Sanctuary

by Gingerfred Man

 

Chapter One – The Pink Nightie

I used to tell myself that none of this would have happened if it weren’t for that darned pink nightie.

When I was thirteen, my body was changing and I was very confused. More confused than the average teenage boy, I guess. I mean, everyone at that age starts to look at the opposite sex. My problem was, I didn’t know who the opposite sex was.

I was getting all kinds of strange signals in my brain. I looked at girls and found them very attractive. That was good, right?

But I found them attractive because I held them up to an ideal that I wanted to achieve, you know?

Maybe I’m not explaining myself well.

I looked at girls and thought, "They’re so pretty." No problem there. But the average boy adds, in his mind, "And man, do I want to stick my cock in their pussies."

Things would have been different for me if I had only thought that way. Instead, my addendum was, "And man, do I want to be pretty too."

Being a boy was fine with me. I had friends and a good life. A good mother and father and a tolerable sister named Maria Luiza. But something was missing.

It was that pink nightie.

Before Mom married Dad, she was a legal secretary and apparently a very good one. Mom was very pretty and in good shape, so with her looks and skills, when I turned 13 and Maria Luiza turned 15, Mom had no problem finding a job.

That was a bit distressing to me, since I had always had a Mom at home for me since I was born. But as Maria Luiza said, with a slap to the back of my head, "Grow up, Paulo."

Odd name, huh? My name is Paulo Malone. Even odder. Irish father. Portuguese mother. Mom met Dad in college when she was a foreign student from Portugal. Woman meets man and man must have his mate.

Mom spoke Portuguese to Maria Luiza and me growing up and for what it was worth, we were fluent.

But back to that nightie. When Mom went back to work, Maria Luiza had her high school activities, so that made me a latchkey kid. Mom was a bit freaked out about that, but it was only for two hours a day, so she got over it.

I didn’t like all the rush Mom’s job added to our lives and I didn’t like less attention from Mom. But what could I do?

After school one day, about a week after Mom went back to work, I passed by Mom’s room and noticed that she and Dad had been in such a rush that they didn’t make their bed. Unlike 99% of the thirteen-year-olds in the universe, I decided to help them out and make it for them.

As I pulled off the pillows, I saw it. Mom’s silky, diaphanous, sheer, horribly sexy, pink, oh-so-short nightie. I wasn’t thinking anything dirty about my Mom. Honest. I just wanted to feel it. I held it up and considered its beauty. It was spectacular, with little pink bows and white lace trim.

My stomach stirred and something unfamiliar happened. My little willie got very, very stiff.

Oh, I thought. How did that happen?

I draped the nightie on a chair, so I could see it as I hastily made my parents’ bed. It was so beautiful. I had never seen my Mom in it. Of course, Dummy, I thought. If she walked around in that, Maria Luiza and I would see everything she had. She probably only wore it when she and Dad were, you know, doing it.

Did they do it? I was only vaguely aware of what "it" was, but I couldn’t imagine my parents doing "it."

Maybe she wore it because it was real comfortable in bed. It sure didn’t look very warm. What would happen, I wondered if I just held it up against me and looked in the mirror? I tried it. Nice. Very nice.

I looked at my watch. Over an hour until anyone would be home. My heart was pounding. My ears were red hot. And you could have cut glass with my poor cock. I didn’t say poor, little cock, because I was well-armed. Six nice inches at 13 years old. And all of those inches hard as stone that afternoon.

I made my decision. I had to try that delicious piece of wisp on.

I was trembling as I removed all my clothes. Oh my goodness. I looked at myself in the mirror. I had a very nice body for a cute, young boy. A plump little bottom and slim waist. Long, well-shaped legs. Slim torso and a nice-looking, sweet face. Looking very scared. And incredibly aroused. If anyone had come in at that moment, I would have expired for sure. But no one did.

I crossed the river. Carefully, I slid the pretty pink nightie over the top and popped my head out. It felt as if every pore the nightie touched was on fire. My cock was throbbing and reaching dangerous levels of arousal. I had never cum, so I wasn’t sure what to watch out for, but I knew something was happening.

The nightie covered my cock. Barely. But I could see my saucy little pink bag peeking from below the hem. I gasped with delight at the sight of myself in the mirror. I knew at that moment that if I tried, I could be pretty – a thought which has tormented and comforted me ever since.

I posed this way and that, gaining in bravery and glowing at my self-compliments about my beauty. Then I did something very odd. I raised the front of the nightie and looked at my suffering prick. It was very red and sore-looking. And my young eyes perceived a gooey liquid oozing from the tip. How curious!

I liked looking at my cock in front of my nightie. It was exciting me. Then I <blush> touched the tip of my cock with one finger, very lightly. It jumped! Oh. It felt so good. I took the same finger and used it to rub a little of that goo all around the head of my cock. Even better.

I was tickling the incredibly sensitive underside of my cockhead when my stomach lurched. Was I sick? I rubbed a little more, teasingly, as I watched the proceedings in the mirror. A big pinch in my gut. Had I eaten something bad at school? The food was all bad in school. Then a complete loss of body control. A rush of pleasure grabbed my midsection and waves took me to a better place. I was able to discern in the mirror that hot, wet globs of a creamy substance were leaping from my cock and covering the mirror. What was worse, in my thrashings, I had deposited a good deal of the sticky stuff on Mom’s pink nightie!

I shook with ecstasy, then continued shaking from fear. Of Mom. And Dad. And Maria Luiza. And being a faggot girlie-dresser. But even if I were to be taken and burned at the stake that moment, I would have done what I did all over again. At that moment, instinct told me who I was.

Still, if you can avoid burning at the stake, it’s worth some effort. I scrambled like a lad possessed to cover my felonies, even to the point of doing some laundry that included my pink tormentor. Delicate-shmelicate. I put everything together, thus ensuring that I would never be asked to launder again. Thank goodness, my new friend survived my laundering incompetence.

That night, I ate dinner with my family as always. But I wasn’t the old Paulo. I wasn’t better or worse. Just aware of much more about myself. Not all of it was welcome news. And it was all confusing. That darn pink nightie.

 

Chapter Two – Oops

The next three weeks were a delight! Every day, except for those darn weekends, I would come home from school, peel off all my boy clothes and put on Mom’s pink nightie. By that time, I was thinking of it as my pink nightie.

I would start getting excited when I woke up in the morning. I imagined that instead of my dippy, blue, boy pajamas, I had been sleeping in my pink nightie. Some mornings I would close my eyes and picture it clearly. I could feel it touching my creamy shoulders, my torso, my <gasp> nipples, my soft, downy tummy, my sore, throbbing cock and my tingling ball bag. I would touch my balls and rub them softly, making my cock even harder. Sometimes just touching my tee tees would make my cock shoot a big load of juice. Sometimes I would tickle the shaft and torment the head to make all my boyish cream eject. It was beautiful!

At school, I would dream about wearing the nightie. Sometimes I would look at my friend Tommy Foster and imagine that I was standing in my Mom’s bedroom looking at myself in my pink nightie and Tommy walked in. In my dream, Tommy would be stricken by my beauty and beg me for a kiss. Shyly, I would agree. Then he would kiss me and it would feel real warm and nice. I didn’t know what a kiss felt like, but I was sure it was nice. When Tommy was kissing me, he would rub up against me. My prick would rub against Tommy Foster and that cumming thing would happen really hard. With lots of sticky goo. All over Tommy Foster. One time it got out of hand at school and I did cum very hard in my pants. Good thing I had dark trousers on that day. I was worried about the Tommy Foster dreams because, I wasn’t sure, but I thought that it was a gay dream. I was taught that gay was wrong by my Mom and Dad. But it was only a dream, wasn’t it?

In the afternoon, I would practically run home from school, strip to the buff, run to Mom’s lingerie drawer and put on the pink nightie. Mom had lots of other pretty things in there, but I liked old reliable best. I would put it on and pose for a good half hour. I was often so excited that I would be crying, but I didn’t want to cum right away. I had learned that cums were much more intense when you prolonged the foreplay.

The second week, I discovered a matching pair of pink stockings. Was I naughty enough to put those on as well? I was. The feeling as I slowly slid each lovely treasure up my boyish legs was exquisite. I came like a firecracker <blush> the first time I put them on. They made my legs look even sexier. I was sure that Tommy Foster would want to kiss me with those stockings on.

Later in the second week, I discovered that Mom’s pink mules were just a tiny bit too big for me. I almost crippled myself when I put on the four-inch high stilettos, but in a couple of afternoons, I could have run a hundred-yard dash in them.

Wow! What a difference those pretty mules made! They made my cute, tiny bottom protrude and my legs looked all toned and prettier. I think Tommy Foster would have begged to kiss me. Little did Tommy Foster know all the boygoo that was being spilled in his honor every afternoon.

On Wednesday of the third week, I experimented with cosmetics. Just lipstick at first. I sat on Mom’s vanity stool and put it on while looking in Mom’s compact mirror. I messed up the first time, but after that, I had very nice, kissable, lipsticked lips. I checked my pretty face out in Mom’s vanity mirror. I looked great! But why was I dreaming about boys kissing me?

Yuck! I think.

Even just flashing the idea through my head made my six, sissy inches go straight up, sticking out in front of my pretty nightie. I was so pretty. I was a princess! I touched myself and my balls stirred. I was mesmerized by my reflection. So beautiful. I stroked my cock in agonizing tickles and touches. I could feel the cum boiling. I squealed with pleasure and came all over my fingers, then screamed with sexual release until I heard, "Paulo!!!!!! What are you doing???"

It was Mom. Oh. Oh. I began to tremble. Then cry. What was she doing here?

She looked at me in horror, then fainted.

If I buried her in the backyard, then got into my boy clothes, no one would ever know.

Not an option.

I ran to Mom and tried to revive her. I knew my pink nightie days were doomed. And so was I. But I was more worried about Mom.

She came around. Then stared at me. Then she began to cry.

I kept saying, "I’m sorry, Mom." Over and over.

I was sorry Mom was upset, but I wasn’t sorry about dressing girlie.

 

Chapter Three – Salvation?

Things were not good for Paulo Malone. Mom kept asking where she failed. Dad almost spanked me, but he was too good and gentle for that. It was clear that he was very disappointed that I liked dressing pretty.

Only Maria Luiza was nice to me. She alone seemed to understand that you have to do what you have to do.

I could hear Mom and Dad discussing how they could "cure" me of my "problem."

What problem?

They did a lot of research and decided that they would send me to the youth group of our town’s DA (Dressers Anonymous). A guy called Reverend Spunkless, who was a determined opponent of my "sin," ran it.

Three days after my apprehension, Mom dropped me off at my first meeting. I thought that in those twelve-step programs, the person first had to admit he had a problem. But Mom wasn’t sticking to any technicalities. She wanted me cured!

The Rev was the only adult in the group. There were boys a bit younger than I, some the same age, and some in their later teens. I was assigned a sponsor, Craig Jansen, a sixteen-year-old with a handsome face, but the fierce zeal of one who has been reformed.

