3- My High School Sweetheart’s Little Sister- pt. 3 (Truth Or Dare)

3- My High School Sweetheart’s Little Sister- pt. 3 (Truth Or Dare)

---------------------Part 3  - TRUTH OR DARE - ---------------------

A lot of things changed in the time that followed. My girlfriend, Chloe, went to another state to attend college. I chose a college in our home town.

I was kinda lost. Chloe and I were still in love, at least I was with her... but I assumed she was seeing other guys at her new school. 

Without Chloe, there wasn’t a legitimate reason for me to hang out at her house anymore. I would drop by to say “hi” every now and then, but it felt rather pathetic to hang around her family when we were apart. 

I missed Chloe. I missed her family. And I really missed Cindy. I constantly fantasized about her, about those movie nights. 

Months went by...

Chloe called me one afternoon, in a bit of a panic. Her older brother had been in an accident. She knew nothing more, except that he was at the Valley Hospital. Her mom and dad were headed down there. She asked if I could run up to the house and let Cindy know, as she would be coming home from school soon and hadn’t heard. This was before cell phones, so they hadn’t been able to contact Cindy.

I drove up to the house as fast as I could. Cindy had just walked in the door. She was surprised to see me, and gave me a big smile when she opened the door. That quickly changed when she saw the look on my face. I told her about the situation and tried to calm her sudden panic. 

      “We have to get to the hospital! Can you drive me to the hospital?”

We ran out to my car and drove out to Valley General. Cindy was pretty stressed during the drive, but we were both relieved to see the happy looks on her parents’ faces when we got to his room. His car was totaled, but he had only suffered a broken arm. He needed to stay for a cast, but all was good. 

I called Chloe and let her know. 

We all stayed there until he was released. They were very appreciative I had grabbed Cindy and brought her to the hospital. They decided to get burgers on the way home and invited me to join. 

Cindy rode with me back to her house. It was a nice drive... polite conversation. At one point I grabbed her hand and told her how much I missed her family and hanging out at her house. She squeezed my hand and said she missed it too. “It’s weird not having Chloe around. And I miss our movie nights on the couch”

        ‘Tell me about it’  I thought to myself. 

Dinner was nice. Her parents asked how school was going, my job, etc. They were being polite and supportive, but I still felt like the odd man out. 

After dinner Cindy said, “Let’s go watch a movie”, and ran downstairs. I feigned boredom...  “Can I help you clean up, or anything?” 

Her mom smiled, “No... you go ahead. I’ll make some popcorn for you.”

I walked downstairs and Cindy was running around, cleaning up the room. I watched her as she moved. She had changed out of her school uniform into a light yellow t-shirt, and red silky shorts. She looked so good... even better than earlier that same day. Tanned arms and legs, thin but muscular, and a firm, round butt. I could tell she was wearing a bra, to my disappointment, but understandable since her parents were still up. 

She turned on the TV and started looking for a good show. Her mom came downstairs with popcorn and some Coke for us. 

I thanked her mom and sat down on the couch, leaving plenty of room to my right for Cindy... more than I would normally, but her mom was watching. 

And Chloe was not there. 

Cindy climbed over the back of the couch and flopped down beside me. She started flipping through channels, but had little luck finding anything that looked interesting. We landed on an old comedy that both had seen before. We chatted through the whole show. It was great talking with her and catching up on everything. She was heavily into sports (that explains her legs and tight little ass). Enjoying school. No boyfriends. 

The next show up was also a dud. 

Cindy huffed... “This is boring. Anything else you want to do?”

I looked at her with a sly grin... “I can think of a few things... do you have a blanket?”

She laughed and poked me in the shoulder. “I haven’t forgotten.”

She looked over to the stairs, then got up and ran upstairs. I heard her talking to her dad, then she came back downstairs and closed the door behind her at the bottom of the stairs.

           She closed the door. 

I have never seen that door closed. This will NOT look normal to her dad. 

