9 comments/ 131243 views/ 29 favorites All the Senior Ladies Ch. 01 By: Irish Moss Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me. Your opinions are welcome but your attacks are not. My attraction to much older women was undeniable and might have been classified as a fetish if I wasn't so particular about the older women I was attracted to. I couldn't really explain where it came from, either. I'd never been molested by a silver-haired woman nor did I ever have a crush on my or any of my friends' grandmothers when I was growing up. At some point as a young adult, I just happened to get lucky with a very fit, much older woman who totally rocked my world. Of course I hadn't stopped sleeping with women my age, or of any other age for that matter, but my preference was for active, older women. It may have been fate or it may have been my subconscious at work when I accepted the managerial position at a location of the chain drugstore I worked for that just happened to be within a few blocks of a high rise that catered to active seniors. I had initially started working for the drugstore chain just because I needed a job and they were hiring. I'd worked my way up from stock boy to cashier to co-manager and it was at that first job where I'd essentially been picked up by a sexy woman old enough to be my grandmother. I'd initially noticed her because she had a very nice physique and didn't try to hide it. When I realized how much older she was, I was actually kind of confused by my attraction at first, but I quickly came to accept it. She came in fairly regularly, so we became friendly and one day, when things were quiet in the store, she expressed an interest in jumping my bones. She ended up over at my apartment for a few hours that day after work and basically altered my perceptions of older women with her enthusiasm and her abilities. We had a pretty healthy sexual relationship up until, for a variety of reasons, she was no longer able to continue. I managed to score on a few random occasions with other older women, though I was also open to sex with women of pretty much any other age as well. I was never going to turn down the opportunity to get laid, I just happened to prefer the experience and enthusiasm of the older women. So, when I realized that my new position at my new location was going to have me in close proximity to a bevy of older women, I was obviously quite stoked. I was not planning to loiter around outside the high rise hoping to meet them as I didn't expect that would be necessary with the proximity of my store and it being the only drugstore that was nearby. I rented a townhome that was within walking distance of both my job and the seniors' high rise. It didn't take long before I encountered a couple of unattached, fit ladies who were interested in maintaining an active sex life with somebody who could keep up with them. The first was Gladys and it was on the first occasion I saw her in the store that things started up between us. I noticed her pretty quickly because she was exactly my type. She had shoulder-length silver hair, a very fit physique and was wearing spandex capris that showed off a really nice ass. I would have put her age definitely over 60, but how far over was difficult to guess because she obviously took good care of herself. I gave her a few minutes before just happening to be in the same aisle that she was. "Can I help you find anything?" I asked. She turned to respond, noticing my name tag and giving me a long once-over. "How about my g-spot?" she replied. I assumed it was a test question to gauge my reaction. It didn't put me off at all; in fact, I took it as an ideal sign. "You lost it?" I asked in response. "No, I can find it. In fact I do quite often," she replied, "but I'd like to see if you can, too." "While I'd be willing to give it a shot right here in the store," I said, "it might cause a bit of a scene. Do you live nearby?" "I live in the high rise," she replied, appearing to be pleased that I was taking up her challenge, "but I can't have you come there. People love to talk." "Well, luckily I live within walking distance," I told her, "and I'm only working for a couple more hours." I took the notepad from my shirt pocket and wrote down my address and phone number, indicating to her through the window the direction of my townhome. I let her go back to shopping as I went about my responsibilities with a smile on my face and thoughts of her naked on my mind. I had allowed myself time to get home and change my clothes before expecting Gladys, so I slipped into jeans and a t-shirt with no underwear and made sure that I brushed my teeth. I was ready and anxious by the time the doorbell rang and I was happy to see that Gladys looked as scrumptious as she had earlier. "Can I get you anything?" I asked as I locked the door behind her. "An orgasm would be nice," she replied. Since she was right to the point, I led her upstairs to my bedroom where we started to make out beside my bed. My hands went down to her ass, which was as toned as it looked, and pulled her against the growing bulge in my jeans. Figuring she was probably good and wet and wanting to confirm as quickly as I could, I moved my hands up from her ass to the bottom of her shirt and started to raise it. We separated and she raised her arms as her sports bra was revealed. Once she was free of her shirt, I tossed it aside and briefly caressed her tits through her bra before starting to remove that as well. Her areolas were small but her nipples were hard so, after brushing my palms over them, I lowered my head to lick and suck them. Gladys was running her fingers through my hair and moaning as I stimulated her nipples with my lips and tongue. I dropped my hands back down to her ass again and was soon sliding her spandex capris down, so I dropped to my knees. I just took her panties down along with her pants and was soon staring at a nicely-groomed, silver bush. Once she'd stepped out of her pants and panties after kicking off her sneakers, I stood and lifted her onto my bed. I had her lie in the middle with her head on the pillows and her legs spread for me. Lying between her legs, I kissed along her toned inner thighs and around her bush before running my tongue up her slit. She moaned and grabbed my head as I lapped at her pussy, tasting the juices that were flowing from it. I was definitely in my element with my face buried in a silver-haired pussy and was planning to make the most of it. As I'd figured from the beginning, if I made the ladies nearby happy, I'd always have somebody