BDSM Story – The Case of the Undercover Dick – Part 2 A Dan Diamond mystery by j.
Did you ever play a parlay card? Probably. Just about anyone who likes making a bet now and then has blown some money on a parlay.
It’s not that great a wager, but it holds out the irresistible dream of a big killing. You know how it works. The card lists all of a day’s top games in some sport — college football, pro hoops, a mix sometimes, whatever — and the bettor has to pick three winning teams or more to cash in. Any misses at all, and he loses. Of course, the more games you try to pick, the bigger the payoff, but the odds of winning are pretty terrible when you go for the big numbers. It can be frustrating to hit on, say, five games and then see the sixth — the one you thought you had a lock on — go down the toilet.
What’s that got to do with Mrs. Stern’s blackmail problems? Well, the half-ripped parlay card that I had just retrieved from under a bush by her front veranda turned out to be very interesting if you were looking for a reason why somebody on Mrs. S.’s staff needed cash badly enough that he or she would risk slipping information to the blackmailer.
Whoever had played the card had tried to pick ten winners. This is not smart. I’ve tried to pick that many myself, but only for the fun of it — risking a couple of bucks or maybe a fiver. But this card had a big “500” in the wager blank. No one puts five hundred dollars on a 10-team parlay unless they are an idiot or very, very rich or an addicted gambler deep in debt and trying desperately to hit a big winner. My bet was on that last possibility — that someone who worked for Mrs. S. had a very large gambling problem.
I wouldn’t have even found the parlay card if Ms. Davis hadn’t decided to punish me with a night out on the veranda, hogtied and naked. When I got back to the room I shared with Delia and Donna after my very strange session with the middle-aged broad who liked having her artificial penis sucked, Ms. Davis — a.k.a. the Dragon Lady — was waiting for me.
“You were very late to dinner this evening, Dorothy,” she said.
That wasn’t my fault, of course. I was tagging along with the fake-dick lady, the client who owned me for the evening. She was the one who was late. But I didn’t try to argue. I knew that the Dragon Lady wanted a piece of my ass for some reason, and I might as well let her get it over with, so I kept my mouth shut and hung my head. Maybe contrite would work, though I used to try that with Sister Mary Agnes, and it didn’t fly then either.
“If you don’t have anything to say for yourself,” Ms. Davis said, “I have no choice but to punish you. Please remove all your clothing.”
There wasn’t anything to the skimpy maid’s outfit except the dress and the lingerie, but I took my time taking them off, fumbling with the garter clips and balancing on one foot and then the other to remove the silk stockings. Delia and Donna sat on their narrow beds watching but being careful not to let Ms. D. catch them staring. As the staff submissives, they had probably seen this scene acted out many times.
Naturally, I had an erection by the time I was standing naked in front of them. I thought that would piss off the Dragon Lady, but she didn’t say anything about it. She had a small black satchel sitting on the floor beside her, something like a doctor’s bag, and she pulled out a short piece of rope and tied my hands tightly behind me. Then she told me to follow her and walked briskly out the door. As I left, I glanced back at Donna and Delia. Donna grinned and gave me a thumbs-up sign. He seemed to regard all this bondage stuff pretty lightly, but I guess any guy with a foot-long hotdog tends to take the optimistic view.
Ms. Davis led me out to the front porch — the veranda when it’s on a house the size of Mrs. Stern’s mansion — and told me to lie down on my belly. That wasn’t easy with my hands tied behind my back, but I managed. She tied my ankles together, brought them up over my butt and tied them to my hands in the classic hogtie position. When I was tightly packaged, she pushed me over onto my side, pulled a dozen clothespins from her little black bag and clipped them onto my nipples, my dick and my balls. They hurt a lot, but not nearly as much as they did when she rolled me back onto my belly, trapping the clothespins and my rigid erection between my naked body and the cold concrete floor of the porch.
“Sleep well,” she said, and then she left.
I didn’t now how I was going to escape a chilly, very uncomfortable night on the porch, but I knew that I had to do something about those clothespins right away. I rocked myself from side to side. It hurt like hell as I rolled back and forth on the clothespins, which pulled at my nipples and pressed painfully into my genitals, but on about my fourth try, I flopped over onto my right side.
