The survey for this new job was just plain weird. Questions like:
“It is better to serve than to command Y/N”
“I’m comfortable in my own skin Y/N”
“Sexuality is a spectrum Y/N”
“Men should be manly and women should be ladylike Y/N”
“You are easily intimidated by others, especially strong men and beautiful women Y/N”
“It’s unfair women have so many clothing options compared to men Y/N”
“On a scale of 1-10, how much of a traditional male are you?”
***
Looking for jobs for three months, I’d begun to get desperate. Postings about housework no longer had me scrolling past. I applied to everything, and still, nothing. So when they contacted me back, I felt a rush of excitement and an even greater pinch of anxiety.
Mature couple seeks maid (male).
Growing older with my great husband has left us with a clearer idea of what we need and what we don’t. Looking for a reliable worker with few other responsibilities to stay with us and take care of our home. Leaving us time to further explore what the world has to offer.
*Dress code required*
Not my ideal, a little weird to be sure, but also, they were offering quite a lot more than I could get elsewhere.
***
Their house was both massive and ultra modern. I went to knock on the door but it opened before me.
“Looks like I got ahead of you there. The name’s Madeline.”
Beauty itself answered the door. 6′ compared to my 5’6 self, a black dress with a leg slit showing more leg than I’d ever seen a girl show in real life.
Trying to hide my frequent searches of “Milf” porn I felt rush to my eyes, I hurried out an, “Oh, haha, I guess so,” and scratched my head.
“Already blushing, how cute, there’s no need to be anxious sweetie.” I’m sure my blushing doubled. “Let’s get you inside, hmm?”
I felt myself shrink behind her.
Sitting on the couch opposite her, “So, looking at you…r resume I think you’re a great fit for the job. You’re about twenty, right?”
Caught off guard by a job offer so soon, I mumbled and looked around.
“Do you have any questions before we start?” She smiled.
Starting work today already? “Um, er, there was one thing. I kinda forgot. Oh yeah, um, I was wondering what was meant by the mention of the dress code?”
“Oh!” She laughed. “Our AC is on the fritz lately, so we don’t want you passing out or anything silly like that. Happened to our last employee. So, this time, no passing out! Light clothing, at least for now. That’s all we meant by it.
“I don’t really have more than I wore” I shrugged: baggy clothes to cover my body I wasn’t all-too-comfortable about. “Maybe I can come back.”
“Well I don’t want you to miss out on today’s pay…but if you’re alright with that…”
Geez. “Actually, uh, yes, I can just stay here.”
“Great! Let me give you some things to borrow,” she extended her hand in agreement but squeezed much, much harder than me. I thought I saw a sly smile creep up one side of her mouth. Then, she patted my thigh and stood up.
***
“This is your room, it was our daughter’s before she moved out, haven’t really touched it since. But we can work on making it fit you later. I’m thinking my clothes might actually fit you a little better than my husband’s I’m sorry to say. I’ll be right back!” What did that mean?
There was so much pink it seemed almost a parody of a teen girl’s room. Oddly, I didn’t notice any pictures of their daughter with her or her friends as I thought would be normal. The dresser caught my eye and I opened it to check the space I’d have for my clothes. A white bralette with the words ‘Daddy’s Girl emblazoned in pink jumped out at me.
What the hell, I thought. I closed it abruptly at the sound of heels approaching.
“Here we are.” She threw some items on the girly bed.
“I’ll let you change in private, honey.”
I wasn’t expecting much but a yellow crop top with flowers, like a sundress, and white high rise shorts? Really? How bad did I still want this job? Bad. As I was appraising the clothes in my hands, a pair of lacy yellow panties with a bow fell out. Must’ve been mixed in during laundry.
Really, though?! Girl clothes? Really, really girly clothes. God, why did I need this money so badly? I was already this far, this close to an actual paycheck. One less day of worrying about rent…I went ahead with it. Only—the high rise shorts completely showed off my underwear. I couldn’t help it. Damn. My eyes inevitably drifted to the panties.
A knock. “Come in.”
“Ooh oh my goodness, you look great! You remind me of my daughter so much really, aside from your being a boy of course,” she winked.
My cheeks burned. Would I ever live this down? The thing was, despite the change in clothing, I might still pass out.
