Gorgeous redheaded Anna, who was so voluptuous she was barely fitting into her pink bikini, with her boobs spilling out the top, said this just after a handsome man slowly walked by as we were at the public pool. He had given her a look that was beyond admiration—even while she was playing with her baby Ben on the towel right next to her.
“Anna, I know you’re smart, but are you just figuring this out now?” I said, in some exasperation, because she was beyond pretty, and yet very obviously a mother. And so of course she was a mother that a lot of people would love to fuck. And my secret shame was that I was among them.
It was my secret shame not only because I wasn’t her husband, but because her husband was my best friend Nick. But Nick was over in Afghanistan for the indefinite future back when this happened, about a dozen years ago. But I still have a very clear memory of all of it.
Before Nick left, he and Anna had taught me how to help care for their baby, which was for now seemingly my main job in life. And that included feeding Ben lots of breast milk, both from the bottle, and by bringing Ben over to Anna’s luscious, milky breasts. They didn’t seem to have any problem letting me see Anna’s breasts, but I was apparently maybe the only one beyond the immediate family treated that way.
When Nick left he made me promise to look after Ben and Anna. I was supposed to keep Anna from being unhappy, and I was trying—sometimes a little too hard.
As I was around Anna more and more, talking with her, getting to know her well, and seeing more and more of her milk-filled tits, I rapidly fell in lust and in love with her at the same time.
She seemed to know at least something of how I felt, and I had even kind-of told her, but most of the time she pretended not be fully aware of my longing for her.
And I pretended the same—at least some of the time.
But we kept getting closer to crossing the line until one day, when we were tipsy on wine, and her breast pump had run out of batteries, she let me nurse one of her painfully overfull breasts when baby Ben was asleep.
Did we let this happen because her breast was too full and hurt? Well, that was the excuse. But it was really because I was desperate for her breast, and for her milk—and she knew it. And she, I found out, was longing for affection and sensuality.
Anna’s milk was so sweet and delicious that it’s difficult to describe. It’s the food of the gods, even if usually only babies get to have it.
As I nursed her that day, a week ago from the point at which I’m picking up the story, behind the locked door of her bedroom, Anna had told me at first it was only for the milk, and to relieve her discomfort. But then she got so turned on by my nursing of her tit, and how I had told her how she tasted so good, that she started fingering her pussy underneath her sweats.
Anna rapidly came, a few times, and as she did so even more milk squirted into my hungry mouth
Then she wanted to help me with my problem—my rock-hard cock under my shorts, which she could see the outlines of and feel. But I just couldn’t take that step quite yet. It was partly that I was a shy virgin, but also that Nick was my best friend. And so I went into the bathroom to take care of my needy dick, calling out Anna’s name as spurts of my sperm came shooting out.
From a certain perspective, maybe I didn’t completely betray Nick that day. But this is the story about how slowly and surely, as more barriers broke between me and Anna, I stabbed my best friend in the back. Or, did I? As I think it over even now, trying to tell it as honestly as I can, I wonder if there’s something in what happened that someone might forgive, at least a little.
Unless you’d actually met Anna and known her the way I did, anyway, you couldn’t understand how it would take someone almost superhuman to resist her. Anna was not just beautiful, but kind, funny, and smart. And she was suffering….
When I’d nursed her that day and she’d fingered herself to orgasm, she told me to promise to keep it a secret from everyone. And I had agreed. In fact, she told me that even between ourselves we had to pretend that it had never happened.
And so, somehow, for a while, we did.
Remember “Doublethink” from George Orwell’s “1984”? The characters have to somehow keep one idea and its opposite in their minds and in their actions at the same time?
Looking back on it, that was kind of me: doublethinking about Anna and my feelings for her, and what we had done.
On one level Anna and I both were pretending that I was still a loyal friend to Nick, a trustworthy friend, who was just taking care of his baby and lovely wife day after day, without desiring her.
But on another level—simultaneously—we both knew that I’d sucked on her breast, had felt her her sweet juice on my tongue and throat, and that my cock was straining with desire for her. And that she, Anna, had been so turned on by my kissing, and then gently nursing, and then strongly suckling on her nipple and breast, that she’d given in to touching herself, coming to a shuddering climax.
And now she was asking me if I knew she was a “MILF.”
To keep up our game, I had to still pretend I wasn’t one of those lusting after her, and so I retreated to an almost college-course question.
“Doesn’t the term MILF bother you? It seems kind of offensive and sexist.”
“Oh yeah, I guess,” Anna said, looking at me with a cute pout on her mouth, “But it beats the alternative.”
“Which is?” I asked, still a little exasperated, even as looking at her freckled swelling tits was in danger, yet again, of giving me a hard-on.
“A Mother you *don’t* want to fuck, of course. That’s what I was to Nick.”
“What!?” I said it a little too loudly, in surprise and shock.
This was totally new information to me that there had been trouble in Nick and Ann’s sex life, and I couldn’t quite believe it.
“What?” I repeated, more quietly, after I noticed a middle-aged woman a few yards away looking over at us.
“You didn’t know that?” Anna said, in almost a conspiratorial whisper, “I thought Nick would have told you that he’d lost most of his desire for me.”
As Anna said this she looked embarrassed, but also like she still wanted to talk about it.
“I had no idea,” I said quietly, and still in shock “Why? You’re so beautiful, Anna.”
I said this simply, but with such truth in my voice, that I realized, not for the first time, that I’d said too much.
“Thanks, David,” Anna said with one of her ironic smiles as she glanced over at me looking at her.
She then looked lovingly down at her baby Ben, who had recently learned, at six months, how to sit up on his own. Then she said,
“David, does it weird you out to think that little Ben came all the way out of my vagina?”
She looked back up at me, studying my reaction.
“Um, well,” I said, in shock again, and stalling for time, “I hadn’t really thought about it much.”
She was still looking at me and waiting for me to say something. I guess she was seeing if I was grossed out.
