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fatblackanduglyasever Member Since October 19, 2009

Caddy gets a loop

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Caddy's player stiffs him...sorta

I got out to the driving range and started to look for the starter to find out who my loop was going to be for the day. Once i spotted the starter I walked over to him and asked him who i was going to be caddying for that day. He informed me that I had a couple named the Davis's. I knew about them they were a relatively good group to caddy for as long as they weren't having marital problems. If they were fighting they seemed to take it out on everyone and everything around them. Mrs. Davis was at the driving range already practicing her mid-irons, although not being very successful. She was probably in her early 40's but kept herself in great shape and always wore proper golf attire. Today she had on a snug fairly low cut Burberry collared shirt w

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hich appeared to fit fairly snug over the upper half of her frame giving me a great view of what seemed to be a fabulous set of tits. To go with her top she wore a skirt that went just barely down to her knees and as she bent down to place another ball on the tee i noticed she was wearing a thong underneath her skirt. I greeted her and asked her how she was doing, she responded by saying fine. She informed me that her husband was going to be late. I then informed her that our tee time was in 5 minutes and since the course was busy we had better get out there now and that her husband could meet us out there when he arrived. We hopped into the golf cart and drove to the first tee. Now since she wasn't a very good golfer Mrs. Davis asked me to set her up on the tee box. As she stood over the ball i also noticed that her form wasn't very good. Instinctively i asked her if i may step behind her and give her a few pointers. I got behind her and adjusted her stance, grip, etc. However when i adjusted her stance she overadjusted and backed herself right into my groin. She just laughed politely and asked if this looked any better. Needless to say i informed her that she looked perfect. Once she hit the ball we hopped into the cart and started driving out to the fairway. I couldn't help but glance at her creamy legs as we rode in the cart, however making sure she didnt see me. We got about three holes in when her phone rang. She answered it and from the way the conversation went it sounded as if her husband wasn't going to make it. Just as i thought when she got off the phone she informed me that her husband was delayed at an airport and wouldnt be home until the next morning. Once we fnished with the front 9 i asked her if she wanted to keep going. She thought about it but decided that nine holes was enough however asked me if i would give her some putting lessons. We got over to the practice green and i stood behind her this time putting my hands directly on her waist and digging my pelvis into her body i took control of her body to position her properly. At this point my dick was forming a semi and i could tell she noticed, and i thought i felt her nudging herself into me ever so slightly. So it was at this point i decided to take a chance that would either get me fired or give me a great story and a great tip. I asked her if she wanted to come back to my place and discuss golf tips over a glass of wine. She laughed and informed me that she was old enough to be my mother but that she could use the golf advice. I told her to meet me at my place around 7 p.m. and gave her my address and number. Later that night i heard a knock at my door and it was her. I opened the door and she looked amazing. She was wearing a red blouse that showed off her ample chest and also her great legs. Her shoes were sexy as hell to as she wore 5 inch red pumps. I invited her in and showed her to the living room. We got to talking about golf which quickly turned into me listening about her husband and how he was never home. I don't know if it was bravery or the wine kicking in but i blurted out, "If i was married to a women like you i would try and be home as much as i could." She was defentely taken back by the comment but she started to blush and then said, "Matt i am old enough to be your mother.""Yea but my mother doesn't come over my house and drink wine at 7 at night does she" i responded. We went into the kitchen to get some more wine at this point.She started puring the wine into a glass and i got behind her placed my glass on the counter next to hers while at the same time sticking my already semi hard cock against her dress. Then i dont know what came over me i started messaging her shoulders and when she didnt protest at all i moved my hands over her huge tits. I started rubbing her tits now with both hands and i could hear soft moans coming from her. I pulled the straps down on her dress and pulled the top of it down over her tits. She showed no resistance so i then took her nipples into my hands and started playing with them, much to her delight. At this point i spun her around and started kissing her. She had beautiful lips, very full and i was taking every inch of them in. It was then that i felt a hand tugging at my crotch, and it was time for her to have some fun. She laughed and got on her knees, all i could do was stare at her huge tits while all this was going on. She pulled my pants and boxers down in one motion and my 8 inch cock sprung out. She took it into her mouth and began sucking on it. There was no doubt she was a little whore on the inside, because the way she sucked my cock made me think it was the last cock she was ever gonna suck. I decided to take it a step further and placed my hand behind her head and began fucking her face. She loved every second of it and so did i. I fucked her face, pumping my cock in and out of her mouth giving her only a second here or there for some air. I felt my balls starting to tighten up so i knew i was going to cum soon. I pulled my cock out of her mouth and blew the biggest load i ever had on her face covering her eyes and mouth with my hot sticky cum. She loved all of it and began licking off her own face. After she cleaned my cock off she stood up and we started kissing again, this time i picked her up by her ass and pinned her up against the wall. I pulled the rest of her dress off and turned her around. I got down on my knees and started rubbing her unbelievable ass. I pulled her thong down exposing a beautiful pink pussy. She was already soaken wet from the previous events, but i wanted to taste her. I started licking her pussy ever so slowly while searching for her clitoris. Once i found that i start playing with that which sent her over the top and she started having violent orgasms. I lapped up all i could then i picked her up and carried her over to the couch. She straddled me and lowered herself down onto my cock. We started kissing again then she started riding my cock like it was going out of style. Her pussy gripped my cock and my cock held on for dear life. She rode my cock for about ten minutes then i took her and bent her over the couch. I took my cock and teased her with it, just rubbing it on her pussy and made her beg me to fuck her. "Fuck me with your cock, im a dirty fucking whore!" she cried out. I took my cock and inserted it into her and started pumping as hard and fast as i could. With every thrust her ass rippled against my thighs, and by the time i was 5 minutes in her ass was so red from me slapping it, that it looked like she had a bad sunburn, but yet she begged me not to stop. I had enough of her pussy so i took my thumb and placed it into her asshole. When i did this she moaned even louder and it was then i decided i was going to bust my nut in her ass. I pulled my cock out ofher pussy and started to insert it into her asshole. It took a few minutes to get the whole thing in but once i did it was amazing. She moaned uncontrolabely ass i fucked her ass while fingering her cunt at the same time. I was close to cumming so i took one last deep thrust, pulled her head back by her hair and shot my hot cum deep into her ass. I pulled my cock out and she cleaned it up once again, not wasting and ounce of my semen. Just then her phone rang and she picked it up, "Oh hi honey. No everything is good im just taking a bath right now getting ready for bed. Another day, well thats okay you have priorities and i understand that, i guess ill just make another tee time for tomorrow then, ok , bye"

