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Because I’m Not Pretty

Category: Mature
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Dan looked up at the big rental van as it pulled in at the house on the next street over. His back yard faced that home’s back yard, there was a five foot tall board fence between the two lots.

He spent a lot of time out in his own overly large back yard, keeping the grass and decorative plants in close to perfect condition. The other home had been vacant for several months. The sweet old lady that had lived there had passed away, so things there were getting to be on the unkempt side.

He had helped the old woman with her yard for many years, but with no idea who now owned the place, he didn’t feel right about just going though the back gate he had installed and taking care of things.

Dan was missing the cookies and milk she always came up with, and the breezy afternoons they had spent. The old woman had been a wealth of wisdom, he had always looked forward to those days.

He watched as a large woman about 40 or so got out of the driver’s seat. A younger version of her got out the other side, they went around back and started unloading boxes. The younger woman was also on the heavy side, although it was hard to really tell much about her from the dumpy clothing she wore.

Her hair was a dirty blond color, cut square across her forehead like she had taken scissors to it. Her cheeks were pudgy, her eyebrows darker and on the bushy side.

“New neighbors, looks like.” Dan thought, and went back to his Rose bushes. He had nearly finished the Roses when he looked up again. The large woman had one end of a huge couch hanging halfway out the rear of the van, the younger girl was inside trying to push.

Nothing was moving it looked like, and the woman on the ground was beginning to struggle.

Dan walked over and tripped the gate, stepped up and grabbed the end of the couch to steady it. Once he had the weight under control, he slid it out the rest of the way.

“Thank you, sir!” The woman said.

“I never would have made it.”

“No problem, welcome to the neighborhood. Can I help with anything else?” He asked, eyeballing a rather monstrous hope chest and some rather big looking chairs.

“Oh, that would be wonderful, thank you!”

That pretty much shot the rest of his afternoon, it was another couple of hours before everything was safely inside.

The older woman introduced herself as Melanie, she told him her daughter’s name was Kathleen. Dan introduced himself, noticing that Kathleen never said a single word, in fact, she never met his eye.

“I would ask you to let me fix you a nice dinner but we don’t have anything here yet. Can we take you out for a bite?” Melanie asked.

It didn’t take much encouragement to get Dan to go out for dinner, he lived alone and out of cans most of the time, and he hated going out to eat by himself.

The evening was one of those pleasant times, just people getting to know each other. Dan found himself talking about his late wife, and how with her gone he had taken early retirement. His pension from the years of teaching high school was enough, Social Security from an earlier job he had held was looming which would help. So he kept himself busy tending his yard, and taking his frequent trips down to the docks to try and catch a fish.

Melanie mentioned that she was divorced, and they had bought the house after selling the other home she had before. They were downsizing to try and stay ahead of things. Now she was hoping to get a job with the local school district herself. Dan was mildly surprised when she mentioned her field was physical education.

She caught his expression, and laughed.

“I might be on the big side but I am also pretty solid.” She told him with a grin.

“I’m sorry, I didn’t mean….”

“That’s OK. You haven’t seen me naked!” She said, laughing.

Dan first blushed, but then he found that funny and he laughed too.

Just a nice evening, he found he enjoyed her company and chit chat. Kathleen barely said a single word, though. She seemed to be very shy.

When they got back to their homes, Dan asked Melanie in for a glass of wine, she accepted. Her daughter excused herself and went home.

The next day he was back out in his yard, using his new riding mower to trim the grass. Melanie came out, her hair was shiny clean and she looked scrubbed, he spotted the hint of makeup on her face. That seemed odd to him since it was barely 9 AM but he thought little of it.

She asked if she could borrow his mower, Dan responded that he would be glad to cut it for her, it gave him something to do.

She asked him to pop in for some coffee and rolls after he was done. He also noticed Kathleen looking out at him from upstairs, when she saw him glance up at her, she quickly moved away from the window.

“She sure is bashful.” He thought to himself as he made short work of the yard. Then he went inside, Melanie served him some sweet coffee and homemade pastry like he hadn’t had in a very long time.

Over the next few weeks, Dan found himself almost daily visiting with them. Kathleen finally warmed up a little bit, but she still seldom had anything to really add.

