The First Time I Slept With My Girlfriend, I Cried

Photo by Molly Frances

I’ve had sexual experiences with Lisa a few times, but a couple of weeks ago, Hubby booked us a hotel room for an evening. He went there early and set the place with flowers, chocolate, and candles because he’s ridiculously supportive of me and adorable. 

Lisa and I sat outside and ate takeout. During those moments that we’re chatting and eating, it felt like hanging out with a friend - someone I trust, enjoy, and with whom I feel comfortable. That also makes it incredibly difficult for me to reach for her hand or lean in for a kiss. I know how to flirt with men and let them know I’d like to move things along. With women, all I’ve ever practiced is keeping my sexual urges inside. Anytime I felt some lustful urge for a woman, I’d distance from her until the friendship ended. Vulnerability was the enemy.

I can’t do that with Lisa. 

Once we were in our hotel room, Lisa donned lingerie for a boudoir photoshoot. She’d wanted to do one for some time and asked me to bring some outfits for her to wear. I’ve taken photos of other women before, but this time it was Lisa... keeping my composure was hard as hell.

In one photo, Lisa is wearing pink satin hot shorts and kneeling on the bed, looking at me over her shoulder. The side of her breast is visible, and her nipple protrudes outward in an enticing way.

Once the camera was away, Lisa (thankfully) made the first move that landed us tangled up in bed.

“What toys did you bring?” she gestured toward my orange roller bag in the corner.

“Um, a couple of different vibrators,” I replied on my way to gather them.

I laid my wand, thrusting rabbit, and we-vibe on the bed.

Wow, you have a lot of toys. I don’t have anything like this,” Lisa had picked up my thrusting vibrator, “It’s a little intimidating,” she set the pink penis down and picked up the Hitachi, “How do you use this one?”

I plugged it in and hit the switch, letting the wand vibrate against Lisa’s leg.

“I want to watch you,” she smiled at me.

I spread out the waterproof blanket from my bag and sat on the bed facing Lisa, my legs spread. I switched on the wand and let it trail up my inner thighs, tease my labia, and finally rest in between my lips just below the swell of my clit. Lisa bit her lip and touched her vulva. My juices were flowing. Just as I moved the wand into direct contact with my clit I shook with the beginning of an orgasm. Lisa gasped, her fingers froze, and she watched me come hard and wet, and long. 

"You come so fast,” she whispered.

“Yeah, then I don’t stop.”

“Show me again.”

A while later, Lisa decided she wanted to try the we-vibe. It’s a tiny little thing shaped like a U that sits both against your clitoris and g-spot. It’s remote-controlled, but being that we were in bed together, the remote didn’t come into play. I helped Lisa put it in place and pushed the button. Lisa’s eyes rolled back, and her full, pouty lips parted in a sigh.

“Oh, that’s good,” she breathed, looking at me.

I kissed her, a deep, needy sort of kiss that said everything that my mouth couldn’t. I touched her softness, enjoying the feel of her quivering under my touch. Then, I reached for the vibrator against her clit and gently wiggled it back and forth.

Lisa clutched me, her fingernails digging into the flesh of my bare ass. Her scream of pleasure only urged me to continue my assault on her sensitive nub. When she relaxed from her orgasm, I moved to pull the vibrator out of her soaked slit. She grabbed my hand.

“No, I want more,” our eyes met, and we dove for each other again.

Later, after we were both spent and ready for sleep, the awkwardness returned.

“Do you mind if I sleep next to you?” I asked, gesturing to where she lay on one of the double beds.

“No,” Lisa shook her head.

We laid there, her curves nestled against mine, and I let the tears fall. These weren’t tears of shame or tears related to my feelings for Lisa - our relationship is still new. I cried because, for the first time in my life, I allowed myself to be sexually uninhibited with a woman. I gave in to my desire to touch her skin, to kiss her lips, and to make her come. I gave into my desire to be me.

I am a woman. I am bisexual. I love a man. I’m falling for a woman.

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