BDSM Story – The Case of the Undercover Dick – Part 3
A Dan Diamond mystery by j.
Those college day memories last and last. You can be pushing middle age, or maybe you’re even old enough to have a couple of kids in school yourself, and you still can’t forget what Mary Alice Jones said to you in first-period algebra at the beginning of freshman college year. Of course, if what Mary Alice told you was that she wanted to fuck your brains out after school that day, maybe it’s easy to understand why the memory lingers on.
My most unforgettable moment in those distant days wasn’t that great. I’d surprised myself by making the varsity basketball team as a freshman, and I was obsessed with looking good in the pre-season practices. When I went out onto the court for the first practice, I saw that a lot of other students, including all the cheerleaders, had turned out to watch. Now I wanted more than ever to show up well, because there was the tall blond babe whose little cheerleader skirt I was dreaming of getting under.
The coach started the practice by having us run wind sprints from one end of the gym to the other, and about the second time down the court, I could feel my balls beginning to burn. I wasn’t sure what was going on, but by the third sprint, they were on fire, and I knew that someone had pulled the old gag of putting Redhot into my jockey strap. That was a lineament used to warm up sore muscles, and if it got on tender skin like the testicles, it was like a blowtorch.
I didn’t know what to do. I didn’t want to run off the court when my first practice was just getting under way, but I forgot all about the wind sprints and stood there hopping around and pulling at the front of my shorts to get the jock away from my balls. The coach blew his whistle, and everyone stopped and looked back at me.
“You don’t feel like running wind sprints, Diamond?” the coach screamed. “Why don’t you get down and give me fifty instead!”
I dropped to the floor and began doing push-ups, but the fire on my balls was too much. I jumped up and ran for the locker room. I guess a lot of people were in on the joke, because everybody was laughing, even the coach. And the worst moment of all came just before I went through the gym door. Three of the cheerleaders were there, giggling so hard that they practically had to hold one another up, and one of them was that tall blonde.
I’m happy to report that I later got under her skirt — and into her panties, too — but the recollection of that is pretty faint compared with the memory of the humiliation in the gym. Oh, and one other thing. Don’t ever try to wash Redhot off your balls. Water makes it worse.
Why bring this up now? Well, before Joey Balls was through with me there on the back lawn of Mrs. Stern’s Montecito mansion, I had a very good reason to remember that horrible high school moment. And it had nothing to do with Balsemo’s nickname.
Like I said before, Mrs. S.’s kid Walter didn’t seem happy to see Joey show up unexpectedly, even though he offered to cover the bet that Walt was trying to make on the pony races. As you know, the ponies were Delia, Dolores, Donna (a.k.a. Darrell) and Dorothy (a.k.a. yours truly), all trussed up in leather harnesses that held our arms tightly behind us but did practically nothing to cover our nakedness. Walt had been trying to put a hundred bucks on Delia, but Joey had a match race in mind — little blond Dolores against me. His money was on the blonde, and that looked like a pretty good bet considering that the driver of my cart was Martha the cook, who apparently had never met a meal she didn’t like. The woman was BIG!
“I don’t want to bet on Dorothy,” Walter complained. “That isn’t fair, because I picked Delia first, and if she’s not in the race, I want Dolores.”
I guess the kid figured that Darrell and I were handicapped a little on the long side. I had the cook as my driver, and Mrs. Stern had put this heavyweight guy named Chalmers in Darrell’s cart. Dolores only had to haul around skinny Ms. Davis, and Delia’s driver was the same young girl who had been tormenting her at the dinner table the night before. The chick was just a little bit of a thing.
“No problem,” said Joey when Walter started whining. “You don’t want to bet on the private dick, I’ll take him. It’s the action that’s the big thing. You oughta know that, Wally!”
Walter’s mouth dropped open. “Dorothy is a private detective!” he said.
Joey Balls had blown my cover, and everyone was staring at me. Mrs. Stern, who must have been worried that the next step would be someone figuring out that she’d hired me to go undercover, jumped in quickly.
“As you are aware, Mr. Balsemo,” she said, “when our guests come here, they leave their everyday identities behind them. We are only concerned with the roles they wish to play here — dominant, submissive, whatever they choose — and we have no interest in their outside life. It is not our business. I would think that you of all people would understand this policy.”
Joey is a very big guy. If they were looking for stand-ins for the Incredible Hulk, he could probably get the job hands down. But he was obviously cowed by Mrs. Stern.
“Yeah, right,” he said. “I was outta line, like. Sorry, Mrs. S. It won’t happen again.”
“Thank you, Joseph,” she said. “I think that’s wise.”
“Anyway, Wally,” Joey said. “You want the blond dame against Diamond — or whatever you call him? Dorothy?”
The offer of a bet that looked like a sure thing got Walter’s attention off my profession and onto how much he could score off Joey. He brightened up immediately, and you could almost see the dollar signs whirling around in his eyeballs. His mother didn’t look as if she was too happy about the betting talk, but she didn’t say anything.
“I don’t have any cash right now,” Walter said, “but you know I’m good for two hundred bucks.”
“Sure,” said Joey, “I’ll take your marker anytime, kid.”
Walter was eager to get the match race under way, but Joey said he wanted to walk me around a little to “check out his gait.” He politely asked Mrs. Karr to get out of the cart for a few minutes and helped her as she struggled out of the little sulky. Then he led me back toward the stable. When we were out of sight of the others, he stopped and took the bit out of my mouth.
“You here for the reason I think you are?” he asked.