I wasn’t sure what I thought as I tried to imagine a baby going through her vagina, and didn’t know what to say, and so just added, lamely, “He was a lot smaller then.”
“Yes you were!” Anna said in a cute baby voice, turning back to Ben, “Or else it wouldn’t have been possible. No. Not possible!”
He smiled at her.
Anna suddenly turned back to me, and said, in a more normal voice:
“I think it sort of freaked Nick out. He was in the hospital room with me during labor, which took forever. There was some blood, as there almost always is. He had said he wanted to cut the umbilical cord, and he did. But he was so pale he was ashen. I think the whole pregnancy and birth thing was just a bit much for him….” Anna trailed off, again studying my face.
“Anna, I don’t know what to say. You know I’m a virgin. I just don’t know anything about any of this stuff. Can’t you talk to one of your girlfriends or your mother about this?”
She looked at me, clearly hurt, and her face started slowly crumpling up. I knew from past experience that she was starting to cry. She’d done a lot of crying since Nick had left for Afghanistan.
“Not really,” she said, as tears welled up in her eyes. She stifled a sob, not very successfully.
A tear spilled down her beautiful freckled face.
I reached out slowly and wiped her tear from her cheek, still marveling at the poetry of her, even in sadness. She gently held my hand, and then put it up to her mouth. She then started gently kissing my index finger with her surprisingly warm mouth and tongue, holding it there, with her warm breath on it. My dick twitched.
Since we were at a public pool I had to be careful about my overly sensitive teenage cock. I very slowly and gently pulled my hand away, and said:
“Um, you can talk about it with me, if you want.”
“OK,” she smiled at me, tears still in her eyes, “Thanks.”
“So,” I said, trying to be helpful, “It started after Ben was born?”
“No,” Anna said with a big sigh, “It started way before that. Really when I was about four months pregnant. Nick found the whole pregnancy thing, and the changes to my body, to be just, well—it turned him off. We hadn’t really planned it you know, and so it was just such a shock to him, I think.”
“Yeah,” I said, not really understanding. But then I remembered how a look of almost disgust would cross like a shadow over Nick’s face a couple of times when he talked about the changes to Anna’s body.
“You’re his best friend, David, and I thought you would have some insight into what was going on with him.”
“Not really,” I said, “I mean, I knew sometimes Nick could be squeamish. But then he also had all this interest in the military, and blood and guts in the movies and stuff, and so I…..I just don’t know what it means.”
“What it means,” Anna said, “Is that I haven’t been getting much for almost a year.”
I thought I knew what she meant, but I was so shy and mostly innocent then, even in my raging horniness, that I didn’t know what to say.
Anna, thinking I was genuinely confused, took the index finger of one her hands, stretched it out, and then inserted it slowly back and forth into the curled up “vagina” of her other hand.
“Yeah, I get it,” I said, blushing and looking down.
“Sorry, David,” she said, “I keep forgetting how innocent you are. Are you still shocked by my raunchy sense of humor?”
“Maybe a little,” I said smiling and looking up at her, “But it’s been one of the pleasures of getting to know you to realize that a woman as beautiful as you can still have a sense of humor kind of like…a guys.”
“So—you think I *am* a MILF?” Anna said, raising her eyebrows and looking funny and sexy at the same time.
“Yes! You’re a MILF!” I said, a little too loudly, and the middle-aged woman looked over at me and glared. I covered my own mouth in shock at what I’d said.
Anna laughed. And her laugh, I should mention, was really like a kind of beautiful music to me. I never got tired of that laugh, which was so magical and unusual.
“Uh, I think we’d better talk about this at home,” I said.
“Yeah,” Anna said, as her laugh finally died down.
“Come on, Ben, let’s go!” She added. She now looked happy. And so did Baby Ben.
Then Anna suddenly glanced at her phone, and a look of worry crossed her face.
“Oh my god. I forgot about Moira.”
“Moira?” I asked, as I thought about her beautiful brunette friend from high college, who was actually in my grade. Moira and I had just graduated, while Anna and Nick had graduated a year ago. Moira was this year’s valedictorian.
“She’s coming over?” I added, worried. I’d sort of gotten used to being around beautiful Anna. But beautiful Moira too—who was also almost certainly the smartest woman in the whole college? I have to admit it made me kind of nervous.
“Yeah, she’s probably already there. Luckily it’s a short drive back. Let’s hurry!”
In spite of what she said, I drove my parents’ old car just regularly. I wasn’t going to bounce Ben on a speed bump in his car seat just because of Moira.
When we got to Anna’s house, which was really also my house, because Anna and Ben lived in the caretaker’s cottage in the back of my parents’ place, Moira was already there, standing impatiently, and looking at her phone.
“Oh, there you are!” Moira said, sounding a little annoyed.
Moira was about as different in looks from Anna as you could imagine. Where Anna was tall, voluptuous, and redheaded, Moira was short, slender, and had almost black hair. But where they were similar was that they were both, in their different ways, very pretty.
“Hey babe!” Moira said to Anna, reaching up for a hug and kiss on the cheek, and then she noticed Anna’s figure with almost a shock.
“You are smokin’ hot girl! Look at your boobs! I haven’t seen you in a bathing suit since,” and here she looked over at little Ben with only mild interest, who I was carrying in his removable car seat.
Like some other women, Moira and Anna liked to compliment each other a lot, sometimes in personal ways.
“I know,” Anna said, smiling, “Remember how I wanted big ones? Now the curse is that I have them.”
“Were a lot of guys at the pool hitting on you?” Moira asked.
“A few looked like they wanted to, but David scared them away. But look at you,” Anna added, “you are a total hottie, as usual.”
Moira had a well-put together Jewish-Hipppie-chick vibe that she did very well. Her breasts were medium-small, but she’d sometimes go braless, as she did today, with stylish and yet casual tops that gave you a good sense of her gravity-defying pointy breasts.