She crawled onto the couch, laying back on my right, on the side pillow, feet towards me. She tucked her bare feet under my legs. 

She was a vision, there beside me. Tan legs, toned body, long blonde hair framing her beautiful face. No makeup hiding her natural beauty. 

We talked a bit more, then I got my courage up and asked, “Wanna play Truth Or Dare?”

She flashed a mischievous smile, “Truth or Dare? ...that depends”

“On...? Depends on what?”

“Depends on if you’re gonna cheat. Depends on if you’re going to use ice.”

Hahaaaa... she does remember. 

I started, “Truth or dare?”

  Cindy: “Truth”

Me: “Have you been a good girl in the past year?”

  Cindy (laughing): “HA- I’ve been a saint”

Me: “No smoking, drinking, or cavorting?”

  Cindy: “No... I’m not sure what cavorting is, but I’m sure I haven’t done any.  My turn... Truth or Dare..”

Me: “Truth”

  Cindy: “Did you miss me?”

Me: “You have no idea. I thought about you every day”

  Cindy: “That’s sweet. You were on my mind as well.   ...truth”

Me: “Have you been seeing anybody?”

  Cindy: “You mean any boys? ...nope”

Me: “Really? No cavorting? No boys? I don’t believe it.          ... truth”

   Cindy:  “What about you? Any girls?”

Me: “No. Just school and work”

   Cindy: “And I don’t believe that either... 


        I had to try and test the waters

Me: “Do you ever think of me when you diddle?”

Cindy looked at me with a surprised look and let out a small giggle. 

  “Diddle? Is that a code word for poking pins into a voodoo doll?”

I laughed and shook my head. “Always the smart-ass. No, not exactly... to be honest, I have been diddling a lot thinking about you”

This left her at a loss of words. She looked at me with a nervous smile. 

I continued, “Are you still a virgin?”

Cindy: “Hey, you’re cheating. It’s my turn. But, yes... I told you I’ve been a saint. My question: When did you lose your virginity?”

I laughed, “I was going to choose ‘dare’, but I’ll answer.. I was fifteen. With a pretty girl I dated before I met Chloe.  My turn. So, a saint, and a virgin? Have you ever touched a boy’s penis?”

She laughed hearing the word ‘penis’. “Well... I was going to choose ‘dare’, but I’ll answer (smiling)... No... I’ve never even seen one... well, except in pictures.”

“Seriously? Never? Not even your brother’s?”

“Nope. Never. Why don’t you show me yours?”

I laughed, “I didn’t choose ‘dare’. You’re not following the rules”

Cindy: “Okay... another question, huh?  Have you ever touched a boy’s ‘penis’ ?” 

She giggled. 

“You aren’t playing this game right” I scolded her, “I take a mulligan on that question.”

Cindy: “What the hell is a ‘mulligan’?”

“That’s where I skip a question because I don’t want to answer”

She frowned at me. “Talk about cheating. You have to answer every question and perform every dare in this game.”

“Oh, so you’re an expert on this game? ...Okay, there might have been some touching a long time ago with my cousin when we both discovered our dicks got stiffies. Enough of that though... My turn”

     Cindy: “Dare”

Finally. I swear she was never going there. I looked over at her and my heart started racing. She was reclining on the couch, perpendicular to me, with her bare feet under my leg, beautiful tanned legs bent, her knees together. I moved my right hand to her feet, “Okay. Remember your rules... you have to perform every dare”

She looked at me with squinted eyes and a mischievous grin. 

Me: “Open your legs”

Her face lost its expression, but her gaze was locked on me. I looked down from her angelic face, and stared at her legs. The muscles relaxed, and her knees parted... just a little. 

I ran my hand up from her foot, up the inside of her calves. “More. Open your legs more... I want to see you better”

Her knees dropped further apart. I stroked my hand up her leg and past her knee, then back down to her foot. I lifted her right foot and moved it to the edge of the couch, then moved her left foot to the back, behind my butt. With her feet spread apart, her knees wanted to fall back together. I stopped them, and eased her knees further apart until they relaxed. 

