Tradition

by: Gingerfred Man

 

Chapter One – Changes

Dad didn’t seem too distressed when Mom ran off with the pizza-delivery guy. She and Dad didn’t ever really get along, except maybe when I was very young. I remember some nice Christmases, but maybe they were just illusions too.

Neither of us held out any hope (or desire) that Mom would come back. She was mostly nasty to both of us, wanting something that we didn’t know how to give her. Now that she has all the pepperoni she can eat, I hope she’s happy.

Anyway, I was thirteen and Mom had been gone for a year when I noticed some changes in Dad.

He seemed nicer somehow. Mellow wasn’t the word. Maybe it was softer.

I had hoped that Dad would start dating again. But he didn’t seem to be meeting any women. At least once a week, one of Dad’s guy friends would come over the house. Dad would cook dinner for us and we would have a nice time. The guys were all very nice to me. Dad had good taste in friends. Usually, when I went to bed, Dad and his friend would be watching a video or talking or something. When I got up the next day, Dad was always in a really good mood. I mean, he was never down really. But he was really up after a visit from one of his three or four friends.

My name is Eric Woods. My Dad’s name is Bradley or Brad. He was a computer consultant working out of our home. I was in the eighth grade at Gouda Junior High in Fromage, Wisconsin. My best friend was Rick Jackson, also 13, also in the eighth grade.

I told Rick about my Dad, but he didn’t see any cause for concern. "He probably doesn’t want to get hurt again, Eric," Rick said. "Anyway, you know he’s not gay, if that’s what worries you. He was married."

Rick was probably right. It’s just that I saw things. Dad’s friends didn’t treat him like most guys treated other guys.

Like the flowers. The guys would always bring me something when they came for dinner. Like a book I wanted or a video or a game. They must have asked Dad, because they were always gifts I liked. But they often brought Dad flowers.

Maybe I was wrong, but it seemed funny that they brought flowers to a man. He would always make a fuss over the flowers, putting them into a vase and saying how pretty they were. That surprised me too.

When I asked Dad about it, he said, "Come on, Eric. It’s 2001. When you go to someone’s home for dinner, you can bring flowers if you want. The flowers are for the home, not the guys in them. Plus, you like flowers, don’t you?"

I hadn’t thought about it. I guess I did. But then there was the touching.

The dinner guests would sometimes touch Dad on the elbow or the hand when they were talking to him. And he didn’t pull away. Most of the time he would smile. I didn’t like that. What was going on?

I asked Dad how he knew these guys and he said they were clients of his. He worked for a lot of big shots, fixing their computer problems. He was very personable and made friends easily, so he didn’t have to have jerky friends like most of us do. He had his pick.

One night, he told me that Craig Bruder would be coming for dinner. This was big news to me, because Mr. Bruder was the principal at my school! I was very nervous about seeing Mr. Bruder in a social situation and hoped that Dad didn’t do anything to tick him off. I didn’t see him much, since I wasn’t one to be sent to the principal, but I didn’t want to be on Mr. Bruder’s bad side, even though I would be graduating from his school in a few weeks.

Mr. Bruder showed up at six-thirty, right on time. And carrying a big bunch of flowers. He leaned over to Dad to give them to him and I almost peed my pants. I thought he was going to kiss Dad, but he stopped short. He fussed over me and gave me a cool video game I really wanted. My pants were safe again.

We had a nice dinner. Dad was a great cook and Mr. Bruder was funny and knew a lot about what kids my age liked. He looked at Dad a strange way, though, like all the dinner guests did. I thought that I was just imagining things and went off to my room to play my new video game. At ten, Dad said time for bed. He kissed me and tucked me in. Maybe I was too old for that, but I still liked it. I drifted off to sleep.

At about midnight, I awoke with a start. I was having a bad dream, something that had happened too often since Mom ran off. Maybe I was a baby, but with no mom, I went to my Dad’s room for comfort. That wasn’t what I got.

As I approached the room, I heard little grunts, moans, gasps and whimpers, along with some tiny squeals that seemed to be based in delight. I had no idea what they meant. Maybe Dad was watching a video. But from outside the door, it appeared that only the moon lit the room.

Puzzled and curious, I slowly, soundlessly opened the door. What to my wondering eyes did appear wasn’t a miniature sleigh and eight tiny reindeer. It was two people who appeared to be wrestling, but seemed to be enjoying the sport very much. The person on top was naked and his bare ass was thrusting back and forth. It looked like Mr. Bruder, but his face was contorted with effort and concentration. Looking more closely, I saw that it was indeed him. Oh, my! What had I stumbled into?

The person on the bottom couldn’t be…..It had to be Dad. Horrors!!!! But it didn’t look like Dad. Maybe it wasn’t. That person was a woman, with soft, blonde curls. Dad was brown-haired. That pretty person’s legs were shaven and were encased in silky black stockings, with sexy painted and pointed toes. Last summer, the last time I had seen them. I remembered Dad’s legs were hairy. The pretty person was also wearing a pretty pink shortie nightgown pulled up to her waist. Dad never wore stuff like that. He was all man. The pretty person’s make-up was expertly done. She had full, red lips and deep, beautiful eyes. She looked like my Dad’s pretty sister. But he was an only child. Did I have an aunt I didn’t know about?

Mr. Bruder was shoving what appeared to be his big cock (I had never seen a man’s cock before) in and out of the pretty person’s pussy. I knew what that was, though I had never seen one. Of course, shocked as I was, I had to keep looking to see what a pussy looked like. What I saw was that Mr. Bruder’s cock was going in and out of the pretty person’s asshole. How was that possible? And that the pretty person had a big cock herself. It was flopping every time Mr. Bruder punctured her pooper.

Disgusted and fascinated, I didn’t make a noise as the truth became clear. My Dad was dressed as a lady and Mr. Bruder was fucking his ass. And they were both enjoying it! A lot!

I was so angry. How could Mr. Bruder humiliate and shame my Dad like that? And me? Why did Dad let him do that? Was Dad a wimp, unable to defend himself while Mr. Bruder forced himself on him?

Oh no. Then a worse thought crossed my mind. What if Mr. Bruder and Dad planned this all along? And Dad did this with all those men who came by? Oh. Oh. I was shaking with disgust. And fear. And something else.

I was getting very excited watching Dad and Mr. Bruder fuck. My little weenie was stiff and sore. They were enjoying it so much that I began to feel a little happy for Dad. He was squealing and giggling like a little girl on the playground. Could a big cock up your ass feel good? Dad needed some happiness in his life. God knows he never had it with Mom.

Mr. Bruder leaned over and kissed Dad on the mouth and whispered, "I’m cumming soon, Honey."

Ewwww. Icky bad. Men kissing. Calling each other "Honey." Better that they should be trying to kill each other in a war. But Dad seemed so much like a woman at that moment. I guessed it was all right. I knew what cumming meant, but I had never done it myself.

Dad kissed Mr. Bruder back and said in a little-girl voice, "OK." I didn’t know Dad could talk like that.

Mr. Bruder began to stroke Dad’s big stiffie more rapidly as he plunged his cock in and out of Dad’s butt. Dad’s eyes gleamed. He looked so happy. Then, suddenly, he winced and squealed. Hot, thick, white juice leaped from his cock, all over his soft, shaved tummy. He smiled and actually purred. Mr. Bruder grunted and moaned loudly, lurching, bucking and shivering as he deposited his own load in Dad’s tender butt. They were both in ecstasy. I slowly slipped out, before they would see me.

What had just happened?

 

Chapter Two – Relief

I lay on my bed, quaking with arousal and confusion.

My Dad was a sissy faggot who got dressed up like a girl and offered his butt to every sailor in port. I didn’t believe all that, but it was a measure of my despair that I could even think it.

Maybe it was just a phase. Something Dad had to do now that he was abandoned and cuckolded.

Maybe Mr. Bruder and those men were blackmailing Dad and he was fucking them to protect me. Though he did seem to be enjoying it a lot. And why did they pick him of all people and dress him up and everything?

How would I ever find out? I could never ask him. And my poor weenie was so stiff and sore. My balls were aching. What could I do about that? At that time, I really didn’t know.

I lay there in several kinds of distress when the door opened softly. Dad came in wearing a nightie, a white dressing gown and his blonde wig. He looked like an angel, though a well fucked one. Globs of Mr. Bruder’s cum were running down his thighs.

"I saw you, Eric. I’m sorry you had to find out about me this way."

I could see that Dad was crying. His mascara was running. Mr. Bruder was probably lying on his back snoring, his limp log drooling cum.

I started crying too. Dad hugged me tight. I could smell his perfume. It was like having a Mom again, only a nice one. I didn’t want to do it, but my stiffie rubbed against him.

"You poor guy," he said. "You need some relief and some answers. Let’s start with relief."

Dad pulled down my pajama bottoms and looked at my stiff willie. It was five inches long and almost purple with excitement. It jerked uncontrollably as I sobbed.

Dad licked the fingers of his right hand and began to skin my little boy up and down, trying to calm me down. Saying, "There, there," like a mother would. Darn he was pretty. No wonder all those homo freaks wanted him.

What he was doing felt so good that my hard sobbing slowed to a gasp, then a little pout and finally, I felt something very good was about to happen to me for the very first time.

"Dad, I…." I said to him.

"It’s OK, Honey. Let yourself feel good. It’s very nice isn’t it?"

I nodded meekly. I felt a tornado brewing in my balls.

"All the pretty girls will want to do this for you pretty soon, Eric. Won’t that be nice?"

It sounded very nice. I whimpered at the thought of my first boy-girl party last month and how good those perfumed, pretty girls in delicious party dresses and stockings had looked to me. We played kissing games, but I never thought they would want to do what Dad was doing to me. Oh, what an image that was! A sweet girl’s soft hand on my cock. Her other hand milking my balls, like Dad’s hand was then. Ohhhhhhhhhh. The cum leaped from me in thick jets. My virgin juice shot onto Dad’s pink nightie. That would be a story to tell my analyst some day. At the time, I didn’t care. I had never felt better in my life. I kept cumming in seven squirts. Dad kept milking me, telling me what a good boy I was. I was gasping for breath and sweating cold sweats, but happy.

Then I looked at my sissified father. OK, I thought. Now what’s the story?

Dad got the non-verbal question and said, "It all started when I was about your age."

This sounded like a really long story, so I settled in for it.

 

Chapter Three – Dad’s Story

[Here’s what Dad told me that night, in his own words.]

You’re a good boy, Eric. Very mature for 13. I’m going to tell you some things about my life that I’ve never told anyone. But you’re my son. And I love you. So here goes.

You know your grandmother is strange, right? [I knew.] Well, when she was young, she was even stranger. When I was your age, she’d been married twice and had had numerous boyfriends. One of those guys was my father, although that’s never really been made clear to me.

