Conversion (transgender – tv)
By Gingerfred Man
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Chapter One – Caught!!!!
If you read a lot of the kinds of true-life, first person accounts on a site like this, you know that the hero(ine) is often CAUGHT!!!!
Caught by his wife while wearing her panties. Then the wife FORCES him into femininity while cuckolding him with a large-cocked alpha male and putting him into chastity gear forever.
Or caught by Mommy while trying on her panties, then gently led into a life of little-girl, sexless petticoating.
Or how about this? Caught by his wife while wearing her black, lace panties; black, seamed, reinforced-heel-and-toe, fully-fashioned stockings; black bra (stuffed with stockings); and impossibly-high pencil heels. Then embraced by his super-beautiful wife, who tells him that having him make passionate love to her while both wear mega-femmy gear is her life-long, secret, heart's desire. After which they fuck like honeymooning rabbits.
Now, judging by the stories one reads, such "caught" incidents happen several hundred times a day across this about-to-be-great-again country of ours. But my "caughtness" was different.
I was caught too.
But not like that.
I was caught by my Mom.
But not like that.
I wasn't wearing panties.
Or any girlie stuff.
In fact, I was naked.
And so was Eric.
Who until three days earlier, when I had graduated from high school, was my classmate.
When Mom stepped in, unexpectedly, to my bedroom, Eric was three or four hip heaves away from leaving his second huge, creamy, cumload of the afternoon inside my tight bumhole.
Yes. It's true. I'm gay.
No one forced me to have sweaty sex with Eric.
I wanted his cock in my bum. And in my mouth too.
Though at the time, I had fooled myself into believing that only Eric, my three other classmates/fuck friends, and I were the only ones who knew I was gay.
Not that I had much of a clue about how to be gay and enjoy it. But that's for a later discussion.
My eyes nearly burned out as I saw the stern look my beautiful mother was giving me as Eric pushed and pulled his way to his gutbuster orgasm.
"It's not what it looks like, Mom" was NOT plausible denial.
Hot adrenaline torched my nervous system.
But I wasn't going to fight my Mom. And flight was difficult. Eric's eight-incher being buried inside me.
Plus where would I flee to?
I lived with my mother. Just my mother. And always had.
She was a good mother. The best. And I guess what really terrified me once a cogent thought penetrated my consciousness was that our great mother-son relationship was mortally wounded.
As it turned out, I was very wrong about that.
But I didn't know that at that horrible moment.
Mom didn't scream or smack me or storm out of the room to call the Gay Police or anything. Instead, she just said, "When you're through, Eric, I'd like a word with Andrew."
Until that moment, Eric had been so involved in his quest for orgasm, that he hadn't seen Mom enter the room.
Eric was the one who screamed. Then pulled his cum-drooling cock from my bumhole, grabbed his clothes and ran off to join the Islamic State or something. I don't know, since I never saw him again.
There I was.
On my bed. In my room. Naked. My bum drooling lots of thick, creamy sex cream. My cock, which had not yet yielded its cummy contribution was still red and angry.
Mom smiled at me as if it were Sunday morning and she had just inquired whether I wanted waffles or pancakes.
Mom took pity on my terrorized personage and began to lay out her findings and recommendations.
"I didn't like what I just saw there, Andrew, though not for the reasons you may suspect."
An odder opening than king's rook's pawn two spaces.
I said nothing. Just trembled.
I suspected that Mom didn't like her only offspring being gay. Thus no grandchildren.
Wasn't that all parents really cared about, grandchildren?
She continued. "I didn't like what I saw because you were sexually mistreated by that Eric person. As well as Glenn last Tuesday, Colin on the 24th and Ben the Saturday before that."
SHE KNEW?!?!?! SHE KNEW ABOUT ALL MY SEX PARTNERS?!?!?!?!
"Yes, Andrew. I know all about them. See that little bump in that corner of your room and the other bump in the other corner? Spy cameras. My friend Will was happy to install them for me. And I was ashamed for you each time. Not that you were doing gay things, really gay things, but that you allowed yourself to give sex without getting love in return. Or at least respectful reciprocation."
Huh? What did Mom mean?
She told me. "These boys stick their cocks in your mouth, you suck them to a nice, creamy cum, then suck until they're hard again. Then they fuck that gorgeous bottom of yours until they cum again. Then they leave. No kisses. No foreplay. No sweetness. They don't even give you an orgasm. You take care of that yourself after they leave, don't you?"
I couldn't answer, of course. I was too astonished. She knew everything.
Did Mom really say my ass was gorgeous? That was something, at least.
But back to my distress. Was she right?
Yes.
I blushed at someone knowing what a cowardly sissyboy I was. I loved cock. And I allowed boys my age to treat me like an unfeeling cum receptacle to get it.
But I wasn't 12 years old anymore. The 12-year-old sissyboys got the older, married, "hetero," romantic men who treated their sissyboys like little princesses as they fucked their bums raw. Those young ones got the "A" treatment because they were hairless and more feminine in appearance than an 18-year-old like me.
Sadly, when I was that young age, I was too chicken to flirt with older men. At 17, when I became ready to flirt, all I could get was guys my own age who were in complete denial about their sexuality.
Eric and the other trio were ashamed to be having orgasms with me. So no way were they sucking my cock. Or touching my cock. Or even just kissing me. So I submitted to their filthy lust with no expectation of my own orgasm. Or their adoration. Or even admiration.
My bar was really low at that time.
Mom was determined to raise it.
"Your days of giving without getting are over, Andrew," she declared prophetically.
A big promise.
Was Mom a politician?
Or did she have a plan?
"Let's talk about me before we plan for you, OK?" Mom asked.