“Oh, shit,” Anna suddenly added, “is this your new car?!”
Sitting on our long driveway was a new emerald green Miata convertible, with its top down.
“Yeah, that’s it,” Moira said, beaming at it with pride as strongly as Anna beamed at baby Ben, “Mom and Dad just gave it to me for choosing boring state U with the full scholarship over much more expensive Wellesley.”
“What is it?” Anna asked, since like some women Anna was a bit vague about cars.
“It’s a Miata,” I said, with genuine admiration, looking at the sports roadster with almost as much longing as I looked at Anna’s breasts, adding: “Very nice car, Moira!”
“Thanks, David,” Moira said, looking at my face and seeming to just notice me. And she seemed to really like me for the first time, even though I’d had AP classes with her for years in high college, because I’d so sincerely complimented her new baby.
“And look at it,” I said, looking down at her little car: “leather, Bose stereo, and even a manual transmission!”
I drove a manual too, but I didn’t think any women my age did.
“You know it, baby,” Moira said, looking at me in a slightly sexy way, and adding, “That’s the only way to go, with the joy stick in your hand.”
Moira got a faux-horny look on her face as she caressed and shifted an invisible shift knob in her hand, almost like it was an erect dick with large head.
“Moira!” Anna laughed.
“Sorry!” Moira mock-said, although clearly she wasn’t, “I was just lost in the moment.”
“Has Vittorio left?” Anna asked, clearly making a point. He was the handsome Italian exchange student that Moira had been dating last year.
“Yeah,” Moira sighed, “how could you tell?”
“Just a hunch,” Anna said, “But maybe you can figure out a way to fuck your car!”
They both laughed.
“Let’s get inside,” I finally said, laughing too, but a little nervously, since this was kind of crude talk if my mother made one of her rare forays out of the big house.
“Ben needs changing,” I added.
“Oh yeah, the little tyke,” Moira said, looking down on him with minimal enthusiasm.
So we went in, and while Anna went to the back to change out of her bikini, I changed Ben.
Moira looked on with barely hidden disgust as I wiped Ben up thoroughly, put him in a fresh huggie, and then dressed in him a cute sailor’s outfit.
“Do you want to hold him?” I said when I was done.
“Not really,” Moira said, “I wouldn’t know what to do.”
“That’s OK,” I said tolerantly, “Ben knows how to sit up now. Don’t you little guy?” And I sat him up and he balanced easily and looked around the room with his green eyes, which were rather like his mother’s, smiling.
“Just play with him with this rattle. I’ll be right back with his bottle.”
I got one of the bottle’s of Anna’s breast milk from the fridge, quickly heated it up in the microwave, and then brought it back over to Ben and Moira on the floor of the living room.
In spite of herself, Moira seemed charmed by Ben, who was smiling at her and flirting up a storm as he shook his rattle in one of his little hands.
“He is kinda cute,” She admitted.
Moira then watched as I squirted some of Anna’s milk from the bottle onto my wrist, checking the temperature. And then I licked it off.
“Ewww!” Moira exclaimed, as Anna walked back into the room.
As she saw Anna, Moira said, “David just licked up some of your breast milk!”
“What’s wrong with that?” Anna said, sitting down on the couch.
Anna had, I saw, dressed herself up much more than she ever did for me, in capri slacks, nice shoes, a stylish blouse, and even quite a bit of make up. I realized not for the first time that women dress for each other much more than they do for men.
“Wow—Anna, you are gorgeous!” Moira said, genuinely wowed.
Anna did suddenly look like a model from a clothes catalog.
“Thanks,” she said modestly, although I could tell she knew it was true, and was enjoying Moira’s compliment.
Ben, seeing his Mom, started reaching out for her, and I knew what he wanted.
Anna started unbuttoning her white designer blouse, while I picked up Ben and brought him over.
Anna unhooked her nursing bra, and I saw for at least the hundredth time the front of her freckled milk-filled right breast, with its large pink areola and medium-sized nipple.
Baby Ben latched on immediately, and started vigorously sucking at Anna’s boob.
“Shit,” Moira said, impressed and even a little shocked at the same time, “that’s quite a show.”
“Does Nick know,” Moira added in a slightly worried voice as she glanced over at me, as I sat down on the living room floor again, “that David’s seeing all this?”
“Oh, yeah, it was his idea. And it’s almost impossible to put a cloth on anyway….Look,” Anna added, and grabbed a cloth and draped it over her breast and baby Ben. Ben almost immediately reached up, grabbed the cloth, and threw it on the ground.
Ben was revealed again, grinning while sucking on Anna’s tit.
“Yeah, I see,” Moira said, looking over at me.
Moira then said to me, “I bet if I told you in high college that you were going to see Anna’s breasts almost every day, you wouldn’t have believed me.”
She was studying me.
“No, I wouldn’t have,” I said, blushing a little and looking down.
“Oh, it doesn’t matter to him. David sees me at my worst pretty much every day: leaking milk, burping, farting. I think at this point point I’m a total turn-off to him. And anyway, he’s the most loyal friend to Nick you could imagine.”
“Yeah,” Moira said, looking back over at Anna, “I saw him changing Ben’s diaper. Even if you’re paying him, that’s total loyalty.”
“I forgot to mention, Moira,” Anna said, suddenly getting a very mischievous smile on her face, “That David’s been trying to screw up the courage to ask you out for coffee.”
“Oh yeah,” Moira said, looking back over at me with an appraising look.
“Yeah,” Anna added, “He says that you’re smart, funny, and really pretty!”
“Anna!” I said, and grabbed a soft couch pillow that was on the floor and threw it at her. She deflected it easily with her arm, and it fell to the floor.
“That’s OK, David,” Moira said, “It’s all true. It’s not like you’re telling me something that I don’t already know!”
