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My Boldest Dream Come True

"The hot landlady finally lets me do her."

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Famous Story

I have always loved old women. When I was young all of my friends were into girls more or less their own age. Once in a while, a friend of mine would find a mother hot but nobody was into old women. Only I was. And I mean old, women in their sixties, which was very old for a teenager. My own grandmother was not even that old at the time. I loved Sunday church because I could oogle the old ladies. At home I would fantasize getting bathed by them and spying on them to get a glimpse of their droopy breasts. It was my favorite and pretty much only masturbation fantasy.

In those days which were the early eighties we didn't have the internet and we could not search for porn. My friends had porn magazines and we would all look at them marveling at the female beauties, except I was making it up. The young women didn't really do it for me. There were no magazines featuring naked women in their sixties. Of course, I kept this all to myself.

When I entered college my taste in women had not changed at all, I was still obsessed with old women. Fortunately, by then there was a porn magazine for sale called "60 Plus MILFs". I would buy it religiously and would masturbate once or twice a day in my dorm room looking at the beauties. I was obsessed with wrinkly saggging breasts, especially the big ones that fell down to the navel or even waist lines; Absolutely arousing. I did have a problem though. I was, and still am, a premature ejaculator. A few strokes and that was it. Regardless how often I masturbated in a row I would never last. If I was really excited I would even ejaculate without touching myself. It was very embarrassing and I was very self-conscious about it. Of course, I had to hide the magazines carefully since I had a roommate and it would have been difficult to explain my preferences.

I knew exactly when the new edition would come out. My favorite book store was right around the corner. The cash register would always be operated by part time college girls. In the beginning I would be very embarrassed by the strange looks they gave me, but eventually I started to enjoy it and made sure that everybody in line would see what I was buying. Once the girl at the register even remarked that it was great for a young guy to be interested in old women and not just the usual barely legal. She smiled at me and I promptly ejaculated in my pants.

This went on for a while until one day I opened my dorm room door and there was my roommate with two girls leafing through a copy of my "Sixty Plus MILFs" magazine. I was mortified.

"Hey Frank, this explains why we never see you with a girl. Maybe I should introduce you to my Grandma," one of the girls giggled.

From that day on I noticed all the odd looks I got from the guys on my floor and I heard all the giggles of the girls. I had become the laughing stock of our floor. I had to find my own place.

There were several apartments available that suited my needs but one place stood out. It was an extra room in a regular house with its own bathroom. And the person living in this house, the landlady, was a shapely women in her sixties. I had to have this place. The woman was quite friendly and told me she would be happy to let me have this place.

A few days later I moved in. I was in love. Anna turned out to be 67 and widowed. She needed the extra income. She was tall with white hair, a little overweight, but in good shape. Best of all, she had a huge bust held in place by a bra that must have been made from steel cables. Every night I beat off fantasizing about releasing those breasts from their steel confinement.

A few days later, it was pretty late, I ran into her in the hallway. She was about to go to bed wearing a long lacy nightgown. I was stunned. Anne did not wear a bra. I scanned down her body, her bust was missing until I saw the protrusion of her nipples in the fabric - right down at her waistline. I stuttered, "I like your night shirt," and quickly disappeared in my room, masturbating within seconds.

I started to plot how I could make a move on her. I asked her whether we could watch football games together. She readily agreed but nothing would ever happen. She would just sit next to me on the couch, her heavy bust resting on her upper thighs. I would be erect most of the time, but she never seemed to notice. I was getting desperate.

One day, I was about to leave the house when I heard the mail slot open and the mail falling on the floor. I bent down to pick it up to put on the side table when I noticed a strange magazine. The magazine had a neutral grey cover taped shut. I picked it up and examined it. I bent it a little and peaked underneath the grey cover. It was a copy of Playgirl Magazine. I was ecstatic. A subscription to Playgirl Magazine meant that she liked at least looking at young men in all their glory. This was my angle and I had a plan.

I went back to my room to get a copy of my "60 Plus MILFs" magazine. I put it on my desk hiding it under a copy of a car magazine, but had it stick out just enough so that you could tell this was some kind of porn magazine. I placd the car magazine on top of it in a way that I would be able to tell if somebody had looked at it.

