In Chapter One, Walter met his summer neighbors at Pond Cove, a secluded area surrounded by a government nature preserve. By the end of the day, he had lost his clothes, his pride, and his virginity.
In Chapter Two, Walter continues telling the story of his Summer at Pond Cove. He finds out for certain that he is a pain slut, and is officially given the name of “weird worm” at the feet of his new Mistress… Mistress Gloria.
This story stands on its own, but may make a little more sense if you have read Chapter One.
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WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain strong or even extreme sexual content. All people and events depicted are fictional and any resemblance to persons living or dead is purely coincidental. Actions, situations, and responses are fictional ONLY and should not be attempted in real life.
If you are under the age or 18 or do not understand the difference between fantasy and reality or if you reside in any state, province, nation, or tribal territory that prohibits the reading of acts depicted in these stories, please stop reading immediately and move to somewhere that exists in the twenty-first century.
Archiving and reposting of this story is permitted, but only if acknowledgment of copyright and statement of limitation of use is included with the article. This story is copyright (c) 2018 by The Technician.
Individual readers may archive and/or print single copies of this story for personal, non-commercial use. Production of multiple copies of this story on paper, disk, or other fixed format is expressly forbidden.
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I don’t know how I ended up being a twenty-three year old virgin. It wasn’t that I didn’t try to lose my virginity. It was just that every try ended up in disaster. To use the old baseball analogy, somewhere between first and second base I always got tagged out… or fell… or just turned and ran for the dugout.
I had several different fantasies about what my first time would be like. Some of those fantasies had me seducing a voluptuous movie star. Some had me taking one of my nice looking college classmates to an expensive dinner and then back to my bed. And some of those fantasies were really weird… I won’t talk about them. But even my weirdest fantasy was not as weird as the reality of being on a blanket with three young, beautiful, naked, submissive girls while three powerful Mistresses sat around us and watched and made lewd comments.
I guess I should say I was with one submissive– and very beautiful– girl on one side of the blanket while two other submissive girls made love on the other half of the blanket. Under any other circumstances, I might have watched cheryl and puddy tat take each other to orgasm.
Actually, I almost did. Cheryl was on top of puddy tat in a scissors position and was frantically rubbing her crotch against puddy tat’s. Her black body was slick with sweat. So was puddy tat’s paler body as they gyrated madly against each other. They were just starting to grunt and moan in earnest when holly reached up and turned my head so that I was looking at her.
“Are you going to watch or fuck?” she asked with a grin.
Holly is truly beautiful. As I looked down at her, her flaming red hair, very pale skin, and emerald green eyes perfectly framed the red lips which were forming a magnificent smile as she looked up at me.
I looked down at her and said, “Uh…..”
How could I tell her that I really didn’t know what to do?
Oh, I knew in general. I knew that my prick went in her cunt. I knew that I should be between her legs– or perhaps behind her. I’d seen some porn videos– OK, I’d seen a lot of porn videos– but just because it’s on the internet doesn’t mean it’s what you should do. Besides, I know that a lot of what they do in those videos is so the camera can see, not for enjoyment.
Holly giggled. “You really are a virgin, aren’t you?” she said with her constant smile.
I nodded and she said softly. “Normally, you should spend some time stroking my skin, slowly stripping off all my clothes, and getting me all turned on, but I’m already naked and very, very wet, so we should get right to it.”
Looking up at Mistress Gloria she added, “Besides, we don’t have much time.”
She reached out and positioned my body between her legs. “Put your hands on the ground on either side of my breasts.” she instructed. “Then move forward so your prick just touches my labia.”
I didn’t move and she added, “That’s my pussy lips.”
I did as she had instructed and felt the tip of Little Bill touch her moist slit.
“Now push in slowly,” she ordered.
I did, but Little Bill just slid down toward the ground.
“Let me put it in position,” she said and reached down to adjust where my prick was. “Sometimes it has to be between my outer lips or it won’t go in.”
“As you get better at this,” she added, “you can reach down yourself if you have to.”
I felt her hand on my prick and then I felt it slide into her slit… and keep sliding in. I had fantasized about fucking a beautiful girl– and had even had a few wet dreams– but my fantasies were never anything like this. I felt like I was inside a warm glove or tunnel. And that tunnel was thrusting up and down on my prick.
My mind was brought back to what I was doing when holly grunted out loudly, “Match my movements, walter.”
I did, and suddenly the sensations became even more intense. As we moved away from each other, it was like she was tightening up on me and pulling on my prick– almost like she was trying to milk me.
