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I started my new job the day after school ended. While most of my friends were lounging around by the pool or hanging out at the movies, my father suggested that I needed to "build some character." Instead of landing a fun job, one that maybe involved a little bit of goofing off, my dad insisted I take a job that will "teach me the value of working for my money." What a jerk. So on the first day of summer vacation before my senior year of high school I was in line at the hardware mega-store, gallons of paint and supplies in my cart, ready to build some character.

My first and only painting job was at my neighbor's. Mrs. Shannon wanted to have most of her interior rooms repainted, a job that guaranteed a month's load of toil. At least it was indoors. As I scanned buckets of paint for the kitchen--her first room to tackle--I smiled to myself. The only bright side of this job, well two bright sides, was Mrs. Shannon and her daughter Amy. Amy was in my year in high school, although we didn't interact much. She was one of the hottest girls in my grade, completely out of my league. Just running into her here and there over the years had caused me to develop a small crush on her. I was excited about the prospect of seeing her a little more often this summer. I was even more excited about seeing her mom, Susan, on a regular basis. Like her daughter, Mrs. Shannon was gorgeous. Unlike Amy, Mrs. Shannon had a mind-blowing rack that made everyone on the street drool when she jogged by. I figured I'd be getting directions from her often enough to keep my mind busy while I painted. Between Amy and her mother, this was going to be a distracting job.

We had agreed that I would start at ten each day. It took longer than I expected to get out of the hardware store, but I made good time heading back home. I had received a text message from Mrs. Shannon that morning telling me to come in when I arrived, no need to knock. I had known the Shannon's forever, although Mr. Shannon had died when I was very young. I did know that they were loaded; most people in my neighborhood were. Hence the need for me to develop some more character. Dad was always worried I'd be spoiled, so he made me earn everything. Not bad parenting, really, but still kind of annoying.

It was five minutes to ten when I parked my car and set the gallons of paint and my rollers. I was about to knock when I remembered Mrs. Shannon gave me a key and had sent a text saying 'just come in when you're ready...no need to knock.' It felt a little weird to have free access to the house, but she wanted me painting even if she was out I guess. I had run into Amy the day before at the store and she actually talked to me for a few minutes, so I was hoping to run into her if she was home, but her car was gone.

I opened the door and announced myself. I heard nothing, so I let myself in. The kitchen was to the right, but I stopped dead when I looked to the left. There, in the middle of their spacious living room, was Mrs. Shannon, asleep on the couch. Not just asleep, but topless. That's right, topless. I stood there, not ten feet away from her, unable to move. Her blonde hair fell about her shoulders, one hand rested on her bare stomach. She wore jeans, and that was it. Her breasts--good god they were even better than I imagined--rose and fell with each breath.

I froze, the hair on my neck standing up as I tried to decide what to do. If she woke up right then I'd be in trouble, I knew that much. I thought I should probably leave quietly and come back later, but then she'd assume I was late and I'd be in trouble. Less trouble for sure, but trouble anyway. Either way I could end up losing my job on the very first day, something I wanted to avoid. I could announce myself again, or step outside and ring the doorbell, even though she explicitly told me not to.

As I stood there thinking of possible actions I was aware of a stirring in my pants. I had fantasized about Mrs. Shannon for years, so to see her topless like this was having a profound impact on me. I found myself running through another series of thoughts, ones involving me and Mrs. Shannon. As I tried to figure out what to do I stared at her massive breasts, her nipples hard from the cool living room. I grinned, thinking of the show I was getting, but also worried that she might wake up any second.

She suddenly stirred slightly and I jumped. She exhaled softly and moved her hand, and then was still. The feelings of excitement and nervousness battled inside me and then I decided that I would never see a woman of this caliber like this again. I set my paint cans down quietly, and cautiously walked closer. I was five or so feet away now. Her flat stomach rose and fell gently. I noted that she probably tanned in the nude, or at least topless, because she had no tanlines. I took as good a look as I could, then quickly took out my phone and snapped a few pictures. Then, just as quietly, I picked up my paint and headed into the kitchen. After all, I didn't want to give the impression that I was late. I banged about, being deliberate in making noise as I set up. I even put my phone on the counter and played music through its external speakers. I figured that if she woke up and asked, I'd say I didn't see her because I had headed straight to the kitchen.