"I’ll help you get through this, Paulo," Craig said. "You’ll never want to wear those faggot clothes again. This group will make a man out of you."

How awful, I thought. I just wanted to get into my pretty nightie, stockings and heels and tickle my weenie until I gooed my panties. Why couldn’t anyone understand that?

Reverend Spunkless was an unusual cleric. He appeared to hate both the sin and the sinner. He told us that unless we purged our souls of our vile addiction, we would suffer the tortures of hell! I didn’t really believe that, but the guy sold it hard.

I was mostly comforted by the fact that I was not the only sissy in town. There were nine other boys besides me and some of them were cute. Even my sponsor Craig, the big Nazi. He had a nice body. I tried to imagine him in a miniskirt with a flutter hem, black stockings, and big, high heels. Couldn’t do it. He was too nasty. But he was one of us or he wouldn’t have been there. We were all "crossdressing little perverts" whose souls were being saved by the Rev.

I had to attend these brainwashing sessions three afternoons a week and I’m proud to say that I didn’t buy into any of it, although I faked it well enough to convince my Mom, Craig and Rev. Spunkwell that I was reforming. Or so I thought.

The day I had to give testimony, I decided to stir the pot a little by telling my story as explicitly as possible. I stood up and said, "Hi, everyone, I’m Paulo and I’m a crossdressing little pervert."

"HI, PAULO!"

I’ve been dressed as the Bible intended for twenty-three days." <Gag>

"When I was sinning, every day I would run home from school and take off all my clothes. I would stand there looking at my beautiful, naked body in my Mom’s full-length mirror and touch myself all over. I would pinch my tender nipples, making them all sore and puffy and ready for anything. I would rub my hands up and down my soft, warm flesh and cup my pretty ball sack with my hand, tickling and rubbing my little treasures ever so softly."

The boys in the audience were squirming in their seats.

"That would make my big cock all stiff and agitated. It’s made of six, luscious inches and it’s uncut, so it has a long, brown, wrinkly foreskin and lots of ridges and blue veins that stick out when it’s excited. And whenever I had my pink nightie nearby, it was VERY excited."

More squirming.

"When my penis was leaking lots of goo, I knew it was time to put on my pretty pink stockings. They were very sheer and felt heavenly sliding over my cute, pointed toes and my sleek legs. I rolled them all the way up to my tiny butt, which was all plump and soft. Then I would put my pink, four-inch stiletto mules on and my bottom would stick out in an open invitation for any fellow sinner."

Will, a 12-year-old in the rear, groaned. Reverend Spunkless was listening so intently, he didn’t notice. He was sweating in a thin sheen all over his face, particularly on his upper lip.

"Most days, I would then sit at my Mom’s vanity table and put lipstick on my big, luscious kissers. Then I would pout at the mirror for a smooch, while stroking my exposed, hot, hard, weenie. I was evil, my brothers, evil."

Jimmy, a 14-year-old, wriggled in his seat and his eyes fluttered. Was he cumming?

"Often, I would put on a pair of my mother’s pretty panties. My perversion passed even that boundary. And I would rub and rub my peeny through the panties until I got a wonderful, but evil feeling in my stomach and I would spurt hot, creamy jets of my cum into my panties! I watched myself in the mirror as I was cumming and it would get me so hot, that in a few minutes, I would be cumming again. And again. My panties would be drenched and filled with my boyish juices. It was heavenly, in an evil way."

Reverend Spunkless looked very uncomfortable. Was he angry at me or excited by me? That stiff Johnson in his trousers answered my question.

"Sometimes, to make myself cum extra hard, I would dream about a boy kissing me and stroking my little love toy. It was always the same boy and now I’m so glad that I never led him into my sin. But in my dreams, he would kiss me and tell me how beautiful I was. Then we would cum all over each other. It was a dream, but the part about me cumming was real. Well, that’s all over now, because I’ve found redemption. That part of me is just gone. I prayed it away. Thank you."

There was polite applause, but the boys’ throats were too dry for verbal accolades. The Rev called a break right after that. He went into his office and closed the door. Everyone else, except Craig and I, went to the boys’ room. I sat next to the boys’ room reading a prayer book and listened to the moans coming from the stalls. Craig stood across the room and looked at me with an enigmatic stare. The jerk.

 

Chapter Four -- Reality

The next day, the Rev congratulated me on my progress and said that I was ready to move to the portion of my program outside the thrice-weekly meetings. Rats. Even worse, I would be spending time discussing my problem with my dear sponsor, Craig, the Hitler Youth boy.

Craig gave me his usual surly look and said that we could meet at his house at noon on Saturday. Ick.

To keep Mom off my back, I agreed to meet at Craig’s, though poison seemed a better option. Mom dropped me off and said she would be back at six.

I knocked and Craig yelled, "It’s open." I walked in and wandered to the sound of Craig’s voice, which was upstairs. Probably on his knees praying to be rid of his curse, I thought.

I entered what appeared to be Craig’s bedroom and saw Craig. At least I thought it was Craig under that tiny, lacy white nightie, sexy, wispy white panties, sleek, seamed white stockings, white stiletto mules, styled hair and perfect make-up. He was gorgeous! A 16-year-old princess of beauty!

My mouth hung open even more when I saw the loveliest, biggest cock, skinned, wet, dark and hard, peeking from his sweet panties.

He smiled at me. It occurred to me that I had never seen him smile before. It was a lovely smile.

I smiled back.

Craig said, "Did you really think I bought into the Rev’s program? None of us do. We just pretend we do to keep our parents off our backs."

"I thought I was….I thought you were."

"I know, Honey," Craig said. And then he kissed me. A soft, sweet, loving kiss.

It was my first kiss and it had me spinning.

When I was thoroughly kissed, Craig said, "We’re who we are, Paulo. We can’t pray away brown eyes and expect to have blue ones the next morning. We can’t decide one day that our eyes are blue when they’re really brown. It seems like such an easy concept, but the world doesn’t get it. The world ridicules us, so we end up hating ourselves for who we are. We can only blame ourselves for that."

I wasn’t sure about the philosophy, but I loved hearing that I wasn’t evil or a freak. And that kissing was awfully good.

"I have a present for you, Paulo, but I want a kiss first."

Gladly. "Mmmmmm."

"Wow. You’re beautiful, Paulo. Here’s your present."

A medium-sized box, nicely packaged. I ripped it open and stared at the contents, then began to cry. It was a pink nightie. And pink stockings. And pink panties. And pink stiletto mules.

I hugged Craig and sobbed.

He began to cry too and said, "We’re all in this together, Paulo. Would you like to dress?"

I was out of that boy crud in milliseconds and dressed in a flash. I was whimpering with joy at being back to my real self. Craig offered me some make-up and I put it on. My prickie was very big and excited, protruding from my panties.

Craig whistled. I blushed. "You’re fantastic, Paulo."

I radiated with pride and delight.

"I would love to adore your gorgeous body. May I?"

He was so direct. I liked that. In a soft voice, I said, "OK."

Craig took me in his arms and kissed me, girl-to-girl, lipstick-to-lipstick, hot, hard, gooey cock to hot, hard, gooey cock. His nightie rubbed against mine and his tongue entered my mouth. That was very nice. Very nice. Too nice. I felt the cummy rhumba in my gut. I wanted to tell Craig, but my mouth was full of his tongue. So all I could do was CUM!!!! All over his panties and cock and pretty nightie. Three pent-up weeks of CUM!!!! Spewing, gushing, sploogeeing hither and thither. I was shaking and whimpering and Craig hugged me and comforted me as my boy’s cream cascaded down his tummy and his thighs.

Then he did the strangest thing. He fell to his pretty knees, pulled my panties down a few inches and took my cummy, half-hard cock into his sweet mouth.

Holy hotlips! My best friend had never visited someone’s mouth before and it made him very happy. I was having a difficult time staying balanced on those pink mules, because all that licking of my gooey cock had me wiggling in delight.

It was heaven. I got hard really fast, then Craig turned his attention to my quivering balls. He bathed them in his hot saliva, kissing and worshiping each bagged testicle until I began squealing and crying softly in sexual agony. When he stopped and kissed my slimy cockhead, I locked eyes with him, groaned softly and covered his pretty face with a torrent of hot gooies. I was mortified. I didn’t mean to cum in his face. But from the smile on his face as he swallowed as much as he could get his lipsticked mouth around, I would say no apology was necessary.

Oooooooo. That was intense. Self-inflicted cummies are wonderful, but the best sex is definitely a duet.

How could I love being pleasured by a guy who fifteen minutes ago I believed hated me for being a crossdressing little pervert? Simple. Because he revealed himself to be a crossdressing little pervert and was a really good kisser and cocksucker. Really good.

I decided to test my skills in this area, but Craig asked that I join him on his bed. I lay next to him. He smelled very nice. Expensive perfume. He lifted my pink nightie and stroked my cock. My cock was too exhausted to even….oooh….it was…..aaah…..getting hard again. When was I going to get to stroke his? He stopped stroking. I wanted to make my move, but it appeared he had a plan. He reached in his drawer and extracted a small jar of Vaseline. He pulled his panties down six inches (hey, I wanted to do that) and rubbed some of the slippery stuff on the big pink tip. I wanted to do that too.

Then he did something I never expected. He put some Vaseline on the tip of my cock and rubbed it ever-so-sweetly with his right hand. He put Vaseline on two fingers of his left hand and slowly, excruciatingly, entered my tiny butthole with those greased wrigglers.

I jumped! I arched my back. I came again, the third time in about a half hour. At that rate, I would need an IV soon. Or a funeral plot.

I was cumming in hard spasms as Craig’s talented fingers plowed on. His pretty face was smiling roguishly and he was driving me insane with lust.

Just as I miraculously managed a fourth cockstand, Craig moved me on my side and spooned behind me. Did he think he was going to fuck me???!!!! I wasn’t ready for that. I was too young. Too tight. Too scared. I opened my mouth to forbid it just as my pooper suffered a penile puncture.

Whoop!

Gasp!

What was the number of that truck?

 

A number of things happened in rapid succession. I’ll try to relate them accurately.

First, I screamed like a little girl. That was, after all, a large object entering my poopie pit!

Then I lost my erection. I mean, it melted.

Then I felt a twinge of pain. Not a fiery rip. Or a blistering spear. It was more like a "Was that pain? I think so?" It felt kind of good actually.

Then I went into a major sexual heat. I quivered with lust and actually pushed back to get the full complement of Craig’s big cock.

Next, my erection came back to sort of a half-mast position. As if it were undecided whether it liked the proceedings.

I didn’t doubt it at all. I loved being fucked. Even by a sissy in white frillies like Craig. I could smell his perfume and taste his lipstick as he fucked me with skill and ardor.

Craig stroked my little boy, but it never got any harder. Even when my throat constricted, my eyes widened, my nipples popped out and I blew a big goostorm all over Craig’s nimble fingers. I screamed again. What a girl I was.

Craig was enjoying himself very much. I looked over my shoulder and licked his tongue. Then he lurched into a gut-wrencher of an orgasm himself. His first. My fourth. What a horny little piece of ass I was too!