I pulled a sheet over my naked body and warily agreed.
"Men like me, would you agree?"
I nodded eagerly at that. Mom was a spectacular beauty and one of the sexiest humans on the planet. She was 34, having given birth to me at age 16, and could have passed for 25. Men, handsome, successful men, worshipped Mom.
Mom continued. "Are the kinds of men who like me the kinds of men you would like to like you?"
Oh, goodness, yes. The cream of the creamers adored Mom. And they were incredibly kind and generous to Mom. In fact, Mom didn't work. Had never worked. Yet we lacked nothing. Because of her men friends' generosity.
The polar opposite of what I was getting.
"Why do you think men like me, Andrew?"
Was she fishing for compliments? "That's so obvious, Mom. You're amazingly beautiful."
Mom smiled. Then got serious. "Not obvious at all, Honey. That's about 40% of it by my reckoning. The other 60% is way more complicated. I don't nag them. I don't manipulate them. I don't emasculate them. Which makes me an almost unique female. That brings us up to 70%."
I had to ask. "What about the other 30%, Mom?"
Mom smiled. "Fifteen percent comes from my making a total effort to satisfy my men's needs. Even their filthiest urges. And the other 15% comes from being as feminine around them as I can be. Men need their women to be feminine. I wear stockings, heels, skirts and lingerie all the time. I let men hold doors for me and thank them for being gentlemanly. They love it."
Mom let that sink in a bit, then said, "Right now, you're at 15%. The filthy urges part. Not enough."
Was all that supposed to make me feel better? It wasn't. I wasn't beautiful. Or feminine. And no one gave me an opportunity to nag, manipulate or emasculate.
Mom said, "You're thinking that you're not beautiful or feminine or ever will be. I say, `Baloney.' We can fix that."
Fix that?
How?
Chapter Two – Focusing on the problem
"First things first, Andrew," Mom said. "You won't be listening to me properly in that state you're in. So lie on your back and pull that sheet off you. That's right. I want you to be naked."
Gulp.
More humiliation!
After I had already experienced my recommended daily allowance.
But one does not say no to Ashley Fairchild, whom I called "Mom."
So, trembling, I showed Mom what I had.
OMG!
She touched IT!
My penis, I mean.
She fondled IT!
And she talked about IT!
"You have a very nice penis, Andrew. It's not too large and not too small. Men, real men, will adore it, once you set the mood. Let me bring you a bit of relief before we continue."
And, son of a gun, she produced a bottle of Slickyboy Masturbation Cream, squirted it liberally onto her pretty right hand, and proceeded to give me the hand job of the millennium.
Mom clearly knew her way around a penis.
Despite my shame and guilt, Mom had me gasping and panting as I neared ejaculation. Then became a cum geyser.
More than I had ever shot.
And it wasn't because of Eric.
It was because of my Mom.
And I didn't even "like" females that way.
So yes, I was VERY confused.
But eager to hear Mom's plan for my better life. Just as soon as I could start breathing again.
Mom allowed me a minimum recuperation period, handed me a wad of Kleenex and began to outline my future.
"You have the beauty, Andrew. We just need to bring it out. You're already eager to do a few of the disgusting things men adore – though I saw no evidence of the really dreadful ones yet. I seriously doubt you would be into nagging, manipulation and emasculation. So the challenge will be to bring out your femininity."
I winced.
"But, Mom. I don't have any femininity to bring out."
Mom laughed.
"Of course you do, princess. And we'll get started on all that tomorrow. Wash up, now. Get that sex smell off you and join me for dinner in an hour. Mommy has to order takeout and make some other calls."
It appeared I had no choice.
Mom was going to feminize me! Just like in those true-life, first-person accounts. Would I be wearing petticoats and a cock cage?
Not exactly, as it turned out.
As I showered, my cock wouldn't go down as I thought of being romanced by men the quality of Mom's paramours.
Could that happen?
Was I wiling to femme up to get there?
What a dull story this would be if I wasn't willing.
At dinner – moo shu chicken and egg rolls – Mom laid out some parameters. "That was the one and only time I'll be milking you, Honey. It's not a mother's role to do such things. Plus, you'll be so busy with all the sexual attention you'll be getting from men that you won't want Mom touching your privates. I just thought you needed relief, especially the kind that was lovingly given to you. There will be lots of that in the future for you. I'll do the dishes tonight. You just scoot off to your room and take a good look at these."
At which point, Mom handed me a stack of six copies of a filthy magazine called "Panty Boy" and a large bottle of Slickyoby Masturbation Cream!
How long had Mom been planning all of that?
Anyway, I skittered off to my room, got naked and lay on my bed. I noted that Mom had bought the new "cum-scented" Slickyboy as I slathered it onto my seven-inch stiffie.
Yes, it's true.
I'm quite hung. Especially for a confirmed "bottom." Which was probably an additional turnoff for the lads who fucked me.
I reached for the magazine on top and saw the lovely cover boy. He was around my age, with a stunningly beautiful face, made up to perfection. He was on his back on his bed, as I was. But with great differences.
He was wearing all black lingerie and stockings and looked magnificent in them. Better than any girl whose pictures I had seen.
And he had been freshly fucked.
His bumhole was gaping and drooling a flood of manly cream.
He was smiling through a mask of sperm.
And his own little four-incher was drooling sissy juices after having shot a tsunami of sperm all over his flat tummy.
I gasped.
The boy was 18 or older. The cover swore to it.
He had had sex with a male who had ensured that he would cum and not just receive anonymous thrusts. He was fucked and happy!
I studied his face. Then considered my own.
And I realized at that moment that I could be as pretty as that boy. I could femme up and get men to love me, not just fuck me.
