A Valentine for Ian

Story Info
A Valentine for Ian.
3.8k words
4.51
32.4k
49
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

-1-

Valentine's Day. And Caitlin was spending the morning doing laundry, and so was feeling a bit blue. Twenty years old and she had no plans for this Valentine's Day -- or for this Valentine's Evening. She and Stewart had broken up (again) two weeks ago and now doing the laundry was the only excitement that was planned for her day. That and studying. At least her brother was home for the long week-end. Two years younger but he was better than she at school. She could probably get him to help her study. Or, just as likely, talk her out of studying.

She was getting a late start this morning. Almost noon and still not dressed. She was still wearing her standard 'pajamas' -- a long T-shirt, no bra, and, depending on her mood, either some underwear or not. Her blonde hair was pulled into a messy pony tail. No makeup of course. She'd get dressed and cleaned up later -- maybe.

As her mind drifted she continued to pull clothes from the hamper, shaking each item out before dropping it into the tub. She grabbed a pair of her underwear and spread it out by its waistband and was about to drop them in the washer. Instead, she frowned and took a closer look. The dark green fabric was flaked with a large dry white stain. She marched out of the laundry room holding her underwear out before her.

In the living room, her brother Ian was also getting a late start to the day. He was just finishing a cup of coffee and taking his time over the paper's sports section. He looked up to see his sister virtually stomping into the room, holding a dark-green pair of panties in front of her. Unfortunately, he recognized the panties.

"Ian! This is SO gross. Look at my underwear! It's covered with... well, it's covered with cum. Seriously? You jerked off into my panties? Well obviously you did. Argghhh!"

She put her fists on her hips, one holding the offending underwear, and waited for a reply.

Ian stared at her trying to think of how he could avoid being blamed, but couldn't come up with any remotely believable alibi.

"Sorry. I meant to get to the laundry before you. I didn't think you'd find out. I'm... sorry."

"OK, you're sorry. But what? I mean why did you do it?" Caitlin wasn't sure what she had expected him to say. "OK, OK I know guys your age jerk off. Well, I guess guys of all ages jerk off. People. People of all ages jerk off."

Ian still stared with nothing to add.

Caitlin continued. "But why would you do it with my panties? Well, OK, I guess I can see why maybe panties, but why MY panties. Don't you have a girlfriend who can lend you some underwear?

Ian continued to stay out of this conversation.

"Right. Right. You don't have a girlfriend. But MY panties? Maybe we could get you some panties of your own. They sell them at the drugstore -- three to a pack. I'll buy you some OK? Can we do that?"

Ian decided that the truth was probably the only logical course here. "Thanks, but that's OK. I'm only interested in your panties. And I get why you're not crazy about the idea. So forget it. I'll stop using your underwear, OK?"

"You'll stop? How many time have you done this? And why are you only interested in MY underwear?"

Ian found that continuing this conversation was getting harder than he had imagined. "I'm interested in your underwear because they're yours. They feel good, and I think of you while I'm using them. They excite me not just because they're panties, but because they're YOUR panties.

Caitlin came further into the room and sat on the chair across from Ian. "How long has this been going on? How long have you been jerking off using my panties?"

Ian took a deep breath. "Well, the summer before last you bought that black bikini. We had a pool party for your birthday, and you wore it for the first time. You looked so beautiful. So sexy. I was transfixed. You ran around. Flirted. Joked with your friends. Swam in the pool. But the whole time I was completely entranced by how sexy you looked in that bikini. Later, you accidentally left the bathroom door open a crack and I saw you changing into dry clothing. The bikini was lying on the bathroom floor, and I saw you naked from behind. You were putting on a pair of dry underwear and some jeans. From then on, although I still thought of you as the older sister I had always loved, I also thought of you as a young women who was sexually arousing. You became more sexy than sister. I started imagining you when I masturbated, and I've felt that way about you ever since."

He continued, "I never thought I would tell you any of this. As long as it was a secret, I could fantasize about it coming true. But now that it's out in the open, I'm pretty sure this is the end of it... right?"

"I don't' know" Caitlin said. "Actually... actually I don't even see how the real me is involved. This is a fantasy you've been having all on your own."

Ian brightened. "So, maybe you might be OK with all this?"

