My Mom's Best Friend by Martin

[kums]

Where do I start? This happened way back in 1987, I at the time I was a 19 year old with a high sex drive and reading more Playboy than actually getting laid. My mom's friend Gail, a 39-year-old sexy divorced woman with wild blonde hair and a big set of tits. Gail's nickname was Dolly because she had real long nails and always wore low cut tops showing off her big tits like Dolly Parton. She slightly resembled Dolly but I always called her Aunt Gail while growing up. Gail was wild and carefree and everyone loved her. She would always secretly flirt with me, as I got older especially when I turned 18. At 19 I was a big kid at an even 6 ft tall and possessed a near nine-inch cock, which I still pack today lol.

Unfortunately at the time I turned 19 I hadn't had a girlfriend in almost a year so there was plenty of jerking off going on. My parents were divorced as well and Gail was over almost every weekend drinking and playing cards with my mom. Sometimes they would go out to a bar. Gail always asked me when I was going to have a few drinks with her and not being able to get in bars I told her she'd have to wait a couple of years. I noticed how since I had turned 19 she would flirt with me even more than before, getting more physical like pinching my butt or sometimes putting her hand up my shirt and scratching my back with those long nails which drove me nuts. She'd massage my shoulders sometimes and always kissed me on the lips to greet me where as before it was on the cheek.

One weekend my mom had to take a short trip to Wisconsin for her job and I had plans so my mom asked Gail if she could watch my sister who was 11 at the time. It was just for Friday night and Gail asked me to cancel my plans and hang out with her. I found this a strange request at the time but she talked me into it. I was only going to a friend's party but the thought of spending time with Gail seemed like a good idea. She seemed real happy when I told her I'd hang out with her. I figured if my sis mentioned anything to my mom I'd just say I didn't feel good and came home early. I had to leave the house until my mom left and Gail was coming over at 7pm.

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My mom was leaving then, it was only a short drive to where she was going. I went and hung out at the record store until about 8 and then went back home. Gail greeted me with a big hug and was in a damn pair of silk pajamas, I remember they were pink and the top was unbuttoned showing her cleavage. She was playing a game with my sis and they were having a good time. Gail told me she was spending the night, which I didn't even know about. I took a shower and went to my room and listened to music and went back downstairs around 10. Gail was getting ready to put my sis to bed. It was around 10:30 when my sis finally went to bed and Gail seemed happy that we were alone. She went and poured herself some wine and asked if I wanted any, I preferred a beer so she brought me one in the living room. Before you know it, it was almost 12:30 and I had put down 5 beers and Gail a few large glasses of wine. That's when she moved over and sat real close to me on the couch.

I just had some jogging shorts on and a t shirt, no underwear and Gail was talking to me real close making my cock start to get hard. She had her arm around me and told me how sexy I had become and all sorts of other drunken nonsense. I noticed somewhere along the way her top was now unbuttoned almost all the way, she obviously did it when I wasn't looking. I could see most of her tits and they were big. My cock was now getting very hard. Gail had her hand on my chest and glanced down at the bulge in my shorts. As she whispered in my ear she moved her hand to my cock. She rubbed it through my shorts and started licking my ear. That's when I turned to kiss her and our tongues met for the first time. We kissed as she gave my cock a good massage and I put my hand on her tits. Man they were big and soft.

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I took her top off all the way and began sucking them. I licked her nipples and squeezed them and she released my cock from my shorts. I slid them off and my full 9 inches was hard as a rock and standing straight up. Gail moved down instantly to my lap and sucked and licked it very eagerly. One thing when I was younger, when I drank I could stay hard for a long time. Seeing those long nails wrapped around my cock while watching it disappear between her painted lips was a real sight. She slipped out of her pajama bottoms and got on top of me so we were in a 69 position. Her pussy was shaved almost completely with just a little strip of hair above her lips. I lapped at her loose cunt lips like a starving animal.

