“Where are you off to on a Friday night, Jason?” Serena asked her son.
“You know. Out. There’s a new club where the girls are supposed to be really hot!” he replied.
“Of course!” she laughed.
Serena was not your typical mom. Divorced for over fifteen years, she had no shortage of lovers during that time but was having a dry spell at the moment. Whenever Jason was going out carousing, she thought of her days as a young promiscuous girl when cute college guys like Jason were familiar targets for her feminine charms.
She rarely missed, but Jason was the result of being with one of those guys. His father gave it a try when she refused an abortion, but after a few years, he decided he wasn’t ready to be a dad or a husband. The divorce was amicable, and she didn’t waste any time returning to her old ways. Most women lamented being a single parent and how it scared even the best prospects off, but Serena saw it as a benefit, not wanting to be tied down again.
“Who’s going with you?” she asked.
“Dave, Pete, and Jorge,” he replied.
“Not Bobby?”
“Mom!” he said in exasperation, having dealt with this subject before.
“Jason, he needs your help! He’ll never get a girl if someone doesn’t show him how!”
“His mother won’t let him go. She has such a tight leash on him and has beaten it into his head that women don’t like sex and that all guys are just trying to get in their pants!”
“I can’t believe she’d tell him that!”
“Believe it! He’d told me. His parents fought like crazy before his dad left, and ever since then, she’s blamed his father for everything and convinced Bobby he should be a quiet and respectful guy with girls. He does attract them, but they’re pretty quickly turned off by what looks to them like a lack of interest.”
“He’s a good-looking guy! Surely they don’t give up on him that easily?”
“It doesn’t take long. But, you know, I think he’s got a bit of a crush on you!”
“Really?” she replied, a little aroused by the thought.
“Yeah. About a week ago, I thought he was gonna have a heart attack when you bent over in the kitchen, and he saw your panties.”
“I wasn’t showing off, Jason!” she said, knowing most of his friends considered her the ‘Hot Mom,’ and on more than one occasion, she’d gotten off on giving them a glimpse of her tits or ass. Their reactions fueled many a successful bout of self-love in her bed.
“I know. That time was accidental,” Jason answered, implying other occasions weren’t. “It’s just that I had been telling him that when a girl lets you see her panties, it means she wants your hand or something else in them!”
“What did he do?”
“He thought you were coming on to him, so what did you expect him to do? He left. In a hurry!” he finished laughing.
“So you’re leaving Bobby at home tonight?” she asked with a different idea in mind.
“Yeah. His mom’s out playing bridge or something,” he said with disgust. “Gotta go! Guys were expecting me ten minutes ago!”
“Have fun!”
“I will!” he replied, knowing she’d be quite happy with him getting some pussy tonight.
Serena poured herself a glass of wine and sat down with Bobby still on her mind. If he’d gone away to college, that environment might have opened him up, but as it was, the poor boy would end up living with his bitter mother his whole life if someone didn’t take him in hand and show him the other side. Jason and Bobby had grown up together, living only a few doors apart, and she’d always had a soft spot for the overly shy and polite boy.
“Hey Jason!” Bobby answered the phone with the caller ID of his best friend’s home number.
“Hello, Bobby!” Serena replied.
“Oh! Hello, Mrs. Harris! How are you?” he said cordially but startled by a female voice.
“I’m fine. How are you?”
“I’m okay. My mom’s not available at the moment,” he replied cautiously, as his mother had taught him not to reveal her absence.
“I’m not looking for your mom. I called for you.”
“Oh! What’s wrong? Do you need some help with something?” he asked, always offering to help Jason’s mom. He liked Mrs. Harris and looked forward to helping her whenever possible. He’d get very embarrassed when he’d see down her blouse or up her skirt, but it also excited him in a way his mom wouldn’t like.
“As a matter of fact, I do. Do you remember all those boxes you helped me pull down from the shelves in the garage? Well, they need to go back up. I can climb the ladder, but I’d prefer having someone hold the ladder while I do,” she told him, knowing he’d enjoyed looking up her skirt that time.
“Oh! Yes! I can come right now if you like,” he said, already getting excited about the prospect.
“That’s great! The garage will be open.”
She could hear the excitement in his voice and went to change her panties to something a little more revealing. While she was at it, she decided to put on that bright red blouse that had her tits squeezing out the top and an even shorter skirt to give him a clearer view.