Cum was tickling my bowels as he pushed the remains of his boner into me, spurting madly, then tapering to a trickle. When his poop-stained rammer popped out, my gaping anus was drooling cum. I was so ashamed. And so ready for more.

Craig lay on his back, breathing heavily.

His cock was limp, drooling cum, and flopped toward his right hip. It looked delicious, so I got on my knees and began to handle it with soft, warm fingers. I had never touched someone’s cock before and it was fun and educational to do so. The little twitches and Craig’s pretty, encouraging smile, led me to kiss it all over. I especially liked kissing Craig’s big, heavy balls and thinking about all the sissycum he was making in there for me.

Craig liked the ball kissing a lot. And the little flutter licks I gave those little darlings were also well-appreciated. His sissy thingie got all big and hard and red again. So I decided to see what cum tasted like. There were some cum drops on the pink head, so I licked them off. Mmmmm. Very nice, but I wanted the warm stuff right from the tap. So I started licking his knob. Around and around. Making lots of girlie giggles at Craig’s wriggling and moaning.

Perhaps that wasn’t the appropriate moment, but I managed a good look at Craig. With his short hair and lack of breasts, he looked like a boy dressing up as a girl. Which, of course, was what he was. But it was more than that. Even when his cock was in my drooling butt, I didn’t think of him as a boy. Or a girl. He was a sissy. Which was what I was and what I was often ashamed to be. But at that moment, I was a sissy on a mission.

Craig’s pink mushroom was leaking sticky stuff and I was lapping it up very quickly. He looked at me, stroked my head, said, "Ohhhhhh!!!" and started spurting long, slinky strands of sissyjuice. Big, leaping ropes that I tried to catch in my mouth, but began to gag from the effort.

I must say, that his cum was yummy. Nice and tangy, with just a bit of saltiness. I wanted to compliment him on that, but he was wincing in sexual torment and arching his back as he shot his goo skyward. I decided to tell him later.

Even the aftershocks were intense, throwing up two short cummy spritzes and a long drool of complete ball evacuation. I must have swallowed a pint, which left another pint scattered throughout his bedroom. Oh, well.

Craig sighed deeply then drew me to him for some soft kisses and hugs. I played idly with his cock as he kissed me and praised my considerable, innate skill in lovemaking.

"I knew you were a hot tamale the day I first saw you," Craig said.

Was that a reference to my Portuguese ethnicity? For the record, we Portuguese don’t make tamales. I wasn’t sure I liked that. But then he went on.

"You’re beautiful! And very hot. The best piece of ass in the Dressers Anonymous group."

OK. He was out of the doghouse. But I had to ask. "You made love to the others?"

"Of course. Many times. We all dress and have sex whenever we can. It’s the only advantage of listening to Reverend Spunkless three days a week. And our families think that whenever we’re together, we’re giving each other support to stop dressing. They even let us have sleepovers at each other’s houses. Say, you didn’t know 12-year-old Will was hot for you, did you? We never let a new person in on our secrets until we know he’s cool."

Will? Oh yeah. Will was very cute. I imagined him in stockings and heels. With his nice, stiff cock. I was so bad.

Craig said, "Would you like me to arrange a sleepover for you at Will’s? The mothers and fathers think I’m the zealot and go along with anything I say."

"I’d love that, Craig. But I believe you have something else you need to do first."

Under my gentle massage, his cock had grown hard enough to cut diamonds. I got on my tummy and scrunched my ass up for him. He smiled, pushed his bruiser into me and fucked me silly.

Twice.

 

Chapter Five – Will

I learned at least two important facts that Saturday with Craig – sex with a fellow sissy was a gut-wrenching delight, and the other boys in our DA group were all still sissies whose guts were very wrenchable.

In addition, I learned about spots on my body that I especially liked having kissed, licked, sucked, caressed, tickled, touched and rubbed.

 

And I began to understand that dressing appeared to be something I was destined to do. For better or for worse.

Mostly better appeared to be my situation at that point when I was 13. When I attended the next Monday’s DA meeting, I saw my fellow "perverts" with new eyes. Craig was now the alpha-sissy, plotting to defeat the Man and help us sissy up and sissy each other to ball-draining climaxes. Each of the boys was now a potential sissy girlfriend and sex partner. When I imagined them en femme, they all looked quite edible.

Will in particular. He was a year younger than I and quite shy and, dare I say, girlish. I felt like a predator regarding Will, much as Craig had been to me. I wasn’t much older and had only one afternoon’s experience, but I wanted to flip that little sweetie on his back and pound his pooper.

Craig must have spoken to him, because he kept giving me little shy looks, which I returned hungrily. He was a real cutie. Short and slim with that great crossed-chromosome look of blond hair and dark brown eyes, with long, curly lashes. I wondered if I could take him into a boy’s room stall and make nice-nice with him. Probably unwise. And it seemed a little "gay" considering we were both dressed as boys. A dumb mindset, but firmly implanted.

We got to talk at one of the breaks and he told me that his mom was calling mine about a Friday sleepover at his place. He also told me that he had new black stockings, with a matching garter belt and strappy, black, stiletto sandals that he was going to wear when we went to bed.

Ooooo.

I needed to upgrade my wardrobe. I told Craig and he was most helpful, lending me some tan, seamed stockings, a white garter belt and a pair of sexy, red, open-toed mules for my big excursion to Will’s.

My Mom was cool with everything. The poor woman thought Will and I would be bonding as former dressers. We would be bonding all right, but coitally.

Mom drove me and I showed up at Will’s with my sissy gear concealed in my backpack. Will’s mom was really nice. She gave us cookies and all that and left us alone in the family room to watch videos.

I wanted to get to bed, but it was only 7:30, so we did the next best thing. Will’s Mom had given us a blanket to cover ourselves as we watched TV. Will and I pulled our pants down to our knees, then shared the covering blanket. Our privates were thus exposed to wandering hands and warm caresses.

I gave Will’s cock a very nice tactile examination, which he enjoyed immensely. He had a pretty little prick, with a small head that leaked goo copiously. I was afraid we would float away, but I massaged him lovingly and he spurted his hot, boyish cream all over my fluttering fingers.

Will returned the favor, giving me an earth-mover himself. I liked this sissy! When we were sure his mom was upstairs, we kissed each other hotly. If we were this excited in boy’s clothes, I couldn’t wait to get into my panties and party.

At ten, Will’s mom said we could go to bed if we wanted and watch TV up there. We readily agreed. Will put the blanket in the wash, saying he had spilled Coke on it. Then we ran up the stairs, hoping that we weren’t too obvious.

We locked Will’s door, stripped each other naked and kissed, rubbing cocks in an exciting dance of passion. Before we knew it, we were cumming buckets all over each other. I felt I had been run over by a truck. This was one hot young sissy!

We cleaned ourselves up and got into our girlie gear, giving each other little teasing glances as we dressed and made our faces up. I looked hot! And so did Will! I loved wearing the stockings and heels and leaving my chest bare. I hoped Will would be drawn to my nipples and give them a good sucking.

Will was a doll. And his cock was miraculously stiff yet again. I dragged him to the bed, and got into a frantic sixty-nine with him. His cock was delicious and it fit into my mouth along with his wrinkled little sack of grapes. I licked him to distraction and when he came with a muffled scream (my cock in his mouth), I sprayed his pretty face with several spurts of love sauce. I loved being a sissy!

It appeared that some fucking would be a logical next agenda item. I believed that as the older boy, that would be my department. I was wrong. In bed, Will was a budding little alpha sissy. He began licking my nipples, driving me into mad squirms and sexy moans. Then he entered my anus with his little fingers and I let a big load spurt all over my tummy. Ohhhhh, my goodness that was a back-archer!

The bad boy kept massaging my pooper and licking my nipples, even giving them a tiny lovebite or two. He had me so worked up that I begged him to fuck me. I lay on my side, thinking he would spoon up to me like Craig did. But no.

Will moved me to the end of the bed. He threw my tan-stockinged, red-open-toed-muled legs over his shoulders and put the drooling tip of his small-but-eager prick at the entrance to paradise. I was a sissy’s sissy, letting this younger boy fuck me on my back. Like a girl. A submissive one at that. And I loved every millisecond of it.

He pushed, I gasped. My sphincter parted to welcome an honored guest. Ohhhhhh. So good. He pumped and pumped. I made soft squeals so we wouldn’t be caught. I looked into Will’s mascaraed, shadowed, lined eyes and his glossed lips parted to smile at me. I loved being fucked so much.

My cock was at full alert during my shagging and Will helped me along by rubbing the gooey head between his thumb and forefinger as he plowed my pasture. He leaned over to kiss me and I grunted, threw my arms around him and came, whimpering like the frilly sissy I was as my cock strained to reject my balljuice. I’m afraid that I got so excited, I bit his shoulder a little. It didn’t break the skin, but I thought I’d better "nip" that habit in the bud.

My pretty-boy fucker straightened up again and resumed his sweet in-and-out. My chest was still heaving from my hot cum explosion, when Will’s pretty eyes ignited and all his goo went up my warm, tender ass. It felt fantastic. Cum cures all ills.

Will fucked me twice more that evening and once more in the morning. I guess I was destined to be the sissy on the bottom. Funny enough, I was fine with that.

I asked Will after the morning shagging if he ever wanted a boy to fuck him like that.

"I’m not sure, Paulo. Sometimes I think I would, but I like fucking little sweethearts like you too much to even think about that now."

Hmmm. "Would you like to make love with girls?"

"I think so, Paulo. But I like this so much, why should I go after girls?"

Good point. "Would you like to make love with gay boys, dressed as a boy?"

"That I’m sure of. No. I love dressing as a girl and loving other sissygirls. That’s all I’m sure off right now."

He was right. I felt the same way. Word for word. And very confused about my sexuality.

 

Chapter Six – Omnivorous

One person who was not confused about his sexuality was Craig. He wanted to screw anything that walked. Except gay boys. He said he was heterosexual.

But one day as we were catching our breath after his third seminal deposit in my pretty butt, he told me that he had dated girls. And boys.

I was very surprised.

"I like girls," Craig said, "and I really like boys. Girls have that nice, gooey pussy between their legs and those soft pillows we call titties. Most of them have bad attitudes, dress like they’re homeless, can get pregnant and fend you off ten days a month – five for the period, five because they hate the world. But they’re soft and warm and you can fuck them face-to-face, rubbing up against their titties and kissing without breaking your neck."

I had no idea he had that kind of experience. "Whom have you dated?"

"Five girls, most of whom you know. But a gentleman doesn’t kiss and tell."

"But you’re not a gentleman. You’re a sissygirl."

"I can be a gentleman when I want to be."

I never thought of that. Seriously. "And boys? How did you manage that?"

"My auntie is cool with me being a girl. I visit her for two weeks every summer and she lets me dress. She was the one who introduced me to Robbie."

"Robbie?"

"A very nice boy with a big cock. He’s a year older than I. When we met, four years ago, he thought I was a girl. Until he got in my panties."

"You let a boy fuck you?" The idea disgusted me. Then why was my cock so red and hard?

"Dozens of times. He’s really gotten good at it, but he had a good teacher."

