Dream Lover Pt. 13

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An attempt to take a MILF on a wide-awake daydream vacation.
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Part 13 of the 25 part series

Updated 06/13/2023
Created 03/04/2018
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Irish Moss
Irish Moss
2,369 Followers

Note: you will understand this story a lot better if you read Part One first.

***

Chapter Eighteen

Once I'd become aware that I could bring my dream subjects along to different places and times just through physical contact, I'd initially limited those interactions to bedtime to pass them off as dreams. With the accidental encounter on the train, I was still presuming that, if I just randomly touched someone and intentionally took them off somewhere, there was a high likelihood of a freak-out that might continue even if I immediately took them back. Other than that was the issue of just randomly touching people to make that skin-on-skin contact. If I just grabbed someone's hand, took them away somewhere, they freaked out and I brought them back, where they were still freaking out and I was holding onto them, it had high potential for more than just awkwardness.

I had a pretty well established methodology to determine where anyone who struck my fancy lived or slept, so it just seemed easier to stick with the dream scenario. The more I thought about it, though, the more I realized that, if I could figure out a more-or-less foolproof way to make incidental physical contact with a stranger and take them someplace that wouldn't cause a freak-out, it would save me a great deal of recon time and effort. Of course, time was irrelevant but I was just thinking that it'd be nice if I saw somebody and could get naked with them without a lot of planning. I might not be able to get it to work and it might take a lot of experimenting and testing but, since time was irrelevant, I figured it could end up being worth it in the long run.

Between the dreams with people who I didn't have a history with and the regular encounters on the train with my new Latina dream lover (whose name, it turned out, was Inez), I always seemed to have a dream scenario ready to go. I hadn't actually had an opportunity to employ any of them with a random stranger to test out the feasibility of such an encounter and was still considering some of the logistics when another opportunity presented itself. Because I rode the train to and from work on a daily basis, there were a lot of people like Inez who I saw regularly but didn't necessarily know. Shelley was a different story because we'd been introduced by my neighbor who used to ride the train and who used to work with Shelley. I also knew from this neighbor that Shelley's husband was a slacker who couldn't hold down a job but also couldn't be bothered to take care of the house or the kids when he wasn't employed. Shelley worked full-time then went home and took care of everything there, too. It was no wonder she quite often looked exhausted. Despite this, though, she was still a MILF. She'd been on my list but I'd never quite gotten around to figuring out where she lived to do some recon. One morning, an opportunity presented itself and I couldn't resist taking a shot. Shelley got on the train, looking exhausted and took the empty seat beside me, giving me a weary smile.

"Everything okay?" I asked.

"I'm just stretched a little thin with the kids, the husband and the job," she replied, "which, unfortunately, doesn't actually translate into being thin."

"Oh stop it," I said, "you look great. It sounds like you need a vacation, though."

"I wish I could afford one," she replied, "both financially and time-wise."

"What if I could help you escape long enough to provide some tranquility," I asked, "without impacting your time or your finances? Do you think you could handle something a little unconventional?"

"What like meditation or something?" she asked, "I think I'm way beyond that at this point."

"Not quite meditation," I replied, "but it would be a pretty dramatic mental escape that would have an incredibly positive impact on your physical self."

"What the hell," she said, "I'm willing to try anything at this point."

She definitely sounded skeptical but also at her wit's end. I didn't expect a freak-out, though I did think it might take some convincing that she hadn't lost her mind. I knew the exact scenario for her so I reached over and touched her hand. Her eyes went wide as she realized we were no longer on the train. She was standing in front of me rather than sitting beside me, which was how I could see this. She was wearing a big, fluffy robe, just as I was, and we were both standing beside massage tables that were set up about ten feet apart. There were also a couple of masseuses nearby.

"Holy fuck," she exclaimed, "Did I crack? Have I lost it?"

"No, Shelley," I replied, "everything is cool. I told you I could take you away but, physically, we're still on the train. We can stay here as long as it takes to get your head straightened out then return to the train at the exact moment we left, except you'll feel 100% better. I promise you that you are still mentally sound and I've just taken you on a vacation outside of your body to get your body and your mind some rehab. Once you're ready, we'll be back on the train, heading to work, and no one will ever know we left except for the two of us."

