Cuckold Stories











Panty fetish discovery leads to progressive enslavement and cuckoldry.




Chapter 1


Every other Thursday afternoon is my time to clean Mistress Anne's house. I am expected to be there at 2:00 pm sharp, with my panties, white stockings and garter, and bra on. By 2:05 I am to be in my maid's dress and high heels, ready to start. Some days Mistress Anne is there when I arrive, and my first task is to take detailed notes as to what she wants done, in addition to my normal routine. Other days she simply leaves a list on the kitchen counter, with no indication when she will return. I am expected to finish by 7:00, after which we usually cook dinner together, have a drink, and then one of several things happens. About half the time, I am expected to help her get ready to go out on a date, and then I am put to bed at 9:00 sharp. Mistress Anne believes sissy little boys should be in bed early. Occasionally we simply visit until 8:45, and then the evening comes to a close with, "It's 8:45 - 15 minutes for all little sissies to be in bed. I don't want to have to tan your bottom - better get moving."


About one time in four, Mistress Anne uses me as her sex toy (more on that in a moment), and once or twice a year she actually rides my dick until I have an orgasm, primarily, I believe, so she can spend the rest of the year reminding me how inadequate I am to be her lover. Of course being shamed is a major turn on for me, and besides, my wife has always found me to more than adequate sexually, so this has just been part of our fun and games.


And every so often, either as a result of accumulated misdeeds (recorded in a book I never get to see) or some grievous error, she tells me while we make dinner that I have a "lesson" coming after dinner. Once a year or so, the "lesson" comes as a result of a call from my wife Joyce to Mistress Anne regarding something I've done to really make her mad, but Joyce is reluctant to use this method. (If Mistress Anne is feeling particularly uncharitable, I get Brussels sprouts and liver for dinner before my lesson.) So I have to endure dinner, trying to swallow my food, knowing what's coming next. "Lessons" are never fun or erotic at Mistress Anne's house; they aren't meant to be, but by the same token, she doesn't make up reasons. They are always well deserved. After dinner I have to strip down to my bra and hose (she, of course, is completely dressed). Then it's a lecture on what I've done wrong. I have to explain why I did what I did, why it's wrong, and what I'm going to do to prevent it in the future. Then it's over her knee for a true ass blistering with a hairbrush, then into the corner with tears streaming down my face. If I'm lucky, I'll be there for 45 minutes, then off to bed. If I'm not, she pulls me out, ties me over a chair with my legs spread, and uses a handful of birch switches to turn the backs and insides of my thighs into a mass of welts. Then it's back into the corner for 30 minutes or so, and off to bed. (I'll be sleeping on my stomach for a week.)


But I should digress and explain how this all came to be. I met Mistress Anne about 10 years ago (Anne to me at the time). She was a loan officer at my bank, and I met her briefly in the course of closing on a mortgage. We then saw each other occasionally at community functions, and managed to remember each other's name. All that changed 5 years ago when she ran into me in the lingerie section at a department store. I'm sure I blushed when I saw her, but since I hadn't selected anything, I could have been shopping for a gift for my wife. So I eased into the nightie section from the bras, but she moved to a few feet away from me, and said in a normal voice, "Be sure and get your size - I'm sure a medium will do." I could have died. If I had just laughed, said I was shopping for a present, and picked something out, that probably would have been the end of it. But instead, I turned deep red, mumbled something I can't remember, and left.


I was of course humiliated, but had no idea what, if anything, would happen. What could she do other than snicker at me? So I didn't think anything more about it after a few days. Three weeks later my wife and I were meeting for lunch, and when I got there, who should be sitting with her but Anne! My face was immediately beet red, and while Joyce giggled, Anne said, "Have a seat, little boy."


To make a long story short, Anne had immediately called my wife (who also knew her from the loan closing) and invited her to lunch the next day. (My wife knew I wore panties and had a submissive streak - we had talked about it often - but had never participated or been willing to have me participate with others.) But somehow Anne put her at ease, convinced her she was much better off to give someone control of me two days a month than to risk me finding someone else to "play" with, and the rest is history. I no longer say Anne; she is Mistress Anne or Ma'am to me. It's actually been a dream come true. I get to fulfill my submissive needs, I don't have to sneak around behind my wife's back, and Mistress Anne and I enjoy each other's friendship. We also socialize occasionally as couples (Joyce and I, Mistress Anne with one of her regular dates).



