Annie: Valentine Mine

Anal

My sister’s life-changing celebration of the 14th

Author’s note: This is my entry for the Valentine’s Day Story Contest 2023. It is a continuation of the Tale of Annie and Brian… and others. Regardless of any contest, voting and constructive criticisms are how I learn how better to please you, the Reader. Enjoy!

*~*~*~*~*

“Aw, nuts!”

This time, I just waited for her to tell me. I didn’t bother asking.

“They’re all sold out.” Okay, so she was going to make me drag it out of her.

“Okay, Annie… who is all sold out of what?”

“Victoria’s Secret. They’re sold out of this really cute red and white Teddy.”

“I didn’t think you liked red. I thought greens and brilliant blues were more your style.”

“It’s not for me.” Okay, at that point I had a pretty good idea who the Teddy was for.

“Jill?”

“Yeah. She did that really nice outfit for me for Christmas and I wanted to give her something.”

“Christmas was over a month ago.”

“I know. I was going to make it a Valentine’s gift.”

Oh. Okay… Only in my world would my sister be gifting expensive, erotic lingerie to my girlfriend for Valentine’s Day. And, yeah… girlfriend. Jill and I were officially dating.

In fact, way back in December…

* * * * *

“Thank you for getting Annie home safely,” my Dad was telling me as I helped schlep my sister’s stuff up to her room. “I could have made the trip, I suppose, but the roads have been getting treacherous and I appreciate you taking it on. I know you’ve got to turn around and head back tomorrow, but at least you’ll have one of Mom’s home cooked dinners and a decent night’s sleep.”

He was absolutely right about the meal. Before her stroke, Mom had been an excellent cook and she loved showing off for family and friends. Since then, for almost the last year, she’d been fighting to get her body back to normal and was doing an amazing job. You could still see a slight limp as she favored her right leg and a slight trembling and weakness in her right hand when she was tired, but otherwise she seemed completely fine. She was back to being able to drive and back to being able to cook.

And based on their trip to visit me and Annie at Thanksgiving, back to fucking the hell out of our father.

The ‘getting a decent night’s sleep’ part, I wasn’t going to bet on. Not with Annie horny all the time and me the object of her lust.

“So, who you gonna call?” she asked me as I helped her put her clothes away. We were in her room, minus the parental units, and she had taken the opportunity to tease me. She’d changed into Daisy Dukes and a thin tank top in front of me. I wasn’t sure how well that would fly with Mom and Dad, but it was her problem, not mine.

“Ghostbusters,” I told her. “You want these jeans hung up in the closet or folded into a drawer?” We’d done laundry before we’d left, so everything we’d brought home was clean. It did seem to me that she’d brought home a lot more than she needed. But again, her problem.

“In the closet,” she decided, “and very funny. You know I’m talking about who you’re gonna boff when I’m not around.” She looked at me for a long moment. “Involuntarily not around,” she added. “I know Jill for sure. You two are almost dating. In fact, you sort of are. But what about Becca? And Abby and Barb and Linda? Well, scratch Linda. I think it’ll be awhile before she needs another cock fix.”

“Annie, please… seriously…” I tried to explain. “I haven’t really thought about it. I’ve been… we’ve been… way too busy and when I go back to school it’s to go back to work and to start fleshing in my thesis.”

“I don’t buy it,” she told me. “I mean, I buy that you haven’t thought about it, but I’m pretty sure that now that you know you can get great sex whenever you want it, you’re gonna want it. A lot.”

“I’ve told you before and I’ll try telling you again,” I answered and I’m sure I sounded annoyed. “What I want to do and what I’m going to do are two different things. They’re all attractive in their own right, so what I want to do is a no-brainer. What I’m going to do is probably sleep with Jill when she wants to, and maybe have sex, again if she wants to, and work and study. But it’s unlikely I’ll do anything else.

“And mostly because you won’t be there and it’s been made abundantly clear that you don’t approve of me fucking around as if I were single. Their loyalty to you is going to trump any horniness, especially when there are other available, attractive options of both sexes. Regardless of what I do or do not want.”

She looked at me for a long time, before going back to putting away her clothes without a word. She was thinking and I knew it. And she knew I knew. And I knew she knew I knew… But we still managed to get to Mom calling dinner in immense silence.

