Younger Babysitting Memory

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Younger memory of babysitting.
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I remember when I was 18 and Dana was 19. Dana was a neighborhood girl who my Aunt Carol knew. She lived three houses down in another single floor cape house in the small cluster of homes outside of Wellfleet Massachusetts. I had yet to meet Dana. I was nervous around girls and especially a new older babysitter. I was curious as to why they would ask her to babysit anyway since I was old enough.

My Aunt told me she was watching the three of us boys after my aunt and her boyfriend was leaving at 7 o'clock to go out for dinner.

I was already at my Aunts house for the weekend hanging out with my guy cousins like boys do, playing Army, building wooden forts from discarded pallets. My cousin Tim was 8 and his brother was 10.

The sun was starting to go down when we heard Aunt Carol yell: "Ok boys lets go were leaving. Danas going to be here soon."

We all ran in the house like brats on four pounds of candy. Jumping and hopping around like assholes. We got yelled at and were told to sit on the damn couch.

"Ok listen. You do not act like this for Dana once she gets here do you understand me?" my Aunt sternly asked the three of us.

"Yes we know," all three us said at the same time.

All of us heard the doorbell ring. My Aunt went over to unlock the door and slowly pulled it open towards the inside. My Aunts boyfriend yelled: "Dana!!" like they had been best friends for years.

"Damn girlfriend look at you! How old are you now? 25? 28?" Rick, my Aunts boyfriend says to her.

"Ah stop it, Rick, I wish I was so I could drink." Dana laughed.

I was a dog in heat the second I saw her standing in the doorway. Hip length orange-red hair in a ponytail, shorts so small I could see the bottom of her butt, and decent breasts for a 19-year-old. Her legs were the finest I had ever seen up until that point in my life. I had seen many legs in my mom's lingerie magazines, but this was like having a supermodel from a dirty movie standing right in front of me.

She flung her sandals off and walked over to the recliner and listened to my Aunt and Rick tell us about the night's plans or whatever, it didn't even matter to me. I couldn't even tell you what they said because my eyes were glued to her body so hard I could've lit her shorts on fire from staring for so long.

The adults left and we had the entire place to ourselves for the night. All four of us sat in the living room for an hour watching TV. My two cousins said they wanted Dana to set up the Nintendo for them so she got up and I caught a shot of her ass in her shorts. Her tiny shorts were wedged in her buttcrack so tight it looked like her ass was trying to eat them off of her.

She led them into the bedroom and squatted down in the doorway and the shorts went even higher, and deeper. I couldn't take it anymore and I had to grab the blanket that was on the couch to cover up my raging erection. At that age, like any boy, I could go for hours and hours and would have fucked anything. She was driving me absolutely crazy.

After getting them set up with Super Mario Brothers and closing the door she walked back over to the chair and sat down with her legs up near her chest. Again, all I could see was right up her shorts, this time I knew without a doubt she wasn't wearing any underwear.

We started talking here and there. I wasn't a professional conversationalist at 18 so I tried to let her do most of the talking. The television was on and I was trying to look at it so she wouldn't feel uncomfortable with me checking out her fine body all night.

"So Mister Ben, what should we do? I'm getting sick of the TV," she asked.

"No idea," I replied even though I knew damn well what I wanted to do, I wanted to bury my face in her butt cheeks and lick her pussy for hours.

We both got up together and opened a closet we thought might have board games. Monopoly was over our heads, Battleship was missing pieces, and Chess might as well be Chinese hieroglyphics to us.

We were standing pretty close to each other in the closet and she says: "Hmm, I got an idea. Ever play truth or dare Benny boy?" she asked me in a quiet and coy voice.

Now I have only heard of "Truth or Dare". It was always for the older kids and it was like Dungeons and Dragons to me: taboo. My heart almost shot out of my chest I was so ecstatic, this older teenage girl wanted to fool around with me.

"Uh, yeah I just didn't know how to play the game. You're going to have to show me," I said nervously.

"Ok, the best place would be here in the closet but we should probably play it on the couch so I can see your cousins and make sure we can see when your Aunt and Rick pull in."

I went over to the couch and got under the blanket while Dana dimmed the lights and made sure the boys weren't killing each other. She plopped down on the other end of the couch and explained the rules. At this point, I could taste adrenaline. The possibilities were endless and this could be the night I could touch my first boob.

"Ben, I go first. Truth...or Dare?"

"Truth,"

"Ok, are you a virgin?"

"False."

"Ben you gotta tell the truth that's why its called Truth or Dare. DUH?!"

"Ok fine truth."

"I thought so. Now you go."

"Truth or Dare?"

"Truth,"

"Are you a virgin?"

"I'm not a virgin."

"How many guys have you..."

"Ben! Gotta wait your turn buddy boy."

"Truth or dare Ben?"

"Dare,"

"I dare you to...pull your shorts down to your ankles,"

So I did. But unknown to her, I pulled them all the way off. I was under the blankets anyway.

"Ok Dana truth or dare?"

"Dare,"

"I dare you to take your shorts off AND your shirt."

She looked outside then at the bedroom where my cousins were playing to make sure the coast was clear. The lights were dimmed and the TV flicker was aimed just out of reach from the couch. She slowly grabbed her shorts near her hips and started pulling them down towards her calfs. She stopped for a second when she saw headlights outside but it was a neighbors car.

