Hard Lesson Learnt Pt. 02

Life carried on, and I thought less about my adventure with Hayley. It was confined to my memory, nobody else knew and that was how it would stay, but then I slipped, and the next stage of my self-inflicted problems was in motion.

The slip came with a client called Gary. He was one of my longest standing clients and also one of the most lucrative. I had recruited him as a client at the old business, just as his company was starting to take off. He came with me when I started this company and our businesses have grown together. Despite this long association, Gary is always looking for extra perks and benefits to keep his business with us and while not worried about trying to chip away at our charges and fees, he likes to be treated to extras, made to feel special.

The regular treat is a game of golf together, at an exclusive course, at my expense of course. Two or three times a year we make a trip away together. Normally to watch some sporting event, with a hotel stay after, and plenty of food and drink. Aside from that, we regularly eat out together, with Rachel and perhaps the current partner of his.

Now, Gary is a client who has become a friend, but he does intimidate me a little. He's approaching the mid-40's, so just a few years older than me, but stands at about 6 ft 3 inches, with an athletic body, you would probably say a swimmer's body, and is, I have to admit, a good-looking individual. Rachel has always admitted that he is good-looking, her description is "rugged." She also admits that he has gotten better with age, his dark hair has flecks of gray, as does his ever present stubble. While Rachel admits that this is one good-looking guy, she also says that he is not her type as he is too self-confident and full of himself. The word she uses is cocky.

Gary uses the looks and self-confidence to good effect, he is one hell of a ladies man. He has been married and divorced twice, both times to beautiful, but 'air-head' women, that's his quote, not mine. He admits himself, though, he can't keep it in his pants, and isn't destined for a long term relationship, yet. He is always looking for a new conquest or one-night stand because, he says, that he needs to screw 4 or 5 times a week, and with no permanent partner he has to try one of his regular 'Fuck buddies' or find a one-night stand. Tinder has been a godsend for him, for when he is at a loose end.

He tells me so many stories during our golf games, and I would normally consider that there is some exaggeration, but I have seen him in action. He sees an attractive woman, and he just walks right up to her and starts talking. Added to his height, build, and looks, it is this utter self-confidence that intimidates me. I could never just walk up to strangers, like that, and start to chat them up. They are always attractive, anything between 20 and 50, and more often than not he is successful. If he gets rejected or can tell that he is not going to get sex, he just moves on.

On our trips, he has never failed to take a girl back to his room for the night. On more than one occasion, post event, we have been out, and he uses me as his wingman. I just stand there and chip in with the occasional amusing comment, while Gary is working tirelessly at charming women back to his room. Twice now, he has managed to get one for each of us, telling them that they are in for a treat as, even though I am quiet, I have a horse cock in my pants, 'it's even bigger than mine,' he tells them. He knows, as it's been discussed and demonstrated, that I won't cheat on Rachel, so he knows that when we get back to the hotel, I will refuse the young lady, admitting to being married and unwilling to cheat. He will fake a mini debate, call me a pussy and take both girls back to his room, promising that he as he has enough for both of them. One of those times, our rooms were adjacent and didn't have the best sound proofing, so I was treated to several hours of moaning, screaming and laughing. He certainly had enough for both!

The reason he claimed that I had a horse cock is that he suspects that it might be true. He talks about Rachel all the time, asking after her, wanting details of our sex life, and wondering what she sees in me. He openly tells me that I am batting well up the order with her, and the only conclusion that he can draw, is that she is with me because of a massive cock. He can see no other reason for it, and if he met a single Rachel, she'd be in his bed before she could blink. Obviously, I don't deny the cock thing, I just laugh and shrug. Truth is, as I have mentioned, I am not sure why she is with me either, but happily, she is.

It is Gary's constant need for something extra, to maintain our working relationship, and his obsession with beautiful women, that led me to add Hayley to the sales admin team dealing with Gary's account. I knew that he would find her a perk and I knew that he would hit on her, but I believed that she was too professional to fall for it. This was before I knew that she was sex obsessed herself, and 'loved to fuck.' Luckily though, she had always rejected Gary, she was as self-confident as he was and just as quick-witted. The first time that I introduced her, he had the biggest grin and a glint in his eye, he was straight in with the smooth chat, but I had warned her and told her to just stand up for herself. She wouldn't bruise his ego.