ready and willing whenever I needed a fix of geriatric snatch. I slurped up her juices while she rocked her pussy toward my face then slipped one finger, quickly followed by a second, into her hot, wet pussy. As I pumped my fingers in and out, I started to lick and suck her clit, causing her to moan loudly. I glanced up along her body and saw a look of raw passion on her face and was happy to have put it there. One of her hands moved up from my head to caress her tits and gently tug on her nipples. I was caught by surprise when she suddenly cried out and her body started to shake. I knew I couldn't take full credit for her cumming so quickly, figuring that some of it was due to pent up sexual frustration and some due to knowing her body really well. Beyond that, I assumed my tongue and fingers played a role, as well. I continued eating her as she rode out her orgasm and, when she gave no indication for me to stop once she settled back down, I just kept going, savoring the opportunity. With my throbbing cock anxious to escape from my jeans, my tongue and lips worked over her clit through several more orgasms. I could feel her pussy only getting even hotter and wetter with each one as my fingers pumped in and out and knew that meant that sliding my cock into her was going to be incredible. I would have kept going until my tongue collapsed from exhaustion but, when Gladys finally indicated that she was ready to be fucked, I was just fine with that, too. I straightened up on my knees and she sat up, reaching for my jeans, so I slipped out of my shirt as she got them open. My cock sprung out as she worked them down and she immediately took it in her hand, stroking it and caressing my balls. I continued working my jeans down as far as I could, then flopped onto my back to get them the rest of the way off. She got my jeans completely off for me and cast them aside, then straddled me. I was gazing up at her mature, fit body looming over me, feeling more aroused than I had in some time. She smiled down at me as she took my cock in her hand and guided it toward her silver bush. I reached for her tits, caressing the soft, smooth flesh and her hard nipples, as she lowered herself onto my throbbing tool. We both moaned as her hot pussy engulfed my cock and she just sat there for a minute, embedded on it, before starting to ride it. She started slowly, appearing to relish the feeling of my throbbing tool buried within her, as I continued to fondle her tits. As she picked up the pace and her tits started bouncing, I let my hands slide around to caress her taut ass as I watched her tits before she leaned forward, her hands on either side of my head. At that point, I was able to start licking and sucking her hard nipples while caressing her ass. I could also push up into her each time she came down so that she was getting as much of my cock penetrating her as we could manage. Our pace was growing more and more frenetic the longer she rode me and my orgasm was beginning to build. Before I was very close, though, Gladys seemed to go into slow motion as a shudder passed through her body. She rode out another long, intense orgasm as I dropped my head back and watched the blissful expression on her face. Given the number of orgasms she'd had as I'd been eating her pussy, I was expecting her to continue riding me once she'd finished cumming and go for a few more. I was a little surprised when, after she'd caught her breath, she climbed off of me but was not disappointed when she knelt between my legs and took my cock in her hand. She pumped it briefly before lowering her head and taking it into her mouth. It was immediately apparent that she was a skilled cocksucker and that combined with her obvious penchant for sex had me thanking a higher power for bringing her into my life. I watched as her mouth traveled up and down my tool while she pumped the base, a curtain of silver hair framing her face, and felt even more aroused by the visual. Her oral skills quickly had my orgasm building faster even though she was setting a slow and sensuous pace. I thought I'd be cumming pretty quickly due to her amazing mouth but she drew out the pleasure I was feeling like a pro. I didn't feel tortured, like she wasn't letting me cum, but just experienced a level and duration of pleasure like I was not expecting. Eventually, however, my cock began to swell even more and, when she realized that I was on the verge of cumming, changed her tactic from drawing out the pleasure to making me cum. Her mouth was moving up and down faster as was her hand on the base. When I exploded into her mouth, I let out a moan and she swallowed my load hungrily. She continued nursing my cock until I was completely spent and starting to soften, then crawled up to lie beside me. We just lay there together recovering, our naked bodies pressed against each other, for a little while. "What are you doing with an old lady like me?" she finally asked, breaking the silence. "Isn't it obvious?" I asked in response, "I'm enjoying and appreciating your experience and your enthusiasm." "Are you just into old ladies?" she continued. "No, not just any old ladies," I replied honestly, "I like hot and horny old ladies like you but the sight of a walker, for example, is not a turn on in general." If she was having any doubts or feeling some insecurity all of a sudden, that seemed to set her mind at ease. We talked a little bit more and appeared to be on the same page regarding what we were hoping to get out of this relationship, which was essentially just sex. She ended up sticking around for a few hours during which we tried out numerous positions and a variety of activities. It wasn't too long after my first encounter with Gladys that I met Dixie, much in the same way. She caught my eye as soon as she entered the store, partly because she was quite pretty, partly because she had long silver hair that reminded me of Judy Collins or Emmylou Harris, and partly because she had one hell of a rack. I found out soon enough that she also had an amazing smile and a bit of a southern accent. Of course I found an excuse to see if there was any way that I could assist her. "Is there anything I can do for you?" I asked as I conveniently crossed paths with her. "Oh, I can think of a few things," she replied, flashing that incredible smile and tempering the suggestiveness of her response with her accent. "You just name it," I told her, "I'd do just about anything to see that smile again." "Anything?" she asked, giving me a sultry look and a once-over. "Absolutely," I confirmed, then