Dream Lover Pt. 14

Note: you will understand this story a lot better if you read at least Part One first though I recommend reading all previous parts.

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Chapter Nineteen

Despite my successes with both Shelley and Inez, I hadn't found another opportunity where I felt comfortable attempting to introduce a casual acquaintance, much less a stranger, into one of my sexual daydreams. I was still concerned about a potential freak-out and had not encountered a situation yet where I was confident enough to give it a shot. That didn't mean that I wasn't constantly considering the women around me, especially the ones I saw on a regular or semi-regular basis. As I had with my dream visits, I just needed to work out a process that would have a high potential for success. In the meantime, I was still expanding my dream visit capabilities with women I already knew since that seemed to be working well and continuing to get better. Among those women I knew, I was also looking for someone open-minded enough like Shelley for a daydream escape but the nighttime dreams being expanded to any place, any time and any age still offered a lot of possibilities.

Right around the time I'd graduated from college, there had been three women in my life that I had been very interested in getting naked with: Linda, Irene and Theresa. Unfortunately, Linda had married young, Irene was dating one of my best friends and Theresa no longer lived nearby so the logistics hadn't been favorable with any of them. Since that time, while they were no less attractive to me, none of them quite had the figure that they'd had back in our early twenties. Of course, this didn't mean I was not interested in making a dream visit to each of them, and they were each definitely on my list but, with the new ability to go back to when I'd originally wanted to get with them, I could see more potential, not only for sexual pleasure but also for being able to convince them that they were just dreaming it. As I did my recon on each of them, I was really torn and ended up pretty sure that I'd be coming up with dream scenarios for both their current and former selves.

When it finally came down to it, I decided to start with Linda for a couple of reasons. One was that, once I'd really gotten to know her better after college, I'd thought that there was potential and chemistry between us but the timing just never seemed to work out; one of us always seemed to be in a relationship with someone else. I figured if she'd felt the same connection, a sex dream wouldn't seem so outlandish, even after all this time. The second reason was that, during my recon, I'd picked up on a bucket list desire of hers to vacation at a villa right on the Mediterranean, with the white sands and the clear blue water. This gave me the perfect place to take her. Although she was happily married for a second time, more happily than the first time for sure, she'd also had several children with her second husband and it didn't look likely that they'd be heading to the Mediterranean any time soon.

Linda was a cute brunette, on the petite side but with substantial tits. Although her tits didn't stand up as firmly as they once had, she was still cute with a decent figure, so while I intended to thoroughly enjoy her pre-children, nineteen- or twenty-year-old body, I was also planning to plant a seed that would make it easier for me to pull off a dream visit with the MILF version of Linda. When I felt that I'd performed enough recon to easily take her into a faux dream, I picked the night and waited as she got ready for bed. Once the lights were out, I waited patiently for that sweet spot when she was almost but not quite asleep. When the time felt right, I sat on the edge of her bed and touched her bare shoulder, instantly taking us to a bedroom where the late morning sun made it brighter than it had been a moment earlier.

"Good morning, sleepyhead," I said, seated beside her with my hand still touching her shoulder, "Here's your coffee. Breakfast is on the patio, whenever you're ready."

I set a cup of coffee on the nightstand and leaned down to kiss her head then got up and walked out the French doors onto the patio. There was a table in the shade with food and more coffee. The view was magnificent so I took a seat and grabbed my own cup of coffee, looking out upon the sea despite an almost overwhelming desire to watch her come outside. I was not only curious to see her reaction but also to see how she looked. There was a robe at the foot of the bed, so I didn't expect her to walk out naked, which might have actually inspired me to ignore the sea, but she'd been naked in bed by my design and I expected that she also would be under the robe. I was really, really looking forward to seeing more of her bare flesh.

"I'm confused," I heard from behind me so I turned to look, "What's going on?"

"It's your dream vacation, sweetie," I said, "while you're still young enough to thoroughly enjoy it."

"So, this is a dream?" she asked, continuing over and taking a seat.

"Isn't it?" I asked, wanting to leave the confirmation to her.

"Well, I looked in the mirror when I got up," she said, sipping her coffee, "and I obviously haven't had any kids. I look like I'm about nineteen or twenty. So do you."