One afternoon a few weeks later they were sitting on the back porch talking and sipping some beers. Kathleen had gone to one of her night classes, Dan had learned from Melanie that she was studying baking with plans to open her own pastry shop one day.

That explained the wonderful different sweet rolls that seemed to be ever present around Melanie’s kitchen. It was another delightful evening, the light breeze felt good, they were relaxing and talking about everything one could imagine.

“Danny, I was wondering…?” Melanie said, changing the subject.

He turned to look at her, she suddenly looked to be at a loss for words.

“I have been wanting to ask you….” She stopped again, blushed.

“You can ask me anything.” Dan told her.

“It’s been a long time, since my husband and I broke up? I don’t know quite how to say it, so I guess I will come straight out…would you like to make love with me?”

Dan looked at her in complete surprise.

Melanie blushed furiously, that wasn’t an easy thing for her to ask, and Dan was floored. He simply had not even thought of her that way.

“I mean…I don’t get very many opportunities, because I am so big…heavy…so if you don’t want to…I will understand.” Her eyes went downcast, that had to be tough for her to say.

Dan had never in his entire life been asked straight out for sex by any woman, and he hadn’t been with anyone since his wife had died. He had actually given up any thought that he ever would again, it already had been years. Now Melanie had asked, that was stimulating, and he felt the glimmerings of a response at the situation.

Of course he had earlier had to deal with everyone he knew introducing him to a long string of white haired ladies in various stages of oversize. But Dan had no interest, his own wife had been over a dozen years younger and women his own age didn’t interest him. Most of them just looked to be little old ladies to him even though in most cases they actually were younger than he was.

His own wife had been on the chunky side, so Dan didn’t mind that one bit, in fact, he liked that part. What he didn’t care for was a female that made him aware of his own advancing age.

With his own hair rapidly receding and developing streaks of silver, the women that he did notice all thought of him as grandpa. The closest he had come to getting anywhere was one gal he had met at a party, she looked to be in her early forties and was interesting.

Dan had made the mistake of showing some serious interest, then he overheard her talking to another woman about her age.

“That old coot was actually hitting on me!” She giggled to the other woman. They both snickered. Dan had beat a hasty retreat soon after.

Now he had Melanie, that he knew was barely 38 years old asking him flat out for sex?

For the first time in a very long time he felt himself begin to respond, her asking him bluntly was so unique and so different his body just took off by itself.

“I…I am surprised, but the truth is I would love to!” He smiled at her.

A huge grin crossed Melanie’s face, she stood up and reached out for his hand.

“Kathleen won’t be home for several hours.” She smiled.

They kissed for the very first time the moment they got into her bedroom. Then she looked at him with slitted eyes and reached for the buttons on her blouse. He just stood and watched, she undid the last one and taking a deep breath, she slid the blouse off her shoulders. Reaching behind her back, she tripped the catch on her heavy bra, letting it drop.

Melanie’s breasts were very large, they had long since partially given up to the forces of gravity. But even sagging heavily, they were still very beautiful. His face flushed with excitement at the blatant display, he reached out with one hand and lifted her left breast, letting his thumb trace across her large nipple, which almost instantly hardened. She let out a small shiver at his touch.

Then they kissed again, she pressed her heavy breasts to his chest, leaning back, she quickly slipped the buttons on his shirt. Then she hugged against him again, mashing her breasts against his bare chest.

“I love this feeling.” She murmured quietly. Then she tugged him towards the bed, they fell onto it side by side. He felt his belt give, then the soft sound of his zipper. Her hand struggled for a moment to find it’s way inside the front of his briefs, she let out her breath in a sigh when she finally succeeded.

Dan was fully erect. Melanie leaned forward so that she could look down at him, her hand slid up and down, then she gripped firmly, sliding his foreskin back.

“There it is!” She mumbled, her palm rubbing the sensitive end of his penis. Hopping up, she quickly slid her own slacks down and off. Dan saw the dark mass of pubic hair for just a moment before she climbed back onto the bed. Her tummy was round, her hips full, she almost shyly kept her legs together.

Reaching out with both hands, rolling the palms back and forth briskly against the head of his erection caused Dan to firm up even more. He reached down to slow her, feeling that he was coming very close to a climax.

