckon that I will be seeing a his dad a whole lot more now that he no longer has to hide from me. One day we’ll have a heart-to-heart, just us girls, and Jack’s dad will commence to confiding in me. Then I’ll be able to learn Jack’s big secret. It’s something that he’s been hiding from the world since he was nine, poor boy. I reckon it’s real dark and sexual.
 
 
Seventh Entry, Bobbi Sue’s Diary, November 2002

With her wife recuperating from cancer, Leslie Kim had lots of time to chat with me. That’s the birth name of Jack’s dad — Leslie Kim — so I guess her parents had some inkling that their baby was actually a girl in a boy’s body. Leslie Kim says she she’s a transsexual, and I’m not to call her a transvestite again. I can’t see much difference between the two words, but I’ll heed Leslie Kim because I like her heaps.

Leslie Kim is a real lady, the kind that only the South produces. She’s normally dressed western -- in slacks, jeans, or an embroidered skirt. Her blouses usually have a Southwestern look; she told me that she bought a whole slew of them when she visited a Navaho reservation in Arizona. Since she dresses practical-like, she’s usually wearing boots or low-heeled shoes. She confided that she wears a cotton bra and panties on days when she knows she’ll be working outdoors, but most of the time she favors satin or silk lingerie. “I want to look as sexy as possible,” Leslie Kim said, “whenever I’m stripping down in front of my wife Lilly.”

I had long talks with Leslie Kim about womanhood. It seems she’s done a lot of thinking about it, and she had quite a few pointers about growing up female. Eventually, with a great deal of fear, I opened up to her. I told her my two big secrets: that I may be a lesbian and that I’m love with Jacqui, a girl who exists only in a photograph. She was real understanding. Leslie Kim even had reassuring words about Jacqui: “She may be more real than you imagine. Have you ever told Jack about your fantasies? Does he know you prefer Jacqui?”

I replied after some reflection: “I don’t recollect that I ever told him; but I let him know that I thought Jacqui was mighty beautiful. I even asked Jack if he ever wished he had real breasts.”

“And what did he reply?” Leslie Kim asked.

“He was real evasive. I don’t know how we got onto it, but he soon had me talking about breast milk. Did you know it’s his favorite beverage?”

Leslie Kim chuckled. “How could I not know? I did, after all, nurse him for nine years. I reckon he’s already told you that.”

I saw an opportunity to get at Jack’s big secret, so I probed: “Jack says you was the one to end the nursing, but he still doesn’t know why you stopped.”

“Jack said that? He was fibbing to you. He rightly knows why the breastfeeding ended. You ask him about his attitude towards women when he was nine. It weren’t very healthy. That’s all I have to say. It’s up to Jack to tell you about the way he reacted to his mom’s cancer. Well, that’s all the chatting we can do right now, ‘cause I should look in on Lilly.”

I practically ran to Jack’s room. He was napping, but I awoke him by jumping on the bed. We embraced, but there wasn’t much passion. How could there be? He now senses that I was only attracted to women. While he was still groggy, I began grilling him: “I’ve been talking to Leslie Kim about breastfeeding. She’s quite an expert on it. She says that she stopped breastfeeding you ‘cause you didn’t respect women. That true?”

“I had my reasons,” Jack pouted.

“Well, you’d better tell me them, ‘cause I’m a woman and you can’t expect me to be your friend if you don’t like my entire sex. Your dad said that it was your mom’s cancer that got you disliking women. How can that be true?”

“She had breast cancer, Bobbi Sue. Breast cancer! She lost both her breasts and she almost died. I never saw a person in such pain and it was because she was a woman. I decided it was hell being a woman.”

“I don’t understand. Your mom’s pain should have made you more sympathetic towards women, not more hostile to ‘em. What was going through your little head?”

“If I tell you a secret, do you promise never to tell it to anyone at school?”

“Have I told any of your many secrets to the kids at school! You should trust me by now.” I replied indignantly.

“Okay, okay. Calm yourself. I just had to be sure, ‘cause I wouldn’t want it to get around that I once had a big craving to be female.”

“When you were little?”

“Yup, I thought I was just like my dad — a girl in a boy’s body — and I refused to wear boy’s clothing once I got old enough to know the difference. I must have been about two years old at the time.”