Both of us were starting to move pretty fast and I could hear the smack of us slamming into each other as we thrust forward. After a few minutes, I could feel cum starting to boil up in my balls. I wasn’t going to be able to last much longer.
“I’m… going… to… cum,” I grunted out in time with my thrusts.
Holly looked up at me and grunted back, “Three… two… one… NOW!”
I felt like my entire being spurted out into holly’s womb. I know I yelled a little bit as my body shuddered and became very stiff. Holly, meanwhile, screamed out really loud and pulled me down on top of herself. She wrapped her legs around my back and crossed her ankles to lock me in place. Once I collapsed against her body, she wrapped her arms tightly around my chest and squeezed even more tightly.
Holly continued to shake and scream and pull herself tightly against me. It was to the point that I was almost having trouble breathing when she sighed and then slowly relaxed and lowered her arms and legs to the blanket.
She looked into my eyes and murmured softly, “So, how was your first time?”
In response, I just sort of grinned at her. Then I said, “I’ve never felt like that before.”
She laughed a little and replied, “Neither have I, and this wasn’t my first time.”
She grinned at me again and said, “Maybe we are meant for each other.”
“Or maybe,” Mistress Gloria said loudly, “you were both meant for me. You are a perfect pair of submissive pain sluts.”
“I’m not a pain slut,” I said defensively.
“Whoa… oh,” she yelled out. “Little weird worm thinks he isn’t a pain slut.”
“What’s a pain slut?” I whispered to holly.
I must have whispered louder than I thought because Mistress Sam yelled out, “He doesn’t know what it is and he still thinks he isn’t one.”
“A pain slut,” Mistress Tracy began, “is someone who would spurt on the ground just because they were lying across my lap getting spanked.”
Mistress Sam laughed and said, “Like you did, worm.”
“But I was naked,” I protested, “on a naked woman’s lap… and I wasn’t used to that. It wasn’t the pain that caused me to… spurt.”
“We were going to call it quits for the day and eat,” Mistress Gloria said, “but I think we have time for an experiment before supper.”
She slapped her hands together and said loudly, “I’ll bet he goes faster than dweeb dave back at school!”
Mistresses Sam and Tracy yelled in unison, “Paddle time!”
Mistress Tracy then yelled out, “Puddy tat, go get the black ropes.”
“Yes, Mistress,” puddy tat replied as she scampered inside the cabin.
“Over here,” Mistress Gloria said harshly.
As I started to get up, I realized that I was still inside holly. “It must take you a little while to get back to being really small,” she said softly. “I like that.”
I felt Little Bill– who wasn’t so little at the time– slide out of holly’s cunt. I looked down at her as I got up and saw that there was a large puddle of cum between her legs. I didn’t think all that came from me, so some of it must have been her pussy juice, or… “Maybe she’s a squirter,” I thought as I turned to follow Mistress Gloria.
She was standing at the end of the porch pointing at the ground. There was a set of steps on that end and two posts about four feet across, one on each side of the steps.
“Stand between the posts,” she ordered, and I did.
“Facing in,” she added angrily and I quickly turned around.
“Put your feet together,” she commanded, “and then reach up and grab the posts as high as you can.”
I did what she said and stood there in a Y shape, not quite on my tiptoes, while Mistress Tracy wound loop after loop of soft, black rope around my wrists. “I had to leave my leather restraints at home,” she said as she started tying the other end of the rope to the poles, “but luckily I know how to tie a rope restraint that won’t cut off circulation.”
After she had both arms pulled tight, Mistress Sam stepped up and shoved her foot between my legs. She then pushed my right leg out and kept pushing until my foot was up against the post. By the time Mistress Tracy had that ankle secured to the post, I had already moved my left foot over to the post… almost. I didn’t quite stretch that far.
“We need to have you do some stretching exercises,” Mistress Sam said with her deep chuckle. “You body is way too stiff.”
She then pushed my foot out until it touched the post. As Mistress Tracy tied that ankle to the post, I could feel things stretching in my groin. My arms were also pulled very tight and I could feel the muscles stretching in my shoulders.
When Mistress Tracy was done, she stepped around in front of me and said, “And THAT is how to properly restrain someone in a tight X.” She shook her head slowly and said, “Some people insist on doing the feet first, but the right way is to do the hands first. Then, the weight of the body helps stretch you tight.”
“Are you tight, worm?” Mistress Sam asked.
“Yes, Mistress,” I quickly replied. It was the truth.
“Now,” Mistress Gloria said ominously, “this is how this is going to work.”
She pointed to the blanket still spread on the floor of the porch and said, “Our regular little subbies are going to kneel here on the porch in front of you in the rest position.”
