May December Ch. 01

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Middle-aged man meets horny teenager.
2.1k words
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Part 1 of the 2 part series

Updated 10/29/2022
Created 05/01/2004
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Sam was in the process of getting a divorce and was temporarily staying at his brother's house. He had been living there for about three weeks when in walked the first woman he lusted after since he had split from his wife. Today Sam's niece, Norma, came home from school with her best friend. They were both eighteen year old seniors in high school.

Normally Sam did not care for younger women, especially teenagers, he thought they didn't know anything and he did not want to have to teach them about sex. He liked a woman who loved sex, knew what she was doing and was nasty to boot. This young lady, whose name is Ruby, changed all of that in a heartbeat.

Ruby's hair matched her name. She had cat green eyes and full lips. Ruby's neck was long and slender. Ruby did not have the body you usually associate with a teenager. She had the classic 19th century hour glass figure. Her waist was barely seventeen inches flowing into a thirty-four inch set of perfectly rounded hips. Ruby also had an ass to die for, tapering down into long shapely legs!. Much to Sam's eyes delight, Ruby had big tits! They were at least a DD cup. Except for her age, Sam could not have designed a more perfect woman!

The first day Ruby came into Sam's brother's house, when Sam was there, he was so mesmerized by her stunning good looks he barely could say hello to her! Ruby was wearing practically nothing at all. Her gorgeous ass was covered in bright blue, tight short shorts. They were more than skin tight. The shorts spread and cupped her cheeks magnificently. The puffy lips of Ruby's pussy were on display behind the tight fabric. Ruby's breasts were covered by a skimpy, see through, white halter top. They stuck straight out with absolutely no sag! Ruby's teenage nipples were straining to stick through the flimsy material as well!

When Ruby looked at Sam she noticed he had gotten an immediate erection! She inwardly laughed and thought I bet he'd like to fuck me! Sam had exactly the same thought.

After the girls left, Sam was left alone with his thoughts and a stiff dick. He went into the bathroom and started a shower. Once Sam was in the warm water and started soaping up, his thoughts turned to Ruby and her fabulous teenaged body. His dick jumped to back to attention. Sam masturbated and fantasized about Ruby until he got the release he needed!

Over the next several weeks Ruby came and went. Each time she left, Sam got hornier and hornier for her! Sam knew he should not act on his lust for the teenager; after all he was way more than twice her age! (Sam was 53)

Ruby was a very aware young woman and Ruby knew the effect she had on Sam. Ruby loved to tease him! She also knew, if she teased him enough, she could posses him. Over the past few weeks, whenever she caused Sam to get an erection, Ruby noticed that it looked like Sam had a big dick! She had to find out! Ruby was a trophy collector and she did not have a middle aged man in her collection. That is, not yet. She wondered if sex with an older man would be different.

Ruby was about to find out! One summer Saturday afternoon she stopped by to see her friend Norma. Sam's niece wasn't home. In fact, Sam was the only one there! Ruby was dressed in her typical sexy way and caused Sam to get hard almost as soon as her saw her!

Ruby looked at Sam's bulging crotch and said to him,

"Wouldn't you like to do something with that?"

Sam turned all red in the face and stammered,

"Do something with what?"

Ruby moved close to Sam and slipped her hand over his bulge and said,

"Do something with this!"

She rubbed her hand all about his hard dick, caressing and gently squeezing it. This was almost too much for Sam. He finally answered,

"Of course I do, but it is just a fantasy! I'm old enough to be your father!"

"I know. I think that is why I'm strangely attracted to you. I've never had sex with anyone older than twenty."

Ruby continued rubbing Sam's dick. He was now nearly ready to cum in his pants! Ruby unzipped Sam's pants and pulled out his stiff dick. Sam was well endowed and his erection impressed the teenaged Ruby!

"OH, this is nice and big!"

She dropped to her knees and took Sam's dick in her young mouth! Ruby has been sexually active for awhile and has learned to give great head. That wouldn't have mattered to Sam at this point. He was so excited, that as soon as Ruby had his dick all the way in her mouth, he came. And cum he did, Sam nearly suffocated Ruby! She was not expecting such a quick reaction, or so much cum!

"I'm sorry, I didn't mean to cum in your mouth! You caught me by surprise!"

Ruby stood up, still holding on to Sam's dick; she wiped off her chin and smiled at him.

"Looks like middle aged dicks work pretty good! They don't taste too bad either!"

"Ruby! We shouldn't be doing this! Especially in my brother's house. He'd kill me if he knew I was lusting after you, let alone acting on my desires!"

"Yeah I know, but how long has it been since you've had sex? Several months I'll bet."

"If you must know, I haven't had sex since I moved in here several months ago!"

"As far as I'm concerned getting a blow job doesn't count as being laid either! You need to have that big thing properly fucked! And I'm the one that's going to take care of that."

"No! We can't do that. Especially here!"

"Yes we can! Besides who says we have to do it here? We can rent a hotel room anywhere! I'll call you in a couple of hours and you can tell me where to meet you tonight at 8:00PM!"

"Are you sure you want to do this?"

Letting go of Sam's still hard dick, Ruby took his hand and placed it over her wet pussy.

"Feel this. What do you think?"

Sam's hand felt the teenager's wet pussy staining the front of her shorts. Ruby's young pussy radiated intense heat. Sam squeezed it gently and said,

"8:00 PM it is!"

