Lana's Extreme Dare

[jackfromnyc]

As soon as Amy logged on to Yahoo, she received a friend request from the Timinator. She accepted and the conversation started.

Tim: How are you?
Amy: Fine, you ?
Tim: Fine. So you have a sub who wants to experience a gang bang?
Amy: Yes, her name is Lana.
Tim: Good. I’ll assume she’s at least 18 years old?
Amy: Yes, just turned 18 this past summer.
Tim: Okay, let me tell you how this works. Midwestern Gangbangs is a group of men and women who enjoy group sex. Most of us engage in some fetish life but we are not all Doms/Dommes and subs. We parties every few weeks where 2 or 3 girls will play with 10 to 15 boys. You might find it odd that we usually have too many girls than we have boys.
Amy: Oh, our girl Lana is trying to complete a dare, she needs to have a gangbang with at least 6 men.
Tim: Our regular parties are usually only open to members and we have enough girls for the next 5 months. But a dare, ey? This sounds interesting. Let me ask you, is she really into this or is she dreading it?

Amy looked at Lana and the girls who were reading over her shoulder. Amy said I’m sooo dreading this.

Amy: She’s dreading it. But she’ll do it because the penalty is worse.
Tim: Can she sit at the keyboard and answer some questions for me?

Amy got up and told Lana to sit down.

Amy: Okay, Lana here.
Tim: Hi Lana. How are you?
Amy: ey, not so good.
Tim: xD don’t worry, if we can work this out it will be fun.
Amy: Its not really my idea of fun but whatever.
Tim: Tell me about yourself.
Amy: Like what?
Tim: Okay, I’ll ask you questions. What is your age, your height and weight?
Amy: I’m 18 and am 4’10” and weigh 94 lbs.
Tim: Wow, you’re tiny. What size bra and jeans do you wear?
Amy: aah, I’m a 32 A and wear a size 0.
Tim: Wow, you really are small? Can you go on Skype?

Lana looks back at Amy who said “yes.”

Amy: Yes
Tim: Okay. Send me your Skype info and I’ll give you mine.

Amy sat down at the computer and entered her Skype info as did Tim. She then logged onto Skype and was soon connected to Tim. As soon as he saw her he exclaimed “Lana!” Amy said “no, I’m Amy. Here’s Lana” as she pointed the webcam at Lana. “No insult intended but you do not look 18. Can you show me your drivers license in the cam?” Amy told Lana to get her license and she did so. Amy took Lana’s license and held it up to the camera. “Yup, you’re 18” said Tim. “Can Lana send me a still shot?” Amy said “I have one in my picture file, let me send it to you. Why do you want it?” Tim replied “I don’t think we can find anything for her in our regular play parties, but I occasionally can get a group of experienced guys for a special night. I’ll need a few days to set it up. I’ll show them this picture. Do you care how many guys are there?” Amy answered “no” at the same time Lana said “yes.” Amy shushed Lana up and continued “All we care is that there is at least six.” “Okay” said Tim. “Give me a few days and I’ll get back to you.” “Kewl” replied Amy. “Oh wait,” said Tim, “I need to know when Lana can come to Chicago for the party?” Again Amy replied for Lana “any weekend. We’ll have to figure out how to get there as none of us have cars here as its not allowed for freshmen.” “Okay, so you’re flexible, that’s good” said Tim. “Oh, and one more thing. This may be obvious but in someone so young I have to ask, is Lana a virgin or is she experienced?” Lana spoke for herself this time “I’m not a virgin. I’ve done stuff. Just not a lot.” “So, she speaks” chuckled Tim. “So you’ve done it all?” Lana replied again “well not it all, I’ve done everything except anal with 2 boys.” “Two at a time, so you are experience” said Tim with a surprise in his voice. “NO” exclaimed Lana. “Not two at a time. I had two boyfriends I’ve had sex with. And I’m not sure I’m experienced. I’ve only had sex like 5 times total.” “Don’t get excited Lana, its okay. The important thing is that you’re into this.” Lana nodded her head yes. “Okay, I’ll text you in a couple of days and tell you what I’ve been able to arrange. Look for it. Bye” said Tim. The girls all said “bye” in unison.

