Archive for ‘Toy Boy Tips’

Be afraid; be very afraid – and be brave. It’s got to be done if you two are getting serious.

Depending on the age disparity between you both, it could be the case that your mum and your ladyfriend are closer in age than you and your ladyfriend are. There’s no getting away from the fact that it’s all going to be a bit weird, isn’t it? Especially so for your mum, who probably didn’t imagine her precious little boy ending up with a much older woman. All parents hope for the perfect partner for their son and also the perfect mother for their grandchildren. So, there might be a few disappointments to negotiate before they feel able to accept your situation. Your mum might be the one to feel this the most – simply because you’re dating a woman almost old enough to be your mother…

On the plus side, the age similarity between your mum and your cougar lady could mean that they have stuff in common – and they might even get along swimmingly because of this. You never know!

Do broach the age thing with your parents before you take Ms Cougar home to meet them. It would be mean to land this shock on them – unless they really are extremely liberal. Perhaps your partner could take some flowers for your mum?

Really, your parents’ main concern ought to be your happiness, and if this cougar toyboy relationship is making you truly happy, then who’s to argue with that? If they do take serious issue with it, then you’ll just have to agree to disagree. Respect on both sides will go a long way to keeping this situation sweet.

1. Well dressed: She looks spick and span and scrubbed up, like someone who takes care over her appearance.
2. Hair dye: She might be sneakily covering up a few silver strands to help disguise her real age.
3. Laughter lines: Look at her eyes – a few crinkles at the corners and on her neck will give you a rough idea of age, especially if she’s flashing you a sexy smile.
4. Come hither looks: She’s looking right at you and holding your gaze for longer than is strictly necessary. It’s enough to makes a young man blush!
5. Venue: She doesn’t look the sort who’s into football or rugby, but you always notice her in the bar where you guys go for your after-training drink.
6. Hands: Well manicured – not dirty broken gardening nails but nails poised and prepared to scratch your back.
7. Feet: In summer, look at her feet – do those little piggies look like they’re waiting for a nibble? Are they clean, polished with a big toe pointing in your direction?
8. Confidence: She’s happy enough to be sipping a cocktail alone in a well-healed bar. She’s not gnawing on her nails, looking like a rabbit caught in the headlights.
9. Mystery: She has an air of mysterious allure about her – a wise countenance as if she’s lived life and is harbouring hidden stories.
10. Forward: She’s just ambled over, winked and waved a leaf from her Moleskine under your nose. Written on it is her number. Call it ­– the rewards will be plenty.

You might want to give your cougar lady a special treat now and again – and they do still have birthdays even if they won’t admit it. Just don’t mention figures! Here are some gift ideas for the older woman, which can also be suitable for cougar toyboy dating:

Do Lingerie: You can sneakily discover her size by looking at the heatedly removed undergarments scattered around the bedroom. Quickly check her size when she pops out to the bathroom. It might be considered too rude to ask. Think sophisticated colours such as deep purples or cream and ‘naked’ colours. Girly pinks, slogans and too many frills might be too teenage. Although she wants to feel young, she doesn’t want to feel like mutton dressed as lamb. You should have a pretty good idea of her preferred colours – take note when checking out the labels. A matching set makes a good gift, which you will both appreciate time and time again…

Do Vouchers from her favourite shop. Many people think vouchers are a last-minute cop-out, but I disagree. It’s nice to have a shopping trip look forward to. Make it a bit more special by offering to come along too. Make a day of it: also do lunch or go to the cinema or a gallery.

Do Spa session: Ladies love a relaxing pamper day. Again, perhaps you could arrange to go together and meet up in the whirlpool after each having a massage. All those bubbles and steam baths can provide for a deeply relaxing precursor to sex. Just try to wait ‘til you get home or you might find yourselves featured in the local rag!

Don’ts:

• Chocolates – she might be watching her weight.
• Cheap perfume – she doesn’t want to smell like a hotel toilet.
• Kitchen utensils/ equipment – now come on toyboys, these are liberated ladies!
• Make-up – she knows what she likes; you probably don’t.

If you fancy the sort of getaway with no chance of escape (from prowling cougars) then perhaps a cougar cruise is just right for you. The word ‘cruise’ is dually appropriate in this instance…

In December, Norwegian Cruise Line took 120 singles – older ladies, younger men – on a three-day break from Florida to the Bahamas. Each single on the trip wore a black ‘available’ wristlet in order that eager cougar toyboy dates could easily identify one another and gain entry to the onboard Cougar Cruise parties. The trip was organised by California’s Singles Travel Company and was the third such adventure.

Satisfied female passengers commented that, in Florida, the ratio of middle-aged women to men of the same age is 20:1. So, it’s a necessary exploit for midlife ladies to go in search of fun among the younger age group where there’s a larger pool teaming with fresh catches waiting to be hooked. Fifty-eight older women and sixty-nine young men cruised the balmy Bahamian seas so there was plenty of choice for the Florida ladies. I expect some managed to trawl a multiple catch so I doubt any toyboys were left high and dry.