She reached for a croissant and nibbled it absently as she was pondering the situation. I enjoyed some fruit and went back to admiring the view while awaiting her verdict. I don't know if it was the view itself or being where she actually did dream of being or whether she was just waiting to wake up and it didn't happen but it didn't take long before she'd made a determination.

"I guess it must be a dream," she finally said.

"So what do you want to do?" I asked and she looked my way. I was definitely more fit than I had been at nineteen or twenty and was wearing only a swimsuit. Her gaze gave her away as she appraised my tan physique.

"I'm definitely not going to sit here, waiting to wake up," she replied, "I'm going to enjoy this while I have the opportunity, even if it turns out not to be real."

"Your swimsuit is inside if you'd like to join me in the water," I said, "and you don't even need to wait 30 minutes after eating since this is a dream."

I watched her as she headed back inside, very pleased with how things were going. The swimsuit I'd conjured for her was a pretty brief string bikini, which I didn't expect that she'd have any issue with, not only because she had her younger figure to fill it but also because it was probably borderline modest for a Mediterranean beach. While she was gone, I worked on my poker face for when she returned and tried not to think of how she looked naked as she was slipping into the bikini; I was hopeful that I'd find out soon enough. I'd stood and walked to the edge of the patio before she'd returned so, when I heard her come back out, I turned and managed to keep my jaw from hitting the ground, instead smiling and nodding appreciatively. She looked absolutely outstanding and her tits bounced a little as she walked toward me.

"You look amazing," I said, not even slightly stretching the truth.

"Thank you," she replied, with a slight blush, "I wish my body still looked like this but we're in the Mediterranean and, like you said, I'm young enough to enjoy it."

I reached for her hand and we walked to the water, looking up and down the beach but not seeing another person or structure. The water was perfectly temperate so we were soon in almost up to our chins, though she reached her chin before I did as she was a bit shorter. We floated and bobbed on the minimal waves and every time she leaned backwards, her tits jutted out of the water while I tried not to gawk at them. Despite how comfortable the water temperature was, her nipples were hard and pressing out against her bikini top. I really, really wanted to get my hands on her tits and my tongue on her hard nipples but I also wanted her to make the first move since this was supposed to be her dream. Fortunately, she had apparently accepted that this was a dream and that I was there rather than her husband for some reason, though I don't know how much thought she had actually given it. As she'd said she would, she was enjoying the opportunity and, ultimately, that ended up not being limited to just the clear blue water.

Our first physical contact was not sexual or romantic; it started with us just grabbing or pushing each other as we were goofing around and progressed to her climbing onto my back as I went into deeper water. Eventually, though, she wrapped her legs around my waist and her arms around my neck on my front side and we were soon kissing as I supported her with my hands on her sweet ass. I wasn't planning to fuck her in the water, despite how hard my cock was, because I wanted to get her naked and thoroughly explore her nubile body. There was a cabana covering what was essentially a bed up on the patio and I'm sure she'd seen it and probably assumed her own subconscious had created it. Whether she figured her subconscious was telling her to fuck me or she just saw the bed and decided to use it for that, she wound up unwrapping herself and taking my hand to lead me out of the water.

"Why didn't we ever end up dating?" she asked as the water grew shallower.

"Well, if we'd dated, you might be married to me now and not have your lovely children," I replied, "or, if we'd dated then broken up, we might not even like each other now. Dreams are much less complicated than wondering what might have been."

As we crossed the white sand, of course it clung to our wet feet but there was a spot to rinse and some towels to dry before we climbed onto the big bed so we weren't rolling around in sand. We crawled onto it and lay together in the middle, immediately beginning to make out. I could only go so long before I had to fondle her big tits so I maneuvered her onto her back and lay beside her as we continued to make out. I brought a hand to her tit and caressed the soft flesh and her hard nipple through her bikini top, switching from one to the other before reaching behind her neck to untie her top. Pulling it down, I resumed caressing her tits, feeling the smooth skin and her hard nipples against my palm. They were, of course, monumental and finally getting my hands on them was everything I'd hoped it would be. I wasn't sure if fondling them was doing anything for her, though I hoped that gently brushing my palm over her hard nipple was stimulating.

