Category Archives: Gay / Bisexual Sex
Playing With Young Gay Love – What Cougar can turn down a beautiful teen whatever his alleged sexuality?
There comes a time in every single woman’s life when she has the thought on a mad night out ‘I’m too old for this.’
It happened to me not long before my thirtieth birthday. After a troublesome few years, I’d scuttled home to Australia to rest, recuperate, mend a broken heart and lose nine stone. I looked (and this is arrogant) hot when I returned. Dropping from a size 28 to a size 12 was hard work, but I must’ve looked good because when I scored a job in a music company I was pretty much the talk of the room. The loud brash exceptionally good-looking Australian. I’m not sure how true that last sentence was but in my mind, I like to think that’s how I was perceived. If anything I had the confidence to think that way and maybe that rubbed off.
Anyway the music company I worked for (at that time) was very hip and cool. It’s a tough industry to crack, even a shitty administration job like I had. Our floor was pretty much full of school leavers on their first jobs, or dreamers like me that worked their for shit money but a great company culture as we planned on how we’d get our big break in music/writing/acting/performing/dancing etc.
Because about ten of us joined at the same time, we were sent on all the training courses together. Enter D (I can’t mention this individual by name because he’s a model and I’m not sure how relevant his sexuality is to his career or if this confession would impact on it in any way and come back to bite me in the arse so to speak). D was truly beautiful. He was Irish and had only just turned 18. He’d done a modelling campaign for ‘Next’ I think and also a massive exclusive photo shoot for a big magazine like GQ or the likes for a designer label along the lines of Armani of Dolce and Gabanna. Talent spotted for both jobs, he’d headed to London on the premise that his modelling career would go from strength to strength and he’d become a professional. He wasn’t a classic catwalk model, because he didn’t have the height. He was five foot nine which immediately restricted his career. He was striking to look at. Not traditionally handsome, he was pale and slim, but had perfect symmetrical bone structure in a very lean, chiselled way. He had thick dark brown hair reached the collar of is short and his styled fringe was perfect to droop in his eyes so he could flick it out flirtatiously when required. All that combines with the eyes greener than the foliage of a tree, you couldn’t take your eyes off him. Eye-catching he was. I could see why he was spotted by agents, but there would be those that would refer to him as ‘ugly-beautiful’ so unusual was his appearance.
Apart from the modelling opportunities, I suspect being in one of the cities the embraced homosexuality (especially as out office was in Soho) held additional appeal. Even the younger women in the office weren’t overly familiar with how to conduct a friendship with a young gay male. Mostly your first gay friendships end up with you having a crush on him. After the first one is out-of-the-way you realize nothing can come of it sexually and instead of instinctively viewing them as ‘potential father’s’ An experienced fag hag from way back, I was more than happy to take him under my wing. Having been out of the entertainment industry for nearly two years, to re-enter the gay scene was a blessing for me. I was happy, funny, confident and loving being back with a very young, very new gay best friend. He was relived to have someone who knew their way around the scene and was willing to accompany him on all kinds of outings. I also acted as a chaperone taking him to open castings. Perhaps the most important time my presence was required when we went to one ‘modelling’ agency that was trying to talk him into working in gay-porn. Not on my watch!
Crushingly as I told my oldest and closest gay friend of D (who he chose to refer to as my ‘new gay puppy’) his reckoning was that D was attracted to my maternal side. Huffily I refused to accept this. I was still hip and down with the kids.
D was living with an American guy he’d met online. Turned out cyber-space didn’t translate to the real world. The American insisted D come and live with him but after a month was retracting the offer. With no money to pay rent, D refused to budge and somehow they managed through tearing each others heart-strings as they went.
In 2007, when McFly were at their peak, they were playing a gig at the old G-A-Y by Tottenham Court Road. There was quite a débâcle at the time because Jeremy Joseph was being an out and out prick, refusing to let young groups of girls attend the concert. I don’t agree with ostracising anyone on any grounds, but in fairness to the repulsive Mr Joseph, screaming teenagers did kill the ambience of G-A-Y considerably. It wasn’t their enthusiasm that was the problem, rather their reaction to being in an ‘Oh My God’ gay club. Looking at the men (and myself who perhaps appeared lesbionic wit stereotypical short hair) they were gaping like they’d discovered aliens. That did piss me of because it does kill the vibe, when straight girls are looking at regular patrons like they’ve gone safari with the wild willy lovers.
