Tess

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A petite redhead on a bi-curious mission...
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I moved to Albany, New York, in April of 2005, and the city couldn't give me much of a welcome. State capitols are never the most interesting places, and I recall Albany as mostly state offices and lobbyists and pricey restaurants to service political types. I was there for the state university, where I was to start graduate studies in History in the fall with the intention of getting my PhD and entering academia. That was a pretty ambitious dream, especially considering that I was nearly broke at the time.

I landed in an old, run-down house near the hospital where four friends were renting rooms and had an empty one for me. Classes didn't start until September, so in the meantime I got a position with a private firm that graded standardized tests. You know those exams you have to take to graduate high school? I graded the essay sections. Me and two-dozen underpaid grad students grading high school essays on computers, all day long. The pay was just enough for me to pay the rent and eat, mainly oatmeal and rice and tubes of Fosters. But a gig is a gig, and I knew what else I could be doing for my money, so I didn't bitch about it...much.

Among the crew was a young woman, maybe twenty-five years old. She was pale and petite, with copper hair in a short, boyish cut over her green eyes. She was quiet and reserved, but I did manage to coax a name out of her: Tess Janssen.

"Forget it, dude," grumbled the chesty brunette who sat at the computer next to me. "She bats for the other team."

I have a history of being attracted to lesbians and I'm curious to know why. Someone once suggested to me that a straight woman has spent her life developing strategies for dealing with men, whether she wants to attract them, or fend them off, in that moment. In any case, the theory went, a man rarely gets to see the woman's authentic self, not until she trusts him, which could take a while. All he sees is the strategy. But a lesbian wouldn't bother with a strategy towards men, since they are deemed sexually irrelevant. They could just be themselves, and that authenticity was what attracted me. Interesting theory, and I have no idea if it's right.

Not to worry, I reassured myself. In September, you'll be at the university, and no doubt the women will cycle through your bed like it was a subway turnstile. I talked to myself like that to keep my spirits up.

In July, the office crew decided to go out to Bombers on Lark Street one Friday night. Lark Street is the Latin Quarter of Albany, just eight blocks deep, and all the college students were down there on the weekends. Bombers had a burrito bar downstairs, greasy and cheap, and upstairs was a red-painted bar decked out in Christmas lights and tinsel and pennants like an amped-up Mexican brothel. It was loud and everyone got fairly drunk in the three hours we were there.

Tess was more outgoing than I'd ever seen her - a little red-headed social butterfly, flitting from woman to woman and ending each encounter with laughter. Maybe she had to get out of the office to perk up, or maybe her 90-pound frame needed just half a raspberry daiquiri to loosen up. She wore jeans with the cuffs rolled up, blue chucks, a tight black tee, and a khaki jacket with a flag I didn't recognize on the shoulder.

As the group broke up at around eleven, we stood together by the old jukebox, and she leaned against me tiredly.

"I'm hungry," she said.

"Not sure if the kitchen's still open," I replied.

She suddenly lit up with a smile.

"I have an idea. Come with me."

I followed her downstairs to the street, where people smoked and chatted outside the bar. She led us a block down the crowded sidewalk, pulled keys from her pocket, and a parked car's lights came on in front of us. It was a Jaguar F-Type convertible, hunter green.

I looked at her as we got in. We were making about ten dollars an hour at the office, pre-tax.

She dropped the top and ran a few red lights on the way to Route 787. When we merged onto the highway, she stomped the pedal and punched up Coltrane's "Giant Steps" on the stereo.

"My parents threw a party at their place on the river last night," she shouted over the wind, motor, and jazz. "There should be a lotta good stuff for us."

Leftovers with the lesbian in the Jag. Why the hell not? I'd been surviving on red beans and rice for three months.

We crossed the river to Rensselaer, then turned south down Rt. 9 through the woods along the Hudson. Tess braked hard when we got to Janssen Island Road and made a squealing right, pulling up to the estate.

And that clarified everything. The Janssens were one of the first settler families in Albany, straight outta Amsterdam in 1620, long before the British captured what is now New York. They were the oldest money in the capitol region, the kind of wealthy people who don't need to show off because everybody already knew. They still had a lot of land and influence up here.

