Entangling Elena – Anal – StoryVa.com


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I wanted something more from my formal education, yet I would need some experience before anyone would allow me the freedom I sought. Four years in the south had been too restrictive, even if Judson had opened a few doors, I was yearning for more from life than the patrician and gentile environment of my classmates. The Judson women knew, or imagined, how every step would be taken, and I felt they were too young to adopt the patrimony. I was alone in my independent views, and my need for agency. My resistance to the toxic femininity of the region, an unapologetic regarding my life choices, and the atmosphere of the small school lead me back to the northeast. I need more of everything, more noise, more energy, more men. I was living my life, and the question in my mind was could I achieve my goals and still discover love.

Sitting quietly at the front table, with a view of the passing pedestrians, Elena considered how much happier she was with the new weekend position. Having completed her degree she was offered several positions in finance, and she took a job in New York. She quickly realized that she wasn’t comfortable working on the large faceless accounts. The hours were not extreme, but she was expected to be at her computer nine to ten hours a day, and on a Tuesday afternoon, five months after she had started she sent her resignation. She had been praised by her manager a week earlier for her focus and diligent work, but now she was unemployed. After a few weeks, her good friend Francine heard she was interested in property sales, and she knew that her father needed some weekend help. Elena accepted the job and was working several days each week at the real estate office. Her new boss Alan liked that Elena knew how to dress, and that she at all times seemed to be smiling, as she occupied the table that served as a front desk.

On a quiet afternoon she met a couple, as it was Saturday and Elena was the only one in the office, and she stood quickly when she noticed the door swing open. The sun was in her eyes as she welcomed the prospective clients, and she failed to notice the look the man and woman exchanged as they reviewed her; one quick glance the two shared, and then a brief hand squeezed. Elena smiled though she couldn’t see the two.

The man spoke as Elena shielded her eyes from the glaring light, “Good day Miss,” but his partner stepped up closer to Elena as she noted the blinding sunlight. Taking Elena’s elbow she said, “Let me help you,” and the two women stepped away from the window.

Elena felt her gentle but sensual gesture, “Thank you, I’m Elena Stern, how can I be of help?”

The couple ask to see two very different homes, and though her boss Alan normally did not allow her to present properties, due to her inexperience, Elena quickly texted him,

‘I have the key codes Alan, and they seem nice’

Alan was on the Island, but he quickly called and directed Elena regarding the presentation and the access keys, “Make plenty of notes, and please share the client’s impressions with me first thing Monday. Oh, and don’t offer any insight about the seller’s intentions Elena.”

Elena spent a pleasant hour showing the properties, and she felt that she had made a good impression, “I’m happy that I could be helpful,” she said when she pulled up to the office and turned off the large office utility vehicle. They didn’t immediately open the door to leave, and so Elena turned to look back at the two in the rear seat, “Is there anything else I might do for you today?”

The couple smiled and the woman reached forward to touch Elena’s hand. They didn’t seem to be married, as Candice’s ring finger was bare. Elena eyes shifted lower, as she noticed that the woman’s dress hem had ridden up on her thighs, exposing her hose’ top, and the glance at her exposed legs caused Candice to move, and pull the material down. Elena saw the action and when she looked back again, Candice smiled. A moment later they stood on the sidewalk.

Elena was dressed in an expensive A-line dress and black shiny heels, and the woman remarked on her outfit. “I saw this dress at L&T the other day, but they didn’t have a size six,” and Elena blushed, while quickly reviewing the woman’s figure, and her eyes fell to Candice’s breasts.

“Maybe I was fortunate Candice to be there early, and I bought the last,” but Elena was pretty certain that Candice’s large bosom wouldn’t fit a six, and she smiled when Candice invited her to a late lunch with Damon.

“We’re famished,” and they all walked over to a restaurant.

Elena smiled as Candice took her hand, and the two women walked ahead of the dark-hair man, “Damon loves to look at you, and you’re witty,” Candice whispered as she glanced back toward Damon, a few paces behind. Elena enjoyed the compliment, yet she thought about the two lovers.

During lunch Elena learned of Candice’s disdain of flashy jewelry, “He’s given me a beautiful stone, and I wear it nearly every day,” and Elena thought, as Damon’s hand moved to caress his seated wife’s bottom.

“Silly, I’m not wearing it now sweetheart,” and Elena thought to herself about where the marriage stone was worn.

