Trapped 37

Trapped

*Note: This contains scenes of light rape, and unwillingness. This is also my first story so I would appreciate any feedback. Hope you enjoy!

Andrew opened his eyes and his head was spinning. He couldn't remember falling asleep last night or even where he was. As he opened his eyes there was even greater confusion as he didn't recognize the room that he was in.

The room was dark and empty. Dark grey walls surrounded him but in front was what looked like a large mirror and a metal door right next to it. Then came the realization.

Andrew was bound, straddling some sort of furniture or chair. It felt like leather straps that were binding his hands and feet to the strange chair. He was positioned as if he was leaning forward on a horse, legs bent and pushed upward, arms hugging the "horse's" neck.

Upon further clarity, Andrew realized the most worrying part, he was not wearing any clothes. The room was warm but not uncomfortable, and the air was still so he did not realize his lack of clothing immediately. With a little wiggle to see if there was any looseness in the binds Andrew realized his genitals were hanging freely in some opening in this "horse".

Andrew called out hoping someone would hear him. "Hello? Is anyone there? Where am I... What is going on?" But no one answered.

Andrew tried to struggle free for a few minutes but found no results, and so he waited.

After about 10 minutes of waiting the door opened and out walked a familiar face. Allison from high school. Andrew couldn't believe what he was seeing. Why would Allison be here? And was she the one who tied him up. But after seeing her face he realized she too was completely nude. Her curly brown hair reached her shoulders and from there he saw her moderately small breasts hanging on her chest. Her flat, and tanned tummy open to the air, and then... he saw it. A penis hung between her legs. It was nothing impressive, Andrew's own was bigger, but the shock of the sight threw Andrew into a panic.

"Allison? What is going on here? Why am I here?" He jutted out. Allison responded calmly "This is going to be one of the greatest days of your life."

Andrew couldn't believe what he had heard. Greatest day of his life? He was tied down and naked, he could not understand how this could be the greatest day of his life.

"What do you mean?" He said curiously

"You're a guy, so you obviously have always wanted a bigger penis, am I wrong?" Alisson asked bluntly

Andrew was never really dissatisfied by his own member. It wasn't particularly big, but it got the job done. But he would be lying if he said he didn't dream of having a much larger penis. "Well yes... But that doesn't answer my questions" replied Andrew almost somewhat frustrated.

"Today, assuming you pass the test, you will walk out of here with a much larger penis, or much smaller, that is up to you" said Alisson mischievously.

"And what will the test be?" Asked Andrew.

"You will know soon enough" Said Alisson as she walked up to him.

Alisson stepped close to Andrew, with her pelvic region even with Andrew's face. Without warning she put her soft cock up to Andrew's lips. "Go on, the sooner you get this hard the sooner you walk out of here with the cock of your dreams"

Andrew couldn't believe what he was hearing. He had to fellate a girl from his high school. They were all in college already and it had been years since they saw each other. Now here she stands, penis near his mouth, promising to give him a bigger penis. The idea somewhat excited Andrew, and almost instinctively he stuck out his tongue to lick the head of her soft penis.

Andrew had never sucked a cock before, and he was surprised with how little it tasted like anything. Then without warning Alisson pushed her hips forward and forced her now hardening cock into Andrew's mouth. He could feel her penis getting harder in his mouth, but it hardly seemed to grow. Andrew estimated it was maybe four inches long, and average width.

Alisson's now rock hard member was pushing the back of Andrew's mouth and so she pulled it out.

"Good job. Now comes the fun part" Alisson said with a smirk.

She walked to Andrew's right, out of sight and within a few seconds Andrew felt a hand on his ass. What felt like a finger rubbed around his hole and then entered. He could feel something very slippery being applied. Andrew realized what was happening then.

"Are you going to fuck me!?" Andrew shouted in panic

"Well of course, I can't just leave dissatisfied. Besides, I am not that big, so it will be fun for the both of us.

Alisson grabbed onto both of Andrew's hips and positioned herself behind him. Andrew could feel the head of her admittedly small penis press up against his hole until it popped in. Alisson pushed further until she was about two inches into Andrew and began thrusting in and out slowly.

