My Best Friend’s Older Sister: Part 1

William Wagner is the richest kid in our school. Heck, his family is likely the richest in the city. That he and I have been best friends since third grade has been the brightest spot of my life. My parents come from humble roots and are hard workers, but they aren’t inherently ambitious. They believe that success is measured in how many hours of overtime they can work in a given week. My older siblings (Tommy and Kari) fall into that same belief system. I’m no stranger to a strong work ethic, but exposure to William and his family have opened my eyes to see that success isn’t defined by only one parameter.

William’s family sees success as identifying problems in people’s lives, finding solutions to them, and marketing them hell of those solutions. The Pasta Fresh and Only Greens fast food alternative restaurants that dot the downtown corridors of every Midwest city is one of their most recent examples. They weren’t in the food industry before those chains popped up, but they identified a need for tasty organic food that were rapidly prepared and not insanely expensive. They figured out how to solve the need in a way that was economically profitable for both their clientele as well as themselves.

With everyone in my house working until eight or nine each night, it’s not hard to understand that I spend more time with William and his family than I do with my own. In fact, my mother thinks having access to a successful family is a good thing for me and for my future. I couldn’t agree more!

It came as no surprise that the Wagner’s invited me to join them during a spring break vacation to Thailand. For Will and I, it was our senior year and their family had a tradition of going on an international vacation during spring breaks. Maddie, Will’s older sister, a Freshman at NorthWestern, would also be joining us, and was the secret reason I pressured my parents to let me go on this trip. I’d had a crush on Maddie since 5th grade. I even remember the childhood moment when I stopped thinking girls were “gross” and started thinking that they were “pretty” and “nice” and… in the case of Maddie, “unbelievably sexy.”

It was the second day of the school year and I was walking between classes with my books held at my side. I’ve always been slim, undersized kid and unfortunately that sometimes made me a target. A group of 6th grade bullies knocked my books out of my hands and kicked them down the hall. All four of them laughed at me and called me wimp, pussy, and other, less attractive names. Maddie came up behind two of them and knocked their books out of their hands in one swift, confident move. “Oops,” she said, in a faux innocent voice, “How careless of me. Let me help you with that…” and then she stomped all over their notebooks and kicked the remnants in all directions. She smirked, and then turned and stood nose to nose with the lead bully, Jimmy Dorset, daring him to hit a girl. “How clumsy of me Jimmy. I guess this hallway is just full of clumsy today.” Jimmy’s face turned beet-red with anger and he huffed out “Bitch,” as he turned and left the hall, his posse in rushing collect his books before rushing to catch up to their leader.

Maddie didn’t miss a beat. She immediately started helping me gather my books and when I bent down to help, I inadvertently caught my very first glimpse of a girl’s lacy bra, and the soft, adolescent flesh underneath it. When she turned to hand me my things, she must have seen my wide eyes looking down her blouse because she said in a voice barely above a whisper, “Eyes up here, Jacob.”

In the span of one heartbeat, I felt my face flush with embarrassment. “Sorry… I… I…” I muttered, incomprehensibly.

Maddie smiled as she handed my books back to me, “I’m out of your league, Squirt.” Then she gave me my very first sultry wink and headed off down the hallway behind me. She slapped my butt as she left, which got a collective squeal from the crowd that had formed to watch Maddie, the prettiest, smartest, most confident girl in school stand up to the worst bully on campus.

* * *

Over the years, I got to know Maddie through my friendship with Will. Maddie was an absolute marvel to me. She was more than the smartest girl in school, she often debated her teachers during class lectures and more often than not won when they were stymied by her arguments. She became a student of Aikido and within four years, was able to best the Dojo Sensei. In her mid-teens, she started designing her own clothes and even modeled her amateur fashion line at Chicago fashion week. She framed the offer letter from she got from Michael Kors due to that show.

From 6th grade to when she graduated high shoot, Maddie had morphed from a pretty school girl to an absolute beauty. She stood a statuesque 5 foot 7 inches, was extremely fit, had a ample (but not oversized) bust, and sported a new hair style every month. She had more brains, skills, and beauty than any young adult in the Twin Cities. While we always got along, I never forgot what she said to me when she was 12, I’m out of your league, Squirt.

* * *

The business class seats the Wagners had bought for the family were beyond amazing. Having only flown coach before, I could now see the benefits of the Wagner’s approach to success. The 787 landed in Bangkok just after sunset and we made it through customs and immigration in no time. The black car service into the city was a different story. We all quickly realized the roads in Bangkok had been designed for a city of 5 million, not the 17 million that inhabited the delta city today. Ninty-three minutes later we made it to the Four Seasons, where we had three suites waiting for us. One for Mr. & Mrs. Wagner, one for Maddie, and one for Will and I to share.