[Rachie]

Great, wish i had know about it last week. You have a lot of talent, and can tell a load through this and your other fantastic story"The Experiment"

Keep writing

Love Rachie
x x x

[ghyt]

I'm waiting for next parts of this story.
One of my favs here!

[jackfromnyc]

The girls went about their business when on Monday Amy received an email. It was Tim from Chicago. The cryptic note read as follows: “Skype, tonight 7 pm.” Amy was ecstatic. When the girls all returned from classes Amy gave them the news. “Tim from Chicago wants to talk to us tonight at 7.” Lana said sheepishly “I don’t think this a good idea.” The other girls were evenly split between those who felt Lana needed to honor her agreement or be ostracized for the remainder of their freshman year and those who believed it was too extreme. Ashley, speaking for the Amy’s side said “I did my truth. These were Lana’s rules. She should follow them.” Amy, taking her familiar queen bee role said “Its decided Lana. You WILL do this.”

At 7pm the Amy fired up the Skype and waited for Tim to call. They were disappointed when by 7:15 Tim didn’t call. The girls were in agreement that Tim wouldn’t call and that it was probably just a hoax. Amy held on to hope and said “I’m going to leave it open anyway.” At a few minutes to 8 the alarm rang on the Skype. It WAS Tim. Amy answered and asked why he was so late. Tim complained “I’m not late, I told you I’d call at 7.” Amy replied “Well its 8 now.” Tim laughed and said “I meant 7 Central time.” Amy laughed back. The girls, including Lana, gathered around the small screen of the notebook. Amy asked “So Tim, what news do you have for us?”

Tim had an excited look in his eyes. “Okay so here’s what I’ve come up with and I think you’ll be very pleased. I’ve been able to find 10 guys for this special gang bang. It has to be this Saturday. Can Lana make it?” Amy and Ashley replied in unison “She’ll be there.” Tim laughed again. “Let Lana get into the camera and answer for herself.” Lana got into position and said tentatively “Yes, I can be there. But how will I get there?” “Don’t you drive?” asked Tim. “Yes I drive but I don’t have a car here. Freshman are not allowed to have a car at St. Eustatius University” replied Lana. Amy chimed in “we can take the bus to Chicago. Megabus is very cheap and it only takes 6 hours.” Tim thought that was a good idea. “Can Lana get here Friday night? I’d like to get to know her and go through some things. She can stay in my apartment on Friday night.” Amy responded “Ah, I’ll be coming along too. And we can take the 5pm bus which arrives at 11 your time.” (Amy had been doing some research into this before the call.)

“The fare is about $100 round trip for each of us. It’s rather expensive for students” complained Amy. Tim was quick to reply “that’ll be no problem I’ll cover it. I know where the Megabus stops so I’ll meet you there at 11. Do you guys have any questions?” Amy looked at Lana and said “I have a load of questions but I’m too overwhelmed.” “I’ll put some stuff in an email and send them to Amy. Anything I don’t cover you can then ask” Tim volunteered. “That will work” said Lana. The girls and Tim said goodbye and disconnected the Skype.

A few hours later Amy came out of her room to look for Lana. The girls couldn’t contain themselves and they all gathered around. “Here’s what Tim emailed Lana.” She continued to read: “Dear Lana, thank you for wanting to experience our particular fetish. As I said I was able to round up 10 men to participate and they all were very impressed by your picture. Its not often when we find such a young women who wants to participate and we hope you find the experience excellent and become a permanent member of our group. Here are the particulars. The party will take place in a suite in a very fancy downtown hotel. We’ve used this hotel before for parties and we like it because we can party without getting interrupted. I can’t give you the name because if they knew this was happening they would probably not take a reservation from my any more. I’ll meet you at Union Station and it’s a short subway ride to my apartment. We can stop for dinner if you girls are hungry. I have a small place but you and Amy can sleep in the king size bed and I’ll stay on the sofa in the living room. We can hang out for as long as you like. On Saturday morning I’ll make you one of my famous breakfasts. We’ll need to go over what’s going to happen later that day and I’ll need you to sign a release form. Please bring 2 forms of ID so I can make sure you’re over 18. At about 3pm, we’ll be able to check in to the hotel. We’ll go at that time so you can get comfortable with the environment. The men will assemble between 5 and 6 and the party will begin at 6. I do have some questions. It there anything that you don’t want to do? Its not really acceptable to have too many limits but if there’s something sexual you don’t want to do that’ll be okay. I’m assuming you want to require condoms for penetration but what about oral? The guys hate wearing condoms for oral and you can do your research about STDs being transmitted that way. Our group does require our members be tested regularly but there can be no guarantees. Look forward to seeing you on Friday. Please let me know if your plans change. Love Tim.”

