My Three Sissies

by Gingerfred Man

 

Chapter One - No Bubs Here

 

I know what you were thinking when you read the title to this story. You thought, this is some Fred McMurray story about Mike and Robbie and Chip. With Ernie in and Mike out later on. And the biggest problem any of them ever has is whether to wear a white or red carnation on their dinner jacket for the prom.

No.

I’m no Fred McMurray and there’s nobody remotely like Bub, who looked an awful lot like Fred Mertz, or his ornery replacement, Uncle Charlie, in this story.

My name is Dave Benson and this is a story about how one day my life was pretty normal, if there is such a thing, and in the next days it was strange by most any definition.

It’s a story of love and hope and dreams fulfilled. Sometimes I felt like a spectator in my own life, but I was able to gain control and now my family is very happy. All of us.

Let me start with the low point. Three years ago, I found out that I didn’t know Alicia, my wife of 16 years as well as I thought I did. In fact, I was clueless. For two years, it turned out, she had been having a lusty affair with my soon-to-be-ex-best friend. An old story, but it hurt very badly, nevertheless.

The kids and I were stifling her spirit, she said, and the only thing she could do was leave us all. Forever.

At first I was devastated, but then I decided that forever was the exactly right amount of time for Alicia to be out of our lives.

Alicia escaped us so quickly and with such cowardice that she left most of her clothes behind. I wanted to burn them, but my mother taught me never to waste. So I just boxed them up and stored them in the basement.

My boys, they weren’t "ours" anymore, were crushed. Greg, 15 at the time, Matt, 13 and Sam, 11 felt horribly abandoned.

I did everything I could for them. I even found a job where I could work from home so I could be with them for all the things they needed. Still, I couldn’t give a mother’s love. Neither, apparently, could Alicia.

What I did give was very appreciated by the boys and I think whatever love they had for their ex-mom was dumped onto my love pile. Then doubled.

Still, it was tough. But we adjusted and grew stronger as a family. A year after Alicia and her stud headed for an unnamed coast, strange things began to happen. Things I don’t yet understand. But have learned to accept and even cherish.

 

Chapter Two -- Things

It’s tough for young kids to tell their friends that their mother found somebody she loved more than she loved them and ran away with him. Greg, Matt and Sam managed to tell their good friends in their own way. And in their own time.

I suspected that their friends were even more important to them than they were to most kids, so our house sort of became the neighborhood clubhouse for boys. I would always have plenty of juice and goodies for them and, except for school nights, there always seemed to be at least two boys sleeping over.

That seemed so innocent to me at the time.

I wasn’t easy on the kids. Just nice. I made sure that there were no drugs or booze or cigarettes. And I would always check on my boys and their guests during the evening and before I went to sleep.

I guess I just wasn’t vigilant enough. Not that it would have made any difference in the long run.

One night when Greg was 16, Matt 14 and Sam 12, Greg had his friend Russ over for the night. Matt had his friend Kenny. Sam was alone.

The boys’ friends were all good kids and I thought of each of them as almost my own. I was proud that their parents trusted me to have them in my house so much.

At around 10, I peeked in on Greg and Russ. They were playing a video game and having an excellent time. They hardly looked up when I said good night. Nice boys.

Matt and Kenny were watching TV. Matt gave me a hug goodnight and so did Kenny. Good kids.

Sam was young enough that he still gave me a nice goodnight kiss.

I walked down the hall to my bedroom smiling contentedly and went to sleep.

I almost always slept through the night, but that time, I awoke at around midnight with a rare headache. I took two aspirins, then, feeling parental, decided to check on the boys.

The house was dark. That was good. Sleepovers at my house weren’t stay-up-all-night affairs. I got to Greg’s door and froze. What were those noises?

I knew what fucking sounded like. Not that I had heard it in a couple of years. But the squeals and grunts and moans I heard from Greg’s room were unmistakable. Did Greg and Russ have girls in there? Or, oh please no, were they gay?

Slowly and soundlessly, I opened Greg’s door. My eyes confirmed my ears. But in a way I never imagined.

My son Greg was wearing a tiny pink nightie, a ribbon in his hair and what appeared to be lipstick! He was on his back, with his legs hooked over Russ’s shoulders. Russ was naked and on top of Greg, fucking his bottom with long, slow strokes of his apparently large and very wet cock. Greg appeared to be enjoying it immensely. He was squealing softly and girlishly and moaning for more. He and Russ both had their eyes closed, so they didn’t see me.

I wanted to scream at them. Or get an ice-cold bucket of water and throw it on them. But the truth was, my kids had been hurt enough. I had to find a better way to deal with this awful turn of events.

I staggered out and closed the door softly. I stood against the wall and breathed very heavily. I’m ashamed to say that the most depressing thing was that I had a major, throbbing erection.

By rote, I moved over to check Matt and his friend Kenny. I stood in front of Matt’s door and listened. Was I hallucinating? I swore I heard more grunting and moaning. I eased Matt’s door open. Kenny was leaning against a wall with his eyes closed. He was enjoying himself very much. My son Matt was wearing a white babydoll, white, seamed stockings and very high-heeled white mules. I could only see his back because he was on his knees, expertly and enthusiastically sucking Kenny’s stiff cock. I was too horrified to look for long, but did see Kenny’s prick erupt a gallon of hot cum into Matt’s giggling face and slurping, eager mouth.

I backed out silently and stood there in shock. What had I just seen? Oh no! Was Sam…..? I rushed to my 12-year-old "baby’s" room and saw him sleeping soundly in his boy’s pajamas. Thank goodness!

What was I to do? I staggered back to my room to think. I lay on my back and my head swam. My boys were gay. I could have accepted that, maybe, but they were <gasp> crossdressers too. Dressing like girls. Sucking boys cocks until the boys made cum on their tarted-up faces. And in their mouths! Then the boys would lift their nighties and put their big, hard things into my Greg’s and Matt’s tight, little holes. Didn’t that hurt? It probably….Oh…..it was…….Please, don’t let me be excited by seeing……..Goodness…..My gut clenched and my cock exploded hot cum. And then again. I was so ashamed. Of myself. And my boys. What would I do?

I tried to figure out why it was happening. Had I failed as a father? I knew it was tough as a single parent. What had I done wrong? Was I being too hard on myself?

Wait, I thought. It must be Alicia’s Uncle Jerry. That was it. The family always suspected Uncle Jerry, the confirmed bachelor. Hah! Him and his fancy ways. Going to the opera and wearing cologne! He even lived in California! He had to be gay! And here I thought Greg and Matt had only met him once or twice. He must be here in Fromage, Wisconsin! Probably sees the boys secretly all the time. Wooing them to that gay lifestyle. Making them choose gayness. Maybe even <gasp> molesting them! I resolved to find that old pervert and kick his ass. Then deprogram my boys somehow. That calmed me down a little, but my cock was still hard as bricks. Thinking about guys dressed as pretty girls. Sucking guys cocks. It was horrible! Still, I would never get to sleep if I didn’t just relieve the tension a little and ohhhhhhhhh. That was better. Uncle Jerry, the faggot. Hmmmppphhh.

 

Chapter Three – Uncle Jerry’s Exoneration

I fell asleep and awoke around seven full of resolve. I got up and made a huge Sunday morning breakfast for my boys and their two houseguests. Oh, I prayed that Russ and Kenny wouldn’t be spreading rumors around school. It wasn’t Greg and Matt’s fault. It was Uncle Jerry.

Forcing myself, I was cheery with everyone and when Russ and Kenny went home, I stood at the door to make sure there weren’t any goodbye kisses. My boys went off to get dressed and straighten their rooms. I slipped into Greg’s room and closed the door.

"Yeah, Dad?" he asked, in that nice, non-gay way I loved.

The direct approach is best in such cases, so I got right to the heart of things. "Greg," I said. "I know all about you and Uncle Jerry." That was the way to put him on the defensive and have him explain himself.

He looked at me oddly, then said, "Who?"

"Don’t act innocent with me, young man. Your mother’s Uncle Jerry."

"Oh, him. I forgot all about him. I haven’t seen him in years."

He seemed to be telling the truth, but as I suspected at the time, all gays lie. I pressed. "Well then, how do you explain Russ pushing his hard penis in and out of your bottom last night while you were dressed as a girl?"

Less direct than the Uncle Jerry line of questioning, but I thought I had reached him with that one.

Poor Greg’s face went ashen. He trembled a little and tears formed in his eyes. I wanted to hug him, but tough love was called for here. I waited.

"Dad, I’m sorry that’s how you found out. I should have told you." Then he really began to sob and the heck with tough love. I held my dear child in my arms and comforted him.

When he calmed a little, I said, "Tell me about it."

"I’m not gay, Dad. And the last thing I would ever want is to harm you."

I knew that.

"I know it looks like I’m gay. I do like making love with boys, but only because I’m really a girl. A sissy is what you might call me, but I’m a girl."

He looked at me, letting that sink in. It pooled up on the surface of my brain, but didn’t penetrate.

