Mama Bear

Story Info
The lonely neighbor lady and I become close.
4.9k words
4.59
146.1k
262

Part 1 of the 3 part series

Updated 09/01/2023
Created 01/04/2022
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A few sprays of cologne and I felt ready to go. I was dressed rather nicely, wearing some designer jeans, a nice, buttoned shirt, and a blazer. I wasn't on my way to a wild party, or a date with a hot chick; I was having dinner with my neighbor, Mrs. Holt.

I lived with my widowed father in a nice neighborhood. My dad was a vice president at this big pharmaceutical company, which meant he was either working at his office, or wining and dining people for work. Thankfully, his huge paycheck meant that I wanted for nothing. Still, I might have seen him maybe once or twice a week, as he often opted to sleep in hotels. This meant that I practically had the house to myself.

This also meant that, more often than not, I had to feed myself. It wasn't a big deal; I had a checking account balance that would make even some of my teachers jealous, so I could order practically anything that I wanted. Whether it was a Brazilian steak house or Waffle House, my options were endless.

It had started over a month ago when I had come home to an empty fridge. After some minor deliberation, I had decided to go down to the local Buffalo Wild Wings, enjoy a nice meal, and possibly watch some Premier League games. It's not like dad would even mind.

After grabbing my keys, I hopped into my car and backed out of the garage. A few miles down the road, while sitting at a four-way stop, I had happened to notice my neighbor Mrs. Holt struggling to unload groceries out of her car. My wanting to help her ended up with her inviting me over for a nice meal. Not only did I enjoy the first home-cooked meal that I'd had in ages, but I was able to enjoy some nice company. After dinner, I stayed for dessert, and was sent home with some gifted leftovers.

It then became a weekly ritual that had been going on for a little over a month. She was happy to invite me over again. The next visit, I was treated to shepherd's pie. A week after that, I was treated to spaghetti and meat sauce. The week after that, I feasted on grilled chicken and baked potatoes.

Even though I was wealthy, popular, and had lots of friends who were the same, I really treasured my weekly dinners with Mrs. Holt. These days, I didn't care much about going to the hottest parties to get blitzed and hook-up with hot chicks. I barely cared when my dad bothered to make an appearance at home. One day a week, I got to eat dinner with a wonderful woman who fussed over me and listened to what I had to say. It was like having a second home.

That Friday after school, dad sent me a text to let me know that he'd be crashing at the Hilton for the weekend. I smiled; usually he didn't bother to text me any notice. Even though I'd been invited out to the lake with my friends, I lied telling them that I had to work on an extra credit project for History class.

Tonight was pot roast and mashed potatoes with Mrs. Holt. I came over at 6 PM sharp, holding an apple pie in my hand that I had picked up from the store. After ringing the doorbell, a clap of thunder could be heard overhead, and a few seconds later, Mrs. Holt opened the front door.

She was a curvy woman in her mid fifties, with long strawberry blonde hair that had streaks of gray. Despite her older age, she was still pretty, though not a former beauty queen, in my opinion. Still, I'm sure she could still turn some heads, possibly if she fixed herself up more.

My hostess hurried me inside and gave me a hug. After closing the door, another round of thunder could be heard. As I walked through the front hallway of her home, a cozy feeling washed over me. Mrs. Holt's house wasn't as chic as mine, but it had all the warmth that my house notably lacked. There were pictures of smiling people on the wall, some fuzzy slippers near the front door, and a bin full of woven blankets.

"Wow!" Mrs. Holt exclaimed. "I think we're due for a storm tonight."

"Sounds like it," I agreed. "I brought some pie for dessert."

"You're so sweet! I have some vanilla ice cream in the freezer that will go great with it."

Before she could even tell me, I made off to the guest bathroom to wash my hands. I looked around the bathroom, smiling at her cute decorative towels and the scented candles. I felt foolish for having lived down the street from her for over 10 years and just now getting to know her.

Mrs. Holt had divorced her husband 2 years ago. She had a son who had moved out long before Mr. Holt had moved out, so she'd been an empty nester. Even before we had become friends, she was undoubtedly one of the nicest people in my neighborhood. When our neighborhood had a block party, she'd made a brisket so good that some of the neighbors insisted she open her own restaurant. There were even a few times that I'd fantasized that she'd maybe ask my dad out for a date, but she wasn't his type; he liked the high-maintenance women with too much makeup and at least one type of completed cosmetic surgery.