Amy said to Lana “we ought to reply to him as soon as possible.” Lana agreed. Amy opened her email and started typing “Dear Tim, Thanks for making the arrangements. I would like to answer your questions and ask a few of my own. I don’t have any objections to anything sexually. I want to experience the full effect of a gang bang.” Amy looked over her shoulder at Lana for approval and Lana looked at her friends. They were all nodding so Lana nodded as well. She continued typing “I agree with you about the condoms and don’t mind giving oral without one but I would really rather not having the guys cum in my mouth.” Amy asked “do you have any questions Lana?” Lana said type this: “I am wondering what are the ages of the men who will be at the gang bang. I’m also wondering how long these usually take. Finally, I don’t want to be tied down and will I have a way to stop the works for like water or bathroom breaks?”

Amy sent off the email. Within minutes Tim replied “Dear Lana, the guys I’ve arranged for Saturday range in age from 18 to 64. You will absolutely NOT be restrained in any way and you will have a safe word to stop the action whenever you want. But I hope you don’t use that word too often ” “SIXTY FOUR” exclaimed the girls. “Eeew.” Lana, being reasonable said “I really don’t care. I’m sure a man of 64 is very experienced.”

Lana didn’t get much sleep that night thinking about the events of the next weekend. The suite was a buzz for the next few days while Lana and Amy planned for their trip on Friday.

[Stormwalker22]

Great chapter cant wait to see what happens next.

[Silvercola]

I love it... more soon

[jackfromnyc]

The time from setting up the appointment and Friday seemed to fly for Lana. She woke for her 8 am class and came right home. Amy, who didn’t have Friday classes was up and sitting at the dining table. “Are you packed?” Amy asked Lana. Lana indicated no and replied “I just don’t know what to bring. Did he give you any indication?” “I sent him an email Wednesday and he said things are fairly informal in Chicago. He said just bring what you normally wear to school.” Lana nodded okay and continued “Did you ask him what I should bring for the gangbang party Amy?” “I did” replied Amy. “He didn’t mention it in his last email.” “Well what do you think I should bring for that” asked Lana. “When he didn’t reply by last night I did some research. I found some sites that had descriptions of what amateur gangbangs are like and looked at some free video clips. It seems to me that the girls are usually wearing some sort of lingerie. You know, something lacy. And then some had on a robe too” offered Amy. “I have that nice silk robe I got from my mom on my birthday. You know it, the one with the red poppies on it. I wear it a lot to the showers. I’m not sure what I could bring that qualifies” asked Lana. “Let’s look and see what you have” Amy offered. The girls went into Lana’s room and looked in her dresser draw with her undies and pj’s. “This looks nice” Amy said picking up a silky camisole and tap pants set with sheer inserts. “It looks flirty.” Lana groaned and said “What about this short nightgown? It has lace on it.” “No way Lana. It has to be sexy” and the Lana took the set and put it in her Vera Bradley duffle. Lana continued the packing process putting in a spare pair of jeans, some tank tops, a spare bra, two pair of boy short panties, and her favorite hoodie. “I’ll only be there for 2 days really since we’re getting in so late” she reasoned. She looked at her underwear and chuckled “my clothes are really utilitarian. I need to update that.”