"Greg, I’ve known you from the instant you were born. Your flesh is my flesh. And I’m sorry, Honey, but you’re a boy."

He looked at me, wondering how to explain. "Dad, I know I have a boy’s body. But my spirit and soul are a girl’s. And they always have been. Didn’t you ever notice that I’m different from the other boys? And that Matt and Sam are different too?"

Goodness! I had almost forgotten about Matt and that Kenny. I would have to deal with that. And poor little Sam. Was he infected by his brothers? My boys were always a bit different. They were nice and polite and seemed to care about other people. I always thought they had been raised well and were naturally good boys. What was he telling me?

"I guess so. How did it happen? This girl stuff." I asked.

"I don’t know, Dad. It’s probably genetic."

Horrors! Had I passed this along? Was I a cocksucker too? It must have been Alicia, although she never showed a lot of interest in sucking my cock.

"Tell me about it. Everything."

Greg did.

 

Chapter Four – Greg’s Story

"Dad, I don’t want to hurt you, but I’ll have to tell you everything and give you some explicit details, OK?"

I gulped and nodded.

"I guess I knew for a long time that I was different. I used to look at little girls at birthday parties and just want so badly to wear those frilly dresses and satin Mary Janes. I never got to wear them, or the frilly socks. I guess I never will. But I knew I wanted to. I still do. And I’ll bet I would look pretty good in them."

The picture formed in my mind. Greg did have sort of a pretty face. And I did always wish that we had had at least one girl. But that was wrong thinking. Blot it out.

"Still, Dad, I thought there was something wrong with me. Something that I could just work at real hard at forgetting and it would go away. It didn’t. Then it all sort of came out at once. Right after Mom left, I was feeling depressed. Jason asked me to spend the night and you said it would be good for me, remember?"

"Vaguely. Go on."

"Well, Jason and I had been friends since the first grade and he was probably the one person in the world, besides you, Matt and Sam, who really understood me."

It was kind of Greg to include me in that list, but it appears that I didn’t understand him very well at all.

"Anyway, Jason and I watched some videos and hung out. Then we went to bed. He has a big double bed in his room so when I stayed over, we would always share it. We always slept in our underwear and stayed on our own sides of the bed, so it was OK."

True, but volatile, nonetheless.

"I was very fragile emotionally from Mom leaving and that night, I began to cry. I thought I was being quiet about it, but Jason heard me and he did the strangest thing. I was lying on my side, facing away from him. He spooned up behind me and hugged me, rubbing my arm and saying, ‘It’s all right, Greg. It’s all right.’

"That was so totally unexpected and so sweet that I rolled onto my back and started sobbing more loudly. Jason got on his back and reached around me and hugged me. He just let me weep as he held me and stroked my arms. Then for about an hour I gasped out all the bad stuff I was thinking about and it just sort of left me. Jason listened really well. I felt something for him at that moment that I had never felt for anyone before. And then it just happened. He kissed me."

<Gasp> Then it was Jason’s fault that my boy was gay! I would kick his ass right after I kicked Uncle Jerry’s, who had to be guilty in some way.

"Dad, it was the greatest moment of my life. I kissed Jason back and he held me in my arms and I felt I was a girl with a boy who understood me.

"It was wonderful, Dad."

It sounded horrible to me. But why was my cock so stiff? "Then what?" I asked him.

Greg blushed a little, then said, in a low voice, "Then he made me cum. A lot."

Oh my goodness. My cock was really becoming distracting.

"Jason reached into my boxers and fondled my balls, tickling them very nicely. And he kept kissing me. I was in heaven. Then he <blush> stroked my penis. It was very nice. Especially when he rubbed the head with his thumb and spread my sticky goo around as he kissed my lips and licked my tongue. I couldn’t help it, Dad. I arched my back, squealed like a little girl and started ejaculating helplessly. Spurt after creamy, sticky spurt. I was gasping for air and crying it was so good. Are you all right, Dad?"

<Gulp> "Yes, Greg. Thank you. I guess I’m just upset by what you’re telling me." Actually, I had cum four thick globs into my Jockey briefs. Thank goodness I had dark pants on that day. Why was I so aroused?

Greg looked very concerned. "Please, Dad. Don’t be upset. You know I love you. I didn’t do any of this to hurt you or the family. It’s how I was made. It’s who I am."

Then my sensitive, sweet Greg hugged me. I hugged him back, keeping him clear of the wet "evidence" by my crotch. I loved him so much, but could I love him as a queer?

"Thanks for the hug, Dad. Please don’t think I’m gay. I’m not. And the next part of the story proves it. I wanted to do something nice for Jason, but he got up and left the room. That upset me a little, but he was back in less than two minutes, carrying something yellow. Jason’s sister Katie was away at college and had left some of her stuff behind. Jason found one of her yellow nighties and asked me to put it on. I blushed again. How did he know? It was a relief to me to know that Jason considered me a girl, so he wasn’t gay either."

I was trying to remember who said, "If it walks like a duck, quacks like a duck and swims like a duck, it’s a duck."

Greg continued. "I stripped off my tshirt and boxers and stood naked before Jason. His eyes were very big, and they illuminated when I slipped my first nightie over my head and posed for him. I sneaked a look in Jason’s mirror. With a little make-up and some work on the hair, I could have passed as a girl. Jason certainly thought so. I could see his big cock throbbing when he removed his boxers and tshirt. I was almost drooling looking at his beautiful body. At the same time, I was enjoying the feel of the cool, silky nightgown as it caressed my nipples and gently scraped my ballbag. I was as hard as a geometry final all over again."

So was I. What was happening to me?

"Jason stepped forward to hold me again and I just let him dominate me completely. He cupped my bottom cheeks in his hands and lifted my mouth to his lips. He rubbed his hard cock against my nightie-covered belly and I was afraid he would cum and I wouldn’t get to fully participate. I broke off our kiss and said, ‘I’m going to get on my knees and suck your cock now, OK?’ I thought the throaty grunt meant yes, so I hit my pretty knees and held my prize – a lovely, stiff cock with a big bag of cum-filled balls! I rubbed it all over with my hands and kissed the velvet head lovingly. Jason liked it a lot. I cupped his balls with my right hand, stirring them a little as I began some serious work on his big, pink mushroom. That gooey stuff was leaking like crazy, but I was licking just as fast as it was dribbling. I loved the salty taste. I loved being in control, yet serving my man and meeting his needs."

Women could take big lessons from my son, I thought.

"Jason grunted a lot, but he managed to tell me how pretty I was and how good a cocksucker I was too. Every girl loves hearing that! Then he kind of lost control and I got my first ‘girl’s big reward for a job well done.’ Jason shot five huge globs of hot cum right into my giggling face. I only saw the first two, because the third one hit my eye. I learned how to avoid that since then. But I felt each hot blast as it doused my face. It was wonderful."

I shifted my bottom uncomfortably. I was afraid my diamond-cutter was going to be naughty again.

"We kissed for a long time after that, Dad, and I told Jason all about how I always wanted to be a girl. He surprised me, Dad. He said he had suspected it for some time. Especially after he had done his research."

"What research?" I asked.

Greg went over to his closet, reached in deeply, and extracted a large, oversized comic book. He handed it to me and said, "This."

It was indeed a comic book entitled, "Making Friends: A Spermco Publication." So it was clearly smut. Just looking at the cover, though, one could only see a well-drawn, detailed, black and white sketch of a pretty teenage girl in a very short skirt and very high heels. She was very attractive, with beautiful legs and a lovely face. Her hair was cut in a boy’s style, but had a very large ribbon atop it. I was about to open it, when Greg said, "Dad, all this talk has me in a bad way. Could you excuse me for a bit while you read that?"

"What is it, Greg?"

"Jason said it was that book that told him what he needed to know about me. Can I take care of my needs, Dad? Please?"

"One last question. How did Matt become a ‘sissy?’ Did you force him?"

"I didn’t even know he was a sissy, Dad. Honest. Please ask him, Dad. We’ll talk later."

Greg was clearly in distress. Was he going in the bathroom to masturbate? Still, he looked so uncomfortable that I let him go and walked back to my room.

 

Chapter Five – Source Material

I dreaded hearing another story like Greg’s from Matt. And I knew that I would have to talk to Greg a lot more before I understood what happened to him and could get him to give it up and return to normal. I only hoped that he didn’t have such a reputation with his peers that we would have to move. All those boys getting their cocks sucked by my Greg and Matt. And putting their big things in my little guys’ tiny holes. It was awful!

 

I began to think about what it would have been like to know sissies like them when I was in high school. Kissing them in the boys’ locker room. Pulling their panties down and fondling their little prickies. Kissing them some more. Making them squeal and cum. Then watching them get on their knees and take my cock in their mouths. Oh. Every boy in school knew about Greg and Matt, I was sure of it. And every boy wanted them. Boys love sissies.

I was very stimulated by the time I got back to my room with the "Making Friends" comic in one hand and my cock in the other. What was happening to me? I clearly needed some relief, but I needed to look at that evil book first.

