Lesbian Milf Seductress: Halloween

Summary:

Teacher's lez side is awakened by chance encounter.

Note 1:

This story is a 2019 Halloween Contest story.

Note 2:

Thanks to Tex Beethoven and Robert for editing.

Note 3:

This story stands on its own, but if you want to read more BREE stories, check out the following (listed in chronological, not date published, order):

Lesbian MILF Seductress: Pre-MILF (in Bree's senior year of high school)

Lesbian MILF Seductress: Mom (late in her senior year)

Lesbian MILF Seductress: Neighbor (late in her senior year)

Lesbian MILF Seductress: Chocolate (immediately following Neighbor)

Lesbian MILF

Seductress: Bakery (a couple weeks after Neighbor & Chocolate)

Lesbian MILF Seductress: 30

th

B'day (late summer, last weekend before her beginning college)

Lesbian MILF Seductress: Halloween (during her first year of college)

Lesbian MILF Seductress: Secret Santa (during her first year of college)

Lesbian MILF Seductress: Nurse (during her first and third years of college)

Lesbian MILF Seductress: Cop (summer after her first year of college)

Lesbian MILF Seductress: Pop Star (summer between

sophomore and junior years of college)

Lesbian MILF Seductress: Church Mom (immediately after Pop Star)

Lesbian MILF Seductress: Spa (during the beginning of her junior year)

Lesbian MILF Seductress: Librarian (during her third year of college)

Lesbian MILF Seductress: Bride (End of third year of college)

Lesbian MILF Seductress: Librarian (During her senior year)

Lesbian MILF Seductress: In Flight (summer job after college)

Lesbian MILF Seductress: Halloween

Bree:

As my first year of college began I was beginning to understand the special 'Spidey' like sense I had: being able to sense when an older woman was unknowingly ready for a sexual awakening.

I was also exploring my own sexuality. I mean I was a Mistress, I could dominate girls and women. I controlled my emotions. I remained in charge. Yet, although I knew I liked being in control, I had experienced being a sub as well (read Lesbian MILF Seductress: Mom for that story), but I was curious what a sexual encounter without a sub-domme relationship would be like.

This is a story of a seduction that began and ended in just a few hours and is much more intimate compared to most of my seductions.

Daphne:

I hated Halloween.

I hated dressing up.

I hated seeing slutty outfits all day.

I hated arguing with my high school senior daughter that her costume was too inappropriate for school or even any other place.

Yet I had agreed to supervise the Halloween school dance. Where I would undoubtedly encounter dozens of inappropriate costumes.

I avoided supervising school dances because they tended to be grind fests, and a Halloween dance seemed like an open invitation for teens to go wild, but my principal was short three supervisors, and so I reluctantly agreed to do the early shift. I would be finished by 9:30 and in bed by 10:00 (only half an hour later than my usual weekday bedtime... I was an 'early bird catches the worm' sort of woman).

My daughter would stay until 11:30 and could drive herself home.

So I needed a costume, since the costume I was wearing today while teaching, my daughter said was the lamest costume ever, and she didn't want me to embarrass her. Add to this the fact that a couple of my teacher colleagues also teased me for lacking creativity and Sarah, my best friend, dressed a little too provocatively for a teacher in my opinion, pointed out this was the day I should let loose.

Letting loose wasn't something I did much of.

Especially after my husband had left me for his much younger secretary.

Nope, instead I buried myself in work, kept working on my Master's, and I watched a ton of Netflix. I also discovered the joys of electronic toys when Sarah held a sex party a couple months after my separation, and I returned home with four sex toys... which was four more than I'd ever had before that day.

I won't bore you with the details, but they were a revelation. The build-up was more exhilarating, the variety of speeds and pulses were more stimulating, the orgasms were more intense, and most importantly, I discovered I could have multiple orgasms... hear that? MULTIPLE ORGASMS!!!

Who the fuck needed a man? My husband had never gone down on me (my only oral orgasm had been from an older guy in college), and I had only come from getting fucked a few times from my husband, and I had to have at least a couple of drinks for that even to happen.

Anyway, I was in a bit of a mood when I stopped at a costume store after school to pick up something, figuring there would be slim pickings on Halloween day itself.

