Double Girls and Double Dares

Rebecca and Cindy was a couple of twenty-one year old identical twins from Vancouver, British Columbia. It was the start of the summer and they had just finished their under graduate studies in English Literature and had decided to take a backpacking trip to the United States before attending graduate school in September.

The girls were a little above average looking, more of your small town or girl next door look. They would individually both be a six or seven on a scale of one to ten, but the fact they were twins obviously drove up their sex appeal.

They were around five foot five inches, about 130 pounds, shoulder length brown hair, brown eyes with average b cup breasts and average curves for girls of their height and weight.

The girls were each other's best friend and very seldom left the other's side. They did everything together. The same growing up such as activities, friends, jobs and even went to the same university. Both did a bit of dating growing up, but didn't really have a lot of time for the opposite sex, since they were always content keeping each other company and kept busy with school and part time jobs.

Now that they were both finished with university for a few months, they thought it would be nice to do some travelling and take in some of the North American cities they had always wanted to see.

The girls saved a bit of money from the part time jobs they worked while going to school, but not a lot, so they were confined to a budget. They purchased one way train tickets to San Francisco, a city they both always wanted to experience, and left Vancouver carrying only a large backpack each.

The train ride was 24 hours long and they were cramped into a row of three seats, with Cindy sitting next to the window and Rebecca in the middle. There was an older Indian guy, probably fifty years old, wearing a turban sitting to Cindy's right in the center isle.

The girls had lots of time to pass, but it was no problem for them. They had developed games to pass time over the years and could always keep each other easily content. First the girls began talking and planning their trip, but the conversation became boring and the girls were getting tired.

It was about 11:00 p.m. when Cindy suggested to Rebecca that they play their double-dare game, which they had played since children and had never gotten old. Rebecca clearly agreed as the challenger always got to give the first dare and neither had ever refused up to this point in their lives. The dares were usually silly and nothing more than a laugh at the other sister's expense, but nothing really that bad.

Rebecca's first dare was, "Cindy, I double-dare you to unbutton your blouse, show your cleavage and order a drink from the steward."

Cindy protested, "Come on, you have to be kidding, he is cute and all but..."

Rebecca countered, "We are on vacation. You say that you never let loose, well here is your chance and besides, the old guy next to me is fast asleep, so he won't see anything."

Cindy looked at Rebecca saying, "So it's going to be like this is it sis? Just remember I have a double-dare for you, too."

With that said, Cindy unbuttoned her shirt clearly down past her chest, close to her belly button. You could clearly see the tops of her milky white breasts and someone standing above would get an even better view.

As the steward walked by Rebecca shouted, "Excuse me, can we get some drinks over here please?"

The steward, a guy in his late twenties, definitely a pretty boy in great shape walked over and you could see his eyes almost pop out of his head as he fixed a glare onto Cindy's cleavage. He began stuttering his words asking the girls what they wanted to order and both girls calmly ordered their drinks.

Cindy looked down at her cleavage showing, smiled and said, "Oh! Sorry about that! This shirt seems to always come open." Cindy then quickly buttoned her shirt back up and the steward went off to grab their drinks.

Both girls giggled and Cindy said, "Fuck! I can't believe you made me do that! You are such a bitch! It's a good thing he was cute, but with that said it's my turn." Cindy looked at Rebecca saying, "OK. Your double-dare is to pretend you're sleeping and put your hand on that Indian guy's crotch. For at least two minutes."

Rebecca challenged, "That's not fair, Cindy! At least the guy I picked for you was good looking! This guy is old and disgusting!"

Cindy countered, "Well at least he won't see your tits and it's just two minutes. He probably won't even know."

Rebecca gave in, "OK, fine."

The Indian guy was in a deep sleep with a line of drool running down his chin and his legs spread wide open. Rebecca leaned back in her chair and reclined it all the way, getting in a position which made her look like she was sleeping. Then she reached her right arm over and gently placed it on the crotch of his cotton slacks. Rebecca could easily feel his cock and balls and made sure her eyes were shut tight, to claim to be sleeping if need be.

No more than thirty seconds after her hand was on the old guy's crotch the steward came back with the girl's drinks. He immediately noticed Rebecca's hand on the Indian passengers crotch and looked at Cindy saying, "Wasn't she wide awake only a minute or two ago and does she know that guy she is sitting with?"

The steward gave both girls drinks to Cindy, but in the process must have woken up the Indian passenger sitting next to Rebecca.

Rebecca could clearly hear the entire conversation as she was just faking being asleep, but couldn't do anything to blow her cover, no matter how bad the situation. Just when she didn't think it would get any worse, she felt a warm hand on top of hers and the cock beginning to grow hard in her hand. The steward had already walked away, but Rebecca had this guy next to her getting a hard-on with her hand cupping him. She felt the Indian guy begin to move his hand up and down to create some sort of friction, this had to stop and suddenly she herd a grunt and then felt some wetness beginning to seep through on her hand. The Indian guy pushed her arm away and then got up and walked away.