I looked at Tess in the moonlight, and now recognized the flag of the Netherlands on her shoulder. The name hadn't clicked before this.

She stopped in front of the old stone estate house, three hundred and fifty years old. The lights were out in the windows.

We went in through the commercial-grade kitchen, which was larger than my entire apartment, and she turned on the lights and started rummaging through the refrigerators.

"See what you can find," she told me.

I pulled open a refrigerator.

"Here's...shrimp? No, it's lobster. In risotto. Looks good."

"I found filet mignon," she said. "And bearnaise sauce, I guess."

"Linguini Bolognese. Wow, it's thick..."

We were going to make full courses, but kept finding more, artisanal asiago and stuffed avocados and bacon-wrapped jalapeños, so instead we just heated things up in the micro and ate them off the kitchen island as they came out. There was a rack of wines to choose from, so I picked Chateau Neuf du Pape, a bottle for each of us. She put on "Kind of Blue;" the kitchen had a better sound system than my apartment. We chatted as we ate, and I felt very fine, better than I had since moving to Albany.

"What are you majoring in?" she asked.

"History," I said. "Are you in school?"

"I finished at Bard," she said.

"Studying what?"

"Fine Arts."

She told me about her adventures in the art world, and I learned a lot about the politics of galleries and shows. I had no idea it was so cutthroat. From the outside, it looked refined and bourgeois. I should've guessed, of course.

"You have any projects planned for the summer?" I asked. I meant gallery shows.

"Yes! I have a big project in mind."

"What's that?"

"Well, this summer, I want to investigate men."

I looked up at her. She was smiling, green eyes holding mine intensely.

I leaned across the table, a bit tentatively because I only half-believed it. She grinned at me, enjoying it.

I kissed her, and she grabbed the back of my head and held our lips firmly together. But she pulled away - she wanted more, right now.

She jumped off the stool, came around the table, and grabbed me by the front of my shirt.

"This way," she said.

She hauled me into the next room, which was a plush lounge for dinner parties, towards the staircase across the room. But her little ass was so adorable as she led me on that I had to give her a quick spank. She turned around with a grin to swat me back; she wasn't shy, so I knew she'd been with women. I got my arms around her waist and grabbed her ass with both hands, pulling her against me and kissing the side of her neck hard.

"The bed's upstairs," she moaned.

I was already pulling her shirt over her head. She was too petite to need a bra, something I'd already noticed in the office. She unclasped my belt and tried to pull my jeans down, but we got tangled up in each other and our clothes and tumbled to the carpeted floor.

"Oh, fuck it. Let's do it here," she laughed.

I had to pull off her sneakers to get her jeans off; she wore split five-toe socks in rainbow colors, which were so cute that I left them on. She had the palest skin I'd ever seen, milky and smooth. I slipped her panties down her thighs and the strip of copper hair over the mound stood out brightly against the white skin.

I wore UnderArmor boxer-briefs under my jeans, and when she got the denim off, she knelt next to me and ran her fingers over the stiff bulge. I laid on my back, and she pulled the boxers off and held my cock delicately.

"Is this, uh, big?" she asked.

"Nah, it's average."

"What's this line here?"

"The circumcision scar."

"Oh."

I put my hand over hers to show her how to stroke it. She knelt over me, straddling my legs, and kissed the swollen head.

"How do I...um..."

I took her hand and licked up and back over her index finger. She repeated everything I did to her finger on my cock, slowly licking the shaft and gently sucking the head. Then I held her hand and let her learn on her own, exploring my cock with her lips and tongue, quickly growing more confident. She rubbed the shaft against her cheek affectionately.

"It's fun," she said with a grin.

I put her finger all the way into my mouth, tonguing it firmly and sucking as I pulled it out. She repeated it on my cock, but went down too far and gagged a little; then she learned how deep she could go, and sucked it slowly and lovingly. I stroked her hair as she learned her way around a man.

