Author: The_other_acct_wink

[M]y [F]irst Time being Pegged

It started as most evenings did with this girl.

I was on the bus home from work, sitting in traffic, and got the usual “you free tonight? :)” text.

It had been a long week, and we were just over the hump. I paused for awhile debating whether I had time when I got a second text: “I have bread :)”

She worked at a bakery in town, and knew that fresh baguette was my absolute weakness.

I responded “I have wine, see you around 7?”

I got back to my condo to get cleaned up and change out of my suit for something more casual. She always said the suits intimidated her, and not in a sexy kinky way.

I liked how simple and carefree she was. Tall but petite brunette. Thin with not a lot in the curves department, but with the cutest and perkiest A cups. She seldom wore bras and I loved it more than I could ever handle. She usually wore overalls covered in flour and paint, and she always seemed to me like someone too good for this world.

We also had the BEST sex. Read more »

[F]rom “Boy’s Day”, to [M]indblowing Public Blowjob, to A Broken Condom

I had moved to A new condo, and had met a girl in the bar adjacent to it at the time. It was a quick and innocent meeting — I had been working late and was getting a cocktail as I finished emails — she was just seeing a girlfriend.

She was brunette, about 5’11, thin/lanky, and had a very deliberate look to her. I could feel her eyes surveying me as I walked in. Her friend was blonde, around 5’4, and curvy. I could tell she wasn’t wearing a bra and could see her pink nipples through her shirt. But I wasn’t there to hit on cute girls, I was there to work.

I order a drink and set up shop at the bar. Overwhelmed with work, and savoring the first sip of my Scotch. I look up from my computer and see her in my peripherals — “my friend and I were wondering if you’d like to join us, it’s Thursday night, after all” gesturing to my work computer. I quickly envision the idea of a threesome with them but the stress of work takes over. I didn’t think my cock could get hard if my life depended on it at this point. I politely decline and ask for a rain check. She asks for my phone and calls herself from it “Great, I have your phone number”, showing me the missed call from my phone. “You can’t avoid me now” and walks away. I instantly feel blood rush to my cock and curse myself for not joining her and her friend. Read more »

[M]et a Redditor [F]or a friendly drink, escalates to FWB. Part 1

Going to make this a 3-part series — because who doesn’t love a good trilogy?

It was Fall, and the weather in PDX was just beginning to turn. Late October is typically when you stop being able to see the tops of tall buildings due to the constant foggy, grey blur that settles in. Days were getting short to the point that by 7 you were ready for bed, and a lot of times could be spent aimlessly wandering Reddit.

I came across her in a local subreddit, asking about good places to skate in PDX — she had just moved to town from SoCal and was still getting her bearings. We talked on Reddit for a few days. It absolutely brought some light to the fog we were experiencing in town, and gave me something to look forward to each night. Not wanting to come off as a compete fuckboi, I kept it pretty pedestrian. We talked about skating, our thoughts on politics, science, and sent a lot of food and beer pics back and fourth. Eventually, we decided we should probably just grab a beer and see if we hated each other or not. Read more »