I could now look straight up between her legs. My eyes looked her up and down, and landed on her crotch. Her red shorts were too big, and loose on her, so I could see a little up inside the leg of her shorts. 

The peek view up the leg of her shorts sent blood racing to my dick, which was already awake. I glanced over to the closed door at the stairs and prayed I could hear it if someone walked down the stairs. My eyes fell back to her crotch. 

“Show me your panties”

Cindy: “I think it’s my turn. Show me your panties... I mean your underwear.”

I looked down at my pants and my excitement was obvious. My dick had created quite the bulge in my pants, still bent down and trying to lift up out of the constraint. I unbuttoned my Levi's and folded the fly open to expose my underwear. Nothing was showing except the fabric. My dick was still curled down below my fly. 

Cindy looked at my underwear, then back at me. 

“You look a little uncomfortable. Why don’t you pull it out?”

I smiled, “My turn... pull your shorts aside and show me your panties.”

Her knees instinctively pulled back together slightly. I reached up and gently spread her legs open again. 

She looked at me and tried to smile, but her lips were quivering. She was very nervous... but she reached down and pulled the leg of her shorts up and to the center, exposing light yellow panties, up around where her bush would be.  

“Down lower... I want to see down lower”

She moved her fingers down and pulled her shorts aside so I could see her panties where they covered her pussy. There was a damp spot in the center. 

       I had been fantasizing about this forever. My dick was about to bust the seams of my jeans. 

“Sorry, I can’t handle this. I need to adjust myself”

I lifted my ass and slid my pants down just a bit, reached down in my underwear, and unfolded my dick so it could straighten out. I didn’t pull it out, but Cindy’s eyes were locked on my movements. 

She was still holding her shorts aside, and her legs actually opened up a little further as she stared at the outline in my underwear. 

“Show... show it to me,” she stammered, her eyes still locked on my underwear. 

“That’s right... you’ve never seen a penis... a ‘cock’? ...is that a better word?”

She didn’t reply. She just stared. Her eyes were wide, and her mouth slightly open. 

“Pull your panties over a little. I want to see your tan lines.” She moved her fingers over to her panties and pulled the leg opening aside a little, exposing her tan line and a little bit of pubic hair on the top. Her hair was light brown, thin and fairly sparse. 

I reached down and held my underwear tight against my hard-on, and opened the fly so the bare skin of my cock showed, about mid-shaft. 

“Pull it out” she whispered. 

“I want to see your pussy. Pull your panties all the way over so I can see everything.”

She moved her grip down on her panties and pulled them completely aside. Looking up between her tan legs, open for my viewing, was her pale bikini line, and a small light-haired bush, topping the most beautiful pussy I had ever seen. Her clitoris poked out from above her light pink lips, and her little pussy was dripping wet. 

My heart was pounding; my mind was racing... so aroused I could barely move- I just froze and stared at her... drinking in every detail.  

She broke my concentration, “Pull it out!” 

I looked up at her face. Her beautiful, innocent face... innocent, but definitely horny. She was almost panting, mouth open, her eyes locked on the bulge in my underwear. 

I replied, “Why don’t you pull it out?”

Without hesitating she reached across, stuffed her hand under the waistband, grabbed my cock, and pulled it out from my underwear. 

“It’s so big” she said, wide-eyed, as she squeezed the shaft. At 8”, I am above average size, but not ‘porno large’. Regardless, my cock looked absolutely huge in her small hand. 

She had released her panties, but they stayed off to the side, and her legs were spread even wider now as she leaned forward. Her exquisite little kitty still in full view. I reached down and lightly rubbed her, sliding my fingers up and down until they were wet. Pulling them back to my mouth I tasted her for the first time. 

