Dianas Tales-student Aid - Cover

Dianas Tales-student Aid

by wendyk52

Copyright© 2022 by wendyk52

Coming of Age Sex Story: I'm proud of the fact I've maintained a 34c-29-35, 129 pounds figure on my 5'6" frame, although I know I'm no model. I have a high sex-drive, though, and having a husband away from home over half the time doesn't help that situation.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/Fa   Consensual   Heterosexual   Fiction   True Story   Cheating   Slut Wife   Interracial   Black Male   White Female   Exhibitionism   Oral Sex   .

DIANA’S TALES: STUDENT AID PT. 01

Oldbroad76

All characters are 18 or older. This story was written in collaboration with Diana R. The story starts a little slow as it builds the story, but it gets there. This story features a relationship between an adulterous older white female (53 yo) and a young black man (18 yo). If that doesn’t appeal to you, then please save yourself the aggravation. If it does appeal to you, we hope you enjoy.

“Diana, I need your help,” Marie pleaded on the phone. “We worked together for over 30 years. Look, you know I wouldn’t call you if there was another way. I know you’re retired, but you’ve got connections with some of our wealthy and most generous alumni. Your husband works with some of them. You’ve got extra pull I just don’t have. Please, can’t you just make some calls?”

I was skeptical, but Marie was a good friend, and she wouldn’t reach out to me unless it was a dire situation. We had worked together for decades as guidance counselors at the community college, although I retired about a year ago. I’m still only 53, but my husband makes a good living, and we could afford for me to retire, although my husband still works. For him, the work sustains and fuels him. For me, the prospect of working until I couldn’t enjoy my retirement just wasn’t appealing, so I quit about a year ago and have enjoyed pursuing all the interests and hobbies I never had time for previously.

“Okay, explain it to me again,” I said, trying to be patient.

“His name’s Dion Gooden. He’s an African American kid from Douglass High School on the southeast side of town. Lived there his whole life, and you know how rough it is down there. He’s 18, just graduated high school this spring. Dion’s a real hard luck case. His dad is in prison, and his mom is a bad addict. He’s been in and out of foster homes the past 5 years, but he’s aged out of that system, so now he’s on his own. He wants to take classes and get an associate’s, but he needs some help.”

“Can’t he just take out student loans or get a Pell grant?” I pointed out.

“He could, but he’s working two minimum wage jobs just to afford a car and a place to stay. You know how crazy rent has gone the past few years, and he’s got some debts he needs to pay back --”

“So, he doesn’t know how to manage his money, and he wants to be bailed out,” I countered.

“I don’t think it’s like that. He’s racked up some medical bills, and he ran into the wrong car. The car damage was his fault, but his insurance didn’t cover the full cost on the other side, so he’s stuck with the extra costs. He took on a second part time job in his senior year, and his grades suffered, and there’s no way he can keep on top of college classes while working 70 hours of manual labor a week. But I’ve met him, and I really think he just needs a break. He’s a good kid, but he’s shy. You’ve got a way with coming through for some of these kids. Do you think you can help him? Just talk to him, and you’ll see what I mean.”

I sighed loudly on the phone. “Can you lay the guilt trip on any thicker?” I asked.

Marie knew I couldn’t pass a hard luck case without helping. It’s part of the reason I became a guidance counselor in the first place. I always loved helping people, and watching kids go from lost to finding a purpose in their lives was always incredibly rewarding. If it wasn’t for the administrative bureaucracy, I might even still be working, but the incessant red tape became frustrating and made the job damn near impossible at times.

“I can set up a meeting,” Marie offered. “After you meet him, I’m sure you’ll want to help.”

“So, he’s in a catch-22,” I said, processing all the information Marie had given. “Take out the loans, and he doesn’t have time for class anyway, and he’ll probably flunk out and be on the hook, for the loans. If he stops working, he can get loans and take classes, but he can’t afford a place to stay. What exactly is it that you think I can do?”

“I don’t know. Just work your magic,” Marie said brightly.

“My magic. Yeah, just let me grab my witch’s broomstick and book of spells,” I joked.

“I don’t know. You always seem to figure something out. I’m sure you will here, too.”

I sighed one last time as I wondered what I was getting myself into.


