Her: “I got some new thigh high socks. Come over.”
Amazing. Last time she came over, we were discussing various turn-ons. I was still relatively inexperienced then, we were 22 and had been tumbling around the city, both in and out of the bedroom. The Playboy aesthetic informed much of what I found sexually attractive at the time and I loved those centerfolds that would wear thigh high socks. (Who am I kidding, I still do) I asked if she had a pair and she told me all about how she’d been exploring the role of pain in her arousal.
…
I hadn’t replied yet.
…
Her: “Just got a wax this week. Seemed like an important detail.”
We were platonic friends through high school and kept in touch through college. She got an internship in the town I had moved to after college. There was always a little bit of something between us and absence of parental oversight allowed for the introduction of naked times to our relationship.
Me: “I’m on my way.”
Her: “Apologies in advance. Craigslist roommate is here.”
She had moved into a spare room found on Craigslist. Her roommates were nice enough, though wildly naive at times.
I arrive 15 minutes later, she lets me in and we sit on one end of the sectional opposite Craigslist roommate. She’s wearing capris with socks I can’t see the tops of and a t shirt and my mind is racing ahead. I hold off rushing things, idle chit chat abounds.
We fill him in on our friendship and some other backstory. To this day, I’m not certain what it was that led to his assumption. Maybe it was the fact that my clothes fit me or our lack of canoodling on the couch. Maybe it was my lack of a backwards hat. Either way, he made an assumption that I was gay; I look at her and we decide to roll with it.
“Well yeah, I went swimsuit shopping today and he’s going to help me pick one for my trip. He’s my lucky charm.” She smiles at me as he sits up, 100% attention.
I watch his eyes flash to her chest, assessing whether she was wearing a bra over her lovely 32Ds. My friend is also blessed with lovely curves and stays in shape, 5’2”. Craigslist has clearly wanted her since she moved in. Bad. The thought of being passed over as swimsuit judge by a gay friend was just more than he could bear.
He pleads. “Wouldn’t you want the straight point of view? Maybe we can do it all together??”
But it was futile. She masterfully feigns polite disappointment. “Sorry, Craigslist roommate. Before my last 3 summer trips, he has had final pick on my swimsuits. Each time, we have gotten together alone, I show him 15-20 options and he picks the top three. And on each of these last 3 trips I have had very favorable encounters with amazing men I have met on these trips. Like I said, he’s my lucky charm!”
She stands. He adjusts his pants, his face agog. She grabs my hand, pivots on her toes and carefully tiptoes toward her bedroom as I follow and play along: “Yes, we really should get started before we lose this amazing lighting. It was great meeting you!”
Her door closes behind us and we are immediately fiercely Frenching. I confirmed what I knew immediately upon entering the apartment (no bra) and was pleasantly surprised by additional revelations (no panties). Before I knew it, I was faced with my beautiful blonde friend wearing nothing but thigh high socks, looking amazingly similar to a mid-90s centerfold and totally embracing the look. She tip toes away from me as I sit on the edge of the bed, my body fully attentive to her every move. She glides back toward me as I drop to my knees and she places her right thigh on my shoulder, introducing me to the recent work of her wax therapist. To taste her at that point was more of a formality, she was already well prepared for our plans.
After we were adequately reacquainted she moved to the California king that belonged to the temporarily gone but never forgotten Craigslist roommate’s roommate and proceeded to crawl away from me on her hands and knees.
Her looking over her shoulder back at me in this moment became a welcome and frequent occurrence that summer. Intertwined by mounting frantic thoughts of, well, mounting, I thought briefly about her interest in pain. We had done hair pulling and spanking, but she wanted surprises and to explore new kinks. I quickly remove my shirt and pants and slide in from behind, starting with slow full strokes and letting her moans guide me.
A few strokes in, I look down and see something that makes everything click: a single, undisturbed hair growing about a quarter of an inch from her asshole, long enough to pinch. Running on instinct, I promptly pinch the hair firmly. “Looks like the wax therapist missed a spot..”
“Huh?” She exhales between thrusts. As she processes what I said, I thrust fully and yank the hair out at the same time. She moan/yelps, now understanding what I meant as she contracts down on me until I go crosseyed.
I am momentarily incapacitated until those wonderful kegel muscles relax. She’s looking back at me again, an intoxicating mix of anger and arousal in her eyes while while she bites her lower lip. I take a handful of her hair and slowly pull while I watch her back arch as my thrusts and her moans pick up tempo.
Eventually even the socks came off and we had a pretty great summer afternoon. While I’m pretty sure he heard us, I couldn’t confirm whether the Craigslist roommate had a new understanding of what had gone down that day because he was long gone when I left.
Source: reddit.com/r/gonewildstories/comments/hn7c4j/summer_fling_mf