My First Real Bisexual Experience

This "first time" story still gives me the chills.

If you've read any of my previous works, you know I spent 18 years in an ultimately failed marriage that ended in divorce about four years ago. The years that followed were not exactly as easy as getting back on a bike. Everything is digital now, including the dating scene, which isn't exactly how I look for real organic connection. And then of course there was the sheer force of habit of doing things the way I had always done them, which didn't exactly blast "single woman," or "available." I would go to some bars with friends or coworkers, but never really to meet someone new. Then when covid swung a wrecking ball into all of our lives, the hope that I might meet a nice, normal, adventurous, smart, fun and single man who just happened to be in his late 40s or early 50s seemed to evaporate, if it ever existed at all.

That sucked. The last few years of my marriage didn't exactly resemble a close, intimate relationship, and I was so past beyond needing to feel closeness, and wanted again. I wanted to feel the vulnerability of a new relationship and rekindle all those things I knew, but had forgotten, about myself. I wanted to be needed. As a woman, as a sexual person, as someone worthwhile and valid. I wanted all of that, and was so frustrated that the state of the world was denying my needs.

I had a few close friends who helped me through those darker times, as well as my sister and a couple of close cousins. But I also didn't want to feel like I was anyone's "project" or charity case. So I'd let them take me out, or cheer me up, but I never really took the bait on fix-ups, or friend-of-a-friend chance meetings, or anything like that. More often than not, I'd ditch most of whatever comprised my "posse" (do we still use that word?) to end up on summer weekends alone with my friend Alyssa, oftentimes on her boat.

I loved visiting the marina, and having a friend with a boat. I hate that that sounds like I am a leach, but that isn't the case at all. I just love the smell of the marina, the short drive to the docks, how different it felt than happy hour at this joint or that, and there were never any crowds or playa operators to deal with, or other friends I had to shine on a happy face for. It was like my little naval escape from the world.

I also loved hanging out with Alyssa, who was always one of my favorite people. We had worked together many years ago at the same high school, but she retired quite early when her dad passed away and she came into a considerable amount of money. I never asked how much she inherited, but she was surely not one of those snobby yacht club string-of-pearls freak shows you see sipping their overpriced martinis trying desperately to be seen by everyone. She still dresses the same (cargo shorts or jeans, t-shirts or hoodies), talks the same, acts the same. And I loved that, because even with no frills, Alyssa always seemed to have a magical radiant sparkle.

She laughed a lot, and easily, and was sweet with her own jokes. She did cute accents and characters when she told stories, and had always been one of my most considerate friends. After a few wines, she would always make me blush sharing an intimate story from some of her exploits, told with lusty vigor. I looked up to her, she was so daring and unafraid and sure of herself. She wasn't what anyone might call "supermodel" beautiful, but at 5' nothing, lightly freckled and perfectly curvy, she just exuded natural beauty and a thrilling sense of wild abandon. I adored her, and as I got to know her better and better during lockdowns, I admit I started to feel a real kinship, and a strong attraction, as well.

I always laugh when someone asks me if I am, or was, "bisexual." I mean, it's a label I've never really been comfy with. My personal theory is that all humans are at least partially bisexual, since I feel like connecting to an individual is so much more important than societal sexual norms. And I know way more women--attractive ones, too--than men. I had to face facts. Starting a "dating" relationship with another man just felt completely daunting to me. It's not like when you were 19 and single and were looking for someone to connect with and plan a life and a future together. Already in my 40s, divorced, with a kid, a job that pretty much prohibited me from moving around the country, I didn't exactly feel like a "catch." And I worried that any guy who would want me at this stage of my life would have something wrong with him. Fair? Probably not. But when you go through a divorce as contested as mine was, you don't exactly come out the other end unscathed.

That was another reason I loved being around Alyssa. She was openly lesbian/bi, hated the contrivance of things like "date night" or "couples anything," always preferring to dance to her own drummer. She would tell me I looked beautiful all the time, or had a great laugh, or looked cute in a certain outfit--she was relentlessly positive and uplifting. Everyone should have a friend like her. I was glad I did.

She would make me laugh loud talking about sex, or sexual histories. She was so transparently nosy that it was hilarious. She would just come out and ask things like "how big was your husband's penis?" or "have you ever had a squirting orgasm?" I'd blush, but chuckle because she asked them as casually as someone would ask "have you ever tried steel cut oatmeal?"

One night we were on her boat, pretty late, and we had had a lot to drink. She told me I shouldn't drive home, and convinced me to stay with her on the boat for the evening. I secretly love that she offered--sleeping on a boat seemed so romantic, even if I wasn't with someone. It seemed cosmopolitan and chic. Even if I was feeling a little woozy.

