MILF and Cookies Ch. 01


Disclaimer: This story is pure fantasy, none of it is real, but is based on real people.

* * *

The name’s Jimmy. I’m a high school senior, football star, and pretty soon I was looking to head for college on a scholarship to play. I only lived with my dad who was proud as can be but because we were always so busy with school and work, we didn’t see much of each other for this final few months.

I was dating Penny Reynolds, hot blonde, thin, busty, volleyball player. She sounds like your typical blonde girl out of high school. She wasn’t the brightest bulb so I was only in it for the sex and hoped she’d even realize that this was only until I was gone to college. Her mother, Nancy, had gotten pregnant after a one night stand with a lawyer from L.A. about a little over a year ago. I wouldn’t even go over to Penny’s simply because her mom was an even better bombshell than her, and I’m sure she had tried to pull some of Penny’s previous boyfriends into traps for her own pleasure.

Penny calls me up one afternoon after I was done practicing and invites me to go see a movie with her. Apparently none of her girlfriends wanted to go watch that new damn Hunger Games book film with her. I teased her making a joke about how she probably never even read the books and reluctantly agreed to take her. I told her I’d pick her up from her house at 7 p.m.

I’m just getting off of practice and drive my truck over to Penny’s. She insists I come inside to wait for her because she just got out of the shower. So now I have to wait for the typical hour or more for a girl to get ready kind of thing when I notice her mother in the living room breastfeeding her baby boy.

Nancy was wearing a plaid button up that was fully unbuttoned and her nursing bra was in full view. Her breasts were sexy and very big. She must have been at least a 36F. She noticed me there and greeted me. “Jimmy, hi baby, how are you?”

“I’m good Ms. Reynolds, thanks”, I responded, trying to cut it short from becoming aroused by watching her nurse. I had never told anyone, not even Penny, but I was more than just a breast man, I craved to be involved in what was known as adult breastfeeding. I always watched videos of women’s lactating breasts online. I almost felt that I almost entirely used my laptop just for them. I had never been breastfed, even as a baby. My mother had died giving birth to me so I assumed it was just natural for me to want breasts the way I did.

“Honey, I told you not to call me that; call me Nancy”, She said with a smile. She almost seemed to open up her blouse more than it already was. Her right breast was still sealed in the bra and was not occupied by the baby. I almost wanted to knell in front of her and attempt to suckle from her.

“Alright, Nancy. Just waiting on Penny to finish up to go catch a movie.”

“Great, but good luck trying to make it. I’m sure she’s going to take forever just trying to get ready”, she mocked.

“Oh I bet so”, I glumly agreed.

Nancy’s baby unlatched and seemed content as he drifted off into sleep. Her breast was exposed and remained exposed as she nestled him up to take him to bed. It was the most beautiful sight I had ever seen. The areola was a dark shade of red and her nipple looked like a large pencil eraser, wet, glistening with the milk that coated it as it leaked out.

She disappeared to take the baby upstairs to his crib and while I was alone in the living room I couldn’t help but reached into my shorts and jerked a little, just to release some tension and stress. A few minutes later Nancy comes back into the living room with a pump in hand and her blouse and breast still open. She unclasps the other cup and now has both breasts free. They meet in the middle due to size and look full of yummy milk. She begins to pump the left breast as it was the one the baby had just suckled.

I was now under the impression that she was pumping in front of me on purpose. She kneaded her left breast as she squeezed the pump’s nozzle down.

“Are you and Penny already making plans for prom later this year?”, she asked as she looked up with a smile, breast still in hand.

I was mesmerized and could not stop watching the milk go down into the container.

“Uh, yeah, uh…um…”, I stuttered out.

I could sense a sinister smile perking up on Nancy’s face as I also heard a tiny giggle followed by,

“Great. I’m sure the two of you will have so much fun.”

A few minutes later she removed the pump from the left side and proceeded to repeat the process again on the right. As she shifted she gave tremendous exaggerated bounce to her breasts and lifted her chest mid-breath as she flashed her confident smile.

She proceeded to pump her right breast, but her left nipple did not cease to slow to a halt with its leakage.

“Jimmy, sweetie, do me a huge favor and grab that small jar and come sit next to me”, she commanded.

