Written by Flagg
10 Nov 2013
School days - Interlude 2
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14 minute read
‘How the fuck did I get myself in this situation…’ I said to myself as I stood there cleaning the pool. Of course I knew, and I shouldn’t have been so naïve as to think that it would end after that first time. It wasn’t that I was complaining about cleaning the pool. It had more to do with the fact that I didn’t have any clothes on, and that there was some kind of ring around my cock to ensure that it remained erect. That, and the fact that I could feel them staring at me through the lounge windows…
When my mom called me and told me that Mrs Smith had called and asked if I could go over to help with the pool, I just knew that I was in trouble. As I walked over, I didn’t know whether to be terrified, exited or horny – I guess it was a mix of all…
As always, she was impeccably dressed in a white shirt and black pants when she opened the door. Although not focusing thereon, I couldn’t help but notice from who Samantha had inherited her massive breasts. Also, just for a moment, I wondered what effect age and gravity must have had on them. The cool and collected manner in which Mrs Smith was observing me, however, brought me back to reality with a bang. She couldn’t have known what I was thinking about… could she?
‘Come in, and take a seat.’ Mrs Smith offered me a seat at their dinner table, and sat down opposite from me. ‘Now, I’m going to keep this short. You impressed me the other day, so don’t screw up now. I want you to be here next Wednesday morning at 10:00 sharp. You do know that it is a public holiday, don’t you? Samantha and her father will be out for the entire day.’
‘At 10:15 you will be outside by the pool, and will already have taken off all your clothes. I don’t want you to have an erection yet. I will help you to fit a penis ring before you do… you do know what a penis ring is, don’t you? It will help you keep your erection for longer – you will need it. Once fitted and once we have your penis as hard as it can get, you will start cleaning the pool, facing towards my lounge windows. I’m expecting my guests to start arriving from 10:45 onwards. It’s a meeting for an upcoming church fundraiser, so I want you to be on your best behaviour – that means no foul language mister.’
‘Now, the guests will be four friends of mine on the planning committee with me – all mature, over 60, and all of good standing in the community. I can assure you that, like me, none of them have seen their husbands’ erections in over 5 or 6 years, so who knows what to expect…or how they will react. For this reason, I want you to be as…what’s the word…“fresh” as possible. If you are planning to have intercourse with my daughter over the weekend, get it done on Saturday evening. What? Do you think I’m unaware of the fact that the two of you are having sex? Don’t insult my intelligence. And, of course, no masturbation from then until Wednesday.’
‘My promise to you, if you come through for me on this one, I will ensure that you are properly rewarded. Take my word for it.’ ‘Okay, you can go now. You know how to let yourself out. Just remember, 10:00 on Wednesday morning and again, absolute discretion of course.’
With that, I was out of there. ‘Fuck me’, I thought as I crossed the street back to our house. ‘What the fuck is this shit? Old church ladies… Rings around my cock… What next… What if Sam finds out…’ Well, I figured that if I didn’t tell her, who will? She certainly wouldn’t find out about it from her mother, now would she! In a way, I will be doing this for her. So, how bad could it be – it did sort of appeal to my exhibitionist streak…
I was there on time. Mrs Smith, again impressively dressed in a blouse, skirt and stockings, let me in and took me through to the pool. ‘Well, get it off. No need to be shy now – you weren’t when you ejaculated over my face the other day.’ With that, I stripped off all my clothes. Although I wasn’t erect yet, I couldn’t help but sport a semi stiff cock. Mrs Smith kneeled down in front of me, and taking hold of my cock and balls slipped the ring around it. This time, however, apparently no longer opposed to touching me, she started rubbing and stroking me. ‘Yes, that’s better’ she commented as I became fully erect. ‘But we want this impressive penis head of yours as swollen as thickly as possible, don’t we?’ With that she surprised me even further by slipping my head between her lipstick covered lips and sucking me so hard that I had to grasp in pain. ‘Now, now’ she said as she took my cock out of her mouth and continued to vigorously jerk it. ‘I just want to ensure that we present our guests with the best possible image of youthful virility…’ ‘Now what the fuck does that mean’ I thought to myself, deciding to rather keep my mouth shut. Getting up, Mrs Smith gave my cock a final couple of jerks, before telling me that her guests would be arriving shortly, and that I had to start cleaning the pool.
