“Sissy Maids: The latest trend in relationships” by c.w. cobblestone

“Sissy Maids: The latest trend in relationships”
By Lolita Lankenstein
(as told to c.w. cobblestone)
Interview #1: Dawn, Mike and Tulip
Dawn and Mike snuggle on the sofa, the evening news muted on the big-screen TV. The amorous couple watches their sissy servant Tulip stoke the fire in the sprawling stone-hearth fireplace that dominates the ski lodge’s living room. Once the flame is sufficiently aroused, Tulip scampers to the kitchen and returns carrying three fresh hot toddies.
This would be a theme during my visit with the polyamorous trio: Dawn and Mike relaxed while Tulip, a man dressed as a woman, did all the work. If that seems strange, then you have not been introduced to the world of sissy maid cuckold relationships.
I hadn’t known about the lifestyle, either until last month, when my editor at CNS (Corundo News Service) handed me a novel assignment: Do a story about this burgeoning subset of the poly lifestyle. He explained that these sissy cuckold triads consist of a married couple and a male lover, although the unions differ from traditional threesomes, in that the three participants are not equal; the husband lives as basically a female slave to his wife and her lover.
Marching orders in hand, I began researching the story. It didn’t take long to track down Dawn, Mike and Todd — or, “Tulip”— who are open about their lifestyle on social media. I reached out to the trio on Facebook, and I Skyped with Dawn and Mike for a few minutes. Tulip was “on punishment,” they explained. I was dying to hear more, but figured it best to wait until I set up the interview, rather than waste possibly good material beforehand. They said they were heading to Colorado for a ski trip, and agreed to meet me in their massive Aspen ski lodge.
I was bursting with anticipation as I made the cross-country flight from CNS’s New York office. After a 45-minute Uber ride from the airport, I arrived at the lodge, which was tucked in a snowy ridge at the foot of the Rockies. Tulip answered the door, dressed in a plain, gray maid’s uniform. If I didn’t already know his background, I’d have never guessed he was a male. The sissy took my coat and introduced me to his wife and her lover. Dawn ordered him to tend to the fire and serve drinks. I eased into a chair across from the couple on the sofa and dug my digital recorder out of my bag.
Once Tulip served the hot toddies (none for him), he sat on the floor at Dawn and Mike’s feet. “He’s not allowed to sit on the furniture,” Dawn explained.
Everyone was settled in, so I pushed the red button on my recorder and began the interview:
CNS: So, thank you for allowing me into your life like this. Let’s start at the beginning: how did the three of you meet?
Dawn: So, Tulip and me were married for three years, and … well, we pretty much had a sexless marriage.
Mike: The little pansy can’t get it up.
Dawn (giggles): Don’t be mean, Mike.
Mike: Well, it’s true. He can’t get it up.
Dawn (sighs): No, he can’t. But at least he was honest about it when we first started dating, and he told me he didn’t mind if I saw other men; he just wanted a relationship with me. He also confessed that he was into crossdressing. Small, effeminate guys aren’t my thing, but with Tulip, I never had to worry about that, because I could be with the kind of men I’m attracted to, and he could do whatever he wanted to do as far as dressing in women’s clothes, as long as I didn’t have to see it — and as long as he kept paying the bills.
Mike: Tulip’s always been a sap for her.
Dawn (to Tulip): Aw, Master’s being mean again, isn’t he? It’s okay if my little Tu-Tu loves his mommy. Do you love your mommy, Tulip?
Tulip (clears his throat): Yes, Mistress.
Dawn: That’s my little baba. So, anyway, after a few dates, I knew Tulip wasn’t going to be much use in the sack, but he had a lot of other things going for him.
Mike (cups his hand over his mouth): Money.
Dawn: Oh, come on. It was more than that.
Mike: Money.
Dawn (laughs): Okay, so he makes a lot of money. But he was really sweet, too, and I found out early on that he had learned to make up for his … um, shortcomings with that tongue of his. We had it pierced. Show the nice lady, baba.
(Tulip sticks out his tongue, displaying three large studs)
Dawn: Those feel great on my toes. Best thing we ever did was getting our little Tulip pierced.
Mike (raises his finger): My idea.
Dawn (kisses him): Yes, it was.
CNS (to Dawn and Mike): So, how did you two meet?
Dawn: He was my personal trainer at the club. When he first started training me, he had a girlfriend, so there was never anything romantic there at first.
Mike: Not that I wasn’t attracted to her.
Dawn: Oh, God, yes! I thought he was hot from the minute I saw him; I mean, just look at him. Anyway, I had been dating around ever since I married Tulip, but at first, Mike was off-limits.
Mike: Until I broke up with Cheryl.
