Truth or Dare with my Sister-in-Law

CDarcy©

A special thank you to Stealthwriter for the help in editing...

***

I was suspicious as soon as I heard the oozing sweetness in her voice. My wife of four years called me at work just before noon to ask me if I would be willing to go "rescue" her 18 year old little sister and bring her back to California. She went on to tell me how her sister had just broken up with her jerk of a boyfriend and was out of a place to live. She then confessed that she had volunteered me to do the four hour each way turn around trip from our place to Vegas.

Six hours later I pulled up outside my sister-in-law's work place to pick her up. We swung by and grabbed a few boxes of her possessions out of her friend's car, and were quickly on our way back across the desert.

As the misfit of the family, she has always leveraged shock value to get attention. She had several tattoos, her hair was always a different color, today it was bleached blond, and she had a sailor's vocabulary. Whereas my wife is an athlete and well put together, the most exercise my sister-in-law seems to get is lifting her fork or rolling a joint. Her weight had spiraled up over the last couple of years, but even with her being 5'5" and close to 200 pounds; still, she is a very attractive girl.

As soon as we were out of town, she asked me if it was okay if she changed from her work clothes and put on something more travel friendly. I told her that it was no problem and I would be happy to stop at the next rest stop. She said, "No need to pull off," as she quickly stripped her shirt over head, as she gave me a great view of her red bra with a sparkling rhinestone in the middle, holding two of the largest jiggling tits I had ever seen. She reached around and grabbed her tank top from her backpack and pulled it on, still showing off her amazing cleavage. She then wiggled out of her pants, and I saw that she wore a matching red thong. She then pulled on some loose fitting cut off sweat shorts over her thick thighs.

She looked at me and, catching me watching her, gave me a coy smile and said, "It's a long drive, let's play a game."

I said, "Sure, what are you up for?"

"I don't know, what do you want to play?" She replied.

"It was your suggestion babe, you pick," I said.

"How about Truth or Dare?" she asked with surprise hint of trepidation.

"Are you sure?" I asked, with my eyebrow cocked.

She giggled and said with mock confidence, "I am sure, unless you want to chicken out!"

I smiled and said, "You're on! We'll play 'Truth or Dare?'"

"Truth," she said.

"Okay, tell me where you got that fantastic bra and panty set," I asked.

"Oh, did you like them?" she smiled and then continued, "I got them at Victoria's Secret." Then she quickly said, "Your turn, Truth or Dare?"

I went for truth to see what kind of tone she was going to take to this game. She turned toward me and said, "Boxers or briefs, which do you wear?"

It was my turn to smile, and I replied, "Neither, I prefer to go commando, it saves on the wash."

Her face looked a bit shocked as my answer had caught her a bit off guard. I continued and asked her, "Truth or Dare?"

"Truth" she replied.

I asked, "When did you lose your virginity."

She tossed her hair over her shoulder and took a deep breath as she shifted in her seat to face me. "In the eighth grade, and it was with Tommy Peterson. We went to the winter formal dance at school and afterwards one thing lead to another. He ended getting about three thrusts in with his four-inch dick before he blew his load. It was so sad and quick, he totally left me frustrated and disappointed. We broke up shortly thereafter."

She raised one of her feet up and rested her chin on her knee while sitting toward me giving me a peek down her loose shorts at her red lacy thong. "Truth or Dare?" she asked.

"Truth," I said as she caught me stealing a look down her shorts.

"Are you enjoying the view?" She asked, while looking downward shyly.

I replied, "I do indeed like the view. I have always thought you were very attractive. But to tell you the truth, because I am driving, I don't get to appreciate it fully."

She squirmed a little and said, "Thank you, you are pretty hot yourself.",

I asked her, "Truth or Dare?"

She answered, "Truth."

"What was your most embarrassing moment," I asked.

She laughed and said, "When I was fourteen. It was that Labor Day party at my Grandparent's pool. You and my sister had just started dating and I had the biggest crush on you. I dove in trying to show off and when I came up my bikini top had slipped down exposing my right tit to you, and my cousin Billy saw it. Billy, the perv, still has never let me live that down."

I laughed with her and said, "I totally remember that you were so cute and adorable and I remember that you turned completely red. You really did look good in that bikini."

She asked me "Truth or Dare?"

"Truth," I replied.

"What do you mean, 'I looked good in that bikini' and what were you thinking when that happened? Remember, it was embarrassing, so please be kind," she said with a smile.

