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But now, there’s been a development. Cheri, who is bisexual, is dating a guy — although they aren’t exclusive.
‘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. ‘He’s less experienced sexually than me, but open to try things.’
This openness is important to Cheri, who enjoys a ‘playful’ relationship with 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 now keen to try pegging.
‘I’ve used a strap on with a female partner, but never with a male partner, and I’m curious.’
So without further ado, here’s how Cheri got on this week…
The following sex diary is, as you might imagine, not safe for work.
He’s broached the subject of exclusivity, but I’m more hesitant. I got my heart broken pretty badly not so long ago, and I want to take things slow.
One area we’re not going slowly in, though, is the bedroom. On our third date, we slept together, and it quickly became clear Jack has a particular interest in anything related to arse play.
He loves rimming, both giving and receiving. I’ve never minded it; I’ve tried anal a few times with a long-term partner before, and I can enjoy it, especially when combined with clitoral stimulation. But Jack’s enthusiasm for it is making me look at it in a different way.
After work, I get home and a package I ordered has arrived. It’s an anal vibrator I saw recommended online. I want to surprise Jack with it, as he mentioned he’s never used one before.
I put the toy on charge, make some dinner for myself, then settle in with a TV show and an early night. I know tomorrow will be a late one.
After work, I head to his place, where he’s busy making spaghetti Bolognese. I convince him to turn off the stove, and things quickly escalate.
We end up on his bed, making out and shedding our clothes. I tell him to wait there while I grab the anal vibrator. He grins when I show him what it is.
He pulls some anal lube from his bedside drawer, and I start by giving him a rim job and hand job, then I grab the toy. I struggle a bit to get the angle right, so he takes over. We start on a low setting, and he clearly enjoys it.
Having sex while he’s still getting used to it feels like a bit much, so I switch to a blowjob instead. He comes hard, moaning my name.
Afterwards, we take a few minutes to cuddle while he recovers, then hop in the shower before finally getting to dinner. We’ve definitely worked up an appetite by this point.
Later, as we get ready for bed, Jack goes down on me, clearly keen to return the favour, and I quickly orgasm. We settle into another cuddle, and he tells me how much he enjoyed the vibrator.
I ask, half-joking, if he’d ever consider pegging. He admits he’s never really thought about it before, but says he’d be open to trying it with me. We agree to give it a go, and I can’t help feeling excited.
At work, I’m distracted, getting flashbacks of the night before. Jack messages me before lunchtime saying he enjoyed it and that he can’t wait to see me again.
Seeing his name on my phone excites me, which scares me at the same time. I haven’t opened any dating apps in weeks.
After work, I meet a friend for dinner. She’s just broken up with her boyfriend and wants to break the cycle of going back to him. I don’t bring up Jack much, since she’s clearly having a hard time, but when she asks, I tell her I’m enjoying it for now.
By the time I get home, I’m exhausted. Last night didn’t involve much sleep so I take a quick shower, make myself a cup of peppermint tea, and climb into bed.
The day is fairly relaxed, which makes a nice change. Around lunch time, I find myself feeling distracted and turned on. I close my laptop for a bit of a break and use my clit sucker on myself. I imagine myself pegging Jack and it gets me so excited.
I orgasm more quickly than usual, but it doesn’t feel like enough. I have to stop though, as its time to get back to work now.
In the evening, I stay in, looking up tips on pegging. As a bisexual woman, I’m curious about how using a strap-on with a man might work. I like to know what I’m doing and I want to get it right.
In the afternoon I read on the balcony, and soon enough, it’s time to get ready for my date with Jack.
We meet at a Korean restaurant I saw recommended on TikTok. He kisses me hello and compliments my short skirt. After splitting a dessert, we head back to my flat, barely making it through the door before we’re kissing.
By the time we reach the bedroom, I pause to ask if he still wants to try being pegged, and he nods, grinning.
I grab the strap-on and the anal vibrator, both freshly cleaned earlier with sex toy cleaner. He starts with the vibrator to relax, and we stay close, kissing as he gets used to the sensation. I’m already so turned on, but focused on making sure he feels comfortable and ready.
I put on the strap-on and with plenty of anal lube and careful communication, we take things slowly. He’s crouched on all fours with me behind him.
Even the initial sensation is intense for him, and we pause, adjust, and build up gradually. I stay close to him the whole time, keeping things gentle and reassuring.
As we find a rhythm, the dynamic shifts, it feels intimate but also unexpectedly powerful. There’s a sense of trust in the moment that makes everything feel heightened. I feel dominant over him. It’s so sexy.
I grab one of my nipples as we go, desperate for release as he’s finding his. It takes time, but when he finally orgasms, it’s intense and leaves us both a little breathless.
