This story is a long-delayed follow up to this story of how I met and seduced the high school best friend of my college girlfriend. It's not particularly important context though.

Katherine and I started fooling around my third year of college. We didn't hook up per se, rather what we did was play with the idea of doing so. We had long conversations about our goals, what we found hot, and what our red lines were. And for the first couple years I knew her, Katherine's red lines involved not hooking up. No kisses on the lips, no touching her too close to her genitalia, etc. But she did love flirting with it. The thrill of teasing the idea and of giving herself over to someone who she trusted to not cross her boundaries. And I found that experience – and the trust it requires – intoxicating.

During my third year of college, Katherine came to campus ostensibly for a famous annual lecture. I don’t know if this was her plan from the get-go, but she never made it to the lecture. Instead, she feigned exhaustion and slipped away from her friends and my girlfriend and found me in my room. She closed the door behind her, looked me in the eye. “I dropped something, can you help me pick it up.”

The tension in the air was palpable. “Would you like a drink” I offered, gesturing to the bar I had just fixed myself one with.

“Yes, but I’ll measure my own liquor because –“

“You’re afraid to pass on any opportunity to control your surroundings.” I finish.

“Better safe than sorry,” she says. “It’s not that I don’t trust you, it’s just good practice.”

“And you’ll feel more comfortable relaxing in my presence if you are certain it’s 100% your choice and not driven by being a little more intoxicated than you though.”

She gave me a long look before laughing “I forgot how perceptive you are.” She admitted, sheepishly accepting a shot glass and a cup of homemade tonic. She poured some gin in and we discussed botanicals, small batch liquor, and pairings.

We sat on opposite sides of the room, about 15 feet apart. As we chatted I slowly undressed her with my eyes, making sure that she saw me do so and then making direct eye contact that asserted that I had deliberately been spotted. I finished my glass and she bit her lip.

I stood up and strode across the room ti the love seat she was lounging in. Katherine certainly knew how to lounge. She wore a maroon skintight dress that hit mid-calf, black tights, and lipstick that matched her dress. A blazer was folded over one arm of the chair and her knees were glued together, denying me even the hint of a hint. She played with her hair with one hand and casually held her empty glass in the other.

“You should take off your heels” I assert as I reached her, offering my hand.

“Oh? Why?” She asked, her eyes sparkling.

“I wouldn’t want you to turn an ankle.”

She removes her shoes and takes my proffered hand, eyes twinkling with excitement. She rises to her feet slowly, hand in mine, and we begin to dance slowly.

After a few tantalizing minutes of my fingers lightly touching her hip, we had meandered to a foot or so away from an open wall. I took my hand off of her waist and pressed my fingers into her breast, pushing her backwards into the wall. She thudded against it, one on my hands on her breast and the other pinning her arm against the wall above her head.

“See?” I say toyingly. “It would really stink to have to pause here and tend to your ankle. Who knows what fun might be derailed by such an injury…”

I started touching her body. Her throat, her face, her hips, her arms. Just running my hands across them, exerting light pressure at times. Katherine had made it very clear that while she was down to get hot and heavy she didn't actually want to hook up with me: her major boundary was about proximity to her genitalia and marks that might show. She often wore thigh highs and used the heuristic of "nothing above beyond the stalking." Of course, this was mostly about the general amount of space that made her feel comfortable and not the actual location her stalking reached.

I played with this boundary to explicitly outline how good I was about following it. I kissed her thighs along the edges of her stalkings, but then I pulled at them gently to raise the line that they reached and used that as an "excuse" to kiss further up. I would let them droop, and act disappointed about the fact I had to move further down her leg to follow the line. Eventually her juices began to run down her thighs, and I changed positions. I move up slightly, my face level with her crotch, and whispered “don’t feel left out. You’ll get my kisses one day."

Another boundary Katherine had was no kissing. So instead I put my face as close to hers as I could, our lips almost touching. "Don't move," I whispered, "I don't want our lips to touch by accident." She moaned into my mouth, our lips just barely not touching. I hovered there, tantalizing centimeters from her lips, and whispered to her about how much I wanted to kiss her, how beautiful she was, and how one day I would do so much more than kiss her.

I stand and look deeply into Katherine's lust-filled eyes. She draws an outline on her neck and shoulders with her finger. “Anything below here won’t show,” she informs me, shrugging in a way that exposed one shoulder more. Hardly one to require a second invite, I sink my teeth into her shoulder. This draws the start of a scream before she covers her own mouth, cutting it off. I suck on her beautiful skin, leaving behind a hickey that would last for three days per the photos she’d later send me.

She grabs my ass and squeezes me tight, pulling my mouth from her shoulder and level with the side of her face. Then I get a devilish idea. Katherine is extremely sensitive to stimulation on her ears; some light sucking and breathing is enough to get her wet out of nowhere. So I decide to treat her ear like I would her clit, biting and teasing and licking until her knees buckle and she's only standing because I'm supporting her.

I lift her and carry her to my bed, tossing her into it roughly. Then I rummage in my desk for my girlfriend's spare dildo and toss it at her. I straighten my clothes in the mirror and walk towards the door. "I'm going to go have loud sex with the slut next door," I say on my way out. "Enjoy yourself." She would later inform me that she did so thoroughly, climaxing in sync with my hookup while imagining it was me inside of her.