I was looking down, and blushing, as Moira added, with halfway mock and halfway real enthusiasm:
“In fact, skip the coffee. I want to pick you up in my car, since you clearly appreciate her, take you on a drive, and then you’ll be like putty in my hands by the time we get up to Lover’s Leap.”
“Could we just go to a movie instead?” I asked, looking up at her, hardly believing my boldness.
“Sure, David. I had no idea you were holding the torch for me,” Moira added. She was sophisticated, and sometimes talked in a kind of old-fashioned way.
“But you’ll need to decide,” she added, “Whether you prefer a statuesque redhead with big boobs, or a sarcastic Jewish girl with small boobs.”
“Moira,” Anna said, “be nice to him! He’s a virgin and he’s really shy!”
“Anna!” I said, genuinely annoyed this time. I sighed.
“That was kind of a low blow, Anna,” Moira said, but then added slyly, in a Groucho Marx voice while holding a pretend cigar, “I would have liked to have found that out myself!”
She raised her eyebrows up and down as she twiddled her pretend cigar, looking me up and down from my face to my still bare chest lasciviously.
I smiled, but was still a little mortified. Moira, seeing this, said in her normal voice, but conspiratorially,
“Just ignore her. She’s just jealous of what we might have together. I know I can teach you a few tricks you haven’t even heard of!”
As I looked into her twinkling brown eyes I smiled again.
Moira winked at me, and then made sexy faces in an exaggerated Hollywood way, finally licking her lips all around.
I cracked up.
“I like him,” Moira announced to Anna, “I think he gets me. Which is more than I can say for Vittorio. We had such a cross-cultural glitch. I was always finding him hilarious, but he usually just didn’t get it.”
“But Vittorio had certain advantages, from what you’ve told me,” Anna said.
“Oh yeah,” Moira said, and her eyes got wide, and she stretched her hands out about a foot apart.
“No!” Anna said.
“I’m exaggerating,” Moira said, moving her hands back together, “More like this.” It still looked substantial.
“How big is that in inches?” Anna asked, seeming genuinely interested.
“Stop it!” Moira said, “You’re shocking the virgin over here.”
It was true, I was shocked. When women in high college were around me, I’d never heard them talk quite this way.
“Now you know,” Moira said, looking back at me and seemingly reading my mind, “This is how women sometimes talk when men aren’t around.”
Baby Ben suddenly de-latched from Anna’s nipple with a wet sound, and then looked over at Moira and smiled.
“We know what’ll keep him happy later in life,” Moira said, and with her hands in front of her she mimed Anna’s big breasts.
“Do you want the other side,” Anna said to Ben, latching up the right side of her bra, and unhooking the left, revealing an equally luscious left breast. She switched Ben around and tried to get him to latch onto her nipple, pushing and tickling it against his face. But Ben was full now, and too amused by Moira’s new and funny voice, and so he couldn’t be interested. Instead he kept looking over and grinning at Moira.
“Awww,” Moira said, “Isn’t he cute. But I can’t believe he’s not interested in that beautiful boob. It looks so good even I almost want to try it!” Moira laughed.
Anna laughed too, and kept trying to comically get him interested in her breast, holding it and pointing it at him, and then tickling his cheek with her pink nipple, which now had a little drip of milk gathering on it.
Moira looked amused, and so Anna took it to the next level.
“Watch this!” Anna said, and as Ben’s face was turned away, as he grinned at Moira, Anna slowly and firmly squeezed her left breast with her left hand.
A surprisingly strong stream of milk squirted out of Anna’s breast. If you’ve seen a woman do this, you know that it’s not just one little stream of milk, but instead half a dozen or more little streams that all come out of the tip of the breast. This was the first time I’d ever seen it, and I was awe-struck. Moira glanced over at me. She was equally awe-struck.
As the milk squirted onto Ben’s face he started in surprise, and then he got a little in his eyes and started crying.
“Sorry Ben. Now look what I’ve done. I didn’t know there would be so much. David, would you take him?”
I came over to Anna and got Ben, as she hooked up her bra and then started buttoning her blouse.
“Jeeze, you two sure make a great team. How much do you pay David? Whatever it is, it’s not enough. Except for the fact that you get to see some of the most beautiful tits ever, every day!”
That was getting a little too close to the truth, and Anna and I suddenly were quiet.
I said, to distract from this, after I’d wiped him up: “Ben seems kind of tired.” This suddenly seemed true. He’d already stopped crying, and now was looking sleepy. “Shall I put him down?
“Please do,” Anna said, “Thanks, David.” She smiled at me warmly, and I smiled back.
Out of the corner of my eye I could see Moira looking at us, and I broke the glance with Anna and took Ben over to his crib in the dim second back bedroom, and gently put him down. Then I came out and quietly closed the door behind me.
“So what’s it taste like?” Moira asked me, as I came back into the living room.
“What?” I said, confused.
“What’s Anna’s milk taste like?”
“Oh, that,” I said, looking over at Anna, who seemed interested in what I was going to say.
“It’s good. It’s really good. You can see why babies are so crazy about it.”
I tried to sound casual, and I think I succeeded.
“Yeah,” Moira said, “but *what* does it taste like?”
“Well, it’s sweet and kind of thin, but at the same time still creamy. I think it’s a lot better than cow’s milk.”
“It’s better for you too,” Anna added.
“Do you want to taste it?” I said, picking up Ben’s bottle which he’d never touched, and holding it out to Moira.
“Drink my best friend’s boob juice? Sounds kinky! But I don’t think I’m up to it today. Sounds like you’ve got a real gourmet taste for the stuff though David.”
“Don’t tease him!” Anna said, trying to protect me on what Anna knew was a delicate subject.
“If I didn’t tease him, how would could he tell it was me, and not some body-snatcher replicant that had taken on my beautiful form to seduce him, take over his body, and then get him to help me take over the planet! Ha-haa-haaa!” Moira ended this surreal attempt at humor with a clichéd evil laugh.
