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 more from her for a few days. As instructed, I continued wearing and washing the knickers, fearful that she would carry out another spot inspection.

oooOOooo

By the next Saturday, seven days later, I had been wearing the same pair for two weeks, faithfully washing them each evening and putting them somewhere to dry for the next day. She was teasing me, and my sexual frustration was growing.

I was becoming frantic for further release. Lying in bed in the evenings, I fondled myself, replaying some or other humiliating encounter with my young neighbour, yet resisting the temptation to cum in case she realised what I'd done. Looking at dirty images online didn't help my frustration, but after so many years without a woman in my life I had become addicted to the habit.

After ten days of no relief, I couldn't hold back any longer, and, after a long session online, I came, partly fuelled by the porn I'd viewed, and partly thinking about how she might choose to punish me, were she to discover my disobedience. As long as the punishment didn't mean Jessica breaking all contact with me, I was beginning to relish the prospect of her making me suffer in some way. The key, for me, was that I wanted her to keep being interested in me.

As it happened, I got away with it, and she didn't seem to suspect that I had disobeyed her instructions to abstain from self-pleasuring.

oooOOooo

It was the next evening, a Wednesday, when my phone buzzed.

Jessica: “I've run out of tampons, Frank. Please drive into town and buy a pack for me. Regular flow. Thx.”

Me: “Now?”

Jessica: “YES! Obviously now!! No point me getting them next week, silly boy!”

Me: “Sorry, Miss.”

Whether what she was saying was true was neither here nor there. I thought it was most likely a trick to humiliate me, but I had no choice other than to comply with her instructions. I stopped what I was doing, drove to a supermarket, bought the tampons and took them around to her.

“Thank you, Frank,” she said, when she opened her front door. “Not too embarrassing, I hope?” she smirked.

“I coped, Miss.”

“Do I owe you anything?”

“Er... no, consider them a gift,” I replied, with a grin.

“Wow! You know how to spoil a girl, darling,” she responded, smiling. “Come in for a beer. Just give me a minute to... you know.” She disappeared into the downstairs toilet, clutching the box of tampons.

Coming out, she beckoned me to sit down on the sofa and went to fetch two beers. Without being told, I produced a £10 note for the drinks and handed it to her. She smiled but made no comment.

“How are things, darling? Are you being a good boy for me?”

“Er... do you mean, have I wanked or looked at porn, Miss Fuller?”

“Well, have you?”

“No, you said don't, so I haven't,” I lied.

She looked at me quizzically, trying to read my mind. “Eleven days is a long time for you, isn't it? So, I'm proud of you, Frank. Very, very proud.” As she said that, she placed a hand on my thigh, midway between my knee and my groin.

“You and I work well as a team,” she continued.

“A team?”

“You're here to serve me and in return I do things that excite you. Please don't tell me you're not finding it exciting being my neighbour. Hmm?”

As she said that, her hand moved to the inside of my thigh. I could feel my penis waking up.

“Yes, I suppose I do, Miss. I... I think you've uncovered a submissive side to me that I wasn't aware of.”

“What?! You didn't know you had a submissive side, darling?” she replied, incredulously. “How could you not know? It was staring me in the face from the start.”

I didn't know what to say, so I contented myself with blushing, which brought a grin to her face.

“You're very sweet, darling,” she remarked. “But do remember that I expect total obedience from you, or you'll be punished—very severely punished.” My penis, which had been partially awake, now sprung fully to attention, causing her to glance down at the tent pole in my trousers.

“Remember,” she added softly, in her polished upper-class accent, “we're a team—we complement one another. You serve me and I arouse you.”

oooOOooo

It was 8 AM the next morning that she next messaged me. Luckily, I was up and dressed because my phone buzzed and I saw there was a message from her.

Jessica: “Do you have a lawn mower, Frank?”

Me: “Yes, Miss Fuller.”

Jessica: “Are your lawn mowing skills better than your plumbing skills?”

Me: “Yes, I hope so, Miss - LOL!!”

Jessica: “A simple 'yes, Miss Fuller' would have sufficed, Frank. Stop wasting my time. Does the gate between our gardens work?”

Me: “It used to, but it hasn't been opened for a long time, Miss Fuller.”

Jessica: “Well, please get it working and then I want you to cut my grass today, while I'm at college.”

Me: “Sorry? You want me to cut your grass?”

Jessica: “YES!! You're supposed to be serving me, Frank, so get serving!”

Me: “Yes, I understand, Miss.” When she'd said we were a team and I was to serve her, this was not what I had in mind, yet I still felt a twinge in my penis with her ordering me to do physical labouring for her.