And that is how I ended up standing naked next to my girlfriend’s pool, sporting an impressive erection, sustained by a cock-ring, and waiting for her mother and her mother’s friends to…to do who knows what to me. It wasn’t too long before I started spotting some movement through the lounge windows. Mrs Smith’s guests have obviously stared arriving and were currently being entertained by, guess what, a naked pool boy cleaning the pool - me. I decided that the best approach would be to keep my head down, my cock up, and keep cleaning.
After a while I noticed that the party moved outside to the patio by the pool. The women were all sipping on glasses of wine, and openly grinning while staring at me. Fortunately, I couldn’t hear what they were discussing. ‘What the fuck is going on at church meetings these days!’ I thought to myself. It wasn’t long, however, before Mrs Smith and one of her ‘friends’ started making their way over to me. She was a mature woman with long grey hair and also dressed in a blouse and skirt. Were it not for her heavy makeup, I would have labelled her as still quite attractive.
‘Well, well, Jane’ she addressed Mrs Smith as they moved up, ‘where on earth did you get such a well-hung pool boy?’ ‘I can’t give away all my secrets, now can I Susan’ Mrs Smith replied with a grin. ‘Look at the massive head capping that penis! Makes me think of a fat strawberry ripe for the picking…’ Susan continued. Mrs Smith just kept on smiling and lead her closer to me. ‘Young man, would you mind if I stroked your penis?’ Without waiting for a response from my side, Susan moved right up to me, firmly gripped the shaft of may cock and began wanking me, my foreskin moving rapidly backward and forward behind the ridge of my cock-head. ‘My, my, now this is something that I haven’t felt or seen for a while…’ Susan said while continuing to jerk me off and to closely examine my cock.
It wasn’t long before I was surrounded by all five ladies, taking turns to touch, rub, stroke or seriously jerk my cock. I even felt the occasional tongue on there, or my cock-head being slipped into a willing, wet mouth. Others were stroking my chest, back or buttocks. While this was going on, I listened with half an ear to a story one of the ladies were telling the group, ‘…now this reminds me of the safari vacations we used to go on while I was a young girl – couldn’t have been older than ten. Dad and the boys went out “hunting” every day, which, according to my mother, meant fucking everything female in the local community older than 12. She found her revenge, if you could call it that, through sitting back at the tented camp, ordering the butler or one of his servants to take out his cock and masturbate for her. I was around most of the time, and couldn’t help but notice how big these chaps were, similar to this boy here. She would make them ejaculate over her shoes and ankles, and then have them clean the shoes with their semen while still wearing them …’
My attention was distracted by Susan, the first lady that came up to me. ‘This is too good to be true, Jane, I’m not going to miss this opportunity’ she told Mrs Smith while unzipping her skirt and taking it off. ‘I don’t mind what the others think, or if they just want to be prudes standing there gawking at it…’ With that she slipped out of her panties as well, giving me a brief glimpse of her hairy pussy.
Walking over to a sturdy outside wooden table, she called over, ‘Young man, come over here. I have a proper task for you.’ Seating herself with her buttocks on the edge of the table, she slowly spread her legs while I walked over. She was already busy finger fucking her pussy, and from the glistering juices on her fingers as it emerged from her vagina, I estimated that she must already be extremely aroused. As I walked up, she spread her legs even further, lifting one and placing her heel on the table as well. With her hairy cunt spread eagled like this, she took my hand, pulled me closer and pushed three of my fingers into her warm dripping vagina. ‘No need to bother with foreplay boy – I want you to get that thick penis of yours into me as fast as possible, and fuck me as hard as you are capable of, understand?’ I did understand, and being an obedient young man with good manners, I did as I was told (I was a bit hazy on how the ‘respecting your elders’ rule fit into this situation, but figured that it must have had to do with not looking into her eyes or kissing her on the mouth...)