A lot of the clothespins had been knocked off during my struggling, but there was still one pinching my left nipple, several on my balls and one really annoying one on the head of my dick. I lay there wondering why I had taken this job. Long minutes passed. My skin went numb where most of the clothespins were fastened, but the sharp pain from the nasty one on my penis persisted. Strange as it may seem, my erection persisted, too.
Where I was lying, my head was a few feet from the edge of the porch, and my only view was the ground under the first of a row of bushes that ran along the front of the house. The bush was next to the winding walk that led up to the porch, and I noticed that someone had dropped a key there. There were several scraps of paper, too, and one of them was that parlay card, ripped halfway through. I didn’t have much to occupy my time, lying there on the porch and getting colder by the minute, so my thoughts focused on the betting card. I was close enough to tell what it was, and I wondered whether the owner had had a winner. Apparently not, if he tore in partly in two and tossed it away.
I didn’t know how long I’d been lying there — though it seemed like a very long time — when I heard someone come onto the porch. Whoever it was began untying the ropes.
“Freezing your balls off, pardner?” Donna said.
“Pretty close,” I said. “Aren’t you going to get in trouble doing that?”
“No way,” he said. “Ms. Davis told me to come out and untie you after an hour.”
“It’s only been an hour!” I said, astonished.
He laughed. “Seems like a lot longer when there’s a clothespin on your dick, doesn’t it?” he said.
“I thought I’d be here all night,” I said.
“Don’t worry,” he said. “Ms. Davis may be a cunt, but she’s not going to let a paying customer lie outside all night and get pneumonia.”
It had slipped my mind for the moment that the staff at Mrs. Stern’s House of Pain and Suffering — my name for it, not hers — thought that I was a submissive client, in town for a fun weekend of agony and humiliation. A real Santa Barbara vaction — beaches, boutiques and butt whipping.
Donna finished unfastening my wrists and ankles. He didn’t offer to remove the clothespins, and I preferred to do that myself. They always hurt worse when they come off. Man, do they hurt! I couldn’t help cursing when the one came off my dick, and Donna winced.
“Anyway, thanks for untying me,” I said. “My real name is Dan, by the way.”
“I’m Darrell,” he said, “and I hear so many jokes about ‘my other brother Darrell’ that I almost prefer Donna.”
“I can always go with that,” I said.
“Probably better,” he said, “because if you slip up and call me Darrell in front of Ms. Davis or Mrs. Stern, your ass is going to be grass again. Mine, too.”
“Okay,” I said, “keep it Donna and Dorothy then.”
We went back into the house, but first I reached under the bush and picked up the parlay ticket. I was curious whether or not it was a winner. Donna led the way back to our room, and I couldn’t keep from thinking that his bottom looked pretty good in the short skirt of his uniform. If I stayed on this case much longer, there was no telling what it was going to do to me.
I glanced down at the parlay card while we were walking. My first thought was that the guy who played it must be an idiot for making ten picks, and then I noticed the amount of the bet. My mom didn’t raise a complete fool, so the old brain cells kicked in. The person who filled in this card was either a lunatic or very desperate for money. Maybe both.
“Wish there was a newspaper around here,” I said to Donna’s back. “I had a hundred down on the Dodgers Thursday night, and I don’t know how it came out.”
“Beats me,” he said.
“You a betting man?” I asked. (Notice how the astute private investigator displays an enormous subtlety in his interrogations?)
“Not me, dude,” he answered. “My dick and I work too hard for our money to blow it in Vegas or at the track.”
“I was hoping there would be someone working here who would know where I could place a bet on a game tomorrow,” I said.
“I don’t know who that would be,” Donna/Darrell said. “We do have one regular client who’s a mob guy or something from L.A., and he’s always phoning in bets when he’s here. But he hasn’t been to the mansion in six or seven months.”