The traffic had caused us to miss our first night’s dinner reservations, so the family decided to chance the street food vendors. The concierge pointed us in the direction of a world class set of street vendors and promised that the food was good, affordable, and (mostly) safe. The food was fantastic and we ate tapas style, where we shared each other’s orders and got to taste a wide variety of Thai dishes. We were all pretty much done when Will ordered one more dish—a curried satay of chicken and local vegetables. It looked great, but the rest of us were way too full to share it with him.

Not quite tired enough to head to bed, the five of us wandered the streets in front of the night clubs. Some of the most beautiful women in the world, wearing some of the sexist evening gowns ever designed, were beckoning Will and I to enter the clubs. Maddie kept smirking and encouraging us, but Mr. Wagner’s frown stopped us from doing anything but saying, “Thanks anyway.”

Mrs. Wagner kept giggling at every approach made to Will and I and finally started to tease her husband, “Let them have fun. We’re in Thailand for God’s sake.” Which was met with a resounding grunt from Will’s dad that everyone interpreted as, “hell no!”

It was close to 10:00pm local time, but since we all slept quite well in Business Class, we were jet lagged and not yet ready to go back. Will complained about not feeling 100% and Maddie poked him in the gut with her lightening fast reflexes, “Not getting food poisoning on the first day, are you?”

Will smirked back and opened his mouth to respond but instead of words coming out, his dinner did.

We got him some water to wash out his mouth, but when he swallowed some, it caused another bout of heaves. We caught a taxi back to the hotel and the concierge got us a ride to a high end health clinic two blocks away. The doctor looked Will over, took his vitals, and had the nurses admit him and place him on an I.V. Will effectively passed out and the doctor told us it could be a while before he’s able to leave on his own.

Mr. and Mrs. Wagner decided to stay with their stricken son but instructed Maddie to take me out and have a good time. They would meet us back at the hotel in the morning for breakfast at 9:00am. Maddie and I complained, saying we would rather be there to support Will, but Mrs. Wagner wouldn’t have it. She pointed to her unconscious son and said, “He won’t even know you’re gone.” Then she turned to us and quietly said, out of range of Mr. Wagner’s ears, “Enjoy the Bangkok night life.” She handed us a stack of local money, of which I only later realized was the equivalent of $1,000 USD.

Maddie quickly grabbed the money, winked at her mom and said, “See you in the morning Mom. We’ll be good… ish!” Then the most beautiful woman in my life grabbed my hand and pulled me, almost running, from the clinic, her auburn hair with light brown highlights flowing behind her.

* * *

When we got outside, she didn’t let go of my hand, like I though she would. Instead she squeezed it and give me a semi-wicked look, “We’re going to have fun tonight!”

Our walk back to the night clubs was magical. I was holding the hand of the prettiest woman in the world—even more beautiful than the club bait that kept trying to get us to go inside their establishments. “We should get a drink. Will would have wanted that.” Maddie pulled her phone from her pocket and looked up a list she had made of private clubs that weren’t too strict on drinking age. She mapped the route to one and we walked there in less than five minutes.

The club cover charge was 300 Baht (about $10). This fee cut out nearly all of the riffraff and the club was populated with a well to do crowd. The music was Euro Techno and not quite loud enough to cause hearing loss, but almost. Maddie, still holding my hand, asked the bouncer for a private room. He raised his hand with two finders extended and another gorgeous Thai lady immediately appeared and asked us for 1,000 Baht. Maddie paid and we were led to through a heavy curtain, down a dark hall, up a half-flight of stairs. The Thai lady slid open a pocket door into a private room that could easily have held eight people. One-way glass let us see the dance floor without letting them see us. The Thai lady introduced herself as “Su,” and asked what we would like to drink. Maddie confidently ordered a bottle of Champagne and two greyhounds. She handed Su 3,000 Baht and told her to keep the change. Su put her hands together in front of her face and bowed to the two of us before she left.

Maddie turned to me as we stood in our private room, still holding my hand in hers. She leaned closer and whispered into my ear, “It’s taken me seven years to get you alone.” He breath was like a feather on my neck, “I’ve dreamt of this since sixth grade, you know.” I was shocked, I think I stopped breathing right then. “Most boys are pigs… obsessed with themselves. But you’re different Jacob. You’ve always treated me with respect. Listened to my stories… laughed at just the right time…” Her lips were brushing lightly against my skin by now, “You’ve never needed to be in the lead, knowing that leading is something that I do need.” She pulled away enough to look into my eyes, “Isn’t that so?”

I opened my mouth to speak, but nothing came out, so I slowly nodded my head, in awe of her declaration.

Her mouth came back to my neck, “I knew it.” She took little nibbles with her lips just below my ear. “And you’ll let me do anything I want to you, won’t you?”

Again, nothing came out of my mouth, so I nodded my head while her tongue assaulted my neck. “Say it Jacob.” She order in a whisper. An order I was powerless to deny.

