Cassandra and Will (Exploring BDSM) – San Francisco Story # 9

Having been doing online research for BDSM for my upcoming novel and was inspired by some of the themes. Also envisioned what if my character dies, what happened then? Can a couple develop a love relationship if they are really into BDSM? According to research it does not happen often...What does death do it all?

I. Fucking vs. Making Love

Will touched Cassandra’s back, gently, as if he was giving her a back massage. He spooned her, and he said in a dreamy voice, as if it was more for his own benefit, than for hers:

“It was that river boat, or rafting trip when I first met you. That same Sunday afternoon, we went to see a movie. You wore a white dress, and you told me that you had not worn any underwear. I couldn’t concentrate; consequently I couldn’t remember anything about that movie. We then went to your place, you played a transvestite porn movie, which was in your VCR, in VHS format, and then you stripped to nothingness, and told me that you were going to sleep. And we agreed that I could stay. But you’d go to sleep. You lay in your bed, and said that you only slept naked. You went to sleep, or it seemed. It was quiet, you may be still awake, I couldn’t tell.”

Will paused, to see if Cassandra was still listening. She was indeed, she could hear her heart beating. Will recounted this same story, of how they first met, Cassandra  still liked to hear it even though she’d heard it many times, every time a little more details were added. She was alert and awake, enjoying that moment of reminiscing.

“You were quiet, I couldn’t tell if you were asleep. But who in the right mind could just go to sleep laying next to you, the naked you. What were you thinking? I went down on you, and tasted you, and woke you up. You had shaved your pussy, you crazy girl. You were bare. Nothing down there, just smooth pussy. I woke you up and then we fucked.”

Will completed telling this story, more accurately, retelling this story. He ran his hand up and down Cassandra’s back, while spooning her. His penis pressing against her buttock, and they fit like a glove.

“I love fucking your pussy. I love the naked you. I love how you shave your pussy for me.” Will continued.

The room’s lights were dimmed. It was a relatively early evening, to Cassandra’s standard. She rarely went to bed before 2 AM. It was about 10 PM at the time.  She was lying in Will’s bed. The bed she occasionally shared with Will, the bedroom, the apartment, which allegedly had been there all along, yet it took her fourteen years to see it for the first time.

The dimmer was turned low but the room was still relatively lit, Cassandra could see Will’s face, his facial frame anyway, His prominent nose, his thin lips and his eyelashes. His eyes were now shut, he was leisurely curving up next to her, his body wrapped in hers, he was so rested around her, he was falling asleep, she was alert, feeling incredibly sexy, sensual and satisfied, as any freshly fucked woman would feel.  

She ran her hand through his blond curls. It felt soft, and airy, like her heart, content, beating at a speed as if she just inhaled ecstasy, euphoric, as if she could fly. She loved fucking Will.  She loved the feeling after being fucked by Will.

“Do you mean now, or before?” Cassandra asked for clarification from Will. She was naked, wrapped around by his arms, just like she was fourteen years ago, and she had shaven her pussy, like she did fourteen years ago.

“I loved fucking you then, I love fucking you now. I love how your pussy feels to me. I love your pussy.” Will declared.

Cassandra felt satisfied with his answer. She let out a moan, like a cat, she moaned like she was that wild cat wandering on the roof top in late evenings, desperately in heat, even though Will had just thoroughly satisfied her. She wanted more. She always wanted more from Will.

They kissed, they couldn’t kiss enough so they kissed whenever they could. She wrapped her arms around Will, as he was back on top of her, his penis was hard again, he was pushing himself into her, while she was lying naked, without any thread of clothing. They were just playing this time, but it felt good to have Will’s hard penis inside of her again as he gently glided in and out of her warm puddle.

She asked that question that made her ache each time she asked of herself, in her head, to her self, but this time, out loud, to Will. “How come we did not end up together?”

“Who says we are not together?”

