Confessions of a Horny Devil Ch. 34

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A man's journey from 18 to 35.
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Part 34 of the 34 part series

Updated 11/02/2022
Created 11/18/2005
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CasperNZ
CasperNZ
39 Followers

The time for me to stop messing around had finally arrived for me following the difficult situation which arose in the mall with Suzie, Sally and her lovely full figured daughter Melissa...

Believe it or not, but for some months I remained single and celibate, merely practising self service during this period. It changed my outlook on life, women and relationships to such an extent that people seemed to treat me differently. Eventually I met the lady I am now married to, she has a fair idea of what my past holds, but she doesn't have a desire to know every sordid little detail....heck, she told me so herself...phew!!

What this leaves me with is a collection of not so successfull attempts at getting together with women I fancied. Also it brings to mind the many embarrassing moments that have occurred in my travels.

So in no particular order let me lay some of my not so proud moments on the table....

During my time with Maggie, the lovely older lady who introduced me to the wonders of uninhibited sex, we had sex in many places. One regularly repeated location was for me to fuck her in the back of the courier van that I had then. We'd park up in a carpark overlooking the motorway, dimly lit and away from any walkways just to avoid the prospect of spectators... So after a few weeks of parking up in the same spot two or three nights a week we wound up with a spectator alright!

In the throes of passion we hadn't heard the police car pull up alongside the van, but when this powerful beam of light shone into the van both Maggie and I freaked out....not the sort of thing you want to happen when you're on the home stretch to an orgasm.

After several seconds a voice simply announced that they were the police, could we get dressed and come out. Both Maggie and I felt rather sheepish, but we clambered into our clothes and opened the sliding door to find a male sergeant and his lady junior constable grinning slightly.... After we'd shown them some ID and had answered all their questions we got a warning for lewd conduct in a public place and with that were sent on our way.....

I know it should have been common sense but I guess this lesson should be called: Don't fuck in the same place too often or at regular intervals....

With my little redhead girlfriend Trish I had a few interesting events....

Trish loved sucking me off in the car, and even though she was jealous as hell she talked about this with one of her work colleagues, Jane, on a regular basis. Now what the deal was with this I don't know, maybe Trish wanted to make Jane jealous, maybe it was something about boasting or showing off....who knows. All I knew at the time was that Jane was a hot little blonde who had the sort of body that most guys would lust after blindly.

I say most guys, 'cause she tried hitting on me during one of the work socials that I attended with Trish, with no effect. OK, I enjoyed looking at her big plastic tits with rather big nipples, but her attitude was just the pits, so in those terms she just wasn't attractive, to me at least.

Anyway, this whole teasing Jane thing had Trish pretty worked up, so much so that she began suggesting I park up in a back alley to let her suck me off, just after picking her up after finishing work. Now we'd done this a couple of times when lo and behold, who comes walking towards us in the alley but Jane!! She sees me, and then the little redhead's mouth bobbing up and down on my throbbing shaft and she just shakes her head and walks past, as if nothing was happening.

People walking past the car whilst I was getting sucked off was pretty rare in this alley, and hell, I just loved getting sucked off so if someone looked then it didn't really bother me. Most folks would just grin and keep walking....

I never thought past the point of cumming in Trish's mouth, for when Jane kept appearing repeatedly I should have known this could not go on without some consequence.

Well, one day instead of Jane it was a trio of police officers who strolled thru the alley. Both of us got arrested, bailed and ended up with a court date. I found out later that Jane had laid a complaint with the police, saying I would wank off in public view of her as she made her way thru the alley. The judge shook her head when she figured out the true nature of the complaint....ie. she is sucking on his dick, but I want to have a go instead...or something along those lines. End result is case against both of us is thrown out.

It did put a different perspective on the future public displays of "affection" we got into.

Oh, and we did pay Jane back a while later, setting her up on a date with one of my buddies, he's got an enormous cock...Jane was hot for big cock....guess we forgot to tell her that her hot date was also gay...but Marcel loved to play the part anyway!!

Another embarrassing moment happened also while I was with Trish, this one in the supermarket on a Friday night. We'd been to the movies and it must have been close to midnight when we did the silley thing of doing the midnight grocery shop before going home to start our regular weekend slumber party and fuckathon....