The next cougar cruise is set to take place in the Mediterranean from April 16^th-21^st 2011. With beautiful views both onboard and out to sea, why not take the plunge to see if it floats your boat as a novel new way to meet the cougar/ toyboy of your dreams?

The first few dates with your cougar conquest will probably involve dining and drinking at some point. Don’t expect her to pay just because she’s older and financially better off than you are.  She’ll appreciate it if you at least offer to pay – it can make someone feel special and cared for, so do be prepared financially for this eventuality. You both might decide on going Dutch, but it’s always nice to be treated from time to time. On the other hand, don’t absolutely insist on always paying – a cougar lady might have been in a one-sided relationship where her former husband held the purse strings. Her financial independence is something she enjoys; she might want to take the initiative and treat the bloke for a change. Whatever the scenario, don’t be afraid to discuss money before the date to save spoiling the atmosphere with awkward fumbling embarrassment over the bill on the night.

Your mature cougar lady might expect certain behaviours that you’re not used to with younger women. Do be chivalrous and open doors for her, and offer a compliment about her attire. Don’t stare at her boobs – keep those eyes above her neckline to show some respect: Although cougar toyboy dating can often be more sex-orientated than more conventional relationships, she doesn’t want to be treated like the raspberry tart you’re having for dessert – at least not over dinner. Drinking too much is also a no-no – it won’t impress. Younger women might be slinging back shots and be happy to drink you under the table, but cougars are more classy than that.

If sex is on the cards then be prepared. Cougar toyboy dating is likely to be centred around sex and you might not be the first young man in her recent history. STIs are rife among your own age group and growing in the middle-age group, so do use ‘something’ – don’t expect to go bareback just because the risk of pregnancy is lower.

If you watch Eastenders, you might have noticed the recent development of a cougar toyboy storyline between Glenda (Ronnie and Roxy’s mum) and the handsome young Leon. While working in the bookies, Glenda performs her ‘come and get me’ cougar magic on him in a bid to prove her unceasing pulling power to frumpy old Carol. Leon has a girlfriend (the feisty Zsa Zsa) but this minor detail doesn’t stop him wanting to have his cougar cake and eat it. He plans a licentious liaison with Glenda before hoping to hit the road on a trip with his girlfriend. Zsa Zsa, being a spunky tough-cookie, finds out and reaps revenge by public humiliation. She lures him on sexual promises then steals all his clothes apart from his birthday suit, leaving him displaying family jewels that Queen Victoria herself would covet.

If you’re in a long-term relationship with Amazon-woman, you might want to think twice about the understandable temptations of that cougar-on-the-side if you want to keep hold of your chances of having children in later life! Of course, we understand that the very danger of this set-up could make the illicit tasting of toyboy cougar dating delights all the more sweet. I do believe, however, that it’s rarely a case of ‘if’ they find out, more a case of ‘when’.

It’s quite conceivable that your secret cougar lady might actually feel flattered that you also have a young attractive girlfriend, suggesting that she is still hot enough to compete with younger women. It could, however, come as quite a blow to a cougar’s self-esteem to discover (if she didn’t already know) that you’re attached to a much younger woman than she is. To the young lady girlfriend it might be insulting to find out you have two-timed her with someone old enough to be her mother. Try to be a good judge of the emotional state of those involved in order to avoid hurting people. ‘Open’ relationships can be ok if all involved are in agreement and know the score, but not if one person is unhappy with the situation. You could end up with more cake than you can manage, or you could be left without one single miserable crumb.

Have you been involved in any cougar toyboy triangles, and what happened? Would you consider having an illicit cougar toyboy affair?

A well-turned-out toyboy is a must for a first date with any sophisticated cougar lady. We’re not necessarily talking formal threads here, but it’s nice to think that a young man has at least seen a bar of soap in an effort to scrub up in preparation; it’s all about respect.

You might be very fond of that Inbetweeners T-shirt stating all manner of side-splitting filth to describe how women flock around you, but being referred to using such vocabulary won’t overly thrill your date. Yes, you probably do possess the powers to attract women, but there really is no need to advertise it with comedy quips emblazoned across your chest. Save that for a night out with mates. We’re not saying that cougars aren’t into puerile humour – I’m sure some of them are – only that she might not want to feel like she’s dating her nephew. And, despite how casual the relationship might be, she certainly wants to feel respected. Such clothing is highly suitable for impressing your peers, but not your older-lady lover.

I suggest going for a casual-but-clean look (depending on where the two of you are going for your cougar/toyboy date). You can’t go wrong with a crisp shirt and trousers or jeans. Add a jacket if you’re dining somewhere swanky. However, you’ll want to feel comfortable in your own skin on the date, so don’t stray too far off your usual beaten track when it comes to fashion choices.

Do plan ahead if there’s any chance that you’ll both end up at your place: When was the last time you laundered the sheets? Snuggling up to three months’ worth of your old skin cells won’t be much of a turn-on. And, does that Arsenal duvet cover really cut the mustard? I hope I’m not generalising too much, but young men aren’t usually renowned for their domestic flair.