Mom was right. As always.
I slathered a bit of Slickyboy Masturbation Cream onto my stiffened penis and opened then Panty Boy magazine.
The coverboy was featured in a story called, "Seduced by an Older Man."
It showed the boy, whose name was Henry, on what seemed to be a dinner date with an older, extremely hunky and apparently hetero man named Mr. Smith.
Henry was dressed as a boy and seemed very nervous in Mr. Smith's presence. Mr. Smith was paying full, seemingly loving attention to Henry's needs and desires. When the meal was over, Mr. Smith asked Henry, "Shall we go back to my place, Linda, and do what you know you need?"
Henry seemed scared and nervous, but gave his consent.
Over the next two pages, Henry became Linda as Mr. Smith lay on the bed, naked and erect. Linda stripped nude, then did her makeup to perfection. After which, she slid on black stockings, garters and bra then five-inch-stiletto pumps.
No panties.
She was a bit hesitant when she presented herself, standing, by Mr. Smith's bedside. She was amazingly beautiful. And feminine.
I was convinced that Mr. Smith would use her for his filthy purposes, then put his pants on and leave Linda in blue-ball hell. Just the way my male "lovers" had left me.
Imagine my surprise when Mr. Smith sat up in bed and, leaning over, took Linda's stiffie into his mouth and gave it the sweetest suck. Linda loved it! Then really loved it two pictures later when she shot her sissy cream all over Mr. Smith's face!
His face!
My "lovers" would have never even imagined touching my penis, let alone sucking and licking it to a delicious conclusion.
And if I had "solied" them in any way with my cum... I would have been in the emergency room for sure.
Mr. Smith wasn't through!
He turned his lover around and, as he was sitting and she was standing on her giant heels, Mr. Smith stuck his tongue deeply into Lina's anus.
His tongue!
Her anus!
Oh!
I spunked!
Before I even applied the Slickyboy Masturbation Cream.
It was such a thrilling idea.
Men. Beautiful, older, manly, hetero men. Serving their ladies' needs on an equal basis with their own.
I wanted that.
Lots of that.
Chapter Three – Fixing it
Three Panty-Boy-induced orgasms later, I fell asleep. Visions of handsome, giving lovers in my head.
The kind of lovers my Mom enjoyed whenever she wanted.
But making the conversion from gay chump to pantyboy winner wouldn't be easy. Or so I thought.
I was ready to be converted.
And told Mom so the next morning at breakfast.
She was delighted.
"I knew you would feel that way, Honey. Or should I call you `Laura?'"
Laura?
"If you had been born a girl, I would have called you Laura. Do you like it?"
I did.
Laura.
"How about this, Laura? Let's go to Timmy's Girlish Secret, the pantyboy's superstore. In fact, I have a makeover appointment for you an hour from now. Sound good?"
It seemed a bit rushed and pre-planned. But I was through with the Erics of the world and every day without sex was a day without sunshine. So I agreed.
Then asked, "What do you mean by makeover, Mom?"
Mom smiled. "All the way, Honey. You'll be bathed and shaved everywhere. Powdered and perfumed. Your face will explode with your beauty when they give you your first makeup lesson. Then they'll dress you in sexy lingerie and a miniskirt. You'll be walking in three-inch heels by mid-afternoon. Then, in one of their relief rooms,' you'll have your first mini-date' with a man."
I spunked.
It was SO embarrassing. Then it wasn't. Mom and I laughed and hugged each other.
Seven hours later, Mom's predictions had all come true. Except for the last one.
Which was only being delayed because neither Mom nor the salesgirls could tear me away from the full-length mirrors that showed me what I should have been seeing since I was 12.
I was astonishingly beautiful! And sexy! And feminine as all get out!!
No boobs. Not 100% steady on my pencil heels.
But my face!
And my stockinged legs!
I couldn't even stop looking at my painted nails.
Then it hit me.
Would men – handsome, hetero, hunky- older men - the kind of men I wanted – think I was some kind of a freak?
Would they want to make love to me – really make love instead of me letting them fuck me and sucking them off?
By Mom's agenda, I would soon find out.
Mom touched me on my bare shoulder and broke the spell.
"Let's go to one of their relief suites, Honey. I'll introduce you to Mr. Smith."
Mr. Smith!
Was I soon going to be with the Mr. Smith from that Panty Boy issue that WRENCHED cum from my testicles?
Would it be THAT Mr. Smith?
Uh, no.
But it was a VERY good Mr. Smith!
Maybe even better than the one in Panty Boy.
Mom led me into Relief Suite Seven, introduced me to my first "date" as a pantyboy, and left.
"Hello, Laura," the beautiful man said.
And I almost creamed my panties.
He was a major hunk!
Wearing a $2,000 power suit and $500 tie. Early 40s. Tall. Hard where he should be. Ridiculously handsome. And fit.
His smile was singing my eyebrows.
I wanted to say hello and that I was happy to meet him. But my cock was so stiff, there was no blood left in my brain.
"Laura, I've been talking to your mother. A lovely woman, but certainly not in your league."
Oh! Was he saying that I was prettier than Mom? Or was he just flattering me to get into my panties?
I so wanted that to be true.
But he was getting into my panties regardless.
He continued. "Your mother explained that you had sexual relationships with men your age as Andrew, but those relationships were unrewarding to you. The men were selfish and unappreciative, no matter how sexually generous you were. Is that correct?"
I nodded. While thinking, is this almost over. Can you fuck me now?
But he continued. "Those young men were FOOLS, Laura. You are exquisite. You should be worshipped by men. And you will be. I hope you'll let me be the first to adore you properly. May I kiss you?"
I moaned.
