Her Daughter’s Friends Pt. 01

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Disclaimer: All characters are 18 or older.


Deanne Taylor was 43 years old and tall, about 5″11″ with dirty blonde hair. She was no skinny model, but she carried her weight proportionally on her large frame. She was getting annoyed at the extra 5 pounds a year she seemed to gain, but regular work outs meant she was in decent shape, though she was now up to around 180 pounds.

She had her daughter, Alana, 18 years ago while in a long-term relationship, but she broke up with Alana’s father before she was born. The father moved out of state, and Deanne was left to raise her daughter on her own. Deanne was a development engineer for a defense contractor, though, and that provided a good life for Alana and herself.

It was Fall Break, and Alana was hanging out with her old high school friends in the finished basement. Alana and her friends all lived in the same neighborhood and grew up together from elementary school to high school, growing closer as the years wore on. The girls in the group all became part of the popular crowd, all of them becoming cheerleaders in high school. The one outlier in the group was Leonard, who lived two houses down, and the only male in the group. He was shorter and didn’t fit in looks-wise with the rest of the group, but he had hung out with them since elementary school, and he kind of always stuck around. As the girls grew into young women, Leonard was too short, had too much acne, and was too socially awkward to appeal to any of the girls, but he proved his worth by helping them on homework and studying for tests. The girls started dating, and some boyfriends briefly entered the circle, but the girls and Leonard were the constants.

After graduation, the group all followed separate paths to different colleges. Alana went to Frostburg State, and the rest of the group was scattered at other universities across the mid-Atlantic. After the challenge of starting over at a new school and having to make new friends, they all jumped at the first chance to catch up with old friends during Fall Break.

“Mom, can we order some pizzas?” a voice called from the basement.

Deanne sighed silently. She had 8 college aged kids in her basement, and it was almost dinner time. She went online and placed an order for delivery.

“Mom, did you hear us?” Alana asked, as her head popped out from the basement door. “We’re starving down here.”

“Just placed the order, honey. It should be here in a half hour or so,” Deanne replied.

Alana ran back down while Deanne returned to cleaning upstairs. She marveled at how grown up her daughter was and wondered where all the years went. Alana was almost a carbon copy of her mother at 18 years old, a statuesque beauty, 5’9″, and with smooth legs on the skinny frame that Deanne missed having.

Soon the pizzas arrived, and Deanne called the kids to come up from the basement to eat. Deanne was glad to have the kids over at her house. After Alana left for college, the house felt empty, and Deanne loved seeing the house full of noise and laughter again. She sat to the side, listening to their chatter as they tore into the pizza. Leonard sat off to the side, attentive but not directly involved in the banter.

The kids wolfed the food down, and then they scurried back downstairs. Deanne took a quick peek to the finished basement. The kids had resumed playing a board game, although she also saw video game controllers scattered about and Netflix on the TV. Looks like they were having fun, doing whatever caught their fancy, she reasoned.

Deanne went back upstairs and retired early to bed. She woke up the next morning and took a quick shower before changing into some grey sweat clothes. Then she went down to the basement to survey the damage. She loved her daughter but cleaning up after herself was not a strength. The kids went home at some point after Deanne went to bed, and she proceeded to clean up the aftermath.

When Deanne came back upstairs, she saw Alana groggily coming down.

“How late did you guys last?” Deanne asked.

Alana yawned sleepily before replying. “Everyone left about 2 AM.”

Deanne looked at the clock in confusion. “It’s only 7 AM. Why didn’t you sleep in?”

“We’re going to spend the day hiking up Old Rag, and we want to get an early start so we can be back for dinner,” her daughter replied.

“When are you leaving then?”

“Right after I finish this muffin,” Alana answered.

True to her word, Alana, quickly inhaled the muffin and then grabbed a small backpack for some water and snacks before heading out to meet her friends.

Deanne returned to cleaning up around the house after Alana left. An hour later, the doorbell rang, and she answered the door. Leonard stood at the doorstep.

“Is Alana here?” he asked.

“No, I’m sorry. She left with the girls. She said they were going hiking.” Deanne realized immediately after she spoke that Leonard must not have been included. casino siteleri She could almost visibly see his hear sink.

“I guess I wasn’t invited,” Leonard replied, looking downtrodden.

“Come in, come in,” Deanne beckoned, feeling sympathetic. “Why don’t you come in and get some breakfast?”