As a lady with plenty of experience in the toy boy dating department, I’d say that clothing with buttons to undo is a great turn-on. Shirt buttons are to a woman what a dress zip is to a man. Imagine unwrapping a longed-for gift, or even ripping that wrapping off in a flurry of heated passion because you just can’t wait to play with what’s hidden inside. Yes, buttons for cougar dating are highly recommended…

You’ve managed to bag a date with the mysterious sexy cougar lady that you’ve had your beady eye on for a while. But what does a young toy boy talk about to an older, much more experienced and worldly woman?

In terms of conversation topics, you mustn’t forget that there is an age gap however insignificant you feel that is. Chances are that she’s more likely to have interests in common with your mother than with you. Don’t, whatever you do, talk about your mother! Try not to mention how you still take your washing home to her on weekends, or that you still live at home, all tucked up with your Ninja Turtles, or similar. It will make you seem far too immature for her to consider any liaison possible. She doesn’t want to feel like a cradle-snatcher.

Don’t say, ‘My mum’s got a dress just like that’, even if she has. We are trying to avoid drawing attention to the age gap issue and the unleapable chasm that it might open up between you. The last thing any older woman wants to feel is just that – old! One of the reasons she’s dating you is that she wants to feel young again, but not quite to the extent that she wants to share all your youthly interests. For example, please don’t expect her to join you in staying up until all hours playing Grand Theft Auto, especially after sex. Not polite, and possibly quite offensive. Unless she’s IT-savvy, there might be gaps in techy-type knowledge too: Don’t be surprised if she glazes over when you flash your new phone with its fifty comedy ringtones and fancy apps.

You could compliment her on her looks – her clothes or jewellery. Not that we’re saying she’s superficial and you can woo her with flattery alone. Try to keep conversation current and up-to-date. You could talk about the latest films you’ve seen, books you’ve read, interesting or funny news items, TV gossip, community events, jobs, travel etc. Happy chatty cougar dating!

Back in the days of the film character that gave this website its name, it was pretty rare for an older woman to date a younger man.

Or rather, if they were involved with someone young enough to be their son, it wasn’t something that the 1960s Mrs Robinsons talked about in public.

But times have changed and many older women are now only too happy to admit that they prefer their men on the good side of 30 – or even younger!

In fact, 2010 is predicted to be the Year of the Cougar – and why not?

An ‘older woman’ these days is likely to be youthful looking, in great physical shape and looking for some excitement in her life. But often, she’s already accomplished a great deal in her career and knows the importance of relationships.

Cue the younger man, stage right.  He’s tired of being given the brush off by trendy teenagers and Twenty-somethings who aren’t interested in him unless he’s got a high flying job and a wardrobe full of designer gear.

In fact, Mrs Robinson is just what he’s looking for. A woman who will appreciate him for what he is. A woman who knows what she wants in life and has the self confidence to go for it.

This can be a refreshing change for a young guy who’s used to dating girls of his own age.  Often, they don’t really know what they want themselves so how on earth is their guy supposed to figure it out 

Older women are usually comfortable with themselves – or at least they’ve got over the complex they had at one time about their ears being too big or their complexion being less than perfect.

Of course, an older woman still expects to be treated decently and complimented on her appearance (that’s a given for any female after all!). But she won’t be constantly looking for reassurance that she looks great and she won’t turn it into a huge drama if you ring her 10 minutes later than you promised.

Even better, an older woman has the kind of level-headed maturity that comes only with life experience. She’s unlikely to be into the kind of dating games that younger women like to play.

And that makes things much less complicated for everyone. She knows what she’s looking for and unlike her younger counterparts, she isn’t too shy to let her younger guy in on the secret.

Then there’s her wealth of experience – both sexual and otherwise.  Many younger men have stumbled through a number of relationships with women of their own age.

But they still don’t really know a lot about what women want because so many younger women are loathe to spell it out. Often, the only thing a guy knows is what she didn’t like!

So Mrs Robinson comes into her own here!  She’s been there and bought the t-shirt – and often she’s only too happy to teach a younger guy a few bedroom tricks.

But of course she has lots of experience outside of the bedroom too and can be a great help in dealing with difficult situations – such as when you’ve had a falling out with your best mate or a tricky situation at work.

Chances are, she’s gone through something similar and knows the pros and cons of the different solutions involved.

And last but not least, she’s often already had her fairytale White Wedding with huge reception, complete with horse drawn carriage and ice sculptures.

So she knows only too well that Happy Ever After isn’t everything it’s cracked up to be and that buying your first home can bring stress, expense and lots of tiring decorating – rather than the perfect married life you see in the movies.

In short, she’s reached a stage in her life when it’s not all about climbing the career ladder, getting kids into the best nursery and owning the biggest house on the street.

It’s more about personal fulfilment, making time for the things that really matter in life and – most of all – having a great time.

But don’t make the mistake of thinking that it’s her younger beau rather than the cougar herself who stands to benefit from the older woman/younger man relationship.

Far from it – there are lots of bonuses for her too as we’ll outline in our next article – What’s In It for the Cougar.