Assisted Living

This story is mostly fiction based on real people, events and circumstances.

Chapter 1: Pervy Pensioner

There's nothing sexier than a hot woman with a talent for teasing. All my adult life I've loved them for it.

My name's Dan, I've been single all my life and I took early retirement years ago. When Angie and I met shortly after I retired she'd been divorced for years, had two grown daughters and was still working. We became friends, but we hadn't had sex, partly because I'd sensed that we weren't sexually compatible: We often competed intellectually and socially and I figured we'd probably be too dominant with each other and clash in bed. Also, I'm not proud of it, but a more shallow reason was that she wasn't my type physically. She was still pretty, but no longer had a body that might have stimulated my libido.

We gradually accepted that sex wasn't a priority at our age, that maintaining our friendship was more important. After months of settling into a sexless relationship we both agreed that we weren't going to "date" others anymore, and I tried to be respectful of that by limiting comments and behavior that evoked "singleness." Our platonic and exclusive partnership was satisfactory for the foreseeable future.

However, I've always lusted for sexy, beautiful females. Years ago I was a part-time fashion and glamour photographer, and I still have an eye for it. It's safe to assume Angie viewed my wandering eye, flirtations and innuendo sometimes were less subtle than I thought. I wondered if she ever felt threatened by it, and I always felt a bit guilty when I realized I'd slipped up.

My most egregious slip-ups involved Brie, one of Angie's two daughters. In my defense, I was a sitting duck who didn't know what hit him. She was a beautiful blonde who sometimes worked as a model for local business promotions. I often appreciated how she presented herself back then, with stylish, often sexy, fashion sense. She worked 9 to 5 in an office, and stopped modeling shortly after I met her mom, though not for that reason, I'm sure.

One thing Angie mentioned to me soon after we met that kept recurring in my brain like an ear worm: After her divorce and before Brie moved out on her own Angie often heard her fucking her boyfriend, "taking care of her needs," and didn't blame them, as Brie was so beautiful and had a strong sex drive. After hearing that bit of news, whenever I saw Brie I thought of her having sex in various positions. But after her breakup I rarely saw her wearing makeup or anything other than shorts or jeans and a T-shirt, to my disappointment.

Brie and I got along well enough, considering I was the retired guy who was seeing her mother. She and her sister often joined us for movies and meals. I found Brie to be smart, perceptive, resourceful, energetic, and pleasant company, with passionate political convictions. We were all on the same page politically.

I knew Brie needed money, so I hired her to clean my house every month. I was glad to be rid of a chore that I hated and often postponed, sometimes for months, with predictable results. I even allowed her to bring her laundry, since she would otherwise have to go to a laundromat. Angie would often make lunch or dinner in my kitchen, so my house was often filled with activity, noises and chats, almost like a family lived in it.

Years earlier, before terminating a sub-par cleaning service, I used to sequester myself while they cleaned, to give them complete freedom to make noise with the vacuum, listen to their own music, and chat among themselves without bothering me. With Brie, that would have been awkward given our social relationship involving her mom, so she'd do her monthly cleaning when Angie and I would usually relax alone together.

At first, Brie's busy presence would normally bother me a little for that reason, but the pleasant chats between the three of us as she cleaned weren't bothersome, and I had to admit, Brie's choice of attire on cleaning day made her distracting presence even less bothersome. Her body reminded me of Sara Foster in the movie "The Big Bounce." (Remember Sara's extended up-skirt panty shot while Charlie and Owen fought over her? That's not something I forget).

The second month of Brie's service found her cleaning in the living room with me on the couch, watching TV. Just out of sight, Angie was fixing lunch in the kitchen, which was just around the corner from the living room. We were listening to music while the TV news was on "mute." Brie had just attended a political protest downtown and was telling us about it, while Angie joined in the conversation from the kitchen by calling out comments and questions.

"Mom, I can't believe how daring some men are! I mean, I was standing on a picnic table so I could see the speaker at the podium and this man, who was as old as Dad, sits down on the bench next to me. At first he's just looking towards the podium like everyone else, but then I notice he's leaning to the side and I catch him trying to peek under my skirt!"

That caught my attention, and I glanced at her, quickly scanning her skirt and legs as she dusted the credenza, and I imagined what a successful peek might reveal. She wore a stone-washed jeans-skirt that looked well worn. It was a miniskirt that was short, but not arrestingly so, reaching about 4 inches below her ass.

Angie replied, "Honey, I don't mean to be devil's advocate but you have to admit your skirt is a bit too short for standing on a table in public."

"Nah, Mom, I beg to differ, nobody could ever see anything unless they got right behind me and actually leaned forward and looked up my skirt, which would be so obvious! And this man did just that, as bold as you please! I mean, he was a good-looking man, but I closed my legs and pulled my skirt tight as soon as I noticed, and I told him, "Hey dude, watch yourself, where are you looking?"