Then she reached down between her legs and started working on herself - languidly at first, then more firmly, and she was working my cock faster, too. She let out little mews of pleasure as she grew more excited.

"My turn," I said as I lifted her off me.

I spread her out on her back, laid down and put my arms under her legs; then I kissed up the insides of her thighs, and she stretched luxuriously on the thick carpet with a long "Mmmmmm..."

Her pussy was tiny, with delicate pink inner lips like petals that I spread with two fingers. I teased her lips and clit with the tip of my tongue, tasting her wetness. She was very responsive, giggling and purring and lifting her hips to me, and I almost chuckled remembering how staid she was in the office.

I pulled the wet skin over the stem of her clit taunt between my fingers and massaged back and forth with the tip of my tongue. She gasped at the sudden intensity, but I only pressed down a little harder in response. I slipped two fingers into her, a bit tentatively, but she was wet and opened easily. I rubbed and pulled over her G-spot as I lapped her slowly.

"Oh, you're torturing me!" she whined.

"Tell me to stop."

"Nooooooo..."

I slowly fucked her with my fingers, turning the knuckles around in her, tonguing her tiny clit the whole time. The tip felt no larger than the head of a pin on my tongue.

"I wanna feel your cock in me," she said dreamily, bucking her hips against my fingers in time with me.

I sat up and knelt between her legs, putting one of her knees over my shoulder; then I slipped my cock inside her slowly, all the way in, watching her reaction. She started panting lightly as I rocked in and out of her, her eyes tightly closed.

Then I leaned forward with her leg still up, tilting her hips back and putting my hands to either side of her head. I pushed in as deeply as I could and held it there, grinding down on her clit. She bit her lip, and I leaned down to kiss her. As I pulled away, I started riding her harder, and she wrapped her arms around my neck, grunting each time my cock drove into her. After a good long ride, I pulled out of her.

"Roll over," I said. "Come up on your knees, but leave your head down." Well, she knew what that was for; she lifted her little ass high and looked back at me over her shoulder, inviting me back in.

I grabbed her hips, got back in her and fucked her hard this time. I noticed how firm and lean her body was - I was banging against her ass, but there was no fat on her body to bounce. Then I grabbed her arms, pulling them back towards me, lifting her off the floor as I fucked her deeply.

"Oh, god, you're strong!" she whined. I'm not strong; she just wasn't used to men.

It didn't take long before she arched her back and came with a squeal, which was good for me since her panting and whining were turning me on so much, I didn't think I'd be able to hold off much longer. She clenched her muscles down on my cock and I came hard, banging into her until it was over.

I let go of her arms and she stretched them out in front of her, cheek to the floor, trying to catch her breath - but she stayed on her knees, and I still slowly fucked her, and I stroked her waist and back and ass until I couldn't stay hard anymore. She looked back at me and smiled tiredly, chuckling, and all at once the exhaustion hit me, too, now that the adrenaline was gone. We picked up our clothes and went upstairs to bed. The socks still looked cute on her.

That was our only night together. After that, we smiled at each other knowingly in the office, but she never had much to say, though she was no longer standoffish. Perhaps she finished her bi-curious experiments, or maybe carried on with someone else. In September, we both left the company; she moved down to Brooklyn to compete against bigger fish, and I started grad school, which kept me busy enough. I followed Tess' career online for a while before getting too involved with other things and other people. I hope she did well in that cutthroat world, so cosmopolitan on the outside and so contentious within.

As for me, life was much easier after the teaching assistant paychecks and financial aid came in, and though I was hardly rich, I could afford better beer. And I did quite well with those university sigma-women, intelligent and career-minded and bookish; it takes a long time for them to let you in (quite literally), but I have to say that they're very good company once they do.

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4 Comments
C21ChoiceC21Choiceover 1 year ago

Love how you wrote this but simply wouldn’t communicate with me. Nice writing op.

SkanderbegSkanderbegover 1 year ago

Loved the pace of the story, it wasn't rushed and flowed to the conclusion.

lc69hunterlc69hunterover 1 year ago

Interesting twist

AnonymousAnonymousover 1 year ago

Always love a redhead story!

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