Be Careful Where You Sleep

As always, I need to thank LittleAlison (a great author on this site) for her endless support. I also want to thank the editor for this story, Bry1977.

Please vote as this is a

Halloween Story Contest 2023

story

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Be Careful Where You Sleep

I awoke to a silken finger moving knowingly in my pussy under the short skirt of my slutty nurse costume. She was also gliding her fingertips up and down my bare arm with her other hand. The combined feelings sent chills up and down my spine. That's how I knew I was awake, no dream is that vivid.

Many thoughts ran through my young, sleep deprived head... First, whose fingers...? I have no clue. Last thing I remembered I fell asleep on the couch of a frat house during a Halloween party. No, I didn't pass out from drinking too much. I was exhausted from not sleeping the night before. My dorm mate, and head cheerleader, Shannon and I had some energy drinks. We pulled an all-nighter studying for midterms. The caffeine must have finally worn off, and I guess I just crashed on that couch.

How did I know it was a woman? I was half sitting up with my back leaning against ample bare breasts. I could feel long hard nipples poking me through the thin material of my slutty nurse crop top. A smooth skinny bare arm was gently wrapped around my bare belly. Each of my hands were resting on two silky smooth, black nylon covered legs. Legs that were wrapped around mine, keeping my legs open. A smooth chin rested lightly on my right shoulder, sweet warm breath tickled my neck. A light perfume with a mysterious bouquet made my nostrils flare.

I found a few more clues about my bed companion while she kept me on edge by slowly circling my clit with her thumb. Enough light was coming from underneath the bedroom door, to illuminate the mirror opposite the bed. I could make out her long red hair under a witches hat. Her naughty smile made her glossy purple lips stand out just under the black mask that disguised the rest of her face.

During Shanon's and my all night study session, I mentioned that I hadn't had sex in six months. Shannon made it her mission to rectify that. "College is a time to party and get laid as much as possible!" She proclaimed. She went right out and bought me a slutty nurse costume that morning.

She put, at least I thought, an excessive amount of makeup on me. Bright red lipstick, eye liner, eye shadow, long fake lashes, the works.

How she convinced me to go without a bra or panties with the crop-top and short skirt costume I'll never know.

Actually, I do know. See, I'm not the type of girl most guys go for. I'm plain looking to the point of being completely unnoticeable. I'm short, small breasted, and have kinky brown hair and brown eyes. Plus, my freshman fifteen turned into at least thirty. I was overweight, the only clothes from home that fit me were sweats and an over-sized sweatshirt.

My hot, blonde, cheerleader dorm mate Shannon told me the only chance I had to get laid that night was to wear that slutty nurse costume and bend over a lot. I'd wished she didn't put it that way, but she was probably right. I also had poor body image and extremely low self esteem. I often gave into peer pressure.

I know what you're thinking, why was a straight girl like me allowing another girl to pleasure me without making any effort to get out of there?

Probably because my one and only sexuality experience up until that point was a complete disaster. It was my prom night, six months ago in the back of my dad's Lexus. I had just turned eighteen. My date, Mark, was a heavy handed, clumsy, clueless oaf. I felt like I was being mauled by a bear. I wasn't even wet when he entered me and it hurt. After the fourth thrust, he came. Then he said, "that was great hon," pulled up his pants, and got out to high five his friends waiting outside the car.

I felt used.

I felt like a dirty whore.

I felt completely humiliated.

I wanted to crawl under a rock.

I hated myself, but my friends told me that everyone loses their virginity by prom night.

Whereas, this woman in bed with me was fingering me better than I ever fingered myself. Plus, her silky legs that were wrapped around mine felt wonderful. Her gentle caress around my waist made me feel wanted.

I never felt trapped. Actually, I was feeling goosebumps and tingles rise on my neck because of her warm breath, and my chest was rising and falling with anticipation.

All that convinced me that I should just let this happen. I told myself that this was just experimentation. Being with a guy wasn't great, maybe being with another girl was. And... I could still tell Shannon that I indeed had sex.

Whose bed was I in? I didn't know that either. But it must have been a guy's bedroom. The faint light let me see the silhouette of football memorabilia on the walls.