“Yes Madeline, you can do anything you want to me.” I used her full name, in a show of respect of her dominance over me.

“Oh Jacob, we’re going to have so much fun tonight.” Her hands moved to my hips and she guided me down to the soft leather couch that lined our private space. “I am going to teach you what it means to please a strong woman.” She started to climb onto of my lap, her hands moving to pin my arms at my side. “Tonight will change you… and you will love every moment of it!”

“Yes Madeline,” it was the only thing I could think of to say. I was less myself than I was her plaything. In the span of one moment, I had completely surrendered to her will. I had become a willing slave to her whims, and no matter where she led, I knew I would happily follow.

Just then, a soft knock came from the other side of the pocket door. Maddie pivoted off my lap and sat next to me. Her hand nestled on my inner thigh, less than an inch from my growing bulge. “Come in,” she called to the door.

Su entered and deposited the drinks and the silver Champagne bucket on the round table in the middle of the room. Ignoring me and looking at Maddie, Su asked, “Anything else Miss?”

Maddie smiled, probably at the recognition that she owned the room instead of me. “No Su, that’s all. Thank you though.” Su bowed again and left us to our drinks. Maddie squeezed my thigh and reached out to hand me one of the drinks. “We should probably discuss some ground rules… I would hate to have to punish you because you disappointed me.” Her right eyebrow raised, showing her seriousness.

“Yes,” I gulped, “That’s a good idea.” Not really know what she was talking about, but knowing that I didn’t want to do anything that could possibly jeopardize this chance with my dream girl.

She reached out for her cocktail clinked the glass against mine and we both took a healthy drink. “First and foremost, I’m always the initiator. You don’t touch me until I put your hands on me or I tell you to touch me.”

“Yes Madeline. I understand.”

“Second, you don’t get to say, ‘no,’ ‘stop,’ or ‘too much.’ Only I can say when you’ve had enough.” She emphasized the point by tightly grabbing my balls in my already tight jeans.

“Yes Madeline, I understand.”

She smiled comfortably at my answer, “Just so you know I’m not a total bitch, if you request that I go slower, or take my time, I’ll consider it, but it’s up to me, not you.”

“Thank you Madeline.”

“And finally, rule number three. You will be available to me and only to me, whenever I demand it.” She took another drink and motioned for me to do the same, “I’m only interested in monogamist relationships, and that means if we’re going to… be an item… then you will refrain from being intimate with anyone else… unless of course, I initiate it.”

At that rule, I smiled back for the first time, “We’re an item?”

Her eyebrow raised, waiting for me formal response.

“Madeline, being monogamist with you has been my dream since the 5th grade.”

“Oh Jacob, you aren’t going to regret this. I’m going to make you the envy of everyone at school—yours and mine!” She put her drink down and spun around back onto my lap once more. She put her hands on my face and kissed me deep—the first open mouthed kiss I’d even had. My hands came up and rested gently on her hips. She immediately reached down and took my left nipple in between the thumb and forefinger of her right. She latched on and twisted hard, causing me to yelp in pain and surprise.

She broke the kiss with an overly hard bite to my lower lip. She pulled it with her as she move away from me, finally letting it snap back to my face when she was far enough away. She looked at me with seriousness in her eyes. “Jacob, what was rule number one?” She asked.

My surprise became informed knowledge. I lifted my hands from her body and carefully put them beside my own legs. Meekly I said, “I don’t get to touch you until you say I can.”

She release my nipple and pain faded immediately. She lightly drew circles through my shirt against the angry flesh, making my breathing flutter. “Good boy.” She kissed my lower lip then said, “You’ll do well to remember the rules, as my punishments tend to escalate.”

My mind raced to find the right response, “Of course Madeline, I would expect nothing less for a repeat mistake.” Then I added, “I’m sorry that I broke one of your rules so quickly. It won’t happen again.”

At that, her tongue dove back into my mouth and she kissed me for what seemed like eternity. When she finally broke the kiss, she had a knowing smile on her face. A smile of victory and future pleasures to come. She disentangled from my lap and poured two glasses from the ice-chilled bottle.

“To the rest of our night together!”

I took the glass she offered me and asked, “Only this night?”

Her already wide smile became wider. “We’ll see how well you do with following instructions and making me happy.” She downed the glass in a set of quick gulps. “Let’s finish this bottle and head back. We only have eight hours until breakfast and I need to fuck you at least a half dozen times by then.”

* * *

Maddie’s suite was a little different from our. She had a single king sized bed where Will and my room had two queens. Since it was on the other side of the corridor, her view was different, but equally as impressive as Will and mine was. The bathroom had the same huge walk-in shower and an oversized tub that could easily fit two (if not more) people. As soon as the door was closed to the hallway, she panted another aggressive kiss on my mouth, she broke it and pushed me to the bed. “Take off your shoes and socks, I’ve got to get a few things.”