So I was surprised by the plethora of costume choices... I had four costumes at home, and I rotated them every four years since I worked at a high school... truth be told, I hadn't bought a new costume in years.

So although I usually bought tame and safe costumes... my daughter's words lingered in my mind, as did Sarah's, and they had me looking for something a little bolder. Not

crazy

bold since I was going to a high school dance, but bold enough to turn a few heads and not to be considered the boring Ms. Jones, having recently returned to my maiden name.

That said, I was quite shocked at the discrepancy between tame and bold.

There seemed to be no middle ground.

Everything had a kinky version to it.

Slutty nurse.

Sexy teacher.

Revealing Snow White.

Inappropriate nun.

Stop traffic cop.

Sultry pirate.

Wild (chaps only) cowgirl.

I was literally lost for what I should wear when a very pretty college-aged girl in a risqué witch costume, which didn't hide her perky breasts or firm ass asked, "Can I help you?"

"I think I'm beyond help," I joked.

"For work or fun?" she asked

"A high school dance," I answered.

"So you're thinking sexy, but not slutty?" she asked, reading my mind.

"That sounds about right," I nodded, before adding, "although all these costumes look too flimsy to hide these." I pointed to my large tits.

"Yes, every costume here will draw attention to those," she said, looking directly at my chest area.

"They've drawn attention my entire life," I sighed, having developed young and always had the biggest beasts of my classmates. They drew attention from the boys and scorn from the girls.

"I understand," she smiled, as she openly admired my chest area.

"So more sexy than slutty?" she repeated, although it was more to herself as she pondered which outfit would work for me.

"Well," I pondered, feeling a little like it was time to show my daughter I was no prude, and for some reason wanting to impress this very pretty girl, "maybe a little more slutty than sexy."

"Perfect," she smiled. "In that case, I know just the costume."

"Sweet," I said, trying to act younger than I was.

She walked away and returned a minute later with a Daphne costume from Scooby Doo. Oddly, I wore a Daphne costume in high school since I was a redhead and, well, my name is Daphne. I laughed, "Figures."

"What?" she asked, looking genuinely concerned.

"My name is Daphne," I said.

"Oh, sorry," she said. "I can find something else."

"No, no," I corrected. "I love it."

"You do?"

"Yes," I nodded. "I dressed as Daphne back in high school."

"You do look exactly how I imagine Daphne would look as an adult," she said, squeezing my hand.

"I'm flattered," I said.

She kept holding my hand as she added, "My first crush as a teen was Daphne."

I felt my cheeks go red.

Was she flirting with me?

"Mine was Fred," I admitted, which may seem corny, but was the truth.

"I always thought Fred was gay," the girl said.

"Really?"

"The ascot?"

"I also imagined Velma and Daphne having their own mysteries to solve when they were alone," she said, her hand still holding mine. Her eyes looking into mine.

"Oh," was all I could muster as a chill went up my spine as her thumb slowly moved in the smallest of circles which felt so nice... relaxing... trusting.

"Yes, Velma is definitely a lesbian," she continued, her eyes not breaking contact with mine.

"I never thought about that," I said, although now I couldn't get it out of my head.

"Do you want to try it on?" she asked.

"What?" I asked confused.

"The costume," she said.

"Oh, yes, sure," I said.

She handed the classic outfit to me and pointed to a change room.

In the room, I got out of my clothes and into the outfit. It was a thinner fabric than I could have possibly imagined. It was also a lot shorter than I'd anticipated.

There was a knock at the door. "Let me see."

"Um, okay," I said.

I opened the door and she entered the tiny room.

"Adorable," she smiled, as she looked at me. "You don't even need a wig."

"Thanks," I said, flattered to get attention from a pretty coed lesbian.

"But it's missing something," she said.

"What?" I asked.

"Nylons," she said.

"Right," I nodded, thinking Daphne always wore pink pantyhose, or sometimes purple in later cartoons.

"Here," she said handing me a pair of pink nylons.

"Thanks," I said.

"Actually let me help," she said.

"Pardon?"

"Sit down," she said.

"Okay," I said tentatively.

She took the nylons and knelt before me.

My eyes went wide.

I learned they weren't pantyhose, but thigh highs when she placed one stocking beside me and rolled up the other one.

I stared as she lifted up my foot and slowly rolled the pink nylon on me.

It was a strange... oddly erotic... feeling.