Ruby spun about and quickly disappeared! Sam slipped his spent member back in his pants and thought to himself,

"OH SHIT! Now what am I going to do? I'd really like to fuck her!"

Sam's dick got hard again and that answered his question for him! Sam called a local hotel and made the arrangements for that evening.

At 8:00 PM sharp there was a soft knock on the door to the suite Sam had rented. When he opened the door he expected to see the teenaged Ruby standing there. Ruby was standing there alright. But she didn't look like a teenager at this moment! Ruby's hair was done up in the fashion of the moment. She was wearing a deep lavender strapless full length evening gown that was slit on both sides clear to her hips! Ruby's lovely legs were encased in nylon stockings, held up by a black garter belt. She did not have on panties. Ruby's very ample breasts were barely contained by the top of her dress. In a word, she was stunning!

Ruby walked past Sam and into the room. She stopped in the center of the room and did a slow pirouette. With sultry eyes she whispered,

"Well?"

Sam's eyes nearly were popping out of his head and all he could mutter was,

"You look good enough to eat!"

"I hope so!"

Sam closed the door and Ruby melted into his open arms. Sam reached down and took Ruby's beautiful ass in his hands. When he squeezed her cheeks, Ruby leaped up and threw her legs about Sam. She tightly squeezed him and rubbed her pussy on his abdomen, which just happed to have his erect dick up against it. Ruby was grinding her pussy on Sam's dick. They were now engaged in a furious tongue swapping and dry humping festival.

Sam carried Ruby, whose hips were wildly humping his constrained dick, into the bedroom. When Sam knees ran into the edge of bed, he fell forward, pinning Ruby on her back. Her legs were still wrapped around his body. Ruby's hips were moving all around, causing her pussy to rub all over Sam's hard dick. He broke their kiss and pulled the top of her dress down. Both of her big, pretty tits popped into his view. Sam stared at both of them for a minute. Then he took her left nipple in his mouth and sucked. When Sam ran his tongue about the hard tip, she moaned in pleasure! Sam worked on both tits for several minutes. Soon Ruby's nipples were aching in desire and her pussy was drenched in her juices. All the while, Ruby was dry humping Sam's dick. Sam figured out the secret to Ruby's dress and soon had it off of her. The teenager was now laying on her back nude, except for the garter belt, stockings and black three inch heels! Ruby's nylon clad legs were spread far apart and framing her pretty pussy. Ruby's huge tits were sticking straight up, begging for more attention! Ruby cupped both breasts and, while pinching her own nipples, offered them to Sam!

"Like I said you look good enough to EAT!"

Sam buried his face between Ruby's legs. He took both lips of her very wet pussy and spread them apart. Sam took her already erect clit, between his teeth, and sucked it to full erection. Ruby's clit was at least two inches in length! Ruby grabbed Sam's head and pulled him into her pussy.

She yelled, "I'm Cuming!"

Ruby clamped her legs about Sam's head and rode his face through her orgasm. When she had calmed down enough to relax her grip on Sam's head, he got up on his knees and undid his pants. When he got his dick free, he slammed it deep into Ruby's waiting pussy.

"You are so tight!"

"That's because you are so big!"

Sam thrust far up inside of Ruby's pussy; Sam's dick reached depths that had never been reached before! Ruby wildly thrashed about beneath Sam. Since Sam had cum earlier today, this one would last quite a while. He sucked and licked Ruby's young breasts and hammered her talented pussy. After a while both of them were nearing release, Ruby for the second time tonight, and Sam for the second time today. As he felt his nuts tighten up, Ruby began to cum! As she reached the top of her orgasm, Sam let loose. He filled Ruby's pussy with cum.

After a short rest, Ruby leaned over to Sam and said, "Once more?"

Without waiting for an answer, Ruby slid around and took Sam's semi-erect dick in her mouth. At the same time she covered Sam's face with her sloppy pussy. Sam is no stranger to eating a pussy filled with cum. He used to eat his ex-wife's messy pussy frequently, especially after he'd filled it with his cum. Sam's ex-wife would go wild whenever he ate her cum filled pussy. There must be something about a man eating a woman's pussy, after he has freshly fucked it, that really excites a woman! Ruby loved it as much as his ex-wife did! She rubbed her pussy all over Sam's mouth.

Soon Ruby's talented mouth had Sam's dick back to full erection. She was deep throating him like a pro. Ruby had Sam's full ten inches completely engulfed in her mouth on every stroke. Both of them were so excited, by their frowned upon May-December tryst, that they were soon on the verge of Cuming again!

Ruby was the first to cum. When she did, her pussy expelled the rest of Sam's cum into his waiting mouth. Mixed with her juices the taste was wild! He could not hold out any longer. Sam's massive dick sprayed the back of Ruby's throat with his seed. He had very little cum left to deliver and Ruby easily swallowed it all!

The next morning they fucked each other again and again to a couple of more orgasms. Finally, they could fuck no more. Both of them took showers and got ready to depart.

When they were parting Sam was sure this was a one time deal. A fantastic fuck, but probably still, this time and this time only!

Ruby said to Sam, "How good do you get if you've had a lady in bed for a few times?"

"A lot better!"

"Good, same time, same place, next week!"

Sam watched Ruby's ass as she walked down the hall to the elevator and his dick got hard again! He could hardly wait!

To Be continued...

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