Confessions of a Horny Devil Ch. 02

At the same time I started uni I also got myself a part time job at a courier depot in town, sorting freight coming off the courier vans for loading onto the linehaul trucks later in the evening.

There would have been around 20 or so youngsters like myself working there, sorting freight for about 3 hours then spending an hour or so hanging around with the couriers and the office crew. This was my introduction to a proper working environment and the social interaction that it can bring.

After a few months of working hard and taking part in the regular Friday night social scene I felt at home here. Then came a bit of a thrill one night when Karen, the branch manager's personal assistant joined in.

Karen had a reputation as a party girl, despite the fact that she was married. After a couple of drinks Karen was getting louder and a bit crude in the jokes she started telling. One of the older couriers, Warren, then asked Karen straight out; How about showing us your big tits? The room went quiet, wondering what Karen would do in response. To my surprise she simply stood up, unbuttoned her blouse and unclipped the front catch on her bra and let her boobs swing free for all to see.

What was most impressive to me was how a set of tits as big as Karen's hardly dropped when set free from their bra...Then again she was only 23 and had no kids, until someone called out that we didn't want to see fake tits...get the silicone girl to cover up and get Nereid to show us her knockers.

Now Nereid was customer services supervisor, about 28 and had a nice curvy build, unlike the skinny Karen. Nereid was already in the social room, trying to hide behind a couple of girls, but as I was to find out it was only mock shame.... Her shame lasted only seconds, before we knew it she's up on a table and gyrating away like a pro, the guys all shouting for her to take it off, take it off!!!

She got her top and bra off, tits nicely swinging free, but while unzipping her skirt the branch manager stormed in and broke up the party...Ooooppss!! Funny thing was, a couple of Friday nights later when I went up to see Karen for the issue of some more uniform gear, I saw her getting nailed on her desk by one of the sales reps.

As I approached the glass door to her office I saw a guys arse, pants around his ankles and Karen with her legs wrapped around his back, holding on for dear life as she got her cunt stuffed.... she looked right at me, smiled, then waved me off...as if to say; Come back later, I'm busy now. Must have been on account of me just standing and looking for too long?

The following Friday was a quieter evening but in many ways much more "productive" for me. There was a lot of discussion amongst the guys about who had the best set of tits, all that sort of useless talk. I was asked by a couple of girls what I thought, my response was an honest one in that I preferred a shapely pair of legs instead of a pair of bowling balls on a woman's chest.

That took the discussion in the room in a different direction, but from then on I was referred to as the legman by a few of the crew.

A few Friday sessions later the discussion again turned to legs, tits and sex appeal....funny how alcohol and talk of sex goes hand in hand for some folks?? It was inevitable I guess, but I got asked the question what I thought made a woman sexually appealing.... Didn't have to think too hard about that, to me it's about her self-confidence, being comfortable in her body, not trying to be someone she's not and feeling free enough to go after what she wants. That drew a few admiring glances from the women in the room, seemed like I was the only one who didn't mention physical characteristics in summing up sex appeal. I thought that I was onto something here, just needed to take my time and not rush this process....

So the Friday evening sessions often turned into group discussions on various subjects, not always sexual, but often ending up on the topic of sex.

It just had to happen one way or another; one night we were again into a full-on discussion and the question I got asked was the one about older women. Thinking carefully I answered that I thought an older woman made an ideal lover for a younger, less experienced man, but only if she was confident and willing to be a teacher. Well, did that bring silence to the room! The guys were looking puzzled and as for the women...well, I noticed the look in the eyes of Margaret, who was our customer services manager, as one of sheer desire.

Later in the evening Margaret ended up standing beside me, brought up the older woman question with me and asked me if I had ever been with an older woman. Since Sally had been older than me I could answer semi-honestly in the affirmative... Margaret then leaned forward a little and asked me if I minded giving her a lift home later on. Yep, was all I said and since it was my turn at the pool table I got back to the game.

Now let me describe Margaret.... she'd have been early forties at the time, tall, trim and long legged. Her black hair fell halfway down her back, and being a mixture of Maori / Portuguese she had a permanent tan. To me she was a good-looking woman who rarely showed off her physique by means of revealing or tight fitting clothing.