I lay on my bed and opened it. Oh my. The drawings were very well done and very erotic. It was a story about a boy about Greg’s age then who was living with his beautiful, sexy, big-breasted, high-heeled aunt. Each day, when he came home from school, the aunt made him dress as a girl. A very sexy girl, with fantastic lingerie, five-inch heels, stockings and very short skirts. He also wore beautiful make-up that made him look like an angel and just the sight of him dressed with his prick sticking up to tent his skirt made my poor over stimulated cock spurt a huge, sticky load. If I had been standing, it would have brought me to my knees. What kind of a world was I entering here? Why had I never been that excited before in the everyday world?

Cum was all over my stomach and my tshirt, but I turned the page. The boy, whose name was Eddie, complained all the time about dressing, but his cock was boulder-hard the whole time he was in girl’s clothes. Up until that point, the aunt had kept Eddie’s dressing a secret, but that day she said to him, "You look beautiful today, Dear. That’s good, because I’ve invited two of your little friends from school over – Spike and Buster."

Eddie, beautiful angelic Eddie, was frozen with fear. He said, "But Auntie, they’re the two worst bullies in school. They’ll hurt me! They’ll ruin my life!"

The aunt said, "Nonsense, Dear. They’re just going to take you for a nice walk in the park."

Eddie was in great distress, but the doorbell rang and the two bruisers were admitted. They leered at the terrified Eddie, whose aunt ignored his tearful pleas to stay home alone. He accompanied the two thugs to his presumed doom. The nasty boys each took one of Eddie’s arms and led him into the woods.

Eddie and the thugs reached a private sylvan spot and they began to tell Eddie how pretty he was. This only made Eddie more scared, but his cock was tenting his miniskirt. Buster kissed Eddie as Spike got on his knees and pulled Eddie’s panties down. Eddie was surprised that they intended to make love to him rather than pulverize him, but that was apparently only marginally better in his view.

Eddie was no homo, he thought, but his cock was outrageously stiff when Spike began to kiss and lick his balls as Buster kissed his neck and skinned the head of Eddie’s prick. Eddie’s face was confused, but his cock knew its mind. He spurted big gobs of cum from all the male attention and so did I when I saw that drawing. What the heck was happening?

I was breathing heavily and was gooed up with sticky cum, but I had to see how the story turned out. Eddie begged Buster and Spike to take him home, but those lads were just getting warmed up. Eddie was sobbing big tears and asking Buster to stop, but his prick was stiff as Buster performed enthusiastic pooper-lingus on Eddie’s tight hole. Despite himself, Eddie erupted another huge load of hot cummies.

Oh my goodness. They were FORCING him and he was sort of resisting, but his cock was blowing out load after load.

Eddie’s worst fears were about to be realized when Buster placed the wet tip of his huge, stiff cock at the entrance to Eddie’s hole. Eddie’s panties were pulled down to mid-thigh and he was stiff as a double bourbon neat. He was still crying, but he wasn’t saying anything because Spike had stuffed his dark, thick cock into Eddie’s mouth.

Poor Eddie. He was being taken against his will. But he was again splashing gob after gob of sticky jism onto the ground. In the next picture, Spike’s cock had erupted and cum was running from Eddie’s mouth and down his chin. In the next, Buster was twitching as he poured a river of goo into Eddie’s bottom. Cum was running down Eddie’s thighs and drooling onto his stockinged thighs. Eddie seemed to have stopped resisting as vigorously as he had been.

I turned the page. In the next picture, Eddie and Spike were lying on their backs. They were kissing with great enthusiasm and ardor. Meanwhile, Buster was kissing and licking Eddie’s once-again spurting cock.

Well, Eddie seemed to have had a change of heart. He was so feminine and innocent. And when he surrendered to his true nature it was so exciting that I……..Oh, no. I was cumming again! Wasn’t I too old for that? Why was I so excited? Why weren’t my balls dried up yet?

Buster and Spike took the cum-covered Eddie back to his aunt. She stood looking out the door as Eddie kissed both boys goodbye, with lots of tongue. And a lot of rubbing bodies. Eddie even got down on his knees and sucked them off in succession – right at the door.

The boys left and Auntie greeted Eddie warmly, with a big, tonguey kiss. Eddie hugged his aunt, who was wearing only lingerie under a black peignoir with very, very high heels. Eddie said, "Oh, thank you dear Auntie for forcing me to do what I always wanted to."

"You’re welcome, Eddie," Auntie said. Then Auntie sat. Eddie got on his knees and fished Auntie’s big, hard cock out of her panties. He sucked it very nicely until Auntie blew a big, hot load into Eddie’s smiling face.

It was the most exciting piece of literature I had ever held. It had all sorts of new ideas for me. Young boys dressing as girls. Against their will. Then willingly. Male-on-sissy sex. Forced. Then willing. Male-and-male-on sissy sex. A beautiful, sexy woman with a cock. Being willingly sucked off by her nephew. Who’s wearing stockings, heels and make-up. Oh my!

My brain was on overload. My balls were arid. I was exhausted. I must have passed out, because I woke up an hour later. I had to resume my role as a father, talking to Matt about his "perversion" and making sure the same didn’t happen to Sam.

First, I had to take a shower. I smelled like a 25-cent video booth at a porn shop. I got in the tub and cleansed myself, aware that my cock was once again stiff and ready. I gave it a pat, but told it to wait. At the end of the day, I was going to give "Making Friends" a closer look. But for then, I dressed and found Matt.

 

Chapter Six – Another Sissy Blooms

Matt was in his room reading a book. Had Greg told him what I knew? Probably. But Matt didn’t seem disturbed about anything.

"Hi, Dad," my middle child said. "I’m sorry you had to learn about Greg and me the way you did."

So. He was taking the lead. I have to say, he had guts. I said, "I can get you and Greg some help, Matt."

Matt smiled. "Dad, we’re sissies. We’ll never change. It’s how we were made."

Why did they keep saying that? It was obviously wrong.

"Did Greg tell you that? Did he make you do all this? Have you been talking to your Uncle Jerry?"

"Who?"

Maybe that theory was a bit leaky.

"Dad, I didn’t even know Greg was a sissy until he and I had been making boys happy for quite some time."

But… "What happened?"

"It all started about a month after Mom left. Actually, it started when I was six years old and I wanted to wear dresses and pretty ribbons and play with dolls, but I could never tell you that."

Matt too? Was I blind? Was I looking at all the wrong things? Was it my fault or the boys’ fault? Was Sam infected too?

"I went to Billy’s house for the night – my first sleepover since Mom left."

This was sounding like Greg’s story. Should I be taking notes for the analysts I would send them to?

Matt continued. "Billy and I had a really good time. We always did. I knew Billy since kindergarten and sometimes I used to imagine that he was a sissy too. But he never let on. When it was time to go to bed, Billy kissed his Dad good night and his Dad hugged me. I always liked Mr. McCue and I felt really bad when his wife, Billy’s mom, died."

Me too. John McCue was a good guy. Mary suffered way too much for a good woman.

"Anyway, we went to Billy’s room and started to get undressed for bed. I got out my pajamas and Billy reached in his drawer and pulled out a pink nightie! Dad, I almost fainted when I saw it. And my penis got very hard. I’m sorry for telling you that, Dad, but it’ll help you understand."

I nodded. My little friend was becoming naughty again too.

"Billy just slipped that nightie over his head as innocent as a lamb. Then he went into the bathroom to brush his teeth. When he came out, I was still standing there, holding my pajamas in one hand, staring at that lovely pink nightie and the boy in it.

"Billy looked at me and said, ‘What? Don’t you wear a nightie? I thought you were a sissy just like me.’

"Dad, you could have waved a feather in the next room and I would have fallen over. I asked him, ‘How did you know?’

"’I don’t know,’ he said. ‘I just knew. Didn’t you know about me?’

"I did. I really did. But I wasn’t confident enough to admit it. I vowed to myself at that moment that I would never miss out on life because I was afraid to accept my own judgment.

"Billy said, ‘Would you like to wear one of my nighties?’

"I wanted that very much, Dad, so he gave me a pretty blue babydoll. With matching panties! I was trembling as I put on my first panties. It was the greatest moment of my life at that time. I was so excited that I gooied my panties in big creamy spurts. I blushed, but Billy was so understanding.

"’It’s OK, Matt,’ Billy said. "You don’t need panties for sleeping.’

"Shuddering with excitement, I slid the nightie over my head. It felt fantastic! Dad, you have to try wearing one."

I harrumphed.

"OK, maybe not. But I loved it. And still do. Billy said I should look at myself in the mirror and I gasped when I saw how pretty I looked. Billy had a big smile on his face when he offered me some lipstick. He put it on first, showing me how. Then I put it on. I felt transformed. I felt pretty. Then I got worried.

"’Won’t your Dad catch us, Billy?’ I asked.

"Billy smiled and told me not to worry about that.

"I was happier than I had ever been. Like me, Billy had short hair and looked like a boy in a nightie wearing lipstick. But he looked like a beauty queen to me. I kissed him. He kissed me back."