I walked out of the bathroom and went to the kitchen. Mrs. Holt handed me a plate and told me to help myself. She allowed me access to the hot food sitting on table while she poured me a glass of lemonade.

As I savored the wonderful meal, we told each other about how our respective weeks went. It was nice to have someone asking how I was doing in school and to fuss about me. Halfway through my first helping, we could hear the torrential rains beginning.

"That pot roast was amazing," I said, mopping my mouth with my napkin.

"You sure that you don't want another helping?" Mrs. Holt asked.

"I'm going to try and save room for dessert."

"You know the drill: some of this is going home with you." She looked out of the window at the windblown rains. "With this weather, I don't think you'll be going home any time soon."

"Fine with me," I said.

"How about we go watch some TV?"

"Sure."

We headed to the living room, where we watched a few episodes of Family Feud, followed by "The Wizard of Oz". About halfway through the movie, the power went out. I turned on the flashlight on my smart phone, and Mrs. Holt did the same. Thankfully, she had a lot of candles around her house, so she lit them and sat next to me on the couch. We sat there in the dimly lit room, which was silent, save for the sound of the falling rain.

"If you want, I can break out some dessert," Mrs. Holt offered.

"My stomach's still working on dinner, thanks," I told her. "As a matter of fact, thanks for always having me over. I really like coming over here."

"It's my pleasure, honestly. An empty nester like me really knows the value of good company."

"You know...your cooking reminds me a lot of my mom. When I was a kid, she was always cooking for me. She made a mean grilled cheese sandwich."

"She sounds like a wonderful person. I used to make my son David grilled cheese when he got home from school." She gave a wistful sigh.

"Is he planning on visiting soon?"

Another sigh. "I barely see him. He's got a nice new job, and he's loving his independence. Sad thing is, I miss taking care of him. I spoiled him rotten since he was my only son. I'd clean his room, cook his food, and even do his laundry when he came home from college."

"That was very sweet of you," I said.

"Yeah, well, it didn't stop him from leaving. Didn't stop his father either, though, I think his secretary might have helped, too. I bet she doesn't even know how to work a stove." She gave me a worried look. "Mark, do you think that I try too hard to please men?"

I found my momentarily caught off guard, but I was quickly able to regain my composure and answer her question.

"With David, I just think he grew up and is enjoying doing things for himself for once. As for your husband, he was a jerk."

Mrs. Holt snorted and laughed at the last part. "Thanks, honey."

"I guess now would be a good time to thank you again for all of the past dinners. It's really been nice to have someone who worries about me."

"Awwww, of course, honey," she said before she pulled me in for a hug. "You're always welcome here."

"It's like...I almost have my mom- "

Mrs. Holt interrupted my last statement by gently maneuvering me so that I was lying sideways on the couch with my head in her lap. In the dim room, she gently stroked my hair and began to hum. I should have been weirded out by this, but it felt so soothing...

My eyes fluttered open. I didn't even remember falling asleep in the first place. The television was back on and so were most of the electronics in the house. I glanced at the battery-operated clock on the wall and saw that it was almost 10 o'clock.

I heard gentle snoring above me and deduced that Mrs. Holt had fallen asleep as well. My head still upon her lap, my view of her face was still obscured by her large bust. I really needed to get home.

As I stirred on her lap, I must have jostled her somehow, because she suddenly fell forward, crushing my face with her enormous breasts. A few seconds later, she awoke and righted herself. I quickly sat up, and we both stretched and yawned.

"Oh, my," she said, rubbing the sleep from her eyes. "How long were we out?"

"I dunno. But it's getting late; I'd better hit the road."

"Okay," she said, rising from her seat. "At least let me pack some leftovers for you."

It was useless to argue. We both sauntered over to the kitchen, and she hastily packed some food into some Tupperware containers. She then saw me to the door, but, after opening it, we were greeted to the sight of rain falling so hard that could be seen against the streetlights.

"Oh, honey, no." Mrs. Holt said almost immediately. "There's no way I can let you drive in this weather. Why don't you crash in David's old room?"

It was no contest; I really didn't feel like trying to navigate through this storm. Mrs. Holt closed the front door and escorted me to her son's room. She offered me some of his old pajamas and left to allow me to change my clothes in private. I felt a bit silly as I looked at the red plaid buttoned shirt and matching pants. Only after putting them on did I realize how great they felt!