She held a very low opinion of men at that time in her life, having had sexual relationships with a lot of bad ones and no good ones. Speaking objectively, she never went anywhere that she could meet a nice guy. There are plenty of them out there. Believe me, I know. You’ve seen a parade of them at the house since your mother left.

My Mom trawled from a bad pool and kept catching nasty, ugly, mean fish. Guys with mullets and tattoos and superior attitudes toward women. She kept thinking she could change them. But they changed her.

In the late 70s, when I was 13, the feminist movement was strong in the country and my Mom started jumping on the bandwagon of some groups that were way out on the fringe. She’d been "wronged’ even though she set the game up so she couldn’t win. She went to a lot of strange meetings and read some pretty crazy stuff. The one that changed my life was a book by Janice Dobbs called, "Feminization for All." Its premise was that mothers with sons should feminize them so that they would grow up happy and peaceable. I saw her reading it, but didn’t think she would do anything that radical to me. Mom also didn’t have much patience for anything beyond a 30-minute TV show.

She probably would have never done anything if she hadn’t met Ginny Landrow at one of those crazy meetings. Ginny told Mom that she had actually applied the techniques of "Feminization for All" on her son Adam, who was now a sissy boy called Heather.

That was what set Mom off and changed my future.

One Saturday, Mom said we were going to see Mrs. Landrow, a good friend of hers. When I complained mildly, Mom said that she had a son just a year older than I was and that we could "play."

I thought, the kid may turn out to be a creep, but at least he’s a kid.

When we showed up, Mrs. Landrow greeted us warmly. She was a very pretty woman – thin, with nice legs and big breasts. She smelled good too, so I liked it a lot when she hugged me and gave me a big kiss on the cheek. I know you’ll find this hard to believe, Eric, but your grandmother was a very attractive woman at that time too.

I was wondering where the promised 14-year-old boy was when a vision of teenage beauty came down the staircase. Her face was drop-dead gorgeous and perfectly made up. Oddly, her hair, though blonde, was cut in a severe, boyish style and she had a large pink ribbon atop her head. That look seemed to make her even sexier. She was wearing a dress like the kind girls wore to parties in those days. It was pink, with lace and white bows and she was wearing white stockings and pink pumps with three-inch heels. She was the prettiest girl I had ever seen by a wide margin. My mouth hung open. My prick stood tall and proud. The ladies noticed both and smirked.

Mrs. Landrow said, Bradley, this is my son, Adam, or Heather as he likes to be called when he’s in his pretty things.

Huh?

"Say hello to Mrs. Woods and Bradley, Heather," Mrs. Landrow said.

"Yes, Mommy," the unusual angel said in a cherubic voice. Then she (I could never think of Heather as a "he") actually curtsied to my mother and said, "Hello. Mrs. Woods. Welcome to our home. Then she turned to confused me, flashed a 1,000-watt smile and said, "Hello, Bradley.’

"He’s very courteous," Mrs. Landrow said. "So much more so than before I feminized him. I see you’re confused and unconvinced, Bradley. Heather, lift your dress and petticoats and show Bradley your little goodies."

Unquestioningly, Heather lifted her dress and showed a stiff, red thin cock and pretty pink bag of tiny balls. She was wearing no panties. The little teaser even struck a pose, turning slightly to her left and lifting her right knee prettily. I was wearing a dazed expression. My cock was outrageously stiff. I didn’t know what I wanted to do, or with whom, but I was excruciatingly horny.

Narrating the little scene, Mrs. Landrow said, "He’s always stiff like that when he’s in his feminine frillies. I let him omit panties because he’s always spurting his boy cream from feminine excitement and ruining panties. Look, that sticky stuff is positively flooding from his excited little weenie. And his little tee tees (such a nicer word than testicles) are aching for release. I think he likes Bradley."

I certainly hoped so. My eyes were locked on her lovely weenie and tee tees. And those creamy thighs with the long white garter straps. Attached to silky white stockings that encased legs to die for. Made even prettier by her smart heels. I found myself wondering what her ass looked like.

Mrs. Landrow had more surprises. She said to my mother, "A sissy must be frequently and properly milked, dear. This gives him a clear complexion and binds him to his mistress even more closely. Observe."

Mrs. Landrow moved to Heather and said, "You poor baby, you’re so excited. Let me help you." Heather was still holding up her skirt and looking at her mother as if Mrs. Landrow were a saint coming to her rescue. Mrs. Landrow took Heather’s foreskin in her fingers and thumb and gently masturbated her to a bone-chilling climax. The poor sissy squealed and whimpered, screaming at the release of five hot ropes of cum into the air.

"Oh, my sissykins, he was so excited," the woman, who I then believed to be crazy, said to her sissified son.

Poor Heather seemed to be blissfully happy and grateful. At mother’s orders, she cleaned the mess she had made.

Then Mrs. Landrow said, "Show our guests your privates again, Heather."

Heather lifted her skirts and frothy petticoats. Miraculously, she was once again in full erection and her pricklet was twitching as if it were ready to erupt.

"Femininity is so exciting to my son," Mrs. Landrow said. "Would you like to show Bradley your room, Heather, while his mother and I talk?"

Heather repeated the only phrase I thought she knew. "Yes, Mommy.’

Heather held my hand and led me to her room. Her hand was soft and warm. What exactly was I dealing with here? We opened the door, walked in and closed it. I felt as if I were in a movie set about girlishness. Everything was frilly and sissy with ruffles and lace and stuffed animals. I blotted it out of my mind and focused on Heather. I wanted something from her but I wasn’t sure what. My erect, throbbing cock knew, but he wasn’t sharing. He would be soon if Heather kept holding my hand like that and talking in a little-girl voice.

"Do you like my room, Bradley?"

"It’s, uh, very nice, Heather."

"Do you like me, Bradley?"

"Very much, Heather. You’re the prettiest girl I’ve ever seen, but, uh. Where did that cock come from?"

"Oh, it’s not a cock, Bradley. Only horrible boys have cocks. I have a clitty. And it’s very excited being here with you, Bradley. Would you like to kiss me?"

Gulp. Would I? I was a virgin, but hoping to shuck that title soon. "Yes, very much," I gasped."

"Well, you can’t."

My heart sank.

"Not while you’re looking like a ghastly boy."

The addition of two and two eluded me for a moment. Then four formed in my tiny brain. "What can I do, Heather?"

"Take those awful boy clothes off and I’ll put something nice on you. Then we can kiss and even go .." and she whispered "all the way."

I wasn’t sure what that meant, but it sounded really good.

I kept thinking of Heather’s creamy thighs, stiff clitty and pink "tee tees" as she helped me undress. My little boy was outrageous by the time he saw the light of day. He was red, sore and twitching and Heather recoiled when she saw him.

"A boy’s cock! How hideous!" she said. "We must get you under control immediately."

I didn’t like the sound of that, but all she meant was that she wanted me into something girlie and feminine. I kept looking for the pod that poor Heather had crawled out of. I guess it was unfair that I wanted to fuck the poor zombie, but she was so damned sexy and my cock was so damned stiff.

I lay naked on her incredibly girlie, perfumed bed. Heather covered my naked goodie package with a pile of frilly panties while she looked for something suitable for me to wear. The panties felt wonderful on my distressed cock. All cool and silky. And the soft, clean bed felt even better. I could learn to like this, I thought.

She found what she wanted and brought it to me – a lacy, frilly, white babydoll nightie. No way was I putting that on! She reached through the panties and stroked my cock. I put the nightie on.

I saw myself in her mirror. I looked like a perfect little sissy. My cock got even harder. I wanted to fuck myself!

"Would you like to kiss me?" my new best friend asked.

"Oh yes!"

"Well you can’t."

More of these games. Heather had already learned to be a woman.

"I could never kiss those rough, boy lips. Not unless you put some lipstick on."

How bad could that be? "OK," I agreed.

Heather applied it and I looked at the mirror again. Thank goodness nothing was brushing up against my cock, because a ladybug landing on it would have made me explode. I was HOT!

"Now lie back on the bed and I’ll make you very happy," Heather said.

I moved about 20 stuffed animals out of the way and lay down on my back, my head on the pillows. Heather stripped to her magnificent white lingerie – bra, garter belt and stockings. Oh my goodness! She had cleavage and small titties. How did she get those?

Heather’s clitty was almost purple with blood from her excitement. I wanted to eat it three meals a day. And lick those tee tees. I still hadn’t seen her ass, but I was feeling lucky.

Heather sissied over to me in her heels, her little pink bag of nuts swaying as her hips swiveled. She joined me on the bed and we lay facing, on our sides. We kissed. Oh, Baby, we kissed. My ears were so hot they were on fire. I was quivering, but I had enough sense to cup her ass with my hands. She squealed in appreciation. I tickled her tee tees and she moaned. Beginner’s luck, I guess.

Heather could have taught a PhD course in kissing. Our lipsticks mingling made everything even sexier. And her stiff clitty rubbing, rubbing against my big boy sent me into my very first orgasmic spin. It was a big one. I came hard all over Heather’s privates and my hot boycream must have been what she needed for her own explosion. I held and kissed her as we both shook and writhed in ecstasy. It was earth-shattering.

Nothing in this world is sexier than a sissy who’s hot for your body. Nothing.

Heather asked me to lie on my back. Everything she asked had worked out so far, so I did. She kneeled next to me on the girliest bed on earth and licked all the cum, mine and hers, off my cock, balls and stomach.

Oh, Eric, I think this story is really exciting you. Would you like more relief?

[Yes, please, Dad. Gasp. Pant.]

Of course, Honey. Here, I’ll just put this nice cream on your privates here. Mmmmm. Now isn’t that cool and comforting? Let me rub it around your cock and balls. That’s a very nice package you have there, Eric. The girls will be on their knees lined up around the block to suck your nice big cock. You’ll like that Eric. Pretty girls with their mouths full. Licking, sucking. Your head back, enjoying it. Every once in a while telling them how pretty they are and what wonderful lovers they are. You’re a lucky boy, Eric. You have thousands of fantastic orgasms ahead of you. Here comes one now! That’s a good boy! Get all that boy cream out of you. Oooo. Another spurt. You must have really needed it. Did you?

[Uuuuuuuhhhh!]

It’s so nice and thick. Maybe I should use it to rub your "tee tees" for a while as I tell you more about my life. How would that be, Eric?

[Pant. Grunt. Great, Dad.]

Your little nuts are already bigger than poor Heather’s were, and she was a year older than you are. And those breasts of hers. Her mother was giving her something, I know she was.

