Road Trip With Alyson and Amanda “AJ” Michalka

I should have known from the moment Alyson called that something was wrong. She had phoned me in the middle of the night from the East Coast to ask me if I’d “rescue” her 20-year-old sister in Las Vegas and escort her back to LA.

“What the hell are you talking about?” I mumbled half asleep. “It’s like 4am right now.”

“Please. Pretty please.” my girlfriend whined through the phone.

“Why doesn’t AJ just fly back to Los Angeles like every other normal human being?” I quipped rhetorically, recalling her phobia to fly.

Funnily enough her “symptoms” seemed to dissipate if and when her sister accompanied her on their cross country flights, but as it was Alyson and her family were visiting relatives in upstate New York while Amanda was now alone and stranded in Las Vegas, and a total wreck.

As it turned out, she had apparently hooked up with some guy she meet in a club who had swept her off her feet and convinced her to spend a dirty weekend away with him in Sin City, only for his true colors to soon emerge and the entire trip to turn ugly.

“Babe, please.” Alyson urged. “She was balling her eyes out over the phone and its breaking my mom’s heart.”

“So what do you want me to do about it?”

“Please go get her.” Alyson begged. “Do it for me, please?”

“You realize it’s an eight hour round trip, right?”

“I love you so much.” was Aly’s only retort. “I promise to make it up to you when I get back to LA, I swear.”

With that said, I hung up the phone and called Amanda to find out exactly where she was and where we would meet.

Six hours later I finally pulled up outside AJ’s motel room to pick her up and pack her suitcase into my truck before we found ourselves out on the open road speeding through the desert and heading back towards Los Angeles.

As the misfit of the family, Amanda had always leveraged shock value to get attention from her older sister so she was notoriously out spoken and usually dressed inappropriately, as was the case that day.

As soon as we passed the city limits she asked me if it was okay for her to change from her “vacation” clothes to something more travel friendly. I told her that it was not a problem and I would be happy to stop at the next rest stop, but she claimed I didn’t have to do that and quickly stripped beside me.

There I watched as she flipped her t-shirt right over her head and offered me a great view of her tight white bikini top which seemed to barely encase two of the firmest set of jiggling tits I had ever seen.

Amanda reached around and grabbed her tank top from her backpack and slipped it on, which now did a great job of framing her ample cleavage and showcasing her hard abdomen.

She then wiggled out of her pants and I noticed that she wore a matching white thong bikini beneath. She then pulled on some loose fitting denim cut offs and grinned smugly to herself when she caught me leering.

“Do you like it?”

“Huh? What?” I stammered.

“My belly ring.” she asked, as she lay back to display it for me. “I just got it a few days ago. ”

“What does your sister think?”

“Ugh. Don’t ask. She thinks it looks trashy.”

“But doesn’t she have the exact same thing?”


We both laughed.

“Hey, she’s your girlfriend.”

“Hey, she’s your sister.”

A minute later there was an awkward silence in the car as AJ proceeded to channel surf the radio stations and couldn’t decide on what she wanted to listen to. Finally after a few minutes she ran her fingers through her long blonde hair and huffed.

“This is going to be a long drive home.”

“You don’t say.” I quipped. “Try doing it by yourself.”

“How about we play a game?”

“Sure, I guess?” I replied. “What did you have in mind?”

“I dunno.” she shrugged. “How about Truth or Dare?”

Even as she made the suggestion she said it with a hint of trepidation.

“Are you sure that’s a good idea?”

AJ giggled and said with mock confidence, “Yeah. I’m sure. Unless you’re too chicken to play?”

“You’re on.” I grinned. “So be it. Let’s play.”

“Hmm. Okay, I’ll start.” she quipped. “I’ll pick, Truth.”

I paused for a moment to think of what to ask her – since she seemed so eager for me to question her – and then looked over at her sexy ensemble.

“Tell me where you got that fantastic bikini from.”

“Oh, you like it?” she beamed widely and then continued. “I stole it from my sister. She’d kill me if she ever found out.”

I had to laugh.

“I knew it looked familiar.”