A little later in the evening Maggie tapped me on the shoulder and asked me if I was ready to go, as I turned I noticed she'd changed from her usual pant suit into a knee length skirt and sleeveless blouse, her 3" heels now putting her eyes level with mine. As we walked to my van I couldn't help but put my arm to her waist, she put her hand a little lower, getting a handful of bum and giving it a gentle squeeze.

In the van she sat in the middle seat, right up against me and asked if the thing about an older woman teaching a younger man was something I was still waiting for, and if so could she be my teacher? Yes please, I said, with my best innocent smile....

Maggie's response was to kiss me on the cheek, then she playfully ran her hand up the inside of my thigh, but stopping short of my crotch. You tease I said, turned to her and while kissing her full on the lips ran my hand up the inside of her thigh. Reaching the hem of her skirt I kept going and before I knew it I had reached her panties. As I rubbed her pussy thru her knickers she shoved her tongue into my mouth.... Maggie eventually pulled back and asked if I actually needed a teacher... Hell yeah, I may have the balls to grab your pussy but I need help refining the rest of my technique. She smiled, put one of her hands on my crotch and while cupping my balls she grinned... Hmmm, nice heavy balls you have young man, now take me home so I can milk them for you.

The drive to Maggie's place took far too long, her hands roaming over my thighs, cock, chest, shoulders and neck. Inside Maggie's house we started by hugging, kissing and fondling each other all over. Over the next few minutes we got each other undressed and ended up tangled up on the couch, Maggie on top of me.

She had a look of lust in her eyes as she crawled into position to lower her cunt onto my throbbing cock, she simply took hold of my dick at the base and rubbed my knob over her trimmed cunt...the lips of which were swollen and coated in her juices. As she used my cock to tease her clit she suddenly grew still, breathed out long and hard then without any warning plunged down onto my dick until my balls were nestled between her arse cheeks. She stayed put until her body stopped the gentle twitching that started when she rubbed her clit with my cock.

I had just experienced my first female orgasm, and was now enjoying the extremely wet and hot cunt of an older woman in heat...man did I love this feeling!! When Maggie started to fuck me with her juicy cunt I felt like I was in heaven, her juices running down onto my balls, the squishing sounds of my cock being devoured by her hungry cunt and the slapping sounds of her arse banging into my thighs and balls...sheer bliss!

Being a young fellow with little experience I didn't last very long, maybe a couple of minutes, before I blew my load into her dripping hole. She lay down on top of me as she savoured my spunk oozing past my cock and out of her fanny.

As Maggie lay there looking at me she smirked a devilish little smirk, I guess this was on account of me having blown my load but my dick still being pretty hard. Not rock hard like before, but hard enough to continue fucking her juicy snatch... So she continued to slowly stroke herself up and down on my rapidly stiffening cock, all the while our combined juices running out of her.

At this time she offered me one of her nipples to suck on, the big brown suck patch being topped by a cherry sized nipple that just needed to be nibbled on. Yeah, just take it into your mouth and suck on it gently, now try biting it gently then alternating with your tongue just lapping at it...Maggie was teaching me how to suck her tits while she was sliding her cunt up and down my cock...What a teacher!

Soon her breathing got ragged again and she closed her eyes, just focusing on her cunt with my stiff young cock inside. She ground her way towards her next orgasm, just about squashing my balls as she ground back and forth, left to right, up and down. As her strokes got faster I held her hips and started thrusting up at her, meeting her strokes midway and banging us together harder than before, causing my balls to really slap against her butt...

It seemed like an eternity, her mouth opened and her lower jaw went slack, her head went back and she slammed herself down onto me and stayed put, my balls aching from being trapped between our bodies, her sweat dripping onto me. Now it was my turn to fuck, slow then fast and before long my balls were emptying themselves again into this hot woman.

Now it was about 10pm on a Friday night, didn't have to go back to work until early Monday morning, and had nothing planned other than to relish my time with Maggie. My mind was in a spin, a hot-blooded older woman who wanted to teach me about sex and in the meantime use me for her own pleasure.... Tough life I suppose??

