Sister's Comfort

Summary: Sister comforts her brother after he catches gf getting spit roasted.

Note 1: This is a Halloween 2022 Contest Story.

Note 2: Thanks to Tex Beethoven for editing this story.

Sister's Comfort

Sometimes life sucks, and other times life surprises the shit out of us, but occasionally life is fucking amazing!

Sometimes all three of these circumstances happen on the same day, or even all at the same time.

But before we get to the crazy Devil's night (another name for Halloween) that changed my life forever, I need to set the scene for you.

First, I have a twin sister named Maya. She's athletically gorgeous, and oh so sweet.

Second, I should note that while I was a brilliant student... but socially not super popular nor an outcast, my sister was both smart and popular. She was on the volleyball and basketball teams, while I was on no teams and a member of no clubs. She loved high school; I tolerated it. We were opposites in many ways, and yet we were surprisingly close. We didn't have any sibling rivalry, and we always got along well together.

Third, I was a virgin. This was partly by choice and partly circumstances. I was a decent looking guy with a decent body (I liked working out) and a slightly-above average dick size at six inches (the average was somewhere between 5.1" and 5.5"... I'd checked... I believe every guy checks). I wanted my first time to be with someone I cared about... a lot. I wanted it to be special, and although I'd dated a few girls in high school and had some fun with them, I'd actually refused sex twice (not the few hand jobs or two blow jobs though, and I'd gone down on three girls... which I'd really enjoyed doing. Listening to a woman moaning is a real turn-on.

Fourth, and this may seem irrelevant right now, I loved Halloween and so did Maya. We always loved dressing up in outfits that matched... which may be corny for a brother and sister, and even more so for twins... but we'd done it every year since we were born... although of course for the first few years it was only because our parents choose our outfits. But once we were old enough to start making some of our own decisions, we continued the tradition, because we enjoyed it. In our freshman year of high school I was Mario, and she was Peach; in our sophomore year we dressed as Peanut Butter and Jelly (I was Peanut Butter). In our junior year I was Fred Flintstone, and she was Wilma (that year it was weird, because she was dressed very skimpily for a brother-sister duo. In our senior year we really outdid ourselves; I was Jon Snow, and she was Daenerys Targaryen. It worked very well since I had long, dark hair (but no beard) and Maya had the light blonde hair and fair skin to match her character.

Yes, once we were in middle school we started getting razzed for wearing our matching sibling costumes, but my very popular sister never gave into the peer pressure and teasing. She was always her own person ad never gave a shit what other people thought. I loved her for that. I was never as brave as she was, but her insistence upon our following our 'tradition' lent me the courage to follow her lead, and even to enjoy myself.

During the next summertime we decided to go old school next Halloween, and for the first time ever, repeat a costume set we'd worn when we were younger... Scooby Doo characters. When we were five, I'd been Shaggy while she was Daphne. We decided to do it again.

.....

Of course, the next fall we entered college. We both attended the same one, which was only two hours away from home... close enough to get back if we needed to, and it was far better than any schools closer to home.

Maya was attending on a sports scholarship (both basketball and volleyball, just like in high school; I was on an academic one (chemistry and math).

She pledged and was accepted into the most popular sorority on campus; I lived in a dorm with a cool roommate named Derek.

During the weekdays, we were both swamped with our studies, so we only saw each other occasionally, but we made a point of spending every Sunday brunch together to stay in touch... and I attended every home game she played volleyball in. (College volleyball began immediately when school did, and her basketball season wouldn't begin until early November.)

By Halloween, one thing had changed in our lives... well, mine more than hers.

I'd found a girlfriend.

Her name was Emma.

She was a hot one.

And a wild one.

A hottie who really brought me out of my shell.

We hadn't had actual sex yet, but she'd blown me in an Uber, in a movie theatre, and in a Victoria Secret change room.

I'd fingered her in the same Uber and movie theatre, and eaten her to an orgasm in Victoria Secret, where embarrassingly for me (but not for her), her orgasmic scream alerted everyone in the store to her climax.

One day (again to my embarrassment but not hers) she even did a cum walk after I'd dropped a load on her face. I was hesitant at first when she wanted me to hold hands with her so everyone would know who her cum donor was, but before long I was feeling quite proud that my accomplishment was being aired right out in public like that.

