Pennys Little Lessie

Penny's little lessie

This story can be read as the third part of a series that begins with, 'The coming of Penny,' and continues with, 'My glistening Penny.' Each of these three stories can be read separately though reading them in sequence will give a more coherent picture of my affair so I have done my best to keep the overlap to a minimum. Finally, if anyone only wants to read of lesbian love and lust, this third part does contain paragraphs that relate heterosexual activities, you have been warned!

Penny - who on our very first encounter had pressed her powerful wand vibrator to my clit and made me come so deliciously violently and, on our second meeting, had sucked, licked and fingered me through a series of six mind blowing orgasms - had offered to teach me how to please her and ever since I had been longing for the day when I became her eager pupil.

Whilst kneeling between her splayed legs, licking her lips and her clit, revelling in her moans and sighs as I tried to bring her to orgasm I had realised just how ignorant I was about female bodies, my body, her body, every woman's body. I owned one and had no idea how it worked, bit like our car really. Penny, on the other hand, was an expert. I had no idea what she had done to my clit with her lips and tongue but she had driven me at speed through a succession of six overwhelmingly intense orgasms. Now I was eager to discover how and return the favour. And, as her pupil, I would have to do as she told me, no arguments, and she would no doubt demand things that made me squirm with embarrassment, things that filled me up with desire and need until I overflowed.

I recalled what I had promised her, 'Penny I want to be your good little lessie, I want to learn how to please you as much as you please me. To learn to please you more if I can. I want to be the one making you scream out with lust.' I'd have to confess that I was her good little lessie as I worshipped her body. I'd have to expose all my most intimate places to her so she could guide me as I played with myself. I shuddered, I expected that she would want me do all kinds of dirty and depraved things... Then the dream faded because I had no real idea about what Penny would want me to do, just that I hoped it would be lewd and rather embarrassing because pleasing Penny pleased me, especially if it was against my better judgment.

For the thousandth time I asked myself, 'Why me?' A woman almost twice her age! What's her fascination with me? I did not understand but I was so grateful things were the way they were and wise enough not to ask questions.

The fly in my ointment was Greg, my husband of eighteen years. Once we had been madly in lust, coupling like rabbits, I'd go without panties for him or only wear them so that I could pull them down later and hand them over to him. He loved that, started telling me when to pull them down and give them to him, telling me to flash my tits at him in restaurants and bars. Had me perform lewd acts for him in the bedroom, first spread my legs and then my lips for him, lie on my back, grab my ankles and spread wide, allsorts. And I had loved it, I had loved him, adored his masterly ways and enjoyed pleasing him. Sadly things had changed.

He still had a manly dominance but now it was the kind that kept a tracker on my phone so he always knew just where I was. We had a doorbell camera, a security camera covering the front door, a security camera covering the back door and those were the ones I knew about. Greg could access all of these devises remotely through his phone and, for all I knew he could listen in to me using our three sets of smart speakers too! He would pop back on his nights out to check 'I was OK.' He texted me a dozen times a day to reassure himself that I was fine, not doing anything 'silly.' He opened my post and read it, he knew my passwords and accessed all of my devices just 'to protect me from harm.' I had to justify every penny I spent and recount every conversation. His consideration for my welfare just grew and grew until he left me stifled and controlled. And if that were not enough he sorted out our money, doling out just enough each day so that I could shop for what we needed.

Over time his evenings out with the lads had grown to be more and more frequent, he arrived home less and less sober and his hangovers grew bigger and bigger. I went to bed early to avoid his anger, our sex life dwindled, catching him both sober and not hungover was an increasing rarity. Worse, he had always been a gifted raconteur, now he was the life and soul of every party and with his swift wit, elephantine memory and endless supply of stories he was really popular. 'Have another and tell us another,' was where his problems had started, he could go out, get pissed six nights a week, never need to buy a single drink and his mates never noticed, never resented it, thought the sun shone from out of his backside and told me how lucky I was to be married to him.