Late that night, Elena was in her bed and she was reading her notes. These were not the notes that she had provided Alan, but from her diary, and the detailed notes about the man and the woman she had shared a meal with this afternoon. She enjoyed the tall sexy man, Damon, and her body became aroused thinking of his packed trousers, as she slipped her moist finger inside her body, “I could ride him,” she whispered. “and Candice, you sexy wifey, you can watch me cum on his fat dick!” she moaned as she climaxed, as her fingers rubbed across her clitoris.

A few days later Elena was at a downtown farmers market and Candice saw her as she selected some vegetables. Elena was surprised, as she quickly reviewed Candice’s outfit, and her choice of shoes; high heels, and she smirked as she studied the femme look that Candice seemed to project. The attraction was apparent and though reserved Elena agreed to have a quick lunch. The afternoon evolved quickly, “Come and see the apartment, as we may have you list it next week,” Candice said while standing very near to Elena.

The apartment was a short walk south in Greenwich Village, and they stopped in front of the four-story eighteenth-century brownstone. Once in the vestibule Elena was surprised to see that the building had a small elevator.

The two women were cramped and when Candice shifted to begin the cab moving up, her shoulder rubbed against Elena’s breasts, “It’s a bit intimate but three flights of stairs in these shoes would be a killer,” and Candice turned as she blushed being so near Elena.

As the cab moved upward Candice smiled and told Elena, “I enjoy being with you and Damon thinks that you are beautiful, and I’m hoping we can spend some time relaxing, as Damon won’t be home for hours.”

Elena considered her words as the door opened on the apartment foyer; she would try and withstand Candice’s advances. When she had unlocked the door, Candice took the small bag of vegetables from Elena, “Welcome to my lair, as Damon calls this place.” The space was gorgeous and well furnished, with high ceilings, and large old windows looking out to a private garden. Elena hadn’t been inside an opulent and richly detailed old apartment such as Candice’s.

“Damon gave this to me after our first year together,” and though it was spacious the apartment had only one bedroom, and a small library, “I really don’t want to sell, but Damon wants me to consider a larger place, or possibly a townhouse,” as she showed Elena the library and the hidden bath. They she stepped into the generous and elegant dressing and bath.

“Damon like’s calling the place a one-bedroom, even though there’s the second bath,” they stood at the door to the dressing room and Elena smiled seeing the closet full of outfits; clearly Candice was a femme. Candice had moved to the dresser, and she smiled, and turning she quickly closed her upper drawer which had been left open.

“I’m sorry you had to see that,” she said, as she fumbled to close the drawer, yet with a quick glance Elena had seen the contents; several shiny metal probes, a leather dildo, several butterfly clitoral devices and a short white wand vibrator; items for personal pleasure that Elena knew well.

Again Candice blushed, “We have to keep this quiet, as Damon can and does please and love my body, yet I am lascivious, and imprudent,” and Candice blushed. “I just need a lot of sex, as my libidinous nature, ah,!” but she stopped speaking.

Candice moved closer, “You understand that I’m attracted to you Elena,” and Elena felt Candice take her hand, “but let’s sit and have some white wine,” and Candice moved passed Elena and stepped to a small wine cooler.

“Candice, you’re married and lovers, and you should do whatever you can and want to stay in love,” as she took the offered stemmed crystal glass; silently Elena recalled how full Damon’s pants were, and she turned trying to distract herself, and she reviewed a small painting on the wall. It was quite old.

Candice came beside her, “Somehow Damon acquired that small oil. It’s a Church, from 1865. He gave it me to remind me of my hometown on the Hudson River.” Elena knew of the artist, but had not met anyone who had such a unique art collection.

During the next few weeks the two spent more time together and were becoming friends. Elena sensed that Candice’s attraction was increasing, yet she wasn’t gonna get entangled, though she had taken to dreaming about Damon’s cock fucking her almost every night. Elena’s diary was filled with her mother’s suggestions and her own adventures, including her recent carnal thoughts regarding her new friends:

‘Damon’s meat is in my mouth, and I so need him deep in my body!’

Elena wanted an affair, as she found that discover a guy who would support her other interests might be difficult. She might enjoy being this woman’s lover, and maybe even sleep with her husband, but she knew that her wish and desire would not be fulfilled.

Sitting in a yellow cab they shared, Elena said, “My mom always said, ‘keep your lover’s separate’, and another she said that made sense is, ‘every woman is different,” and Candice laughed. “I agreed,” but Elena smiled, again considering Damon’s body as she sat riding north on Madison Avenue. Candice might be a good female friend, yet she would watch her carefully, and Elena knew she would masturbate later with her mind filled with her lewd memories of Damon.