Anyway, D decided that he, his flat mate and a visiting friend should go see the concert with me. How could I refuse his irresistible green eyes? I agreed and meeting them high I was as mellow as they come. Having bought our tickets thanks to D’s age we were checked. D bought his passport to confirm he was eighteen and we skipped passed the hordes of screaming girls begging to be let in.
All was going well in my knee-high boots and extraordinarily short dress. Until some old man was trying the moves on me. He was clearly gay but as he was facing a dry night I think he adopted the mentality that every hole is a goal. Bumping and grinding against me, I pushed him away gently. The second time a little more forcefully but with a smile. The third time I snapped and told him to get away from me. He then proceeded to throw a pint on me. The pint drenched me from head to toe, I could feel my make up sticky and probably likely to be running down my face and my dressed reeked of beer. It was only midnight and we were due to be out till 6am, so I was less than impressed with his actions. Fortunately so to was the Australian gay guy behind me who caught a few splashed himself. He and his boyfriend turned on the guy, to chastise him for his behaviour towards a woman and fellow county.
I did my best to calm everyone down and try to drop it (after all I was the one who’d be suffering all night) but D’s flatmate decided to find him and fill him in on the event that had taken over. Leaping down from the stage where he’d been dancing, he stormed up to the repugnant man in his late 60s early seventies and was shouting why he’d done it. I grabbed D to draw him back and tell him not to worry and let it spoil out evening, but he was furious demanding to know what the guys problem was. In an instance, the seventy year old gay guy landed a quick jab and caught D on the cheek.
It was my turn to rage. D was reeling but still upright. Seeing only red I grabbed the guy by the shirt cussing and swearing and telling him I was going to fucking kill him for hitting a kid like that. The old man pushed me off, the Australian gay guy saw it. His partner steadied me on my four-inch heels and the Australian then started rough-housing. Amongst all this action was a significant proportion of screaming young teens looking shocked at the aggression and violence taking place on the dance floor. Don’t blame the boys, girls – I was equally up for a fight.
Security entered to split everyone up. The Australian was defending our part but D, myself and the old codger were ejected from the main club. Discussing the issue with management, I could hear McFly preparing to come on stage and realized we were going to miss the highlight and purpose of our evening. D obviously thought the same because he put on a spectacular scene about me being his chaperone for a massive photo-shoot with Versace and now he’d most likely lose the job because of the bruise. He demanded to know what they’d do about and was insisting he wanted names to pass on to his employer and that kind of empty but potentially dangerous threats. I have to say, is efforts were so strong I was inclined to suggest acting if the modelling didn’t work out. The next thing I know security have their arms on us dragging us through the absolutely jammed club to get us to the front of the stage to watch McFly. Yes seeing McFly up close and personal was a great experience, no having an entire club HATE you for a public display of favouritism when many had queued for their positions wasn’t fun.
With thousands of evil eyes glaring at me, my liquid foundation running and exuding an aroma of beer, there and ten instead of seeing it as fun or an adventure I thought ‘I’m too old for this!’ – I was.
That was my last night out with D and his friends. My socializing and love of drama was diminishing the closer I got to thirty. We still spent whatever time we could at work and remained close.
One morning I get a call from his asking if I’ll come round and help him put his tanning lotion on. It was a Sunday and I had no inclination leave the bed or my TV, but our night out hadn’t been his fault so being seen to punish him was unfair.
Accommodating himself in the nearly redeveloped area of Canary Wharf the flat, within which he was staying rent free until the American online ex could boot him out, was out of this world in terms of size, layout, the quality and modern sleek urban look of the place. I could fully understand why he didn’t leave. The view, the facilities on offer and high tech gadgets made it a playground for anyone who loved luxury and opulence.
I chatted to his mates who had been out the previous night and were debating on whether or not to head out again. D declined the offer of drugs, as did I, because he was a clean living guy that loved life not alcohol and drugs.
Entering his bedroom, he stripped off the his shirt. Even though I’d lost weight he remained rake thin. Squeezing the lotion in my hand and then rubbing his torso had me flummoxed. He was a friend. This was a normal thing to do. But no one can deny a physical appreciation of another human being whatever their sex life is like behind private doors.
It was hard not to be turned on when I was running my hands all over his him. Shoulder blades protruding, his back was lengthy with a straight spine and no hair whatsoever. Tackling the front of him was worse because we had to make eye contact and conversation. Aimless chit chatter, all the while I’m caressing this chest and washboard stomach that was an eight pack as opposed to a six pack.