Will meant what he said. But he also knew what Cassandra meant. She was a married woman, with her husband of twelve years, they had a child, a little girl named Emily, now ten.  Yet, on this Wednesday evening, lying in Will’s bed, was not a married woman in heart, but a woman who had finally reunited with her lover. She was with Will, one of her past lovers, someone who she had known before the existence of her husband, before many of her ex boyfriends came and went, before she knew what love was.  Will, her very first guy who went to a particular school for graduate studies in Boston, which caused a domino effect later on as she dated several in a row after Will from the same school, half by coincidence, half by conscious choice, she was in demand, and there were a lot of those people around San Francisco back in the 90s.

Will was her very first guy who she felt that physical pull, greater than emotional connection, greater than anything she had felt in a while, just that pure physical connection.

She never got to know him at a deep level. She never tried. She had no time to get to know him. When Cassandra was near Will, all she ever wanted to do, was to fuck, to use Will’s word.

II. The Illicit Affair

When Will first met up with her several months ago, when it was just the turn of the fall, when this illicit affair just started, she would wince whenever he used the word “fuck”, or “pussy”, it was vulgar, coming from Will, a scholar, a professor from that renowned university just down the Peninsula, it felt peculiar, but Will chose words carefully, she later learned.  He did not waste any words, he meant what he said, he fucked her because that was all that was. She had innocently asked him once, “What was the difference between fucking and making love?”

Will answered by saying “They were the same to me.”

Cassandra realized later on, to Will, they WERE the same. Fucking equated Making Love. He couldn’t love the way ordinary people loved. She felt the way he loved her, was through fucking.

She was, and is his fantasy girl, his sexual slave, his BDSM partner. The level of intimacy had grown over the past few months. She felt that he was opening up to her. Well, as much as he could, for someone who was so private and emotionally distant.

She sometimes felt that ache when he dropped off the face of earth, her earth anyway, when she wanted to hear from him, she wanted to feel him and see more of him. So she withdrew also, by going into that world of writing, or to mind her family life.

Cassandra believed Will came into her life for a reason. Perhaps Will came back into her life to remind her what a great, vibrant, intelligent, fun and attractive woman she had grown into.  And he reawakened the writer in her.

But she didn’t think that was enough. She wanted a deeper purpose. Like perhaps he saved her from her miserable life, but she didn’t have a miserable life to speak of. She was content, satisfied, and even happy with her career, her friends, her family, and her situation. All but one situation. She was fresh off an affair, a man who also went to the same graduate school back east, who was the same age as Will, who was independently wealthy, and who was curiously obsessed with her. She was creeped out by it.  She wanted out, she got out. Will came to her because of it. That was what fate brought her, Will, the handsome man whom she would always fall for, the man who she knew so little about, yet kept in touch with for these many years, because deep down, she knew, perhaps, one day, Will would be able to give her what she wanted.  Sex, sexual freedom, sexual exploration beyond her wildest dreams, the BDSM stuff.

They met up at a restaurant, near the university, where Will taught computer science, in the upper peninsula, it was a funky restaurant with a young college crowd. Cassandra was not nearly as comfortable as she should, it was really out of her element. One, it was not one of those fancy restaurants in the city, where she worked; two, she was in a restaurant full of twenty year old students.

They caught up on their respective lives. She learned that he had also become a father, and divorced. He had married a woman whom fathered his child, they fought constantly, she was domineering, and had strong opinions and lived a carefree life. He wanted out before she wanted out, but it was mutual in the end. She was quite successful in her line of work, she sold software for a large conglomerate firm, and she was happy on her own, without him. They divorced and shared child custody. He stayed at their house in Palo Alto, now only under her name, on some evenings when she was traveling, and on other evenings, he returned to his apartment that he always, somehow, kept, in the city. 

Cassandra came to see him on those rare nights, where Will had let her in now freely, whereas fourteen years ago, she never knew where he lived. She was never invited to his place back then. She knew nothing about the child Will fathered, or the child’s mother, she never asked, nor would it mattered. What mattered to her was Will. She felt that for the first time, for the second time actually, there could be a chance of getting to know Will.

