Annas Milk

This story is in part about breastfeeding, although there's more to it than that. It has a slow warm up...

*****

Anna was a drop-dead gorgeous redhead in my high school with long legs, curves in all the right places, a beautiful face with lots of freckles, and almost tomato-juice colored hair. She was beyond pretty, and closer to take-your-breath-away-and-stare lovely, while at the same time still being the wholesome girl-next-door type. None of that might have mattered much to me if she was a bitch, but Anna was also seemingly one of the nicest, least pretentious, and kindest people you'd ever meet.

But she was also going out with my best friend Nick, and so she was off limits—not that I would have had much of a chance with her anyway. This is the story of how Nick trusted me, Anna trusted me, my parents trusted me, and I sort of even trusted myself. But I ended up letting everyone down. Or did I? You decide.

This was more than a dozen years ago, and Anna and Nick were a year ahead of me in high school, and getting very serious. In part because I was Nick's best friend, Anna always trusted me, and even flirted with me in an innocent way. I think also she really wasn't aware of how attractive she was to me. In fact, I wasn't sure she really knew in general just how beautiful she was, or of the destabilizing effect she had on most men—and I bet on some women too.

Anyway, back to the story, because there's a bit of explaining to do...

I was mostly happy for Nick and Anna as they got hot and heavy their senior year. But, I admit, I was also sometimes jealous because Anna had mostly taken away my best friend. And I was a bit jealous too of how Nick was fucking, as he told me in some detail, this flame-haired goddess almost all of the time.

I should admit that at this point I was a shy virgin who had never gotten beyond kissing, and hadn't even done much of that.

Then, shortly after they graduated from our high school, Anna got pregnant. It was an accident and a shock, but they decided to keep the baby and get married. But for some people they didn't do it quickly enough, because by the time of the wedding Anna was showing a medium amount. It was a little bit of a scandal in our upper-middle class enclave, and I heard some of my Mom's friends, and even my Mom, talking about it.

Nick then joined the National Guard to help support his new family, and to pay for his tuition at the local community college. Nick was pretty smart, but only a B/B+ student, and the same was true of Anna, and so neither of them had even bothered to apply to the good state colleges.

As all this was happening, suddenly both of them became literally closer to me, because they moved into my parents' carriage house in the back of our big house behind the pool. Our yard was pretty big, and in the back was a small gardner's or caretaker's house. It had just one floor with two bedrooms, a small kitchen, one bathroom, and a small living room-dining room. The whole thing was about 900 square feet, and so about the smallest regular house you could imagine. My parents sometimes rented it out, and sometimes just had it for guests, and it happened to be available after Nick's slightly scandalous marriage to the obviously pregnant Anna. Since Anna's Mom and my Mom were friends, it was worked out for them to live there, although they were still charged rent, even if it was a couple of hundred dollars a month less than market.

Soon Anna and Nick's baby, little Ben, was born, and they were seemingly a happy if exhausted couple in the back of our house. Nick was going to college full-time, and Anna taking time off for several months as the baby grew. Once baby Ben was a few months old, reddish-blond and cute as could be, with smiles for almost everyone, I began to get trained to do some babysitting for them, including learning to change little Ben's diaper.

And, when I was over there, I really saw Anna breastfeeding for the first time. She was as beautiful as ever, maybe even more so since the birth, but the exhaustion of motherhood had given her dark circles under her beautiful green eyes. And her breasts, always shapely and good sized, and I'm afraid the focus of my attention for the last couple of years of high school, were now even bigger. And Anna now wore loose blouses and, of course, nursing bras.

One day when I was over there visiting with Nick and Anna in their living room, we were talking about where I was going to go to college when I graduated from HS in a few months (full scholarship at the state's flagship U), and we were also giving advice to Nick on what classes he might take during the summer, and discussing whether Anna should resume her job at the public library, where I also worked. Then baby Ben woke up from his nap in the back room and started crying.

Nick and Anna both smiled. Nick went back to get the baby while Anna kept talking to me, while simultaneously unbuttoning her blouse. She had a bra on underneath, but I could see quite a bit of cleavage, and I knew what was about to happen. Nick came back in with the crying baby, and I started to get up to go, but Nick and Anna said at the same time that I should stay, that it was beautiful watching a baby get precious nourishment, and that I needed to learn what to do. They'd gone to some La Leche classes together, and were big supporters of breastfeeding, including in public.