My pussy agreed as I felt a slight gush leak out of me. As my leg was lifted, this stranger had a direct look at my panty-covered pussy and, I feared, a wet spot.

As her hands moved up to my thigh, I trembled. No one had touched me in months, and although she was a girl, my body was reacting to her touch.

She paused when the first thigh high was on, and definitely glanced at my crotch. She smiled ever so slyly, before she reached for the second thigh high and repeated the supposedly innocent, yet incredibly erotic act.

Once both were on, she stood up and pulled me to my feet. "Let's take a look in one of the full mirrors."

"Okay," I said, for some reason just doing whatever she told me.

She left the stall, and I followed.

Curious what I looked like in this rather sexy outfit, I looked at myself in the mirror.

"Oh my," I said, looking pretty fucking hot if I said so myself.

"You look ravishing."

"Thanks, that's not a word usually used to describe me," I responded, although I was flattered to get a compliment from a girl half my age.

"I'm the one dressed as a witch, but I think

you

have

me

under a spell," she said, really checking me out.

I laughed, "It's not me, it's the costume."

"No, it's you," she disagreed, indeed enamoured with me.

I had never been with a girl, never even considered it, but I was indeed flattered. I wasn't sure what to say, as my pussy was on fire, but my moral code, my straightness and the fact she was half my age had me trying to remain calm, so I simply said, "Thanks."

"No problem," she said, before I returned to the dressing room. As I got out of the costume, I looked at my panties and found there wasn't just a wet spot... there was a wet lake.

Were they wet because a pretty college girl was flirting with me?

Was I wet because I looked so hot?

Why was I wet?

Shit, I really needed to get laid.

I changed back into my more casual attire and went to pay. I was oddly a little disappointed when the college girl wasn't at the till, but another cute girl.

I paid and looked around for the college girl... I don't know why... what was I hoping for? I left the store and saw her leaning against the wall and a chill went up my spine. The kind of chill I used to get when I was younger and a boy I liked showed an interest in me. Was she waiting for me? Did I want her to be waiting for me? What was happening to me?

She said, "You should have kept it on."

"I had to pay for it," I said, walking to her.

"I guess," she laughed.

"I wanted to thank you," I said.

"For what?" she asked.

"For helping me with the costume," I said. "You were a great help."

"It was my pleasure," she said, in a sexy tone.

Oh, you brought me pleasure

, I thought to myself, but of course wasn't brazen enough to say that out loud. I asked, "Are you off work?"

"Oh, I don't work there," she said.

"You don't?" I asked, surprised.

"No, I just saw you, thought you were cute and came over to help you," she said brazenly... like I wish I could be.

"Oh," was all I could muster as I processed her words.

"Give me your phone," she ordered.

I should have asked why. I should likely have said no. Yet I mindlessly unlocked it and handed it to her, completely captivated by her.

She quickly typed something and said, "Once your dance is done, you should stop by the campus. We're having a Halloween party."

"Oh, thanks," I said, unsure what else to say... although as I felt more wetness gush into my panties I knew the reason they were wet.

"I expect to see you there," she said as she handed me back my phone.

"I'll try," I said noncommittally, taken aback by the offer, by her sudden more authoritative tone although all the while smiling, and by my own physical reaction. I had never considered being with another woman in my life. Sure, I knew when someone was pretty, but other than a couple kisses in college to tease the boys, I hadn't considered it. Plus, her firm tone triggered another gush in my panties as I recalled my college submissive relationship with Wayne... a guy who knew exactly what I needed sexually... something my husband never really understood.

"No," she said, moving directly in front of me, the scent of her perfume noticeable, as she added, one more word, "Do."

"Okay," I agreed, unable to disobey her firm words.

"Good," she said,

"Okay," I said, "but it may be late."

"I'll be waiting up for you," she said, before adding, as she leaned into my ear, "and you won't regret it."

Another gush of wetness flooded my panties as she added, "I'll be easy to spot. I'll be the one in a slutty Velma costume."

She then, in a mall full of people, leaned forward and kissed me.

It lasted two seconds.

It lingered forever.

Then... she simply... walked away.

I stood there in a stunned daze.

Realizing a couple strangers were staring at me, I quickly left the mall, my head spinning, my face flushed and my pussy leaking... fuck, I really needed to get laid.