She pointed to the wooden chairs and said, “Mistress Tracy and I will sit behind them and observe.”
Stepping up right in front of me she gave me a twisted grin and said, “That leaves Mistress Sam to whap your ass with one of the paddles.”
“Puddy tat!” Mistress Tracy yelled, “go get the long paddle.”
As puddy tat was hurrying inside, she added, “… the wooden one.”
I suddenly felt tight in my stomach as well as my muscles. I had never been spanked before… well, unless you count on Mistress Tracy’s lap. But that wasn’t really a spanking. I was so turned on she could have done anything to me.
Puddy tat ran back out from the cabin carrying a long wooden paddle. The paddle, itself, was a little under two feet long and about three inches wide before tapering down to a handle that had been slightly rounded and wrapped with leather for a better grip. She knelt on the floor and held the paddle out on both hands to Mistress Sam almost as if making an offering to a goddess.
Mistress Sam took the paddle from puddy tat’s open palms and slowly began smacking it against her palm. “Except for the most complete pain slut,” she said slowly, “you have to be a little turned on to begin with or this is just pain.”
She stood in front of me and said, “You’ve gotten used to seeing us all naked so you have finally reverted to your concealed size.” After a laugh, she asked, “What do you call your prick, worm? I can’t just call it worm’s worm… or maybe I can.”
“I call it Little Bill,” I blurted out. Then I sputtered, “But I never say that out loud.”
“OK,” she laughed and then turned to holly and said, “Fluff him. Just enough to wake up Little Bill. We don’t want it turning into Big Ben until later. Got that?”
“Yes, Mistress Sam,” holly replied loudly.
She then crawled forward until she was kneeling directly in front of me. She reached out and stroked my stomach and I groaned softly. Then she stuck out her tongue and flicked the very tip of my penis. Little Bill must have been peeking out at least a little because I could feel it on most of my glans. She then opened her mouth and slid it down over my prick. I could feel her tongue slowly slurping against the bottom of the shaft as she suckled on me.
“That’s enough!” Mistress Sam yelled and holly quickly jumped back from me and returned to her position on the blanket.
“This is a scientific experiment,” Mistress Tracy said as she stood in front of me, “so we are going to us the Peter Meter scale to measure whether or not worm here is turned on by pain.”
She laughed and said, “Or maybe we should call it the Little Bill Meter in worm’s case.”
She reached out and lifted my prick slightly with her hand. “We will call this zero on the angle of the dangle scale.” She laughed again and added, “If it gets to ninety degrees, we will know that worm here is a certified pain slut.”
As she held my prick, the peter meter moved a little off zero, and someone called out, “Things are stirring.”
The sudden flood of humiliation as I fully realized that I was now willingly standing naked tied between two posts in front of a bunch of naked women, ready to be paddled, caused the peter meter to firm up an additional notch or two, but dangle remained close to zero.
Mistress Sam stepped behind me and stroked my ass a couple of times. I twitched away from her touch, and she laughed lightly and said, “That is just to enhance the sexual nature of what I am going to do.” Then looking at Mistress Gloria, she added, “Besides, he has a really nice ass.”
I was just starting to ask myself once again what in the hell I had gotten myself into when suddenly there was a loud smack and fire erupted into my body through my ass cheeks. Mistress Sam had slammed that paddle against me with all of her strength.
“That was just to get your attention,” she said. She then began working over my ass like an expert. She would spank relatively softly for a few strokes then really lay one on. She would vary the tempo from several right in a row to long pauses that almost made me wonder whether or not she had stopped. Sometimes she struck from the right and then she would evidently swing the paddle like a sword to backhand my ass and come in from the left. She made it impossible to anticipate what was going to happen next.
I could feel the intense pain. This wasn’t at all pleasurable! Then I remembered what I had done and what had happened on Mistress Tracy’s lap. I closed my eyes and “went into the pain.” I think that’s the term they use on the porn sites. No, I don’t know what that means or exactly what happens, but evidently when you stop avoiding the pain, but rather embrace it, everything changes. It is almost as if a switch is thrown that takes the pain impulses off the pain track and sends them down the pleasure track.
I gave myself to the pain, and after a moment or two, the switch threw. The pain train was now roaring down the pleasure track and heading uphill at full steam. Suddenly Mistress Sam stopped everything. I don’t know how many swats she had given me at that point, but I do know that the peter meter was reaching well above 90 degrees. Little Bill was almost looking at the ceiling of the porch.
She stepped around me to look out at the group that had gathered on the floor to watch. “My God, holly,” she cried out, “your eyes are glazing over. You are really getting into this.” She then said in an almost little girl sing-song voice “We just might have more than one perfect pain slut with us tonight.”