They'd already told me about this, and I had agreed, but I was still shy and uncertain. Anyway, I sat down. In the past, when we'd been in a park, or at my parents' house, and the baby had needed to eat, Anna had somewhat awkwardly draped a cloth over her chest and the baby, but apparently since it was just me, one of her best friends and her husband's best friend, as well as their new main babysitter, she didn't bother. And so to my wonder, before I could look away, as Nick handed her the baby, Anna unhooked her bra over her left breast, and it opened up and revealed most of her engorged and freckled breast with its large areola and medium-sized pink nipple. The crying baby, also seeing this, quickly stopped crying. With her right hand under her breast and nipple, she gently angled her nipple toward the baby, who latched on and started suckling down the milk.

It really was a beautiful sight, and I was happy for the baby, but I'm afraid I was also thinking: wow, I just saw Anna's breast. This was something I didn't think I'd see in my whole life. I'm ashamed to say that my dick twitched in my jeans. Anna and Nick kept chattering on, as if it were the most natural thing in the world, which I suppose it was, and then the baby needed to be burped and to change sides. They wanted me to learn how to do this, and so as the baby de-latched, Anna had one breast visible again, but now there was a little drop of milk on her nipple. As I glanced at this, Nick first gave me a cloth for my shoulder, while Anna hooked her bra back up. And then they taught me how to gently pat the baby while he was draped over me. Baby Ben did indeed burp, which, if you know babies, was more like a little vomit, but when this happened successfully it made Anna and Nick very happy. Clearly I had to been able to pass yet another test on my way to being able to babysit their little treasure.

Nick said, "Since you've got him, would you give Ben to Anna so he can nurse the other side."

"Yes," I said, hoping they wouldn't notice that I was blushing.

As I brought Ben slowly over to her on the couch, gently supporting his head and neck as they'd taught me, Anna unfastened the other side, revealing her equally beautiful and engorged right breast, which I couldn't help looking at quite closely as I brought little Ben in for the touchdown. Using her left hand this time, she angled her nipple for him. Anna smiled a beautiful smile at me as the baby latched, and I saw Ben sucking away at the nipple of her other tit. Again, I'm ashamed, but I was somewhat turned on.

And I continued to be as I saw Anna's breasts almost daily from this point on. Each night, alone in my bedroom, I would put lotion on my hard and straining cock, and as I thought about Anna's luscious breasts literally dripping with milk, and then of what was between her legs, after just a few minutes of stroking my sperm would come squirting out into the waiting tissues.

I don't think they knew how it was affecting me. Thank goodness. Probably they thought: perhaps this is a little turn on for him, but boy do we need a cheap, reliable, available babysitter, and no one is more trustworthy than David.

And then, suddenly, Nick's National Guard unit was called into active duty and shipped over to Afghanistan, leaving Anna alone with the baby. Of course, she had a support network, which when it came down to it consisted mainly of her Mom, me, my Mom, plus one of her girlfriends.

It was arranged before Nick left that I would babysit five days a week for four hours a day, allowing Anna to get out of the house, run a few errands, and resume working several hours a week at the public library, where I also worked. I was supposed to get $6 an hour, which if you know how much work it is to really look after, care for, feed, clean, and entertain a baby, is really not much money. It was more of a favor and obligation to them, my best friends. But I have to admit it was fun. Baby Ben really started bonding with me, and life was really enriched by the little guy's smiles and noises and everything else, even though there were lots of poppy diapers and lots of burps to clean up. I would feed Ben with breast milk from a bottle that Anna had expressed with an electric pump from her milk-filled breasts.