The feeling of something in his ass wasn't completely foreign to Andrew, he had put a few fingers in there before, but a penis is something completely else. He didn't know what to think. Andrew knew he was being violated but there was a slight pleasure in knowing there was nothing he could do, and Alisson wasn't too large so there was hardly any stretching being done.

After a minute or so of small steady thrusts Alisson began to thrust deeper and faster into Andrew's ass, forcing Andrew to let out a slight gasp.

Alisson heard the gasp and understood it to mean he was enjoying himself so she began to pound Andrew's ass as fast as she could, letting out some moans herself.

For the first time since the fucking started Andrew thought about his own penis and could feel that it was solid as a rock. "Fuck, Alisson can you at least give me a handjob or something while you do this" asked Andrew between baited breaths.

"Oh no, that I cannot do. The process won't work if you cum like that" replied Alisson barely able to get the words out from her own pleasurable moans.

Andrew was somewhat disappointed but the feeling of her cock inside of him really did seem to be enough for the time being, so he relaxed and enjoyed the sensation.

Moments later Alisson began to breath very heavily and Andrew knew what was happening. Alisson gave a few large thrusts and let out long and loud moan in ecstasy as she shot her sizable load inside of Andrew. Shot after shot of cum burst from her cock, filling Andrew's rectum. After a few moments of rest inside of him Alisson pulled out.

"So now when do I get my big dick?" asked Andrew excitedly

"You're not done yet. You still have a lot more to get done. That was only the beginning" said Alisson.

Before Andrew could respond, the door opened again and out stepped another familiar face. A good friend of Alisson's and someone he was much closer with in high school. Her name was Mackenzie, but everyone just called her Kenzie. She was tall, about 5'10, and always had her dirty blonde hair in a ponytail, today was no different. Her height and hair weren't why all the boys liked her though. She had an hourglass figure, and almost perfectly sized tits. Her wide hips and large butt had always made Andrew look twice at her, but he was never brave enough to ask her out. Unlike Alisson, Kenzie came out with some clothes on. A thin, silk like wrapped skirt, and a bra.

Alisson walked out of the same door she came in and it was just Andrew and Kenzie.

"You look like you had some fun" said Kenzie behind a smirk

"I suppose I am in for some more

fun

"

Andrew shot back, pausing before he said "fun" in a sarcastic tone.

"Well it depends on what you like, but most would say I am a bit more fun"

Kenzie unclasped her bra revealing her shapely c-cup boobs, with puffy nipples. She let her bra drop to the floor and began to unbutton her skirt revealing a penis of her own. Compared to Alisson, Kenzie's soft cock didn't seem to different. Perhaps a bit thicker but Andrew could hardly tell.

Without another word Kenzie walked up to Andrew and just as Alisson did, put her dick into his mouth. It tasted no different to Andrew, but he quickly realized something was different. As Kenzie grew in his mouth, he realized that her cock was quite a bit larger than Alisson's. Kenzie seemed to enjoy his mouth much more than Alisson did, and began to really get into his. She thrusted her wide hips forward pushing her cock as far into Andrew's throat as she could, where she let out a loud moan.

Kenzie pulled her now fully erect penis out of Andrew's mouth and walked to his side and unbound his right hand. She rotated back to his front and told him "use your hand too"

Andrew grabbed Kenzie's dick and immediately realized she was slightly bigger than him. Where he was just about six inches and somewhat skinny around, hers was an easy six inches and much thicker, his hand less easily wrapping around her cock than his own.

Andrew began to stroke her cock, paying special attention to the head. He put his head back down onto it and stroked in tandem with the movement of his head up and down her throbbing cock, taking a breath every once in a while, quickly stroking with his hand.

Kenzie pulled back from his head and grabbed his hand and once again binding it in the leather strap. She walked behind him, and without warning pushed nearly all six inches directly into his ass. Andrew let out a yelp as the sudden stretching of his anus caused a bit of pain.

Kenzie was merciless. Where Alisson started slow, Kenzie was full speed from the beginning, not giving Andrew a chance to adjust to her larger tool. Andrew was somewhat blinded by the mix of pain and pleasure as Kenzie drilled him hard.

After what felt like an eternity Andrew began to adjust to Kenzie and the pain became almost completely overtaken by pleasure. He couldn't hold in his moans and began to let out his sounds of pleasure with every thrust.

