A Valentine's Boyfriend for Anna

Thanks for reading my Valentine's Day 2025 story. For reference, it's in the T side of I/T, and there's spoilers for the movie "Babygirl ".

===

I looked suspiciously at the drink my niece was sipping. "What the hell is that?"

Anna poked out her tongue. "A decaf white chocolate mocha frappuccino with almond milk. I'm not a boring boomer who thinks a flat white is the height of sophistication."

"It may not be sophisticated, but at least it resembles coffee. And I'm not a boomer. Missed that tag by ten years." My phone pinged, and I opened up the message. "That's Lisa. She's going to be at least another half hour. They have to do a factory reset on her iPad, and then reload her stuff."

"Oh well. I thought she was being optimistic, thinking it was only going to be five minutes. Saturday here is always crazy. I'm surprised it's not longer."

"You know your aunt. The eternal optimist." I looked up at Anna after I replied. "So, is there anywhere you want to go, or are you happy sitting here?"

She stared out at the Valentine's Day decorations in the mall, sighed, and shook her head. "No, no. It's all good. I'm happy here."

"Mmm. I know that look. Your mum and aunt have the same one when they're upset, but don't want to tell anyone. You're not ok."

Anna looked down at her drink and shrugged. "It's fine. Nothing to worry about. Just got some stuff on my mind."

"Fair enough." I knew enough from my experience not to push it, and just leave it until she was ready to talk to someone. I sat back and looked at the florist across the walkway. VD was two weeks away, but the place was filled with roses, probably at an exorbitant price. "Hey Anna, what do you think about Valentine's Day? Should I get Lis something? Never been into it, but it seems to be the thing to do with you young ones."

That triggered a reaction. Her face fell, and she looked on the verge of tears. Going from happy to sad in a blink was not what I expected, and I knew there was definitely something wrong. Still, I just figuratively bit my tongue and drank my coffee.

After a while, she sighed and said quietly, "It's nice to do something on the day, especially when all your friends are doing something with their partners and you're just sitting at home."

Bang. I was right, but kept on with my question. "Oh. Ok. I may get you to help me with that. I'm not romantic at all."

"Actually, I think you are. Whenever I've visited, you make Lisa dinner, you rub her feet and massage her neck, you surprise her with chocolate and coffee, you snuggle on the couch and watch shows like Bridgerton, which you hate. To me, that's everyday romance. Just the little things that make the difference between just hanging out for whatever reason and something deeper." Anna shrugged. "I haven't had that, and I guess that's what's making me a bit sad."

"Ah. Well, all that's just what I, we, do." I shifted uncomfortably on the seat and scratched my head, wondering how to phrase my next, definitely awkward question. "I know you've had boyfriends. They haven't been, umm, great, I assume? Is it possible you are actually interested in, err, the other half of the population?"

Anna stared at me, mouth slightly open, and I wondered if I'd just made a monumental error. After an eternity, she started giggling. "I can't believe my uncle just asked if I'm a lesbian. That's so funny. No, I like guys and what they have. Oh my god!" She sat bolt upright and put her hand over her mouth, blushing a deep red. "I can't believe I just said that."

I waved the thought away. "I started it by asking a dumb question. You're 22. You can say what you think with us, and you know we won't judge. We're your cool pseudo-parents, so if you want fun times with a guy or a girl, then as long as you're sensible about it, we'll have your back." I reached over and held her hand. "And I'm happy to see you laugh. Sorry things haven't worked out so far, but you are a gorgeous young woman. You will find someone."

She slowly nodded and kissed my fingers. "Thanks Ben. Yeah, I suppose there's a guy out there, somewhere. Like, Dad found Mum, and he's the biggest doofus around. I still don't know why she married him, but I'm glad she did."

"What can I say? He was persistent, and he made her laugh." I let go of her hand and sat back. "Maybe you need a break now the Christmas and New Year sales are done. What about you take a few days off and come and visit? You're welcome anytime, you know."

"Thanks, I might just do that."

===

"I'm really happy Poppy's thinking of visiting, but it still doesn't change the fact she'll be alone on Valentine's Day. She'll see all those Insta posts from her friends, and that'll make her upset again," Lisa said, after I told her about Anna's spot of sadness.

"I know, but I guess we'll need a way to keep her occupied. Maybe see a movie, go for a walk on the beach, go out for dinner. You know, romantic sort of stuff."

"Not very romantic with her aunt and uncle, and I'm not sure I could get the day off. I know I'm going to be tied up with a client until after six. Maybe you could take her out?"