A week later, I walked into a cafe to meet Dion. Marie had provided his contact info, and, after a few phone calls and texts, he agreed to meet on Tuesday afternoon at a café close to campus. As I stepped through the door, I saw a young black man, about 5’11” and 175 pounds waiting nervously at a table. He was the only black person in the café, and his eyes studied me, seemingly trying to figure out if I might be his appointment.

“Hi, I’m Diana,” I said with a warm smile as I extended my hand.

“Uh, I’m Dion. It’s nice to meet you,” he answered. He shook my hand, but his voice was soft and lacked any confidence or conviction.

I took a seat with him at a small round table, and we ordered some coffees. He had dark features and looked strong and clean cut. His curly hair was cut short by a razor, and he looked freshly shaved. He dressed in nice slacks and a polo shirt. I couldn’t discern if this was his normal attire, or if he dressed especially for this occasion.

“So, Marie tells me you want to go to college,” I began.

“Yes, ma’am. I’d like that. I like criminal justice. I’d like to get a degree so I can work in that field.”

“Why criminal justice?” I asked, trying to gauge how serious was his pursuit.

“Well, I think it’s interesting. And where I come from, sometimes life is tough. A lot of gangs, a lot of drugs, and I seen a lot of my friends end up on the wrong end of a gun or knife when they didn’t do nothing wrong. I want to do my part to try to clean up those streets and make it a safe place to live.”

His voice gained confidence as he spoke. It was clear he’d given a lot of thought to his aspirations and that those goals filled him with purpose.

“So, what do you need to do to make that happen?” I followed up.

“That’s what I don’t understand. The college costs ain’t a big deal. I know I can get a Pell grant. That’s the easy part, but short of free room and board, I don’t see how. These two jobs I’m working got me running around like crazy all week. I ain’t got no time to take classes. I’ll do the work; I ain’t afraid of that. But rent ain’t cheap, you know. I need my car to get to work and to class. I ran into someone a year ago, messed up some rich dude’s ride. My insurance only covered part of the damage. I’m still on the hook for the rest, so I’m paying through the nose on car insurance and still paying that dude off. And I got sickle cell, so I’m in the hospital about once a year, and now I’m paying that note, too. It’s just bills, bills, bills. This whole adulting thing ain’t no joke.”

Marie was right. This kid had some tough breaks and a huge hole to climb out of. Nothing is impossible, but most people have a short period in their lives after high school to try to get set on their feet. The whole key to life is to have a skill set. Whether you get a degree, a certification, or make/ sell something, you have to have a special skill or talent to get ahead in life. If you don’t get set on a good path in young adulthood, it can be hard to recover as marriage and kids come into the picture. Some people do make something of their lives, but many don’t because it’s a thousand times harder, and Dion seemed to have the deck stacked against him through little fault of his own.

“Isn’t there someone who can help you out? An aunt or uncle? A brother, sister, or cousin? Grandparent?” I pointed out.

Dion shook his head. “My pop’s in prison. I never even met my grandparents on his side. God knows where my mom is. Ain’t seen her in 4 years. God knows my grandparents on my mom’s side. He’s got them up in heaven with him. I’m the oldest. My brothers and sisters are still in foster care. I got a cousin, but she’s shacked up with a druggie. Ain’t no one else. So, you tell me what options I have?”

“Girlfriend?”

Dion scoffed. “I wish. Can’t even afford to take care of myself.”

“It’s okay,” I conceded. “Having a girlfriend to split rent with might help. It can also distract you from classes. I’ve seen way too many kids let their schoolwork slip for some girl. How about a roommate?”

“I’ve got a roommate, and that’s just a small piece of what I owe, anyway. Look, I want this. I don’t see how right now, but if there’s a way, I’ll do it. I just can’t be working in grease pits and mopping floors the rest of my life. But I’ll do what I got to do to get there.”

“Okay, look. I can’t promise anything, but let me make some calls,” I told him. “Give me your work info. I want to check in with them. If they vouch for you, I know some people who often donate to the college. Maybe I can arrange for room/ board in place of scholarship. Now if I can get that arranged, you’ve got to promise to earn it. I’m sticking my neck out for you; don’t make me regret it,” I warned him sternly.

