Philly's First

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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I was always uncomfortable being in Aunt Jane’s bedroom. Any 14 year old boy would be. It seemed to me to be the most feminine place on earth, rivaled only by my own mother’s bedroom. Both are single mothers now, and their bedrooms are full of pink and pastel, cushiony furniture with soft dainty pillows and lavish vanities piled with girly make-up and stuff. But why was all the lingerie strewn about the room? Stockings and lacy garments covered the furniture and hung about the room.

Being naked in front of Mom and Aunt Jane didn’t help either. Not that it was unusual for me to be naked, especially since I was serving the first week of a two-week punishment. All punishments in our family are served naked. But I have never been naked in Aunt Jane’s bedroom. “What’s going on?,” I wondered to myself, but dared not to ask. The slightest of infractions would earn more spankings while on punishment.

“My goodness, Sally!” Aunt Jane broke the silence. “Look at how hard your little dickie is!” They both gasped and giggled as they pointed and looked at it. My name is Salvatore and I hate it when they call me Sally, but I learned long ago the price of complaining.

I haven’t started puberty yet. My body is completely hairless and I am the smallest of stature among my classmates. My little dickie (which is what I must always call it or risk punishment) stood a thin inch-and-a-half when hard, and not much thicker than a pencil. It all but disappeared when it wasn’t hard. It got rock hard whenever I was embarrassed, and in being naked Aunt Jane’s room with my Mom with all those sexy garments around had me as hard as ever. My little nut sack, walnut sized at best, was pulled up tight and almost invisible.

And why did they always have to wear those sheer little nighties? Don’t they know how embarrassed a boy like me is seeing his Mom and Aunt dressed so scantily? The constant teasing and touching didn’t help, either. They also let my sisters and girl cousins tease me, but that’s a story for another day. All it ever made me want to do is rub on my pillow and have a nice dry cummy, since I haven’t started wet cummies yet.

Mom broke the silence, “I bet you’re wondering what we’re doing here, right? Well, you saw what happened to your cousin Philly yesterday. He had his first wet cummy!”

Of course, I saw it. My little dickie was twitching just thinking about how embarrassed he must have been. Phil is Aunt Jane’s 14 year old son. We’re only a few months apart and go to the same school. I guess it’s genetic that his physical attributes match my own. He’s a bit taller and his little dickie is just a tad bigger than mine, but still totally bald. We are the only two males in the family, by the way. Mom and Aunt Jane each have two girls. My sisters are 15 and 17. My girl cousins are 18 and 16.

I thought back to what happened...

The girls were tickling Philly as part of his punishment and it just happened. Right in front of everyone. Not that it was much of anything, just a drop of clear liquid. If my little sister didn’t shriek when the little drop touched her thigh I’m not sure anyone would have noticed. “Mommy! Mommy! Philly peed on me!”, she screamed.

Mom and Aunt Jane ran over to investigate and once they realized what happened, you would have thought they hit the lottery the way the carried on.

“Oh, my Goodness!” Aunt Jane cried.

“Little Philly is growing up!” Mom sang.

“Philly’s little dickie came!”

“Everybody! Come look at Philly’s wet cummy!”

Phil’s dripping little dickie was carefully examined by all of the girls, giggling and gasping all the while. God, he must have been humiliated. He stayed hard the entire time from the sheer embarrassment.

Once all the commotion calmed down, Mom called me over. “Sally, come look at Philly’s little dickie! He had his first real wet cummy!”

Is it weird that I wanted to see? That my little dickie was hard? That I wanted to add to his embarrassment? That I wanted to touch it? Well, I got my chance. I took a good hard look. It was Just a droplet of clear liquid with a few white streaks. He stayed hard, looking at me with pleading eyes.

I reached out and put the tip of my finger to the wet tip of Philly’s little dickie and made a little circle just under the head. Philly moaned and another little drop came out.

I pulled my hand away in shock. “Did I make him do it again?”

All the females giggled uncontrollably and teased Philly unmercifully. In the confusion, no none noticed my own dry cummy. No one was even touching my little dickie. That never happened to me before without being touched.

