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"Elise is cheating on me. She has been for almost half a year. She finally fessed up last night. I didn't believe her at first. Then she showed me the pictures. Showed me the texts. I was crushed. Still kind in shock about the whole deal. She's leaving tonight. Probably already gone. I'm just so bad at relationships." Calli was in tears.
Calli was my yoga instructor. A classic California beauty. Long, dirty blond hair totally unshaven, a balcony you could do Shakespeare from, could bend like a pretzel. I was crushing on her from the first class. It took four or five classes before I realized she was a card-carrying lesbian. Somehow, I'd become her confidant, nonetheless.
We were sitting in the coffeeshop after class, as usual. She was twirling a straw absentmindedly in her latte.
"I'm sorry, Tanner. I don't want to burden you. You don't need to hear my problems."
"It's fine, Calli. You know you can talk to me about anything." I replied.
"You're the best, Tanner." She smiled sadly at my platitude. I sipped my Chai and nodded.
Somehow the fact that I was a Cis male, made me easier to talk to. Calli had fallen hard for her first girlfriend back in high school and they'd stayed together for almost four years. A star forward on the Soccer team, her girlfriend had fallen in love with the backup goalie senior year in college and broke things off with Calli. It was done.
Calli was devastated. Then she found Audrey and yoga. Six years. They'd talked about getting married, and then one day Calli came home and all Audrey's stuff was gone. There was a note on the kitchen table apologizing for the sudden departure. No further words followed.
There was a yearlong gap before she'd met Elise. Calli was healing, sure that Elise was the one. In the bedroom, it was nothing short of magical. They finished each other's sentences. And if Elise had had a somewhat checkered past, surely Calli's love transcended that, did it not? At least it had for a while. Elise had always had a wild streak, and eventually it played out.
"I'm thirty-four freakin' years old, Tanner. And I'm back to square one." Calli said. "Why can't I catch a break?"
"Look. You're overthinking this. You're a beautiful woman. This is just a bump in the road." I said.
"Yeah, maybe so. It just feels like I'm never enough." Calli confessed.
"Hey. Let's get dinner tomorrow night. My treat. Get your mind off things." I suggested. "There's a new Vegan place that just opened on 7th. You game?"
"Okay. Better than sitting home moping, I suppose." Calli agreed.
"Don't the two of you make a lovely couple!" the host flattered as he led us to our table. Calli and I side-eyed each other.
We ordered the Tempeh stuffed peppers, and a nice garden salad. I got a bottle of organically grown white wine. Calli confessed that she wasn't much of a drinker and did her best to nurse her glass through the meal.
It was a nice evening. Calli had indulged in a second glass and left it half finished by the time the check came. She was just a little tipsy.
"Ya know Tanner, I owe you a debt of gratitude for getting my sorry ass out of the house." Calli intoned as I dropped her off in front of her place.
"No problem. We're buddies. That's what buddies do for each other." I grinned.
"Thanks, buddy!" Calli gave me a big hug. I could feel her tits pressing against my chest for a moment or three... or four.
"Goodnight Calli." I said softly as she unlocked the door and turned the porch light on for me.
The hug stuck with me. It had definitely exceeded the duration of social propriety, and then some. But then Calli had been feeling tipsy, so there was that excuse. Whatever, Calli made no mention of it a few days later when we were getting our usual coffee after class.
The weekend was approaching and Calli seemed a little unsettled.
"Anything fun planned?" She asked.
"I don't know. I was thinking of driving out into the country and doing one of those vineyard tour things. You know live music, get some fresh air and sunshine. Why don't you come with." I suggested.
"Maybe. Can I let you know?" Calli asked.
"Sure. Let me know." I replied.
A day later she called.
"Hey, Tanner, it's Calli. You still going on that vineyard tour?" She said.
"Yeah. You in?" I asked.
"I'm in." Calli confirmed.
"I'll pick you up at your place. Bring sunscreen." I said.
Calli looked great, in a sleeveless lilac top with her cute tufts of underarm hair peeking out, white pedal pushers and sneakers. Perfection. We made small talk on the drive out. The weather was sunny and warm. The vineyard was up a long gravel road, nestled in the foothills.