We laugh when we realise the mess we’ve made, and he insists on sorting the sheets while I catch my breath. Afterwards, we curl up together, but I admit I’m still worked up.
He immediately goes down on meand the way he focuses on me feels almost like a thank you. I end up climaxing twice before we finally settle.
Exhausted, we fall asleep spooning.
Instead, we hop in the shower together and then head out for brunch. We go for a walk in the park after and chat. Jack asks if I’ve thought more about being exclusive, saying he feels like we’re being too vulnerable with each other to still be dating other people.
I feel a little nervous, given my past experiences, but I agree this is going somewhere and we should give it a go. Jack looks really pleased. He kisses me, one hand slipping under my shirt, and suggests heading back to mine.
We spend the rest of the day making out and watching films. We pause to wash the sheets and make toasties for lunch. Jack says he should probably leave but doesn’t want to, and I tell him he can stay another night.
Later, we’re back in my bedroom and I’m riding him when he stops and asks if I’d want to peg him again, almost shy about bringing it up. I agree, I like how much he enjoys it, and that I can provide this for him.
This time, we try a different position, with him lying down and his legs raised so we can keep eye contact. The angle is tricky, so we eventually switch back to doggie style.
It’s still tiring for me, but Jack finishes quicker this time, warning me just in time so we don’t make another mess. Afterwards, we shower again and curl up together on the sofa. I feel happy with our decision to be exclusive.
I ask him if I’ll be pegging him more often now, and he says whenever I like. I also ask if we’ll still have ‘regular’ sex, and he says that as much as he enjoys pegging, it doesn’t replace the intimacy of penetrative sex with me.
I’m a bit sore from all the sexual activity this week, but I still meet a friend for a spinning class and a coffee. I fill her in on how things are going with Jack, though I don’t mention the pegging, that’s our little secret.
My boyfriend agreed to fulfil my fantasy — this is what it’s like to peg a man
This week we hear from Cheri*, 29, who last spoke with Metro in July 2025, when she told us she prefers no-strings sex, because she falls ‘too hard, too soon’.But now, there’s been a development. Cheri, who is bisexual, is dating a guy — although they aren’t exclusive.
‘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. ‘He’s less experienced sexually than me, but open to try things.’
This openness is important to Cheri, who enjoys a ‘playful’ relationship with 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 now keen to try pegging.
‘I’ve used a strap on with a female partner, but never with a male partner, and I’m curious.’
So without further ado, here’s how Cheri got on this week…
The following sex diary is, as you might imagine, not safe for work.
Monday
Jack* messages me to plan a date for tomorrow night. We’ve been seeing each other for six weeks, since we met on Hinge.He’s broached the subject of exclusivity, but I’m more hesitant. I got my heart broken pretty badly not so long ago, and I want to take things slow.
One area we’re not going slowly in, though, is the bedroom. On our third date, we slept together, and it quickly became clear Jack has a particular interest in anything related to arse play.
He loves rimming, both giving and receiving. I’ve never minded it; I’ve tried anal a few times with a long-term partner before, and I can enjoy it, especially when combined with clitoral stimulation. But Jack’s enthusiasm for it is making me look at it in a different way.
After work, I get home and a package I ordered has arrived. It’s an anal vibrator I saw recommended online. I want to surprise Jack with it, as he mentioned he’s never used one before.
I put the toy on charge, make some dinner for myself, then settle in with a TV show and an early night. I know tomorrow will be a late one.
Tuesday
All day, I’m impatient to see Jack. He messages me at lunchtime saying he’s excited, and I tell him I have a surprise. I try to focus on assignments that I have due, but it’s difficult.After work, I head to his place, where he’s busy making spaghetti Bolognese. I convince him to turn off the stove, and things quickly escalate.
We end up on his bed, making out and shedding our clothes. I tell him to wait there while I grab the anal vibrator. He grins when I show him what it is.
He pulls some anal lube from his bedside drawer, and I start by giving him a rim job and hand job, then I grab the toy. I struggle a bit to get the angle right, so he takes over. We start on a low setting, and he clearly enjoys it.
Having sex while he’s still getting used to it feels like a bit much, so I switch to a blowjob instead. He comes hard, moaning my name.
Afterwards, we take a few minutes to cuddle while he recovers, then hop in the shower before finally getting to dinner. We’ve definitely worked up an appetite by this point.
Later, as we get ready for bed, Jack goes down on me, clearly keen to return the favour, and I quickly orgasm. We settle into another cuddle, and he tells me how much he enjoyed the vibrator.
I ask, half-joking, if he’d ever consider pegging. He admits he’s never really thought about it before, but says he’d be open to trying it with me. We agree to give it a go, and I can’t help feeling excited.
