Meet Jake, Age 56
One of the unexpected benefits of my prostate surgery is how it has allowed me to refine my skills in oral sex
When Cassie and I began our sexual relationship two years ago, I was still recovering from my impotence after undergoing prostate surgery. Dealing with an occasionally unresponsive penis was less than ideal when starting a new romantic connection.
Fortunately, Cassie and I were already long-time friends, so discussing my erectile struggles with her wasn’t as intimidating as it would have been with a stranger. The beauty of falling in love with a lifelong friend is the absence of pretense. Cassie was still mourning the loss of her husband when we got together, but she didn’t have to hide her feelings from me. I had been there for her throughout the years following his passing, so I understood the depth of her emotions.
The fact that we were friends first and foremost made discussing sex easier. When I initiated flirting with Cassie, I sent her a text asking, “Should I bring a toothbrush next time I come over?”
An upside to my prostate surgery is that it has allowed me to improve my skills in oral sex. The first time I performed oral sex on Cassie, she was hesitant. She felt self-conscious about her body and doubted whether I could genuinely enjoy pleasuring her in that way. However, I proved my enthusiasm and took my time. I don’t just give superficial licks for a couple of minutes. Instead, I strive to titillate her for a minimum of 15 minutes.
Although my penis now functions much better, I prefer to let my tongue take the lead. I find it easier to maintain an erection when I’m upright, so doggy-style is a common position for us. If Cassie is on top, my erection may begin to fade after around five minutes, which can be frustrating. However, we persevere because it has become our favorite position.
Currently, we don’t live together as our children from previous relationships are our top priority. During the week, I like to send Cassie cheeky videos to build anticipation for our next date. If her daughter is out of the house, I’ll stay over at Cassie’s. It’s a bit unusual for people in their late 50s to wait for their teenage daughter to leave the house so they can have passionate sex, but we both feel fortunate to experience the excitement of love-struck teenagers.
Introducing Cassie, Age 58
Struggling to balance the phone and take photos is a challenge for me
In my previous relationship, I felt pressured to dress up for sex. My husband was highly visually stimulated, like many men. In the later years of his life, our sexual encounters were infrequent, but when they did happen, he expected me to wear red lipstick, put my hair up, and parade around in high heels like a porn star.
However, Jake has a different perspective. The first time he stayed over, I adorned myself in black “sexy” lingerie, and he was taken aback. He gently suggested that I might want to take it off.
Once I stopped wearing revealing outfits, I found that I started to enjoy sex on a much deeper level. I have a curvier figure, and I used to worry about my husband seeing certain parts of my body in bed. I would constantly adjust my silky fabrics to conceal and shape myself. However, when Jake touches me, I can feel his genuine affection for my
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