“That’s hard to say, Joey,” I answered, “because I don’t know what you think.”
“I’m up here because a little bird told me that someone has been trying to stiff Mrs. Stern’s customers by threatening to rat on ’em,” he said. “They haven’t got around to me yet, and I wanta make sure they don’t. I figure maybe Mrs. S. hired you to check it out, just like Spanky did.”
“The thing with Spanky turned out to be a swindle,” I pointed out. “She was lying the whole way.”
“Yeah, but I don’t figure Mrs. Stern for that,” he said. “I’ve known her a long time, and she wouldn’t mess around with some two-bit scam like this. She makes too much off this joint to risk screwing it up.”
“So who do you figure for the leak, Joey?” I asked. “What about Walter? Looks like the kid has a bad gambling problem and could use the money.”
“No way,” he said. “The jerk is scared to death of his mother. Besides, he’s the little bird who tipped me off that something was going on. He’s into me for a couple of grand, but I don’t mind lettin’ him ride if it keeps me in good with Mrs. S.”
“I’m fresh out of suspects then,” I said.
“Well, if you wanta stay healthy, Diamond,” he threatened, “you better find some new ones pronto. You got a big payback coming for squealing on me to the cops, but I’m gonna give you a pass while you’re trying to figure this thing out.”
“Fair enough,” I said, and I guess Joey decided that our little chat was over, because he put the bit back in my mouth.
He walked over to a shelf on the stable wall, took down a large plastic bottle and poured some of the contents out into his hand. He came back to me and rubbed the thick liquid onto my welted bottom. Immediately, it began to burn, and I hopped around between the shafts of the cart, making noises through that wooden gag.
“Looks like this stuff is the ticket,” Joey said. “If they use it on the nags to help ’em run faster, I guess it will work on an asshole private dick.”
He reached down with one hand and popped the butt-plug horse tail out of my anus. He coated it with the liquid remaining on his other hand, and he was grinning when he shoved the plug back between my buttocks. The noises I’d been making went up about a hundred decibels.
“Try that up your ass, smart boy,” he said. “I might give you a pass on breaking your legs, but that don’t mean you get off with nothing for rattin’ on me.”
The high school memory of the Redhot in my jock strap flashed through my mind, and then all I could think about was the fiery poker that had been shoved up me. Joey jerked my head around and pulled me out of the stable and back onto the lawn. I must have looked like a spooked thoroughbred whose handler was trying desperately to guide him into the starting gate, because my knees were pumping and my butt was twitching. I was high-stepping along like the second line at a New Orleans funeral.
It took all of Joey’s strength to hold me in place as big, fat Martha was helped back into my cart. They got Dolores’ cart lined up next to mine, and even while I was hopping around, I could see that Walter had a sick look on his face after seeing me in action. He already knew that he’d been had by Joey Balls. He could kiss his two hundred bucks good-bye.
“Out to the far end of the field and back two times,” Joey said. “Okay, Wally?”
Joey chanted a “1-2-3” and a “Go!” Dolores took off across the lawn, but Joey didn’t even let go of my harness for a moment, giving the little blond a head start before he slapped me hard on the buttocks to set me off. It took a while to get the cart rolling with Martha on board, but then I was flying low. All I could think about was trying to run away from that butt plug that was roasting my rectum, but it went along for the ride.
I was closing on Dolores by the time we reached the turn, and I passed her halfway down the backstretch. On the second lap, it was a runaway, but I didn’t slow down, and I took the turn so fast the next time that the cart went up on one wheel. Martha screamed and almost fell out. By the time I got back, the burn in my bottom had diminished from molten lava to smoldering embers, but I was still hopping up and down in discomfort. Mrs. Stern gave Joey a sour look and yanked the plug out of my anus.
“I think that we’ll excuse Dorothy from the rest of the races,” she said. “If you would take her to the main discipline room, Mrs. Hudson, perhaps you could tie her over the punishment barrel and let her air out a little.”
I was unharnessed and taken back to the house, where Mrs. H. took me up the back stairs to a large room at the rear of the house. It was as well-furnished with bondage equipment as any of the rooms I’d seen at The Castle in L.A. or the Spitfire Club in San Francisco. The “barrel” that Mrs. Stern had mentioned wasn’t a barrel actually but a kind of curving, wood-slatted box with a round top that a victim could be bent over with his or her butt high in the air. The big blonde tied me over it with my legs spread wide.
“Your asshole is winking at me,” she said with a giggle — it was the closest I’d heard her come to laughing since I met her. “It keeps puckering in and out like it’s trying to breathe. I guess Joey Balls put horse lineament on that butt plug?”
“Either that or I got some really bad chilies at the Mexican joint where I ate on the way up here,” I answered.
“You’ve got a smart mouth,” she said.
“So I’ve been told,” I said.
“Are you really a private investigator?” she asked.
“Joey Balls seems to think so,” I answered.
“I wouldn’t want to be on his bad side,” she said. “It’s hard to believe that a big mean man like that has such peculiar sexual fantasies. If I could tell you about them, you wouldn’t believe it.”
“You don’t have to tell me,” I said. “I already know about Joey’s thing for getting diapered up and pooping in his pants. I met a dame who used to do the diapering.”
“That’s Joey alright,” she said. “I wonder how he’d like a little hot sauce in his diaper sometime? We can be as tough here as our clients like, but putting horse lineament in somebody’s rectum is carrying it too far. That could seriously hurt someone.”
“You’re telling me,” I said.
“Stay right there for a minute,” she said. “I’ve got something that might help.”