He stepped toward me, took me into his virile arms, and kissed me within a micron of my life.
Closed-mouthed at first. Then full-Frenchie.
It was the most erotic moment of my life.
Then it got better.
As he kissed me, the rascal reached behind and unzipped my dress! When he broke the kiss, he helped me pull the dress over my head. And I stood before him in black bra, stockings, garters, big heels and severely tented panties.
At that point, having NOT kissed me, one of my lunkhead boyfriends would have forced me to my knees, pulled out his cock and shoved it into my mouth.
But Mr. Smith was a keeper.
He led me into the suite's adjoining bedroom, sat on the bed facing me and gently pulled my panties up and over my rampaging erection.
I had expended so much precum that if he had thrown my panties against the wall, they would have stuck.
He helped me step out of my panties (not easy in stilettos) and there I was.
Vulnerable.
Pantiless.
Throbbing throbber throbbing away.
Oh!
He took my cockhead into his mouth!
No had ever...
Oh!
He was running his tongue all around the glans!
Just the way I did for Andrew's cowardly dolts.
But better.
Whoa!
Was that his finger rubbing my anus?
Entering it?
All new sensations.
Delicious.
Oh!
I cried out.
And gushed the first cumload I had expended while in another person's company (excluding Mom's kind action that time).
I heaved.
He swallowed.
In love.
Oh!
When I returned to the home planet, I was eager to recompense Mr. Smith for the pleasure he had given me. But he wasn't through being generous.
The naughty man had me sit on his lap, unhooked my bra, and assaulted my nipples with his tongue and lips.
Another all-new experience.
And a delightful one.
As he suckled me, he stroked my cock most thrillingly.
You'll never guess what happened.
Aww. You guessed.
I spunked again.
Two for me. None for him.
Stunning.
And it was only starting.
Mr. Smith turned me around. I was still standing. He was still sitting on the bed. He asked me if I could touch my toes.
I was young enough that it was easy to do so.'
I leaned over and...
Bazinga!
His TONGUE was in my bumhole!
Really in my bumhole!
I was getting the entire enchilada. And tostada. And burrito. Combo plate number seven.
All my disgusting needs in one love session, it seemed.
Where had men like Mr. Smith been all my life?
No matter. He was with me at that moment. And he was spectacular.
He was spelunking deliciously in my love cave.
I stood to get more comfortable, then reached back with both hands to spread my cheeks for him.
Giving him complete and total access to my most private area.
Someone I had met less than an hour earlier.
Was I a little sissy slut? Apparently.
I was Ok with that.
Oh!
He stopped licking. Asked me to get on all fours. On the bed.
He was going to fuck me.
At last!!
It took him about five seconds to strip to an awesome nude.
Proving that I excited him.
I was very happy and proud of that.
Had I been in charge of the proceedings at that time, I would have laid him on his back, knelt beside him and, with my mouth and tongue, made him happy he had been born a man.
But there was always time for that later.
Mr. Smith had held his animal instincts at bay long enough.
He wanted to fuck me. and he wanted to fuck me NOW!!
The man flung me semi-roughly onto my back, lifted and spread my knees, and slid two pillows under my hips.
He was a rampant, raging beast.
"Get it wet, Babydoll," the wild creature said as he shoved his long, thick cock into my mouth.
I trembled with the fear of the prey as I did so.
It was almost fatally exciting!
He tasted so much better than those silly boys I once submitted to.
But he was just as impatient.
Telling me that I was THAT exciting to him.
I gave him all the saliva I could muster. Three long strokes worth.
Then he pulled out, rearranged his position, and entered my pootie with its biggest invader to date.
It hurt a little.
But my tears were joyful.
The man was making sure he rubbed my prostate with each stroke. And he was manipulating my knoblet with his strong fingers as he fucked me.
Quadrupling my pleasure.
Even though the fuck was payback for the excellent attention he had already given me, I spunked first.
Hard.
It was debilitating.
And I would recommend doing it at least five times daily.
My incredibly giving lover was finally lost in his own pursuit of orgasm. I gave him the best tongue-kisses I could muster.
And I even [blush} slid my right hand around and entered his bottom hole with a naughty finger.
He yelped manfully. Kissed me harder. And drenched me with his sperm.
I was ready to plan our wedding.
But Mom was banging on the door saying, "Five minutes, Honey. Mommy has a date tonight."
I thought I saw something in Mr. Smith's expression that said, "Let's run away together. Find a grass hut under a coconut tree. And fuck all day and all night. But what he said was, "I hope we can see each other again. And I hope that you can see your potential. It's enormous."
So was his cock.
Which I ached to suck.
But Mom was my benefactor in my new life and I wasn't going to piss her off in any way.
So I slid my dress back on and left my panties with Mr. Smith.
I kissed him goodbye and left Relief Suite Seven. Wondering vaguely if such relief was good or better in suites one through six.
Mom was all smiles as we walked to the car.
When we got in, she asked that I crack a window.
"Next time, a shower, Honey," she said. "Now tell me everything."
I did. All the way home. In great detail. She was delighted. And proud of herself.
As we walked from the car to the house, she said, "Laura, as sure as when you drop a slice of buttered bread it falls butter-side down, my gentlemen friends will want to get you into bed."
Uh-oh. It looked like the "Stay off my turf" speech was coming.
But no.
"If you like any of them, go ahead and fuck them. There are plenty more where they came from. And any man fucking both of us is twice as likely to be `generous' with the mortgage and grocery bills."
Wow!
Mom had about a dozen lovers?
Would any of them...?
Chapter Four – Laura makes new friends
You may be wondering at this point, it was my post-high-school-graduation summer. What were my plans? Was I going to college?