Kenzie leaned forward so her breasts were touching his back, and began breathing into Andrew's ears. Andrew could feel Kenzie grow even larger inside of him and could tell what was happening. With a small scream, and one final push deep into his ass, she unloaded into Andrew. Kenzie continued to cum for 30 seconds each blast filling Andrew more and more.

Kenzie gave one last small twitch and pulled her only half hard cock from Andrew's ass. Without a word she knelt down next to Andrew's face and gave him a small kiss on the cheek. As she walked out of the room she turned to Andrew and said "good luck" with a small giggle.

Andrew watched the door closed and pondered her parting words to him. They gave him a lot of time to think as no one came out of the door for another ten minutes. Andrew's mind began racing. How many more dicks will he have to suck? Will there be a man? He had had fun so far, but he wasn't sure how much more he could take of all this.

The door opened and Andrew realized why Kenzie had wished him good luck. Out stepped another girl from High School, Jennifer. She was a bit of a nerdy looking girl with a round face framed by her long blonde hair. She also touted heavy breasts with large ghost nipples. But Andrew wasn't looking at her face or chest. He could not take his eye off of what was between her legs. She was already rock hard, and it was big. Andrew guessed at least nine inches, and thick as a can of Red Bull.

Jennifer walked up to Andrew, her massive member swaying side to side with each step. When she was in front of him she quietly took hold of her cock and lifted it so it was pointing up. She moved forward to rest it on Andrew's face.

"I told them it was bigger" said Jennifer amusedly. Andrew realized what she meant; her cock was longer than his entire head. This realization terrified him and he began to panic.

"Please, do not fuck me with that. I don't think I could take it, it could really hurt me" pleaded Andrew

Jennifer responded with a slight sound of disappointment in her voice; "What about your new big penis? Isn't that what you want? This is a once in a lifetime opportunity, I wouldn't want you to squander it..."

"I don't want it anymore; it just isn't worth it!" Stated Andrew in desperation.

Jennifer looked down at Andrew's face, but she seemed to have no sympathy. "Well as you can see, you have put on quite a show and have gotten me all worked up. And I will not allow you to get out of here without helping me solve my... big problem." Without another word Jennifer walked behind Andrew to his helpless ass and began pressing the tip of her engorged penis against his anus.

"No! Please! I will do anything! Just don't put it in! shouted Andrew, tears filling his eyes.

Jennifer ignored the trapped man's pleas and pushed the head in, causing a loud sob from Andrew. The sound prompted a smirk from Jennifer, and she pushed until the top of her shaft entered. Andrew could feel his anus stretching beyond anything he had ever imagined. It felt as though a tree was being pushed into him.

Once about half of her nine inches were inside, Jennifer began thrusting in and out slowly. "You see? I will take it slow for you; I want to make sure you have a good time here as well. But, of course, I want to enjoy my time here, and I must say you feel very good around me." Jennifer said gently.

Andrew couldn't focus on her words. With his body feeling like it was being split in half he just stayed still and tried to relax. And it seemed to be working. Andrew could feel his body relaxing and was even getting some semblance of pleasure from the fleshy rod buried inside of him. Though there was still a significant amount of discomfort.

After a few minutes Jennifer began to pick up the pace and push deeper but the pleasure only built for Andrew. He had gotten used to her large size and it began to fully feel good, coaxing out slight moans from the bound man. Jennifer took this as an opportunity to fully commit and began long dicking Andrew fast.

Within Andrew grew an almost familiar but completely foreign feeling. Deep inside began a slow burn. Andrew's first thought was he was perhaps injured on the inside, but the feeling began to become pleasurable. Andrew's mind began to fade as he gave in to the feeling within his pelvis. But a sudden buzzer snapped him out of it. From what sounded like a speaker somewhere in the room came a familiar voice, but one he could not pin on anyone in particular. "He cannot cum yet, slow it down, maybe go shallow."

With a disgruntled sigh Jennifer pulled most of her long rod out, and shallowly fucked Andrew. Andrew seemed more disappointed than her, and realized he was about to have a complete anal orgasm, but that voice stopped him.