She moved to stand directly in front of holly and said, “Or is it just that he is your perfect pain slut match?”
I opened my eyes and saw holly kneeling sitting on the floor in front of me with the other girls. Everyone turned to look at her, and she scrunched herself lower as she mumbled softly, “No, I…. uh….”
Mistress Gloria got out of her chair and walked over to her. “Holly,” she began, “you can kneel and deny what you are feeling or you can stand up and show us just how turned on this is making you.”
A suggestion from a Mistress is actually an order, but holly remained kneeling. Then, after what seemed like several minutes of absolute silence, she slowly stood up. As she stood up it was obvious to everyone that she was very wet between her legs. In fact, there was so much moisture dribbling down her legs that it almost looked like she had peed herself.
“Go over,” Mistress Gloria continued, “and loop your hands over his neck so you are standing there face to face. That will allow us to smack both of your asses at the same time while you press your bodies together.”
Holly’s eyes were definitely glazed over as she came over and stood in front of me and looked up into my eyes for several moments. Finally, she reached up and clasped her hands behind my neck and pulled herself tightly against me. As she did so my penis was forced upward between us and pressed against both our stomachs. Even though I couldn’t see it, I was pretty sure at this point that the peter meter was only a little below 100 per cent.
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“Puddy tat!” screamed Mistress Tracey, “we need a couple of ping pong paddles.”
Puddy tat jumped to her feet and ran into the cabin. When she returned she scurried over to Mistress Gloria and handed her one paddle. She then ran to hand the other paddle to Mistress Sam.
“Take the long paddle back into the cabin and put it away,” Mistress Tracy said firmly and puddy tat ran back into the cabin with the long wooden paddle.
“Your serve,” Mistress Sam said with a laugh and Mistress Gloria slammed the paddle into holly’s ass.
The two mistresses were standing slightly to the side of us so they could swing the ping pong paddles most effectively. It was obvious that they had worked together like this before. They seemed to know what the other was thinking. Sometimes they would both strike at exactly the same time, sometimes they would alternate with Mistress Sam striking me and then Mistress Gloria smacking holly. Sometimes they would even time it so that one paddle would strike just ahead or behind the other.
I am not exactly sure when we started, but both holly and I began to press and rub against one another as our bodies were driven by the paddles. My peter meter was no longer visible, but there was no doubt in anyone’s mind that I was very turned on. There was no doubt about holly either. Her moans and cries soon filled the air. Then suddenly she pulled herself upward by her arms, wrapped her legs around my waist, and lowered herself down on my prick.
The mistresses took that as a cue to change their paddling to a continuous rhythm of first holly and then me, driving us back and forth. We rocked back and forth to the rhythm, feeling the sting of the paddle and the pleasure of intercourse until holly and I exploded in a mutual orgasm.
Mistress Sam and Mistress Gloria immediately stopped paddling and holly and I clung to each other in a sweaty embrace.
“Well,” Mistress Sam said loudly from behind me, “I don’t think there is any doubt that weird worm here is a masochist.”
“And I don’t think that there is any doubt,” Mistress Gloria added, almost laughing, “that there is more than maschocism and submission going on here.”
She walked up and stroked holly’s back lightly and said, “We seem to have a pair of love birds.”
For some reason that caused holly to bury her head against my shoulder, turning redder and redder and redder with embarrassment. As Mistress Sam came back onto the porch to join the others, holly continued to bury her face in my shoulder as she hung from my neck, supporting herself with her legs wrapped around my waist. My now deflated penis was still buried inside her.
Mistress Sam came over to us and also laughed slightly, “When you are ready, holly,” she said, “just pull yourself up off of him and let yourself slide back down to the ground.”
Looking me directly in the face, she added, “Then I’ll get you untied so you can go home… or whatever.”
Holly quickly lifted herself up to pull Little Bill totally out of herself and slid down the front of my body. She then hurried to kneel with her sister slaves on the blanket.
“What if I don’t want to go home?” I asked as Mistress Sam and Mistress Tracy were untying the ropes.
They both looked at me with really weird looks on their faces. I didn’t know if they were upset or surprised or just curious.
As soon as I was free, I stood on the porch in front of all three Mistresses and sputtered out, “I’ve got to check in with my family every night on Skype or they get worried, but that is just a two or three minute call. I could run back and make the call and then paddle back here in one of the kayaks after that.”
“Let me get this clear,” Mistress Gloria said slowly. “Are you saying that you want to come back here to be our little worm slave, or are you saying that you want to be with your new-found love-slave, holly?