But I was quite amused, and even transfixed by Moira’s sexy sense of humor, which was only rarely on display during my years in high college with her. That word seduced sounded very promising, even though I knew she was almost certainly joking.
“Seriously, David,” Moira looked over at me, and suddenly did sound almost serious, “I think you need to get out of this house more. You’re spending too much time here with Anna and the baby.”
“Moira! He’s my main help! Do you want to come over here and change poopy diapers!”
Anna seemed genuinely indignant. It was not the first time she’d used the word “help” to describe me either, which was sort of insulting, but it is true that babies are a huge amount of work, and without Nick she really did need a lot of help.
“No!” Moira said, laughing again and getting up, “I can barely deal with my own shit. I can’t cope at this point with much of anyone else’s, especially a baby’s.”
Moira went over to the couch where Anna was, leaned down and gave her a hug and a big kiss on the cheek.
“Hang in there, babe,” Moira said, “Sometime when David’s babysitting call me, and we can have a girls’ night out.”
“And David,” she said, turning to me, “I’ll call you about that date, since I have a feeling that if I wait for you to call it could be a while. Stand up. Give me a hug and a kiss.”
Moira hugged me with her slender form, but I could feel her braless medium-small breasts through her blouse against my bare chest, even through her blouse, which felt very nice. And then she looked up to kiss me. I looked down into her beautiful liquid brown eyes, which were sparkling with mischief and sexiness, and then tried awkwardly to kiss her cheek.
“No,” she said, moving my face gently back to center with her hands, “let’s do it on the lips and get it over with,” and she leaned up and gave me a quick but nice kiss right on the lips.
She separated herself, turned to Anna and said, “I learned that from a movie. It was Al Pacino, I think, who told this woman at the start of their first date that they should kiss right away, so they wouldn’t have to worry about that first kiss for hours. It seemed totally the right approach for David here.”
I was looking at Moira with a happy smile filled with more than a little wonder at her sense of humor and other charms, including her soft lips.
“Awww, look at him,” Moira said, glancing back at me, “He’s like a happy puppy dog. I’d give you another kiss, sailor, but I want you to have something to look forward to. And I don’t want to gross out my friend here with the heavy tongue action of that second kiss.”
And now Moira stuck her tongue out a little and vibrated it in almost a butterfly-like way.
I couldn’t help but laugh.
“What?!” Moira looked mock-surprised, “You know you want it!”
I kept laughing and blushing, but she was right: I always knew Moira was pretty and smart, but now that she was shamelessly flirting with me she was suddenly mesmerizing.
“OK! I gotta go and figure out how to fuck my Miata!”
We laughed again, and Moira added thoughtfully, “As long as I clean the gear shift it should be all right, don’t you think?”
“Moira, you’re crazy!” Anna said, laughing some more.
“Seriously, take care you two!” Moira said, as she grabbed her small black designer purse from the table, and then, glancing one last time at both of us, quickly breezed out the door and closed it behind her.
We could hear her car starting outside, and then the slightly whining sound of her transmission as she backed out of the driveway.
A couch pillow hit me in the head as I was staring at the door, lost in thought about Moira and our future date.
“What?” I said, as the spell was broken.
When I looked back at Anna, I was shocked to see that she had gone from laughing a minute ago to clearly on the edge of tears.
“I thought you only looked at me that way,” she said, clearly trying to breathe evenly and stop the tears from welling up in here eyes.
“Oh Anna,” I said, trying to be sensitive, “You’re being silly, what man couldn’t look at Moira that way when she flirted like that. And, besides, you’re married!”
I knew I was stating the obvious, but suddenly it seemed like it needed to be said—to both of us.
“Anyway, you’re welcome,” Anna said, with a slight hint of bitterness.
“For what?” I said, slow on the uptake.
“For setting you up with Moira, of course. You’ll probably have fun, but I’m not sure it will all that you seem to be hoping for.”
At this point, I was hoping for quite a bit, and so it was a let down to hear that. I was already trying to picture losing my virginity to Moira.
But I just said, “You mean she’s not going to kiss me with her tongue like that,” trying to recapture the humor of a few minutes before.
“Oh, she’ll probably do that, and maybe a whole lot more—if she likes you, which she seems to so far.”
I think I looked shocked and puzzled at the same time. How could it be a whole lot more and not what I was expecting at the same time? But Anna asked,
“Have you ever even seen a woman naked, David? I mean, aside from my boobs.”
“No, your boobs pretty much cover it. Aside from, I have to admit, a few women on the web.”
I blushed as I said this, and looked down, as I confessed to Anna what she must already know, that I looked at porn. What I didn’t add, and was now thinking about, was that I tried to look for women who looked like Anna, which wasn’t easy. I’ve mentioned several times that Anna was pretty, but now I’ll mention that she looked rather like Amy Pond in the later Dr. Who TV show that would be on almost ten years later.
“I can tell you what Moira looks like naked, if you want,” Anna said, clearly just letting pass as obvious that I looked at nude women on the web.
“How did you see her naked?” I asked, and then got really shocked, as I blurted out, “Have you two….? Oh my god!”
“No,” now Anna was laughing again, “But I thought about it. If I ever do it with a woman, I hope it’s with her. She has kind of made a pass at me, but that was before I was even pregnant.”
“You mean she’s….?” Again, I couldn’t finish the sentence.
“Bisexual? Yeah. But in practice she seems to mostly go out with men.”
“But then how did you see her naked?” I asked again.
“Oh, we used to have plenty of sleepovers before Nick, and she’s very casual about nudity. She basically would flaunt herself in front of me, and then taunt me to take off my clothes too.”
“And did you?” I said, still getting over my shock.
“Yeah, more often than not,” Anna admitted, “And we did give each other back massages. And we also compared our breasts and pussies and stuff. But we never actually had sex.”
“Oh my god,” I said, taking this in.
“Does that turn you on, thinking about me and Moira together naked?” Anna asked.
“I suppose it might, if I could just get over the shock.”