By the time she got to the garage, Bobby was standing outside as the door rose.
“Hi, Mrs. Harris!” he greeted her in his loose slacks and dull T-shirt.
“Oh my! You were fast! Will you get the ladder?” she said as she walked over to the stack of boxes she really hadn’t done anything with yet. He put the ladder in place, and she climbed up a couple of steps. “Hand me the first one, Bobby?”
“Here you go,” he said, handing her the first box.
She took another two steps up the ladder to be sure her skirt was well above eye level. She glanced down, smiling at his reaction to seeing the narrow strip of fabric that covered her pussy and disappeared between her ass cheeks.
Bobby was excited by what he saw. His mother’s admonitions nagged at him, but he couldn’t resist looking. He also thought briefly about Jason telling him what it meant when a girl lets you see her panties, but those thoughts vanished when she asked for the next box.
He handed it up, but she couldn’t quite reach it, so she had him take the first step up the ladder, positioning herself so his head would be practically up her skirt when he did. She smiled when she saw him breathing heavily as he stepped back down.
For the last box, she took another step up, and with his head nearly up her skirt again, she feigned being unsteady and asked him to hold her legs. The poor boy was so rattled she almost regretted putting him through it; almost.
“Bobby! Are you okay?” she asked when she climbed down the ladder and saw his flushed face. “Come inside for a drink!” she added when he didn’t respond.
In the kitchen, she refilled her wine glass after pouring him his drink of choice, a Coke.
“Let’s have a seat,” she suggested, leading him into the living room to sit side by side on the sofa. “Are you okay now?”
“Yes, Mrs. Harris,” he replied meekly.
“What was wrong? You looked like you’d seen a ghost,” she remarked. She’d also noticed that despite his baggy pants, there was a bulge that suggested a larger-than-expected cock.
“It’s nothing. It’s just … you’re always so nice to me, and you’re … you’re so pretty!”
“Thank you, Bobby! You’re a very handsome boy, you know!” she said, putting her hand on his thigh.
“That’s what my mom says, but …”
“But?”
“But she says I shouldn’t take advantage of girls just because they like how I look.”
“Are there many girls who like how you look?”
“There have been a … a few. More than I expected, but I’m kinda shy. You know, so they move on to the other guys,” he said, looking down sheepishly.
“Why do you think they do that?”
“My mom says that girls don’t like it when boys are always trying to … to, you know, touch them and have sex, but they sure seem to like it when they go to the other guys. I’ve seen how they react when guys put their hands on their bottoms and even … even between their legs. They certainly don’t run away like they do with me!”
“Your mother’s partially right. There are some girls who don’t like that kind of attention, don’t want to be touched like that, and feel they should be married before they have sex, but not most girls, Bobby,” she said, shifting on the couch to get her skirt to ride up and let him see her panties again.
“Mrs. Harris!” he said with alarm.
“What’s wrong?”
“Um. Jason told me that …”
“I know what Jason told you, and he’s right!” she said as she took his right hand and, holding it with both of hers, placed it right on her pussy, moving it in circles on the tiny triangle of fabric that covered it. “Most girls like to have their pussy touched like this,” she said softly.
“Oh my God, Mrs. Harris! Are you sure you want …”
“Yes, Bobby. Very sure! But Jason told you they’d like to have your hand in their panties, didn’t he?” she said as she pulled the gusset aside, and she could feel his hand move, wanting to touch it again. “That’s it! Mmm, feel how wet and slippery it is?” He nodded, unable to get a word out. “That tells you I really like what you’re doing!”
He stared with fascination at what the woman he’d long had a crush on was letting him do. His mother’s warnings tried to intrude, but he fought them back, if only for this time.
“Here. Wait a minute,” she said, pulling his hand away and noticing the expression of a boy having his toy taken away. Reaching for the waist of her tiny panties, she pulled them down and let them fall once past her knees. “Oh, that’s better. Now use just your finger like this!” she instructed, taking his middle finger and pushing it into her moist slit.
“Wow! You’re really wet, Mrs. Harris!” he said as he slid his finger up and down, enjoying the silky smoothness of her delicate folds.
“Mmm, that’s good!” she said, unusually aroused despite his amateur efforts. There was something about this innocent boy and his reactions to her teaching. “Now, right at the bottom. Feel the hole? Yeah, right there. Put your finger in! Ooo! Now, in and out. Yeah! That’s it! You’re fucking me with your finger, Bobby!” she said to his smiling face.