Afterwards, Madeline showed me around and let me know what was expected with the couple’s cleanliness standards.
***
Madeline told me she wanted their newly cleaned laundry brought to her. It was only a few things so she took them out of the basket as I held it. She had some pretty racy lingerie and had no qualms about holding sexy bras up to her large breasts.
“Hmm…sweetheart, I have an odd question but don’t feel off, it’s just necessary given the job. Did you happen to spot a pair of yellow…panties anywhere?
My heart dropped. Um. Her eyes pierced me with a strange omniscience. The floor felt wobbly, my eyes started to darken—and then I woke up.
***
A cold face cloth was being dabbed onto my forehead. Madeline’s breasts were nuzzling against my arm as I came to.
Horrified, I quickly explained that my anxiety made it hard to hold down a regular job and I was really sorry and I’d do anything to keep this job.
“Oh baby, mo…my husband and I, rather, perfectly understand. You can have all the time in the world getting used to your duties. No pressure. However, you did have another…accident with your…accident I’m afraid. A little wet spot was on your shorts after you passed out.I tried to fit you with my husband’s boxers, just in case, but they were far too loose as you might—well.” She gazed down at my blanket-covered crotch almost longingly.
I felt hot and my cheeks felt redder than ever.It had been slowly building since I woke up but something about the situation, the unfamiliar affection, the vulnerability, I don’t know, got to me.
“Oh dear,” she covered her eyes as my ‘tent’ became too obvious. “Wow, I was not expecting that. Listen, dear, my husband is a great massage therapist. He came home as you were having your beauty sleep. Maybe he can help you relax?”
I nodded sheepishly. Not willing to undermine my chances anymore.
“Turn over baby. That’s it.” I removed the blanket only to see myself in a black thong with a red lace trim.
Her husband was going to see me like this? Another man? And my boss?!…I started shaking. Her warm arms enfolded me, squeezing me tight. The best hug of my lonely life. So warm and enfolding.
“Sweetie, it’s okay, whatever you’re afraid of, it’s nothing, he’s a professional and you’re still on the clock. Don’t let your little head get in the way, mhmm?” She led me away by the hand. Overwhelmed, I’d just started following directions without thinking..
Face-down, my ass in the air much more than I was prepared for. This massage table seemed a little off. I just kept thinking of that hug.
A bassy voice drifted in from the hallway. I thought I felt my skin vibrate to it, near-imperceptibly.”Not even poking out of a thong, my god babe,” I heard the unmistakable sound of a wet kiss from outside the room.
He stepped in. “Not the best way to be introduced I’m sure, but I heard about everything and I think I can help.” I hadn’t even seen his face!
At first his hands were cold.
“Are you always this warm?” he asked.
“Um”
“Forget it, just relax.”
Soon, as our temperatures adjusted, I couldn’t help but notice the massive hands, the strength behind them, and how easily my body moved and adjusted to his touch.
“Ugh,” I let out involuntarily.
“That’s it, let go, focus completely on letting go.”
My nipples rubbed against the leather as he pushed me against the table. I’d forgotten my bulging panties in all the things happening at once. Back and forth into the soft material; against the table, irrevocably sandwiched between. I could maybe still hold it off. I tried to hold my hips hard against the table so my upper body swayed more than my bottom half.
But then:
“Stop me if this is too far.” Those massive, strong hands began to knead my nearly bare ass…my bulging panties rubbing against my cockhead…giving up control of my body to an older man…
“Oh no, oh God, ugh….nghhh….mmmmmmm,” I bit my lip. “Uuuughhhh.”
“What the hell. Did this little boy just cum?”
I felt myself being turned over. White, sticky cum was dripping into my thighs. My legs were still shaking. The panties were obviously very wet, and my receding bulge made it look like I was almost a girl. I’d never felt so humiliated.
“Oh it’s okay, baby,” she came from behind and rubbed my shoulder caringly. I didn’t know Madeline had stayed in the room. “There’s nothing to be embarrassed about! It happens more often than you think.”
I began to look up into her eyes with a remaining spark of trust.
“Maddy…” he started.
“Two panties in one day?” Madeline chuckled. “Well, good thing we have a new maid.”