Leonard took a deep breath and then took up her offer. He took a seat at the breakfast nook, his shoulders still slumped.

“We have some muffins and bagels. Or I could fry you up some eggs and bacon, if you’d like,” Deanne cheerfully offered.

“It’s alright,” he replied sullenly. “I’ll just have a muffin.” Leonard half-heartedly grabbed one, but he made no attempt to actually eat.”

“What’s bothering you? I’m sorry they left you behind. Maybe — ” Deanne started.

“How long ago did they leave?” Leonard interrupted.

“About an hour,” she answered.

Leonard shook his head. “It’s pointless. It’s no use going now. I don’t want them to sit around for an hour just waiting for me to catch up.”

“It’s ok, I’m sure they just forgot to invite you,” Deanne tried to reassure him.

“Exactly. They forgot. I’m an afterthought,” Leonard said in exasperation.

“No, not like that.”

“It’s ok, Miss Taylor. I’m used to it by now. I get it. I was only useful to them in high school. I helped them keep up their grades, studied with them, and helped with their homework. But I was never good enough to be anything more than that. And now that we’re all in different schools, taking different classes, now they have no use for me.”

Deanne bit her lip. She knew there was a lot of truth to Leonard’s rant. He was smaller, probably around 5’4″, and shorter than all the girls in the group. He tagged along on a lot of their activities, but that was just it, he tagged along. He always came off like the runt of the group. A hanger on. During high school, as his dark hair grew out and he started wearing glasses, he was teased for bearing a more than passing resemblance to his namesake on the Big Bang Theory tv show.

“I’m sure it’s just an honest mistake,” Deanne tried to console him.

“It’s not. They don’t want me around. I probably just need to move on. I just wish — ” Leonard’s voice trailed off.

“Wish what?”

Leonard looked at Deanne for a long moment before answering. “It just hurts. I know I’m not good looking. Or athletic. Or smooth talking. But I watch them all go out with their string of boyfriends, and I wish… I wish… I just wish they’d look at me just once the way they look at those other guys.”

“I’m sorry.”

“It’s not your fault. You know I actually went on a date with a girl last month. My first one ever. I think she maybe even liked me. But then she wanted to do more, and I… I… it’s like I didn’t know how to do anything. She got frustrated and cut the night short.” Leonard shook his head in frustration. “I’m just tired of being lonely.”

“Leonard,” Deanne tried to comfort him. “You’re a good guy. Lots of girls would be lucky to have you. You just need to find the right girl who appreciates you.”

“That date I went on,” Leonard continued, “that girl, she laughed at me. I think she was interested in me, and she wanted to… to play, but I didn’t know what I was doing, and she just gave up and walked out.”

“It’s not your fault.”

“Yes, it was,” Leonard almost sobbed. “No girl will want me. I don’t even know what I’m doing. I was trying to reach for stuff, I don’t even know what I was reaching for. It was so embarrassing.”

“I’m sure it wasn’t as bad as you think.” Deanne placed a hand on Leonard, trying to reassure him.

“This is embarrassing to talk about with you, but I had a hand in her pants,” Leonard continued confessing. “I tried to touch her down below, but nothing seemed to do anything for her. I begged her to let me try again, and she let me, except then evidently I put my fingers in the wrong hole, and that’s when she just up and left.”

Deanne stifled a laugh. “I’m sorry.”

“Well, it’s not like I have access to the female anatomy to figure it all out. I told you, I don’t know what I’m doing down there.”

“Didn’t you take anatomy class?” Deanne asked.

“I’m not trying to give birth. They didn’t cover the parts that help with what I was trying to do.” Leonard wiped tears from his eyes.

Deanne took a deep breath. She saw the clear frustration on Leonard’s face and felt sorry for him. She wanted to help him, and she had an idea but was conflicted. After a few seconds, she decided her pity outweighed her trepidation.

“Alright. I’ll help you, but you can’t tell anyone,” Deanne final blurted out.

“What do you mean help me?” Leonard asked.

“I mean it. You can’t tell anyone,” she reiterated.

“Ok. I won’t tell.”

“You promise?”

“I promise,” he vowed.

“Don’t make me regret this,” she emphasized. “Now follow me.”

Deanne led Leonard into her bedroom.

“Sit,” güvenilir casino she ordered, pointing to the foot of the bed while she sat at the head.

“I’ll give you that anatomy lesson, ok, so the next time you’re with a girl,” Deanne winked, “maybe you’ll know you’re way around.”