When I think about it now, she had probably had fucked several men. She had some big pussy lips that hung down. I gave her a good tongue fucking until she came. Her pussy got really wet and creamy and being young and eager I tried lapping it all down. She flipped around and sat on my cock and started riding me on the couch. I prayed my sis wouldn't walk in, we were lost in the heat of the moment. I didn't last long in her pussy and came so hard I thought I was going to pass out. She milked me for every drop and then dismounted me and cleaned my cock with her mouth.

She kept right on sucking for another five minutes until I was rock hard again. She told me to fuck her again and she got on the couch on her hands and knees. I grabbed her hips and put my cock between those huge pussy lips and fucked her hard for a good ten minutes. I came hard again deep in her pussy. A little later I went to my room and Gail came in and spent another hour with me in there and I ended up eating her cunt for a good half hour and then fucked her again filling her pussy with another load of cum, although this one was not as powerful, I was tanked out.

I really got an education that night and throughout the next 3 years I must have fucked Gail another 70 or 80 times and even got to pound her asshole a few dozen times. I see her now and then and as she gets close to 60 she still looks damn good although now being married all we can do is talk about "the good old days"

[kums]

Back in the late 90's, I was in my late teens. I was a fairly attractive athletic guy who was fairly intelligent for my age. I had met and moved in with a woman who was in her mid 40's. Your connection was purely sexual. She had been married previously, divorced, dated and was single once again. She was what you would call a biker chick. She was a natural redhead, petite and had small A or B tits. She wore leather and fit the part perfectly. She was loud in bed and had an appitite for cum. You could fuck her twice a day and she'd still be ready for more.

As a young single guy, my goals were quite simple, I wanted to fuck women. I didn't try to hide it either. From the begining, I made it very clear that my intent was purely sexual. By not hiding behind the false lies of love and romance, this left me free to experiment and be myself.

After a few months of meeting up randomly, I decided it would be a good change to live away from home and made arrangements to live with her in her apartment.

The best part about being with an older woman is the experience you pick up. You can keep the shy, young girls as far as I'm concerned. They may be nicer to look at, but that is about it. She'd worship my feet, sucking my toes until moving on to giving a rimjob and massaging my prostate while sucking me off nearly every night if I was up for it. She was also pretty demanding though. I'd wake up with her rubbing her cunt in my face. She'd make a joke and say something like, "Rents due."

[kums]

I didn't mind at all. That is what I was there for. I love eating pussy. At that age, I was always wanting to push my experience further. So while 69'ing, I was watching her light brown asshole winking at be as I ran my tongue over her clit. I figured what the hell, and started running my tongue over her asshole. She seemed pretty receptive of it. She would make noises and wiggle her hips a bit. I decided to make it apart of my pussy eating skill set.

As the weeks went by, she became more verbal about it. I'd be watching TV, and she would approach in her underwear and say, "How about you come lick my asshole while I fuck this dildo?"

I didn't turn her down. During fucking sessions, I began rubbing her asshole with my thumb. She was receptive of it, and I started putting my thumb in her ass when fucking her doggy style. She seemed to really like it. It made her more vocal when cumming.

Finally, I had been awake most of the night. She had slept because she was going to work that morning. It was summer time and already getting light out around 5am. I was at desk in her room. Since it was warm, her covers were thrown off and her ass was exposed. I thought to myself, "How hot would that be to butt-fuck her?" I set out in an attempt to make it happen.

[kums]

I crawled into the bed behind her and started fingering her slit. After a few minutes, she rolled onto her back partially awake. I started licking her clit. She naturally spread her legs and made some receptive noises. After a few minutes of licking her, I told her to roll over. She complied. I spread her ass cheeks and began licking her tail bone and traced my tongue down the crack of her ass over her asshole. I slid my tongue in her pussy and pressed my nose against her asshole. After a few minutes, she told me, "Fuck me," in a low sexy voice.

I slid my cock easily into her wet cunt and started pumping her from behind slowly. She reached beneath herself and was playing with her clit. As usual, I pushed my thumb slowly into her asshole. I pushed in past the outer ring and all the way to the last knuckle. Pressing downward, I could feel my cock sliding in and out of her cunt through the thin skin.

