I Just Had My First Same-Sex Experience — with My Best Friend
Confused, guilty, and craving more
My first sexual experience with a woman was far from typical. I wasn’t kissing a classmate at a high school party during spin the bottle. I wasn’t experimenting with my girlfriends during college. I didn’t go out in my twenties, drinking with friends and fooling around with another woman to see if maybe that aspect of my sexuality existed.
I never felt sexually attracted to another woman — at least, not in those days. I truly admired feminine beauty and the female form, but I never wanted to have sex with a woman. In fact, oral sex with a woman seemed like such a turn-off to me that I wasn’t sure how men did it. For a long time, I felt like I was as straight as they come.
And then I met Charlotte. The woman who turned everything I thought I knew about myself upside down.
The night we hooked up, her husband was asleep in the other room. My loving fiance was at home. It was completely unexpected and unplanned. It was incredible and satisfying, but it also left me feeling guilty and confused.
Were we cheating on the men we loved more than anyone? Did we just ruin one of the best, most genuine female friendships I’d ever experienced?
And, the question that screamed louder than all the others — when could we do it again?
Falling for my best friend
Charlotte and I first met when we were cast in a local theater production together. We were both lead roles, which is a set-up that often leads to insecurity and cut-throat social drama, especially with the competitiveness among young female actors. But for us, it wasn’t like that. She wasn’t threatening, she wasn’t a diva, she didn’t have an attitude.
And, eventually, she made it clear she found me attractive. One night after rehearsal, we were at a bar for a friend’s birthday. I joined her outside in the freezing cold while she smoked. I don’t smoke, but I love to sneak away with her and chat whenever she does.
“I’m honestly straight,” Charlotte said. “But…I’m also, honestly, attracted to you.”
“So, maybe not completely straight?” I asked, nicely buzzed and giggling.
“I don’t know why,” she said. “I’m just — very attracted to you.”
“I feel the same way about you,” I replied. “It’s something about you…I’m not sure what it is, but I think you’re fucking, like, amazing.” (This really is how I talk — there’s a reason I’m a writer, not a public speaker.)
And, I meant it. I felt closer to her than the female friends I’d had for ten years. Something about our personalities clicked. She was like my twin, as far as our personalities went. And, she was very attractive.
Most importantly, I felt safe and comfortable with her. Like I could tell her anything. We told each other our secrets. I trusted her. I felt adventurous with her.
I kissed a girl — and I certainly liked it
As the months went by, we got closer. The show ended, but we kept hanging out every single week. Hanging out with friends weekly is no easy task for a working momma like me. But, I was so enamored of her that I always seemed to be able to make time for her.
She was a woman, and I was falling for her. I’d never experienced anything like it.
During a small get-together at my house, we snuck away to the porch so she could smoke. Both of us had been drinking, and we were as relaxed as could be.
When she told me she wanted to kiss me, I didn’t talk. She’s about four inches taller than me, so I just looked up at her and didn’t say a word as she leaned in. I was happy she was brave enough to make the first move.
I need that. I need someone who can take control and do what I’m usually too scared to do: initiate. That is Charlotte’s specialty.
Her lips were soft, incredibly soft, and fuller than mine. It was nice to feel my lips being overwhelmed by a plumper, juicier, more feminine pair.
Her skin was soft too. I remember thinking what a nice change of pace it was, not feeling a beard scratch my skin like sandpaper. When her tongue explored my tongue, I sighed into her mouth. She was gentle, yet probing. And distinctly feminine.
It was like nothing I’d ever experienced.
Connecting on a deeper level
One night, a month or so later, we were drinking together at her place. It was when the stay-at-home order first began. Gatherings were to be limited to ten people or less.
Our circle was tight, and we were only socializing with a select few — a couple of whom were in our show.
On this particular night, we’d hung out with one of our fellow castmates. It was a guy I knew she was into. And honestly, I was drawn to him as well. We left his place and went to hers, where we shared another bottle of wine.
After talking on the porch for an hour or so, I was in no state to drive, so she led me to the guest bedroom and quickly left me to settle in. I assumed she was joining her sleeping husband in their master bedroom.
Once I snuggled into bed, I was just about to turn the lamp off. That’s when Charlotte suddenly reappeared.
I complimented her on her cute and simple pajamas: short shorts and a black tank with no bra. I knew for sure there was no bra because she had generous breasts. They’re a little smaller than mine. Maybe a C-cup to my D.
Without a word, she hopped into bed with me. It was nothing unusual for us really. We loved to hug. To flirt. To just be close to each other — as friends.
But after we chatted in bed for a bit, I could sense the energy was different this time. She had that same determined look in her eyes. The one she had when she’d first decided to kiss me.
And so, we kissed again. Only this time, we were in bed together. By ourselves. And we were both very much aroused.
I know this because she told me. And I told her. Communication with Charlotte is the easiest thing in the world.
When her hands started exploring underneath my t-shirt as we kissed, I paused things. I sat up and did the thing with my bra — where you take the bra off but keep the shirt on. That’s how shy I am about my body.
But she understood. She continued to kiss me as she felt my breasts underneath my shirt.
Her other hand made its way into the waistband of my panties, and she promptly began massaging me between my legs.