<Gasp> "You fucked him too?"

"Of course not, Silly. Girls don’t fuck boys. I was a girl and I became a girl in every way I could."

"Did you have a girl name?"

"Cheryl. Do you like it?"

I did. But none of us sissies had girl names. It seemed like a line we didn’t want to cross. "Would you like to be a girl always?" I couldn’t believe I was asking that.

Craig considered me, then said, "Maybe. How about you?"

ME??!!!! I didn’t. I wouldn’t. I thought about wearing pretty dresses out in the street and going to parties in lovely frocks and hugging whomever I wanted to and having boys adore me and even kissing boys and my cock burst. It spouted and spewed. I shuddered, then spurted more cum. Craig held me and said, "It’s OK, Sweetheart. It’s OK."

I was confused and scared and my head was swirling with the possibilities for my future.

 

Chapter Seven – Freshman Year

When I was a freshman, Craig was a senior and Will was in the 8^th grade. As the year progressed, I seemed to be spending more time with Will and less with Craig. Will was always the sexual aggressor. He would dress himself like and act like a complete sissy, then throw me on my back and fuck me silly. I sucked his cock a lot and never really thought about putting my prick in his poopie passage. In fact, I had a number of liaisons with the fine group of young sissies in our DA group and I was always the one getting my pit punctured. And I loved it.

I mean, they didn’t dominate me or anything. It was just kind of understood that I was the one getting hosed. And understood that I liked it. I didn’t know what happened when two of the aggressive sissies got together and I didn’t care. I loved dressing up and I loved cumming and making my friends cum.

In January of my freshman year, a disturbing thing happened. My sister, Maria Luiza, a junior, asked me about Craig. She thought he was cute. My sister liked my sissy sister!

I told Maria Luiza that I thought Craig was seeing someone, that he might be gay, that he was hygienically challenged and that he had plotted armed insurrection against the United States, but she was relentless.

She flirted with Craig and they began dating in February. One Saturday afternoon in March as I was removing my stockinged legs from Craig’s shoulders and feeling my asshole tingle from a big load of his hot cum, I asked him what his intentions were with my sister.

He laughed. "Maria Luiza is a sweet girl. Just like her brother. We’re just having fun."

"Are you fucking her?" I asked.

Craig denied it, but after hundreds of his hot loads in my butt and mouth, I knew him well enough to know he was lying. What was the deal with Craig? Why couldn’t he just pick a team and stay on it?

And by the way. What was MY team?

Craig and Maria Luiza ended up going to the senior prom. I wore my slinkiest outfit that afternoon and drained six cummy loads from his aching balls. At least my sister wouldn’t be going out with Craig at his horniest.

They came in that next morning around four and very quietly fucked on the couch. I sneaked a peek and saw Maria Luiza on her back, with her black-stockinged legs wrapped around Craig’s torso as he kissed her lips and ground his pelvis into her. They both came hard together, then Craig began to fuck her again without withdrawing. Where did he get all that goo?

I slinked off to bed wondering whether I would ever get to make love to a girl. Or whether I would want to.

 

Chapter Eight – A Vision of Normality

When Craig went off to college, I kind of lost touch with him and so did Maria Luiza. She was resilient, though, and found a boyfriend even I liked.

No girls came my way in high school, but I have to say, I didn’t actively pursue them either. I was having an incredible time with my sisters from DA. Some great new sissies joined my sophomore year and there was always a dress-up sleepover, ending in a good pounding of my tiny butt. It was paradise.

Mom and Dad worried a little that I wasn’t dating, but I assured them I didn’t need any more distractions beyond DA if I wanted to get into a good college.

As it turned out, I did get into a good college – an Ivy League school, and no one was more surprised than I. I guess I was pretty smart. But I think having my balls drained more than anyone in the school was probably why I could concentrate in class better than other kids.

When I got to college, I despaired for my sissy life. I missed Will and my other sisters tremendously and didn’t even have the privacy I needed to dress.

Maybe it was time to see what was behind the curtain. Maybe I should see if a "normal" life with a wife and kids and men’s clothes was what I wanted. At that point, I had little choice, so I began to pay attention to girls.

They weren’t all bad. There was Vicki in my English Comp class and Rachel in Western Civ. And then there was Melanie.

Melanie Stevens was a hetero guy’s dream. She was tall and slim, with long, straight, brown hair, killer legs, big boobs, a tight butt and beautiful features. She was also reported to be quite wealthy.

I didn’t really date Melanie or any other girl freshman year, but my group of guys hung out with Melanie’s group of girls, so we would talk sometimes. I began to dream about a life with Melanie, raising a family, wearing men’s underwear and not sneaking around all the time. Aspects of it were pretty attractive.

Did I feel sexually attracted to Melanie? Sure. Who wouldn’t be? Yeah. Kind of. Yeah.

I could see a "normal" life with her. Out in the open. Normal.

 

Chapter Nine – "Bad" Habits Revisited

When freshman year ended, I had received no encouragement from Melanie and my balls were bursting with cum. I decided to pay a little visit to my friend Will, who had just graduated from high school. He had a summer job at an outdoor music festival, so he worked nights and was home alone during the day as his Mom worked a normal schedule.

I resurrected my sissy gear and toted it to Will’s house. We kissed hotly, for the first time in nine months. Was I crazy not to see him at Christmas? Yes. I was trying to deny my sissiness.

But now I was back in my sheer, black stockings, frilly garter belt, black bikini panties, black, five-inch pumps and black bra. I added some eye enhancements, foundation, blusher and lipgloss and I was ready for a fun afternoon.

In his baby blue cami, with matching stockings and garter belt, Will looked good enough to eat. We kissed and stroked each other and tickled and teased each other’s pussyholes. When I was mega-hot, I flipped on my back, spreading my legs and bending my knees so Will could fuck me.

Surprise, surprise. He did the same for me. Flopped on his back. Ready for my cock. Did I walk in in the middle of the movie?

He whimpered for me to fuck him, so, for the first time, I was on top with a sissy sister. I propped his butt up with three pillows. Then I rubbed my cock and balls against his to get him even warmer. His balls were boiling rapidly when I pushed the gooey tip of my stiffie against his sissy hole. He gasped sissily as I inserted the nut. It felt wonderful! Much better than the thousands of blowjobs I had exchanged with my sisters. I pushed more in and he whimpered like a little girl. How nice. I could feel his anal walls rubbing and gripping my sensitive glans. I pushed the last of it in and he gave a little gulping sound. Was that what I sounded like?

I got into a lovely fucking motion with Will. We both knew what one of those was, and I tickled his balls and stroked his poker. He was very excited, squealing like I used to when I was being pounded. Then he gasped, scrunched his pretty face, and came a bucket all over his cami and garter belt. It was very exciting and within two minutes, I left my first load in a sissy’s ass. An incredible feeling!

As we lay in repose, I asked him why he was submissive all of a sudden.

Will blushed and said, "I have a boyfriend now. He fucks me like you did all the time."

"What?" I leave for a year and everyone just does whatever he or she wants?

"His name’s Kenny," Will said. "He calls me Tara and he’s really nice to me. I got brave when you went off to college, Paulo."

"You sure did. Tell me about it while I skin your little peeny."

"That feels very nice. Oooh. Well, I decided that I would see if I could walk around in the world dressed as a girl, instead of just putting on some lingerie and fucking. Not that it wasn’t fun. But I wanted to see if I could be a girl, not just a dress-up sissy. I used the money from my paper route to buy a couple of outfits and one day, when my mother was working and there was a teacher conference, I put on a black, 14-inch mini, tucked my poker in my panties and went out the door. I didn’t know where to go exactly, so I just walked over to the park in my big, spiky heels and fed the ducks. Other than men and boys checking out my legs and butt, no one bothered me. I guess I passed. Could you massage my balls a little bit too, Paulo. You’re so good at that."

Will or Tara was right. I was good at it.

"I figured I had been brave enough for one day, when I noticed this nice boy about my age, feeding the ducks too. I could tell he was checking me out and I got the funniest feeling in my stomach, you know?"

I knew. I put two wiggly fingers in Will’s anus.

"I was very shy, but he was very brave. He came over to me and chatted me up. He asked me my name and I panicked, because the only name I had ready was Will. I pulled up Tara from somewhere, maybe "Gone with the Wind," and he told me what a pretty name that was. His name was Kenny and he was senior at West High across town. We sat on a bench and talked for an hour. I was terrified that he would discover I wasn’t a total girl. But he didn’t. Of course he ended up asking me for my phone number and I almost fainted. I said it would be better if he gave me his number and he acted as if that was just fine. He wanted to walk me home, but of course that was out of the question. I was going to throw his number away. I couldn’t right then because I didn’t see a basket. And I don’t litter. I forgot to throw it away when I got home.

"That night, as I was lying on my bed in my boy t-shirt and boy shorts, I wondered what it would be like to dress up for Kenny and even maybe, under very strict conditions, go somewhere with him. A movie. Or pizza. Just as friends. I would tell him about being a boy and he would say OK, because you’re still pretty and funny and sweet. And then he would try to kiss me. And I would let him. More than once. I was so excited thinking about kissing Kenny. More excited than I had ever been with you and Craig and the kids at DA. Just thinking of kissing him made me….just like you’re doing in my……I wanted him to…….that’s very nice………Uhhhhhhh. Oh. Oh. Oh. Eeeee!"

The little doll threw goo all over, just from telling me about meeting that Kenny guy. And dreaming of kissing him. I’ll bet he’s hot, I thought. Then I hated myself for thinking that way. Like a faggot. I wasn’t. I was just dressing a few times that summer and that was it. Straight and normal for Paulo Malone from here on in. House. Kids. Wife. Straight.

"That was wonderful, Paulo. Thank you. Would you like to hear the rest of the story?"

I did and I said so.

"Great," Tara said. I guessed I could call her that. She was definitely in Tara mode. "I’ll just skin your nice big guy here while I tell you about Kenny and me. "I’d forgotten how big and hard you are Paulo. It’s very hot and gooey too."

I moaned a little, but it had nothing to do with thinking of Kenny doing Tara.

Tara continued. "I didn’t call Kenny. I guessed I wanted to, but I was scared. What if he liked me? What if he didn’t like me? What if he rejected me when he found out about my stiff little secret? What if I told him my secret and he still wanted me? You know what I mean, Paulo."

I nodded, but I wasn’t really sure what she meant.

"Anyway, I decided I would call him, but then I couldn’t find his number. I tore the house apart and couldn’t find it. I sobbed for an hour. Then I decided to dress and go back to the park. I did that and he wasn’t there. So I went back the next day and still no Kenny. What an ass I was, I thought. On the third day, I went to the park, despairing of ever seeing Kenny again and there he was! Feeding the ducks. He smiled like Christmas morning when he saw me and I guess I did too, because he came over to me. He hugged me and I was crying, because I was happy and scared and feeling cheap and confused. Kenny looked concerned and he asked me what was wrong. I just sobbed harder and he led me to a park bench. I don’t know where I got the courage, but I told him everything. About dressing and DA and Reverend Spunkless and my sissy sisters. I was trembling waiting for his reaction and then I got it."