It was time to leave to get the Mega bus. The suite mates bid Lana and Amy goodbye and they went to the station. Amy went to the ticket window and gave her name as Tim had instructed. The agent, a nice grandmotherly type said “Oh yes dear, two round trip tickets to Chicago fully paid. Somebody must want to see you girls badly.” Lana blushed. “Everybody can tell why I’m going to Chicago” she thought. Waiting on line to enter the bus, Lana expressed her concerns to Amy. “I’m worried Amy. This is not like me at all.” Amy confided in Lana. “Lana, I’ve been into the BDSM lifestyle for 2 years now. Sometimes I’m the dominant and sometimes I’m the submissive. You wouldn’t believe the things I’ve done. It’s exciting Lana. Just go with the flow and enjoy it. If you’re like me you’ll get an adrenalin rush that makes up for all the worry.” “You have! What kind of things have you done?” asked Lana. Amy replied “oh the usual stuff – pain and bondage.” “Have you ever done it naked with so many men around?” asked Lana. Amy nodded and took out her iphone and showed Lana pictures of her suspended, being spanked, clips on her nipples, etc. “What’s the worse thing you’ve done” asked Lana. “Well to me the worst is the best. The most extreme thing I’ve done was at a public play party, which is when a group rents a place and there’s all sorts of equipment and people are free to do what they wish. They asked who wanted to be auctioned off for charity and I thought it sounded interesting. Anyone willing to pay $200 to the charity could do anything they wanted within my limits. Three guys and a woman agreed and they said they would do it at the same time. I was stripped, bent over a bench, caned and had a large butt plug inserted. That REALLY hurt. Then I was suspended by my arms and had my legs spread in a device to keep your legs apart and was whipped and paddled. Finally, they used a powerful vibrator on me and I came so much the butt plug popped out.” “When did this happen” asked Lana. “Remember when I went out over the holiday weekend and came home and spent 2 days in bed? Everyone thought I had the flu but it happened then.” “That was only a month ago!” exclaimed Lana. Amy nodded. While the girls were chatting the bus started its engine and left the station.

The ride to Chicago from Cleveland was a boring 6 ½ hours. After about an hour of listening to their ipods, Lana took out a deck of cards and asked Lana if she wanted to play. “You brought cards?” asked Amy. “Yes” replied Lana, “mother always brought them on long car trips.” The girls giggled. “Sure, why not” said Amy. “Do you know how to play poker?” Amy asked. Lana said she played it with her brothers a lot. “But I don’t have any money to lose gambling” said Amy. “Its okay, let’s bid like we had $1000 each and keep score. The one with the least money when we get to Chicago has to do any dare the winner says.” Amy agreed. As luck would have it, within 3 hours Amy had all of Lana’s fake money. “Looks like you win Amy” Lana conceded. “What do I have to do?” Amy thought for a moment and said, “I’m not sure yet, I’ll let you know when I am.” Before long the bus was pulling into the station in Chicago. The girls retrieved their luggage and looked on the platform. There, at the end, was a dreamy guy in a white tee and ripped jeans and just enough of a beard to make him look like a bad boy. Tim walked up to the girls and said “You must be Lana and Amy.” He shook Amy’s hand and when Lana extended hers he reached in and gave her a big hug. The action was not lost on Amy. But it left Lana wondering “what did THAT mean?”

[Rachie]

Great 2 chapters, can't wait to read more soon

Love Rachie
x x x x

[Stormwalker22]

Very Nice I love the story please continue

[jackfromnyc]

The valiums had an immediate effect on Lana. She fell quickly and deeply to sleep. The effects didn’t last that long though and she woke to some noise coming from the apartment outside the bedroom door. Lana glanced at the clock. It read 3:20. Lana groaned to herself but decided to get up to use the toilet. “Hmm, wonder where Amy is” Lana thought. She got out of bed and walked in the dark to the door. She opened it slightly to a sight she thought would be the most incredible thing she’d ever see. (She was wrong about this by the way.)