I finally got up the courage to say, "Lets do something different."

She looked back at me sexily and said, "Whatcha got in mind?"

"You ever been fucked in the ass before?" I asked casually. I flexed my thumb still buried in her shitter.

"Oh, no. I tried once, but had to stop," she said a little surprised.

I asked, "What was the problem?"

"My ass was too tight," she responded.

I said confidently, "Well, get ready to try again." I felt her asshole clench down on my thumb.

Nervously, she said, " Ok, but you have to go really slow, and we might have to stop."
"Deal," I said.

[kums]

I pulled my cock And thumb from her body and let her get up on her knees. She then put a large pillow under her chest to lay on. She then asked if I wanted a condom because it might be dirty. I bent down and stuck my tongue in her asshole, and asked, "You think I'm worried about it?"

I slid my cock back into her cunt and pumped her for a few minutes while I poured KY on her ass. I rubbed it into her asshole with my thumb.

I pulled my 6 and a half inch thick, cut cock out of her and rubbed more KY on my it. I pushed the head of my cock against her asshole. I spread her ass cheeks with my hands while guiding my cock with my thumbs. I had the perfect view.
She reiterated, "Go slow and easy," nervously.

It took several tries to get the head to start penetrating her. As soon as it slipped past her anal ring, she started breathing hard and deep. Her hand reached back and pressed against my hip to act as a non verbal cue on how to proceed. Her other hand rubbed her clit rabidly. I spread her asshole with my thumbs trying to stretch her little asshole. We sat there for about 4 minutes not moving. Finally she said, "A little more."

There was significant resistance to get my cock to slip in deeper. Most pushing simply pushed her entire ass in. Like the tin man, I kept applying drops of KY on the shaft of my cock hoping some would run in. I figured she would need some verbal stimuli to keep her mood up. I asked her, "A year ago, would you ever had expected that you'd be getting fucked in the ass by a man more than half your age?"

[kums]

She moaned deeply, and said, "No, how about you?"

"Me? Think that I'd have my cock in a womans ass who is older than my mother? Never," I said smiling.

She moaned and said, "More..."

I pushed my cock in about half way. I pulled back so only the head was in her and pushed back in half way. "OH SHIT!" she said loudly.

"What?" I asked concerned.

"That's intense..." she explained.

"You like hard young cock up your ass?" I questioned.

"More..." she said firmly.

I pulled out again so only the head remained and pushed it slowly back in about 3/4 of the way in. "OH god..." she pleaded through the moans. "It hurts, but I don't care," she explained short of breath.

I pumped her again, her reaction was similar. She said, "It's OK, give me all of it."

I asked her, "You want my cock in your ass?" She moaned, "Uh huuuu..."

I pulled out and pushed all the way in slowly. I was grinding my pubic hair against her spread ass. "OH MY GOD!" she moaned loudly. I put my hands on her hips and clawed into her sides.

I told her, "You've got a nice tight asshole [her name deleted]."

She moaned deeply and said, "Fuck me up the ass, baby."

[kums]

I pumped her ass slowly for 15 minutes. I'd slow down before I would cum in order to make it last. I made comments to her while pumping her like, "Every man you have ever fucked wished he was doing this to you." "You're going to have to go to work today will a colon full of my cum." "Your ass is going to be sore for days, and you'll know I'm the one who did it to you." "You're going to remember this for the rest of your life."

She was into woman power and feminism, so I figured I'd use that on her as well. "You like the idea of a man using your body for his own pleasure?" I asked her.

"Using me? You'd stop if I asked," she stated while getting pumped.

I laid against her and spoke into her ear, "Maybe I wouldn't. Maybe I'd hold you down and pump your ass until I'm finished with you." her body went limp under me. I pressed her against her pillow and stroked her ass hard. She yelled, "OH MY GOD, IM GOING TO CUM!!! FUCK ME IN THE ASS [my name deleted]!!!"

