Should I take on a Toyboy? And would a Toyboy take on me? A young, virile, male equipped with all the expertise and enthusiasm to keep me satiated with his sexy routines and energy (will mine wane, however?), not to mention his loving lust. In my previous life as a wicked wench, I’d never been tempted to traipse around with a Toyboy, but my current sexual landscape, post 50, invited a whole new approach to my pleasure. Bored with my old dildo whose rubbery mould was wearing thin from over use and with its batteries needing constant changing after too many work outs, I decided to explore new horizons with the Real Thing! Too much solo sex certainly didn’t deliver the squeals of delight my body demanded; a scenario far too limited where I longed for a more intimate encounter. My fantasies could no longer keep up with the hot rush of excitement I experienced at bedtime; leaving me feeling deprived and denied of my just desserts.
There was a time in my mid 40s when I flirted with the fantasy (or was it reality?) of a younger man; a gorgeous hunk I once worked with as we enjoyed a decadent dialogue of frivolous fun across our desks. Disappointingly, he did not seem to fancy a fling with me. At quiet moments in the workplace, we swapped stories about our sexual experience, but I clearly failed to turn him on in the same way he inspired me. He was 18 years my junior and charmingly cute, with a risqué repartee that inspired my lust and had me laughing a lot over the computer. We started enjoying drinks after work at my place (he didn’t have a steady girl-friend at the time), watching football together on TV and indulging in some banter about my sporting heroes. Over a few months, we developed a friendship that offered me the brother I’d always wanted but never had, as consummating our verbal intimacy in any other way was strictly out of bounds. One night, with my bravado burning after too many red wines, I tried to push it further, placing my hand deliberately on his dick (on the outside, I didn’t go so far as trying to disrobe him), but he turned and fled out the front door without as much as a goodbye. I was left feeling a trifle ashamed and embarrassed at my antics. Now I really knew what the score was, awarding him full marks for his fanfare of flirting, but assigning him a miserly zero out of 10 for engaging in nothing more than loquacious foreplay. (How easily we are led astray with words spiced with sexual innuendo!) I had since disappeared from our shared workplace, trying to establish a new routine as a freelancer working from home. I didn’t hear from him for a few days, thinking he had abandoned our mutual pursuit of pleasure, if only of the lip service variety. I rang him instead; with a suitable apology about my desire running out of control and I still wanted to know him, albeit in a fraternal way. I hoped he still wanted to know me, too. (I realised he was just an incorrigible flirt! As I was, too!) All these years later, we are still friends, though he now has a stunning, young wife and two, beautiful children.
But would I cope with rejection again; this time as an older and hopefully, wiser woman? And where would I find another young man to play out my carnal cravings? What manner of youth was I looking for, contemplating my new gambit for months until I exhausted all my night time musings and started to roam RSVP on the Internet. There seemed to be no one with the right recipe of ingredients for a romp and I quickly abandoned that avenue of men and took to a few bars in the city. That was far worse, where sexy young men and women in their 20s and 30s lounged closely together, looking askance at me as I sat alone with my chilled champagne. (They don’t realise what they’re missing out on was my deluded consolation, wondering on the whereabouts of men aged 50 plus!) Bars were certainly no longer my scene and I departed to return to RSVP with renewed vigour and hope. This time I wouldn’t give up; I perused the profiles relentlessly for weeks until one of them grabbed my attention. A young man of 34 was searching for an older woman, without children, for fun and good times; dinners, movies and whatever else ensued. I loved eating out (though dining alone in restaurants isn’t much fun and I do that quite often); I’m also a movie addict (at least no one can see you sitting alone in the dark!), so I took a punt and responded. (Hope he doesn’t want a Mother Figure!) Maybe I could finally play the Older Woman who had met the Right Student to share some amorous adventures.
There was a huge age gap though I was remiss at telling him exactly how old I was – suffice to say I stayed at 50 plus and that was accepted. He appeared to be of pleasing appearance – dark brown eyes and fair hair, an IT boffin (I need to hone my computer skills) who was looking for a cure for long, lonely nights. I told him I was self-employed, single and searching for some fun with stimulating conversation and lots of laughs! We arranged to meet at a bar in the city (would the young patrons think I was his mother!) and take it from there. I made a great effort to be dazzling – slinky, black leggings and a loose black dress that flowed around me (I was glad it was summer as I was sporting a bronze beach glow) and I espied him sitting at the bar in the courtyard (I told him I was a smoker who had to sit outside – yes, I should know better) with a bunch of pink carnations lying on the table. (Where were the roses? Was he a cheapskate?) I sauntered sexily towards him as I caught his eye and smiled. James? I asked as I sat down. Indeed, you must be Sari? Of course, I hadn’t told him my real name and wondered whether he had told me. Dismissing that as totally insignificant, he bought me a champagne ( a reliable aphrodisiac ) and then we talked for what seemed a long time. I asked most of the questions (why are some men such conversational cripples?) and as he recanted his life history, I realised we had been designed on different planets. But I tried to listen, adding a few of my own anecdotes in between brief moments of silence and as the night got weary, so did I. After about four drinks, I started to wilt, my eyelids drooping and a sense of expectation for the hours ahead torn asunder. I wanted to go home alone. Doing the sensible thing, he asked – “Do you want to catch a movie at the weekend?” I quickly nodded assent and we arranged a date for Saturday night. (I normally didn’t like going out on Saturday nights as it was the night everyone tried too hard to have a good time!).