Anyway, on this particular day, about 5-6 weeks after my Hayley incident, I was out with Gary on a round of golf. The normal course of conversation was a bit of business chat, a bit of sport talk, then he would review his recent sexual conquests, always in great detail, before asking after Rachel and talking about Hayley. How he'd like to add her to his list of regulars and asking me to bring her on one of our trips, so that he can have some dedicated time with her, which was never going to happen.

On this round, we were sharing a buggy and Gary had got on to the events of the previous weekend, which he had heralded as one of the best in years. He was almost giddy as he started talking. Now, this isn't my story, but I'll repeat what he told me as it does lead in to my situation.

He said, "I was at a birthday bash for my friend, Tom, last Friday night. I've known him since college, I was with him when he first met his wife, Suzy, I've watched their daughter grow up. I know most of his family. Anyway, they had hired out this bar that they like going to, out in the sticks, and I'm there, doing the usual, moving around chatting to people, keeping my eyes open, if you know what I mean." I did know! "And I get this tap on the shoulder, it's Tom's daughter, Becky. Now, I've not seen Becky for a few years, she was away at college and done some travelling, but here she is, and she has turned in to this super hot 21 year old red head with a banging body. I couldn't believe it!"

I looked across at him, driving the golf cart, suspecting what he was about to tell me, "You didn't?" I said, but he ignored the question and carried on.

Gary - "So, we're chatting away, and she has really matured, she's really open and confident, and I'm totally forgetting that I've known her since she was born. I'm just seeing this fit 21-year-old, and I'm giving her compliments about the way she has grown up, how she looks in her dress, I even dropped a line about how she reminded me of one of my first girlfriends, who was sexy as hell."

Gary - "Well, Becky is coming back at me with compliments about how I look for my age, touching my arm, hand on the chest, that sort of stuff, and she had the twinkle in her eye. Now I know the signs and I knew I was on to a sure thing, so I tell her that I need to step outside for a while, and sure enough, 30 seconds later, she walks out after me, takes me by the hand and leads me in to the car park." He's grinning like a Cheshire Cat.

I repeated, "Gary, you didn't, your best friend's daughter?"

Gary - "I fucking did!" he said. The story was stopping and starting, as we played golf shots, at which, as was usual, he was beating me. He continued, "She took the lead man, she dragged me to the far side of the car park, to a pickup truck with an open flatbed. She said it'll do fine, that it was her uncles. I still wasn't sure how far she would go, so tested her. I pointed out that he dress would get dirty in there, and that would be a giveaway when she went back inside, and fuck me Dave, she never hesitated. The dress came off over her head and she hung in on the door mirror, the panties were straight off, no bra, so she was stood there naked, but left her heels on. It was an orgasmic sight! She had a knockout body and, although the light wasn't great, I could see that she was shaved smooth, just how I like my women."

I looked at him, all I could say was "Jesus."

Gary - "Then she puts one foot on the rear wheel and hauls herself in to the truck, totally naked, ass in to my face, turned around and said, 'You coming?' I told her, I will be soon. She told me not to worry, she is on the contraceptive pill since her steady boyfriend in college. So I jumped in, dropped my jeans to my ankles and went straight at it. She was already sopping wet, but tight as anything. I remember thinking, with how tight she was, that her college boyfriend either didn't take advantage of her very often, or was one of those small dicked guys."

Gary - "She obviously hadn't had a cock as big as mine inside her, she just shouted 'Jesus fucking Christ' when I rammed it home, she was moaning and wailing the whole time. At one point, I put my hand over her mouth in case someone stepped outside and heard her. Christ, they could have probably heard her while stood at the fucking bar. So, I'm there pounding away for about 15 minutes, she must have cum 3 or 4 times, she was shaking and almost passed out at one point. She was soaking wet as well, so you could hear my cock splashing in to her. It was awesome. I added more wet when I came, I warned her, and she told me to cum deep inside her, so I did. We lay and got our breath back, and I was just thinking, wow, I've just fucked little Becky, and she's a fucking animal."

As usual, Gary's story was full of detail and was getting me a little excited. I said, "Wow, Gary, I can see why that was such a great weekend." But he said, "No, it gets better, much better." We had pulled up at the next tee, so got out of the cart and played our shots.