III The adventure of BDSM and other kinky sex

“Will Mendelson, I know nothing about you.” Cassandra announced it to him the other night, while he was drifting to sleep, after he had thoroughly devoured her, tied her up, chained her up, spanked her silly, and fucked her in the ass, her second time, the first time was just a couple of weeks ago. He stuffed his cock in her mouth so that she could suck on it until he was good and ready, and then he jammed his cock in her pussy while she was tied down, her butt cheeks exposed, tight. After a while, he took his cock out and forced himself into her ass while she screamed. The pain, was excruciating.

She had never had anal sex before Will, and she liked the pain despite of it, she wanted more of it.  She realized that she had never been good at mundane sex, she wanted bondage, S&M stuff that hurt her, and she wanted kinky stuff. She wanted him to pee on her, that visual was first introduced to her via one of Henry Miller’s books, formally banned in the U.S. She read in the book about a young girl, only 16 of age, tied down by her mother, while men fucked her and her mother looked on. She read about men peed on women while they fucked, and had those women drink their pee in those books. She read about women getting fucked in their asses.  She was only twenty when she stumbled onto Henry Miller and Anaïs Nin’s work.  She was aroused.

Until then, and even afterwards, she always thought it was because she was a sick person, she thought she was fucked up in the head.  But then she realized that she was just wired differently. As she had gotten older, she realized what she wanted, was not just any man peeing on her, she wanted that particular brand of men, those who were otherwise tidy, anal retentive, fashionable, metrosexual, clean and lovely men to get dirty on her. She wanted Will Mendelson.  The clean shaven, blue eyes, blonde curly hair, trimmed glasses, white teeth, boyish smile, slim, fit, fashionable William Mendelson.

That was the kind of sex she wanted, sex with the full extent of erotica, sex without the feeling of constraint and boundaries. She trusted Will, she wanted to please Will, in a full extended version of slave and master version, she was the submissive one, the one who would become Will’s sex slave, have him do to her as he pleased. She wanted that relationship to grow, to flourish into something only described in Henry Miller’s books.

But often times, they were caught up with realities. Reality was, Will had a tenure track to pursue, lectures to give across the country, research to do, and a little child to raise.

Cassandra had a busy career herself. She worked at a consulting firm specialized in energy trading. On a bad year, her bonus was more than most people made in a year in salary.  Money was never the issue.  But when money was not the issue, people tend to seek others things to fret about. For Cassandra, it was the lackluster of her marriage. Cassandra wanted a full on BDSM relationship, which was not something that her husband would want to venture into, or talk about. She stumbled onto it with Will.

They lay awake for a few nights a months, no more than two by the last count of it, they fuck with abandon, during those rare moments, Cassandra felt loved, even belonged. Then they both leave for work for the next day, and they won’t talk, email for days, she had no idea what Will’s daily life was like, she had somewhat an idea as to what her boundary was. She suspected that Will would not be happy if she called him, she was not allowed to go and visit him in his office. She did not know whether Will had a girlfriend, another lover like her, a student he fancied when she was not with him, or for that matter, Will’s relationship with his ex wife.

She suspected all of the above were happening behind her back. Yet, strangely when they were together, Will made her feel like she was the only person who mattered. There was a certain amount of trust, trust that was implicit, when one entered into a BDSM relationship.

She had been reading up on literature and psychology behind a BDSM relationship. It was a quite complex situation; it required trust, a lot of it, a sense of bond that nothing else could break, or replace, it required a sense of removal from the reality. According to these literatures, it often was highly addictive, she was addicted to Will. She began to understand why Will always asked her to be quiet - it was part of the script. She began to realize why Will needed her and talked to her in such a way as if he owned her, and told her that she could do things when she did not ask to be permitted. 