Chapter 2


Now to what happened few weeks ago. Mistress Anne enjoys reminding me how sexually inadequate I am for her. It's a general statement, but she also applies it specifically to my cock. I'm average in size - probably 6 inches by 1 1/2 inches - but it is true that my cock is lost in her cunt. I've thought for these 5 years it was just a result of childbirth. I learned differently this week.


Anyhow, about a month ago Mistress Anne began playfully taunting me, saying, "I bet you couldn't even pick up a horny secretary in a bar - they could sense you are a wimp just looking at you."


I asked if that was a dare. There was a long pause and then she said with a twinkle in her eye, "If you want to make it one."


"What are the stakes?" I asked.


"Let's see. If you can pick up a girl, bring her back here, and fuck her consensually, no lessons for one year."


"And if I fail?"

"Oh, the usual, but now you will have to actively agree with me every time I tell you how inadequate you are."


"One last question. Do I have to go in cold, or can I use the Internet, personal ads, etc to find a potential date."


"Sure, little boy. Use whatever you like. You're a sissy, and any woman can tell it. The only thing I want is proof that it actually happened. I've got a little pocket tape recorder you can carry to collect the evidence. And just to make the challenge legitimate, you can't abandon your sissy underwear until you actually get someone in the bed. That will be a little tricky, but I'm sure you can manage it."


It sounded like an easy bet to win given the lack of restrictions, so I got busy on the net, and within the day had struck up a email conversation with not one, but two, women who were looking for a man 40-45 to play with together. They specified "single, divorced, or separated," so I chose the latter. I figured it was okay for a one-night stand. I responded to their ad, we qualified each other for fit, and then went far enough to know we were all interested. We swapped phone numbers, did the verification thing, and then exchanged pictures. Karen was a little chubby, but she and Diane were both descent looking and sounded fun, so we started looking for a time to meet. In the meantime, we were having fun with email chat back and forth about all the things we enjoyed sexually.


Mistress Anne was of course demanding regular updates, which I provided with a gloat. She insisted I call them from her house a couple of times just to "see if this is real." There was a week coming up when Joyce was going to be traveling on business Monday-Wednesday (this week), so Mistress Anne pressed me to prove I could do it by setting up a meeting. We picked Wednesday, agreed on a bar, and all was set. The underwear thing concerned me just a little, but since this wasn't going to be romance. just sex. there wouldn't be any hugging or kissing, and I could just strip in the bathroom and put on a robe.


Mistress Anne, sensing defeat, then sprung one additional condition - I had to wear a bra and panties to the bar under my clothes. I of course said, "Are you kidding - when they see that - they will run the other way."


"Don't be silly - I don't expect you to let them see it. You can go to the bathroom as soon as you get them home or to a hotel and take them off. I just think it's only fair you prove you can do it while you are dressed like you always dress."


Feeling pretty confident, I said, "OK."


So here I was in a bar two nights ago on my third drink with Karen and Diane. Mistress Anne had made me stop at her house on the way to make sure I was dressed as expected. Karen and Diane's pictures had been flattering. They were not nearly so attractive in person. There were two hot looking ladies standing 5 feet farther down the bar, but hey, I wasn't going to be choosy, I just wanted to win the bet. I had the tape recorder in my sport coat pocket, and we were all getting loose enough to head to someplace more private. I needed to pee (they of course had already been once, but God bless them, at least they didn't go together) so I excused myself. There was only one stall, and since I had to pull my panties down to pee, I had to wait until someone finished using it, so it took several minutes.


As I came back to the bar, I knew immediately something was very wrong. There was Mistress Anne talking to Karen and Diane! They were talking intently. Diane looked sort of confused or consternated, but Karen was smiling and sort of laughing. Momentum kept me walking toward them, and as I got within earshot, I heard her saying, "Here he comes now - I can prove it." She grabbed me by the shirt, quickly undid two of my shirt buttons, and before I could react, said in too loud a voice, "See, he's even wearing a bra tonight."


"What in the hell are you doing?" I said.


