Time with Anna is Precious

Time With Anna is Precious

Sometimes, the person who's been there for everyone else needs someone to be there for them. Author Unknown

This story contains sexual activities and situations between consenting adults. All characters are above the age of eighteen. Any similarity to any individual, living or deceased, or location is coincidental and unintended. From now on, the story will be told in the first person.

You were first introduced to Anna in the 'Caught Feminine in Seattle' series. She then played a minor role in the stories, beginning with 'The Second Sunday in February' in the series Party, Party, Party. Today, you will learn more about Anna.

Anna is Always There When You Need Her

My vision of Anna always takes me back to the first time I saw her. Anna is a stunning Asian woman. She was wearing a black lace corset with garters that highlighted her perky breasts. Her black stockings were embellished with glittery crystals, and her 3" red stilettos complemented the red shimmery thong she wore outside the garter straps.

When I watched Anna walk away, I admired her round booty; a small light shone from her thong crease. Yes, she was wearing a lighted anal plug.

From that night forward, Anna has become a great friend with benefits. She has always been more than a kinky little sex object! Now, Anna's kinky and naughty persona is not something you would want to alter.

Anna works as a server at the Fetish Club. Whenever I was in Seattle, I spent many evenings there, and when I was on a temporary assignment for six months, I was there almost every night they were open. Even though I almost always went with friends, Anna always had my back, Jenn's back!

Whether it was having my favorite cocktail ready for me. Or finding me suitable play partners or guiding me away from a potentially troubling situation. Or finding a private space to gather my thoughts and regain composure. Or a sweet kiss on the lips. Or perhaps a gentle squeeze of my caged or uncaged sissy clit. Anna has always been there for me.

Tonight was no different, but with a little twist. Anna and I have been to dinner together, slept in the same bed, and enjoyed each other sexually. Tonight's twist is the first night she meets Jenn as Jameson, and she's fixing dinner for two.

Jameson Arrives for Dinner

Anna's condo was not far from the Fetish Club and inconvenient for Grace and Stephanie's townhome on Capitol Hill. Changing personas before dinner was not expedient. Spending time with Anna tonight was more important.

She said six o'clock, so I arrived right on time. I brought an oaky California chardonnay to match her expected seafood dinner. Before I could knock on the door, Anna opened it. That would be Anna.

She was shocked. "Wow, Jenn, err, Jameson, you are one handsome dude!" Stepping back, she said, "Let me look at you!" I did a twirl for her as I entered the condo. Once inside, we embraced. We exchanged kisses--not pecks on the cheek, but a passionate kiss. She placed her arms around my neck; I held her at the waist.

I nuzzled my face next to her neck, giving her sweet kisses. Taking a deep breath, I whispered, "You smell delightful, Anna!"

She pushed back, quickly adding, "I spent too much time preparing dinner. Let's have cocktails." She turned, leading me to her open kitchen. I dropped my overnight satchel by the door. Inside was a change of clothes, including a lacy thong, a pair of red 3" stilettos, a purse, and a travel make-up kit. Yes, I planned to spend the night.

As I said earlier, Anna's round booty is almost flawless. Her tight, black leather pants had me drooling. She was wearing her trademark red stilettos. Two Italian spritzers awaited us. I have gotten her hooked on one of my favorite cocktails. Cheese, crispy crackers, and a perfectly sliced apple graced a platter on the counter.

Anna took her cocktail straight to the stove. She added, "Sit Jameson. I've got this!" I offered my help, but she gently refused. She said, "Just Relax!" So, I did.

She turned to face me, hesitantly asking, "Do I call you Jameson or Jenn?"

"Either way, I prefer Jameson when I dress as a male. It's one way to ensure my identity is not publicly compromised." I paused, then added, "On the exterior, I may be Jameson, but underneath, I am all Jenn." I placed both hands on my chest, adding, "Well, almost all Jenn." I was not wearing my breast forms.

"Whew! Do you wear femme clothes underneath Jameson? "

I replied, "I no longer own male undies, and in honor of you, I could slip into my red 3" stilettos!" We both giggled. Anna just smiled at me, but to prove it to her, I took my stilettos out of my satchel and slipped them on.

Returning to the kitchen counter, I smiled and said, "Anna, you look gorgeous tonight. Your emerald corset is stunning, and it perfectly matches your green eyes. And you know I'm not just saying that!" Holding her glass high, she smiled back at me and mouthed, ' Thank you!'

