All the Senior Ladies

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.