Matt’s story was doing it to me again. I felt the first warning for an orgasm. That was an improvement. The others just knocked me flat without warning. How would I have any credibility with my sons if I kept cumming in my pants when they told me their sins?

"It was wonderful, Dad. It was my first kiss and it couldn’t have been better. We rubbed our cocks against each other and Billy fed me his tongue. We kissed hungrily and rubbed. And kissed. And then creamy cum spurted from my cock. It went all over Billy and he made a big cummy mess too! Oh, Dad, it was intense. My knees buckled."

Mine quivered as I made sticky cream yet again in my pants. I hoped Matt didn’t notice, but the lad never missed much.

"Then we got into bed. I lifted my nightie and Matt began to kiss my nipples really nicely. There must be some rope that goes from the nipples to the balls, Dad, because I came again, really hard. Billy giggled and then as I was still cumming, he capped my cock with his mouth and caught the last two big spurts. He kept sucking me until I got hard again, then came into his warm, wet mouth. Oh, Dad, I’m sorry. Can you excuse me?"

Matt ran into the bathroom as I sat there stunned. My son was in there whacking his wiener because of my intensive interrogation technique.

I was almost fainting myself, and would have been happy to go to my room, lock the door and read the world’s nastiest comic book for about eight hours.

But I needed to get the truth out of Matt. That didn’t seem to be very difficult, since he was giving not only the truth, but telling it in detail.

He looked flushed, but a bit relieved when he emerged from the bathroom.

I started things off. "Ahem. So, did you do ‘things’ to Billy too, Matt?"

"Oh, yes, Dad. I couldn’t wait to suck Billy’s cock and swallow his cum. I put him on his back; lifted his nightie and licked off all the cum from our kissing explosion. I had never tasted cum before, and I loved it! All of us sissies do, Dad. Billy was squirming and making little squeals. He was really enjoying it and that made me really happy. Then I took his little pink prick in my mouth and licked. Mmmmmm. I was tickling his balls and licking and sucking his pretty mushroom and he was gasping and panting. Then he screamed and blew wads of hot cum into my mouth. Mmmmm. I swallowed it all. Being a sissy is the most fun there is, Dad!

"Then things got a bit more interesting. The door opened and Mr. McCue looked in. Billy was on his back gasping for air, holding his pink nightie up to his nipples. I was on my knees, wearing a blue nightie, with my bare bottom wiggling as I sucked his son’s cock and swallowed his cum. Busted!!!!! My heart sank. Then I realized that Mr. McCue was wearing a long black nightie, with four-inch heeled mules, make-up and a long, blonde wig.

"’Everything all right, fellas?’ Mr. McCue asked.

"’Yes, Dad,’ Billy gasped.

"’OK. Enjoy yourselves. I’ll see you in the morning.’ And he closed the door.

John McCue was a cross-dresser? And he let my boy suck his son’s cock right in the house? I was outraged! I was sick to my stomach! I was wondering how he looked in his girlie things. I was pretty sure he looked cute. He had such a sweet face and was very slim. But I was still outraged!

Oh my goodness, did I need to relieve myself again? I did. "I’ve heard enough for now, Matt. I don’t know what I’ll have to do, but I’ll have to get you boys cured."

Matt looked at me with eyes too old for his years. He said, "It’s not about curing, Dad. It’s about accepting. And I know you love us so much and we love you so much that when you understand a little better, you’ll accept us."

What a mature, though totally wrong thing to say! I was impressed. I was also firm in my resolve to cure my boys. Right after I rubbed my prick until it exploded whatever cum was still hanging around the walls of my ball sack.

Matt ran for his bathroom and I ran for my room. I locked the door, grabbed "Making Friends" as I pulled my pants and boxers down, and lay on my back.

I patted my big, thick, rock-hard monster. It was having an energetic day. I opened the book to a picture of Eddie bouncing up and down on Spike’s cock as Buster fed Eddie his meat stick. Cum was drooling from Eddie’s cock, bottom and mouth. Eddie was so humiliated, that he was crying. The shame of being a boy who was USED by other boys for sex was intense. Yet Eddie’s cock was hard and spewing. And spewing. There was no pretense that Eddie was a girl in a boy’s body. He didn’t have a girl’s name or haircut. He was wearing stockings and heels, but he was a boy, servicing members of his own sex. Being degraded by them. A cocksucking sissy. Horribly shamed. And totally orgasmic.

Why couldn’t real life be like that, I thought as I shuddered and came for the who-knew-how-manyeth time that day. Then I thought, for my boys, it was.

I didn’t really mean any of that. Strike that. That was my cock talking.

Were my dear children sucking off all the boys in Greg’s high school? And Matt’s junior high? Oh, please no. That Billy McCue boy started it all with Matt. The little faggot! And his queer father. I should go over there and give John McCue holy hockeysticks, I thought.

But what if I got there when John was <gasp> dressed? What if he invited me in and tried to seduce me? Casting some queer spell on me and sucking my cock. On his knees in his pretty lingerie, stockings and heels. Oh…..No….I was cumming again!!!

I was going to need to walk around with an IV bottle if this continued. There was no doubt about it.

I was as screwed up as my boys were at that moment. Or were they screwed up? Maybe I was the one who was screwed up. Of course not. I had society behind me! And society is never wrong! OK, about the holocaust, slavery and burning witches. And about absolute monarchies and electing Richard Nixon. But that was it! I was clearly RIGHT!! Still, the idea of visiting John McCue made my heart beat very fast.

Somehow, I got myself together and went to check in on Sam. He was outside throwing a ball against the wall. Thank goodness! A boy’s activity.

"Hi, Dad," he said.

"Hi, Sam. Everything all right?"

"Sure, Dad. How about you?"

"OK. Say, Sam. Did you notice anything unusual about your brothers?"

"Unusual? No, Dad."

I treaded cautiously. "I mean, with their friends and all."

Sam thought. "Oh, you mean that they’re sissies and have sex with boys all the time? I thought you said something unusual."

It was worse that I thought.

 

Chapter Seven – Sticky Situation

Thank goodness, Sam had noticed but wasn’t participating. The sensible boy told me he was too young (12) for all that. Anyway, he wasn’t sure what he was yet. Maybe I could save him, at least. But how?

The rest of the day was a blur. I couldn’t go through any more of those openly gay stories from Greg and Matt, so I sort of avoided them both. We ate together, but talked of other things. They didn’t seem gay, whatever that was.

Now that the cat had escaped the bag, Matt and Greg wore pretty little nighties for sleeping. They admitted that they had been drawing their femmy supplies from their mother’s things that I should have thrown away.

They came and kissed me goodnight and tears came to my eyes. It was almost like having daughters. But they weren’t, really. What were they?

I went to bed exhausted and fell right to sleep. Sometime during the night, I heard noises. Someone was in my room with me. But I knew I had locked the door. I looked and saw my two giggling sons, Greg and Matt. They were fully made up, even wearing long blonde wigs and very short nighties, stockings and garter belts! I slept naked as always and Matt pulled the covers off me. Matt lay on top of me and kissed me, putting his tongue into my mouth. It was wrong and evil. I wanted to push him off me and shout, but I couldn’t do either. Then Greg began to stroke my cock and tickle my balls. It felt incredible. But I was trembling from shame. And lust. Matt kept kissing me and he began to rub his stiffie against my stomach. Then Greg took my cock in his mouth and began to suck me better than his mother ever had. Oh, Sweet Goodness! The evil, incestuous boy wet his two fingers and slipped them into my bottomhole, something his mother was very good at. He moved them in and out as he sucked my cock. I didn’t want it, but it was happening. I tried to scream. I tried to get away. But instead, I blew the biggest cum load of my life.

Then I screamed.

Then I woke up.

My chest was heaving and I was sweating cold bullets.

My stomach and the sheets were sopping wet with cum.

What was happening to me?

The next morning as the boys and I were having breakfast before school, I asked Sam to leave us.

"Boys," I said to Matt and Greg, "I want an honest answer. Do you ever have sex with each other?"

I got an honest answer. They both screwed up their faces and said, "Ewwww, Dad. That’s sick. Of course not."

My first good news. Of course I was still a sick pervert for dreaming about such things. Freud said you can’t blame yourself for what you feel. Was he right?

 

Chapter Seven – More Unwanted Revelations

That afternoon, when the boys got home from school, I had screwed up the courage to ask them for more details. I had also cum six times looking at that darned "Making Friends" book.

Sam was in his room doing his homework when I asked Matt and Greg about their days. As usual, they startled me with their frankness.

"It was like every day, Dad," Greg said. "The boys were all over me. They all love sissies."

"What does ‘all over you’ mean, Greg?"

He looked at Matt and they exchanged a knowing smile. Greg said, "Well, I’m not the only sissy in the school. This is Fromage, Dad. But I think I’m the prettiest. James Nicholas took me into the third floor boys’ room at lunch. We got into a stall and he started kissing me. He’s a good kisser. Then he pulled my khakis down and reached into my silky panties."

I blinked. "You wear panties to school?"