And sure enough, the very next day I could see the position of the magazine had changed. Anne had found and looked at it.

I often watched TV in her living room when she was not home. So I went down, turned on the TV, and rifled through her magazine rack.  There it was hidden in a copy of Vogue Magazine, "Playgirl: Campus Hunks". The magazine was full of pictorials of young men with fit athletic bodies and rather large cocks in various stages of arousal.

I knew Anne was coming home shortly. I waited until I heard the door open. I quickly grabbed the magazine and pretended to be deeply absorbed reading it. Anne came into the living room. She was about to say hello, but stopped.

"What are you doing?"

"I was just reading one of your magazines, Playgirl: Campus Hunks."

"So you think because I'm old I can't enjoy looking at young men."

"Not at all, I think it's great. Age has nothing to do with it."

She gave me a long look and sat down next to me on the couch.

"I just love these young fit bodies. I love their cocks and how hard they are," she said running her finger along the model's naked body. 

"Look at his cock, huge, hard, sticking out straight."

She turned the page.

"And this guy, his cock pointing straight up almost touching his stomach. I always wonder whether they know how to use these magnificent tools."

She suddenly got up. I heard her walking up the stairs to my room and returning. She threw my '60 Plus MILFs' magazine on my lap.

"And what about you?"

"Well, I'm the opposite, I have always been attracted to old women, even as a teenager."

"No girlfriends?"

"They are too young, I just don't find them compelling."

"And what is it that attracts you to older women?"

With that she sat down, open the magazine and pointed to a woman.

"What about her?"

I was getting aroused and the more aroused I became, the more I had the urge to confess my fetish.

"I love her wrinkly skin, look at these big saggy boobs and droopy nipples. Her snatch, hairy, wide open, and ready to get screwed at any time. Her big clit, waiting to be sucked on."

"Whow," Anne exclaimed, "you are a little pervert, aren't you?"

That was the end of our conversation.

The next evening, I was again watching TV in her living room. Anne came in wearing her white lacy night gown.

"That's the one you like," she greeted me.

"Looks excellent on you," I replied.

Anne sat down right next to me.

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Again she was not wearing a bra underneath. As she sat down her heavy saggy breasts hit her upper thighs and then fell off to each side, her right breast resting against my arm and back of my hand. I instantly became hard. Then my curse hit me again. I spontaneously ejaculated in my pants.

"Frank, would you strip for me like those young studs in my Playgirl Magazine," she whispered.

"I don't know," I stammered.

"Of course you do."

I got up slowly, stood in front of the TV and started to unbutton my shirt. Anne watched me intently. After the shirt off came the shoes, pants, and socks. I stood in front of her in my boxer briefs building a giant tent.

"Please come over here."

I walked up to her. She started caressing my abs, chest, and pinched my nipples.

She then grabbed the waist band of my boxer briefs and quickly yanked them down to my knees. My rock hard cock sprung free like a steel coil.

"Not bad, Frank. Didn't expect you to be that big. What is it, 7 inches? And what is all that come in your underwear. Did you ejaculate without touching your self?"

"I'm afraid so." I confirmed pointing my cock right at her face.

She grabbed it firmly with her left hand, while the right was cupping my balls and caressing my put. She then leaned back, pulled up her night gown.

"Fuck me Frank and fuck me good."

I stared at her hairy pussy, which looked moist and gaping. I grabbed her by the hips and with one push I was deep inside her. I started with slow long thrusts. I pulled her night gown over her head to see the objects of my deep lust - huge saggy tubular tits with large dark areolas. It was too much. I ejaculated again.

"That's ok, Frank, I'm sure you'll be ready again in a minute."

She caressed my balls and started slowly sucking on my cock, deliberately, like a lollipop. I immediately became rock hard. She released me and I grabbed her and pushed in, fucking her furiously. Unfortunately, I again lasted for less than a minute. This time I saw the disappointment in her face.

"Looks like you got a little problem here,Frank. You are a premature ejaculator."

"Yes, I am," I confessed."

"Then, you have to eat me out, I really need to come."

I got on my knees and buried my face in her pussy. My tongue circled her clit. Her juices mixed with my come started flowing freely. Anne moaned and started humping my face. Her breathing became labored. Suddenly with a loud scream she came, her entire body shuddering.

