Not long ago Cindy would’ve said it’s wrong for a 64 year old woman to seduce an 18 year old guy and fuck him senseless. She would never have imagined doing such a thing, but it’s funny how people can change. For most of her life Cindy held conservative views on sex and relationships, and she still does. However, last week young Tommy completely altered her view of sex and intimacy. Cindy would be lying if she claimed it ‘just happened’. It didn’t just happen. Cindy knew what she was doing and it was completely premeditated. It was an afternoon she will never forget. The sexual chemistry was different to anything she’d ever experienced before. Cindy’s passion overflowed. Tommy allowed Cindy to unleash herself. She explored her most intimate desires and learned a lot about herself that day. And of course, Tommy enjoyed it just as much Cindy, which isn’t a surprise since many young men are attracted to older women. Especially beautiful, curvaceous, mature women.
Cindy Santos was born in 1954 to very well off parents who ensured she had everything she needed, such as private schooling, overseas holidays, a trust fund, and so on. During her childhood Cindy always got whatever she desired, and that extended through to her adult life. Her father was a well off businessman from Brazil who made a lot of money running building projects and housing developments. Her mother was an accountant from Mexico. Cindy’s mother was an astute investor, so money was never a problem for the family. As Cindy’s grandmother used to say, Cindy’s father made the money, but her mother multiplied it. To put it bluntly, Cindy has always been very wealthy.
During the late 1950s and early 1960s Cindy and her parents lived in California. She has nothing but good memories of her childhood, even if her father was rarely home. He was a loving father, but work consumed his life. After finishing high-school Cindy moved abroad to attend Oxford University in the UK. She arrived in 1973 and dated two guys during her first two years of study. The first guy was Dave. Dave took Cindy’s virginity, which was a difficult thing for Cindy to go through. Throughout her Catholic upbringing she’d been told that sex out of marriage was a sin. Rather than being a wonderful experience, Cindy felt pangs of guilt and regret for weeks. As a result, her relationship with Dave never developed and they broke up soon after getting together. Cindy’s second boyfriend was Peter. After having sex with him things became awkward, just as it was with Dave. Within a month Cindy was single again.
Outside of those brief relationships Cindy avoided sex. One night stands didn’t interest Cindy and she had to fend off numerous drunken advances from Oxford students. These advances were inevitable. Cindy was extremely beautiful and blessed with an eye-popping figure. At the age of 15 she graduated from a training-bra to a C-cup bra. By the time she started university, three years later, her breasts had grown to EE, and her generous, plump bubble-butt was more than developed. Cindy’s measurements at the age of 18 were 36-24-38. As a result, it seemed as though every guy who met her wanted to fuck her senseless. Cindy’s Brazilian and Mexican roots gave her an exotic look that made her stand out 1970s Britain. However, Cindy wasn’t interested. She was very conservative, especially in comparison to the liberal culture throughout universities in the 1970s. This was largely due to her religious upbringing at private Catholic schools. Those values stayed with Cindy throughout her childhood and teenage years, and although she drifted away from Catholicism at university, Cindy has remained sexually conservative. She’s never been sexually risque, which is why her recent passion filled afternoon with Tommy was so out of character.
In 1976, during her final year as an undergrad, Cindy met her future husband – David Smith. They connected instantly, but David took things slow with Cindy. He understood her needs and was the perfect gentleman in every respect. Cindy fell deeply in love with him. She always felt in control and David allowed Cindy’s intimacy to blossom at her own pace. After dating for two years they got married. Cindy Santos became Cindy Smith. That sounds quick, but back in those days it was common to get married after being together for only a couple of years. In 1980 Cindy finished her PhD in human geography and David gained his PhD in economics. Like Cindy, David came from a rich family and he soon took over his father’s investment business. Cindy’s parents thought he was amazing, especially her mother. Whenever they were all together David and his mother in law talked non-stop about dividends, interest rates, and other economic issues that bored Cindy to death. Sometimes she wondered if her mother loved David more than herself.