Jessica: “Push your money through the door when you've finished. Understood?”

Me: “I have to pay you?”

Jessica: “YES!! You're my little paypig, remember?! DO PAY ATTENTION!!” It was that phrase again—little paypig! And, somehow, even in a WhatsApp message, she was able to demonstrate her impatience with me.

Me: “Yes, Miss, but how much?”

Jessica: “Use your brain, Frank. Find out what the going rate is for grass cutting. Okay?”

Me: “Yes, Miss Fuller.”

Jessica: “Drop your trousers and send me a photo to show you're wearing your knickers. I expect the pic to arrive in the next minute.”

Hastily, I quickly dropped my trousers and took a selfie of myself below the waist. I sent the image but, as I half-expected, there was no reply, despite it having been received.

Going outside at 9 AM, I tried the gate. It was stiff, but a few drops of oil got it working again. The grass had dew on but I guessed it would be dry enough to cut in a couple of hours. In the meanwhile, I did some searches online to find out how much local gardeners charged for cutting lawns and decided that £30 sounded reasonable for one Jessica's size.

I then set about mowing, feeling myself becoming aroused as I replayed how she was treating me. It was humiliating but, at the same time, it was turning me on. When I'd finished, I pushed £30 through her letterbox. As I had come to expect, I heard nothing more from her for a couple of days.

oooOOooo

Her next contact was on the Saturday afternoon, two weeks after she had made me hump the carpet. Spring had given way to early summer, and we were enjoying a hot spell. Looking out of my back bedroom window, I could see she was sunbathing in her garden, but I was careful to make sure she didn't spot me staring.

Then there was a buzz on my phone. I panicked, thinking she had seen me, so there was a sense of relief when I found that wasn't the case.

Jessica: “I need you to do something for me, Frank. Come round now.”

Me: “Yes, Miss Fuller.”

A few minutes later I presented myself in her garden. She was lying on her back, wearing the skimpiest of bikinis. I didn't know where to look and she was well aware of my predicament. “Don't gawp, Frank, it's not what gentlemen do.”

“Sorry, Miss.”

“Over there's a bottle of sunscreen. I want you to rub it into my back.” She turned over so she was lying on her stomach. “You'll need to undo my bra top. Just be careful where you're putting your hands, Frank. I don't need the front doing.”

I instantly felt my penis engorging as she gave me these clear directions, especially her telling me what was off limits. My fingers were trembling as I undid the clip of her bikini top and eased it off her back so that I could apply the cream. I squirted some of the stuff onto my hands and then gently massaged it into her skin.

It was the first time I had touched her and I was doing so almost intimately. I was so close to parts of her anatomy that were out of bounds, yet the thought of being that close was arousing. Luckily, as she was lying on her stomach, she was blissfully unaware of my semi-erection.

She started moaning. I don't mean she was complaining—no, she was enjoying what I was doing. “Keep massaging, darling. You're so good at it,” she remarked.

To take my mind off my erection, I tried to make casual conversation. “It'll be school holidays, soon, Miss,” I commented.

“Haha!” she replied, sarcastically. “Do you think teachers have nothing to do over the holidays, Frank, except sit around all day like retired people? If only! It's none stop work! I'll barely get a minute to myself.”

“Oh, I'm sorry to hear that, because I was hoping to see more of you, Miss.”

“What, more than you're seeing now, Frank? Sorry, but you won't be seeing any more of my body than this!” she laughed.

“Sorry, I didn't mean more of your body... although obviously it would be lovely—no, sorry, forget what I'm saying. What I mean is, I like spending time chatting with you,” I rambled.

“You do tie yourself up in knots, Frankie. Just remember that your role is to serve me, okay? Don't get ideas above your station. We are friends, but we are not an item. I'm still looking for a boyfriend my own age, but there'll always be a special place for you, Frank, have no fear.”

“Yes, Miss,” I replied. My erection, which had been shrinking, suddenly went back to full size as I processed her remarks.

It was several minutes before she told me to stop the massaging, saying, “That felt wonderful, darling. You're a good boy and you have a talent for massaging.”

I felt myself glowing with pride, especially being called “darling” and a “good boy”, but I didn't know what to say. Suggesting it had been wonderful for me as well seemed inappropriate and could be misconstrued. Luckily, she continued, “I might need you again, Frank, so go over by the house, in the shade. I don't want to feel I'm being scrutinised by you, so turn your back on me.”