I pounded her shit pipe as hard as I could. I felt her hips rise up off the bed slowly. Finally she broke loose and started bucking as she came. Her asshole clenched down tight. She squeezed my cock so tight it hurt. I kept pumping her anyway. The exitement and the tightness were too much to contain. I told her, "I'm going to cum in your ass."

She said, "Pump it in me!"

I broke loose and buried my cock in her ass as I started to cum. It felt like the most I had ever came. I could feel wave after wave of cum squirting up her ass. I laid on top of her with my cock buried in her ass for a few minutes. I told her, "Time for you to go to work, whore."

[kums]

I pulled my cock slowly from her ass. Her asshole remained open as a trickle of jizz leaked out. She staggered to her feet and waddled into the bathroom to start the shower. As we got in, I rinsed my still rock hard cock off in the warm water. She dropped to her knees and started sucking and kissing my cock quietly. Almost what I would call cock worshipping.

"Off to work for you with a colon full of jizz," I told her as we getting out.

It was time for bed for me. I saw her out the door. She had a dazed look in her eyes. I told her, "Think about what I did to you all day."

After she left, I went to bed quite pleased with myself.

When she returned home, she started bitching about how much her ass hurt.

I said, "Let me see your ass."

she pulled her pants and underwear down and bent over. Her asshole was puckered, red and still open a bit. I said with a sly smile, "Looks like you got fucked in the ass."
"No shit," she said sarcasticly.

I asked her, "So, when do you want to do it again?"

She said, "As soon as I heal up!"

[kums]

Bob had been my best friend ever since I could remember. Since we were little kids, I spent almost every school holiday over at his place. Being the only child in our families, we were like brothers to each other. Furthermore, our parents were close family friends so my Mum would just leave me Bob's place for days at a go without the least of worries.

Now Bob lived in a huge mansion in the middle of a plantation, coz his father was managing the place for a large international corporation, and as one the benefits, his family gets to stay in that mansion as long as he works for them. The place was surrounded by acres and acres of greenery so it was very peaceful and no one ever drives by. However, Bob's father was very busy and always travelling around, so I saw very little of him. His Mum on the other hand, was a full-time housewife and rarely left the house. Aunt Serene was a lovely, gentle lady with a very kind heart; she saw to everything in the house including the cooking, laundry and the overall household chores. But being the wife of a rich plantation manager also meant that she could afford the best-looking clothes and beauty products available! Aunt Serene always looked her best no matter what she was doing, be it during dinner, dipping in the pool, or even while vacuuming the living room! When I was there during the holidays, she'd make sure both Bob and I had awesome snacks to eat, various activities to do and even gives us hugs and goodnight kisses before bedtime! And every time we played in the pool, she'd make sure to apply sunblock lotion for us and stayed in the pool with us to make sure nothing goes wrong. As a result, I really liked Aunt Serene even from a very tender age. However, one incident made me very strongly attracted to her in a very different sort of way.

One day, after we had enough fun in the pool, Aunt Serene told us that she had prepared an extra special local snack for teabreak, and asked us to go shower before enjoying it. Both of us were excited (and very hungry, to be honest) so we dashed from the poolside all the way to her bedroom bathroom for our shower. We usually took our showers there because it was the only bathroom that could fit the two of us at the same time. Being the little boys that we were, we yanked down our trunks to the floor and had a quick shower, each boy trying to be faster than the other. As usual, Bob finished first, dressed up and again dashed to the kitchen towards the awaiting snacks. I followed closely behind but before I could get to the table, I remembered that I had left my trunks on the bathroom floor! Mum always said that it is rude to leave clothes strewn around, so I let out a long sigh and ran back up the stairs, hoping that Bob would not finish my share!

