Big Tit Tiffany

The local grocery store was not that crowded. A bunch of kids, a few senior citizens, and middle-aged men and women taking care of their everyday chores. Mr. Matthews was there also. He taught math at the local high school, so it was not that uncommon for him to run into old students or their parents. Most of the time if that happened he waited for them to greet him first and today was no different.

His eye had been caught by a buxom blonde buying some watermelons. When she saw Mr. Matthews staring at her she waved happily and greeted him like an excited puppy. It took some effort but then he also recognized that they knew each other from the past. Tiffany was an old student of hers from a few years back.

She was oh so happy to run into Mr. Matthews. He had always been super nice to her. After he heard she found it hard to pass her college math classes he immediately volunteered to help her out. Pro bono of course he added. She had no idea what that meant so she had to ask. And he explained it was free of charge. How lucky for her.

Then he helped her with the melons. She was not sure what size to get and he assured her the pair she was holding, no matter how large they were, were not at all too big for her. He gave her his phone number and they agreed on a time for the tutoring session. She had a strangest feeling that Mr. Matthews kept staring at her when she was walking away but she guessed he was just so surprised how much his old pupil had grown.

When the day of the tutoring came she was at his place early. It was quite a hot day and she wore some hot pants and a flannel shirt tied down under her large tear-shaped breasts in Daisy Duke's fashion. Mr. Matthews' mouth hung wide open when he opened the door for her. Tiffany was wondering if he was after all the right choice for tutoring her. He had always seemed so smart but now he seemed somewhat slow. Like maybe he had gotten too old and lost his wits.

But when they got to the math problems he was back on track and Tiffany listened to him in awe. She did not understand that much of his explanations but he definitely sounded very vise. He even had a stand-alone whiteboard where he was writing down the example problems and she was impressed by his professionalism.

Tiffany was sitting down in front of him like a good student and tried her best. But all the numbers just kept mixing up in her girly brain and finally, she had to admit to him she could not follow what he was saying. Mr. Matthews suggested a break and that was more than welcomed by Tiffany. She made a huge stretch pushing her arms and shoulders back in order to relax a little. If she would have looked then she could have seen her old math teacher staring down at her boobs and practically drooling.

They were just about to start again when something caught Tiffany's eye.

"Is there something wrong with your pants Mr. Matthews? I mean there is some strange-looking bump on the front," she asked and pointed at his crotch with her finger.

"Ah well yes. Sorry about that. Never mind." he tried to make her ignore it but she was now so perplexed she could not let it go.

"I'm pretty sure that wasn't there when we started. You have been standing in front of me the whole time and I'm sure I would have noticed. What is it? Is it some sort of condition?" she inquired more.

He was a bit lost on the fact that Tiffany did not understand what was going on. And somehow being caught having an erection right there in front of this young blonde with her big boobs made him even harder. He was not sure if she was just playing with him but decided to go along with it anyway,

"Well yes, in fact, I do have this terrible medical condition. It's a bit embarrassing but since you are so nice I will tell you about it. Sometimes my penis swells terribly and a great deal of my blood stays there making it bigger."

"How horrible," she exclaimed holding her cheeks with her hands and making her mouth into an o-shaped ring. Then she continued, "Is it dangerous? I mean do we need to get you into a doctor or something?"

Mr. Matthews decided to go all in,

"Well we do not need a doctor but sometimes massaging it helps. But not if I do it myself, it has to be some other person. And Mrs. Matthews, let's just say she hasn't been that keen on helping me lately."

"Oh my," answered Tiffany with an astonished expression on her face, and then went all serious. Her lips showed her determination in the cutest pout and she continued, "Since you have helped me with my math I think the least I can do is to help you with your problem."

As she started to unbuckle his belt Mr. Matthews was having a hard time believing it was happening. The busty 19-year-old was pulling his trousers open in order to "fix" his penis problem by massaging it. His proud cock sprung free and yet another "oh my" escaped her lips.

As she took hold of his penis Mr. Matthews felt dizzy.

"I better sit down dear. Could you make some room for me, please?" he asked and she obeyed.