He was dumbfounded that she let him touch her like this. He’d never felt himself so hard and thought briefly about masturbating, but he wanted the lesson to continue.
“Okay, put another finger in. Yeah, two fingers. Ohh! Yeah, that’s it! Faster! Mmm! Ooo, now you’re gonna find my clit! This is important! It’s the most sensitive thing down there, and girls will love having you rub it. Leave your fingers in my cunt …”
‘Oh my God, I’m fingering her cunt!’ he thought at the mention of the vulgar word.
“… and look here,” she said, using her fingers to pull the hood back and reveal her stiff little nub. “Rub it with your thumb. Oh yeah! Ooo, now keep rubbing my clit and finger-fuck me at the same time! Oh yeah! Oh yeah! Don’t stop! Faster! Don’t … don’t … ohhhh fuck!” she cried continuously until she came.
“Oh my God, Mrs. Harris! Did you just have an orgasm!?” he gasped as he felt her pussy getting much wetter. She smiled as she nodded, her heavy breathing causing her chest to rise, pushing her tits up within the confines of her tight blouse. Brimming with pride, he turned to see the pleasure in her face.
“You did good, Bobby! See? And girls will like it when you do that to them!”
“Wow, I never knew I could do so much with just my hand!”
“You understand that you still have to have their permission, right?” she said to the eager boy.
“Yeah, I do. I think this one girl, Mandy, wanted me to do that to her. She kept holding my hand against her belly. Do you think she did?”
“Probably, but you take it slow at first and make sure she wants you to, okay? Are you ready for another lesson?” she said, placing her hand on the bulge in his slacks.
“Oh God! Yes, please!” he said, already reacting to her touch.
“Some girls will tell you they want you by doing this,” she said, stroking the shaft she could feel uncomfortably twisted in his briefs. “If it’s your girlfriend, she might open your pants and slip her hand inside, like this,” she said in a sensual tone with her hand in his pants, stroking over his underwear, “but it’s hard for a guy to enjoy it without at least pulling your pants down.”
Bobby’s eyes were wide open as she slid off the sofa to kneel between his legs and reach for the waist of his pants. He lifted his hips to let her pull them off with a mixture of excitement and embarrassment, as only his mother had ever seen down there, and even she hadn’t in years.
“Bobby! Aren’t you a revelation!”
“Um, what does that mean?”
“It means your cock is huge!”
“Oh! Um, it is? Oh, God!” he stammered as she took him in both hands with the tip still protruding out the top.
“It feels good, doesn’t it?” she said as she gently stroked the length of the shaft with one hand while the other teased the tip.
“Oh my God! I’ve never … no one’s ever! Ohhh!” he moaned when she cradled his sac while stroking his shaft faster.
She’d considered taking him in her mouth but thought he might explode, and not in a good way. Maybe she would teach him about oral sex another time because it would probably blow his mind right now.
“Mrs. Harris!! I’m gonna …”
“C’mon, Bobby! Cum for me!” she said as she reached for her panties and wrapped the tip in the still-damp fabric. “Hold on as long as you can! Okay, now let go!” she said when she could hear the strain in his voice.
“Oh! Ohh! Ohhhhmmmm!” he cried out as his body shook, and she could feel three pulses of his seed hit her panties.
“Good boy, Bobby! Did that feel good?” She waited to ask when his eyes finally opened again.
“Holy shit! That was amazing! Girls will do that when they want me to finger them?”
“Not exactly. They may just rub your crotch a bit if they think you’re not getting the message. You have to pay attention to what they say and do, and be gentle as you feel your way through. She may push you away if you come on too strong, but she may let you if you’re kind and gentle. Or she may just ask you to stop.”
“Wow! It seems so complicated, but you make it sound easy!”
“Would you like one more lesson?” she said, climbing on his lap with his legs between hers. She took hold of his flaccid cock, still larger than most guys she’d had, and gently massaged it between her legs, paying particular attention to the tip. He just nodded. “Would you like to fuck me, Bobby?”
“Oh my God! Really? I mean, yes!” he said.
“Take my blouse off!”
He clumsily found the bottom hem of her blouse and pulled it up at the sides, the front caught on her tits. She used her hand to pull the front over them and let him continue to pull it up over her head. Again, his eyes revealed the utter shock of such a display.