Amanda then went on to explain how she had convinced her sister to buy several bikinis and lingerie the last time they had shopped at Victoria’s Secret, but since Alyson rarely wore any of the garments she decided to “borrow” them for a few days, hoping Aly wouldn’t notice them missing.

“Don’t worry, your secret is safe with me.” I reassured her. “By the way, it really looks good on you.”

As I spoke, I had to remind myself not to stare directly at her tits which at this point looked absolutely phenomenal.

“Okay your turn,” she quickly said. “Truth or Dare?”

I went for “Truth” to see what kind of tone she was going to take the game to. AJ turned toward me and grinned.

“Boxers or briefs, which do you wear?”

It was now my turn to smile as I revealed my secret.

“Actually, neither. I prefer to go commando, if you must know.”

To my amusement, Amanda actually looked a little shocked before I turned the tables and asked her the same question.

“Truth or Dare?”

“Truth,” she replied enthusiastically.

“When was the first time you ever had sex?”

With a huge grin on her face, the blonde bombshell tossed her hair over her shoulder and lit up a cigarette as she recalled the first time she popped her cherry.

“It was back in 2006, while Aly and I were on tour with our band 78violet.” she claimed. “I was 15, and I lost it to one of the roadies.”

“Really?” I snickered. “Why you little sly thing. Who was he?”

“He was much older than me, but I had a crush on him. So after one of our shows in Tampa I snuck into his hotel room down the hall and one thing led to another.”

“Wow. Did Alyson ever find out?”

“Hell no.” she giggled. “She’d kill me. Not to mention get him fired.”

“He still works with you guys?”

Amanda nodded.

“He kinda works around the house for my dad when we’re not touring. He’s kinda the local handyman.”

“Handy-Man, eh? I’ll say. How old is he?”

“I think he’s in his mid to late 30’s?”

In truth, Geoff had only recently celebrated his 44th birthday the week before.

“Jesus. And he popped your cherry? I guess you wanted your first time to be with someone with a lot of experience, huh?”

“Meh. Not really.” she claimed. “It was actually kind of a letdown.”

“How so?”

“The poor guy was so drunk and worked up that he only got about three thrusts in before he blew his load and literally passed out.”

“Wow.” I chuckled.

“It was so sad and quick, he totally left me lying there frustrated.”

“Did you guys at least try it again?”

“Nah. That was officially the first and last time I gave him a shot at my cookie.”

As Amanda spoke, she raised her feet up and rested her chin on her knees while sitting toward me giving me a peek down her loose fitting shorts and her white thong bikini bottoms.

“Truth or Dare?” she then asked me with a sly grin.

“Truth.” I answered as she caught me stealing glances down between her legs.

“Enjoying the view?”

“Err, is that your question?” I chuckled. “Yeah, sure. What can I say, I’m busted.”

Amanda rolled her eyes as she enjoyed her cigarette.

“Sorry, but that body.” I confessed. “I mean seriously, AJ. You look so much like your sister it’s not even funny.”

“Yeah, but I’m a lot more fun.” she grinned while blowing smoke in my direction. “Aly’s way too uptight, especially when it comes to sex.”

I simply shrugged, trying my best to keep my mouth shut.

“If you say so.”

“So what are you saying?” she probed. “You think I’m pretty?”

“What? You don’t know that already?”

“Yeah, I guess. I just like hearing you say it.”

“I doubt you need my approval, AJ.” I told her. “Besides, I’ve always thought you were cute. Even your sister knows that.”

“Oh yeah, that’s right.” she beamed. “The night you hooked up with Aly, you were initially hitting on me remember?”

“Ha!” I laughed. “I don’t remember it happening that way.”

We both laughed.

“If anything, you were coming onto me but then you hooked up with that bar tender dude.”

“Hmm. So my sister was a consolation prize? Interesting.”

“Not exactly. She just didn’t fuck me around that night like you did.”

As we spoke, I found myself leering at her bikini bottoms again and realized that the material was wedged up so tightly against her sex that I could clearly see a camel toe forming.

Unfortunately for me AJ soon caught me leering there again but to my surprise didn’t seem to care and continued to sit in a way which showed off the groove of her mound.

“Interesting thought though,” she added. “Who knows how things would have turned out if we had hooked up instead.”