She began to see a pattern. He would occasionally write, “Yes you can come to see me.” He needed to give her the permission. When she asked or suggested things, he would not always agree to it, he needed to have final say. She was frustrated most of the time, saddened by his lack of response, she hid in a corner, in private, she would cry because he had deprived her of the basic needs, the need to connect with him, yet she felt belonged, not to him, but with him. His oddball behavior made sense to Cassandra, his sense of domination spilled over to life itself, as if he was waiting for her to show up and now she had showed up, he was able to exercise his power on her. 

Cassandra begged to be with Will on days when he was free, in daylight.

“I had not seen you in daylight, not ever.” She commented on the fact they often stayed inside of his apartment when they did manage to meet up.

“But you did see me in daylight, when we went to Ocean Beach.”  Will answered. Cassandra was not sure to hit him over the head with the book she was reading, or to laugh at his weird sense of space-time continuum.

“Darling, it was fourteen years ago.” Cassandra reminded Will.

“We flew kites.” Will made a comment as if it took place yesterday.

“On top of it, I had no memory of it.” Cassandra countered.

She reached for his balls, and she touched his penis, gently massaged it until it became hard, and she fed it into her pussy, now wet like a puddle, he glided into her, while spooning her, rocking her, so very tenderly. The contrast, between the tying her up, spanking her, entering her by force, and to cradle her as if she was this most fragile flower, his fragile flower, made the relationship in a way, so powerfully intoxicating.

Cassandra read it somewhere BDSM couples often form a bond that was not necessarily love, but a deep trust that nothing else would break. She felt that with Will, despite his largely absent presence in her life. When she was with Will, she was complete, he brought the most natural side of her out, and she felt that she was bringing that side of him out as well. The side where he whispered quietly into her ears, in public, and told her how much he enjoyed putting a collar on her, and wanted to take her to public places while holding the leash that was tied to the collar around her neck.

She wished – on those nights, on most nights, when she was away from him, what it was like to be with him always, to belong to him, not just with him, but thoroughly belonged to him. She wondered if their lives would be drastically different, if her logical, sensible side would win out, or if her natural, instinctual, sexual perversity would win out.

IV The Tide Changes

On those evenings, which was the majorities of Cassandra’s evenings, she wondered about Will, what Will was up to, whether he was with someone else, or whether he wanted to see her more often.

On those evenings, Will thought of the same thing. He finally was able to open up to someone, someone whom he always adored. Someone he could love, give all that he was able to give. Will’s lugubrious enthusiasm was often shown early in the morning, when he was alone, alert and most energetic. He was a morning person, after his run, he would sing, in the shower, he would plan the day with a thoughtful note to himself, to send Cassandra a loving note, to tell her how much he enjoyed their last play date, and how much he wanted her body, and he would expect a note from Cassandra, of course, before his own reply to her, because she was always the person who sent him a note first, and he would reply gingerly, playfully, and teasingly.

He loved this game, this game of BDSM, this game of controlling every move in this chess game. He was a good chess player in college, he knew how everything worked statically, he knew he was in control, had an upper hand, and he had her in his pocket, unlike the first time, fourteen years ago, when she slipped away like an eel in water. They did fly kite that day in Ocean Beach, she was fumbling with the rope, and he caught her, he kissed her in that convertible he drove her in, just like he kissed her now, but she was slippery like an eel then, she kissed with abandon, she laughed like a little girl, and she walked away when he insisted on playing based on his ground rules.

But not this time, Will told himself. She came to good senses, she knew that I needed the control. I was the dominant one in this game, and I called the shots.

Cassandra knew that about Will this time too. She entered this relationship knowing what she would have to give up her power, her way of things.  She liked it for a while. She put up with Will’s temperament, his changeable ways, his last minute cancellation and his excuses.  She knew she needed Will for that deep, dark, secret fantasies and she was strangely OK with all of it. So she thought.

Then one day, it was just another normal day in Cassandra and Will’s world. Cassandra went about her day, kissed her daughter Emily goodbye when she dropped her off in school, and her husband, Robert, the man who was never to be mentioned again in this story, but for all intense and purposes, would show up now, because dear readers, this story was about to end. She was waiting for her BART to arrive, when a text message showed up.

