This is how we do it: ‘We trade cheeky nudes when we’re apart, like lovestruck teens’

  • 9/2/2023
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Jake, 56 One upside of my prostate surgery is that I’ve been able to hone my oral sex skills When Cassie and I first started sleeping together, two years ago, I was recovering from a bout of impotence. I had just undergone prostate surgery, and one of my side-effects was an occasionally uncooperative penis – which is not ideal when you are trying to begin a whirlwind romance. Luckily, Cassie and I were already old friends, so warning her about my unreliable erections was less terrifying than it would have been if she were a stranger. The lovely thing about falling in love with someone you’ve known for decades is that there is very little opportunity for pretence. Cassie was still grieving for her husband when we got together, but she didn’t have to hide that from me; I had been there for her in the years since his death, so I understood what she still felt for him. The fact that we are friends first and foremost makes it easier to be straightforward about sex. When I started flirting with Cassie I sent her a text, saying: “Next time I come over, shall I pack a toothbrush?” One upside of my prostate surgery is that I’ve been able to hone my oral sex skills. The first time I went down on Cassie, she was a little hesitant. She felt shy about her body and she didn’t believe I could really enjoy kissing her there. But I proved my enthusiasm. I don’t do token two-minute licks. I like to titillate for at least 15 minutes. My penis behaves itself a lot better these days, but I still let my tongue lead the way. It’s easier for me to stay hard if I’m upright, so we do doggy-style a lot. If Cassie’s on top my erection will begin to fade after about five minutes, which can be frustrating, but we persevere as it’s become our favourite position. We don’t live together yet, as we both have kids at home who remain our priority. During the week I might send her a cheeky video to build anticipation for our next date. If her daughter’s out of the house, I’ll stay at Cassie’s. It’s a bit of a role-reversal: being in your late 50s, and waiting for your teenage daughter to leave the house so you can have loud sex. But I think we both feel lucky to be behaving like love-struck teens. Cassie, 58 I find it very difficult to balance the phone and click the camera at the same time In my previous relationship, I felt under pressure to dress up for sex. My husband was very visually stimulated, as a lot of men are. When we did have sex – which was rare in the last few years of his life – he wanted me to put red lipstick on, and put my hair up, and totter around in high heels like a porn star. But Jake isn’t interested in seeing me in a silky babydoll, and that’s a tremendous relief. The first time he slept over, I disappeared into the bathroom and emerged trussed up in black “sexy” underwear, and he was a bit nonplussed. He suggested (very gently) that I might want to take it off. Once I stopped wearing silly little outfits, I found I enjoyed the physical experience of sex a lot more. I’ve got quite a large tummy and I used to worry about my husband seeing it in bed. I was constantly adjusting all my silky fabrics to keep bits of myself hidden, and cinched in. I can tell from the way Jake touches me that he loves my curves, and that has allowed me to stop visualising all my bad angles through his eyes. When he goes down on me I let myself really feel it, rather than tensing up because I’m frightened of what my body might look like caught off-guard. Jake has his own body hang-ups. He used to apologise over and over again if he ever went limp, but I told him: I’m not bothered in the slightest. Now, if he ever loses his erection he’s much less cut up over it. We’ve learned that switching positions so that Jake’s on top usually rectifies the problem. And quite frankly, foreplay is just as important to us as penetrative sex. We plan to move in together at 60, once we’ve both hit retirement, but I quite enjoy our current set-up. I still get butterflies before I see him. Jake and I trade nudes when we’re apart but I’m not very good at them. I find it very difficult to balance the phone and click the camera at the same time. It’s easier for men: they just have to look down and snap. It’s a bit like Ab Fab in my house at the moment. My teenage daughter is terribly sensible and I’m locked in the bathroom, trying to take a photo of my fanny.

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