Dion’s eyes bled with gratitude. “You won’t regret it,” he promised, his eyes nearly tearing up. “If I got a place to stay, I can just work one part time job to cover my other bills. I promise you, if you can get me that deal, I’ll make good on it.”

I smiled, admiring his determination as he pushed across a slip of paper with his current job info. “Okay. Give me about a week. Let me see what I can shake loose,” I told him.


First, I checked up with Dion’s employers. One employer was a breakfast diner, and the other was a janitorial service, and both vouched for him, saying he was a reliable employee who didn’t cause any trouble.

I called Marie and had her send me a copy of his high school transcript, and I talked to his high school guidance counselors. Again, no red flags, and everything indicated he was just a hard luck case who needed a break in life. In fact, he was a good student, who probably could’ve gotten into 4-year colleges if he had the money. His story pulled at my heartstrings. He was dealt a crappy hand and had every reason to throw in the towel. So many other kids in his situation either went for the allure of the street life or submitted to a lifetime of menial existence, and I was resolved to at least give him a chance in life.

I was acquaintances with some of the larger college donors, and I contacted them if they could help, but all of them passed. I reached out to Section 8 to see if they could help him get subsidized housing, but the wait list was so long, it would take years to process his request. He probably wouldn’t qualify, anyway, since he had no kids and had income from two jobs.

There was one last ditch option that I had intentionally avoided, but I didn’t see any other way. My husband was away on business, but I called him and told him about Dion’s case. I recapped his whole story from his time in foster care to his more recent struggles with medical bills and debts with no family to help.

“God damn it, Diana, he’s not our problem. Why do we have to help?” he complained.

“Honey, his life is at a make or break point. He didn’t have parents like we did. It’s a miracle he’s gotten as far as he has. Most kids with his trauma and abandonment, they’ve got demons they can’t overcome. He’s still fighting to get somewhere and do something with his life. I’m afraid he’ll be lost if we don’t step in.”

“So, what are you suggesting exactly?” he demanded to know.

I took a deep breath before I let the words come out. “I’m suggesting he stay with us for a while.”

My husband burst in mock laughter. “And what if it doesn’t work out? What if he’s a nightmare? If he steals stuff. Plays loud music at all hours. Makes a mess of the house. Throws wild parties. Invites over unsavory friends. Has a girlfriend that basically moves in with him. Or if he refuses to ever move out. What then?”

“I’ll set ground rules. I’ll be responsible for all that, and you can blame me if I’m wrong about him. But I’m telling you, he’s a good kid. We won’t have any of those issues. Look, you’re away over half the time on business, anyway. You’ll hardly ever even see him.”

“I don’t know Diana. “ He paused for a long moment, his breathing the only sound coming across the line as he considered my proposal. “Fine, do it your way, but, if anything goes wrong, this is all on you. I don’t want anything to do with it.”

I exhaled deeply as I hung up the phone. My husband clearly wasn’t thrilled with the prospect of taking in Dion, but he relented in the end, and now my body shook with the prospect of that reality. I was sure taking Dion in was the right thing to do, but I knew it also played into my own greatest weakness. Taking in Dion was playing with fire with regards to my own predilections.

I was widowed by my first husband over a decade ago, which partly led to my decision to retire early. After his death, I realized that life was too short, so I resolved to live life to the fullest. I remarried a few years back, and my husband is a dear, but he’s frequently away from home on business, sometimes for weeks at a time. He provides well for us, but I realized after marriage that I was often left alone in the house. I traveled with him on a few of his business trips, but he’s a workaholic, often pulling 12-hour days, so I was left mostly waiting around a hotel suite in a strange city for him to come back. After a few of those trips, I opted to at least wait for him in the comfort of my own home. That said, even when he’s home, he still routinely works 12-hour days, so I’m left on my own a lot anyway.

I’ve at least managed to keep myself in shape, watching what I eat and exercising regularly. I keep my auburn hair short, although, at 53, some greys are creeping in. I play with myself a lot, but I still find myself making excuses to stray from time to time. I figure my own physical affairs just counterbalance his emotional abandonment, so it all works out even in the end. Besides, what you don’t know can’t hurt you, I’ve reasoned.

That said, I knew inviting Dion, a young man, to live in our house would play into all my worst temptations. I love my husband, but he is a few years older than me, and his work schedule doesn’t leave time for staying in shape. Having a young strong man in the house would be nice, although I wondered if Dion would have any interest in an older woman like myself. Still, it wouldn’t hurt to have some eye candy in the house and give me something to think about while I masturbate.

