What is the definition of transgression?

1to violate a command or law
2to go beyond a boundary or limit


Welcome to Episode 27 of F*ck Like a Woman. This episode is an erotic story about one woman who found herself enticed by the forbidden: her roommate’s boyfriend. This moral dilemma left her puzzled and conflicted as to why this transgression was so alluring.

As a coach who is greatly inspired by Esther Perel, I’ve always known that the world is not black and white, strictly good or bad. There’s an infinite amount of grey that complicates our human experience, and when we immediately condemn and demonize before we have even sought to understand why, we miss the lessons within the journey, and we disillusion ourselves into believing that mere morality will inoculate us from history repeating itself.

To quote Esther Perel in ‘The State of Affairs’, “The intricacies of love and desires don’t yield to simple categorizations of good and bad, victim and culprit. And to be clear, not condemning doesn’t mean condoning. And there’s a world of difference between understanding and justifying. But when we reduce the conversation to simply passing judgement, we are left with no conversation at all.”


The next weekend, Jessica introduced Samantha to her boyfriend John. John was cute in a nerdy funny way and had nice eyes, full lips, and jet black hair. He was dressed in a black hoodie with torn jeans and Chuck Taylors. When they first met, John couldn’t look away from Samantha. She felt a little shy because she wondered if Jessica could pick up on the vibe John was sending her way. Every time they made eye contact, Samantha would catch John staring deeply at her, before she had to look away. John wasn’t intentionally staring at her or trying to make Sam uncomfortable, but it seemed he couldn’t help himself. He thought she was beautiful, but didn’t have enough self-awareness to hide it.

Every day when Samantha came home from work, Jessica and John were already home in the living room drinking and watching TV. One night, Samantha came home with some food to cook dinner for all of them. She started laying everything out on the counter to wash and prep the food. As she was washing vegetables at the sink, Jessica went upstairs to change out of her work clothes and John walked over to the counter in front of Sam and sat down. He started making conversation and joking around with her, playfully flirting. Sam laughed and kept washing the food. When she looked up from the sink, she noticed that John was staring right at her chest as she scrubbed the potatoes. She noticed it was because her shirt dipped down, showing the top of her bra, and her chest jiggled when she scrubbed. Realizing this, she stopped washing and walked away to prep the other food. When she turned around to get her knife, she caught John staring at her ass. He quickly looked away when he realized she saw him, and embarrassingly changed the subject. Jessica came back downstairs and they all had dinner together, but John avoided long eye contact with Samantha the rest of the night.

The next weekend, Samantha and Jessica made plans to go out with some friends to a bar downtown, and John tagged along. After Samantha got dressed and ready, she walked downstairs wearing tight black leather pants and thigh high boots. When John looked up from his drink and saw her sexy legs gracefully gliding down the stairs, he got excited. His eyes took her all in, working his way up from her sexy heels, to her thick thighs and curvy hips, up toward her small waist and round breasts, draped with a low-cut sweater. He watched her chest bounce up and down as she gracefully landed on each step. Samantha could tell that John was watching her, but she avoided looking at him because it was easier to pretend it wasn’t happening, and she didn’t want to bring more attention to it with Jessica right there. Excitedly, they all piled into a cab and met their friends down at the bar.

An hour into the night, Samantha was having a great time with all her friends, relishing the fact that she had started a new life for herself in this big city. She was feeling so carefree dancing to the music. Jessica grabbed her hand and pulled her onto the dance floor, then waved at John to follow. He followed them onto the dance floor where they all started dancing freely with each other, playfully sandwiching John between the two of them. The next song that came on was loud and sultry so they started grinding harder on each other, with Samantha in front, John behind her, and Jessica in the back. By that point in the night, they were all getting tipsy and naturally their boundaries started getting a little fuzzy. What Jessica might have otherwise considered too close for dancing with her roommate, she was now encouraging John to do with Samantha in the name of having a good time. Jessica seemed to find their dancing entertaining and amusing. In light of Jessica’s relaxed attitude, John decided put his hand on Sam’s waist as they danced. And, seeing that she didn’t push his hand away, he moved it down onto her hips, slowly edging his hand around toward the front of her hips, gently pulling her body in toward his pelvis. Samantha felt a rush of anticipation surge throughout her body. John and Sam grinded in sync with each other for another song, and by this point she could feel his pelvis getting firmer and warmer up against her ass. But to Samantha’s surprise, she didn’t want to push him away, she was getting turned on by how firmly he was pulling her hips toward his waist. She was even turned on that he was getting hard rubbing up against her. She felt so conflicted by the loyalty she felt for her new friend and roommate, yet she was getting so wet feeling his hand in such close proximity to her pussy, knowing at any second he could slip his hand between her legs and no one would know because the bar was so crowded. The thought was driving her crazy, and the alcohol was so strong. Jessica tapped them on the shoulder to go get another drink from the bar. Samantha was partly relieved because she wasn’t sure how much steamier things were going to get with John. When Sam slipped away to go to the bathroom, she was surprised to find her thong was soaked. She was a little embarrassed because John wasn’t even her type, but the way he desired her was incredibly arousing.