"As if you didn't know! What did he say?" Angie called out.

"He said, "Sorry, you're so beautiful and no one is watching us back here, and at my age I can't afford to miss the opportunity to see what color your panties are." Can you believe that? Shocked the hell out of me!"

Me, too.

"Wow! What did you say?" Angie asked.

"I didn't know what to say at first. I think I caught him just in time, but I stepped down from the table and stood on the bench, right next to where he was sitting so he couldn't see up my skirt, and I could still see over the crowd. I told him that he'd better not try that again, and he nodded and said okay and I thought that was the end of it."

"There's more? What happened next?" Angie asked. I stayed silent, enjoying the titillating story and imagined myself sitting on that bench as I occasionally glanced at Brie's ass and thighs from behind my coffee table. She was now standing on a footstool and wiping off components in the entertainment center, so I had a nice view.

"It's embarrassing, but I gotta admit it excited me, too. For an older man to be so daring, the thought that he wanted to see my panties so much that he risked being caught publicly was flattering. I wasn't really concerned for my safety since we were in public. And so I didn't walk away, I just stood there!

"I can imagine, you were conflicted, right?" Angie said, "It's a lot to process. What a situation!"

"Yeah, it reminded me of high school, when I finally discovered that guys couldn't resist looking when I flashed them. And just like in those high school days, I realized I was getting really excited, just standing there and thinking about what that man did and said."

I was shocked to hear Brie talk so frankly about her panties and getting excited, a little too sexy for polite conversation. But Angie was unfazed, apparently.

"Yes, I can understand that, honey. It really is flattering when a man gets so hot for you that he loses his mind. And I'm not surprised, you really do have hot legs, like your mother. Right, Dan?"

Surprised that Angie had mentioned another female's legs to me, even in fun, I glanced at Brie's legs just as she turned on the stool to see my reaction, and I chimed in as casually as I could, "Yip-per, she does at that," and then turned my eyes back to the TV. In reality, I just wanted to stare at Brie's legs and ass as she cleaned and told her risqué story.

I did take Angie's comment as possible evidence of her missing sex. And for that matter, as far as I knew Brie hadn't had a boyfriend in months, and sometimes kidded about her hope to meet a fireman, so I wondered how horny Brie was these days and if that influenced her response to the situation at that picnic table. I preferred to think it did.

"So he didn't try it again?" Angie asked.

Brie stepped down from the stool and walked over to me, got behind the coffee table and stood just to my right, which I thought was a little odd. I looked up to question her with a confused expression, but she didn't look at me, she just watched the TV as she stood with her back to me, her hands folded in front and holding her dust cloth. Was she taking a break from cleaning? Was she interested in the Leaf Guard ad for gutters on TV? Not likely.

"Well," she said, "since I didn't run away from him I guess he decided I wasn't was as offended as he thought. He stood up from the bench and got behind me. He asked to see my big poster-board that was leaning on the bench, and he propped it up on our left side and then propped up his own poster on our right side, sort of sandwiching us on the bench. Then he told me I had the best legs he's seen in decades and asked if he could touch them so he could have nice memories in his bed tonight, and that no one could see because the posters were hiding us."

"Oh my god, he said that?" asked Angie. "What a line! What did you say?"

I hardly believed what I heard. That old dude must be clinically insane! But no denying he was justifiably tempted.

"Well!" said Brie, "I was shocked again, but not as much as before, and I was already turned on, and he did ask, so I just told him the first thing that came to mind. I said, "Well, okay, you can touch a little, but don't try to peek up my skirt again. We'll never see each other again after today, mister!"

"Wow!" Angie called out, which is what I was thinking.

"I know, right? I couldn't believe I said that to a total stranger! But it made sense to me at the time, 'cuz he would've been caught immediately if he'd dropped low enough and tried to look up my skirt, but now he could touch my legs without being seen since the posters were hiding us. So I was okay with that."

Brie was close enough that if I'd dropped to my right side on the couch I could easily look up her skirt, but that would be crude and presumptuous, so I just sat there and admired her ass and thighs with her peaches-and-cream skin. I wondered what color her panties were, and if they were damp from earlier, which happened maybe less than an hour before.

"So, did he touch your legs?" Angie asked, which is what I was wondering, too, along with why she was still standing beside me. So I could admire her legs?

"Yes, he did as soon as I gave him permission. He started at my calf and slowly worked his way up." Brie swayed her ass from side to side, and I noticed.