"Okay," she said, "if I have lost my mind, I might as well enjoy it, and if I haven't I should still enjoy it."

"Attagirl," I said and started to untie my robe. I turned toward the table behind me and my masseuse approached. With my back to Shelley, I removed my robe, exposing my bare ass to her, and handed it to my masseuse then slipped under the sheet on the table. I made sure to expose my cock briefly to Shelley as I situated myself while she still stood there. I placed my face on the doughnut-shaped pillow, never looking over at Shelley because I was hoping to see her naked soon enough. She apparently stripped down as well and took a similar position on her massage table. We managed to have a conversation through the pillow holes, mostly just clarifying things further for her regarding what was going on and how we got where we were. Once we were on our backs, the conversation was a little bit easier and she seemed to be more open-minded the longer she was being massaged. When my massage was finished, I sat up on the edge of the table with the sheet still over my lap but otherwise naked.

"Feeling better?" I asked.

"I feel amazing," she replied, "and even if this isn't really my body that is being massaged, I really believe that I will feel it in my body when we go back."

"And, like I said, we're in no rush to go back," I reminded her, "so, once we're done here, we have a couple of options: there are showers where we can go separately to wash off the massage oil or there is a room where couples can go to wash each other to make sure all of the oil comes off. What's your preference?"

I was trying to sound offhand but I'd have been disappointed if she'd decided to shower alone.

"Well, since this isn't really happening physically," she replied, "I guess there's nothing wrong with getting cleaned up together. It doesn't make sense to go off on my own since you're my guide for this experience. I trust that you'll continue to provide guidance to help me get the most out of this."

I think she was trying to sound offhand, as well, but I got the vibe that she was interested in having some consensual fun. I was happy that she was embracing the situation and, between her and Inez, I was feeling more confident already about the possibilities of spur-of-the-moment daydream encounters. My masseuse appeared with my robe, so I slipped into it without exposing myself fully to Shelley, in part because I was at half-mast just thinking about getting her all cleaned up. My fluffy robe covered my semi-erection, though, and I stepped to the side with my masseuse, ostensibly to discuss getting cleaned up together rather than individually. Really, it was just to give Shelley an opportunity to get up and get into her robe without me staring at her. Once she was ready, my masseuse led us through a door, down a short hallway with a couple of other doors then through a door at the end of the hallway.

The room was everything I wanted, which made sense since it had come from my imagination. There was a large, rectangular tub in the middle, set into the floor. It was about as deep as a hot tub with seating around the inside of it and big enough for two people to comfortably bathe together. There were hooks for our robes, piles of towels, and all kinds of soaps and body washes and shampoos, loofas and sponges but the best thing was that it was lit entirely by sunlight pouring through a huge skylight. Shelley and I stood there for a moment, taking it all in, before I turned to her and untied the belt of her robe. Rather than immediately opening it, though, I moved around behind her once it was untied and slipped her robe off of her shoulders. I admired her from behind as I hung her robe then I slipped out of my own and hung it as well.

I took her hand and led her to the tub where we stepped down onto the seat then I had her sit on a cushion that was conveniently positioned on the edge. I stepped down off the seat and turned to face her then knelt on the seat directly in front of her. I was admiring her body and I know that she noticed that my cock was nearly rigid but rather than just starting to fuck her, I first leaned in and kissed her. We progressed from kissing to making out as I fondled her boobs, which were on the larger side but not huge. Her nipples were hard, though, so it didn't take long before I was lowering my head to lick and suck them. I continued to head south, kissing my way over her ribs and stomach until I was staring at her bush. It was dark brown, despite the rest of her hair being reddish-brown, and it was nicely groomed so I dove right in and started licking her slit. She let out a moan and leaned back while spreading her legs even more. I glanced upward as I was lapping at her pussy, admiring her curves and appreciating her body and the opportunity to see her naked. My cock was rigid but I was going to make her cum first before slipping it into her.