This was at the beginning of November, and we spent that summer together doing allsorts of naughty, delightful and delicious things together. Maggie seemed to relish the fact that she could ride my cock half a dozen times a day, everyday! It brought out a side of her that was hidden away before, she taught me how to make love to a woman without abandon or selfishness, I regularly complimented her on her hot body and great looks, this seemingly brought out a confidence in Maggie to wear shorter skirts to show off her gorgeous legs.

In the end, with Maggie in the right mood she would go out wearing shortish skirts without underwear, highish heels to accentuate her calf muscles and tight fitting tops to showcase her firm small breasts with big nipples. In short, I guess my interest in her took her back to her younger years and it possibly encouraged her to dress more provocatively. On the other hand it's also possible that she enjoyed dressing sexily because of the reaction it got from me, rock hard and ready to ride....

Even though we didn't fuck in many public places, both of us being a little shy... she did suck me off in a movie theatre, even though we weren't sitting in the back row, this in a cinema where about half of the seats were occupied.

During my training period the thing that Maggie took most delight in was the fact that she managed to teach me self-control, developing the ability to pretty much decide when to cum. The way Margaret described it, she judged a guy by how long he could hold out while she was sucking on his cock for the first time...if he could resist her mouth for only a minute or two how would he last long enough inside her juicy snatch to give her a thorough shafting and bring her to orgasm?

By the time she'd been coaching me for a while, she just loved being able to ride my young throbbing cock for half an hour before I got to the point of emptying my balls. A lady should be allowed to cum first, she always said.

A few months after getting together with Maggie she told me she wanted to take me shopping for some tight fitting jeans, commenting that she loved to look at my bum...and also to see my big heavy balls and cock wrapped up tight and on display.... OK, I thought, this could be interesting.

Then when Maggie let on that she wanted to take me to a particular jeans store, where a girlfriend of hers worked...a girlfriend who loved younger guys.... I knew it could be very interesting.

When I asked her what the idea was, Maggie was not exactly direct in answering but I had the feeling that if Mary and I liked each other then Maggie was happy to lend me out....or something like that! On the day in question Maggie turned up in a short skirt, high heels and a simple tight fitting T-shirt that left no doubt as to the bra question, nice!

We arrived at the clothing store shortly before closing, walked in the door and were immediately greeted by Mary, a tall dark haired lady, part European, part Polynesian. Her mocha skin colour, bright green eyes and smiling facial expression made her look a lot like one of Maggie's sisters....

The way she looked me up and down as Maggie introduced me had me wondering just what Maggie had told her about me...?? Not that I was ashamed of anything Maggie and I had been up to, just feeling a little like being put onto the "meat market" so to speak. Looking at Maggie after the introduction I could see her rock hard nipples poking thru her T-shirt so something was up!

The girls selected several pairs of jeans with while Mary's shop assistant looked on with boredom all over her face. In the big dressing room in the corner Mary placed the jeans and tops on the bench seat and told me to come on out when you're ready.

Looking around the 9 foot square room I noticed two walls had floor to ceiling mirrors, while the entry door wall started at least a foot off the floor and ended about six feet up. As I was putting on the first pair of jeans, in the mirror I saw Mary's head poke over the top of the dressing room wall, pretended that I didn't see her and carried on. A few seconds later her head disappeared.

Donning one of the tops I stepped out of the dressing room as both Maggie and Mary looked on. Not tight enough, try on a smaller pair Mary immediately said. Yeah, you gotta show off your wares more, Maggie whispered. As Mary went off to get a smaller pair of jeans in the style I was wearing I told Maggie about seeing Mary perve over the top of the wall. I know, Maggie said, I told her to. When you try the next pair of jeans on, make sure you swing your dick in the breeze for us girls to see!! When I looked at her questioningly Maggie just told me to go with the flow, and that Mary already had commented to Maggie that she'd love to have a young fellow like me take her!