She was gone for longer than that, but maybe it wasn’t as long as it seemed. When you’re left alone with your thoughts and a burning butthole, time tends to drag. When she returned, she stood behind me, and I could feel a finger spreading something cool around the rim of my anus and then probing inside. I don’t know what kind of lotion she was using, but it felt good. Things cooled off rapidly. She kept sliding her finger in and out, making sure she didn’t miss a spot deep down inside. Maybe the Norwegian Nightmare wasn’t so bad after all.
“You must like this, Dorothy,” she said. “Your penis is getting hard again.” She pulled out her finger and slapped me hard across my buttocks. “I think you like it too much maybe.”
She rested one hand in the small of my back, leaned over and spanked me a dozen times on my tender bottom. I guess she thought she’d been too nice to me.
“So what’s a detective doing here getting his ass whipped?” she asked. “Is it about that blackmail thing?”
“You know about that?” I asked.
“Everybody knows about it,” she said. “Mrs. Stern told Walter for some reason, and that little jerk can never keep his mouth shut.”
“Wally blabs, huh?” I said.
“Constantly,” she said. “He probably even wrote about it in one of his stories.”
“What stories?” I asked.
“He thinks he’s some great author, and he’s always writing about the stuff that goes on here,” she said. “I don’t think his mother knows about it, because he doesn’t let many people see them — except he broke down and showed one to me once. He even used the real names of some of the clients. He just had initials for the last names, but some of them are pretty well-known people and you could figure out who they were real easy. Like, if he’s writing about a big Hollywood actor and he calls him Brad P., don’t you think anyone would know who that is?”
“You mean THAT guy is a client here?” I asked in amazement.
“No, no! Of course not!” she laughed. “I was just using an example. I wish he was, though. I’d like to have that bare bottom across my knee.”
She may have decided then that she’d told me too much, because she said that she wanted to see the rest of the pony races and that I should stay there and cool off. I didn’t have much choice, so I lay there over the curved slats, staring at the floor and wondering who might come by next to take a shot at my upturned buttocks. Still, there was a new wrinkle to consider on the detecting end of things. Even if Joey Balls was right and Walter was too big a chicken to sell information to the blackmailer, someone might have gotten their hands on his stories and deciphered the names of the clients.
I was so wrapped up in my thoughts that I didn’t know someone else had come into the room until I felt another finger in my anus. My butthole seemed to have become an irresistible attraction for anybody and everybody.
“What happened to your horse tail, Dorothy?” asked Samantha (a.k.a. Sam, a.k.a. Miss Golden Oldie), the good-looking middle-aged broad who’d had me sent up to her room the day before. “You looked really cute with that tail waving between your buns.”
Sam had a thing for odd sexual attachments. When she took me to bed, she’d worn an artificial penis, but she hadn’t tried to screw me with it. Instead, she wanted me to reach around and fondle it while I skewered her rear end with the real thing. I guess that was a kind of a new wrinkle on an old fetish. She liked to take a male role, but she wanted to play a man getting fucked by another guy. I don’t know what you call that kind of a caper, but as I was soon to find out, it was only one of her many interests when it came to fun and games in the bedroom.
She wiggled her finger around a few times like a conscientious pump jockey checking the oil, and then she withdrew it and wiped it off on my right buttock. She began untying me from the spanking block.
“Mrs. Stern said that she had plans for you later on tonight,” she said, “but I get to play with you until dinner. Where’s your maid’s outfit? Back in your room? I want you wearing that.”
Maybe Samantha wanted to take a different approach when she strapped on her dong thong this time. Maybe she wanted to bend me over and turn me into the girl. Maybe I was about to find out. Actually, I don’t think there was any “maybe” about it. I told her that, yes, the short black dress and the garter belt and the high heels and the tiny panties were back in the little room I was sharing with Delia and Donna/Darrell, and when she finished untying me, we headed off to get the stuff. I suppose that I was even looking forward to finding out what this imaginative lady had in mind, because my erection was full-blown and bouncing as we went downstairs to the submissives’ quarters in the rear of the mansion.
When we got to the room I’d been assigned, Ms. Davis was just bringing Delia and Darrell back from the pony races. They’d been stripped of the harnesses, but for some reason, Delia still had the butt-plug tail in her bottom. It did look kind of cute swinging around back there. Ms. Davis was glowering at Darrell and Delia because they were in the midst of a heated argument, but Delia was so wrought up that she didn’t even notice the Dragon Lady’s frosty look.
“It’s not fair!” she said as soon as she saw me. “I should have won, but Darrell had a hard-on, and his big old thing was sticking straight out, and they said he won by a couple of inches, but if they hadn’t have counted his hard-on, I would have won by almost a foot! That’s not fair! Dicks shouldn’t count!”
Darrell grinned at me. “I guess Delia never heard of winning by a head,” he said.
“You two shut up!” snarled Ms. Davis. “If you don’t stop arguing, I’m going to go get that horse lineament that Mr. Balsemo used on Dorothy!”
Silence fell quicker than a hooker’s drawers after a C-note sighting.
Samantha was staring admiringly at Darrell’s penis, which wasn’t fully erect but was still pretty impressive. And she spun Delia around to get a look at the tail protruding from her buttocks.
“Is there any chance that I could have these two for an hour or so along with Dorothy?” she asked Ms. Davis.
“I don’t see why not,” the Dragon Lady answered. “Most of the other dominants are attending one of Mrs. Stern’s seminars for the rest of the afternoon, so I don’t think anyone will need Donna or Delia. But why don’t I bind up Donna and Dorothy a little so they’ll be easier for you to handle?”