Like I said, she was wild... and she did a great job of helping me to get comfortable with college, and to do more than just study, work out and play video games, which had always filled my non-studying hours back in high school.

Which leads us to my horrific, shocking... but also my thrilling escapades of Halloween 2022.

.....

First, the horrific... although it was supposed to be thrilling.

But wait... first there was some wickedly good:

Emma decided to dress up as Velma, and I mean a hot Velma, with orange thigh high stockings (which I didn't even know anyone sold instead of just the unsexy socks). She also told me, "Tonight's the night!"

She didn't need to say anything else to clarify her intent. I replied, "Yeah? That's so cool!" agreeing that if she was up for it, it was indeed time. I wasn't sure I loved her, but she was amazing, and however the future went for us, I knew I'd never regret losing my virginity to her.

The party we went to was at a sorority house (not Maya's). We all posed for a great selfie with me grinning like a fool with my arms around the waists of Emma and Maya... which of course was Shaggy's ultimate dream... to be between Velma and Daphne, who were dressed in authentic, but slutty as fuck, outfits. Maya's Daphne costume was living hotness, with Daphne's exact shade of purple pantyhose... which just like the Emma's orange thigh highs, I hadn't known was a thing. If she weren't my sister I'd want to fuck her.

Okay, truth be told, I had wanted to fuck Maya for the past few years. She was ridiculously hot, and that night her being dressed like Daphne made her almost irresistible... which was made clear by all the guys (and some girls) drooling all over her.

Maya went off to dance with some of her girlfriends while Emma and I danced and drank together.

We were both on drink number four (or maybe more) when I needed to break the seal and piss...which took a lot longer than one might think, since the line was ridiculous. And then when I returned to the main party, I couldn't find Emma anywhere.

I looked for her for a good twenty minutes, worried she'd gotten sick (she tended to really hit the booze at these parties... which got her even wilder... like the time she'd blown me on someone's back porch while people squeezed past us. I was embarrassed by being caught in the act over and over without pause, but she hadn't minded at all.

I was going upstairs to the bedrooms, thinking maybe she'd passed out somewhere, when Maya appeared out of nowhere and stepped right in front of me, stopping me in my tracks.

"Don't go up there, Bruce," she said, having stopped me halfway up the stairs.

"What? Why not?" I asked.

"Just don't," she insisted, giving me no explanation, but with deep sadness and worry in her eyes... something was very wrong.

"But why not?" I demanded.

"Bruce, just trust me," she insisted sorrowfully. She obviously knew something I didn't, and whatever it was, it was so awful she didn't want me to know what it was!

Concerned, worried and confused, I pushed past her. "I have to find Emma, Maya!"

I hurried past some other students who gave me looks that could only be described as pitying... but I couldn't figure out why, as I pushed myself through the crowded hallway and made it through to a marginally open door.

"Don't go in there, Bruce," Maya called out from about twenty feet behind me. "Just DON'T!"

Not at all expecting to see what I was about to see, I pushed open the door, stumbled in, and froze in my tracks.

Emma was on a bed... completely naked except for the thigh highs she'd told me earlier today she'd bought just for me... just for our special night... knowing my fascination and kink for nylons... my pervy fetish I didn't really understand... I just found them hot.

She was on all fours on the bed getting spit-roasted, a term I'd learned from watching a lot of porn, while Barry (a senior football player who was already getting talked about becoming a first-round pick for the NFL draft) was fucking her from behind, while Perry (the richest asshole who'd attended my high school) was pumping his dick in her mouth.

And this fuck fest was obviously consensual, since Emma was vigorously bouncing back onto the well-built Barry before rocking forward to take all of Perry's dick in her mouth... while she moaned like I'd never heard her do before when I'd fingered her or eaten her out.

Perry caught sight of me, so he smirked as he pulled out of her mouth and shot his load all over her face... and Barry paused.

Emma moaned, "Yes you hot stud, give me that cum shower," while she stopped bouncing and begged the asshole to come on her face.

Barry then resumed slamming into my girlfriend as she moaned, even while her face was now covered in cum, and she said nastily, words I'd never heard my girlfriend use, "Oh yes, fuck my pussy with your big fucking dick!"