Caitlin was having trouble processing the situation. "Well, I just found out that my little brother has sexual fantasies about me, and that he's been masturbating with my panties for over a year. I'm not sure how I feel about all this. It's kind of a shock, really."

Ian got up and went to the counter. He refilled his coffee cup. "I'm sorry you found out about this. Are you sorry you found out?"

"Well. I don't feel sorry exactly. It is interesting. I don't know how I feel about it yet. Is this a normal thing? Do younger brothers think about their older sisters sexually as part of their 'sexual awakening'? I don't know. Nobody talks about this stuff. Except to say that it's wrong. I mean, I guess the problem is that I know they say it's wrong, but they don't say how common it is. Do your friends lust after their sisters?"

Ian took a sip of coffee. "Actually, I don't know. We talk about a lot of sex stuff, but it's mostly bluster. 'Sisters' is an area that doesn't come up. Is that because they don't lust after their sisters, or is it because they don't want to talk about it? I don't know. I do remember a guy in gym class saying that he sometimes had sex with his sister. And he implied that he might have had sex with his mom. But he often bragged about things no one believed. I guess we all were curious, but we assumed none of it was true. But how could you not be intrigued?"

Ian returned to the sofa with his coffee.

Caitlin nodded, thinking.

Ian continued "So, yeah, I lust after my sister. You. But I've never told anyone. I didn't even want to tell you."

Caitlin held up the underwear. "But my cum-soaked panties led us here."

"Yeah. I guess I didn't do a very good job of covering my tracks this time. But come on - this is the first time you've noticed and I've been doing this for quite a while. But OK, I can stop using your panties. And I'll try and stop fantasizing about you. OK?

Caitlin leaned back in the chair. "Look - I don't want to be in charge of your fantasy sex-life. Just remember that it's a fantasy -- not a realistic goal. Right? Anyway - I have to think about all of this a bit. OK?"

She got up and returned to the doorway. She looked back at Ian wishing there was some way to summarize all this.

Ian just gave a little shrug.

Caitlin continued. "But, I guess, I want you to do what turns you on and satisfies you. If that involves a fantasy me? Well I'm not responsible for the fantasy me. So I guess enjoy yourself. I don't think that you're actually harming my underwear. Just, I guess, only use the panties from the laundry. Stay out of my clean underwear drawer. Right?

Ian nodded. "Of course. I only use panties from the laundry. But it's OK? You're not grossed out? I can still use your laundry underwear?" He paused. "I actually prefer them used". Another shrug.

"Ewww, Ian! Please!" She paused. "I guess you can keep using them. I'm confused about what it all means, but evidently this has been going on for over a year and I didn't even notice. So for now... Well I guess you can keep 'enjoying' my used underwear. You know how pervy that sounds, right?"

Ian did. "Well, I've always realized that my fixation might be pervy. But it seems to be what turns me on..."

Caitlin seemed resigned. "All of this is more than I really needed to know, but I did say I was curious. So, thanks for talking. For being honest. I'm going to finish the laundry."

She got up from the chair and started out of the room.

"So, can I borrow those green panties?" Ian asked with some embarrassment.

"These? No! They're gross! They're going into the washer."

Ian wasn't surprised, but was disappointed. Caitlin stopped and turned back toward him. She lifted her T-Shirt revealing the small blue panties underneath. She slid them down to her ankles, stepped out of them, and threw them over to Ian.

"Love you." she said as she headed toward the laundry room.

Ian looked at the panties that had landed near him, and then up at the empty doorway.

-2-

Shortly after Noon, Caitlin's mother (Jennifer) was in her bedroom also getting ready for the day. Her blonde hair needed brushing and was still damp from the shower. Wearing a pair of lacey white panties and a white bra, she was going through her closet looking for a dress for the day. She pulled a yellow one from a hanger and held it up.

A soft knock on the door was accompanied by "Mom, it's me, Caitlin. You said you wanted to talk?"

"Come in. Yes I want to talk to you about tonight".

Jennifer turned as Caitlin entered the room closing the door behind her.

"Oh, Caitlin. You're wearing your black bikini! I haven't seen you wear that in ages".

Catlin looked in the bedroom mirror examining the suit. "Yeah, I thought I'd hang out by the pool this afternoon".

"I'm surprised it still fits! In fact I think the top looks a bit tight"

"Mom!" Caitlin put one hand on each of her breasts and squirmed in an effort to get a better fit.