I set up my brushes and rollers. I began edging, because I had painted my own house and had it down to a science. It was after seeing my handiwork that she hired me. And the thousand dollars she was going to pay me was what had gotten me initially interested in the job. Now, after seeing her breasts on display, I would have done it for free. I had run the first coat of edges and had started brushing the corners when something filled me with panic. If Amy came home, and saw her mother topless on the couch, how would I explain myself?

"Nice work, Henry," I heard from behind me. I jumped, almost dropping a paint-laden brush on her tiles. Mrs. Shannon was standing there, now wearing a tight button up shirt. It was white and clearly a size or two too small; I could make out her breasts underneath but tried not to stare.

"Hi," I said, a little jumpier than I should have been. "I came in and wanted to get right to work," I added, a little too quickly.

She nodded with a smile, eyeing my work so far. "I am glad this color looks good on the wall. You never know from the samples."

"Oh, it will dry a little darker. If you want I can change it."

"No, it's fine," she said, looking the room over. "I'm sure it will be fine when it dries. How's it going so far? I see you're not using tape."

"I don't need it," I said. "But if it makes you nervous I can."

"No, no, you're fine," she said, waving a hand. "If you don't mind, I'm going to run some errands. I must have dozed off this morning, and I've got to get some things from the store."

I avoided eye contact and told her I'd be fine on my own. I couldn't let my face betray me as she talked about 'dozing off.' When she returned hours later both coats of paint were dry to the touch and I was just touching a few things up around the room.

"Wow," she said, setting her bags on the table. "You're fast."

"Thanks," I said, "I've got it down pat so I don't waste time. If you see anything I missed let me know and I'll get it in the morning before I start the front hallway. I'm going to do the easy stuff on the first floor before I tackle the bathrooms and the living room. Those vaulted ceilings take a while."

"It looks great," she said. "When I saw what you did at your house I knew you'd do a good job."

"Well, I am done for the day. Is it okay if I leave my brushes and the paint in the garage? If not, I can drag them home, but I figure I can start faster that way."

"Sure, Henry," she said. "But if you aren't too worn out, could you give me a hand with something when you're done?"

I nodded, and hauled my stuff to the garage, setting everything in a corner. When I returned Susan had a box of light bulbs on the counter and a stepladder.

"Even with the stepladder I can't reach the tallest fixtures. Would you mind putting these in for me? I got those new, high efficiency bulbs."

"Sure, Mrs. Shannon," I said, climbing the ladder.

"Call me Susan, Henry," she said. "And you'll need an oven mitt to get the ones that have been on all day."

When I looked down and took the first bulb from her, I almost fell over. Somewhere in the course of the day several buttons of her shirt had come undone. She was nowhere near immodest, but from my vantage point I could see a lot of her cleavage. While I preferred her breasts unfettered by clothing, this view was amazing. I took the bulb, switched out the incandescent, and handed it to her.

"So what are your plans this summer, besides painting my house," she asked casually as I took another bulb. I tried not to stare overtly down her shirt, but I did anyway.

"Oh, I don't know. Maybe catch some movies. I really like catching them on the big screen."

"So does Amy, you should ask her to go sometime."

"Oh, I don't think she'd want to go with me. We aren't friends."

"You've been neighbors your whole lives. Besides, she's a big movie fan."

"I didn't know that," I said.

"You should ask her to join you next time," she said. It was a funny idea, but I was sure Amy did not want to go to the movies in any context with me.

"So what else is on your agenda this break? Hanging out with friends I am sure. Anything else? A major hobby? A girlfriend?"

"My major hobby seems to be house painting these days," I said with a laugh. "Actually I like to paint watercolors as well, believe it not. And I'll probably spend my free time hanging with my friends; I don't have a girlfriend."

"Amy is a homebody," she said, handing me yet another bulb. "I'm surprised she's out as much as she has been today. Has she been home? I mean, she usually has her nose in a book upstairs."

We did this for all twenty lightbulbs in the kitchen and living room, and by the time I was done I was sporting a fierce erection.