Alyssa was in rare form, pouring more drinks, laughing, telling stories and asking questions galore. We were talking about the stunning dearth of available men my age, and jokingly added with an eyebrow wiggle, "you could always come over to the dark side." I laughed along with her, but the thought hadn't exactly been new to me. Through my life, I had intermittently been attracted to several women, and frequently fantasized about them. It felt exciting and dangerous. I liked that. I liked that she mentioned it.

"The dark side, huh?" I smiled back at her, hoping she would keep the conversation alive. She did by cupping her huge breasts and giving them a jiggle, snapping, "don't tell me you don't want a piece of these babies." I laughed again, too afraid and self conscious to test the waters there. She then continued, "speaking of which--it's midnight and we're all alone. Why the hell am I still wearing a bra?" She proceeded to wrestle out of it without taking her tee off with impressive ease.

"Ah, better." She sighed. Indeed it was. I nervously looked at her, and the way her heavy tits stretched the soft cotton of her tee, the protrusion of her stiffening nipples quite apparent under the light blue top. I was too tipsy to look away.

I am an E cup myself, so I am used to the stares and attention that comes with the territory, and being much larger than me, I knew Alyssa knew the drill, too. She smiled and arched her back a little in the light breeze topside, staring into my eyes in a way she never had, as if she was testing me out. She took a few steps toward me and topped off my wine, and softly wondered, "would you like to take yours off too? You're still staying here tonight, right?"

I was. I was staying. I started to feel very aroused, but did my best not to let on. I did want to take my bra off also, now that she mentioned it, but I was wearing a fitted button down, and so I couldn't attempt the same shimmy escape move Alyssa did in her tee. "Do you have something for me to wear?" I wondered. "Eventually," Alyssa whispered with a fiery mischief in her eyes.

She reached across to me and started to slowly, silently, unbutton my top. "Is this ok, Kristi?" she asked. All I could do was nod. "Good," she responded, and unbuttoned my entire top, painstakingly slowly, before leaning in to gently brush my lips with hers. "Is this ok," she asked again. This time I answered by kissing her back.

Oh my god, was this really happening? Are we really kissing? Am I even bisexual?? What the hell was this amazing girl doing to me? My mind was reeling and my heart was pounding. When Alyssa managed to unclasp my front-clasp bra with the ease of much experience, I whimpered feeling my breasts wag free to her caresses. We weren't doing much more than kissing and light petting, but standing there, feeling the breeze of openness, the slight chill in the night air, the heat of her skin and kisses, and the way she devilishly pulled on my new nipple piercings, I could feel my climax coming on. She purred, rolling my steel studs, "bad girl, these are new."

"Keep doing that," was all I could manage. She grinned and leaned in. "Are you sure you don't want me to do this instead?" And with that, she opened her mouth over my pierced nipple, and rolled her tongue over and over in lazy, sensuous circles until I was almost crying, whimpering. My eyes scanned the scene to make sure nobody was walking along the dock, but I stopped caring when she moved to my other nipple and gave it the same treatment. All I could do was close my eyes, hug her head to my chest, and pray this girl would never stop sucking my nipples like this for the rest of my natural life. I felt her hand part my legs just enough to rub my pussy over the fabric of my shorts, but it was enough to send me over the edge. I pulled her hair, pushed my tits hard to her lapping tongue and climaxed almost violently, panting and shuddering against her.

I must have said "oh my god" a hundred times in a row. I couldn't believe that just happened. I couldn't believe how my body responded, and how expert she was at playing me like a sexual instrument. My legs were jelly and I was incoherent.

"It's ok Kristi." Alyssa assured me. "All of this is ok." My life felt like it ricocheted in a completely new and insanely exciting direction, I had no idea if I was ever supposed to feel this way, but whatever this feeling was, I knew I wanted more of it. "I'll get you a t-shirt" she finally offered with a twinkle in her eye. She looked exciting as she walked away to leave me on deck alone for just a minute before returning.

Well, I thought to myself. That was something. Dear god, was it ever.

Alyssa reappeared holding an Orange Crush soda t-shirt that I already knew was going to be skin tight on me. "This looks about your size," she smiled. I smiled back, and quickly put the tee on, hoping nobody was around to witness what just happened. Alyssa read my mind, "Nobody can see you here," she teased. "At least not this time, Kristi."

This time? There would be more times? She took my hand and led me below, but I felt like I was barely touching the ground.

And the night was just beginning.