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:
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.
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.
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 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.