A Week in the Sex Life: Cheri's Journey with Pegging and Intimacy
Welcome to How I Do It, a series offering a seven-day glimpse into the intimate world of a stranger. This week, we hear from Cheri*, a 29-year-old bisexual woman who previously discussed her preference for no-strings sex with Metro in July 2025. Now, she's navigating a new chapter with a male partner, focusing on emotional caution and sexual exploration.
Setting the Scene: A Slow-Burning Connection
Cheri is dating a man, though they are not exclusive initially. We're taking things slow emotionally, as I've been hurt a few times in the past year and want to avoid being love bombed again, she explains. Her partner is less experienced sexually but open to trying new things, which aligns with Cheri's playful approach to sex. I try new things to see what I like and don't like. It's how I discovered I enjoy spit play and role play. Now, I'm keen to try pegging, she shares, noting her curiosity after using a strap-on with female partners but never with a man.
Monday: Planning and Preparation
Jack* messages Cheri to plan a date for Tuesday night. They've been seeing each other for six weeks since meeting on Hinge. While Jack has broached exclusivity, Cheri remains hesitant due to past heartbreak. However, their sexual chemistry is undeniable, with Jack showing a particular interest in anal play. After work, Cheri receives an anal vibrator she ordered online, charging it in anticipation of surprising Jack.
Tuesday: First Steps with Anal Play
Cheri feels impatient all day, and after work, she heads to Jack's place. They quickly escalate from cooking to the bedroom, where Cheri introduces the anal vibrator. Jack enjoys it, and they switch to a blowjob for his climax. Later, as they cuddle, Cheri jokingly asks about pegging, and Jack admits he's never considered it but is open to trying with her. They agree to give it a go, sparking excitement in Cheri.
Wednesday: Reflection and Distraction
The next morning, Cheri rushes off after a quick kiss, feeling distracted at work by flashbacks of the night. Jack's messages excite her, but she also feels scared, realizing she hasn't used dating apps in weeks. After meeting a friend for dinner, she returns home exhausted, opting for an early night.
Thursday: Anticipation and Research
Working from home, Cheri takes a run and later finds herself turned on, using a clit sucker while imagining pegging Jack. In the evening, she researches pegging tips, wanting to ensure she gets it right as a bisexual woman exploring this dynamic with a man.
Friday: The Pegging Experience
After a Pilates class and errands, Cheri meets Jack for a Korean dinner. Back at her flat, they confirm their desire to try pegging. Using a strap-on and anal vibrator, they proceed slowly with plenty of lube and communication. The experience feels intimate and powerful, with Cheri enjoying a dominant role. Jack orgasms intensely, and they laugh at the mess before he focuses on pleasuring Cheri, leading to multiple climaxes.
Saturday: Deepening Connection and Exclusivity
Waking up together, they attempt sex but pause due to tiredness. After brunch and a walk, Jack asks about exclusivity, citing their vulnerability. Cheri agrees, feeling nervous but optimistic. They spend the day making out and watching films, and later, Jack shyly requests pegging again. They try a new position but revert to doggie style, with Jack finishing quicker. They shower and cuddle, with Cheri feeling happy about their exclusive decision.
Sunday: Reflection and Moving Forward
Jack leaves for plans with friends, kissing Cheri goodbye. She asks if pegging will become regular, and he says whenever she likes, assuring that it doesn't replace traditional intimacy. Sore but satisfied, Cheri meets a friend for a spinning class, keeping the pegging details private. She reflects on a week of exploration, trust, and emotional growth.