Despite my own hesitancy, I knew I was talking myself into inviting Dion to stay with us. In my heart, I knew it was the right thing to do, but I also knew I was opening Pandora’s Box. Nevertheless, I made up my mind and decided to accept the consequences, come what may.


A week later, Dion and I were sitting at the same table again in the same cafe near campus.

“So, what now? Did you find some help?” Dion eagerly asked.

“I called a lot of people, and not a one was able to help,” I started to explain.

“I knew it!” he muttered in obvious frustration.

“No, no wait,” I tried to reassure him. “I don’t give up that easy, and neither should you. None of them was willing to help, but maybe there’s another option.”

Dion’s ears perked up, although he appeared skeptical. He sat, his brows raised and his eyes laser focused as he waited for me to elaborate.

“Look, this may sound strange,” I continued to explain, “but you can move in with my husband and myself. We have a furnished basement. There’s already a bed and a bathroom down there. Usually it’s for guests, but it’s yours if you want it. It’s a walk out-basement, so you can have some privacy. You can stay, rent free, and we’ll feed you. That way, you don’t have to worry about housing costs. Then Marie can help you with the Pell Grant for tuition costs, and then you just need to work enough to cover your other debts.”

His face softened as he heard my proposal and realized that my offer was legitimate.

“I - I -- I don’t know what to say,” he said softly.

“Listen. There’s ground rules if you live with us. I see your grades, and you’ve got to get good grades. No loud music, no drugs, no drinking. No girlfriends staying over. Do your own dishes and laundry. Don’t make a mess. Keep the basement clean. Any questions?”

Dion’s face showed that he was still processing the proposal, and I waited patiently while he considered it.

Finally, he spoke, asking “How long can I stay?”

“It’s a two-year degree, right?”

He nodded his head.

“Two years then,” I answered with a smile. “Provided you can follow the rules. Are you in?”

“I’m in,” he quickly answered.

“Good. Classes start next week. The timing is tight, but I think Marie can pull some strings to get you fully enrolled. When do you think you’ll move in?” I asked.

“Is this weekend ok? I’ve got a co-worker at the diner. He’s trying to move out of his mama’s. He’d take over my lease.”

“That sounds perfect. This weekend it is. Here’s the address,” I said as I slipped him a piece of paper. “You already have my cell phone. Just let me know what time you’ll arrive. Till then, good luck.”


Marie called me the next day, and she was excited to process Dion’s paperwork to get him registered and enrolled. Then Saturday came, and Dion arrived just after lunch to move in. He drove a small older model Honda Civic hatchback, and his world of belongings fit in his car.

“Nice house you got here, Mrs. --”

“It’s Diana,” I corrected him, “just call me Diana.”

He got his boxes and bags moved into the basement, and then he came up to see the rest of the house.

“Where’s your husband?” Dion asked. “I wanted to thank him, also.”

“Oh, he’s out of the house,” I breezily replied. “He’s a senior engineer for an oil company. He’s always off setting up new sites, so he’s away a lot, sometimes for weeks at a time. He won’t be back for at least another week.”

“Oh yeah, you mentioned that before. Must be nice for him getting to travel all around like that.”

“I suppose. Leaves me home alone a lot though.”

“Who’s this? You got a kid?” he asked, pointing at an old family portrait hanging on the wall.

“That’s Bradley. He’s 20 now. Not such a kid anymore. He goes to college far away from here He has to fly home for visits, but he’s been doing an internship/ co-op at a corporation near his school for the past year, so it’s been a while since we’ve seen him.”

“He’s lucky to grow up with you,” Dion observed, obviously struck by the opportunities our son had in life.

A silence lingered after that last line, only interrupted by the sound drifting in through the open windows of the wind rustling through the leaves.

“Alright, get settled in,” I said, breaking the silence. “I’ll have some dinner ready at 7 pm. You eat what I make, otherwise, you’re on your own. There’s snacks in the pantry. There’s a TV in the den, and there’s one down in the basement, too. Both have satellite and are connected to some streaming services. If there’s anything else you need, let me know. Make yourself at home. Okay?”