My boys looked at me as if I were in the slow group. "Dad, we always wear panties. Why do you think Matt and I volunteered to help you by doing laundry? We’re not saints!"

Good point.

"Anyway," Greg said, "James is a really great kisser and I was getting very hot and my cock was dripping sissy goo. James was using his thumb to rub my spermies all around my pink mushroom and it felt so good. James is so big and strong. And handsome. But he’s crazy in love with me, you know?"

I didn’t. But I nodded.

"All the other sissies in school are so jealous that James loves me."

"Are there lots of other sissies in school?" I asked.

Greg and Matt giggled. "Of course, Dad. There are LOTS of us," Greg said. "James says that my sissy cream is the tastiest thing in the world. He stood me on the toilet seat, pulled my panties down to my knees and pulled my cock out. James went after it like a starving man, licking and slurping its tender, sensitive head in his mouth. Telling me how much he loves me. Tickling my balls and then <gasp> putting his two big, thick fingers into my bottomhole and massaging my prostate with them. Matt, <Pant> could you?"

"Sure, Honey," Matt said. And to my amazement, my middle son pulled my eldest’s pants, then panties down and began to skin his cockhead, up and down. Slowly, sensuously, until BAM, Greg, whimpering, spurted three big globs of sissy cream into Matt’s handy Kleenex.

"Thank you, Sweetie," Greg said to his brother. Then he kissed him lightly on the lips.

I was angry! "You boys lied to me! You told me you didn’t have sex with each other and you did that?"

The boys looked genuinely puzzled. "Dad, that wasn’t sex. That was milking. Sissies need to be milked several times a day or we get sick. It’s a medical fact. Didn’t you know that?"

I did know that, but had only learned it earlier that day when I looked up a lot of things about sissies on the Internet and found that, as from the beginning, they were telling me the absolute truth about everything, including milking. And sissies shouldn’t be milking themselves. It was OK when other sissies did it, better when boys did it, best when men milked the cream from their baby balls.

"Can I tell you about the rest of my day?" Greg asked sweetly.

I surrendered and asked him to proceed. If I hadn’t been cumming all day long, I would have been running off to the bathroom myself.

"James really loves me, Dad. I keep telling him I’m too young for a relationship, but he tells me he dreams about me all the time. I have that effect on boys, and so does Matt. Remember when he slept over last weekend? He porked my little pooper all night long! Eight times! I was kind of sore, but sissies don’t deny their boyfriends. He kept waking me up. A couple times, he just sucked me off and swallowed my sissy cream while I was still sleeping. He’s crazy for me! Anyway, James was wiggling his big, thick fingers in there so very nicely and licking my cockhead and I made a big cummy mess all over his face. But he didn’t stop. He kept it up and made me cum two more times until lunch period was over. Oh, Matt. Are you OK?"

Matt looked very uncomfortable. Greg asked, "Should I….?"

Matt looked at him, then me, and said, "Maybe Dad could milk me."

The little tramp! I couldn’t. My throat went dry. And my cock was boring through my belly button.

Matt pulled a beautiful penile specimen out, stroked it a little and, batting his beautiful eyes said, "Could you, Dad? It really hurts. And I really need it."

Oh. Would I laugh with the sinners or cry with the saints? Would I choose convention or help my distressed baby boy?

Trembling, I touched Matt’s foreskin. He gasped, then sighed as I worked my hand up and down his throbbing little jewel. Matt shuddered with pleasure. Even though it was just a medical procedure. He kept looking at me shyly through beautiful, though downcast eyes. Oh my. Was this my future? I resolved that milking would be as far as I would go with my boys. And I have to tell you right now that I’ve kept that resolve. Although I have added a few innocent refinements over the years, such as some light kissing and prostate massage before, during and after the medical procedure.

Matt’s breathing told me he was close. Greg produced a Kleenex and captured the majority of Matt’s thick juices as they escaped his sore, red pole. He looked at me lovingly and I knew that my relationship with my boys would never be the same.

Greg smiled, hugged me and said, "Thanks for understanding, Dad. Can you take care of me like that before bed, when I have my pretty nightie on?"

Who made these boys such teasers?

Maybe things wouldn’t be so bad around our house after all.

 

Chapter Eight – More Research

I was horribly confused and agitated, but tried to act "normally" the rest of the evening. We had meat loaf, mashed potatoes and green beans. The boys did their homework, then Sam sat down to watch the first half of Monday Night Football. A good sign for him, no? Matt and Greg were in their rooms listening to music and on the phone with, I imagined, some of their legion of male admirers.

At ten o’clock, Sam went to bed and my two lovelies came out for their bedtime milkings. They were gorgeous little angels! Sissy perfection in perfect make-up and matching pink babydoll nighties with little white lace and ribbons. Their legs were shaved and their toenails were painted hot pink.

It was wrong!!!! But what could I do? Just because you don’t believe in gravity doesn’t mean you won’t fall when you jump out a window. They were sissies. That was reality. I had to deal with the world as it was.

I was hoping that we could keep this as clinical as possible, but the boys had other plans. Each sat on one of my knees and, in succession, gave me a sweet, no-tongue-but-full-lips kiss.

Oh.

Parents weren’t made to handle situations like this. Then Greg stood and pulled his wispy pink panties down, exposing a thin, but beautiful sissy stick, with throbbing veins and a lovely bag of spherical accessories. Matt stood behind him. I touched Greg’s cock and he moaned with delight. I pulled the skin down, exposing all his pink parts. He gave the cutest little squeal. No wonder that James character loved my boy. He was feminine perfection. I continued to manipulate his little charmer in the best way I knew how. Then Greg grunted softly. Matt’s had entered Greg’s anus with two fingers.

Greg began to pant as Matt and I worked in unison to relieve Greg’s tensions. My tensions were about to cause me to expire, but my boys’ needs came first.

Greg began to squirm and whimper and then Matt produced several Kleenex. Matt placed them in just the right spot and Greg said, "I love you both," and spurted his sissy cream over and over, trembling with gut-wrenching pleasure.

I couldn’t do this any more. My own situation was too desperate. I would just have to tell the boys that I….

As Greg gasped for air, Matt said, "Dad, we know you need relief too. A good milker always does. And you’re a very good milker."

What did he mean?

Matt showed me. He unzipped my fly and, despite my weak protests, pulled out my distressed, leaking stiffie. Now that was really wrong! But it was mentioned in the Internet material that milkers must be assisted as well. Now I knew what that meant.

Each boy once again sat on a knee. Their sweet delicate fingers tickled and teased my cock and balls as first Matt, then Greg lovingly kissed my lips. It was a horrible, guilty pleasure, which was the only real kind of pleasure, after all.

No man could last long under that twin assault and I came very hard, spurting manly goo in five big globs into my boys’ fingers. But that didn’t stop them. They kept up their kissing and this time, gooey, stroking, until I came, exhausted and whimpering, twice more.

Greg asked me at one point during the cummy proceedings, if it would be OK for Matt and him to wear girl’s clothes around the house. I agreed. I would have agreed that the earth was flat. Matt, seeing an opportunity, asked if we could go out as a family with Greg and him en femme. Again, the sun revolving around the earth was fine with me.

Poor Matt. He hadn’t been milked yet, I thought. Then I saw that the entire front of his nightie was soaked with his creamy spendings. Just to be fair, though, I milked him as Greg massaged his tender prostate, making him unleash yet another cummy torrent.

In abject shame, yet in eager anticipation of more the next evening, I kissed my two sissies good night and wished them sweet dreams.

Maybe society was wrong after all.

 

Chapter Nine – Two Points to Resolve

There was a lot about all that had happened that concerned me, but two issues seemed to require my immediate attention.

First, were Greg and Matt telling the truth about not having actual sex (oral and anal) with each other? I would not allow that!

Second, I had to know what role John McCue and his son Billy had played in all this. Billy had sissified my Matt. If I understood it better, maybe it was reversible. If that was what I truly wanted.

After spending the morning looking in vain through old boxes, I went out and purchased a new set of baby monitors. I hid the transmitters in the rooms of Matt and Greg, then put a receiver in mine.

I was going to hear what really went on in there!

The boys got home around three-thirty and, as they had promised, went into their rooms to put on make-up, skirts, garter belts and heels. I hoped they had been thoroughly milked by their classmates that day, so I wouldn’t have to milk them too often. Well, maybe once or twice.

I went to my room to listen. As usual, my sweet sissies spent time on the phone. That time, I was able to hear one-sided conversations with some of their many admirers.

I heard Matt saying, "Oh, Brad, stop it. I’m not the prettiest sissy in school. Well, OK, maybe I am. I’m going to give your balls a nice tongue bath tomorrow for all that flattery."

Oh my.

I heard Greg saying, "Now Ron, don’t get yourself upset. You know I love you. I just couldn’t see you at lunch today. You know on Tuesdays Will takes me into the broom closet and eats my pootie and then puts his thing in me until I cum. All right. You can have Wednesdays. Kisses!"

Well, I thought, at least they’re popular.

There was silence for a good half hour, then I heard, "Oh, Matt, you look so beautiful dressed like that!"