Dinner is Served

We 'quick' chilled the wine. Anna plated a dinner of poached salmon, mixed zucchini, and cauliflower, which paired exceptionally well. A spinach salad complemented the flavors. We took our plates and wine to the dining area.

Every time Anna and I get together, we learn more about each other. Anna knows that I work for an airline and am in Seattle on a temporary assignment. I currently reside in San Francisco. She's more familiar with my alter ego, Jennifer Nicole, but she is experiencing Jameson tonight.

Tonight, I learned that Anna's family lives in the Bay Area. She is of Japanese descent and attended Seattle University, where she earned a degree in Design. While she was in school, she began working at the Fetish Club. The club is an exciting workplace, but she wants to return to school for her Master's degree.

Then she added, "There are three Buts in my life right now. The money I make at the Club is fantastic. The atmosphere is captivating." Pausing, she added, " And I haven't found the right job in my field. That's why I think I want to go back to school. "

But the biggest Buts are my two older brothers, Ryan and Ethan. They want me, almost insisting I return home, settle down, and marry. " She paused, looking at me directly, adding, "They have no idea where I work. All they know is that I'm a waitress!" As a tear formed in her eye, Anna hesitated, adding, "And I might be more interested in marrying a woman than a man!" She hesitated, then added, "Then they will freak!"

I remained silent, just listening to Anna talk. It was not my nature to do so, but she hadn't asked for advice.

Anna continued, "Besides, I'm not ready to settle down. I like fucking different men and women. And I crave the power exchange dynamics." I was focused on her words. Her green eyes were aimed at me. She added, "I just want to meet my person!"

"Jameson, I don't know what I should do?"

Serious Talk

The conversation had turned serious. She was not looking for answers; Anna was just at a crossroads in her life. I wanted to be profound, so I said, "Anna, I have never had all the answers myself. But I'm reminded of a quote I read somewhere. It goes like this: 'We often want it so badly that we ruin it before it begins by overthinking, fantasizing, imagining, expecting, worrying, and doubting. Just let it evolve naturally.' She looked quizzically.

I added, "If you want more freedom, face your fears. Problem-solving will evolve naturally but not without work on your part, and joy and money can be abundant if you let the gates open."

"That said, I have two dear friends, Naomi and Kendall, in San Francisco who are also in the design industry. Their new business is thriving. I want you to reach out to them." I made a mental note to call them first.

Anna chuckled, "Friends with benefits?"

Smiling, I added, "Of course, they are kinky and naughty like us. And they are Significant Others. I share a flat with them in San Francisco. And they will love you!" She flashed a warm smile at me.

On that note, we gathered the dirty dishes and took them to the kitchen. We loaded the dishwasher and left the pans to soak in the sink. This conversation was not finished, but Anna had other ideas.

Passionate Kisses Lead To... More Passionate Kisses

She turned to me, leaning in closer, and we exchanged passionate kisses rather than just simple pecks on the cheek. I nestled my face against her neck, kissing her gently. Anna softly cupped my chin, kissing me tenderly as I replied with more gentle kisses. I felt my heart start to race, but there was no rush at all. I held her close, wrapping my arms around her waist while she snugly encircled my neck with her embrace. Anna softly drew my upper lip into her mouth, exhaling warm breath at the same time.

I turn my head slightly and gently kiss her lower lip. The heat between us intensifies. She releases my lip, and I release hers. Anna traces her tongue along the edge of my cheek. I moan softly. She pulls back a bit. It's my turn; I gently peck my way to her right earlobe, kissing and licking the lower lobe. As I softly blow into her ear, I nibble on it. I can feel the warmth radiating from her body.

Pushing back slightly, I move my hands up her body, gently placing them on her head and tilting it to the left. Softly, I run my fingers along her earlobe and then smoothly down her neck. I am not rushing; I take my time.

I trace my fingers with gentle kisses and playful nibbles. Anna whimpers, and I break the silence, saying, "Anna, you smell wonderful; your skin is so soft!" Now, it's my turn to softly moan.

Anna removed her arms from around my neck and swiftly unbuckled my belt, allowing my pants to fall to the floor around my ankles. This revealed my lingerie-clad body beneath my boyish attire. My black mesh garter and thong trimmed with scalloped lace were now visible. I pushed my lace-top stockings against Anna's soft black leather pants. I felt a chill throughout my exposed lower body.