If the wiseguy hadn’t been to Mrs. Stern’s spank-and-thank bordello for a while, the card hadn’t been filled out by him, because the games on the card were played only a week ago. It must have belonged to someone who was keeping their gambling habit a secret.
When we got back to the room, I got a nice surprise. Delia was sitting on her bed naked. That figured, because the only clothing that Mrs. Stern allowed her submissives — clients and staff members alike — were their maid uniforms. You couldn’t wear those to bed, or they’d end up very wrinkled. That had to be a no-no.
“Did she put those clothespins on you?” Delia asked.
“Afraid so,” I replied. “Not much fun either.”
“You ought to see how it feels when she puts one on your clit,” she said.
“No thanks,” I said, “but I can imagine.”
“No you can’t,” she said. “You really can’t.”
Donna/Darrell took off his uniform, too, and hung it carefully on one of the clothes hooks. There we were, just a bunch of naked folks sitting around talking. But D/D apparently wanted to call it a night. He crawled into bed, pulled the thin sheet over himself and rolled over with his face to the wall. Delia and I sat there staring at each other. How do you make small talk with a naked submissive?
“It’s a little hard to get used to sitting around without your clothes on,” I said.
“Oh, I don’t know. It’s not that bad,” Delia said. “When you’ve got a roommate who’s hung like Darrell, it sort of improves the scenery.”
I glanced over at his bed to see what his reaction would be to that comment, but he’d apparently gone immediately to sleep.
“For you, I guess,” I told Delia. “But it tends to give another guy an inferiority complex.”
“I wouldn’t worry,” she replied. “You’ll get by in that department. But doesn’t your thing ever go down?”
“It’s had a lot on its mind today,” I said. “Besides, Clyde tends to perk up when I’m chatting it up with a pretty lady who forgot her undies.”
She smiled at that but didn’t say anything. We sat there silently for a few minutes more.
“It gets cold in here at night with just a sheet for covers,” she said at last. “Want to share my bunk so we can keep warm?”
“Don’t mind if I do,” I said.
After a long day of very kinky stuff, straight sex in the good old missionary position felt pretty nice. Delia apparently thought so, too, because after we had been going at it for a while, she started making a lot of noise.
“You’re going to wake up Darrell,” I told her between thrusts.
“I’m already awake,” came the voice from the next bed. “But don’t worry about me. I promise not to watch.”
Knowing that Donna/Darrell was listening didn’t seem to bother Delia. Didn’t bother me much either by that point, and there was a lot of grunts and groans from both of us as we wound things up in very satisfactory fashion. We fell asleep immediately, and we didn’t wake up until the light in the ceiling came on and someone hit the bottom rail of the iron bed with a hard object.
“Shameless!” the someone shouted.
My blurry vision came into focus on a tall blond woman standing at the end of the bed. She was a Scandinavian type, probably in her mid-thirties, and she could have been very attractive if it hadn’t been for the frump-cut gray dress and the severe bun of her hair. She was pretty attractive anyway, if you happen to go for Hitler Youth pinup girls. The only staff members that I hadn’t met were Mrs. Hudson, the housekeeping czarina, and Martha Karr, the cook. This had to be the divine Mrs. H.
“Get out of that bed immediately,” she screamed, smacking her riding crop on the rail again.
We scrambled out of bed and stood there blinking at her. We were in deep doo-doo this time for sure. She drove us naked out of the room and down the hall to the back door, slashing our buttocks with the riding crop to hurry us along. The sun was coming up when we got out on the back lawn, but it was still very chilly, and Delia and I were shivering more from the cold than from fright.
In the middle of the lawn several large iron stakes with rings in their ends had been driven deep into the ground, and chains with real honest-to-god manacles on their ends were attached to the stakes. Mrs. Hudson manacled each of us by an ankle, gave us each three more sharp strokes with the crop as a parting gesture and went away around the corner of the house. I wondered where she was going, and I quickly found out. The lawn sprinklers came on. In a few seconds, we were soaked and shivering so hard that our teeth were chattering. Delia looked miserable, with her hair plastered down her head and her lips and nipples turning blue, but she grinned at me.
“Was it worth it?” she asked.