Well, Andrew was kind of a lump about such things. He kind of figured he would find some nice sugar daddy who wanted a gay twink to help him get through the night. Though that was not going to happen. Plus, if British nobility could take a "gap year" between Eton and Oxford, why couldn't Andrew?
Laura (I) could already see that my former identity was a blockhead.
Laura's plan was far better. I was going to find SEVERAL sugar daddies who wanted a beautiful pantyboy to help them get through the night. Just as Mom did.
The day after Mom and Mr. Smith had rearranged my notions about what sex could be, I spent much of the day rearranging my bedroom.
Mom had bought me an extensive wardrobe of lingerie and outside clothes, as well as some nice girlie touches for my room.
Good thinking, Mom.
She didn't want to bring the Mr. Smiths of the world into a bedroom whose walls were covered in sports and Slayer posters.
I finished around three p.m. and showed Mom.
She was very pleased.
And had a plan for me that evening.
Though it was a shocker.
"Your friend Ryan Spunkup will be coming in two hours for a sleepover. Let's get you washed and ready."
Huh!
I protested. "Mom, Ryan isn't gay. He doesn't know I'm gay. I don't even know him that well."
Mom tsk tsked. "Honey, everyone knew Andrew was gay. But Laura isn't gay. She's a girl who loves men. And Honey, Ryan is much more comfortable as Nancy."
Ryan was a crossdresser!
Mom knew everything.
What was my Svengali Mom doing by introducing Ryan into my conversion? Did she want to see if I was attracted to other pantyboys? Did she think knowing another pantyboy would make me more secure as a pantyboy? Or eager to be a pantyboy? Did Mom think that Ryan could teach me a thing or two about being a pantyboy? Or was she just trying to get me sexually interested in Ryan so that I would be less interested in poaching her boyfriends?
I guessed I would learn soon enough.
Mom helped me with my makeup and got me into what she called my "play clothes." Pink, frilly garter belt, stockings, panties, and three-inch-stiletto sandals.
Topped off by the sheerest, shortest babydoll nightie in captivity.
Mom smiled maternally as she watched me admire myself in one of my three full-length mirrors. "No genetic woman except me perhaps, would wear stockings, garter belt and babydoll for a love session. Though such a combination drives men lust-wild. Sometimes, it's just pathetically easy for pantyboys to get all the best men."
At least I think that was what she said. I was too busy admiring my sexy beauty.
And wondering what Ryan would think.
I had never been attracted to Ryan when I was Andrew. He wasn't the manly, take-charge-and-shove-it-up-the-kiester type Andrew favored.
Ryan was more of a cutie. Had I known more about pantyboys, perhaps I would have seen him as one.
I was looking forward to meeting "Nancy," Ryan's pantyboy self. Was I mostly interested in out- beautying her as Laura? Or did I want to take her panties off and see what happened?
I didn't have to wait long.
Ryan, as Ryan, arrived at 6 p.m. He seemed shy around me. And why wouldn't he? I was a babe. And in my own mind at least, a mega-babe.
Mom was very welcoming, kissing him on both cheeks. "I see you brought your cosmetics. Good, Honey. I left you some playclothes on Laura's bed. Why don't you get ready while Laura and I have a girlie salad dinner. You said you already ate, right?"
Ryan nodded shyly.
I felt pretty good knowing I was about to win my first beauty contest.
Forty minutes later, Mom and I were cleaning up after dinner when Nancy entered the kitchen.
Really entered the kitchen!
She was SMOKING hot!
Wearing her yellow "playclothes." Garter belt, stockings, panties and FOUR-inch stiletto sandal mules.
She moved like a girl. Unlike my still-boyish lumbering.
And her panty tent was every bit as big as mine.
I was in love already. Even though I had just lost my first beauty contest.
Nancy came up to me, kissed me full on the lips and, in a girlish voice said, "I'm so happy to meet you, Laura. You're very beautiful. Shall we go to bed now?"
Oh, yes!!
We said goodnight to a smirking Mom.
Then double-timed up the stairs to my bedroom.
Which, thank goodness, had a queen-sized bed (big enough for two queens) and an en suite bathroom.
I locked the door. Didn't want Mom coming in taking polaroids or something.
Then I remembered she had the spy cameras. Would she be watching us?
That actually excited me more than it repulsed me.
I turned from locking the door and Nancy encircled me with her arms. Her beautiful lips found mine. Her cock tip found mine. We tongue-kissed hungrily and rubbed peeholes desperately.
I didn't want to cum so soon, but she was so beautiful and dressed so sexily and she wanted me so badly and oh...!
I cried out most sissily and began to fill my pretty, pink panties with spunk.
Seconds later, Nancy joined me in Spunk Nirvana.
When I was able to reconnect my brain cells, it occurred to me that I was self-identified as gay. Yet, I was flamingly excited by Nancy, who, except from my Mom, was the most feminine person I had ever met.
Perhaps I just loved cock.
Or I loved men and I saw Nancy as a friend and colleague in my quest for cock.
Who cared?
Nancy made my cock hard.
And she was someone I looked at as a role model.
Miss Beautiful and I took off our spunky panties and our heels and got onto my bed.
Oh dear.
Nancy went after my nipples with her lipsticked mouth. And she knew her nipple-licking.
It was exquisite.
And mind-shuffling.
Why was I so wildly sexed up by the girliest person I had ever met?
And what the heck was she doing with her tongue and lips on my nipples?
Until the day before, I had never even thought about my nipples.
I decided that a) as Laura, I liked every bit of sex as I was getting and b) I was going to see what else was out there.
So, although I was whimpering with nipplic pleasure, I didn't want to cum from that.