Anna's right hand gently caresses my cock through my thong. She squeezes; looking up into my eyes, she says, "I promised you dessert; I want you inside me." I quickly stepped out of my pants and eagerly followed her to her cozy bedroom.

Reaching her bedroom, Anna sat on the edge of her bed. She removed her heels and unbuckled her pants. I hurriedly removed my shirt, revealing my black bralette for the first time.

Anna spoke, "Indeed, you are all girl underneath your boy clothes." She paused, adding, "Jenn, now help me out of my pants." I knelt before her to gently tug the tight leather down her legs. Her emerald side-tied G-string that matched her corset barely covered her landing strip that led directly to her sex.

Dessert Awaits

Anna pushed back towards the middle of the bed, wiggling her finger at me, remarking, "It's time for dessert, girlfriend!" I hurriedly crawled after her, eventually floating over the top of her supine body, and gently ran my tongue over her flat stomach. Soft whimpers escaped her body.

"Your smooth body tastes so good." I gave Anna a colossal smile.

Her hands reach around to unclasp my bralette; it drops gently, exposing my nipples. Leaning in, Anna's tongue finds my left nipple and twirls her tongue around my areola. My nipple hardens at her touch. I moan. Anna softly says, "Jenn, you taste amazing too. I can't get enough of you!" She moves her mouth to my right nipple; her tongue twirls around my tiny pink areola, and I feel small bursts of warm air from her mouth.

Anna's neck is now fully exposed. I kiss and nibble along the back of her neck below the hairline as I gently caress her perky breasts through her corset. Anna tenderly grabs my waist, turning me over onto my back and rolling on top of my body. She pulls my arms through my bralette straps, tossing my bra aside, out of her way.

My cock is fully aroused, poking its way out of my thong. I raised my booty slightly; she helped me wiggle out of my thong. Naturally, I wore my thong over my garter straps. She tosses the thong aside.

Is It Possible for Dessert to Be More than One Serving?

I spread my legs, enabling Anna to kneel between my legs. My now freed cock, fully aroused, is bobbing up and down and sideways.

I stare at her honey-toned body, her perky boobs peeking out from her corset and barely covered pussy. I so want to lick, kiss, and finger her to ecstasy. Anna, at the moment, has other ideas.

Anna breaks the silence. "Jenn, I have been thinking about your cock inside me all day!" Leaning forward, she pins my arms to the bed, pulling my knees up; she squats over me. Her side-tied G-string is now visibly wet. As she loosens the delicate ties, her glistening pussy is revealed.

She presses her knees and shins to the bed, guiding my bobbing cock towards her pussy. She slides down my shaft, slowly moving up and down my stiff cock. Anna is entirely in control; as she straddles my body, I rest my hands on her knees, gently squeezing them and assisting her in maintaining the rhythm between us. Anna is whimpering. Anna leans back against my knees, and with each thrust, we find a pleasurable rhythm. My cock slides in deeper with each thrust. Anna wiggles her lower torso guiding my cock in search of her elusive G-spot. Her whimpers have shifted to moans.

My hands are now free to roam all over her body. Anna guides my hand to her clit, placing two fingers on the right spot. She pushes down on my fingers, guiding the motion. She knows what works, and she is teaching me what she needs.

As Anna's body tenses, she screams at me, "Faster, Jenn, faster!" I keep pressing her clit with my fingers, wiggling them in the same motion. Her movements are controlling the penetration of my cock inside her. Her body trembles. The bed is shaking. Anna pushes my fingers down hard on her clit. She screams louder this time. Her orgasm is intense and powerful. I am excited just being a part of it. Using my other hand, I gently caress her hip to help ease her into her pleasure.

The Pleasure Builds Again

As she relaxes, she realizes that I have not orgasmed. Anna starts moving again on my hard cock, wiggling her booty as she rides me. I push up; we're back in rhythm now. I push my cock in deeper. Anna leaned forward, pressing her arms onto mine. I lift my ass to get deeper penetration, meeting her wiggle. Then Anna screams again, "Faster Jenn, faster!" Anna has caught her second wave. She screams, "Oh, Oh, Oh!" I see her bite her lower lip.

This time, I am right there with her. My body tenses when I spurt my cream inside her vagina. My cock is throbbing; I spurt again, catching her at the top of her second wave. Her body is quivering; her second wave quickly subsides as it's less powerful. She falls entirely forward over my body. I wrap my arms around her. Tilting her head, Anna kisses me full on the lips. We embrace. My hard cock is pulsing inside her.