Day at the pool

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"Man it's hot out today", I said to my buddy.He shook his head in agreement.
"You know my aunt and uncle have a nice in-ground pool we could probably go in" he said to me.
"Well call them up see if we can go" I responded.

 About twenty minutes later after Jim had called and left a message his aunt called him back saying it would be fine if we went swimming in the pool. We went back to my house so I could grab my trunks then we headed off to cool down.
 When we got there a woman who looked to be in her late forties answered the door, and greeted her nephew, I introduced myself and went inside the house. I couldnt help but notice that although not stunning this woman was pretty hot for an older woman. She was about 5'7" with

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curly blonde hair, but her best features were by far her curves. I mean she had bombs they looked like they were at least d's, and her ass was very round and looked to be fairly firm. Â Â She was wearing a denim tight fitting blouse that went down just below her thighs, while the top showed a decent amount of cleavage. Jim used the bathroom to change and she had told me to go into her room to change as it was right next to the bathroom. When I went into her room I couldn't help but open the top drawer of her dresser and se what I could find. Just as I suspected the first item I found was a black lacey bra upon which the tag read, "38D". I sifted through the drawer looking at her various forms of lingerie and what not.
 Looking at all this sexy underwear had given me a semi, but I thought nothing of it, that is until I walked out of the room and she was standing right there making sure everything was all set. I wasn't sure if she had seen my semi erection but I thought she may have. Jim and I had been in the pool for about 35 minutes, drinking a couple of beers that we had brought when his cell phone rang. It was my other buddy saying they were going to play homerun derby and if he wanted to join. He asked if I wanted to I said not really but he should go play. After making sure I didn't care he got out dried off and had my buddy pick him up, I had said I was gonna go in the jacuzzi they had and then help clean up before I left, but that I would meet him there.
 About fifteen minutes after he left I got out of the pool and was cleaning up the beer bottles when I heard the sliding door open. I turned around and it was his Aunt,Vicky. SHe asked if I had, had a good time and if I was heading out.
 `"Actually since Jim took off i was gonna hit the hot tub up or a few minutes before i headed out, then I'll clean up the rest of this mess", I said
 "Well i was about to go in myself she said but its plenty big for both of us if you dont mind being in it with your friend's aunt?"
 "No it's no problem, I dont care at all", i responded
 So I took the cover off the hot tub and fired it up. I grabbed a couple of beers and hopped in the Jacuzzi. About 5 minutes went by when Vicky came out. Boy, did she look great. She had on a one piece bathing suit but it was very tight, and when she turned to shut the door her ass was sticking out the bottom of it and on top, it made her tits look even bigger than they were. She got in alongside of me and i offered her a beer.
 After about 10 minutes of us talking about everything under the sun, including her husband who was always going to conferences and what not, I decided i was gonna go for it"
 "Geez with all this going on i can't believe your not tense or uptight or anything" i said.
 "Well i am a little bit, i was gonna go to a spa today but since you guys called i figured id just put it off until tomorrow", she responded.
 "Well I'm not an expert or anything but if you wanted i could give your shoulders a nice massage while we are in here that way I don't feel to bad" i said.
 "You don't mind" she replied.
 "No come on, get over here" I barked.
 She slid over in front of me and I started rubbing her shoulders. I didn't know exactly what i was doing but i had a hot older woman in front of me letting me rub her shoulders(while i stared down her suit" and how hard could it be to give a decent massage. I noticed however that halfway through she had started gently rubbing my legs. A lot of thoughts were racing through my head so naturally my cock begin to harden again. I was nervous at first but it seemed everytime my cock hardened the more she seemed to ease herself against me. I took this as a sign and decided to go for it. I took one strap on her suit and pulled it down over her shoulder, while kissing her neck. Seeing no resistance i did the same with the other strap. Now the top of her suit was almost completely off her tits so I just started rubbing the top of her shoulders, moving my hands closer to her tits, until finally my hands were gently massaging her huge tits. She was softly moaning, and had her eyes shut as my hands moved over her nipples and I began to pull softly on them.