I got to inspect those breasts as she was licking my cock. I reached for her bra and she stopped licking the cum off me for a moment to remove it. I’ll tell you. Almost every set of titties I’ve seen since that day were bigger than Heather’s were, but I never saw any sexier. They were like little plums. Mostly dark brown nipple. She stopped "cleaning" me for a while and let me lick and suck them. She got very excited and began to quiver and squeal. It seemed I had found a key to Heather’s heart. Instinct brought my hands back to cup her ass as I sucked her tits, mostly to steady her, as she was shaking so badly. Inadvertently, my finger brushed her little puckered asshole. That was another G-spot for her. Tittie sucking and rosebud touching did Heather in. Her beautiful eyes locked with mine and widened, she gasped, then squealed and, without even getting hard, she blew a huge load of her precious goo on my leg. I had now seen Heather cum three times in less than an hour and she didn’t seem flagged at all. In fact, once her pulse rate came back down below 200, she started to get another erection. This was a sissy who loved being a sissy. And loved sex. How lucky was I?

Heather asked me to sit on the side of the bed, since she wanted to give me a proper sissy blowjob. She said she would suck my clitty and get out all my girlie juice. Hey. A good blowjob trumps a fight over semantics. I mean I was in a babydoll nightie wearing red lipstick.

Heather got on her knees on the floor and gently lifted my ball sack. She kissed each of my nuts, then swirled her very talented tongue all over each one, including the underside, which is often neglected. Don’t worry, Eric. I’ll rub you there. How does that feel? I thought so.

Anyway, Heather had me in a high dither, with my cock at full parade attention. I was stroking her short hair and playing with the pink ribbon, when the door flung open and Mrs. Landrow and Mom came in. Were we busted? Could they just wait until I orgasmed before Mom grounded me for life?

Mrs. Landrow gave her lupine smile. Mom just stared. Mrs. Landrow said, "Very good, Heather. I see you’re making friends with Bradley very nicely." Then she turned to Mom and said, "He’s such an excellent cocksucker. I trained him myself. All good sissyboys are expert cocksuckers. And men seem to sense it."

I was sure that the white truck to the asylum would be by for Mrs. Landrow soon, but since she didn’t mind Heather sucking the life out of me, I was liberal on the subject as well. It was strange getting head in front of my Mom, but it had been an odd day. If Mom didn’t drag me out off there after seeing me in a baby doll nightie, wearing lipstick and getting my cock sucked by a boy dressed as a girl, who was I to argue?

"Heather, you’re doing very nicely, Dear. But perhaps Bradley would enjoy that little extra that you ask Mommy to do for you. Remember?"

"Yes, Mommy." There it was again. I hoped that white truck would come soon.

Heather asked me to stand in front of her as she continued kneeling. Heather licked two of her fingers, then proceeded to lick and suck my cock to perfection. My first blowjob was administered by a world-class lover. To prove it, Heather added the "little extra." She entered my anus with her middle finger. Ohhhhhh. That was good. Combined with the sucking assault on the thousands of nerve endings usually covered by my foreskin, I almost fainted. Then she added the second finger and moved them in and out exactly 1.72 times. At that nanosecond, my balls evacuated at hurricane force. I was so overcome, that I actually fell back on the bed.

I didn’t know what craziness tomorrow would bring, and craziness appeared to be a safe bet, but at that moment, I had an estate in heaven.

Mrs. Landrow applauded and hugged and kissed Heather. "I’m so proud of you, Honey," she said. "And you even got Bradley dressed properly for love. What a good sissy you are."

Heather beamed and said, "Thank you, Mommy," a slight variation on "Yes, Mommy," but promising.

Mrs. Landrow continued. "Bradley, how did you like your first experience with sissy love?"

"It was fantastic, Mrs. Landrow."

"So much better than that awful boy-girl shamelessness, don’t you think?"

I gave the answer with the most promising possibilities for more ball draining. "Yes, Ma’am."

"And do you like the frilly things and the lipstick, Bradley?"

Honestly, I said, "Yes, ma’am." I was not very different from Heather in my responses, was I? The nightie and the lipstick made dirty sex even dirtier. I liked it. And still do, as you can see, Eric. How does that ball massage feel?"

[Uuuuhhh. Gooooood, Dad.]

You’re getting all stiff again. I’ll take care of that in a little bit. Anyway, Mrs. Landrow said she and my Mom had some things to discuss for about two hours and they were going back downstairs. They would call us when it was time for me to go home. Yeowie! More Heather time, I thought.

I was right. Heather was glowing with praise from her mother and ready for anything. I desperately wanted to suck her cock. I didn’t know where the urge came from, but from the moment I saw it, skinned and proud against her garter belt, I wanted it in my mouth and her cum in my stomach.

Heather was game. More than game. She stood up and had me get into proper cock-sucking position – on my knees. I kissed her clitty head. She moaned softly and looked at me with something akin to love, in a zombie sort of way. I took the head in my mouth, officially becoming a cocksucker. It was utterly delicious. A little salty, but the sexiest smell and taste, along with an aroused pussy, on this earth. I sucked. She stopped me. "It’s more about licking," she said. Sage advice that has made many sissies, boys and men happy over the years.

I considered giving her the little extra and did, parting her lovely, soft ass cheeks with my hand and inserting first one, then two loving fingers. She moaned and squeaked. Then, without further warning, she came all over my face. I had to move quickly to get any to swallow. It was the tastiest meal I had had at that point in my life. Heather drew me to my feet and kissed me, licking all her cum off her face, purring and saying, "I think we still have time to go all the way. Do you want to?"

Sinatra said it’s no good unless he loves you all the way. Who was I to argue?

Heather got on her stomach, then raised her ass, presenting it for my pleasure. It was a work of art beyond measure. Soft and creamy, with only a fine down of soft hair. Heart-shaped and pink, with the white garter straps in contrast. Her little puckered hole was winking at me, all brown and pink and pretty. But Heather was sniffling and whimpering.

"What’s the matter, Honey?" I asked.

"Mommy said I should do this for you if you were nice and you were. But it hurts."

I didn’t want to hurt her. "Have you done it before?"

"Yes. With other sissies."

Maybe they didn’t do it right. I had an idea. "Maybe if I take some time to lubricate you and relax you, it won’t hurt. And if it does, we just won’t keep doing it, OK?"

Sniffle. "You’re very nice, Bradley."

"So are you, Heather."

I kissed her pretty butt all over the cheeks. She liked that a lot. I could see her stiff cock and dangling balls through her gorgeous thighs. Then I tentatively licked her pretty hole. That sent her into orbit. Heather shook and came hard. She moaned my name and pushed her butt back to get more of my tongue in her special place. I accommodated her, licking and adoring her hot ass to another shuddering, paralyzing cum. That girl was the hottest on the planet. And I hadn’t even penetrated her yet.

"Please fuck me now, Bradley. I want you inside me."

Heather wiggled her ass, whimpering and begging for my cock. Does it get any better than that? I placed it at the door and popped the head in.

Heather gasped and said, "That’s so wonderful, Bradley! Put it all in, please. Now!"

I did my chivalrous duty, commencing my first fuck with an insertion to my pubic hairs. Heather squealed with lust. I groaned with joy and began to pump in and out. My cock was on fire. Every nerve was assaulted. Her ass was so tight, I could barely move, so my foreskin was rubbing all the sensitive parts that it should. I reached around Heather to massage her nipples. They were erect as two little cocks. She gave a little animal sound and miraculously produced more creamy girlie juice. I was pulled up into the cyclone of her lust and dropped into the path of the Cum Express! Wooo wooo! Slam! My balls exploded and I felt the cum blast from each of my toes (metaphorically, of course). The whole thing must have lasted 20 seconds, but I treasure the memory of each moment.

Heather was crying. Had I hurt her? I pulled my cock out and lay next to her, holding her in my arms. "What’s the matter, Honey?" I asked.

"I think I love you, Bradley. And Mommy may not approve of you."

"I know I love you, Heather and we’ll figure something out." Kiss. Cuddle. Coo.

We hugged and kissed sweetly for a half hour. Then the Dragon Lady and your grandmother reappeared. My Mom was carrying a big bag of stuff.

"Play time is over, children," Mrs. Landrow said. "Bradley needs to get home and begin his sissy training with Mrs. Woods. Won’t that be wonderful, Bradley?"

Best to play along if I wanted to see Heather again. And I wanted that very much. "Yes, Ma’am."

"Very good, Bradley. You may wear those horrid boy clothes home, but Mother has some pretty underthings for you to wear under them."

My Mom handed me a pair of black, silky stockings, rolled into doughnuts, a black garter belt and lacey, satin panties. Despite my hard cocksman work and my determination to remain a boy, my soldier sprang to attention just at the sight of those things. I rolled the stockings on, hooked them up to the garter belt and stood there, panties in hand, in raging sexual distress.

Mom said, "You’ll never get those panties on like that. I need to milk you first, Lisa."

Lisa? That was the girl name mom had chosen for me. Not bad. I use it today.

It didn’t take much milking. I was highly excited by the frillies and the audience and I quickly blew a thick, warm load into Mom’s hand. I pulled my first panties on [Ooooh!], kissed Heather goodbye (she gave me LOTS of tongue), got dressed in my boy duds and left with my Mom. Mom babbled something about my training all during the car ride home, but I just fingered my garter snaps and thought about Heather’s tight ass and luscious nipples.

I knew Mom wouldn’t have the persistence to go through with it. She’s never even finished a jigsaw puzzle. And I was right. But I kept wearing the lingerie under my boy clothes, on my own volition.

I was worried about Heather and the crazy lady. The white truck from the asylum never came for Mrs. Landrow, but a week later, she was crossing the street preoccupied with thoughts of ways to torture her "son" when an 18-wheeler sent her where she couldn’t mess with Heather’s mind any more. Heather was taken in by a sweet aunt, who gave Heather what she needed to be a girl without dominating her. Heather and I became lifelong friends and lovers and she introduced me to her sissy friends. I even dabbled in sissiness myself.

I’ll tell you all about that at another time, Eric, but it seems you need some more attention. Lie still and let me just lubricate these two fingers. There. How do they feel in your warm, tight butt?

[Oh Dad! That feels fantastic. Please keep doing that.]

Of course, Honey. Now let me just tease your foreskin and peehole with the other hand. Isn’t that wonderful, Eric? I’ve been negligent. A young boy your age needs to be milked regularly, but not by me. You should have pretty girls milking you with their soft hands, red lips, wet pussies or tight assholes. Or, if you’re lucky enough to meet a pretty sissy, she should be milking you in ways that only sissies and men understand. You could even get together with your friend, Rick and lie side by side in your bed, both in your underwear. Pulling your jockies down to your knees. Feeling your own cocks, then tentatively reaching for each other’s. Skinning each other up and down, up and down. Wanting to kiss, but knowing that it’s gay. Tickling, teasing, giggling. Oh, Eric, you’re being naughty again. Look at all that goo!

