Smaller Is Good

I'm 38, my name's Dave and no - I'm not an alcoholic but I am single and have a couple of jobs. My main job is working in an outdoor equipment store but I'm also what's called a 'resource person' for a few of the local schools. Basically, if they need help with an outdoor oriented activity, they can arrange for me to come in and assist the teachers. My work is cool with it because I always put a good word in for their gear, I'm easily able to take a day off work when needed and the school covers about 90% of my normal days' pay. As an added bonus I get to enjoy quite a bit of 'eye candy' in the halls and in class.

My most recent group was a grade 12 class doing a combination of orienteering, knots and tree identification over a couple of weeks. Seeing as it was a nice warm May there were quite a few lower cut tops, tight shorts, short skirts and the occasional female student who decided not to wear a bra which made it that much more enjoyable.

I'd just finished the last day and some of the students were helping me carry the gear back out to my truck before they went home. It was cooler than the rest of the week had been and was raining a bit but one of the girls - Alyssa - didn't seem like she was in a hurry to leave and once the others had left she said, "I'd like...can I.....I was wondering....oh fuck" and stopped then continued, "I don't even know if I should ask you or not but I need to ask someone" and then stopped again.

She was stammering and blushing so I was pretty sure it wasn't a question about any of the stuff I'd covered with her class so I gave her a few seconds and said, "Alyssa - how old are you?"

She gave me a bit of a puzzled look and said, "I just turned 18."

"Ok, so whatever you're trying to ask me - are you asking as a student or an adult?"

She thought for a couple of seconds before replying, "As an adult."

"Well, if you're 18 and asking as an adult then go ahead and ask and I'll do my best to give you an honest answer. Are you ok if we sit in the truck to talk so we don't get wet?"

My reply seemed to calm her down so she nodded and we sat in the truck. Once inside, she took a deep breath and kind of blurted out, "Why do guys only seem to like girls with big tits?"

I'd been trying to figure out what she was trying to ask but her question still caught me a bit off guard. There was no doubt why she was asking - she was slim, about 5'4 but at best she had an 'A' cup and seeing as she was one of the ones who didn't always wear a bra I'd noticed that instead of rounded, they were also somewhat pointy and her nipples were often hard.

"Have you asked your mom?"

"Yes, she said not to worry - that I'd meet someone who wouldn't care that I wasn't big in the chest. I can't ask any of the teachers because I know that's not a conversation they can easily have with a student, I wouldn't want to ask any of mom's friends either and dad left years ago so I can't even ask him if I wanted to. You seem pretty cool so I thought that maybe..." and then her voice kind of trailed off to nothing again.

I could tell she was almost in tears so I took a chance and put my hand on her shoulder saying, "I'll bet the way your mom said it, you're thinking that you'd just be settling for someone who doesn't care whether or not you've got big boobs."

That got the first bit of a smile, "Ya, pretty much."

"Well, if it helps - I'd look at it more as 'wait for someone who looks at you and goes - damn she's hot and I'd love to go out with her'."

"Ok, that makes me feel better but I'm still wondering why guys prefer big tits."

"Not sure I can help you on that one. Everyone generally has some sort of preference - long/short hair, blonde/brunette, big ass/small ass but yes guys, at least younger guys do seem to prefer big boobs."

"Ok, kinda makes sense. You said you're not sure if you can help - does that mean you prefer small boobs to big ones?"

Now it was my turn to be a bit embarrassed, "well....um...it's not the size of the boob that I find attractive."

I wasn't sure I wanted or should go any further but when I saw her puzzled look, I continued with, "Well, you were mature enough to ask me an embarrasing question so the least I can do is be mature enough to answer yours. I guess I'm more of a 'nipple' guy."

"What do you mean a nipple guy?"

"Well, I certainly enjoy looking at a ladies' boobs but what really catches me is seeing a nipple - especially if it's hard, long, puffy or once I get to know her it's a big turn on if she's got really sensitive nipples."

"Even if the boobs were as small as mine?"

"For sure - I've often found that women with smaller boobs have firmer, more sensitive nipples."

I could tell she was feeling much better and was definitely more relaxed. "Well, they're certainly sensitive - I just wish they were bigger."

Without thinking, I replied "they looked fine to me."