"The better question is what in the hell are you doing. I've explained to these two ladies that you are a complete sissy, but that I didn't know you were a cheat also. They've told me all about how you passed yourself off as an unattached stud. That couldn't be farther from the truth. You have a very faithful wife, and you have me to keep you in line."


"But you put me up to this - this was all part of our bet."


Now Karen weighed in. "Oh, so is that your story. That's even more disgusting. Not only are you a freak, but you hustle women on a bet?"


I was completely speechless. I couldn't change the bra. If I argued the bet angle, it just got worse with Karen. If I denied what Mistress Anne said, she was just going to keep telling them more, and I could tell the two hot ladies plus two guys were starting to notice what was going on.


Before I said another word, Mistress Anne said, "Give me your wallet."




"Now, or this gets worse for you fast."






"Yes Ma'am."


"That's better. And your car keys. And what's that bulge in your coat pocket?"


I had my hand in my pants pocket pulling out my car keys, so before I could react, Mistress Anne pulled out the tape recorder.


"Is this a tape recorder? Were you taping this?"


"Mistress Anne, I...I...I was just doing."


SLAP! Diane, who had been watching all this in stunned silence, had come alive and slapped me, hard.


"You're disgusting," she said, and by now, one of the women in the group of five or six looking on said, "Yeah, go girl."


"Ken, you get your sorry ass out of here," said Mistress Anne. "I'm keeping your car - here's a dollar for the bus. By the time you get to my house, it will be after your bedtime, so I better find you in bed, in your pink nightie, asleep when I get home. And you don't need this," she said, holding up my two-thirds full scotch and water. She pulled out my waist, pulled the top of my panties up and away from my stomach, and turned to Karen and Diane, by now completely surrounded by three other women and two men. "Any one want to do the honors."


"I'd love to," said Karen, taking the glass and pouring it into my panties. "Oooohh. Iced panties."


"I don't need this either," said Diane, holding up her full bloody Mary.


"Pour it in," said Mistress Anne, and the crowd collapsed in laughter.


I was wearing light tan slacks, which were now completely sticky with tomato juice on the inside and looking like I had peed in them three times from the outside. But nothing was darker than my face.


I turned and ran out of the bar. Mistress Anne said, "No masturbating," as I was turning, and one of the guys yelled, "Fag on the loose," as I went through the door.


It took me an hour and a half to figure out the bus routes and get to Mistress Anne's house. I got lots of funny looks, but nothing could be as bad as what happened in the bar. I heard Mistress Anne come in very late, but she didn't come in my room, and I wasn't about to go see her.



Chapter 3



I awoke the next morning to Mistress Anne's hand on my cheek. "Poor little sissy. Did Mistress abuse him too much last night?"


"Ma'am, I have never been so humiliated in all my life."


"Should I take that as a thank-you? You've always talked about being publicly humiliated when we talked about your fantasies."


"I know. But you caught me by such complete surprise."


"That's the only way it would work. And don't tell me you didn't get a rush out of it."


With that, she started feeling under my nightie for my dick, and damned if it didn't betray me.


"See, your little dickie is getting hard just talking about it."


"But why did you do it?" I said.


"Well, when I first teased you about not being able to pick up a woman, you were far too quick to pick up on the dare. I didn't know where it would lead, but if you were really willing to cheat on Joyce, by God, I wanted to teach you a lesson you would never forget. And you, little dick brain, played right into my hand."


"I'm sorry, Mistress Anne, I guess you are right. But you were the one tempting me. I thought that made it OK."


"Little sissy," she said, "There will always be temptations. You are the one who has to resist."


"We'll, thank god it's over."


"Over? You think it's over? I've got your tape recording. I recorded the calls you made from my phone. Remember those? And best of all, I don't have to explain it to Joyce - she saw it all!"




"Oh yes, once we knew what night your ?big event' was going to be, she changed her plans to come back a day early. She wouldn't have missed it. She knew in advance," said Mistress Anne. "At first she was furious. She wanted to throw you out. But I convinced her not to get mad, just get even. See, you just don't realize how nice I am to you." She laughed.


"We'll, she knew it was just a dare. Didn't that make a difference?"