Tim and Amy were on the opened sofa bed. Amy was on her back with her hands tied to each corner of the bed. Her legs were similarly tied to the same corners with ropes at her knees. This made Amy’s legs spread wide apart with her legs bent at the knees. Lana didn’t continue opening the door but stood silently. Tim on his knees bent at the waist eating Amy. She was moaning like she was enjoying it and about to reach orgasm. As Amy was about to let loose, Tim bent straight up and said “not so fast, you won’t cum until I tell you too.” And he got off the mattress and walked to the coffee table. Lana closed the door a bit so not to be discovered. But the door was open enough for her to see Tim open the small drawer in the coffee table and take out this red thing. “That looks like the rubber toy my dog plays with” Lana thought. Lana glanced at Amy and realized that her vagina and anus were completely exposed. Lana saw Tim get back to the mattress and put some liquid on the red rubber thing. She saw him place it up to Amy’s anus and with a slow turning motion begin to push. “Nooo,” whispered Amy. Tim responded “if you want me to stop use the safe word.” Lana didn’t know at the time what that meant. Amy replied “no, I won’t use it. I’m tougher than that.” Tim continued to push while Amy made noises of pain and displeasure. Lana couldn’t believe that the huge rubber thing was going to fit up Amy’s ass. But Tim kept on pushing and turning until it was in up to the red stopper at the end. Tim stood up as if to admire his work. Tim was also naked and Lana couldn’t help notice how buff he was. He leaned over Amy and asked “how’s that?” “It hurts you mother fucker. It’s huge. My asshole feels like its on fire” replied Amy. “Good” was Tim’s retort. Tim looked over to the bedroom door which was now only open a sliver and said “I’m assuming your friend is out to the world with that valium.” He reached to the floor and emerged with a piece round dowel-like of wood about 3 feet in length. He said “Now for your next ordeal” and Tim began to rhythmically swing the dowel hitting Amy on the butt. Each stroke left a red line and each one seemed to get harder and harder. Amy began with little squeaks but after 10 or 12 strokes when her ass was covered with red lines the squeaks became louder and turned into cries. Lana thought she should stop this but despite the cries Amy seemed to be enjoying this strange behavior. At about stroke 25 each stroke made Amy’s body jerk up off the mattress. Tim stopped and asked Amy if she wanted to use her safe word but Lana could see her shake her head no, so Tim just continued the beating. In all, Lana counted around 75 strokes and Amy’s ass had a few rivulets of blood trickling down. She watched Tim take a bottle off the lamp table and pour the clear liquid on a paper towel. “Here, this alcohol will make sure you don’t get any infections” as he vigorously rubbed the red and swollen butt. Amy screeched in pain again and said “I hope I don’t wake up Lana, she’s not ready to know about my lifestyle.” Tim gave Amy a drink from a vodka bottle and asked if she were ready to continue. Amy nodded yes.

Lana observed Tim get up to Amy and he put a half-erect penis into her mouth. Soon Lana could hear muffled sounds of gagging and gurgling. Tim removed a now fully erect and very large dick from Amy’s mouth. He moved back to a position in line with Amy’s vagina and quickly and without any warning thrust it into her. Her sound was that of a surprised inhale. He started pumping his dick into her pussy. It was not like the sex that Lana had experienced the summer before college. This was rough, raw, animal sex. Lana was also surprised that Tim didn’t wear a condom. “Not very wise of Amy” she thought. The pumping lasted about 15 minutes. A few times Lana could hear the sounds of pre-orgasm coming from Amy and each time Tim warned in a stern voice “not yet.” After the third time, Tim pulled out of Amy. Lana was surprised that Tim didn’t come. Her ex-bf always liked cumming even thought he complained Lana insisted he had to use a condom. Tim’s dick was shimmering with Amy’s mucosa when Tim reached down and abruptly pulled on the red rubber plug in Amy’s ass. Again Amy let out a shriek of pain. Lana could see that the anus had not gone back to its tight normal size. In almost one fluid motion, Tim inserted his dick into Amy’s ass. Lana watched as Tim took three fingers and inserted it into Amy’s pussy as he was pumping away into her asshole. Again Amy tried to orgasm and each time Tim told her “No.” Finally, after what Lana thought was about 20 minutes, Tim said “you now have my permission to cum.” After a few more thrusts and now four fingers in her vagina, Amy sounded like she was cumming. Tim’s thrusts became harder and he also came. He pulled out of Amy’s ass and fell backwards as if he had spent all his energy. Lana could see the gaping hole left in Amy’s ass with all this cum dripping out of it. Tim recovered and gently untied Amy. Lana watched him sit her up in his arms and he cradled her and asked her if she were alright. She nodded but was silent. Lana quietly closed the door and tip-toed back to the bed. She glanced at the clock and noticed it was 5 am. Her thoughts were filled with what she had seen. She fully didn’t understand it but she thought there must be a connection to this fetish website thing. She ultimately fell asleep but had strange dreams all night. Her last conscious thought was “if Amy and Tim are really into this kinky stuff, what will tomorrow be like for me?”