I snapped back to the present by a sharp slap on my sore bottom. “Wake up, Sally!” Mom yelled. “We’re going to have a little party for Philly on Saturday to celebrate his first wet cummy, and Aunt Jane wants you to help pick out his outfit.”

Aunt Jane added, “Yes. I’m so happy that you made him have another cummy so quickly and then helped him clean up.” They made us take a bath together, which is nothing new. But I never had to clean his little dickie and tiny nut sack before.

I was confused. If I was to pick Philly’s outfit, why wasn’t I in his bedroom looking at his clothes? Why was I in Aunt Jane’s room? Why was I surrounded by this frilly girly lingerie?

A dry cummy hit when I realized what was going on. Philly was going to be dressed in this girly lingerie for his wet cummy party, and I was going to help pick out his outfit!

“Sally, did you have a dry cummy without even being touched?” Mom showed how well she knows me. “Has that happened to you before?”

I blushed profusely, but knew from experience that I shouldn’t lie. “Just one other time, Mom. When I made Philly have his second wet cummy and you all started teasing him.”

“That’s OK Little Sally. Being sensitive and having no control of cummies is common among the boys in our family. Must be genetic. Maybe we’ll mention it to your doctor next time I take you.” I caught her winking at Aunt Jane when she said that. She bent over, her grand cleavage in my face, nipples barely covered by her sheer nightie. “You tell me whenever that happens from now on, OK?”

“I promise, Mom.” I replied.

“Let’s get started,” Aunt Jane interrupted, “Start looking at the panties. See what you like and we’ll go to the store and get whatever you like in Philly’s size.”

Mom added, “And make sure you take into account that our whole family will be here and some of our friends will be invited.”

Most of Mom and Aunt Jane’s friends were single mothers, too. The party will be almost all ladies and girls. It was a bit overwhelming. Is it mean that I want Philly totally humiliated in front of them by the outfit I was picking? I want something very girly, but also something revealing.

Mom reached from behind and started lightly caressing my tight little nut sack as I looked through the panties. I lost count of the dry cummies I had as I selected Philly’s outfit. Of course, I was a good boy and told Mom and Aunt Jane every time it happened, as if they couldn’t tell.

Mom and Aunt Jane explained a lot about ladies’ underwear as I sifted through it all. The whole process not only affected me, but I could see it was affecting them too. Their nipples were as hard and big as I’ve ever seen, poking the thin material of their nighties and I noticed wet spots on their panties. I’ve seen them and the girls get aroused when teasing Philly and me, but never like this.

They pushed me out of the room quickly and slammed the door as soon as I was done.

The week dragged by, but it was finally party time on Saturday night! I was so embarrassed to have to be naked, since I was still under punishment. I begged to be allowed to wear clothes, but Mom refused to make an exception. She paddled me for making such a fuss and I had a bright red bottom to add to my humiliation. Fortunately, the guests were all familiar with our family’s punishment routines and it wasn’t out of the ordinary for there to be a naked boy or girl around. Today, I was the only one naked, and hard as a rock, of course.

All the ladies and girls were dressed for a party. I don’t think the moms would let their daughters wear such revealing clothing out in public. Everyone was so sexy and keeping me aroused as I served. Cleavage, panty shots and stocking tops were all over the room.

Mom and Aunt Jane waited with Philly in Aunt Jane’s room until all the guests arrived and were seated. Mom came out first and took her seat. Aunt Jane followed and took a minute to thank everyone for coming and explained that we were here to celebrate Little Philly’s first wet cummy. I blushed when she explained how I made him have his second. They all gasped and giggled away. I felt a dry cummy building, but held it back somehow. “His face is redder than his bottom,” one of the girls shouted to more laughter.

Auntie Jane then explained that I had selected Philly’s outfit for the day. I could hardly wait to finally see him in it. I hoped that with all of Mom’s and Aunt Jane’s suggestions that he looked good and was totally humiliated.

“Philly, please come out now!” Aunt Jane shouted. An interesting choice of words.

The room was silent except for the click of heels until Philly finally came around the corner to loud cheering and applause.