"Oh, I didn't bother her with those little details. I just told her to find your emails and postings on the Internet - it looked like you were trolling the whole world!" said Mistress Anne. "And then I played her the tapes of your calls from my phone, and of course now we have a one hour tape of last night. We were sitting at a table in the back until you went to the rest room, so we obviously don't know what's on it, but I bet it's good."


"Well, I'll explain it to her."


"Lot's of luck. I think you are a little short on evidence, my little cuckold."


"Oh dear, how will I ever face her... Hey, what do you mean, cuckold?" I said.


"Oh, silly sissy. I told you I convinced her to get even, not mad. I left her last night with Paul. Remember him? We all went to dinner about six months ago. That's why I took your car - they needed it to go out to dinner. Paul was one of the guys standing there at the end. I'm surprised you didn't recognize him. But then, you were a little preoccupied. I'm sure they had fun. Now get up, sissy, and put on a robe. I'll take you to your house so you can get dressed for work. You're due back here at 2:00."


When we reached our house, my car was back in the garage, but Joyce's was gone. I was confused, but glad I wouldn't have to face Joyce just yet. I figured she must have had an early meeting until I went into the kitchen. On the kitchen counter was a note:


Dear Sweetie,

I had to leave early and drop Paul by his condo. Please put clean sheets on our bed before you go to work and put the dirty ones in the washing machine. They're a dirty, sticky mess! And put a couple of bottles of white wine in the fridge too. Thanks, sweetie.







Chapter Four


Yesterday afternoon I arrived at Mistress Anne's at the appointed time, found my list, and proceeded about my maidly duties. I thought about Joyce a lot - was last night just a one-time occurrence to get even? She had never been interested in any type of kinky play - it was hard to imagine she would take this very far. But then what were the two bottles of wine for?


Mistress Anne got home about 5:00 and was in a very good, talkative mood. We finished dinner and went into the den. Mistress Anne sat down and said, "You've got some more work to do - strip down to your bra and hose and get your head under my dress." I knew what that meant - I was now going to spend a significant amount of time orally servicing her cavernous cunt. Last night was no exception. After at least twenty minutes of kneeling between her legs while she pushed my head into her cunt (resulting in two orgasms for her), she said, "On the floor, sissy." I lay down on my back and watch her dripping, hairy cunt descend on my face. She was facing my feet so she could bury my nose in her cunt while I licked her clit. With her quite ample thighs gripping my face and her cunt spread across my nose, she started grinding her cunt down on me relentlessly. After another 15 minutes and two orgasms, she finally relented. My face was raw - I knew I would look wind burned for several days.


Mistress Anne then slid forward, positioning her ass directly over me, and sat down with all her weight. I knew my job - tongue her asshole as deep as I could before she smothered me. She always made sure she bent forward periodically to give me just enough air, but the effect was one of being completely absorbed into her ass.


She then did something a little surprising - she leaned all the way forward and started licking my cock. My hard on got harder, and within the minute I was struggling not to have an orgasm (which would have earned me an immediate lesson). Mistress Anne then rocked back and said, "Does sissy want to actually get to fuck me tonight - does he think he can do it?"


I said, "Oh please, Ma'am, it's been so long. I know I could make you happy. Please fuck me."


"Well, after last night, I'm feeling a little sorry for you," she said. "Let me make one phone call, and then maybe, just maybe, we'll fuck."


With that, Mistress Anne got up, walked out of the room, and came back 10 seconds later with the portable phone. She straddled me again in the same fashion, but this time just teasing my tongue so that I was licking her cunt and ass very lightly. She then dialed and started talking to someone without ever saying his or her name. I could tell pretty quickly that they are talking about where to go on some (presumably double) date. After a while it became apparent they were talking about tonight, which almost dashed my hopes of getting laid, but then Mistress Anne said, "Be here at 9:00," and I thought perhaps I still had a chance. However, the conversation seemed to go on and on about nothing. When she finally hung up and stood up, I could see immediately that it was now 8:40 - she had talked for 40 minutes while I was hoping to get laid! However, Mistress Anne appeared not to notice the clock, because she came back and straddled me, this time with her cunt over my cock, and started to rub her cunt over my cock. "Perhaps she doesn't notice the time," I thought, but sure enough, at exactly 8:45, Mistress Anne said, "Awwww, poor sissy. It's your bedtime, and I know getting your little dickie in my cunt isn't worth an ass blistering for being late to bed. You go get ready for bed. I'll throw on some clothes, and come tuck you in before I go out."