"That's it," she said as I climbed down. She still had not put on a bra, and it was hard to concentration on anything else. "Let me pay you extra for helping with the lights."

"You don't have to Mrs. Shannon. I mean, Susan. It's fine, I don't mind."

"Are you sure?" she said. "I don't want to take advantage of your time."

"No, it's no trouble at all, I'm glad to do it."

"Well, you're very sweet for doing it. It's hard to get these kinds of handy things done around here with just me and Amy, so I appreciate it. So I'll see you tomorrow, ten o'clock?"

"Sounds good," I said, turning to head out the door. She put her hand on my arm, stopping me.

"Before you go, I wanted to apologize," she said. She paused, biting her lip, before continuing. "For this morning." She waited for me to say something but I decided to feign ignorance. "For falling asleep on the couch, without a shirt. I had no intention of making you uncomfortable."

"You know, I walked right into the kitchen and got to work," I said, my eyes making contact with hers and not breaking away. "I did announce myself twice, though."

"I can't imagine what you must think," she said. "I'm so embarrassed."

"Really, I didn't even see anything," I said. "Besides, it's not anything I haven't already seen."

She laughed, patting me on the arm. "You remember that, huh?"

It was years ago, I must have been eight or nine. We had gone over to the Shannon's for a cookout and pool party. I had accidentally walked in on Susan as she changed, and for a brief second saw her topless. It was an old memory, a powerful one, that explained my deep desire for her.

"Next time I'll knock louder," I said.

"Well, just remember to come in as you please, you have a key after all. And next time, I'll try to keep my shirt on."

"I won't complain if you don't," I said, then stopped short. I had meant it as a joke, but who was I to say that to her anyway? I was relieved when she started to laugh, her breasts jiggling.

"I but you wouldn't," she said. "I haven't had a compliment like that in years." She then patted me on the arm and walked me to the door.

That night I lay in bed, unable to sleep. I was tired from painting, my arms sore, but my mind raced through the events of the day. I unlocked my phone screen and pulled up my secret camera roll. I had already moved the picture off of my normal camera roll in case anyone decided to snoop. There, on the screen, was Susan lying on the couch. My free hand slipped under the covers and found my erect penis waiting. I slowly stroked myself, eventually turning off the screen and imagining her walking around topless, her breasts swaying with each step. Of her on her knees, my penis thrusting between her breasts, fucking them until I came...

And then I came, cum spurting onto my stomach as I stroked myself furiously. I kept at it until the last of my semen dribbled out. I tensed up my muscles and focused, a trick I had been practicing for the day I might actually get it on with a girl, and kept my erection up. I waited, slowly stroking myself, and imagined her now taking me into her mouth, sucking me slowly as my cum dripped off her breasts. I stoked faster now, knowing it would take longer for the second orgasm. I came after some time, my penis still hard and throbbing, and this time I imagined her fully nude, leading me to her bedroom, where I would fuck her until she cried out pleasure. When I was finally finished, my penis spent and flaccid, I was covered in my own semen. I sighed contentedly, drifting off to sleep with visions of Susan Shannon in my head.
I didn't know what to expect the next day, but when I arrived Susan was not home. She left a note on the counter letting me know to start as I pleased, and that she would be back that afternoon. I took the time to touch up the kitchen, noticing that the new lighting showed a few places I missed the day before. I had already started working on the front hallway when I heard footsteps coming down the stairs. It was Amy, still groggy and looking like she just woke up.

While Susan had massive breasts and inspiring curves, Amy was trim and athletic, with as ass that commanded my attention when she walked. She was blonde, with shorter hair than her mothers, which she tended to wear in short, high pigtails. It was a sexy hairstyle, but to be honest anything she did was pretty much sexy. In her tank top and running shorts, it was hard not to stare at her.

"Hey, Henry," she said half asleep. She stopped, looking over the hallway. "So you're going to be here half the summer, with all the painting my mom wants."

"Yeah," I said, trying to avoid making eye contact. Amy still made me nervous; she was in a different league than I was.

"Well, I hope it's not weird, for you. You know, working at my house all summer."