As I approached the bedroom, I noticed that the door was closed. However, In my eagerness, I forgot to knock and opened the door to enter. The room was empty as we had left it, but there was the sound of running water. "Damn it! I must have forgotten to turn off the shower!!" I thought. So I walked towards the open entrance of the bathroom and as I neared it, I saw a sight that I would never forget. Aunt Serene was standing in the shower, back facing me, without the shower curtains closed, and more significantly, without any clothes on!! I mean, I was used to seeing her in the pool with only a bikini on, but in the nude?!! It was definitely a first for me!! Aunt Serene always took good care of her figure and oh how it had paid off! I just stood there staring, unable to move or speak!! She continued washing herself and humming a tune at the same time. Then she turned a little to her left to get some shower foam. And that was when she saw me!! I was dead meat!! I knew it!!

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But to my surprise, Aunt Serene didn't freak out or scream at me like I had expected! Instead, she calmly and gracefully placed her left arm over her breasts to cover them while turning to face me, although that movement also caused a cleavage to form, enhancing her already full bosom! "Looking for this?" she said with a slight smile, picking up my trunks and holding them out in my direction with her right hand. "Er... yeah..." I said shyly, slowly inching forward to retrieve the piece of swimwear. As soon as I got hold of it, I muttered a quick 'thank you' and sped out of there!

From that day onwards, I started to look at Aunt Serene's attractive body in a new light, as if I have never noticed it at all before! Whenever she walked past me, I would steal a glance at her buttocks. Whenever she bend down while going the housework, I would hope to catch a glimpse of her cleavage. But nothing realy happened, and I continued to spend my holidays at Bob's place over the years.

But in life, nothing remains forever. In my case, Bob had to move abroad as his father was transfered to another country to take care of a new plantation. I never saw Bob or Aunt Serene for several years, although we kept in touch by telephone or mail. Slowly, those phone calls and mails grew less and less...... I finished my studies, got a job in another city, and had a life of my own.

Then one night, I received an unexpected call - it was Bob!! I was elated and we chatted on the phone for hours!! There was just so much to catch up on! And I was even happier when he told me they were coming back for good!! He went on to say he wanted to introduce his new girlfriend to me and that we could all hang out together, just like old times! He said that he and his girlfriend would be coming back first with Aunt Serene, as his father had to settle some matters and would only joined them later. I took note of when theyd be arriving and immediately applied for leave just so I could be back in my hometown to meet him after so many years!

After a few weeks, the day was finally here!! I had told Bob that I'd drive over to his old place to spend some time with him and also get him back to speed on how much has changed since he left. I was really excited on my way there and my mind was just going wild over the things we'd do during my stay there! It's be just like old times indeed!

I pulled into the large parking lot and got my stuff out. The place looked pretty much the same as I remembered it - peaceful and serene with lots of flower beds in front, and the pool by the side. As I got to the door, I rang the doorbell and waited with my heart beating like crazy! Gosh was I excited, like a little boy again! After a few moments, the door opened and in the doorway was a familiar, gently face. It was Aunt Serene!! It was as if she didn't age a day! In fact, she looked slimmer and more shapely than before! But her lovely, warm smile remained the same, and she spread her arms to give me a welcome hug.

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"Oh my goodness how you have grown!! You're a fine young man now! And you're so tall!"

"And you look even more beautiful than before, Aunt Serene!"

"Oooh, you flatter this old lady....... but I like that nonetheless!!" and we both burst into laughter.

"Come on in and have a seat!" she said and led me into the living room to sit on on the sofa. Aunt Serene was wearing a dark blue dress with a rather low neckline. I couldn't help but notice that right away!

"So.... where's Bob at? Is he sleeping again?" I asked, since he was nowhere to be seen.

"Well, about that...... I have some bad news to tell you. You see, just a day before we were to fly back here, Bob's girlfriend Katie met an accident and had to be hospitalised. Bob wanted to stay by her side while she was admitted so he asked me to come over first. He said he was really sorry and will call to apologize soon. In fact, let me just give him a ring to tell him you're here."

Aunt Serene got through to Bob and then passed the receiver to me. Bob said he felt really bad but he had to accompany Katie. He promised that he'd be here in a few days, as soon as Katie was discharged. Anyway, I felt relieved to hear that it wasn't anything serious and she should recover in about a week.