“So what did your folks do about a boy who insisted he was a girl?” I asked.

Jake shrugged: “What could they do? They raised me as a girl.”

“As Jacqui?”

“Yup, and everything was going fine until my mom got breast cancer. I reacted badly. Or maybe it was sensibly. Anyhow, I couldn’t see any advantage to becoming female. I became a boy — with a vengeance. I guess I was making up for lost time. I told everyone how lucky I was to be a boy -- the superior sex, I said. I was constantly sneering at “females”, so my dad punished me by withdrawing his breast. I miss it even now.”

“Serves you right. It sounds like you were a real chauvinist pig.”

“I reckon I was.”

“So what changed? You ain’t bad now.”

“It was mom. She was mighty depressed after she lost her breasts. She moped around the house for years, refusing to paint. When I was thirteen, she caught a fever and she didn’t seem to have any fight in her. My dad and I feared she was going to die.”

“Is that why you dressed up like a ballerina? To cheer her up?”

“Yup, and it worked! My mom was so pleased to see Jacqui again — for the first time in six years — that she started painting again. Even mo’ important, she got back her zest for life.”

“I don’t entirely understand,” I said. “Why was your mom pleased to see Jacqui again? Doesn’t she want you to be a boy?”

Jack replied in a real low voice, so soft-like that I could barely hear him: “She just wants me to be happy and she reckons that I am happiest when I’m Jacqui. She blamed herself, her illness, for making me fear my feminine side.”

I reckoned there was one shoe left to drop. How many had there been so far? Enough to keep all the Dallas Cowboy cheerleaders shod! So I simply asserted: “Of course, you’ve been dressing like Jacqui ever since you were thirteen. How come you haven’t let me see Jacqui in person? Why have I had to make do with a photograph?”

Bashfully, Jack replied: “I get real confused when I dress like Jacqui. So I try not to do it real often.”

“You been taking hormones?”

He nodded. “But not a lot — just enough to slow down puberty. My folks say I should keep my options open.”

I shocked him: “Well, I think you should be taking a lot more — enough to give you big, ripe breasts that I could love.”

Tentatively he asked, “You mean … you wish … I really was Jacqui?”

“Of course, silly. Haven’t you figured out that I’m a lesbian? I can only love Jacqui.”

Jack hesitated, not knowing what to do next, so I asked, “Does Jacqui have a sexy negligee or outfit she wears to bed?” When Jack nodded shyly, I commanded, “Well, Jacqui, go put on your makeup and something real sexy, ‘cause we’re going to be making some hot and heavy girl-love.”

Sixty-nine minutes later, as Jacqui and I lay naked in her bed, finally satisfied, I made it clear that she was my girlfriend from now on, and I didn’t want to see her in boys’ clothes ever again.

It was an order she had been hoping to hear all her life. She smiled real big like she was the happiest girl in the world, like she wasn’t keeping a secret from anyone. Or was she holding something back? That question was puzzling me a mite as I fell asleep in my lover’s arms.
 
 
Eighth Entry: Bobbi Sue’s Diary, May 2003

It had been bugging me for months. I should have been in seventh heaven! I finally had my lesbian lover! After all, Jacqui had finally emerged — fully dressed — out of the closet. We’d been spending as much time as possible at her house, where Jacqui had the privacy to be herself. I made sure that she didn’t forget to take her maximum-strength estro-glan pills and testosterone suppressants. Whenever we made love — which was at least once a day -- I lovingly applied breast cream after using my mouth on her nipples like a breast pump.

We were both taking triple-strength mammary supplements. Jacqui bet me that she’d have breast milk before I did. I reckoned I couldn’t lose that bet: I was looking forward to the ultimate sixty-nine. I always said that Jack looked like a milk-fed country boy, and I was looking forward to making turns home deliveries with Jacqui.

Jacqui was turning into a blond goddess. I called her my Sweet Swede.

Jacqui parents were looking into a private school for Jacqui in Dallas, starting this September, so that Jacqui could, by living 24/7 as a female, qualify as quick as possible for sexual-reassignment surgery. I knew I could talk my parents into letting me go to the same school: They had the money and they were always fretting about the “freaks” and “druggies” at my high school. Naturally, my folks didn’t know about Jacqui; they reckoned that Jack had stopped calling on me ‘cause he was dating another girl. I let ‘em think that.