lowered my voice, "In fact, I'm really curious about whether I'd see that amazing smile when you're cumming." "There's really only one way to know for sure," she replied and I was absolutely certain that we were on the same page. We went through the same discussion I'd had with Gladys regarding where she lived and where I lived and I similarly gave her my contact information and let her know when I'd be off work. She called later that day before walking over and, again as with Gladys, I was ready and anxious to see her when she arrived. She was wearing the same dress she'd been wearing earlier, which had buttons all the way up the front, including a few just below the collar that looked like they were ready to burst right off. I was looking forward to unbuttoning every single one. I led her into my living room and indicated that she should take a seat in my recliner. "My word is that a big chair," she said as she stood before it. It was an oversized recliner that I'd purchased not just because I wanted a comfy chair in front of the TV but also because it was perfect for a variety of sexual positions. I'd found that a change of pace from the bed and the couch was typically welcome. I had her sit as I knelt before her and immediately began to unbutton her dress from the hem upward. As her thighs were exposed, I began to kiss them, alternating from one side to the other and working my way up. Once her panties were visible, a very sexy pair trimmed with lace which made me wonder if she'd put them on after we'd made plans, I stopped unbuttoning and kissed around them while lightly caressing the front before starting to slide them down. She lifted her ass for me as I exposed her well-groomed silver bush, then spread her legs once I'd cast her panties aside. I ran my tongue up her slit, tasting the copious juices that she was producing and causing her to moan. She started running her fingers through my hair as I lapped at her pussy, devouring her pungent nectar and making her squirm. When I shifted my focus to her clit and was licking and sucking that, I slipped first one then a second finger into her slippery pussy. She was humping my face in rhythm with my fingers sliding in and out of her. I glanced up, wanting to make sure I could see past her monumental tits when she came, and was able to see the look of passion on her beautiful face. I smiled, satisfied that I was achieving my goal of providing pleasure to her, and returned my focus to making her cum. If I hadn't been able to see the look on her face, I could have figured that I was doing right by her based on how loud her moans were becoming and how hard she was starting to force her pussy toward my face. I was perfectly okay with her cumming quickly, since I was assuming that this would not end up being my only opportunity to bury my face in her pussy, but I was going to keep eating her after she came until she had me stop. I thought she might enjoy a few orgasms right up front just as Gladys had. She started tensing up a bit just before she came but all the tension appeared to leave when she let out a cry and her body started to shake. I kept my fingers pumping and continued licking and sucking her clit while looking up quickly as she rode out a long, intense orgasm. That amazing smile did reappear on her face to replace a look of intense concentration, which answered one of my questions about her. There were still many things I wanted to learn about her, though. When she went still, she took my face in her hands and turned it up toward her face since I'd gone back to focusing on her pussy. "Let me see your cock now," she said, so I slipped my fingers out of her and stood up. She sat up and started working on opening my jeans, so I slipped my fingers into my mouth and sucked her juices off of them. Since I was sans underwear, my cock sprung out in her face and, naturally, she immediately took it into her mouth while continuing to push my jeans down. I savored the feel of her mouth until she had to abandon my cock in order to get my jeans the rest of the way off. I went ahead and shed my t-shirt so that, once I'd stepped out of my jeans, I was standing naked before her with my cock sticking straight out. She stroked my cock as she stood and indicated for me to sit. I had planned to finish unbuttoning her dress myself, but I found myself perfectly content to sit there watching as she did it. She continued from where I'd left off and a sexy, lacy bra that matched her panties was soon revealed. My attention was fixed as she reached back to unfasten her bra and I was not disappointed as it slid down her arms and those beauties were revealed. Letting her bra drop to the floor, she hefted them in her hands with a smile on her face. "You like them?" she asked and I nodded dumbly. She brought them closer, climbing onto the chair and straddling me, but before I started to fondle them, I reclined us. They jiggled enticingly as we hit our new position, so I reached for them as she reached for my cock. I caressed the soft, smooth flesh and ran my palms over her hard nipples as she guided my cock to her pussy and lowered herself onto it. We both moaned as her pussy engulfed my throbbing tool and, while I played with her tits, she just sat for a moment before starting to ride it. She braced herself on the back of the chair over my head, putting her tits right in my face, then started to move up and down on my cock. I continued to caress her swinging, bouncing tits as I licked and sucked her hard nipples. Her hot, wet pussy felt outstanding and, despite being pretty distracted by her awesome tits, I was well aware of how it felt sliding up and down my cock. My initial desire had been to fuck her and I considered her impressive chest essentially a bonus. Seeing her tits and getting my hands on those beauties did not detract from the fulfillment I was feeling from scoring with another mature beauty. I was pushing up into her each time she came down on my tool, savoring the slippery wetness of her pussy, and I couldn't help but eventually slide my hands around to squeeze her ass. My lips and tongue continued to work on her nipples and areolas but I knew her ass, though not as toned as Gladys', was a thing of beauty as well. I squeezed and caressed her cheeks as I continued pushing up into her, feeling the stirrings of an orgasm as her pussy seemed to get even hotter and wetter the longer we went at it. Of course my hands did not remain on her ass and were alternating between it and her succulent tits as she got louder and rode me harder. All the Senior Ladies Ch. 