"How can you say that? You haven't seen them."

I wasn't sure I should explain but figured I was in this far. "Well, maybe not all of them but you seldom wear a bra and more than once you wore a fairly loose top so I certainly saw enough a few times when you bent over to say that they looked fine to me."

Alyssa blushed a little before saying, "Oh...sorry, I didn't know I was showing that much."

I just smiled and said, "Don't be sorry - I certainly didn't mind the view."

"How much did I show?"

My smile got even bigger thinking about it before I replied, "Well, certainly not all the nipple but enough to know that you fit into the 'puffy' category."

"And you didn't think they were too small or funny looking?"

"I likely shouldn't say this but I think we're already past the line of what we should or shouldn't be saying so yes, I liked what I saw - definitely 'able' looking."

"What do you mean 'able' looking?"

I chuckled a bit before answering, "touch-able, kiss-able, nibble-able, suck-able."

"Oh...wow, ok...I don't think I've ever had anyone describe my nipples that way - but I like it."

"I can tell!"

At first Alyssa looked at me and then seeing where I was looking she looked down at her shirt and the combination of cool, damp and braless meant her nipples were showing plainly against the fabric. I didn't realize how long we'd been there but after a bit of silence she looked at me kind of shyly and said, "You said you've already seen some of me - would you like to see more?"

I took a look around and realized that the parking area was almost empty. "I would, but we could both get in a lot of trouble if anyone saw you."

"Ya, I guess." and then she surprised me by quickly flipping up her top to show me two of the smallest but sexiest tits I'd ever seen. Likely no more than 2 inches across at her chest, sticking out less than 2 inches with beautifully puffy areola's and nipples that were rock hard.

There's a good chance that even having her in the truck with me would be frowned upon by some people but we hadn't really done anything that would get us in real trouble, at least not yet. As soon as I saw her nipples come into view, my mind immediately went in two different directions. One was that she needed to pull her top back down before anything else happened and the other was that I shouldn't lose the opportunity to find out just how nice they felt.

I'd like to say that the 'proper' side won but instead I reached over and gently touched one nipple and then the other. When she didn't pull back, hit me or yell, I repeated the touching and then started gently squeezing and rolling her nipples between my fingers which got an immediate moan from her and now her nipples were even harder and almost a half inch long.

When common sense finally kicked in, I pulled back and after looking at each other for a second or two we both said, "Wow" at almost the same time. Thankfully that broke any tension there was and Alyssa pulled her top back down before I needed to decide if I was going to repeat my touching or just be happy that I didn't get caught the first time and that she didn't mind.

Seeing as it was raining harder, I asked if she needed a ride home. She said she'd appreciate it and when I asked her how to get there, it turned out she was in a subdivision south of the river while I lived on the north side. When we got there, I took a chance and gave her a card saying, "just in case there's anything else I can help you with."

Alyssa just smiled and got out of the truck. I'm not sure what she did when she got inside but I know when I got home it wasn't long before I was laying on the bed stroking myself until I shot a huge load of cum.

I didn't hear anything back from her and figured that she was either too embarrassed or she'd gotten the answer she needed. Then a couple of weeks later I was about 15 minutes into a walk in the woods when I heard, "hey, Mr. Carson!"

When I looked back, I saw Alyssa coming toward me. We talked for a few minutes about school and other general stuff. I thought a few times she wanted to say something more but seemed to stop herself so I finally said, "If you want to talk about what happened in the truck, I'm fine with it."

The look on her face told me I'd pretty much hit on what she was thinking and she said, "I didn't know how to bring it up so I'm glad you did. Do you ever think that there's a reason that things happen?"

That kind of surprised me but I said, "Yes, why?"

"Well, I've thought about what we talked about and what happened quite a bit and every time I did, I got turned on wondering how much better the 'licking, nibbling, kissing and sucking' would feel than just the touching but I couldn't quite get up the nerve to contact you again. I thought about it but I really couldn't just ask some guy at school if he'd like to suck my nipples so I could find out what it felt like. Now today I go out for a walk and you're here too...maybe...well would you..."

I was pretty sure I knew exactly what she was thinking so I said, "I'd be lying if I said I hadn't thought about how good it felt to touch you last time too so if you'd like to find out what it would be like to feel a mouth on your nipples, I'd be more than happy to show you."