So here I am with the shopping trolley in the cereal section, Trish has just walked back to the deli to get something and I just feel this pair of hands sliding around my waist, ending up on my crotch, squeezing my ever responsive dick. It's when I look down to see it's not Trish doing some playful groping that I think, oh shit!!

OK, what the fuck is going on here I said out loud, only to find my old colleague Christina standing there with one of her girlfriends. Looking like they're in the middle of a good night out, all dolled up and looking nice and slutty, Trish sees Christina's hands on my crotch groping me and she just yelled out from a distance; What the fuck are you doing bitch!?

Well, suffice to say that the weekend of lazy fucking and lounging around was off the menu....

I suppose I learned that if one is out shopping with his current squeeze, keep her nearby at all times to ward off the old flame syndrome....

Another difficult situation with Trish involved her mother. Now to take the mystery out of the situation, yes her mother had seen me fucking Trish on more than one occasion. But no, I never did fuck her mother, even though she tried to take me to this dangerous place.

The first time was when Trish had some serious dental work done, her mother had taken her to the dentist and then brought her home to our little apartment. Trish was well and truly doped up and out of it when I came home from work.

With Trish asleep on the bed I offered Faye, her mother, a cup of coffee. We sat down and went thru the dental procedure, what I had to do for Trish while she recovered from her anaesthetic etc. Nothing untoward was talked about, we ended with Faye saying goodbye and walking out the front door at the same time as I headed for the shower.

A few minutes later as I am soaping myself, imagine my surprise when into the shower steps a stark naked Faye, and to make it worse she just grabs onto my almost rigid cock as she hops in.... I didn't jump or freak out physically, but my mind was in a spin.

She tells me how she's been hot to get hold of my cock since she saw me pounding her daughter doggie style on her lounge floor a few months back. My husband used to do me in much the same way in the same place, she told me with a sad look on her face, all this whilst firmly tugging on my now rocksolid cock.

How do you tell your girlfriend's mother that you don't want to do anything silly when your cock is throbbing in her hand? Yeah, well, all I did was tell her that I couldn't do this...all emotions conflicting...heck, I felt sorry for her not having been looked after sexually since her husband's death, but at the same time she WAS still my girlfriends mother.....

The situation ended as soon as it had started, with Faye getting out of the shower and leaving me to it. When I got out she had gone. We didn't talk about what had happened, even though next time I saw her we were both a little uneasy.

The summer holidays, which followed a month or so after this difficult event, had always been a family gathering at the beach house they owned. This summer only Trish's brother and his wife would be joining us and her mother. A happy little fivesome?? Not exactly.

With her brother and a few friends out on the boat, Trish joining them, but not me on account of having been sunburned the day before....this left Faye, myself and Pauline, her brothers wife at the beach house. With Pauline sunning herself on the back deck, me inside reading a book, still hiidng from the sun... Faye came over to bring me a cold drink, then as she kneeled down alongside me I got this weird feeling she was up to something.

OK, I thought, what is up now. With Pauline just outside the door, snoozing in the sun after several alcoholic drinks mixed up by Faye, I got worried. With Faye now somewhat drunk on her favouorite, G & T, she rested her hand on the crotch of my shorts. Immediately my cock hardened in response to her touch, instead of jumping up and getting of her reach I just quietly told her, please no!

She obviously didn't understand that the way I meant it, possibly on account of my cock swelling to full tilt in about 2 seconds? It was when her hand went up the leg of the shorts and withdrew the now proudly erect cock that things started to head out of control. With Faye now giving me a firm pumping with her hand, her other hand cupping my hefty nuts I closed my eyes momentarily....I was enjoying this immensely and yet at the same time I was trying to put a stop to it, admittedly I wasn't trying very hard.

It was when Pauline called out and got no response that she rolled over to look into the house. Luckily for me, Pauline was fairly drunk by now, the sunlight was very bright outside, and combined with it being pretty dark inside it took her several seconds before she could see what was going on.