She continued. "What did you want to talk about?"

Caitlin's mom bent, stretching her white panties to their limit, and pulled a pair of sandals out of the closet. "I'm going out tonight, and I wanted to make sure that you and Ian are OK being on your own for dinner. She stood and faced Caitlin shoes in one hand and the yellow dress in the other.

"Mom! A Valentine's date? Good for you!"

"Yes, Robert asked me to dinner. I'm a bit nervous, really"

"Isn't this about your third date? Is this getting serious?"

"Yes. I mean no, it's not getting serious. Yes it's our third 'date'. So do you need me to leave some money for a pizza or something? I'll probably be a bit late"

"No, we're grown up. We can take care of our own dinner. But how late? You mean 'bringing a toothbrush and clean underwear' late?"

"Caitlin!"

"Come on Mom. Valentine's Day? Dinner? And look at you -- in a bra and panties and you're hot!"

Jennifer slipped the dress over her head and smoothed it into place. "Never mind. I'm going down to the Mall. Let Ian know about dinner."

"O.K., I will. I'm going to go hang by the pool for a while."

Caitlin opened the bedroom door. As she started to exit her mom commented "Well, the bikini bottom still fits. I think you've grown into it."

Caitlin looked over her shoulder at her reflection in the bedroom mirror. She tugged the bottoms up giving them an even tighter fit. She slapped herself on the ass and exited.

-3-

As she headed for the back yard, Ian was just heading for his room. He was a bit shocked to see what she was wearing. "You're wearing the black bikini. Is that for me?"

Caitlin stood up straighter and pushed her chest out a little. "Oh, I just thought I'd hang by the pool for a while. You reminded me I haven't worn this for a long time." She looked Ian in the eyes and continued "Mom's going out for a while. Come out and join me if you want." She turned and headed out the French doors with a towel and sun block in her hands. She stopped and turned back. "Would you bring me a glass of white wine when you come? Thanks." She continued on out to the pool area.

Ian started for the upstairs to change, then started for the kitchen for the wine, then realized he should get changed first and headed up the stairs still not sure what Caitlin was up to.

By the pool, Caitlin put her towel down on one of the lounges and lay down. Although it was February, the afternoon sun was still fairly direct. She closed her eyes and made a mental note to put on sun block before being out here much longer.

She heard the French door open and realized Ian was joining her. She opened one eye and saw that he was bringing a bottle of white wine and two glasses. Their mom wasn't completely against Ian having the occasional drink as long as he was staying home and he didn't over-do it. Evidently he had no Valentine's Day plans either.

"Hey" Caitlin said as she got up from the lounge. She walked over to the edge of the pool. "I'm going in. Join me?"

Ian put the wine down on the table and looked at her. "I'm surprised that bikini still fits you."

"Ian!"

"Well", Ian continued, "the top actually does look a bit tight."

Caitlin started to adjust the top and then stopped herself. "It fits fine".

"The bottom looks great though" Ian said.

Caitlin turned away from Ian and pulled the bottom up tighter. She looked over her shoulder at him, then bent accenting her ass and dove into the pool.

Ian sat down on one of the lounges and poured himself some wine.

Caitlin swam two laps, one underwater. When she surfaced she shook out her hair and called to Ian. "Come on in. Swim with me. It's nice".

Ian put his wine down, got up and dove into the pool. He also swam a lap and came up standing right next to her. They were both in water half-way between their hips and shoulders. Ian stood very close to Caitlin. She still looked so sexy in that bikini. Being shorter, Caitlin looked up at him. "I told you it was nice". He looked down at her, and then looked down a little further to admire her cleavage. "Yes, it is nice." She caught his meaning.

He continued, "But a little cool. I think I'll get out and lay in the sun."

Caitlin agreed. "Yeah, me too. Let me put some sun block on you." She headed for the shallow end of the pool and climbed the steps. Ian took the faster way and climbed out over the edge.

They reached the lounges and she stood very close to him. "Are you ready for some sun block?" she asked. She reached down to the table to pick up the bottle and brushed against him. She took a step closer and they were almost touching. "Would you hand me my wine?" she asked without taking her eyes off him.

He smiled, turned, and got her glass. He handed it to her. As she took it she pushed out her chest causing her tits to just brush against him.

Caitlin took a sip, still holding his look. "Have you had a chance to use those panties I gave you this morning?" she asked.