The following week she was shopping at Bergdorf’s and the two again saw each other. Elena was perusing the lingerie collection, and Candice was selecting a new dress, and in a blink she saw Candice skipping across the retail space; she had been seen and Candice was near.

“I wanted a new dress and shoes, quite willful of me,” Candice explained. They continue to shop together, and Candice requested that Elena accompany her to the ladies dress booths to affirm her selection. As Candice removed her dress, Elena swooned.

“I need to sit,” and she quickly moved the other selected dress from the seat and rested.

“Elena, are you okay?” Candice asks as she moved down to her hose’ covered knees.

Elena watched this quick move, and she felt Candice’s hand on her own thigh, “It’s just, Candice, ahh, being near you, as you removed your garments, well, it caused me to feel light-headed.”

Candice looked up to Elena’s face, but her fingers moved up Elena’s thighs, pausing at the loose hem of her dress, “I think that you are becoming excited being with me!”

Though Elena was trying to withstand the clear pass, she stood up quickly, “I think that it would be better if I waited outside the booth, and try and control my superficial thoughts,” and she opened the door and stepped out, and now she saw that a salesperson was near.

“Miss, we do not allow two people to gather in the changing rooms,” and Elena apologized and stood holding her small clutch. A moment later she opened the purse and checked her face using the mirror attached to the booth’s outer door. As she re-applied her rouge lipcolor the doorknob turned and she quickly stepped back, and her tall satin red heels almost caused her fall backward.

In a blink the booth door was open, and Elena stood looking at Candice who was smiling, “Is this what’s the cause of the excitement? It’s a true mystery to see the visible, humm?” Elena realized that Candice was misquoting Oscar Wilde, and she was nearly naked, except for a ting thong and the loose hose’, dangling since she removed her garter clasps, and Elena’s eyes smiled as she starred at Candice’s gorgeous breasts, then her eyes dropped to Candice’s flat tummy, and Elena saw the slight tenting at Candice’s tiny thong, and she watched as Candice’s fingers caressed her naked breasts.

“I’m trying to get your attention Elena,” and Candice stepped closer. “As I need you to be a lover,” but Candice heard the saleswoman returning, and quickly moved and slammed the door.

The woman was carrying a box and looking at her phone, “Did that one fit nicely?” The woman asked, but Candice now held the door just slightly ajar, so that the woman couldn’t see her nakedness.

Elena smirked, “She was not comfortable with the size eight. Do you think you could see if you have that in a six?” And Elena heard Candice agreeing through the small gap of the door.

Elena moved to lean close to the nearly closed door, “A size six for such a perfect body, right Candice?”, and Elena heard a soft moan.

“If you could only understand how I have been longing for you to touch me,” and Candice swung the door wide as Elena shushed her, but again she smiled, as she noticed that the thong panel had parted Candice’s plump labia.

“This risqué behavior is curious from a married woman Candice! The salesperson will return,” and just then she did appear, only from a different direction.

“I appreciate that you are being helpful to your friend. This six may be too tight, but here,” and she again left the small anteroom. Now Elena held the garment, considering the situation. This new girlfriend might be serious, but Elena thought about what she’d seen, as seeing the thong caused her arousal, but she didn’t feel that the store was the proper place to discuss the pass nor Candice’s anatomy.

“I have the size six, but Candice please try to behave when I open this door,” and she saw the knob turn, and a hand extend.

“I am sad that we can’t be together in here, but I will respect your decision Elena,” and she took the dress without further exposing herself, “but you saw that my labia are quite pronounced Elena,” and Candice giggled as she closed the door.

A few minutes later Candice completed the purchase and looked around for Elena, and she found her looking at a piece of jewelry, a bracelet, and she immediately offered the attendant her credit card.

“I’m going to buy the piece for you Elena,” and Elena smiled, but tried to pause the transaction.

“Maybe this one instead Candice?” Elena said and smirked thinking of how clearly Candice was interested in her. She did like Candice, but she would need to discover a moment and explain how inappropriate the dressing booth incident was, and she needed to consider her other worries.

Once in the taxi and heading north from fifty-seven street Candice sensed the discomfort, “I shouldn’t have done that, and I don’t know why I get crazy and act risky. It could have been embarrassing for both of us Elena.”

