I was having a slumber party for my birthday and five of my girlfriends were sleeping over. We were all in my bedroom in playing truth or dare.
“OK, truth. How many of us are still virgins?” asked Katherine.
I raised my hand along with three others causing Katherine and Jessica to burst out laughing.
“OK, truth. How many of are still ‘technically’ virgins?”
I didn’t realize until it was too late that my three virgin friends had raised their hands.
“What? Cccinnddyy… you’re the only 100% virgin here? You’re considered the prettiest girl in school. You’re a 38D flaxen blonde.” laughed Jessica.
“We all need to get a move on helping Cindy here lose her virginity. FAST!” joked Katherine.
For the first time I felt a little guilty about being a virgin and realized I did need to get more adventurous with boys. But the problem with all the boys at school was they were boys and far too immature.
“I’ve got the ultimate dare for Cindy. Giving her brother Caleb a hard on.” said Katherine.
Everyone doubled over in hysterical laughter.
Everyone except me. I tried to brush it off as a joke. “That’s funny. One of you can try it if you want to. He’s downstairs playing video games in the basement.”
“Oh come on. That’s no fun. Teenage boys are too easy to seduce. They masturbate on average every two hours. But Cindy giving her own brother hard. Now that’s funny. Go on Cindy. Put on a sexy nightgown and go into the basement and try giving Caleb a boner. Set your cell phone to video and hide it somewhere so we can watch from upstairs. Go on.” urged Jessica.
Now I was really starting to worry. They were actually starting to look serious about this. Once again I tried to laugh it off. “Come on. I’m his sister. He can’t get turned on by me.”
“Wanna bet? This is the ultimate test. Are teenage boys really so horny that they’ll go after their own sisters? Some on Cindy. You’re taking a bold step for womankind.” said Katherine.
My five friends wrapped around me doing my makeup and styling my curly flaxen hair. I took off my T shirt and barrowed Katherine’s peach colored sink nightgown. It was so short it barely passed my hips and really enhanced my already massive cleavage. Hayden let me barrow a heart shaped locket to dangle between by breasts. “It really turns guys on.” she assured me.
Just as I was about to leave my bedroom Katherine stopped me. “Wait. Panties off.”
“You heard me.” And she held out her hand.
I reached underneath my nightgown and slipped off my panties handing them to her.
Katherine ordered, “Now go. And don’t forget, we’ll be watching.”
As I walked down the stairs I enjoyed the cool breeze between my legs as my thighs rubbed together. I’d never gone pantiless before but I now understood why so many girls did. I knocked on the basement door as if I was meeting my executioner.
My brother answered, “Yeah what?” After unlocking the door Caleb immediately returned to his videogames not even looking in my direction to acknowledge my presence. He sat there cross legged in his pajamas eyes fixed to the TV screen.
I inconspicuously rested the cell phone on the entertainment center so it had a perfect view of Caleb, and locked the door behind me. My parents were upstairs and if they walked in they would send me to a convent after castrating my brother.
“Aren’t you having your sleep over?” he asked coldly.
“Yes. But I was more interested in what you were doing.” He was still too focused on his video games to answer. I sat down next to him as close as I could practically in his lap. “That’s some joystick.” I said seductively.
“What?!” shouted Caleb. Simultaneously a ‘Dragnet’ theme sounded from the TV. “Now look what you made me do! I died!”
“Well here. Let me play with you.” I said. Again is a seductive voice. I reached over a grabbed a controller. A new game started but I didn’t even look at the screen. Instead I held the controller close to my stomach and turned to Caleb asking, “What does this button do?” Of course my brother couldn’t see the button or controller. They were buried underneath my very inviting cleavage.
Caleb looked away very embarrassed. “What button?”
“This button. This button right here.”
“It shoots.” he answered looking away from me.
“No this button. What does this button do?” Each time I spoke I bounced up and down adding a little giggle to my cleavage.
“It’s Atari. There’s only one button.” he answered, now working up enough courage to glance in my direction.
“No this button.” I asked bouncing up and down more and more. “This button. This button right here.” Now my brother couldn’t look away no matter how hard he tried. “This button. This button right here. I need you to touch my button and show me how it works.” I continued to bounce. For a moment I thought I saw a run of saliva escape his lips. He was actually drooling!
I took him by this wrist and brought his egger hand over to rest on the controller at the base of my stomach. “This button right here… Oh Caleb, what a strong right hand you have. It’s so muscular. You must use it a lot playing by yourself. I mean playing video games by yourself.”
“Umm yeah.” he said nervously, freeing his hand from mine and wiping away the escaping saliva embarrassed by his body’s instinctive actions.
Since it would be too obvious to look directly at my brother’s crotch to see if he had an erection I merely reached into his lap and grabbed his controller. I deliberately rubbed my hand against him and brushed up against something VERY hard. “The reason you play so hard by yourself is the size of your joystick.” I flirtatiously moved the stick controller back and forth. “See your joystick much much bigger than most. You must have happy endings every time you play by yourself. Play video games by yourself.” I placed the controller back in his lap to confirm what I had felt earlier. He was hard as a rock. His brain was completely emptied of blood.
I stood up and stretched my arms seductively. “Well I’ve neglected my girls. The six of us were comparing breast sizes and I won. Now we’re all going to take a big bubble bath together.” As I was leaving I knocked the cell phone off of the chest. “Oh my. I’ve dropped my cell phone.” I bent over fully at the waist so my brother could see my pantiless body.
I giggled all the way back upstairs. I couldn’t believe what I’d just done. TO MY OWN BROTHER! Me, such a shy girl. I was excited by the way the whole experience had made me feel. I was pretty. Truly pretty enough to excite a man. It’s one thing to hear, “You’re pretty.” from your grandparents. But to be sexy enough to turn your own brother on. That was the ultimate compliment.