But Cindy loved David too. They had a good marriage. Well, it was good for the first 25 years or so. Their sex life was great – he always made Cindy wet and she had no trouble climaxing. He was tender, romantic, and sensual. Cindy was unable to have children, but that didn’t bother David. He said he was happy with his career and he never wanted kids. Cindy wasn’t bothered by her inability to have children either. Becoming a mother never really interested her. After university she had plans to develop a career within academia or governance, but that failed to materialize. She had a good job within a government department in London in the early 1980s. Her career path looked promising, but before she could work her way up they moved to New York for David’s work. His career came before Cindy’s. Throughout most of the 1980s they lived in New York where David became very successful within the finance industry. Meanwhile, Cindy’s life started to resemble that of a socialite. She attended David’s work functions – he would go to these events to secure contracts and deals. Cindy, meanwhile, played the role of the trophy wife.
Most of David’s associates would be happy to work with him once they met Cindy. Or more accurately, once they laid eyes on Cindy. Her body was a curvaceous work of art. The men at David’s social functions were all alpha-males who thought with their dick, rather than their brain. When Cindy attended these events she was dolled up it tight designer dresses, revealing her generous assets. During that time, when Cindy was 27-37 years old, she had a pair of plump, gravity-defying FF breasts. Most of David’s work associates would stare directly at her tits when talking to Cindy. They’d only take their eyes off her chest to glance down at her big, round ass. Since Cindy was only 5’4″ inches tall, her curves were pronounced, and she always wore high-heels.
Cindy spent her time in wealthy circles, and unfortunately was often groped at functions. Those who restrained themselves would only offer inappropriate prepositions – often with the most vulgar language imaginable. Since David was trying to cut deals with these people Cindy had to smile, then do her best to avoid them for the rest of the night. Cindy never had a problem with men admiring her body, but the last thing she wanted was to be grabbed, or told “my cock would look good between your tits” (she was told that numerous times – usually by the most powerful men). Wealthy alpha-males disgust Cindy, as do alpha-males in general. She prefers men to be quiet, reserved, honest, and caring men. Her husband David was exactly that. He was a real gentleman. Cindy loved the way David treated her. It was the opposite of how most men had treated her for as long as she could remember.
That was Cindy’s life for a number of years; she was a posh socialite who attended the fanciest parties in New York where she would meet the most disgusting men in the world. Her own circle of friends back then included other trophy wives. They’d spend their days in beauty parlors preening themselves, or at the gym maintaining their figues. Apart from the cocaine and alcohol fuelled social events, Cindy enjoyed those days. She was also involved in a number of charities, as most of her friends were. There were social events and auctions where the attendees would bid silly money on things they didn’t want, and most certainly didn’t need. However, Cindy prefered to get involved with NGOs and charities at a board level. Cindy was very useful to these organizations thanks to her academic background and contacts via David. She helped them apply for funding, put forward policy proposals, and even carried out research for them. Doing that work kept Cindy grounded. It helped her to understand what life was like for those outside of the New York elite bubble she lived in.
In 1996 they left New York. Through the late 1990s and early 2000s David and Cindy lived in a number of places around the world including Hong Kong, London, Paris, Singapore and Dubai. These cities were wonderful places to live, but the men David worked with in the finance industry never changed. It didn’t matter where in the world they were, if they were at a social event, the men assumed they were entitled to Cindy’s body. Even at the age of 50 Cindy was subjected to leers and indecent proposals. However, to be fair, she did look young for her age, Moreover, Cindy’s breasts and ass were always on display. Those social events were unpleasant to say the least, but the rest of her life was great. She holidayed often with David, or with her girlfriends. They always visited the finest resorts around the world.
Cindy looks back fondly on those years, but the 2007 Global Financial Crisis changed everything. David was overworked and stressed out. As a result, Cindy and David hardly saw each other and their sex life became non-existent. They were fine financially, but David lost his work-life balance and Cindy missed spending quality time with him. For the first time in her life Cindy purchased a vibrator and started watching porn. Buying a vibrator was a big step for her. Of course, she’d always masterbated, but using a sex-toy was different. After she turned 50 Cindy’s appetite for sex increased, while at the same time, the amount of sex she was having decreased.
