Sweet Gwendoline Ch. 20

By the time I returned home, I was emotionally and physically exhausted.

I mean... I have plenty of experience when it comes to receiving harsh, soul-scorching spankings, but involving people from my childhood in those humiliating spanking games is something I'm not used to. Bringing my mother and a girl from my childhood into my most recent spanking had left me feeling wobbly and violated.

That was Lyndsay for you. She was something of a genius when it came to formulating ways to humiliate and shock me. The longer I knew her, the more emotional levers and buttons she discovered within me that she could pull and push. She had become an expert at turning my life into an erotic, emotional rollercoaster.

Of course, the fact that I was home didn't mean that the rollercoaster ride was over. Ms. Knauss had issued a list of rules for me to follow now that she was my disciplinarian. One of those rules mandated that I was to report to her immediately whenever I returned home.

Ms. Knauss made it easy this time out. I took a few steps into the foyer, and there she was, waiting for me and looking for the entire world like a stern, disapproving headmistress. I hadn't even done anything wrong, but the look she gave me made my legs turn wobbly and I felt an irrational urge to fall to my knees and beg for forgiveness.

"Gwendoline," she said, drawing out each syllable of my name slowly and deliberately, "did you enjoy your time in the outside world?"

"It was fine," I said, and even though I hadn't done anything wrong, I felt like collapsing to my knees and confessing that I was somehow guilty of something.

"Well, you're home now," she replied, "You know you're not to wear clothing at home. Will you strip voluntarily, or should I remove your clothes by force?"

Ms. Knauss had the sort of voice that demanded obedience and cooperation. I began to shed my clothes before she had even finished asking her question.

After I slipped my panties off and added them to my pile of surrendered garments, Ms. Knauss turned to Lyndsay and inquired, "And did Gwendoline behave herself while she was galivanting about?"

"She did everything she was told," Lyndsay assured the disciplinarian, and then Ms. Knauss turned to me and ordered me to stand with my hands up against the wall, my legs far apart and my knees straight.

Ms. Knauss took a lot of time to make certain that every detail of my position conformed to her specifications. It seemed to me that it was designed to make me feel as vulnerable and exposed as possible. As Ms. Knauss prepared to perform a body cavity search on me, Julie and Lyndsay were invited to watch.

Much to my surprise, both Julie and Lyndsay declared that they wished to stay and witness my humiliation. Then Ms. Knauss snapped on a latex glove and got into position behind me.

I waited and waited. Every part of my body went tense, waiting for a latex, clad finger to penetrate a very tender part of my anatomy, however my disciplinarian was content to make me wait. I held the position so long that my legs started to feel weak and sweat began to form on my torso and underneath my arms.

Then, when I thought I couldn't take the suspense anymore, I felt two of Ms. Knauss's fingers slide deep into my vagina.

I moaned and felt an orgasm approaching as she fingered me, making only the slightest pretense of doing a cavity search, she roughly fingered my aching cunt and got me closer and closer to a screaming orgasm. I knew that if I had an orgasm without permission, I'd be punished horribly, but there was little I could do to stop it.

Then, just when it seemed that it was impossible to stop a shuddering orgasm from ripping through my body, Ms. Knauss pinched one of my pubic lips and then withdrew her fingers from my aching cunt.

I began to sob, and hot, wet tears slid down my face. I wasn't certain if I was crying because of the humiliation of having my vagina overzealously probed by this domineering woman while my friends watched or because of the sexual frustration. Somehow, I endured both and held the required position, although I trembled and shook slightly as I cried over what was being done to my poor, defenseless body.

Then, without warning a huge blob of cold gel was forced against my tender, tiny anus, and a finger forced its way inside of me.

"That's cold!" I exclaimed, almost falling over because of the shock of the finger coated in cold gel being forced into anal cavity.

"What was that?" I heard Ms. Knauss's stern voice ask, while the finger wriggled and probed inside of me. "Slave girls are not allowed to complain."

It was hard for me to think with that finger moving around inside of me, but I knew I was in trouble. Ms. Knauss was constantly looking for excuses to punish me, and I had just given her one.

"You'll have to be punished for that," Ms. Knauss informed me. "Just as soon as I've finished searching you."