Rebecca opened her eyes, looked at her sister who clearly saw the entire thing and was bursting with laughter. Rebecca said, "Oh my fucking God! That was the most disgusting thing I have ever experienced! I gave him a fucking hand job, that wasn't in the dare!"

Cindy laughed, "Ha-ha! Good job! You should be proud. It only took like thirty seconds, but the down side is that you didn't complete your dare. I told you to keep your hand there for two minutes and it was only there for one minute. I guess the next dare is yours, but I will let you take a break for now."

Rebecca cried, "That's not fair! He left on his own and I went way further with my dare than you did. Either way I am getting you back, you had it way too easy with yours."

Cindy chuckled, "OK fine, well maybe we should get some sleep, especially before your friend comes back after getting cleaned up."

Rebecca agreed, "Yea, very true, well at least we should be there by the time we get up and I don't want to be tired on our first day."

The girls both cuddled up as best they could to try and get some sleep before arriving at San Francisco.

At 7:00 a.m. both girls woke to the sound of the train whistle arriving at their destination. Thankfully, Rebecca's Indian friend was already gone, but he left a note with his number on a business card next to Rebecca. Both girls laughed again and Rebecca ripped up the card and threw it on the floor.

The girls exited the train and were excited to begin their first day of their new adventure. The weather was great, giving them an opportunity to wear their fitted t-shirts and short shorts with flip flops while they worked on their tans. They first hit all of the tourist spots like the Golden Gate Bridge, The Palace of Fine Arts Theatre, and finished later in the evening at Pier 39 Marketplace. The only down side to the trip at this point was the very high number of homeless people they noticed in various places downtown, they seemed to be everywhere.

It was later in the evening and the girls decided they should probably check into the hostel, something they probably should have done much earlier, but didn't. Luckily, there was one just a few minutes away, but to their surprise the attendant told them they were completely full. The attendant advised them it was very late and the hostels book up very quickly and gave them a list of the seven hostels in the area and access to their phone. To the girls' disappointment after calling all seven, they were all completely full. It was probably because of the time of year with all of the college students being off for the summer.

Rebecca said, "Well maybe we should just throw out the extra cash and get a hotel room for the night."

"Rebecca, are you crazy? Hotel rooms are a fortune here and we don't' really have that much money. It's going to tap into our entire budget for this vacation."

Rebecca asked, "Well what do you suggest?"

"Well it's our first day here. We could always explore for tonight and maybe catch a few hours on a park bench or something and then check into a hostel first thing in the morning for tomorrow."

Cindy asked, "Are you serious? You are insane."

"Come on Becky, it's just one night and we must have counted a hundred homeless people today. If they can do it all the time we can certainly do it for one night."

"Yea, I guess you have a point, but let's make sure we get to a hostel early tomorrow and check in."

The girls began their stroll of the down town core of San Francisco, enjoying the buskers and culture, trying to make the best of their situation. By the time 3:00 a.m. rolled around, the girls began to get tired and their feet became sore from carrying their backpacks. They strolled into a close by park area and were lucky enough to find a bench that wasn't occupied. There was however, another bench next to it with an old wino homeless guy curled up on top of it, hugging his paper bag containing a bottle of cheap alcohol.

The old guy looked to be in his sixties, skinny build, white greasy beard and hair and wearing tattered old clothing. He wasn't bothering anyone and was probably just completely intoxicated and minding his own business.

The girls settled on the bench across from him in a foot to head position, to maximize space on the small bench and used their backpacks as pillows. It still wasn't very comfortable and the girls were having trouble sleeping.

Cindy spoke up saying, "I can't sleep."

Rebecca agreed, "Me neither. This is so uncomfortable! I don't know how that guy is sleeping so good, I guess he is used to it."

Cindy, "Yea, I know, he is out like a light. Since we both can't sleep, let's play double-dare."

Rebecca shrugged, "OK, sure, let's get this over with."

Cindy murmured, "Hmmm, OK, since you didn't finish your last one, I double-dare you to put your hand on that guy's crotch for the one minute you have left from your last double-dare."

Rebecca gasped, "NO WAY!! That's even worse than before, what's up with you wanting me to touch ugly guy's crotches?"

Cindy laughed, "Hey, if you finished your dare last time you wouldn't have to do this one."

Rebecca reluctantly agreed, "Fine, but you remember it's my turn to dare you next."

Rebecca then got up quietly, walked over to the old drunk and knelt down beside his waist area. She then very softly lowered her right hand down and placed it directly on his crotch. The old wino didn't budge and inch and clearly didn't know this cute university grad had her hand on his cock.

Rebecca looked over at Cindy and mouthed with her lips, "BITCH," and laughed.

Cindy looked at Rebecca and counted down with the fingers on her hand, five, four, three, two, one.

Finally Rebecca was done and her double-dare was completed and surprisingly it wasn't that bad after all. She then softly walked back to the bench where her sister was laying and lid down beside her.