[Dad!! Rick!!!! Ohhhhhhhhhh!!!!]

Let it all out, Honey! That’s a good boy. You can even learn to milk yourself. I can help you get started there.

I’m going to say good night now, Eric. You need your sleep and Mr. Bruder’s had some time to rest. His cock will be rock hard again. It’ll taste so good when I lick it. His ball bag has had time to fill up with hot, creamy cum and I want to eat it all up. Then he can rest again for a few hours and give my tight butt a good seeing-to and another creamy load before he goes off to work. Good night, Eric. I love you. [Kiss]

[Night, Dad. Love you too. ]

 

Chapter Four – The Next Day

Dazed and confused, with a throbbing erection, I awoke at 11 a.m. Since it was a Friday during the school year, I wondered why Dad didn’t wake me.

I stumbled into his home office in my pajamas to ask him. Confirming that the strangest night of my life had indeed happened, I saw Dad at his computer, working and humming away, wearing a pretty, light-blue, ribbed tank top, well filled with what I presumed were breast forms, tight black miniskirt, silky stockings over his long, shapely legs and four-inch slingback heels. He had the same curly-blonde, natural-looking wig as last night, sexy make-up, appropriate accessories and subtle perfume. No wonder these guys all wanted into his panties. My Dad was a babe!

He noticed me and moved over to kiss me. "Good morning, Sweetie. Did you sleep well?"

"Yeah, but isn’t today a school day?"

"Mr. Bruder saw to it that you were excused today. It was the least he could do after I was so nice to him, don’t you think?"

"Uh-huh. Thanks, Dad. Do you dress like this every day when I’m at school?"

"About half the time. It’s so much work switching back and forth from male to female. Now that you know about me, I’ve decided to start in full-time as a woman.’

I liked that idea. It made Dad happy and he was really pretty as a woman. "Dad, what about your business? What will your clients think?"

"They all need me very badly, so they won’t leave. Plus, I’ve entertained all the nice ones and they would die before giving me up. Men love their sissies, Eric. We have an understanding."

"Are you a sissy, Dad?"

"Yes, I am. I denied it for years. Even got married to try to blot it out of my personality. Don’t blame your mother for everything, Eric. I never dressed in front of her. But she knew I wasn’t like other men. Pretend though I might. I love being a woman and I love having sex with a man when I’m dressed. And they love me."

"Dad, could I hear more of your life story?"

"Sure, son. Do you think you’ll be naughty again? I don’t want to make you uncomfortable. Here, I’ll put a towel over my lap to protect my new skirt and you sit on it while I tell you more. Why don’t you just take those pajama bottoms off, then I can give you relief more easily?"

"Can I take the top off too, Dad?"

"You little teaser. I guess you are like me. I wonder how much."

I shucked off my peejays and sat naked on Dad’s lap. He smelled like a field of wildflowers. He praised my beauty in general and added some specifics. "Look at these pretty nipples you have, Eric. So dark and erect!" Dad wet one manicured finger and teased my right nipple. "I see you like that. You’re a little sexpot, Eric. You’re going to make a lot of people and yourself very happy."

My willie got very stiff. Dad smiled and stroked it as he began his story.

"Even though your Grandma never put any effort into dominating me into sissiehood, I was fascinated by the idea of being a sissy. She never even noticed when I took the stuff that Mrs. Landrow had given her and used it myself.

"There was some great stuff in there. Frilly nighties, sexy lingerie, including six colors of stockings, and acres of pretty panties, all in my size or thereabouts. There were also lots of female hormones. But I never took any hormones until your mother left last year. Yes, I’m growing nice titties, which I’ve been hiding, and my beard has retreated a lot. I’ll show you my titties when they’ve gotten a little bigger.

"There was also this how-to guide for feminizing your unwilling son. Femininity has to be something you want. I would never force it on you, Eric. Let me show you. See this silky pair of royal blue panties I’m sliding up and down your cock? You don’t have to wear them unless you want to. I would never force you. Of course they do feel good don’t they, Eric?"

"They feel fantastic, Dad."

"Do you have to spurt again, Eric? It’s OK. I know young boys enjoy their milkings. I see you’re going to. WOW! That’s a gusher, son. ZOWIE! Five big, creamy globs. Nicely done."

"So good, Dad. Uhhhhhhhhh." I was in heaven.

"Let me get a fresh pair of panties to rub you with. Here we are. So then I started wearing panties and stockings all the time, except on days when I had gym. Just seeing myself in them got me red hot. I needed to wank myself all the time. I had to dress in the dark or I could never get to school.

"Heather’s aunt only lived five blocks from us, so when she was settled, I stopped by to pay my condolences about Mrs. Landrow to her and Heather. Aunt Helen was so sweet. She told me Heather would be very happy to see me. Aunt Helen knew that Heather didn’t want to be Adam again, crazy mother or not.

"Heather was upstairs when I was talking to her aunt. She squealed when she heard my voice and came running to me instantly. She hugged me and rocked back and forth, crying with joy to see me.

"She looked fantastic. No longer a zombie slave, she was in a loving home and was getting everything she needed, including hormones. I told her I was now Lisa at least part time and said I wanted to be her boyfriend or girlfriend, whichever she preferred. She said that she and her two sissy friends were having a sissy slumber party that Friday night. Could Lisa attend? Could I? Wow!

"Mom agreed to let me go. I dressed in one of the pretty dresses the late Mrs. Landrow had selected for me, with two-inch heels and pretty stockings, packed a bag of lingerie, sleepwear and lubricant and headed off to every guy’s fuck dream. Three beautiful young sissies and me. Well, four, counting me.

"You have to remember, Eric, that this was my first time out dressed and, even though I knew Heather, ahem, very well, her Aunt Helen had only see me as a boy. And then there was the issue of the other two young sissies. I was a bit nervous when I knocked on the door and a very excited, jumping-up-and-down Heather greeted me.

"Away from Minga the Merciless, Heather had already assumed a personality that was closer to her true self. And it was a good one. She was vivacious and loquacious, with firm opinions and a keen wit. She was also so damned sexy that I was ready to cream my panties just from looking at her. Did I love Heather?

"She ushered me in and introduced me to Aunt Helen as Lisa. Aunt Helen knew Bradley, but treated Lisa as an entirely different person. A femmy one. I liked that. Heather was in good hands.

"Aunt Helen praised my hair (two little pigtails), my dress (this old thing?) and my beauty. I agreed. I made a very pretty girl."

"You still do, Dad. Unnnnnhhhh. And you’re a world-class boy-milker."

"Thank you, Eric. You’re so sweet. Anyway, the other two sissies rushed downstairs to meet me. They were already in their babydolls and they were dolls, Baby. Taneesha was an African-American girl with long, silky legs and a Miss America face. Her braided hair fell over her soft, dark shoulders and she looked outstanding in her skimpy, lime-green, wispy nightie that barely covered her tiny panties. Amber was a dark-haired beauty whose brown eyes invited men to the bedroom with unspoken, but explicit promises. She was wearing a white nightie with white thigh-highs. Yummy! Did I mention that Heather was wearing the pink babydoll that we had cum buckets on together just a few short weeks before?"

"Aunt Helen gave us snacks and juice to take to Heather’s room then told us to be good girls and she would see us in the morning. What a wonderful lady.

"We rushed off to Heather’s room giggling and grabbing each other’s perky little butts. ‘You’d better get ready for bed, Lisa,’ Heather said.

"I unpacked my black babydoll and started to undress. I looked over at the girls and they were all on their backs, with their panties down to mid-thigh, looking at me as they stroked big erections. Wow. They were licking their lips too. I dressed quickly, omitting the panties and joined the girls on the bed. I covered Heather’s perfect body with my own and kissed her completely. She sighed and purred with contentment. Then she dug her fingernails in my back to show me she had spirit and a desire for energetic love. We rubbed cocks, dripping pre-cum all over each other. Taneesha and Amber joined in. Taneesha lubed a finger and found my prostate with it. Amber did the same for Heather. We kissed urgently. Then I exploded, firing cum all over Heather’s tender tee tees. The hot cum ball bath did it for Heather. She squealed softly, kissed me harder, and blew jets of cum all over my mid-section. The evening was off to a good start.

"’You were right, Heather," Taneesha said. ‘Lisa is definitely in love with you. Are you going to hog all that cum for yourself or can we play too?’

"The girls ganged up on our privates, licking off all the cum until we were ready and randy all over again. Taneesha lay on her back and invited Amber to sit on her face. I hadn’t seen that before and found it fascinating. Amber was on her knees, straddling Taneesha’s shoulders, facing Taneesha’s feet. Amber eased her pretty butt onto Taneesha’s long tongue and squealed and squirmed happily as Taneesha feasted on her lovehole. Taneesha pushed Amber’s nightie up, revealing two nice, budding titties, which she fondled expertly. Then Amber’s cock twitched. She whimpered, scrunched her pretty face, and blew a high, hard load.

"Being a sissy is so much fun. Why did I ever stray? Amber then leaned over and took Taneesha’s nice sissy meat into her hot, wet mouth. She knew how to skin, lick, suck, tease, tickle, fondle, slurp and swallow in ways no girl ever could. She had Taneesha on the verge, then pushed her over. Taneesha screamed so loud, I was sure Aunt Helen would be there with the EMTs. But she just left us alone.

"Heather and I were tired of watching. I kissed her into a stupor and sucked her titties as I fingered her tight hole until she came all over herself. Then she did the same for me! I had never had my nipples sucked before and it was magnificent. Have you ever had it done, Eric?"

Gasp! "No, Dad. Is it fun?"

"Is it fun? Let me show you."

Dad proceeded to lick my nipples and wank my weenie until I came twice and almost fainted. But I still wanted to hear the rest of the story.

Dad went on. "Next I wanted my cock in Heather’s butt, but she suggested that it was her turn to do me. That was all new for me, but I was eager. Remembering the kind attention I had given to Heather’s girlie hole the last time we had made love, Heather turned me on my tummy, lifted my tiny nightie and ate my butt for a good half hour. The other girls were coitally joined, but Amber and Taneesha kept sneaking looks at Heather’s enthusiastic ass-licking. She was good at it and my poor butt was having the night of its life. I came hard during the adoration, but Heather licked on. Finally, she pronounced me ready and aimed her sissystick at my little heinie. I was scared, but told her to press on. Oh! She popped the head in. It felt fantastic! A little more of her girlie pole. Mmmmm. Then all of it. Aaaaah. I love a hard cock in my ass and I hope you will too, Eric. The ass was made for cock. I was filled up that night.