01 I got the sense that this was going to be another fairly quick orgasm for her, which was much better than having a fairly quick one myself and leaving her high and dry. It didn't feel like we were rushing, though, which was good; it felt more like we were just enthusiastic. Knowing that we had at the very least several hours available to spend together, I was okay with being enthusiastic now and savoring later. My orgasm was beginning to build in earnest with her pussy feeling hotter and wetter as she rode me harder, but she was a few steps ahead of me. I didn't know whether it was because she'd had one orgasm already which made the second one come along more easily or if she was just pent up and super horny, but she suddenly went into slow motion as a shudder passed through her and that amazing smile appeared on her face again. I raised my head to look at her face as she came, though I continued to fondle her tits. This orgasm seemed even longer and more intense than the previous one, which made me feel pretty confident that this encounter was just going to lead to even more. She collapsed on top of me when she'd finished cumming and just lay there catching her breath momentarily. My cock was still embedded in her and still throbbing, but I waited until she was ready to get going again. When she raised her head, she smiled at me then stuck her tongue in my mouth. We made out for a moment before she climbed off of my cock and knelt beside me. She stroked my cock then lowered her head and wrapped her lips around it while pumping the base. I could feel my orgasm starting to build again due to her undeniable oral skills, but there was something else that I still wanted to do. "Would you mind if I fucked your tits?" I asked before it was too late. "Do you know how long it has been since somebody asked me that?" she replied after slipping my cock from her mouth and turning to look at me. "Even if nobody has asked, I'm sure a lot of guys have fantasized about it," I assured her. "You're sweet," she replied, "but you don't have to butter me up." "You just gave me an idea," I said, "I wonder how much butter I have." "Silly," she said as we maneuvered around so that she was on her back and I was straddling her. I lay my cock between her tits and she squeezed them together around it, then I started to slowly slide it between them. The soft, smooth flesh felt outstanding as it rubbed against my aching tool and I knew it wouldn't be long before I was spewing. I was supporting myself on the back of the chair, over her head, but was looking down at her succulent boobs as I was fucking them. Her attention was on my cock as it appeared and disappeared within her cleavage. I tried to move slowly and savor the slow build up, but the better it felt, the more difficult that was. I was pretty close to blowing my load on her sternum when she spoke up. "Will you cum in my mouth please?" she asked. "Slide down so we don't tip the chair over," I told her, "because I'm just about there." She released her tits and slid down the chair until my cock was right in her face, then she wrapped her lips around it while grabbing my ass. I slipped my cock deeply into her mouth and savored her outstanding oral skills again. Ultimately, I was fucking her mouth more than she was sucking my cock, but she didn't just lie there with her lips wrapped around my tool; she had something going on with her hot mouth that had my cock swelling even more almost immediately. I was moving slowly, savoring the high levels of pleasure and wanting to enjoy it for as long as possible, but it wasn't long before I couldn't help but explode into her mouth with a grunt. She hungrily devoured my load and continued to nurse my cock even once I was spent. She even seemed a bit reluctant to release it when I started to move off of her. "It has been a while since I've had both a hard cock and an orgasm at the same time," she revealed as I lay beside her, "The hard cocks don't tend to stay hard long enough and the orgasms usually occur when I'm alone." "Well I'm certainly happy to be of service," I replied, "and I hope you realize that you are welcome to visit any time you're feeling horny." "Good thing you live nearby," she said, "because I'm horny a lot." "So am I," I confessed. "Just for old ladies?" she asked. "Just for hot, horny, sexy ladies regardless of age," I told her, "though I am kind of partial to the experience and enthusiasm of certain older ladies." "Well I'm glad we found each other, then," she said. We lay there in my recliner, chatting and recovering, but didn't remain stationary for long. By the time she left that night, we'd given both the chair and my bed a thorough workout and had even played in the bathroom a little after a shower together. I couldn't imagine that I'd find any other ladies from the active senior high-rise who'd be as hot and horny as Gladys and Dixie were, though I did always keep my options open. All the Senior Ladies Ch. 02 Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me. Your opinions are welcome but your attacks are not. Note: If you haven't already, read All the Senior Ladies Ch. 01, which is the prequel to this story. Gladys and I were lying around one day, naked after an enthusiastic bout of sex, and she mentioned something about her weekly one-hour massage. "Male or female masseuse?" I asked. "Male, of course," she replied. "What do you think about while you're lying there naked and his hands are all over you?" I asked. "Fucking him, sucking his cock," she replied, "What do you think?" "Have you ever done it with him?" I asked. "No and I don't plan to," she replied, "He's an incredible masseuse and I'd hate to mess things up. Plus, I know that, after I get all worked up, I can come over here and you'll take care of me." I got to thinking about another way to take care of her, though. I did a little research and did a little planning and, one day when I knew Gladys was coming over, I rented a massage table. It couldn't be just any massage table, though, because I expected that it was going to see some real action; I made sure it was a sturdy one. I dressed in a pair of white scrub pants and a white t-shirt, which surprised her until she looked past me into the living room and saw the set-up for her fantasy massage. "Your hour starts once you're undressed and under the sheet," I said as her mouth hung open, "Would you like me to leave you alone to undress." "No, that's fine," she replied, coming back to herself, "No sense in being shy if I'm going to be naked for the massage anyway." We had moved over