Alyssa just smiled and nodded so we walked a bit further before I turned onto a smaller trail that led up to a field and then a turn to a more heavily wooded area. Once I was sure that we would be able to see anyone before they could see us, I looked at Alyssa and asked, "Are you sure?"

Instead of answering, she just smiled and pulled her halter top down so both tits were on full display. Now that I was in front of her, I had a much better view so I took a few seconds to enjoy it - her tiny, cone shaped tits ended in a beautifully puffy areola that looked like a paler Hershey Kiss and then a wonderfully erect nipple topping it all off.

After I'd enjoyed the view for a few seconds, I reached up with both hands to feel the nipples against my hands and to trace lines around and across the areolas. Her slight moan told me she was enjoying the touch so I continued touching and teasing on one tit with my fingers at the same time I leaned down and started tracing the same paths on the other one except using my tongue. That quickly got more moans so I spent the next few minutes switching from one to the other until eventually instead of licking, I was sucking pretty much her whole tiny tit into my mouth. Keeping a gentle suction, I slowly pulled back until just her nipple was left between my lips and then while I while I kept sucking, I flicked the tip of my tongue back and forth over her nipple.

After only a few flicks of my tongue she moaned louder and said, "Oh fuck that feels so good!"

That was the only incentive I needed to spend about the next 10 or so minutes licking, sucking and kissing back and forth from tit to tit. The more I did, the more she moaned until finally she let out a loud, "Oh fuck!" and pulled my mouth away from her tits. At first, I wasn't sure what was wrong - I was afraid maybe someone had come up on us that I didn't hear. When I looked at her, her face was totally flushed and she was almost panting. Then I looked down and when I saw a growing wet mark on the crotch of her shorts everything made sense.

"Is that from me sucking your tits?"

At first all she could do was nod and said quietly, "I'm so embarrassed...I think I just pee'd myself when I came!"

I just smiled and said, "I doubt you pee'd - I'll bet you either got really wet from cumming or maybe you squirted." On impulse, I slid my hand into her shorts, slid my fingers in between her pussy lips and then pulled them back out. After a quick sniff and a taste, I looked at her and said, "definitely not pee...and you taste great!"

That made her smile and say, "That makes me feel a lot better!" She thought for a few seconds and then continued, " I'd love to have you do the same thing to my pussy that you did with my nipples but I'd like to save that for someone I'm actually dating - I hope that's ok?"

As much as I'd been hoping to be tasting and maybe even fucking her, I did understand and told her so which got me a smile, a hug and a quick kiss before she pulled her top up and said, "I think I'd better head back."

When I got home, I had another great jerk off session as I thought about her nipples in my mouth and enjoyed the trace of her scent on my fingers. I heard nothing for another couple of weeks and then out of the blue I got an email from her that said, "You were right - I finally found a guy who loves my tits just the way they are and the rest of me too - his name's Darrin and he's one of the guys at the place I was working after school...thanks so much for helping me realize I was desirable!"

Oh well, so much for the idea of any other fun there but I'd certainly enjoyed what we'd done. A few weeks after that, I was out for a walk and saw her walking toward me with a woman that I assumed was her mom. I wasn't really sure if I should say anything or not when Alyssa said, "Hi Mr. Carson - how's your summer going?"

"Going pretty good...how about you?"

By now I could see her mom looking at Alyssa, then me and back to Alyssa again. Alyssa must have noticed too because she said quickly, "I'm sorry... Mr. Carson this is my mom...mom this is Mr. Carson - he helped with all the outdoor activities for our class this year."

I smiled at her mom and said, "Glad to meet you - feel free to call me Dave instead of Mr. Carson."

She just laughed and said, "Only if you agree to call me Debbie instead of mom."

That broke the ice and we chatted a bit more before Alyssa said, "I was trying to show mom that nesting eagle that you mentioned in class but I can't find it -- can you show us?"

"Sure, it's not too far from here."

"That'd be great - do you know if the eagle's still using it?"

"There was one there the last time I was by there so good chance they're still around."

