tagMaturePerks For the Paper Boy

Perks For the Paper Boy


Back in the 1970's a young man named Chip Wilson had a paper route, and while it wasn't all that lucrative the job allowed him to be done working in time to get to school on time. Chip kept the job for several years, even continuing into his early college career until he finally gave it up.

Because he delivered so early he rarely had contact with some people, but there were a few folks who were often waiting at the door for him to arrive, most of them being older folks who lived at the senior apartment building that was part of Chip's route.

One of them, Shirley Brooke, had just moved into the building, and she seemed to take a special interest in Chip, even giving him cookies from time to time when he would deliver the paper. One morning however, as Chip himself tells it here, Mrs. Brooke offered the lad more than baked goods.


When I was a kid, I was constantly told that I looked like the boy who played Dennis the Menace on the TV show that was popular in my youth. That wasn't so bad I supposed, but it wore thin after a while because even as I got older, I didn't change much.

At 5'6" and about 120 pounds, I wasn't much different in stature at 18 than I was at 13, and my baby-face and dimples didn't help. My Mom bought me an electric razor once Christmas and it stayed in the box until I was well out of my teens.

I was the kind of kid that aunts and other older ladies loved to fuss over, ruffling my dirty blonde hair and pinching my cheek while clucking over me and telling me what a sweet boy I was.

That wasn't something I cared much for until I got older and started to notice girls. I didn't fare very well with females my age who thought I looked too much like a kid but I soon discovered that there were older women that wanted to do more than pinch my cheek, and to my surprise many of them were pretty sexy in their own ways.

Shirley Brooke was one of those cute ladies, a petite little widowed gal who lived at the senior apartment building I delivered to. To live there you had to be at least 55 but I suspect Mrs. Brooke might closer to 65, with short silver hair and a nice smile, and she also made great chocolate chip cookies.

Originally I thought that she was just a sweet old lady until one morning when I learned that she had what she later referred to as a "naughty" side. Little did she know that compared to her I was downright perverted, proving that you can't judge a book by its cover because she thought I was a choir boy. We found out the truth about each other one Sunday morning in July of 1974.

It wasn't uncommon to catch people coming to their doors wearing their bathrobes, since the apartment house halls were interior and carpeted and looked much like a hotel. Some folks would duck back inside their apartments because they weren't expecting to see somebody out there at about 6 or so, but some didn't and on this particular morning Mrs. Brooke didn't duck back inside.

Instead she stood there smiling and although she was technically wearing the pale blue bathrobe that was draped over her shoulders, it was not cinched together at the waist but was hanging wide open. It was as if Mrs. Brooke had left it wide open for my benefit, and I suppose if I was a gentleman I would have looked away, but I was a horny teenager and what the elderly lady was showing me wasn't bad at all.

Mrs. Brooke had only a baggy pair of beige panties on under that robe, along with tiny white socks that went up to her ankles. Everything else was there for the looking, and I sure did look.

Oh, I glanced at her pale, child-like legs which were pretty shapely with only a couple of veins visible on her thighs and I noted her stomach was flat as well, but what got my attention was Mrs. Brooke's breasts.

Like I said Mrs. Brooke was a petite lady, so when I saw the size of her tits I was stunned. Even though they weren't much bigger than grapefruits they looked enormous on her skinny frame, and while they sagged a little bit they looked plenty good to me.

Her nipples were amazing though; large pebbled crimson areolas with incredibly plump bullets in the centers that looked very suck-able, and although Mrs. Brooke let out a gasp when she saw where my eyes were fixed, her shock sounded fake and she made no effort to close her robe either.

"Morning Chip." she chirped. "You startled me."

"Sorry," I replied, making us both liars, and then I pawed at the carpet and told her she was really pretty.

"Oh, you're sweet honey, but shame on me," she clucked, closing her robe slightly as she spoke.

"No really Mrs. Brooke," I mumbled shyly and then added brazenly and I nodded towards her bosom, "They look like they would be fun to play with."

"Well Chip," she responded, letting her robe open up again for my benefit, "It's too bad that you have to deliver papers or else you could find out for sure."

"I'm almost done," I answered as I sprinted down the hall to drop off the last three papers before hurrying back.

"Done," I announced as I caught my breath.