"No, it's not weird," I said. I paused, "is it weird for you?"
"A little," she said, then quickly added, "not you, I mean. Sorry, that sounded wrong. It's just weird having my neighbor and classmate over here working. It's not like we're hanging out, watching movies or something. It's kind of employer-employee, it's strange."

I needed to salvage this situation. This was the longest conversation I had had with Amy since eighth grade, and it was turning into a business transaction. "Technically I'm working for your mom, so we're cool, you and I," I added lamely.

"At least we'll finally get to get to know each other better. I haven't seen you much since high school started," she said.

I grinned. Amy was being very nice, although she always was very nice. Looking at her now, I realized the barriers to talking to her were probably of my own design and construction.

"Well, I've got to paint this hallway today," I said, "but if you're free tonight, do you want to catch a movie?"

"Is this a date, or as neighbors?" she asked.

I blurted out "neighbors," a little too quickly, making her laugh.

"All right," she said. "It's a date, or whatever you want to call it." She paused, stretching, revealing a few inches of her toned stomach. "I'm going to grab some breakfast, do you want anything?"

"No, I better start before your mom gets back. I don't want to look like a slacker."

"Alright," she said, and trotted off to the kitchen. She returned a few minutes later with a bowl of cereal and sat cross-legged in the hall, out of my way, while I painted.

She ate and we talked, and she stayed afterward, chatting as I worked. She offered to help a few times but, to be honest, I had my technique down and any 'help' would just slow me down. We talked while I painted, and I was surprised by how much we had in common. We were both avid readers, and big movie fans. I had always liked her growing up, but in high school I assumed she was stuck up and ran with the popular k**s.

"I don't," she said, when we got to that subject. "I've got my small group of friends, but none of them are the popular k**s. I always wondered why you turned snobby."

"Me?" I said, and then realized she was right. My assumptions about her kept me from talking to her, so who was the snob? "I guess I had you figured out wrong."

"Oh, I don't think you'll ever figure me out," she said with a giggle. Just then we heard her mother come in. Amy's mood instantly changed. She looked at me, then her mother, in an odd way. She was nice to her mom but definitely not what I would call warm. As her mother made idle chitchat with me, Amy scurried off, giving us one last glance before she bounded up the stairs.

"It's nice that you're visiting with Amy," Susan said. "And I see it didn't slow you down at all." She stepped closer to me. I was on the ladder, and once again I could see right down her shirt. Her breasts were threatening to push out of her tank top, and I wondered if her choice in shirts was for my benefit.

She had lunch ready for me in a few minutes, and Amy came downstairs to join us. She had a t-shirt and some different running shorts on that were even shorter than the last pair. The two women eyed each other and the conversation seemed strained. I finished and returned to the hall, where Amy sat with me. I was sitting now, doing the bottom of the wall with the edger. Amy sat with her knees up, talking about which movie to see. She seemed much happier when her mom wasn't around and I felt sorry for her; it must not be easy with just one parent around, just the two of them to focus all their energy and attention on.

As we continued to chat I started to sneak covert glances at her legs, which were very toned. As I secretly followed the line of her thigh downward, I had to struggle not to react when I saw up her shorts. She wore nothing underneath, and there I sat, looking at her blonde bushy vagina. It wasn't excessively hairy, to be honest I liked a well-groomed bush, and I had to tear my eyes away from her. But we sat there, talking while I painted, her entire glory on display to me. I could see the bottom of her ass as well, and my penis was throbbing with each heartbeat. I tried to maintain eye contact, but even her beautiful blue eyes weren't enough to keep my brain wandering back.

"Well," she finally said, getting up, "I'm going to go run for a while." Her mother had just entered the room and I wondered if Amy was aware of what I could see. "I'll see you tonight," she said, and left.

"Tonight?" Susan said after Amy had left.

"Oh, we're going to the movies," I said casually, resuming my painting.

"A date?" Susan asked, her eyebrow raised.

"No, just neighbors," I said.

"I see," Susan said cryptically. She left after a few moments but returned as I was finishing up.

"It looks good," she said. "If you don't mind, I'm going to take a nap in the living room." She saw my expression and grinned, adding, "with my shirt on this time."
"Do you usually take a nap topless?" I asked casually. I figured that after yesterday, we could talk about it like adults.