I resisted the urge to see them for as long as I could, solely because I was definitely enjoying having her tongue exploring my mouth as mine explored hers, but ultimately I had to start kissing my way toward them. I kissed her neck and down over her chest then raised my head and admired the big beauties before beginning to lick and suck her hard nipples. This at least caused her to moan as I alternated back and forth between them. Her areolas were quite large so I ran my tongue around them, as well, in case that provided her with any pleasure. Given that my cock was like a steel rod by this point, I considered that her pussy was probably wet and figured that I could provide her with even more stimulation as I indulged myself with her big titties. I slipped a hand down over her flat stomach and over the front of her bikini bottom, feeling her bush through the material. I ran my fingers over her pussy through her swimsuit briefly before slipping my hand into it. Her bush was trim and well-groomed and, just below it, I found her pussy overflowing with her juices. The only thing that probably could have distracted me from her succulent tits was the idea of slurping up her juicy pussy.

Before I headed even further south, I was gently stroking her clit alternately with sliding my finger in and out of her snug, slippery pussy. Between that and still licking and sucking her hard nipples, I knew that she'd be heading for an orgasm but I decided I'd rather get her the rest of the way there with my face buried in her pussy. Slipping my hand out of her bikini bottom, I got up on my knees and, as I was gazing at her awesome tits, I moved down the bed then started to untie the strings on her hips, holding her bikini bottom together. My gaze shifted down so that, as I started to remove her bikini bottom, I was watching as her dark brown bush was revealed. As I'd expected, it was neatly groomed and, as I was tossing her bikini bottom aside, I repositioned myself between her spread legs. I lowered my head toward her pussy, kissing around her bush before running my tongue up along her slit, causing her to moan.

I lay on my stomach as best I could with my cock as rigid as it was. After slurping up the juices that she was producing and realizing that, the more I slurped, the more she produced, I switched to licking and sucking her clit while sliding a finger in and out of her pussy. She started moaning even louder and I suspected it wouldn't take very long before she was cumming. Of course, I was in no rush to make her cum, wanting only to make sure that she experienced the highest level of pleasure, but I was definitely looking forward to slipping my achingly hard cock into her. I was also in no rush because I wanted to savor this opportunity to have my head between her thighs, having thought about it so many times, especially in the last few days leading up to this dream.

I could feel her pussy becoming even hotter, wetter and more engorged the longer I was eating it and she was moaning and writhing more, too. Gazing up along her body, I could barely see her face beyond the mountain range of her tits, which were standing upright firmly. I could tell, though, that her eyes were closed and the expression on her face seemed to indicate a high degree of pleasure being experienced, which had been one of my main goals. When she started tensing up while holding my head tightly, I knew she was close but I didn't change anything because my technique seemed to be working just fine. Right before she came, she went momentarily quiet and rigid then went completely limp, shaking and crying out as her orgasm overtook her. I continued to eat her as she was cumming, feeling her pussy flooded with even more lubrication. Only once I was certain that she'd finished cumming did I raise my head and slip my finger from her pussy.

I sucked her juices from my finger then crawled up next to her, further admiring her naked body as I did. We went back to making out but, when she reached down and discovered how rigid my tool was, she pushed me onto my back and got up onto her knees. As I stared wide-eyed at her body, she finished removing her bikini top then untied the drawstring on my swimsuit and slid it off. Once she'd cast it aside, she was immediately straddling me and guiding my cock toward her pussy. We both moaned as she lowered herself onto it and just sat there for a moment, feeling it filling her snug pussy. I reached up to fondle her big tits while I waited for her to start riding my cock, but I didn't stop fondling them once she started. She was initially moving up and down pretty slowly, which still felt absolutely amazing given how snug and slippery her pussy was. As she gradually picked up the pace, it only felt even better. Eventually, she was riding hard and fast enough that her tits were bouncing steadily, which would have been the only thing that could have gotten me to remove my hands from them. As I was watching them bounce, in danger of becoming hypnotized, I reached around to caress her sweet ass instead.