"Well then come in honey," Mrs. Brooke said as she stepped aside to let me into her place, which was decorated in typical old lady style that reminded me of my grandmother's house.

I was brought into the living room and led to the couch, and after refusing her offer for milk and cookies she sat next to me and patted my bare knee just below my shorts.

"Oh my Chip, you have hairy legs," she noted as she rubbed my calf. "The hair is so blonde I could hardly see it."

"Yes ma'am."

"What grade are you going to be in come fall honey?"

"Freshman ma'am," I replied, not thinking to add that it was college I was talking about because I figured she could tell I wasn't no 9th grader.

"Good for you Chip. I'm sure the girls will be swarming over you pretty soon, as cute as you are," she opined and I shrugged.

"Haven't had much company," Mrs. Brooke noted. "Certainly no gentleman callers, but then again I haven't had any fellows look at me like you did."

"Sorry ma'am," I mumbled.

"Don't be," I was told. "But please called me Shirley. Mrs. Brooke and ma'am make me feel as old as I actually am and I like to consider myself young at heart."

"Okay Shirley."

"Now I did lure you in here for something as I recall," Mrs. Brooke said as she wiggled her upper torso out of her robe. "Too bad you didn't see them when I was your age."

"They look great now," I assured her.

"Haven't you even touched a woman's breasts before? she asked.

"Once my first girlfriend let me put my hands under her blouse," I related. "Hers weren't nearly as big as yours though."

"Well go ahead honey," she offered as she thrust her chest out for me, and I played my part at least in the beginning and pretended I was scared when I tentatively cupped the globes in my palms and squeezed the very pliant flesh tenderly.

"You like?" she asked as her incredible nipples got even bigger under my grasp.

"Sure do. Am I hurting you?"

"No honey, what you're doing is perfect," Mrs. Brooke sighed as she leaned back into the couch.

I leaned closer to her and really started kneading them, digging my hands into the doughy tits while a floral scent filled of nostrils. My eyes went over to Mrs. Brooke's underarm which was exposed when she had put her arm over the back of the sofa, and when she saw me smile Shirley asked why.

"You have peach fuzz under your arms," I noted, although there was only a few tiny brown hairs in the center of an otherwise creamy and deep armpit.

"Oh dear," she gasped.

"It's okay. I think it looks sexy," I told her.

"Oh. Well, in that case," Mrs. Brooke replied as she put her arm back up where it was and added, And Chip, if there's anything else you would like to do with my breasts..."

"Really?" I asked, and after she smiled and nodded I leaned down and start sucking on those blooming nipples like an animal.

Back and forth I went, squeezing and kneading the one that wasn't in my mouth as Mrs. Brooke's chest started heaving and sweat started beading up on my forehead while my shorts started to get very uncomfortable.

"Oh my," a flushed Mrs. Brooke exclaimed when I came up for air after a while, and when she reached over to get a tissue to dab my head with she added, "You're sweating. It's getting very warm in here."

"Just excited I guess," I told her and then impulsively leaned down and gave her armpit butterfly kisses before adding, "You smell really nice."

"Oh!" she gasped, but after I apologized she shook her head and told me, 'That was something my late husband used to do to me. Brought back a nice memory."

"Oh, okay," I said before going to her other underarm and repeated the action, making her giggle in response.

"You're such a sweet sweet boy," she told me, cupping my cheeks and giving me a kiss that I'm sure left a little of her lipstick behind. "The only thing is that, well I may be old but I remember how back in my day boys would get really excited at times like this. Not really fair that I'm doing that to you."

"That's okay," I said with a pout.

"No, it's not Chip. Are you excited?"

"Yes Shirley. I'm really excited," I admitted, thankful that my erection was jammed down between my legs.

"Would you like me to help give you relief honey?"

"What do you mean?"

"If you take off your shorts I will pleasure you."

"Pleasure me?"

"Yes. Just stand up and we'll get those shorts off of you."

"You aren't going to laugh at me, are you Shirley?" I asked as I stood up


"Yes. We had to change for gym at school and when the guys saw me naked they made fun of me," I confessed, and while that was a true story one time they weren't laughing for the reason one might think.

"Boys are so mean," Shirley told me as she fumbled with the button on my shorts. "But then again so are girls."