Sam wanted Darrell and me in our full maid regalia, so we pulled on the silk hose, clipped them to our garter belts and slipped the black uniforms over our heads. (She told us to forget about panties.) Then Ms. Davis pulled our arms up behind us and tied them firmly in place, wrists to elbows. When she had us trussed up to her satisfaction, she handed our new mistress her riding crop and said that she could borrow it “in case the girls get unruly.” Darrell, Delia and I were herded out into the hall and up the back stairs, which were a little hard for Darrell and I to negotiate with high heels and no hands for the stair rail. If we’d fallen, Delia would have been no help; she was still muttering under her breath about getting cheated in the pony race.
Sam had her dress and her underwear off almost as soon as we got through the door of her room. She stood there looking at the three of us like a kid on Christmas morning who doesn’t know which toy to play with first. I glanced at Darrell, and I could tell that he was thinking the same thing that I’d thought when I first saw Miss G.O. stripped to the skin. For a middle-aged broad, she had one fine body.
The old-fashioned bed frame had a low wooden rail across the foot, and while Sam was strapping on her artificial penis, she told Delia to tie me over the rail, bottom up. By this point in my adventures through the curious world of B&D, a dildo in my butt was no big thing, but I felt a little odd about Darrell and Delia watching. Strangers were one thing, but getting buggered in front of friends, even if they were new ones, was a little harder to handle.
What was coming, though, was not what I expected. When Delia had me tied down securely, Samantha told her that she could “fluff up Donna,” and the little sub obediently dropped onto her knees on the carpet next to the bed, lifted the front of Darrell’s skirt and took his giant organ into her mouth. While I was absorbing the implications of that, Sam swatted me a few times on the buttocks with the crop. Compared with some of the whippings I’d gotten in the last few months, her strokes were baby taps. She had chosen to attend Mrs. Stern’s bondage weekend as a dominant, but it was obvious that handing out punishment wasn’t really her thing. On the other hand, I’d have taken a good beating any day in place of having Darrell’s king-size dick up my backside, and it was beginning to look as if that’s what Sam had in mind.
“Come over here, Donna,” ordered Samantha. “Since your arms are tied, I’m going to have to help you put it in.” (That eliminated any doubt lingering in my mind about where Darrell’s erection was going.) “Oh, my God!” Sam exclaimed a moment later. “I’ve never my hands around anything like this!”
No one said anything for several minutes. Bent head-down over the back of the bed, I couldn’t see what was going on, but I could hear little noises — “Uums!” and “Ahhhs!” — from Sam and Darrell, so I figured his erection must be undergoing a pretty thorough inspection. Then my skirt was flipped up, and I felt the hard head of Darrell’s dick pushing between my buttocks and gave up to the inevitable. I tried to relax the ring of my anus to make the penetration as painless as possible, but my orders apparently weren’t getting through to the sphincter, which puckered up like a Georgia kid’s mouth at persimmon time. Like my penis, my anus had a mind of its own at times like these.
I was lost. But then was saved! The penis was pulled away.
“I’m sorry, Dorothy,” Samantha said. “You can’t have this lovely thing. I want it all for myself.”
She braced her hands on my buttocks, supporting herself as she bent over and offered her bottom up to Darrell.
“I don’t think I can get to it if you keep the dildo on,” Darrell said.
“Not that hole, love,” Sam said. “I want it in my butt. Help him get it in, Delia. That’s a good girl.”
A lot of grunting and groaning followed. I could hear Samantha gasp a couple of times as Delia and Darrell struggled to push the erection past that all-important first inch. And then it was in, and Sam went, “Ooooh!” Once she’d been plugged, I figured, she would slide into a position where she could slip her dildo into me. But she stayed bent over, head down, and what I felt instead of the aritifical penis was her tongue rolling around my anus. It probed inside, emerged and slid down across the taint and took a big lick on the bottom of my balls. I felt her head pushed against me as Darrell began to fuck her backside, but she kept licking energetically.
I was beginning to like this woman a lot. Samantha had some very different ideas about how a dom was supposed to operate — the things she liked seemed more like sub territory to me — but I guess she just wanted to be the boss, to call the shots. And the shots she was calling were just fine with me. Things went along very pleasantly for a while. Sam was moaning with pleasure while Darrell buggered her, but she didn’t forget about me, and her tongue danced back and forth between my balls and anus. I could have done with a hand on my dick, and I was about to ask Delia to jump right in when she had some suggestions of her own.
“What about me?” she complained. “Am I just supposed to stand here and watch? That’s not fair!”
“I’m sorry, Delia,” Sam said, withdrawing her tongue from my bottom. “Come bend over the bed. And get that horse tail out of your ass. I want to see it in Dorothy. She looked so cute at the pony races.”
I heard the squish as the plug popped out of Delia’s bottom, and then it was shoved into my own anus, already well-lubricated by Sam’s tongue. Sam’s hands lifted from my butt as she moved to Delia’s side of the bed. Delia’s head was now level with mine as she bent over the bed rail, and she looked over and stuck out her tongue at me. She didn’t need to gloat!
The fun continued, but now I was the one left out. All I had was that tail up my butt. I tried to rub my throbbing erection on the end of the bed, but the rail kept me from getting close enough.
Oh, well, forget it! I slumped across the rail and waited for them to finish. It took quite a while, but all three seemed to get there about the same time, with a lot of noise. I was feeling a little glum when they finally got me up from the bed rail, but I felt better when I saw Samantha’s happy face. When I first met her, she’d looked sour and mean, but the salt air at Mrs. Stern’s Santa Barbara Health Spa and Pleasure Palace apparently agreed with her.