So when Mary gave me the smaller pair of jeans I took them into the dressing room, making sure to accidentally not close the door properly. And following Maggie's instruction, I took off not just the jeans but my jocks as well. I swear I heard a little gasp from outside the door. Turning just a little, making sure that Mary got a good view thru the slit in the door, I could feel my balls hanging heavy in my sack, dick swelling up a fair bit but still hanging down.

As I tucked my nuts into the jeans carefully I heard another faint moan come from just outside, so when I had to tuck my dick into this pretty tight pair of jeans I took my time, this time hearing several heavy breathes from the door.

Taking one last look in the mirror I was surprised at how much this tight pair of jeans showed my balls and cock! Stepping from the dressing room, Maggie let out a wolf whistle, which caused the shop assistant to take a look, she grinned as she saw both women perving at me, smiling at me when our eyes met briefly. Mary looked at my crotch without any shame and said that this pair was much better. Maggie was grinning broadly as she'd seen the whole spectacle unfold, her nipples showing thru her T-shirt....now I was wondering how much of this had been a setup.

OK, let's take this pair, Maggie said, just pin them up for length while he's wearing them and then he can try on another pair. As Mary went onto her knees to pin this tight pair of jeans I saw the shop assistant look on with interest, my dick twitched as Mary took her time pinning the hem, taking lots of time to look up at me, or my crotch to be precise. From this vantage point I could also see down Mary's cleavage, the lacy edges of her bra just visible from up here. When she'd finished the pinning Mary got up from her knees looking just a little flushed.

When Maggie suggested I try on a pair of the stretch jeans in a size smaller than what I was now wearing I saw Mary's eyes roll a little, she must have been thinking the same thing?? Back into the dressing room I stripped off completely and squeezed myself into the stretch pair of jeans with some difficulty, by the time I was tucking myself in and zipping up I once again sensed a pair of perving eyes at the slit in the door. Looking in the mirror I was almost embarrassed at how this pair left little to the imagination, you could clearly see my balls separately and the way my now half hard cock lay across was almost obscene. Nevertheless when I stepped out of the dressing room both women tried to maintain their composure. The shop assistant was now taking in the spectacle with some interest, when Maggie said to Mary to pin this pair as well it took only a second or so for her to be on her knees again in front of me.

This caused the shop assistant to break out in a lusty grin, and even though closing time was a few minutes off she went and closed the front door.... She must have sensed what was coming next huh? While Mary was fidgeting with the hem I noticed her blouse now had a couple more buttons undone and I could clearly see the half cup bra fighting a losing battle to hold in her nipples.

The shop assistant returned to her counter and leaned on her elbows to take in the view, smiling and licking her lips at the same time, something which was not lost on Maggie, who only grinned a lusty grin to both of us as we watched Mary finishing off the hem pinning. When she was done she just sat there on her knees, skirt riding halfway up her bare thighs, her high heels gone...now I realised that what I was hoping for would actually happen.

Mary sat up on her knees, bringing her face level with the bulge in my jeans, her hands travelling slowly up my legs, causing my dick to swell and twitch in its confined space. As she reached my dick she firmly kneaded my now rigid shaft with one hand, while the other was rapidly undoing the button and unzipping me.

Mary peeled back the tight jeans and in doing so my dick slapped her in the cheek as it sprang free. Without any hesitation she opened her mouth and sucked me deep into her mouth, pulling the jeans down my thighs at the same time as she was face fucking me. The shop assistant by now was wide eyed, Maggie sitting back in one of the chairs in the dressing room area, just looking on contentedly.

When Mary had managed to wriggle me out of the jeans she dragged me onto the floor on my back, yanked her skirt up and promptly sat on my face, rubbing her musky cunt across my mouth as she resumed sucking my dick. The excitement of the situation was intense, but once I focused only on licking Mary's juicy cunt and sucking her clit I forgot about where I was....just allowing myself to enjoy what was happening.

After a few minutes of probing her snatch with my tongue I could sense Mary was on the verge of her first climax, so I held her tight as I went to town on her swollen clit. When she came, the taste of her juices was exquisite! Giving her a few moments to come down a little, she attacked my dick with renewed ferocity, now taking turns sucking my knob and then my balls.