I followed her order and grabbed a clean small jar and nervously sat next to her. I izmir escort was so, so close to her boobs. They were there, just bare, milky and ready for me inches from my own anatomy as she continued to instruct me with,

“Okay now don’t be weirded out, but I need you to hold that jar against my boob right here.”

She perked her left breast out to me. My tongue ran across my lips instinctively and I lowered the jar softly around the nipple and pressed ever so gently onto the areola.

The milk drops fell slowly but continuously into the jar, sliding in the form of orbs off the tip of the nipple. With confidence, I extended my free arm and placed my hand around the same breast.

I swore I could have heard a tiny moan escape her lips. I gently kneaded and squeezed her breast as I watched the milk drip faster into the jar.

“Good God, Jimmy, baby boy, you seem to know exactly how to do this.” She whispered with a low gasp.

“Health class Nancy” I lied.

This was my time. This is my moment. This is where I was meant to be. She is mine. Her milk is mine.

I pull back the jar and place it on the coffee table next to us. I continue to hold her breast in my hand and bring my body in closer to her. I look up into her eyes, parting my lips just slightly and within few inches from her nipple. My body language asks her for her permission and she smiles down at me all sexy and nonchalantly.

She ceases her pump, removes it from her right breast and places it next to the jar that I just set down.

She brings her arm around my shoulders and pulls me in.

“Alright sweetie, let’s see what else you learned in health class”, she whispered in arousal.

My lips bump with her nipple and slowly make its way between my teeth and onto my tongue. As she holds me closer she fills my whole mouth with her areola and I begin to suck away.

“Here you go baby. Is this what you want?” She teased me as she began to squeeze the breast I sucked on.

Her milk comes in hot and runny. It’s sweet. It’s delicious. It’s all I’ve ever wanted. My tongue dances around and across her nipple. Her tit flesh remains warm and soft against my face. Her milk runs like a stream into my cheeks as I suck and torrent down my throat as I swallow. It takes identical to the leftover milk at the bottom of a sugar cereal bowl and is as thin as coconut milk.

I give we nursed for about 5 minutes solid until we hear footsteps coming down the stairs. It broke my heart, but we part lips from breast, body from body. She rapidly buttons up a few buttons on her shirt and retreats the pump to her chest. I return across the coffee table from her.

For a second I found myself asking if this really just happened. Did my dream become a partial reality? I look down at the jar with about an ounce of milk in it on the table and then I look at her. She flashes me a quick wink and awaits Penny’s presence.

Penny appears in the room in bathrobe and grabs a makeup kit from a cabinet near.

“Babe come upstairs for a sec before I finish up”, she whined.


She leaves and I make a quick flash over to Nancy. I kneel in front of her and she proceeds to open up her right side again. This one had not had my touch yet. I dig in and begin to nurse again.

“Baby boy as much as I want you to keep sucking these tits, go see what my daughter wants. I promise this won’t be the last time. Here take a few more sucks”, she says as she squeezes her breast with force and lands some kisses on my forehead.

My cheeks flood with lots of milk and I swallow the torrent slowly, savoring it, and unlatch. I nodded in agreement with her and headed upstairs.

My head was spinning, my mind was still with Nancy, still at her breasts. My body was another entity, just a vessel that had not purpose. My reality snaps back into place as I approach the doorway to Penny’s room. Penny is half naked in a pair of black jeans. Her tits are gorgeous hanging perky as she is bracing a red bra around her belly. She begins to pull it up to conceal them but stops when she lands her eyes on my shorts.

“Wow babe, have I really turned you on just by watching my boobs?” she asked in a very amused tone.

My mind had not processed that the arousal that Nancy left me from suckling was still very much alive.

I walked over to her and sat on the edge of her bed in front of her and pulled her in close.

“Yeah babe. I love your tits”, I played along as I landed my tongue and lips around one of her breasts. Penny’s breasts were not too far from what her mother’s looked like. One could confuse them for sister boobs, Penny’s obviously were smaller and perkier but only by a fraction of a couple of sizes and she didn’t lactate.

I continued to play with them, nibbled her nipples and squeezed them together.

“Ohhhh.” She let out a high pitched moan. Her hands went to below my shorts and fondled my cock.

She released her grip and backed off to finish sliding her bra into place.

“Babe as much as I’d love to ride your cock right now, I really want to catch the movie”, she said in a small giggle.

