In Her Dreams Shaylah's First Entry

"Dear Diary,

I dreamt of him again. Even though I just masterbated and came harder than I have in years, I can't tell if I'm excited about it or frustrated. There's no way he's going to live up to the hype, even if I muster up enough courage to ask him out...right? I've been single now for over a year, and I've had several hookups- but there's something about him. Something that makes me....nervous? Enthusiastic? Horny as hell? Well... The last one is obvious since I wake up wet thinking of him nearly every other day.

The constant push and pull I have dealing with my own emotions on this is giving me whiplash, and it's pissing me off. Shit- I just looked at the time, obviously my enjoyment lasted way longer than it should have, I have to get ready for work. I'm coming back to tell you about my dream. This one was one of the best ones yet."

***

Shaylah closed her diary, and threw it in her purse so she wouldn't forget to bring it to work. She didn't want to wait too long to write about her dream- she wanted every detail still in her head.

Hopping out of bed, she walked to her bathroom. Glancing around her apartment where she had been living alone, she still felt a wave of gratitude for her independence. No longer was she forced to be the caretaker of a grown, and fully capable, man. If laundry was on the floor, or the dishes weren't done, it was her responsibility alone. Not only that, but she took care of those things immediately. Never one for interior decorating, she was still working on making the apartment her very own. Her best friend, Mia, had already come and waved her magic wand over several rooms with the smallest but significant changes. Her walls were in desperate need of art, and Shaylah was eager to make the space represent her own personal style.

***

Shaylah had been married twice in her life. When she was nineteen she married her high school sweetheart. And, yes, it was because he was in the military. Somewhere inside she always knew it wouldn't work out, but she was in heavy defiance of everyone else in her life telling her it was a terrible idea. When she was in the process of divorce at twenty two, she met who she viewed as the antithesis of her soon to be ex-husband, and that seemed more attractive to her than anything else.

Casey was a good man, but he was still a child in so many ways. Their marriage lasted for nearly ten years, and while Shaylah learned a lot from the relationship, she ultimately knew splitting up was the right thing to do. In the last few years of their marriage she realized she had never really had a partner. Not just with Casey, but with any man.

When Shaylah loved, she devoted herself. Not in a submissive fashion, but it was natural to her to pour herself into supporting those she loves. She didn't realize until it was too late that it wasn't reciprocated fairly. Casey also had sexually ignored her for about three years. Perhaps it had something to do with his depression, or drinking. She knew in her bones he wasn't ever cheating on her, it wasn't even something that she had given a second thought. She remembers almost wishing he was being unfaithful so there would be a reason, more ammo for a fight. The lack of any tangible reason for his lack of interest in sex fucked with her self confidence, an unfortunate affliction that would would still rear its nasty head from time to time.

Shaylah had quite a beautiful body for someone who never did anything to exercise it. She knew that if she put forth the effort to work out that she would really look phenomenal, and not just someone who lucked out with incredible tits, but she was comfortable with her body just the way it was. She had a real love of lingerie, and had recently started getting back into wearing it. Casey never really seemed excited when she would wear it, so her collection had started to diminish. The guys that she had fucked since her split certainly responded well to her newly purchased pieces, and while their reaction made her feel powerful, she really just enjoyed dressing up for herself.

The freedom of her new single life was intoxicating, and Shaylah found that she was thriving. She had no interest in dating apps since the experiences she had heard from friends seemed more often to be horror stories rather than rom-com meet-cutes. Most of her connections stemmed from people she already knew. There had been several "I've always wanted to be with you" confessions and "I always said if you were ever single again..." type of pick up lines. The majority of hook-ups were merely okay, some were really bad, and only a couple had been really great.

She had a long standing relationship with a very reliable fuck buddy that started before she was married. The great thing about Aaron was that he was up for absolutely anything. Anything. They were friendly in the outside world, but had only ever seen each other maybe a couple times a year at events with mutual friends. They respected each other above all else, and grew to have a specific relationship that was never uncomfortable in the sense of jealousy or judgment. They both loved having sex with each other, and they had a safe place to express fantasies, or try things they had never done. Shaylah knew she was far more inexperienced than Aaron was, but he never made her feel any type of way about it. He introduced her to a good amount of voyeurism, and ideas about group sex. He loved getting fucked in the ass, and she found she loved doing that for him.

He had an incredible, Adonis-like body; sculpted and fit. His addiction to cross fit was certainly obvious, and Shaylah found admiration in the way he honored his health. He was bisexual, but not exactly out about it. A big hand was owed to him for making Shaylah feel strong in her sexuality and feminine power. Up until that point, no one in her life had ever consistently reacted the way he did when she would send him any level of suggestive picture. From a sexy look to completely naked, he acted like it was the first time he had ever laid eyes on something beautiful. She was grateful to him for that. She was grateful to him for many things.

When either of them would start to see someone seriously, they both mutually backed off and wished the other luck in the relationship. A true and honest sentiment full of support and encouragement. Shaylah knew they'd never have a relationship outside of their sexual one, and she was perfectly comfortable with that. Their connection was exactly what it needed to be for both of them.

