I spanked her on her panties, every smack sending a shock to my already aching erection. She was moaning and giggling, wriggling her bottom to encourage me, and yet deep within me there was still a voice telling me that she couldn’t possibly be enjoying what was being done to her. It was Matthew who told me to take her panties down. Her response was a low purr, but still I hesitated, at which she stuck up her bottom and spoke two simple words, “yes, please”. So I did it. I took hold of the waistband of those pretty black lace panties and peeled them slowly down over her peach of a bottom to reveal her completely, naked and glorious, her full, cheeky moon slightly parted to show off the tight brown dimple of her anus, and between her thighs the pouted lips of her distinctly wet pussy.
And I spanked her, bare bottom, over the knee, the classic pose, long and firm, with her husband watching in amusement and her moans and cries growing gradually more urgent, until at last Matthew declared that she’d had enough. I thought that was it, and my regret as she rose from my lap was a physical pain, but he wasn’t done with her. He made her masturbate in front of us, with her skirt tucked up and her panties around her thighs, her bare red bottom showing to the room as she fiddled with herself until she came in a welter of shame and ecstasy.
He was grinning like a wolf as he asked, very casually, if he could borrow a bedroom for a few minutes. I could hardly refuse, and was left sitting there in an agony of frustration as I listened to her getting another spanking and then being fucked in the spare bedroom directly above my head. I’d have masturbated if I’d dared, but it was just as well I didn’t, because Matthew came down alone and told me that Maggie was waiting for me and would suck me off. I could scarcely believe my ears, but I went, and she did, kneeling on the floor in front of the bed with her red bottom pushed well out as she sucked my cock, and all the while with her husband coolly sipping gin and tonic in the room below.
That was twenty years ago now and I have never looked back. In one drawer of my desk is a little note book recording all the names of the girls I’ve spanked, alongside a few details. There are twenty-seven different names, and my only regret? That I didn’t start earlier.
ALISTAIR - Winchester
Strawberry Girl
I remember it like it was yesterday. She was called Poppy and she was the daughter of the place where I used to work helping look after the soft fruit. She was so fresh, and so lovely, blonde and beautiful, and such a bitch. She used to drive me wild. Unfortunately she was engaged, to the son of the owner of a local farm machinery hire firm, a good catch, or at least much better than me, a student with no particular prospects doing casual work on her father’s farm to make ends meet until the following term.
That didn’t stop me thinking about her, or watching her. She knew as well, and she used to dress to tease, and what with her father and I being the only two men working there I knew it was aimed at me. The shirts she wore were bad enough, or really the way she wore them, tied up under her tits with the buttons undone to leave her tummy bare and cleavage on show, so that you always thought that the next time she bent down to pick a strawberry her tits would fall out. Of course they never did, but if her shirts used to drive me to distraction her shorts were worse, because it wasn’t so much a case of her accidentally showing off her bum as that most of it was on show already. They were cut-down jeans shorts, so tight they showed off every contour of her pussy at the front and her cheeks behind, or at least every contour that wasn’t already spilling out at the sides, because they were not only indecently short but badly frayed. When she bent over she showed everything, and I do mean everything. She knew I watched, and if we were both working in the strawberry fields and her old man wasn’t about she’d get into her tightest, shortest pair and then deliberately bend down in front of me, with most of her bum spilling out to either side and the frayed denim crotch pulled up so tight over her pussy so that the lips stuck out to either side, while if she straightened up suddenly and they went loose I’d get the full view, and she was always wet.
You’d have thought she was up for it, and I did, at first. When I suggested that she might like to nip up among the raspberry fences where we wouldn’t be seen she told me in no uncertain terms that I could look but I’d better not touch, and that if I tried anything she tell her fiancé. He was a great red-faced thug, with a bitter temper and a reputation for getting into fights, which he won. I did as I was told.
