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
The success of my dream visit with Linda had me eager to return but I knew I needed to be patient and space out my visits. Fortunately, I still had Theresa and Irene with whom to coordinate dream visits and my success with Linda had provided me with additional confidence. Drawing inspiration from the Mediterranean beach with Linda, I had a good idea of how to go about it with Theresa so I started with her. Back at the end of high school, a group of us had gone to the beach after the prom to stay up and watch the sun rise. With that accomplished, many of us promptly fell asleep on our blankets, snuggled together under additional blankets for warmth. I just happened to be spooned up against Theresa and, had we been alone, I might have done something more than just pressed my body against hers and wrapped my arm around her. With the others around, including our dates, that didn't seem like the best idea, though I did feel comfortable that Theresa would have been receptive.
In thinking about where our dream should take place, I decided to take things to that next step on the beach back when we were both eighteen but to then transform that scene to a much warmer tropical locale. I'd considered the Mediterranean villa but decided on a more generic tropical beach with just the cabana and bed on a wooden deck with an adjacent shower to keep things simple and focused. As I was developing this plan, I was also doing recon and, as with Linda, the more I saw Theresa undressing and showering, the more I wanted to be with both her eighteen-year-old self and her current MILF self. Once the plan was completely figured out, I took the first opportunity and, as she was just on the verge of dozing, I slipped into bed with her, spooning her as I did that night on the beach, then took her there with me. I suspect it was the crashing waves that let her know that she was no longer in her bed though it also could have been the feeling of being fully dressed. She turned toward me to see who had an arm around her and actually smiled when she saw that it was eighteen-year-old me.
"Remember that night after the prom?" I asked as we looked into each other's eyes.
"Of course," she replied, "I remember wishing it was just the two of us and now it looks like it is."
"So what should we do now that we couldn't do then?" I asked.
"This for starters," she said before reaching up to pull my face closer to hers and pressing her lips against mine. This was going exactly the way I'd hoped it would, meaning it was starting out the way I wished it had actually gone on that night. We were quickly making out as she lay on her back and I was on my side. We had made out briefly on a few occasions during the course of our long friendship but it had been a long time so I was relishing the opportunity to do it again. Of course I couldn't resist bringing my hand up to cup her tit, caressing it through her shirt and bra. I had never done that before in real life and, although I was savoring it, I was soon sliding my hand up under her shirt. As we continued to make out, I briefly caressed each of her tits through the thin material of her bra before unfastening a conveniently located front clasp and releasing them. I resumed caressing each of them, this time the bare, smooth flesh and her hard nipples as she moaned softly into my mouth.
My cock was rigid but I was not expecting to use it here in this scenario mainly because my primary goal was to get her off but also because we were fully dressed and I knew there was an easier way to shed all of our clothes than fumbling around here in this memory. I wanted to get her off then get my cock inside her but there was definitely potential to revisit this scenario and play it out completely. I just wasn't patient enough to do it this first time.
After fondling her bare tits for a bit, I slipped my hand down and first massaged her pussy through her jeans then, upon receiving a positive response to that, I started to open them. I unbuttoned and unzipped her jeans then slipped my hand inside, feeling the coarse texture of her bush through her panties. I caressed her pussy through her panties, feeling the moist heat emanating through them, then slipped my hand inside. Her bush felt well-groomed and her pussy felt hot and wet. As I started to slide my finger in and out, she pulled her mouth away from mine so she could moan loudly and continuously. She was subtly gyrating her hips in response to my stimulation, which I alternated between sliding my finger in and out of her snug, wet pussy and gently caressing her clit with my fingertip.
When she started to tense up slightly, I suspected that she was close to cumming. I wasn't trying to rush things so I could get to fucking her nor was I trying to draw out the pleasure for too long. I was really just happy for the opportunity to be here again, playing things out the way I'd fantasized for so many years after. Also being able to provide her with pleasure just made it even sweeter. The tension suddenly left her body and, as she went limp, she also cried out as her body started shaking. I continued to stimulate her, hoping it would draw out her orgasm and heighten her pleasure. Only once she'd gone still and had let out a sigh did I stop and slip my hand out of her panties, licking her juices from my fingers as she recovered.
"That was everything I'd hoped it would have been," she finally said, looking into my eyes.
"I'm so glad," I replied, "but let's continue this someplace warmer and sunnier."
There was a slight sense of vertigo as we continued to stare into each other's eyes while I transported us from a chilly May morning lying on a New Jersey beach to standing in the tropical sun with significantly less clothing on. We both blinked hard to clear our heads then looked around to see the pristine beach with a lot of palm trees and the cabana with the shower as well as the clear blue water. My attention was then quickly on Theresa with her eighteen-year-old physique in a brief string bikini. I'd never had the opportunity to see her in a bikini when we'd been that age but I knew she'd be smoking hot in one and I was definitely not disappointed. There were clothes of hers that I remembered from back then that I also knew I'd be peeling her out of in future dreams as well as potentially fully playing out the early morning on that New Jersey beach. At that moment, though, I wanted to enjoy her in that bikini for a bit before stripping her out of it.
Because I was the architect of this dream, I'd made sure that my physique was more defined than the skinny kid I'd been in high school and I was glad to catch Theresa appreciating it. I took her hand and led her into water that was perfectly temperate, so we were soon almost fully submerged. There was no build up as there had been with Linda; we just started making out and running our hands over each other's bodies. Her ass, which had been spectacular when we were in high school and which I had actually caressed on those few occasions when we'd made out, felt absolutely outstanding. My cock was throbbing and Theresa didn't fail to notice as she humped her pussy against it. Rather than continue with an underwater dry-hump, she untied my swimsuit drawstring and extracted my rigid tool. She pumped it a few times before wrapping her legs around me while I held her up, pulling her bikini bottom aside and guiding my cock into her hot pussy. We both moaned as my cock filled her and she slowly moved up and down on it.
Unlike with Linda, who I'd already had naked and had fucked by the time we were doing this, I was much more into having Theresa, still in her bikini, riding my cock in the water because I knew we were just getting started. I had a feeling that our first orgasms were going to be pretty quick ones so this seemed like a good position for a quick fuck. I bounced her up and down once she'd wrapped her arms around my neck, pushing deeply into her each time she came down. She was moaning almost immediately and, as snug and wet as her pussy felt, I could feel my orgasm building right away. I didn't plan to do anything to hold it off unless it seemed like I was going to cum before she did, which generally did not happen in these dream scenarios. I wasn't fucking her hard enough to bounce her right up out of the water, but we did get a good, steady rhythm going and it felt amazing to be sliding my cock in and out of her hot, snug pussy.
My cock swelled even more as I was getting closer to cumming and I think that is what finally pushed Theresa over the edge. She let out a cry and started shaking while her pussy was flooded with even more lubrication, making fucking her feel unbelievably even better. Her orgasm was just starting to taper off when I blasted into her with a grunt. I continued thrusting and spurting into her while she rode out the last of her orgasm. My thrusting diminished as my spurting did until I was fully spent. I was still holding her up with my softening cock still inside her but she hopped down, her arms still around me, and we kissed. I couldn't help but return to caressing her sweet ass while I had the chance.