“You bet,” I said.
After a while, the sprinklers stopped, but it was still cold sitting there on the wet grass. The sun climbed higher into the sky, and it got a little warmer. Then the back door opened. Mrs. Stern and several of her guests walked out onto the lawn, coffee cups in hand, to have a look at the bad little girl and boy — or the two bad little girls if you went by Mrs. S.’s nomenclature. Mrs. Stern surveyed us sternly. (How else?)
“I’m very disappointed in both of you,” she said. “Dorothy is new to our little family, which may be some slight excuse, but you should certainly know better, Delia.” She paused to see if we had anything to say for ourselves. We didn’t. “Since neither of you seems to have a great deal of self-discipline,” she continued, “I’ve asked Ms. Davis and Mrs. Hudson to provide some special instruction that may be helpful in increasing your obedience. We’re all looking forward to seeing your training.”
Right on cue, the Dragon Lady and the Norwegian Nightmare emerged from the back door, smacking their riding crops lightly against their leather-gloved palms in that time-honored promise of punishment to come. They unfastened Delia and me from the stakes and drove us toward the back of the grounds, with the coffee klatch trailing us in anticipation of a little early-morning entertainment. There were several outbuildings on the far side of the large back lawn, including one long, low structure that looked to me like a stable. The original owner probably kept horses, but I had a strong suspicion that there were no four-legged creatures living there under Mrs. Stern’s regime.
I was wrong. When we turned the corner of the low building and looked down a wide alleyway between rows of stalls, I stepped in a mound of something that I realized was unmistakably fresh horse shit. And there was the nag himself in the first stall, head hanging over the door to see whether we’d brought along his morning oats.
But then I was right, too. I wasn’t expecting any horses because I thought that Mrs. Stern had probably converted the stable to a home for her clients with some very special fantasy-fulfillment requirements. And there was indeed one of those in the second stall — a naked young woman, lying on a skimpy bed of straw spread across the earth floor, her face and body grubby with dirt and her dark hair flecked with wisps of straw. She got up onto her hands and knees, lowering her head and staring at the ground like a well-trained plow horse waiting for its harness.
There were a number of harnesses hanging on nails between the stalls, but they proved to be for two-legged beasts, not plow horses. Ms. Davis and Mrs. Hudson pawed through them until they found the ones they liked, and then they began buckling them onto Delia and me. The tangle of leather straps went around our upper bodies, holding our arms tightly in place behind us, and there were large rings on either side of the harnesses where the shafts of a cart could be attached. Wooden bits were pushed into our mouths and fastened around our heads with leather cords. Reins hung from small rings at the end of the bits.
We were now ready to pull the light, two-wheeled pony carts that I saw standing in the aisle of the stable, but the Dragon Lady and the Norwegian Nightmare still had to add the finishing touches. Clamps with little metal bells dangling from them were attached to our nipples, so that they would jingle when we broke into a trot. Mrs. Hudson smiled sweetly at me as she buckled three little straps tightly around my erection, one near the base, one in the middle and the third just under the head. A bell hung from each.
Then came the final indignity. We were bent over and some kind of grease was applied liberally to the rims of our anuses, with Mrs. H.’s finger probing inside me before she was satisfied that I was well-oiled. Ms. Davis stood in front of us to show us the two large butt plugs that were to be inserted in our rectums. A long tail of horsehair was attached to each one. She handed one to Mrs. Hudson, and I felt the hard end of a plug pressing hard against my sphincter and slipping inside. Mrs. H. rammed it home, and I felt as if I’d been skewered by a telephone pole, maybe one with a lineman still clinging to it. There was a loud gasp from Delia, and I knew that she’d just grown an instant tail, too.
Now that the ladies were satisfied with our horsey look, they led us out of the stable and onto the lawn, where the others had been waiting to see the show. In fact, the crowd had grown. I saw most of the people who’d been at the dinner table the night before. Mrs. Stern’s kid Walter was standing next to his mom, looking glum, but he brightened at the sight of us.