"Thank you, Greg," the baby monitor said. "You get me so hot when you compliment me. Is your ass pussy all greased like you promised?"

"It’s always greased for you, Matt," Greg’s voice said. "Do you want to put your big, hot cock in me now?"

"Yeah! Let me just pull your panties down and put it…..Ahhhhh. Your ass feels so good around my cock."

Those liars! Those incestuous little…… The monitor began to issue grunts and moans. I ran down to Greg’s room, flung the door open and saw a snickering, fully dressed, en femme Greg and Matt sitting across the room from each other making grunts and moans. The baby monitor, which I had hidden, was sitting on Greg’s bed.

I had been fished.

"Dad, you really need to trust us," Greg said. "We won’t ever lie to you, so trust us, OK?"

Score one for the boys.

I apologized, then milked them very nicely and all was well again. Did I mention that they looked fantastic dressed as girls? Fantastic. They walked in big heels as if they had been in them all their lives. And their stockinged legs were magnificent. When I was done, I needed an extra large milking myself and they gave it to me. Twice.

Nice thing, this milking business.

That evening, after dinner, I left Greg, Matt, and Sam alone to go to the McCue’s house. I had made an appointment with John, whom I had known since third grade, for 7:30.

 

I arrived a few minutes early and considered what I would say. Since John seemed to be a lot farther down the sissy road than I was, I would just ask for John’s advice on dealing with my boys, all of them. I knew John "dressed," but I had no idea how good he would look as a woman.

I knocked. The door opened. John greeted me warmly. Although it didn’t look like the John I knew. This John was wearing a pretty red dress, black stockings, red, four-inch sandals, gold hoops and beautiful make-up. Despite his male haircut and his absence of big boobs, John was gorgeous. And his smile would melt steel.

Would someone please tell me what planet I was suddenly on? All this had been going on around me and I had been oblivious. My only certainty was that, once again, my cock was thick, hard and standing at attention.

John made it worse when he kissed me on the cheek in friendly greeting. As a woman would. But he wasn’t a woman. So what was he?

"You look confused, Dave," John said. "Handsome, but confused. I guess your boys told you. I’m a sissy, just like them. And my son Billy."

I couldn’t help staring at John. He was so feminine and cute and pretty.

He invited me in. I sat in a chair. John sat on the sofa. And crossed his delicious legs. Oh my goodness. Was I trying to look up his dress? I thought I caught just a hint of panty.

We small-talked a bit, then his young sissy Billy wiggled into the room. He was 14 and dressed similarly to his father. He looked extraordinarily hot, shaking his little ass as he sissied around in his too-high heels. The little teaser said, "Hi, Mr. Benson. Welcome to our home! I’m so happy you’re learning to accept Matt and Greg. And you’re <blush> milking them so nicely."

I was humiliated. How did the little prickteaser know that? Would his father call the police? John was only smiling sweetly at me. Damn, he was cute. Had I become gay in only three days?

Then Billy did the unthinkable. He sat in my lap, ground his pantied ass into my stiff cock and kissed me nicely on the lips. Then he said, "I was so excited that you were coming tonight. I was hoping that you would milk me. A man hasn’t milked me in a long time. Boys are always pulling my panties down and putting their big things into me, but I never get milked by men. Daddy’s so sweet. He milks me all the time, but he’s a sissy. I want a man to milk me. A man like you."

Whew! He kept grinding that hot little ass. What should I do?

I must have looked very distressed, because John said, "Billy’s a hot little piece of tail, isn’t he? I’ve given up trying to control his urges. They’re too strong. I would consider it a favor if you would milk Billy for me."

A favor. Oh. I gulped. And nodded.

Billy squealed with delight. He stood, then pulled his panties all the way down, stepping out of them one high-heeled foot at a time. Then he got back into my lap, lifted his skirt and presented his nice little pink cock and baby balls for milking. I looked at John once again. He smiled and nodded. That could probably be used as mitigation in the sentencing portion of my trial.

I grasped Billy’s prick. He quivered with delight and gasped. I stroked it nicely, stopping now and then to stir his balls. Then the little scamp kissed me. And since there were no incest lines between him and me, he put his delicious tongue right into my mouth.

Good golly, Miss Molly.

He even remembered that milkers need relief too. Despite his intense feelings, he made the effort to remove my prick from its cotton confinement. He stroked it lovingly as I kissed his lips and brought him closer and closer to ecstasy and then, BAM! he began to shoot his sticky cream, whimpering and panting. He threw his head back and squealed. And continued to caress my cock until it was alive with pleasure. My balls bubbled, then boiled over. He giggled each time I made a sticky spurt, then licked his cummy hand clean, and smiled so cutely at me.

It appeared that he wanted a second go and I wasn’t complaining, but his father said, "Sweetie, don’t you think you should go to your room and finish your ‘homework’ with Roger?"

"But, Daddy," The little cockhound said, "Mr. Benson is a man and his cock is out and you know sissies need men."

"That’s right, Billy," John said. "But Roger’s waiting upstairs with a full bag of sissy treats for you. And sissies of ALL ages need men. "

Oh! Did John mean….?

Billy seemed to connect the dots. "OK, Daddy. I’ll see you soon, Mr. Benson." Then he gave me a big, tonguey kiss. It was incredibly erotic, then more so when he dropped to his knees. He kissed the dripping head of my cock, then took it in his mouth and gave it one long, tantalizing suck along my cock’s entire length. Aaaaaahhhh. It was a miracle that I didn’t cum.

Billy picked up his panties and wiggled off in his high heels to his room and a very lucky boy named Roger.

John spoke parentally. "I know he’s a prickteaser, But I was too at that age. And some say I still am. I’m not crazy about having boys over on school nights, but Billy gets all his homework done and his grades are terrific. And, since it’s just the two of us, he needs more milking than I can give him. Your boys are so lucky to have each other for support. And you and Sam for milking."

I panicked. "Sam is milking them?"

John saw my concern and said, "That was just my guess. Sam is not a sissy and Greg and Matt need milking. He probably helps them out."

There was good news in there. I asked, "Why do you think Sam’s not a sissy?"

"It takes one to know one, Dave. All the sissies who know Sam say he’s not sissy material. It’s not a choice, Dave. Either you’re made that way or you’re not."

I was beginning to believe that. And getting more comfortable with it. Still, I was happy that I only had two sissies.

John and I chatted about challenges and tips on raising happy, healthy sissies. He was full of useful information and I was very grateful. It was a little distracting hearing the moans and squeals coming from Billy’s room, but the evening was going much better than I thought.

Then the subject of milking came up. John said, "You know, I’m older, but still a sissy, and I love to be milked by a man."

That sounded like a hint to me. What do you think?

I sort of cleared my throat and the next thing I knew, John was sitting on my lap. He smelled incredible. And he felt very good in my arms.

What the hell! I kissed him.

It was the best kiss of my life. There was a lot behind his kiss. He was someone I knew I could love, even at that early stage of our relationship. Oh, I was so excited. And happy. I kissed him back and held his sweet body in my arms.

Then I considered his needs. And mine. I began to kiss him again, then reached under his skirt. I had never seen John’s cock. It felt short, but chubby. And it was very hard. He sighed when I touched it through his silky panties. He was wearing a garter belt!!!

John broke our kiss, gave me a laser smile, then reached under the skirts of his pretty dress, hooked his thumbs in the hips of his panties, and teasingly pulled the little pink teasers down and off. I was shuddering with lust.

John got very comfortable in my lap and locked lips once again. I licked his tongue, then devoured it, getting very hot in the process. I reached for his little stiffie once again and felt its naked beauty. John lifted his skirts to allow me better access. I teased my fingers up and down its throbbing glory. John gasped. I cuddled his balls, John hugged me tightly, kissing me ferociously. I rubbed his peehole gently with my thumb. He liked that. John squealed. Tears filled his pretty eyes. He spurted warm sissy cream, then more. And more. My hand was soaked with his sweet nectar.

Then I did something I had never done in my life. I licked John’s hot, sticky juices from my hand, looking into John’s eyes as I did so. Looking back, I think that was the moment John began to fall in love with me. And I with John

He certainly seemed to like me a lot at that moment. I wasn’t sure when he got off my lap, but I was confident when he got on his knees, asked me to stand, pulled out my cock and began to lick it.

Alicia, my ex, didn’t like sucking cock. She pretended to like it when we were going together. But I don’t think she did it ten times when we were married. And she NEVER swallowed. At that moment with John, I believed that I could say, with true confidence that John’s love of cocksucking was only matched by his enormous, world-class skill. I almost screamed from pleasure as he licked my pole, tormented its head, sucked my balls and for dessert, entered my virgin asshole with two agonizingly adept fingers. I’m embarrassed to admit that my gut wrenched and I came, spasming, in about two minutes. And John swallowed it all! And didn’t stop! Over the next 23 minutes, he brought me to two more trembling, nuclear orgasms. And he lost nary a drop.