Rebecca shook her head and looked at Cindy saying, "You are unreal, I can't believe you made me do that! With that said, now it's my turn and I double-dare you to put your hands in that hobo's pants and give him a hand job until he cums...just like you made me do to that Indian guy on the train."

Cindy chuckled, "That's all you got is it sis? I thought you were going to get me back."

Cindy then got up off the bench, strutted to the homeless guy and sat on the bench next to his head, not being careful at all and pushing him over to make room.

The hobo slurred, "It's my bench, get your own."

Cindy didn't say anything. She just leaned forward and moved both her hands to the hobo's crotch area.

The hobo grunted and said, "Vicky, I told ya I got no money. You can beat me off, but it will have to be in the IOU bank."

Cindy looked over at her sister and said, "Well, I guess he thinks I'm someone else."

Cindy fumbled with his stained jeans and could smell a pungent odor just from unzipping the zipper. To her surprise as soon as the zipper opened out sprung a 6 inch uncut cock, surrounded by mounds of grey pubic hair. Cindy wrapped her right hand around it and began to tug on it. She didn't have much experience with guys, but knew the basic principals of a hand job. She also knew that if she wanted to get this over with she had to make him cum, so the faster the better.

Cindy stood up and then completely unbuckled his belt and pulled his pants down to his knees. She then got on the bench and sat on his knees and faced him, this gave her easy access to jerk him off with one hand and play with his balls with the other. Cindy did as she planned and continued, working his cock hard and trying her best to make him cum. This must have gone on for fifteen minutes or so and she thought it would have been over by now, but guessed that his whisky dick was giving him extended stamina.

Cindy knew she had to do something so that her double-dare was completed. She went this far and didn't want to fail giving her sister the chance to give her the next dare. She then hooked both hands under her t-shirt and pulled it over her head and quickly unclasped her bra and threw both to the side of the bench.

Cindy then leaned forward and slapped the hobo in the face waking him up.

He responded, "What the fuck, I got no fucking money!"

Then he looked down at his hard cock and the cute twenty-one year old topless female with her hands wrapped around his cock, rubbing the head of it on her nipples.

Cindy spoke up, "How do you like that? What do I have to do to get you to cum?"

The hobo responded, "Well you're doing pretty good for starters, but how about you do some sucking down there too."

Cindy had never given a blow job before, but was always curious. She just didn't want it to be with this guy.

She replied, "Well, how about we compromise. Rebecca, pass me a package of that crystal light."

Rebecca complied, throwing Cindy a small serving pack and was curious what her sister had in mind. Cindy spit on the hobo's cock and began to spread her saliva around the hobo's cock. She opened the pack of pineapple-orange flavored crystal light and poured it on his wet, spit smeared erection as it stuck on.

Cindy then lowered her head and pinched her nose with her right hand and held his cock up with her left. She then stuck her tongue out and began to lick the base of the hobo's cock, licking the drink mix off of his cock.

Cindy looked up saying, "It's a good thing I like pineapple or you wouldn't be getting this treatment. Believe me."

The hobo looked down at the sexy beauty licking his glistening shaft and said, "Hey, do you mind if I sit up for a bit?"

Cindy replied, "If that will make you cum faster, please do."

The two shifted positions and the hobo sat on the bench with his pants around his ankles as Cindy knelt on the ground just in front of him, between his legs. She continued to jerk his cock while giving him a random lick. The old hobo reached down with his dirty right hand and began to twist Cindy's hard, perky nipples and she gave a quick yelp.

Cindy glared and said, "Now Mr. I don't mind you playing with my breasts, but be gentle!"

The hobo laughed and followed it with a loud grunt. Cindy felt his haft begin to stiffen harder and his body began to squirm. She knew he was enjoying his treat and continued to pump his cock with her head directly above it. Suddenly he popped and a huge wad of cum spurted up hitting Cindy on the bottom of her chin. She backed up and the next eruption shot up and arced down to her breast, followed by the last which hit her arm that was still holding his cock.

Cindy stood up wearing only her short-shorts and flip-flops and looked over at her sister. She had the vagrant's cum dripping from her chin, down her neck, running down her breasts and on her arm. She was a mess.

The hobo spoke up, "If you like pineapple, you should have a taste of what's falling off your tits there."

Cindy out of curiosity took her arm and held it in front of her mouth, gently touching the white cream with her tongue.

Cindy looked back at the hobo saying, "Nice try, guy! It tastes nothing like pineapple, not bad, but nothing like pineapple."

Cindy then said to her sister, "See I knew I could do it, but wow I am a mess! Can you throw me a towel?"

Rebecca threw Cindy a small towel which she had in her backpack and replied, "Wow, I am impressed! You really followed through with it. I am nervous to find out what you will dare me to do next."

Rebecca helped Cindy clean up and the next thing they knew, the sun was coming out. The girls walked to the hostel and booked a room and took a shower.

Their adventure on the road had just begun.