The tour was largely conducted from a tractor towed trailer. There were four or five other groups of two or three people. But mostly couples. It was clear that everyone assumed that's what Calli and I were as well. Apparently we gave off this Barbie and Ken vibe wherever we went.
There was a little bluegrass band back at the barrel house and Calli and I even danced a couple numbers when some favorite song of hers came up. We sampled the different wines, ate some salads with cheeses and bread. Again, the alcohol had Calli more vociferous than usual.
The band had just finished an up-tempo number and we were still on the floor when the band slowed things down. I thought Calli would want to sit this one out, but instead found her hands on my hips and her tits pushed against my chest.
"Thanks Tanner. This has been such a perfect day. I swear, if you had a pussy I would be so up in your junk for this." She whispered in my ear, and then kissed my cheek.
It was the hug incident, only times 100. And we both knew that this was going to be the subject of a future discussion. Calli's buzz soon faded, and the drive home was subdued and contemplative.
It was a week later.
"No. See, that's the problem, Tanner. I meant every word of it." Calli admitted.
We were sitting in her living room. Her with a bottled water, me with a beer.
"But why bother saying it out loud?" I asked.
"I don't know. Something just came over me and I blurted it out. Since Elise left, you're pretty much the only person who's been there for me. Like a bestie. Like a girlfriend." She hazarded.
"I'm a guy, though, and you're a lesbian, through and through." I pointed out. "So there's that..."
"Am I? The night I hugged you. I had a hell of a time falling asleep later. There was nothing rational about it. I just wanted to feel another human being's touch. Everyone I've ever touched has been female, but that's been by choice." She tried to explain. "I was shocked that hugging you didn't feel radically fucked up."
"What about the dance?" I asked.
"Shit, Tanner. All I could think of is that if you were a girl, and you were being this nice to me, I'd be cleaning out a drawer for you in my bedroom dresser, and making sure you had someplace to put your toothbrush." Calli said.
"So, what's holding you back?" I asked.
"You're a guy for starters. I've never been with a man. Never wanted to be. But I'm weird when it comes to you. I'm a 34-year-old lesbian, so probably the earth would open up and swallow me whole if I changed teams." She said. "Not that I would."
"So you've actually thought about this?" I asked. "Given it consideration?"
"Okay, yeah. I admit it. I have. So what?" She said belligerently.
"Calm down, Calli. It's all hypothetical. Chances are you're going to meet a new girlfriend and then this'll be some anecdote you guys share when you talk about the most embarrassing thing that ever happened to you." I suggested.
"That doesn't even make sense, Tanner. Will you do me a favor? Shut up and fucking kiss me already?" Calli said. It was on.
Turning to face me, she was suddenly there with her arms around me, our mouths together. She tasted nice. Peach lip balm. She smelled like salt sweat and sunshine. Her breasts pressed into me and she rubbed them lightly against me as her tongue found its way into my mouth. Her eyes were closed, and she swayed slightly against me as she deepened the kiss. I was blown away.
After about a minute or so, she pulled back and opened her eyes, her arms still around me and mine now around her. "Not too bad..." she sighed.
She smiled sweetly at me and resumed our kiss. I felt like a teenager. I moved my hand up and lightly massaged her breast. She moaned encouragingly into my mouth, pressing her other breast harder into me, slow grinding it. Moaning that it felt good.
Pulling back once more she chuckled. "I'm pleasantly surprised, Tanner. You're a very good kisser... but your boobs are so tiny!"
"Yours more than make up for them." I laughed.
Taking my hand she led me toward the bedroom. We sat on the edge of the bed and resumed kissing. Ever so slowly we removed each other's clothing. She was an absolute unshaven goddess. Laying her back on the bed, I kissed my way down to her breasts taking my time and listening to her cues as my teasing took its toll and her arousal grew.
I continued down until I reached her bush. Her hand was on my head softly directing me onward as she tilted her luscious hips back. Sliding one finger into her wetness I lightly suckled her clit, feeling it swell and grow harder as I did so. She moaned and lightly quivered. The soft downy hair on her legs standing on end as my tongue circled round and she bucked lightly against my mouth, shaking slightly harder.