 I turned her around and she straddled me, as I began sucking on her tits. They were so big I needed both hands to work one breast. As i did this her hand moved down below my waist and she began tugging my swim trunks down, trying to expose my now fully erect penis. I switched my attentions from her tits to her ass as I bunched up the back of her suit and now had a hand on each ass cheek just squeezing her round ass as we kissed. She urged me to get out of the hot tub and sit on the edge, which I did without protesting. She yanked my trunks down and out popped my 8 1/2 inch full erect cock. She smiled and informed me that her husbands cock was barely half this size, and that was why she had often slept with younger men.
 I took the back of her head and guided it towards my cock. Her lips were very fully and although older she defentely knew how to suck cock. She was going almost all the way down on my cock and was giving a very wet,sloppy blowjob which I like. As i was sitting there with her sucking my cock i reached over and started slapping her ass. She loved this and told me not to stop. I couldn't hold out too long in this situation, and after about 7 or 8 minutes I shot my load all over her tits.
 After this happened she though I was done but this time i informed her to sit on the edge of the hot tub. SHe smiled and complied. I pulled off her bathing suit completely exposing her huge tits completelety and her pussy. She wasn't completely shaven but it was alot better than i had anticipated. I got between her legs and started massaging her pussy and clit with my tongue. I switched my rythym from slow to fast, and fast to slow being sure to be thurough, as I wanted to give her an orgasm beyond belief. She was burying my face into her pussy screaming uncontrollably until finally i felt her shake violently and it was then i tasted her sweet juices. I worked my way back up to her tits and started sucking on them again then i kissed her on the lips and told her now I wanted to fuck her.
 We sat back down in the hot tub and started kissing again and then she straddled me. She grabbed my hard cock and guided into her hot,sticky pussy. Man, did it feel incredible. At first she started off slow, as she rode me I was grabbed her tits and was kissing her all over, then she started to get a little more aggressive. She took my hands and put them on her ass, and she started riding up and down on my cock very hard. After a few minutes of that I bent her over the side of the hot tub and began to fuck her from the back. Sensing she liked it a little rough i grabbed her by the hair and started yanking as i thrust my cock into her waiting pussy. With one hand i pulled her hair, and with the other i was slapping her on the ass. Again i turned her over and now she was on her back half in the hot tub, half out. I was on top of her, and i picked both her legs up bringing them towards her chest, and i began pumping ass hard as i could. I continued to do this for about 10 minutes, after which I shot my load of hot sticky cum deep inside her pussy, as she moaned one last time in absoulte content. We kissed for about 5 minutes as my cock lay inside her, and i groped her tits once again for good measure.
 We got out of the hot tub, walked back inside the house and i took a shower as she cleaned herself up as well. When i got out of the shower i got dressed and walked downstairs when i saw her husband. I thought i was in deep shit but i played it cool, and said hello.
 "You must be Jim's friend" he said
 "Yea, Jim took off earlier, I stayed a little bit later to help your wife clean up around the pool area" i responded.
 He looked at me as if he knew what happened, but what are the chances, i mean i had gone swimming then showered to get the cholrine off, thats all.
 "Well thanks for that, hey anytime you want to come over your welcome to, my wife appreciates the help" he said.
 "Oh, well thankyou" i responded, "maybe i will" i replied as i headed out the door winking at Vicky as I left. I left the house but as i was walking down the driveway i could of sworn i heard, "Hey honey how was your day did everything go well"
 "Yea, Matt was great here today" i heard her say.
 "And did you remember to record it this time?"
 "Of course!"............

could be a part two in the works lemme know if you liked it.ONly my 2nd story so far