***

Shaylah whisked her thick, long hair into a ponytail as she swirled mouthwash back and forth. She had spent so long with her fingers on her pussy reliving her dream that she only had time to put on a bit of mascara and eyeliner. Running to her closet, she grabbed a well fitted black t-shirt and some dark denim jeans. In only a few minutes, she was out the door.

One of her neighbors was trudging past as she opened the door, and she smiled warmly at him. Unsurprisingly, his gaze quickly flicked down to her breasts. Being that she had been well-endowed since the seventh grade, she was more than used to this occurrence. Pretending not to notice, she shifted her bag onto her shoulder and kept walking. As she opened the door to the outside she glanced down at her front, maybe she had toothpaste on her shirt and he wasn't being a total guy. But there was no hiding the real eye-catching reason for his glance, her nipples were at full attention and noticeable beneath her tight top.

"Poor guy..." she chuckled to herself. "Never stood a chance."

While driving to work, she realized that she needed to put the thoughts about her vivid dream on hold. She was having a hard enough time concentrating as it was. Lunch time, she decided. That would be when she and her diary would be sure to file away every last detail. Just the thought of getting to relive the dream one more time made her nipples grow hard under her shirt again.

***

11:46....11:54....11:59.....

NOON!

Her heart was pounding as she grabbed her purse and made her way to her office.

***

"Dear Diary,

Alright, so you ready for this one? Yes, it was Tristan again. I don't know if I'll ever even really talk to this guy, but I'll happily keep these scorching hot dreams in my memory bank. He was working at the bar where we met. I came in with a few girlfriends and we sat at the end. The place was filled with customers and he didn't seem to notice us, only offering a quick glance. Another bartender took our drink orders and chatted with us for a bit. I purposefully wore a zip up jacket...really hoping to find a reaction when I decided it was just too warm in there. After a couple glasses of wine I got brave enough to allow my eyes to linger on him while he worked. Watching a good bartender do their job is always a pleasant experience. They move so smoothly, a sort of synchronized series of movements, effortlessly mixing drinks with machine-like speed and artful flourishes. He would smile and chat with customers while answering questions from his coworkers, all the while seamlessly creating cocktails and pouring beer. He made everything seem so... fluid. It made me fantasize about how good he must be at multitasking in...other areas.

I couldn't be sure, but it started to feel like he was peering in my direction a bit more than before. This made me smile and flip my hair a few more times than necessary while talking with my girls. I was genuinely having a good time, and hoping that this light flirtation was't completely in my head. Then my friends both excused themselves, one needed to make a call and the other took a trip to the restroom. I noticed the room had emptied out and Tristan was now the only one behind the bar.

"All alone?" I heard his silky voice address me.

"For the moment, it seems." I did my best to keep my voice steady.

He smiled and moved to be right across from my seat. He was close enough that I could smell him, and my skin began to tingle. He looked casual and relaxed as he cleaned glassware,but his gaze was boring right into me. Suddenly, the room felt like a sauna, and I unzipped my jacket as nonchalantly as I could manage. As relaxed as he appeared, it was not lost on me that his eyes followed my zipper as it glided slowly down to unveil my breasts, then continuing on to expose my torso before finally breaking free at my hips. I slid the sleeves off my arms, revealing a dark, plum colored blouse, cut so low that from the side you could easily make out the curves of my breasts. It's the kind of blouse that beckons you slide your hand in and feel how the hell it's even staying up.

"I've been waiting for that all night." comes a gravelly voice just louder than a whisper.

I snapped my head up and saw that he was staring me down so intently that my legs began to shake. My eyes grew wide and before I could even begin to stammer out a response, my friends returned. He continued to serve us, as charming as ever, but there was no question he was watching me now. The night came to a close and the girls were ready to leave. I scanned the bar for him, but he must have stepped out back. A server took our payment and I felt disappointed to say the least. There was no doubt that the sexual energy had been building and I was certain I wasn't imagining it. I was more than ready to find out if the tension was mutual.

My place was nearby so I decided to walk. Perhaps not the smartest move as dream-me was wearing three and a half inch black matte heels with sheer thigh-high stockings attached to a garter barely hiding under a short skirt. I distracted myself as I walked, thinking about the lingerie I had on, and how I had hoped to find out what he thought of it. A brisk breeze suddenly hit me and I shivered. Then suddenly it dawned on me... Shit. I left my jacket at the bar. I really didn't want to go back and appear desperate, like I had intentionally forgotten something, but that's my favorite one so I'm not leaving it. I turned around and headed back the way I had come, my heels clicking with every step on the pavement. My tits bounced as I quickened my pace, and I couldn't help but wonder how they stayed contained. The bar was in my sight and I crossed the street. Just as I was about to approach the door when I heard a voice from the shadowy area at the corner of the building.

"Forget something?"

I jumped and turned. Tristan stood in a short alleyway with a cigarette in one hand and my jacket clutched in the other.

"Oh...yeah, I just realized I wasn't wearing it." My heart was pounding as I slowly stepped towards him.

He smiled at me and put his cigarette out as I drew within a few feet of where he stood.

"I'm glad you came back for it," he confessed with a sly look.