"I hope you won't mind staying here while waiting for Bob"

"Of course not! I bet you need all the help you can get unpacking your stuff anyway!"

"Yeap, but that can wait till tomorrow. You must be tired after the long drive here. Why don't you go up to my bathroom and freshen up? Oooh, and then you can come join me in the pool!!" Aunt Serene chirped.

Her bathroom? I started to feel turned on already!

I took my stuff upstairs and changed to my board shorts and went outside to the pool. Aunt Serene was already in her bikini, applying sunblock lotion on herself. She wore a white bikini top with small yellow flowers on it, and a matching bottom. I must admit she didn't change a bit! In fact, I think she had an even better figure than before! She had a tanned complexion, firm buttocks and a very full bosom. Her bikini top was obviously straining to contain her heavy assets!

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"There you are! Could you be a dear and help me apply some lotion on my back, please?"

I jumped at the opportunity and began touch her smooth skin, being as gentle as I could, enjoying every moment, occasionally peeking over her shoulder to glimpse at her breasts. The view was amazing from where I was seated, I must say!! Aunt Serene then helped apply sunblock on my body, caressing my chest, arms, back and even my thighs. I prayed that she didn't notice that growing lump at my crotch area! If she indeed saw it, she certainly didn't show any sign of it!

Then she led me into the pool and we swam and frolicked about, chatted about my life, as well as her life overseas. She kept quite close to me in the pool, occasionally putting her arms around me, and showering me with attention. However, during our conversation, she did mentioned that she found out her husband has been having an affair, and that because of that, they haven't been on talking terms. They slept on the same bed, sure, but they might as well be on different continents. She was just holding on for the sake of Bob. I listened to her and comforted her in every way I could. After a while, she felt better and we changed to happier topics such as my first crush in school and stuff.

Hours went by and soon, the sky started to turn orange. Aunt Serene got out of the pool and dried herself.

"I'll go upstairs to have my shower first, then make dinner. You can stay here a while longer, or you can go watch TV in the living room." she said.

I nodded and watched her walk back into the house, a devious thought forming in my mind. Would history repeat itself? Would I get to see her in the shower again! I wanted so much to see her naked. No, in fact, I HAD to see her naked again!

[kums]

So after a few minutes of pondering, I nervously made my way upstairs to the master bedroom still in my swimwear and a towel draped around my neck. I could hear the sound of running water as I got closer. The door wasn't closed! I tiptoed silently into the bedroom, and just like that fateful day those years before, the bathroom door was left open!! And beyond the door was the most amazing sight!! Standing under the shower was Aunt Serene, back facing me, without a single piece of clothing on!! The bikini she was wearing a while ago ended up as just a small pile on the bathroom floor.

Water was flowing down her smooth back, her perky buttocks, thighs and calves. Her arms were held up as her hands were running through her short hair. If only she would turn around to show me the rest of her gorgeous body. And after a while, she did just that! Well, not to show me her body, of course, but it seems she was about to reach for the shower cream when she realised I was standing behind her! And just like before, instead of reacting in shock, Aunt Serene just gracefull lifted her left arm across her chest to cover her breasts.

"Oh, you're up early! I thought you'd spend some more time at the pool" she said calmly. I'll still need some time in the shower. You can wait in my room if you want...."

"Ah, I'm so sorry to interrupt, I thought you were done so I came in to have my shower. Sorry for not knocking when I came in," I lied nervously.

"That's all right, sweetheart. You know.....actually, since you're up here already..... why don't you come join me?", and as she said this, she lowered her slender arm which was not doing such a good job in covering her huge bosom anyway.

I could not believe what I just heard. And I could not believe what my eyes were seeing! Aunt Serene was now standing naked in front of me, with her big, heavy, breasts in full view! She had very nice nipples and light pinkish areolas. And now that they have no support whatsoever, they was a little drooped, but most probably due to their sheer weight than because of Aunt Serene's age. Oh my god, her breasts were more beautiful and bigger than I had imagined! My jaw must have reached the bedroom floor!