As we got back in, Gary started talking again, "I had jumped out of the truck and lifted her down, her legs were all over the place. She said to me, 'That was fucking awesome, I've never been fucked that well before,' which was obvious, so I just said that we might get to do it again some time, and she started begging me, (he mimicked in a high pitch voice), 'Oh god, Gary please, anytime, I'll send you my number, text me anytime you want me, and I'm yours.' So that's another regular available, and this one's, young, hot, tight and with the added twist that she used to call me Uncle Gary!" He laughed, but I thought that made it a bit creepy.

Gary - "I left her by the truck trying to wipe all the juices that were falling out of her pussy. She was using her panties, so I know that she couldn't put them back on. She probably dumped them in a bush. She was going to follow me in, but as I got to the bar door Suzy, Becky's mom, comes out, grabbed my hand and started dragging me toward the side of the bar, where there is a little picnic area. She said, I've been looking for you, come on, I need it!"

"Need what?" I asked, suspecting I knew the answer.

"My cock." He laughed, I first fucked Suzy just before her and Tom got married. We'd always had a bit of heat but never did anything, then she asked me to screw her. She said that she needed one last fling, a one off, before she got married. She'd noticed my cock, in my shorts, one time at the beach, and she had to try it before she settled down. Who was I to deny her?"

Gary - "A couple of years later, there was a group of us on a ski trip. I'd hurt my knee so had to have a day off. Tom, my then wife and the others went out, but Suzy was not skiing that week, she had come along but had not long had little baby Becky so was looking after her in the chalet all week. So, mid-morning, she puts Becky down for a nap and walks back out of the bedroom totally naked. She said,' Fuck me Gary, I need that cock of yours,' She'd always told herslef that she wouldn't cheat, but realised that she needed a real cock now and then. Turns out Toms is only about 6 inches and not very thick, she said it does her fine, but her need for a real fuck had been building up."

Gary - "So I fuck her all ways for a couple of hours, which wasn't easy with my knee, and have been her casual call ever since. Probably about a dozen times in the 20 years. Apparently I'm the only one she does it with, I'm enough to satisfy her needs. The last couple of times, though, she was saying she wanted me more. Her sex drive was going up with her age, and Tom wasn't cutting it. Anyway, she's keeps herself fit and is quite a looker, so I'm happy to oblige.

Gar - "Then, as we get to the corner of the bar, I looked back across the car park and Becky is standing there watching her mother drag me away. She must have known what was happening"

"No...., mother and daughter? That's a fantasy come true." I said.

Gary - "Well, I'd already collected the set when I fucked Becky as I'd already done Suzy, but in the same night is even better. Obviously I just dumped my load so still needed to be seen how long it would take before I could go again. Suzy dragged me to a dark corner and pushed me against a wall, she sat down on a bench next to it so that she was level with my cock and undid my jeans and pulled it out, saying she had missed it and was overdue a proper fuck, but then she stopped. She said 'Your cock is soaking wet,' she sniffed it, 'have you just been fucking someone?' I told her that I had, then she asked, 'from the party? Who? I know most of the women here, who was it?'"

Gary - "I was in a playful mood but wasn't about to reveal that my cock had just been buried in her own daughter, she might have stopped, so I told her to lick it, and asked her what she tasted like?"

I was a little shocked, "She didn't, did she?"

Gary - "Yes she did, and she said that she tasted great. She again asked me who it was, she was sucking more and more of my cock in and moaning, saying she needed to know who this woman was, she tasted unbelievable, and she might have to taste it at the source. That made me laugh, so I told her to clean all the juices off and get me fully hard, and I'll tell her more. She went to work on me, sucking and licking, pumping the base of my cock that couldn't fit in her mouth."

The story was getting me horny, I couldn't believe the balls on him, literal and figurative. I also noted that he'd said his cock filled Suzy's mouth and still had enough to be pumped. It certainly sounded like he put me in the shade.

He carried on, "While I watched her bobbing on my cock, I thought about the situation, a hot mother and daughter combo who both wanted to fuck me, and a small cocked husband, who Suzy had once revealed a secret about. It gave me an idea. I asked her to confirm what she had told me that time. She'd said that she thought that Tom suspected she screwed someone else occasionally, and that she thought she would get away with it anyway, if he found out. That was because, while drunk, he had admitted that he fantasized about her humiliating him by screwing other men."