Not wanting to take any chances, I was in bed with the lights off by 8:55. A few minutes later the doorbell rang and I heard Mistress Anne answer the door. "Come on in. I'll just be a minute - I've got to tuck sissy in bed and I'll be ready to go."


My face must have been hot enough to burn by the time she walked the short distance to the bedroom. Who was this that knew about me?

I didn't have to wait long to find out. Mistress Anne swept into the room, dressed in pretty revealing clothes, bent down to kiss me (I love the touch of her heavy breasts as she does so), and said, "Don't worry, it's just Joyce and John - Paul and I are going out with them. Oh, that's right, you don't know John. I'll make sure you meet him soon - no need to remain strangers to the other half of the family."


I buried my head in my pillow in shame as they leave. I'd spent the evening eating Mistress Anne cunt and ass while she talked on the phone to my wife about where she and my wife would go on a "date" with another man! And then they'd come to this house and picked up Mistress Anne, completely indifferent to how humiliating it was to me. And who was this John? And where were they going? Paul was along too - last night he was fucking Joyce - now he was with Mistress Anne and Joyce was with someone else. All to win a bet to get a chance to fuck a lady that was 14 years older than me, because as she had clearly demonstrated to me, that was the best I could ever hope to do.



Chapter Five


Somehow I finally went to sleep, shamed and humiliated as I was. I awoke seemingly only moments later to the smell of Mistress Anne's perfume.


"I'm back, little boy," she whispered. "Just wanted to make sure you were OK, and also make sure you haven't been playing with yourself - I know how exciting this all must be."


With that, she turned on the lamp, pulled down my covers, and spread my legs. I should mention that Mistress Anne insists I wear pink acetate panties, so any precum makes a stain that is impossible to conceal. "Good boy," she said. "Looks like you've behaved yourself. Since you're awake, you've got just a little more maid duty." With that, she whisked off her panties, climbed up on the bed, and straddled my face. I suspected what was coming - her cunt was dripping with cum, and there were large globs of cum stuck and dried in her pubic hair. I was beyond further shame, and dutifully licked and sucked until I had eaten every drop of cum her boyfriend had left.


"You've been such a good little maid today, maybe I can make an exception to your bedtime rules. Do you want to get fucked?"


Without thinking, I said, "Oh yes Ma'am. With what's going on with Joyce, that would at least let me feel somewhat like a man."


"Yes, I guess it would make you seem like a man of sorts. Get your hose, garters, heels, and bra back on and meet me in the playroom."


The playroom is a sitting room that adjoins Mistress Anne bedroom, so I guess I just expected to go from there to her bed. But it also has her toy collection, including "the horse," so I should have clicked as to what was about to happen, even though I had missed the earlier clues. But I was still just waking up, and my dick was running the show.


So there I was standing in the playroom when Mistress Anne came out of the bedroom. She had on a low cut bra, which barely supported her heavy breasts, black stockings, a garter, heels, and what looked like an 8" strap-on dildo between her legs!


"Wa, wa, wait. I thought..."


"You thought with your dick, little sissy," said Mistress Anne, cutting me off. I just asked if you wanted to get fucked, I didn't say whether you were the fucker or the fuckee. And I almost cracked up when you said it would make you feel like a man. You're going to feel like a man, all right. You're going to feel like a fag's wife. Over the horse, wife."


I was frozen in place. Once again, my dick-brain was bringing me shame and suffering.


"Now, or I'm going to fuck a blistered ass, not just an ass. Move it," she said.


I meekly turned toward the horse. The horse resembles a vaulting horse - it has an A-frame construction and an 8" wide padded top. Half way up on each of the four legs are cradles into which rest the victims knees and elbows, so that his weight is balanced between his chest, resting on the horse and his arms and legs. There are then straps that go behind the knees and over the forearms, making it virtually inescapable. And of course the key feature is that the legs are spread and the ass and balls are completely accessible.