“I want to see you.” He told her, pressing her back on the bed. He put his right hand on her left knee, pushed her legs open. The engorged mass of multicolored flesh between her legs came into view. She turned her head away, Dan saw another small blush cross her face. Reaching down, he stroked his fingers up and over her sex. Her hips rose slightly, then more as he repeated the motion.

“Put it in, put it in!” She muttered, her hips beginning to thrust now. Dan got on top of her, reached down and spread her lips apart with two fingers and pushed. He felt himself slide all the way inside in one motion, she felt so very wet. Her inner muscles gripped at him, folding to fit his shape as she let out a long groan.

Her first climax made her body tremble, her nipples became like needles, Dan could feel them poking his chest. She had another huge climax, her pussy felt like it was gripping him, then she relaxed and gripped him again. The first time was very quick, it had been a long time for both of them.

When her insides began to spasm, that did it, he had no way to hold back, letting his body jam firmly against her pubic mound as his own orgasm hit him.

They lay like that for several minutes, then as he softened, his member slipped out.

“God that felt good!” Melanie told him. Dan rolled over on his back to rest, realizing he was soaked in sweat.

He felt himself begin to doze lightly, then a voice woke him up.

“Mom?” He heard Kathleen call out again from the other room. Quickly he tugged the covers back, and drew them up and over them, just in time as the door swung open.

“Mom? I am ho…” Kathleen stopped, staring at them in surprise.

“Oh! I am sorry! I didn’t know you guys were…” She quickly retreated, closing the door.

“Well, I didn’t expect that.” Melanie giggled.

“She is an adult, she should understand.” Dan told her.

“I hope so, she has never….at least I don’t think so anyway.”

“Really? She is nineteen? That has to almost be a record!” They both giggled at that, then snuggled up for some exploring. It wasn’t too long before Dan managed a second turn, he noticed that Melanie was trying very hard to be quiet that time.

Things developed into quite an affair after that, Melanie would slip out of the house late at night after she thought Kathleen was asleep and join Dan in his bed.

She wasn’t quiet at all during those times.

But Dan knew that Kathleen knew all about it, he saw the sidelong glances she gave him from time to time.

One afternoon about two months later, he was sitting on his porch when he looked up and saw Kathleen coming through the gate. That was a surprise, she had never come over by herself up to that point.

“Hi! Want some iced Tea?” He asked her.

“OK.” She sat on the step, looked at him and glanced away. Dan got her a glass, handed it to her and sat back down. She obviously had something on her mind, so he just waited.

“Are you going to marry Mom?” She asked suddenly.

That was another surprise.

“I…I guess we haven’t even thought about that.”

“I know you guys are having sex..a lot.” She blurted out.

“Well, when two people like each other…”

“I guess. What is sex like?” She looked up at Dan for a moment.

“’s..pleasure, honey….I don’t know, it’s hard to explain.”

“I don’t think I will ever get to know.”

“Why not? There is no reason why you won’t find a nice boy someday and…”

“I’m not pretty, no boys ever like me or even look at me.”

“Oh, you are too! You are a very pretty young woman!”

“No, I’m not! I am big and my face is ugly and they all ignore me.” She was nearly whimpering.

“Attracting someone is often just a matter of taking advantage of your best features, and using your personality, honey.”

“I don’t know how to do any of that.”

“Maybe I can help you, if you want me too? Your Mom can teach you about dressing differently, changing your hairstyle?”

“Mom tries but I feel all funny, people look at me and see that I am so big….”

“You are pretty enough on your own, but some things like that can help. How about we take you to someone I know and get some professional help?””

“Oh, will you? Really? That would be great! Mom got called by the school and she starts as a temp next week, so we have some time then, OK?”

Her sudden change to being eager caught him by surprise.

“OK.” Dan told her, wondering what he had just gotten himself into.

The next Monday Kathleen showed up on his doorstep, Melanie had left for school just moments before. She had on the usual shapeless sweater that buttoned up the front and a pair of corduroy pants.

“What’s first?” She asked. She seemed to be excited, it was the first time Dan had really seen her that way.

“Well, let’s go down to the hair salon first, then maybe do some shopping?”

“OK!” She turned and headed for his car. He followed along with a chuckle. Dan knew Sally down at the shop where he got his own hair cut, he took her there.