"I guess I could, but I don't know if Anna would like hanging around with her geriatric uncle. She did call me a boomer."

Lis kissed me on the cheek and rolled over. "Poppy, and I really need to lose that habit, Anna loves you. Plan a day for her like she was your girlfriend, but keep it a surprise. She'll be so excited."

"Fair enough, can do. We'll see if she accepts the offer to stay and go from there." I kissed Lisa's shoulder and rolled over. Treat my niece like my girlfriend? I had ideas, but my thoughts never went to the obvious. Anna was still our little girl, even though she had blossomed into a willowy red haired, freckled beauty. Well, we thought she was beautiful, even if she doubted herself.

===

Anna decided to take up our invitation and arrived with her pillow and an overnight bag. We hadn't told her too much of what was planned, only that she was going out for dinner at a top restaurant so a nice dress would be appropriate.

"Hi everyone, I'm home," she called out as she came in the front door. We yelled "Hi" back, me from the kitchen, and Lisa from the spare bedroom she was still fussing over.

We all hugged, and Anna tossed her bags in her room. "Good drive? And can I get you a drink?" I asked.

"Drive was fine. Not too many idiots on the road, and I'll have a mineral water, thanks. It's hot out there."

I poured the drinks, and we sat on the couch. "Thanks for having me," said Anna. "I really think I needed a break. The lead up to Christmas was a shocker, and the Boxing Day sales manic. That day was just the final straw for me, I guess."

"Ah, no worries. You know you're welcome anytime, and it's not like we're on the other side of the country anymore. Just relax and make yourself at home. Ben's got a couple of things planned for tomorrow, but apart from that, the rest of the weekend is yours," Lisa said, smiling.

Anna looked from Lisa to me, and back. Puzzled, she asked, "Tomorrow's Friday. Aren't you working?"

Lisa smiled. "I am, and until late. Ben's not. He's going to be your Valentine's boyfriend, and we, he, plans on showing you a good time. The details are sort of a surprise, but we hope you'll love it."

"If you're ok with having a boyfriend that's thirty years older than you," I added.

"Umm, wow. Did not expect that." Anna smiled and slowly shook her head. "You two are the best aunt and uncle I have. Crazy, but still the best. Of course I'm happy you're my BF for the day. This is going to be so cool!"

"Great. Well, I'll finish making dinner, and you and Lisa can talk about essential oils or whatever," I said.

"Spoken like a true boyfriend. Come on Po... Anna. I've got some new blends I think you'd like."

"You can still call me Poppy, Lisa. I don't mind when you do it, it's others doing it that annoys me," Anna said and followed Lis off to her office.

After dinner, the two girls changed into their summer weight sleepwear and moved to the couch. Anna had her head in Lisa's lap and I had her feet to gently massage. MasterChef was the program of choice, but I was more interested in the occasional flash of red curls in her short pyjama pants. I don't think Anna knew, or if she did, cared she was flashing her pubes. I'd never noticed them before, and I wondered if going commando was a new thing.

"You've lost none of your touch, Unc," Anna groaned. "My feet hurt, but in a good way."

I walked my thumbs around an ankle and up towards her knee. "You've got some very tight muscles for someone who walks around a shop all day. You really should do some stretches if this always happens."

"I don't walk that much. I spend most of my time standing behind the register now." She rolled onto her back and rearranged her shorts, giving me another flash of fire. "I don't think I told you. I'm the assistant manager now, so yeah, standing is a big part of the job."

"Congratulations! That's great," I said and kissed her big toe. Lisa echoed my thoughts and kissed her head.

"Thank you." Anna giggled and wiggled her toes. "Aren't they a bit stinky? They've been in shoes all day."

"Nah, they're fine. I've kissed much grosser things." I held my hand to the side of my mouth and whispered, "Your grandma at Christmas."

"Hey, that's my mother you're making fun of, but you're not wrong. That woman should stay away from the gin," Lisa said.

"I know!" Anna replied. "I was afraid she'd go boom if she went near the candles."

"The things we do for family," I said with an exaggerated sigh, then licked Anna's big toe.

Anna squirmed and flexed her feet, but held her toe up for more. "You are definitely crazy."

I slowly kissed around her toe, then decided to suck it. Anna's eyes rolled back, a faint smile on her face. I kissed her other toes and went back to gently massaging her legs.