Having finished, he removed his jeans for me to do his legs as well. Running my hands up and down the length of his chicken-like legs, was too intimate and strange given the length (five months) and nature (platonic) of our relationship. He obviously thought the same because when I dared to raise my eyes to the white tight legged boxers I could see he was erect. I could also see he had a proper porno cock. My head was telling me one thing, my hormones another.
Whether I was drooling, I’m not sure, but seeing my unsubtle examination of the package with one hand he pulled down the front of is boxers slowly. Bare chested and pubescent in appearance, he looked like a little boy. The thatch of hair from naval to crotch was non-existent. He was teasing me deliberately, moving his hand down his stomach, exposing the flesh leading to his pubic region slowly. The bush may have been untamed, but it wasn’t like he needed to trim the area to make him look ‘bigger’ (as some men chose to. Releasing a seven and a half-inch wonder, my eyes watered and I got was soaking wet in an instant, I could feel it on my knickers.
‘You can suck me off if you want,’ he said simply.
I wanted to, my god how I wanted to. Licking from the base of his cock to the head I’d run out of saliva. I couldn’t just use my tongue to lube him for my mouth, I’d have to spit in my hand to work the shaft. I already knew due to the thickness of his bratwurst-shaped penis, I’d struggle to swallow much of him. He was young enough not to exercise any caution or consider the repercussions on our friendship if this was to go ahead.
Standing up he decided to remind me he had fucked women before and had a girlfriend in Ireland who he slept with regularly before outing himself on arrival in London.
I always swore never to sleep with friends, but was he a friend or just a work college I clicked with.
‘Fuck it,’ I thought and undid my jeans and dropped my drawers. D closed and locked the door to his bedroom. Without further ado he bent me over the bed. He was so slight I wasn’t sure where his strength emanated from. As I felt my feet involuntarily moving to adopt a stance to allow him to penetrate me, I did think it prudent I raise the issue of protection. Unfazed by the request, I was taken aback he had such a supply of them in his bedside drawer. Breaking the first one in his urgency to get laid, he retrieved another within seconds. Arms resting on the bed, pussy dripping I was ready to go.
No warning, just a sharp thrust to penetrate me. The shock of the size of the fat cock had me panting, gripping the bed and riding the length down to bump on his pubic region. When I felt my pussy lips springing off from his pubic hair I knew I was imbibing his full length.
It was hard, fast, rough and ready. I liked it. There was no affection or caressing of areas that differentiated the two of us physically in accordance to our gender. My clit and breasts were neglected. This wasn’t a major problem for me, because with my head planted firmly on the mattress I could use one hand to reach my climax anyway.
Rubbing my bud, it was easy to bring myself to the brink and go with the flow. D on the other hand wasn’t as fluid in movements as myself. He happily pumped and pounded my cunt, relishing in delight at my grunts as he shoved deep in me. Slamming into me with such force that the bed was moving round the room with me, I guess the pneumatic drill approach may well be best if you’re having sex with someone you wouldn’t normally. I support this statement with the fact that he came, because he came very speedily. Groaning loudly, I was in no doubt his collection of friends knew exactly what was going on.
Suffice to say my departure was imminent. I left with a wave and have a nice night. Within a couple of weeks I’m pleased to say the American managed to boot D out. With no savings, he was forced to return to Ireland, ensuring his only option was to skive off his parents. I don’t mean it in a horrible way, BUT as fun as it is to hold your hand up and say I’m twenty-nine and I fucked a teenage gay model the aftermath and awkwardness did mean losing a friend. The nature of the friendship changed irrevocably. We’d gone down a path we shouldn’t have. It affirmed my belief that you shouldn’t sleep with friends. It affirmed me that as a highly sexed woman, I still had it even with the most difficult erotic scenarios.
In fact, D’s departure from London had occurred before the rub on tanning lotion finally came off. A heavily tanned arse (brown bum) conflicting with my pale and porcelain skin was a major passion killer. I won’t lie to you. There a significant price to pay for carrying out a little taboo barely legal gay sex. I couldn’t risk sexual rejection, thus was obligated to put my sex life on hold while the tanning lotion faded. For the one woman wanting the one hundred dicks it was a daunting process.
By rite of passage most women at some point encounter their first gay-best-friend. This normally results in developing an irrational crush on an unavailable an impossible dream. That said depending on what age or even what stage you both are at sexually that doesn’t mean the gay-best-friend is without sexual benefit.