The chair she had been using had room only for one and she fell on her knees in front of it on the floor. Testingly squeezing and pulling his penis.

"Hmm...little more up and down...for the love of god thats it. Just like that." the old teacher muttered as Tiffany found the right pressure and rhythm. He asked her to cup his balls with her other hand and she followed his orders staring at his penis.

"It sure is full of blood Mr. Matthews. All purple and veiny. Are you sure I am helping it seems like it's getting harder and harder."

Mr. Mathews was staring at Tiffany's cleavage. Her boobs bounced as she was jerking his cock faster and faster. A single long blonde curl of her hair was circling on top of her left boob. Just as he was about to cum he jumped up and barked an order to Tiffany to open her mouth. She was still wondering what would it mean when Mr. Matthews pushed his cock into her lips and then past them to her mouth.

A warm and salty load filled her mouth. She was not exactly sure what to do with it but somehow instinctively she started sucking on his cock like it was a particularly tasty lollipop. Likewise, instinctively she gulped all of it down to her stomach as she was afraid some of it would spill out from her mouth.

The stream of cum diminished but Mr. Matthews hold her there by gripping her blonde hair. On the floor, on her knees, and mouth full of cock and cum. He even reached down to her other boob and groped it with affection.

"What's he doing down there? My boobs aren't sore. No need to massage them," she was thinking but carried on. He deposited the final spoonful of his hot sperm in her mouth and only then collapsed back to his chair.

"What was all that about?" Tiffany asked giggling, "I thought I was supposed to massage it but didn't know I would need to use my mouth to do it."

Mr. Matthews let out a satisfied sigh.

"Well I did not want to make a mess so this was just an idea on how to avoid smudging our clothes and your hair and make-up," he explained not really thinking that she would buy it.

"How smart you are indeed. No wonder you're a math teacher." was all that Tiffany said to it.

Tiffany had to leave but they agreed on another tutoring session for later. But she must have forgotten the actual time and she arrived one hour early. At the front door, she ran into Mrs. Mathews who was just about to leave for her mother's place.

"How may I help you?" asked Mrs. Matthews from Tiffany looking at her from head to toe, disapproving of the revealing outfit.

"Well hello. I'm Tiffany and I'm here for my math tutoring. Is Mr. Matthews ready for me?" she asked perkily. Then she made a bubble gum bubble burst with an audible 'pop' sound to her painted lips and was picking the gum back into her mouth with her tongue.

Even Mrs. Matthews was staring at her huge natural breasts squeezed in by her one-size-too-small tank top and was about to explode,

"Mr. Mathews is not ready and I'm afraid he won't be able to Tutor you at all. And aren't you a little old for high school Math anyway?" she inquired with a suppressed voice.

Tiffany explained to the older woman that yes indeed she was nineteen and in college but Mr. Matthews had been kind enough to help her anyway.

"I see," said Mrs. Matthews and repeated that the tutoring was most certainly canceled. And not just for today but indefinitely.

Tiffany was disappointed and was leaving but as her last words she still managed to ask Mrs. Matthews to tell her greetings to Mr. Matthews and that she is hoping that he is better now. And that his terrible lower body swelling wouldn't come back. Mrs. Matthews was not going to visit her mother anymore - she had some things to discuss with her husband.

Since the math tutoring was off Tiffany had some spare time and she decided to go and see the seashore. There was always such a nice atmosphere at the docks. And right on, almost as soon as she arrived, a really friendly surfer dude came to talk to her.

His name was Ted and he had cool semi-long sunburned hair. His unbuttoned shirt revealed a well-tanned six-pack. Ted told her he knew this awesome place a little further along the beach he would like to show her. She was immediately interested and told Ted she would be more than happy to follow him and see what he had in mind for them.

But when Ted showed him the secluded public building where people could change their swimsuits she told him she wouldn't be fooled that easily. There probably was nothing to see there. But since Ted insisted and she was in a good mood she decided to go along with it anyway.

The sight was however a disappointment just like she knew it would be. In one of the individual locker rooms, there was a hole in the wall where one could spy on the people in the other stall. But since it was a quiet day there was nothing to be seen. There was no one changing their clothes there.

