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 Twenty-six
My focus wasn't entirely on fucking women from work just because I'd found a system that was working pretty well. As always, there was recon going on for women I hadn't been with, there were revisits to women I'd previously visited successfully and there were new dream encounters, some with women from work and some not. There always seemed to be something or someone that inspired me and I wasn't anywhere close to getting tired of any of it. Social media, of course, was full of inspiration but occasionally something would really jump out at me.
A good friend of mine has a couple of older sisters who I also keep in touch with on social media because I've known them pretty well for so long. I'd definitely crushed on his oldest sister, Kathy, back when I'd see her regularly while I was hanging out with him and they all still lived at home. Now when I'd see her postings on social media, the feelings that I'd experience reminded me that, even if it wasn't a major one, I still carried a bit of a torch for her. Naturally, I'd invisibly visited her on multiple occasions and was definitely interested in getting with her and her MILF bod but I really wanted to find a good situation to get our younger selves together and experience her in her early-20s. Social media finally gave me a good situation when she took a cruise to Alaska then posted a ton of photos. I commented on a few of the photos and asked some questions so I got some response from her which I expected would help my dream scenario.
I had immediately thought about how well things had gone with Shelley when I'd whisked her away to a cruise ship but I didn't want to just replicate that with Kathy. Since she'd left out of Seattle, I started her dream with the younger but still adult versions of us sitting on an upper deck of the ship, looking out at the Seattle skyline. She seemed surprised when she found a young version of me sitting beside her then somehow must have realized that she was a younger version of herself, too. I gave her a moment to process what was happening then began asking questions about her cruise as I had on social media. She was responding and must have come to a realization that this wasn't actually happening but was something triggered by our recent interactions and her recent vacation.
"Can I see the stateroom you stayed in?" I finally asked.
"Yeah, it has a verandah," she said, excitedly, "so the views were just amazing."
We got up and headed inside to an elevator lobby and, as we were waiting, she could see a reflection of herself and confirmed that it was a younger version. Since I was close beside her, I slipped my arm around her.
"You knew I had a crush on you back then, didn't you?" I asked.
"I suspected," she replied, "but we couldn't have done anything anyway because you're Robbie's friend."
"What about now though?" I asked, "We're both adults and we're on a cruise together."
Before she could answer, the elevator finally arrived, by my design of course. She stepped toward it but took my hand as she did. Inside the elevator alone, again by my design, we slipped into each other's arms and kissed, more romantically than passionately. When the elevator stopped, she took my hand again and led me down a hallway which was all coming from her memory because she had not posted any photos of the hallways on the ship, or the elevators for that matter. Outside one of the staterooms, she stopped but must not have expected to have a keycard on her so I produced one and handed it to her. She used it to unlock the door and we stepped inside. You could see the entire thing from just inside the door: the tiny bathroom immediately to the right, then the bed, then a sitting area with a small couch and finally the door out onto the verandah.
"Do you want to see the verandah?" she asked as the door closed behind us and we stood by the foot of the bed.
"Not yet," I replied and took her in my arms again. We kissed but this time progressed quickly to making out passionately. I dropped my hands down to her ass and massaged it while pulling her against my stiffening cock. I ended up picking her up and carrying her onto the bed where we continued making out with her lying on her back and me on my side. Both she and her sister had amazing tits and, though I'd enjoyed the opportunity to see them as they currently were during my recon visits, I was pretty psyched to see and fondle and fuck the younger version of them. This started with fondling them through her shirt and bra while we were making out. I could have had her braless if I'd wanted but I was looking forward to slipping her bra off of her which I'd most definitely fantasized about many times back when I'd been crushing on her. I also didn't have her wearing what she'd had on the day she actually left on her cruise, though I had seen photos, instead opting to have her wearing shorts and a t-shirt that I had a strong memory of seeing her wearing at this age. The shorts were brief enough that her long legs looked even longer and the t-shirt was snug enough to display her ample boobs.
Rather than unfastening her bra as we were making out to get my hands on her bare boobs, I slipped my hand down between her legs, first massaging her pussy though her shorts then slipping my hand into her shorts. I caressed her pussy though her panties briefly before slipping my hand into them, as well. My fingertips passed through her bush then found her pussy practically overflowing with juices. I slipped a finger easily inside, finding her both snug and incredibly wet. While we continued to make out, I was alternately sliding my finger in and out and lightly caressing her clit. She was rocking her hips and, after a while, she had to pull her mouth away from mine so that she could moan. She pressed her face into my neck and moaned longer and louder as her pussy was becoming even wetter and more engorged. I was looking forward to slipping my cock, which was now fully rigid, into her snug, slippery pussy but I wanted to make sure she had at least one orgasm first. Again, it wasn't that I was worried that I'd spew immediately since I had some control over that but I wanted to make sure that her dream put her needs first.
She was holding onto me more tightly and tensing up somewhat the longer I was stimulating her, though her moaning was pretty consistent. She finally went limp and cried out, her entire body then shaking as her orgasm started. I continued gently caressing her clit as she was cumming, hoping that would draw out the pleasure she was feeling. Whether it did or not, her orgasm appeared to be both long and intensely pleasurable. When she finally went still and quiet, I slipped my hand out of her panties and tasted her flavor on my finger. She lay there catching her breath and recovering for a moment but was soon ready to continue.