The cavity search was humiliating and demoralizing, and I wanted it over as soon as possible, but as soon as it was over, Ms. Knauss was going to punish me. The body cavity search seemed to go on forever, while simultaneously ending all too soon.

Ms. Knauss led me out into the living room for my punishment. She sat down on an ottoman and had me drape myself across her lap. My bottom was already sore from the spanking my mother had given me, so as Ms. Knauss delivered a spanking to my poor, innocent bottom every blow was painful.

But, as I squirmed and cried out in pain, something unexpected happened. As Ms. Knauss reddened my ass, I felt the beginnings of an orgasm deep within my loins. I had been filed with so much sexual tension of late that my body had become confused. Ms. Knauss didn't even touch my vulva as I lay across her lap, however, as my bottom flared with pain, an unexpected orgasm blossomed inside of me. It was as if the pain of the spanking reverberated through my loins, and even the indirect and painful stimulation of being spanked was enough to make me come.

My pathetic screams of pain masked my powerful orgasm as I squirmed and bounced across Ms. Knauss's lap. I sobbed and whimpered and hot, wet teared dripped down my face as I experienced wanton orgasmic bliss.

* * *

I had promised Tricia that I would make her part of my social life and invite her to participate in some of my life's amusing diversions. And in the days and weeks that followed, I complied with that promise. Lyndsay had suggested that it might be fun to go skinny-dipping in the decent-sized lake in her family's back yard. I suggested that Tricia might want to join us.

"What a splendid idea," my girlfriend enthused. I called Tricia and invited her over. Lyndsay proceeded to call Collen, and it turned into a regular social gathering with the four of us swimming, splashing around and having girlish fun.

Lyndsay's home had an Olympic-sized swimming pool, however, Lyndsay insisted that skinny-dipping was a rite of youthful revelry and wildness and that a manmade swimming pool was just too civilized.

"Skinny dipping is about being wild, carefree and primitive," Lyndsay explained, "It totally destroys the primal vibe if there's a stainless-steel lifeguard's chair and somebody chronically checking the chlorine levels."

I'm usually kept naked at home, however, Lyndsay decided that the four of us should engage in the ritualistic shedding of our clothes before getting into the water. As a result, I was permitted to wear clothing until Tricia and Colleen arrived.

Tricia was the first to arrive. She let out a girlish laugh when saw me, rushed up, hugged me and kissed me on the cheek. I found myself gripped with a confused mixture of emotions. For years Tricia was the geeky, emotionally needy kid who annoyed me. Then she was the woman who aided and abetted Lyndsay in humiliating me and witnessing me getting an over the knee spanking.

Tricia's affectionate hug didn't seem to fit neatly into either role, and I felt perplexed and uncertain how I should respond. Eventually I ceased trying to figure it out, and I slipped my arms around the teenager and pressed my body against hers.

It was right about this time that Colleen arrived in the back yard and announced herself.

"Well, the two of you look chummy," she observed.

Coleen was a tall, athletic, dominant woman. And the last time I had seen her, she cruelly pinched my nipples and fingered me to orgasm while I was naked, bound and helpless. In my mind she was categorized as one of my cruel stepsisters.

But then, Colleen confused me by wrapping her arms around me and embracing me in an affectionate hug, much like the hug from which Tricia had just released me. It seemed bewildering and wrong for a wicked stepsister to envelop Cinderella in warmhearted, friendly hug, but despite my confusion, I hugged her back.

I was respectably clothed and being treated with friendly affection. Collen held me close and allowed me to rest my head comfortably on her shoulder. All of this seemed like a violation of slave/mistress etiquette, but Lyndsay was in charge. She had set all of this up. If this was the way she wanted things to proceed, I'd go along with it.

After all the hugs and small talk, Lyndsay suggested that it was time for everybody to get naked, and she raised her eyebrows at me. I took the hint and began to disrobe.

My t-shirt and bra came off easily. Then I unsnapped the front of my jeans and unzipped. And then I hooked my thumbs in the waistband of my panties and pulled them down. I was sort of expecting Tricia and Colleen to ogle my naked body at that point, but instead they proceeded to take off their own clothes and get just as naked as me. Finally, Lyndsay shed her clothing, grabbed my hand and pulled me along as she eagerly ran towards the lake.