The action had wound up just in time, because Ms. Davis arrived to collect Delia, Darrell and me. She told Sam that she could probably have me back around midnight, when whatever special entertainment Mrs. Stern was planning after dinner had been completed.
“I need to take these three down and get them ready,” the Dragon Lady explained. “I don’t know what you’ve been doing with them, but it looks like they can all use a good scrubbing.”
“They’ve all been very good little girls,” Sam said, “but you’re welcome to them. What I need right now is a long nap.”
Ms. Davis took up back to our room, but only long enough for Darrell and I to be stripped of our uniforms. Then she took the three of us naked onto the back lawn and hosed us down. When we were soaked with cold water, she made us hold our hands on top of our heads while she scrubbed us with what looked suspiciously like a toilet brush. She didn’t spare the tender parts, and I was afraid that Delia was going to pop her one when the Dragon Lady brushed her boobies. She looked mad as hell, but Darrell just kept grinning, even when Ms. Davis scrubbed his erection. Nothing seemed to bother the guy.
While the Dragon Lady was cleaning us up, several people stopped to watch, including Walter. He was making notes in a little spiral pad, probably collecting a little local color for one of those stories he wrote. Wally may not have been leaking stuff directly to the blackmailer who was hitting up Mrs. Stern’s clients, but I was pretty sure that someone outside the mansion staff was getting at look at his literary gems. I had to figure out who and how.
Just as our cold bath was over, Mrs. Stern herself came by. She told Ms. Davis that she’d had a complaint about me and wanted to talk with me in her office. That was all bullshit, of course. What she wanted to do was talk about my so-called undercover investigation, but that meant I was going to have to bend over her desk and get a loud paddling to convince anyone who might be listening outside her office that I was being punished.
I was right about that, but I was startled when Mrs. S. first took my semi-erect penis in her hand and pulled on it thoughtfully. It hardened in her fingers, and she smiled and squeezed. But then she told me to bend across the desk, just as I expected, and I got a noisy smack on my bottom from the leather paddle she kept lying there.
“There has been an unusual development, Mr. Diamond,” she said between swats. “One of my clients has had another blackmail call, but it appears to be from an entirely different person. This caller was a woman, not a man, and there was no pretense of a supposed magazine article. She just asked for money, and she seemed surprised when my client mentioned the earlier call.”
This news made me even more certain that Walter’s stories were somehow involved, but I didn’t want to risk telling Mrs. Stern that her kid might be to blame unless I had a lot more evidence. She apparently expected some kind of response, though, because she smacked me very hard with an undercutting swing that lifted my buttocks and almost sent me sprawling across the desk.
“Son of a bitch!” I gasped. “Take it easy, Mrs. Stern! I’m not one of your clients!”
“No, indeed you’re not, Mr. Diamond,” she agreed. “But your buttocks get such a lovely glow. And you do like it, you know. The more you’re paddled, the more your erection swells.”
“And I guess you think — ow, damn it!” I replied. “I guess you think that’s pretty strange, huh?”
“Not at all, Mr. Diamond. Not at all,” she said. “In fact, it has been my experience that such a reaction is the rule rather than the exception among men who enjoy corporal chastisement.”
“I’ll take your word for it,” I said. “Nothing much surprises me these days when it comes to weird sex — not even Joey Balls and his baby routine. But I’d hate to be the one who has to change that guy’s diaper.”
“I agree, Mr. Diamond,” she replied. “That is a very bizarre sight, even for someone as experienced as myself. However, it’s not a moment that we will have to repeat again. Mr. Balsemo is no longer a client.”
“No kidding!” I exclaimed. “How come?”
“Frankly, it’s because of what he did to you,” she said. “That could have caused serious damage in an extremely vulnerable area. We can be very strict with our clients, and sometimes a good deal of pain is involved, but we are careful to avoid anything that could result in a lasting injury.”
“Aren’t you worried about what Joey might do?” I asked. “And I guess you know that your kid owes him a few grand?”
“That debt has been paid,” she said. “And, no, I’m not particularly worried about Mr. Balsemo. One of my strictest rules is no photography of clients without their permission, but in the case of a person with a reputation as sordid as Mr. Balsemo’s, I made an exception. I think you might say, to use a somewhat vulgar phrase, that we’ve ‘got the goods’ on him.”
Well, that was bad news for Joey but good news for me. I had him out of my hair for a while at least, and I could get on with whatever I’d been getting on with. Actually, that wasn’t much so far, except for the hunch that Walter’s stories were involved in the blackmailing. But that was more than a hunch. I’d have put money on it.
Mrs. Stern was done with discussing the case, but she pushed me back down on the desk when I began to get up and whacked me three more times. My bottom was pretty hot by then, and she ran her hand over it, cupping each buttock in her palm and squeezing gently. Her hand went down between my legs and fondled my balls. I had no idea what that was all about, but if her strategy was to get me under her thumb a bit more, it was working. Mrs. S. was a nice-looking lady, but she had at least ten years on me, and she wouldn’t normally have rung my chimes. Right now, though, my dick was so eager to be touched that I could have rubbed myself off on the top of the desk. But she made me stand up and gave me that little smile again and sent me off to my room to wait for the evening’s festivities. I departed with my erection standing straight out and a string of pre-cum dangling from its end.