I then added, “What do you mean, comparing your breasts and…stuff?”
“Oh, that. Once-in-a-while I think some women who are *really* close friends do that. We tell each other how sexy and beautiful the other one is, while comparing and contrasting. I loved Moira’s pointy breasts. They look almost like large and wide champagne glasses with little nipples. She let me touch them. They’re very soft, and warm, and yet firm….” Anna was looking at me to see what effect this might be having.
She saw me looking at her with wonder and growing horniness at this description of what I might soon see—maybe on even the second date? I was calculating.
“Shall I go on?” Anna said slyly, in a sexy voice.
“Sure,” I said, a little hoarse.
“Well, the other thing about Anna is that she doesn’t shave much, and so she’s kind of hairy.”
“Hairy?” I said, almost in a trance.
“Yes,” Anna said, seeming to enjoy the effect her description was having on me, even though it was about another woman, “Of course I am too. But Moira has a very beautiful black-haired pussy, and when she spreads her legs you can see her dark red pussy lips inside….”
My mouth opened with awe, and my cock started rising visibly in my swim trunks, which I still had on. At this point, I was beyond caring: what did she expect would happen when she talked that way to a horny 18-year old guy?
“But,” Anna added, in a suddenly brisk way, “She makes it clear to almost all of her lovers that she’ll never really fall in love with them, and probably won’t ever commit.” I saw Anna glancing down for a small fraction of a second at the tent in my swim trunks.
“I don’t understand,” I said.
“She’s a ‘friends with benefits’ kind of gal. She has a big speech about it that she gives to people. I’ve heard it too, and she told me she tells a variant of it to almost all of her fuck buddies.”
“Oh,” I said.
I really couldn’t tell how appealing this was to me, to be just one of a number of Moira’s friends with benefits. My dick seemed to know and started rapidly wilting. I had no idea that brilliant Valedictorian Moira had this kind of sex life.
“David, let me ask you something, and I want you really to think about it,” Anna said, in a different tone of voice.
“Yes,” I said, puzzled.
“Do you love Ben?”
“What? That’s quite a change of subject!”
“Just think about it and tell me: Do you love Ben?”
I thought about it, and I realized with wonder as I searched my strong feelings that I did love the little tyke.
“Oh my god,” I said quietly, and even a little choked up, “I do.”
“I thought you did,” Anna said, beaming, but with tears again suddenly brimming in her eyes.
“Oh David, give me a hug!” I hugged her in a genuinely loving way for half a minute, and then separated, and said with amazement:
“It just kind of snuck up on me. It took you asking for me to realize it, but I do love Ben.”
“He loves you too, I know it,” Anna said, still on the verge of tears.
“I’m so glad you love him.”
And then she paused and added: “And how do you feel about his mother?”
“Oh, Anna, I don’t think we should be talking like this….” I was shocked yet again, wondering how I could be shocked in so many ways in such a few minutes. I almost felt like I had psychological whiplash.
“But you do care for me?” Anna said, seeming to know the answer.
“Of course I do. Very much! You’re my best friend. In fact, I think in this short time you’ve probably become the best friend I’ve ever had.”
“And you think I’m beautiful,” Anna added. It was a statement, not a question.
“Of course you’re beautiful! Every guy at the pool knows that—you don’t need me to tell you.”
“But I do need you to tell me, because I don’t really care about those guys at the pool.”
“Anna, this is getting very weird. Nick would not want us to be talking this way. He trusts us,” I said, feeling very worried and exasperated at the direction the conversation was going. I added:
“This is why it’s good I’m going out with Moira. Thanks for setting that up.”
“Why do you think she wants to go out with you?” Anna asked, simply, as if asking a child.
“Um, I don’t know. I think she likes me, but….”
“She does,” Anna said, “You’re cuter than I think you know, with your curly brown hair, your thin and muscular build, and your shy and bashful looks. And seeing how capable you are with Ben I think makes some women think, including my Mother as you saw, that you would probably have skills in other area. Like pleasing a woman. Or, that at least you’d be teachable. And that you’d really want to please a woman that pleased you. Isn’t that right?”
“Yeah, I guess,” I said, blushing.
I was hoping I could figure out how to please a woman. Or at least be be taught how to please a woman.
“But I think it’s more than that that’s making Moira flirt with you so much. Try and put two and two together.”
Since I was better at math than Anna was (although not as good as Moira), this seemed like an insulting question. But suddenly it dawned on me. I couldn’t quite say it. But Anna could.
“She’s going out with you to try to keep us apart,” Anna said quietly.
“Oh shit,” I said, knowing it was true. And then I walked over to where the bottle of breast milk was still sitting on the living room floor several feet away. I picked it up, and started sucking down the sweet juice of Anna for comfort.
I stopped nursing on the bottle, and then suddenly laughed at the absurdity of the whole situation, and said:
“I’m sure glad Moira can’t see this! What would she say?”
“I can barely imagine,” Anna said, “But it would be some kind of horrified, sarcastic joke.”
“How’s the milk?” Anna added, as I kept nursing it down.
“Delicious, as always,” I said, somewhat sarcastically myself, shaking my head at the craziness of it all, and yet tipping the bottle up and sucking some more of it down just for the heck of it.
“Oh fuck,” I suddenly stopped. “I think I should be drinking whisky instead and getting shit-faced. But I hate whisky with a passion….”
“Please don’t drink—unless it’s my milk, or get a glass or water,” Anna said quietly, “I’m going to take a bath and try to relax, and I’d like you to listen for Ben and get him if he wakes up.”
“OK,” I said, standing in the middle of the living room, still holding the bottle. As Anna passed by me on the way to the bathroom, she patted my tummy with her hand affectionately.
She closed the door behind her, and soon I could hear the water pouring into the tub.