Really Penny? Really? My erection was not going to go down by any means soon. The taste of Nancy’s milk still lingered in my mouth and sucking Penny’s tits now also had me wanting sex. But I kept in mind what Nancy said and maintained my patience.

* * *

“Hope you all enjoyed the show, come back next weekend!” the ushers yelled as they escorted everyone out of the theater.

“Thanks for bringing me to the movies babe. I had a good time”, Penny said as she clung her body closer onto me as we walked out.

Movie? What fucking movie? My mind was still with Nancy, in that living room, breasts nourishing me with their milk.

“Welcome babe. Let’s get you home now”, I stoically responded.

The drive is fast and short and I insist myself into her house with her as soon as we pull in. Perhaps I can find myself another opportunity again tonight with Nancy.

“I think my mom went out with her girlfriends. Ollie isn’t here either, so you know what that means.” She winked as she walked up the stairs.

We shut her room door and she sat on her bed waiting for me. I lifted up her shirt and pulled her bra away from her breasts. I landed kisses and nibbles on her tits.

“Oh God, yes baby, enjoy these tits babe!”

I suckled her boobs just as I did her mother’s and she was loving it. Her top comes off completely and then her pants follow. My clothes somehow disappear within our heat and I’m fully nude over her sucking her tits as my left hand is playing with her clit. My body travels down and like a predator I take over her. My arms clutch her legs and I bend my tongue forward into her opening.

At this point she’s yelping in pleasure and holding my head down onto her clit, running her fingers through my hair. My tongue boxes with her clit, going back and forth giving hooks and uppercuts. Five minutes go by and like a dagger I plunge my cock into her.

I grab her ass and dig in further and begin to thrust and buck back and forth. Her legs wrap around my waist as she pulls in my head towards her breasts again.

I proceed to strike again and again within her, my mind drifting in and between my reality and my moment with Nancy. I could see her tits again, lactating, feeding me. Her sexy blonde hair tickling my face as it falls around the both of us. Her sexy body despite giving birth to another child.

My reality shifts back and my mouth is engulfing Penny’s left breast, suckling it like it had milk. With Nancy in mind my cock felt like it was thickening even more and my thrusting became faster and faster.

Penny was now shrieking good pleasure. I could not tell you how long I was going but in terms of speed and endurance, I was making plenty of rapid smacking noises.

About 30 minutes go by and thinking of Nancy is bringing me closer and closer to the edge. I need to pull out soon to prevent coming inside her. Penny’s vaginal muscles give a final constrict to my cock and she screams out in ecstasy. She’s coming hard and I’m still thrusting. In any case I’d let it go inside her but I was not going to end up with Penny for sure.

Penny’s climax subsides and I pull out of her. I climb up a little and cute her recovery period short as I pull her blonde hair towards me. She looks up at me doll-eyed and nods as she pulls my cock into her mouth. I feel her tongue slither up and down my shaft as she’s blowing me, and finally the fireworks go off for me.

My body tenses up and she senses it as she begins to suck my cock exclusively to swallow me as well. I can feel her consuming me like a fresh beverage, but I can feel that this is a storm compared to other orgasms and her cheeks cannot contain the last few spurts. They land on her tits and down her neck. She finishes cleanup by sucking the last of it from my cock and even the aftermath.

“Damn babe that was a lot more than usual”, she said with a smile as she holds up her tits with her forearm.

“Sure was”, I agreed, surprised at my own produce.

* * *

My phone blinked with the “New Text Message” icon. I opened it up seeing it as an unrecognized number. The text read, “Hey sweetie, this is Nancy. I stole your number from Penny’s phone. I told her I’d be out on a date today. She’s away with her Dad today so I’m basically asking you out on a date.”

Oh boy, here was my next opportunity!

I replied with, “Sounds good. When do I pick you up?”

Later that day I drove my truck over to their house. Like a gentleman I went to the door to wait for my date. Normally I wouldn’t do this often, even for Penny. Today was a major exception. I had a hidden glove compartment in the truck that had a fresh box of condoms and my account was safe for spending whatever it took for more milk.

The door opens and Nancy is wearing a khaki capris pants with a tight button up blouse and a dark tank top underneath. She looked like a typical mom, but of course with us being on an official date no one would notice so it would give us a good view.