Well, she didn't see exactly what was going on, but she saw Faye giving me a drink while I sat up to conceal my cock and balls standing at full attention. Pauline did ask something along the lines of, what the hell are you two doing there, but as Faye got up she walked outside to find Pauline just blithering away. Drunk and under the influence of too much sun was the verdict.

This was just too close a call for me, and it must have been for Faye too as this was the end of her attempts to make me do something which we both knew we shouldn't.

Oh well, I can laugh about it now, but the thoughts of Trish finding out I had been screwing her mother (or at least been on the verge of doing so) were enough to hold me back....if only just. Regardless, my relationship with Trish lasted four year and ended when we both got caught up in becoming too career focused.....sigh!

Perhaps one of my most embarrassing moments came after having a fling with one of the ladies at work, Lois the department head at he firm where a whole lot women worked, much to the chagrin of one of the younger girls who had been trying to get me interested in her.

Now, OK, Lois was a hot blooded mature woman who had a demeanour which was initially a little intimidating to most around her, but combined with her playful and saucy nature she was well liked by most women...as well as lusted after by a good number of the guys.

Renee on the other hand, was one of the computer "geeks" who looked after the substantial IT needs of the firm. Geek isn't really the right description of her, for she had the body, but lacked the right attitude, perhaps this was why I hadn't responded to her many feeble advances?

It was after I left this job that Renee managed to "accidentally" run into me at the shopping mall one saturday afternoon, although I quickly found out there was nothing accidental about it. She was now dressed to kill, literally, with a tight fitting pencil skirt, black patent high heels and a figure hugging white blouse. Her long hair was tied up in a simple single tieback, exposing her beautiful face nicely. Her attitude was different too, she seemed more open, warm and radiant, rather sexy combined with the sexy clothing she now wore.

The next hour or so we spent together, strolling thru shops, having a bite to eat and just enjoying each others company. Renee did ask about Lois, what I was thinking in banging an old bird like her, instead of giving someone my own age a bit of attention. This was not a new concept as Melissa had often commented on this as well, although in more sarcastic tones.

So as we walked out of the mall Renee had me set up on a date with her for the next weekend. I was to meet her at her house, have some dinner and then we'd head off into town for some clubbing.

Sounded OK, except that on the day in question I found not just Renee at her house, but also several women from the same firm, Michelle the married receptionist, Amanda from accounts, Melanie from sales and Wendy from customer services. All women were dressed up for a night on the town, Melanie in particular looked like a little blonde bombshell in her skintight little black dress!!

Renee seemed to be the ringleader of this group however, now dressed in a tiny little skirt, hideously high heels and a tubetop which showed her stiff nipples proudly. As Renee invited me in, the minute the door closed behind me the women swarmed around me, and began stripping my clothes off roughly, tearing my shirt and yanking my jeans open far enough to rip the zipper at the bottom.

I was alarmed by now, but when I was handcuffed to the central stairway, stark naked by now, with my hands behind my back I was nevertheless fully erect. Comfy in this position, asked Renee in an absentminded manner, not bothering to wait for my response.

This was at about 6pm on saturday evening, and the girls spent the next two hours just teasing me mercilessly. My cock was twitching away something chronic, they kept rubbing me with their young hot bodies, occasionally letting my cock touch their firm tits and nipples... The problem here was that I didn't know how this was going to end, the most sexual thing that happened was getting a saliva covered hand jerking my knob....

My balls were ready to pop, my cock was aching for release and yet all the girls kept doing was just teasing me.... Then the doorbell rang, and as Renee opened the door I saw Lois, the hot little redhead I had fucked a few times, enter the house...and she looked pissed!

So now there is six women here, all dressed for a night on the town and I am naked, tied up and aching to blow a load of cum to release the pressure on my heavy nuts.....

"Well well, what have we here," Lois started as she came up to me, grasping my throbbing cock with one hand and then slapping it with the palm of her other hand. Whack, her hand went as she did so, and it sent a strange shiver of excitement thru my body.

Obviously Lois didn't like the response she got, my dick throbbing even harder in her hand, so she whacked me again, this time much more forcefully. Even though it hurt a little the response was much the same, my dick just kept throbbing nnd twitching in her hand....