Dawn: Mmmm, that was the best news I’d ever heard, you breaking up with that bitch. When you mentioned it during our session, I wanted to jump your bones right then and there.
Mike: Oh, I’d been thinking that from the minute you signed up at the gym. But I’m not a cheater, and I was in a relationship with —
Dawn (sneers): With that stupid heifer.
Mike: Well, she’s long gone now. And I’m a one-woman man — and you’re my woman.
Dawn (snuggles closer to Mike): Mmmmm … you got that right.
CNS: So, you two started seeing each other —
Dawn: He made his move not long after he broke up with Cheryl. Of course, I wasn’t exactly hiding the fact that I wanted him to.
CNS: Did he know you were married at first?
Dawn: Oh, I had told him about Tulip even before he broke up with her.
CNS: What did you tell him?
Dawn: I told the truth: that my husband was a wimp crossdresser who couldn’t get it up, and that I had sex with other men. That Tulip worked all day and then came home and cleaned the house. That he was basically my maid, not my husband.
CNS (to Mike): How did that make you feel?
Mike: Shit, I thought it was sexy as hell. Made me want her even more, knowing her husband couldn’t have her.
CNS (to Dawn and Mike): Is it okay if I ask Todd a question?
Dawn: Oh, please call him Tulip. That’s his name now; we’re actually talking about getting it formally changed when we get home. But, go ahead; you can ask him anything,.
CNS (to Tulip): So, tell me about the first time you met Mike.
Tulip: Uh, my mistress had been talking about him for a long time, even before he broke up with his girlfriend, so I’d known about him for a while.
Dawn: I couldn’t shut up about my hot trainer, could I, Tu-Tu?
Tulip: No, Mistress.
CNS (to Tulip): What was your reaction when they started dating? When did you first meet him?
Tulip: Um, my Mistress had been dating Mr. Mike for a few weeks, and then she invited him home for dinner.
Dawn: I made Tulip clean the whole house, top to bottom. Then, I made him do it again.
CNS (to Tulip): Were you nervous?
Tulip: Yes, ma’am, very much so. I’d met my mistress’s boyfriends before, and that’s always nerve-wracking. But I knew from the way she’d been talking about Mr. Mike that he was different. She always made me clean the house when guys came over, but she never made me clean it twice.
CNS: And what did you think when you met him? I mean, he’s obviously built like a Greek god, and you’re … well, not to be mean, but you’re not.
Tulip: Uh, I know I’m inferior to my master, and so I’m glad my mistress has him to take care of her, because I … I can’t.
Dawn: No, Tulip, you can’t.
Mike (chuckled): Don’t worry, Tulip, I’ll pick up the slack.
CNS: So, when did you all decide to move in together and make this an official cuckold triad relationship?
Dawn: I mean, we fell in love. And Tulip has nothing to say about it. So, it kind of just happened.
Mike: We’d been talking about me moving in together for a while, and we finally had Tulip do it when we went to the Bahamas.
Dawn: Yeah, that was Tulip’s wedding anniversary gift: a trip to the Bahamas for my baby and me, and when we got back, Mike was all moved in — just like magic.
CNS (to Tulip): So, you paid for your wife and her boyfriend to go to the Bahamas, and you moved him into your home all by yourself? That must’ve been hard to deal with.
Tulip: Um, I’m just happy my mistress and master are happy.
Dawn: Go ahead, Tulip; speak freely. Was it hard when you had to move all Mike’s stuff into the house?
Tulip (bows his head): Yes, Mistress. It was very hard. It was one of the hardest things I’ve ever had to do. I felt like I was losing everything.
Mike: Quit whining, sissy, or I’ll take a switch to your ass.
Dawn (chuckles): Poor Tulip. I told you to answer and you get in trouble anyway. Can’t catch a break, can you?
Tulip: No, Mistress, thank you, Mistress.
CNS: By the way, that reminds me: When we Skyped last week, you said Tulip was ‘on punishment.’ What was that all about?
Mike: There were eggshells in my damn eggs, so I blistered his pansy ass.
Dawn: It’s one of Mike’s pet peeves, so he went to town with the cane.
CNS: Do you punish him often?
Dawn: Not as much as we did at first. Other than the occasional screw-up, like with Mike’s eggs, Tulip’s learning how we like things done, so we don’t have to whip him as often.
Mike: Except when you ask me to whip him because it makes you horny.
CNS (to Dawn): It does?
Dawn: Oh, Gawd, yes. I swear, seeing my man beat him into a blubbering mess … to see him crying, and begging and pleading … and the sad, confused look on his poor little face, wondering why I had him whipped when he didn’t do anything wrong … yeah, it makes me horny. Like you wouldn’t believe.