I pulled my shoes and socks off without taking my eyes off Maddie. She went to her suitcase and pulled out a smaller black bag. It was the size of a mid-sized purse, but it was black nylon and had a heavy duty zipper down one side. She opened it, away from my probing eyes, and pulled a blindfold out. Her lips curved to a mischievous grin and she tossed the blind fold to me. “Take your pants off and put this on.” I complied and she interrupted, “Boxers too.”

Nervously, I pulled my underwear off, exposing myself to the woman of my dreams. I was embarrassed that she would think my penis was on the smallish side. My insecurity had caused my penis to soften as soon as she had opened the door to her room. Thankfully, her response warmed my heart, “Oh, that’s perfect.” Then more forcefully, “Put the blindfold on and lay down, spread eagle.

I complied.

I could hear her hand rustle around in nylon bag and then again when she put the bag down. The bed shifted as I felt her weight next to me on the mattress. Her breath was in my ear again as she whispered, “Stay relaxed, I’m going to touch you, but I don’t want you to get hard—not yet at least.” She kissed my neck again, “Can you do that for me, Jacob?”

“I think so…” I croaked, starting to shake in anticipation of having one of the most beautiful women in the world touch my sex.

She rubbed something super slippery around my scrotum and over my shaft. I tried not to react, not certain how successful I was being. She gently, but swiftly pulled my balls through a ring of some kind and then maneuvered my still soft shaft through it as well. I had seen cock rings while watching porn on the internet, and this seemed to be something similar. Her breath was back on my neck again, “You’re doing good, just a little bit longer.”

I shuttered again and whispered back, “Please hurry. I don’t know how long I can stay soft.” She kissed my neck with a peck and returned to my crotch with urgency. I felt her maneuver my shaft into a tube, like a mechanical masturbation device of some kind. The sensation was getting to be too much and I could feel myself losing the battle to stay soft. Maddie must have finished though, as I felt her get off the bed.

“That part is done. Now for the next bit.”

I heard her working through the nylon bag again, getting more items. “Don’t move, Jacob.” she warned as she used what felt like a satin sash to tie my ankles and wrists to the feet of the bed frame. Keeping me spread eagle.

I could feel my penis trying to get hard, but something was preventing it. I was experiencing an odd pressure, but no real pain. It was strange, but oddly sexy. I couldn’t wait to see what she had done to my manhood.

“Almost done, my Sweet,” she said, making me shudder in anticipation. She kissed me passionately, all around my mouth, making me stretch to reach her lips and tongue. I felt a ring being put into my open mouth, resting behind my teeth, forcing my mouth open. It wasn’t uncomfortable, but it was odd not to be able to close my mouth. Maddie fastened the ring in place with a strap that went around the base of my head. “How does that feel? Did I make it too tight?”

“Mmmggrrmghh.” I said. Apparently with a ring in my mouth, I couldn’t speak too well.

Maddie giggled at my predicament then she placed a pillow behind my head, raising my face at a slight angle that she must have thought would be good for licking her pussy. “That’s funny. Just nod for yes or shake for no. Is the gag comfortable?”

I nodded, letting her know it was okay… weird, but okay.

“Now we can really begin.” I heard the zipper of her jeans fly come down, followed by the efficient struggle of a sexy woman wiggling out of a pair of skinny jeans. There was some more rustling noises that made me think her top had come off as well. Once again her hands were on my chest, but this time to unbutton my shirt and to pull it open. My tied wrists made it impossible for her to take my shirt completely off, but she still had unrestricted access to my entire body.

Once again I felt her straddle me and my penis pressed against the restrictive tube she had place on me. Her hands caressed my face and her lips nibbled at the open circle that was my mouth. She pulled back a bit and started to scoot up my chest, and she whispered, “Here it comes, big boy.”

A fleshy shaft entered my mouth through the ring. I gurgled in surprise as it slid into my mouth. My first reflex was to close my mouth, but the gag effectively prevented my mouth from closing. My next reflex was to push it out with my tongue, which resulted in a sexy groan from Maddie, “Yes, run your tongue over my cock.”

Her cock?!? I must have misunderstood what she said. She’s a beautiful, stunning woman, she couldn’t have a cock, could she?

The warm shaft kept going deeper into my mouth and started to tickle the entrance of my throat. I could feel my gag reflex threatening to kick in, but suppressed it much as I could.

“Oh that’s nice.” She kept the shaft right at the entrance of my throat. The she pulled it out a bit and started to slide it back in and out and in again with a smooth motion. “Jacob Sweetie, you have a very fuckable mouth.”

“Haaannkyuuu.” I gurgled.

“Mmmm…” she said as she started to increase the length of travel that her cock stroked my mouth. A slow rhythmic motion that took her from the tip of my lips to the entrance of my throat. “Relax Jacob. You’re doing great.”