I took a deep breath and confessed, "That little black bikini was hot and left little to the imagination. You had bloomed so early and you already had a great chest. The thought of that cute pink nipple that was hard and puckered has been the subject of more than one lonely evening fantasy for me. Out of curiosity, how big was your bust then?"

She smirked, "Humm... at 14? I was only a 34 c. What do you mean 'lonely evening fantasy?'"

I shifted in my seat, "Um, you know, things to think about when the only date I have is my right hand."

She laughed and said, "I had NO IDEA, you have ever thought of me in that way."

I said, "Truth or Dare?"

"Truth," she said as she slowly waved her bent leg back and forth slowly exposing more and more of her panties to me.

I asked, "So, when did your crush on me end?"

She bit her bottom lip a little and sheepishly answered, "Who said it ended?"

She looked up and I smiled, which seemed to reassure her a bit as I said, "Well, I am very flattered and deeply honored."

She looked over at me and said "I drank 2 big cups of coffee this afternoon at work; I've got to stop and pee at the next gas station."

I told her, "I have to do the same. I'll keep my eye out."

She asked me, "Truth or Dare?"

"Truth," I said.

She replied, "What was the kinkiest thing I had done while making this drive to Vegas before?"

I answered, "Your sister and I would always play on this stretch of road. She would flash truckers, she would suck me off, I would play with her, and we would stop on the side of the road and screw. We even found a glory hole in one of the rest stops once and played for an hour with anonymous travelers. Yeah, the kinkiest time had to be the time at the glory hole."

My wife can come off as a prude, so this shocked her. She blushed and said, "I had no idea, I thought I was the wild one. Tell me what happened?"

I continued, "Well, we stopped at the rest stop and I noticed there was a 3-inch hole drilled between two of the stalls in the men's bathroom. I told her about it but she didn't believe me. The bathroom was empty so I took her in to show her. We heard footsteps coming, so we ducked into the handicapped stall and locked the door. We hear the door next to us open then close and the sound of a zipper. I peeked through the hole and saw the guy pissing. As his stream ended he started fondling his dick until it got hard. Your sister pushed me out of the way to take a look just as he pushed his hard dick through the hole. I whispered to her to take hold of it and help the guy out. She reached out and started stroking him slowly. She picked up speed as we heard additional footsteps coming down the steps outside. I could see the guys fingers grasp the top of the stall as he grunted and started to shoot all over your sister's hands."

"Oh my god!" she squealed.

"There's more," I said. "The guy pulled back and opened the door and we could hear him acknowledge the man from the other footsteps who had entered the bathroom. We heard the door on the stall next to us open and shut again and I peeked through the hole. I could see a perfectly shaped and sized cock pointing towards us as he gently fed it through the hole. I asked your sister if she was ready for another one and suggested that she take this one in her mouth. She leaned down and stroked the guy two or three times before leaning down and took him in her mouth. As she was bent over, I pulled up her skirt and moved her panties to the side to begin fingering her. She was so soaked and turned on, and she was moaning on the guys cock. I moved in behind her and started to fuck her as she sucked the strangers cock. I could tell by the guys groaning that he was close, and within a couple of minutes he started cuming in your sister's mouth. She was so turned on by the whole experience that her pussy started to clamp down on my dick as she came, forcing me over the edge. Yeah, that was the kinkiest thing we've ever done on this trip across the desert anyway." I finished with a wink.

My sister-in-law had her mouth agape in shock and she was flushed across her chest; "Truth or Dare?" I asked.

"Truth," she answered, still reeling from my recent revelation.

I replied, "Tell me about one of your kinkiest desires."

She looked down and squirmed a little. She looked over at me and said, "Do you really want to know?"

I said, "I'd love to know you a bit better, try and shock me."

She smiled and looked me dead in the eyes, "Pee turns me on."

"Really, what part of it turns you on?" I asked.

"Watching and being watched. Just talking about it causes me to tingle," she said.

Her bravado seemed to come back as she asked me, "Truth or Dare?"

"Dare," I answered.

That seemed to catch her a bit off guard. She thought for a moment and said, "I dare you to prove you aren't wearing any underwear."

I thought of whipping out my cock for her, but decided to go with a bit more build up. I pulled the side of my shorts up to the waistband to show her that I wasn't wearing underwear; then I adjusted my cock as I pulled the leg back down.

I asked her, "Truth or Dare?"