I couldn't move a muscle... or speak.

I was stunned. And still motionless.

Then the scene got even worse when Jake, another jock asshole, an ex of my sister's no less who'd also gone to my high school, got onto the bed and asked, "Want some more cock, Emma?"

"Yeah, shove that nasty cock in my mouth," Emma said lustily, cum dripping off her chin.

"You're sure?" he asked, sneering at me while all I could do was stare back helplessly.

"Yes, give me that dick," she said, and then she too turned towards me, and her eyes went wide. "Oh shit! BRUCE! I...."

The guilty look on her face was then replaced by Jake's dick as he slid it into her mouth.

"Sorry, man, those are the breaks," Jake shrugged as he began fucking her face.

"You assholes," I finally managed to break my paralysis and cried, as began moving toward the bed.

I felt someone pulling on my arm, so I looked, and saw Maya clinging to me with tears streaming down her face. She begged, "Bruce, please don't torture yourself, she's not worth it... let's get out of here!"

I wasn't sure what I'd been about to attempt since any one of those three fuckers could kick the shit out of me without much effort, so I gave in to my sister pulling me out while she yelled at her ex, "Jake, you're really a piece of shit!"

"It's not my fault your brother's girlfriend loves doing what you always refused," Jake taunted her just as we reached the hallway.

Maya led me downstairs through throngs of people, all of them obviously knowing about the sex show upstairs... most of them making fun of me, a few others looking sympathetic and perhaps saying kind words. Maya said, "Whatever they say, don't answer. In fact, don't even look at them; just keep following me outside!"

Once we were outside, I broke down completely while my sweet sister comforted me. I was so lost in my pain that she even needed to hold me up or I would have collapsed on the lawn.

"I saw a few sympathetic faces, but most of those people are fucking assholes!" Maya said, really pissed by what had just happened.

"Y-y-y-yeah," I agreed, openly sobbing for the first time since our father died.

"You deserve way better than that skank," Maya added, wrapping her arms around me and pulling me tightly against her... and I was suddenly able to smell her sweet perfume, feel her large, firm breasts pressing against my chest and her leg against my dick... which for reasons I still can't explain after what I'd just witnessed... was rock hard.

"She told me we were going to have sex tonight for the first time," I said, not sure why she needed to know that, but I had nobody else to tell.

"And instead she's the centrepiece in an orgy? That's just shitty," she said, still holding me tightly in her arms.

"Yeah," I said, and then I added through a sigh, my cock inadvertently twitching against her leg, "Nineteen years and counting."

"Huh? What do you mean?" she asked, giving me a confused look, I guess partly because of what I'd just said, and very probably because of my hard dick pressed against her leg. She then apparently caught on, since she looked at me sadly while she leaned away from me and said, "Wait! Bruce, you're not saying you're a virgin, are you?"

"Yeah, I am," I admitted.

"But what about Kimberly?" she asked. "And Carrie?"

"No and no," I said. "I wanted to lose it to someone really special."

"Really?" she asked, astonished by my answer.

"Yeah, I know. Stupid, right?"

"No, it's not stupid at all," she said as she wiped away a tear rolling down my cheek, which made me feel so pathetic. "I think it's sweet."

"Yeah, because any guy wants to hear that he's sweet," I sighed. "That, and 'you're a nice guy'."

"You are a nice guy," she insisted.

"Such flattery. And how many 'sweet nice guys' have you ever dated?" I asked.

She sighed now. "Not any. Which has always been my mistake. Jake for instance... he's a real asshole!"

"That's every girl's mistake unfortunately," I consoled her.

"Yeah," she said, pondering our conversation while I sat down on a bench.

"I knew she wasn't the one," I said, "but she was a lot of fun."

"You seemed happier with her than I'd ever seen you before," she said as she sat down beside me.

"Yeah," I said. "I was." Then after a pause I added, "I guess."

"You guess?"

"Yeah, she was fun, wild, and well... hot," I said, "but she didn't have much substance."

"I see."

"Sadly, who I really need is someone just like you,"

"Like me?"

"Yeah, exactly like you," I said. I wasn't hitting on her, just stating facts. "You're hot, and you're sweet, funny and smart."

