I’m sexting the manager at the prison where my ex is locked up

It’s a murky situation for this week’s diarist (Picture: Myles Goode) Welcome to How I Do It, the series in which we give you a seven-day sneak peek into the sex life of a stranger. This week, we hear from Lara*, a 38-year-old journalist and mum-of-one from Cornwall. She split up with her partner of two years in May 2021, 18 months after he was jailed for drug offences. But Lara is now involved with another man in the criminal justice system — she’s currently sexting a 57-year-old prison manager, who runs the prison where her ex is serving a sentence. Finn* slid into her Facebook DMs in July after the pair both commented on a local news article. She’d already spied Finn at the prison when visiting her ex, and the pair soon started exchanging texts. ‘As a single woman I love that I now have freedom to do whatever exciting thing takes my fancy,’ Lara says. ‘Sometimes I feel I wasted my teens, twenties and early thirties in a long-term relationship with one guy, while everyone else was out having fun. ‘Nowadays, I really like having my own house and social life. I don’t believe that sex needs to come with a conventional relationship.’ While, she hasn’t met Finn in person yet, things have become increasingly sexual over messages – and they’re planning to meet next month. Ask Metro Use AI to go deeper into the stories you care about – powered by Metro and trusted publications. There’s just one problem: Finn is married. So without further ado, here’s how Lara got on this week… The following sex diary is, as you might imagine, not safe for work. Monday I wake up to two videos from Finn, who’s on an early shift. The first is a very explicit video he’d promised me of himself masturbating. In the second, he’s just out of the shower and getting ready, while chatting about his day. He looks hot. I love that he’s tall and much more heavily built than me. I’m notoriously bad at figuring out when a man is interested, so it wasn’t until he asked why I was single over messages – after repeatedly telling me how hot he thought I was – that I realised he might actually fancy me. A mutual friend told me they’d previously been in the same WhatsApp group with Finn and that I’m not the first person he’s cheated on his wife with — he also had a fling with a colleague. Strangely, I’m turned on by the fact he’s had an affair before. There’s something about the whole forbidden, other-woman dynamic that I find incredibly appealing, even though I’m appalled by the reality of it. And it works for me. I love my life with my daughter, in our own house, and I don’t want a man around full-time. Tuesday Historically, I have minimal patience for any man who asks me for pictures or videos. I normally outright refuse. It’s a dreadful waste of time. You have to put makeup on, shave your legs and find appealing underwear, all to not actually have sex. So when Finn first asked me to send him a naked video, eight days after we started messaging, I laughed and told him absolutely no way. Then, for reasons I still can’t entirely explain, I changed my mind. We’ve now been exchanging videos for over a month. Today, after the school run, I lie on my bed in my bra and thong, with my MacBook propped up at the bottom of the bed, and film myself touching myself. Despite having no idea what I’m doing, I feel confident and empowered filming it. I orgasm, send the video to Finn and he loves it. Wednesday We spend the morning chatting about life on WhatsApp, including family, gardening and our past relationships. I feel a huge surge of guilt every time he mentions his wife. He says they never have sex because she’s midway through the menopause and disinterested, but married men always have an excuse. As a feminist, I know there’s no justification for exchanging sexual videos with another woman’s husband without her full, informed consent. I can’t rationalise it. Yet I also can’t stop myself. We also live miles apart from each other, hence why we haven’t met yet, so the chances of her finding out are slim. But then there’s the guilt about my own ex. I know it’s murky — I’m having phone sex with the man responsible for overseeing my ex’s detention. Interestingly, Finn also brings up his affair with the female colleague, which ended around a year ago. She still works at the prison and they’re friends now. She’s around my age and we look extremely similar. He clearly has a type. It doesn’t bother me. Thursday I’m up early and send Finn a photo of myself naked, sitting cross-legged in front of my huge bedroom mirror while blow-drying my hair. He’s getting ready for work, while his wife collects their toddler grandchild, and calls me. We end up having phone sex. I still find it slightly horrifying that I’m turned on by him in his prison officer uniform. That uniform represents a time when the state unexpectedly ripped my then-boyfriend away from me, bringing an abrupt end to our happy, carefree relationship – and, with it, a brilliant sex life. Part of me still feels like I’d be sleeping with the enemy, if we actually had sex. Nonetheless, we both masturbate while talking about what we want to do when we finally meet. I tell him I want to put my mouth on him and feel him getting hard. He tells me he wants my nipples in his mouth. Infuriatingly, I get a work call and realise I can’t avoid dealing with it. Neither of us climaxes, leaving us both sexually frustrated. Friday Last week, Finn offered to buy me a sex toy. Today, he tells me to choose one or he’ll pick for me. I’m writing to a deadline, so I don’t reply. Not long afterwards, he sends me a screenshot of what he’s bought instead. For a moment, I assume he’s joking. It’s enormous. I checked the measurements and it would stretch from between my legs to about a third of the way between my tummy button and my boobs. I tell him I will be sending it back, so he orders me a much less terrifying, cute purple rabbit instead. Saturday This morning, I’m complaining about my job in a video message. Finn says that I should come and work in the prison with him. He pauses and smirks, saying: ‘Or become a prisoner in it.’ I’m horrified. After everything that happened with my ex, I’m secretly still sensitive to the hint of losing my freedom and being away from my child. I don’t let him know he’s rattled me. Instead I tell him he should be locked inside a small room while I decide whether he’s behaved well enough to be allowed out that day. I add that I won’t be sending him any further naked photos and videos until he apologises. He even demand a video of himself pleasuring himself. It is a risk. I haven’t yet established whether he’s a dominant kind of bloke – and I wonder whether he’ll find me suddenly turning the tables on him exciting or think I’ve gone too far. He is noticeably hesitant about my demand. Thirty minutes later, I get my video and multiple apologies. Sunday My parcel arrives, and I try the purple rabbit and wonder whether to make a video with it. It’s quite exciting and there’s a risqué element too, as there’s an unwritten rule you’re supposed to hate the hot guy who used to lock up your ex. Yet, I’m sending him videos of myself using a sex toy he sent in the post. I fully subscribe to the whole ‘doing it for the plot’ ethos in life. The 19-year age gap is a huge turn-on too, because of his experience and confidence. I’ve never slept with anyone older before. He asks if I’ve space in my diary to see him. After nearly two months, we’re finally going to physically meet. 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