First Time with a Couple [MMF] [37M]

Maybe about ten years ago, I was up late cruising Craigslist ads, looking for a hookup…as one does. I came across an ad for a male/female couple looking for a guy to join. At this point, I had only been with guys. I was, and still consider myself, gay, but I was open to the idea of playing with them. So I replied to their ad. A few email exchanges later and a ten minute drive found me inside their bedroom.

They were maybe in their mid to late 30s. He was short, kind of round, with a scraggly beard. Definitely not my type. She was what some might describe as a bigger beautiful woman, with blonde hair just past her shoulder, and large breasts. I met them in their porch and then walked with them inside the house and into their bedroom.

I undressed as they watched me. They sensed excited to have a younger guy over. She commented at how skinny I was, even though I was really a few pounds over average. She watched me from the bed, a sheet covering her.

He Took Me to a Party. I Filled Him with Cum [MM] [37]

I came out sort of late in life, in my early 20’s. All my life, I’ve been the conservative, buttoned-up, responsible, and often painfully socially awkward one. Figuring out being gay was sort of a challenge, but with some fun surprises mixed in.

I met a guy when I was out somewhere. I don’t even remember exactly where. Let’s call him Sam. Sam and I friended each other on Facebook, which was definitely more popular for the 20-something crowd back in the mid-aughts than it is today. For a while, we fairly regularly chatted and commented on each other’s posts.

Sam was maybe a year younger than me. He was this fun mix of flamboyant, flaming, feminine, gay and southern redneck. I’m 5’11”, and he was maybe 5’6”. He was pretty. Blue eyes, dark long eyelashes. He wore just a hint of makeup, smoothing out his already near perfect complexion while also adding a bit of rosiness to his cheeks. He was colorful and outgoing. Just about everything I wasn’t.

After weeks of chatting and flirting online, he invited me to his friend’s party. I gladly accepted and looked forward to the event.