“My goodness!” I thought to myself. “He must be so totally humiliated. I can’t believe how girly he looks!” He walked out to the middle of the room, as instructed.

He teetered on his heels and the sound drew my eyes to his feet at first. I picked out platform pumps, or stripper pumps like Mom called them. The tops were clear plastic so that his feet were completely exposed. I could see the red toe nail polish, which matched his fingernails, through his sheer black stockings. My little dickie was throbbing.

Letting my eyes move up I came to the lacy stocking tops, just above Philly’s mid-thigh. I decided on stockings that stay up by themselves. Sure, a garter belt is girly and would have been embarrassing. Aunt Jane suggested that I leave it out, since she convinced me that it would take attention away from other places that I admitted I wanted everyone to focus on.

I looked higher up to Philly’s chest, forcing myself to leave the best for last. Philly had no chest, of course, so Mom suggested that instead of a bra, I dress him in a black camisole that matched his panties. It was sheer, with a flowery lace pattern.

I looked closer at Philly’s chest. Could it be? It can’t be! Did he have little titties? I’d seen my sisters and cousins sprouting titties when they were punished and I could swear that Philly had sprouted titties! My little dickie was throbbing at the thought.

I could barely tear my eyes away from Philly’s little titties, but I wanted to see the rest. I wasn’t disappointed. It was a perfect sight. Philly’s rock hard little dickie pushed the sheer lacy fabric of his panties out. Its underside was clearly visible as was his walnut sized nut sack. Mom and Aunt Jane picked out the perfect size. I chose a full cut, so that he would have big, ladies’ panties, but they were so sheer as to be not there at all.

Philly glared at me, but didn’t dare say anything. I knew what he was thinking. “How could Sally do this to me?” I then noticed that Philly had some make-up on, and he had a black lacy ribbon in his hair to match his panties.

Then it happened. I couldn’t have planned this humiliation any better. Philly’s little dickie erupted. His latest wet cummy was clearly visible through his sheer panties. He nearly fell over. In fact, it was so powerful that it spurted out of the fabric a bit. Everyone cheered loudly followed by gasps and laughter.

Philly stood humiliated in the middle of the room dressed in girly lingerie. Surrounded by scantily dressed ladies and girls. His little dicky was still rock hard and dripped with a wet cummy that was much bigger than any he had before. He knew that he had to remain there, or risk severe punishment. Earlier, Mom and Aunt Jane threatened to punish his little dicky if he didn’t behave. He had to take whatever was dished out.

When everyone calmed down, Mom stood and said, “Sally, show everyone how you helped Philly after his first wet cummy.”

I wasn’t expecting this, but I so wanted to participate in his humiliation. I was trembling as I walked up to Philly. Our eyes met and he mouthed silently to me, “Don’t ... Please don’t...” But we both knew that we had no choice. I know I didn’t want any more punishment, especially on my little dickie, so I reached out with a shaking finger.

“Not like that!” Mom interrupted. “He dirtied his panties and they need to come off! Help him so he doesn’t fall over on his heels.”

“Come on Philly, let’s get this over with,” I said softly. “You know we have to do it. Hold on to my shoulders.”

He put his hands on my shoulders and I lowered his stained sheer panties, completely exposing his rock hard little dickie. He lifted one foot, then the other as I slipped his panties over his heels and completely off and laid them aside. I noticed that there was a lot more liquid than his first wet one. It was all over his little dickie, and I really wanted to touch it.

I reached out and touched the tip of Philly’s little dickie, just as I did after his first wet cummy. The ladies were all but silent, just a few moans sneaked out. Why were they rocking their legs back and forth so much?

I moved my finger in circles underneath the head and just like last time, Philly had another wet cummy, only this time it spurted out and landed on the floor, not once but three times! How humiliating for him! He had to hold onto my shoulder for dear life to keep from falling over.

That was the last straw. I couldn’t hold back my dry cummy. It hit when I stepped back from Philly and was facing all the ladies. I moaned and humped the air in front of me. When it was over, I blushed, looking down in shame and humiliation. I noticed a small drop of clear liquid at the end of my little dickie!

(End of File)