What is the definition of transgression?
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.