summer of fey (pt. 1)

A peek inside my relationship with my college gf, Anna, + some car sex with the most beautiful girl I'd ever seen, Fey, who had a penchant for dressing up – this time as a ballerina.

ANNA WON’T PEG

When Anna, my college girlfriend, wasn't in class or smoking weed, she decorated the walls of our apartment with paintings she bought from museum shops and secondhand stores. We liked the same music, metal and alt rock, and when I was feeling up to it, she'd bring me to yoga class with her. Our relationship was sort of boring but fine overall — and very sexually charged, obviously. 

At yoga, Anna would take water breaks between almost every pose (lazy cutie) and I loved to watch her ass stick up in the air as her lips sucked greedily from the straw of her thermos. She’d be in one of her two yoga outfits: the baggy one or the tight one. The former she wore when she was in her lazy mood (often), and when I saw her in the other one – a matching pair of light pink spandex pants and a too-tight sports bra that barely held in her breasts – I wouldn't be able to think about anything else other than fucking her. 

Watching her plump, taut ass wriggle up into downward dog in those pink yoga pants was a trip. Actually, just watching her ass in general – whether it was moving underneath the fabric of her yoga pants, a pair of jeans, or naked pressing against my thighs in bed – was the main event of too many days. I wasted hours of my life, probably days when you add it all up, staring at Anna's ass. 

She used to stand next to me in the mirror of the apartment we shared, and we’d ogle her thick ass next to my smaller one. Our asses made a beautiful juxtaposition. Hers plump, mine tight; hers a creamy olive, mine a pale white. 

After yoga, Anna would usually go out with her friends for cocktails and poutine at the hipster bar down the street from the studio, all of them dripping sweat in their slutty gym outfits. Being surrounded by a dozen hot girls in minimal clothing striking poses that seemed to beg for penetration was too much for me, so I'd pass on food & drinks and instead go home and arrange myself on the couch with my laptop balanced on my belly, clicking through images of pulsing cocks and imagining them next to Anna's fat ass. I'd rub my pussy until I came. 

Sometimes it wouldn't be enough. I craved penetration, but not by a cock – I wanted to be pegged by another girl. In order to fulfill this need, I saw others on the side. Anna didn't mind. She wasn't into pegging but she understood it as a need for me, one that first developed in high school as a revenge tactic against my boyfriend, my first love, a porn addict. One time in the middle of sex, he asked if he could pull something up on his phone in order to finish, and I let him. I couldn't see what it was because he'd covered my face with a pillow, but the cacophony of squeals and grunts suggested some sort of threesome scenario.

Insecure and pissed, I left his place and texted my lesbian friend, Rana. She came to my parents' house and pegged me. I'll never forget her eyelashes, so long and curled that the tips seemed to reach up to her eyebrows, and her breasts, the nipples all puffy and rosy. That was the first time I was pegged by a woman. It was glorious.

ENTER FEY

The summer I worked as a receptionist at a pool company is the period I refer to as "The Summer of Fey" because it seems that all I did that summer was meet up with Fey and get pegged by her (or vice versa) for what felt like hours at a time. It didn't begin that way, though. It began with a few different women – mostly older, in their late 20s or 30s – eating me out in the backseat of my car during my breaks at work. 

My hookup would appear in the office parking lot and I'd tell my boss and coworkers that she was just a friend who'd come to meet me for lunch. At the time, my type were girls who acted like management consultants – older than me, well-dressed and somewhat stern. I'd hear them before I saw them, heels click-clacking down the sidewalk approximately ten minutes before our prearranged meeting time. I'd glance out the window from my desk to catch a glimpse of a dark-haired head – never blonde – with black sunglasses set against a slicked back bun. 

I'd invite them into the office and their perfumes were always barely detectable, like a fragrant flower held at arm's length. I remember how my boss, a man in his late 50s, used to gawk at them. And full disclosure: I love big tits. So me and the boss would pretend not to stare at the pair of fat tits that I’d have the luck of shoving my face into in less than 10 minutes (at which time he'd probably be jacking off in his office). And that summer, the summer I turned 19 and was in love with Anna, I never hooked up with the same girl twice… until I met up with Fey. 

Fey was the most beautiful girl I'd ever seen. From every angle, her body deceived you. From the front, you thought she was a skinny but well-endowed girl-next-door. From the back, you mistook her for a chunky JLo lookalike. But from the side… that's when you realized that she was the most beautiful girl you'd ever seen. The underside of her breasts hung heavy against the top of her ribs, but her breasts were still somehow perfectly firm. Her lower back flared out into an unbelievable ass which sat above thick, milk-colored thighs. 

From the very first moment I saw her, I wanted to fuck her for the rest of my life. She was the oldest and prettiest of four sisters from the same small town as me, and I can't tell you how many fantasies I used to have about them – individually, all together, in differently configured pairs…

We first hooked up the summer after high school, and during college we made it a habit to see each other whenever we could.

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Read Part Two.