Anne was putting her bag together for her overnight stay that she had arranged with Jason. She smiled at the thought, as that was how they first started their affair, around eighteen months ago.

She thought back to that time.

***

Eighteen months ago

Anne had been married to Neil for a few years following a tough divorce; in fact, Neil had been married before too.

Paula was Anne’s best friend, and they grew closer following Paula’s divorce, which was just as tough and involved two teenage children as well. Working together for a period, being similar ages, and having gone through tough divorces; their friendship seemed strong.

The holiday was planned as a welcomed break, and secretly Anne was excited as she had a crush on Jason, Paula’s husband, and wanted to see what he looked like in his swimming trunks.

Anne had worked with Jason when she worked with Paula and always got on with him and liked him straight away. She couldn’t be sure whether Jason liked her too, but it was clear Paula fancied him.

Paula was the more forward one and soon started dating Jason. Anne was happy for her, but jealous.

Her husband, Neil, was pushing fifty years old, whilst Anne was forty-three at the time, and she was a little bored. Jason just seemed more interesting and was only forty years old, almost a decade younger than Neil.

Paula became a little boastful, too, of marrying Jason within eight months of dating him, and referred to herself as a cougar, being forty-one, a year older.

***

They shared a villa for four nights in Spain. It was a short break away in the sun. On the first night, they arrived late and went straight to bed. They all got on well and were excited about the holiday.

The next morning, they all awoke and met by the pool. Paula was wearing a skimpy white bikini. She was short, around five-feet-one and had such a slim figure, barely a size eight, and had a kind of blonde-grey dyed shoulder-length hair. Considering she had two children, she had the body of a twenty-year-old.

Neil often mentioned how toned Paula was, to Anne’s displeasure. She was unsure, ironically, whether he fancied her.

When Anne saw Jason in his swimming shorts, she fancied him even more. He was around five-foot-ten, medium build with greying hair but had a hairy chest, which she didn’t realise, and she liked hairy chests.

When she looked at Neil, as nice a man as he was, he was too boring for her. This holiday made that even more clear.

Anne did have a brief fling with a director at work; it went on for a few months, but when it got out, she had to leave. Since then, there had been only Neil.

Paula and Jason were kissing and holding hands, whilst Anne and Neil were reading books; occasionally Anne looked up from her book to look at Jason as he played in the pool. They both teased Anne about getting in the pool, but she wasn’t in the mood and was sunbathing.

Anne caught Jason looking up at her. She was wearing quite short shorts, which showed off her shapely legs, but it was her vest top that seemed to be getting his attention, or the cleavage it had on show. Anne was a different shape to Paula, taller, around five-foot-six, curvier, a good size 14, and she had shorter brown hair.

Anne, despite covering them up in frumpy clothes, had a massive pair of jugs.

Jason kept looking across at her and Anne was sure Paula caught him too.

The more Anne watched them prancing around in the pool, the more she wanted Jason.

***

In the evening they went to a restaurant, as they just had a few snacks on the first night. All excited and having a good time, they had a few bottles of wine.

Anne felt Jason stare at her chest. She was wearing a dark yellow dress, not low cut, but it was straining on her chest.

“Bloody hell, I didn’t realise you were so well-endowed, Anne,” Paula said as she was in the toilet with Anne.

“Well, I do cover myself up a lot. I can’t wear all the trendy clothes like you, Paula.”

“Seriously, they are big ones you have. Mine are nothing in comparison.”

“But you are so slim and athletic. You look like a twenty-year-old in your bikini.”

Paula looked at herself in the mirror, smiled and went back to the meal.

It wasn’t the first time Anne had caught Paula starring at her chest. Although she covered it up, you could still tell she was well-endowed, and it was clear that Paula was jealous.

***

On the way back, Jason spoke to Anne for the first time on his own. Paula was ahead with Neil looking for a bar.

“Look at Paula there… she wants to stay out late again, Jason.”

“She sure does… it’s nice to get some time to talk to you. We used to talk loads when we worked together.”

Anne could sense Jason watching her bosom bounce under her dress as she walked. Maybe he was a boob man, and if that were the case, well, maybe she would get the chance to see more of him.