“Er... yes, Miss. You mean, like face the wall, as if I were at school?” I stated, trying to introduce some subtle humour to conceal my embarrassment.

“Hmm... yes... now you mention it, that's exactly what I mean, Frank. Go and face the wall, and stay there. Get your nose as close as possible to the bricks.”

Feeling like a disobedient student, I stood facing the wall, waiting for a further command from her. I was there for ages, frightened to move, yet desperate to move. The time passed interminably slowly. I tried counting seconds but soon gave up. Only after what seemed like a couple of hours did she beckon me. “Come back over here, Frank.”

I did and she observed, “Sorry, I fell asleep. How long were you there for?”

“It seemed like hours, Miss,” I truthfully replied, but her question was rhetorical as I watched her, still lying on her stomach, scrolling through her phone.

“Don't exaggerate! I messaged you fifty minutes ago, so you've only been facing the wall for about half-an-hour. If it seemed longer, then consider that to be a reminder of what might happen if I have to punish you.”

“Yes, Miss.”

“Now, do my bikini top up again, then you can go home.”

She could have done the clip up herself, but she preferred to tease me. I struggled a little to pull the two ends together and to arrange the shoulder straps, but I managed. “Off you go, darling. There's nothing more for you to see here. Push some money through my letter box this evening. Be generous, my little paypig, because I'm sure you've enjoyed yourself.”

Little paypig? She did like that term, and, yes, I could see it was an accurate term to define my role. I felt a strong twitch from my penis as I contemplated the further embarrassment she was heaping on me.

It was pointless for me to ask her how much she wanted her “little paypig” to fork out, so I decided on £25. Serving Jessica was becoming expensive.

Despite being wracked by guilt, on getting home, I turned on my laptop, found some nude photos of women looking the spitting image of Jessica, and I masturbated. By defying her instructions, I was playing with fire, but she was teasing me so much that I couldn't help myself. But, unbeknown to me, my life was soon to change.

oooOOooo

I heard from Jessica again the next day, Sunday, when she appeared at my front door. She looked drop-dead gorgeous, in a very short black skirt topped with a white blouse, through which I could see the outline of one of her lacy white bras—although obviously I was careful not to stare.

“Have you been a good boy, Frank?” she asked, giving me one of her seductive smiles. “I do like boys who are obedient but, having said that, I'm sure I would also take pleasure in punishing those who aren't. Have you been good? It's been fifteen days now, darling. A long time, eh? Have you obeyed me?”

I felt myself redden being spoken to as if I were younger than her, rather than being thirty years older. “Er... yes, I have, Miss Fuller.”

She stared at me, inquisitively. “Hmm... ? Is there anything you want to confess, Frank?”

“Er... no, no, there isn't,” I replied, while my subconscious was shouting, tell her about how you've defied her by masturbating twice without permission, including yesterday.

“You sound nervous, Frank. Are you nervous?”

“No! Not at all,” I fibbed.

“Hmm... I've think you're forgetting my rule about honesty, Frank. You don't have a very good memory, do you? Now I'm here, shall we have a look at your browsing history?”

“Er... well... yes, yes, you can, Miss,” I replied, with growing confidence.

“A little hesitation there to start, I think. Show me your computer.”

I fetched my laptop and woke it up for her. She took the command of the keyboard and was soon inspecting my browsing history. “Well, to my absolute amazement, it's clean, darling. No dodgy sites that I can see.” She was giving me one of her flirtatious smiles.

“No, nothing, Miss Fuller.” I gave a silent sigh of relief, congratulating myself that I had had the foresight to do all my “illegal” browsing using incognito mode.

But then the sweet smile disappeared from her face and, turning to me, she whispered, “You've been browsing in private mode, haven't you, so there's no record left of the porn you've been viewing? Am I right, Frank?”

“Er...”

“You need say no more, Frank. 'Er' says all I need to know. Pass me your phone and unlock it, then go and stand in the corner while I make some modifications.”

I did as instructed, while she worked away for a while.

“All done, Frank. Parental control software purchased, downloaded and installed on both laptop and phone. That will put an end to your squalid little habits, won't it?”

“Er... well...”

“Unless you have any other devices that access the internet, Frank. Do I need to search the house?”

“No, Miss, I've nothing else, I promise you.”

“There will be serious consequences if I later find you're telling fibs, Frank.”

“I promise there's nothing else.”

“Good! I'll leave you to it. I hope you don't get too bored with your entertainment gone. Oh, by the way, the software was £50, so please push some money through my letterbox at your earliest convenience.”

My God, yet another expense, and one that was for depriving me of pleasure.