After that she got worse, tying her skirts tighter still and wearing her shorts pulled up tight so that even just standing she’d make me shake with need, and she never lost an opportunity to bend over and show me what she’d got in even more detail. I hated it, but it was like a drug and I couldn’t stop myself. Not that I had much choice with her working alongside me, and was technically my boss so I had to do as she said, something she never seemed to tire of pointing out. I’d have left only I needed the money and work was hard to come by, or at least I’d have tried to leave. I’m not sure I could have done it. I needed her, and she knew it.
She really did know it. She knew she had me on a string and she also knew I was harmless, not just because I was wary of her horrible fiancé, but because I’m a gentle, passive person and it shows. I’m human though, and male, and believe me she drove me to the limit of my endurance over the course of that summer.
I couldn’t help my reaction. I’d get hard, and she’d see, and laugh at me. I never did like to masturbate, because it makes me feel such a loser, and I hated the thought of masturbating over her. Only I couldn’t stop myself. Just being with her made me ache with need, and by lunchtime I’d have blue balls, for which the only relief was a trip to the ramshackle loos and a couple of minutes of frantic tugging, all the while with her mocking laughter ringing in my head and pictures of her lovely body and the way she used to show off running through my mind. I’m sure she guessed, and whenever I came back from the loos she’d be wearing a little smile that was just pure contempt.
As the summer moved on she grew more confident in the hold she had over me, and bolder. One day when we were working cutting back excess foliage from the raspberry bushes she told me she was hot and was going to take off her shirt, and that I was to go into the next row and not to watch. If she caught me peeping she’d tell her boyfriend. I went, not one row away but several, because I knew I couldn’t stand it. She ordered me back, telling me sharply to do as I was told. I had no choice but to comply, and to spend the rest of the morning working in the hot sun with her on the far side of the fence, topless, with her beautiful round breasts naked to the air, not fully visible, but not exactly invisible either, because I was constantly getting hints of naked, creamy flesh through the gaps in the bushes. She had me rock hard, and in the end I just couldn’t stand it any more. I knew we were alone, we always were, so I moved a little way down the line, turned my back to the bushes and whipped out my cock, to jerk off in double-quick time to the images of her naked breasts that were flooding my mind. I thought I’d got away with it, because I’d waited until she’d gone to the end of the row with a bundle of cuttings, but even as I stood there with my eyes closed in pained ecstasy and the mess dribbling down my hand I heard her laughter from the far side of the bushes, as silvery and light as it was mocking.
After that I thought she was finally beginning to grow bored of tormenting me, simply because she’d pushed me to the limit and there was no more fun to be had. I could not have been more wrong. For a few days she was relatively well behaved, dressed as before but just ignoring me rather than deliberately teasing. I began to relax a little, until one day after work when she came up to me and told me that she was going down to the lake to swim, that she would be in the nude, and that if I tried to watch I’d be in trouble.
If she hadn’t told me I would never have known. The lake wasn’t somewhere I usually went, never mind after a hard days work when all I could usually think of was bed, and her body. She could have gone down there, swum naked for as long as she pleased and nobody would ever have
been the wiser. As it was, I knew, and I had no way of fighting the ache that her words brought except to go down there.
I did not want to give her the satisfaction of knowing she’d got to me, and I definitely did not want her to carry out her threat of telling her fiancé, but I couldn’t stop myself from going. To just walk there would have been foolish, so I set off down the road as if I was going down to the village, sure she’d be watching, and then struck off across the fields and around the behind the wood that bordered the far side of the lake. Once there I was more cautious still, going forward carefully until I’d found a place where I could look out from among the bushes with no risk of being seen.