beside the table and Gladys pulled her shirt up over her head as I watched her sexy bra come into view. She'd taken to wearing a lot of sexy lingerie when she knew we were going to be together, though sometimes I still liked to see her in her athletic gear. She dropped her capris next and made as though she was carefully setting her clothes aside while actually making sure I got a good look at her in just her matching bra and panties. My cock was tenting out my scrubs since I hadn't bothered with underwear myself and this didn't escape her notice as she faced me again. She reached back to unfasten her bra as she stared at my bulging pants then let it slide down her arms, exposing her tits and hard nipples to me. Finally, she started to slide her panties down, revealing her trim, silver bush. Again, she made sure her clothes were just so in order to let me get a good look at her naked from both sides. She climbed onto the table on her stomach with the sheet over her as I grabbed a bottle of massage oil. I folded the sheet down to expose her from her shoulders to her hips and went about massaging her back, shoulders, arms and neck. Once that was done, I pulled the sheet back up and folded it from her legs up to just below her ass. I started with her feet and massaged my way up her calves and thighs, spending additional time on her smooth inner thighs just below her pussy. I could tell by how she was moving and moaning that I was getting her nice and worked up. To continue, as well as to indulge myself a little, I folded the sheet up a bit further and thoroughly massaged her awesome ass. I loved those toned cheeks and took any opportunity to get my hands on them. Before having her roll over onto her back, I drizzled a bit more oil between her ass cheeks, spread it up and down her crack, then penetrated her ass with a well-lubed finger. I had only pumped it in and out a couple of times when I felt her trembling as she came. We had experimented a little bit with anal penetration up to this point, but I hadn't fucked her ass yet. I had been thinking that, with all of the massage oil available, that might change before the night was over. I had her roll over onto her back and started with her legs again, massaging her feet and shins and up her thighs, which I then spread apart as I lowered my head to lick her pussy. I knew that, despite the orgasm due to the anal penetration, her pussy would be on fire and overflowing with juices. I slurped up her nectar as she moaned loudly, then slipped a couple of fingers into her and lapped at her clit. I always loved eating her pussy, probably almost as much as she loved having it eaten, so this break was as much for me as it was for her. She grabbed my head and was pushing her ass up off the massage table as she tensed up while getting closer and closer to cumming. I wasn't expecting it to take her very long to cum under these circumstances so I savored the taste and feel of her pussy for as long as I could before I had to get back to massaging her to finish out the fantasy. She let out a cry and dropped back onto the table, shaking as she came. I continued eating her pussy until she went still, then straightened up, pushed her legs together and covered them with the sheet. The top of the sheet was in a bit of a disarray so, as she was still recovering, I folded it down to expose her tits. I drizzled more oil onto them and caressed and fondled them more than actually massaging them. Her chest was still heaving as she caught her breath so I just enjoyed her tits until she opened her eyes and smiled up at me. "Your hour isn't up yet," I told her, "Is there anything else you'd like massaged?" "I'd like you to massage the inside of my ass with your hard cock," she replied. "It would be my pleasure," I assured her. She slipped out from under the sheet and sat up, untying the drawstring of my pants as I pulled my t-shirt up over my head. My pants dropped right to my ankles, so I stepped out of them as she stroked my throbbing tool. I offered her some massage oil, which she used to lube up my stiff cock. When she was ready, she got on all-fours on the table and I got behind her on my knees. I drizzled more oil between her cheeks, spreading it around her asshole, then took my cock in hand and eased it into her ass. She was moaning loudly as I penetrated her and, feeling how tight her asshole was, I couldn't help but join her. As much as I enjoyed fucking both her and Dixie, neither of their pussies could be considered tight, which really was no surprise. I'd never had an issue with it, however, because they were always so hot and wet. Slipping into Gladys' ass was a sensation that was beyond description. I knew that I wouldn't be good for very long but, since she'd already cum twice, I wasn't too concerned about shooting off quickly. I wasn't surprised, however, when shortly after I started sliding my cock in and out of her tight ass, she started to tremble as she came again. I was fucking her slowly, relishing the feeling and being careful not to cause her any discomfort. I noticed that she had both of her hands reaching back under her and could just imagine what they were doing. As quickly as it felt like my orgasm was building up, hers was clearly coming on even faster because I felt her cumming again as I was continuing to savor the pleasure I was feeling. I gradually increased my pace the longer I was fucking her and she seemed to be fine with it. I finally exploded deep into her ass with a moan and she started cumming again as my cock was spasming inside her. I continued fucking her until I no longer could, then pulled out and we lay together on the massage table, catching our breath. "Oh my God, that was fantastic," she finally said, "I think, after all these years, I am now a fan of anal sex." "I'm glad to hear you say that," I replied, "because I thought it was pretty fucking awesome, too." She was comfortable enough at my place by that point that, when she got up to use the bathroom soon after, she just went ahead and soaked a washcloth in hot water and brought it back. She wiped down my cock and it was no surprise that it started stirring again. Realizing this, she sucked it briefly as I remained laying on the table. I wasn't reviving that quickly but she had another idea in the meantime. "How about if I show you what I'd do if I was a masseuse and you were my client?" she suggested. I was game so I rolled onto my stomach and she went through the pretense of laying the sheet over me, then oiled up her hands and massaged my back and shoulders. It felt nice though