“Wow! They’re so … so big!”
“Touch them!” she laughed, “Go ahead. Squeeze them. Kiss them. Girls really like it when you lick their nipples! That’s it! No, gently! Just the tip of your tongue!” she said, all the while stroking his cock back to life. She hadn’t had such a large one in a long time and couldn’t wait to feel his.
She inched forward so his cock was between her splayed lips. She pushed it against her slit and rocked her hips, stroking several inches of him with her pussy. Distracted by her tits, he didn’t feel it until she called attention to it.
“Mmm, feel your cock in my slit, Bobby? Ooo, it feels so good, so hard! Are you ready to fuck me?” she whispered.
“Uh-huh!” he said, still in shock at the offer.
Serena rose up and had to come off one knee to get it underneath her. She teased the tip running it through her slit to his gasping approval. With the head at the opening of her tunnel, she slowly impaled herself on his XL cock, rising back up a few times before descending further. A shuddering breath accompanied the final push, and she couldn’t remember when she felt so full.
“Oh God, Mrs. Harris! You feel so good inside!” he said as she squirmed in his lap, still getting comfortable with so much meat in her cunt.
Ready to start her ride, she put her hands on his shoulders, told him to keep his hands on her tits, rose as high as she could, and gasped on the way down like he was pushing the oxygen out of her lungs. A few more lifts, and she started riding smoothly and accelerating. Feeling the onrush of a climax coming, she bounced in his lap, crying, “Fuck me!” until the implosion came, her body quaking and shaking.
“Are you okay, Mrs. Harris?” he asked, stunned by her trembling body.
“Yes, I just came! Think you can make me cum again?” she asked, rising up on her knees.
“I don’t know! Can I?” he asked, mystified.
“You do it now! Push your cock into my pussy! That’s it! Slowly at first, but gradually faster. Oh fuck!” she cried as he now eclipsed her pace from minutes before.
“Like this?” he asked, his breathing getting ragged.
“Yeah! Yeah! Like that! Oh! Ohh!” she gasped, rendered speechless as with the energy of youth, he was pounding her pussy like a jackhammer.
She was so close, and he was, too, holding on to her tits with a death grip. She looked down at his blurred cock, unable to tell whether it was going in or coming out, but it didn’t matter as every nerve ending in her crotch was firing, and seconds later, they both came moments apart.
“Holy fuck, Bobby!” she cried when she could speak, laying against his chest as he lay back against the sofa cushion.
“I’m sorry, Mrs. Harris! I should have pulled out, shouldn’t I? Are you going to get pregnant?” he said; his naivete would be cute if he weren’t so clueless.
“No,” she laughed in short gasps, “I can’t get pregnant, but that’s a good thought. You should keep a condom handy just in case.”
“Do you think I can get a girl to do that with me?”
She wanted to say that once the size of his cock got around, he’d have to beat them off with a stick, but she didn’t want him to get a swelled head, so she answered honestly but gently.
“Remember what I said about paying attention. If it seems like she’s coming on to you, gently find your way. You can tell a lot about what she wants from a kiss and then let your hands wander a bit if she seems to like it. Maybe try with someone you already think is interested. What was that girl? Mandy?”
“Yeah, I think she might be the one to try. She’s really cute and very nice, too.”
It didn’t take long to dress as Bobby just needed to pull his pants up, and Serena put her blouse and panties back on. She laughed when she remembered a similar situation with a boy on a sofa in her exploring years, but even then, she was the one leading.
“Thank you, Mrs. Harris! Really! I was beginning to feel left out with the guys, but I was always worried about what my mom would say.”
“Your mother’s not entirely wrong. There are girls who think like she says, but not that many. That doesn’t mean all girls want to do what we just did, but when you find someone you care about, it oughta come together naturally now that you know a little more.”
They walked together to the door, but she had one more word of caution before she opened it.
“You know you can’t tell anyone about what we did, don’t you? Especially your mom and Jason, okay?”
“Yes,” he said, leaning in unexpectedly to kiss her on the lips. If it had been anyone else but him kissing her like that, they’d be heading for the bedroom. “I understand.”
‘He’ll do just fine,’ she thought as she watched him walk down the path to the street.
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Wish I had a neighbor like Serena! I hope you enjoyed this GIF inspired story and will offer ‘Likes,’ ‘Favorites,’ and comments if you did and … THANKS FOR READING!