Wednesday
The next morning, we only have time for a quick kiss and cup of coffee before I rush off to a meeting.At work, I’m distracted, getting flashbacks of the night before. Jack messages me before lunchtime saying he enjoyed it and that he can’t wait to see me again.
Seeing his name on my phone excites me, which scares me at the same time. I haven’t opened any dating apps in weeks.
After work, I meet a friend for dinner. She’s just broken up with her boyfriend and wants to break the cycle of going back to him. I don’t bring up Jack much, since she’s clearly having a hard time, but when she asks, I tell her I’m enjoying it for now.
By the time I get home, I’m exhausted. Last night didn’t involve much sleep so I take a quick shower, make myself a cup of peppermint tea, and climb into bed.
Thursday
I’m working from home so I stay in bed a little longer. Eventually, I go for a quick run around the local park, before jumping in the shower.The day is fairly relaxed, which makes a nice change. Around lunch time, I find myself feeling distracted and turned on. I close my laptop for a bit of a break and use my clit sucker on myself. I imagine myself pegging Jack and it gets me so excited.
I orgasm more quickly than usual, but it doesn’t feel like enough. I have to stop though, as its time to get back to work now.
In the evening, I stay in, looking up tips on pegging. As a bisexual woman, I’m curious about how using a strap-on with a man might work. I like to know what I’m doing and I want to get it right.
Friday
I head to a reformer Pilates class in the morning, then run errands.In the afternoon I read on the balcony, and soon enough, it’s time to get ready for my date with Jack.
We meet at a Korean restaurant I saw recommended on TikTok. He kisses me hello and compliments my short skirt. After splitting a dessert, we head back to my flat, barely making it through the door before we’re kissing.
By the time we reach the bedroom, I pause to ask if he still wants to try being pegged, and he nods, grinning.
I grab the strap-on and the anal vibrator, both freshly cleaned earlier with sex toy cleaner. He starts with the vibrator to relax, and we stay close, kissing as he gets used to the sensation. I’m already so turned on, but focused on making sure he feels comfortable and ready.
I put on the strap-on and with plenty of anal lube and careful communication, we take things slowly. He’s crouched on all fours with me behind him.
Even the initial sensation is intense for him, and we pause, adjust, and build up gradually. I stay close to him the whole time, keeping things gentle and reassuring.
As we find a rhythm, the dynamic shifts, it feels intimate but also unexpectedly powerful. There’s a sense of trust in the moment that makes everything feel heightened. I feel dominant over him. It’s so sexy.
I grab one of my nipples as we go, desperate for release as he’s finding his. It takes time, but when he finally orgasms, it’s intense and leaves us both a little breathless.
We laugh when we realise the mess we’ve made, and he insists on sorting the sheets while I catch my breath. Afterwards, we curl up together, but I admit I’m still worked up.
He immediately goes down on meand the way he focuses on me feels almost like a thank you. I end up climaxing twice before we finally settle.
Exhausted, we fall asleep spooning.
Saturday
We wake up and I can feel Jack’s erection pressed against me. We start to have sex, but he stops and says he’s actually too tired. I don’t mind either way.Instead, we hop in the shower together and then head out for brunch. We go for a walk in the park after and chat. Jack asks if I’ve thought more about being exclusive, saying he feels like we’re being too vulnerable with each other to still be dating other people.
I feel a little nervous, given my past experiences, but I agree this is going somewhere and we should give it a go. Jack looks really pleased. He kisses me, one hand slipping under my shirt, and suggests heading back to mine.
We spend the rest of the day making out and watching films. We pause to wash the sheets and make toasties for lunch. Jack says he should probably leave but doesn’t want to, and I tell him he can stay another night.
Later, we’re back in my bedroom and I’m riding him when he stops and asks if I’d want to peg him again, almost shy about bringing it up. I agree, I like how much he enjoys it, and that I can provide this for him.
This time, we try a different position, with him lying down and his legs raised so we can keep eye contact. The angle is tricky, so we eventually switch back to doggie style.
It’s still tiring for me, but Jack finishes quicker this time, warning me just in time so we don’t make another mess. Afterwards, we shower again and curl up together on the sofa. I feel happy with our decision to be exclusive.
Sunday
Jack has plans with friends, so he leaves by 10am. He kisses me before he goes and says he really enjoyed our weekend together.I ask him if I’ll be pegging him more often now, and he says whenever I like. I also ask if we’ll still have ‘regular’ sex, and he says that as much as he enjoys pegging, it doesn’t replace the intimacy of penetrative sex with me.
I’m a bit sore from all the sexual activity this week, but I still meet a friend for a spinning class and a coffee. I fill her in on how things are going with Jack, though I don’t mention the pegging, that’s our little secret.