She returned a few minutes later, having changed into a nightgown and robe, carrying some fresh linens. I insisted on making the bed, but she overruled me again. A warm feeling overtook me as I watched her meticulously spreading the comforter and placing a pillow on my bed.

"Well, that should do it," Mrs. Holt declared as she gave the made bed a few pats. "You should be snug as a bug."

"I really appreciate it, Mrs. Holt," I said.

"Have a good night, honey," she said as she pulled me in for a hug.

That turned out to be a bad idea, but it didn't know it right away. I don't know if it was the wonderful meal, the cozy pajamas, or the overall hospitality of my host, but that warm, fuzzy feeling caused me to react in a certain way. Mrs. Holt let out a small yelp, and after we stepped away from each other we both looked down at the protrusion from crotch, which was pointing accusingly at Mrs. Holt.

"Shit!" I cried. I then covered my mouth, embarrassed at having let a swear word fly in front of Mrs. Holt.

"It's okay, Mark," she said, blushing and trying to cover her grinning mouth. "I...I'm actually flattered that I can still make that happen at my age."

I quickly spun around and put both hands over my crotch, mentally praying for this erection to subside.

"Mark, it's okay," she assured me. "I'm 55 years old, so I'm pretty sure you don't have anything down there that I haven't seen. Would you like me to help you with that?"

Not bothering to turn around I asked her, "Um...help me how?"

Without a word, she walked up to me, grabbed my arm, and guided me over to the bed. Placing her hands on my shoulders, she gently made me sit on the side of the bed and then sat down beside me. My eyes went big as saucers as I watched Mrs. Holt reach over and deftly undo the buttons on the barn door of my pajama pants and then pull at the boxers below, allowing my prick to spring out of its hiding place. Grinning, she immediately grabbed my erection and started to move her fist up and down. My eyes fluttered and a low moan came out of my mouth.

"Boy, Mark," Mrs. Holt said. "I never would have imagined that you were hiding something like this! I'm impressed."

My only was response was to grip the sheets and groan with pleasure. Her hand was so soft and so warm. My toes curled as I struggled to weather the waves of ecstasy washing over me.

"Shhh, it's okay," Mrs. Holt cooed. She put her arm around me and pulled me close, resting my head on her massive bosom. "Mama's here. Just squirt any time you want to; don't fight it. Or do you want me to stop?"

"Nooooooo," I moaned.

"Okay, love. I'll keep going until you're done."

Mrs. Holt kissed the top of my head and began humming a song. I was powerless in her grip. This wasn't the first handjob I'd received, but she was working me like a pro. I could feel the precum leaking out of me, making Mrs. Holt's movements much more enjoyable as it lubricated both my shaft and her palm. Even though she had told me to cum, I wanted this to last forever.

I shut my eyes as I climaxed loudly, with my roars muffled by Mrs. Holt's chest. Three glorious spurts were produced by my still-hard cock, and I could feel wetness on my lap. I collapsed back onto the bed and Mrs. Holt let go of me.

"Mark, you did such a good job!" She said. "Did that feel good?"

"Yes," I panted, wiping the sweat from my brow.

I peeked an eye open and saw her standing over me, her left hand glistening with my juices. Both eyes opened wide with amazement as she started licking my cum off of her hand. I sat up and put my semi-hard cock back into my pants.

"Don't feel embarrassed, hon," she said. "Davey used to make this whole room sticky when he was your age. It's a perfectly natural thing to do."

"Right," I agreed. "Um...thank you."

"You're very welcome. Well, I'm going to turn in. If you ever need anything, I'm right down the hall. And don't worry about the pajamas. I'll wash them first thing in the morning."

I looked down at the cum stains on my crotch and muttered, "Yeah, sorry about that."

"I told you, it's not a problem. Good night!"

She left the room, closing the door behind her. Even after I had turned off the lights and crawled under the covers, the entire thing seemed surreal; one minute, I was eating dinner with this wonderful woman, and the next minute, I was making knuckle children with her on her son's bed. The events replayed themselves in my head until I fell asleep.

I awoke the next morning feeling refreshed, but uncertain of what kind of conversation I was going to have with my hostess. I looked at the time displayed on my smart phone; it was still early, about 8 o'clock. My heart was pounding as I got out of the bed and exited the room.

When I walked into the living room, I found Mrs. Holt on the couch, sipping some coffee and watching television. She was still wearing the robe and nightgown from last night. She smiled at me and put down her mug.

"Good morning, sleepyhead," she said brightly. "Feeling okay?"