After slurping up her copious juices for a bit, I focused my tongue on her clit as I slipped a finger into her pussy. It was hot and wet which made me even more anxious to slip my cock into her but instead I added a second finger to the first. As I was sliding them in and out, I was licking and sucking her clit which had her moaning even louder and longer. She reclined even farther, conveniently finding a big pillow behind her, while reaching down to hold my head as she humped her pussy toward my face. I glanced up again, seeing her tits squeezed between her arms, and thought that it would probably feel awesome to fuck her tits before we were back on the train. This inspired me even more to make sure that she had a highly pleasurable orgasm, figuring the more pleasure she experienced, the more generous she'd feel when it came to my satisfaction.

I didn't really change my technique any but just made sure that I was focused on getting her the rest of the way there. Her pussy was becoming even wetter and more engorged the longer I was eating her and the louder she was moaning. She was starting to tense up slightly while arching her back a little so I knew she was getting pretty close. I was enjoying the opportunity to eat her pussy while she was laid out naked before me but I was also looking forward to slipping my cock into her now even hotter and wetter pussy. With a gasp, she finally went limp as her body started shaking but I just continued to devour her pussy, hoping to provide the highest level of pleasure as she was cumming. As I'd hoped, her orgasm appeared to be intensely pleasurable and it was definitely a nice long one. I didn't stop sliding my fingers in and out or licking and sucking her clit until she'd gone still and had let out a sigh. At that point, I raised my head, slipped my fingers from her pussy into my mouth and straightened up on my knees.

Looking over her naked body, I couldn't wait any longer to fuck her so I grabbed my cock and guided it to her pussy. We both moaned as I easily slipped my full length inside her. Her hot, wet pussy felt even more amazing than I'd expected so I immediately started to slide my cock in and out of her. I knew that continuing to kneel was going to get uncomfortable pretty quickly so, after savoring her pussy for a few minutes, I helped her sit up then picked her up. I turned and stepped off of the seat then lowered us into the water as I sat with her on my lap. She immediately started riding me and, as I leaned back, I started to fondle her tits. Even submerged in the warm water, her pussy felt outstanding and I was enjoying the feel of it moving up and down my cock. Shelley was clearly enjoying it, as well, based on the sounds she was making and how hard she was riding me.

Because of the level of the water, her tits weren't bouncing freely as they would have out of the water. They still had a little bounce and a little buoyancy so I would run my hands around to caress her ass or hold her waist while watching them. Fucking them was still in the back of my mind but, feeling her hot pussy moving up and down my cock, I was definitely more focused on enjoying that at the moment. I could feel an orgasm building but I knew I'd be able to hold it off until she'd cum again. I wasn't thinking about switching positions once she'd cum, though, because I thought we should go ahead and clean up then I could show her what else was beyond this room. I wanted to make sure she got in some significant relaxation and more sex before we went back to the train and on to work.

As she continued riding me harder, making waves in the tub, I started pushing up into her each time she came down to make sure that she was getting maximum penetration. Her eyes were closed and she was moaning continuously while her pussy continued to feel even hotter and wetter than it already had been. I was watching her tits more than her face, though, while holding her waist as I pushed up. I think the water slowed us down just a little but that really just helped to draw out the pleasure for even longer. When she dropped down onto my lap and didn't raise herself up again, I likewise dropped onto the seat and just waited. Suddenly, she started shaking as she cried out, another orgasm ripping through her. It appeared to be another long and intense one, so I was pleased to have helped her get there.

I waited patiently as she rode out her orgasm and gave her a few minutes to recover once she'd finished but then started gently pushing up into her again. She leaned in to kiss me as she went back to slowly riding my cock while I brought my hands up to fondle her tits some more. Since she'd already cum, I more proactively pursued my own orgasm and it didn't take long with her hot pussy riding my cock before it was building up again. I was savoring the feel of her pussy and the feel of her tits, not because I was concerned that I might not get another chance, but because, although Shelley had been on my list, I hadn't really spent much time considering her. Now that she was riding my cock, I was glad that this opportunity had not only come up but also that Shelley had been open-minded about it.