It made her think back to her fling with a previous director where she once worked. Anne always dressed professionally, if a little frumpy, but one summer, her top was a little low-cut and the next minute, he was standing above her asking questions, blatantly staring down her top. He had a reputation, too, but Anne liked having that attention. Emails followed, gifts, then the sex, which was good. He loved playing with her big boobs.

“Yes, we did, I guess Paula doesn’t leave your side much.”

“Don’t say anything, drink talking here. I know you are friends, but I think she sees you as a bit of a threat.”

“A threat?”

“Yes, we were friends first, you know, before me and Paula got together.”

“I guess.”

“And I… had a bit of a crush on you.”

“What?” Anne said and blushed, coming to a stop as they walked.

“Yes, I know it sounds silly now, but I did.”

“Well, so did I on you.”

They both smiled at each other and stopped in the street. Anne wished they were alone and she wasn’t married; she felt herself getting carried away.

“Well, those were the days, you’re all married like me now, Jason.”

“Ha, I know…”

They smiled at each other. Paula and Neil were still a good fifty yards ahead of them.

“Please, take this as a compliment, but if you had a crush on me, you hid it well, Anne.”

“Well, so did you.”

In the distance Paula and Neil had stopped and waved towards them, having stopped; Jason and Anne were getting further behind them. Jason waved back and they started to walk towards Paula and Neil again.

“You also hid those boobs too… they are massive,” whispered Jason, making Anne blush, a little.

“Well, I like to cover myself up.”

“I hope you don’t tomorrow… looking forward to seeing you in some swimwear.”

***

“Is this bikini a little too small, Neil?" Anne asked as they were preparing to go down.

“Well… it’s a little tight... what’s happened there?”

“Oh, we haven’t been abroad for a few years, I guess I should have bought a new one for this trip.”

Anne looked in the mirror. She had quite a curvy body, but the brown patterned bikini top was probably a size too small, and some boob flesh was exposed on the sides. Turning to the side and around, her bikini bottoms still fitted okay. The weight gain over the past few years must have gone more to her bust.

She hoped Jason liked it and was sure he would.

“Can you hear that, Anne?”

“What?”

“Shh… listen closely…”

They both stood still in silence.

They could hear Jason and Paula having sex, the sound of the bed rocking and the giggling sound of lovers exploring their bodies.

Anne was fantasising it was her and not Paula being fucked by Jason. She felt herself feeling quite turned on.

Anne smiled at Neil. “Would you have a problem if I went topless sunbathing?”

With that, she untied the back of the halter neck bikini and let it drop to the floor. Her big boobs just bounced straight out of it.

Looking at Neil, Anne could tell it made no impression on him. Neil used to love her body and her massive boobs. When they dated, he couldn’t take his mouth off her breasts.

Her two moulds of white flesh were just hanging there, all their width and size, and he looked away within a second.

“No, Anne…come on…it’s not that type of trip.”

Anne wasn’t surprised; Neil wasn’t as interested in sex as Anne was.

Anne tried to tease Neil a bit. “Would you not like Jason to see them?”

“What?”

“My boobs, all out… would that worry you?”

“What are you going on about? Is this because Paula was in that skimpy bikini yesterday?”

“Seems you are giving her more attention than your wife.”

“This is going nowhere… I’m going downstairs.”

As Neil left and Anne bent down to pick up her bikini top, she could still hear them having sex.

Looking at herself in the mirror, stood topless, she looked at her breasts hanging there. They were saggy, mainly due to their size, but she did have a big pair of boobs.

If she went topless by the pool today. Jason wouldn’t be able to take his eyes off them, and hopefully his hands and mouth.

***

Jason and Paula went down later in the morning to find Neil and Anne relaxing by the pool.

Paula walked past Anne and whispered, “Sorry we were late, but Jason was rather frisky this morning!"

“Lucky you, I’ve just been sat reading with Neil all morning.”

They both laughed.

“Fancy going on a boat trip later, Anne?”

“Oh, no… not for me, I don’t do boats. Neil will go, though.”

“Are you sure?”

“Definitely, I often get sea sickness. I will go for a walk instead, maybe to one of the beaches.”

“Well, we will be gone a few hours.”

“You will all enjoy it. Like I said, Neil loves it!"