As I knocked on my bedroom door I felt a sudden feeling of sadness. The excitement was over. I would never again feel such a high. The sadness was not just for myself but for Caleb as well I’d left him all alone to just play with his joystick after giving him such a sensation and teasing his body’s male instincts. I felt like turning around and telling him how sorry I was for playing with him. To build up his excitement and leave him empty and unsatisfied.
Inside my bedroom we all laughed ourselves silly. Another cell phone had recorded the entire event. Oh the look on my brother’s face. He pitched a tent in his pajamas big enough for a three ring circus when I bounced up and down. “We should put this on YouTube!” laughed Jessica. “We have proof. Boys really are horney enough to have sex with their own sisters!”
After at least half an hour of nonstop laughing. Katherine raised another evil eyebrow. “You know, your brother looks pretty big.”
“Yeah.” chimed in Jessica. “I’d say seven, maybe even eight inches.”
“So tell us Cindy, how big is your brother?” asked Katherine.
“How should I know?”
“Well certainly you must have accidentally walked in on him in the shower, getting dressed, or doing something else naked sometime in your life?” asked Jessica.
“Well then. There’s really only one way to know for sure. Measure it Cindy.”
“You heard me. Measure your brother’s penis and report back to us with the results. Once again we’ll be watching via cell phone.” commanded Katherine.
This time around I put up no resistance. It was like riding a roller coaster. A sudden rush of excitement.
When I knocked my brother rushed to open the door for me. “Hey sis! Want to play videogames?”
I hid the cell phone again and held up a measuring tape. “No, I’ve been sent down here to take measurements.”
“Measurements?” a feeling of dread came over my brother’s face.
“Yes. You see the girls want to know how big you are to see if you’re worth doing.”
After our last encounter I thought he would be egger to oblige but the look of dread still haunted his face. I had no idea why.
“Oh come on Caleb. Let me measure you and you can have your choice of any girl in that room.”
My brother still looked down ashamed.
“What’s the matter Caleb? How about any two girls in that room? Would that make you feel better?”
He looked so upset I seriously thought he would start crying. “It’s not that sis. It’s that I’m kind of on the small side. The girls would just laugh at me.”
“Oh come Caleb. I don’t think you’re small. Tell you what, I’ll add an inch or so when I make my report upstairs. Now enough stalling. Down with your PJs.”
I’d never seen a penis in real life before and my eyes bulged as my brother took down his pajama pants letting them rest at his ankles embarrassingly.
“Oh Caleb dear. You have to stand at attention.”
“I can’t.” he answered.
“Nonsense. You saluted me earlier, you can do it again.” Without anymore argument I immediately dove into my recent gymnastics routine spreading my legs and holding them above my head wearing nothing more than the sexy silk nightgown which easily revealed my naked front and rear.
A few minutes later I looked back at my fully erect brother. I seized the opportunity and wrapped the measuring tape around his hot flesh. He was still standing with his pajama pants around his ankles. Even though I was barely touching him he was gasping for breaths, his chest heaving in and out.
“There we go. 6.3 inches long and 2.7 inches around. All that fuss from such a well endowed young man.” He smiled at my flattering comments. “That’s a good size for a boy of your age, any age. But I’ll add an extra inch on for the girls upstairs. You’ll be neck deep in pussy.”
The second flirtatious experience had been exciting for both of us. But still I felt sad for both of us. I didn’t want the wonderful new feelings I was having to ever end. And I wanted to do something more for my poor lonely brother.
As soon as I came back inside my bedroom Katherine’s wicked mind was already on to phase 3! “OK, great work Cindy. Your next assignment is to bring back a sperm sample.” We all screamed with delight.
Then Hayden held up a cell phone. “Um I think Caleb’s already ahead of you on that.”
I’d forgotten the other cell phone in the basement! My brother was sitting on his bed, his pajama pants still around his ankles clearly stroking off.
“Hurry! Stop him Cindy before he cums!” ordered Katherine.
Without thinking I rushed downstairs. The wind caressing my naked crotch. I banged on the basement door. “Caleb. Don’t cum. Wait for me. Don’t cum yet.”
I continued to bang on the door oblivious to the danger of my parents hearing me. No matter how hard I banged Caleb wouldn’t answer. Well of course! What teenage boy would answer at a time like this? Desperate I began slamming my shoulder against the door and kicking at it with my bare legs. How my parents didn’t hear this I’ll never know.
Eventually the door gave way and I rushed inside just in time. My brother’s eyes were rolled into the back of his head and he was letting out a final climactic moan. I held out my hands together to form a cup and tried my best to capture the waves of creamy white semen. Of course some of it squirted onto the nightgown and got caught in hair.
Caleb was in too much ecstasy to even comprehend what I was doing. But I quickly commented. “Good. I needed a sperm sample.” Fearing my brother’s nectar would literally slip through my fingers I raced back upstairs.
I entered my bedroom carrying my own brother sperm in my bare hands. My five friends looked at my hands longingly. Without a word they all got on their knees and drank my brother’s sperm out of my hands savoring every delicious drop.
I glanced at the cell phone and saw that Caleb was lying naked on his bed fast asleep with a smile ear to ear.
“Yum yum. Your brother tastes great.” said Hayden.
Katherine raised another evil eye. “Umm that was delicious. But Cindy? You’re the only one of us who hasn’t enjoyed the pleasure.”
I licked my hands clean savoring the taste of semen for the very first time in my life. And lucky me. I had a steady supply right in my own house.
All my friends agreed. It was the best sleepover ever!!!
The next day after school my brother knocked on my door. “Umm. You said I could have any girl in that room I wanted right?”
“Yes. I promised.” I answered.
“Well, I know which one I want.”