I also kept telling ‘em that I couldn’t find a suitable replacement for Jack in a hick town like Lake Roberts, so they’d have to let me do my schooling in Dallas. “Too many of the boys here have the devil in ‘em,” I explained. “I’m more likely to find a good, clean-living Christian in Dallas.” For some reason, they believed me. Maybe it’s ‘cause their favorite televangelist has a church in Dallas.

Everything should have been perfect. But it weren’t. I just knew that Jacqui was holding something back from me. She was as secretive as Jack. I didn’t have my love’s total trust. And that’s no basis for a marriage. There was still had a big secret to uncover.

Until I learnt it, my mind was prey to the wildest fancies. Was Jacqui cheating on me with another girl? Was she a whore? Was she selling naked pictures of herself to raise money for her surgery? Was she really interested in boys, and using me as a fag hag for cover? Had she lied to me about her dad? Had he really been her second mom? Or was he a molester? A perv? What about Jacqui’s mother? Had she used her sexual wiles to turn her son into a lesbian? I even wondered why Jacqui was always going horse-riding alone: Was she always on top?

The questions were eating me up. I had to know the big secret that Jack was sharing with Jacqui. So I did the ladylike thing: I threw a tantrum. I accused Jacqui of cheating on me with Brad Starr, a cornerback for the Lake Robert Fighting Roosters. I’d never seen them together, but it oddly pleasured me to fantasize about brawny Brad throwing my girl to the ground.

It was quite a scene. My tears were soon real enough. And poor Jacqui — she was bawling her eyes out. Finally, I made it real clear: Either she told me the big secret that she’d been hiding from me or I’d always fear the worst. We’d be torn apart. Forever.

Jacqui’s body was shaking, as she fought for some breath, but soon enough she spit out the truth: “Bobbi Sue, forgive me. I have been holding something back, but I was doing it for us! It’s ‘cause I love you so much that I’ve been carrying this weight around. You’re right. I do have a big secret. It’s got the power to drive us apart. Are you sure you really need to know it? Can’t you take my word that I’ve never cheated on you, and that you’re the only one in the entire world who’s seen me naked, leastwise since I was a babe?”

I shook my head. Vigorously.

“Bobbi Sue, you’ve got fine folks, but they’re mighty pious …”

“I know that, Jacqui. That’s why they must never know about your relationship to Jack. When we get married, you’ll be a legal woman. That’s all they’ll need to know. But what’s this got to do with the secret you’ve been keeping from me?”

“I suppose your folks will be wanting a church wedding?”

I nodded: “I reckon.”

“That’s the problem, Bobbi Sue. Y’all are members of the Worldwide Pentecostal Assembly of Christ the Nazarene and the Latter-Day Disciples of Jehovah. And me, I’m neither Pentecostal nor evangelical.”

“Well, what are you?” I asked — with some dread. I was fearing that he was going to own up to being a member of one of them liberal churches that don’t even believe in God. My folks would go wearing sackcloth and ashes if I married an Episcopalian.

“Bobbi Sue, I’m ………..Jewish.”

I was mighty shocked. It was impossible. Jacqui didn’t look Jewish. She was my sweet Swede! I finally blurted out: “Jacqui, now don’t you go joshing about something as important as religion. You couldn’t possibly be Jewish. You’ve got those beautiful blue eyes and I don’t know anybody as blond as you. You can’t be Jewish. You’ve got to be Nordic!”

“Maybe I’m descended from one of the northern tribes of Israel — one of the lost tribes. I don’t know much about my ancestors, but I know that I’m Jewish.”

So that was that! With a heavy heart, I said farewell to Jacqui. We weren’t ever going to get married. I wasn’t even willing to change schools for her. It’s not that I’m a bigot. Heck, if I were straight, I’d even marry a Jewish guy — irregardless of what my folks said. It would be so cool being a doctor’s wife. But I’ve heard enough bad about Jewish princesses to know that there’s no way I’m going to marry a Jewish girl!!!

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Jack's Big Secret © Dawn DeWinter 2003. All rights reserved.