"Did you just call me hot?"

"Yeah, and I'm not the only one who thinks that. Everyone thinks you're hot," I said. "Even some gay guys think you're hot."

"You know your attractiveness is lots more than just looks."

"That's what I thought in high school," I said. "Once I got into college, everything would be different. Yet here I am: different school, same shit."

"Trust me, I know," she said, her hand dropping onto my leg.

"How would you know?" I asked, knowing her high school experience had been substantially different from mine."

"How would I know? You know how everyone sees you as smart, but that's all they see?"

"Yeah."

"Everyone sees me as a hot chick athlete," she said. "And nothing else."

"And that's bad?"

"Nobody ever notices my intellect. They don't even care if I have any smarts or not," she said. "I'm just some babe playing sports whose ass looks good in shorts."

"I've never thought of you that way."

"Guys also assume I'm a sure thing."

"I guess," I said, never having thought my sister had any problems. Certainly not any social ones.

"And whenever I tell a guy no he automatically asks if I'm a lesbian."

"Every guy's dream," I joked. "Fucking a lesbian so she changes sides."

"You guys are all the same," she said, shaking her head and giving my leg a squeeze.

"Yes, we really are," I said, placing my hand on the side of her leg and feeling the sheer silkiness of her purple pantyhose.

"Actually, I don't think you're nearly as bad as most guys. I think it's cool that you're waiting for someone who really touches your heart to make your first time special."

"Most guys would call me a pussy for wanting that, instead of just banging some fox and moving on," I shrugged, wishing I could move my hand up and down my sister's pantyhose-clad legs. But I didn't, for obvious reasons.

"In hindsight, I wish I'd waited too," she said, resting her head onto my shoulder.

"You do?"

"Yeah, doing it in the backseat of Ralph's car all cluttered with fast food containers wasn't very romantic."

"I guess not."

"And both he and the sex were completely forgettable."

"That's a shame."

"Yeah, and he lasted less than two minutes."

"That's such a travesty!" I gasped, hoping I'd last much longer my first time. I'd jerked off four times today, hoping it would help me last longer tonight.

"Yeah, and I didn't even come close to getting off," she added. "And after he finished, he just drove me home, without either of us saying a word. Not even Good night'."

"That's inexcusable," I said as she stood up, her nylon-clad leg rubbing against my leg.

"Let's go," she said.

"Where?" I asked.

"If you don't mind, I'd like you to walk me back to my sorority house," she said. "I don't need to be anywhere near this one anymore."

"For you? No way would I ever mind doing anything you wanted me to," I said. I stood up and she inserted her arm inside mine. It would have been so romantic if she weren't my sister, and I hadn't just seen my girlfriend getting spit roasted. No, she was my ex-girlfriend now, and we didn't need any official breaking up talk... what she'd done had made it plenty official.

"Really? In that case, I want you to be a better man than all the other boys around here."

"How would I do that?"

"It's not hard. Just be who you already are, she said, "but also make sure the woman you're with gets off too."

"I couldn't imagine ever not doing that!"

"Then you're part of a tiny minority of nice guys. And I'm sorry, but you are nice... really nice... and I'm not putting you down by calling you that."

"Really?" I asked, that kind of courtesy from a guy just seemed like common sense. Why would a woman want to be with a guy, if he didn't make sure she enjoyed the experience too?

"Yeah, really. Would you like to hear a true confession?"

"Sure, if it's something you want to tell me."

"I've never come from having sex with a guy."

"But you have with a girl?"

"I didn't say that you pervert," she scolded playfully, squeezing my arm.

"You didn't not say it either," I countered, a visual of my sister having lesbian sex a very hot one.

"Fine, nosey! I've only ever come from using my fingers, my toys, and with another girl," she said. "Is that what you wanted to hear?"

"Um, that's not exactly what I wanted to hear about my sweet sister," I pointed out, and then I slyly adjusted myself while we continued walking.

"Did you just adjust yourself?" she asked.

"I plead the Fifth," I grinned sheepishly.

"That's an American thing," she pointed out. "We live in New Brunswick."

"I still plead the Fifth," I said. "But it's terrible that no guy has ever been a real man for you."