Her praise made my face blush. I could feel the heat on my cheeks and I ran my tongue faster around her shaft and when she nearly pulled out on each back stroke, I swaddled her thick, bulbous cock head with as much motion as my tongue could produce.

“Mmmm…” she said again, “You are a natural cock sucker. I had a feeling you would be.”

“Haaannkyuuu.”

“Now focus on relaxing your throat. I’m only about half way in your mouth right now, but I want you to take all of me. Okay Sweetie?”

“Mmmmm Hmmm.” I said with a subtle nod

“That’s a good boy.” I felt her reach back and fondle my exposed scrotum. My penis was encased, but apparently my scrotum was free and able to be played with, which she started doing with her expert fingers.

Her next stroke poked the back of my throat and I felt like I needed to gag. Following her request, I relaxed as best I could, focusing on the pleasure she was giving my scrotum. Twice more she poked the back of my throat and I almost gagged but then she poked through and I could feel the head of her cock leave my mouth and enter my neck. So many emotions flashed through me at the same instant. Satisfaction at being able to deep throat Maddie, Tenderness as she massaged my scrotum while I pleased her orally, Passion that I had for the woman I’ve had a crush on for over a third of my life… and Panic at the realization that I couldn’t breathe when her cock was down my throat.

The panic quickly subsided as Maddie kept up the steady pace of pulling nearly all the way out and back in again. Once the fleshy head left my throat I took an in breath and just before it re-entered, I made an out breath. We both found a rhythm in the motion and made the most of our different roles. With each stroke, she went just a little deeper than the one before and after a few short minutes, my nose was up against her pelvis on the in stroke. Luckily, there was no pubic hair on my nose or I may have had to sneeze. I don’t want to think about how much a sneeze would hurt with her monster cock entombed deep in my neck.

“You’re going to make me cum, Jacob.” She whispered, making me groan in pleasure, “When I cum, I’m going to bury myself in your throat until I’m done.” One hand gently held the side of my face as she described what she was going to do to me. “I don’t want you to be frightened. You won’t be able to breathe, but it will only be for a short while, less than a minute.” Her strokes started to get just a little faster and harder now. “You’ll be a good boy and you won’t panic, right?”

“Mmmmmm Hmmm.” I said around her cock on the next out stroke.

“Oh Sweetie, you make me so happy.” Her pace continued to pick up. She dropped my scrotum and put both hand along side my head. Her position shifted a bit and my head tilted back as she placed her pelvis directly over my face. “I just love fucking this beautiful mouth of yours!”

Her increased pace started making it difficult for me to get a full breath on each stroke, so I alternated, in breath on one stroke, out breath on the next.

Her pelvis was smashing my nose flat each time she bottomed out and her moans became grunts. A few more nose smashing thrusts and then she held my head against her pelvis, jerking her hips against my face. I couldn’t taste her cum, but I could feel it squirt through my esophagus and straight into my stomach. I was glad the pounding was over, but now my need to breathe started to become urgent. Remembering that she said it would be less than a minute, I tried to relax and just wait. Her spasms were lessening and finally she pulled my face deep between her legs one last time as she jerked her last spasm down my gullet. She slowly pulled her monster out of my neck but left the tip to rest in my mouth as I caught my breath the first time in what seemed like ten minutes.

“Jacob… Wow.” She kept moving her cock head around my mouth, spreading a small amount of her left over semen over my tongue. “I’ve never had a blowjob that good before. You’re a natural!”

“Haaannkyuuu Aaadddeeee.”

That caused her to laugh, “You deserve a little treat…” I felt her sit up a bit, leaving her slowly softening cock in her mouth. A few drops of her cream dripped from her cock head as she used her fingers and squeezed it out of her shaft, onto my tongue. “Ahh, there you go Sweetie. A little taste for you to enjoy.”

I swirled her gift around my mouth and to my own surprise, I enjoyed the taste. The taste of Maddie, my dream girl. The corners of my mouth must have curled up a pinch because Maddie could tell I was smiling at receiving her gift. “I’m so glad you liked it. I’m sure you’re going to get a whole lot more before spring break is over.”

She pulled out of my mouth and removed my blindfold. The smile that greeted me was radiant. I’m not certain how, but she was more beautiful to me now than she had ever been. She reached behind my head and unbuckled the strap on the gag and carefully lifted it out of my mouth. I was surprised as how much of my own drool had covered my lower face and neck. Maddie took the tail of my shirt and mopped up the mess. She bent down and give me a long, slow, passionate kiss. During the kiss, she started fondling my scrotum again, causing my growing member to strain against the restraint again. She broke the kiss and showed me the pink plastic device that encircled my penis.