The next evening we fucked again. This time she had brought a tube of desensitizing cream. I rubbed it on the head of my cock and without much foreplay I penetrated her moist and ready pussy. The cream on my cock felt weird, kind of numb. Unfortunately I still lasted a minute only. Anne was kind of mad, but I did eat her out until she came.

Regardless of how often I fucked her I could never make her come. I was a premature ejaculator and I could see it was getting on Anne's nerves. I was afraid to lose her and would do anything to keep her interest.  I just told her.

"Anne, I don't know what to do. I can't help it. I'll do anything to make you happy."

"I know that Frank. There is one thing you can do. I have another young friend like you. He has the same problem, though not as bad as you do."

"You have another boyfriend?" I was shocked and felt rejected.

"Come on Frank, I'm a woman of voracious appetites and I do like you, but I need more. Here is what I'm proposing. I invite him over tomorrow and the two of you take turns fucking me until I come. That seems like a good solution and fair to everybody. His name is Phil and I'm sure you'll like him."

Phil arrived the next evening. He was tall, slender and very athletic in his early twenties. I was jealous, but I did have to admit he was a stud and I knew he too was a premature ejaculator. We talked and had a couple of beers to relax. Then finally Anne came to the point.

"You both are premature ejaculators. It's fine except I never come and getting eaten out is not the same thing. Let's go to the bedroom, get all naked and fuck. I want you both hard and ready. Frank fucks me first, as soon as he comes he withdraws, rolls to the side and Phil takes over. By the time Phil comes I expect Frank to be hard again. We do this over and over until I'm satisfied. OK?"

I looked at Phil. He had built a giant tent in his pants. It obviously was a go. We went to the bedroom, stripped naked and looked at each other. Phil's cock was about the same size as mine, it was cleanly circumcised and standing straight up, almost touching his stomach. I could see why Anne would like it inside her.

I was ready. Anne was on her back. Without any foreplay whatsoever I plunged my cock into Anne's moist and loose hole. A few thrusts and there I was again prematurely ejaculating in Anne's cunt. I quickly withdrew and rolled to the side. Phil immediately took over. His cock plunged into the moist gooey hole. He was whipping up my sperm to a froth. He did last a bit longer. He withdrew. I was ready again. This went on for three rounds. Anne's cunt was overflowing. Our orgasms did become dry, no more come. Phil did come through. Right before he came Anne's squealed loudly, shuddered, and came hard.

"You see that wasn't too hard. Everybody is happy. Let's take a break. I have one more request."

We rested on the bed for about 20 minutes. Both Phil and I were hard again.

"What a beautiful sight, the two of you are. Now, I want Frank to put his dick up my ass and Phil to lick my pussy until I come. Frank, do not come, just keep it in there. I just want the feeling of being full while Phil eats me out."

I had never done anal. I was ready to try. I could see the disappointment in Phil's face. He would have loved to trade places.

Anne reached for her cunt and scooped up a generous amount of her juices mixed with our six loads of come. Scooping it up with her hand she liberally coated my cock and told me to lie on my back. She slowly squatted and lowered herself. I watched my cock disappear in her butt. What an incredible feeling. Tight, moist, and warm. I did not come, I just lay there motionless listened to Phil eating her out.

Anne started to moan and was breathing hard. Her body shuddered as she screamed. I was still in her ass motionless.

"Go ahead, shoot your load, Frank."

I didn't need any encouragement. Two thrusts and it was over.

I pulled out.

"Can I do it too," Phil asked.

"Alright," Anne said.

She got on all four displaying her butt and gaping butthole, stretched out by my cock. Phil quickly inserted, thrust three times and was done. He did not withdraw, just staying in there. He probably wanted to go for another round.

"That's enough now, Phil," Anne admonsied him.

Phil withdrew and we all called it a night. My cock was hurting from all this fucking and coming. A good feeling though.

This arrangement went on until I graduated and moved away. I missed it very much. Don't know what happened to Phil and Anne. I' got married shortly thereafter to somebody my own age. I still lust for old women. My wife knows about my obsession. She thinks it's cute and to this day encourages me to keep buying my favorite magazine, "60 Plus MILFs". We read it together and I tell her what I would like to do to those awsome old ladies.

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Written by riederfrank
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