I was on the right track. I added a second finger alongside the first my thumb lightly rubbing her anus. She came suddenly and intensely, her back arching off the mattress and a long sibilant groan releasing from deep within her core.
We were naked together, on an open plain. Both of us reaching for something and finding each other at the end of our fingertips.
"Holy Shit, Tanner. Just Holy Shit." She said, pulling me up into another kiss, and licking her juices off my mouth and chin.
Reaching down her hand found my hard cock and by instinct her fingers wrapped around it.
"Wow. I've never seen one of these in real life before." She gave it a stroke. "What do I do?"
"Well you can stroke it, kiss it. Whatever. Think of it as a very long thick clitoris." I grinned.
Her hand felt nice. She had a good touch. She bent down and took it in her mouth, moaning a little bit as her mouth grew full. My shaft twitched as she stroked and sucked me. I felt a little precum escape. Looking up at me she smiled innocently, making sure she was doing it okay.
"I like it, Tanner. It tastes nice." She beamed. "Um... would you like to sheath this sword?"
"Um... I'm sure you're not on birth control and..." I began.
"Just finished my period yesterday. I'm sure I'm safe. Man, talk about things you never thought you'd hear coming out of your own mouth." She giggled. "Let's go."
"Okay then. Lay back and relax." I moved into position on top of her. "Now take it in your hand and rub it between your pussy lips. Get it nice and wet."
"Wow, Tanner. That feels good. I can't believe I'm about to do this." Calli said.
I pushed forward, feeling myself sliding inside her. It seemed strangely contradictory. A beautiful 34-year-old woman, and I was technically taking her virginity. It was a teenage thing, but somehow it resonated in profound ways in my subconscious.
"How's it feel. Any pain?" I asked.
"No, but I feel really full. It's different from a toy. Are you all the way in?" She asked.
"Not yet. I just wanted to make sure you were alright before going further." I said, going further.
"Can we kiss some more?" Calli asked.
I began kissing her, felt her pussy gripping and releasing my shaft. She was close to her first PIV Orgasm, and when it happened, it happened big. Her whole core shook as I thrusted in and out of her. Her eyes were like saucers glued to mine. Her right hand slapped the sheets, her left on my hip riding in and out with each stroke. A full body haymaker.
I slowed my pace and let her recover. Rolling over and pulling her on top of me when she was ready. To some extent, this had to be familiar territory for Calli. But the textures and the geometry were different for sure. I let her ride me at her own pace, playing with those perfect breasts and teasing her nipples making her gasp with pleasure.
She began to swing her hips, having taken my full length, she was riding me as if her life depended on it, collapsing on my chest with a squeal as she bounced into another orgasm.
"Tanner... are you... close?" Calli asked trying to catch her breath.
"Not yet, Calli... Soon. Okay?" I replied.
"Okay... Good!" Calli smiled.
I had her on all fours. Her breasts swaying in time with my thrusts. Slow and deep. I could feel her shivering. Floating in the zone. It was truly beautiful. I could feel the flutter beginning, and started picking up the pace. Her thighs humming like a tuning fork against my legs as I started slamming her as hard as I could. I grabbed her long hair and pulled her head back.
She was over the edge. Keening like a banshee as my cock exploded inside her. It was the best orgasm I'd ever had. Rolling off her we held each other and kissed until we landed back on earth.
"Well, as far as experiments go, how did you think it went?" I asked.
"I'm not sure. Let's have dinner and re-evaluate again, afterward." She grinned.
"I'm down for that." I said.
Three weeks later I was looking at my spare toothbrush in the toothbrush holder in her bathroom.
"Tanner, would you get in here, honey! I need some loving." Calli sang out sweetly.
"Be right there, baby!" I replied reaching down to feel my cock already swelling with anticipation. We hadn't slowed down even a little bit since that first night. Like Calli was trying to make up for lost time. Sometimes you choose love. But sometimes it just finds you.
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