"What was it, Tara?"

"Oh, that’s so sweet. You called me Tara. Am I frigging you right? Oh, look at all that sticky stuff. I guess I am. He kissed me, Paulo! And hugged me. He said he really liked me and wanted to see if we could go together. It was a dream come true!"

Not my dream. I was hetero.

"I had to tell my Mom about him and all my dressing if I was going to have a relationship with Kenny, so I did. Mom was fantastic. She realized that if five years at DA didn’t "cure" me, she was trying to change something that couldn’t be changed. She said I could dress whenever I wanted and could date Kenny!"

Omigosh! That sounded so wonderful! Dressing and a boyfriend! No it was gay! Icky bad! I wanted normal. Ohhhhhhhh! My poor cock betrayed me. It was blowing gooies all over as Tara teased and milked the juice out.

Tara kissed me through my orgasm and the aftershocks. It was delicious, but I still wanted to know more of the Kenny story.

"Kenny and I started off slowly. He picked me up at my house and took me for pizza and a movie over on his side of town. Mom and he got along very well. I guess he was the son Mom never had. Anyway, he introduced me to all his friends and treated me like a precious jewel, opening doors, asking if I was OK. I was being given large globs of masculine attention and I loved it! He held my hand during the movie and it felt warm and a little hairy. I kept wondering what I should do and how I should act when I took him home. I mean, I had sucked more cock than most $25 hookers, but it was all sissy cock. I wanted him inside me, but I wanted him to respect me too, you know?"

I nodded. Yet another conundrum.

"After the movie, he drove me home and we chatted like old friends, which we were fast becoming. At my doorstep, he told me how much he enjoyed being with me and asked if he could kiss me. For some reason, that was sexier than if he had just pushed his rammer up my pooper. In my big heels, I was still an inch or two shorter than Kenny. I could smell his pheromones and his Old Spice. Mom had given me some of her expensive perfume and I could tell he liked it. Or maybe he just liked me. He put his hands on my shoulders and kissed me, gently and maddeningly sexily. No tongue or anything in his kiss, but I almost creamed my panties. A good thing I had given myself a firm tuck, because I was very hot! After about 30 seconds of transportation to heaven, he stopped, nuked me with a smile, and said good night. Great Caesar’s Ghost! No body parts except lips, shoulders and hands and I was trembling with lust. Are you OK, Paulo?"

My willie had made a full recovery. I choked out a "Yeah." Tara saw my predicament and put a couple of her sweet fingers up my pussypit as she continued the story.

"We had three more incredible dates before we did anything beyond a goodnight kiss. Mom was out with her friends and after a walk in the mall, we went to my house. I invited him in and he was nervous. I was too, isn’t that crazy after six years of non-stop sissy sex? It’s different with boys, Paulo. It’s much more exciting. Anyway, Kenny sat on the couch and I sat next to him. We began to kiss and we were both in a state of high arousal when I made the first tiny advance. I unzipped his pants, reached in and extracted his cock and balls. He liked that. I got on my knees and bathed his balls. He really liked that. I took my cock in his mouth and used every trick I had learned. Kenny was in paradise. I giggled when he warned me about his imminent cummy explosion, then took six big blasts in my pretty face as he wriggled and scrunched his face in orgasmic agony. Oh, Paulo. It’s spurting out again, you bad boy. I’ve never seen you so excited!"

It was true. Tara’s tale of loving a boy had my balls in an uproar. Good golly! A real boy. A manly one. Treating you like a lady. Putting his thing in you. Taking you places. Gagging you with his cock. Adoring you. It was almost enough to make me reconsider my plan to lead a normal life. But it wasn’t.

Tara went on about how Kenny put her on her back and fucked her that night and about a hundred times after and how she wore a beautiful dress to Kenny’s senior prom and all, but I didn’t want to hear all that gay nonsense. I was a boy and I was going to start living as one. Right after that summer. And about 60 more sex sessions with Tara. But right after.

 

Chapter Ten – Normal at Last

I actually did manage to make that summer a turning point in my life. When I went back to school, it was as a young man, bent on the wooing of a young woman. Wonder of wonders, Melanie did become attracted to me. We dated for the next three years and when I went home, I visited my old DA friends, but didn’t dress and didn’t even kiss them. Tara, it turned out, with her mother’s help, had gotten breast implants and was taking hormones. I saw her once or twice and the change was startling. She looked fantastic. She and Kenny became engaged and married after their sophomore, my junior year. The wedding was in Vermont, so I couldn’t go, but I sent a nice gift.

I didn’t even wear panties. I felt a dull ache every day. But I knew I was doing the right thing. My senior year, I got my big reward. Melanie went to bed with me and I suddenly had all the sex I could handle once again. She was sweet and loving and never once caught on that when I was involved in intercourse with her, I was pretending that I was the one being fucked. It was still hetero sex, right? I mean, give me a break here.

Then I went out on a bigger limb. In March of my senior year, I asked Melanie to marry me. She cried happy tears and said yes. How wonderful! My normal life was assured.

 

Chapter Eleven – Honesty

Immediately after college graduation, Melanie and I got jobs in the same accounting firm in my hometown and were married that December. It was a lovely wedding and Melanie looked gorgeous in her gown. The thought that I would have looked better in it flashed through my mind, but I suppressed it!

We had a wonderful marriage, lots of laughter and good conversation and knock-down-drag-out sex. It seemed to get better and a year into the marriage, when our sweet daughter Jenny was born, life was just about perfect. Except for the constant, dull ache I felt being in men’s clothing. And missing my sissy friends. And playing macho guy all the time.

One day, four years into what I wanted to be a lifelong commitment, Melanie and I were talking about honesty and how important it was to a successful marriage. We mustn’t keep anything from each other, she said. Of course she was right. Melanie made me cry by telling me how an uncle once tried to have sex with her. It was a horrible story. I hugged her and kissed her and told her it was all right. I wanted to share something with her that would prove that I loved her and was totally honest with her.

So I told her about my dressing. And sex with my sister sissies. And the urges I had to continue dressing. And how I fantasized that she was fucking me instead if vice versa.

I knew this would lead to a better, more solid, loving marriage.

Was I nuts?

She took a few moments to digest it all, then she screamed for me to get out of the house. She called me all kinds of horrible names and was racked with sobs. She almost got violent when I tried to talk to her.

I gathered a few things into a suitcase and ran out in despair.

 

Chapter Twelve – Renewing a Friendship

Tears were streaming from my eyes as I drove away. My marriage was over, but worse, how would I ever see my daughter with her mother hating me. And probably taking me to court. And slandering me wherever she could. Melanie screamed that she would tell everyone at work that I was a faggot sissy, not a man. If I wanted to go back there, life would be difficult. Most of my possessions were in the house I had just left and we were too young to have much of a bank account. I was ashamed to face my Mom and Dad.

I was in bad shape.

Strangely, my thoughts turned to my first lover and mentor, Craig. I hadn’t seen Craig in years, but I knew he could help me. It was still early evening, so I called his mother.

"Paulo, it’s so nice to hear from you. You’re a good boy."

I wasn’t good and I wasn’t always sure I was a boy. "Can I have Craig’s phone number?"

"Oh, sure, it’s 555-5678. He’s changed since you saw him last, though, Paulo."

"Changed how?"

"Call him. Goodnight."

I called Craig’s number. A woman answered.

"Yes, ma’am, this is Paulo Malone. May I speak to Craig, please?" I prayed I had the right number.

Hesitance on the line. Then the woman said, "Paulo?"

Hesitance from me. "Craig? I thought the person speaking was a woman."

"Where are you?"

I began to cry and told him the whole story. He gave me his address and asked me to come over. I sped. Nice house. Two-car garage. Craig was 29 now, still three years older than I. Probably doing all right for himself. I knocked.

A lovely woman answered the door. She was dressed in a pretty A-line dress, stockings and heels. Her blonde hair shone and her beautiful face was made to perfection. It was… I said, "Craig?"

She hugged me. "It’s Cheryl now, Paulo. Come in, please, my dear friend."

A man came out of the kitchen. Good-looking, tall and friendly. Cheryl said, "Paulo, this is my husband, Robbie Pierce."

Husband? Robbie moved forward and shook my hand. "It’s wonderful to meet you, Paulo. Cheryl has always spoken so well of you."

What a nice guy.

I sat on the couch and Cheryl rocked me in her arms as I told her and Robbie what had happened. They both asked excellent questions and were a great comfort to me.

Still, I had no job, no home, no wife, no child, no money, and had been exposed to be what many in the world believe to be a pervert. What could I do?

Cheryl and Robbie took me to a pleasant guest room. Cheryl laid out a pretty nightie for me. Robbie said, "You can stay here as long as you like, Paulo, but tomorrow, we’re going to get you down to the folks at Sanctuary. We’ll tell you more about that in the morning.

Sanctuary?

 

Chapter Thirteen – Memories

I slept better than I thought I would that night, although the sounds of Robbie and Cheryl making turbulent love did make me a bit jealous. Of Robbie. Or maybe Cheryl.

The nightie felt delicious. The only good experience in an awful predicament.

Another reason I slept so well was that I was so excited by the nightie that I spilled my sploogee several times before I went to sleep. Listening to all that fucking and the feel of my first femmy things in more than seven years made me remember all the good times I had with my sissy friends from DA.

In particular, my thoughts focused on a going-away-to-college party we had eleven years ago, for Craig (now Cheryl) at Craig’s house one Saturday afternoon while his Mom was at work.

My goodness, there must have been ten of us little mincers there that day. We all decided to just wear sheer, black stockings, black garter belts, strappy heels and our prettiest panties. We wanted to show Craig a good time before he went into the Land-of-those-who-despise-us. And he had it.

It was the orgiest orgy I had ever been to.

Craig was very excited. He should have been, looking at nine pretty teen sissies, sissying in our heels, with out cocks sticking up over our panties. He had his choice of nine mouths to kiss or have his prick lovingly sucked with. He had nine pretty poopers to pork. And he had nine ball bags full of cum that would explode from nine very stiff cocks, accompanied by high-pitched sissy screams and squeals. We were all looking at Craig and smiling, but also stealing peeks at each other. There were some hot sissies there.

Harry had a big cock. I mean a big one, but he was probably the sissiest of us all. He loved pink and it was difficult to get him back into guy mode after some sissying. We didn’t want him to be caught. Harry was making little giggles and teases at me, when Craig said he would like me to suck his cock first.

It was a great honor, plus, I would get the creamiest, thickest cum in my tummy and I wouldn’t have any of the other sissies’ poopie on his cock when I sucked it. Some said that added to the fun. Well, they would.

I got on my knees and began to kiss and stroke Craig’s rammer, which had gotten quite large. His balls were beauties, big and goo-filled. I gave them a few special kisses and licks too. Already Craig was moaning when Casey began to kiss him. The little twelve-year-old tramp. He wore those platforms that day just so he could do that, I bet. Richie got up behind Craig and began to kiss his neck as he entered Craig’s butt with his lubed fingers. Was he going to fuck Craig while I was blowing him?