“It’s called a Holy Trainer. It’s a chastity device.” She reached down and gripped the device. She pulled it forward so I could see it better. “It prevents you from getting an erection or from masturbating.” A wicked smile crossed her lovely face, “From now on, my Sweet, I control your pleasure. And you won’t be getting any pleasure from this.” she jiggled the Holy Trainer, making my penis once again strain against the confines of the tube.

She got off the bed, leaving me tied up, and went to her nylon bag again. She pulled out a black rubber, egg-shaped device with what looked like a round foot attached to the base. It had a tube running about two feet to a squeeze bulb. She showed it to me and the started to squeeze the bulb, causing the egg to inflate. She spun a little metal valve near the bulb and the egg deflated to it’s original shape. As she upended a bottle of clear liquid and dripped a few drops onto the egg, she said, “I need to get you ready for our next session. It’s going to feel a little weird at first, but I promise you’ll soon love it.”

“Umm… Maddie,” I started squirming, thinking about where that egg was headed. “I don’t know about this…”

Her smile instantly vanished. Replaced by what looked like a scowl. “Jacob, what is rule number two?”

Oh crap, I thought, trying to remember our conversation in the night club and thinking that it seemed like a week ago. “That I don’t get to say no?” I said as more of a question. I must have gotten it right though as Maddie’s smile returned to its full glory.

“Good, you remembered. I’ll be lenient this one time, since this looks a little intimidating.” She motioned to the inflatable butt plug. “You need to trust that in our time together, you may experience some discomfort and maybe a little pain, but I will never cause you injury or real harm.”

I lay, bound, completely still. My eyes bugging out at the size of the egg that she was getting ready to shove into my ass.

“Jacob.” She slapped my belly. My fright retreated an a portion of my rational mind returned.

“Uhh.. yes.” I spat out, “I know that you won’t injure me. Thank you Madeline.” It must have been the right response, since her smile returned again and she placed the head of the egg at the entrance to my sphincter.

“Try to relax. I promise this won’t hurt if you relax.” She bent down and started kissing and nibbling on my left nipple. An immediate groan escaped my lips and she started moving the tip of the butt plug around my asshole, spreading the lube. She alternated kissing, licking, and nibbling on my nipple and it was wonderful. The movement of the egg-shaped plug against me started to feel really nice. So nice that I started to grind my body against it to maximize the sensations. Maddie looked up from my chest, my nipple caught between her teeth. “I told you that you’d love it.” I smiled and dropped my head back to the pillow, letting my eyes drift shut so I could focus on the pleasure she was giving me.

“Yes Madeline. I do. Please give me more.” And with that, the butt plug was pushed all the way in. I gasped and clinched, but in an instant I started feeling better. Within seconds I was rotating my hips again, helping the plug move around inside of me. Maddie still had her fingers on the base of the plug and was manipulating the plug in my ass, massaging the inside of my anus. She seemed to find what she was looking for and started pressing the plug against a particular spot that gave me significant pleasure.

“That’s your prostate.” She said.

“Mmm Hmm.” Was all I could say in return, my hips still rotating uncontrollably.

“That’s how you’re going to get your pleasure. Not through your penis, understand?”

“Okay…” I said again, not really knowing what she was talking about, a thin film of sweat forming on my upper lip.

“Good.” I could hear the smile on her face as she said the word. A sound like a sigh came from between my legs and I jerked in surprise. I opened my eyes and saw her other hand on the squeeze bulb. She attacked my nipple again, which caused my hips to move, which keyed her to trigger another squeeze.

“Ah…” was all I could say. It was a strange, filling feeling, but it wasn’t painful at all. Within moments, I was moving again, wanting more stimulation from the butt plug and was rewarded with a third pump. “Oooo…” I gasped.

“Jacob, Honey, you’re doing so good. I’m so proud.” Her praise made me smile. “Three pumps is about the size of a ripe lemon. Five is like a small apple. Ten gets to be a good sized orange.” I couldn’t imagine something the size of an orange in my rectum, but I knew Maddie could. “We need to get you comfortable with and even wanting more than seven pumps. Once you’ve grown accustomed to that, then you’ll be ready for me.”

I had been so focused on my anus that I had completely forgotten Maddie had a cock, and one long enough to go half way down my throat. “Show it to me.” I whispered, like an addict needing to see a needle.

The wicked grin reappeared on Maddie’s face and she pumped another bulb of air into the plug. She stood up along side the bed and I saw her beautiful cock for the very first time. It was soft, but not fully so. It hung down from her pelvis about five inches and was substantially thicker than mine when it was fully erect. It was golden bronze in color and the head was a shade darker. Her cock was just like the rest of her—absolutely flawless. A small drop was forming at the tip and I couldn’t stop myself from asking to taste it.