It was heartbreaking when Nick had to say goodbye. When he and I were alone the day before he left, drinking beer together, he told me to take care of Anna and the baby for him as best as I could. And I promised I would. And then he told me to watch out for any of her former boyfriends, or any guys that might try to get to her while he was gone. He told me something that I agreed with, that Anna was not quite aware of how beautiful she was or her effect on men. This was especially true after the pregnancy, he told me, because she'd gained twenty pounds, and there had been other changes to her body. As he said this, a look of almost disgust crossed his face for a second. She felt, he told me, like she was ugly compared to what she had used to be. Anyway, would I watch out for her, care for her and for baby Ben, keep her company, and keep her from getting lonely? That was a lot to ask. But my friend was facing possible death, and so I promised I would do my best.

The first days after Nick left were difficult. Anna cried a lot, and I hung out with her and Ben many hours beyond the four hours of babysitting that I did. It was summer, and my schedule was pretty free. And with my best friend gone, and no girlfriend for me in sight, I was free to be with Anna and help with the baby.

And Anna, even in her exhausted and somewhat depressed state, still wove her magic. You know when a woman is so pretty, and yet also nice, and she actually likes you and is being genuinely friendly to you, and even trying to charm you sometimes, how it feels like you're in a magic spell of beauty and laughter? That's how I felt around Anna most of the time. You may have figured it out by now that I wasn't just really attracted to Anna, but I realized began to admit to myself that I loved her too.

But I could tell she was having a tough time keeping it together, and she was crying a fair amount. For obvious reasons, she was depressed sometimes, and I knew I needed to get her out of the house and try to help her feel better about herself.

"Hey Alice," I said one day, when Nick had been gone for about three weeks, "Why don't we go to the public pool!"

"Why?" She answered in a rather flat way. "We can just go swimming in your pool."

"Well, we might meet some people we know. And, in any case, we can show off this handsome guy," and as I said this I grinned at baby Ben, who was in my arms, and he grinned a gummy smile back at me as if he knew what I was talking about.

"I'm not sure I can," Anna said, with a pained look on her face.

"What do you mean? Why?"

"Well, my Mom got me a new bikini to fit my 'new shape,'" She said this ironically, clearly quoting her mother, "but I just...I'm not sure I feel comfortable being in public looking the way I do, down there," she said, and looked down at her belly.

"Nonsense!" I said, "It'll be fine!"

"You say that now, but you haven't yet seen what I look like," she said, still seeming dejected.

It was true that I'd seen the tips of her breasts a lot for the last several weeks, but I hadn't seen much more of her than that. And I remembered, before her pregnancy, of how much of a stunner she was in her bikini.

"Well," I said smiling, "get into your swimsuit, and I'll tell you what I think."

"Really?" Alice said, "you promise to tell me what you really think?"

"I promise."

"OK!" She said, suddenly seeming excited, and she left me and Ben to go into the bedroom to change.

A few minutes later she came strolling out in her new bikini, and said, "Well?"

Her breasts were magnificent in her new pink bikini top. She had told me that she had been a C cup before, and since Ben was born was now a D cup, and I saw what she meant. Her breasts had gone from medium to larger, and her bikini top showed an impressive amount of cleavage. As much as I'd seen the tips of her breasts in the nursing bra, seeing them this way was different. I couldn't help but look at her with an almost awe-struck and typical teenage male expression that often happens when you see a woman like that. I composed myself quickly, but one word was all I could manage:

"Wow!"

Anna smiled a smile like a perfect spring day, and then she laughed. The sound of her laughter was like joyful music. She looked really happy as she said, "I can tell you're not lying—about these," she said gently touching the tops of her boobs, "but what I'm more worried about is down here," and she moved her hands down and directed my eyes to her belly, and added, "See?"

It's true that her stomach wasn't like it was before. Where before it had been perfectly flat, now it swelled out some, and there were several white stretch marks on her skin. But it wasn't a big deal to me. And as I looked slightly down at her pink bikini bottom, I wondered, as some men do, what her pussy looked like underneath. And then I continued looking down to her still muscular and slender legs, down to her pretty feet with their painted-pink toenails.

Having made that trek, I looked back up at her beautiful green eyes in her lovely face, and said something I'd wanted to say for years:

"Anna. You're beautiful," I said, simply and honestly. "In fact, you're still the most beautiful woman in our whole high school."

She couldn't doubt my sincerity, and smiled and looked happy. But as soon as it came out I realized I'd said too much.