Cassandra never knew how to use text, but she knew this was from Will, she somehow instinctively knew. It was indeed from Will.  It read, “Baby, I got into a terrible car accident, in hospital now. Chances are not good.”

There was a sense of panic. Cassandra got back to her house, located the hospital Will was at, and took her car to the hospital instead of going to work that day. There she found Will lying, helpless, bandaged up, came out of a surgery, with IV drip. It was not happening. It couldn’t be happening. This could not happen. Cassandra told herself. She repeated it as if those words would somehow alter the outcome of Will lying in a hospital, dying.

She leaned over to kiss him. He smiled, or attempted to smile. His deep blue eyes seemed gray that day. His head covered in bandages, his legs lifted up, he said that the texts were sent by a helpful nurse. “You know, baby, I know you don’t do text. I am sorry, I couldn’t find a laptop they’d let me borrow”. Will was trying to be funny.

Cassandra was all of sudden in tears. She turned around to wipe them dry and returned back to face Will, flashing her beautiful, bright smiles. She didn’t want those to be the last parting words. The strange thing about people, who were involved in a relationship, was that they might not know that they were in a relationship, until it was too late.

All this time, Cassandra had pretended this part of her life, was a tucked away secret compartment that got opened twice a month, at the very most.  Will, was the last person to require her attention, and she was not sure if he needed that attention anyway. He was always the decision maker in their BDSM relationship. He paid the dinner bills, he put on her coat, he extended his arm out so she could loop her arm through his while they walked on the hilly San Francisco streets, he paid for parking and he took charge in ordering food. This was a pre-defined relationship that required every step of the way to be well thought out. She was not a kept a woman by all means, but in this submissive woman / dominant man dynamic, she was, strangely, Will’s property, twice a month, on his terms, always on his schedule. And it worked, until now.

Lying in the hospital’s bed, was this helpless man, a freaky car accident had reduced him to this normal calm-voiced man who once made Cassandra weak in her knees every time she was near him. He was not in control for once. He was in fact, losing his battle. She saw his lights dimming, she saw how he reached out to her, caressing her for possibly the last time. She wanted to cry again.  But she couldn’t. She for once needed to be strong. She had to find her strength. So she smiled.

IV Nostalgia is a brand of Narcotic

“Hi Baby.” She touched the lose strand of his curly blond hair. 

“Did you remember that you had asked me, how we first met, on that trip of ours to Portland, where you came to visit me and stayed with me? And I said that I couldn’t remember?”

“Well, I did remember, I found it in my journal dated 1998. You were right, we went to a restaurant, I ran into a colleague of mine there, and we had Italian food. You were right, we did go out. Though I still don’t have any actual memory of it. You were right to ask me to dig out those journals.” Cassandra told Will. 

“We had fun that night. You were right.” She continued.

Will smiled, she saw that boyish smile under the bandaged face. She touched his face tenderly, she remembered those rare nights when she spent with him, how after he had tied her up, spanked her silly, and how he forced himself into her ass, and how much pain she felt, and how much she enjoyed it. Afterwards, she liked to curl up next to him, sometimes putting her head on his chest, and touched his full set of curly hair, and how he said that he liked the way she touched him.

Cassandra wanted to cry again, not because of seeing the lights slowly leaving Will, but for her sudden urge of declaration of love. The word she never used in this context of relationship. The scholarly view of BDSM was that it would very rarely turn into a love relationship; it was often an intense, emotional, psychological relationship, but not love. But what was love anyway?

Could love exist when everything else failed to explain the emotions she felt for Will? And what if there was really nothing else mattered in this world but her sense of loss, the loss that when Will ceased to exist, she too would cease to exist? What if in this process, she had, despite her better senses, become a person who utterly, completely, resolutely, belonged to Will?