Ted asked her to look carefully anyway and tell him all the details she could see. As she bent over to the hole she could feel Ted right behind him crouching over her. Pushing his crotch against her ass. She giggled and commented that Ted was most certainly not able to look through the hole at the same time with her but he insisted and soon he was practically on her back. Tiffany could feel Ted's hands taking hold of her soft titties and she giggled some more.

Ted was all excited and when he wanted to lift the hem of her dress and drop her panties down she let him do that. It seemed it made Ted so happy so why not? Then Ted did something that had not been agreed on. He had taken his pee-pee out of his pants and started to insert it into Tiffany's vagina from behind. It felt awfully big to Tiffany. Much bigger than Mr. Mathews had been.

When Tiffany asked Ted what he was doing back there with his pee-pee Ted's only answer was that since it was 8 and a half inches she should be calling it a cock. Then he entered Tiffany's pussy with force. Now she was also excited and tested how this new word would fit into her mouth.

"Cock" she whispered. It sounded forbidden and nasty. Then again and again. Soon she was chanting it and pushing her ass back towards Ted. He glued himself on her back and pulled her tits into the open. Then he started mauling the low-hanging udders with rough hands. If there would have been someone on the other side of the hole in the wall those people would definitely have had something worth watching for.

Ted bit a small love bite on her neck when he came deep into Tiffany's pussy. After he withdraw himself Tiffany was able to see his "cock" and it sure was big. Like a mid-size zucchini or something like that. Glistening from their combined juices. Her pussy was throbbing and Tiffany was thinking that while it may be very good for Ted to have such a handsome cock her pussy may have been a couple of clicks too small for such a piece of meat.

Tiffany walked back home with wobbly legs. Amused by the fact that her pussy was leaking to her bare thighs. Ted had wanted to keep her panties as a trophy.

She could have seen Ted again but it happened so that a few days later she found herself a steady boyfriend. To be honest she was not that disappointed for not being able to see Ted since her pussy was just raw after he had used it so relentlessly.

Bob, her new boyfriend on the other hand was just too perfect for her. They had first met just by accident. She had been walking on the street in her skimpiest one-piece pink miniskirt. And Bob just happened to stop by with his Maserati sports car right next to her asking for some instructions on how to get to a certain Louis Vuitton luxury item shop.

As it happened Tiffany knew exactly where the shop was and promised to show him. It was a bit hard for her to get into the low-riding Maserati so that her panties would not be visible to Bob but she tried to do it as elegantly as possible. It was a good coincident that she had just shaven her pussy that morning and selected her smallest white underwear so even if Bob was able to take a glimpse at least she would not seem to be untidy.

They hit it off so well on the way to the shop that Bob invited her to join him in there. And he insisted on buying lots of stuff for her. After shopping they had some lunch and then Bob wanted to show her his apartment. The drive to his place in the hills took nearly 30 minutes. And apparently, there was some sort of epidemic among the men going on since also Bob had that same condition where his penis turned hard just from being near Tiffany.

Luckily for both of them, she knew now exactly how to handle it, and although the interior space of the Maserati was small she managed to crouch over to his seat and massage his penis with her mouth for the most of their drive.

Bob's pants felt expensive when Tiffany opened the zipper and dug out his penis. The pubic hair on Bob's genitalia was trimmed and grey. It surprised her since she had never seen grey ones. But it did make sense since his hair was silvery gray also. Over lunch, Bob had told her his age. At 56 he was 37 years older than her.

He gently caressed Tiffany's blonde hair as she delicately run her lips up and down on his hard penis. When he filled her mouth, as Mr. Matthews had done earlier, he gave lots of compliments on how skillful Tiffany was at sucking his penis and how lucky he had been to find her.

His apartment was this huge mansion where one could get lost. He gave her the grand tour and she was astonished by it all. She lived with her single-parent mum in this two-bedroom condo and Bob's place was so much more.