I sat, my chest heaving, but I was to surprise myself once more. Gasping, I beckoned John to stand in front of me. He raised his skirt and I was able to get a good look at his lovely little jewel, which was once again rock-like. I kissed it. He smiled with surprise and delight. I gave it a lick along its length. He squealed happily. I kissed his balls, then, shocking myself, took his lovely cock into my warm, wet mouth. I rolled my tongue around his semen-leaking cockhead. I caressed the naked globes of his bottom. My technique was lacking, but John loved my enthusiasm. He reacted so girlishly that I forgot I had a cock in my mouth. I was making oral love to my sissy girlfriend. And loving it.

The inevitable near-death experience seized my new lover and he gave little screams as he gushed his sticky cream into my mouth. It was delicious. And plentiful. Like his son, John was a hot piece of tail.

I stood. John threw himself into my arms. I think he was in love too. What did it all mean?

Who cared? I had never been happier.

I kissed John goodbye. He made a brilliant suggestion. On Friday, Greg and Matt would have boyfriends sleep over. John and Billy would sleep over too. Billy with Sam, my non-sissy, but apparently heartthrob of sissies. John with me. All night. Whatever I wanted. In his sweet bottom. And mouth. OK. I agreed. It was time for Sam to macho up anyway.

And I wanted John very badly.

I was floating when I got home at 10:15 and was greeted by a scene that would have floored me a week before. Greg and Matt were in their nighties (darn they were cute!). Greg had two fingers in Matt’s perfect bottomhole as Sam frigged Matt’s doodle to a crushing orgasm.

When Matt had returned to our planet, I said, "Hi, Guys!"

"Hi, Dad," Greg said. "We were tired and were going to bed, but had to be milked first and Sam was helping out. Didn’t know when you would be home. Did you and Billy and his Dad have a good time?"

Did they know or suspect? No matter. "I’m sorry you didn’t wait. I was looking forward to milking you both."

My sissies giggled. Matt cupped his balls, rubbed them suggestively and said, "There’s plenty more sissy cream in these, Daddy. And Greg hasn’t even been milked once yet"

Sissy parenthood has its rewards.

 

Chapter Ten – A Not-Much-Sleep Over

Friday couldn’t come quickly enough for me. I was very eager to have my grown-up sissy John in my bed. And explore unrestricted sissy delights.

Sam was a bit nervous about sleeping with two-years-older Billy. The boy had milked his sissy brothers many times, but had never had a real, unrestricted sissy love experience. Sam and I were even on that score and were both very "up" for the experience.

Since we had dropped all pretense about Greg and Matt merely having friends over for a video-games-and-pizza sleepover, the pretty sissies dolled themselves up to a tee. They had short, tight skirts, black stockings, garter belts and big stiletto sandals and were wearing make-up that set off erections over a three-mile radius.

Steve and Rick, the lucky lads for the evening, arrived early and eager. Their eyes almost left their heads when they saw my beautiful, feminine teens. I took the boys aside and lectured them about being good to my "girls" then left them to their intense and prolonged pleasures.

John and Billy arrived a few minutes afterward. My heart almost stopped when I saw John. He was a living doll. Forget those young, little cockteasing sissies who had been tormenting my psyche the past few days. John was an exquisite, mature beauty.

He was dazzling in a delicious, little black dress that highlighted the perfection that was his black-stockinged legs. His heels were five full inches and the thinnest of stilettos, yet he walked on them with full feminine grace. The shoes pushed his tasty-looking bottom back and his chest forward. Were those breasts peeking above the dress? Oh, my! His eyes were made up to bedroom dazzle and his lips invited serial kissing. Holy goodness! I was in love. With a man. A beautiful, sweet, sexy, feminine man.

Billy was wearing something or other, I didn’t notice. But Sam did. His roommate for the evening had Sam’s tongue hanging out. I was sure Sam would be using that tongue to full advantage as the night rolled on.

John kissed me ever so sweetly. I was intoxicated by his perfume and womanly scent. I noticed that he and Billy each had a small suitcase. As I grabbed the cases, John whispered to me, "I thought we could stay the weekend. Was that too presumptuous of me?"

Oh my!

Billy and Sam ran off, hand in hand. Sam looked scared and horny. A prescription for a great night. My feelings were similar.

I sat on the couch and John sat next to me. I kissed him. We embraced. I said, "You’re so feminine and incredibly beautiful. Do you have a female name?"

John looked at me with his sex-drenched eyes. "I was saving it for when I would be full-time as a woman. But that’s what you make me want to do. It’s Jennifer."

I looked at lovely, delicious Jennifer and said, "I think I’m falling in love with you."

Jennifer kissed me and said, "You’re easy to love too, Dave."

She took my hand (from that moment on, I could only think of my Jennifer as a woman) and we went upstairs. There were some interesting noises coming from the rooms of Greg, Matt and Sam, but I hardly noticed.

We entered my room and closed the door. I sat as Jennifer removed some things from her case. Then she excused herself and went into the bathroom.

"You may want to undress, Dave."

A thrilling suggestion.

I stripped to just me and sat, a bit anxiously.

The waiting was worth it. Jennifer had added a long, blonde wig and had changed to a black peignoir over black panties, stockings, garter belt and heels.

I almost came right then.

She was literally the sexiest woman I had ever imagined. And the big surprise? She had small, but beautiful breasts.

I stared at them. "How……?"

"I’ve been preparing for a transition since my wife died, Dave. Hormones and tiny surgeries. Meeting you and your family makes me want to speed it up. You have a beautiful body. Do you like my titties?"

As an answer, I stood and strode over to her. I held her and kissed her, then laid her on the bed. I opened her peignoir and touched her left breast with gentle fingers. She purred. I teased the nipple with the tip of my finger. Her back arched slightly. Mmmmm. Sensitive.

Her nipples were very erect and deliciously beautiful. I kissed the right, brown treasure and she said, "Ohhhhhh. No one’s ever done that. Please don’t stop."

I had no such intention.

I softly kissed, licked and sucked each pointed jewel. She whimpered and trembled with pleasure. Then I upped the ante a bit by rubbing my palm against her stiff little pricklet as I worshiped her titties.

She screamed. Not an uncommon sound in my house that night. And began to jet spunk into her panties. I reached in to feel the gooey warmth of her bare clittypole and rubbed her sweet, sticky semen all around the sensitive head to prolong her pleasure.

Her eyes were filled with tears as she kissed me and threw her body against mine.

She began to kiss me all over my face, saying over and over, "I love you."

I responded in kind. Jennifer was mine from that moment forward. Isn’t love, when you find it, the best thing there is?

Things soon grew too hot for the verbal. Jennifer removed her peignoir, moved to the side of the bed, lay flat on her delicious titties and raised up on her knees. She wiggled her shaved, soft, perfect ass at me and begged for the fucking she said she deserved.

All right. You men out there. How often do you hear that? I thought so.

I heard it that night and I was enchanted. I peeled off her sopping panties and saw her brown and pink entrance to the world’s finest delights. It looked too dry for me to apply my weapon right away, but I was distracted anyway by her dangling pink bag. Jennifer was gasping and wiggling her perfect bottom and her balls were swinging like a clock pendulum. I decided to investigate.

I stood behind her, bent at the waist, grabbed a warm thigh in each hand and from the rear, took her balls into my mouth. She yelped with surprise and delight. I was extraordinarily careful not to hurt her, but I sucked each testicle as I licked it.

Jennifer squealed as if she had been shot. Then I felt her left testicle stir on my tongue and she began to ejaculate helplessly. Whimpering with passion. Glob after sticky glob. Would I have to call 911? Like me, she was in her late 30s and her heart was strong. But I felt her surrender to any agenda I had in mind. She liked what had happened thus far.

I began to lick the inner folds of her bottom. She quivered with ecstasy. I tipped her pink and brown hole with my tongue. She cried out, then pushed her bottom back so I could have freer access. I must have been doing it right. I dug deeply with my tongue for an expended period, during which she orgasmed hard again. Then again. My Jennifer was one hot tamale.

I hadn’t cum even once and I was very aroused. I stopped licking, listened to Jennifer mew for a fucking, then made us both very happy. I pushed my cock into an ass for the first time. And it was the best ass on earth as far as I was concerned.

Jennifer was an active participant in our lovemaking. She moved. She made noises. She even came again, this time without getting hard and making only little sissy dribbles of cream. But her cum was still intense.

When I filled her bottom with boiling sperm, I saw the solar system as I had never seen it before. We had a life together. A man, his tgirl wife, three sissies and a lucky boy.

Jennifer kissed me for a long time after our first fuck. Then she insisted on nursing on my cock until I came in her mouth twice and we fell asleep, exhausted. At 3 a.m., she woke me, got on her back, raised her legs, and guided my big guy into her private place. I loved fucking her that way. It felt as if I were her master. And she loved being the master’s woman. Somehow, Jennifer managed to get hard twice during this exquisite liaison and she came a bucket the first time and a half bucket the second. When I filled her with my sticky juices and it drooled from her perfect hole, there was cum everywhere.

I liked that a lot.

Of course we had another go in the morning; that time I was spooned behind Jennifer and I skinned her doodle and kissed her as I pounded her spectacular pooper.