Using her thumb, with just the right pressure, she circled my clit while I watched her middle finger disappear inside me, only to reappear glossy wet. The fingertips on her other hand were tenderly gliding up and down my arm. I couldn't resist moaning in delight. Suddenly I heard the naked masked woman whisper in a sweet voice, "Do you want me to stop Cassie?"

Shit, she knows my name! And she sounds like an older woman! Do I know her? I thought about telling her to stop. But the wonderful tingles that were happily traveling throughout my body kept me from saying anything for several minutes. I just kept breathing deeply thinking that I found heaven. I wondered what would come out of my mouth.

I finally stuttered out, "Oh God...I... I don't know who you are... so... so I want to say, yes, p...please stop... but I can't." I let out a long sigh that turned into a moan. "You're ma...ma... making me feel things I've n... n... never felt before."

"Good girl Cassie. Now, will you let me play with your sweet young pussy for as long as I want?"

Her voice sounded angelic, she smelled wonderful, and her fingers, on both hands, were instruments of pure pleasure. What choice did I have?

She began kissing and nibbling my neck. I finally gave in and hissed out, "yesssss..."

"That's great Cassie, I just love playing with young pussy until it's dripping wet." My wetness was apparent by the sounds her fingers were making, easily gliding in and out of my pussy.

The hand that wasn't stirring up a tingle tornado in my pussy, reached under my flimsy, slutty crop top that barely covered my breasts and started gently rolling my left nipple between her fingers. Then she started lightly nibbling on my earlobe... That always drives me crazy.

"Oh, fuucckk yesss!" I moaned loudly.

I was about to fall off that glorious edge. I couldn't wait to feel that sense of falling when... she stopped all of her attention on me. She brought her soaked fingers up to my mouth. I knew what she wanted, but I refused.

"Do you want me to make you cum Cassie?" She gently whispered. I nodded yes. "Then suck your juices off my fingers sweetheart." It wouldn't be the first time I've tasted myself. But doing it in front of her, someone I didn't even know, felt like I was putting my most intimate moments on display. But again, what choice did I have?

I opened my mouth and licked and sucked on her skilled fingers. The abundance of my juices surprised me. The sweet, salty flavor was stronger than I remembered. My lover hummed with approval as I sucked her fingers. Then she went back to fingering me and rubbing my clit. I was once again well on my way to a spine tingling orgasm.

Feeling the momentum building, she went back to nibbling my earlobe again. Her lips brushed against my ear as she whispered, "you are such a beautiful young girl Cassie and you have such a beautiful young body, I'm so glad that you're letting me play with you."

I knew I wasn't beautiful or had a beautiful body, But thinking that there was someone in this world who thought I was, felt wonderful. My heart skipped a beat just hearing the words 'you're such a beautiful girl'.

I was on the precipice of a mind numbing orgasm once again when she suddenly stopped what she was doing once more.

"Oh God, why did you stop?" I whimpered. She brought her fingers to my mouth again. This time I eagerly sucked her fingers dry of my juices. And at the same time she said, "If you want me to continue Cassie, you must ask me nicely."

I certainly would ask her, but my curiosity about who I was with piqued. "Do I know you? What's your name?"

"If everything goes as planned Cassie, you will never know who I am. But you may call me any term of endearment you would like. Personally, I like it when my wife calls me 'darling'."

"You're married? And you're cheating on your wife with me?

"No my dear Cassie, my wife and I have an understanding. She knows exactly what I'm doing tonight. See, she and I had a wild and varied sex life before we got married. So monogamy was difficult for both of us. We decided we would let ourselves go crazy a few nights a year. We call it a 'free' night.

"We picked Halloween as one of those nights because we both loved to dress up in slutty costumes anyway. We gave each other permission to do anything we wanted, no matter how slutty or sex crazed it was.

"Tonight, my wife dressed up as slutty nurse too, only... her skirt was so short, it left nothing to the imagination. Her pussy and ass were openly on display. And I'm sure that's exactly what she wanted.

"My witch outfit is almost as bad, the black fabric for this costume is pretty sheer. In the right light, my black lacy bralette and narrow thong are completely visible. My black thigh-high stockings have some nice lace on them too.

But the real slutty thing about my costume is that it is held together in the back by three small pieces of Velcro. One quick tug and I'm a slut, ready for anything.