Gary - "I asked if I'd remebered that right. She stopped sucking and told me that he had told her a load of times, he wanted to be emasculated, it was always when drunk and they were talking sex, but never discussed it while sober."

Gary - "My cock was hard again by now, and she looked up and told me it was ready and asked me to fuck her now. I told her no, I had a better idea. She wanted to know who I had fucked, and I would only tell her if she completed a task. She was interested, so I told her I wanted her to suck me to completion within 10 minutes, then walk in to the bar with my cum still in her mouth and snowball her husband. She was like, 'what, in there, spit your cum in his mouth, in front of everyone. No way!' I reached up her skirt and started rubbing her pussy to get her mind back on sex and said, 'look, most of them are drunk and won't take any notice of what you are doing, if you're discreet. Plus you'll get to find who the mystery woman is, and you will fulfill Tom's humiliation fantasies on his birthday. Think what a turn on it will be, for both of you! Plus, if you do it, I promise to meet up soon and fuck you stupid. If you refuse, that's fine, I'll head in now, and you'll never have me again. I was rubbing her pussy quickly now."

I asked him, "What did she say?"

Gary - "She thought about it for a few seconds, but I could tell that her will was bending, she made me promise that I would fuck her properly, soon, then she pushed me back upright and started on my cock like a demon. She was rubbing herself off now with her other hand. I'd come up with the idea, partly from what she had said and partly because, I had suspected Tom of being a submissive guy, the way he did everything she told him, and he never took the lead in any talk of sex or fooling around when we were younger. I wondered in the past, if he was one of those cuckold guys, that had come back to me tonight, and this was the chance to find out."

Gary - "It was an opportunity, out of nowhere, to put a theory to the test, and get some benefit myself. I never thought she would go for it. She'd had a few to drink, mind. Anyway, she was going for it and got me off, but she missed the 10-minute deadline by about a minute. I let that slide as I was now keen to see what happened next. I told her that I was about to cum and to catch it all, which she did. She opened up and showed me, and it was quite a load considering I had already filled up Becky. So, I pulled her to her feet and started rubbing her pussy again, she started moaning, she was horny as hell. I told her not to lose a drop and that she had to go through with it now, she was committed and there were loads of upsides, and that she should give me two minutes to get inside and find Tom. I'd make sure he was in a quiet spot for her, and then I could witness it. She nodded, so I headed in."

I was due to take my next shot but had lost concentration on golf, I wanted to know what happened, "And?"

Gary - "I went in and found Tom, talking to someone. I told him that he needed to come and sit down, Suzy was coming with a surprise for him. He just said, 'oh, I wondered where she was' and came with me. I never intended to take him to a quiet spot, I sat him next to the table with his parents and sisters, plus Becky, who was giving me a hard stare. I just winked at her."

"The family table? You evil bastard!" I laughed.

Gary - "Yep, by the time Suzy came in and saw where he was sat, he'd seen her, so couldn't turn round. She broke step for a second and I wondered if she was going to bottle it, but she walked over to Tom, smiling but obviously closed lips and sat on his lap, with her back to the family. She went in for the kiss, which Tom returned but obviously was hesitant about an open mouth kiss in front of his family, but she persisted, and he opened his mouth. I was watching, and his eyes opened wide as he realized that she was pushing something in to his mouth, but he wouldn't have known what. When she had passed it all across, Suzy pulled back and grinned at him, he sat there with his mouth clenched shut. Then she was brilliant."

Gary - "She said, Happy Birthday, Honey, my gift is something that you always said that you wanted. Tom was looking a bit puzzled and still obviously holding it all in his mouth, then his mom called across asking what the surprise was. Suzy said 'I'll sort the details out with Tom later, but I'm getting more help around the house, I might have a new gardener, or a handyman, or a pool boy. Whoever it is, Tom will reap the benefit.' I don't think anyone picked up the subtle comment that 'she would have', but I think Tom was starting to get the gist and might be working out what was in his mouth. Becky was looking at him as well and his tightly shut mouth."