“Come on,” I laughed. “We’d drive each other crazy. We would’ve probably killed each other by now.”

Amanda paused for a moment and flashed a sexy smile.

“Yeah, but imagine how great the (hate) sex would have been.”

Feeling bold, I then asked her “Truth or Dare” again, to which she chose “Truth.”

“What is your most embarrassing moment?” I asked.

AJ laughed.

“What sexually, or just in general?”


“It was probably that time my sister invited you over to our folks place for that Labor Day weekend BBQ? You guys had just started dating and I had the biggest crush on you. I dove into the pool trying to show off and when I came up out of the water my bikini top had slipped down exposing my tits in front of everyone! Remember?”

We both laughed again.

“Remember? How could I forget. All I remember is hearing your sister gasp out loud and when I looked over my shoulder there you were standing in the middle of the pool clutching your chest and turning beet red. Man that was funny.”

“Ha. Ha.” she replied sarcastically. “I was so traumatized I didn’t wear a bikini for a week.”

“But seriously, you looked amazing that day.” I added. “You usually do.”

“Truth or Dare?”

“Truth,” I replied.

“What do you mean, I usually do?” AJ inquired, fishing for more compliments.

I took a deep breath and confessed.

“Well, what I mean is you usually manage to look good no matter where you are or what occasion it is, and that day in the pool was no exception.” I admitted. “Let’s just say that entire incident was definitely memorable, and gave some inspiration on those long lonely nights when your sister was out of town.”

AJ smirked, “What do you mean, inspiration?”

I shifted in my seat.

“You know, things to think about when the only date I have is my right hand.”

“Oh god. Really? I had no idea.” she giggled. “You really beat off to me?”

“Err, well. When you say it like that, you make it sound so weird.”

I quickly tried to change the topic.

“Err, Truth or Dare?”

“Truth,” she said as she stretched her long bare legs and placed them on the dashboard in front of her while scratching an inch.

“So, when did your crush on me end?”

Amanda bit her bottom lip a little and sheepishly answered, “Who ever said it ended?”

I smiled back and told her that I was flattered, as Amanda then placed her hands on her abdomen and seemed concerned.

“Ugh. I think I drank too much coffee today. I’ve got to stop and pee at the next gas station.”

“Me too.” I chimed in. “I’ll keep my eye out.”

She then added, “Truth or Dare?”


“What’s the kinkiest thing you’ve ever done on a road trip?”

“Honestly? Well your sister and I have been known to have some fun out on the open road.”

“Bullshit, really?”

“Absolutely. Sometimes she’d flash truckers or she’d give me head knowing that other motorists can see us as they pass us by.”

“Rubbish.” AJ quipped. “This is my sister, Alyson Michalka you’re talking about?”

I snickered as I went on.

“Other times I’d play with her, and we’d get so riled up that I’d have to stop on the side of the road to fuck.”

Amanda seemed shocked, especially as she realized I was serious.

“I know your sister can come off as a little prude, but believe me Aly definitely has a wild side to her personality.”

“Wow. I’m shocked.” AJ blushed. “And here I thought I was the slut of the family.”

“You say that as if you’re disappointed.” I laughed. “That Aly might turn out to be a bigger slut than you?”

“I doubt it.” she scoffed. “That’s really the kinkiest thing you guys have done? Sex on the side of the road?”

“Well, alright.” I continued. “There was this onetime over holiday break when we were driving back from San Diego and we stopped at a rest stop to screw around.”

“Yeah, go on.”

“So inside we ducked into the handicapped stall and locked the door, and as we started to fool around we noticed this 3-inch hole drilled into the side of the wall, which allowed you to see straight into the other stall. Fortunately for us the bathroom was empty, but as we began to screw around we heard the door next to us open then close and the sound of a zipper.”

At this point of the story AJ seemed on the edge of her seat, squirming with anticipation.

“So we peeked through the hole and saw some dude taking a leak. Your sister pushed me out of the way to take a look while I decided to have fun and proceeded to fuck her from behind as she watched him.”

“So?” Amanda shrugged, apparently unimpressed. “That doesn’t sound so bad.”

“Yes until, the other dude soon noticed us screwing in the stall next door and he started jacking off while listening to your sister carry on.” I explained. “He then slid his cock through the hole and offered his dick to her.”