Lyndsay sprinted into the water, and her momentum didn't stop until the two of us were up to our waists in clear, cold water of the lake. It was cold enough to be invigorating without freezing me to death. Lyndsay broke out in goosebumps and her nipples became instantly erect. Then she smiled and called out to our friends, "Hey, Gwen and I aren't doing this alone! Get your asses in here!"

Even though all four of us were naked, and all four of us were very attractive and sexually appealing, there was very little sexual tension going on. We swam and we splashed and laughed like schoolgirls. The four of us engaged in playful banter as we swam and eventually our banter drifted into a discussion of which of us was the most athletic.

"You and Colleen both have bodies that look like they were sculpted by the gods," Tricia remarked, "especially your legs. How do you get legs like that?"

"I took years of ballet training," I remarked, "ballet teachers and chorographers would work me until I dropped from exhaustion."

"I did track and field for years," remarked Colleen, "sprinting, pole vaulting, the long jump, that sort of thing. It was grueling work, but it pays off dividends in endurance, strong legs and strong abs."

"You're both amazing," Tricia said as she proceeded to shower us both with compliments, "I mean, I'm totally happy with my body, but you and Gwen are goddesses. The two of you are awesome."

This somehow led to a discussion of which of us were the most athletic. Only one of us could be the best, and Lyndsay suggested a series of competitions to see who was worthy of the title. Colleen suggested a swimming competition. I was a strong swimmer, so I readily agreed. We swam from one side of the lake to the other to see who finished first, but we were too evenly matched. We both reached the finish line at exactly the same time.

"Okay, I know," Lyndsay exclaimed, "let's have a wrestling match."

I thought the idea of a wrestling match was stupid, but Colleen, Lyndsay and Tricia all thought it was a great idea. I was outvoted three to one, and as soon as everyone got out of the water, I was forced to wrestle against Colleen.

And to make matters more interesting, Lyndsay declared that the loser would get spanked by the winner.

"And if that isn't enough to motivate you to do your best," Lyndsay added, "the winner gets her vagina licked by the loser."

Colleen raised one eyebrow quizzically and asked, "Licked how many times?"

"As many times as it takes to bring the winner to an earth-shattering orgasm," Lyndsay replied.

Now, I had training in ballet and gymnastics, but I had zero experience in wrestling. And from the enthusiastic look in Colleen's eyes, I was assuming that she'd wrestled before. As soon as the match started, Colleen and I began to roll around on the ground, with me struggling and Colleen moving quickly and deftly to make me helpless.

Struggling against Colleen while we were both naked and rolling around on the grass covered lawn felt even more primitive than skinny-dipping. Colleen was strong and knew a number of wrestling holds. She used her strength and skill to grab me, flip me around, immobilize my upper body and pin me to the ground.

At one point she had me in a half nelson with her legs wrapped around my hips, during which time she proceeded to grab my breasts and fondle them roughly. I squirmed and tried to break free from her grip, but for all my struggles, I was unable to squirm out of her grasp.

Lyndsay and Tricia were enjoying the spectacle as I struggled vainly to break free from Colleen's wrestling holds, so they encouraged us to continue our competition for as long as possible.

At some point Colleen got me into a full nelson and left me helpless from the waist up. I could stamp my feet and flail my arms helplessly, but I couldn't do a damn thing to break free. At this point, Tricia went and found her phone and proceeded to take pictures of me as I struggled to break free from Colleen's expert grip.

Tricia enjoyed the spectacle of my humiliation and helplessness as Colleen sat on my back and applied a move she called the chinlock. In this move, she pulled my head and torso backwards causing agonizing pain as she arched my spine backwards into an extreme arch. While I grunted and struggled, Lyndsay pointed out to Tricia how the way Colleen was forcing my spine to arch caused my breasts to be prominently displayed and thrust out for lucky spectators like herself.

A few seconds later Colleen, still While behind me, grabbed both of my arms and locked them tightly together. She used both arms at first, but when she had better leverage, she was able to use one arm to grip them just underneath the elbows and hold them together, immobilizing my arms and causing me to grunt and gasp in pain as she put pressure on my shoulders and forced my elbows tightly together.