She got under the covers and the soles of her feet brushed up against the underside of my penis. She realized what had happened and sat up after apologizing. Then her shirt came off. We were in my personal version of heaven. Naked on a couch with a gorgeous redhead with a raging erection.

"Ok. Truth or Dare?"

"Dare,"

"I dare you to grab my boob real quick."

I pulled the blanket over my head and crawled towards her breasts, or at least where I thought her breast would be. My tongue was out and I brushed it up against something that felt like an armpit and kinda tasted like it too. It made her giggle when we both realized it was her pussy that I had licked. I shot back towards my side of the couch and she had her hand over her mouth laughing.

"Oh, Ben. Nice one, nice one."

I didn't know what to do other than enjoy my first pussy kiss and get right back into the game. And now I had to get creative. I wanted IN.

"Truth or dare?"

"Dare,"

"I dare you to get out of the blanket and bend over so I can see your butt."

"OK,"

Dana tossed the blanket off her upper body and looked around again. She flipped over and bent her hips. I could see her butthole and her pussy. I had never seen a butthole before. I couldn't believe how nice hers was.

"Ben, I dare you to lick my ass."

The second I got up to put my tongue in her crack, we saw lights pull into the driveway. The both of us froze instantly like deer in headlights. My cousin heard the doors shut and ran out into the living room. Dana tossed the blanket over the both of us and told me she would handle this. The door opened and My Aunt and Rick picked up my cousins and hugged them both. He told them it was bedtime and gave us a dirty look. We didn't know what to do. So we stayed put, both of us naked and I had a full-blown hard-on.

My Aunt laughed at us and went right into her bedroom. Rick put the kids to bed and came out into the living room. He stopped in the middle of the room and grabbed his belt and begun to take it off. I really thought he was going to hit me with it, instead, he pulled his pants down to his ankles and kicked his pants across the room. He then sits on the couch between us and asks us how we were doing.

"Uh, good Rick. What are you doing?" Dana asked.

The way she responded made me think they were attracted to each other. Dana asked him if Aunt Carol and the kids were in bed for the night and he nodded his head. She said "Good" and leaned over and started kissing him with her tongue. She leaned out of the blankets enough so I could see her butt. Ricks penis started to get hard little by little.

Rick was in pretty decent shape for a 35-year-old guy. He was blonde and six feet tall. Blue eyes, almost Nordic. I've never been in front of anything like this and it actually made me really hard. Watching him getting pleased by her was very nice. His penis was incredibly long. It was like the size of my forearm! He grabbed her hand and pulled the blanket off of me at the same time. My cock was exposed and I was shivering from the cold and being so nervous.

"Ahh, Ben you look freezing, come here," Dana said to me with her arms outstretched.

I crawled across Ricks cock and snuggled with Dana. I turned around so that Dana and I were both facing Rick. I could feel her huge breasts on my back. She moved her head closer to my forehead and kissed it. She then took my right hand and brought it down towards her crotch, and I could feel her pussy. I could feel wetness and flesh and it was warm, so when she pressed my fingers into the fleshy part they slid right in. She moved my fingers in and out of her hole. After a few minutes, she led my right ring finger towards her butt hole and started to do the same thing. Her butt hole wasn't as wet but she kept spitting on my finger for moisture I guess.

I turned my head back a little and Dana and I started kissing with our tongues. All of a sudden I felt a hand touch my cock. It was definitely Ricks hand because it was pretty large and manly. I then feel something slippery and freaked out and had to see what the heck he was doing to my cock.

"Sorry, dude! Its ok, just some lubricant so I can jerk your cock a lot easier. Just sit back and keep fingering Dana. You're gonna like this big boy."

I can honestly say I did! Ricks hands even though they were large, seemed to know every part of my cock that was sensitive. This was the first time I had ever had any kind of sex with anyone and here I am fingering a hot redhead and getting my cock jerked off by my Aunts boyfriend.

I was trying my best not to ejaculate but it was getting really difficult. The sensations I was feeling were indescribable. At this point, Rick very slowly and carefully sticks his finger in my butthole. Same lubricant he is using for my cock. After a few minutes of his finger, he asks me if I wanted the real thing. I wanted his cock and bad, I never knew how bad until he asked me.

Dana said "Hold on you two. I'm getting some too. Ben, let me see your dick."

I turn over and my cock slaps her in her knee. She grabs it and holds it while she bends over in front of me and licks her right hand, and spreads her pussy lips with her middle and ring fingers. She's looking at me and brings my cock to her pussy and guides it right inside. Rick says: "Oh hell yeah!" then tells me to bend over while I'm fucking Dana. That's when he slowly guides his huge cock into my butthole. It was awesome!! I rode his cock. I was pounding Dana.

Rick came first and I could feel every time he came inside me. He fell back and I could feel all if his cock veins rub against my asshole as he pulled out and fell backward. Cum was pouring out of my ass onto the couch. Right before I came Dana told me to put my dick inside her asshole, which made me come as soon as I slid it inside of her. Then I fell forward while she rubbed her pussy and squirted all over my stomach.

The next thing I remember was waking up, all three of us under the blankets around 10 o'clock the next morning to the sound of my Aunt making breakfast in the kitchen. She saw me open my eyes and came out to us and said: "You guys are crazy. Breakfast is ready, and it's my turn next."

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