The rest of the morning, there was some small talk, but Anne lay in her sun lounger in her sarong, reading with Neil, whilst Paula and Jason played in the pool.

When they came out to rest on their sun loungers, Jason started looking at Anne again. 

Knowing she had Jason’s attention. Anne stood up and slowly took her sarong off to reveal her bikini. Discreetly she looked down at Jason and saw him staring at her boobs.

“Put them udders away, Anne,” called out Paula in a joking tone, but Anne could tell she was jealous.

“Stop teasing her,” Jason said.

“I think I’ve got a bit bigger since I last wore this bikini,” Anne replied.

“You must have,” Jason said, and smiled at Anne.

Paula gave Jason a nasty look, all whilst Neil sat, still reading his book.

Jason was finding himself wanting Anne; he always fancied her, but seeing her in that bikini and those boobs of hers, he couldn’t get it out of his head.

When Paula wanted sex in the morning, he was thinking of Anne throughout. He felt that Paula was making an extra effort again; her bikini was so skimpy, he even caught Neil looking at it. It was another white one, but it was strapless, like a boob tube, but Paula only had small boobs. Her little white bikini bottoms were quite high cut, so she was showing a lot of her trim body off.

All Jason was thinking was what Anne’s boobs would look like and what her bra size was.

Jason felt himself get hard and was thankful of being able to fake sleeping lying on his front.

After the little talk with Anne, he wanted time on his own with her, and following Paula talking about a boat trip, which he wasn’t keen on, he thought of a plan.

***

Jason was approaching the villa, knowing he would be alone with Anne for at least a few hours. 

When Jason, Paula and Neil were about to board the ship, Jason pretended to feel sick and was worried about sea sickness. Both Paula and Neil offered not to go, but they both were still excited, so it didn’t take much reassurance from Jason that they should still go.

As he went into the villa, Jason could see Anne stood up by the pool. He looked her body up and down. Paula was more of a straight line. Anne was curvy, carrying a little more weight, but looked good in that bikini. Maybe that was because those big moulds of flesh were barely contained.

“Are you OK there, Anne?”

“Oh, Jason what…”

“I told them I didn’t feel too good and needed to come back. Paula and Neil still went on the trip.”

Jason was only a yard away from Anne now. They were looking at each other, both having the same thoughts.

Jason took the extra step and started to kiss Anne and she responded. They embraced themselves and Anne could feel Jason’s hairy chest against her body and his hardening cock against her pussy, a feeling she hadn’t felt in months. They moaned as they kissed and embraced, stood up by the pool.

“I saw you looking at me today, last night too, this was all I could think of…I heard you this morning fucking Paula. I wanted it to be me.”

“I wanted it to be you too.”

Anne broke away from the embrace. “Come on…let’s go inside.”

Jason watched as Anne’s boobs wobbled as she took his hand and led him inside; looking down, he saw her bum wobble too. He couldn’t wait to get that bikini off her.

Anne led Jason straight to her bedroom. 

“Well, are these what you have been looking at all day?” Anne teased Jason as she put her hands under her boobs and moved them up.

Jason was now fully erect.

“I’ve definitely been thinking about getting my hands on them.”

“What would you have done if I went topless?”

Saying that, Anne undid the bow in her halter neck bikini and slowly took it off. Her big tear-shaped boobs tumbled out, spilling and covering her chest.

Anne watched how Jason’s mouth opened. This confirmed that Jason was, without doubt, a boob man. Smiling to herself, Anne thought, how Jason had found the right woman.

Without saying anything, Jason moved forward, pulled Anne’s bikini bottoms down and pushed her onto the bed. As Anne used her legs and feet to kick them off, she was moaning loudly as she felt Jason’s mouth and tongue flicking and licking against her clitoris.

Anne was at the end of the bed, legs open, whilst Jason feasted on her pussy whilst being knelt. He licked away on her pussy, with its little tuft of brown pubic hair. As he looked up, he could see Anne’s boobs wobbling around as she was on her back.

Feeling his cock against the end of the bed, he couldn’t take any more.

Anne moaned and groaned with every flick and lick but wanted those boobs of hers to be wrapped around his cock. Using her legs, she thrust herself forward and spun to her side to get off the bed, as Jason took his pants off, his cock springing forward.