In my case I managed to avoid falling for some pretty boy that would woo me with attention, use my looks, status and wit as a public accessory and then eventually become so immersed in Gaysville I’d end up being yesterday’s news. No as I was being wooed and wheeled out to his posse of gay friends, I found another guy that was infinitely funnier who I thought was gay (he wasn’t) and focussed my attentions on him. Thus I never experienced any jealousy or feelings of being an attentive plaything or my presence required merely as a means to prop up an ego.
That doesn’t mean I escaped sleeping with a gay man (or two or three). The first though in question was at the bi-curious stage. But for me the old adage Bi-Now, Gay Later holds a lot of weight.
My heavy immersion into gay culture was helped by the fact that I worked in the theatrical industry which has (thank god) a high percentage of lovely gay men – because there is nothing better than being surrounded by pretty, creative men – does wonders for the ego (and image).
The place I found my gay liaison was in the old G-A-Y by Tottenham Court Road, on a night when me and my theatre’s gang had decided to see Erasure playing live there. You couldn’t have had a gayer evening, with Andy Bell dancing round stage with his feather boa and artificial hip.
Still they were only doing a short set so our evening was filled with a lot of alcohol, a lot of gossip, a lot of dancing to old skool cheesy pop tunes and much flirting and making friends regardless of sexuality.
As the minute and hour hand moved precariously round to the time the concert was due to start the auditorium filled up and the throng dancing on the stage began to climb down and push back the die-hard fans that had been dancing by the stage all night to reserve a pole front row position.
I myself was a die-hard fan so stood ground as the young boys climbed down and realised they were being sent by a tidal wave of bopping bodies to the back of the club. Our group were huddled close and I was feeling exceptionally excited about Andy and Vince taking the stage. I was also enjoying the friendly ambience of the venue (Erasure didn’t really warrant screaming teen girls so there was no heterophobic vibes emanating from Jeremy Joseph’s crew as is the case when McFly or One Direction play such gigs).
Sitting on the stage, looking rather wasted was a guy who was not a pretty, young, thing. He wasn’t unpretty and he wasn’t old, but he wasn’t ‘a type’. In fact I guess the term ‘straight acting’ could be applied. He was mid 20s, with a pleasant tanned mannish face and mousy blonde hair in curtains that had grown out and hung appealingly in his eyes. His thighs filled out his jeans and the bulge looked promising. He was wearing a loose t-shirt and in fairness is was not an outfit designed to peacock his gym acquired frame.
As the crowd heaved forward I took the opportunity to press myself between his thighs; him sitting on the stage, me standing between his legs. With more movement and bustle I steadied myself by gripping his upper things. This tactile and intimate physical contact mustered him out of his alcoholic daze.
I asked his name and he told me (I won’t pretend for a second I can remember it). He asked mine and given his drunkenness, the roar of a full nightclub my Australia accent and the announcer drumming up the ever enthusiastic crowd after about 50 repeats I got him to understand it.
From there the game began. Tact was never a strength when it came to me quickly assorting potential fucks in such a sparse sexual heterosexual hunting ground. So I just blarted out the question if he was gay. He slowly shook his head and shrugged that he was there with his mates. When I asked where his mates were, he didn’t know. When I asked their names, he couldn’t remember. Being open and honest I said I didn’t think he’d come with mates.
By now he appreciated there was sex up for grabs (maybe not in the package he’d been hoping for but every hole’s a goal as they say) so began to come round and add a little coherency to the conversation if the invitation was not to be be retracted. He amended his story saying his friends had told him Erasure were a really good band so on their advice he thought he’d come see them – it just so happened to be at a gay venue. I pressed on as to why he hadn’t seen them at the Albert Hall (or some such major venue) earlier in the evening with his friends rather than going solo to a 1am gig at G-A-Y.
Eventually he caved; mumbling about sleeping with women but…kind of liking men…trying it out. I’m not one to usually go down that path – it doesn’t do a lot for me – the sexually confused thing. Basically I’d done it myself some years earlier and been not so kind to some lesbians because I decided I was curious. I suspect in hindsight feelings may have been hurt whilst I wanted to try some new things out, selfishly considering my own feelings and emotions on the matter.
But as I smiled and went to walk away, Erasure landed on stage, he slid off the stage and had me in a clinch and I was unable to resist his lips pressing down on mine. It was like the merest hint of sex had sobered him and he was pulling me to him, kissing me feverishly and placing my hand on that ever expanding bulge of denim by his crutch. Coupled with Erasure belting out a more mellow number my resolve weakened. I began to feel wave of heterophobia growing as a seemingly ‘straight’ couple made a very public display of affection in front of a notoriously gay crowd, in a gay venue with a very gay band.