Although my attention was on her bouncing tits, I was absolutely relishing the pleasurable feeling of her snug, slippery pussy sliding up and down my tool. It was good that she was setting a pace that started slowly and gradually increased; I doubt I could have resisted fucking her hard and fast had I been in control. Of course I could feel my orgasm beginning to build from the second my cock had been engulfed in her sweet pussy but it also appeared that she was headed for a second one herself. When I could manage to draw my attention away from her tits, I noted that the expression on her face indicated that she was again experiencing a high degree of pleasure. She was undeniably cute, both as a twenty-something and as a MILF, which was not at all lost on me even though I seemed to be strictly focused on her hot body. That said, for the moment my attention was mainly on her bouncing tits. With my hands on her ass, I was pushing up into her each time she dropped down, which gave her tits just little more jiggle.

It didn't surprise me or cause me any consternation when she dropped down onto my cock and just sat there for a moment. It was just brief pause before her body started shaking as she experienced another long and apparently intense orgasm. I went back to fondling her tits as she was cumming while watching an expression of pure ecstasy on her face which made me happy that I'd been able to help put it there. When she'd finished cumming, she sat there for a moment catching her breath before moving backwards, my cock slipping out of her. Kneeling between my spread legs, she took my cock in her hand, pumped it while licking my balls then engulfed it in her hot mouth. I moaned due to the sheer pleasure her mouth provided but quickly pulled a couple of pillows up under my head so I could experience the visual pleasure as well. This was where I more fully appreciated how cute she was as my cock disappeared into her mouth and she'd occasionally gaze up at me. I was so happy not only that this was actually happening but also that she appeared to be enjoying the whole experience just as much as I was. Her talent as a cocksucker was undeniable and I suspected that, when she was actually that age, she probably wasn't quite as good so I was glad to have the MILF skills with the twenty-something body.

I could feel my own orgasm building as a result of her talent but she did manage to draw the pleasure out as I tried to just relax and enjoy it. I didn't necessarily want to be done having her blow me but I knew that my orgasm was going to be monumental. I savored every second and knew that I'd be working on a way to get my cock into her talented mouth again. As my cock swelled even more the closer I was getting to orgasm, she remained undaunted though she adjusted her technique to get me to cum rather than continuing to draw out the pleasure. When I exploded into her mouth with a grunt, she swallowed my load and continued to suck me off until I was completely spent. She let my softening cock fall from her mouth and crawled up to lie beside me.

"That was outstanding," I told her.

"Thanks," she replied, "it has been a long time since I sucked a different guy's cock, even if it is just in a dream. I'm glad it was yours, though."

"So am I," I said, "I'm going to have to figure out how to get into your dreams on a regular basis."

"Well, after this dream," she said, "I doubt I'll be going to bed without thinking of you first for a while."

This, of course, absolutely worked in my favor, though I'd argue that future dream visits would be something we'd both benefit from. We lay there for a bit, just enjoying the scenery and each other's company while I was deciding that I wasn't quite ready for this dream to end yet. Fortunately, she didn't seem to be ready, either.

"There's no one else around, is there?" she finally asked.

"I haven't seen anyone," I replied.

"I wonder why I dreamed us in swimsuits then," she said.

"Presumably because that's how we'd typically swim," I suggested.

"I think we should go skinny dipping," she said.

"Let's go," I replied. We got up and, as I watched her walking naked from the patio to the beach to the water, I could feel my cock beginning to revive. Once again, the water felt perfect so we were quickly in and mostly submerged. This time, however, I was caressing her ass and fondling her tits as she assisted in the continuing revival of my cock. We were "swimming" but we couldn't seem to keep our hands off of each other and, after making out passionately as well, we were pretty worked up again. I picked her up and guided my cock into her as I was standing and she was half floating and half hanging onto me. Her pussy felt outstanding and, based on the noises she was making, fucking like this felt good to her but I couldn't do much more than hold her ass; it was too difficult to continue making out and I couldn't see or fondle her tits. Ever the trouper, though, I stuck with it while I was thinking of something other than going back to the cabana. Glancing back toward the beach, aside from the cabana on the left and the table where we'd been sitting just outside the French doors, there was a chaise on the lower patio on the right. It was wide enough to accommodate two and well padded. I didn't even need to think about it.