"As Heather made me her sissygirl, Taneesha moved over and offered me her cock. It was drooping and covered with dripping cum. It looked delicious and I took it all in my mouth, stuffing myself at both ends. Mmmmm. Amber lubed three fingers and massaged Heather’s prostate as Heather fucked me. I still dream about that scene. I swallowed Taneesha’s delicious spunk and Heather filled my virgin hole with hers. Amber’s kind lubing made Heather wide open for my distressed girlie pole. I put her on her back, moved her ankles to my shoulders and fucked her silly. Amber had Taneesha in the same position and we gave them all they wanted and then some.

"That was the first of many sissy slumber parties the four of us had together. The other girls were all full-time sissygirls. I was the only dabbler. Something kept me from committing until last night. The girls’ titties kept growing and they kept getting prettier and more femmy. Though they lied to make me feel good, I kept getting more (yuck) masculine.

"The parties weren’t all fucking. We would do each other’s hair and paint each other’s toenails. Then we would fuck. We talked a lot too. About boys mostly. None of us had ever been with a boy until one night when we were fifteen. Someone (I still suspect Amber) must have tipped off four boys from my high school that we held a sissy slumber party every Friday night because one Friday, after we had only fucked each other once and were gabbing about the boys we knew, we saw a ladder appear at Heather’s bedroom window. Followed by a boy. It was Jimmy Winslow from my English class. We screamed and ran around putting our panties back on. It was very exciting. Jimmy stepped in and said, ‘Hi, Ladies. May we join you?’ We?

"Three more cute boys came up the ladder and into the room. The moment of truth was there. Did we scream for Aunt Helen to call the police or did we remove our panties and have boy-girl fun?"

"Dad, I think I know what you did and this is some exciting story," I said. "Could you do that thing with your fingers in my tushie while you finish it?"

"Sure, Honey. Heather was the first to remove her panties and she went over and kissed Jimmy. I wasn’t really jealous because it was different with boys. Tommy Jamison came over and kissed me. He was an excellent kisser. Before I knew it, the bad boy had my panties off, had me on my back on the bed and was giving me seven stiff inches. It was so different being fucked by a boy. I loved it. I loved sissy love, but fucking with boys was even better. The poor dear was grunting and straining for his orgasm. I helped him along by tickling his balls just right, then teasing his butthole the way I know boys like it. What a hot load he gave me! The first of hundreds from boys and men, but one I’ll always remember. A little shyly, he asked to suck my cock. I coached him along and he was so proud of himself when I wiggled and squirmed and made loud girlie noises until I came all over his cute face.

"We didn’t invite the boys to all our slumber parties after that, but they sure spiced up the ones they attended.

"Eric, I think you’re going to make cummies again, aren’t you, Sweetie?"

"It’s those fingers of yours, Dad. And those silk panties rubbing my cock. And those stories. Unnh. What a life you’ve had. Oh!"

"You can do all that and more, Eric. It’s all up to you. Now let’s get that old boy juice out of you and let you make some fresh stuff. How’s this?"

"Ohhhhhhhh, Dadddddddddd!" Dad kissed my naked shoulders as he pistoned my butt with his fingers. I let it all go and quivered violently. Worse, I let out a girlie scream. Was I becoming girlie? Dad made a little smile.

 

Chapter Five – Fun with Myself

Dad insisted that I clean myself up and get outside for some fresh air while he did his work. After a nice dinner, Dad escorted me to my room and said he had some presents for me. They were a large jar of Vaseline, three boxes of Kleenex and an oversized comic book called "The Miniskirt Club." The cover said it was a Spremco publication and was drawn by an artist named Teri. It portrayed three very pretty girls in miniskirts, black stockings and very high heels. Two of the girls appeared to be around 16. The third was around 13. They all had big smiles and big bulges in their miniskirts. The detail was incredible.

I opened the book. On the inside cover was an ad for breast forms made by Spremco. I glanced over that to a drawing of three boys walking home from school. The two older boys were saying to the younger one, "You’ll love it, Brian. Trust us." Whatever "it" was, Brian looked nervous.

On the next page, all three boys were naked. They were gorgeous! Pink, sexy bodies with delicious cocks and pretty ball bags. The artist showed us Brian’s tight asshole, with an exaggerated pucker. Mmmmmm. I was getting a stiffie already.

The next page showed the boys slowly, sensuously rolling black stockings up their legs. Brian was watching the older boys with awe and lust. His six-incher was stiff and self-lubricating liberally.

Then Brian, now Linda, got her stockings on and stood in her four-inch heels. She had hooked a garter belt on and her big, stiff girlie pole was standing tall against her belly. The older "girls" were similarly aroused. I opened the jar of Vaseline and slathered some on my fingers. Then I rubbed it all over my balls and put a thick coat of it on my cock, all the way up to the tiny peehole lips. This was getting exciting.

In the next drawing, one of the older "girls," Denise, was on her knees in front of Linda, sucking her to a creamy emission. Linda, was wincing with intense pleasure. The third "girl," Marcia, was stroking herself and cumming on Linda’s cock and Denise’s smiling face.

I rubbed my cock and teased the head with my slippery hand. It felt wonderful! Sex with sissies looked like so much fun.

Then Marcia was kissing Denise and licking all the cum off her face. Linda was stroking her cock to another firm erection.

Apparently, Denise and Marcia had been dressing in miniskirts, stockings and heels, then sucking each other off, for some time. Linda was new blood (or cum) in the Miniskirt Club.

In the next drawing, the girls were dressed in their pretty tops and bulging miniskirts. They had applied make-up to become even more gorgeous. I couldn’t help it. The whole idea of becoming a girl like that was so exciting to me that I just blew a big load. I bucked and arched my back, squealing like a girl again. I was going to have to watch that.

I pressed on. In the next drawing, there were three cute boys at the door. Two looked to be around Marcia and Denise’s age, one was definitely for Linda.

Then the boys were let in. They were not shy. They were kissing the three girls, had reached under their miniskirts, pulled their panties to mid-thigh and were stroking their cocks. The girls were already cumming, hot goo dribbling down their cocks and all over the boys’ fingers. My stiffie was back.

The youngest boy pulled out his Johnson. Linda was on her knees sucking it lovingly. The boy’s face was beatific.

In the next drawing, the youngest boy was cumming on Linda’s delighted face. The other four, two naked boys and two girls in their lingerie, were kissing and watching.

Then Limda was on her back, with her skirt up, lacy, tiny panties down around one ankle, and ankles on her boyfriend’s shoulders. He was entering her tight butthole slowly with his hot, hard cock. Linda appeared a little nervous, but very excited. Her clitty was skinned, hard and at full attention.

Then the boy’s cock was completely in Linda’s tender, virgin anus. Her head was thrown back and her clitty was spurting wildly.

There was more, but I couldn’t make it through. I applied every one of Dad’s techniques and milked myself twice in a row, cumming almost as hard as I had when Dad sucked my nipples. I wondered if Dad had any more of those books. I wondered if I could get a boy to suck my nipples. I wondered if I wanted to.

 

Chapter Six – Megan

The next day was a Saturday and Dad announced that we were going to Mr. Bruder’s house for dinner that night. He said that Mr. Bruder had a daughter a year older than I and that I would like her a lot.

How did he know that?

Dad spent the afternoon primping for his big night out with the man who had fucked him silly two nights earlier. I spent the afternoon with "The Miniskirt Club." In later drawings, Linda got to suck off all the boys and her fellow girls. She was covered with cum, but giggling with delight. One older boy fucked her and another was sucked by her as her girlie friends sucked her nipples. The youngest boy courteously licked her cock to a Force 10 cum. I had two nines, a ten and a certain eleven.

I had to remember to ask Dad for some more Vaseline and Kleenex.

After cleaning myself off, I got to see Dad in all his glory. He looked incredible. His little black dress showed lots of firm, shapely thigh. His five-inch heels toned his legs to perfection and made his butt stick out provocatively. His wonder bra gave him a lot of lift and cleavage. His gold earrings and white pearls were the perfect accessories. My Dad was babe-a-licious.

How he drove the car in five-inch heels I’ll never know, but we arrived at the Bruder’s safely at seven. Mr. Bruder’s eyes got very big when he saw Dad. And so did the bulge in his pants. This time, he kissed Dad in front of me. And I thought I saw some tongue.

Where was this girl I was sure to like? Mr. Bruder called upstairs, "Megan, honey. Our guests are here."

A bedroom door opened, "Coming, Daddy," I heard a sweet voice say. Then I looked up the stairs and saw the most stunning girl in the galaxy.

She glowed with beauty as she regally descended the stairs, putting one shapely, white-stockinged, high-heeled leg in front of the other. Her white, girlie dress was an A-line with very short, pleated skirts that flounced prettily as she moved. Her radiant smile nearly blinded me as she said, "Hello, Eric" in a tinkling splendor. I almost fainted when she kissed me on the cheek. Dad was right. I liked her.

Megan’s delightfully pretty face was framed by a headful of blonde curls. Her brown eyes sparkled with fun and intelligence.

I trembled. I was not worthy of this girl. I had spent the afternoon wanking my weenie. Yesterday I had sat naked on my Dad’s lap and had him wank me and suck my nipples.

Tongue-tied at first, I was able to converse with her, thanks to her kind and gentle attempts to relax me. We found that we had many of the same interests in music. Megan even loved baseball. The perfect woman!

We had a lovely dinner and Dad and Mr. Bruder told Megan and me to relax in the family room. They would do the dishes.

Alone at last. Now what?

"Your Dad is very nice," Megan said. "I think my Dad is falling in love."

I had to ask. "Don’t you think it’s a bit odd? You know. Two dads?"

"Certainly not," she said. "Do you?"

I backpedaled quickly. "No. I love my Dad very much, but I’ve only known that he’s also Lisa for two days now. I’m still getting used to it. I’m glad you’re OK with it."

Megan smiled that 1,000-watter. I puddled. She went on, "I know, Eric. You’re a very nice boy. Would you like to kiss me?"

Wow! "Very much. I mean, if it’s OK, with your Dad in the kitchen and everything."

Megan giggled. "Silly Eric. Do you really think they’re doing dishes? Right now, my Dad has Lisa bent over the sink and he’s filling her girliepussy with his cum. Didn’t you see the way they were looking at each other all night?"

I felt dumb and a bit taken back at her language. But she said everything so sweetly and without malice that I was feeling very good at that moment. "May I kiss you now, Megan?"

She patted the couch next to her and said, "Sure. Come sit by me."

Eagerly, I sat to her left, putting my right arm around her creamy shoulders. She pouted her red, soft lips for a kiss and I dove in. Zowie! My first passionate kiss (those kissing games didn’t count) was a great one. She was very patient with me. Helping me develop technique without being bossy. Then she threw her tongue into things, making it twice as nice.