How to see Penny again? How to be her diligent student, her good little lessie without Greg finding out? I had confided in my friend, Alice, who lived across the road and who knew Penny really well. She told me we'd just have to make a chance whenever Greg was away, which was not often. My most likely opportunities were when his team played far from home and he travelled up or down the night before the game. We could have met up at Alice's but Alice already had a reputation, she had parties, quite a lot of parties. Some of them, the parties her neighbours were not invited to, had exclusively female guests some of whom arrived clad very scantily: Greg would not approve of me spending whole evenings at Alice's. No one local, except me, knew for sure what went on, it was all rumour but rumour was more than enough for Greg. And what did I actually know? Well Penny had described them as Sapphic orgies and she was the expert since she was a regular attendee.

Then Greg announced a night was coming up when he'd have to set off early and only be back in the small hours and I became frantic. Alice, bless her, sorted everything. She made sure that Penny cleared her diary for me and she devised 'the plan.' Sarah, another regular at Alice's more intimate gatherings led my yoga classes on Monday and Friday mornings. But, in addition, she also held several less demanding classes in a church hall near Penny on a Tuesday evening. For these much larger classes she always had one or two assistants and that Tuesday I could officially be one of her little helpers. The key to Alice's plan was that as a helper I would have to stash my phone in a metal locker where there would be no signal whatsoever so Greg could not contact me. Her idea was that as I walked past the hall I would tuck my phone in a metal box and carry on to Penny's house and then return the phone to my bag as I passed the hall on my way home. This would mean that from a quarter to six until a quarter past nine I would be as free as air. Greg would be annoyed but not incensed.

At first I kept calm and trusted Alice completely but as the days crawled by I was so anxious that it might not happen that I allowed myself one call to Penny. "It's Gwen here. Just checking next Tuesday is still fine... Yes Penny, I'll be your good little lessie from the moment I arrive until it is time for me to go home... Yes Penny we'll do whatever you decide... No Penny I won't hold back at all, your good little lessie will not disappoint you... not in any way... Yes that is a promise... Yes Penny, I realise that you might test my determination but whatever you ask me to do I will not let you down."

As the call disconnected I wondered what I had just let myself in for? I had literally promised to do anything that Penny wanted, anything at all! And Penny liked to tease me, to make me squirm a little. I was so excited, I felt the familiar squidgey feeling between my legs, I felt lead weights somersaulting in my tummy. Within ten minutes I knew that I had to dash upstairs and masturbate. I had to masturbate for Penny and Penny's good little lessie should do something dirty for her. What was kinky enough for Penny? Then I knew what I must do, put on a show for her with no holding back.

First I stripped off, well first I closed the curtains and then I stripped off. I stood in front of our full length mirror and examined what I saw critically: moles, too many moles but what could I do? Still Penny has moles too and she is gorgeous. I saw breasts that were starting to sag a little and nipples that sag a little more, whatever does Penny see in me? She has firm little breasts with the most delightful plumped up nipples, like nothing I have ever seen before. Nipples that demand to be sucked, to be made firm and erect. I saw a face that is starting to be lined around the eyes and under the mouth. Then there's my neck, let's not discuss my scrawny neck. Whereas Penny is young with blond hair that covers her breasts when it swings free and skin that is totally free of the slightest blemish. At least we have our hairy muffs in common, I suppose that's something. Isn't it?

I unearthed my little, ancient, underpowered vibrator wondering how to sequester enough funds from the housekeeping money - the money that Greg dispensed so grudgingly - so I could buy something newer, better and more powerful. I sighed, my old one would have to do for quite a while longer. I switched it on and set it between my legs. Oh my, I had already been daydreaming about Penny causing its impact on my clit to feel electric. My knees gave way and I sat down on the bed with a bump, an orgasm rising fast. The vibrator was making my hips buck as if I were trying to hump it. I recalled how I had elected to please Penny and watched myself in the mirror as I spread my legs wide displaying myself masturbating brazenly: if only Penny were here to really see me, to reassure her little lessie that she was putting on a lewd enough performance for her precious Penny. Still joyous as my fast approaching clit based orgasm would be I did not think that would be much of a show so, with a huge effort of will, I jerked the toy away from me right before I came.