Leonard’s eyes widened in surprised confusion, unsure if he heard Alana’s mom correctly. Deanne saw his bewilderment.

“You heard me. Now I ain’t no model, and I’ve been thru childbirth. Hell, it’s been a while since I even did any trimming down there. But I can promise you all women got the same parts. Are you in?” Deanne glared at Leonard, waiting for an answer.

Still looking shocked, he slowly nodded his head.

With that, Deanne slid down her grey sweatpants, revealing her plain cotton panties. Well, it’s the moment of truth, thought Deanne. She slid down her panties, revealing her vagina to Leonard. Deanne sat with her back straight against the headboard and spread her legs in front of Leonard to give him an unobstructed view of her exposed private parts.

Leonard’s eyes bulged, and his mouth hung agape. Deanne couldn’t help but think he looked pathetic, but she hoped maybe he’d actually learn something from this tutorial. She looked down and saw her mound on full display, her old pussy with white hairs starting to show and in need of a trim. She felt secure there was nothing remotely sexy about the goods she was displaying.

“This is a vagina,” she started to say as Leonard’s eyes remained fixed on her private parts. “You need to know your way around a woman’s privates if you want to bring her pleasure. Now this outside part is the vulva. And then these flaps are like lips.”

Deanne’s fingers reached down and spread her lips, revealing her pink flesh. “The lips that I just spread, those are called labia. And inside here, toward the top, under this little flesh, that’s my clitoris, or clit. And then here below the clit, there’s an opening. That’s my vagina. If you make love to a woman, that’s where your penis goes.”

“So, if you masturbate, you finger yourself right there?” Leonard asked, finally, finding his voice.

Deanne blushed before responding. “A lot of women masturbate that way. I do, too, sometimes, but, personally, I like to stimulate my clit.”

“Can I get a closer look?” Leonard asked.

“I suppose,” Deanne conceded.

Leonard came forward, carefully studying her sex organ.

“That’s the clitoris there,” Leonard pointed.

“Well, that’s a hood. If you lift that flap, my clit is lying behind it.”

Leonard’s finger came forward to lift her clit hood, revealing her clitoris.

“So that’s your favorite spot?” he asked.

“Yes, it is,” she replied dryly.

“Can I touch it?”

Deanne was unsure, but she figured she already let things go this far. “Just a touch,” she replied.

Leonard’s finger rubbed it, and Deanne tried to hide her body’s reaction to his touch. She drew a quick breath and then bit her lip. Leonard continued rubbing.

“So, if a man goes down on a woman, he should lick the clitoris?”

“That’s my preference,” Deanne confessed.

“What does it taste like?”

“I’m not sure. I’ve never gone down on a woman,” Deanne said, laughing.

“Can I lick it?” Leonard inquired.

“I’m not sure that’s a good idea.” Deanne was starting to become a little uncomfortable.

“Just one lick,” he implored.

Deanne didn’t reply, but Leonard reached his face forward and kissed her clit gently. Then he stuck his tongue out and licked her.

Deanne felt herself becoming aroused.

“Is that right?” he asked innocently.

“Maybe a little more pressure and a little longer,” Deanne answered. She hadn’t intended for him to get actual practice, but she also wanted Leonard to be confident next time he was with a woman.

“More like this then?” And he continues licking her clit.

Deanne’s body responded, tingly sensations of pleasure shooting through her body.

“So, your vagina is through here?” Leonard asked as he briefly paused licking her clit.

Before she could respond, he slipped a finger in her hole.

“What is all this wetness?” Leonard questioned.

“That happens when a woman becomes aroused,” Deanne responded in embarrassment.

“Are you getting turned on Miss Taylor?”

“Maybe just a little,” Deanne admitted.

And then Leonard inserted a second finger into her vagina. And then a third.

“How large is this hole?” he asked.

“I mean, Alana passed through there when she was born,” Deanne pointed out, thinking that might dissuade Leonard. Instead, he inserted a 4th finger. And then the next thing she knew, his entire hand was inside her. She felt his hand open inside her, his fingers exploring inside her vaginal cavity.

Deanne’s defenses were quickly crumbling.

“Am I doing this right?” Leonard asked, as he continued to lap away at her clitoris. canlı casino The stimulation on her clit combined with the fist inserted into her vagina made Deanne quickly become highly aroused. She sank down flat onto the bed, submitting to the oral pleasures Leonard was giving her. As her breathing grew heavier, she felt his other hand reach under her sweatshirt and quickly find her braless tits, fondling her C cup breasts.

