Dandy Dennis

[ bf, sissy, solo, ws, cross ]

philipspencer74@gmail.com

Published: 1-Nov-2012

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This work is Copyrighted to the author. All people and events in this story are entirely fictitious.

I'm twelve going on thirteen. Last week I started the eighth grade, but this weekend we're off because today is Labor Day. My sister Marybeth has just started as a freshman in high school, and last Friday evening she invited some of her friends for a sleepover to celebrate her 14th birthday.

We have a three-bedroom, split level house. The kitchen, eating area, family room, and one bathroom are on the ground floor, while the living room, master bedroom, and a second bathroom are on the middle level. Marybeth and I have rooms on the top level, and there is a bathroom between our two rooms.

I don't think anyone else is aware of it, but in our bathroom there is a two-inch gap between the door and the floor; about four months ago I discovered that if I lay on my side on the floor of the bathroom, I could spy on my sister. She has a really nice bod for a sister.

On Friday, I shared dinner and birthday cake with Marybeth and her friends, but she refused to let me join them for the rest of the festivities, so I went to my room. Bored with rereading "The Hunger Games," I decided to spy on the girls. At first nothing happened except boring gossip, but my ears perked up when Marybeth suggested they change into their pajamas. I was in heaven! Five hot girls (including my sister) plus chubby Kathy L. were going to get undressed right before my eyes. My jeans went to my knees as soon as I saw Jodie K's bra. Other tops came off and I could see white, polka dot, and striped panties.

All of a sudden Sheryl B. opened the door to the bathroom. She screamed when she saw me. "Marybeth, look at your brother!"

All six girls ran over. Christine O. laughed. "That isn't such a big deal!" she said.

"Whadya mean? Have you seen a guy's dick before? When? Whose? Where? I don't believe ya! Really?" the questions all came at once. I was as embarrassed as could be, but with the new focus on Christine I was able to pull up my pants.

"Do you remember when I went out with that guy in high school last summer? Mike Knowland?" she boasted. "He's a senior now, and his parents bought him a car. Well, it was the second time we went out, and we were parked in his car, you know..."

If I had been wiser and more prudent, I would have retreated to my bedroom, locked the door, and taken things (or at least one thing) safely in hand. But I was just as eager for gossip as any of the girls, so I stayed behind to listen.

"Did you let him feel you up?" asked Margie S.

"Just a minute, I'm getting to that part," said Christine. "I let him feel me through my blouse, you know, while we were making out, and somehow he got his hands under my blouse too. He tried to unfasten my bra, but he couldn't do it, so I reached in back and did it for him. He wanted to see my tits and suck on them, but I wouldn't let him. Then he unfastened his pants and asked me to suck his dick, but I said no again. It was only the second time we'd gone out!

"To make a long story short, he insisted I jerk him off, and I did," she said proudly.

"How was it? Did you suck him then? Did you taste his come? Did he have a lot of come?" the questions came all at once.

"I jerked him off, and I think he liked it because he shot his sperm into the air, but it was really dark and I couldn't see well," the girl stated nonchalantly. "But I didn't taste it because I've heard it's really gross tasting, and I certainly didn't suck him or anything. I was kinda scared, so I've never gone out with him again. Anyway, that's how I know that Dennis's dick isn't all that big, really."

Everyone looked at me, and I blushed even redder than before. It's bad enough to have your sister and five of her friends watch you jerk off; it's even worse being told your cock is not up to par.

"Dennis, you're a real creep, do you know that?" Marybeth said. "How many times have you played with yourself while I've gotten undressed? And now today. You're really in trouble; I'm gonna go tell Mom and Dad."

"Wait, Marybeth," said Margie . "Let's have some fun first."

"What do you mean?" asked Maybeth, echoed by one or two of the others.

"You can always complain to your parents," Margie said, "but right now he's our prisoner, and I bet we can make him do whatever we want. So the question is, what do we want him to do?" "Make him sing a song," suggested Jodie. "Not something like 'Happy Birthday,' but something cool, like..."

"No, we have to really punish him somehow," insisted Margie. "Something nasty.

"When we caught him spying on us, he had his pants down, but I didn't get a good look at his dick," said Kathy. "Let's make him strip naked!"

"Yeah! Cool! Good idea!" cried the other girls.