She didn’t answer me, but she moved to sit on my chest, inching up to get her beautiful cock close to my mouth. When it was within reach, I took the tip between my lips and alternated sucking and swirling my tongue around the head. The pre-cum was sweet and slippery with just a hint of salt. It could have been the syrup on an exotic desert. Another pump filled my ass and after a moment of surprise, I attacked her cock with even more fervor. The sensation of my ass being filled as I sucked on my dream girl was all encompassing. She pumped bulb after bulb into my ass until I was squirming with desire. Wanting more than just volume in my anus, but not certain what it was I needed.

Her cock was close to being fully erect and I could see it was ten inches long and the diameter of my shaving gel can. I couldn’t get enough of her cock in my mouth and started to force it down my own throat by raising my head off the pillow. “Ahhhh,” she sighed as she started rocking her hips in sync with my head bobs. She inched up on my chest and again positioned herself with her pelvis directly over my face. I let my head rest on the pillow as she slowly, lovingly fucked my throat for the second time in 10 minutes. Another pump filled my ass, then another. My bottom was fuller than it had ever been before, yet it felt absolutely wonderful. Just then, Maddie pulled completely out of my mouth at the same time the plug deflated. A feeling of desperation replaced my contentment and caused me to whimper.

She moved beside me on the bed, one hand teasing my right nipple, the other working the squeeze pump. Maddie started talking to me as she slowly pumped the plug back up, “That was ten pumps on your first try!” She had a huge, proud smile, “You are a butt slut, Jacob. Did you know that?” She kept pumping and I kept squirming.

“Uhh… no.. Mmmmm…”

“That’s ten again—how do you feel with an orange-sized toy in your ass?”

“More please.” I whispered, unable to help myself.

“Eleven…” She slowly squeezed the next one in, “Twelve…” My squirming become uncontrollable and my I started to pant, “Thirteen…” The world started to fade away from me. The only thing that mattered was the fullness of my rectum and how wonderful it felt. “Fourteen…” I made some kind of noise, but didn’t know what it was. Maddie must have interpreted it as ‘more,’ since her next word was, “Fifteen… Wow. I think we’ll stop here for a bit, my sexy little anal whore!” Her pet name made me smile and blush at the same time.

She put the squeeze bulb on my abdomen reached down to fondle my scrotum. My squirming continued as even subtle movement of the huge plug in my ass was enjoyable. “Sweetie, I’m going to leave you here for a moment while I go to the bathroom. You might start to feel a bit uncomfortable with the plug inflated that large, but it won’t injure you. It’s getting you ready for what’s coming next.” She gave my scrotum one last tug and then went to her suitcase. She pulled out something red, black, and lacy and disappeared into the bathroom. The next five minutes started off as glorious. The new discovery of anal pleasure coupled with being bedded by the woman of my dreams. Glorious quickly became a feeling of fullness, which degraded to pressure, which then became induced cramping.

“Ugh.” I gasped as the first cramp came, my body involuntarily trying to eject the anal invader, but my sphincter was too small to pass the now grapefruit-sized plug. “Ummm.” The second cramp came a few moments later, then a rapid succession of cramp after cramp. “Mmaadddie…” I groaned, my lower body shaking. “Heelllpp…”

Just then the door to the bathroom opened and there stood Maddie in a lacy, one-piece teddy. She posed in the doorway with one hand on the door jam, above her head. The teddy only covered the bottom quarter of her breasts, leaving her cleavage and nipples fully exposed. Her substantial bosom was enhanced by the cut of the cloth. The teddy narrowed down to her slim waist and was cut in a sharp V where it disappeared under her crotch. A cutout in the teddy exposed her fully erect cock, which stood more than ten inches from her groin and a smooth, hairless scrotum hung daintily below her monster shaft. The impact on me was instant. I could feel my penis strain in the plastic tube of the Holy Trainer and the cramping ceased immediately as the impulse of sex overtook the impulse of fullness. My colon, while still full to the brim, actually wanted another pump of the bulb.

“Jacob, sweetie,” She said with a huge twinkle in her eye, “Are you ready to lose your virginity tonight?”

“Yes!” I heaved. “Please make love to me now…” I begged. “Please…” I was delirious with frustration and needed relief of any kind. In my heart, I knew that having her deep in my bowels would give me relief even though my mind questioned that logic.

She brought a bath towel with her from the bathroom and grabbed a condom and the lube from her nylon bag. First, she let a little bit of air out of the butt plug and the comfort washed through me in a rush. She then had me move my hips as she put the towel under my bottom. Then she carefully put on the condom. I watched her open the ‘Magnum’ labeled wrapper and felt a shiver. “We didn’t get the opportunity to fully clean you out, so I’ll need to wear this.” She winked and me and continued, “The next time we’ll get you squeaky clean first so this isn’t necessary.” Once the condom was fully unrolled, it only covered a little more than half of her cock, but she seemed satisfied. Then she untied my ankles and pushed my knees up to my chest. She took the squeeze bulb in her hand and slowly deflated the plug to it’s normal size. I felt my breathing return to normal and realized I hadn’t even known I was panting when the grapefruit-sized toy had filled my anal cavity. She slipped the plug out without any resistance from my stretched sphincter and laid it on the bath towel. It was surprisingly clean considering where it had just been. Maddie then dribbled some lube on top of her condom and I let a few drops spill onto my anus. I was surprised how little she used. She must have read my mind, because she said, “This is a silicon-based lubricant. It’s a hundred times slicker than water-based lube, and it doesn’t wash off easy, so we can use it in the shower and tub.”