“Leonard, that is probably enough,” Deanne tried to protest.

“I think I’m starting to get the hang of this,” he replied enthusiastically.

Deanne felt an orgasm quickly forming. She spread her legs wider, implicitly urging Leonard to continue pleasuring her. And pleasure her he did, relentlessly working her clitoris with his tongue while he fisted her with one hand and teased her nipples with his other. She raised up her sweatshirt to expose her titties as the sensations inside her quickly intensified into an orgasm.

She tried to suppress her climax, but her body betrayed her, and she shook as the surges rippled through, and her own voice couldn’t contain her passion. She felt Leonard pull back from her and opened her eyes to the sight of Leonard positioned in front of her, his cock now exposed and rock hard.

Deanne’s eyes widened. Her initial reaction was trepidation, however, her own arousal swiftly consumed her again as she felt Leonard’s cock enter her pussy.

“It slides in so easily,” he observed. “All that wetness down there, it’s amazing how different it is compared to before we started.”

Deanne closed her eyes again and submitted to Leonard as he fucked her. Leonard was short, but his cock was still at least 6 inches, and she was afraid to admit how easily she was already feeling a second orgasm forming.

Leonard grabbed her ankles and pushed her legs back until her feet were almost at her ears. Deanne opened her eyes again and looked down at the sight of Leonard’s 18-year-old cock fucking her. She saw him slide in and out. She looked up and saw his face focused on hers, studying her reaction to getting fucked. Watching her every moan and response as her sexual stimulation increased. Leonard took in the sight of her C cup titties bouncing from side to side as he pounded into her.

Deanne abandoned all pretenses and screamed uncontrollably, giving in to her carnal desires. As her second orgasm overtook her body, she saw Leonard smile mischievously. As her own orgasm subsided, she felt Leonard’s body tighten on top of her, and he grunted loudly as his orgasm shot a load of cum deep inside her.

“Oh God, what did you do?” Deanne screamed.

“I’m sorry. I think I got a little carried away,” Leonard answered breathlessly.

Leonard pulled out of her.

“I do appreciate the lesson you gave, Miss Taylor,” Leonard said earnestly. “That was amazing.”

Deanne instinctively covered up her body with the bedsheets.

“That’s alright. We took that a little farther than I intended,” Deanne admitted between breaths. “But you seemed to get the hang of it pretty quickly. Next time you need to remember to practice safe sex.” Deanne winced after realizing she hinted there might be a next time. “We can’t speak of this. To anyone. Do you understand me?”

“Don’t worry, it’s our little secret. I really appreciate you doing this for me.” Leonard smiled and then turned around to get dressed.

A few minutes later he left the house.

“Thanks again, Miss Taylor,” Leonard said as he left. “I’m sure next time I have a date, I’ll actually know what to do. This is probably the most fun lesson I’ve ever had.”

“Just go home, Leonard,” Deanne said, urging him out the door. Deanne was just thankful she wasn’t ovulating, so she probably wasn’t pregnant, but she was disappointed and embarrassed she let things with Leonard get way out of hand.


Alana returned from her hiking excursion that evening, and Deanne and her daughter were sitting around the dining table, just talking while eating dinner.

“Leonard stopped by earlier. I think he was sad you guys didn’t invite him to go hiking,” Deanne informed her daughter.

“Oh, he was invited. He said he’d rather sleep in.”

Deanne was confused. “He was? I thought — anyway, it seems like maybe he’s not as close with everyone else in the gang like he was before. It seemed like he wasn’t a part of your guys conversations or playing games — he was more just off on his own last night.”

Alana nodded her head in agreement. “Yeah, I noticed it, too. I kind of feel sorry for him. Actually, I’ll tell you a little a secret, mom. Don’t be mad, but last summer, he was really down. I mean, he has a hard time with girls, being short, socially awkward, and not so great looking. Anyway, I don’t know, but I guess I took pity on him. I took his virginity. I kind of let him practice how to do oral sex on me, and we ended up having sex. I’m not really proud of it, but I think it really helped his confidence, so I’m glad I did it.”

Deanne just stared open mouthed at her daughter, not wanting to admit she had evidently fallen for the same ploy.

“Mom? Mom?” Alana asked imploringly as Deanne’s head fell into her hands in regret and distress.

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