Ed heard drunken laughter coming from downstairs, and knew his mother was home. Their neighbor – one of her best friends – had taken a job in another city, and would be leaving in a couple of days. His mom had obviously tied one on at the going away party.

As much as his mother was going to miss her, he wondered if he wasn’t going to miss her more. He had caught more than a few glimpses of her in various states of undress through his bedroom window. While she was his mother’s age, and had a sort of librarian look, seeing any skin was a rarity for an unpopular guy like him.

He’d seen a lot of skin the last couple of months. He half wondered if she wasn’t purposely stepping in front of the window in nothing but a pair of panties, considering how frequently it was happening. She didn’t have huge tits, and they were pendulous, but they were real.

Ms. Keller had dominated his spank bank since the first time he saw her naked tits. His most vivid fantasy was of her stepping in front of that window to let him see her, and then playing with herself, while imagining him jerking off. It was just close enough to plausible to really make him come hard.

His thoughts drifting that direction from the sound of her voice had his dick throbbing in no time.

Indistinct conversation and a lot of laughter drifted up the stairs for the next hour or so, and then things quieted down a little. Not long after, he heard them coming up the stairs. There was a bit of stumbling, a little more laughter, and then the sound faded when his mother’s bedroom door closed.

Ed glanced out his window, wondering if Ms. Keller would put on a show that night. Maybe she’d even come in front of the window completely naked, if she was drunk. That morphed into a fantasy of her playing with herself in front of the window, making his dick throb hard.

He sat fantasizing and half listening for the sound of her going down the stairs, anxious to let off the pressure that was building.

Finally, he did hear the bedroom door open, and his anticipation spiked. He heard the footsteps approaching, but when he should have heard the creak of the stairs, those footsteps continued to grow louder.

Ed quickly yanked the covers over the tent in his boxers, just as a light knock sounded on the door. Before he could say anything, the doorknob turned, and the door opened.

He stared in confusion – and not a small amount of embarrassment, considering what he’d been thinking about – when Ms. Keller stuck her head in the room.

“Mind if I come in?” she asked in a voice just above a whisper.

“Uhh...” He shrugged and said, “Okay.”

She came into the room and closed the door behind her. “Your Mom is passed out. She had a little too much to drink at the party. You do understand this was a special occasion, and not something she does very often, right?”

“Yeah.”

“I probably had a few too many too,” she said as she took another couple of steps, and sat down on the foot of the bed.

She was wearing a skirt, and while it wasn’t all that short, the act of sitting down had caused it to ride up a little, exposing more of her legs. His eyes snapped to them of their own accord. Ed caught himself and looked back up, but it was too late. Her half grin and raised eyebrows announced that he was caught.

“It’s okay,” she whispered and reached out to pat his leg. “Your mom was a little worried that you weren’t interested in girls, but I told her that I’d caught you looking at me a few times, so she shouldn’t worry about that.”

That escalated quickly. His face burned, and he looked down, unable to meet her gaze.

“No need to be embarrassed. It’s natural at your age, and frankly a little flattering to an old girl like me. Seen anything interesting through the window lately?”

Though he still couldn’t look at her, Ed’s eyes widened and his mouth opened. She knew he’d been looking at her.

A little chuckle escaped her and she said, “You did. I thought so, but I wasn’t sure. I honestly needed that confidence boost.”

He was sitting there embarrassed beyond belief and fidgeting, having no idea what to say or think.

“I’m moving the day after tomorrow, you know,” she said, and then waited a couple of seconds. “Would you like a closer look before I go?”

That made him look up. Was she serious?

She reached up to the top button of her blouse, popped it open, and then raised her eyebrows. When all he could do was stare in confused shock, she popped open a second, reached for the third, and asked, “Yes?”

Some primal thing deep inside him broke free and caused him to nod his head, even though most of his brain was completely frozen.

She smiled, giggled, and proceeded to pop open that next button. On the one that followed, he could see her bra. The next thing he knew, her top was hanging open. She shrugged it off and draped it over the footboard of the bed.

Ms. Keller raised a finger to her lips in a shush motion, and then reached behind her back with both hands. Ed sucked in a fast, deep breath when he saw the band of her bra go slack.

She was all business as she slipped her left arm out of the strap, and let her bra fall. His eyes locked onto her pendulous breasts, watching them swing and jiggle as she finished removing her bra. It found a place right next to her top.

Ms. Keller cupped the globes in her hands and pushed them together. “Like them?” When he tore his eyes away from her tits at the sound of her voice, but didn’t immediately respond, she lifted her eyebrows and slowly nodded.