"I just love your hairy legs," she repeated after my shorts went down and she rubbed them on her way up. "Now let's get rid of these."

While I wish that I had a camera going during all of this, I remember it so vividly it's like it was yesterday. Shirley's old wrinkled fingers grabbed the elastic of my boxers and tugged them downward, and I think she started thinking something was up when she reached my little nest of pubic hair.

My dick was clamped in a downward direction so all so unveiled was the beige shaft of my cock with the solitary serpentine vein running along to the glans. Down they came, slowly, while Shirley's perky face registered confusion. Then came the ridge of the fat mushroom head and my dick was free, slapping the elderly lady's chin as it sprang upwards after being released from captivity.

"Oh dear," Shirley gasped as my cock swayed in front of her eyes, the weird way it curved a little bit to the right and upwards adding to the bizarre sight of a runt like me having a cock this big.

"You promised you wouldn't laugh," I reminded Mrs. Brooke whose eyes followed the swaying prong like a tennis match.

"I'm not laughing dear," she assured me as she brought her tiny vein-riddled hand up to try and grab me. "Not laughing at all, it's just that I wasn't expecting anything like this."

"Ooh!" I sighed when she wrapped her hand most of the way around the base of the shaft and squeezed it gently.

"I can feel you throbbing, Chip honey," she exclaimed as she moved over to the edge of the couch cushion and leaned forward, and after looking up at me looking down at her, flicked her tongue at the tip of the crown and then slid her lips down the head to the ridge.

"Maybe you better sit down honey," Mrs. Brooke told me, and so I went back down and slouched on the sofa, my erection curved back onto my stomach.

"Such a big boy you are," Shirley cooed as she turned to face me, reaching over and bringing my cock upright and looking at it wistfully. "My husband, rest his soul, now he was what you would call well endowed too, but even he wasn't as large as you are honey."

"Is that bad?" I asked while trying not to laugh.

"Not at all Chip," Mrs. Brooke assured me as she leaned over to flick the tender opening with her tongue before taking a deep breath and slipping the head of my cock in her mouth before moving her lips downward.

"OH! Shirley!" I cried out, and not being dramatic either because after her mouth stopped moving downwards and headed back up, she had coated about half of my 9" with her saliva and lipstick, and as her head bobbed up and down she went down even further.

"You like that Chip honey?" Mrs. Brooke asked when she came up for air briefly, and after I nodded like an eager puppy she added, "Guess it's like riding a bike in that you don't forget how."

Then Shirley went back to work, and out of the dozen or so mouths my dick had been in by then, she was the best. She was almost deep-throating me, her lips brushing against the hand she had wrapped around the stump, and if it wasn't for the curve of my cock she might have been able to do it.

Glancing over her painfully slender shoulder, I saw that her free hand was under her baggy panties and she was busy frigging herself. At this point, the way Mrs. Brooke was going I was going to cum way too fast, so I gently lifted her face off of me.

"I want to pleasure you too," I told you, using the odd terminology that sounded more natural coming out of her mouth than it did mine.

"You don't have to honey," Shirley told me, but her tone was unconvincing and when I said emphatically that I knew I didn't have to, I wanted to, she shrugged and stood up.

"Don't look too closely dear," she said nervously as she lowered the beige bloomers.

The slightly wrinkled stomach didn't faze me, and the sight of her wide triangle of light brown and silver was pleasing to my eye. While her pubic hair grew wide and high and was probably dense at one time, the bush had thinned considerably which made her wonderfully plump labia very visible through the curls.

"Where should we?" Shirley asked and she crossed her hands over her magnificent tits for some reason, and it seemed she was considering taking me to the bedroom before I pulled her down to the couch.

Spreading her skinny thighs wide while I scrambled down to my knees and got between them, I rubbed my palm up and down her hairy delta, and Shirley shivered when my hand rubbed over her pussy lips. This brought the aroma of her pussy out, and I was blasted with her ripe scent while lowering my face into the fold.

"Oh heavens! Heavens!" Shirley was warbling as I put her legs over my shoulders and lapped away, and while I had noticed that older women sometimes had a problem with moisture down there, Mrs. Brooke wasn't one of them.

Shirley's pussy was wet before I went down on her and she only got wetter as my tongue danced inside of her. Peeking up through her bush I saw her clawing at her tits and squirming against the back of the sofa, and Before she could come I lifted my head up.