And if this wasn't humiliating enough, Colleen proceeded to hook her legs around mine and once hers were securely in control of mine, and, once hers were securely in control of mine, she spread her legs apart, forcing my own legs to spread wide. I struggled to close my legs, however, Colleen used her superior strength and/or leverage to overpower me, and my legs were helplessly forced wide apart, giving Tricia the opportunity to take more humiliating photos.

Eventually Colleen ran out of ideas for how she could use wrestling holds to humiliate me, and we moved on to the portion of the entertainment where Colleen got to spank me.

"You have really great glutes," Colleen assured me, "If you told me back in high school that one day I'd be spanking your perfect bottom, I wouldn't have believed you."

Colleen sat on a blanket, and, following Lyndsay's orders, I crawled across her lap, arched my back and raised my butt up for Colleen to smack. Then Colleen looked up at Lyndsay and asked, "So, do you want me to actually hurt your girlfriend and turn her ass red? Or would you rather I just left a few handprints on her ass?"

"I want you to turn her ass red," Lyndsay insisted, "Gwen has a high tolerance for pain. You'll need to rain down an intense barrage of hard swats to make a memorable impression on her."

"Is that true, Gwen?" Colleen asked as she ran her hand across my upraised buttocks and the backs of my thighs.

"It's true," I responded, "I've been spanked a lot. I've got a lot of experience with having a red ass."

Colleen asked a few more questions about the proper way to spank my bare buttocks, and then there was a loud CRACK and a sharp, stinging sensation as Colleen's strong right hand swatted my vulnerable hindquarters.

My whole body shuddered, and I tensed up. Colleen took to spanking like a duck takes to water. The pain was staggering, and each blow stung my naked skin more than the blow that preceded it. I writhed and bounced across Colleen's lap, and cries of pain soon escaped my girlish lips.

I arched my back and raised my bottom for Colleen to punish. From the way my bottom was stinging, I could tell my ass was rapidly turning red. I attempted to remain in position across Colleen's lap, however, the pain was so severe that I found myself kicking my legs uncontrollably and writhing with each blow. I cried out in pain and was soon sobbing. I was spanked again and again, Colleen's strong right hand catching the sensitive underside of my bottom near the delicious crease where the lower curve of the buttocks meets the backs of the thighs.

I moaned and squirmed and kicked, but Colleen held me tightly around the waist and kept me from squirming off her lap. She spanked me harder and harder. My breasts heaved, my hips squirmed, and I sobbed and cried out like a poor, defenseless Cinderella being tormented by a wicked stepsister.

Then, while I was still sobbing, Colleen stood up and I was ordered to kneel and place my face between her legs so I could lick her to orgasm. Colleen claimed not to be a lesbian, however, she immensely enjoyed having my tongue lap at her vagina and her swollen clitoris sucked into my mouth. She moaned and gasped in libidinous appreciation as I ushered her into orgasmic bliss.

Tricia took photos of the whole thing and opined that my reddened ass, my humiliating defeat as I struggled against Colleen's wrestling holds and me performing cunnilingus while on my knees was "magical" and "bewitching" and that she hoped to be invited back if Lyndsay planned to do amazing stuff like this with me again.

Of course, the very next day Lyndsay invited both Colleen and Tricia to play some more. We basically did exactly the same stuff as before. First, we swam, then Colleen and I had a rematch, which I lost. Colleen obviously had some sort of training in wrestling and I never had a chance.

"Do I have to get spanked again?" I asked, already knowing the answer, but feeling obligated to ask. It seemed like the sort of thing Cinderella would ask before being punished by one of her sadistic stepsisters.

"You know the rules," Lyndsay said, "the loser gets spanked. There's no way of getting around that."

"When do I get to spank her?" Tricia asked. She looked me over enthusiastically, and then her eyes darted in Lyndsay's direction.

"When you beat her in some sort of athletic competition," Lyndsay replied adamantly. "There are rules and ancient traditions that need to be followed, and you haven't even challenged Gwen to anything yet."

The traditions Lyndsay was referring to were only a few days old, but nobody was willing to argue with her. Rather than contradict Lyndsay, Tricia challenged me to a game of soccer.

"The first one to score a goal wins," Tricia said, "The goal line for me will be there, the goal line for you will be there."

I had never played soccer before, however the rules seemed simple enough. You kicked a ball and chased after it. I had strong legs, I could kick, and I could run exceptionally fast. It was possible I could win this time.