Darrell and Delia weren’t there when I got back to our room, so I sat on my bed and began masturbating. The doors of all the rooms used by the subs had been removed from their frames, so anyone walking past could look in and see me, but by this point, that didn’t bother me much. I needed some relief. Then Delia and Darrell did walk in, catching me in the act, and Delia asked if I’d like her to “handle that.” That sounded good to me, but I was a little embarrassed about Darrell and glanced in his direction. He said, “Don’t mind me,” and went over, stretched out on his bed and turned his face to the wall. Delia sat down next to me, grabbed my dick and got busy. After a half dozen strokes, she leaned over and took my erection in her mouth.
Things were going great, but you can probably guess what happened next? You’re right. Ms. Davis came in to round us up for the soiree that Mrs. Stern had planned that evening, and instead of an orgasm, I got a tirade from the Dragon Lady and three good strokes with her crop. So did Delia and Darrell, which seemed especially unfair for Darrell, since he wasn’t even watching. But he just grinned — like always.
Ms. Davis had all three of us get into garter belts, hose and high heels, but the uniforms and panties stayed hanging on the hooks on the bedroom wall. As I’d found out before, I felt even more naked and exposed with those few things on than if I’d been wearing nothing at all. The garter belt, the diagonal lines of the garter straps and the lace tops of the stockings seemed to focus attention on my bare thighs and my dangling penis.
When we were ready, the Dragon Lady took us down to the dining room and fastened us by the wrists to iron rings that had been set into the wall just below the plate rail that topped the paneling.
“What’s up for tonight?” Darrell asked cheerfully.
Ms. Davis stared at him, trying to decide whether to answer.
“We’re going to have a little contest after dinner,” she said. “You and Delia will compete against Dorothy and her partner.”
“So who’s my partner?” I asked. (I was getting used to being called Dorothy.)
She didn’t answer this time. She just stalked out of the room, leaving us hanging there. But we didn’t have to wait long to find out who was making the fourth. The Dragon Lady came back leading a naked Samantha by a cord fastened by a metal clip to one of her nipples.
I was stunned, but I suppose I shouldn’t have been. Sam might have signed up for Mrs. Stern’s weekend as a dominant, but the things that she’d had Darrell and me do to her had submissive written all over them. She was blushing a fiery red and practically tembling with excitement — or maybe fear, probably both — and I guessed that this was the first time this nearly middle-aged lady had finally yielded completely to her fantasies. Good for her, I thought. She had on the uniform of the day — just garter belt, hose and heels — and the lips in the shaven delta between her thighs were glistening with moisture. She looked great.
As Ms. Davis was fastening Samantha to a fourth ring on the wall, Mrs. Stern’s guests began arriving for dinner — dominants, submissives tagging along, the staff, the usual suspects. A few of them detoured for a minute or two to check us out with little pokes and pinches, but the No. 1 item on the agenda was finding a place at the table. Even at a place like this, if the vacation package came with meals, the paying customers were going to make sure they got their money’s worth. Call the B&D crowd what you like, but don’t call ’em late to dinner.
The meal went on for an hour or so. Dessert was served by the subbie maids. Then Mrs. Stern tinkled the little crystal bell sitting beside her plate, and the conversation around the table died down.
“I’m sure that many of you have plans for later this evening in our punishment rooms,” she said, “but first we have a brief entertainment planned. Hopefully, you will find it stimulating as you approach the evening ahead. Delia and Donna will be matched against Dorothy and Diva in several unusual contests. The losers, I’m afraid, will have to pay the forfeit of a rather brisk spanking by our Ms. Davis and Mrs. Hudson — and by anyone else who wishes to lend a hand. The winners? Well, the winners will no doubt be spanked themselves at some point, but they will be spared for the moment.”
I had a pretty silly immediate reaction to that little speech. I wondered why Samantha got tagged with a neat sub name like Diva, while I had to make do with something as ordinary as Dorothy. Even Dot would have been better. As I said, it was a silly thought. When I started worrying about my slave name, I was probably getting way too serious about the S&M lifestyle. Anyway, that momentary reaction was quickly followed by a wave of panic about the threat to my backside. This was a contest that Samantha and I were going to have to win!
The guests pushed back their chairs and turned them so they faced the large open area at the end of the dining room. The four of us were untied from the rings by Ms. Davis and Mrs. Hudson, and Darrell and I were instructed to lie on our backs on the floor, erections pointing at the ceiling. The first round of the contest was pretty simple and not really very exciting. Delia and Sam were each given a half dozen rope rings about five inches across for a little game of Ring the Penis. First one with three ringers was the winner.
The problem was that my erection, which had been stiff as a carrot all through dinner, was drooping sideways now, and Sam had an extremely difficult target. Darrell’s dick was sticking up like a Maypole, of course. The girls stood behind an imaginary line about a dozen feet away, and when Ms. Davis gave the starting signal, they began tossing the rings. Delia got two ringers on her first six throws, while Sam didn’t manage to get a single one around my misbehaving dick.
The girls ran up to get their rings to throw them again, and Samantha fell to her knees next to me, took my penis in her hand and lowered her mouth onto it for an emergency fluffing. The spectators had been shouting encouragement to the girls all along, but when Sam made her move, the crowd — like they say — went wild. Her first-aid did the job, and when she lifted her head, my erection was in full bloom again. It was way too late. Delia already had ringed Darrell’s dick for the third time.
“Delia and Darrell win the first round,” Mrs. Stern announced. “Diva and Dorothy, I’m afraid you’re going to have to do much better if you wish to escape a paddling.”