"I have another idea," stated Marybeth. "Christine told us that she gave that Knowland guy a handjob; she can show us how it's done, using Dennis as her guinea pig."

"That isn't much of a punishment," pointed out Jodie. "He'd love it."

"Not if we make him shoot into a cup and then drink it," insisted Marybeth.

Everyone else agreed that would be an appropriate punishment for a spy, so they made me pull my pants down, and Christine jacked me off. She really didn't know how to do it right, and twice I had to stop her from almost yanking my dick off, but then to everyone's delight I shot my semen into a paper cup, filling it about 1/4 of the way. They made me drink the stuff down, and right then and there I decided I could never be gay.

"Now what?" asked one of the girls.

"Well, he wanted to come to the girls' party..."

"Well, he came all right!" pointed out Sheryl. "A lot!"

Margie ignored the pun. "Dennis wanted to come to the girls' party, so I say we should let him," she declared. "But let's make him dress like a girl! And change his name to 'Denise.'"

The other girls agreed that would be fun until Jodie asked, "Marybeth do you have a razor?"

"In the bathroom. Why?"

"For his balls," she stated casually.

"No way!" I cried. "I'll do anything you want, but I'm not going to let you cut my balls off!"

Jodie laughed. "All that hair is ugly; I just want to shave the hair, not castrate you," she said. "And if you're going to look like a girl, we have to shave your legs and armpits too."

Reluctantly, I went along. I insisted on shaving my own balls - I didn't trust any of them with a razor in that area. All six girls watched eagerly (and they cringed as loudly as I did when I nicked myself, leading someone to suggest dousing the area with perfume, since it had alcohol in it. That hurt even more than the razor!), and then they took turns on my legs and under my arms. Marybeth pulled a pair of pink panties from a drawer, and Christine took off her bra and made me put it on. They stuffed it with tissue, but the cool part was that I got to see Christine's lemon-sized tits.

Marybeth then produced a skirt and a midriff top; Jodie contributed "Hello Kitty" sneakers and knee-length socks. My hair is rather long - shoulder-length, so they made it into pigtails and put bright red clips in it. They put so much make-up on me that if my dad had seen me, he would have said, "You look like a two-bit whore."

(I doubt there are any whores who charge only a quarter, but that's what Dad says whenever Marybeth puts on too much makeup.)

"Uh, girls, I have to go to the bathroom," I said.

They looked at one another and finally Margie said, "Okay, but we get to watch."

"No, wait," said Kathy. "See that empty pop bottle? He can pee into the bottle, and that way we can all watch. Then he can drink it."

"Good idea!" said Jodie. "But let's take it further. Christine got to give him a handjob, and I think all of us want to try. Except Marybeth, 'cuz Denise is her brother, and that would be weird. So why doesn't Marybeth hold her little brother's dick while he pees into the bottle?"

It was embarrassing to pee in front of all the girls, but even worse that my sister was guiding my dick. Neither can compare to the awful, extremely salty taste of urine, which is even worse than the taste of semen - something I hadn't thought possible.

Kathy said she had to pee next, and one of the girls gave her the pop bottle as she went into the john. The other girls all followed in turn, and by the time they were finished there was over half a quart of warm, smelly liquid. They wanted me to drink it all down at once, but I could only stand it in small quantities; by promising to drink everything, they relented and told me to take my time.

It was still early, so they decided to gossip about boys. Matt W., Paul C., Mark S., John L. - the list goes on. Most of the boys are in high school, and while I know some of them by name, I don't really know any of them well.

Throughout the entire discussion, Jodie had her hand up my skirt and inside my panties. For the most part, I had a hard-on, but if I ever got soft, Jodie jacked me right up again. Finally she was animated to talk about a boy named Jim H., and she gave me a really good handjob. I didn't tell her when I was going to come, so she had to catch my semen in her hand. She made me lick it off, but that was sorta erotic so I didn't mind the taste that much.

The girls went on to naming boys from my class in middle school, and since I had seen most of them in the locker room at one time or another, I was expected to give an assessment of their private parts. The truth is that I had never paid much attention, so I just bull-shitted my way through this. (Edward? Uncircumcised. Kinda small. Spunky? Big, even for a black guy. Pepe? You've got to be kidding. You'll need tweezers.) For some reason, I got a boner again.

