Inspired by a conversation I had with my friend Paul about the merits of straight boys and what it was like being a gay teenager a decade before GLEE (ie, the days where being a camp-as-a-tent queer teen WASN’T accepted) I wrote this short story detailing one of my memories from those days.
If mild-ish sexual content isn’t your cup of tea then please avert your eyes now. Otherwise, read on and enjoy!
THE MILF AND THE STRAIGHT BOY
(sometime in the mid-90′s)
Remember when you were a teenager and everyone else’s Mum seemed way cooler than yours? There were several Cool Mums amongst the kids in my class at school – not the least of which was Dina – my friend Nicki’s trendy, rock-chick mother with a pierced nose and hipster jeans. Dina was pretty cool. She always let us hang out after school and play music, bash on the drumkit and on the occasional weekend she let us have parties upstairs at the house she shared with her husband and two kids.
On a seemingly unremarkable Saturday night after not having been to one of Nicki’s parties for a while due to some acting commitments I arrived with the party in full swing. One of the great things about Dina was that, not only was she a MILF, she allowed us to drink and quite often supplied alcohol – as long as she was there to keep an eye us. Nicki was one of those who had friends in every one of the cliques at school. She was pretty enough to be A-List, smart and friendly enough to win over the B-Crowd and alternative enough to be part of the group of musicians, artists, actors and stoners. Consequently her parties featured a good mix of these types and this night was no exception.
I was still milling around in the metaphorical closet at this point, wondering whether or not I should step out. I think Dina knew the truth. She was wordly – surely she did. Dina used to flirt harmlessly with most of the boys but I feel, when it came to me, there was a glint of knowing in her eye. As MTV pumped from the television I danced with Dina in the raunchy, seductive way she was known for, especially on night’s such as this where her husband was overseas for business. We moved like prospective lovers courting, her hips gyrating, gradually pushing harder against my groin and, despite my apparent homo-ness, there was a stirring down there.
The song finished and Dina looked straight into my eyes and smiled a wry little smile before sauntering off to go dance with one of the other boys or pour another drink or something. I didn’t know. My head was swimming from the music, the cheap booze and the thoughts crackling like lightning in my brain. I flopped onto the couch next to some of the others I knew, threw back another vodka and sang along to the pop songs playing on MTV. Time blurred in that way that it does when you’re lightly intoxicated and I floated around the various rooms interacting with various people until I found myself emerging from the bathroom out in the pool-house. I needed to pee really bad and knew there’d be no one out there as it wasn’t quite hot enough to be by the pool.
As I moved through the garden back towards the house I could see, in the small slice of moonlight breaking the darkness, the rounded, smooth little ass of Justin – one of the boys from the A-List group. Facing him, her hand rubbing slowly around his crotch was Dina. Justin’s hand was up inside her shirt and he was massaging her breast as they kissed. Either out of shock or awe or intoxication I stood, staring at their interlude until Dina noticed I was there and shifted her hand away from Justin’s goods. He turned, they had been sprung and moved to cover himself until Dina slowed him with a touch of her hand on his arm. With her other, she started stroking him again, smirking at me as she did so. Justin relaxed under her touch and Dina flicked her head at me, beckoning me over silently with a confidence I found reassuring.
Once there, Dina leant in and kissed me hard on the mouth, her tongue darting between my lips with vigour. Before I knew it, her spare hand was rubbing my package through the fabric of my shorts and my pulse beat in my ears, a nervous cacophony that I was rapidly getting lost in. Dina whispered something to Justin who was, by now, full erect in her other hand, and I didn’t care what they were saying or doing – I had given in to what was happening. Without warning, Dina stopped kissing me and moved her hand to the back of my head, guiding me toward Justin’s lips. It was him that kissed me gingerly, pulling back momentarily like he had been startled by something unexpected. Justin kissed me again, more passionately this time but still somewhat unsurely as Dina resumed fingering the bulge in the front of my pants for a few minutes before her hand left it’s station again to take control and lead my head down toward Justin’s hard tool. He didn’t resist as I took it in my mouth and started working it while Dina ran her fingers through both of our heads of hair.
I was on my knees now and Dina had stepped back a little to allow Justin freedom of movement to fuck my face hard. I had known this boy nearly my whole life and could scarcely believe that my mouth was slurping greedily on his cock. I looked up at Justin, his face contorted in a mix of concentration and power. Dina watched on, merely a bystander now as Justin grabbed the back of my head with both hands and slammed hard into my mouth with one last powerful thrust, pulling me toward him until I nearly choked, making sure he got maximum pleasure from his orgasm.
And with that it was over. Justin retreated from my mouth once I had cleaned him up, zipped his pants and went back inside the party. Dina tidied her hair, smoothed her top and smiled at me before leading me back inside. I was high on smug satisfaction for the rest of the evening and when I woke the next morning and made my way into the kitchen Dina smiled but looked a little embarrassed. Nicki was blissfully unaware and a couple of the other girls whispered that they heard Justin had fucked Dina last night. Wow. Justin had gone home hours before the rest of us crashed and, despite the silly grin plastered on my face, I had resigned myself to the fact that it was a one-time deal.
Except it wasn’t a one-time deal. But I didn’t know that yet.