Cindy’s circle of friends were in the same boat as herself. Once the Global Financial Crisis hit, their husbands worked non-stop, and they were left sexually frustrated too. Most of those women were younger than Cindy and many of them had affairs – gym instructors, pool boys, friends of their husbands, or random guys they picked up at bars when their husbands were away. But Cindy never cheated on David. Not once. She just couldn’t bring herself to do it. Cheating just never felt right for Cindy. She couldn’t understand how her friends did it. That’s not to say she never had the opportunity.
It wasn’t a surprise to have men hit on Cindy, even after the age of 50. She knew she was attractive. She’d been told this throughout her life, time and again. Her friends reminded Cindy constantly. They’d often bemoan their own figure, and tell Cindy how lucky she was. Her breasts and ass were a common topic of conversation once they’d had a few drinks. Unfortunately for them, they had to resort to the surgeon’s knife to get the curves Cindy was born with. Whenever Cindy walked into a room eyes were drawn to her, and this has never changed, even as she aged. In addition to her shapely assets, Cindy possesses an innate grace and poise, as well as a beautiful smile that stopped men in their tracks. She oozes elegance.
Cindy’s smoothe, caramel coloured skin is the result of her Brazilian and Mexican roots. Since she doesn’t have to sunbathe to get a tan, Cindy hasn’t spent too much time under the sun. Her skin remains in very good condition. She has some wrinkles on her face, but they are minor considering her age. Cindy has eaten healthy food all her life and regularly visits spa retreats. Her beauty regime has always been important to her. In 2011 she started lifting weights, which helps keep her body firm. Also, she frequently does cardio and practices yoga to keep fit.
Cindy’s good genes extend beyond her good skin and youthful appearance. She has large almond-shaped eyes, thanks to her mother. Cindy has also been blessed with big pouty lips, high cheekbones, a firm but feminine jaw, and thick luscious black hair. The Brazillian women on her father’s side of the family all have extremely curvaceous bodies – big bums and large busts. Furthermore, the Mexican women on her mother’s side are also rubenesque. Cindy has large, suggestive curves. It was as if God created Cindy to be fucked, but that wasn’t in her nature.
In 2016, after almost a decade of going through the motions, Cindy’s marriage came to an abrupt end. David told her he’d been seeing his young secretary. He said they were in love. Cindy had a feeling something was going on, but David didn’t seem like the kind of guy to have an affair. Cindy was in a state of shock. However, after a year or so, Cindy was able to move on with her life. In many ways it was a relief to be free from what had become a passionless marriage. David was fair throughout the divorce proceedings and he ensured Cindy got half of what he owned, which was a lot. It was an eight figure settlement. That sounds like a lot of money to most people, but when you’ve lived the life Cindy has, it’s a fairly routine amount of money. At the age of 61 she had millions in the bank and was free to do what she wanted. So she travelled.
From 2016 to 2018 Cindy visited her friends. They were scattered around the world; Paris, Berlin, Venice, Miami, and Milan. Cindy briefly dated a guy in Milan – his name was Antonio. They were introduced by Cindy’s friend Maria at a dinner party. She went out with Antonio a few times, but Cindy always felt nervous when she was with him. One night after dinner he invited Cindy back to his place, but she couldn’t do it. She just didn’t feel comfortable.
Since 2008, when Cindy’s relationship with her husband began to deteriorate, she gradually put on weight. In 2008, at the age of 53, her measurements were 39-28-41. Since then her curves have grown. Cindy had periods of time where she’d comfort eat and skip workouts. She even stopped doing yoga for a couple of years, which was unusual for her because she’s been doing yoga since she was 16. By 2014 Cindy’s measurements were 44-31-45. Five years later, in 2019, Cindy’s measurements had increased to 47-34-49. Her breasts are now a large GG, and although they’ve dropped a bit, they remain surprisingly perky for a mature woman. Similarly, her large, plump ass remains firm and round. The stretch marks she developed around her breasts and legs have been filled in as she gained weight. Her body does show signs of aging, but her curves are remarkably firm for a woman in her 60s. Thanks to a regular and intensive exercise program over the past few years Cindy is still turning heads. Cindy’s weight gain hasn’t bothered her. Her curves are all in the right places. She likes her curves and it seems men do too.