We kissed for a long time. I smelled her musky perfume and inhaled her femininity. It was a wonderful moment and I could have died happy right then. But there was much more to come.

I didn’t want to offend Megan, so I didn’t try to grab her titties or anything. I just hugged her and kissed her from the neck up. My poor cock was in great distress, however and my balls were aching for release. I hoped I wouldn’t explode and embarrass myself. Then things changed.

Megan put her hand on my cock. At first, I thought it was a mistake. Then she began to feel my cock through my khakis. That was no mistake.

"I’m going to give you some nice relief now, Eric, OK?"

Relief sounded wonderful. "Thank you, Megan."

Shockingly, Megan unzipped my pants and pulled them and my jockeys down to my ankles! She looked me in the eyes as she fondled my stiff rammer, skinning the foreskin and teasing the head. Megan knew her art.

I was the luckiest guy on earth. Then the solar system, because Megan got on her knees on the floor and took my pole in her beauty-queen mouth, licking and slurping me to distraction. "Unnnhhhhhhhhhhh!" I moaned as I received the very first blowjob of my young life."

Megan stopped sucking and giggled. "It’s OK, Honey. I know it’s your first. Enjoy it." Then she started licking and sucking again, keeping eye contact with me the whole time. I tried to hold back, but I was a goner in about two minutes. I squealed in an involuntary and most unmanly manner, filling Megan’s pretty mouth with a large load of boy juice.

Megan moaned and grunted softly as she swallowed and lapped it up. Then she rose to sit on the couch and kissed me sweetly. "Thanks so much for letting me be your first, Eric. It was awesome!"

All I could say was, "Oh, Megan." And I kissed her again. She was kissing back very passionately, so I decided to make a move of my own. I slowly ran my hand up her leg to her soft thigh. She didn’t resist, only kissed me more passionately. I took this as encouragement. I moved slowly up her thigh toward man’s true goal. Slowly I progressed. Step by step. Inch by inch. I reached her panties, then moved my hand to her crotch and felt – a hot, churning bag of balls!

Megan Bruder, the most beautiful, most feminine person on the earth, had a bag of balls. And a very stiff cock. I hesitated for a few microseconds, then let sanity take over. I insinuated my hand in her wispy panties and stroked her cock the way I like mine stroked. She purred nicely and kept kissing me. Then she whispered, "Let’s go to my room. I want to cum, more than once, but I don’t want to ruin my pretty dress."

Lead on. Holding hands, we scooted to Megan’s girlie room. She teasingly took off her dress, asking me to get naked as she did. When I stood there in the essence of Eric, she whistled. Wow.

The dress being nicely hung, I could see that Megan was too. She had a nice six-inch piece of meat sticking out of those frilly panties and it looked like a choice cut. She removed her bra and two A-cup beauties with large nipples popped out. How was that possible? Who cared? I wanted to fuck. She left her white stockings, stiletto mule heels and garter belt on, but that girl would have looked femmy dressed for football practice.

She minced over to me and rubbed her body against mine, rubbing cocks sweetly and kissing. I wanted Megan to feel really good, so I asked if I could kiss her all over on that nice bed. She liked that idea. I lay on my back. With her stiletto mules still on, she lay on top of me. We kissed. I moved her up so I could suck her titties, applying some of the technique Dad had taught me the day before. I held her by her incredible ass as I licked and sucked her boobs. Her cock rubbed urgently against my stomach and then it blew goo all over me. She whimpered with lust.

My chest was covered with Megan’s cum and I never felt better. Megan looked at me lovingly. What girl doesn’t enjoy a good cum after an elegant round of titty sucking? I was proud that I had led the way on that one.

But then I deferred to Megan’s obvious experience.

"I want you inside me Eric. I want your cum in my tiny pussy. Will you do that for me, Eric?"

I believe I can accommodate you, my dear. "Uh, sure. What do I do?"

"Get my pussy all wet and relaxed, Sweetie. Just lie there and I’ll lower my ass onto your face. Just lick my teeny hole and make it all hot and wet and ready for you."

Can do.

Megan flipped around and squatted on my face. She was facing my feet. I looked at her excellent ass. It was an expanse of heaven. Soft and downy. Clear skin with tiny pores and the freshest, sweetest smell. Even Megan’s puckered hole smelled clean and fresh. I tickled it with my tongue. Megan gurgled. I pushed my tongue in. She squeaked. I swirled my tongue along the walls of her ass. She screamed. I didn’t know I had that in me. I licked around in there some more. Megan bucked, shuddered and came again, spraying more hot girl juice on my chest. That surprised the both of us. I guess I was a natural. Megan’s cock and balls were dangling centimeters from my face. I reached up and took both of her pretty pink tee tees in my mouth and licked then lovingly. Megan sprang another erection and groaned my name. My own little boy was disgracefully stiff. I licked and sucked her balls, then went back to excavating her scrumptious ass. Megan was so overcome, she was crying. She begged me to stop, then flipped around and kissed me wildly, saying I was an excellent lover and she wanted me inside her now.

"Just lie still, Honey. Megan will help you."

Facing me, Megan moved to her knees, straddled my erection and slowly, agonizingly sat on it. My first fuck and still one of my best. She eased me into her, with lots of appreciative sound effects. I love those, don’t you? I felt like a sexy vise had clamped my cock and was killing me with fantastic friction. Megan began to slide up and down.

I decided to be a man.

Gently, I moved us onto our sides. Then I slid Megan on her back, the way men fuck their girls. She liked the dominance and whimpered prettily for me as she hooked her ankles on my shoulders. I seemed to be able to move in and out better this way and I certainly felt more in charge.

"Fuck me, Baby," she moaned. An oldie, but a goodie for arousing a lad.

I did my best and it seemed plenty good enough for Megan. As we fucked, I skinned her foreskin up and down and tickled her balls. Her eyes got very wide. She looked at me, muttered something, trembled, and came, the cum leaping in thick globs onto her tummy. The act of cumming made her ass clench my cock in the sexiest way and I could hold off no more. I filled her up with all the goo I had, then watched happily as it oozed out of her butt.

I lay next to Megan, kissing her and fondling her private spots. She cooed like a woman in love.

Let’s see. Had my life improved in the last 48 hours? Why, yes it had.

A few minutes later, Megan said, "That was awesome, Eric. You’re terrific."

I puffed up my cum-covered chest proudly. "I was excited by your beauty, Megan." Good answer!

"Do you like me, Eric?"

"Let’s see. You’re the most beautiful girl in the world. You’re smart, funny and nice. And you make love incredibly well. I believe I do like you, Megan. But there’s so much I don’t know about you. How did you get that beautiful clitty and pink ball bag?"

"I was born with it. Let’s fuck."

We did.

I persisted. "So you were once a boy?"

"Right again. Let’s fuck."

Only a fool would turn that invitation down. I sensed a reluctance to discuss her history. But we still fucked.

We were both exhausted and drenched in cum. I asked her once again.

"OK, Eric. I was born a boy, but I always knew I was really a girl. My Daddy figured that out and took me to a psychologist when I was ten. Mom couldn’t live with the idea, so she left. Daddy has raised me and he’s been very good at it."

"Yes he has. How did you grow titties and that beautiful body?"

"My Daddy hooked me up with some nice people at an organization called Prisoner Exchange and he sent me to a great school for girls like me. Miss Cynthia’s. [See "Lovelife" for more about Miss Cynthia’s] Everyone in the school is a sissy and we’re all little sexpots. We have girl’s bodies and boy’s sex drives. But you wore me out tonight, you little studmuffin."

Didn’t Dad mention something about Miss Cynthia’s to me once? It sounded like a wonderful place, I remembered. But why did it sound wonderful to me, a boy?

"What do you think our dads are doing?" I asked.

"Same thing we just did. Did your Dad tell you that you were staying the night?"

"No," but boy did that sound good.

"You saw them fucking, didn’t you, Eric. Dad told me. It’s OK, Honey. I saw them too. They’re really in love."

"I know, Megan. My Dad needs some happiness."

"Are you tired, Eric?"

"Yeah." And my balls were on E.

"Let’s get some sleep. When we wake up, our clitties will be stiff and our tee tees full of yummy cum again."

I had a cock and balls, not a clitty and tee tees, but it wasn’t worth arguing.

"I’m going to wash up, get out of these stockings and heels and put on the skimpiest, sexiest nightie for you, Eric. I hope it doesn’t excite you so much that you can’t sleep."

She was a little teaser. "I just realized, I didn’t bring anything like pajamas," I said.

"I have something you can wear."

We went into the bathroom, filled the tub and bathed each other all over with face cloths, soap and hot kisses. We each came one more time, but it couldn’t be helped.

When we went back to Megan’s room, she handed me a silky nightie and a pair of wispy panties.

"I can’t wear these, Megan."

"Yes you can. I won’t have you sleeping naked and what I gave you is very comfy. Wear them for me, please?"

I would have stormed a Taliban stronghold after a request like that. Megan put on this black, see-through number that would have raised the dead. Mine was light blue, with frills, ribbons and lace and matching panties.

I slipped on the panties first. They felt very good. Cool and smooth. I sneaked a look at myself in Megan’s mirror. She noticed. I looked hot already. Like one of those girls in "The Miniskirt Club." Then I put the nightie over my head. Oh my. That felt fine. Why do men get to wear all the disgusting stuff and women all the good stuff? I felt as if I had been reborn into someone else. This time I looked at myself openly in the mirror.

Megan said, "You look beautiful. A little make-up and some coaching and the boys would be on their knees around the block to suck your clitty."

There was a new image. It gave me a raging erection. Megan noticed that too. We got in bed and she nursed on my cock until I came in her mouth and we fell asleep.

 

Chapter Seven – More about Dad

As we drove home from the Bruders, Dad and I talked about our night.

"I’m sorry you had to wear that nightie last night, Eric. And those panties you’re wearing now. I should have brought stuff for you. I wasn’t sure we’d be spending the night. It was really up to you and Megan. I think you two liked each other."

"I think you’re right, Dad. Megan is a better boy milker than you are. [Giggle.]"

I told Dad what we had done and what I liked about it. I even shared my feelings on wearing the girlie clothes. That piqued Dad’s interest.

"Have you ever been attracted to boys and men, Eric?"

"I didn’t really think about it, Dad until you mentioned Rick and me wanking each other. And when Megan said I would have boys on their knees lined up around the block to suck my clitty. I got that picture in my mind and I got the stiffest woodie. It was a very exciting thought, Dad."

"Hmmmm. I had thoughts like that and tried to suppress them. In high school, other than those sissy slumber parties, I was living most of my life as a boy. The only sex I had with boys was at those parties. I openly dated Heather, but as a boy. I even took her to the prom.