It suddenly dawned on me that Brie might be offering me a feel, and hiding it from her mother who was only 30 feet away! I guess my age and manner suggested that I, too, was sex-starved and would appreciate it as much as any stranger in the park, maybe more so. Maybe she knew her mother and I were not having sex. Maybe she was offering me a one-time feel of her young, silky flesh on bare thighs, now available to my exploring hands if I dared to accept.

And accept I finally did. I tentatively clasped the swell of her right calf in one hand to see her reaction. She didn't move, so I got bolder, smoothing my palm up over the back of her knee to her lower thigh.

"How far up did he get?" asked Angie, jarring me with her timing. "Oh, sorry, I hope this isn't getting too personal. Dan, you don't mind, do you? Are your ears burning? Are you leaving the room yet?" she giggled.

"No, not at all, don't mind me, I find it interesting, actually, just like an anthropology lecture, about the mating habits and rituals of the local natives," I babbled. I would have said anything to keep my hand on the back of Brie's leg. By this time my right hand was at the hem of her skirt, stroking and squeezing her right upper thigh. It felt fabulous! "More interesting than the TV news, for sure."

"Mom, it was so surreal, it felt so dangerous, but also felt like a movie or a dream. I'd gotten so used to his slow, gentle touch that when I felt his hand cup my bottom through my skirt I was surprised but I didn't stop him, I didn't feel threatened at all. Hidden between the posters like that, he felt my bottom for a good minute outside my skirt with one hand, while he felt my thighs with his other hand. It felt so weird and exciting, being pawed in public like that and not being noticed."

My cock had already started growing, but what I did in response to her obvious invitation made me hard as a rock. There was no way I'd turn down this chance, so I placed the palm of my left hand on the outside of her left thigh and stroked it, and moved my right hand up to cup her right ass cheek through her denim skirt and squeezed, feeling how firm and shapely it was. I was intrigued and gratified that Brie was inviting me to recreate her exciting encounter in the park!

Her upright stance made her ass feel naturally relaxed, not misleadingly tight in the way bending over would feel, so I was able to accurately gauge the firmness, which I diligently did, on as much real estate of her ass as possible. I explored the yielding underside of both cheeks, which felt so delightful when I cupped, squeezed and hefted them, even with her skirt as a barrier. I could only dream of sticking my hand all the way up her skirt for a better feel, but the limited access she was granting me now was fabulous enough. No doubt it would feed many jerk-off sessions for me, which I wildly imagined for her, too.

"Show me!" Brie whispered, and I saw she was looking down to her left and could see, just beyond her arm, the huge bulge of my cock through my shorts. My immediate, conflicting thoughts were, "No way, sorry, that's crossing the line!" and "Hey, no fair, your pussy isn't naked!" But I was afraid she'd withdraw if I refused, and I figured Brie should get what she asks for, given what she was giving me, and after all, red lines were already being crossed, anyway. So, in for a penny...

Hearing that her mother was still busy in the kitchen, I quickly unzipped and pulled out my boner, and just as quickly resumed my grope of Brie's ass and caress of her silky thigh, confident that I could zip up quickly enough if needed.

I had to lean forward to shift my left palm around to the front and then inside her left thigh, where her skin was like a baby's. I boldly moved an inch farther up and used my thumb to caress higher, just beyond the hem of her skirt, and I felt a thrill when she opened wider for me as she stared at my naked boner. I was suddenly afraid to continue at this heightened level of danger and intimacy. Would she actually let me touch her panties? Should I even try it, and risk her friendship and her mother's by going too far? It was almost unthinkable.

Brie hadn't moved, and stood there in a wide stance, staring at my hard-on, which I took as an invitation to continue. But I was still conflicted, worried about how this might change things between Brie and me, or with her mother if she ever found out. But the feel of her silky, warm, firm flesh was too amazing to stop my exploration, so I only hoped Brie knew how thrilled I was, knew that I would expect nothing from her after this special treat, that we'd pretend it never happened. I felt so lucky, and knew I'd remember this fondly forever.

In my lust I decided to try and reach her panties, front and back. I was so aroused that I felt a bead of my pre-cum emerging at the tip of my throbbing cock, which she was still staring at, her lips open in concentration. With my right hand still feeling the firmness of her ass cheeks, my left hand stroked a little higher up her inner thigh, but I paused immediately when I felt wetness on my thumb. A droplet was running down her leg!

I now realized how aroused she was, which actually surprised me. It hadn't occurred to me, as enthralled as I was to be the object of her teasing, that I wasn't the only one so turned-on. But her panties obviously were not doing their job anymore, and under more private circumstances it would be up to me, as a gentleman, to make her come in whichever manner she wanted. But I couldn't do it here, I couldn't touch her in her most intimate area in this dangerous setting. Could I?

My focus on Brie had suspended my sense of time and place, and Angie's next comment jolted me back.

"You must have been in shock," Angie called out. "I can't imagine you'd allow that if you'd been in your right mind. Did he do anything else?"