I sat down on the couch, and turned on the TV, watching an old episode of Star Trek: The Next Generation to distract myself. I couldn’t help but wonder how Picard, Data, or Troi would deal with this situation. I realized they’d never be in this kind of situation, but somehow I could imagine Troi saying, sympathetically, “How do you feel about Anna?”
Then I heard Ben cry, and I went to get him up. I was about to get him a bottle, when I heard Anna shout from behind the bathroom door: “I think he’s ready for his first real bath!”
Up to this point, we’d given Ben his baths in a small blue plastic tub that we put in the kitchen sink, but now that he could sit up really well, it did seem like it was time for a real bath.
“Should I wait for you to come out?” I asked through the door, holding Ben. He seemed puzzled by what was going on, and was looking between me and the sound of his mother’s voice behind the door.
“No. He’s needs someone with him in the bath. Bring him in to me.”
“Um, Anna, I’m not sure that’s a good idea.”
“Don’t be silly,” She said, “I’m taking a bubble bath. You’ll see less than you’ll see when I’m nursing him. I’m already draining it out so that it will be shallow for him. Get him undressed.”
It all seemed to make sense. And so I undressed Ben and got him completely naked, which he seemed patient with, although looking like he might cry if given a provocation. Then I said through the door:
“OK. He’s ready. Are you ready?”
“Yes,” she said, “Come on in!”
And so I opened the door, and a billow of steamy air greeted us that was scented with Anna’s delicious-smelling coconut-flavored bubble bath. Even though she’d drained the water down to about six inches, she’d strategically arranged the bubbles over her nipples so that I couldn’t see even them.
“See?” She said, as Ben reached out for his Mom.
“Yeah,” I said, smiling and laughing a little at my worry, “Here he is!” And I put him down slowly between her legs.
He was delighted by the warmth of the water and the bubbled. You could see it in his happy face. He started splashing.
“Thanks, David,” Anna said.
“Sure,” I said, smiling, “I’ll be out watching TV. Just call when you want me to get him.”
“OK,” Anna said happily, smiling at her splashing baby boy, “Just keep the door open so you can hear me better.”
I went out and watched some more Next Gen, suddenly feeling happy and at peace with the world.
About twenty minutes later, Anna said, “He’s ready. Come and get him!”
I walked into the bathroom and went over to the tub , and then as I started to lean down to get Ben, I froze. The bubbles had almost all popped. And the water was pretty low. I’d seen Anna’s luscious generous breasts before, heavy and yet still slightly pointed, with their pink areolas and pink nipples. And there they were again. But looking down between Anna’s legs I now saw that she was indeed a natural redhead.
For between her legs was the most beautiful sight I’d ever seen in my life, or will ever see: the triangle of Anna’s red-haired cunt, halfway in and halfway out of the water.
Her legs were somewhat spread because Ben was between her legs, and so I saw not just the triangle of her pussy, but right between her legs the the slit of the pink inner lips of her vagina, and up toward the top, covered by a fleshy hood, that magical thing the clitoris that I’d heard about and seen a few pictures of.
I wish I could say I was cool about it, but I just bluntly stared, for several seconds, seemingly paralyzed. Since Ben was right between her legs, to get him I’d have to reach my hand in within a couple of inches of Anna’s cunt, and I wasn’t sure how to do that without maybe touching her pussy.
My breath was coming rapidly as my cock started rising for the second time that day in my bathing suit.
“Sorry about that,” Anna said playfully, “the bubbles popped,” she said stating the obvious.
“Although,” she said now looking at the growing tent of my soon raging erection, “I can tell you like what you see.” She seemed turned on too.
“Go ahead,” She said, “You can still get him out. It won’t bite….”
She added, “I know it’s your first time seeing a woman naked, but remember your first job is to keep Ben safe. Concentrate on that!”
“Yeah,” I said, swallowing. And then addressing Ben, I said in my higher baby voice for him:
“OK, little guy, we’re going to get you out,” and I reached between Anna’s legs, having no choice but to slightly brush against the tips of her curly wet red cunt hair, and then I slowly scooped him up into a towel and stood up. Walking very carefully, I took him out of the bathroom and to the living room, and laid him down to diaper and dress him.
A few minutes later, Anna came out in a dressing gown.
“Anna,” I said, not waiting for her to speak, “I need to go home and think about all this.”
“I’ll bet!” Anna said ironically, clearly guessing that I was about to whack off while thinking of her beautiful pussy.
That was true, but I was also going to try to think about what she’d said about love, and about Moira.
But I just said, “Yeah,” and looked down bashfully, more or less confirming what she’d just implied.
I rushed off then to do as she’d guessed, and didn’t see her again until the next day. That morning, Moira, true to her promise, had called me, and in a funny conversation we’d begun to plan out our date.
When I headed out to the back late the next morning, I saw Anna sitting on an easy chair by the pool in her pink bikini. Ben was nowhere around, but I noticed she had the baby monitor on the table near her, and so I knew Ben was napping. I walked over closer, and saw that there were a couple of other things next to the baby monitor.
“I was going to get you to go to the pool with me again, but, since Ben’s sleeping,” Anna suddenly picked up what I now saw was one of two small loaded kid’s water pistols, made of clear green plastic, and started rapidly shooting me in the face, chest, and crotch, “I thought we could play Assassin instead!”
“Anna!” the squirts of water were cold, and she was relentless. Plus I was unarmed and dressed.
“OK, OK,” I said, “I give,” as she squirted my face, and then added with pretend indignance, “How could you shoot an unarmed man like me? I thought you were in favor of gun control?”
“I am,” she said with a mock-evil voice, still relentlessly squirting my face so I couldn’t see, “as long as I’m in control!”
“You’re crazy,” I said, and I meant it in more ways than one, as I walked away and yelled behind me: “I’m going to go get on my swimsuit, and then I’m going to get even. Like maybe throw you in my parents’ barely-heated pool!”
She laughed, “I’d like to see you try!”