“Oh my gosh. What did she do?” AJ gasped. “Did she totally scream and run out of there?”

“Hell no. I told your sister that if she really wanted to turn me on, that she should grab his cock and jerk him off while I fuck her.”

“No fucking way!” Amanda squealed. “Alyson actually did that?”

I grinned smugly at her shocked reaction.

“Are you sure this happened with Alyson, and not just some floozy you were banging at the time?”

“No trust me, it was with Alyson.” I reassured her. “You’re so called uptight sister.”

“Wow. Aly actually whacked off some stranger?”

“Oh. There’s more.” I chuckled.

“Alyson was so turned on by the whole affair that she ultimately leaned down and just took his black cock into her mouth.”

“Wait, what?!” Amanda almost shrieked. “He was black?”

I had to laugh.

“Oh yeah. And the size of his black cock was fucking mind blowing.” I admitted. “I’d say a good eight or nine inches, at least.”

For the first time since our seedy conversation Amanda appeared to fall silent, her mouth agape.

“Anyways, she was so fucking wet from the pounding that she moaned around the guys cock and within a couple of minutes he shot his load all over your sister’s face. She was a complete fucking mess.”

At this point AJ looked utterly bewildered, lost for words.

“So yeah,” I finished with a wink. “That was about the kinkiest thing I’ve ever done on a road trip I’d say. Sharing my girlfriend with some stranger in a bathroom.”

Pausing for a moment I then added, “So, um. Yeah. Truth or Dare?”

“Truth,” Amanda answered slowly, still reeling from my recent revelation.

“Tell me about one of your kinkiest experiences. Have you ever gone black, like your big sis has?”

“No. Absolutely not.” she claimed. “But maybe I will, one day.”

“So go on, tell me one of your secrets.”

Amanda looked down and squirmed a little as she finished her cigarette.

“Do you really want to know?”

“Absolutely.” I said. “Try and shock me. I bet you can’t.”

AJ smiled and looked me dead in the eyes.

“Honestly? Anal really turns me on.”

“Bullshit.” I quipped. “You’re just saying that to get a rise out of me.”

“No, really. I’m not lying, I swear.”

“Really?” I replied. “What part of it turns you on?”

“It just seems so dirty and taboo.” she said. “Just talking about it makes me to tingle all over.”

“And you’ve done it before?”

Amanda scoffed, “Done it? I can’t stop doing it. I do it even when I masturbate.”


“Absolutely. It just really gets me off like nothing else.”

Her bravado seemed to come back as she asked me another “Truth or Dare” question.

“Dare,” I answered without thinking.

This seemed to catch her off guard a little. She thought for a moment before she responded.

“Okay. I dare you to prove you aren’t wearing any underwear right now.”

I thought of whipping out my cock for her, but decided to be a little more tactful than that. I pulled the side of my shorts up to the waistband to show her that I indeed was not wearing underwear, before I adjusted my cock and pulled the leg back down.

“Okay, now your turn. Truth or Dare?”

“Dare.” she bravely answered.

Without missing beat I dared her to take off her bikini top.

She smiled as she reached under her tank top to pull it off over her shoulders leaving her tank top intact. Without her bikini top on I could clearly make out the outline of her taut nipples that had hardened and were visibly standing at attention. She tossed her garment at me and giggled.

“You guys are such pigs.” she quipped in mock anger. “All you care about is T-and-A.”

She then looked at me and asked, “Truth or Dare?”

I took another truth and she asked me what I thought about her.

“No, be honest.” she insisted. “Tell me the truth. Do you find me attractive?”

I told her that although I thought she a little verbose at times, I thought that she was beautiful in her own right and suspected she was an absolute fiend in bed.

“Hmm.” she grinned smugly. “You have no idea, sweetheart.”

“I don’t doubt it.” I added. “With a mouth like that, and those lips. My friends and I suspect you’d suck a mean cock, AJ.”

“Mm. I do.” she purred seductively.

“Okay, Truth or Dare?” I then quipped back.

“Truth,” she answered.

“How turned on are you right now?”