Ed briefly – but rapidly – nodded his head.

She smiled and scooted closer. “Get a good look. Would you like to touch them?”

“Really?” he blurted out in amazement.

She shushed him once again. “Yes. Go ahead.”

He lifted his hand an inch or so once, twice, and then a third time, but he was too nervous. She took matters into her own hands by grabbing his wrist and lifting it to her chest.

Ed gasped as he felt the soft, warm flesh beneath his palm. He squeezed and explored them with his fingers, which drew a quiet moan from her. The bumps surrounding her nipples fascinated him, but not nearly as much as how stiff the points were when he brushed the right one with his thumb.

“Are these your first?”

He nodded, his eyes still locked on her tits as he played with them.

“I guessed that they were. What did you do when you saw them through the window?”

He gasped and looked up at her when her hand settled between his legs. He had rapidly drooped when she entered his room, and his nerves were still on edge. He was only half hard despite the naked titties right in front of him.

“Did you play with this?” she asked as she rocked her hand over his half erect member, causing it to throb.

His face burned.

“It’s okay. You don’t have to say it, and you don’t have to be embarrassed about it. Can I tell you a secret? Every time I let you see me, that’s what I did. I was thinking about you stroking your cock and thinking about me.”

He could barely believe it. His fantasy was real. She actually had fingered her pussy while he was jacking off.

She curled her fingers and gathered up the bedclothes covering him. “Can I have a peek?” She tugged, and though he let her pull the covers away from his boxers, it made his ears burn so hot that he thought they might set his hair on fire.

Once again, she didn’t tease or waste any time. She simply tugged down the front of his boxers, and fished out his cock.

“A little nervous? That’s okay,” she said, and then brought two fingers to her lips. She licked and sucked them for a moment.

Ed shivered from the sight and then gasped when she rubbed the slippery digits over his cock.

“There you go,” she cooed as the touch overrode his shame, causing his manhood to rapidly straighten.

He groaned from her touch as she stroked him with her fingertips. In no time, his cock was bobbing up toward her caressing digits, at full erection. Ms. Keller curled her fingers around it and moaned. He sucked in a shuddering breath and throbbed in her grasp.

“I know you’re wondering because all boys do. No, it’s not small. You’re average size. Perfectly adequate to satisfy a girl, if you do it right.” She moaned again. “You’re as hard as a rock.”

It was his turn to moan when she began to stroke her hand up and down his shaft. It felt so different and so much more amazing than when he jacked off. Her hand was soft, and the motion made her tits quiver.

She asked, “Feel good?”

“Yeah.”

She paused at the top of the next stroke. Her thumb stretched out, and she rubbed it back and forth on the underside of his cockhead. The sensation made him throb hard, grunt, and ooze a drop of pre-cum.

Ms. Keller rubbed the slippery drop into his skin, and then went back to stroking him. “I think you need a little push to come out of your shell, so I’m going to make you come. Okay?”

A ridiculously wide grin spread across his face as he enthusiastically nodded.

She chuckled and said, “Just relax, enjoy it, and shush.”

That was easier said than done when she cupped his balls in her other hand and began to stroke his cock faster. She gently rolled his family jewels and rotated her hand in little half turns as it slid up and down his shaft.

It didn’t take long for the wicked itch to arise in the head of his cock and spread. Ed breathed hard through his nose. His teeth clenched from fighting the moans and groans trying desperately to escape him. Her hand moved faster and faster, producing a fap sound whenever it slid over the ridge of the mushroom tip. When he glanced up at her, Ms. Keller was wearing a sultry smile and watching his face.

His balls tightened, pulling up toward his body. Though he fought it with every ounce of his will – because he never wanted it to end – the inevitable was approaching fast.

“Mmm hmm,” she moaned, stroking him fast.

Choked-off grunts caught in his throat as he drew near to the edge.

This time, her moan was higher in pitch, and sounded excited. “Mmm hmm!” She leaned in, causing her right breast to settle on his leg. She aimed the head of his cock at her tits and jerked him hard.

He came with a gurgly-sounding grunt.

“There you go,” she whispered as he sprayed cum on her chest and tits. She held him tight, just below the head, and rubbed the skin over the hard core. Another spurt further decorated her with semen.

Ed clawed at the sheets and bucked his hips as ropes of cum continued to splatter all over her. When he ceased to spurt, she rubbed the tip directly against her soft breast, making him dribble onto it. His cum slowly oozed down her breast to her nipple, where it clung tenaciously to the stiff point.