Dion nodded his head and then headed back to the basement to unpack his things.


Dion got settled in over the next few days.

He quit his job at the breakfast diner to free up his time to take classes during the day, but he kept his second janitorial job in the evenings to pay for his debt, car, gas, and insurance, although he cut back on his hours, so he’d have time to study. Since he had a friend to sublease his apartment, Dion was able to put the money he saved for next month’s rent toward his tuition costs until his Pell grant came through.

He was so excited Monday morning when he left for his first classes that he came home and pored over all his new books, already trying to work ahead.

I admit it was nice having someone else in the house. With my husband away so much, a woman can get lonely. Just having someone to talk to was a pleasant change. At first, Dion kind of hid away in the basement, but, by mid-week, he became more comfortable spending time in the rest of the house. You might think that our 35-year age difference left us with little in common, but the community college gave us a shared topic, and we seemed to find a lot of other mutual interests.

He spent a lot of time in the basement shirtless, and seeing his young, strong body like that, I have to admit, he looked physically tempting. The original trepidation I felt to invite him into my home proved prophetic.

On Thursday that first week, I caught him swiping through tinder profiles on his phone.

“You cut back on work hours, and now you’ve got all kinds of time to go chasing girls,” I teased him.

Dion just smiled sheepishly, knowing he’d been called out.

“Look, I know a man has needs, but you’re only in your first week of school,” I warned him. “I’ve seen this story before. A boy gets hung up on some sweet thing, and next thing he knows, he spends all his time chasing after her, and then school gets left behind. Now you’re in college, and you’re supposed to be thinking with your brain and not with that,” I said as I wagged a finger at his crotch. I could swear I saw the bulge in his pants pop out in response.

“I’m sorry. I just -- I guess - before I didn’t have time for a girlfriend,” Dion stammered. “I didn’t have time to think. I just worked and slept and worked and slept. And now I don’t know. I’m sorry. You’re right. I don’t want to mess this up. I’m really thankful for everything you’re doing for me.”

“It’s alright. I know it’s hard,” I reassured him. “I get it. I was once young, too. But I pulled a lot of strings and had to really sweet talk my husband into letting you move in. I bet on you, so please don’t fail me.”

We laughed about it and then sat down for dinner. Dion was starting to become more comfortable, like he was starting to feel at home, and I was happy to see that everything was working out so well.


I got a call from my husband that weekend. There was trouble at another drilling site, and he had to go there to fix it, so he needed to stay another week to see them through. I was used to it by now, but it helped having Dion around, at least. We lived in a safe neighborhood, and I certainly never considered myself a helpless damsel, but the house feels big sometimes, and the emptiness and stillness at nights can fill you with fright and loneliness. Just having someone else there to bring comfort against the things that go bump in the night can make a huge difference.

I had caught Dion on Tinder, but he wasn’t the only one who had desires. It was never good when my husband was out of the house for long periods. I have way too high a sex drive to be left alone for long periods of time, let alone with a virile young man in the house. Dion was constantly shirtless in the house, though I would swear he was just raised that way, and that it was a sign he felt at home. Nevertheless, I found myself staring at his physique several times, and I’d almost swear he caught me admiring him a few times. After a while, I couldn’t help but wonder if it wasn’t just an accident that he was always shirtless in the house, and that maybe he was even showing off to me.

During his second week, I went downstairs to call him up for dinner, and I clearly caught him unaware. I guess I should have called down or announced my presence in some way, but the tv show masked the sound of my foot steps as I descended the stairs and leaned over the railing to the sight of Dion laid out on his bed with his pants pulled down and his cock in his hands. I stopped in my tracks, transfixed by the sight of him jerking off. His cock was dark black, even darker than the rest of him, and it somehow looked dangerous in his hands, almost like a weapon. Then he caught sight of me out of the corner of his eye, and, clearly embarrassed, he panicked and pulled his pants up.

“Dinner’s ready when you are,” I calmly said before I turned around and headed back up the stairs. Maybe I should’ve been embarrassed to be silently watching him in a private moment like that, but all I could think about was the image of his cock as he jerked off.

We shared a quiet meal that night. Dion was clearly embarrassed, so he acted withdrawn, and we endured a painful awkwardness through the main course. As a guidance counselor, I was used to broaching uncomfortable subjects with people, so I sought to clear the air.