She answered, "Dare."

I dared her to take off her bra. She smiled and reached under her tank top to pull her bra off over her shoulders leaving her tank top on. Without her bra I could make out the outline of her nipples that had hardened and were standing at attention. She tossed her bra at me and I looked at the tag, it read "40DD."

She smacked me and said, "Guys are such pigs." She then looked at me and said, "Truth or Dare?"

I took another truth and she asked what I thought about her, "Am I pretty," she asked. I told her that, although she was bigger, I thought that she was beautiful in her own right.

I asked her, "Truth or Dare?"

"Truth," she answered.

I asked her, "How turned on are you right now?"

She opened her legs and pulled her shorts to the side, showing me the large wet spot that had soaked through her red panties. She said, "What do you think? Look at what you have done to me. This certainly isn't pee, although I really do have to go." Then she said, "Your turn, Truth or Dare?"

I said, "I have to go too, and it looks like we are still a ways off to the next gas station. I'll take a dare this time."

She reached back and found an empty Gatorade bottle as she said, "I dare you to pee in this."

I cocked my eyebrow at her told her to hold on to the wheel. At 75 miles an hour I took out my penis and stuck the tip in the bottle then started to fill it up. She moved her head down for a close up and said, "That is one of the hottest things I've ever seen."

I finished and tucked myself back in, then told her that it was her turn.

She said, "I don't think I can aim that well."

I laughed and told her it was her turn for Truth or Dare.

She said, "Truth." I asked her if she was having fun. She told me that indeed she was and added that she had been attracted to me for a long time. She also added "Seeing you piss made me have to go even worse. I need you to pull over now!"

I found a side road where we could exit so she could pee. When we slowed to a stop she jumped out and dropped her shorts and red panties and squatted next to the truck. I could hear the pee hitting the ground and asked her to see her panties. She smiled and tossed them to me. As I caught them, I noticed how the crotch was wet. I looked at the tag and saw that she was a size 16. Then I tossed them in the back of my truck along with her matching bra. As she pissed she looked directly at me and, with a wicked smile, asked me if I wanted to watch.

I scooted over in the seat and, as she continued to squat, she pulled her lips apart so I could watch. Her piss streamed in an arc before hitting the ground.

She finished, pulled up her shorts and jumped back in. She said, "Thank you, I really needed that."

As we returned to the road, she asked me, "Truth or Dare?"

"Truth," I responded.

"Did it turn you on to watch me pee?" She asked.

I answered, "Very much. I wish I had seen more, but just the sound of it, along with your wicked grin, was a huge turn on for me." I was anxious for the game to continue, "Truth or Dare?"

"Dare," she replied.

"I dare you to flash the next trucker we pass," I said.

She said, "Okay, Truth or Dare?"

"Truth," I answered.

"What is your favorite sexual thing to do?" she asked.

"Mmmm," I thought before answering. "I like almost anything sexual, but my favorite thing is making a woman squirt. There really is no comparison to the feeling of satisfaction that I get to have my partner, after back to back orgasms, culminate in the ultimate orgasmic expression by squirting all over the place." "I'm almost afraid to ask," she replied, "but what do you mean?"

I turned to her and said, "A woman can have two distinct orgasms, the first that radiates out of your clit, the second from deep inside you connected with your g-spot."

As I was finishing my explanation, I pointed at a truck we were about to pass. I slowed down to the pace of the truck while she turned to the window and lifted her shirt. The trucker smiled from ear to ear and waved back to us. My sister-in-law pulled her shirt down and sat back saying, "Wow, that was really more exciting than I expected."

I looked at her tank top to see the nipples jutting at attention, and I nodded and said with a smile, "Yes, I can see that." I then said, "Truth or Dare?"

"Truth," she said.

I asked, "What is the most orgasms you have had in a single session?"

She looked at me quizzically and said, "Uh, just one."

"So far," I quipped with a grin.

"So far then," she smiled and asked, "Truth or Dare?"

"I'll take a dare," I replied.

She thought for a moment and said, "I dare you to let me touch your cock."

I pulled the leg of my shorts aside and presented my semi-stiff member to her. She slid over and took my shaft in one hand, while with her other, she caressed my hairless balls. She cooed as my penis stiffened in her hand. Taking a couple of slow strokes she inhaled deeply and said, "Very, very nice. I especially love how smooth you feel." After another minute of this, she sat back and said, "I'll take a dare."