She turned up a few minutes later, walking out onto the little wooden jetty at the far side, dressed in those same shorts and a red shirt on top. She was looking and listening, and I could guess it was for me. Something must have made her think I was watching, because she suddenly began to put on an act, first taking off her shoes and dangling her feet in the water, then untying her shirt and peeling it off. She spent some time like that, topless in the warm evening sun, deliberately posing to show her breasts off to best advantage, before suddenly lifting her bottom and pushing off her shorts. Nude, she stood up, disporting herself as if merely for the pleasure of being naked, but knowing full well she was showing off. Again she spent a lot of time like that, before diving in, only to emerge from the water almost immediately, her lovely, naked body now dripping wet, and to dive in again. For a full hour she stayed there, deliberately showing off and no doubt imagining me among the bushes with a sore cock in one hand, because she knew full well that as long as she was naked I’d never be able to leave.
She was right, both that I couldn’t leave and that I had a sore cock in my hand, because I’d come three times just watching her, and for all my rubbed skin and the ache in my balls I could hardly force myself to keep my hand away. She was wrong about where I was though, because the moment she was dressed she suddenly ran into a group of trees just to one side of the track that led back to the farm, only to emerge a moment later looking puzzled. She’d obviously thought I was hiding there and had hoped to catch me red-handed, and for all my frustration it felt good to have got the better of her at least in one small way.
Actually I’d done rather more than that. I’d hurt her pride. She really thought I hadn’t been there, but she concluded, perhaps not surprisingly but I’m sure also because it was good for her ego, that the reason was that I was scared of her fiancé. I was, but I’d have risked ten of him to see her naked, and now I had, only she didn’t know.
The very next day she told me that she was going to swim again that evening, and that she’d be naked. That wasn’t all though. She asked if I’d like to see her naked, in that same mocking tone and quite obviously expecting the answer to be yes, or for my eyes, and my cock, to betray me if I tried to deny it. I did try, telling her she’d made me suffer enough and that I didn’t care any more. It was the first time I’d actually admitted my feelings, although we both knew, and I swear that the cruelty in the smile she gave me on hearing my words wouldn’t have been out of place on the face of a devil.
And yet I had planted a seed of doubt in her mind, because she made a point of telling me she’d be swimming that evening one more time, but instead of threatening me with her fiancé she simply told me that she’d better not catch me looking or she’d tell her father and get me sacked. That was altogether different, and it was a lie, because if there was one thing I was sure of it was that she loved to torture me, and if I got the sack it would all be over. That made me realise something else, that if she set her fiancé on me it would all be over anyway. He’d tell her father, and I’d be out, maybe not if it was just for looking at her, but definitely if it was for watching her bathe naked. I couldn’t see either of them being too pleased about her going nude in the lake either, even if they would take her word against mine when she accused me of peeping at her.
I could have called her bluff. I could have said I’d be there and expected to enjoy the show. She’d have been furious, and maybe she’d have been powerless to do anything about it. But she wouldn’t have gone down to the lake, and she might just have been spiteful enough to set her boyfriend on me to get her revenge. So I stuck with the same line and said I didn’t want to see her anyway, which we both knew was a lie.
That evening I took the same route and hid in the same place, only this time she was already there, not on the jetty but in among the trees. I guessed she’d been watching the path, and obviously she hadn’t seen me, which was presumably why she looked so indecisive, standing on the jetty and fidgeting, as if she wasn’t quite sure what to do. After a while she ran into the trees again, came back out, took her shoes off and spent a while just dangling her bare feet in the water, then jumped up and stormed off. I was laughing.
The next day she was in her tiniest shorts and her tightest top, obviously determined to get a reaction out of me. She even flirted openly, which she’d never done before, asking if I liked the way she dressed and promising that the next time we worked up among the raspberries she go topless again as long as I promised not to try and touch. She also spent a lot of time bending over, as close to me as she could get, time and again showing off the bulge of her pussy lips to either side of the crotch of her shorts, down on all fours too, which was new and a view fit to make me burst. I took it all in, when I could, but pretended to ignore her and answered her teasing by telling her once more that I didn’t care any more. Now she didn’t seem quite so sure that I was lying.