Why, yes he was. An interesting spectacle for the four uninvolved sissies, who wisely paired off and began their own extensive lubrications and excavations.

It’s difficult to suck someone’s weenie while his butt is being plowed. But I’m sure you knew that. The fucker tends to push the fuckee all over the place, making the sucker’s task quite turbulent. Still, I soldiered on and the combination of emotions, participants and pleasant friction brought Craig to a shuddering, paralyzing, creamy conclusion.

Craig’s cum was a wave of goo, filling my mouth, streaming down my throat and chest, and highlighting my 15-year-old, pretty face. I sucked and licked hungrily.

Craig’s butt was blasted by a cumstorm from Richie’s ample prick and that got Craig back to half-hardness, as I continued to suck him. When he was fully stiff again, he left Richie and Casey to their own carnal lusts and took me to a corner, where we were alone.

"You always knew I loved you the most, didn’t you, Paulo?"

I didn’t. But now I could see that it was true. Eight other sisisies ripe for whatever he wanted. His first, creamiest load he gave me. He was about to give me his first fuck. I WAS special to Craig.

Lying in bed that awful night, I could feel Craig fucking me eleven years before. He was on top of me and our lipsticked mouths kissed hungrily. Craig’s big cock entered my pooper like the old, familiar ground it was. He embraced me, telling me he loved me and kissed me sweetly as he fucked me.

The memories were too much. I reached under my pretty nightie and rubbed my sore cockhead vigorously. I remembered that orgy where all the guest of honor wanted was me. And now Craig was a woman named Cheryl, making animal noises as her husband fucked her for what I counted as the third time that night. Omigosh! Craig! Cheryl! Being fucked by a man. Fingers in my pussyhole then. Aaaaaaaah. I spilled my cream. Oh. More delicious juice. Again. And two more. I was shuddering and in a cold sweat.

It was good to be a sissy again.

 

Chapter Fourteen – A Place of Hope

We caught up at breakfast.

It turned out that Cheryl and Robbie had been married for five years.

After college, Craig moved in with his aunt and became Cheryl full time. Robbie had been in love with her for years and begged her to marry him. She underwent some surgery and had some hormonal enhancements. They helped her become a stunning woman. But it was her self-confidence and belief in her rights as a human being that were what really made Cheryl Pierce attractive.

When Cheryl and Robbie were married, they moved back to our town because of Sanctuary. Cheryl took a key personnel job and moved up with incredible speed to become the director of Sanctuary just two months prior to my domestic eviction.

But what was Sanctuary?

"It’s an international refuge and resource for transgendered persons," Cheryl said. "But even more, it’s a symbol of dignity and hope."

Huh?

She went on. "Did Melanie even try to understand you last night, Paulo?"

No. "Not at all."

"Did she ever consider the possibility that your genetics made you a crossdresser, not your choice?"

"No."

"Do you think you had a choice?"

Good question. "I chose not to for a while."

"And were you OK with that choice?"

A small tear dropped from my right eye. I sighed. "I wanted to dress every day for more than seven years and didn’t."

"I’m sorry, Paulo. That hurt you very much didn’t it?"

I sobbed softly and nodded.

"Why did you deny yourself, Paulo?"

"I wanted to be normal."

"No. You didn’t. You wanted people to think you were ‘normal.’"

I saw the difference.

"But we’re not what people think of as normal, Paulo. And everyone wants us to change. Most people ridicule us and think we’re pathetic. Popular culture mocks us. We can’t change, Paulo. It’s who we are. Why can’t the rest of the world change?"

As stupid as my admission sounds, I had never considered that. But Cheryl had.

"Sanctuary helps people like you get back on their feet again after their world rejects them. But we also help restore dignity and a feeling of self-worth."

"It sounds great, but what does that mean to me?"

"It could mean quite a bit. Let’s get you dressed and take you to Sanctuary. Would you like to dress as a man or a woman today?"

A startling choice. "A woman," I told my friend.

"Then we have work to do," Cheryl replied honestly. She was right. I was no Cheryl at that point in my life.

 

Chapter Fifteen – On the Grounds

Cheryl and I spent two hours slapping together enough of a girlie look to get me to Sanctuary. I was out of practice and needed everything. Fortunately, Cheryl had everything I needed.

Still, I would have only looked like a girl to someone with a kind heart and poor vision. Cheryl looked as if she had stepped out of Vogue, which made me look even worse. But at least I was back in my femmies.

We got to Sanctuary at 10 a.m. and Cheryl took me on a full tour, introducing me to all of the staff, who worked for Cheryl, and many of Sanctuary’s 100 or so clients, all of whom Cheryl knew by name.

The first stop was the beauty parlor, where I met Susan, the beauty director. Susan was a gorgeous, thirty-something, feminine masterpiece who frowned, tut-tutted and said, "You have good basic material, Paulo. I’ll schedule you for a 2 p.m. emergency appointment."

I was getting the idea that my femmy looks needed honing. I didn’t want to go too far, of course, because I would have to get back en homme to start looking for a job again. Wouldn’t I?

I asked Cheryl, "Is Susan a man?"

"None of us are men, Sweetie," my long-time friend said. "But we were all born into male bodies."

Was she including me? I didn’t think so. I was just there temporarily. Until I could get back on my feet again. And go back to being a man. In the straight world.

Cheryl showed me the reception area, where new clients were met and cared for. It was a lovely place, with warm colors and the friendliest three ladies. They were in their 40s and 50s and so sweet and sincere that I felt comfortable with them immediately.

I asked, "Who comes here?"

One of the ladies, Marla, said, "Whoever needs us, Paulo. Most are like you. They think they can live as men. They build what they believe are loving relationships, then share their

Secret. Nuclear explosion. End of relationship. Is that your situation, dear?"

Tears filled my eyes. "Yes."

The other two ladies, Brenda and Peggy, hugged me. Brenda said, "The only successful, long-term relationships are built on deceit, Paulo. If people shared all their intimate thoughts, they would kill each other the first year together. That’s true of all relationships. Truth is vastly overrated."

She was right, of course. Even mainstream relationships. What a revelation.

I met some of the clients who had experienced similar situations. They were all enjoying the companionship and true understanding of Sanctuary and missing what could have been in their former lives. They also all were dressing very femmy. And they all looked better than I. I hoped Susan was a magician.

Cheryl and I went by the counseling department, but all the counselors were busy with clients at that time. I knew I would receive counseling. We also saw the living quarters (quite nice) and the job training and placement centers.

We got back to Cheryl’s office around twelve, where I met Nancy, her secretary, a sweet, sixtyish TG, dressed very smartly. No one wore pants or pantyhose in Sanctuary. It was skirts and stockings. And big, high heels.

Cheryl excused herself and went into her office for a few minutes while I chatted with Nancy. Then she buzzed Nancy and asked to send me in and not disturb us for an hour.

Cheryl was behind her desk in her lovely, femmy-power office. I thought she would invite me to sit. Instead, she stood.

Oh my. Cheryl had already removed her skirt, slip and panties and was beginning to remove her jacket, blouse and bra. She did so and stood before me in heels, garter belt and black stockings.

I gulped.

"I missed you, so much, Paulo," Cheryl said. "It’s wonderful to have you back in my life."

Cheryl was the sexiest person I had ever seen. How she had ever grown those titties should be recorded and studied. They were C-cup beauties with huge, dark nipples and a perfect shape. They stood high and proud against her chest. Cheryl’s legs were shapely and exquisite and as she twirled for me, I could see that her ass was as well. Oh how I wanted to put my throbber in her pretty bottom!

She was the picture of feminine perfection except for one thing. Her cock didn’t look pink, hairless and petite, as one might expect. It was HUGE and VEINED and HAIRY. Really hairy. It was at least eight inches and it ended in a point, not a mushroom. Her balls were also enormous. Hairy and ponderous and surely stuffed with gallons of hot, creamy cum.

It was as if someone had stuck a superstud’s cock on a beauty queen’s body and didn’t consider the context. It was earth-shatteringly, mind-bogglingly incongruous. And I almost came on the spot, it was so damned sexy.

I did the only thing I could do. I fell to my stockinged knees and kissed, frigged, smooched, licked, tickled, teased, skinned, sucked and manipulated Cheryl’s spear of love until it gushed a tidal wave of cum onto my face and down my throat. I hadn’t sucked a cock in four years and I needed to do that very badly.

If her wigglings, squeals, groans, gasps and shudders were sincere, I guessed Cheryl enjoyed herself too.

She took me into her beautiful arms and kissed me for a long time. I knew again what I must do. I had just lived four years as a man. Cheryl was now a woman. I needed to be the aggressor and fill her poopie pit with my hard cock. I was the man.

Why then were my panties dangling from my right foot as I laid my back on Cheryl’s desk? Why was her rejuvenated rammer poking at my special place? Then entering it?

Ohhhhhhhh.

It was paradise. Cheryl was fucking me. Just like the old days when she was Craig and I was, well, me. Why did I ever give those days up?

That big cock shoving into me. Her soft fingers frigging my foreskin. Talking sweetly to me. Leaning over to kiss me. Fucking me hard and harder. Grunting as if she were nearing her own crisis. Scrunching her pretty face and shoving hard! Oh. Oh. I lost my hot load all over myself. Fuck me, Cheryl. Fuck me, Baby.

Cheryl milked me dry as she pounded my poor underused ass and squirted her gooies into my bowels. I was so happy.

We kissed and cleaned up.

I shyly said, "That was so good, Cheryl, but is Robbie going to hunt me down and kill me?"

She laughed. A beautiful sound. "Robbie knows I still have my dear sissy friends. Many of them are his friends too. And Robbie has no complaints. I give him all he can handle 365 days a year."

I bet she did.

I managed to put myself together and get to my "emergency" beauty appointment. Susan did absolute wonders in four hours and I was feeling much prettier and much happier about things in general.

I even let her pierce my ears. Which was silly, right? Cause this was only temporary.

Swaying my hips a bit more confidently, I went to the cafeteria for dinner, where I was welcomed warmly by several "girls," who had been evicted by their wives as I had.

They all had girl’s names and were surprised that I didn’t.

Lying in my nice, temporary bed in my nice, temporary guest room at Sanctuary, I thought about many things. What was holding me back from taking a girl’s name? I always liked my grandmother’s name, Daniella. Maybe that was what I would call myself. Temporarily.

And what was keeping me from a relationship with a man? Thinking about it, I realized that I was probably the only one of my sissy group who hadn’t been mounted and adored by a man. Or several men.

I thought back to when I was a junior in high school, spending a ball-draining sleepover with a senior named Doug.

Doug was a pretty one. He was wearing the sissiest blue nightie, with white ribbons. He had tiny, wispy blue panties and tan stockings with a white garter belt. He had a ribbon and a barrette in his hair. And he had just fucked my ass four times, making me cum a trembling bucket every time.

We were exhausted and dehydrated. And very happy.

We were both sure we were done for the night. Or maybe the year. We cuddled sweetly. Then Doug told me about his man.