"You are just a horny little bastard aren't you Nick," Lois sarcastically said. "Us girls are off to town now, but we're bringing in Justine to look after you while we're out enjoying ourselves," Lois continued, "she'll cure you of having a hard prick in no time!"

With that Lois opened the front door and let Justine into the house. Now Justine is what I would call a big beautiful woman, she's the team leader for one of the customer services teams and even though I would not normally chase after such women, the thought of being naked in front of her was rather arousing...

"Bye bye, horny little fucker," the girls said pretty much in unison as they left me tied to the stairway naked.

"Mmmmmm, what are we going to do for the next five or six hours then," Justine asked me somewhat embarrassed at the situation she found herself in.

"Crikey, I was hoping you would have had a plan for that," I said as calmly as I could, given the difficult circumstances I found myself in.

"Actually, I do," Justine said as she picked up her cellphone and called someone. Minutes later the doorbell rang and in walked a butch looking woman, whose face broke into a huge smile as she saw me tied up, naked and fully erect.

"Hey Justine, how are you doing babe," the newcomer said as she wrapped her arms around Justine and kissed her passionately.

I didn't say it, but my mind just whirled at the thought of being naked and tied in the presence of two lesbians.....this could get tricky, as if the whole situation wasn't already tricky enough!

The newcomer walked over to me, said; "Hey horny man, I am Katie, Justine's part time lover and she tells me she needs help looking after a prisoner," leaving the last word hanging in the air. At this she grasps my still turgid shaft and starts to slowly pump my cock, cupping my now aching nuts and smiling broadly. "Ooohh, I think her likes being jerked," Katie said with a giggle.

"Yeah, well I am sure Nick would also love to be sucked, so why don't you give that a try as well," Justine quipped. Before I could say suck me, Katie leaned down and sucked my rigid dick between her lips, sucking me briefly then spitting me out and walking back to Justine.

For the next five hours these two women took turns teasing the hell out of me, I was so frustrated at their ability to take me almost to the point of cumming and then slowing me down again. Man, my balls felt like they were the size of tennis balls!!

It was somewhere around 1am that Renee and her troupe returned. With Lois leading the charge, Renee, Amanda, Michelle, Wendy and Melanie all stood around me as I was still tied in the same position. About an hour or so ago, Justine had let me piss in a bucket, after me threatening to just piss on the ground....

Now with Katie and Justine joining in, 8 women in total standing around me, Lois started; "Nick, you were one of the better fucks in my life, but when you stopped returning my calls I just got pissed, so let this be a little reminder....just to make sure you return a woman's calls."

Now Lois took my soft cock in her hands and gingerly stroked me, rapidly swelling to full size I was soon at the point of blowing my wad.

Then Lois continued her speech; "Even if you don't want to see a woman again, why can't you at least be a man and tell her?" Her face got slightly contorted as she slapped my now rigid cock firmly, all girls cheering her on.....

My mind was in a spin, I wanted to cum, no I needed to cum, and here is 8 women grinning at my discomfort....never before or since have I felt so vulnerable!!

"So what do you think girls, shall I let him cum or do we want to tease him some more," Lois asked the group.

"Actually, Justine and i have teased him for hours already," Katie piped up.

"Cool, that means he'll blow a huge load then," Lois grinned viciously. "Grab the wine glass, so we can catch this load then," Lois ordered.

With that Lois kneeled in front of me, now jacking me off with purpose, wine glass at the ready held by Renee.

Finally, I was on the home stretch, and as I came in the wine glass pumping spurt after spurt of thick white gooey spunk the girls clapped in response to my groaning....fuck this was weird!!

But it got weirder still. Once Lois had milked my softening cock completely dry of its last few drops she held the wine glass up for all the girls to see. "OK, girls, I bet he will be able to drink all this cum in one big swallow," Lois triumphantly announced.

The chorus of girls seemed to think I would not be able to do so, but Lois had no problems holding my nose shut with one hand and then bringing the wine glass to my lips. "Go on Nick, I know you love the taste of cum," she urged as she playfully placed her thigh against my soft cock.

CasperNZ
CasperNZ
39 Followers
12