CNS (to Tulip): That seems pretty unfair: You didn’t do anything wrong and you still get punished, after you work so hard to make life easy for them. Doesn’t that bother you at all?
Tulip: I’m just here for my mistress and master to use however they want, and I appreciate it when they take the time to discipline me.
Dawn (to Tulip): Tell the reporter how you thank Mike for your punishment.
Tulip: Um … I … uh … I suck him.
CNS (to Tulip) You mean to tell me you have to give your wife’s boyfriend a blowjob to thank him for whipping you?
Tulip: Yes, Ma’am.
CNS: Wow. That’s incredible. Okay, so, sex-wise, how does this work? Mike, are you bisexual? Do you and Tulip ever have sex?
Mike: I don’t know if you could say he’s actually having sex. Bill Clinton said a blowjob doesn’t count as sex, so I guess I’m safe.
CNS: So, Tulip, you don’t have sex at all, other than giving oral?
Tulip: Uh, no, giving my mistress and master pleasure is my sex life.
CNS: So, I assume you masturbate a whole lot, if you’re not getting any other action.
Mike: Oh, hell no. He only gets to cum once every few months. Otherwise, he gets lazy.
Dawn: And he runs his mouth after he’s cum, too. Tulip, tell the nice lady what your master did the last time we let you cum, and you gave me backtalk.
Tulip: Uh, Master gave me 50 with the cane and I had to sleep in the shed for a week.
Dawn (giggles): It gets cold out there, doesn’t it?
Tulip: Yes, Mistress.
Dawn: I’ve told you a million times: Don’t piss him off. (She snuggles her cheek into Mike’s bicep). My baby is such a bad-ass.
CNS: Let’s back up. You said Tulip only cums once every few months? Seems hard to do; how do you know he’s not cheating and masturbating in the bathroom or something?
Dawn: Oh, I assumed you knew already. We have him caged.
Mike: Tulip, get up and lift your dress; show the nice reporter your cage.
(Tulip stands and hikes his dress, revealing a pink plastic tube covering what’s obviously a tiny penis).
CNS: Oh, my gawd! I’ve heard about these chastity devices, but I’ve never actually seen one. Isn’t that uncomfortable?
Mike: How the hell am I supposed to know? You wouldn’t catch me wearing something like that in a million years.
Dawn: That’s because you’re a real man, and he’s a little sissy.
CNS (to Tulip): Is it uncomfortable?
Tulip: Um, I’m used to it, but sometimes it does feel a little tight.
Mike: Good thing you can’t get that little weenie up, ain’t it? That would make it even tighter.
Tulip: Yes, sir.
CNS: So, what’s the living arrangements? Does Tulip have his own room?
Dawn: He sleeps on the floor down in the basement, in the laundry room.
Mike: If he’s good, we let him sleep on his little blanket.
Dawn: We go by the point system. If he screws up during the day, we give him points. Three points, no blanket.
Mike: Shells in my eggs? That was ten points.
Dawn: So, no blanket for three days.
CNS: And you make him sleep in the shed for the really bad infractions?
Dawn: That’s Mike’s thing. (giggles) He’s so bad.
Mike: Hey, sometimes you gotta let the little pansy know who’s boss. So, I put his ass in the shed for a few days.
Dawn: Or a week.
Mike: Yeah, when he really makes me mad.
CNS: Tulip, what’s that like sleeping in the shed?
Tulip: I don’t like it, ma’am, but my master knows what’s best for me, and he sends me to the shed so I’ll learn my lesson.
CNS: But what’s it like?
Tulip: It’s freezing in the winter, and in the summer the bugs eat you up. That’s why I try hard to serve my mistress and master well, so they don’t send me out there.
CNS: And then when you sleep in the shed, you’ve got to get up and go to work?
Tulip: Yes, ma’am.
CNS: And then you come home and do housework? That sounds like a long day. You must get tired.
Dawn: Sissies aren’t allowed to get tired. (Giggles) Although I admit, we do leave messes sometimes. The poor little pansy was up all night last Monday cleaning the wine stain out of the carpet, and then Mike kept him up until nearly 3 in the morning the next night polishing his Range Rover.
Mike: Hey, I was meeting my buds for some golf and I wanted my ride looking sharp. What’s the point in having a sissy around if you’ve got to worry that he might be a little tired.
CNS: Well, it’s getting late, so I’m going to wrap this up. It’s been fascinating, to say the least.
Dawn: Maybe you could find a little sissy maid of your own who’ll pay the bills and let you have a love life with a real man. It’s the best, believe me.
CNS: Well, I’m certainly tempted.
NEXT MONTH: My journey into the world of sissy cuckold triads continues with my interview with Kimberly, her lover, James, and their servant Daisy.
Until then, I’m your CNS roving reporter, Lolita Lankenstein