it wasn't necessarily arousing me any more than I already was. When she worked on my legs and her hands moved up near my ass, I could feel the blood flowing a little bit more. She had me roll onto my back and, rather than oiling me up and massaging me, she wiped the oil off her hands and started to caress my cock and balls. It didn't take much of her attention before my cock was growing again and, before it was completely stiff, she climbed up onto the table, straddling my head, and wrapped her lips around it. Her silver pussy was above my face so, as I ran my hands over her ass, I ran my tongue up her slit, tasting her pungent juices. My cock was reviving quickly under her oral attention and I wondered whether she was going to suck me off to completion or whether she'd want to get fucked. I slipped a couple of fingers into her, determined to enjoy her pussy and her mouth regardless of what she decided. I contemplated slipping a finger into her ass and figured I'd wait until she was on the verge of cumming to push her the rest of the way. She must have decided she wanted her pussy rather than her mouth full of cock for the moment because once I was fully rigid, she crawled away from my tongue and fingers and straddled my hips, her ass still aimed in my direction. As she guided my throbbing tool into her hot, wet pussy, I ran my hands over her taut ass. She lowered herself onto my cock and started to slowly ride me, one of her hands going right to her pussy to stroke her clit. I wondered if she was imagining that I was her masseuse as I watched her pussy sliding up and down my tool. I never had any trouble getting her heated up and making her cum, but I suspected that this forbidden fantasy certainly wouldn't hurt the cause, either. It didn't take long before she was riding me harder and faster so I was pushing up into her each time she came down, thinking I might be able to cum again simultaneously with her. I decided against penetrating her ass again, at least this time, and instead was holding her by her waist, pulling her down as I pushed up into her. Her ass was slapping against my upper thighs and her moans were growing louder and longer. We'd been together enough times by then that I could better tell when she was on the verge of cumming and could often time my own orgasm to coincide with hers. It was definitely building up as a result of her hot, wet pussy sliding up and down my cock, so even if I didn't cum right with her I knew we'd be close. The massage table was shaking a little as she bounced up and down on my tool but was definitely sturdy enough to endure it. When she started to cum, she slowed down and savored the feelings of pleasure washing over her. My building orgasm was temporarily on hold, which was okay with me because I knew it would still be incredible. I gradually started fucking her again as she appeared to be recovering and she was soon bouncing up and down on me again as my cock grew thicker. With a moan, I exploded into her, giving her another load of my goo. She continued to ride me until I was spent, then climbed off of my shrinking cock and turned around, laying on top of me. We made out a little bit before she nuzzled against my neck. "You're so good to me," she said, "but I get to fulfill one of your fantasies next time." The whole event had gone so well that I was immediately thinking about a way to do something similar for Dixie. We'd talked many times, usually after sex, about her growing up in the south in the late 50s and early 60s and how she'd repressed her sexuality for so long. She basically had to pretend she wasn't horny while frigging herself like mad every night from the time she was an adolescent. She'd been lucky to be married young to somebody she'd loved, and continued to fuck, right up until his passing. While I couldn't provide her with a big, black cock if that ended up being the fantasy of a southern belle, I did get to thinking about some of the times she might have been incredibly horny and had to suppress it. I steered a few conversations along those lines until I finally had a plan. I told her one night that we'd be going out because I had a surprise for her but, before we got going, I wanted to try something. I asked her if she had a dress in a style similar to what she might have worn as a teenager when she was being courted by her husband. She said that she had something close enough without looking like she'd actually saved it from back then. I requested that, with that dress and anything else she could come up with, she dress as though it was back then. I did a little research myself into what her future husband might have been wearing and driving. When I opened the door to let her in that night, we were both pleasantly surprised. "This isn't really your surprise," I told her, "though it is related to it. We have some time first, however, so I thought it might be about time to reenact something in the way that you would have had it go if you'd had the complete freedom to do so." I led her over to the couch and we sat down together. "Let's imagine we are at your house and I've come to visit with you," I said, "and that we don't have to worry about any interruptions from your parents." We started to make out and her hand went right to my lap, where it massaged my quickly-rising cock. I fondled her tits and could tell that she was wearing a serious bra under her dress. It didn't take very long before she had my pants open and had extracted my cock from my underwear. She was giving me a very nice handjob as we continued to make out and my hand remained on her tits. I was thinking that, as horny as she'd told me she'd have been in a situation like this, that she was probably dripping wet by then. I decided that I'd need to take care of her in some way before we left my place even though I was certain that she'd end up more than satisfied by the real surprise part of our evening. "I might take this all the way to completion on this and a few subsequent nights," she said after pulling her mouth from mine, "before moving on to what I'm about to do, so I just wanted to let you know that what I'm doing might not be exactly as I might have done it back then." She moved off of the couch and knelt before me, taking my cock in her hand again as I worked my pants down a bit farther. She wrapped her lips around my tool and started to bob her head up and down while gently pumping the base. I certainly appreciated that she didn't revert to her teenage skill level as she sucked my cock even though just having my cock in her hot mouth was incredibly