The day after she arranged it so we were working among the raspberries. She went topless again, this time peeling off right in front of me and only then calling me a pervert and telling me to get into the next row and not to look. I just shrugged and went. That got to her, and at lunch she told me she was taking an hour off and would be sunbathing at the top of the field, in the nude. Again I shrugged, and even though it took all my willpower I took my own lunch in the orchard, well away from her.
The next day she had a new tactic. I was to rub oil into her back while she sunbathed in nothing but her shorts. I couldn’t bring myself to refuse, for all that it meant she was turning the tables on me once again, but for all the pain of my frustration and my aching erection as I massaged her back there was a sense of triumph too. My hands were on her body, not that intimately perhaps, but touching her, and if her fiancé had known he would have been furious.
It was good for her too. She found a new game, and as always she wanted to take it further. Telling me she wanted to get a proper tan, she said she’d strip the next day, and I could do her back and legs, maybe her stomach, but if I let my hands stray elsewhere I’d be in trouble, while I was to wear a sack over my head to make sure I didn’t peep. The sack was almost a humiliation too far, but the thought of touching her while she was naked was too much. I’d lost, once more her pathetic slave, and I would have to content myself with what she gave me, nothing more.
I did it though, letting her put the sack over my head and tie it off loosely to make sure I couldn’t see. She made me kneel, holding the tub of cream while she undressed, and with every article she discarded she told me how she look, barefoot, and with no top, and naked, asking me if I’d like to see her breasts and bottom and pussy and then assuring me that I never, ever would and that I should have taken my chance to watch her swim.
Her voice was full of cruelty as she spoke, and of excitement too, while for all my humiliation my cock had gone hard in my pants. She saw, and laughed as always, calling me a pervert and little wanker, then once more warning me to keep my hands where she allowed as she got down. I had no choice but to obey and began to rub in the cream, first into her shoulders and neck, lower down her back, her calves and feet and thighs before she rolled over to let me do her front, all but her breasts and the triangular area around her pussy.
One touch and I’d have come in my pants, but I bit my lip, struggling to tell myself that it wasn’t be
cause of the way she tortured me that I was so turned on and determined to do my best to hide my feelings. She was just as determined to extract every last ounce of emotion, or so it seemed, demanding that I do her back and legs once more, only the second time as I kneaded her lovely supple flesh she had begun to sigh.
I took no notice, thinking it was a trick, only to have her suddenly say that I could do her bottom, her voice still rich with contempt, trying to make it sound as if she was giving me a privilege far beyond what I deserved, but there was something else there too. Just to touch those soft, smooth little cheeks was too much for me. This was sex, my hands on my darling’s bottom and with that first touch my cock jerked in my pants and I’d come.
That didn’t stop me. Now she was sighing openly and even though all my attention was on her bare and now well oiled bottom she seemed quite happy for me to carry on, at least until she rolled over and told me to rub cream into her breasts. Now there was no more dissembling. It was a straightforward order, not to torment me, but because she wanted her breasts touched.
I’d come, and that gave me control, allowing me to make it slow and sensual, gradually rubbing the oil in to those two lovely mounds, and when I deliberately began to play with her nipples her response was a low moan. I could have laughed. She’d sealed her own fate, demanding something too intimate to allow her to control her own feelings, while I’d already come in my pants and could handle my own. I took the bag off my head and there she was, my beautiful Poppy, naked and lovely, her head tilted a little bit to one side, her mouth open in pleasure, her legs ever so slightly raised and a little apart.
I went back to massaging her and now she was moaning openly, with her legs coming slowly wider as I rubbed her nipples and gently squeezed her breasts. With my heart in my mouth I began to go lower, still paying plenty of attention to her breasts, but allowing my hands to go every closer to the Holy Grail, her pussy. Her legs were apart before I touched that pretty pink slit, open and moist with her excitement, her bottom hole a tiny pink dimple between her sweetly turned cheeks. I put a little oil on her mound and there was no resistance, only a soft purr. I began to rub it in and still no resistance, but her legs came wider apart. I slid one finger into her eager hole and she moaned and arched her back.
Confessions 2 Page 4