I placed the tip of the vibrator to my glistening entrance and pressed gently but firmly. I could feel the vibrator opening me up, I could feel the vibrator exploring deeper inside of me, filling me. In the mirror I could see the vibrator disappearing inside of me, my hungry muff swallowing it up. 'Oh my God,' there, just there mmmmmmmmmm! That felt so... I watched myself in the mirror humping my vibrator, working my hips back and forth to make it shaft me. I pinched a nipple and squeezed. I watched my mouth open wide as I vented a huge sigh of pure pleasure. Soon I would be coming from humping my plastic friend, my orgasm was building rapidly. There, right there... that spot, it brought me so much joy. I humped the vibrator lewdly, crying aloud with the delight of a big strong orgasm bursting forth, making me sigh, making me moan, making me groan, making me puff and pant. I tried to keep my eyes open, to watch myself come but it simply felt too good and I doubtless disappointed Penny by missing parts of my own performance, though hopefully she missed nothing.

Still now to really be Penny's good little lessie, to prove to her that I was willing to do anything for her. I withdrew the vibrator, now liberally coated with my own juices, placed the tip against my lips, took it into my mouth and then sucked and licked it clean. I hoped that my performance pleased Penny, showed her that I would do whatever she demanded of me. I hoped that when we really met up she'd find something to test me with properly so I could really prove to her how badly I wanted her. As I licked my sexual juices from the vibrator I wished they were was fresh from Penny, that it was she who I was tasting after I just made her come hard for me: I had relieved my own needs but how much more joyous it would have been to have relived hers.

The weekend that followed, it was Hell, I kept wondering what Penny would make me do and my conjectures worked me to a frenzy. Just before Saturday lunch I caught Greg fully recovered from his last hangover and still sober and I was so horny that I seduced him with an offer of doggy. I ripped my clothes off and bent over the back of one of the dining room chairs and he took me from behind. Usually he comes before I do, he watches his member reaming back and forth in me and it makes him really short fused but that day I was so worked up I came pretty well as he did. Oh that felt so good, if only it could happen more often. But then if it happened more often I'd still be the good little wife who was not lusting after a woman half her age.

Sunday evening, before he went out for, 'just a little bevvy with the lads' my dreams of Penny had made me so desperate that I seduced Greg again. This time we were sitting in the lounge, me reading the newspaper he watching footy on the television. When his team went three one down he started losing interest. If I wasn't careful he'd be off to the fridge for a can of beer to console himself with and that would be the beginning of the end. I swiftly announced I needed a shower, stripped off right there and then, didn't even pause to close the curtains and then strutted off towards the stairs wiggling my rear provocatively. As I ran the water hot I heard Greg following me up the stairs, 'Bingo!' Well he stripped off and washed my back. rubbing his hard cock up and down along the crack of my bum. We didn't even dry off just grabbed towels and threw them on the bed.

Greg was even thoughtful, well thoughtful for Greg, he rolled me onto my back and doubled my legs up over my chest before clambering on top of me and sinking his hard member inside of me. I do enjoy that position, his cock makes me feel delightfully full and catches against all the right places and he even took his time pistoning me slowly and steadily with that extra little thrust at the end so his body ground against me over my clit. I closed my eyes and enjoyed the waves of pleasure as he shafted me to orgasm: except suddenly I realised it wasn't Greg on top of me but Penny reaming me with a big dildo and, secure in the knowledge that I was being her good little lessie, I let go and exploded, a shattering climax that left me dazed and breathless. Then back to Earth with a bump, I must have tightened up on Greg's cock because he was now groaning with pleasure, speeding up and then grunting with joy as he spurted his all deep inside of me. Still he had satisfied me for a little while, curbed my appetites. Or had he? Had Greg done that for me or had it been Penny who had set me coming so forcefully?