Sally looked her over, then went right to work. The straight hair with square cut bangs changed to a nice blended pageboy style with colors and highlights. It really did look good on her. Then Sally called out to Marcus, a skinny and obviously gay African man that worked for her.

“Do some magic!” She told him.

“Oh, goody!” Marcus clapped his hand together.

“I will make you absolutely gorgeous, sweetie!”

In about an hour Kathleen’s face looked more slender, but she nearly came right out of the chair when Marcus reached down and unbuttoned three buttons of her sweater. The tops of her large bust now showed clear to the edge of her white bra.

“Honey, you have really nice big titties, you just have to let them breathe a little bit. You need a different bra, too. That one just isn’t you at all! They are supposed to show, not hide!”

Marcus reached down and jiggled her large bust with his fingers.

“That thing is like iron, honey. You need to let the bait bounce a little bit.”

Kathleen turned bright red at that, looked at Dan who was doing his very best to keep a straight face, then she looked down at herself like she had never seen her own breasts before.

“Clothes, sweetie! We just have to get you some clothes! Sally, I need a couple of hours here, this is an emergency!”

Sally just laughed and nodded.

“Come on then!” Marcus grabbed Kathleen’s hand and took her in tow down the street. She glanced back at Dan as he followed along, she was helpless to resist.

The next couple of hours were a whirlwind of different outfits, at first Kathleen was very shy about it but then she got into it.

Marcus found a flimsy bra that was red, and a pair of panties that matched. She took them and went into the small dressing room, looking at the outfit hesitantly. He darted off across the store and was back in seconds with several dresses. He jerked the curtain open just as Kathleen was sliding her pants down, she squealed and instantly tugged it back closed.

“Relax, sweetie, we have all seen girls before.” He told her through the curtain.

“There are people out there!” She protested.

“This is going to be such a job!” Marcus told Dan, pouting with one hand on his hip.

Dan smiled to himself but didn’t say anything. Kathleen finally came out wearing the dress, she really did look good.

With the baggy pants and heavy bra gone, she looked much more slender. Dan kept his mouth shut as Marcus ran back and forth from the clothes rack to the dressing room. Once when he jerked the curtain back and went in Kathleen was standing there in front of the mirror in the red panties and a matching lacy bra, she saw Dan looking at her and quickly turned her back. Dan realized that Kathleen was just big and curvy, her body didn’t look fat at all in the quick glimpse he got of her.

Marcus paid no attention at all to her semi nudity, he was having fun.

At one point Kathleen came out in a filmy patterned skirt that was on the short side. Her legs looked muscular, somehow the combination of the skirt and matching blouse made her look much thinner. When she turned, Dan realized that she didn’t have a bra on at all this time, that was also a surprise. She was beginning to relax.

Finally they settled on three new outfits, by now Marcus was going right inside the dressing room with her every time and she wasn’t objecting.

“Oh, she has just the greatest breasts, I would kill for a pair like that!” He exclaimed to Dan.

Kathleen smiled shyly at that.

Finally they were headed back home, she was grinning the whole trip.

Inside, Dan made some Tea and they sat and talked about it. Gone was the dumpy looking girl, it was replaced by a full figured but pretty young woman.

Kathleen learned fast, now each time Dan saw her she had on the traces of makeup, her hair fixed up. The drab colors were all gone, replaced with brighter outfits.

Melanie and Dan talked about it, she was pleased that he had helped. Their own relationship had progressed to the point where Dan was thinking about making it permanent.

So he asked her to marry him. Melanie hesitated, then hugged him.

“I really like you, Danny. And it’s great to have sex with you, but we are having fun. I don’t want to be married, I did that once and I like things better this way.”

Dan really wasn’t that upset, thinking about it he realized he liked things the way they were, too.

Of course now with Melanie working, she didn’t slip over to his bed on week nights much any more. She did come over on weekends, and they often went out on Friday evenings.

Then one Friday she told Dan she had a date, one of the teachers had asked her out.

“You don’t mind, do you?” She asked.

In fact Dan did mind a bit. He even watched out the window for the man to arrive, the guy was younger and tall and slender. Dan felt a flash of jealousy, but it quickly passed. It was just the way it was, he couldn’t blame Melanie.