He grabbed my wrist to pull me a way, but I was with my friends. I shook my head and said he was here to try new things and doubtless in an hour or two he could walk out with the goods he intended rather than a substitute. As ‘Give A Little Respect’ came on, my friends enticed me back for a dance and the boy became lost in the crowd.
A few hours later though, whilst the club was emptying and I was waiting for my friends to return with their coats he appeared staggering up the staircase from the men’s toilets – alone.
‘I knew I’d get to fuck you tonight,’ was all he said. And he did.
Resigned myself I took him back to my single room at the YWCA. The security guards, either because they got off on the idea of illicit sex happening in a Christian residence, too tired to argue or just easygoingness let him through with me; without me having to sign him in or explain his nocturnal visit.
For a guy that was preparing to change teams, I have to admit, to his credit, he’d obviously served well and done a decent tour of duty with the heteros. I mean doggedly (though not in style) determined to rut he took his time undressing me. I was by no means dressed for play in tasselled cargos and singlet with netted top over it. But his masculinity was impressive as he dis-robed me item by item. The top was easy to get off. He reached round the back to unhook my bra only to find I was wearing a sports bra. Not to let that dampen the affair he at first just forced the bra down so both my boobs spring out and he nuzzled them for a good time – breathing in the scent of me. Almost delighting in the femininity of me. After spending what I was beginning to think an inordinate amount of attention on my breasts he pulled the sports bra back up and over my head and arms so I could slip out.
Still standing he dropped to his knees and pressed his face against my tummy. I felt the hands creep up to massage my boobs again. I’ve never been too keen on breast play (until recently) so whilst he honked them like some 4 year old in one of those 50p stable car rides you find in supermarkets with steering wheels and horns, I kinda felt it was getting a little Oedipus-like in nature.
Impressively whilst groping my breasts he managed to undo the button and zip on my trousers. The button ok, it was quite loose but I worried about his teeth pulling down the zipper – surely metal can do damage to teeth and the zipper was quite stiff? Once again he was nuzzling my snatch, breathing in from where all my woman hood stemmed. He peeled how my knickers and flicked his tongue round my clit. Without further ado he pushed me to the bed to continue his servicing of me.
The trousers were restrictive, making for an awkward leg spread. I was left rather ungraciously and certainly with allure was kicking at least one leg out of the trousers to allow for a wide spread and better access to my clit. I think maybe in his drunken stupor he didn’t have the faculties to see how unsexy the action being carried out was. He was so intent on not only attempting to give me a clitoral orgasm but taste all of me I had time to remove the trousers hanging onto my right calf and pull off the thick woollen socks that were a favourite of mine at that most wonderful time of the year.
After the correct amount of moans to provide him with the notion he’d bought me to orgasm (he didn’t) he pushed his face as deep in my slit as possible. Smearing his face in juices. Pushing 3 fingers from both hands in as deep as they could go, twisting them pleasurably and then licking them on exit.
He stood up and unbuckled his jeans, unleashing a hard average cock. I was grateful I avoided blow job duties as he rubbed it round my entrance. With the bi-curious thing in mind and my sexual background I insisted on a condom. As silent as he’d been since leaving the club he reached in his wallet produced one and slid it on and then slid straight into me. He remained in missionary the entire time, fucking; my hands gripping his buttocks. The biggest change was me raising my legs over his shoulders. This seemed to please him as he could get deeper and once in deep he went slower a lot harder. In fact the slower he went, the deeper he went the more I moaned in pain the more it seemed to pleasure him. It was almost as if when he went as deep as I could take it, so that my own hands were on his hips trying to prevent him hurting me by going deeper that he came to a complete standstill and came.
He shuddered and lay still on me. Face again in my tits. Suckling them like a giant baby which freaked me. It all seemed more maternal and a celebration of ‘woman’ rather than one night stand sex. He was clearly experienced with women but something was amiss and perhaps that’s why he was moving (or at least temporarily visiting) pastures new. A penis might provide the answers that that a cunt can’t. I moved to reposition myself and that was all it took.
He stood up, removed the condom, wiped his cock with his hand, smeared his hand with the remaining cum on my face as he tossed the condom in the waste-paper basket and did up his jeans.
I was a little lost for words if I’m honest. The breast suckling, then having my face used as a cum flannel was all a bit bizarre.
He sniffed, shook his head, opened the door (me exposed and naked on the bed for the other 300 residents to see), said ‘I knew I’d get to fuck you tonight’ and left. He was right.