She snapped out of whatever mood she was in, just in time for dinner and it was a nice family gathering like the old days. Mom oğuzeli escort had done her signature cheesy apple stuffed pork chops, garlic mashed potatoes, asparagus tips with bacon and a cheesecake for dessert. It was amazing and I was stuffed.

“I know you kids like video games to relax,” Mom commented during dessert. “The old Xbox systems are still hooked up, if you want. Let me know when you want to be up and out of here in the morning, Brian, and I’ll make sure you’ve got breakfast and something to-go.”

“I figure if I’m on the road not later than eight,” I told her, “I’ll make it back in time for a nap before I have to go to work.”

“Then I’ll have food ready by seven,” she decided. “I’ve been a bit tired recently, so I’m going to be a party-pooper and head for bed as soon as the dishes are done. You kids can just tidy up after yourselves when you go to bed.”

“I’ve got the dishes, Mom,” Annie spoke up. “It’s the least I can do. And unlike Brian, I know how you want the leftovers put away, so I’ll deal with that, too. No need to break in the hired help.”

“You’re being a little unfair to the help,” Mom chided her with a smile. “After all, he is the chauffer, not the maid.”

Okay, so they were teasing, but I wasn’t going to let it get to me. I just finished my cheesecake and sighed. “Too bad it’s going to be Christmas before another wonderful home-cooked meal,” I told Mom and by inference Annie. “Guess I’ll just have to suffer along on popcorn and grape Kool-Aid.”

That got a pause… and then a muttered and sarcastic “yeah, right!” from Annie.

“You should rotate the flavors of Kool-Aid, son,” was Mom’s sage advice. With a smile.

“Well, if you two are going to fire up the Xbox,” Dad decided, “I think I’ll take my reading to my office. Like your Mom, though, I’m not going to be staying up late. Let me know if there’s anything you need.”

We all agreed it was a plan and I helped clear the dishes, then left Annie to them while I went to fire up the game. We had an old Xbox 360 Mom still used for Minecraft, and an Xbox One that I’d given to Annie when I left for college. She still had the COD: Black Ops II disc, so I figured some Zombies would be cool. I was running some solo stuff when Annie joined me, and shortly after that Mom and Dad said goodnight.

“How about Mob of the Dead instead?” Annie asked as she sat down next to me and picked up a controller. I was running Buried at the time.

“Not a problem,” I told her and let myself get swarmed, went back to the lobby and selected Mob.

Annie and I worked well as a team, even against Brutus, and we were almost to midnight when she brought it up.

“So do I sneak into your room tonight? Or do you sneak into mine?”

“Annie, come on… please?…” I knew we were going to be separated for ten whole days, or whatever it was, but you’d think after the party the night before, that she’d be sated.

Not a chance.

“Hey, it’s going to be like, forever before I see you at Christmas,” she pouted. “And Jill’s going to be boffing you every night while I lie here alone, thinking about you.”

“Jill is not going to be boffing me every night,” I objected. “I’m going to be working and you know it. Plus I’m sure she and her friends have their own plans. If I’m very lucky, I’ll see her a couple of times, and sex isn’t a given.”

“Wanna bet?” she countered. “Besides, that doesn’t have anything to do with me not getting laid before Christmas.”

“Hey, you’re eighteen,” I pointed out. “Go out to one of the dance clubs. I’m sure there will be a lot of studs tripping over their tongues to get together with you.” Okay, so the glare I got told me I’d said exactly the wrong thing.

“Whaaat?” I drawled, dreading the answer.

“If you think I’m some kind of slut that’ll go cruising the clubs to get her ashes hauled, you have a serious re-think coming,” she told me levelly. “I’m not interested in any other guy. I’m interested in you. Period. And you’re going to be 300 miles south of me.”

I sighed. What else was I going to do? I’d never hear the end of it if I opted to not fuck her before I left. I was going to have to get her to ease up on her fixation. Maybe I could enlist Jill’s help. Regardless, tonight I needed to risk the wrath of our parents and take care of her.

“Will cuddling and a soft screw be okay?” I asked. Maybe I thought I was negotiating.

“That’s a good start,” she told me, shifting to a smile. There was that mercurial thing again.

“Okay, then let’s wrap this up and head for bed,” I decided. I shut down the game and she helped me pick up, then headed to my bedroom with me.

“If we get caught, it looks better if I came to you,” she explained. “Maybe something about missing you and wanting to cuddle before you left, and you just letting me sleep with you.”