Later that evening Penny sent me a text, 'No more masturbating. I want a horny little lessie visiting me.' Well first of all I deleted her message in a panic, Greg absolutely must not see that and he was into all my devices all of the time. Secondly, I needed to have a word with Penny about Greg and explain just how controlling he was. Thirdly, well do you have you any idea how much you suddenly need to finger yourself as soon as you are told not to masturbate? All the good work Greg and Penny had done just an hour or two earlier was gone to waste in the blink of an eye.

Monday crawled along and every now and then I would conjecture on what Penny might actually do with and to her little lessie and I would want to finger myself gently to relive the itch. But Penny had said no and I had to resist the temptation. Forbidden fruit always looks so juicy. Monday night I tossed and turned and was visited by a series of strange erotic dreams. I had more partners that night than I had had in the whole of my life, an endless stream of men and women lining up to use me. Tuesday I woke up and I wanted sex, I needed sex and sex is not masturbating so sex had not been explicitly forbidden, so sex was OK; anyway I needed something. I shook Greg to wake him and was cursed for my trouble, his head ached and he needed sleep. I went downstairs, brewed tea and stared at my hands pressed firmly against the table top to stop me from touching myself; it was going to be a very long day.

After lunch I was so desperate for something to distract me that I wondered about visiting Alice. But then she already knew enough about this evening to tease me and Alice could be a dreadful tease. I'd already had her enquire as to 'why was I off to Penny's house?' And when I went red and kept silent she asked, "cat got your tongue? Or is that the answer? Is it Penny's pussy that's going to get your tongue? Penny has a very affectionate pussy but it demands a hell of a lot of petting." I was scarlet. In the end I discovered that my rather more vanilla friend and neighbour Mandy was free, thank God, and off I went for a very long gossip.

When I arrived home Greg was getting ready to set off, he had a two hour drive each way which would keep him safely out of my hair until the wee hours. Then, as soon as I was sure he was gone, I almost had a meltdown: what was I going to wear for Penny? Would she prefer sexy panties, simple everyday panties, maybe a thong, perhaps even a g-string? That first time we met she had eyed my frilly red panties with their big bow with open amusement. On our second time she had ripped down my plain white panties in no time at all. I had no clue what kind of panties Penny wore, both times I had seen her she had not been wearing any at all. Damn, that was another possibility: perhaps I should not to wear any panties at all?

Should I wear a bra? My breasts aren't that big, apart from when I am exercising I don't need a bra but my breasts are beginning to sag a little and I do look better in a bra, especially once my - blouse, dress, top? Christ, yet another decision I needed to take. Dress perhaps? Top or blouse meant choosing a skirt or some trousers or maybe shorts? It was a bit cold for shorts. Was a good little lessie; slutty, sensuous, sexy, demure, modest? Just how was I supposed to look for Penny? I had no idea. The first time I met her she was wearing a dress, sandals and nothing else at all, the second time she was simply wearing nothing else at all and wasted no time in stripping me. Of course, were I being sensible, that was the answer, she'd have me naked so quickly that it did not matter what I wore for her. But right then all I could think of was that I had to be perfect for her and I had no clue what perfect might be.

As I got myself ready every decision was an agony, I ended up half dressed and then undressed again three times over before selecting a pair of frilly black panties, a thin black skirt festooned with big red flowers and a light cream top that really showed off my nipples. Bare legs and sandals, did I need to shave my legs? I ought to really. I undressed for a forth time, shaved my legs and then dressed again. There I was, a grown woman just short of forty behaving like a scatty teenager on her first date. That's how Penny makes me feel all the time, I crave her approval so badly.

Finally it really was time to go. Rummaging under my skirt I discovered that I was already so wet and slippery but then hastily snatched that exploring finger away, it was feeling just a little bit too good. I placed my phone and that all important little tin box that had once held a small fruit cake from Betty's into my little pink Herschel rucksack, grabbed a coat because it was rather cold out, especially with bare legs and sandals, locked up, dropped the keys into my bag and set off. I had not gone thirty meters when I turned back, my sandals would not do, they were well strapped and I wanted some that would slip off easily once I arrived. So many things to think of, so much to decide, so many details to pay attention to if I was to be the perfect little lessie for Penny.