It was the best night of my life. Except for every night since then.

 

Chapter Eleven – Full Time

As we rose from our coital arena, Jennifer announced that she would never dress as a man or pretend to be a man from that day forward. I was delighted and told her so. We kissed and somehow ended up in bed again, rolling in cummy sheets and joyously spurting our cream.

 

Jennifer also told me that Billy, who wanted to be called Erin and be referred to as a girl, would from that day also be living full time. They would be able to grow and style their hair, grow and paint their nails, pierce their ears and remove hair growing in all the wrong places. Wow!

I wondered if Matt and Greg had girl names and wanted to be called girls.

We showered together and, of course drained our remaining, meager cum reserves. Then we went to fix breakfast, but found that Steve and Rick were already gone and Sam and my three sissies had already eaten.

They smiled slyly at Jennifer and me as we entered the kitchen. True to her word, Jennifer was wearing skirt and heels. So were the sissies.

"Well," Greg said, "Did you sleep well?"

All six of us started giggling at that and couldn’t stop for a long time.

Jennifer announced that she and Erin were going full-time. Everyone cheered as Erin hugged Jennifer and said, "Oh thank you, Daddy!" Then Erin went over and sat in Sam’s lap and began to kiss him very nicely. They apparently had also enjoyed their evening.

I asked Greg and Matt. "Would you like to be full-time girls, forever?"

They didn’t hesitate. They jumped up and down, squealing and said, "Oh, yes, Daddy, please!!!"

"What would your names be?"

Greg wanted Gia and Matt wanted Megan.

I hugged my girls and said, "Well, then we’d better spend the day shopping."

What girl doesn’t like to hear that?

 

Chapter Twelve – Shopping

I had never been to the Shady Rest Mall, which was a small center in one of Fromage’s western suburbs, but apparently all sissies knew about the mall and Shady Rest. [More about this community in G-Man’s "Panty Town."]

It was a mostly sissy community, right next to the town I grew up in, and I had never heard of it. Nor had Sam. But my gorgeous sissy posse ached to go there.

Had I been asleep for 38 years?

The stores all catered to sissy tastes – petticoats, crinolines, impossibly high heels, the naughtiest of lingerie and the trampiest of everyday clothes. And mountains of panties. I spent $3,438.45, but at last my girls, including my adored Jennifer’s Erin, had wardrobes that would allow them to hold their sissy heads high.

By 1 p.m., my bankbook had lost several pages, but my girls were very happy. And horribly excited from trying on and buying all those gorgeous things. They could hardly eat lunch and were in severe need of an industrial-strength milking. But where?

My wise Jennifer said, "This mall is famous for its Sissy Milking Station. It’s just around the corner."

"A milking station?"

"Oh, yes. It’s free too. It’s run by the nicest middle-aged male volunteers. And they’re trained and bonded by the American Sissification Institute."

How did Jennifer know so much about it? I asked, "Have you been milked there?"

Jennifer blushed. "Once or twice. It’s very nice."

Gia and Megan and Erin began begging me. "Please Daddy, please!"

How could I resist?

We entered the station. It looked like a doctor’s office waiting room, except the six of us were the only "patients."

A pleasant-looking, middle-aged woman (she looked like a woman) was sitting behind a receptionist desk. She smiled at Jennifer. "Hello Mr. McCue. It’s wonderful to see you. Are you and Billy here for complete milking or just a little toss-off to ease the pressure of shopping?"

Jennifer had the good sense to be embarrassed. She blushed, smiled sheepishly at me, and said, "No, Mrs. Campbell. And I’m Jennifer now and my daughter is now Erin."

Mrs. Campbell? She had been here enough that they knew each other that well? I was reminded of an old Ray Charles song with a great line: "You said before we met that your life was awful tame; then I took you to a nightclub and the whole band knew your name." Still, better that Jennifer took care of her needs at a "clinic" like this, than with some guy she picked up. I resolved to forget both our pasts. It was our future that was important.

Mrs. Campbell got up from the desk and hugged Jennifer and Erin. "How wonderful," she said. "I’m presuming it’s because of your young man?" And she smiled at me. A nice lady.

"I love Dave very much, Mrs. Campbell. And his sissies, Gia and Megan, and his son, Sam."

Mrs. Campbell considered Gia, Megan and Sam. Then she looked at me. "A fine family you have here, Mister. Your children are sweet and attractive. I hope the girls are full-time?"

"As of today and $3,438.45 in clothes and accessories," I quipped.

Mrs. Campbell laughed. Then she considered Sam. "Oh, yes. You’ll be very popular with your sisters’ friends, young Sam. Very popular."

Sam smiled and blushed. Then looked at Erin, who was licking her red lips.

"Well," a businesslike Mrs. Campbell said. "Let’s get you milked. We have all our milkers on duty today, so how many do we need?"

I hated to leave Sam without Erin, but I said, "Three." I certainly wasn’t going to stand by while some old perv milked my sweet Jennifer. Medical procedure or not.

"Good. Erin, room four with Mr. Beasley.

Erin squealed. "He’s the best!" she said. Then she realized what she had said and looked at Sam. "For an older guy, that is. But I’ll be taking your hard cock in my mouth and bottom all night again, Sam."

Sam melted. Erin knew how to control her men.

"Gia, room six with Mr. Fisher and Megan, room one, with Mr. Carter."

"They’re all great, Erin whispered to her fellow sissies as they sissied back for their full milkings. Which included quite a bit of milk extracted from the milkers as well. And some very squishy bottoms and full, cummy tummies for the sissies.

Mrs. Campbell said to Jennifer, Sam and me, "A full milking takes about three hours. Would you and your lady care to use one of our guest suites for her full milking?"

Oh yes, I thought as I saw Jennifer wiggle with lust and lift her already short skirt. But what about Sam?

Just at that moment, the door opened and the most beautiful thirteen-year-old sissy in the world’s history walked in. Her gorgeous face, blonde sausage curls, perfect make-up, stunning legs and lovely painted toes would be illegal in eight Middle Eastern countries. But her beautiful features were scrunched in severe, sissy-milking distress.

"Oh, Mrs. Campbell. I’ve been trying on panties all day and I overexcited myself. I’m going to explode if I don’t get a full milking right now.’

Mrs. Campbell said, "I’m sorry, Lisa. Three of our milkers called in sick today. There’s no one to help you."

Wait, I thought. Didn’t she say they had plenty of milkers ready? Was she harming that angel on purpose?

Then I saw what was happening. Mrs. Campbell said, "But Lisa, this fine young man named Sam has two sissy sisters and is an experienced, loving milker. He could take you to one of our guest rooms for a very nice full milking."

Lisa looked at Sam. She liked what she saw. She grabbed his hand, kissed him and pulled him back to the milking rooms.

"Room nine," she called to Lisa, chuckling.

Nicely done, Mrs. Campbell.

Jennifer and I spent a delicious, cummy three hours and at the end, it slipped out. Just as my cock slipped into Jennifer’s bottom for the fourth time that afternoon. She was on her back, filled with cock and moaning when I asked, "Will you marry me?"

Jennifer began to sob. And squeeze my prick with her bottom muscles. Then she kissed me, spurted her sissy cream for the seventh time that afternoon and screamed, "OHHHHHH, YESSSSSSSS!!!!! I’ll marry you! YESSSSSS!!!!"

 

Chapter Thirteen – The Rest is History

Jennifer and I were married six months later. She was the happiest, most beautiful bride ever. Her traditional white gown was made of heavy bridal satin, with long Juliette sleeves which buttoned almost to her elbows and puffed out at the shoulders. The gown also had a long cathedral train that trailed after her majestically. Her face was framed by a veil, which cascaded down from a beautifully beaded headpiece. But the best feature of the gown was the daring décolletage, which put Jennifer's now DD breasts (I gave them to her as a wedding gift) on display, making all the women in attendance jealous of her and all the men envious of me. I wore a matching white tuxedo, and we made a most handsome couple, if I do say so myself. We even got a picture in the Fromage Curder society pages.

Sam was my best man. I was surprised that he had time, considering that Lisa had hooked him up with dozens of sissies in Panty Town and he was just about the studmeister of the sissy condo complex at age 13. He stopped fooling with Erin, because I adopted her and you can milk your sister, but that’s it.

Gia, Megan and Erin, were incredibly beautiful bridesmaids. Their gowns were similar to Jennifer’s but without the long train and made of pale burgundy taffeta. Also, the necklines were cut more modestly as befitting their unmarried, "virginal" status. But, since we had started them on hormones as soon as they went full time and they were developing full feminine physical characteristics, including excellent titties, the girls insisted at least a little of their developing bosoms be uncovered.

Despite the changes in their bodies, the former boys’ cocks were still hard and spewing. All day long and most of the night. I know, because Sam and I are called on for this important duty often. But the majority of milking is done by the hordes of boys who circle our home, besieging my girls in an infatuated search for love, sex and the perfect babe.

My three sissies are as close to perfect as you can get.

 

 

 

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