In late 2018, after leaving Milan, Cindy decided to visit her friend in Auckland, New Zealand. Her best friend Tracey had migrated to Auckland with her husband a year before Cindy arrived. Tracey couldn’t speak highly enough about the place. Within a few days of staying in Auckland Cindy knew she loved it too. Before long she’d bought herself a house. Twice a week she volunteered with a local think-tank that produces research and policy ideas related to urban issues. Auckland is a city with numerous issues, such as the high cost of housing and transport problems. Working with others involved in the think-tank was very enjoyable for Cindy. She got to know local people and her skills were valued by everyone in the office.
The house Cindy purchased is stunning. It’s a near-new three story house. It has a stone exterior, with neutral tones and high quality fittings throughout. The ground floor has a living room, bedroom, dining area, and a very large kitchen. There’s also an indoor swimming pool, with big glass sliding doors opening out onto a large deck in the backyard. The master bedroom on the second floor includes a large ensuite and a walk-in closet. It opens out onto another balcony. On the second floor there’s also another living room and a small movie theatre. The third floor has two more bedrooms. From the living room on the first floor there’s a door that opens to a small corridor, which leads to the gym and a Jacuzzi room. The gym and Jacuzzi are separated by a glass sliding door. Cindy exercises almost daily in the gym, before soaking in the Jacuzzi. The Jacuzzi is reasonably big. It’s surrounded by tropical plants. Throughout the house there are five bathrooms in total, four bedrooms, and three living rooms. Just to top it off, it’s close to the central city and very private thanks to the surrounding native trees.
Cindy’s life was good, but she was a bit lonely. She dated a few local guys she met through a dating-site, however, Cindy found these guys to be extremely pushy. She wasn’t attracted to any of them and none of them got a second date. Most of the men she met had the alpha-male attitude she was repulsed by. They talked non-stop about what they owned and how important their job was, then they’d expect sex. These men assumed Cindy would simply open her legs and beg them to fuck her because they owned a yacht and a successful business. Time and again Cindy found herself telling them no repeatedly at the end of a date. The worst of these men was a guy called Greg. They went out for a nice meal, however, the conversation left a lot to be desired. He talked non-stop about his investment portfolio. Once they finished eating he suggested they drive to the Auckland waterfront for a walk, but as soon as they got in his car he demanded they go back to his place. Cindy told him she didn’t want to do that, but he insisted. He was one of those men who wasn’t used to hearing the word no. Cindy asked to be dropped home, but he refused. Eventually Cindy threatened to call the police if he didn’t let her out of his car immediately. He dropped her off at the side of the road and Cindy caught a taxi home. That was the last date Cindy went on. She was losing faith in men. She wanted to feel like more than something to be conquered, or a piece of meat. Within a few months of settling in Auckland Cindy found herself using her vibrator more and more.
During the months after that horrible evening with Greg Cindy spent a lot of time alone. She started to use her vibrator more often – at least daily, sometimes more. She was watching a lot of porn and found herself fantasizing regularly. During the late Auckland summer, in March 2019, Cindy got into the habit of having a cup of tea on the balcony outside her bedroom after her afternoon workout. She enjoyed the view over the trees lining her property onto the busy streets below. She’d watch the university students walking to the nearby station to catch the train home. More often than not Cindy’s fingers would drift down to her moistening pussy while she spied on the handsome young students through the trees. Some days she would even finger herself to climax while sitting in the balcony, but most days she’d go back into her bedroom and pleasure herself with her trusty dildo. Before long this became a pattern; most afternoons Cindy found herself fucking her wet pussy with her dildo as she fantasized about those young university boys.
This behaviour was spurred on by what Cindy was viewing on the internet. Cindy got hooked on mature porn. She loved watching slim, young guys fucking plump, older women. There was something erotic about the vast age difference and how it challenged the common assumptions of what a desirable woman looked like. Instead of young, thin women, these porn actresses were old and large. The young guys they fucked more than enjoyed it. Cindy loved seeing their young cocks getting sucked and fucked by curvaceous, mature women. Most of all, Cindy enjoyed seeing these young men jizz all over the faces of the older women. The comments under the video were vulgar, but they echoed Cindy’s thoughts. She often watched these videos while pleasuring herself with her vibrator. The orgasms she experienced were much stronger if she was watching a young guy fuck an old lady senseless. Every time those videos left her pussy dripping wet.