She realized at that moment all those things that she ever wanted to tell Will, would be too late, if she didn’t tell him then. Like how much she had wished that he’d written more to her, talked to her more often on the phone, shared his life more with her, how she wished that he would demanded more of her time with him, even though he might be rejected because she had a life outside of his too?

She sat by the side of the hospital bed, the bed that was so decidedly small, utilitarian, and made strange squeaky noises like alien giving birth if you touched it just so. Her face transfixed on the monitor, Will was fast drifting to sleep under the morphine drip. And Cassandra started to tell Will this story.

“You know how you always told me how you met me for the first time? It was probably the best moment you had remembered me by. I was happy, you were happy. I was elated to have met you, my beautiful Will. I had no memory of that, so I appreciate you telling me each time.

You know what, I never told you this, but, Will, of all the moments that we shared fourteen years ago, there was one moment I truly remembered, I bet you don’t remember this. I remember how it was like for you to leave me.

You had an early meeting, in Eugene, and you stayed with me in Portland, it was crazy, it was so far away. Two hours of drive. But you wanted to stay with me. I liked it, a lot.

That morning you woke up, and you had taken a shower, and I was still asleep, it was 6 AM, you always got up a lot earlier than I did. You said that you’d go back to San Francisco that evening. You hugged me and said ‘go back to sleep little girl." I had thought I had one more night with you, in Portland, I thought you said that you were going to spend two nights with me, but you changed your schedule, just like you often do now.

Did you know what you told me? You told me that you’d see me back in San Francisco, on Thursday evening, when I returned from my project. You never called, or emailed. I waited for you to get in touch with me. I knew somehow in my gut you would not but I waited for you anyhow. You made promises, and you broke them, like you often do now. I never got mad at you. I was disappointed, even sad, but I knew you were you, you’d never change. I didn’t expect you to. That’s how I decided to end things fourteen years ago. I knew I could never count on you, not on a day to day basis anyway.

You remembered the happier times, how we met, how I stripped down to nothingness, shaven pussy, a white dress with no underwear on. How you went down on me, woke me up with your lips, but I remember how you left me, so nonchalantly, so full of promise, so full of hope and desire for a bright tomorrow. That tomorrow never came, not for me anyway.

Here I am, I found you again, fourteen years later. And you know what, I just realized this, our tomorrow would never come, again.”

Will was fast asleep by the time this long monologue ended. Cassandra found herself in tears, inconsolable.  Will was only 47. He would be dead, or not, depending on how exaggerated he was with his texts, sent by the good-hearted nurse, but Cassandra knew one thing was for sure. Whatever it was there between Will and her, it was to be severed. She was trying to fix a past mistake. She had her heart torn out by a charismatic young man fourteen years ago. She wanted her heart back, the complete heart, not the one that was patched up and could be broken into pieces anytime. She might have what it took to survive this BDSM dynamic, but she would never be completely herself outside of this BDSM relationship. She wanted more, Will, was incapable of giving more.

Will would never change, he would no longer be afforded an opportunity to change now, he could be dead tomorrow, or in a month, he would not be the domineering man who demanded things or permitted her to do things. He would not be there to take care of her, cradle her after her secret desires were fulfilled: some were pure pleasure, some were pain, but there was always the pleasure after. She would lose this one man who knew it all, saw it all, and he would never knew how much he hurt her, not physically, but emotionally. Yet she strangely desired and loved him unconditionally.

She wanted this to be the way to end it all. She wrote a note, in haste. “My Dear Will, take care of yourself. I love you, always.” She knew what this note would mean to Will. He had never permitted her to express herself freely, and she knew, instinctively, that dominating persona Will put up would not have appreciated reading this note, or this story, in fact, it would probably drive him away or make her less desirable to him. But that other Will, the one she knew perhaps really cared about her deeply, the Will who rarely came out to play, who remembered her in that white dress with fondness, who fell asleep soundly with his arm wrapped around her, would appreciate the sentiment.

With that, Cassandra picked up her purse, scarf and hat, and walked out of the door.

She would not return. She knew it in her heart, this was truly the ending Will wanted too.