They had no more than left for the evening when there was a knock at his door.

“Hi, Kathleen!” He said, opening the door to find her standing there with a small tray of pasties.

“I made these for you, Danny.”

“Thank you, come on in.” He noticed she was wearing one of the pretty skirt and blouse combos Marcus had picked out for her.

She sat down in the chair opposite him.

“Are you mad at Mom?” She asked straight out.

“No, not really. We don’t have any commitments to each other.”

“I asked Mom if she was going to sleep with that guy but she said she didn’t know him well enough yet.”

“Oh. Well, I guess…”

“I know you well enough.” She gave Dan a sly smile.


“I know you well enough!” Her chin came up with a determined look. It registered on Dan what she was saying.

“I don’t think…”

“I do! Don’t you like me?” She stood up.

“I like you just fine, but you are only nineteen, and I am…?”

“I am twenty now! And I want to. I have for a long time but Mom saw you first. Now she is out with someone else, so I want to! I want you to be the one…”

“Honey, I don’t think it’s a good idea, you should save yourself for….”

“I don’t want to save myself, I am tired of that. I am grown up now. Mom can have sex and so does everyone I know. Why can’t I?”

“Well, you can, but it should be with the right…?

“That’s crap, Danny!”

“Sex really should be between two people who like each other, and…” Dan felt himself searching for the right thing to say.

“Don’t you like me?” She looked stubborn, this was completely new.

“Honey, I like you just fine.”

“Then teach me about sex?”

Dan just looked at her, not quite sure what to say.


Kathleen reached down and quickly undid the buttons on her blouse. Then she reached back and tripped her flimsy bra. In seconds she was standing there naked to the waist, and Marcus has been correct.

Her breasts were perfect, full and round, her nipples pink. There was no hint of a sag at all.

“Oh, God.” Dan groaned, reaching for her. She stepped forward willingly, tipped her head up for a kiss.

“All right. Come on.” He told her, taking her hand. He led her into the bedroom, turned her to stand there. Then he sat on the edge of the bed.

“OK. Strip for me.”

She hesitated, not expecting that. Dan halfway expected her to chicken out.

She didn’t. Her hands came down and slid the filmy skirt down her legs. Then she stood there, wearing just a pantie that had matched her bra.

“What do you want me to do?” She asked, her neck beginning to flare red.

“The rest. Show yourself to me, I want to see everything.” Dan was fully erect now.

Her hands came up and tugged at the waistband of her pantie, she stripped it down and stepped out of it. She was completely hairless, he hadn’t expected that, either.

“I..I shaved it all off, I read online that men like that.” Her voice once again took on a shyness. Dan was beginning to enjoy this.

“You really are beautiful, I like the way you look standing there like that.”

“I have never….just at the Doctor.” She managed.

“Well, Marcus saw my…but he is…”

Dan reached out and took her hand, pulled her down onto the bed. She lay back with her legs together.

“Spread your legs.” He told her.

She opened then a few inches.

“Wider, as wide as you can. I want to see you.”

Kathleen opened her legs, her pussy was just a slit before but her outer lips folded open right in the center of her vagina.

“Pull your knees up.” She glanced at him but complied. He reached down, slid his index finger into her opening, getting a gasp from her. The flesh surrounding his finger was extremely tight, he had to work a bit, then he felt it slip. He pressed his finger inside all the way to his knuckle, turning his hand upwards to lightly stroke her.

She let out a small gasp, then her hips bucked. Dan leaned forward and slid his tongue up and over her, getting rewarded with another gasp. Glancing up, he could see her nipples contracting into tight little buttons.

He just kept up his stimulation, she was gasping and jerking her lower body. It was like she was having a struggle, not knowing exactly what to do but also losing control over what was happening to her.

Then she let out a loud moan, her hips thrust up solidly against his face and held there for several long seconds. When she collapsed, he kept on for a moment before he felt her try to pull back as her body went overly sensitive.

Dan stood up, began to remove his clothing. She watched him through slitted eyes, as he stripped down his jeans and underwear, standing there with his erection burgeoning outwards. Her legs were still splayed open, he could see a trickle of moisture sliding down her lips.

Climbing up on top of her, he rubbed the end of his penis up and down her slit to moisten it, then pressed. It was like pushing against a wall, her body was resisting his efforts because each time he pressed, she tensed up.