Amanda responded to this question by simply opening her legs and pulling her shorts to the side, showing me the large wet spot that had formed through her white bikini bottoms.

“What do you think?” she grinned. “Look what this mere conversation has done to me.”

“Jesus.” I let out, as she then remarked something about dying to go to the bathroom to relieve her bladder.

“Seriously. If we don’t find a place soon I don’t know what I’m going to do.”

“Yep. You and me both sister.” I agreed. “I have to go too, and it looks like we’re still a ways off to the next gas station. Maybe next time around I’ll take a Dare instead of a Truth.”

With that said, Amanda reached back and found an empty Gatorade bottle and remarked, “Okay. I dare you to pee in this bottle.”

I cocked my eyebrow and told her to hold onto the wheel. At 80 miles per hour I took out my cock and placed the tip in the bottle then started to fill it. Amanda exclaimed loudly and moved her head down for a closer look and seemed genuinely fascinated by the display.

“Oh My God. That is one of the hottest things I’ve ever seen.”

Once I finished my business I tucked myself back in, then told her that it was her turn to fill the bottle.

“Err, I don’t think I can aim that well.” she giggled, as I teased her with another “Truth or Dare.”

She answered with “Truth” so I asked her if she was having fun, and if she’d agree that whatever happened or was discussed on the trip would strictly stay between us, and us alone. She happily agreed.

“You know, seeing you pee that way makes me have to go even worse now.” she squirmed in her seat. “You better pull over right now or I’m going to pee in this seat.”

Thinking quickly, I immediately veered my truck into a side road so she could pee.

When we slowed to a crawl she instantly jumped out of the passenger side door and dropped her shorts and bikini bottoms in one fell swoop, and squatted beside the vehicle. I couldn’t help but laugh out loud at the unexpected spectacle as she crouched there peeing in some ditch.

As Amanda relieved herself she looked directly at me with a wicked expression on her face, a combination of shame and contentment.

“You don’t have to look away if you don’t want to.” she smirked, as she relieved her full bladder. “I don’t care if you watch me.”

I felt my face blush with shame as I openly ogled her doing her business, and found the seedy action incredibly fascinating. There on the side of the road, AJ reached down with her left hand and pulled her lips apart so I could see everything.

Her urine streamed out in an arc before hitting the ground, as I suddenly felt extremely dirty for watching her in such an intimate act. After another minute, I looked up the main road and glanced back at her only to find she was still peeing. I was actually surprised to see just how much urine her body could hold.

The girl peed like a race house. Several moments later Amanda finally pulled up her shorts and hopped back into the truck.

“Wow.” I sighed. “That was incredible. How much coffee did you actually drink?”

“Thanks, I really needed that.” she sighed with relief. “I thought I was going to burst.”

As we returned to the road, I tried to shake my head of the lewd imagery but instead couldn’t stop seeing it in my head.

“So, Truth or Dare?” she remarked a minute later.

“Truth,” I responded.

“Back there. Did that turn you on, watching me I mean?”

“Of course not.” I scoffed. “I’m not a complete pervert you know.”

AJ simply smiled and waited for me to crack.

“Okay, what the hell.” I finally confessed. “I have to admit, that was kinda hot.”

Amanda laughed out loud.

“I had a feeling that’d turn you on.”

“Aside from Alyson,” I explained. “I don’t think I’ve ever seen another woman do that before.”

“Wait, you’ve seen my sister do it too?” she replied, sounding a little disappointed.

“Sure. We may or may not have experimented in the shower a few times in the past.”

“Okay. Now you’re totally blowing my mind.” Amanda snickered. “What are you saying, that you and my sister are into some kind of water sports of something?”

“What? No!” I laughed. “I never say that. We’re just very open in our relationship, I guess.”

“Besides,” I added. “There was just something so sexy about the way you sat there peeing with a wicked grin on your face. Like you were getting off on having me and all those passing truckers watch you.”

“Maybe.” AJ shrugged. “I guess I’d be lying if I said I wasn’t a bit of an exhibitionist.”

I was anxious for the game to continue, “Truth or Dare?”

“Dare,” she finally replied.

“Well, considering our conversation. I dare you to flash the next trucker we pass.”

“Okay, fine. Truth or Dare?”