Anne got on her knees, licked his smooth big cock, and then used her hands to put it in her boobs and completely engulfed it in her heaving bosom.

“Do you like this, Jason?”

Jealous of Paula and the sex she had with Jason in the morning, Anne couldn’t help but add, “I don’t think Paula can do this to your cock, Jason.”

Jason couldn’t say anything as he moaned in pleasure, feeling his cock against the cool fatty flesh of her tits.

Anne loved the feeling of Jason’s cock in her boobs. It was maybe seven inches, but it could have been over nine inches and it would have been swallowed up in them. Next time she would make sure she had oil to cover her big boobs in first.

She wanted more than just a summer fling on holiday, and by the sounds and looks on Jason’s face, he would be wanting many, many more sessions.

Letting her bust drop to the side, Anne started to suck Jason’s cock. She suddenly felt like it was a competition with her friend Paula. Anne had heard them have sex in the morning, then Paula gloating. Paula knew Anne could hear and probably thought Anne wished it were her in that bed.

Anne was going to make sure Jason wanted her more. As she came off his mouth, she then climbed on top of Jason and used her hand to guide Jason’s throbbing cock into her pussy. She moaned, feeling his cock inside her, and started to ride Jason. She had missed sex, let alone wanting to fuck Jason.

Jason was lying back, mesmerised by the sight of her boobs wobbling above him, back and forth, like waves of fleshy, doughy tissues.

Anne was so turned on and fucked so hard, she soon shouted out loudly as she climaxed.

As she paused on top of him, Jason watched how her boobs slowly jiggled less and then rested, like two massive, perfectly shaped teardrops. Her perfectly shaped areolas and nipples rested at the end of each teardrop, erect and pointing at him.

Jason imagined what Anne’s boobs were like in her twenties, when they would have been perter, or maybe they never were; they were too heavy to be pert. Reaching up, he cupped each fleshy breast with his hands, squeezed them and pretended to weigh them, and smiled.

Anne giggled, loving the attention she was getting. She had her boobs out for her husband this morning and he wasn’t interested. Jason was obsessed with them already.

“How big are these things?”

“Things?”

“Well, you know…boobs. Do they have a name?”

“I refer to them as my Girls and they seem to like you.”

They both giggled, as they flirted with and teased each other.

“I’m a big girl, Jason,” Anne said as she lowered her hands down and rested them at either side of him, her boobs now touching and squashing against his hairy chest. She giggled at the sensation of her nipples and breast tissue against Jason’s hairy chest.

“They like that then, Anne… a hairy chest…make you giggle?”

“Oh, they do…Jason.”

Slowly Anne rubbed them against his chest and she could feel Jason’s head swelling inside her.

“So how big?”

“Big enough?”

“They are the biggest I’ve ever seen.”

“Well, I’m a 36H.”

“Oh, fucking hell.”

Jason felt even more turned on knowing their size and started to thrust his cock forward, and Anne started to ride him again, faster than last time as Jason moved more but couldn’t keep up with Anne’s quick burst.

Her pussy was so hungry for sex, being deprived of sex for months, she moaned as she orgasmed again.

Jason, wanting to take control, leaned up and Anne slowly got off him. He was a little forceful and moved Anne around him in the bed so her bum was facing him, and he forced his cock into her pussy doggy style and started to fuck her.

“You like that bum of mine too, Jason.”

“Anne, I want to fuck all of you.”

“Oh, Jason… fucking hell.”

They both moaned as Jason fucked her hard. He loved the sound of her huge H-cup boobs clapping together and against her own skin as he fucked her hard.

He wanted Anne so much.

“Fucking hell, Anne… you busty bitch.”

Jason ejaculated all inside her.

After that, they both couldn’t keep their hands off each other, and their affair had started. Anne, having less and less sex with Neil and Paula just not satisfying Jason like Anne could.

Jason loved big boobs.

***

Another lady, twenty years older, was leaving shortly and heading to the same hotel as Anne.

Like Anne, she had some dirty thoughts of what she was planning to do to someone and like Anne was packed with a little treat for them.

Just like Anne, she was a little wet with excitement at what she had planned for that person too.