Last but not least, Bob introduced her to his bedroom. There he wanted to play a little more with her. Dropping her dress down he placed her on the bed under him and believe it or not he wanted to insert his stiff penis between her boobs. As he was her new boyfriend she naturally let him do it and buried his whole shaft inside the volume of her milky white boobs.

Bob went crazy and literally titty-fucked her like there was no tomorrow. Tiffany found it to be quite amusing how he huffed and puffed on top of her in ecstasy. When he had had enough he lowered himself between her legs and entered her pussy. She noticed he wasn't as big as surfer Ted had been but moaned lustily into his ear how big and hard he felt anyway.

Bob was clearly a boob man and most of the time he was fucking her, he had his face buried in her tits. Sucking and biting the large nipples of her tits, licking all over them, and motorboating between them. She pushed her tits together with her hands so that they would please him as much as possible. She was not able to focus on him for the whole time as she was still amazed by his car and his mansion and all the pretty items he had bought her. But Bob was so focused on her breasts that he did not notice a thing. When he finally came inside of her roaring he was completely exhausted.

Tiffany had to go home and she asked if she could borrow his Maserati. This was not okay with Bob since he thought that the 911 Porche in his garage was far more suitable for a girl to ride. So he gave her that one. Tiffany's mother could not believe that she had met such a high-class gentleman. She even joked that Tiffany should ask if he had any single friends with similar status.

As Bob was so perfect for Tiffany there came a time when she wanted her mom Bethany and Bob to meet each other. Bob's eyes were wide as he took in that Tiffany had clearly inherited all her curves from her mother. Bethany was a few years short of forty and not as lean as her 18-year-old daughter but the extra pounds she had were equally distributed into her body. Making her a very very voluptuous milf.

They had a fun afternoon at his place and were chit-chatting this and that. Bethany also marveled at Bob's mansion out loud and bitched about the leaking faucet she had back at her own place. And the stupid landlord who could not get a handyman to fix her plumbing.

Bob laughed at her sincere rant about the faucet and told her he had a guy for almost everything and as a friendly gesture he would like to send a handyman called Rex to her place. And she should not worry about the costs, Bob would take care of those. What he did not mention was that Rex was a legendary pussy-hound and it amused Bob that Rex would definitely make a move on a woman like Bethany. Her huge ass and titties would be irresistible to him. In his mind, this was the next best thing as he knew it would be inappropriate to make a pass on her by himself now that he was dating her daughter.

Tiffany was in her own room when Rex came by. Bethany met him at the door and was surprised to see a six-foot-five muscular black dude. The tool belt on his swaggering hips told her that he was the guy but they shook hands and gave their names anyway.

Bethany was everything Bob had told Rex and he was eating her phat ass with his eyes the whole way to the kitchen. The faucet was fixed in no time and after that, Bethany offered him some lemonade. He accepted it and over the glass of refreshment, he flirted with her outrageously. It was something Bethany was not at all accustomed to.

She had had Tiffany at a very early age. And since Tiffany's father never took any responsibility for her Bethany had just focused on raising Tiffany by herself. She worked at the beauty salon and sometimes helped out at the local parish. Catering for the homeless and so on.

Of course, there had been some men giving her compliments over the years but she thought herself to be fat and old and never gave them a chance. She was not even sure how to proceed with potential boyfriend candidates even if she would have wanted to. The single men at her parish were not assertive enough to make a move and not desirable enough for her to take the initiative.

But now she had this handsome dark handyman flirting with her in her own home. He was giving straight-out sexual hints about her sexy appearance. About how she looked like the type of girl who might have some tasks for him in the bedroom as well as in the kitchen. On top of all the flirting his eyes were definitely lingering far too long on her massive bust.

"Oh my is it hot in here?" she asked as she could feel her own cheeks burning. And that wasn't even all of it. She could clearly feel how her nipples were getting harder and pussy moistening up under his wolfish stare.

He leaned into her and lowered his voice,

"I can definitely see something hot from where I am standing."

Then he kissed her and it was not a kiss of two high school sweethearts under the apple tree but more like this possessive and powerful "soon I'm going to fuck you silly" -type of heated kiss straight on her mouth. Immediately his hands took liberties on her huge ass and she did not resist to any degree.