After a less thrilling few minutes Jennifer began to pick up the pace, and even started thrusting deep again. With a loud groan and a few quick pumps Andrew could feel himself fill with more cum.

Jennifer pulled out, still very hard, but seemingly satisfied. She walked up in front of Andrew and knelt down to whisper "You'll get what you want soon". After a quick peck on the cheek she turned to walk out of the room.

Dazed from his recent experience Andrew let go and relaxed, doing his best to lay down on the contraption that bound him. Whether a minute passed, or an hour Andrew couldn't tell, his entire body felt like it had melted besides the tension within his pelvis, begging for release. Then she walked out, and Andrew recognized the voice, one more girl from high school: Lilith.

Andrew wondered how he hadn't predicted it. All of the girls from that clique had come out already, so it had to be Lilith. A bit shorter than Andrew, around 5'5 Lilith sported light blond hair in a short and somewhat curly pixie cut. Her skin was pale as milk complimented by small pink nipples on her shapely a-cup breasts. For some reason Andrew was always attracted to Lilith's boyish figure. The most boyish thing about her now though was what was between her legs. A soft penis sat protruding from her crotch, and it was already twice the size of Andrew's fully erect.

Lilith walked up to Andrew and looked down at the dazed man. "You are so close to getting what you want; given you don't back out now" said Lilith in an almost professional tone.

Andrew looked up at the beautiful girl standing before him with almost empty eyes. "I will not back out. Please do what you will."

Lilith smiled. "You're smarter than I remember"

Lilith lifted her long and floppy cock and guided it into Andrew's awaiting mouth. Without a beat Andrew began licking her frenulum. After a few licks it began to grow quickly, and Andrew closed his lips around the head of Lilith's large member and began to suck with the limited movement his head had.

After a minute of sucking Lilith was fully erect, and Andrew noticed how far away she was from him. Lilith stood well over a foot away with the head of her penis in Andrew's mouth. Being fully erect Lilith straightened herself out in front of Andrew and grabbed his head. She began to push her cock deeper into his mouth and past his throat barrier. She slid easily into his throat and Andrew just accepted the intrusion.

Lilith lightly face fucked Andrew for a few minutes at a steady pace. Andrew desperately wanted to touch his own cock but knew there was no hope of any such thing occurring at the moment.

Finally, Lilith was satisfied with Andrew's mouth and pulled her cock out. Andrew realized she had only pushed about half of her full size in as she pulled away. Lilith walked behind Andrew and with no warming up put that same half into his ass. Andrew felt no pain from this sudden penetration. Though a few inches longer than Jennifer, Lilith had slightly less girth, so there was little stretching that had to be done by Andrew.

Just as she pushed in with no warning, she thrusted hard with just as little of a warning. Lilith quickly pounded Andrew immediately pushing about as far as Jennifer could reach with each thrust.

Andrew wanted to get the orgasm he was deprived of, so he spoke up. "Please fuck me harder, fuck me!" he pleaded to his hung captor.

Lilith silently and with no reaction began to push deeper with each thrust. Andrew recognized immediately and let out a joyful moan. Within a few thrusts the two were skin to skin, Lilith pushing as far as she could reach inside of Andrew.

Within a minute the feeling returned. Andrew felt a small burning sensation inside of him that quickly turned to growing pleasure. Andrew felt as though he couldn't hold on much longer and through gasps let out "Can... can I please... cum." Lilith did not respond, she just continued her steady pace of deep fucking.

Lilith herself began to breathe heavier as she fucked. Within a few more thrusts she finally let out a large moan and released inside of Andrew. Andrew could feel her grow that little bit more inside of him and it pushed him over the edge. The room began to spin and go dark. Every nerve in his body was screaming, but in the best way imaginable. He began to slightly convulse and let out sounds that no one would consciously make. Finally, the darkness crept in enough to fill his vision, and Andrew's last sight of the experience was the large mirror, and metal door.

Andrew woke up in his bed. His whole body felt sore, his ass especially. He couldn't quite remember what had happened the night before, he just remembered the faces of a few girls from his high school, and odd thoughts of penises. As he sat up he felt the head of his penis brush something in his pants. As he lifted the belt line he saw that his penis was twice as thick, and twice as long as he was hard, but this time it was soft.