In the car, I checked my phone and saw she had texted herself:

Hi Bree, I will be there tonight. Pet Daphne.

Bree. Somehow that just seemed like the right name for her.

Pet Daphne. What did that even mean?

I returned home, my pussy on fire. I went directly to my room. I pulled up some porn on my iPad. I fucked myself with my vibrator. As I came, I imagined Bree kissing me.

As I recovered from my orgasm, I couldn't help but wonder... what would it be like to be with a woman? Bree had awakened things inside me I didn't know existed.

I suddenly felt ashamed.

I was a mother.

I wasn't a lesbian.

I wasn't even bi.

I couldn't meet a college girl.

At nine or later.

.....

After dinner, I put on my costume and realized it was too short to wear to a high school dance.

Yet I wanted to wear it, so I compromised. Instead of the thigh highs, I put on a pair of black leggings that would make the outfit less authentic, but also less slutty. That said, for some reason, for the one percent possibility I'd end up going to the college, I put the thigh high stockings in my purse.

I went to the dance.

Got compliments on my outfit.

My daughter even complimented me.

Around nine, my phone buzzed.

It was a text.

From Bree.

Are you coming? And by that I don't mean are you CUMMING... that is a guarantee... I mean are you coming NOW?

I gasped.

My friend Sarah was beside me and asked, "What?"

"Nothing," I said too quickly.

"That expression on your face could be a lot of things, but

nothing

is not one of them," she assessed accurately.

"I met someone today, and they want me to meet them at a party," I said, avoiding the gender pronoun. I was a terrible liar.

"Reeeeeeaaaaally?" she said, in that way she did.

"Yeah," I nodded, feeling oddly excited by the fact I had someone interested in me. Even if it was a girl... a younger girl... a much younger girl.

"Where did you meet him?" she asked.

Continuing to ignore the pronoun, I answered, "While picking up this costume."

"Serendipity," she said.

"Maybe," I shrugged and then pondered that concept. There were a lot of things that had to line up to make that meeting with Bree work.

1. I had to agree to supervise a dance I didn't want to attend.

2. I had to let the criticisms of my being too conservative build up until I felt the need to make a sexy statement.

3. I had to choose that store, in that mall.

4. Bree had to be there the same time as I was.

5. Bree had to come over and help.

6. I had to let loose a bit.

7. She had to see me. She had to be intrigued by me.

8. She had to find a way to push my buttons.

Serendipity.

So although I wasn't a lesbian, Bree had me curious.

"Perhaps," I said non-committally.

"You're going to go and meet him?" she said, although it wasn't really a question, it was a statement... an order.

"Perhaps," I repeated.

"No one needs to get laid more than you do," she said.

"I really just need my pussy licked," I replied bluntly.

"You can go to Karen for that," Sarah laughed. Karen was our not very attractive school secretary who had announced last week she was bi.

I laughed, "If I was going to lez out, I hope I could do better than that."

"I imagine you'd be a great lesbian," she laughed back.

"You think so?" I said with a smile, giving her my seductive look.

"You'd definitely be the femme," she added.

"What does that mean?" I asked.

"You wouldn't be the one wearing the strap-on," she quipped.

"I could wear a strap-on," I argued, although that hadn't even popped into my head as a possibility, as my phone buzzed again.

Sarah laughed but asked, "Is that him again?"

"I don't have telepathy," I joked, as I pulled my phone out. It was her.

Respond, my pet. We both know you want to CUM!

I felt my face flush, my panties dampen, and Sarah snatching my phone from my hand.

"Sarah, no!" I gasped, grabbing for my phone.

"I just want to see what your mystery man is saying," she insisted, stepping away from me.

I stood there helplessly as she read the two sentences and scrolled up to the rest of the short one-sided conversation.

The look on her face shifted from amused and playful to one that was, the best I can describe as surprised.

As she held my phone, it buzzed again. Sarah handed me back the phone, "You should probably reply."

I took the phone and read the new message, both mortified to have such a conversation discovered by my best friend and yet oddly excited to read the message:

Answer now, my pet!"

I looked up to Sarah, who was looking at me.

I looked back down at the message.

Sarah said, surprising me, "It's okay, Daphne."

"What is?" I asked, a mix of confusion.

"To want to go," she said.