I wanted to FUCK Nancy. Not the way that knucklehead Eric and those other louts claimed to fuck me.
I wanted to make LOVE to Nancy with my fuck.
A lovey fuck.
With lots of kissing and stroking. And mutual satisfaction.
And I wanted to do it right away.
So, being a millennial and aware of the rules regarding sexual harassment, I groaned out, "I want to fuck you so bad. May I fuck you?"
Nancy stopped nipplizing me and said, "Of course, you impetuous girl. But you'll have to eat me out first. I forgot the Spermbutt Anal Lubricant and we can't go dry, can we?"
We certainly couldn't.
But I was a bit wary about the tongue in the bum thing.
Though Mr. Smith had performed such an unnatural act on me and it was wildly exciting for both of us.
Nancy didn't give me much time to think about it all. I was already on my back so she just reverse-straddled my shoulders, on her knees, and her bumhole was inches from my face.
It looked delicious.
All pink, with a hint of brown.
Wrinkled and pretty.
Was it winking at me?
I kissed it.
She moaned.
I licked it.
She squealed.
I dug my tongue in there good and proper and she screamed. But she made no attempt to dislodge me.
I was having a wonderful time.
And so was my cock. Which, by the way, Nancy had bent forward and was giving "Little Laura" the nicest kisses and suckees.
What fun it was being a girl so far. An "enhanced" girl at that.
I got Nancy's pootie all nice and wet and Nancy managed to excite me without making me cum. And we were ready.
Nancy got onto all fours, but, being the top, I changed the position. Nancy lay on her back. I was on my left side on her right. I had Nancy lift her right knee. And I swung my torso around so that I was entering Nancy's "pussy" from the side.
Nice, deep penetration. Easy access to kisses. Yum.
My cock slid right in. Which spoke volumes about Nancy's backstory.
No matter how many times Nancy had entertained visitors, however, it was clear to me that she was enjoying our fuck.
We were two pretty, well-lingeried, girlie boys in our sexual prime, rutting away in hot lust.
I managed to skin Nancy's penis throughout our fuck and she showed her appreciation by spunking before I did.
I managed to hold back for an amazing eight minutes and change,
Wow!
That was fun!
Nancy obviously thought so. She pelted me with kisses and endearments.
And said she wanted to fuck me next.
Just as I had for her, she ate me out. I must admit that she was better at that than I was. But I was eager to improve.
Then she fucked me.
I had been fucked a lot. First by the inconsiderate lunkheads. Then by the amazing Mr. Smith. But the fuck with Nancy was better.
Was I becoming a lesbian now?
My head was in turmoil, but my testicles knew what to do.
A nice ballblaster for the ages.
After that we napped.
And awoke. And fucked. And so on until morning. When we showered together, got ourselves fixed up and went downstairs for breakfast with Mom.
By "fixed up" I meant a little lipstick, a filmy peignoir and some comfy slippers. Nancy wore a filmy peignoir too, but she put a bit more effort into her makeup, especially around her eyes, and wore big, spiky heels.
Mom wasn't in the kitchen yet. But her stud du jour, Bart, was.
Bart's eyes got wide and his cock got hard when he saw Nancy and me in our girlie gear.
Bart was a nice guy who was ten years younger than Mom and 50 times studlier than I would have ever been as a man.
It was startling to see him, but I amazed myself by not being embarrassed. Laura was who I was and I didn't care who knew it.
Bart knew me a little as Andrew so he figured out who Laura was pretty quickly. He had never met Nancy.
Nancy set out to change that.
She giggled and said, "Oh, dear. This handsome man has caught us in our night clothes. What he must think of us." Giggle.
Oh my! Was Nancy flirting with Bart?
She was. And pretty well.
Bart turned away from me and aimed his virility at Nancy.
"You look so pretty in your night clothes, Miss. May I get you some coffee or fix you breakfast?"
And so on.
I was going to have to get in the game if I was going to keep up with Nancy.
After about five minutes of flirtarama, Mom entered the kitchen.
How much had she heard?
Considering the "back off" look she gave both Bart and Nancy, quite a bit. But when she saw them cower at her power, she resumed her good cheer.
"My son, Andrew, is now my daughter, Laura, Bart. Isn't she lovely?"
"Very much so," he said with a leer at me. As if Mom's announcement was as common as, "I went to the dentist yesterday and had no cavities."
"And this is Laura's new friend, Nancy. She's also a former boy. I believe these two have been fucking and sucking all night, just like you and me, Bart. Am I right, girls?"
Nancy and I nodded dumbly. Mom really was a force of nature.
Then Mom started acting like a Mom. Putting out plates and serving us fruit, milk, toast, coffee and cold cereal.
Nancy made sure she sat next to Bart during breakfast as Bart talked about his job as an airline pilot. She laughed at all his jokes. And touched his hand now and then.
Mom smiled at all that.
When breakfast was done, Mom said, "I can see the attraction between Bart and Nancy. Why don't you two go up to our guest bedroom and have fun for a couple of hours? Laura and I will clean up."
They eagerly agreed and were gone in ten seconds.
And there I was. Thrown under the bus. By my Mom.
But it was a real teaching moment. "I hope you learned a big lesson today, Laura," she said. "A girl should always look her best. She never knows when she'll meet a man whom she wants to fuck her. And shameless flirting is often a good thing,"
Mom was wise.
She and I made good use of the time Nancy and Bart were fucking. She drilled me in some feminine mannerisms, I learned to wear four-inch heels, and she had me put on and take off full makeup three times.
Bart and Nancy joined us for lunch. Nancy had the glow of the well-fucked. She was dressed in a lovely summer frock and wearing three-inch heels.