A couple hours later, their whole group moved back onto the dance floor, and John found his way behind Samantha again. Testing the waters, he put his hand on the small of her back, and Sam kept dancing, tacitly encouraging him without being too forward. As he moved closer behind her, he lightly grazed her ass all the way down with his hand. Her bottle tingled at his fingers. Feeling more daring this time, John slipped his hand under her sweater around her waist and softly touched her skin, tracing the tips of his fingers across her stomach, caressing her body. Then moving his hand upward underneath her sweater, he slowly traveled all the way up to her breast, touching and squeezing it lightly, stopping to feel and stroke her hardening nipple. Samantha’s knees started to weaken, feeling like her body could collapse into his. She was completely out of her element doing this in public and especially with her roommate’s boyfriend. But she was tipsy and the bar was so packed that their friends couldn’t see what John was doing to her. And yet this made it all the more exciting, knowing they could get caught at any moment, but they were too enthralled in the passion of the moment.

A couple songs later, it was last call and the lights started coming on so they all got back in a cab and rode home. On the way home, John and Samantha tried their best not to give anything away, acting as normal as possible. When they got home, Jessica passed out on the couch downstairs. Still in a foggy haze, John had made his way over to the couch next to Samantha, right next to where Jessica was sleeping. One thing led to another and they started kissing. He put his hand on her leg, rubbing up her thigh, loving how her body felt in her leather pants. Samantha was already so turned on that she could barely wait before she unbuttoned her pants, and shoved his hand on her pussy. When he felt how wet her thong was, his dick got so hard. He rubbed her pussy, wanting to be inside her. She climbed on top of him and started grinding against his dick through his pants. He gripped her hips and shoved her toward him with each thrust. Wanting to move someplace quieter, they climbed the upstairs, step by step barely making it up each one as he followed closely behind her, squeezing, kissing, and biting her ass  through her tight pants. They made it to her bed where he slid off her boots and tight pants. He started kissing her pussy and getting her juices all over his face. She was so wet and messy from all the build-up and anticipation of what as about to happen. He unzipped his pants and stroked himself as he smelled and licked her pussy. After a few minutes, he could tell she was getting close so he slid his finger in her pussy to get it wet, and slipped it into her ass as he licked harder on her clit. She went wild. He put a rubber on and thrust himself inside her. Her pussy was so tight that he erupted with a loud moan when he felt himself inside her. He flipped her over so she could finish on top of him. Gripping her ass with one hand and smacking her ass with the other, she rode him harder, going wild. As she bent down to ride him with her breasts pushed up against his chest, he teasingly pulled her hair and told her, “don’t stop”. She lost it and screamed in ecstasy. Feeling her pussy tightening and pulsating around his dick made him lose it.

Samantha found herself unbelievably turned on by the fact that they could get caught at any moment. At the same time, she felt like a horrible person to her new roommate, but it felt like she couldn’t stop. The more turned on John got, the more turned on she got. They both knew it was wrong and yet that’s exactly what made her want it more. As time passed, Samantha found herself going back to this night as a frequent fantasy and couldn’t figure out why it was so enticing to her. She likes to think she would never do something like that again if the opportunity presented itself, but she still wonders what it was about that fantasy that remains so sexually appealing out of all the other experiences she’s had since.

