I was a fifty-five-year-old widower when I first encountered Jessica, who had recently moved into the house next door. She was much younger than me and could only be in her twenties. I knew she was out of my league, both in terms of age and looks. Not that I was ugly, but I was no picture either, though I did try to keep myself fit with regular exercise. Jessica also kept herself trim, but, in contrast to me, she was a pi...

As we had agreed, that afternoon I met Jessica in her garden and gave her the money to compensate her for having to call in an emergency plumber. She was genuinely thankful, and we were sat, side-by-side, on a bench. For a good while we chatted casually with one other, drinking our beers, and then the conversation took a more serious turn. “I'm sorry I almost lost my temper earlier, Frank. It was so wrong of me. Daddy say...

Jessica had manipulated me into buying a pair of her panties and then masturbating into them three times in twenty-four hours. She had then told me that I was not to wank again until she gave me permission. I was humiliated, and common sense should have caused me to step away from her, yet, like a moth is unable to resist being drawn to a light, so I felt compelled to comply with her demands. Without doubt, she knew how t...

Jessica had humiliated me by “making” me masturbate into the knickers she'd sold me. Moreover, she had “made” me do it by humping the carpet. I had then spent the rest of the day wearing the cum-encrusted underwear, my jism glued to my short and curlies, causing twinges of pain so I could never forget what I had done. She had threatened to return to check I was obeying her, but she didn't come back, and I heard nothing mo...

Jessica had installed parental control software on my phone and laptop. I could no longer look at porn, and I started wondering what she would do next. Nothing happened for a couple of days, and then she messaged me early one morning. Jessica: “Rise and shine, Frank, I'm coming round. I've something for you.” What was she up to? Just minutes later she was at my front door, and I welcomed her in. “Hello, Frankie,” she said...

As well as preventing me from looking online at porn, Jessica had now insisted I was locked into a chastity device. She was taking control of my life! The next morning, she again dropped in on her way to work. “Now, how's the cage going?” she asked, once I had invited her inside. “I'm still finding it difficult, Miss. I don't think I'll ever get used to it.” “Of course you will, stop being so defeatist. It's still early d...

Jessica had fined me £40 for not keeping my house clean. As I was running short of cash, she agreed that I could pay off my fine by doing her bidding for two hours, and I was expected to report to her house at 1 PM on Saturday. I was therefore surprised when I heard her letting herself into my house at 10.30 AM that day, with the key I'd given her. I got up from my armchair and went to greet her. She looked pleased to see...

It was Sunday, and I was still feeling tired from my exertions the previous afternoon, when Jessica had made me spend two hours moving logs, an utterly futile activity imposed as a punishment. But, afterwards, she had allowed me to worship her toes, while also awarding me the privilege of looking up her skirt as I did so. I'd not expected to see her again until Monday, so it was a surprise to receive a message from her on...

I had difficulty sleeping on Sunday night, my brain replaying the events of the previous afternoon when Jessica had allowed me to worship her pussy and had then rewarded me with a hand job. This marked a new direction for our relationship, and I was sure that it would not be long before she was again desirous of my attention. Of course, she had locked me up again, reminding me that I was still in a submissive relationship...

For the second night running, my sleep was disturbed by my encounters with Jessica. On consecutive days, she had required me to pleasure her with my mouth, and, on the second occasion, the blindfold had slipped, and I had seen her gorgeous pussy for the first time. She had not been pleased but absolved me from blame, despite telling me I should have shut my eyes. Nonetheless, I didn't get the impression that she wished me...

On getting home from Jessica's friend, Mandy, I immediately changed out of her ex-boyfriend's clothes and put some of my own on. That evening, I was still in a state of shock yet buzzing with excitement. I found it hard to believe that Mandy, on our first meeting, had allowed me to pleasure her using a dildo gag. What's more, she had had no issues with me seeing her naked or touching her. Needless to say, she had sworn me...

After Mandy had “forced me” to make love to her using a strapped-on dildo, I was left with a guilty conscience, knowing I had been disloyal to Jessica. Mandy had sworn me to secrecy, but I was uncomfortable with the knowledge I had. My sleep that night was troubled, and I was up early. I heard the postman push something through the letter box. It was a padded envelope, bearing just my first name and my address, written in...

Following my caning from Jessica, and Mandy's spanking, the three of us had enjoyed a pot of tea with some biscuits. It was all so typically English, cups of tea being the answer to everything, but, in this case, it seemed to work, and our differences were healed. Mandy and I had seen a new side of Jessica, and, despite our painful experiences, I felt neither of us regretted her strict approach. And, of course, we'd both...