As he reached out to hand it over his thumb grazed the back of my hand, which sent electric shocks straight to my pussy. I couldn't hold it in anymore. I dropped my jacket as my hands reached for his face, pulling him passionately to my lips. He returned the urgency and pushed me up against the cold building, pinning me gently, never breaking contact from my mouth. His kiss was perfect; soft and sweet with an exciting bite of dominance and desire. His teeth found my lower lip and claimed it. I let out a moan and with this sound of approbation, he pushed my entire body fiercely into the wall. I could feel his cock and it was damn hard.

Suddenly, I put my hands on his firm chest and pushed him back. He stumbled and searched my eyes for an answer. Before I could hesitate, I grabbed the neckline of my blouse and ripped it wide open, fully exposing my supple breasts. I'm not sure if it was the wine, or the bold confidence of dream-me, but all I knew was that I wanted him to see every inch of me. My nipples were hard and his eyes were burning as he took in the sight in front of him. I looked straight into his eyes, and then I heard myself telling him to touch me.

Without a second of hesitation, his mouth locked onto my round left tit, and his tongue began to urgently tease my erect nipple. At the same time, I felt his soft, yet firm, grasp on my right breast. The cool night air left a strong chill on everything his saliva touched, and it made my skin more sensitive to his touch. After a few minutes, he released me from his lips and his eyes found mine. Suddenly, I felt his free hand as it worked its way up my thigh and started rubbing lightly through the delicate fabric of my thong, directly on my clit. I could barely control my breathing and I had to remind myself we were completely exposed. Anyone could have walked past us and seen it all. Before another thought could enter my brain, I felt his finger move past the thin material concealing my sex, and he plunged it deep inside. His mouth found its way back to my breasts, the right one this time, and I felt a groan escape my mouth as he simultaneously sucked on my tit and finger-fucked my dripping pussy. As the pleasure began to build, I slammed my hand over my mouth to keep from screaming. My shoulders stayed firmly planted on the wall, but I thrust my hips toward him, grinding my body with the pleasure he was providing.

I could have stayed this way all night, but I could feel a deep need starting to rise inside of me. When the sensation would not allow itself to be ignored any longer, I removed his hand from my cunt and raised it to my lips. My lips locked around his wet fingers and I started sucking, tasting my own arousal. His forehead leaned on mine as he took in the view with immense gratification and awe. I planted a light kiss on his lips and felt my own secret joy that my pussy was now on his face.

I felt so excited for what was to come next, that without even moving from my spot, I dropped to my knees. With focused determination, I undid his belt and unzipped his pants. When I peeled back the last layer to my prize, my eyes lit up as his cock was revealed. I reveled in this satisfaction and peered up through my eyelashes at his waiting, wanting expression. Without breaking eye contact, I opened my mouth and took him in. I savored the feel of his smooth dick entering my mouth, the taste of his precum on my lips. His cock was delicious, and my tongue wrapped around every curve as I drew him and out. I made sure his entire length was deeply lubricated with my spit as I used my hand in conjunction with my wet lips to pump his thick cock back and forth.

He sucked air in through his teeth and I heard him shakily utter, "Fuuuuck, girl."

With that approval I plunged him deep into the back of my throat. I kept him there as long as I could before a gag forced him out. I love this game. As I continued to deepthroat him I realized he was pushing my head against the wall and that he was straight fucking my mouth. I was in ecstasy. He backed out and a huge trail of saliva hung between us, connecting his cock to my lips. Tristan looked down into my eyes with a silent question.

I know there's so much more to explore but I can't wait.

"Cum in my mouth." I demand, answering his unvoiced query.

I grabbed his ass and returned him forcefully to my eager mouth. His perfect shaft fit like it was made just for me. Spit coated my chin, but I didn't care. I bring one hand up to cup his balls and started massaging them well. Placing the other hand back on his cock, I started to synchronize movements with my mouth. I could feel the build up in his entire body as he began to stiffen slightly. He punched the back of my throat harder and harder until his cock exploded a massive amount of warm cum into my mouth, filling it completely. I kept his cock there, reveling in the feeling of the aftershocks of his orgasm. I swallowed his cum, and every little tremor he made only added to the massive sense of satisfaction I felt coursing through me. I couldn't help but wonder if he was aware of how wet my pussy still was.

After a few silent moments he leaned down and lifted me back to my feet. His body leaned into mine and we stayed that way until our breathing had calmed. His fingers trailed under my chin, lifting my mouth to his and he unabashedly kissed me deeply. This is one of the sexiest things a man can do, in my opinion, to not treat my mouth as if it were off limits when it's been on his cock or tasted his cum.

During this kiss was when things started to get fuzzy and I woke up. Like I said, there's no way it can be that good if it were to happen in real life, right? Am I building this all up way too much in my head? Perhaps I'll take Mia to the bar tonight for a little reconnaissance. She can help me see if he takes notice of me in the way he does while I'm dreaming. At the very least I'm sure I'll gather more fodder for my dream-self's sexual appetite.

Kisses,

Shay

***

Shaylah closed her journal and crossed her legs. She could feel the hot moisture between her thighs, a slight dampness in her panties, and that brought a smile to her lips.