pleasurable. She put the skills she'd developed during her marriage and had previously demonstrated on me into action, including licking and sucking my balls while continuing to pump my cock in her hand. I was leaning back on the couch, watching as her mouth moved up and down my tool and her long, silver hair hung around her face. Because we had plans, I wasn't intent on drawing this spectacular blowjob out and I got the impression that she wasn't, either. We both knew, even though she wasn't aware of our exact plans, that this was merely an appetizer. Because she was more focused on making me cum than on drawing out the pleasure, it wasn't long at all before I was feeling my orgasm rapidly building. I couldn't recall her ever blowing me to completion while still fully dressed, so that only added to the eroticism of the moment. I could easily imagine her at 18, so horny that she was blowing a guy in the parlor while her parents were in the other room. It was all too much for me and I soon exploded into her mouth with a grunt of pleasure. She swallowed my load and nursed my cock until it was spent then sat back on her heels and smiled up at me. "Before we go," I said, looking down at her, "I'd like to give you a quick orgasm to tide you over, but I'd like to stick with the theme of the night, too." I had her get back up on the couch beside me then ran my hand up along her inner thigh, under her dress. Encountering her panties, I caressed the front of them before seeking the waistband so I could slip my hand into them. I was a little surprised initially until I realized that she was basically wearing period-appropriate undergarments, which also explained the substantial bra. I had to move my hand up pretty far under her dress before I could slip it into her panties. Once I encountered her pussy, however, I found it overflowing with juices, indicating that she was incredibly worked up, so I was glad that I had decided to do this rather than wait. My intention was to manually bring her to orgasm just as I might if we'd actually been in her parents' parlor. As she nuzzled against my neck, I had one arm around her shoulders and one hand caressing her pussy. She spread her legs for me so that I could pump a couple of fingers in and out of her slippery pussy when I wasn't gently caressing her clit. I was pretty sure that I'd never gotten her off this way before but I had enough experience from my own teen years to recall what typically worked best. As I put my technique to work, Dixie was humping her pussy toward my hand and moaning softly, so I knew I was on the right track. It was pretty erotic since I couldn't remember the last time I'd had my hand up a woman's dress and down her panties instead of just stripping off most of our clothing. I wasn't ready to go again yet, but I knew I would be when the time came. She was getting louder and wriggling more the longer I fingered her hot pussy and, because I knew she was worked up from sucking my cock, I wasn't expecting it to take much longer for her to cum. In fact, since knowing her I'd realized that I never expected it to take very long for her to cum. I was curious about who typically came faster - her or Gladys – but hadn't figured out how to determine that because I had no interest in staring at a clock while getting either of them off. If I could get them together and work on them at the same time, on the other hand, I might be able to make a determination. Dixie started to tense up just before she came so I knew she was right on the verge, then her body relaxed as it twitched and shook while she was cumming. I continued to caress her clit until she let out a long sigh and went still then slipped my hand from her panties as she kissed me. She adjusted her panties and pulled the hem of her skirt back down as I got my underwear and pants back up. We both stood and made sure that we were presentable before we left. "I want you to wait right here," I said on my front step, "I'll be right back." I'd done some research and made some calls until I was able to find a period-appropriate vehicle that I could rent. I'd picked it up earlier that day and had it in my garage while my own car sat over in the parking lot where I'd rented it from. I drove around the building and pulled up at the end of the walk, then stepped out and watched Dixie's eyes go wide. "My best friend's big brother had a car like that," she said as she joined me standing near it. All the Senior Ladies Ch. 02 "Did he ever take you parking in it?" I asked. "No, I was much too young for him," she replied, "but I dreamed of being old enough that he would." "Well if you want to pretend that I am him," I told her as I helped her into the passenger seat, "I won't be at all offended." She didn't respond as I walked back around to the driver's seat and I assumed that she was experiencing a few flashes of nostalgia. We drove in silence for a few minutes before she came out of her reverie. "I'm not going to ask where we're going," she finally said, "because I know it isn't someplace where people are going to think that it is cute that you are taking your grandmother out on a date. In fact, if I know anything at all, I know I'm going to get laid in the backseat of this car before the night is over." "You know me too well," I replied, "but there's definitely a theme to the night." I think she was looking for clues as we were driving along and it came immediately to her as I turned onto a particular road. "We're going to the drive-in!" she exclaimed then kissed me as best she could without causing me to crash. There was still one operating drive-in not far from where we lived and I couldn't imagine a better place to relive her youth with less restraint than in the backseat of a classic car at the drive-in. I didn't care if anyone looked into the car at the entrance and thought our disparate ages were odd; in fact, I didn't care if anyone looked into the car and saw us fucking and thought our disparate ages were odd. I knew without a doubt that things were going to be hot at the drive-in that night and that we'd both be unconcerned about anyone else. I bought the tickets and Dixie didn't even get a second look from the bored-looking booth attendant. We selected a spot that wouldn't be too obviously out of the way but that also wouldn't result in a lot of people looking through our back window rather than at the screen. Since we weren't planning to watch the movie, we didn't bother tuning to the radio station that carried the audio and just jumped into the backseat once I'd turned the car off. Dixie