My parents had promised to take us to a lake the next day, but since it was a long drive we had to get up very early. All this time the girls except Sheryl and Christine had been sitting around with nothing on except their bras and panties; Sheryl had slipped on a Chicago Cubs jersey that she wore as a nightgown while Christine wasn't even wearing a bra. After letting me see them in their underwear it seemed rather silly for them to put their pajamas on (no, there weren't any sexy nightgowns), but that's what they wanted to do before going to sleep.

Margie went into the bathroom to change, and when she came out she waved her blue and white polka dot panties in my face. "I've heard guys like sniffing girl's panties," she said. "Would you like to sniff mine? By the way, I'm completely naked under this thin cloth."

I grabbed the panties and held them to my nose. Mostly they had the lavender aroma one associated with fabric softener; I was trying to figure out the slight musky odor out when Marybeth threw a nightgown at me. "Put this on, Denise," she ordered. "By the way, you owe me $5 for the panties you've ruined with your come stains."

"I don't think Denise should wear panties under her nightgown," opined Sheryl. "That way we can reach up and play with um... her penis... her penis... uh, that sound really amusing, but you know what I mean. I don't think she should be wearing panties."

She pulled up the nightgown and yanked my panties down; I immediately got an erection again, and she grasped me firmly.

"We're supposed to get up at 7:00, aren't we Marybeth?" asked Margie. Marybeth nodded and grunted something, so Margie continued. "I think we should go to bed, so we can get up early. And I think you're right, Sheryl - Denise doesn't need panties in bed; take them off.

"Okay, so now for sleeping. Since it's Sheryl's turn, let's put Denise in the middle of the bed, and Sheryl on her right side. I'll take the left side. The rest of you guys can sleep in the sleeping bags on the floor. Marybeth, you can use mine."

"That's not fair!" protested Kathy. "I want to masturbate him... er, her, too!"

"Yeah, and we should keep a nightlight on so everyone can see what is happening," pointed out Jodie.

"Well, I don't think everyone should be on the bed," said Margie defensively. "The light's okay, but three of us girls-Sheryl, me, and Denise - is enough. It'll be too crowded if the rest of you guys get into bed too!"

"I have an idea," said Christine. "We'll all take turns - and remember, we can't let Denise get soft. Make her come into a glass and drink it! And don't forget to drink your pee, Denise."

I took a swig of urine and Christine continued, "First it was me, and then Marybeth, and Jodie was third. Now Sheryl; she'll sleep next to Denise and keep him hard all night. Margie is next. When Sheryl makes Denise come, Margie can take over, and Kathy can take Sheryl's place on the bed. I think it's only fair that she should take Sheryl's place and sleep next to Denise, because she'll be last. But then we'll start over: me, Marybeth if she wants to have sex with her... uh... sister. After that, it's Jodie, Sheryl, Margie, and then Kathy again. How many times do you think she'll come in one night?"

"She's already come twice; I'll bet each of us can make her come," suggested Sheryl, who was stroking me quite fast. "Quick! I think he's gonna come! A cup! Get me a cup!"

All eyes were on me as I ejaculated into the paper cup; even I was disappointed that it had neither the force nor the quantity of the first two ejaculations, but what did they expect: it was my third come in as many hours. The silver lining was that there was less to drink.

Margie took over while Sheryl changed places with Kathy; the bed got noticeably smaller. Margie stroked me slowly but I could not get an erection. I was tired and I needed some time to recuperate, so she spent her time exploring me. Without a warning she suddenly kissed my shaft, but my body still wasn't ready to respond. "What's the matter? Don't you like me?" she asked in whisper.

"Yeah, Margie, I like you a lot; I like you the best," I whispered back. "But you have to give me more time."

"How much?"

"I don't know," I admitted. "I never look at the clock. 15 minutes; 20 or 25 tops. Don't worry; I'll come: you just have to be patient. Maybe you should use your mouth some more."

"Yeah, maybe," she agreed before suddenly changing direction. She cried, "Christine, how big did you say that high school guy's dick was?"