I had a lovelier summer frock and was wearing four-inch heels.
Take that, girlfriend!
Bart kissed and thanked Mom and was gone.
"Nancy, I would appreciate it if you would take Laura for a nice walk in the Town Park. It's a lovely day and you girls look so beautiful. It would be a shame to hide that beauty indoors."
Nancy eagerly agreed. I agreed too, since Mom's wishes were orders to me. But I wasn't eager to be out and about as a girl for the first time.
Nancy assured me that she had my back. And also that she wasn't going to just sit back and let me scoop up the best men.
And we were off.
Walking down my street. Garters tugging at my stockings with each step. Feeling the breeze up my skirts. Hoping that a gust of wind didn't come along and reveal my pointed panties to the world.
Balancing on those heels.
I loved it.
And I loved the hot stares that Nancy and I got from every man we passed.
We entered the park and Nancy led me over to the duck pond. "Oh dear," she said, rather more loudly than she needed to. "We don't have anything to feed the ducks."
I thought that was silly. I wasn't concerned about ducks. I was...
"Excuse me, Miss. My friend and I have plenty of duck food. We would be glad to share with you two lovely ladies."
Oh!
The speaker was a 30-something master of virility. And his friend was equally hunky.
I just HAD to get Nancy to teach me how to do that!
"Well, that's very kind, sir. But my friend and I certainly wouldn't want to put you out."
"No problem at all, Miss. My name is Barry and this is my friend Dave."
"Thank you so much. I'm Nancy and this is Laura."
I nodded. Feeling like the third-grader auditing a doctoral class.
I may have been dazed and mute, but my eyes locked in on Dave and he locked back.
Oh!
Was that a spark I felt?
I sure felt it in my penis, which was outrageous.
Dave offered to share his duck food with me and I managed to speak. "Thank you."
We did manage to chat a bit as we fed the ducks. Dave was very nice and sweet. And obviously a duck lover.
After a half an hour or so, I realized that Nancy and Barry were not in sight.
Half an hour later, they reappeared. Nancy's face was a bit flushed. And her hair and lipstick were a little mussed.
I HAD to get those lessons from Nancy soon!
"Hi, Laura and Dave," Nancy said brightly. "Barry was just showing me the park and he came up with a delightful idea, didn't you, Barry?"
Barry nodded obediently.
Again, Nancy was my superhero.
"Here's the idea," Nancy said. "Barry has a lovely apartment in town. He and Dave are on their lunch hour and need to go to work now. But they get off work at five. We could all meet at Barry's apartment at six and Barry and Dave could strip us to our lingerie and fuck us all night. How does that sound?"
It sounded amazing to me. And I marveled at Nancy's directness. But surely the men would think that was too pushy and too forward and too much too soon. Too too.
Wrong again.
"That sounds great!" Dave said quickly and loudly. "I mean, if it's OK with Laura. You're the prettiest, sexiest girl I ever met and I certainly don't want to tick you off."
I trembled at the thought of my first all-nighter with a man. A hetero, mature man. Who would treat me like his princess instead of his filthy secret.
But I didn't know Dave. He said he was an accountant. But he could be a serial killer accountant, couldn't he?
And what would be his reaction when he saw my "things?"
Nancy, of course, had thought of everything. "Barry knows we have penises, Linda. I even let him suck all the creamies out of mine. Is that OK with you, Dave?"
Dave looked stunned. But then his face ignited. "That's better than OK. I can't wait to make you happy, Laura. All of you."
Could it be that easy?
If you're with Nancy, apparently so.
The guys said goodbye to us with long, tonguey kisses. Dave was such a good kisser and the situation was so sex-charged that I spunked my panties.
As we walked home, I told Nancy how awestruck I was by her sexual power.
She smiled at that, thanked me, and said, "That will be you in a week or two, Honey. We have what men want and we actually give it to them. So we're in charge. And we can have just about any man we want. In the next three hours, we could get three more dates for tonight. But let's go back to your place, rest our feet and our testicles and get ready for our dates tonight.
Great plan.
Chapter Five – Laura and the Man
Mom was so excited about her "little girl's big afternoon" that she drove us to Barry's apartment.
She even made us stand outside, dressed in our best fuck-me lingerie, minidresses and skyscraper heels as she threatened mortal consequences to Barry and Dave if they harmed us in any way.
They believed her.
Then she kissed us lightly, to avoid messing up our slutty makeup, and left us to our fate.
It was a little embarrassing to have my Mom threaten slow, painful castration to my first real man date. But it certainly put me at ease.
Nancy and I would be as safe as we wanted to be.
The lads looked a bit stunned after Hurricane Mom, but they recovered quickly enough to ooh and aah at our slutty beauty.
Nancy and I set down two cases that held our nightwear, cosmetics, toothbrushes, Spermbutt Anal Lubricant, and clothes for the morning.
Then we proceeded with the evening's agenda.
The gentlemen held us in their manly arms and French kissed us until I was almost overwrought with arousal.
Dave then took me by the hand, grabbed my case, and led me into Barry's guest bedroom.
It was a very masculine room. But very neat and tidy.
With a bigger bed than I would have expected.
Had Barry and Dave been pulling that "feed the ducks" trick successfully often?
Anyway, I was submissive, the way men like, as Dave stood behind me, kissed my long neck and rubbed his stiff, clothed cock against my clothed bum.
I moaned.
Dave liked that.
He unzipped me. And helped me pull the dress over my head.
My personal shopper and fashion consultant, Mom, had set out all-black lingerie for me: Lacy boy-bra; frilly garter belt; the obligatory, seamed, fully-fashioned, reinforced-heel-and-toe stockings; wispy panties; and big, patent-leather pumps.