We left the bar and he leaned over to kiss me goodnight when I realised I didn’t want to kiss him. He was pleasant enough; he did have a nice face (at least his RSVP photo was real!) and whatever words had passed between us, there had been no intimate connection and not much fun. I was an automaton; my feelings unflamed, where I couldn’t care less about his divorced parents (albeit ultra-conservative, with him the runaway renegade and that did portend of something more promising)), a brother he didn’t get on with and a job in IT he found ultimately boring. It was an exchange of chit chat that went nowhere; too serious and too heavy, an excuse to fill in a lonely night, maybe for both of us ( This Femmosexual does want company sometimes, too). But I did kiss him goodnight (I still haven’t mastered the art of avoiding that without worrying I’d hurt him) but it was a sexy surprise and I was glad I indulged. He made it on that count and I thought instead of the movies, I would ask him over to my place for dinner. (I now had a one track mind!)
Should I or shouldn’t I? And was there a dangerous risk? Maybe he’d turn out to be an axe murderer, a rampant rapist or a drunken misogynist …Should I hedge my bets and dive in…yes, dinner would be great! (I had already invested in one of those portable battery operated alarm systems that lived in my cupboard) It was just three nights away, and what would I cook? What would I wear? On this occasion, I decided on just a couple of drinks so I’d be sober and cool if anything I did want to happen actually happened. (I didn’t want to fall asleep too early as was my habit) Sharing bedtime was clearly my focus and hoped it was his, too. I would look glamorous again, donning my favourite apparel of black leggings with a black and white loose, silk top, embroidered in black lace around the low neck (not too low) that looked sophisticated and stylish. He turned up in jeans and a black T-shirt (he looked casually comfortable) bringing a bottle of Verve Cliquot, my preferred champagne, French style, to match my meal (He’s not a cheapskate!). I was no culinary champion, indeed, I didn’t enjoy kitchen routines very much at all, but I’d concocted a lobster mornay with fresh greens and garlic rice and this time round, he seemed more relaxed. He recited some funny tales about his travels (he’d lived in Paris for six months as an IT whiz kid) and we exchanged European experiences that made the hours tick over in enjoyment.
Then, it came time for Something to happen. I had elaborated on being much older than him, asking why he wanted an Older Woman. “ They’re usually more together, without too many hang ups and few hassles; specially like you if they’ve got no kids,” was the gist of it. I acquiesced; telling him I wanted no more than a fling and some company on dinner dates. But was anything going to happen, as he didn’t even try and kiss me as we sat on the settee drinking coffee and Drambuie (my all time best liqueur). Then, it all came tumbling out. Lulled into a safe sense of security, his feelings flowed as he wrestled with his truth in the dim glow of my apartment. He was GAY! Not what I expected at all, and dumb struck, I said nothing. Sure, he wasn’t a Mommy’s boy, what he wanted I conjectured, was a maiden aunt to confess to and confide in. He hadn’t told his family and wanted an understanding and platonic friend not a lusty liaison. I couldn’t have been that understanding as it didn’t register with me at all. Why do I have all the luck? (Pardon my sarcasm, but I wasn’t feeling too smart right then) Certainly, there would be no frightening fears in bed, hardly; I just didn’t know what to say. Then, another bombshell to shock my mute response – “Are you sure you’re not gay too, as after all, you’ve never been married?” Now I’m a closet lesbian to talk to and make friends with so we could both Come Out together! This wasn’t the script I wrote for the evening.
A few moments passed in private reverie and it was all over until I just laughed, a raucous roar of a kind that resonated through the room while he just sat there and looked away. “Um sorry,” he began, “think I better go.” Good idea, was all I replied, there’s the door. He made his exit, leaving me absolutely stunned and at the same time, pitying his predicament. So be it; I contemplated, here we go again, the same repititive rant that any woman who’s never married (even divorce is a quiet badge of normalcy in our society) is really a secret dike that clings to men for fear of being found out! This time I smiled to myself; lamenting my loss of libido and all expectations of some fun in bed. But I was still alive and would live to tell the tale. Clearly, I didn’t have to cope with the pain of rejection of the usual kind; he had even told me I was a very attractive Older Woman as he shut the door and that was a compliment I found reassuring (Was that my compensation?) Finally, I closed the chapter on chasing a Toyboy, hoping he would find the confidence to Come Out on his own while I knew I’d never try a Toyboy again!