"I was working out at the high school gym one afternoon three months ago," Doug began. "I always made sure I was the last one to leave because I don’t want anyone to see my panties. I had taken a nice, hot shower and was at my locker getting dressed. For some reason, I thought about Mr. Hansen, my trigonometry teacher and the assistant soccer coach. He’s very handsome and manly and I was just thinking about how it would be to be to make love with him.

"I got very excited and decided to give myself a little relief before putting my boy clothes back on, so I put on a pretty blue bra and matching skimpy panties, but I only brought the panties up to the bottom of my pretty little butt. I took a little cream from my locker and used the fingertips of my left hand to lightly tease my nipples to a hard stand. Then I lubed up two fingers of my right hand and inserted them slowly into my little hole. Mmmmm. It felt so good. I pushed my fingers in and out of my pooper and slowly tormented my nipples, all the while thinking of Mr. Hansen. I moaned his name softly as I thought about wearing girlie clothes and my prettiest lingerie to class one day and letting him see my panties and my bare thighs above my stockings. I knew he would like me and want me. I imagined him lusting after me and wanting to kiss me and rub my willie. I moaned, ‘Oh, Mr. Hansen.’ And my untouched cock was very hard and making little twitches. I closed my eyes and I could almost see Mr. Hansen. I called for him again. I opened my eyes and I DID SEE MR. HANSEN!!! He was standing there with a towel wrapped around him on his way to the shower. He had a huge bulge in his towel.

"I squealed in fear, then did a very sissy thing. I peed myself. All over the floor. I couldn’t help it. I was petrified about what would happen to me. What did happen was very nice.

"Mr. Hansen dropped his towel and I saw his whole, beautiful, manly body. Including a world-class, hairy cock that had a knob shaped like a helmet and the size of a plum. It was cascading goo and twitching. I looked in his eyes fearfully, but saw only lust. Mr. Hansen took three steps toward me and pulled me to him, out of the pee mess I had made. He took me in his sweaty, naked arms and kissed me hungrily. We rubbed cocks and I couldn’t help it, Paulo. I cried out and shot four big wads of my cream all over Mr. Hansen’s tummy. That set him completely on fire. He turned me around and sort of gently slammed me against Alan Curry’s locker. He crushed me against the locker with his body, then rudely entered me with his huge, nine-inch, hairy pole. All in one push. It’s a good thing I’ve had a lot of visits up there, because he was big. And aroused. He was frantic with desire, drawing out six inches, then shoving it back in. I felt my bowels ignite each time he did it and I squealed like a little girl. I was crushed against the locker, very uncomfortable, completely dominated and unable to do anything but grunt and squeal and pray we weren’t caught, but my cock was stiffer than it had ever been. On Mr. Hansen’s twentieth power stroke, my balls caught fire and I blew hot cum all over myself and Alan’s locker. I was crying it was so intense. I thought I was at the gates of paradise. On the twenty-fifth stroke, Mr. Hansen quivered, grunted and made four rapid strokes that produced a cumstorm that saturated my bowels and left me for dead.

"But he wasn’t through with me. He turned me around and kissed me again. We were both sweat, pee and cum-soaked. He picked me up as if I weighed nothing and carried me to the shower, where he washed every pore of my body as I washed him. By that time we were clean and rested enough for another go. That time he put my back to the shower wall, picked me up by my asscheeks and, defying gravity, bounced me up and down on his cock and kissed me until I came twice and he came, magnificently, copiously, once. My ass was sore for a week, but I had found my man. Oh, Paulo, look at you. I thought you were done for the night. You have a bigger stiffie than I’ve ever seen from you. And look, so do I."

Doug was right. I was furiously excited by his tale of being fucked and mastered by a man. He fucked me twice more that night, then told me about all the encounters he and Mr. Hansen had had since the locker room and got us both excited enough for two more rounds.

Maybe I was missing something by ignoring men. Like the comfort of a big male cock up my ass. And the affectionate attention due a lady.

 

Chapter Sixteen – Counsel

The next morning, I saw my counselor, a Dr. Ginger Fredman. Dr. Fredman was a fortyish lady in a smart business suit, with great legs tipped with five-inch heels, and a sweet smile.

I told her my story and cried uncontrollably for about ten minutes. I was worried that our hour was up, but she said that we didn’t watch the clock at Sanctuary.

"Do you want visitation with Jenny?" the psychologist asked.

I sobbed, "Very much."

"Will Melanie fight you?"

I sobbed harder, "I think so."

"Will you fight Melanie?"

I considered that. "Yes. Yes I will."

"Good!" she said, abandoning all her non-directive training. "You need to swim with ‘The Shark’"

Huh?

"Doris Goodson is ‘The Shark.’ She’s one of five attorneys here, but clearly the most vigorous advocate."

I left Dr. Fredman and went to see the Shark, who impressed me with her compassion and utter disdain for her opponents.

"Tell me what you want. I’ll get it," Ms. Doris Goodson, Esq. Said.

All I wanted was half the marital property and the right to be a father to Jenny. Even as I was dressing more like her mother. Confused? Let’s hope a judge wasn’t.

I met Cheryl for lunch that day and updated her on my goings-on. She seemed pleased that I had decided to fight for Jenny and my self-respect.

Then I sort of ruined her good mood by crying about the fact that I didn’t even have a job to pay a lawyer. I knew Sanctuary would help, but I told Cheryl that I didn’t want to be a leech.

"Paulo, you don’t know how valuable you can be to me. I want to offer you a job. And it’s not charity. You’d be doing me a big favor."

I was very surprised. "What could I do?"

"Did you notice that we have tgirls from all over the world here at Sanctuary? The fastest growing segment is ‘travestis’ from Brazil. They’re an interesting bunch. Strong-willed, yet needy of our services. I need someone I trust who speaks Portuguese to help me serve their needs without driving me crazy. Interested?

Finally, at age 26, a use for my Portuguese. I was interested. "I’ll do it," I told Cheryl.

Cheryl squealed happily. Then hugged me. She’s such a girl.

Then she sobered a bit and said, "The travestis of Brazil are one of the reasons Sanctuary was founded. Their culture on the subject of transgenderism varies greatly from ours. Impoverished young boys are given huge amounts of female hormones from an early age. Many develop into stunning beauties, with perfect female bodies and some of the biggest cocks on the planet. Here, let me show you."

Cheryl reached into her briefcase and extracted an album of nude Brazilian she-males in provocative poses. They all had huge, stiff cocks, voluptuous bodies and happy smiles. My goodness. My little friend was getting all agitated.

"They’re fantastic," I said.

"Of course, they’re not all 10s," Cheryl said. "And their society treats them like crap. They’re considered to be homosexuals by society and even think of themselves as homosexual. So they don’t think of themselves as women. Many, many Brazilian men lust after them, but reject them in public. Many travestis end up as porn models or porn video stars. Many more become prostitutes. Fortunately, a few come to Sanctuary to start lives as women."

"I hope I can help."

"I knew you would. Would you like to start a new life as a woman……Daniella?"

I gulped. It meant leaving some things behind and running to others. "I do, Cheryl."

Cheryl hugged me and said, over and over, "Daniella, Daniella."

 

Chapter Seventeen – Culture Shock

I spent the next few days in counseling with Dr. Fredman, in strategy sessions with the Shark, in the Sanctuary library researching travestis and opportunities for them in America, and in bed with Cheryl.

I had also begun hormone treatments and was scheduled for some medical and cosmetic procedures that would help me in my new life.

Melanie and her bottom-feeding lawyer, Jack Adams, filed papers against me and had managed to get a restraining order keeping me from my Jenny. The Shark told me that it was better that I didn’t confuse the three-year-old at that point anyway.

She was right, of course, but boy did I miss Jenny.

When I felt I was ready, Cheryl assigned me my first travestis. Nanda and Raquel were roommates at Sanctuary and had known each other in Brazil. They had come to the United States on student visas and were now here illegally. They were born as slum boys whose families allowed nasty men to pump them full of female hormones from age seven. The results, while the product of evil and economic despair, were spectacular. Nanda was a beautiful woman, with long, blonde (thank you Clairol) hair, large, firm, natural breasts and a full, lush, female body. She was no waif, either – five foot ten and a size twelve, at least. Raquel was a startling beauty. Feminine, but with just a whiff of mannishness in her features that made her all the more attractive to men. She was perhaps an inch shorter than Nanda, with long, brown hair, a slim, yet curvy body, and the biggest, most luscious, pincushion lips I had ever seen.

I scheduled an appointment to meet them in their rooms and when I showed up on time, I knocked and said who I was, in Portuguese. In kind, they told me to come in.

Whoa!

Nanda and Raquel were naked in bed, thrashing toward orgasm. Raquel, who appeared to have a rammer of massive girth, was entertaining Nanda’s welcoming asshole. Nanda was squealing ha  a big, hairy bag. Still, what girl doesn’t ache for the whopper now and then?

"OK," I said, in the tiniest voice.

Nanda smiled and went back to sucking lovingly and expertly. Raquel smiled and moved behind me with a tube of lube. I grimaced as Raquel entered me with three slick fingers. Ohhhhh. That was good already. Nanda’s sucking was exquisite. She locked eyes with me. Raquel was massaging my prostate. Ohhh ohhhh. I felt it. Nanda felt me feeling it and stepped up her assault on my clitty. Raquel spoke softly and lovingly to me in that strange version of Portuguese the Brazilians speak. There it was!!! Oh, cum. Oh, balls. Oh, fuck. Blooey!!!!

Nanda sucked and licked happily, swallowing my girlish cream. Raquel wiggled her fingers, then removed them. Maybe this wasn’t a good idea. I whimpered a little. Then I felt an entire leg enter my teeny butt. At least that was how I felt. I think it was Raquel’s cock, but it felt like a railroad tie. It hurt!!! Then it didn’t. She was all in and I was bent over, enjoying an almost unique experience. It was heavenly. Big cock! Stuffed. Feeling like a real woman. Mmmmm.

Nanda sat on the bed and I could reach her little peeny with my mouth, so I did. It was delicious. I could get used to these girls from Brazil. Nanda was excited from watching me get the fucking of my life. I could have fit three more cocks Nanda’s size in my mouth, but I was really enjoying her. My clitty had recovered from the shock my butt felt and was once again stiff and red.

Raquel told me I had a beautiful ass and a lovely face. She praised my legs, my clothes and my docility during sex. Then she told me that I would be getting a hot cum enema in less than a minute. That image, Nanda’s hot mouth, and the relentless rubbing of my prostate made me wince with sexual agony. My eyes filled with tears. My balls were on fire. They THREW cum from my clitty. Then BLEW another load. I cried out. Then I shot the biggest load of all!

That set Raquel off. She dug into the national cum reserves of Brazil or something and gave me the wettest, hottest, most copious injection I had ever had in my private spot. My knees buckled, but I kept my balance. Cum was oozing from my hole, down my thighs, over my stockings and onto my heels. Where did she get it all?

What a great job that was going to be.