She was sitting Indian style on the seat facing me, and I could tell that she was soaking through the crotch on her shorts. "I dare you to let me taste your juices," I said. She pulled her shorts aside and her plump, glistening, shaved pussy came into view. Her lips were slightly parted and I could see her creamy white juices oozing out. She leaned back and said, "Here you go." I took a finger and, while sliding it slowly up her slit, her juices coated the end of my finger, and I could feel her legs shutter. I then took this finger and put it in my mouth, tasting the sweet, citrus taste of her pussy. She moaned deeply while watching me lick my finger clean.

I looked at her and, with a wink, said, "Dare."

She told me that she needed an orgasm in the worst way, and could I finger her while we were driving. She put her feet on the dash, leaned the seat back, and I went to work. In five minutes she was screaming in orgasm and, afterward, said, "Oh My God that was amazing!"

I told her, "That was only the beginning; it gets a lot better." Then I smiled.

She said, "Pull off the road."

We pulled off onto another side road. I came around her side of the truck, laid her back on the seat and took off her shorts. Then I pulled her tank top over her head. Going down on her I began slowly licking her clit, while putting two fingers deep inside to rub her G-Spot.

She said, "Oh my god, what are you doing down there it feels fucking amazing!" as she writhed all over the seat.

I stopped licking and said, "I am going to make you squirt," then I went back to nibbling her clit.

She was moaning and groaning and I was licking, sucking and plunging my fingers faster and faster. She grabbed my head with one hand and the steering wheel with the other as her thighs started to tremble. I slowed my fingers while increasing the flicking of my tongue. Her juices were flowing, her nipples rigid and hard, and the veins in her neck contracted as she started to orgasm. While her pussy tightened around my fingers, I started to rub her g-spot. While one orgasm subsided, a second started to build. I had two fingers massaging her g-spot while i shifted my body up, taking a nipple in my mouth. I sucked and nibbled on one nipple, while with my other hand, I caressed the other. I could feel her build, as she her spread legs and started to quiver. Her whole body began to convulse as she screamed in pleasure, "Holy Fuuuuuuuck!"

I then lowered myself back down her body and, putting one of her legs on each of my shoulders, my tongue went back to work on her erect clit. She was sweating and panting and trying to catch her breath as she squirmed under my touch. I took some of the juices that were running down her pussy and lubed my other index finger, then slid it under her to her ass hole. I applied a little bit of pressure as I continued to lap her pussy.

Her next orgasm hit within seconds as I wiggled my finger on her ass and flicked my tongue over her clit.

"This is too much, but oh my god, it feels so amazing!" She moaned.

I switched back to rubbing her g-spot, while rising up her to kiss her and caress her body. Her orgasms were building and climaxing faster and harder. She reached up to grab the steering wheel and pull her knees up to her chest, leaving her pussy gaping open while my fingers continued to work their magic inside her. Her body tightened up and she exploded, squiring all over me and the seat. She ejaculated in such quantity that it soaked into the seat and filled the air with the pungent smell of sweat and citrus.

Her eyes got wide as she said, "What the fuck was that?"

I told her, "That my dear, is you squirting."

She said, "Oh my god, that was the most amazing thing that I have ever experienced. I have never even read about something that good."

She could feel my hard cock on her leg as we lay beside each other. Giving it a squeeze, she said, "You poor man, we need to take care of you."

She rolled me on my back and took my shirt and shorts off, exposing my shaved cock and balls at full attention, and pulsating with my heart beat. She cupped my balls and leaned down to slowly suck my dick and lick the underside of my head. She then straddled me and guided my hard manhood into her soft, plump, wet pussy as she sat on me. I reached up and took hold of her massive tits and started massaging them as she slowly started sliding up and down my shaft.

Her pace quickened while I told her how beautiful she was, and how much I appreciated the view. While she rode me her huge breasts bounced up and down. The veins running through her nipples from her neck and chest were clearly visible on her milky white skin. She screamed from another orgasm, causing her pussy to contract around my shaft. I thrust my hips upward to bury myself deeper inside her. I grabbed her hips as I shoot my load into her womb. She collapsed on top of me while we kissed. Our tongues danced together as I softened and slipped from her.

She said, "That was amazing. Thank you, thank you and thank you again."

I told her that I felt the same but that we should get back on the road. The sun was setting as we dressed and as we turned onto the freeway with 200 miles still to go; I saw the twinkle in her eye as she said, "Truth or Dare..."