My big cock was straining my panties, even though they were the special panties only sold at Timmy's Girlish Secret. Sheer and feminine, but built to stretch with an erection.
Oh dear.
Dave was undoing my bra.
Would he be disappointed that I only had puffy nipples?
Then he eased my panties up and over my erection. And gazed in wonder at the splendor of my girlish penis.
He asked me to kick off my heels. I did so. And stood before my ravager-to-be wearing only stockings and garters.
I don't know why, but as he undressed, I covered my nipples with my right arm and tried to conceal my penis with my left hand.
Acting like the virgin I almost was.
Dave loved it.
Dave was naked.
I was "sexy naked."
Time to do things.
He was very tender. Kissing me and holding me in his arms.
As we kissed, he slid his hand across my tummy and located my stiffie.
Dave, I believe, wanted to show me right away that he was Ok with the whole "girl-with-penis" thing.
So he gave me a lovely rub-up as we kissed. Probably rubbing me the way he liked himself to be rubbed.
Which is a pretty good argument for boys being the best girlfriends too.
It was lovely.
I was very sexed up.
I soon began to ejaculate helplessly. In thick, creamy ropes.
He liked that.
I really liked that.
And it was a great icebreaker.
Dave didn't skimp on the foreplay.
After I spunked, he laid me on my back on the bed. He made little finger swirls with the sperm on my tummy.
He slid two spermy fingers into my bumhole.
I gasped.
Then he attached his mouth to my right nipple.
I squealed.
It was superb.
He spent a good ten minutes torturing me in both fashions. Then he disengaged his mouth from my nipple and attached it to my almost-recovered penis. While massaging my prostate better than anyone should ever hope for.
I soon spermed, of course. In an agony of delight.
And I was ready to sign over the keys to my heart to him.
As it happened, he wanted to unlock a different part of my anatomy.
The Spermbutt Anal Lubricant came out.
He lubed up my bumhole with it, the slathered it onto his outrageously stiff throbber.
He had me lie on my side. Got behind me. And shoved it all in.
I had been fucked before, of course.
But this was fucking the way fucking should be.
A loving, hetero man preparing his girlfriend (of either the with or without penis variety) with ample, multiple-orgasm-inducing foreplay.
Unselfish fucking.
Was I in love?
Maybe.
Did I feel good about the way my life was going since my "conversion?"
Definitely!!
Please tell me what you think at bc20002015@hotmail.com
My other stories on nifty:
"Stunners" transgender -- tv
"Acting Up" transgender -- control
"Panty Pleasures" transgender -- young friends
"Woodville" transgender -- tv
"Mothered" transgender -- control
"Panty Town" transgender -- teen
"Tradition" transgender -- teen
"Punished" transgender -- high school
"Panty Paradise" transgender -- teen
"Kevin and Molly Go to Camp" -- transgender -- teen
"Lovelife" -- transgender -- high school
"My Three Sissies" -- transgender -- tv
"Acting Out" -- transgender -- high school
"Explorers" -- transgender -- high school
"Pantied" -- transgender -- young friends
"Rebuilding" -- transgender -- teen
"The Au Pair" -- transgender -- surgery
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"Genes" -- transgender -- high school
"Brothers in Panties" -- transgender -- teen
"Coach" -- transgender -- control
"Intervention" -- transgender -- high school
"Winners" -- transgender -- teen
"Teased" transgender -- high school
"Irish Girls" transgender -- teen
"Finished" -- transgender -- teen
"Role Model" -- transgender -- high school
"Freedom" -- transgender -- high school
"Panty Fiesta" -- transgender -- control
"Experiments" -- transgender college
"One Fine Day" -- transgender -- teen
"Stiff Resistance" -- transgender -- teen
"Poker" -- transgender -- tv
"Panty Sabbatical" -- transgender -- high school
"Published" -- transgender -- tv
"Stripped" -- transgender -- high school
"Trained" -- transgender -- control
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"Fulfilled" -- transgender -- tv
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"Somewhere" -- transgender -- high school
"Next Door Bride" -- transgender -- chemical (though I don't think it has
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"Service" -- transgender -- tv
"Test Driven" -- transgender -- tv
"Sissy Stepmother" -- transgender -- tv
"Slacker Moms" -- transgender -- tv
"Sissies and the City" -- transgender -- tv
"Paid in Full" -- transgender -- tv
"Alternative Education" -- transgender -- control
"The Boy Bride" -- transgender -- high school
"Stiff Competition" -- transgender -- teen
"Reservations" -- transgender -- tv
"Panty Pride" -- transgender -- tv
"The Panty Life" -- transgender -- tv
"Super" -- transgender -- tv
"Stocking Boys" -- transgender -- tv
"Panty Secrets" -- transgender -- tv
"Auntie's New Panties" -- transgender -- tv
"Good Riddance" -- transgender -- tv
"Generations" -- transgender -- tv
"Fully Fashioned" -- transgender -- tv
"Tommy's Summer Job" -- transgender -- tv
"Tuition Assistance" -- transgender -- tv
"Sweeties" -- transgender -- young friends
"Pretty Boy" -- transgender -- high school
"Competition" -- transgender -- high school
"Strokes" -- transgender -- high school
"Hosed" -- transgender tv
"Sanctuary" -- transgender – tv
"Happily Married" – transgender – tv
"Late Vocation" – transgender – tv
"Kelly in Miniskirts" – transgender - tv
"Best Neighborhood Ever" – transgender - tv
"Chrissie Goes to College" – transgender - tv
"Corporate Incentives" – transgender - tv
"The Pink Side" – transgender - tv
"Babydoll Boys" transgender - college