“Why don’t we have some races?” he asked with such excitement in his voice that you’d have thought he had a grand on the winning quinella at Santa Anita. “We could bet on them!”
Now there was a clue if I ever saw one. Between the hogties and the icy outdoor showers and the session with Samantha, the fake-dick lady, I hadn’t had much time for detective work, but I had been lucky enough to stumble across that very interesting parlay card, and now I had at least one candidate for the person who tossed it away. It looked as if Little Walter was a betting man.
“I’m afraid that these two naughty girls need a great deal more training before they can be counted on for a good performance in a race,” his mother said. “I suggest that we adjourn for breakfast and leave them in the care of Ms. Davis and Mrs. Hudson. When they have been thoroughly instructed, perhaps we can have a competition.”
Walter looked disappointed, but he went along with his mother and the others as they trooped back into the house. The Dragon Lady glared at us.
“I’m going to miss my breakfast because of you two,” she said. “You’re going to be very sorry about that!” She turned to Mrs. Hudson. “I want to give them both a good cropping first,” she said. “Take out their tails so they don’t get in the way.”
Mrs. H. pulled the butt plugs out of us with very audible squishes, and I was relieved for a moment to lose that annoying feeling of an impending bowel movement that you can’t quite squeeze out. But I knew there was worse to come. Ms. Davis bent Delia over and gave her four hard licks across her buttocks, leaving a criss-cross pattern of red welts. Mrs. Hudson grabbed my hair and yanked my head down, too, bending me over for Ms. Davis’ crop. The Dragon Lady gave me six good ones, and when Mrs. H. let go of my hair, I hopped from one foot to the other in pain, with the bells on my bobbing erection tinkling merrily.
They forced us both to bend over once again, and the horse-tailed butt plugs were shoved back in. I could feel the morning breeze on my naked body, and the tightness of the harness holding my arms behind me, and the wooden bit in my mouth, and the weight of the little bells pulling down on my nipples, and the horsehair tail tickling the inside of my thighs, and the thickness of the plug filling my rectum, and the leather straps squeezing my erection, and the burning stripes across my bottom. People paid Mrs. Stern for treatment like this, and I could understand why. It wasn’t a Sunday school picnic, but it sure wasn’t boring. Your brain spun from the assault of sensations, all as erotic as they were painful.
They took us back into the stable, stood us between the shafts of a couple of the little carts and attached the shafts to the large rings on our body harnesses. Then they led us back outside, pulling the two pony carts. They were light, with large wheels, and they were very easy to pull — very easy until Ms. Davis and Mrs. Hudson got into them. They had traded in their riding crops for long buggy whips with little knots of leather on the ends of the lashes, and the Dragon Lady, who had climbed into my cart, flicked me on the right buttock. There was a loud pop, and it felt as if I’d been bitten by a very large and well-toothed horsefly.
As I jerked into motion, I heard another pop. Mrs. Hudson had snapped Delia’s butt, too. And then we were both trotting around the lawn, trying to escape any more cracks from the whips of those wonderful ladies. Of course, we were taking our tormenters along with us, and our bottoms were wonderful targets, bouncing up and down within easy reach. It was much harder pulling the carts with people in them, even a skinny broad like Ms. Davis. Poor Delia had the Norse goddess to haul around. I felt sorry for her, but not too sorry. Better her than me.
They whipped us around the lawn a couple of times, guiding us around in a large circle with the reins attached to the wooden bits in our mouths. When they finally jerked us to a halt, we were both gasping for breath. The two women got out of the carts, told us not to move from where we were standing and walked back to the house. I suppose they were going for their breakfasts. They probably had a big appetite just from watching us work out.
Delia looked at me, trying to grin despite the gag-like bit in her mouth. I could see a large fly walking down her left boob and onto the nipple, and I could swear I saw the breast twitch like the skin of a real horse trying to shake off some biting insect. The flies were honing in on us now, drawn by our sweat and whatever it was that Mrs. Hudson and Ms. Davis had used to grease our assholes before sticking in the butt plugs. I could feel them around my anus, and I wiggled my butt to discourage them. I almost wished that was a real tail hanging down between my thighs so I could use it to swat the damn things. Both of us were shifting from foot to foot now, tryng to escape the biting insects.