As he grew sensitive, he began to grunt, and she slowly uncurled her fingers from around his cock. He gasped and let his head fall heavily to the pillow. He panted for breath with his eyes closed for a few moments, until he heard another moan.

Every muscle in his body stiffened when he saw her licking his cum off her hand.

“So much cum,” she said while looking into his eyes. “It tastes so good.” Then she upped the ante by lifting her breast, and sucking the cum off her nipple.

He watched in stunned amazement as she gathered up his cum on her fingers, licked them clean, and then went back for more. By the time she pulled her fingers from her mouth with a final moan, her tits were shimmering from the cum smeared all over them.

She smiled, reached out, and with a finger and thumb on either side, tugged his boxers back over his softening cock. She gave it a soft pat before turning to recover her bra.

Though it caused uncomfortable twinges from his spent and sensitive organ, he watched every moment as she put back on her bra, settled her tits into it, and then buttoned back on her top.

“Our secret?” she asked once she was dressed.

He nodded, almost in disbelief that it had actually happened.

“Good. I’ll tell you a secret, though. Mandy Chambers likes you.”

His eyes narrowed and his brow furrowed. Mandy was a school friend. They had never hung out after school, but they had similar interests and had talked almost daily at school.

She was the one girl he’d seriously considered asking out. Then, seemingly out of nowhere over the summer, she’d sprouted boobs. Huge ones. Other guys started paying attention to her after that, and he assumed those big titties put her firmly out of his league. He’d been on edge whenever he talked to her in the years since, but sorely missed it now that they had both graduated.

“Yes, it’s true,” Ms. Keller said, sensing his doubts. “She needs a nice boy who likes her for more than her body. Ask her out. She’ll say yes. I think the two of you are perfect for each other.”

“I... Are you sure?”

She rolled her eyes and sighed. “I guess you need a little more of an intervention. Do you have her phone number?”

He shook his head.

“Facebook? Instagram?”

She had wanted to see his photos from the Smithsonian, and had added him as a friend on Instagram after looking at them. “Yeah. Instagram.”

“Where’s your phone? Is she in your friend list?”

Before he could answer the first question, she saw his phone and stood up to grab it. He said, “Yeah, she friended me.”

Ms. Keller handed him the phone so he could unlock it. She playfully snatched it out of his hand as soon as the home screen opened. She tapped and swiped with unexpected skill for someone from his Mom’s generation, and soon she was tapping a message.

She handed him back the phone when she was finished. The direct message read, “Would you like to go out sometime?”

“All you have to do is hit send,” she encouraged him.

He stared at his phone – his stomach doing flip-flops – and couldn’t bring himself to tap the button.

Ms. Keller leaned over and did it for him.

He thought for certain he was going to die from embarrassment, fully expecting a rejection. To his shock, Mandy almost immediately replied that she’d love to, and suggested going to a movie that he wanted to see as well.

Ms. Keller laughed when she saw his mouth hanging open in amazement. “Answer her, silly.”

He typed a message saying that he wanted to see the same flick. She came right back with a message asking if the seven o’clock showing was okay. A couple of messages later, he had a date.

“I told you,” Ms. Keller said as she stood up and straightened her skirt. “Don’t worry. She knows you, and she’s not going to be surprised when you’re ridiculously nervous. Just remember that she likes you, say that she looks pretty, don’t get handsy, or expect a kiss on the first date. I’m sure that and other things will come around soon enough.”

His cheeks warmed and he smiled when she twitched her eyebrows at him.

She continued, “Be just a slightly more confident version of yourself. You’re just what she wants, and just what she needs. You’re already friends. Start from there. You should probably...” She made a jerking off motion with her hand. “Let off that pressure before you go pick her up.”

With that, she turned and headed for the door. He watched her butt swaying as she walked. She opened the door a crack, peeked out, and then turned back toward him.

“I don’t mind if you think about tonight when you do that. And I probably will be in a few minutes.” She pointed toward the window, and then slipped out the door.

As she hinted, he watched her window through his. When the glow of the bedroom light came on, he walked over to the window.

Ms. Keller pushed open the curtains, and stood right in front of the window in nothing but her panties. Then, she hooked her thumbs in the waistband and pushed them down as well.

Ed drank in the sight of her hairy pussy while she ran her hands over her body. She bent over – her breasts hanging and swaying – to pick up something off the windowsill. It was a dildo. She slipped it into her mouth, sucked on it, and then turned away. She held her hand behind her bare butt and gave a finger-waggling wave before vanishing and turning out the light.

Ed let off some pressure not long after, knowing she was doing the same.