"Let's fuck," she said, laughing when I raised my eyebrows. I kissed her then started to get up on my knees, pulling her up with me. I grabbed the hem of her t-shirt and began to raise it, so she lifted her arms and her bra was quickly revealed. As I fondled her tits through her bra she was working on getting my shirt up over my head so I had to quit. I went back to fondling them for a moment before reaching behind her to unfasten her bra. This was the moment of truth for me or at least one of them. I slid her bra down her arms, revealing her substantial tits topped with large areolas and hard, thick nipples. I could have stared at them all day but, once I had set her bra aside, my hands went right to them, caressing the soft, smooth flesh. She indulged me for a minute or two but then reached down to massage my rigid cock through my shorts, reminding me that she was eager to fuck. I figured we could accomplish that and I could fondle her sweet boobies at the same time.
I unbuttoned and unzipped my shorts while she continued to massage my cock then she reached into my shorts and massaged it through my briefs. When I flopped onto my back and started to slide my shorts and underwear down she gripped my rigid cock as it sprang out, stroking it as I stared at her tits, bouncing and swinging. She ended up releasing my cock and helping me get my shorts and underwear completely off then slipped out of her own shorts. She pushed them down to her knees, leaving her panties in place, then stood on the bed and stepped out of them while I gazed up at her wearing nothing but panties. She was tall with long legs and, of course, big boobs and her dark brown hair was long and mostly straight. If my cock hadn't already been rigid, it wouldn't have taken more than seeing her standing there. Rather than just lay there and watch, though, I sat up and grabbed her panties at her hips, sliding them down myself. Her dark brown bush was neatly groomed and, if she'd moved a little closer and straddled my face, I'd have been more than happy to eat her pussy. Instead, though, she stepped out of her panties then got down on her knees again while pushing me onto my back. She straddled me and, as she was guiding my cock toward her pussy, I reached up to fondle her big, beautiful tits.
She lowered herself onto my cock, both of us moaning as her snug, slippery pussy easily engulfed me. She paused briefly then began to move slowly up and down on my tool. While I was fondling her boobs, I was initially gazing at her pussy as my cock disappeared repeatedly into it. My gaze did move up to her face, not just because it was pleasant to look at anyway, but also to watch her expression as it displayed both pleasure and passion. It was nice to see that finally getting the opportunity to fuck her was not just meeting my expectations but she seemed to be getting a fair amount out of it, too. Her pace was gradually picking up and, as her boobs started bouncing, I moved my hands around to caress her ass so that I could watch them. I was pushing up into her each time she came down, endeavoring to give her the full length of my cock.
I didn't know for sure whether, because she'd just had an orgasm not long prior, she'd be more likely to cum quickly with a second one but I didn't really want this to happen too quickly since it was something I'd wanted for so long. My desire at that moment was to enjoy the opportunity to finally have sex with her for as long as possible. Of course I also wanted the door to be open for future encounters but, since this first one was so highly anticipated, I also wanted it to be highly memorable. I didn't think that I had control over how long it took her to cum or how much pleasure she experienced but at one time I didn't think I could visit people outside of my body and convince them that sex with me was occurring in a dream. When Kathy continued to ride me harder and faster while clearly experiencing a great deal of pleasure as she was building toward a momentous orgasm, I started to wonder whether any of it was my doing. My wondering was brief, however, because her pussy also just continued to feel even hotter and wetter the longer she was riding me so my focus was on just how damn good that felt.
As she was clearly getting closer to cumming, I was perfectly okay with it because, again, it was her dream and I wanted her to experience a high level of pleasure. I also had a plan for after she'd cum so I could further enjoy her big boobs. When she finally was right there, she dropped down onto my cock and just sat there then, a moment later, she let out a cry and started shaking. Since her boobs were no longer bouncing, I brought my hands around from her ass to fondle them some more. Her orgasm appeared to be another long and highly pleasurable one which, as always, made me glad that she was getting at least as much out of this "dream" as I was. When it was clear that she'd finished cumming, I rolled her to the side and slipped out of her pussy. I moved up and straddled her, laying my cock between her sumptuous breasts, then brought them together against it. As I felt the soft, smooth flesh both in my hands and against my cock, I started to slowly slide my cock between them. The feeling was incredible, despite having just slipped out of her snug, slippery pussy. This was something I also wanted to make sure was not over too quickly.
Gazing down, not only at her tits, large areolas and hard, thick nipples, but also at her face as she watched my cock appearing repeatedly from her cleavage, was even more arousing than just the feel of her tits against my cock. I was less concerned about making sure this lasted a sufficient amount of time than I had been with her riding my cock but I still planned to enjoy it for a bit before cumming. By this point, I fully expected that this would not be my only opportunity and that I'd also be fucking her titties in their current MILF form before too long after this dream. I knew that she wasn't really getting anything out of this but she had cum twice already so I figured it was fair to indulge myself, especially given how incredible her tits were. I also didn't anticipate being done once I'd cum; I was planning to enjoy her young body for a bit longer before wrapping up this dream.