"Usually, unless I have my neighbor over to paint," she added. "To be honest, I don't like to wear a lot of clothing. Amy hates it, but I'm not usually out here when she's home." She paused, touching an area of dried paint before asking "speaking of which, did you really rush past without looking yesterday? Be honest, I won't get mad."

"Um, well, to tell the truth, I may have taken a quick look. But I wasn't trying to be creepy, and I did announce myself twice first."

"I'm not upset. It's normal, male curiosity. So then let me ask you another question that you can feel free to answer honestly. What did you think?"

"Think?" I asked, a little slow to pick up what she meant.

"About my breasts," she said slowly, to make sure I understood. "I'd like your opinion of them."

I paused, and she looked at me expectantly, adding, "your honest appraisal. I'm thirty-eight, I can handle it." Her eyes twinkled like Amy's.

"I don't know," I said. "My memory's fuzzy."

I meant it as a joke, and for a fraction of a second she did nothing, and I was terrified I had offended her. I was about to apologize for my comment when the unexpected happened. Without a word she reached up and tugged her tank top down. It had spaghetti straps and came right down and bunched up on her waist. There, not two feet away from me, were her breasts. I stared and she stared right back at me, waiting.

"There you go, to jog your memory," she said casually, her hands on her hips. I said nothing for a moment, keenly aware that I had to say something.

"Um," I said, buying myself a few seconds. "Whoa."

"Can you be a little more articulate, or should I pull my shirt back on to give you some time?"

"No, wait," I blurted out, causing her to laugh. "Okay, okay. Um, they're amazing. Definitely amazing?"

"The nicest you've seen?" she prompted.

"The only ones I've seen. At least not on the internet. But, yes, the nicest I've seen, real or online."

She smiled. I kept expecting her to pull her up top but she didn't. "Well now that you've seen them, I don't really care if you see them again. Would you like that, for me to go around here topless when Amy's not around?"

I nodded feebly, completely entranced by her breasts, and her offer. Was she serious? How could I possibly paint with those things on display?

As if reading my mind, she said, "I'm going to run upstairs and let you finish up." She then walked down the hall and out of sight. My penis throbbed painfully from all of the stimulation that day, but I managed to finish my work and pack up my things. As I was about to leave Susan came back downstairs, her tank top still pulled down.

"Have fun tonight," she said with a grin. I was about to say goodbye when she took me by the hand and gave me a peck on the cheek. "Thanks for making my day," she said. As I headed out the door, she pulled her top back up, adjusting it as if nothing had happened.

I had just enough time to shower and get dressed before I needed to pick up Amy. I had contemplated jerking off in the shower to relieve the tension but knew I'd be pushing it, time-wise. At a young age I figure out how to cum more than once, and I was too greedy to do it just once. Better to wait and fully enjoy it, I thought.

Amy was walking across my lawn when I exited the house.

"I thought I'd meet you halfway," she said. She had the same shorts and t-shirt on, and my mind immediately returned to the memory of seeing up those shorts earlier. Had she put anything on underneath? She kept glancing over her shoulder toward her house as we walked to my car.

"Everything okay?" I asked.

"Oh, yeah," she said distractedly. "My mom won't let up about me going to the movies with you."

"I thought she was okay with it," I said, a little nervous. I felt a little strange going to the movies with Amy after critiquing her mother's breasts an hour earlier.

"She is. She's just pestering me," Amy explained. "It's not you she has a problem with, it's me. She's just so, so nosy," she finished.

We had picked an adventure movie about the end of the world and sat in the very back. The ads were still cycling before the previews, and Amy turned to face me.

"Okay, Henry, I need you to be honest with me."

I panicked inside, worried she knew about her mother, but she added "is this a date?"

I ran through the possible answers but decided on the truth. "I think I'd like it to be."

"Good," she said simply, and raised the armrest between us, scooting closer to me so our thighs were touching. "Because I was worried you were only interested in me as a neighbor. In fact, I was hoping your feelings were a lot more than neighborly."

I couldn't believe my ears, and then she took one more step and shocked me further. She kissed me on the lips, softly. But when I kissed her back her tongue darted into my mouth and before I knew if the movie was already in full swing. We paused, looking at each other. The theater was half-empty and no one was around us.