"My wife's slutty indulgence is to be a unicorn at a swingers Halloween party. Right now, she's having sex with a dozen or so costumed women AND men. My slutty perversion is making barely legal, young pretty girls, my sex toy for the night. Most girls are about one third my age."

"Oh my... so you're fifty-four?"

"Fifty-five actually."

"And I'm your sex toy for the night?" I said with a crooked smile. Thinking that someone thinks I'm sexy enough to BE a sex toy.

"Are you OK with that Cassie?"

"I guess so, but being with you so far tonight has been life changing for me. It saddens me that we can't do this again."

"Trust me Cassie, there are many girls on this campus that would love to be with you. I can tell you right now, that your dorm mate Shannon is one of them. She was my sex toy in her freshman year, and like you, she loved what I did to her."

"Oh my God! Really?

"Yes, now can we get back to you being my sex toy...? Where were we? Oh yes, You have to ask me nicely to let you cum."

"Can... Can I call you Mistress?"

"If it helps feed into whatever fantasy you're trying to fulfill, you certainly may."

Like a lot of college girls, I watched lesbian porn sometimes while masturbating. I especially liked it when one woman calls the other, Mistress. I wasn't sure if an opportunity like this would ever come along again, so I thought, why not let myself go wild? She is.

I turned my head toward hers and whispered. "Oh my darling Mistress Witch, please reach under my skirt and use my pussy as you wish, please rub my clit, please use your magic hands and make me cum."

"That was so sweet Cassie, I loved how you said that. But there's one more thing you must agree to, or everything stops right now... For as many times that I make you cum, you must return the favor... is that clear?"

My mistress went back to expertly fingering my pussy as I contemplated my answer. I knew what she was doing. She was getting me sooo aroused that I would have no other choice but to say yes.

I never touched another female that way in my life. And I'm not even sure I have the know-how to make another woman cum. As if she could read my mind, she whispered, "don't overthink it, Cassie, whatever you do to yourself, will also work for me."

"My beautiful, darling mistress, I will try my best to make you cum as many times as you make me cum... Can you please make me cum now... please?"

"You are so sweet Cassie... kiss me."

Up until then, I was receiving all the attention. I was a passive but willing participant. I was so nervous about looking inexperienced I hesitated. And now that I think about it, Mark and I barely kissed on our prom night.

While all that was going through my head. My mistress was back to fingering the life out of me, circling my clit and tweaking my nipple under my thin costume. My pulse quickened and my breathing deepened.

"You'll be fine, just kiss me sweetheart," she reiterated.

The tingle storm was brewing again. I leaned to the left, craned my neck to the right, our lips met. Her lips were incredibly soft, her tongue requested immediate entrance into my mouth which I happily gave. My heart began to pound in my chest. I caressed the back of her neck. I didn't want the deep passionate kiss to end. All the amazing sensations had me moaning into her mouth.

I was just about to cum, and I knew I'd be screaming so I broke our kiss. "No sweet Cassie, I need to suck on your tongue while you cum... I want to feel you cum."

I let her suck my tongue, and the overload of sensations sent me to a sexual stratosphere I never imagined existed.

I moaned loudly into her mouth as my pussy shot electric tingles to every part of my body. My legs, still wrapped up with hers, trembled uncontrollably. My eyes rolled into the back of my head. My stomach and neck muscles tightened almost to the point of being painful.

My lovely Mistress Witch never stopped sexually stimulating me. I swear the overload of tingles caused me to have an out of body experience. My body felt both numb and electrified. I felt a river of juices flow out of me.

She finally stopped when I pushed her hand away from my pussy because it was over-stimulated. She stopped sucking my tongue long enough to put her fingers in HER mouth this time. I pouted because she didn't put her fingers in my mouth. "Please my wonderful darling Mistress, please let me lick your fingers."

"No, my sweet dear Cassie. If you want some of this tasty treat, you're going to have to use your own fingers."

I was emboldened, I gave up any semblance of modesty. I dipped my fingers into my own pussy, looked at my mistress, and sucked my fingers clean. Then I did it a second time, then a third. My juices tasted so delicious and I wanted more.

We took turns fingering my drenched pussy and licking off the juices. I tried to see her eyes through the shadows of the dim light. But then my mistress smiled naughtily at me, which made me giggle, then she giggled. I spun in place, hugging her and we laughed into each other's shoulders.