MasterChef finished in its usual dramatic fashion, and Lisa switched to a British murder mystery. Anna rolled onto her back so Lisa could run her fingers through our niece's long hair, and I cuddled her feet. When the Sister started to daydream about being a movie star, Anna shuffled her bum and bent one leg up, knee knocking against the couch back. I now could see more than just curls out of the corner of my eye, and I was pretty sure our innocent little girl was flashing me deliberately.

I had no idea why she was doing that, but the sight of her pink bits opening and closing really started to create havoc with me. "Ice cream, anyone?" I asked, looking for an excuse to stand and rearrange myself.

"Yes please," the girls said, so I carefully extracted myself and went to the kitchen where I stuffed paper towel over my heavily leaking cock. I loaded up three bowls with ice cream and hundreds and thousands, took a deep breath, and went back to the lounge room. Anna and Lisa were sitting up, and the smile Anna gave me made me unsure if the flash was deliberate. It wasn't a "I know where you were looking and you enjoyed it" smile, more a "YAY, ICE CREAM!" smile. Still, my dick appreciated her inner labia waving hello. It didn't care that she was family, it was a young, warm vagina that it needed to fuck.

"So, my new boyfriend, what are we doing tomorrow?" Anna asked as Lisa took the bowls out to the kitchen.

"Well, my darling, I was planning to surprise you with breakfast in bed, then it depends. I thought catching a movie of your choice at one of the gold class cinemas, then dinner at..." I did a drum roll on the couch arm rest.

"Yes?"

"Dinner at..."

"The dramatic pause is getting a bit much, Ben"

"Grossi Campania."

Anna squealed and her hands flew up to cover her mouth. Grossi Campania was one of the top Italian restaurants in the state, whose hand made ravioli was legendary. Getting a dinner reservation was difficult on normal days, but managing to get one on Valentine's Day was extraordinarily lucky. I was in the right place at the right time, and knowing the right people. Lisa was very jealous, as I'd been promising to take her there for ages.

"Grossi Campania and gold class! That's amazing! Really, you don't have to. Tonight was pretty good, just lying around. I'd be happy with just that."

"Ah, but your boyfriend wants tomorrow to be extra special, something you'll remember forever." I put my arms around her waist and pulled her close. "So, the morning and evening are locked in, but the middle depends on what you want to see and when it's on."

Anna draped her arms over my shoulders. "Any movie?"

I nodded. "As long as it's showing through the day. Dinner is at 7."

She pursed her lips and frowned. "Hmm. Can I think about it overnight?"

"Yep, no worries. I'll be knocking on your door around eight with French toast and orange juice, and I'll probably need to make a booking by nine."

She released me from the hug and gave one to Lisa. "Thank you thank you thank you, this is so cool of you."

"Whatever cheers you up, Poppy. You looked so sad at the mall." Lisa brushed a wisp of red hair off her niece's face. "Have a fun day. Ben is all yours to command. In the nicest possible way."

"Thanks Lisa. I think I'd better go to bed. It's going to be a great day." She gave both of us a kiss on the cheek and skipped off to her bedroom.

"She seems happy with the plan," I said.

"You're taking her to Grossi Campania. Of course she's happy." Lisa said dryly and patted my shoulder as we headed to bed. "You'd better pull that same magic soon for me, mister. I'm dying to try their chicken scaloppini."

===

I balanced the breakfast tray on one hand and knocked on the door. "Good morning Anna, this is your breakfast delivery. Are you decent?"

I waited, but not hearing a sound, I tapped on the door again. Knowing our niece could sleep through anything, including her alarm, I opened the door and poked my head in. She was sound asleep. And naked. Her bare back was facing me, and I just stood and admired the young woman, long red hair forming a pool by her shoulder. Finally, I put the tray on the floor and carefully pulled the sheet back over her. The movement woke her, and she rolled onto her back, yawning.

"Happy Valentine's Day, gorgeous. Sorry to wake you, but I, umm, have breakfast."

"Thank you Ben. Oh..." Anna started to sit up, then remembered she was naked. "Could you turn around for a sec while I put my top on? It was pretty warm last night, so I wasn't wearing anything."

I turned and bit my bottom lip, wondering if I should say something.

I heard a rustle of material, and she continued. "Sorry I wasn't awake. The alarm went off, but I must have turned it off. Ok, I'm dressed, sort of."

I picked up the tray and turned. "Here you go. Hope you like it."

"Looks great," she said, taking the tray from me. "And a rose. Thank you." She patted the bed, and I sat on the edge.