Now a couple of the male subs were carrying in a large metal washtub holding a block of ice. They set it on the floor, went back to the kitchen and returned with another, which they set down next to the first one. Ms. Davis placed a single olive on each block of ice, and Mrs. Stern explained the rules: One member of each team would run from the starting line on the other side of the room, pick up the olive from a block of ice using only his or her buttocks and carry it across the room –no hands — and drop it into the mouth of the waiting partner, lying behind the starting line. Then the partner ate it, jumped up and repeated the process with another olive. First team to gobble down both of their olives won.
The girls went first. At the starting signal, they ran across to the blocks of ice and lowered themselves onto the olives. There were loud squeals when their bottoms hit the freezing surface. They wiggled around for a while, got up and turned to see if they’d been successful. Both olives were still resting on the ice. They sat down again, and there were more squeals and more wiggling, and then they got up and came waddling slowly across the room, buttocks clenched tight, to where Darrell and I were lying.
Samantha straddled me and lowered her buttocks over my face. The olive wasn’t quite over my mouth, and I could see it slipping out of Sam’s crack, so I lunged sideways with my head just in time to catch the falling prize in my mouth. As Sam stepped aside, I sat up, bolting down the olive and feeling as proud as if I’d just made a game-winning catch in the World Series. But the pride turned to dismay when I saw that Darrell was already scrambling to his feet and heading back to the ice.
I got up and raced after him, but I wasn’t prepared for the shock when my descending balls hit the icy surface. I gasped and jumped up, but when I saw Darrell looking at me with his usual shit-eating grin while he shifted his butt around trying to pick up his olive, I lowered my bottom back onto the ice. I was lucky. I sat down with the olive directly in the crack of my buttocks, and I clenched them together and stood up. Darrell apparently had his in place, too, and we both began shuffling in a knees-spread position across the dining room, cheeks squeezed tight to keep from dropping the olives.
In my brief but very eventful career as a submissive, I had been stripped, spanked and speared on any number of occasions. I’d been laughed at by two girls in the hall of Miss D.’s while I searched desperately for a bathroom with an enema up my butt and my balls covered with clothespins. I’d been paddled and poked for the entertainment of the audience at one of the shows at The Castle, back in the Valley. I’d had to stand naked while I was groped by a ring of joking customers at the Spitfire Club in San Francisco. I’d had to haul a pony cart around with a horse tail stuffed into my ass. But I’d never felt as humiliated as I did now, waddling across the floor trying to keep that olive from falling, with the dinner guests roaring with jeers and laughter.
Darrell and I reached the girls at the same time. I squatted over Samantha’s head, lowering my buttocks as far as I could, but I couldn’t let go of the damn olive! I tried to make my cheeks spread wider. The olive stayed put. Then I felt Sam’s tongue curl up the crack, probe for the olive and carry it away into her open mouth. I looked over at Darrell just in time to see his falling olive miss Delia’s mouth and go bouncing away across the floor. I had a fleeting moment of triumph before Sam sat up too quickly, and the top of her head smacked hard into my balls.
A wave of sickening pain swept all the way to my head and back to my toes again, and I bent over clutching my testicles. All I could see was a red haze, but I could faintly hear Mrs. Stern’s voice, and her words got through to me.
“Very well done, Dorothy and Diva,” she said. “We now have a tie, and the final contest will decide our winners. Diva and Delia will take the active roles, with each trying to induce an orgasm from the other member of the opposite team. Dorothy and Donna will play less active but perhaps more difficult parts. Their job is simply to resist. Not physically, of course. They must stand and submit. Their resistance will be of a more subtle kind. The first to reach orgasm will lose the competition for his — or, I should say, her — team.”
She paused and looked at me, still bent over in an agony that was slowly receding. My erection had disappeared, and my penis had shriveled to a nub.
“I believe that Dorothy may now have a slight advantage in this final contest,” she said. “Be that as it may, let the games go on!”
“That’s not fair,” Delia began, but she got a warning look from Ms. Davis and clamped her lips together in an angry grimace.
I was able to straighten up enough to stand erect, while Delia knelt next to me. Across the room, Darrell and Samantha were in the same positions. Ms. Davis gave the starting signal, and Delia’s tongue went searching for my penis. It curled around the few inches into which it had telescoped and tried to coax it out of hiding. My dick wasn’t having any of that at first, but then it began to stir, to come out of hibernation, to raise its head again.
I looked over at Darrell to see whether Samantha had him on the verge of cumming, and I couldn’t believe what I was seeing. She was sitting on the floor at his feet, and one hand was reaching up to hold his penis. But she wasn’t doing anything! She and Darrell were both just watching us and smiling. Darrell looked as if he was about to break out laughing.
Sam was throwing the game! She wanted to poke her little bottom into the air and have it paddled in front of her fellow guests! She wanted to feel her butt burning! She wanted to savor the humiliation! Fair enough, but couldn’t the broad think about me?
My shoulders slumped, and I gave in to the inevitable. So did my dick. Delia licked my erection into a throbbing shaft of flesh. Her tongue swirled around the head, and she enveloped it with her mouth. The tongue patrolled up and down the length of the organ’s underside. And when she felt my orgasm coming, she lifted off her mouth, gave my balls a farewell lick and displayed my penis triumphantly to the guests in her tightly clenched hand as the cum came cascading out.
“Clean him off,” Ms. Davis ordered Delia, tossing her a towel, and before I knew it, two chairs had been pulling into the open space, and Sam and I were across the laps of Mrs. Hudson and Ms. Davis, bottoms up and staring at each other across the gap between the chairs. Sam gave me a little “I’m sorry” shrug, and then the spanking began.