“Whatever you want, Annie,” I told her as I stripped off my clothes. “Let’s just oğuzeli escort bayan keep it quiet and try to not get caught.”

She giggled and stripped and slipped into bed.

We were accustomed to sleeping together. And fucking, for that matter, in a bunch of different ways. But the one least likely to bring our parents down on our heads was spooning, her in front of me, docked. With her face in a pillow. A nice, long, slow screw driving her inexorably to her peak, several times if I could last that long, before I’d finally lose it to her hot, wet, tight pussy and cum.

I am completely in love with my sister. In lust, too, but love was becoming the most important thing. She had completely waylaid my rational mind when she pulled her sneak attack on my libido — and emotions — on the float trip and now I was having to really work at keeping some reason in our relationship. Plus I had the added distraction of Jill, who was also burrowing into my heart.

I figured I’d have a little time to try and sort things out, away from Annie’s direct influence, while she was at home and I was back at school. For now, though, I was going to make her as happy as I could, then get some sleep.

“Oh, fuck, Brian…” she moaned into the pillow. “God, you fill me up so good! Just… keep… doing… that… oh, yeah! oh, yeah! oh, fuck, YEAH! OHFKNCMMN!!!”

This last was pretty much screamed into the pillow, but she did a fairly good job of muffling herself. The way her pussy was milking me, though, was going to make it tough for me to last. I eased up as she came down the far side of her climax, which allowed me to back off some, too. Enough that I could start the slow, rhythmic, drive-her-nuts fucking again and go for getting her off a second time.

The same thing happened and I managed not to cum. I went for the third and lost it at the same time she went over. I’m pretty sure her pulsing on me is what took me over.

“Oh, fuck, Annie…” I groaned as quietly as I could while my balls pulled up and I hit my peak, jettisoning strong pulses of my cum deep in her pussy. She didn’t say anything. She just moaned into the pillow as her own climax took over.

I was going soft and starting to pull out when she reached back and grabbed my ass.

“Stay!” she hissed.

“Woof!” I whispered back.

“Just stay there, Brian,” she came back. “I want you to stay in me for as long as physically possible.”

“That’d be a good way of getting you pregnant,” I commented as I snuggled back up against her. “Good thing we’re not.”

“We’re not?”

There was a long pause while I battled it out between it being a joke and her comment on the float trip about being protected and sort of wishing she wasn’t. I decided to relax and go with the joke.

“Not funny,” I told her. “We can’t, either of us, afford to ruin our lives that way.”

“Okay, fine,” she groused. “But it is a fantasy. When you shrivel up and fall out, I’ll head on back to my bed and let you get some sleep. You need to be awake for the drive back tomorrow. Don’t want any accidents on the way.”

I thought about making some quip about how gracious that was of her, but decided to just let it go.

“Agreed,” I told her. “No accidents allowed.”

Sometime later, I did shrivel up and fall out and she left for her room after a soul-touching kiss. Whether I wanted to admit it or not, I was really going to miss her.

* * * * *

It had been a moderately uneventful trip back, with the Almighty holding onto the snowstorm that was promised until after I got back. Mom had met me at seven with breakfast, after I’d managed to wake up at six-thirty and grab a shower — don’t ask me how. I was finishing up and getting ready to leave when Annie kind of stumbled in and wobbled straight up to me, throwing her arms around my neck and pulling me into a major kiss. In front of Mom. By the time Annie let up, I had the obligatory embarrassed look, complete with the blush and chubbing up.

“Annie,” Mom chided her, “fantasies or not, you shouldn’t tease your brother that way. It can be embarrassing.”

“But Mom,” she pouted and I wasn’t sure if it was real or not, “I’m going to miss him so much! Whether he likes it or not, he’s kind of become my center of sanity.” I figured I’d better get ahead of this one.

“Thank you for the compliment, Sis, and… I need to get going. I’ll see you at Christmas. Just be your awesome self and help Mom and Dad out around here, okay?”

“My awesome self?” she smiled.

“Your awesome self. It’s less than two weeks to Christmas and I’ll be back.”

“I’m going to miss you so much!” she iterated, to me this time. She grabbed me in a Death Hug and I just went ahead and hugged her back. Eventually she let up and I was able to make my escape. Mom, Dad and Annie walked me out to my car, we said our goodbyes and I headed off.

I cued up a playlist on my car’s Bluetooth escort oğuzeli and just drove.