I moved my hand back to her pussy and slid one finger inside her. I could barely slide it in past the first knuckle. She was so tight. She certainly wasn’t lying about being a virgin.

Still holding my cock, she used her left hand to push my hand away... pushing my finger out of her. One finger was uncomfortable for her. 

     One finger... not even all the way in. 

I looked back at her delicate hand wrapped around my cock and thought “never in a million years”.  My tongue, however...

She squeezed and released my cock, and moved her hand all over it, getting her palm wet when she ran it over the head. She moved her hand down to my balls, gently cupping each one, then going back to my cock. She ran her finger over the veins and up around the head, completely mesmerized. She gave it a final squeeze, then lay back against the side pillow. 

I licked my fingers and started to rub her little button- she closed her eyes.

“Yes... I like that. Keep doing that” 

Her right hand fell to her panties, and pulled them harder to the side. She pushed downwards on her feet, spread her knees further apart, and arched her pelvis upwards against my hand. 

The was no expression in her face now. Her mouth was slightly open and hers eyes were darting around like mad under the closed eyelids. 

I licked my fingers again, and went back to rubbing her pussy, concentrating on the little button on top. Her head started nodding up and down lightly, telling me that was the right place... keep doing that. 

Her legs started shaking a bit, and her muscles tightened. I increased the tempo and pressure on my fingers, and watched her face as she climaxed. Completely silent, her face turned red and her eyes tightened as she rode it through. 

It looked like a strong climax, but I know I enjoyed it much more than she did. The vision of her beautiful face, that innocent face that I had known for so long, rolling through a climax, is one I will treasure forever. 

Her body relaxed and she let out a large breath and sank into the couch. 

I pulled my hand away and sucked on my fingers, savoring every bit of her. She opened her eyes and smiled, then looked back at my cock. 

“I wanna see you cum”


It was her dad’s voice. 

We froze hearing it from upstairs. We had both assumed her parents were asleep by now. 

      “Cindy! Come upstairs!”

Cindy jumped up in a panic. I stuffed my dick in my pants and buttoned them back up faster than I have ever before. I pulled the pillow over my lap to hide my erection. 

Cindy opened the door and ran up the stairs. 

I was glad he hadn’t called my name. 

A few minutes passed. I could hear them talking, but couldn’t tell what was being said. Cindy came back down and said I had to go. She had to get to bed. I tucked everything in place and walked up to the front door.  I thought of saying goodnight to her parents as Cindy let me out the front door, but decided it was better staying quiet. 

I whispered to Cindy “unlock the downstairs side door and put on your nightshirt. I’ll sneak back into your room in a bit”

I left before she could comment. 

....................Next: Part 4  - Sneaking back in -

Similar stories

Skyrim: The Adventures of Carthalo Part 1

Carthalo stroked her cheek, feeling her smooth, cold skin and brushing the jet black hair out of her eyes. Lydia, he said, his gravelly voice brought to a whisper in her ear relax. This is not another burden for you to bear. he unclasped her shirt and she shuddered slightly at the touch. This is not a command from your Thane. his strong hands picked her up by the waist and he carried her to the bed. The floorboards creaked as he carried her up the stairs of Breezehome. He laid her down on the bed gently and began to kiss...


Likes 0

Charles Helps His Mother Feel Pleasure Again Chapter 7

Words from the Author: Hello everyone thank you for reading my story thus far, it has come to my attention from a very honest reader that my story has become very boring, I sorry if you feel that way, on my other forum I’ve never really had anyone tell me this so I’ve never considered it. Also some of you might be noticing grammar and spelling errors, some are simply by mistake, I’m not a professional writer and writing isn’t in my job description so you won’t see much in the way of advanced typing tech with me, also when it...