We talked some more as we walked and I quickly realized a few things - Debbie was pretty much an older version of her daughter, a little taller, just as pretty, a great smile, fit and maybe a bit bigger ass but it looked great on her. What caught me the most were the two small mounds on her chest that were almost hidden except for the outline of her nipples which showed very nicely against her shirt. To make it even better, she seemed like a really fun person - she enjoyed hiking, biking and camping and could hold a good conversation.

By the time we got back to where the cars were parked, we were chatting like old friends. It turned out she'd had Alyssa when she was 19 as a result of a college romance and the marriage had broken up by the time Alyssa was 8. I already knew I'd enjoy seeing more of Debbie so I asked her if she'd like to go for a bike ride the next weekend and she said she'd love to. Over the next few weeks we went for a couple of bike rides and another hike. At the end of the last hike I said to her, "I've really enjoyed getting together with you the last few weeks - I was thinking of taking the canoe out next weekend and paddling down the river - would you like to join me and then stay for dinner?"

Right away Debbie said, "I'd love to! It's been years since I've been in a canoe and dinner sounds great. I've enjoyed the last few weeks a lot too...I'm so glad you were helping with Alyssa's class or we'd never have met!" and then gave me a nice hug and a kiss on the cheek.

We decided that we'd meet the next Saturday where I'd be taking the canoe out of the water and then drive together to where I planned on putting it in. When she got there, she was dressed in a pair of quick dry shorts, a thin t-shirt, a sun hat and a pair of sandals. I was pretty sure that she was braless too and she looked damn good. When I told her that I thought she looked great, I got a nice smile, a "thank you!" and an even longer hug than the one a few days earlier. This time I decided to take a chance and as we parted from the hug, I gave her a quick kiss on the lips. I was pretty sure it wouldn't upset her but I wasn't quite prepared for her arms around my neck and her lips pressed back against mine for a long, passionate kiss.

This time when we pulled away I said, "wow, that was quite the kiss!"

A little shyly she said, "I'd been hoping you'd kiss me since the second hike so when you kissed me I wanted to make sure you knew it was mutual."

"Oh, it's certainly mutual!" and with that I pulled her to me for a long series of kisses before we finally decided we'd best get the canoe in the water and save any more kisses for later. It was only a 20-minute drive to where I was planning on putting the canoe in with us chatting all the way.

Once we were on the water, it didn't take long to see that while she hadn't been in a canoe for a while, she certainly remembered how to paddle. We were soon enjoying a nice quiet, leisurely paddle and enjoying seeing turtles, herons and even a deer. At about the halfway point Debbie asked if I could pull in to shore because she had to go pee. She was in luck, there was an easy spot to pull into right ahead and as she got out she jokingly made me promise not to leave her there.

We got out and I held the canoe to make sure it stayed put while she headed for the bushes to relieve herself. Everything went well until she was almost back to the canoe, that's where she slipped on the mud and pretty much slid on her back, feet first down the slope and right into the water. She wasn't hurt but when I helped her up and out, her face, hair and shirt were totally wet and the back of her shirt, shorts and legs were covered in mud. We both laughed a bit and without thinking, she grabbed the bottom of her shirt and pulled it up to wipe off her face. I immediately realized that not only had I been right and she was braless but she was built almost identical to Alyssa - very small boobs that looked like little cones with puffy areola topped off with nice, perky nipples. The only real difference was that her areolae were chocolate brown rather than pink like Alyssa's. Ok, getting dunked in the cool water likely had something to do with the nipples being so perky but they were great to look at.

As she wiped her face, she obviously realized that she was giving me a bit of a show and quickly pulled her shirt back down saying, "sorry but it's not like there's anything there worth seeing anyway."

"Well, I'll agree there may not be a lot there but what there is looked incredibly good to me!"

"If my ex had thought that way, maybe he wouldn't be my ex." was her quick reply.

She'd never really talked about her ex and I hadn't asked but that made me say, "You've never really said much about him so maybe I shouldn't ask but what did he think?"

"Well, among other things, he thought that my boobs looked like a little girl and did everything he could to convince me to get a boob job. He figured anything under 36C wasn't enough. There were quite a few other things he didn't like too and I finally got tired of it, took Alyssa and left him. Last time I saw him he was with some chick that had like 44 EE tits that were obviously store bought."