"Yeah, like a rock." I said. I looked out of the window, noticing that while last night's storm had passed, it was still very cloudy outside. "Thanks again for letting me crash here."

"You can crash here any time," she said, rising from her seat. "Are you ready for some breakfast? I was thinking about making some pancakes and bacon."

"That sounds good."

"Great! I'll go get it started. You just sit here and watch some television."

As Mrs. Holt sauntered off to the kitchen, I caught sight of her large, swaying backside, which made my dick throb. A few seconds ago, I wasn't really sure how to feel about her, but I did now. I walked up behind her, threw my arms around her waist, and embraced her from behind, making sure to grind my full erection against her butt.

The few seconds we stood there seemed to go on forever. There was an unbearable silence between us, and then I felt Mrs. Holt gently grab my left hand and lift it away from her. My heart sank, fearing that I had somehow misunderstood her feelings. As I prepared for her to give me some gentle reproach, she put my left hand on her left breast. After I gave it some gentle squeezes, I heard her softly moan.

"Is this what you want, Mark?" Mrs. Holt asked, her voice husky with desire.

"Yes, absolutely."

She then took my right hand from her waist and placed on her crotch. "And what about this?"

"Yes, please," I whispered as I nuzzled the back of her head.

"You poor boy. Nothing would make me happier."

I then proceeded to grind and dry-hump her, fondling her massive teat and rubbing her loins. We both writhed and moaned, our desire for each other growing each second. I then released my hold on her and she turned around. We both seemed to have the same idea, and we embraced each other before sharing a kiss. Mrs. Holt grabbed my butt with both hands and rammed her tongue into my mouth.

I couldn't remember the last time that I had ever been so aroused; I was genuinely afraid that I was going to blow my load right there. When she was done probing my young mouth with her tongue, I forced it back into her mouth to do some probing of my own. The taste of black coffee and morning breath greeted me, but it did not detract from my arousal in the slightest. Before I could even react, her right hand abandoned my ass cheek and grasped the large lump in the front of my pants. I broke our kiss to let out a loud moan.

"I want this, Mark," Mrs. Holt said. "Are you going to give it to me?"

"Yes, Mrs. Holt!"

"Mmm, good. Come with me."

Still holding my rod, she led me out of the living room and into her bedroom. Once she had closed the door behind us, she relinquished her grip on me. When I saw her undoing the belt on her robe, I removed my clothes in a matter of seconds.

"My, my," Mrs. Holt said. "I like what I see."

I grunted and started to stroke myself as I watched Mrs. Holt take off her robe and throw it away. My ears and face burned as I watched the older woman's eyes roving all over my naked body. I shamelessly dripped pre-cum onto her bedroom carpet.

"I should warn you, Mark, that I haven't really done much in grooming, so I hope you're not scared of body hair."

"Mrs. Holt, please!" I begged her. "Take it all off."

"Okay, dearie. Have a look."

I watched with joy as Mrs. Holt undid the buttons on the top of her nightgown before grabbing the hem and pulling it over her head. My cock throbbed at the sight of her chunky thighs, pudgy belly, and fat breasts. She stood there blushing, and I could see a large wet spot in the front of her underwear. I walked up to her and embraced her again, enjoying the feel of her bare skin against mine. She pulled me in for another kiss and grasped my cock again.

After another round of passionate kissing, she pulled away from me and pulled down her underwear. After kicking them away, she climbed into the bed and lounged on her side. I didn't wait for her to invite me to follow her and quickly got in bed with her. I then dove on top of her, pressed my face into her left breast, and took her nipple into my mouth.

"Oooooh! My goodness!" Mrs. Holt cried out.

I reached over to fondle the other breast before closing my eyes. I humped her leg madly, feeling the bristly hairs upon it brushing against my skin. My tongue prodded the hard nipple as I sucked it madly.

"Oh, Mark! You're making me so wet! Here, feel!"

She wrested my hand from her tit and put it between her legs. My fingers felt a deluge of love juices, mingled with hair and flesh. Unbidden, I put my fingers inside of Mrs. Holt, as she howled madly as I explored her womanhood.

"Mark, pleeeeease," she moaned. "Be in me! Give it to me!"

I lifted myself away from her breast. Once parted, she put her hands behind her head, baring her furry armpits to me. She then spread her legs wide, and I could clearly see the bramble of hair that crowned her nethers. She was right to warn me of her lack of trimming, but I didn't care. I quickly took my place between her thighs and stuck myself into her.

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