"I'm not that interested in the movie anyway," she said, and we started kissing again. My hand found her knee, and she put her hand on mine and slid it halfway up her thigh. We continued to kiss and I slowly, slowly made my way closer to her running shorts, hoping that she had not bothered to change at all since I last saw her. She made soft panting noises whenever our lips broke apart. As my hand traveled further up her thigh I wondered how close I could get. I felt the first contact with the fabric of her shorts and realized I was an inch way from her pussy. She kissed me harder, and bucked her hips forward, and my fingers made contact with her soft pubic hair.

She was soaking wet.

Whatever sequence of events led me to that moment, one thing was perfectly clear to me. Amy was very horny and was more than happy to let me have access to her. As my right hand gently brushed her wet labia my left went behind her back and pulled her close to me. I held her tightly as I continued to stroke her labia, marveling at how slippery she was down there. She panted and kissed me as my fingers gently stroked her labia, traveling slightly north and rubbing her tiny clit. She responded instantly, spreading her legs wider and jutting her hips out. I rubbed her clit slowly, putting firm pressure on it as I made tiny circles on and around it. I had no idea what I was doing. This was by far the most experience I had ever had with a girl, but I took my cues from what made her breathe harder, and the rest seemed to come by instinct. No one else was on our row or in front of us, but the thought that we could be caught any second seemed to heighten the fun for both of us.

"Don't stop," she whispered, "I'm close."

I kept the rhythm and pressure the same, and she kissed me harder, her whole body tensing up. I could feel her back muscles tense her her legs spread wider as she started to buck her hips. Amy was coming.

She squirmed and gasped and thrashed against me but I knew better than to stop or changing anything. I kept rubbing her pussy until she slumped against me. My hand was soaked and I could feel the heat radiating from her.

"Where did you learn to do that?" she asked.

"Right here, just now," I said in a whisper.

"Can you do it again?" she asked.

I answered by resuming rubbing her. This time she threw her right leg over my thighs and I moved my left hand lower and gripped her ass. I had dreamed about her ass for years and here I was, cupping it as I rubbed her out on our first date. It took her much less time to come this time, and I kept rubbing her until she came a third time. She was slumped back in the seat, her eyes glassy and her legs spread wide. The credits started to roll and she sat up, kissing me deeply.

"I don't have time to pay you back," she said sheepishly. "I guess I got a little greedy."

"It's okay," I said, and meant it. "Next time."

"You're on," she said, kissing me.

We had milkshakes at an all night diner, just talking about things. Our hobbies, interests. We had a lot in common, including a complete lack of physical experience.

"Can I tell you something totally embarrassing," she asked. "That was my first kiss. And, well, my first time doing that."

"Me too," I said, blushing.

"I can't imagine what you think of me," she said. "That was pretty forward."

"Um, I think you can imaging what I think," I said with a grin. She laughed, and leaned over to kiss me.

"I think I'm going to enjoy this," she said, kissing me again.

I dropped her off an hour later and headed straight up to my room. I had already kissed her on her front door, our bodies pressed together. I had to leave or else I would have ended up rubbing her off on her doorstep. My parents were already asleep and I couldn't wait any longer to relieve the pressure in my penis. After seeing Amy's pussy that morning, and her mom's breasts, and then rubbing Amy out while we kissed at the movies, I was about to explode. I lay on my bed, both hands stroking my engorged penis as I thought about the feeling of Amy's wet pussy, her firm ass, her lips on mine.

As I stroked myself another vision came to mind, competing with my focus on Amy. It was Susan. Topless, her breasts swaying while she walked. How unlike her daughter and yet how they both preoccupied by thoughts. Images of the two darted in and out of focus until I came, spurting jets of cum up my t-shirt. I kept stroking through that orgasm, once again staying hard as I kept at it, thinking of Amy and Susan until I came again. With each successive orgasm less semen issued forth from my penis, but the sensations of each orgasm intensified. Finally, spent after three climaxes, I drifted off to sleep, my penis flopped against my leg, my shirt streaked with my cum.

Life was definitely getting more interesting.