At first, I was glad that I was bent over Mrs. Hudson’s lap. I figured she wasn’t nearly as mean as the Dragon Lady. But I’d forgotten that Mrs. H. was a big, healthy girl, and her hand was coming down hard, covering my upturned bottom with stinging blows. She spanked me with her bare hand until my rear was hot and more painful with each blow. Her hand must have been getting sore, too, because she switched to a small leather paddle. I looked up and saw that Ms. Davis had done the same thing, and she was bringing it down with loud smacks on Samantha’s buttocks. Sam’s eyes looked as if they were about to pop out of her head, and her mouth was wide open in shock. I think that she’d just realized that she was going to get more than she’d expected.
She looked over sideways at the applauding guests, and I knew that all she was seeing was an ocean of faces, all staring at her, all laughing at her. Right about now, she probably felt as if she was nothing but a swelling, burning bottom, clenching for the next swat. She went “Ooohh” each time the paddle fell, and then she was begging Ms. Davis to stop, pleading with her, with her legs kicking in the air and all her dignity gone. Tears were running down her face, and she was soon crying so hard that her pleas were nothing but incoherent gasps. I was so fascinated by the sight that I almost lost track of the blows that were falling on my own buttocks, and I didn’t even notice at first that Mrs. Stern was calling the paddling to a halt.
“I believe that Dorothy and Diva have received the necessary punishment,” she was saying. “I had hoped to let others of you join Ms. Davis and Mrs. Hudson in chastising them, but I’m afraid that our little show has gone on too long. I’m sure that you all have a great many interesting activities planned for this last evening in our little weekend, and time is growing short. I’m very pleased to have had all of you join us, and if you have any need of anything at all this evening, please let Ms. Davis or me know.”
Mrs. Stern knew what she was doing. She knew how to punish, but she knew when to stop. After Samantha’s bottom stopped burning, she was probably going to get turned on all over again whenever she thought about the spanking she’d received. But if it had gone on any longer, she would have been left with nothing but resentment and a bad memory.
Mrs. Hudson led Sam away, still sobbing, and Darrell, Delia and I were told to go back to our room and wait there in case any of the dominants felt the need for another butt to abuse. Delia was in a good mood, happy over winning the contest and finally willing to forgive Darrell for edging her by a penis head in the pony races.
“I could have gotten you to cum first even if Samanatha had gone ahead and tried to get Darrell off,” she told me as we walked down the hall.
“Probably,” I said, not wanting to argue.
“Those games were really fun,” she said. “I bet Walter puts them in his Internet stories.”
I stopped walking and grabbed her by the arm.
“Say that again,” I said.
“Ow! You’re hurting me,” she said, pulling her arm away. “All I said was that Walter might write about all that stuff in the stories he puts on the Internet.”
“Walter puts his stories with real people’s names in them on the Internet?” I asked.
“Right,” Delia said. “He sends them to some free bondage website. It’s called B&D Diner or something like that. Something about a restaurant anyway. I don’t know exactly what it is. But they’ve used a whole bunch of his stories.”
I turned around and began walking back toward Mrs. Stern’s office. I didn’t bother to go put on the uniform hanging back in my room. I went naked except for the heels and hose and the red glow on my butt. Now that I knew where the blackmailers were getting the information, I wanted to wrap this case up in a hurry. On the way, I met Ms. Davis and I just waved her aside. She didn’t try to stop me.
Mrs. Stern was in her office when I got there. She picked up the paddle from her desk, apparently intending to carry on the charade of punishing me to cover our conversation. I told her not to bother and proceeded to lay the whole thing out for her. She sat down at her desk while I was talking, and she didn’t say a word until I finished. Then she sighed deeply and looked up.
“Thank you, Mr. Diamond,” she said. “I want you to know that your findings are a great relief to me. I didn’t want to admit it even to myself, but I was very much afraid that Walter was somehow involved in this. Now I know that he was not unfaithful to his mother. He was just being very, very stupid.”
I was in total agreement with her on the stupid bit, but I didn’t say so. No mom likes to have her kid run down. Besides I was thinking that I might like to come back to the Stern mansion as a paying customer sometime, and I didn’t want to get on Mrs. S.’s bad side. She must have been reading my mind. She stood up, came around the desk and took my penis into her hand.
“If you should ever care to visit us again,” she said. “we will be most pleased to welcome you. My partner and I are very grateful, and I’m sure he joins me in expressing our appreciation.”
“I didn’t know you had a partner,” I said. “I guess you’ll want to call him and let him know the problem is solved?”
“I won’t have to call him,” she said. “He works here at the mansion.”
She gave me a final squeeze and a little smile, and released my penis, leaving me with a rising erection to remember her by. I knew it was time to say good-bye. I’d never met anyone who could remain so dignified while holding on to your dick. In fact, I’d never had a client who shook my dick instead of my hand at the end of a case.
While I was walking back to the room, I was wondering who Mr. Stern’s partner was. I thought that the only man on the staff was Walter. There must be someone else I hadn’t met. When I got to the room, I asked Darrell about it.
“Maybe he operates undercover, like you did,” Darrell said.
“You mean he poses as one of the guests?” I asked.
“Maybe,” he said. “Or maybe he likes bondage himself. Maybe he works as a submissive so he can do what he enjoys most without anyone knowing he’s one of the owners.”
I stared at him.
“Are you telling me what I think you’re telling me?” I said.
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