It felt funny watching my semi naked niece eat. She'd put on a pale blue spaghetti string tank top, which did a poor job of covering her little breasts. I chuckled a little to myself. I'd now officially seen Anna completely naked. Admittedly, it was a compilation over three sessions, but it wasn't something I'd ever expected to see."

Anna noticed the chuckle. "What's up?" she asked, and leaned forward to pick up the rose I had placed on the tray, flashing her pair of pink nipples.

"Oh, nothing much. Just thinking about today, and how to describe what's happened to anyone."

"It's just us having fun, isn't it? Boyfriend - girlfriend sort of thing." She put the rose down. "Are you having second thoughts? You look worried."

I sighed and shook my head. "No, god no. I umm. Shit. Ok. Let's just say you've given me an unexpected flash of inspiration last night and today, and I'm not sure what to think about it."

"Oh." Her eyes widened as she realised what I had said, and a deep, deep blush coloured her face and breasts. She whispered, "Ooohhh... I didn't have any undies on last night, did I?"

"Nope. And you were naked when I came in. I covered you with the sheet."

"Ah. Well, that's embarrassing." Anna started laughing and put the empty tray on the floor. "Well, I guess seeming all of my boyfriends - the whole three till now, have seen me naked, you should as well. Even if it's only for the day."

"It's a bit late to unsee what I saw, and it all looked very nice."

"Thank you Ben. Even my dangly girly bits?"

"Especially your dangly girly bits."

Anna looked relieved at that, and flicked the sheet off. "Well, I guess seeming you've seen all of me, no point in staying covered. Snuggle? I know it's a bit naughty, but you are my boyfriend."

"Sure, but I'd better stay clothed." I moved in behind her and rested an arm across her belly. She squiggled her bum, and it would have been very obvious I was hard.

"Spoilsport, but ok. By the feel of what's poking into my back, I really don't want you leaking over me." She took a deep breath and sighed happily. "I like snuggling."

"Me too. The world needs more of it."

Anna lifted her head so she could rest it on my other arm. I let it fall over the edge of the bed, but she lifted it back on and bent the elbow towards her. "It's just my boob," she mumbled as my hand fell across her.

This was way more than what Lisa and I had planned, but I rationalised that it wasn't that much difference to her wearing a bikini. It was a bit hard keeping that train of thought as her nipple rose and pressed into my palm. I tried to steady my voice and asked, "Any thoughts on a movie?"

"Can we see Babygirl? All my friends are going to see that today."

"Umm... Sure." I didn't think that was the movie I should be watching with Anna, especially considering the position in bed we were in, but I couldn't say no. I did say any movie. "Not a problem. I'll go book."

"Not yet. Can you please stay a bit? I need this."

"Sure. As long as you want." I gently kissed the back of her neck and she placed her hand on my hand that was covering her breast. By the sound of her breathing, Anna had relaxed and dropped off again. I didn't mind. Why would I? We were family, and I was comforting a girl who'd had a bit of a rough time. Two of her boyfriends had been real arseholes, but the last was a really nice guy who had to move interstate for his job. They tried to make it work, but 3,000 kilometres was too much distance to overcome. She was heartbroken when they decided to just stay friends, just before Valentine's Day.

Anna finally sighed and rolled over to face me. Our noses touched, and I looked into her deep green eyes. "You had a nice snooze," I said.

"Just needed that little bit extra nap time." She bopped my nose with a finger and swung out of bed. "Well, boyfriend Ben, I think I'll have a shower while you book the movie."

"Yep. I think I'd better have one too. I don't know why, but I seem to be a bit... sticky in places."

Anna put her head back around the door frame. "Well, be quick with the call, and have one after me. You've seen me nude, I think it's only fair I see you."

"Well, ok, but you've pretty much seen me at the beach."

"Only the top half, and I've felt the rest today." Anna blew me a kiss and headed to the bathroom.

"This was not on the plan," I said to myself. "Lisa is going to kill me if she finds out."

I took the breakfast tray out to the kitchen and glanced through the open bathroom door at Anna. I was, frankly, confused. Things had taken a sharp turn quickly down a road I didn't want to be on. Being honest, though, it was more like a road I knew I shouldn't be on, but here I was, slowly getting deeper and deeper into the woods. What was Anna thinking? Was it all innocent fun? Would it, could it, should it go further?

"Of course not. She's our little girl who just happens to have different parents," I growled to myself as I booked the seats online. "Just settle. Shower in the other one. Calm things down."