[Stormwalker22]

MMMM very good cant wait for the next chapter

[Public Harbinger]

wow! love it! more!

[ljfairy]

I like... please can we have more!

[erick92]

From one chapter they are getting off the buss and talking to Tim and in the next chapter we find Lana falling asleep because of a valium in the hotel room. It looks like a major part was left out and it'd be nice to read it.

[jackfromnyc]

Oops, This was left off the begining of the last chapter.

Tim looked just like his pictures. He said he was a waiter looking to break into modeling and he looked every bit of an underwear model. After the introductions Tim asked the girls if they were hungry. The girls replied yes but said they were too tired from the ride to go to a restaurant. Tim suggested Chinese take out. The girls agreed. Tim’s apartment was just 3 subway stops from the bus station. It wasn’t the best of neighborhoods but Tim told the girls that it was safe enough. This was little solace to the two privileged suburbanites. They stopped at a Chinese take out place and Tim ordered more food than either of them could eat in a week. He asked what they wanted to drink. Being underage to drink in the US, they both said “coke.” Tim laughed and offered them beer, wine, or booze. Amy looked at Lana and said “I don’t think you should be drinking booze. You don’t want to have a hangover tomorrow.” Tim agreed. Without thinking, Lana said “beer makes me fart” at which both Tim and Amy broke out laughing. “If beer makes you fart you probably don’t want to drink that either with the party tomorrow. Or maybe you do. It would be interesting” Tim said laughing. Amy suggested wine and Tim went into the store to get some wine for their meal. They got to Tim’s apartment. It was small and it looked like a boy lived there. Tim showed them around which took about 2 minutes. There was a small kitchen, a bathroom with an old fashioned tub and shower, one bedroom and a living room. He put the food on the coffee table and got some plates. “You girls will sleep in the bedroom. It’s a queen sized bed so it should be big enough. I’ll sleep on the pull out sofa. The trio ate their food and drank a full bottle of wine. Tim opened the second one. Lana took a drink but Amy said she had enough.

Tim suggested that they needed to get some of the business of tomorrow out of the way. Amy asked “what business” and Tim explained that for legal purposes he needed to check and photocopy Lana’s ID and she had to sign some release forms. Then he said he wanted to explain what would happen tomorrow so it wouldn’t be a surprise to Lana. Lana said she didn’t want to talk about the “business” tonight and Tim said tomorrow would be time enough. “Lana, you really are tiny. I can see why nobody thinks you’re 18. Can I ask exactly what your measurements are?” Lana blushed and said it was okay. “I’m 5 feet tall, weigh 90 lbs., my boobs are a 30A and I wear a size 00 in most things.” “Nobody is going to believe you are 18. Would you mind if I made a copy of it to have on hand if they ask. I will block out your last name and address if you want” asked Tim. “Oh its okay as long as you block out my info” sighed Lana. It was nearly 2 am when Lana said she was going to try to go to sleep. “What do you mean try Lana you must be very tired.” asked Tim. “I am tired but I’m so nervous I’m not sure I can actually sleep tonight” replied Lana. Tim went into the bathroom and come out with two pills. “You can have these if you want Lana. They will help you sleep.” “What are they” asked Lana. “They’re valium. A very mild sedative. They’ll help you relax.” “They’re alright to take Lana, my mom uses them when she’s stressed” chimed in Amy. “Ah, I’m tiny, I’ll take one” said Lana. She took the pill from Tim and swallowed it with some water.

Lana got up from the sofa, got her duffle, and went into the bathroom. “Oh shoot!” exclaimed Lana. “In all the rushing to pack I forgot something to sleep in. Oh well, I’ll sleep in this tee shirt and panties. I’ll have to shower in the morning anyway” she thought.