Rolling over, we continue to kiss. Anna radiates warmth; her golden hue resembles liquid honey, lovingly drizzling from a spoon. We take deep breaths together. Anna speaks first, "Thank you, Jenn!" My cock slowly pops out of her pussy. Anna ran her fingers along my shaft; she added, "I wanted your cock tonight. I needed it, and I got it!" she paused and added, "And I didn't have to share with anyone else."

My hand is now caressing her booty. I whispered, "I needed you too, Anna!" We kiss.

Anna snuggles into my arms, gently nuzzling my neck. I stroke her hair as we remain quiet. No words are necessary. We drift off, holding onto each other.

The Morning Sun - Time for Breakfast

At some point, we became wholly naked and crawled under the bed covers. I awoke and snuggled into Anna's backside. My cock was semi-aroused. I pushed my hardness into the crease of her booty. With my left hand, I freely roam all over her body. Anna is moaning at my soft touch. Anna is now awake and guides my hand to her clit, placing two fingers on the right spot. She pushes down on my fingers, guiding the motion. Her whimpers heighten at my touch. My now hard cock pushes against her booty. Anna raises her hip, allowing me access to her pussy.

The head of my cock quickly finds the lips of Anna's aching pussy. As I push the covers off of our bodies, I slowly push the tip of my shaft into her vagina. A soft, easy cuddle fuck ensues, but Anna wants more.

She positions herself at the edge of the bed, twisting her lower body like a pretzel and raising her leg across her body with her knees bent. I stand upright with one leg on the floor; I straddle over her lower leg and thrust my cock deeper into her vagina. Leaning over Anna, I firmly grasp her booty and thigh and pound away. My cock deeply penetrates her. When I hit her G-spot, Anna screams, "That's it, that's it, faster." My thrusts are steady and deep. I feel her body tense, then slowly calm. She falls silent for a moment.

As my throbbing cock continues to push deeper inside Anna, her hand hastily rubs her mound. Her whimpers now match my deep thrusts. This time, it's my body that tenses, filling Anna's pussy with my load. She recoils into her second orgasm. I spurt inside her again. Her eyes are closed tightly. My body calms. As she opens her eyes, smiling, she pulls me closer. We kiss. I softly whispered, "Good morning, Anna; breakfast has been wonderful! " Pausing, I added, "But I have to go to work!"

She broke our embrace, jumped off the bed, and took my hand. "Okay, Jenn, let's take a warm shower."

Jenn Emerges as Jameson

Running my fingers all over Anna's softness and smoothness excited us both. When she caressed my cock with her wet soapy hands, I became aroused once again. Anna softly whispered, "Jenn, I cannot resist you." She hurriedly dropped to her knees. Her tongue and lips slurped my hard cock as if it was a candied popsicle. My legs became weak; to brace myself, I pushed against the side wall of the shower.

I became fully aroused in her soft mouth as she slurped and tongued my cockhead. I won't last enough to be an all-day popsicle. I could feel my body tense as my legs became weaker. I quickly shot the cream deep into Anna's mouth. She swallowed as much as she could.

Anna slowly kissed my stomach and chest; reaching my mouth, she gently kissed me full on my lips, parting my lips with her tongue, pushing my cream into my mouth. We kissed passionately. Water cascaded down our bodies. Ultimately, we broke our embrace. We needed to wash the soapy suds from our naked bodies.

Anna stepped out of the shower. First, she handed me a dry towel; she folded her towel over her head, covering her wet hair. As I finished drying off, she returned with my satchel.

I made myself presentable for work. A man on the outside, girly underneath. Anna was sitting at the counter with a fresh cup of Seattle's finest, waiting for me. Her hair was still in the towel; she remained naked from the neck down.

As I entered the kitchen, she remarked, "Jameson, do you have time to drink your coffee here, or do you want a go cup?"

"Here is perfect Anna. I don't want to depart just yet. Spending time with you is precious. I paused and added, "Anna, we didn't finish our conversation about you last night. When you're ready, I'm here for you."

Anna smiled, "Jameson, can we meet for coffee or lunch on Friday? If you come back here, we will never have that chat, and I want to talk with you, not just fuck you."

I finished my coffee, replying, " Does lunch work on Friday? Pick a place near my office?" She nodded, then stood to embrace me. We kissed. I held her waist tenderly. As I needed to go, I reluctantly avoided touching her naked booty.