Candice turned say this and Elena smiled, “But I like how you apologized, with the Yurman bracelet Candice, so no problem. You seem quite able to focus on my desiderata.”

Candice considered her use of the word and offered, “I’m a woman with a greedy, almost male gaze, and I love looking at you Elena,” and she paused, “My ardor is only beginning.”

Now Elena slowly turned, “I don’t want to feel pressure to have sex. Your promiscuity, ah, is almost predatorial, yet I think it’s just your raw sexual manner. You aren’t a typical lesbian, as you have Damon, therefore you don’t loath men,” and she looked into Candice’s eyes. “I enjoy knowing that I fill your mind, but I will not be easily seduced Candice,” and she saw Candice smile.

“I choose to train my gaze on men,” Elena stated, but she then signaled the driver, as she remembered that she had to stop at seventy-sixth street. “Listen, I need to pick something up,” and as the cab moved to the curb she explained that her doctor was on the block. “You take the ride as I need to pick up something from an office.” She looked at Candice, “I’ll just say that ‘safe’ is an old feeling, but it’s something I need as a woman,” and Elena closed the door and waving she walked down seventy-sixth street.

That evening Elena went upstairs to see Christina, “There’s was only good news from Dr. Tray, as she’s feeling my adjusted meds are working much better.” Elena had a minor heart condition, and the doctor felt that she was gonna get it under control with the medication.

Christina was forty-six and had been like a mother to Elena these last five years, as Elena’s family had been destroyed, first by a divorce, and then a death. The relationship with Christina had become important to Elena, as she negotiated her education and found her own way.

Elena decided to distribute the afternoon at Bergdorf, “There is some doubt, as I saw,” and she paused, considering how excited she had become. “Well Mumm, Candice is risque’, and she exposed herself in the dress booth, and she has quite pronounced outer lips between her thighs,” and she paused. “She has a stunning figure,” and Elena noticed that her breathing had changed, and Christina smiled.

“You were excited?”

Elena giggled, “Oh yes Mumm, she has a wonder body, with wide hips and a generous bosom,” as Christina poured the deep red Napa Cabernet.

Christina noted Elena’s focus on the genitalia of her new friend then inquired, “You have met her husband, Damon?”

Elena explained her immediate attraction, “You know how much I like slightly older men, and his package was noticeable,” and Christina chuckled, as Elena explained her nightly sex play, “I have wild fantasies about Damon, and I’ve nicknamed my large toy!”

Christina was well aware of Elena’s needs, as they had shared a bed many times, but not recently, as Elena determined that her desire of men needed to be addressed, “Just share with Candice the circumstances of the passing of your mother and your decision to attend school in the South,” and Elena agreed.

It was three days later when Candice called her new friend, “Are you still angry about the dressing booth thing Elena?”

“No way, I’ve just been overloaded though, but I could have lunch tomorrow. Could you make that?”

Candice had determined to distribute with her friend some things about her sexual interests. Elena was still surprised, and yet happy that Candice was attracted to her, though she wouldn’t screw up Candice’s marriage, she lusted for Damon. Though she was bisexual, most of her lesbian friends were very limited by their need and love of pussy, and some couldn’t find out penetration, let alone reciprocate. The sight of this gorgeous woman and her comfort with her nakedness the other day had paused Elena, and she felt that they should discuss the attraction.

After one on Wednesday, Candice awaited Elena at the small bistro on Seventy Street. She was at a table along the street window, and she watched as a car stopped and the taxi driver ran around the car and opened the door. Elena swung her long legs free, as the hem of her dress rode up her thighs, and Candice smiled as she saw the clips holding up Elena’s hose’ and her naked upper thighs above the hose’ welt. Surely their afternoon would be interesting, she wondered as she moved her hand atop her mons pubis, teasing her body, but she paused, trying to get control of the building excitement between her thighs, because she saw Elena turn, and she watched as Elena was helping another long-legged woman from the backseat. Elena turned and smiled; she had noticed Candice behind the glass, watching her. Elena helped her Mumm, Christina, who was dressed in an elegant black dress and heels. The older woman was a little taller than Elena. The two stood on the sidewalk speaking and then the mature beauty reached to Elena and kissed her cheek, and she walked south as Elena walked to the restaurant doorway. Candice watched the other woman until she was out of view, and considered the bottom concealed by the taunt black dress fabric. Once Elena had entered the bistro she approached the table and Elena noticed where Candice’s right hand was, and she smiled, thinking how naughty Candice was.

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