As she stimulated my clit with her fingers — now wet with my arousal — she kissed my mouth and my neck. I alternated between closing my eyes to enjoy the sensation, and opening my eyes to watch her face up close.
Yes, I’d been drinking, but I was completely aware of what was going on and more than happy to be a participant. I’d been waiting for something like this to happen. Yearning for it.
And Charlotte knew just how to get me going with her hand. She knew the right pressure, the right speed, the right intensity. She masturbated me with her hand in the same way she would get herself off.
And it was very much working.
“Are you close?” she whispered in my ear. “I think you are.”
I opened my legs wider, felt her hand get slicker. I was fucking close.
“Yes,” I whispered. “Keep — keep doing that. Fuck.”
And she kept doing that. She had me melting down in an orgasm not five minutes after she’d started. I was liquid in her hands. I was a goner.
I felt more for her than friendship. I’d felt more for her than friendship for some time. Only now, I couldn’t deny it.
Then — it was my turn.
Gone were my fears of another woman’s vagina. I was ready to explore.
I started by straddling her and kissing her as I ran my fingers through her straight, blonde hair. She responded by thrusting her pelvis into mine. It was lovely to feel her writhing beneath me — but the whole point was for me to get on the other side of her. That way, I could use my right hand.
I shifted to the side and gently snaked my fingers beneath the waistline of Charlotte’s shorts. My friend has generous breast like mine, and a soft belly like mine — so her curves felt wonderful beneath my fingers as I explored her.
I teased her skin just below her panty line. She was shaved, like me. See? We’re twins in a lot of ways. Both of us enjoy maintaining a smoothly shaved pussy.
It wasn’t enough for me to just fondle her breasts under her shirt either — I wanted to see them. To taste them. With my free hand, I shoved the neck of her tank top below her breasts and gently explored them with my lips.
They were beautiful. Younger than mine. They hadn’t known the stress of giving birth and breastfeeding. I remember placing my lips on her nipple. It was a big moment for me. I enjoyed flicking my tongue over her hard pink bud, back and forth.
And her response from my tongue — it was sensational. Her back arched and she cried out. Then she clamped a hand over her own mouth to stifle her sounds.
I raised my head and looked toward the door.
“Shhh,” she whispered, a finger over her mouth. “We have to be quiet.”
I kissed her lips to keep her quiet as I trailed my fingers downward, finally exploring the wet warmth between her legs.
Velvet, I thought. Charlotte honestly feels like velvet. Does that sound like a cliche? Maybe. But it’s honestly the first thought that came to my mind as I felt my way inside her cunt with my fingers. Smooth, soft, warm. Velvet.
This wasn’t scary. This wasn’t intimidating. Now — now I could see the appeal of the female anatomy. I was drawn to it like a moth to the flame. Like so many of the men in my life.
Now that I was experiencing it for myself, I was entranced.
I wanted to do my best to make her feel as good as she made me feel — I’m a perfectionist by nature. But this was a first time for me. Charlotte had had a similar fling with a friend of hers years ago, and her experience definitely showed.
When I glided my wet fingers over the folds of her labia and traveled upward, trying to zone in on her clit, she kindly took my hand and moved it back down, planting me in the right spot. I had gone too high, but now that I knew where it was — I went to town.
I started with the rhythm and pressure that I liked. Slow and smooth, with long generous glides up and down alternating with slow circles. I listened to her breathing quicken, and I quickened my pace along with it.
Soon, she had her hand over her mouth again. We couldn’t wake her husband — a man I was friends with. A man I’d been crushing on for months, and she knew it. A man whose sharp wit and humor and good looks constantly floored me — and a man I hoped could one day watch me and his wife together.
But that day wasn’t this day. She’d told me she wanted me to herself first.
And I savored every moment. I kissed her and nibbled her ears and licked her nipples and rubbed her clit until she came, loudly, into her hand.
Then, I did what I did to myself after I orgasm. I kept going.
Just like she did the first time, she vocalized when she was getting close. God, her communication was fucking stellar and I loved that so much.
Not two minutes later, she came at my hands a second time. I was amazed at her sensitivity. It takes a lot more time and effort for me to come twice. I was in awe of her enthusiasm. Her obvious love of pleasure.
I was falling even further.
When we were done, she fixed her clothing and went to bed — with her husband.
Feeling rejected
Since that night, nothing sexual has happened. Not a kiss. Not so much as a cuddle. Our friendship remained strong, until this last month or so, when things started to open up in our state and she started spending more time with other friends.
Since then, we’ve spent less and less time together.
It’s bound to happen. Friends grow apart. We go through periods of seeing certain friends all the time to not seeing them much at all, depending on how busy we get.
I’m trying to play it cool, but I can’t help but feel hurt. I want to explore more with her. More of her body, more of her mind. And…I miss her.
I’ve never done anything like that with a girlfriend before. I’ve never felt comfortable enough or close enough to explore this part of myself with another woman. The part of myself that feels a magnetic attraction to a gorgeous, fun, and loving friend.
She’s my kindred spirit.
She also coming over tomorrow night. For the first time in a long time. I suspect it will be a typical, innocent catch-up over coffee or drinks. Nothing more.
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