Likes 0

Phone Sex With Patricia

As I recently drove to my next business trip destination, I thought about the hot letter my beautiful wife had sent to my last location. My wife Patricia is a gorgeous brunette with beautiful 35D breasts, a hot ass and thighs to match! The letter read: My Dearest Lover, I am thinking so much about you right now... My loins are aching. I just did something naughty and sexy... I hope you like it! I shaved ALL the hair off my pussy. Ooo, Baby! Then I went in the shower and lathered up. It was hot!! I wish you could have...


Likes 0

New Beginnings - Pt 4 Ch 03

Darn! No sex in this one at all! Just a bunch of people talking! Chapter 3 “Someone came through the wormhole in Lisa’s Grotto?” Alicia asked, her eyes wide with surprise. “Who was it? Anyone we know?” “No,” Jake replied. “Some pregnant girl from Canada and her boyfriend. The girl claimed she met Beth once, evidently. And Beth initiated her.” “Beth was a long time ago, Jake,” Frank said. “You mean she’s a long-lifer? Like us?” “Yep! Both her and her boyfriend,” Jake replied. “What’s her boyfriend like?” Tanya asked, grinning mischievously. “He must be pretty virile if he got the...


Likes 0

Lessons From The Barnyard, Part IV

Bobby stepped into the shower first with her new husband right behind her. Junior cuddled up next to her from the rear and put his arms around her shoulders, hugging her in the most loving manner. They had been married less than a day and he had declared his love for her so many times in so many ways. He absolutely adored his young wife and now more than ever, he was going to make sure nothing ever happened to her because, after all, she was carrying his child. They got married that morning at his home so their baby would...


Likes 0

Alternate Time

I am the warden of a special prison complex in central South America, and my prisoners are of a unique category owing to the nature of their crimes. The prisoners here are all attractive females...and have been given the option of serving three months here doing filthy porn videos...or serving ten years in the government prisons...an unpleasant alternative at best. The government prisons are overcrowded...and mismanaged, and corrupt...and women who serve time there are unavoidably damaged physically and mentally for life...if they are fortunate enough to survive the ordeal at all. The women who come here have committed less serious crimes...


Likes 0

The Week I Cheated - part 1

I didn’t really want to go out, but it was better than being alone and bored to death in the barracks that Friday night. Being the oldest guy in the platoon, and the only married one, I figured there wasn’t going to be much for me to do at the base club. If nothing else, I figured I would just grab a couple beers and play some pool while my buddies made their moves and tried to score some dirty dancing with the local ladies. At the very least, I’d get to see a decent bar fight – one of which...


Likes 0

First Timer_(0)

**this is a fantasy. yeah. a fantasy. uh huh.** i went to the walmart and was checking out the new DVDs and games. as i was standing there a kid came up and started playing a game. he was about 11 or 12. i am not always attracted to guys much younger than me, but this kid was fucking hot. looked like a little skater boy with his baggy shorts. he was quite a bit shorter than me, blonde with brown eyes. as i watched him he kept adjusting his crotch. i was getting hard. i wanted to approach him, but...


Likes 0

Something Extra Part 2_(1)

This is Chapter two in a series. Make sure you read the first part first! After the disaster with Matt I was torn as to who to date next. I still wanted a real man inside me in spite of how good as Tina was with the dildo. On the other hand, I was kind of over my passive stage and wanted to fuck some ass. I didn’t care who it belonged to… The week flew by and I figured I’d go to 'Eric's', one of my favorite clubs Saturday night and just pick up whoever I could. At this point...


Likes 0

Our liberating holiday - part 1

Alice and I had holidayed together for several years, twice a year we would go to Europe somewhere for a week to catch the sun as neither of our partners enjoyed the heat. We both had hectic jobs and appreciated the relaxation that a girlie holiday could offer. I was a tall brunette, good bones, large bust, I guess you’d call me Amazonian in body structure. Alice was petite, very fair, with a lovely set of boobs but very fine and dainty. We always had a laugh together, relaxed in our own skins and comfortable to be together, often sleeping in...


Likes 0

Popular searches


Report this video here.