"What? Huh?" Mrs. Brooke mumbled as I stood up, my cock still hard and waving in front of me.

"Climb on," I said as I sat on the couch next to her and tried to pull her over onto me, and while she was confused at first Shirley managed to kneel on the couch cushion with her left leg and then lift her right leg over me, straddling my swollen weapon.

"Oh my!" Shirley gasped as I helped her lower herself down while holding my erection upright, and when the knob of my dick entered her the old lady moaned, her eyes rolling in her head.

Tight beyond belief, and while I suspect it hurt Shirley she didn't stop lowering herself down until she had taken about half of me, and my hands went under her arms to keep her from getting fully impaled right away.

"Chip honey - you're so big - don't know if I can..."

"Sure you can," I encouraged while guiding her up and down gently, and while I was no weightlifter Mrs. Brooke was so light it was no problem.

Shirley leaned a little forward and braced her hands on the back of the couch behind me while starting to move up and down on her own, and this gave me perfect access to her dangling breasts.

"Oh dear," Shirley kept repeating as my hands kneaded her very pliant tits roughly as she bounced on me, the sloshing noises coming from her pussy getting louder as she kept taking more of my dick. "How I've missed this."

The silver haired senior was wild-eyed as she skinny body moved up and down like she was on a merry-go-round, and as she started bouncing up and down faster and harder I sensed the end was near for her. That was just as well because I was having trouble holding my orgasm back.

Shirley let out a very loud groan, and as her pussy convulsed around my cock I erupted inside of her, sending what felt like a ridiculous amount of cum deep into her womb as she collapsed onto me.

The senior's pale skin was damp with sweat as I embraced her, and she stayed on top of me until my dick deflated and slithered out of Mrs. Brooke, the sensation pleasurable to me as well as her I guessed because she let out a gasp when I plopped out.

"What you must think of me," Shirley said as it seemed like the reality of what she had done hit her, but I kissed her and smiled.

"I think you're great," I replied. "That was amazing."

"You've done this before haven't you honey?" Shirley asked as she prepared to stand up. "Probably to other gals in this complex right? Sorry. None of my business, but you were too good to be as innocent as you look."

I said nothing but just smiled and tried to assist Mrs. Brooke in getting to her feet, and after she did her knees buckled a little but I had my hands on her hips to catch Shirley as she got her balance.

Standing there with her legs spread apart as if she was still on me, my eyes went to her pussy where my cum and her juices were drooling out from her puffy labia and hanging on her pubic hair, confirming that I had really popped a load inside of her.

"Need help?" I offered but Mrs. Brooke declined as she waddled towards the bathroom, her slightly droopy butt wiggling as she walked, and after she returned I went in to give myself a brief rinse off before rejoining Shirley.

"Guess I better get going," I said as I tried to get my clothes together.

"Too bad. I would love to have you walk around the place as you are all day," Shirley told me as she grabbed my cock and pulled me close. "First time I've seen this thing of yours soft, and it's still huge. May I say goodbye to it?"

"Sure," I responded and watched as her lips went all the way down to my pubes before sliding back to the tip, and I knew if she did that a couple more times I wouldn't be leaving.

"Say," I mentioned after I got dressed. "If you ever want to - you know - again?"

"Might be a while before I recover but..." Mrs. Brooke told me at the door.

"Just give me a hint that you're in the mood," I suggested as I cupped her dangling breasts once last time. "Maybe giving me a peek of these beauties when I deliver?"

"Deal," she said, but then told me to wait as she scurried to the kitchen, and when she returned she had a baggie of cookies for me to take. "I know how you like the chocolate chips."

"I do," I said in thanks but then added, "Today though, they'll only be the second most delicious thing I've eaten."

"Oh Chip!" Shirley blushed as I left, and as I went down the hall of the building I smiled as I passed the doors of a few of the other residents that had given me more than cookies since I had started delivering.

"This is the best job I've had yet," I mumbled as I headed home, having already had a day's worth of fun before breakfast.


Thanks for reading.

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byVeryDirtyMind© 7 comments/ 61053 views/ 30 favorites
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by Anonymous

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by amorone01/26/18

Loved it

Thanks for a very erotic tale. Well written and I am envious of Chip.

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