"I loved being a girl and I loved sex with sissies and boys. But I also wanted to be ‘normal.’ I wanted a family with 2.5 genetic kids and a white picket fence. Nothing wrong with that, but I should have known it wasn’t for me.

"I met your Mom in college and I looked at her as a ticket to the straight life. Heather and I still saw each other, even after she married a really nice guy she’s still married to today."

"Where is Heather now, Dad?"

"You know her, Eric. She was your sixth and seventh grade English teacher."

What? "Mrs. Anderson? Mrs. Heather Anderson?" Mrs. Anderson was every junior high boy’s fuck dream. She was the prettiest, sexiest, most feminine junior high teacher in the history of the world. She was also the best teacher in the school.

"The same. I still love her. But I need to be with a man. And so does she. We sissy girls dally with each other, but we’re meant for men."

"So why did you choose a woman, Dad?"

"Stupid, stupid, stupid. I wanted a ‘normal’ life. Still, I have you and that makes the misery more than worth it."

"Thanks, Dad. Did you date men when Mom was around?"

"I’m sorry to say, I did. I should have been more truthful to Mom. And more faithful, I guess. I stayed away from men for fifteen years. Then a couple of years ago I met Craig Bruder. I was fixing his computer system at school. It was a real mess and he and I spent some late nights together. We talked about our lives and Craig recognized that I was a sissygirl in male drag. Good, sensitive men can spot us, Eric. Craig was drawn to me and told me so. I kissed him right there in his office one night and before you knew it, he was porking my pooper on his desk. I felt funny about making love with him in men’s clothing, but Craig saw me, not the clothes. Beware of the so-called sissy admirers who love you when you’re dressed, but can’t stand to see you as a man. They’re also the kind who would never dare introduce you to someone they know. Craig isn’t gay. He loves me and my femininity. My cock and balls are nice extras. After that, I was always en femme when we made love.

"I started seeing other men too. Mostly clients. Once I quit my self-delusion, men who loved sissies could spot me from miles away. And they all wanted me."

"You’re very hot, Dad."

"Thanks, Eric. Son, I don’t want to influence you at all, but if you’re forced into the same mistakes and missed opportunities I was, I’ll never forgive myself. Would you like to explore your feminine side?"

I considered that. "I would."

"Do you have a girl name picked out?"

I considered that too. "I like Caitlyn, Dad."

"OK. When you’re dressed, you’ll be Caitlyn. I’ll take some measurements and get you some things during the week. We’ll shoot for a trip into the world next weekend. You can begin wearing panties right away. Do you like panties, son?"

"Very much, Dad. The silkiness caresses my balls when I walk. And who doesn’t like his balls caressed? Two questions, Dad. When can I see Megan again and do you have any more of those books like ‘The Miniskirt Club?’"

"Megan and Mr. Bruder will be at our house for a sleepover on Wednesday and I have a nice one entitled, "Getting an A from Teacher."

Zowie and zowie!

 

Chapter Eight – Caitlyn Peeks Out

That Sunday night, I went to my room and took another look at the magnificent drawings in "The Miniskirt Club," trying to decide if I identified more with the sissies or their lovers. I concluded that I was most aroused by thoughts of being Brian/Linda, the youngest, newest member of the club. I was stroking myself looking at a picture of Linda cumming when Dad came into my room. I stopped stroking to talk to him.

Dad was wearing his bra and panties, pretty, white thigh-highs and white heels, even though it was a week before Memorial Day. Naughty Dad. H e was also carrying another book for me, entitled, "Getting an A from Teacher."

"I knew you would like ‘The Miniskirt Club,’ son. I’ve spent many, ahem, pleasant hours with it myself. I always identified with that young girl in that story. She had a real future ahead of her as a sissygirl. This new one will give you an idea of what sex with men is like for sissygirls."

"Thanks, Dad." I couldn’t wait to "read" it. You look great, Dad. Could I ask you a favor?"

"Sure, Honey."

I asked him nervously. "Could you show me your titties. I’m really curious."

"Of course. I should have shown you them before." Dad unhooked his bra and two small, but pretty puppies fell out. He was very proud of them and he should have been. The nipples were dark and large -- very attractive boobs. He sat next to me on the bed. My cock was out, slicked up with Vaseline and he was bare-tittied, but neither of us was self-conscious. We’d evolved in the last three days.

"Can I touch them, Dad?"

"Sure. Do you like them. Oh, that feels very nice, Eric. Pinch gently now. Mmmmmmm."

"Dad, do you need relief?"

"What a nice boy you are." Dad shimmied his panties over his stiff clitty and for the first time I saw the paternal prick at close range. It was huge compared to mine, and very dark. His foreskin was so long that it covered the whole head. I reached over and slipped it back, exposing the soft skin of his clitty head. Dad groaned.

"That’s very nice, Eric."

I was fascinated by my first handling of a man’s prick. I looked at his nipples. They had erected fiercely as I was stroking him. On a lusty impulse, I sucked Dad’s left nipple. He shuddered and came globs over my fingers. Then again. And again.

I was very pleased that I could give my Dad pleasure. He thanked me, kissed me gently on the mouth, hitched up his panties over his cummy privates and said good night. I think that was as far as he ever wanted things to go between us, so he left. A good rule.

Alone, I turned to "Getting an A from Teacher." I had a raging stiffie. Something in that book would help me relieve that, I was sure.

The cover identified it as a Spermco publication in the "Young Lovers" series, again by the magnificent Teri. It showed a very pretty girl of around 16 in a short skirt, stockings and heels holding a test paper, on which the letter "B" had been written large. Under the B was written "See me. Mr. Miller." The girl had a disappointed look on her face. In the background, a large, football-player type man, who was obviously Mr. Miller, her teacher, was standing with his arms folded. He appeared to be leering at the girl and you could make out the beginnings of a stiffie in his pants.

The inside cover advertised SmoothPanties, a Spermco product for Tgirls who didn’t want their little secrets exposed to the wrong people at the wrong time.

On the first page, class was breaking up and the girl, whose name was Julie, was moving up to see the teacher at his desk. The other students were leaving and it was plain that Julie was the only person in the room displaying any femininity. The other so-called girls were in jeans, flannel shirts and t-shirts. They looked more like Ray Romano than girls. Julie looked anxious. It appeared she really needed that "A."

Mr. Miller and she waited until everyone had left, then he lifted Julie’s mini, pulled her panties down to her creamy thighs and extracted her long, thin clitty and pretty balls. He stroked her clitty as he was kissing her. She was leaking sticky goo and enjoying the attention very much. They had obviously been through this before.

In the next panel, Mr. Miller’s pants and underpants were around his ankles and Julie was stroking his enormous cock as they kissed. She was already cumming over his big, meaty hand. He was leaking pre-goo on her tiny, manicured fingers. She had skinned his foreskin and it revealed a plum-sized cockhead, dark red and aroused. His peach-sized balls hung six inches down in their dark, hairy sack. She looked so tiny next to him. And so aroused.

One panel showed Julie licking Mr. Miller’s oversized cock. The big meat was drawn in exquisite detail, showing every vein, hair and ridge. It was hot, throbbing and gushing the man’s cum as she adored every pore with her tongue.

Julie stripped to her tiny, thong panties, black thigh-highs and four-inch-heeled, black stiletto mules. Her ample titties were being sucked by Mr. Miller as he lifted her by her asscheeks so he could suck without bending. She was squealing happily and rubbing her cock against his hairy naked body.

I let a four-star blaster go from my pubic area. I was vastly turned on by pretending to be a pretty girl submitting to a powerful man.

Then Mr. Miller, still holding her as if she were weightless as they stood facing each other, eased Julie down on his monster cock. I hoped she had lubed up before. Apparently she had, because it was obviously pure pleasure for her. And for him. An angle from the floor showed her little flower stretched to its outer limit, but holding steady. Mr. Miller was lubricating freely and goo could be seen drooling from Julie’s asshole.

In the next picture, Julie’s orgasm overtook her. She was cumming all over her older lover’s chest, head thrown back in ecstasy as he continued to dominate her and possess her anally.

The thought of being anally possessed by a big, hairy, large-cocked man sent me over the top again. I shuddered and came with another of those annoying girlie squeals. Was my larynx telling me something?

Flipping ahead, I peeked at the last panel. It showed an out-of-breath, but smiling Julie. She was covered with cum and it was oozing from her cock, mouth and asshole. But she was proudly holding up her paper, which was now marked with a very big A+. So that’s what I’ll have to do in school, I thought. I was OK with that.

Having had enough excitement for one day, I put the books away, cleaned up, and slipped a borrowed-from-Dad babydoll over my head. Then I pulled on the matching panties and got into bed. I just thought they were comfortable, OK?

 

I wore panties to school that week too, because I thought they were comfortable. OK?

I was counting the minutes until Wednesday when I could see Megan again. And I was not disappointed.

Miss Cynthia’s was a boarding school, but it wasn’t a prison. Mr. Bruder picked Megan up after school for our "sleepover."

Megan was wearing her school uniform when she came to our house. A tight, frilly, white blouse, the world’s tiniest, pleated miniskirt, black stockings, whose tops were almost visible and impossibly high heels. I almost fainted from anemia. Every drop of blood in my body had rushed to my prick.

We kissed. Dad and Mr. Bruder kissed. The hell with dinner. I took Megan to my room. Rats! I had forgotten to put "The Miniskirt Club" and "Getting an A from Teacher" away. Megan spotted them and flipped through them with great interest.

"Well, Eric," Megan said. "By all these sticky pages, I see that you have an interest not only in me, but in my sissy sisters. Or are you interested in becoming one of us?"

"Who cares?" I said, having learned from Megan herself. "Let’s fuck."

It worked.

Five fucks later, we were both naked, lying there in an exhausted, cummy heap. Megan was cuddled up to me, swirling her pretty, manicured right index finger around the head of my left-for-dead cock. It wasn’t responding.

Megan kept doing that and said, "Our school is so much fun, Eric. There’s a boys’ school near us called Manley Academy and all the boys fuck us sissygirls. I love fucking boys, Eric. And men. My Daddy’s friend from the Army stayed with us last summer and we fucked. A lot. He had a nice, fat cock and he loved when I licked it and kissed it till all his cum jumped out. Wouldn’t you like to do that, Eric? Suck a big, hairy man’s cock? Not a gay man. A straight man who loves us sissies. It tastes so good. Oh, I know you’ve sucked my cock, Eric and you’re very good. But a man! Mmmmmmm."

My poor dead cock was stiffer than it had been all night. She was right. Sucking a man’s cock. Having him make love to me. Dominate me. Possess me. Mmmmm. And a boy doing it would be a close second.