I got on my swim trunks again, but felt that they weren’t really a safe thing to wear around Anna now. I couldn’t believe that the day before I’d gotten boners twice in front of Anna that were clearly visible. I vowed to try to stay in more control today. But a water fight seemed safe enough.
When I came out, however, Anna was nowhere to be seen. Both squirt guns, as well as the baby monitor, were still on the pool-side table, and the door to the back house was ajar. I realized that this was my opportunity for revenge, and grabbed the one still loaded water pistol and walked rapidly into the carriage house, closing the door behind me.
Anna was in the kitchen in her bikini, getting herself a snack of cheese and nuts.
“Wait,” she said with mock innocence, turning around, “I’m unarmed. You couldn’t shoot me, could you? Plus we’re inside.”
“Oh yeah,” I said and laughed, and started shooting her relentlessly as she had shot me. I was nicer than she was though, and avoided her face, and instead shot her left boob with several squirts, and then her right boob, and then down to her bikini bottom and started squirting several times there.
“Are you enjoying yourself,” she said slyly.
“Yes,” I said, getting breathless, and still squirting where I knew her pussy was, over and over, aiming for her clitoris.
She walked slowly closer as she did this, and I kept squirting her cunt under her bathing suit.
“That tickles,” she said tolerantly and even gently, “but it feels kind of good.”
“Come here,” she said, “you’re pretty much out of water.”
She took the water gun and put it on the kitchen counter.
I looked directly into her beautiful green eyes and freckled face as she took me by the hand and led me to her back bedroom. She closed the door behind us and locked it.
“What?” I said, “Do you have a hidden weapon here?”
“Yes,” she said, and moved over and started gently wrestling me to the floor.
I didn’t resist.
Now she was sitting on my stomach as I lay on my back, and she reached back and untied her bikini top, which she dropped to the floor.
Anna’s luscious breasts were now looming over me, looking bigger than they ever had.
“See?” She said, smiling, “And I’m not afraid to use them.”
With this she leaned her right breast over my face, so that I was looking up at a now seemingly very large pink areola and nipple, and with her right hand she took her breast and gently squeezed.
Several little streams of Anna’s milk squirted out of the tip of her breast and onto my face. Like with Ben the other day a little got in my eye, but it didn’t hurt and I didn’t cry.
Instead I stuck out tongue.
Obliging, she angled her right breast right into my mouth from above, squeezing it again as I nursed on Anna’s astonishingly lovely and milky tit.
“It’s so good, isn’t it?” Anna said with a knowing and horny voice.
“Yes,” I said breathlessly, and then glanced over at her other breast.
“Oh, you greedy man. I can see you want the other one too. Well here you go.”
And Anna now put her other luscious breast into my mouth, squeezing it and letting me nurse on it for more of her sweet, lovely juice. Her boob juice, as Moira called it.
My dick during this was rising up to full boner-hood.
She took it out and let me breathe again.
“Thank you,” I said breathlessly.
“Sure. I thought you needed that. But I want some milk too.”
I saw her looking down at my nipples, and making an intentionally funny nursing mouth like she was going to suck on them.
“Sorry!” I said, “I don’t have any milk!”
“Oh yeah?” she said, and then she leaned over my nipples, one at a time, and squeezed some of her milk on them. And then sat at my side, leaned over, and started nursing on one.
“Ow!” I said, “That’s kind of sensitive.”
“I know,” she said, and then kept sucking and nursing just as hard.
“I want more of David’s milk,” she said, as if to herself, and I saw her glance down at the straining cock in my swim suit.
“Wait,” I said.
She replied sternly, “I gave you my milk. It’s only fair.”
And she untied and removed my trunks somewhat roughly, not giving me time to protest.
“Oh, look at this big nipple,” she said, looking down at the reddish mushroom-like head of my circumcised six inch cock, which was straining and throbbing.
“I’m going to nurse on it,” Anna said sternly and yet playfully, “And get the milk out.”
Without pausing she lifted up my throbbing dick and immediately plunged her lips and mouth around it, sucking and nursing on my it with powerful suction.
“Ahhh!” I moaned.
She continued sucking and nursing, plunging my cock deep into her sweet mouth.
“uhhhh.” I said, breathless.
She emerged, and said, “Is that all you can say? I want you to say what you said in the bathroom that time when you were stroking yourself.”
“What?” I said breathlessly not knowing that she had heard.
And she then did a surprisingly good imitation of my voice, saying, as I had when whacking off and thinking of her: “Anna. Anna! Annnaauuugh! uuuh! Uuuh! Uhh!”
I couldn’t help myself, and laughed at her sense of humor and in embarrassment.
“If you can do it for the mirror, thinking about me, surely you can do it again, with me really here.”
“Yes,” I said.
“Promise?” She said.
“Yes,” I said, “please!”
“Oh, you really want me to get your milk out now, don’t you?”
“Yes,” I said quietly.
She plunged her mouth back down over my cock, sucking it in a most amazing and firm way, nursing it. Anna was nursing me for my cock milk.
“Anna,” I said.
And then I couldn’t talk for a minute because the sensations were too powerful. As Anna sucked my cock I though of how I’d sucked on her beautiful breasts, getting her sweet juice out.
“uhh! Anna! Annnuuuuuh!!”
My dick felt “sweet” as I felt a huge jeweled load of my sperm start shooting into her mouth.
Uhhh! Uhhhh! uhhg” I moaned, as several more squirts went into her mouth, until I was empty.
She came back over to me, and I leaned up to look at her.
She opened her mouth and revealed a pool of my whitish cum-milk on her tongue and filling her mouth.
“Ah’ve got milk!” She was barely able to say, as a little spilled out of her lips, which she caught with her finger and tried to stick back in, laughing.
Then she closed her mouth, closed her eyes, concentrated, and swallowed it all down in a few gulps.
“Ahh,” she breathed, “ahhh.”
“That was a lot of milk you had for me. It was pretty good. But I think my milk tastes better.”