We headed to the mall so that she could buy new nursing bras. I got to see a few of her selections but did not get to see her in them unfortunately. We’d go from store to store and all I could think about was when I could get to suckle again. Finally we stopped at Panera for some lunch.

“So, Jimmy, now that we have a minute to ourselves, what drove you to do what you did the other night in my living room?” she began small talk as we began our meal.

“Well, um…health class tau-…” I dragged out in deceit.

“Baby. Don’t lie to me.” She teased.

“Very well then”, I began in agreement and continued with, “I lost my mom when I was a baby, and for whatever reason I guess that plays a part in the kind of porn I watch.”

“I’m sorry to hear that sweetie. No wonder you seemed to need that closeness. Now what exactly do you mean by the porn that you watch?”

“I watch a lot of lactation and adult nursing videos online. I’ve always got turned on by things like that and that’s why I decided to take action on you.” I honestly admitted.

“I see. Well thank you for not being silent about any of this, and good for you on taking initiative with a woman. I can see why Penny likes you so much. I mean besides the obvious anyway.” She said with a sexy gaze.

“What do you mean by that Nancy?” I perked up silently.

“Baby I could feel your penis pressing against me the night you suckled from me. You’re pretty fucking huge.” She giggled as she said.

“Ummm…thanks”, was all I could reply with.

“Tell you what; I know what you are mainly expecting out of this date. Let’s get some conditions down ok?” She began.

“Alright.” I responded.

“I will treat you to your entire fantasy, nurse you, and feed you all the milk you want and need. I’ll be your mommy for tonight and as a matter of fact, since I know that having breast-y won’t be enough for you just once I can be your mommy for pretty much forever” she said confidently with a wink and a bra strap adjustment.

“But?” I questioned, waiting for her side to the deal.

“I want your cock in me as well sweetie”, she whispered as she ran her palm over my shorts and clutched my dick.

“You didn’t think that nursing you didn’t turn me way on did you? I’m sure Penny got all of what was meant between us in her huh?” she asked as she continued to slowly stroke me.

I smiled and nodded. We continued to eat and almost all the way through the meal she threw out silly suggestions.

“You know you could knock her up if you wanted to. You’d stay with us and then you’d have 4 delicious milky boobies to drink from. I make plenty of money from my business and Ollie’s dad always sends a fat child support check every month.” She joked.

“Not a bad idea, but I don’t know how I’d feel becoming a dad this young.” I answered, sternly.

“I had Penny at 16” she shot back.

“I’d have to really think about it though.” I responding, trying to drop the subject.

* * *

We arrive back to Nancy’s house and settle in the same living room as before. Friends was on the tv and she laid out a big, soft blanket and pillow setting for us to get comfortable in. She went to change into pajama shorts and had her blouse fully unbuttoned, revealing a lavender nursing bra designed to look like a lace bra. Nancy looked even better than Penny. Penny would look like she was at a slumber party if she wore what her mom wore. Nancy was a milf and was loosening her hair when she had me sit close to her. She had me lay with her to watch the show.

My cheek rested on her left breast, still covered within the bra. I took in her aroma and could smell the essence of her milk.

“Sweetie. How do you want your fantasy to come true?” she whispered as she continued to watch Jennifer Aniston on the screen and as she landed her kisses on my forehead.

“I want you to mommy me, feed me all the milk I could ever have.” I whispered back in a needy tone.

“Well lucky for you I don’t actually get dry or run out of it, it just keeps going as long as you suck. However, you will need to demonstrate to me that you are hungry. Mama needs to know when to feed her baby boy”, she cooed as she caressed my hair.

My fantasy was becoming a reality. She was playing along. I thought of how my loss of my mother affected me. I thought of how I needed the support over the years, of how I missed out on what every other kid in my school got. I literally began to cry softly. Tears ran down my cheeks and I whimpered and nuzzled my face into her breasts.

“Oh no, my baby needs to eat” she began as she adjusted my body across her lap. She fiddled with the snap of her left cup and after a tiny pop, the clasp fell down, loosening the cup. She cradled my head up to align me to her left breast.

I whimpered and jerked some more tears. “Jesus honey you’re actually going to make me let-down all this milk with all of your emotion,” Nancy said in surprise.