“Truth,” I answered back.

“What’s your favorite sexual fetish?” she asked.

“Hmm.” I thought before answering.

“Do you have a foot fetish? Are you into rubber, S&M, golden showers, what?”

I simply snickered at her various theories.

“I guess I like just about anything, but my favorite thing is making a woman squirt.”


“Sure. There really is no comparison to the feeling of satisfaction I get from having my partner enjoy back to back orgasms, which then culminate with her squirting all over the place.”

“Oh wow. I’m almost afraid to ask.” Amanda replied, referring to her sister. “Are you saying Aly can do that?”

“Not always. But sometimes if I fuck her hard enough for long enough and don’t let her cum, then take that back massager you bought her for Christmas and grind it against her clit… she goes absolutely nuts and squirts all over the bed.”

As I spoke I could see my lewd descriptions were having an effect on her as Amanda now fidgeted in her seat.

As I was finishing my explanation, I pointed at a truck we were about to pass and reminded her of the dare. I slowed down to the pace of the prime mover while she turned to the window and lifted her shirt.

The trucker smiled from ear to ear and honked his air horn before Amanda pulled her shirt down and giggled.

“ohmigod! Get out of here, quick.” she blushed. “Speed up or something.”

I couldn’t stop laughing as we slowly pulled away from the 18-Wheeler.

“Well that was more exciting than I expected.” she claimed while she looked around for another cigarette.

I looked at her tank top to see her nipples jutting out at full attention, and had to agree.

“Yeah, I can see that.” I remarked, “Truth or Dare?”

“Truth,” she answered.

“What’s the most amount of orgasms you’ve had in a single session?”

She looked at me quizzically and said she had only ever had one or two at the most.

“Really?” I replied a little surprised.

“I could probably have a lot more,” she tried to explain her answer. “But usually I just roll over and fall asleep.”

“Jesus, you’re just like a guy.”

“Yeah,” she laughed. “A guy with great tits.”

“Truth or Dare?” she then countered.

“I’ll take a dare.” I told her.

Amanda thought long and hard for a moment as I watched her eyes roam over my body before she finally made a bold suggestion.

“Um, okay. I dare you to take out your cock and stroke it for a full minute.”

Considering how riled up we both were I didn’t hesitate.

“Okay. I’ll do it.” I agreed, as I pulled the leg of my shorts aside. “But you have to give me something to work with.”

“Like what?”

“Like, show me your tits again.” I insisted. “Play with your nipples or something while I whack off here.”

“Hmm. I think something can be arranged.” she grinned, before I watched her slip her tank top over her head leaving her seated beside me in nothing but her denim cut-offs.

To my delight her nipples were extremely hard and stood at full attention, just begging to be sucked. In fact in all the time I had dated Alyson, I couldn’t remember seeing her nipples look so aroused. They really were spectacular.

“So go on then,” she teased. “Play with your cock. I want to see you stroke it for me.”

“Sure, why not.” I replied as I watched her fingertips gently glide across her bare breasts, causing tiny goose pimples to break out all over her skin.

“You know, you should really take those shorts off too.” I daringly challenged.

“What, and sit here totally and completely naked? Yeah right.”

“Sure. You did mention how turned on you were flashing that trucker earlier. Imagine how exciting it’d be to sit here totally naked, while I beat off no less.”

To my surprise not only did Amanda agree but she eagerly striped in record time, leaving her to sit there naked as the day she was born. I immediately gasped with delight as I now studied her pristine sex and noted how different she was to her sister.

While Alyson kept a meticulously trimmed triangle above her clit, AJ appeared to be totally shaved clean and as smooth as a babies bottom. In fact she was completely bare and so aroused, that her pussy actually glistened with excitement as she sat back and placed her feet up on the dashboard.

“Truth or Dare?” I then quizzed her with a grin.

But playing coy, she answered with “Truth.”

“How many times do you masturbate? And what do you think about when you do it?”

Amanda blushed as she considered how to answer my loaded question.

“I probably do it at least two or three times a day, without fail.” she claimed.

“Really, that much? Do you use any toys?”

“Nah. I know my sister prefers vibes and stuff, but I just prefer to use my god given fingers.”