I wondered to myself if it had something to do with conforming to others’ expectations of her, maybe from striving to be a good girl who didn’t act outside what was expected from her. It seems to be the kind of indiscretion that society expects from men at some point in their life, excusing it as being biologically wrapped up in their DNA, but the story is told differently for women. Maybe she was rebelling against what others expected from her as someone who had always been a people pleaser. I also wondered if there was something intrinsically alluring about doing something so bad. Like a child disobeying her parent, Samantha had knowingly subverted the relationship authority of Jessica and John, right under her nose. John wasn’t even someone Samantha would normally ever be attracted to, but she was erotically hypnotized by the enticement of the forbidden. Samantha was crossing a line, a line that is often considered one of the worst a person could cross, and was doing it almost outright, in a bold and daring demonstration of her freedom and desires. It was as though she was establishing her own authority and autonomy in doing so. My hope for Samantha is that she finds other healthy ways to express herself in the bedroom that can elicit a similar feeling of sexual excitement without the risk and endangerment to another person’s relationship.


That’s it for today everyone, stay tuned for next week’s episode where I talk with hot sex advisor to millions, the famous Susan Bratton, as she talks about all the ways women can orgasm, how to initiate dirty talk, her favorite sex toys, and much more. Subscribe to the show so you don’t miss out.



Welcome to Episode 24 of F*ck Like a Woman. Today’s show is a story about an affair. Marco, a successful businessman, finds himself unexpectedly in the throws of an affair, and is left conflicted about the dilemmas facing his marriage. (Names and identifying details have been changed to protect the privacy of individuals.)


I met Marco on a business trip to the East coast while waiting for my flight. He was alone at the airport bar having a drink when I sat down next to him. Our heads turned toward each other and nodded as a courteous acknowledgement of the other. When I looked in his eyes I could see a kind and gentle soul looking back at me through soft, green eyes with an inviting smile. He was a strikingly handsome man in his mid 40s, well dressed and polished with a sophisticated yet modern air. We exchanged pleasantries and somehow quickly wandered into the kind of conversation you only share with a close friend. As distant travelers passing through the exact same moment in time and space, we were able to share a window into each other’s most private emotions and personal stories. I was touched to be entrusted with such an honor.

Marco was the owner of a highly successful real estate firm in Miami. He was married to his wife of nearly 20 years and they had three children together. But under the surface, his marriage had been in disrepair for over a year in the aftermath of an affair. They had recently gotten back together after a brief separation and were trying to make it work for their children’s sake. To Marco, the thought of separating their family and having his beautiful children grow up without a father living under the same roof together killed him. He couldn’t bear the thought of splitting up their family as the price he would pay to gain freedom, even if it would liberate him to live his truest self unshackled by his experience of marital constraints.

Their downfall began a couple of years ago at dinner, when his mother, after having had too much to drink at dinner, confessed secrets from their family’s past that had spent the last few decades seeking asylum. There was always some distant recollection from his childhood that he never could put his finger on and now he learned why. His father, the principal of a private school, had molested a 14 year old girl from the school he was overseeing, and not only that, but his father was extremely violent to his mother and him as a child.

As one can imagine, Marco was devastated. A flood of memories rushed back to him the more it all sank in. It made sense now why there were always emotional shadows lurking that continued to elude him. When he went to his wife, a Cuban woman raised in a very traditional household, to tell her about the disturbing news, she said, “What are you going to do, sit and cry about it? Be a man.” Marco was crushed. In that instant, he felt as though the person he should have been able to confide in with complete support had shut him down and boarded up her walls.

In the aftermath of processing this kind of emotional devastation, Marco sought the comfort and healing he was needing from an attractive woman he ran into frequently at networking events. Jennifer was fun, spontaneous, and receptive. Marco hadn’t started out with the intention of an affair – all he was looking for in the beginning was just a compassionate ear to listen to all that he was going through. He wanted someone to hear him, to see him, to validate the twists and turns he was experiencing, and more than anything to make him not feel like he was alone. In moments like these that bring us to our knees, we default to our most basic human needs to ground us back to what we know. We go through a grueling process of painfully negating the story we once thought was real, and then mentally reconstructing the entire past in light of a new unsettling truth.