went first and my hands were all over her ass as she climbed over the front seat. Once I was back there with her, I had her lie down on the long, large back seat as I pushed the hem of her skirt up and exposed a pair of panties like I had only seen before while watching Animal House. "Pretty sexy, huh?" she asked as she watched my reaction. They were actually sexier to me than she could have imagined, in part because they were on her. The whole 60s motif was arousing as well since I'd only really seen it on TV and in the movies. I ran my hand over the front of those panties before she lifted her ass so that I could slide them off. With her legs spread wide and the hem of her skirt up around her waist, I lowered my head and started to lick her pussy. She immediately started moaning and grabbed my head, making me glad I'd forgotten to roll down the windows so we wouldn't get too hot. I ran my tongue up her slit, tasting her plentiful juices, before slipping a couple of fingers into her. As I pumped my fingers in and out, I started licking and sucking her clit, causing her to moan even longer and louder. It occurred to me that, if we were truly reenacting a potential teenage date, I should probably have given her pussy a couple of cursory licks, then stuck my cock into her, pumped three times and been done. Instead, I focused on an idealized teenage date since one of my favorite things was licking her pussy and I often continued to do it even after she'd cum. My cock was reviving as I licked and sucked her clit so I was certain that, whenever she was ready, I'd be up to the task of fucking her here in the backseat. I could feel her pussy becoming wetter and more engorged the longer I ate her and knew that she was building up to one of her typically long and intense orgasms. It didn't surprise me when she started to shake as she came. I continued to lick and finger her, planning to stop only if she wanted me to, but she grabbed my head when she'd finished cumming. "I want your cock inside me now," she said and I had no intention of arguing. I slipped my fingers out of her and licked her juices from them, then opened my pants and pushed them to my knees along with my underwear. Kneeling between her spread legs, I guided my cock into her and we both moaned as I started to slowly fuck her. I liked that there was enough room in the backseat for us to basically spread out and fuck, but the position I'd selected ended up being a bit awkward. I stuck with it for a little while, pumping my cock slowly in and out of her hot pussy while looking down on her, but I knew there was a better way. "Wrap your arms around my neck," I said after a while. When she did, I grabbed her behind the back and pivoted so that I was sitting in the middle of the backseat and she was straddling me. "That was smooth," she said with a smile, then leaned down and kissed me. While she started to bounce up and down on my lap, I reached behind her and slid the zipper down her back. As I started to slide the top of the dress over her shoulders, she pulled her mouth from mine and leaned back so I could see the bra she was sporting. It was an engineering marvel that had transformed her substantial breasts that were typically losing a battle against gravity into two white torpedoes that were aimed right at me. I ran my hands over them and could detect the soft flesh restrained within but this article had taken the sexy right out of them. I examined it briefly before reaching behind her and unfastening a long row of hooks. I slid the bra down her arms and set it aside then started to caress the soft, smooth flesh that was now exposed. As I was losing myself in her tits once again, Dixie was still riding my cock and had dropped a hand down under her skirt to caress her clit as she did. Her pussy was already hot and slippery and felt amazing as it slid up and down my tool, but it just felt better the longer she rode me. I was pushing up into her, my ass coming up off the seat, just to try to help her feel even more pleasure and I started to wonder if we had the car visibly rocking. Her tits were definitely bouncing and, when I wasn't fondling them, I was watching them with a smile on my face. I could feel the first stirrings of my orgasm but knew that she'd beat me to the punch as she typically did. One of the many things that I liked about her was that I never had to worry about leaving her high and dry. I wasn't surprised when she let out a longer moan and her body began to tremble. She rode me slower as she came and I continued to caress her hard nipples. When she'd finished cumming, she sat on my cock and smiled that dazzling smile at me as she caught her breath. "How about we get rid of this dress," I said, thinking that it would be even hotter to have her completely naked in the backseat of a car at the drive-in. She moved off of my cock and slid the dress down to her ankles, throwing it over the front seat. I got my pants off, too, to give me a bit more range of movement, then had her turn around. As she rested her arms on the front seat and her chin on her arms, I held her by the hips and slipped into her from behind. There was enough light that I could see the slight jiggle of her awesome ass each time my hips tapped against it, but I knew that her tits were swinging freely, too, so I slid my hands up to cup them. My orgasm was building more quickly now and I was fucking her harder, not necessarily wanting to cum faster but enjoying the level of pleasure I was feeling. My hands moved back to her waist so that I could pull her back each time I pushed into her, my hips smacking against her ass. My cock swelled even more the closer I got to cumming and Dixie was moaning louder as I reached the verge of an orgasm. With a soft cry of pleasure, I started to spew into her, thrusting with each spurt until I was spent. She sat back on my lap with my cock still embedded in her until it slipped out and we kissed. The movie was well underway by that point and there was no point in trying to catch up, but we watched it for a bit while we recovered. Before we left that night, we did it doggie-style in the backseat and I fucked her tits. I really thought I was completely spent as we headed toward her high-rise, where she was okay with me dropping her off this time. She asked me to park in one of the lots surrounding it, however, and went down on me in the front seat until I spewed down her throat. "I truly believe that every good date should end in this fashion," she said, wiping her mouth before she got out, "and this was absolutely a good date."