 

Chapter Eighteen – Dating

Over the next few weeks, I felt that I was doing some good for the travestis of Sanctuary. Besides them fucking me, of course. Once again, I was the one getting pounded. I looked all over my body for a tattoo that said "Fuck Toy" or some other sign that alerted people, but couldn’t find it.

I was helping the Brazilian girls a lot. I ran interference for them with the INS, helped them with their English classes, and acted as a liaison to our culture. They expressed their gratitude the only way they knew how. With sex. Lots of it. Great sex. Still, something was missing.

One day, Nanda asked if I would like her to find me a date.

"I have lots of dates, Sweetie," I said. "Sometimes I have four or five dates a day."

Nanda smiled. "I mean with a man."

A man?

Nanda pressed on "I know you love us girls. We love other girls too. But we all like men and date them whenever we can."

I knew that the travestis left Sanctuary for overnights now and then. They weren’t inmates. I said, "But I never….."

"I know, Daniella. Maybe it’s time for you to feel a nice man’s body on top of you. Rubbing his hairy chest over your tender nipples."

My nipples were then quite perky and my breasts were a full A-cup. It did sound kind of nice.

"Then a man would kiss your nipples, giving each one a little lick and suck. He would make little kisses all the way down to your belly button, then give it a teasing little tonguing. Would that make your clitty hard, Daniella? Oh, I can see it already has. Raquel and I know a very nice man named Brian who would be a nice first date for you tonight. What do you say? "

"Tonight? Oh. What would I wear? Tonight? What time? Where would we go? Brian’s his name? What’s he like?"

It was settled. Nanda helped me get ready and even calmed me down the way she knows best. Even three-inch Nanda got to fuck my ass. I think I was the omega-sissy of the world.

I wore a pretty black dress that showed off my legs, expensive perfume, very high heels, large gold hoops and a very worried expression as Nanda introduced me to Brian. He was maybe five years older than I and dressed very nicely in a Brooks Brothers blue suit. He was sort of handsome, but his manner added points. He was very deferential to me and knew how to treat a lady. Which was what I was. At least that night.

He took me to dinner at a lovely place. We had sparkling conversation. Then he brought me home to Sanctuary and gave me a closed-mouth kiss on the lips. Oh, my. My first kiss from a man and it was wildly erotic. I waved goodbye to Brian and he promised to call me. Would he? Should I run after his car in my heels and beg him to come upstairs and fuck me? Yes! No. Too late. He already left. Well, that was interesting. Would he call? Would I want to live if he didn’t? Oh. This girl-guy stuff was brutal

I lay in bed that night in my prettiest nightie, tickling my doodle and thinking of Brian on top of me. Grunting and kissing me. Filling my gorgeous butt with cum. But would he even call?

He called. Two days later. I knew a woman’s torment waiting for that call and I didn’t even know how much I liked Brian. He asked me to the symphony two days later. I said yes. Should I have been coy? Was I a coy boy toy?

Thank goodness I had another nice dress. Nanda and Raquel were my friends, but their stuff was too slutty to borrow for the symphony. Or anything. I wanted to give them some fashion tips, but they apparently were very happy dressing that way. A legion of men agreed.

Brian was on time again and looked very edible. I mean it wasn’t as if I didn’t know what a cock was. Or what to do with it. I had swallowed an ocean of cum and had a river pumped up my butt. But Brian was a man. Not a sissy or a she-male. This was different.

We had another lovely dinner and the music was divine. Brian held my hand during the third movement and there was movement in my panties. When we got back to Sanctuary, I invited him in. He hesitated, then accepted.

Well, well. There I was. Almost 27. A cocksucker since I was 13. Hetero. And I was alone in my room for the first time with a man. A big man. Friendly. With broad shoulders. And a vocabulary. Well, well.

Brian got the coffee going and I gave him a little thank you kiss. Somehow, my tongue ended up in his mouth. It just seemed to. Then he had me in his arms and was kissing me into a foamy lather. Mmmmmm.

The next thing I knew, my wispy little panties were down to my ankles and Brian’s strong right hand was gently massaging my pretty butt. He was still doing that kissing thing and I was in a high state of arousal. DEFCON four at least. Full alert. My clitty was big and throbbing as Brian extracted his equally sized weapon. He lifted my skirts and rubbed the heads of our love sticks together. I was drooling goo and so was Brian. Had I ever been so excited?

I mumbled something and Brian helped me out of my dress and slip. I lay on my back as I watched that mannish man strip down to his manliness. He mounted me, kissing me as he removed my bra. Rubbing cocks together. Kissing. I felt his hairy chest against my nipples, just as Nanda had said. Yum. That was fantastic. So sexy. Our sensitive cock tips mixed our goo, producing a mingled, sticky rivulet. Then Brian slipped down my body to adore my nipples. Ohhh. He did that better than anyone. Ever. There was some string connecting my cock and my nipples or something, because I felt every nipple lick squarely in my groin. And it felt great. Great.

Why did I deny myself this for so long?

Society said it was wrong. The same society that wanted to deny me everything else I liked. If I took away all that, what was left? Not enough.

I wrapped my black-stockinged legs around Brian’s back and rubbed them up and down his skin. He liked it even more when I stuck a painted big toe between his asscheeks and nipped his anus with a red toenail. I was nasty. Brian saw that and was very impressed.

"I think you need a good, vigorous fucking, sweet lady," my new friend said.

"Oh, yes, please," I answered. "With no mercy!"

I had been fucked before. Hundreds of times. Maybe thousands; who’s counting? But this was different. This was a man. And he was intent on making me ask for the number of the truck that hit me.

He began by licking my pussy hole with vigor and affection. Most of my sissy lovers thought that was icky bad. Not young Brian. He acted as if it were a summer Sunday at the park and Mom just bought him an ice cream cone. He began by laying about fifty kisses on the inner cheeks of my butt. The last ten were right on the sweet spot. Then he made micro licks of my anus ring. Each one made me twitch and my clitty jump. When he dug his tongue in, I was already on another planet. That blasted me out of the solar system. I moaned and squirmed, but as requested, he gave no mercy. Pushing with his tongue. Licking hard. Then softly. Then digging like an archeologist. He didn’t even slow down when I whimperingly told him that I was cumming. The rogue licked me harder as I flooded my frillies with my sweet, girlish cream. He did stop for a second to smile at me as my heart rate dropped below 300. Then he did something so nasty, maybe I shouldn’t even tell you. OK. You twisted my arm. He used his tongue to transport the goo from my tummy and apply it to my asshole. I almost cum every time I think about how dirty that was. My little girl got all big again when he did that.

My asshole was now slick as an ice rink and ready for Brian’s extended visit. I was on my back. Helpless. Rampantly erect and ready to offer my tooth fillings to this man if he wanted them. I couldn’t have stopped him from taking them. Helpless. Little girl. Big man. Big cock. Looking me right in the eye. Peehole dripping goo furiously. Brian grabbed my hips, lifted them with both hands, and stuck his lollapalooza right in the only cunt I’ll ever have. The whole eight inches. With one push. Owwie. Tiny pain. Big pleasure. BIG pleasure. Balls slapping against my pink bag. Heavy balls. Ohhhhh. Fucking MEEEEE. It was so wonderful. Pushing in. My eyes couldn’t focus. My nipples were like little rocks. I screamed with pleasure. Brian fucked me harder. I let another load of my precious juice go. Hot. Wet. Sticky. The second load wasn’t coming. It couldn’t get out because of the way my asshole was stuffed. Or so it seemed. It was painful. Then it started to jump out and the pleasure was multiplied by ten. Then a hundred. And still Brian pumped. My third glob was boiling in my balls, my stomach clutched. I squealed Brian’s name. My eyes widened. I dug my nails into his back and SHOT another big portion of my girlish treasure onto Brian’s pumping tummy. I was frantic waiting for that fourth glob that was there but hiding a little, maybe. It was on deck and moving to the plate and ripped my gut as it burst into cummy splendor.

One orgasm. A four-act performance. Twenty fantastic seconds of my life. Oh my.

My partner in love was very pleased with himself, but now intent on his own pleasure. It was imminent. I reached for his balls and stirred them gently, then offered him these loving words, "Fuck me, you fucker. Fuck me and fill my pussy with your cum. Give me all that hot, sticky cum now, Fucker. Fuck me."

Limited in vocabulary, but strong in imagery.

The gentleman complied. His face was a mask of sweet agony. He came so much and so hard that I thought he wouldn’t be able to fuck me again that night. I was wrong three times.

 

Chapter Nineteen – Courting

Well my life changed after that night all right. I saw Brain quite often, but I became quite the little Miss Popularity, "dating" lots of young fellows and enjoying much pleasing companionship. And some great fucking.

I certainly didn’t abandon my old friends like Nanda, who was now working as a receptionist for an advertising agency. In an amazing turn of fortune, the agency gained fifteen new clients the first month Nanda worked there. And the clients who wanted the agency to schlep over to the clients’ offices now wanted to have all their meetings at the agency. They all get there early too and had lots to say to the receptionist. It was fortunate that the agency got rid of that silly old rule about its receptionist having to speak good English. And the prohibition against dating clients. Nanda saw a client mostly every night. And often came to work directly from a client meeting. Nanda had five substantial raises in her first two months and was taking private English lessons in the CEO’s office. Twice a day. For an hour each. But her English didn’t seem to get any better. And no one seemed to care.

Of course I was happy in one way, but sad that I hadn’t been able to see Jenny for over four months. My now-shrewish Melanie and her accomplice, Jack Adams, Esq. kept me in deposition after deposition. I attended them all with The Shark, dressed entirely en femme and insisted on being called Daniella, which was then my legal name.

Adams used what he had to try and win. He went after me as being immoral. OK, I was fucking four, maybe five guys a week and an equal number of shemales. Several times each. But he didn’t know that. And that wasn’t his point. He was trying to portray transgenderism as evil. Much as you would say a left-handed person was a Satanist. What a bunch of crap. But it could have swayed a stupid judge. Thank goodness we had a smart one.

Anyway, we finally got our day in court and The Shark smoked Melanie and her shyster. I got equal custody, effective immediately and an equal share of community property. Melanie was so angry that she slapped Adams right in court. That wasn’t fair. He tried to defend her interests using every tool, fair and unfair, that he had. I had a better lawyer, but not by much.

Shark and I hugged and I was mentally planning my first outing with Jenny. Jack Adams stood there looking at me, Melanie’s hand imprint on his left cheek.

He approached me rather shyly. "Ms. Malone, I do a lot of things to help my clients. Some make me feel dirty. That’s what happened this time. I’m sorry, Ma’am. You’re a fine lady and I wish you a great life and much happiness with your daughter."

Wow. Respect. That’s what Sanctuary gives you and allows you to accept.

I smiled and said, "Thank you Mr. Adams. Perhaps you would like to have a cup of coffee some time."

His eyes lit up. "I’d like that very much, Ma’am." He nodded at me and left the courtroom.

We TGs must never forget to give respect too.

Sanctuary helped me see what’s right. Doing it will be up to me.

But the only real sanctuary is within the permission we give ourselves to be who we are. With pride. And the same dignity as anyone else.

 

 

 

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© 2002 by Gingerfred Man. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.