As my orgasm was getting closer, I dropped my hands down from her tits to her ass as I was pushing up into her harder and faster. It ended up being difficult to continue making out so we stopped that with both of us then freely moaning. I didn't expect that she was going to cum again but my cock was swelling even more the closer I got so I presumed that was feeling pretty good to her. When I finally exploded into her, the pleasure was incredibly intense and went on for as long as I was spurting into her. I continued thrusting until I was fully spent but she remained sitting on my cock even as it began to soften. When she climbed off of my lap, it was more to stretch her legs a bit but I also stood and we made out in the middle of the tub before beginning to wash each other.

I figured we'd end up completely worked up again by the time we were done but I kind of wanted to still have that edge as we left there and further explored so that we'd definitely end up having more sex before we were finished and ready to go on to work. We thoroughly soaped each other up, washed each other's hair, rinsed off in the still temperate water then finally climbed out and dried off ourselves and each other. Conveniently once again, there were clothes there for us to slip into but, of course, no underwear. There was a short sundress for Shelley, which she slipped into and had me immediately thinking about pushing it up and fucking her, but I managed to resist the urge. I slipped into a pair of shorts and a cabana shirt and we each donned a pair of sandals then we headed out another door. We passed through a hallway and into a reception area, where we were each handed a tropical drink before we exited the main doorway.

"Oh my gosh," Shelley exclaimed, "we're on a cruise ship!"

"Your vacation should be more than just a trip to the spa," I said and raised my drink in her direction. She toasted with me and we each took a sip then we started walking until we were out on an upper deck. We strolled around in the sunshine, enjoying our drinks and checking things out, both on the ship and off. We had something to eat once I'd shared with her how we wouldn't gain weight or feel full or bloated as well as how we wouldn't get drunk. She was definitely embracing everything about this escape but she did make it clear to me that there was something else she wanted more of.

"Do we have a stateroom?" she asked after we'd seen a lot of what there was to see.

"Of course," I replied, "are you ready to see it?"

"Absolutely," she said, snuggling up against me as we walked. I led her to a door, produced a key card from my pocket and opened it. We stepped into an impressive suite with a huge bed, lots of windows and a large verandah.

"Oh my gosh," she exclaimed, "I may never want to leave here!"

We checked the whole place out before we ended up out on the verandah, watching the ocean going by. I hadn't stopped thinking about how she was naked under her sundress and, out on the verandah, the breeze was lifting it a little, almost exposing her ass. I finally couldn't wait any longer so I moved behind her as she was leaning on the railing and slipped my hands up under her sundress. I cupped her bare tits as I was pressing the bulge in my shorts against her bare ass but that wasn't really going to do it for either of us so I released her tits and opened my shorts. As they dropped to my ankles, I had my cock in hand and was guiding it to Shelley's pussy from behind. We both moaned as I eased it in, finding her pussy already incredibly hot and wet, then I kicked my shorts aside and started to slowly fuck her. She was pushing back against my incoming thrusts right away and, once we had a consistent rhythm going, I slipped my hands back up to her tits again.

I was feeling fortunate once again that she'd not only been so accepting of this experience but also that she was really into the sex. It wouldn't have surprised me at all if one of the casualties of her exhaustion due to all of her responsibilities was her sex life. My initial goal had been just to get her a much needed if brief vacation while I tried to get a little sex for myself but I was certainly glad that she was as into the sex as she was the opportunity to relax with no responsibilities. As she was gradually pushing back harder and faster, picking up the pace, she dropped one arm down from the railing and reached back between her legs to stimulate her clit. Even over the ship's engines and other noise out on the verandah, I could hear her moaning louder and longer while her pussy was once again becoming even hotter and wetter. Had I realized how close she was to cumming, I might have released her tits and fucked her harder and faster while holding her hips but she didn't tense up at all this time; she just suddenly cried out and her body started shaking.

Irish Moss
Irish Moss
2,369 Followers
12