“Dion, we need to talk about what happened earlier when I walked in the basement,” I started off.

His face went pale, as if he wished his body could melt and ooze back down into the basement to escape this conversation.

“I’m sorry you - “ His voice trailed off, the words failing him. Having come from a broken home, it’s not surprising he was so defensive and scared.

“It’s alright. I’m not here to lecture you,” I tried to reassure him. Dion sat dumbfounded and unmoving. “Look, I get it. We all have needs.” His eyes grew as big as saucers. “It’s ok. It’s natural. We don’t talk about it a lot, so that makes it seem weird, but it shouldn’t be, right? Anyway, I already dissuaded you from having a girlfriend, so what did I expect? Everyone needs an outlet, right?”

“I don’t know what to say,” Dion said, his face a look of confusion.

“You don’t have to say anything. You don’t have to apologize. Actually, I should apologize. I didn’t knock before I came down.”

“You weren’t offended or anything by what you saw?” he asked in disbelief.

I laughed. “You know, I’ve got some girlfriends that pay decent money to go to a club downtown about once a month to get a peek at what I saw a little bit ago.”

Dion smiled sheepishly, and I was satisfied I had sufficiently set him at ease.

“Now how about some dessert?” I offered as I reached for the apple pie.


The next day Dion and I were watching tv, and we got to talking.

I saw him wag his tongue at some young blonde thing on one of those competition reality tv shows. She was obviously cast to be eye candy.

“Is that the kind of woman you’re into?” I openly asked him.

“Oh, I don’t know. She’s alright,” he answered, probably too shy to talk over those kinds of details.

“I see what you like. Young and skinny. Can’t say I blame you. She’s a beauty,” I agreed.

“She’s pretty. I mean, you ain’t so bad. For an old woman and all.”

“Ouch,” I winced, feigning hurt.

“I didn’t mean it like that. I mean, your husband’s a lucky man.”

“You want to tell him that. He’s been away for almost 4 weeks,” I reminded him.

An obvious sexual tension hung in the air between us. Dion had an awkward shyness about him, and I found it innocently endearing.

“Have you ever had a girlfriend?” I asked, breaking the silence.

“Of course, I have,” he answered defensively, a little too quickly.

“How long ago?”

“Well, it wasn’t anything serious. I mean, I hooked up with some girls at parties back in high school. I’ve been with women, if that’s what you’re asking.”

“It must be lonely,” I told him.

“What do you mean?”

“I mean, growing up, you went into foster care and kind of bounced from family to family. Your mom disappeared. No stable presence in your life. No parental figure. No siblings. Then the next thing you know, you’re working so much, there’s no time for a relationship.”

Dion just sat there in silent agreement before speaking. “It seems you’re lonely, too sometimes. What with your husband away so much and all.”

“It’s ok. We all get lonely sometimes. I can understand why you were looking for someone on tinder. It’s only natural to want some companionship,” I conceded.

“So, what then?”

We sat staring across at each other. I knew my own weaknesses, and I was trying to read his face if he shared similar thoughts. The last thing I wanted to do was embarrass myself, but I bit my lip and then decided to plow ahead.

“Can I be honest with you?” I asked.

“What you think we’ve been doing?” he asked incredulously.

“Do you find me attractive?” There, I’d put myself out there.

He hesitated, and I rushed to fill the silence. “I mean, I know I’m a lot older than any of the women, really girls, that you’re really interested in. But if you’re lonely - and I’m lonely - well, I want you to do well in school. I could -- “ I swallowed hard, trying to choose my words carefully, “We could be like friends with benefits.”

My proposal hung awkwardly in the air as Dion sat with a stunned look on his face. I saw him look me over, probably eyeing me sexually for the first time.

“You can say no,” I continued, again trying to fill the silence. “I’m not trying to force myself on you, I just thought maybe it could be ... mutually beneficial.”

“So, what then?” Dion croaked, finally finding his voice, his face still in disbelief.

Now it was my turn to sheepishly grin. “Well, I have a pretty high sex drive, to be honest. You could probably fuck me any time you want. I mean, I don’t do anal, so don’t go there. I have limits, but I enjoy taking care of a man, and I don’t mind a man taking charge of me.”

 
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