Breathing deeply, I lifted my head and said, "My God, I've never cum like that before in my life. Is that what it's like for you every time?"

She gave me a silly smile, "No sweetheart, sometimes it's even better."

I giggled as I rested my head sideways just above her soft full breasts. I just started to recover when I asked. "Mistress, how did I get up to this room? Last I knew, I fell asleep on the couch."

"Well, the Halloween party at this frat house is the best on campus. It's great because they go overboard with the Halloween decorations, spooky lighting, and fun music. Everyone always wears some wonderfully naughty costumes. So I usually hang out here looking for my next sexy young plaything.

"I saw you and Shannon walk in and thought your slutty nurse costume was adorable, it reminded me of my wife's. And Shannon's Black Cat costume was over the top because it looked super tight. But when she walked by me, I realized it was body paint. Talk about taking slutty to the next level! She was actually nude with just body paint! Save for fury cat ears which contrasted nicely with her blonde hair. And her bushy cat tail, which must have been a butt-plug. But I already had her, so I picked you.

"I watched you sit on the couch while Shannon went to get you some punch. By the time she fought through the crowd and returned, you were already leaning to one side, fast asleep. She put your drink on the end table next to you and found some hunk to flirt with.

"I also noticed that your short skirt had ridden up, and you weren't hiding anything. I noticed some frat boys pointing at you, and from their body language, it looked like they were up to no good.

"I quickly sat down next to you, spread my witch costume dress, thin as it was, over your legs. I sat next to you for several hours, keeping watch over you.

"Around 11 pm the party thinned out a little. I noticed a tall male student of mine who was failing my class. He just happened to be in this fraternity. I made him a deal. If he could carry you upstairs to his bedroom, then make sure we were not disturbed. I would give him a passing grade on his midterm. And by the end of the semester, if he kept his mouth shut about the whole thing, I would give him a B for the class. He assured me that no one would ever know because he needed that B to graduate.

He laid you on the bed, face down, nodded at me, put a necktie on the doorknob, and shut the door. I locked the door behind him and got undressed, except for my stockings, mask and hat. I arranged all the pillows against the headboard. It wasn't easy, but I was able to roll your body on top of mine, then scooch up and lay your body against me.

Finally, I pulled back your slutly nurse skirt and gazed at your sweet young pussy. I loved the way it was neatly trimmed. I couldn't help myself and started rubbing your pussy. I know I took advantage of you, I'm sorry. There's just something in me that loves young pussy. I started fingering you too. It felt so good I couldn't stop. And that's when you woke up."

"Actually Mistress, I don't mind that you did those things. You probably saved me from a worse fate by those boys."

"Yeah, well... I wasn't much better," she said sadly.

"It's OK my lovely darling Mistress Witch, I forgive you."

I rested my head back down on her chest. I became reflective, and I had to ask. "Mistress... why did you say I was beautiful when you know that I'm not?

"Oh my dear sweet Cassie, but you are beautiful, hasn't anyone ever told you that?"

"No, no one, ever," I said as I kept my head down.

"We'll, I promise you Cassie, by the time you leave this university you will be able to stand in front of a mirror and call yourself beautiful."

"I... I find that hard to believe." Whispering in a somber tone.

"Oh honey, I've seen thousands of girls come through here over my many years of teaching. Yes, today you may think that you are plain or not beautiful, but you will grow into your features, you will join a sport, you will learn how to use makeup effectively, and finally, you will exude confidence.

The difference my dear sweet Cassie is, I can see THAT woman today, right now... that's why I called you beautiful... And one last word on the subject. In my limited time with you, I can see that you're sweet and beautiful on the inside as well. I can tell, no matter where you go in life, you will be a success."

I smiled broadly, hoping, praying that what she said would one day come true. What she said made me feel closer to her as well. It also made me feel better about myself.

But now it's my turn to return the favor I thought. Drawing on my viewing of lesbian porn I decided to see if I could make her cum by licking her pussy. I know that's a big leap for a newbie like myself. But pleasing my Mistress was all I could think of at that moment. Plus I thought, what the hell, I loved the taste of my own pussy, hers probably tastes good too.