Marco and Jennifer’s affair lasted several months and was possibly the most connected Marco had ever felt physically, and perhaps emotionally, to another person in his whole life. He was able to experience sharing himself with another through sexual intimacy at an extremely deep level, and it was a way to escape his pain of the past and his problems at home. Being with Jennifer brought him back to life.

She was adventurous, curious, and inviting. Jennifer did things with and for Marco sexually that his wife would never even allow a conversation about, let alone actually do them. For the first time since he had been with his wife, Marco experienced the most exquisite blow job. Jennifer loved going down on him and got off on pleasing him. She would kiss and lick him as though he was a dessert to be savored – passionate and sensual, yet wild and adventurous.

The difference in his experience with his wife and Jennifer was that Jennifer wanted sex just as badly as Marco did, and unlike his wife, Jennifer didn’t treat sex as obligatory or as though she was fulfilling her “duty” to him. Marco found acceptance from Jennifer and she indulged his sexual fantasies, which included sex play in bathrooms, at parties, and secretly at work events. Most importantly, it made him feel special that a woman was so entranced by his dick that she couldn’t get enough of it. It was the kind of attention and recognition of his sexuality at its most quintessential level that his wife had always ignored and put to shame.

To Marco, it was nurturing a part of himself that had long been neglected by his wife and restored a sense of self that he desperately needed to feel wanted and longed for. Marco wanted to be with a woman who didn’t just lie on the bed like a manikin in their usual missionary position – remaining uninterested, distant, and waiting for her time to be up. What he wanted was a woman who would come to life when he touched her, someone who couldn’t get enough of him and made him feel vibrant and on fire. Jennifer made him feel alive.

Marco eventually came to a point where he knew this affair had to end. Not only did he end his relationship with Jennifer, but he confessed to his wife. He described his wife’s response to the whole ordeal with just a few words, “As long as you didn’t get her pregnant,” she responded. Her reaction was both relieving and painful, further driving the knife in his wound – deepening his feeling that she didn’t care enough about him to even become jealous or express heartbreak. Thankfully this time he didn’t run back to his lover because he knew that he wanted his family together for his children’s sake more than he wanted a lover.

Marco and I touch base every now and again and I’m happy to hear that he hasn’t engaged in any more extramarital affairs, but it certainly doesn’t prove that his marriage is any better off. His wife continues to refuse going to therapy, and Marco continues to crave the connection of another. My mind conjures questions that I dare not ask him, though I can’t help but wonder – has he considered seeking professional help for his own sake? Has he studied his wife to know what gentle seeds he could plant that would soften her and allow for some open conversation over a period of time? Does he know how satisfied she is in their marriage? What is it that she truly longs for that she’s not getting? How does she self-define her role as mother and wife? What was it that attracted her to him in the beginning, and him to her? Has he tried recreating that in various scenarios? There are countless other questions I want to ask, but the truth is that none of these questions matter if he has mentally passed the point of reconciliation. Although he is still wearing the role of husband and father, he has long been departed from their marriage.

While we will never know the other side to this story and there is much left untold, Marco’s wife certainly deserves the respect and courtesy of acknowledging that she did not deserve to be on the receiving end of his affair. But it certainly doesn’t make her an innocent party either. So too did she break her wedding vows to Marco with the years of neglect, emotional stonewalling, avoiding therapy, and not even being willing to discuss the state of their relationship. And who says she alone gets to control the sexual and emotional intimacy that affects two people, not just one? Hurt and suffering come in many forms in a relationship, and the kind that happens gradually and spanning several years or even decades is oftentimes no less worthy of repentance than the gutting experience of uncovering an affair.

Ultimately, it all comes down to this: the only person in any given situation we have some form of control over is ourselves. And usually, when we change ourselves, we change the other, but unfortunately it doesn’t always work that way. Sometimes there are forces so great existing outside our control, that in the end, we are left with difficult choices ahead of us.

A relationship is like an ongoing negotiation that is always in flux, subject to addendums and alterations. It will ebb and flow as its creators continue to evolve in life and love. It should also be said that every couple has autonomy to decide what kind of bargain they will strike with their partner, and from the outside that bargain might not always make sense. But we can hope that those living within it can find some sort of balance of happiness and satisfaction that works for whatever stage of life they find themselves in, and above all, that they continue seeking the courage to be honest with themselves and their partner about what ingredients they need to live their best life and truest self.