Entering her pussy was quite a different feeling than what I had gotten used to with Sam. My cock didn’t encounter any resistance at all - it was just enveloped by that magical warmth and wetness. As requested, I proceeded to ram my cock into her as hard, fast and deep as I could, her buttocks actually bouncing on the table with the force of it. Although this didn’t have too much effect on my lasting power as a result to the lack of resistance, Susan was soon grasping at her breath and breathing deeply. By now, the other woman had formed a circle around us and, surprisingly enough, was clapping and cheering me on: ‘…HARDER…FASTER…HARDER…’ Out of the corner of my eye, I saw that one of the other ladies, older still and quite a bit more chubby, had taken off her pants and was warming up her pussy by rubbing it through the thong she was wearing. I guessed correctly that she would be next in line. For now, however, I focused on Susan, and slammed my cock into her even faster. This was sufficient to trigger her, and she reached her orgasm with a loud moan, clasping me to her. As I withdrew from her, her pussy was still squirting juices freely, with it running down her legs.
As her friends helped her off the table, while congratulating and hugging her, the other lady without her pants on approached me, and asked me for a ride. ‘Please, just don’t ravage me as fiercely as you did Susan’ I took that to mean that I should take it a bit slower with her. With a smile, I agreed, and helped her slip off her thong. Meanwhile, I saw that Susan was standing amongst her friends laughing, lighting a cigarette, while still toying with her wet lips. One of the other ladies was wiping her cum from her legs. I turned back to my second customer for the morning, and while again assuring her that I will be gentle, pushed her up against the table. ‘No, I want you to take me from behind if you can…’ She asked. Turning around, she bend herself down over the table, lifting up her round white buttocks and exposing her fat shaved pussy lips. Not thinking about it twice, I moved in behind her, and taking hold of my shaft, slowly slipped my cock-head into her also already wet vagina. At least she felt a bit tighter than my first encounter of the day.
All the ladies had gathered around us again, but weren’t cheering so much now. They just looked on as I slowly and rhythmically pumped my cock in and out of her. We continued like this for quite a while before the lady beneath me also neared her orgasm, evident from the low moaning sounds she was emitting. Starting up their cheering again, the group of ladies encouraged me to speed things up a bit. As I increased the pace and force of my intrusions into her pussy, I started to feel the now familiar contractions around my cock-head deep in her. It was so much fainter than was usually the case when Sam reached her orgasm.
After she started to relax and breathe more slowly, I pulled my cock from her and helped her get up off the table to further cheering from the ladies. Apparently this was all the fucking I would have to do for the day. The remaining two ladies still had all their clothes on and gave no indication that this would change soon. One of them helped the old lady get back into her underwear and pants, with the remainder gathering around me again to continue tugging on my now drenched and slimy cock.
It was Mrs Smith that came up and suggested to them that they should start getting serious with their jerking and try to make me ejaculate. This of course lead them back to the story about the butler having to cum on and clean shoes. It was immediately decided that this would also be my fate for the day. With this, the intensity of the cock jerking increased significantly. As I neared orgasm, three of the woman positioned themselves in a row in front of me, waiting for the semen to flow. I noticed that two of them were those who decided against being fucked in front of their friends. This left Mrs Smith, Jane, and Susan, still without her panties and skirt back on, to continue jerking my cock furiously. Not long after, jets of cum sprayed from my cock over the feet of the lined up ladies, with me trying to get as much as possible thereof on their shoes.
And that was how I ended up naked next to my girlfriend’s pool, still sporting an impressive erection, sustained by a cock-ring, and shining the shoes of mature church going ladies with my own semen.
Afterwards, when the guests have left, Mrs Smith came over to me. ‘From now on, I insist that you call me Jane.’ ‘Thanks Mrs Smith’ I replied. ‘Now for your reward’ she continued, apparently without noticing, ‘you have a choice. This time I will allow you to ejaculate over any part of my body – your choice. You will also not have to get yourself to orgasm – I will suck and lick your penis until you ejaculate. Alternatively, and it you could stomach more hairy mature pussy, you can finger fuck, suck on, or lick mine for as long as you like. Who knows, if you do it properly, you might even get to experience a full and proper she-jaculation, if you know what I mean…’