Ian was surprised. "No. No, I'm saving them for later".

She glanced down at his suit. Although baggy, it was clear that he had an erection. "It looks like you could use them now". She looked back up at him.

"You're trying to give me an erection. And you have. What do you want me to do with it?"

She smiled. "I want you to lie down, if you can, and I'll put sun block on your back. OK?"

Ian had to arrange himself a bit, but was able to lie on the lounge. Caitlin straddled his legs and began rubbing lotion on him. "Does that feel good?"

"Yes. But feeling you sitting on my legs isn't helping with my hard-on."

Caitlin finished, got off him, and lay on the other lounge. "OK. You do me now. Maybe that will help". She handed him the lotion without looking at him.

Ian started applying lotion to her back. She stopped him. "Undo the top strap. It will make it easier for you. And this top is too tight anyway".

Ian obliged. He unclasped the strap and let the two sides fall beside her. He then applied lotion from her shoulders down to her bikini bottom.

"All right. Thanks. I'm going to roll over now, you can get up."

Ian moved over to his lounge and sat. Caitlin rolled over into a sitting position. She held her bikini top against her breasts with one hand. She reached over with her other hand and took her wine glass from the table and took a sip. She glanced over at Ian. He still had a noticeable erection.

"Look away. I'm going to apply lotion to my front" Caitlin said.

Ian turned away so he was facing the house.

Caitlin let her top fall to her lap, and started rubbing sun block all over her front, including her breasts. The stimulation caused her nipples to harden.

Ian turned back, looking at her naked breasts as she applied more lotion.

Caitlin put her hands over her breasts. "I told you to look away!"

"I did. But you didn't say for how long. Should I look away again?"

Caitlin picked up the bikini top and dropped it to the deck. "No. I'm going to get an even tan. You can ogle my tits if it turns you on. And I can see that it does" She gave him a knowing smile.

Ian re-filled his glass from the bottle.

Caitlin put the lotion bottle on the table and lay back on the lounge, closing her eyes. "Maybe you want to go get the panties I gave you this morning. It looks like you could use them." Without moving her head she opened one eye and made eye contact with him.

"Go get them? You mean bring them out here? You want to watch?"

"Well, I'm lying here topless. It seems like something you might fantasize about. Would that turn you on if I watched?"

Caitlin put one foot on either side of her lounge so that her legs were spread apart. The thin strip of material that ran between her legs revealed as much as it covered.

"Do you want to watch?" He asked. As he said this, Ian stood. His erection was straining against his swim suit clearly visible.

Caitlin sat up and repositioned the lounge so she wasn't facing the sun. "I've been thinking about it since this morning, and I think I might." She sat back down and pulled her knees up to her chest. The area between her legs was still clearly visible. "I dare you".

Ian looked at her. He took his trunks by the waistband and pulled them to his ankles. When he stood his cock jutted out fully erect. He took it in his hand and began to slowly masturbate. After a few strokes, he picked up the bottle of sun block and applied lotion to his hand. He then resumed masturbating, his cock growing even bigger.

Caitlin was transfixed. "Do you like having me watch?" she asked.

"Yes. I like you watching. I like seeing your tits. I like seeing between your legs. I like seeing your bikini bottom and imagining what's under it".

"Are you going to come?"

"Yes"

"Even with me watching?"

"Especially with you watching." He continued to stroke.

"Even without panties?"

"Yes"

"Would you like some panties? I want to see you do it with my panties." Caitlin started rubbing her nipples making them harder.

"I don't want to stop and get them. I want to come"

Caitlin lifted her butt and pulled off her bikini bottoms. "Here, use these. They're like panties".

Ian took the black bikini bottoms and wrapped them around his stiff cock. He increased the pace of stroking. He looked down at Caitlin. She was now naked, one hand massaging her tits, the other had found its way between her legs and she was starting to masturbate along with him. She lay back with tits fully exposed and her legs as far apart as she could get them. Her fingers rubbed rhythmically at her clitoris.

She locked eyes with him and smiled. "This is so fucking exciting. I love watching you jerk off into my bikini. I'm going to come with you".

He started stroking even faster. His eyes were on her hands, her tits, her pussy. His hand was at full speed and he felt the first spurt start to shoot from his cock. He held the bikini bottom away so that Caitlin could see each spurt as it hit its target.

12