Megan continued to swirl the flowing pre-cum around my ccckhead with her index finger and persisted with her narrated torture. "And the feeling when his big cock goes in your oh-so-tiny hole. You’re afraid that you’ll rip down there, but you don’t. He pumps you with his cock. In and out. In and out. He’s grunting and sweating. He wants a big cum, but not too quickly. You stroke yourself. You can’t get away, Eric. You’re just a helpless little girl and he’s your master. He’s too big. And strong. He’s fucking you. He…….Oh, Eric. Look what you’re doing. And I thought you were empty. Ohh. More? And again? That’s the biggest one all night. I think you liked what I was talking about.

My balls ached from overwork. I was soaked with cum. And I wanted a man’s cock in my butt.

Megan knew. She kissed me and said. "It’s all right, Sweetie. You’re fine. You’re just one of us, Caitlyn."

Caitlyn?

 

Chapter Nine – Out and about

That Saturday began Memorial Day Weekend. And it was memorable for me. I was to venture into the outside world for the first time as Caitlyn.

Dad was helping me get ready. First I bathed with fine oils, then patted dry. I perfumed and powdered myself, then put my bra (with Spermco breast forms), panties, stockings and garter belt on. I had a big woodie already. Then Dad helped me blow dry and style my hair. As he helped me with my make-up, I asked him about dating men and boys.

"It’s not all about sex, Caitlyn," Dad said. "Although that’s the most fun. <Giggle> I love when the man shyly asks for the date and how delighted he is when I accept. I love when he brings me little things and holds the door for me. And considers my feelings and needs. I like to be treated as a lady."

"Do men do that for you, Dad?"

"All the ones who got a second date did, Caitlyn."

"What was your first date with Mr. Bruder like, Dad?"

"Since Mom was still around, I packed a bag and went to his house. He had given me a key, so I got there early and got en femme before he got home. When he came home I had his dinner cooked for him. Just like a real wife. One who cooks and cares about her man. He kissed me and held me in his arms as if I were the world’s greatest treasure. Craig cherishes me, Caitlyn. There’s nothing like it. I gave him a fine meal, then he insisted on taking me to this swing dancing club he used to go to. I didn’t think I could do much dancing in the four-inch heels I had on that night, but he told me he wanted to show me off. He was proud of me, Caitlyn, and those four-inch heels were walking on air.

"I was a little worried someone would recognize me. I was a married man. But when I’m Lisa, which I am for life now, I’m a different person. A happy one who was swing dancing with the best of them. When we got home, it was too late to go in with him. I had to get home to you and your mother. I didn’t even have time to suck Craig’s cock. But neither of us cared. We bonded that night and knew that we would be together someday. Now look, Caitlyn. You were crying and ruined your mascara. I’ll have to fix it."

"Sorry, Dad. It’s just so beautiful what you and Craig have. You’re a terrific person, Dad."

Dad cried too. And hugged me.

I realized I had been doing Dad a disservice. "Now that you’re a full time woman, would you like me to call you something other than Dad?"

"I’ll always be your Dad, Honey. Now let’s see if we can get your face on without bawling again."

From that moment on, I thought of Dad as a woman and used feminine pronouns for her.

Dad was proud of what she had done. She uncovered a mirror and showed me Little Miss Fromage, Wisconsin of 2001. And a pretty little thing I was. It takes effort, ladies. Look at the women in the South. They’re pretty because they work at it. I intended to do just that.

Dad had a frilly summer dress for me, with flouncing skirts that fluttered in the wind. I was a little nervous about feeling that breeze on my pantied butt, but Dad said I would get used to it. I had been practicing with three-inch heels all week and had even gotten my wiggle down pat.

We drove to the neighboring town of Gouda and walked through their downtown shopping area. We were the only appropriately dressed women in the town, so the men were turning their heads quite obviously. Dad took me into a lingerie shop and I was almost overcome by all the pretty things.

"You can never have too many pretty panties, Caitlyn. And teddies. And stockings."

It was so much fun picking out that stuff, but I had a big woodie the whole time. Maybe I should have bought some SmoothPanties.

Then we went to a shoe store. Dad insisted that I buy three pairs of heels – sexy four-inch, red stiletto pumps, black, strappy, four-inch strappy sandals, and four-inch white mules. I felt so sexy trying them on. A small crowd of men had gathered and was watching through the shoe store window.

We laughed a lot as we teased the poor men, just by walking around. I loved the attention and wanted to see if a couple of those men were sissy fanciers. Dad discouraged that. We had a girlie salad lunch and arrived home at three, tired, but happy.

I kicked off my heels and sat on the couch.

"I have one more nice surprise if you want it, Honey," Dad said.

"What?" I asked eagerly.

"I’ve invited your best friend Rick for a sleepover tonight. For Caitlyn, not Eric."

I gasped for breath. Rick? Here? With me as a girl? I hadn’t seen Rick in the last nine, life-altering days, except at school. He had some band event and didn’t have any time either.

"Dad, does he know?"

"I made some hints and he was fine about it. Eager, in fact. I saw him in person. As Lisa. So I had some explaining to do. Don’t worry, Caitlyn, you just make yourself pretty. I’ll explain it all to Rick when he arrives at seven. Why don’t you take a little rest now. I’ll put these things away. I’ll lay out some clothes for you."

Had all the air left the room? I was going to sleep with Rick. My best friend. Whom I wanted to kiss since I was six, if the truth be known. Dad was helping me fulfill my every fantasy. She’s the best Dad ever!

The time came. I was very nervous, but knew I was a knockout when I finished dressing at seven. A pretty dress, stockings and heels. And my first eye shadow. Deep breaths. The doorbell rang. Dad answered it. They spoke for 15 minutes, then Dad called, "Caitlyn. Rick’s here."

I descended the staircase, just as Megan had for me a week earlier. It was so exciting to watch Rick’s jaw drop and cock rise. I felt my garters tug and my pantied bottom quiver for the cock I knew would be in there soon enough.

I kissed Rick on the cheek. He inhaled my perfume and trembled. We had been best friends since we were six and now we could be lovers. It was stimulating, but very confusing for us both. I was gentle and loving with him and he with me.

Dad took us in the family room. He wished us a good night and went off to his room.

"Your Dad is so pretty, Eric, I mean Caitlyn," Rick said.

"Yes she is, thank you, Rick. All those years she was really a woman and we never knew it. She’ll be much happier now."

"Does she have a boyfriend?"

"She does, but you know him, so I can’t tell."

Rick then made 20 wrong guesses as to the identity of my Dad’s lover. The last three were Sean Connery, Pierce Brosnan and Brad Pitt. We were giggling.

When we stopped, I asked, "Would you like to kiss me, Rick?"

"Very much, Caitlyn. You’re the prettiest girl in Fromage."

He hadn’t met Megan yet, but maybe he was right.

We kissed. Sparks flew. So that’s what kissing boys is like. Not bad. He rubbed my silky knee. I took that as a good sign of taking charge.

"Your legs are incredible, Caitlyn. So sexy." And another sign.

Then he reached under my dress and stroked my bare thigh above my stocking tops. I was getting hot and slipped Rick some tongue. That gave him all the confidence he needed to reach inside my panties and rub my bare pricklet as we kissed. Now we were getting somewhere. H e skinned my clittyhead and I squealed. He liked that. I liked that, but dresses aren’t cheap. I whispered, "I don’t want cum stains on my dress, Rick. Let’s get naked."

I believe that was a confidence boost for the lad as well. We went to my room and I gave him a Vegas strip show to my skimpies. Rick peeled all the way. Yummy, did he have a nice body. Hard and soft in all the right places. I had never seen his cock and balls and they were outstanding. Plump and juicy and ready for action. Dad must have given him some suggestions, because he laid me on my tummy on the bed, then got on his knees and began to lick my asshole. I had been the administrator of that pleasure, but not the recipient. I lasted one minute and 48 seconds. Then I had my first boy-induced cum. Rick was fascinated and delighted that he could make me cum. Then he got back to work to ensure that I was prepped for pork.

He licked me for ten more minutes and I had to think of spelling words and dates in American history to keep from cumming again. I wanted to let it go when he was filling me up. Finally the exquisite torture ended and he asked me if I would wet him for the attack. I rolled over onto my back and he straddled my shoulders, feeding me his cock. It tasted magnificent! The lad was fatally aroused and leaking pre-cum in buckets. I was licking the sticky stuff as it emerged. I kind of messed up his very sound plan by wetting his cock too much and kind of making him cum in my mouth. It was Rick’s first cum and it took him by surprise. Experience is the only teacher and his first experience was a ball-buster. When he settled down, he noticed that I was sucking him to a new erection. Being goal-oriented, Rick liked that a lot. Dad must have told him to fuck me in the ass, so he wanted to do that first. I had to shape the boy a little, but that would come later.

In a few moments, Rick’s cock was stiff and my pussyhole was wet and slippery. Ready, set, go. Rick kissed me, kissed my cock, licked my balls and placed my ankles on his shoulders. Then he poked around until I helped him put his cock in my secret place.

I had had fingers in there and they were very good. But the feel of Rick’s hot prick in my most intimate spot was beyond fantastic. I felt no pain, only a little pressure. Rick was obviously overcome with pleasure as well.

Every push rubbed against my tender prostate, drawing a whimper of ecstasy from my painted lips. Every push rubbed Rick’s tender foreskin against his sensitive cockhead. Every push erected my tiny nipples more, making them sore and sensitive to Rick’s tender licks and kisses. Every push rubbed my own little clitty against my soft tummy. Every push made me a happy girl.

We grunted and strained with animal lust. We emptied our balls, kissed, re-coupled and re-emptied.

I was a girl now. I knew it. I couldn’t give all this up for boyhood. Dad was right. I shouldn’t make the same mistakes he did

 

Chapter Ten – What Next?

I had an incredible night riding Rick’s thick bone. Then a better morning. Sex is something you apparently get better at. The boy was smitten with me. I guess I can smite with the best of them. He went home with sweet regrets, but honest promises of future passion.

Dad and I talked a lot that morning. I told her I was a sissygirl, like her, and that’s how I wanted to lead my life.

I was so stuck on my own issues that I didn’t notice that Mr. Bruder had visited Dad last night. He got on his knee and asked Dad to marry him. Dad said yes! The details would be tricky, but they were going to do it. Dad would wear a white satin wedding gown and Megan and I were to be bridesmaids. Hurray!!!!!! My sweet Dad, dearest Lisa, got her man.

She showed me her engagement ring. A two-carat rock. Dad and I hugged and kissed and cried happy tears. Dad said she would help me attend Miss Cynthia’s next year and I could live the life she was only beginning now.

We have a plan. We’re going to live happily ever after.

 

 

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© 2001 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.