"It looked a lot bigger than Denise's," she claimed. "Mike's was about six inches long and an inch or more thick. Denise's looks like a short pencil." (Bitch! This morning I borrowed a tape measure from Mom, and I found that my dick is almost five inches long and 2 1/2 inches around; using the formula d = C ÷ pi that I learned last year in math class, my penis has a diameter of 0.797757471 inch.)

The girls all laughed at Christine's comment, but Margie was nice. She whispered, "I don't care if your penis is small; I think it's cute."

We chatted some more, and time seemed to fly. I guessed that my body had built up its lost strength, and I asked, "Margie, do you wanna make out?"

We made out, and her hand went to my dick. I tried rubbing her crotch also, and I could feel that she got wet there. That really excited me, and I suggested she kiss my dick once again. She kissed me several times, up and down my shaft, and she actually licked pre-cum off the tip. I reached inside her pajamas bottoms and I felt her hair, but she pulled my hand out before I could actually feel her slit. Even so, I found Margie's actions stimulating, and I made the mistake of telling her that I was going to come. She grabbed a glass and I shot my wad in that; if I had kept my big mouth shut, I'm sure I would have drenched her face.

Next it was Kathy's turn. Without a word, she took my dick in her mouth and started sucking on it. It was cool to see her take my dick into her mouth, but I don't think she did a very good job. Perhaps it wasn't really her fault; I'd come several times already, and although I was as hard as could be, I couldn't come in her mouth. I tried to tell her to twirl her tongue around the tip of my dick, but she didn't seem to understand what I was saying.

Despite the fact that she wasn't perfect, Kathy's efforts didn't result as I would have liked. Eventually we gave up and decided to go to sleep. About an hour or so later I woke up, and Kathy's mouth was on my dick again. This time I was more ready, and I knew I was going to come, but for some reason, I didn't. I ended up having to jerk off into her mouth because she couldn't make me ejaculate otherwise. She smiled a toothy grin, opened her mouth to show me the come, and swallowed hard. "I don't understand what the big deal is," she declared. "It doesn't taste so bad."

Christine and Marybeth argued about who would get to play with me last; Marybeth claimed she should since she hadn't had a chance to masturbate me earlier. Christine insisted it was her turn and pointed out that Marybeth could have sex with me any time she wanted. Marybeth finally gave in; when Christine told me she was going to take over, I explained how I needed to recuperate. She understood, took her time, and I had a sixth ejaculation shortly before dawn.

We had to get up early to go to the lake. The girls made put Margie's panties on (and I had to pay her $5) over my regular clothes so Mom and Dad wouldn't catch on to what had gone down the night before. When I packed my things for the beach, they made sure that I didn't pack my swim trunks, and since I was wearing jeans, I couldn't simply swim in my shorts. Marybeth packed two bathing suits, which sounds odd, but she is actually quite weird and nobody would think it strange coming from her.

After packing, it was time for breakfast: Kathy took the last of the pee to the table and told my mom it was apple juice; I tried to smile when I drank it down. Later we drove to the beach (Dad has this huge SUV and all of us fit), where I suddenly "discovered" I'd forgotten my trunks. Marybeth came to my rescue; lo and behold, she had two! The drawback is that both were one-piece suits, and she planned to wear the solid red one, leaving only the one with yellow and green flowers.

Since I was wearing jeans, I had to change. I tried to weasel out of it, but Mom insisted I had to go swimming at least for a while-we hadn't come all this way, blah, blah, blah. I was horrified when she suggested I swim in my underwear -what would Dad say when he saw my blue-and-white polka dot panties? Mom kept up the pressure, and finally I went along with the flowered suit.

The girls teased me to no end, and later that day when we got home, Jodie, Sheryl, Christine, and Kathy all gave me their panties-perhaps "sold" is a better word, since I had to give each of them $5. They informed me that they planned to come over on Tuesday after school, and I would be expected to wear one pair. I gave Kathy her size 38 panties back; there was no way I could wear them, but she still insisted I give her $5 like everyone else.

Marybeth and her friends were convinced they had gotten the better on me, but like Brer Rabbit in the Uncle Remus stories, the joke was on them. Little did the girls know that I had once secretly jerked off into a pair of my sister's panties, and that on two separate occasions, when I was home alone, I had tried on her clothes. So I was actually looking forward to playing dress up with five foxy girls and fat Kathy L!

The End

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