I looked down at my feet. I could feel myself getting redder and redder and redder. Finally I blurted out, “Yes, Mistress Gloria.”
“Yes what?!” she replied harshly. “Do you want to be my slave or do you want to be with slave holly?”
“Both,” I said softly.
Mistress Sam laughed very loudly. “Well, Gloria,” she said, “it looks as if you have a slave couple to play with.”
“Only if I’m willing,” Mistress Gloria said firmly. “And only if slave holly is willing to have the weird worm as her partner.”
She looked over at Mistress Sam and said, “Remember, all of this is consensual at all levels. One safe word and they”– pointing at the three girls still kneeling on the porch– “walk away.”
Mistress Gloria motioned for holly to come over and she jumped to her feet and hurried over to stand beside me.
“Do you love him?” Mistress Gloria asked.
Holly nodded her head up and down vigorously.
“Use your words, slave,” Mistress Gloria said firmly. “Do you love weird worm?”
“Yes, Mistress Gloria,” holly replied, “I love weird worm.”
“And you,” she said, pointing at me, “do you love slave holly?”
“Yes, Mistress Gloria,” I almost shouted.
“There’s one more thing,” Mistress Gloria said and then pointed down at the floor in front of her feet.
I didn’t know what she wanted, but holly dropped to her knees and bowed down very low so that her head was almost touching the wooden floor. Her hands were extended out in front of her so that she was almost touching Mistress Gloria’s feet. I quickly copied what she had done.
“You learn fast, little worm,” Mistress Gloria said. Then her voice changed. She almost sounded like she was standing in front of a classroom as she explained, “What we are going to do now is called an act of submission. I won’t put a collar on you… yet, but what you are doing is proclaiming to the world– and to yourself– that you are my slave. Do you understand that?”
“Yes, Mistress Gloria,” I said. I tried to sound confident and secure in what I was saying, but I could hear my voice quiver.
“Holly,” she continued, “tell him what to say. … And you, worm, just repeat what she says, only louder.”
“Ready?” holly asked softly.
“Um hmm,” I answered, nodding my head even though she couldn’t see me.
“I, Walter,” she whispered.
“I, Walter,” I said loudly. Then I followed her whispered words as I proclaimed, “I, Walter, willingly submit myself to you, Gloria, as my Mistress and give you complete control over my actions and my body for as long as I remain your slave.”
“I accept your offer of submission,” Mistress Gloria said, “and I officially give you the name ‘weird worm’ as your slave name.”
She then paused and asked, “What shall be your safe word?”
When I didn’t answer for a long time, she said in her school teacher voice, “A safe word is something you say to stop whatever is going on. There are a few other uses for a safe word, but we can get into that later. Do you understand that?”
“Yes, Mistress Gloria,” I answered without raising my head.
“Your safe word,” she continued, “should be a word or phrase that you would always remember, but would not be likely to say accidentally. Or at least, it would be obvious that you weren’t meaning it to be your safe word if you used it in normal conversation.”
Suddenly I could hear… and see… a phrase in my mind. “Uncle Walter,” I called out. “Uncle Walter will be my safe word.”
“Now one more thing,” Mistress Gloria said, “and you both need to answer this together. Do you, as a couple, submit yourself to me as fully as you have submitted yourselves individually?”
“Yes, Mistress Gloria,” holly and I replied together.
“I now pronounce you husband and wife,” Mistress Gloria said with a laugh. As the other two mistresses joined in her laughter, she added, “… though I’m really not sure which is which in this particular arrangement.”
“Let’s eat,” Mistress Tracy said. “There’s almost a full moon tonight, so after supper you will be able to walk the beach to get back to your cabin.”
“And you can take holly with you,” Mistress Gloria said, “so that each of you can tow back extra kayaks.”
“All holly’s Uncle Cornelius left here,” added Mistress Tracy, “are some fiberglassed plywood canoes from the 60’s. Each of them is big enough to hold all of us, but they weigh a ton.”
“Just don’t be taking time for any monkey business on the beach before your come back,” Mistress Sam said harshly.
She really didn’t need to warn me about that. I had already cum three times today. I wasn’t sure I wanted to– or could– go for four. Though as I thought about it, Little Bill started to stir slightly.
“You four slaves get inside and prepare supper,” Mistress Gloria ordered with a clap of her hands. “And in honor of this special occasion, you may eat at the table with your Mistresses.”
“Thank you, Mistress Gloria” I immediately replied. It wasn’t until I started into the cabin that I realized that I had said that exactly in unison with holly, puddy tat, and cheryl.
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END OF STORY (For now. Further chapters may follow.)
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