Just then I thought about her fucking me while in the shower and my eyes rolled back and I moaned in anticipated delight.

“Aren’t you just precious. Dreaming about being fucked in the tub and shower.” She reached down and fondled my caged penis and scrotum while she lined up the head of her steel hard cock to the welcoming opening of my ass. “Don’t worry Sweetie, we’ll get to that… in time. First, I need to take your virginity and make you MINE.” She emphasized her ownership with that word by piercing me all the way to the hilt in a single swift motion.

“Uggghhhh…” I cried out, my ass spasming around her massive tool. While my colon had been spread wide enough with the inflatable toy, it hadn’t been stretched deep enough. My sphincter muscles were also rebelling since the girth of the uninflated toy was less than half of Maddie’s erect penis. That rebellion resulted in uncontrolled spasmodic contractions around her enormous cock. She didn’t move, but squealed in delight as I masturbated her phallus with my pulsing muscles. It took more than half a minute before my muscles calmed down. I don’t know if it was because they had exhausted themselves or if they grew accustomed to the size of Maddie’s intruder, but they relaxed and Maddie started to slowly move in and out of me. I felt like I was on a tightrope, having to maintain balance or else I would fall into a world of pain.

Maddie put her hands on my chest and rubbed my nipples with her thumb nails. “Breathe Sweetie, breathe.” I followed her instructions and within moments the smooth motions of her movements, the stretching and stimulation of my anus, the filling and emptying of my colon, and the sharp tings of almost-pain on my hardened nipples culminated into extreme sexual desire. My eyes flew open and locked onto hers.

“Kiss me…” I whispered and she complied. Speeding her movements, increasing both her pace and the depth of her stroke. She started grunting with each in thrust and I could feel her bucking against my ass cheeks, slowly pushing me up the bed with each stroke. She must have been aiming for my prostate, because each thrust brought the same pleasing pressure as when she was manipulating the butt plug within me earlier. I could feel a build up, but it was different than when I would masturbate. This was a slow, steady buildup that seemed to peak and stay peaked instead of ending in the crescendo and subsequent let down of an ejaculatory orgasm. It was like I was riding the wave instead of having the wave wash over me.

I was in absolute bliss. The entire world seemed to melt away. I was only aware of my sphincter being stimulated and my prostate being rubbed. Even Maddie’s grunts were drowned in the sound of the sexual wave I was riding. It could have been ten minutes or a week, but eventually I heard Maddie whisper in my ear. “I’m close, Honey.” A small portion of my mind came back into my head when she spoke, but I couldn’t focus very well, so I moaned in acknowledgement. “I’m going to cum in your mouth.” She whispered. I heard that and a little bit of anxiety followed. I liked giving her pleasure with my mouth, but I having her deposit her entire load of sperm still seemed a little alien. “I will always cum in your mouth, Sweetie.” She said. “It’s the reward for being a good cum slut.” The smile she gave me when she said that was one of ownership and total control. “You want my reward, don’t you Jacob?”

“Yes Madeline.” I was unable to disagree with my goddess in any way. “I always want to eat your cum.” Part of my mind couldn’t believe what I was saying, but the other part continued, “Please feed me your cum now… and always.”

With that, she doubled up on intensity of her thrusts until the pulled completely out of me, leaving my poor prostate unstimulated and alone, ceasing my wave in an instant. She rolled to the side, yanked off the shiny condom an started jacking herself like there was no tomorrow. “Open up,” she commanded and I complied. She place the head of cock behind my lips and keep jacking. “Use your tongue, Sweetie.” Again I complied. Her other hand went to her left nipple and she pinched it until I though milk would come out. With a building groan, she pivoted over my head and shot stream after stream into my hungry mouth. Her jerking movements made it hard to keep my lips over her cock head, but I kept every bit of cum she shot into my mouth. After about a dozen ejaculations, she took a pause and squeezed her urethra from the base to the tip, depositing another large dollop into my ever greedy mouth. With that, she withdrew and told me not to swallow just yet. She reached to the nightstand and grabbed her phone. Aiming the camera at my face she said, “Open up and say, ‘Cheese.’” Of course I followed instructions, smiling as big as I could without losing any of the precious salty seed she had given me to consume. The flash made my eyes blink and when she was happy with the photo she said, “Okay, now you can swallow your reward. You earned it!”

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