The Interstate was its usual boring, I was well over the limit and I made it back to my place around one-thirty. Jill wasn’t there when I went in, so I finished off the snacks and drink I’d been munching on and sacked out. I set my alarms for four-thirty and five, figuring that would give me time to get up and make a lunch to take with me before I had to go to work. It was oddly quiet without Annie around, but I did manage to fall out.

I woke when my alarm went off. I struggled out of bed, headed to the bathroom, relieved myself and grabbed a quick shower. Toweling off my head, I went in search of sandwich makings to make a lunch to take to work. I rounded the corner to the kitchen, still toweling off my hair, and ran smack into Jill.

Well, I didn’t exactly run into her. She was sitting at the kitchen table with a cup of coffee, a book and her phone, doing something on the latter. She looked up and smiled as I entered.

“Now that’s a fine sight to see,” she grinned. “Welcome back.”

“Thanks,” I told her. “Not staying long. Have to pack a lunch and head to work.”

“Your lunch is in the fridge with your name on it,” she told me. “Dinner and a note will be here when you get back. I won’t be.”

“Okay,” I told her, putting the towel around my neck and going over to start a cup of coffee. “So what’s happening?”

“I’m running Abby home so she can pick up some stuff she wants at the house. Mostly kitchen stuff, I guess. We’ll overnight at her folks’ place and come back tomorrow. So I won’t be here tonight. Regardless, though, you and I need to have a one-on-one about expectations when Annie isn’t around. My guess is, she’s panicking about who you’re going to be boffing in her absence.”

“I don’t know if it’s panicking,” I told her. “But you’re right… she’s agitated and we need to talk. You’ve got a key and my work schedule… feel free, whenever you want to be here.”

“Thanks!” she smiled, standing up and stuffing the book in her bag. “It’s good to see you back, safely.” She walked over to me, turned me to face her and slipped into a hug and kiss with me. Next to Annie, she had the most awesome kisses. “See you later,” she added as she let herself out. I finished my coffee, got dressed and ready for work, and headed out.

Just like at Thanksgiving, work was boring. The winter break meant most people went home or were off on vacation. Barring an unforeseen catastrophe, it would be like that until the weekend before classes started. I was determined to use it to my advantage with not having Annie as a distraction. Or, I should say, having her as less of a distraction. She was still calling me once a day to see how things were going.

The first time she did it, on Monday, I was on my way out the door for work. I had to remind her of my work schedule and suggested she pick another time to try to reach me. She did. The next time she called, it was 7am Tuesday and I was still asleep. I had to remind her that I didn’t get in from work until after midnight and she needed to not wake me up. So she settled on calling me around noon each day, figuring I should be up and it was well before work. Which was Wednesday, of course.

The first time she caught me when I was out shopping, on Thursday and hence rather brusque with her, she started to give me shit about being available to talk and I had to point out to her that I had life-maintenance chores to do on a regular basis, whether she was with me or not, and she really needed to lose the attitude that I should be at her beck and call. That must have stung, because she didn’t call me the next day and weirdly enough, I missed having her call. It turns out, she’d called Jill, instead.

“Hey, Brian,” Jill caught me on my cell while I was getting ready for work. “Mind if I stay over tonight?”

“Why would I mind? You’re pretty much allowed to be here whenever you want,” I answered. “Obviously, I’m going to work, but you have a key and everything. Knock yourself out.”

“Thanks… I’ll have some dinner for you when you get back. See you then.”

We rang off and I went to work. Per usual, I was back at the apartment by midnight-thirty. Not so usual, Jill was up, waiting for me.

“There’s turkey divan casserole in the fridge to be nuked,” she told me. “You can scrounge dessert and whatever you want to drink. When you’re settled, we need to talk.”

“Okay,” I answered with a knot starting in my gut and imaginary ominous music in my head. If we needed to talk, there was some kind of trouble. And it probably involved Annie.

I did as she suggested… nuked the casserole, made up my usual Don Q and cranapple, and decided to skip the dessert. Jill sat and watched me, sipping on some wine, while I got settled and fed. Then she opened the conversation.

“Annie called me,” she told me. “As opposed to you. Apparently, she was feeling ‘put in her place’. And by my read, she was both pissed and scared. Pissed that you told her to basically back off, and scared that you told her to back off. Her rather fertile imagination was going crazy with ideas of you off partying all the time and keeping it hidden, especially since I wasn’t around you all the time, and so forth.

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