"Thanks, David," she said quietly, looking pleased.

But then a little look of worry crossed her face. Seemingly she was beginning to figure out for the first time how I really felt about her.

"But," she added, "there's no way I was ever the prettiest girl in the whole school, unless you especially like redheads. What about Lisa Gardner?"

Lisa was a gorgeous blond goddess.

"Lisa," I admitted, "is *very* pretty. But almost too pretty and 'perfect.' And she seems kind of bratty."

"Yeah, that's Lisa. Little Miss Perfect. And she is kind of a bitch!" Anna laughed. "David, I didn't know you were so perceptive!"

"But what about Moira?" Anna then said, referring to a stunning brunette in our school.

"Oh, you're right," I said," "Moira is very beautiful, and she's actually fairly nice too. I would worship the ground she walks on—if she'd let me. She's actually kind of a friend. And she's smart too. Maybe I'll even try to ask her out someday, just for coffee, since we're going to be going to the same University."

I felt I had defused the tension of saying Anna was the most beautiful in our school, but then I couldn't help myself, and added:

"Anna, to me you're still the most beautiful. And the nicest. Nick is the luckiest man in the world."

"Oh, David," Anna said, looking both complimented and a little more worried. She paused, then added, with an attempt at a defusing laugh, "How long have you felt this way?"

"Oh for years," I laughed, blushing and trying again to defuse the situation, "Like about two hundred other boys in our high school."

Anna laughed again, seemingly acknowledging her popularity with the boys at our old high school. Since she'd graduated more than a year ago, however, that must have begun to seem like the distant past to her.

"But if you felt that way, why didn't you ever ask me out? Some of those other guys did." She seemed genuinely puzzled and curious.

"You are *way* out of my league!" I said and laughed again, because it was true. I was handsome enough, but not in her league at all, and also very shy. "And, anyway, you know I couldn't be happier for you and Nick. And I'm a very loyal friend."

Anna smiled, looking relieved, and said, "Yes, you are a loyal friend. Thank you so much for all you've been doing for Nick, for me, and especially for little Ben. You're right, we should get out of this damn house. Let's just go right now. We can put on sunblock there. Would you get a bottle of milk for the baby?"

I said yes, and we gathered up our towels, sunblock, and everything else we needed, and headed out for the pool, which was only a short drive away. Baby Ben was locked into his car seat and mostly quiet as I drove their old car that my parents had given me, a ten-year old Accord.

Anna suddenly said, "You know, I would have said yes if you'd asked me out."

"Really?" I said, laughing and rather doubting it..

"Yeah, really. I always liked you."

"Just another example of how you're the nicest of the gorgeous girls in our high school: you would even go out on a 'pity date'!"

"Really, David, you should have more confidence!" She seemed to be almost lecturing me now, as she added, "Anyway, what girls did did you ask out?"

"None of them."

"Why?"

"I'm just too shy, I guess. It was easier just hanging out with Nick."

"And then I came along and took him away from you."

"I don't blame him at all. That was an easy choice! And I gained you as a friend," I said, as I turned into the parking lot of the pool.

The pool was medium crowded, but we found a place to put our towels, and I put baby Ben in his removable car seat with its sun shade gently down on the concrete. And then we started sunblocking ourselves. Anna had already attracted some rather bold stares from a few men of various ages. She acted like she didn't notice, but I have a feeling she did.

She seemed happy, in any case, as she lay on her stomach on a towel and asked me, after I'd done myself and the baby, to do her back.

"Sure," I said, acting casual and like this was normal.

As I warmed up the lotion by rubbing it in my hands, I was able to study the skin of her back for the first time. Like many redheads, she was quite fair, and had a generous sprinkling of freckles across her body. I gently but firmly rubbed in the lotion.

Anna said, "That feels good, David!"

It was a little tricky to do it around where the back straps of her top were, but I managed to lift it up with one hand, and rub underneath with the other. It was a little exciting rubbing next to the swell of her butt, but I kept thinking of ice cubes, and managed to stay soft. I was efficient and fast, and when I was done she returned the favor in a similar way.

"Hey, do you mind if I leave you two here," she said, glancing at Ben, "while I go for a swim?"