"Not much, aside from repeating "so nice! so nice!" as he felt up my bottom, but when I felt him press his... his erection in his pants against the back of my legs I got cold feet, thinking he might start humping me like a dog, or try to feel me under my skirt, or even pull out his thing and masturbate, so I finally closed my legs tight and turned around and told him that was enough. He looked disappointed, but he thanked me, kissed my hand, and took his poster and walked away."

Brie hadn't moved, despite her words. The bead of pre-cum at the tip of my throbbing cock oozed out and became a rivulet and threatened to drip onto my shorts. This development tipped the scales for my conflicted feelings, and I had to act fast. Keeping my right hand on her ass, I dropped my left hand quickly from between her wet thighs and grabbed my cock to prevent my pre-cum from staining my shorts. Brie's mouth opened wider as she watched.

"Well, what a crazy experience!" Angie called out. "And it could have turned out much worse! Good thing he was sort of a gentleman, right? Asking your permission like he did? Heck, he could have just unzipped himself behind you without you knowing and left the back of your legs... well... pretty messy, right?"

I was pretty far gone already, and the feel of my dripping, hard cock in one hand and her sexy ass in my other hand was incentive enough to continue on this new course, so I started to jerk off as she watched. It was another phase that I relished, being allowed to jerk off to the luxurious feeling of her delectable ass in my other hand. It was extremely risky, but fondling her ass, even outside her skirt, felt too good to stop. I could feel myself building to an orgasm, as primed as I was for so long. I knew Brie would watch to the end, if I let her.

"I know, I guess he was probably a little crazy. I got spooked, but honestly, it wouldn't have offended me that much if he had done that, you know? It's the ultimate compliment, isn't it? And it would have been easy to just wipe off my legs afterwards, anyway."

"Gonna cum!" I whispered. Well past the point of no return now, I suddenly realized with dismay that I was about to spurt my load all over myself. I wanted her to see me come, for our memories, but Angie would notice the cum stains. I glanced around quickly for something I could squirt on and then hide from Angie and wash later, like a throw-pillow on the couch. Not wanting to leave Brie's ass for a second, I quickly reached for the pillow to my left, briefly leaving my cock bouncing, the inflamed head swelling and clearly about to erupt.

To my surprise, before I could employ the pillow, Brie stepped over my legs, still facing the TV, and sat down with steady precision, pulling the back of her skirt out of the way to ensure that my cock would be covered. I felt her panties land on my boner, and one wiggle of her ass wedged my shaft between her cheeks. Then she scooted backwards so her ass pressed into my stomach and her naked thighs felt warm on mine.

With her backward shift the head of my cock slid from her ass to her soaking crotch, and I could feel the warm, wet cloth pressing against the head, her thighs clasping the shaft between them. It was just in time, because my orgasm hit me hard as I gripped her hips in both hands, huffing and sighing and trying not to groan out in ecstasy. My spasms continued for a full minute as Brie quietly sat on my lap and rocked her hips back and forth. Her firm ass cheeks in her panties felt fantastic rubbing against my stomach as she rocked against me, coaxing my pent-up semen from my balls.

I couldn't see her face as she sat and rocked on me like that, so I didn't know how she was feeling. I knew what I was doing to her panties, they'd be quite a mess. Her thighs, too, maybe. I wondered if she had any pro lap dance experience, or if it was all just evidence of her sexy mind. I preferred to think the latter. It was too much to hope that she, too, had an orgasm, but I did hope she enjoyed giving me mine, anyway.

"Mom, I'll come and help you in a minute!" Brie called out as she carefully got up from my lap. She stuck the dust cloth up the front of her skirt and held it there as she walked awkwardly to the guest bathroom, while I struggled to stuff my leaking cock quickly back into my shorts without staining them.

I'd just come all over the panty crotch of my partner's daughter and I'd yet to even see her panties, much less touch them with my fingers. It was a wonderful world, like I was on a hot date in high school again!

"No need, folks, lunch is ready!" Angie called from the kitchen. Brie had been "cleaning" for only 15 minutes before making me come, while her mother made lunch.

"In a minute!" Brie called out just before closing the bathroom door behind her. I pictured Brie wiping her crotch and thighs with tissues, and I thanked Mother Nature for oblivious mothers and nature-loving models.

And I was grateful that Brie pretended that nothing had happened even as she sat at the table for lunch. She never even gave me a knowing look. I thought of my cum stains on her panties, then wondered if she might have taken them off. After all, they'd probably be pretty uncomfortable, as wet as we'd both made them. For the whole lunch, all I could think about was that Brie was sitting at the table wearing no panties or soaking-wet panties. It made me fantasize about fucking her, or giving her head under the table, at least.