As Mistress Anne strapped me in, she said, "You probably want to know who John is. He's a dear friend of mine, 38 years old, and body hard as a rock, and the thickest dick I've ever seen. It must be 2 to 2 1/4 inches in diameter. He's the reason my cunt is so large - between his size and his stamina, nothing else ever seems quite as good after you've had John. I still see him occasionally, but we both like a lot of variety, and frankly, if I hadn't stopped fucking him so often, I was never going to enjoy anyone else."


So... Mistress Anne's cunt wasn't huge just from childbirth, it was John! He had stretched her to the point that she found my normal dick unsatisfying. And now Joyce was probably somewhere fucking him as we spoke!


"Something else," Mistress Anne said. "Joyce and I talked. Right now her period is during one of the weeks you come clean my house. We agreed you would come next week, and then back on a two-week cycle. That way, her period is during one of the weeks you don't clean for me, and the two weeks you do, she isn't out of commission. So be here again next Thursday - understand?"


I was so consumed by the implications of this that I didn't respond. WHAP. Mistress Anne had hit me as hard as show could with a paddle. "I asked you a question," said Mistress Anne.

"Yes Ma'am."


"Yes Ma'am what?"


"Yes Ma'am I will come again next week."


"... Again next week why?" said Mistress Anne


"So Joyce's period..." WHAP "Yes Ma'am I will come again next week so Joyce's period does not fall on one of my cleaning weeks."


"Now you're getting it," said Mistress Anne.


Boy was I getting it all right. Mistress Anne's big dildo was pushing itself into my ass. She's kept me very loose with regular dildoings, so she was plunging away within a minute or so. Horny as I was, I was soon bucking back, trying to drive her cock into my ass as fast and hard as she wanted to. I felt her tense and shudder, and I knew she had orgasmed at my expense for the fourth time that day.


Mistress Anne, after taking a minute to regain her composure, withdrew her cock abruptly, leaving my ass wide open. She was gone for 10 minutes or so - I could hear her in the bathroom. I heard the phone ring once, but it didn't seem like she talked long. She came back obviously dressed for bed with a blanket in her hand.


"That horse actually looks pretty comfortable. Is it?"


"Yes Ma'am, it's not bad."


"Good," she said as she through a blanket over me. "I think I'll let you spend the rest of the night there. That was Joyce on the phone - John may spend the night with me instead of drive all the way back to Alpharetta. It just depends on how much longer he stays at your house. That view of you would be an appropriate introduction."


"Oh, and I hope your wife fucked him long and hard. You don't want him still horny when he sees you. I'd have to get a bigger dildo just to keep it from falling out of you if he gets a piece of you."


I was almost asleep when I heard the key in the front door. Cold air hit me as he pulled the blanket off. Ten minutes later I was still in a cold sweat as his semen ran out of my gaping asshole down my legs. I heard him say to Mistress Anne as he got into bed with her, "Her cunt got so sore she rolled over and begged me to fuck her ass. That's the first time I've every fucked ?his and her' asses in the same night."






Postscript - Six Months Later


Despite all the humiliation, the cuckolding, the ass reaming, the most perplexing thing about this new era in my life is what I don't know. I've thought about it for hours. All I really know is that Mistress Anne set me up - that much she admits, but only to me. Was it a reaction to my willingness to take the dare, or had she in fact started the whole conversation to lure me into a trap? And what about Joyce's involvement? Did Mistress Anne set the trap and then bring Joyce in at the last minute, or had Joyce been "in the know" from the start? Or had Joyce even been the mastermind?


Joyce and Mistress Anne absolutely will not talk about it, and in fact have made it very clear that additional questioning on my part will be punished severely. So I come to clean Mistress Anne' house every other Thursday just like I have for the last five years. I have no idea what Joyce does while I'm here. One time a couple of weeks after John enlarged my ass, when I got in bed on Friday night, there was dried cum all over the sheets on my side of the bed, including the pillow. Joyce said it was silly to clean the sheets - they had just been changed the day before, so I had to sleep in some unknown man's dried cum for 6 nights. But otherwise, I have absolutely no idea. Since one of my off-weeks is now Joyce's period, I get to fuck her less often than I used to. And it seems like she is looser than she used to be - but we are all getting older. I try not to think about it too much. Whatever she's doing, it's my own dickbrain fault, so I guess I'll take whatever comes my way.

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