“Take a deep breath and hold it.” He coaxed.

She sucked in a deep breath.

“Now blow it out!” She released in a gush, Dan pushed at the same time. He felt himself pass her tight outer opening, then she relaxed. He slid inwards completely, her face winced in pain so he stopped.

They lay like that for a few seconds, then he felt her hips jerk. He thrust again, her body responded.

“Oh…God!” She reached up and wrapped her arms around his back.

Dan did his best to last as long as possible, but when her body went into convulsions, he lost control. Now she was slick, it was getting easier. Her mouth was open and her eyes were squeezed shut firmly, then her eyelids began to flutter. She was still so snug that he didn’t even fully lose his erection, they lay like that for several minutes, joined but not moving.

“So that is what it is like.” She said, after a he softened and slipped out.

“Honey, that is as good as it gets, you are really special.” He told her.

“I liked that, I never felt like that before. Can we do it again?” She grinned.

“I think it will be awhile.” Dan admitted.

“Can I touch you?”

“Sure.” Dan almost laughed at that. She reached down and took hold of him, began to play and look at his now limp cock.

“This is pretty big, I didn’t think it would fit when I first saw it.”

“It took a little bit, but they always fit.” Dan laughed.

“I never saw one before, are they all this big?”

“Some are even bigger, some are smaller I guess.”

“Look! It’s starting to get bigger again!” She sat upright, took hold of him with both hands.

“You are a virgin, aren’t you? But I noticed you didn’t bleed any?”

“I stuck a hairbrush handle up there once and that made it bleed, I think that did it.” She giggled.

“A hairbrush?” Dan laughed at that.

“Yea, but this is better. I think we can do it again now, let’s see.” She straddled him, settled down. His erection slipped right in. She began to swing her big hips back and forth.

“Am I doing this right?” She gasped.

“You are doing just fine!” The second time lasted much longer, Kathleen was dripping with sweat long before Dan finally let go again.

Dan woke up, looked at the clock. It was nearly 10 in the morning. He looked over at Kathleen, she lay beside him, still naked on top of the covers. He reached out and stroked her breast, she let out a small moan but didn’t wake up.

Sliding out of bed, he went into the bathroom and took a shower. Kathleen was standing there still nude when he stepped out.

“My turn!” She said, sliding by him. He went back into the bedroom and got dressed. She came out drying herself with a towel.

“Oh, you got dressed? I was thinking maybe we could do some more sex?” She smiled. All of her shyness seemed to have vanished.

“Honey, I am an old man, you are going to kill me.”

“If I don’t then Mom will.” She grinned.

Dan looked at her.

“What are we going to tell your Mom?” He asked her.

“Mom already knows, she is the one that told me to get you to do it. She said you would be good, not like her first time.”

“What? Really?” Dan was shocked at that.

“Yes. That is why she went out on that date, so you would feel comfortable. She told me you might try to resist and that I had to be stubborn.”

“You mean she doesn’t mind?”

“It was her idea. Mine too. We like you, and we can have lots more sex if you want to.”

“We? You mean, both you and your Mom?”

“Yea. She wants me to learn everything, but she told me she likes to do it with you too, so we decided that we both would.” Kathleen grinned at him.

“That’s all right, isn’t it?” She asked.

“Uhhh…Yes, I think that will be just fine.” His head was spinning, things were coming at him pretty fast.

Dan sat down on the edge of the bed, she finished drying herself off and came over and sat beside him.

“Can you do that thing you did last night to me again?” She asked.

“Which part?”

“Where you used your finger and licked me at the same time?”

Dan was happy to comply. This was amazing, different. A mother and daughter?

Kathleen’s pussy tasted sweet and fresh. He was very busy trying to stay in place on her thrusting hips when somewhere in the back of his mind he heard the phone ringing.

He disengaged, picked it up.

“How is it going?” Melanie’s voice asked with a hint of laughter in it.

“Just fine! Hey, want to come over and help?” He asked.

There was a short moment of hesitation.

“Be right over! Hey, did you teach her how to use her mouth yet?” She asked with a giggle.

“No, not yet.”

“OK. I will be right there!” She hung up.

It was going to be one hell of a Summer.

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