Truth or Dare?
Posted: Sat Oct 19, 2024 4:55 am
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. She asked 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 smiled and said to her, “I remember how adorable you looked back then, and how you blushed. You looked absolutely stunning in that bikini.”
She asked me "Truth or Dare?"
"Truth," I replied.
She laughed and said, "What did you mean when you said, 'I looked great in that bikini'? What were you thinking when that happened? Remember, it was an embarrassing moment, so please be kind in your response."
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?"
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.
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 smiled and said to her, “I remember how adorable you looked back then, and how you blushed. You looked absolutely stunning in that bikini.”
She asked me "Truth or Dare?"
"Truth," I replied.
She laughed and said, "What did you mean when you said, 'I looked great in that bikini'? What were you thinking when that happened? Remember, it was an embarrassing moment, so please be kind in your response."
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?"
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.