I was so miserable that I was actually relieved when I finally saw Ms. D. and Mrs. H. returning, followed by the whole group that Mrs. Stern had taken to eat breakfast an hour earlier. Walter was beaming as he followed his mother across the lawn.
“Can’t we round up some more ponies?” he said as the group stopped in front of us. “It’s not nearly as much fun when you’ve just got two of them to race.”
“An excellent idea,” Mrs. Stern said. “Ms. Davis, why don’t you bring out Donna and Dolores? I believe they’re in their rooms. And why don’t you ask Mrs. Karr to join us, too. She always enjoys a ride with one of our ponies.”
While the Dragon Lady was gone to fetch some fresh victims, some the others took turns trotting us around the lawn. One of them was Sam of fake-dick fame, and while she was taking her ride, she told me not to tire myself out too much because she wanted a repeat performance that night of our earlier session. And having told me to take it easy, she promptly snapped me on the butt with the buggy whip to get me moving faster. I jerked forward, and the horsehair plume flipped up between my buttocks.
“I love that tail,” she said. “Be sure and wear it this evening.”
By the time she drove me back to the others, Ms. Davis had returned with Donna and Dolores. Donna/Darrell didn’t look too worried, which is what I expected from him, but Dolores was clearly terrified. Since she was a submissive customer, and not one of Mrs. Stern’s staffers, this could have been her first experience with the pony carts. She was a tiny little blonde, and I wondered how she could even pull a cart and driver, much less take part in a race.
While the Dragon Lady was gone, Mrs. Hudson had fetched two more sets of harnesses from the stable, and Darrell and Dolores were bitted and buckled up. I guess there were only two plugs with tails available, because the new ponies were spared having something shoved up their buttholes. Walter and another man had wheeled two more carts out of the stable, and Dolores and Donna were fastened to the shafts.
“To make everything fair, I believe we need some sort of handicap for Donna and Dorothy,” Mrs. Stern said. “Mr. Chalmers is a large man, and if he doesn’t mind, I’d like him to drive Donna. And here is Dorothy’s driver now. Thank you for joining us, Mrs. Karr.”
I looked back over my shoulder. Waddling across the lawn was a woman nearly as broad as she was tall. If this was Martha Karr the cook, I thought, she must enjoy her own cooking. The dame must have weighed well over two hundred pounds. Was I supposed to haul this lardass around? She climbed into my cart, and it seemed to sink into the thick grass. I could see that there were going to be real long odds on a Dorothy/Dan victory in the pony-girl sweepstakes.
“I’ll bet a hundred dollars that Delia beats everyone,” Walter said excitedly. “Three times around the lawn, right?”
No one offered to take him up on the bet.
“How about fifty dollars?” he said. “Or twenty? Just to make it more fun.”
Mrs. Stern sighed like any mom whose kid has developed a real bad habit, but there was no other response from the people standing around the carts.
“Doesn’t anyone want to bet?” Walter pleaded.
“I gotcha covered, kid!” boomed a voice from the back of the crowd. “I gotta C-note right here that says the little blond chick beats the asshole with the fat broad on his cart.”
Everyone looked around. This very big guy was standing there, leaning on a cane. He came limping forward.
“Why it’s Mr. Balsemo!” Mrs. Stern said. “This is an unexpected pleasure!”
Walter may have found someone who wanted to cover his wager, but he didn’t look very happy about the newcomer’s arrival. It didn’t cheer me up much either. The last time I saw that big guy he was getting pushed into a squad car by a bunch of L.A. cops, and I was the one who had blown the whistle on him. He made his slow way over to where I was standing in the shafts of the cart, naked and helpless.
“Hey, Diamond! Long time no see,” said Joey Balls.
Coleen is a writer, photographer and film maker at Wasteland and Sssh.com.
Here at BDSMCafe.com, she is editor and curator of this comprehensive library of BDSM fiction, informational articles and other educational features that date back to the early days of the internet in 1996 when the site was first launched.
