In the days before swiping, I made a profile on an online dating website.
I was in a six-month rut, coming off a particularly strange relationship where I unintentionally started a love triangle that didn’t end in my favor. (They’re happily married now, congrats.)
Following that relationship ending, I put myself out there emotionally. I made myself vulnerable and wanted nothing more than a *relationship*. Sure, sex would be great, but what I truly longed for was someone to go on dates with, watch movies with, just hang out with.
I had a couple of friends that I thought were cute. The time of crushes, how innocent. The slight nervousness, the uncertainty of what could happen next. Back then, and maybe still now, I thought it was best just to be candid. I told my crushes how I felt, and they didn’t feel the same. The rut continued.
That’s when I made the profile. Everyone on the dating site was someone I knew from high school. I didn’t message a single person—the thought of dating someone I was aware of from high school filled me with dread. I turned off my profile.
A few months later, I got a job and moved to a new city—a small one where the people were friendly and the winters were cold. I made some new friends; work was challenging yet enjoyable. Life was better. But my heart still longed for something more.
I turned my dating profile back on, took new photos, and rewrote my bio. It was quiet at first. I tried to write thoughtful and friendly messages to women who legitimately seemed like someone I’d be interested in getting to know.
Someone responded to one of my messages. We talked for a bit but never met up in person. The connection wasn’t there, even from the messages. And that seemed all right.
Another person responded, Olivia. She was cute and funny. We had a similar sense of humor. We chatted for a few days and planned a dinner date. We went to a small tavern downtown.
Olivia was a comely, curvy woman with dark hair, and I was immediately taken with her physical appearance. Her dress was covered in sunflowers.
We were seated against the back wall. We both ordered a beer and a burger. It was during the World Cup. Neither of us followed the games, but loud cheers and yells at the referee interrupted our conversation. The beers, the burgers, and the company were all wonderful. My cheeks hurt from smiling.
I tried to be a gentleman and pay for dinner, but she insisted we split it. I thought that meant she didn’t have a good time. We walked down the city streets, the mid-summer sun setting. We got maple creemees, and she let me pay for both of them. We held hands while we ate our ice cream.
“Thanks for the nice night. It was great getting to know you,” I said after we finished our soft-serve. To me, it was a perfect first date.
We hugged and walked our separate ways.
Once home, I showered and got ready for bed. Box fan blowing, I laid above my comforter and tried to sleep, but I couldn’t. I looked at my phone. There was an unread text from Olivia. “I had a lot of fun tonight.”
“Me too,” I replied.
“You’re really attractive.”
No one had ever been so forward with me before. I was taken aback and wide awake. “I think you’re so beautiful.”
“Would it be all right if I sent you a nude photo?”
I was unsure. This was moving fast, too fast. *I’m not the kind of guy who moves so fast, am I? I just want to find a nice person, get to know them, move slowly.* My flesh broke out in goosebumps. My penis stiffened; desire took over.
“Only if I can send you one.”
“Deal.”
I jumped out of bed, turned on the light, and pulled down my boxers. I took a selfie in the mirror of me smiling, my penis erect. I sent her the photo.
She responded right away with a photo of her lips pursed, topless, ghostly nipples punctuating her pillowy breasts resting off the sides of her upper-body.
“Wow, you went for it right away,” she said. “Sexy! Want another of down below?”
“Yes, please.”
She sent a photo of her legs spread, her mons pubis freshly shaved and her lips open.
“You’re so sexy, seriously,” I replied.
“God, I’m so horny right now. I’m rubbing my clit and looking at the photo you sent.”
I started to stroke my cock, looking at the photos of Olivia. I was sweating, the box fan not enough to cool down the hot summer night.
“I want you, so bad,” Olivia said. “Can you come over?”
*Am I the kind of person who has* sex *on the first date?* Up until that night, I thought not.
“I’ll be over right away.” I pulled on clothes, nearly tripping over myself trying to put shorts on. She sent me her address. I knew the street—it was across town. I hopped on my bike. Cicadas buzzed. The dim light of the street lamps was barely enough to see the road in the dead of night.
Olivia lived in a one-bedroom apartment on the first floor of an old house that was split into separate units. I saw the light on in her window. I texted her, “I’m out front.”
She opened the door to her apartment. She was wearing a simple cream nightdress. “Hey, sexy,” she said. I floated up the stairs to the small wooden porch that led to her front door. We embraced. “Let’s go inside.”
“Let me lock up my bike first.” I did.
We went inside. Succulents and plants filled her entire living room. She had a couch, a coffee table, and tons of books. No television. “Want anything to drink?”
“No, thanks.”
She led me by hand to her bed.
Our tongues danced. We took off our clothes. Our hands and mouths explored each other’s bodies—every curve, bump, muscle, and mark new to each of us.
I kissed her wonderful breasts and ran my tongue around her nipples. It felt like I wasn’t even touching the bed.
She opened the drawer of her bedside table and pulled out a sleep mask. “I’d like you to wear this while I use my mouth. Want to give it a try?”
“I’m not sure…” I said. I had seen videos with blindfolds and whips and ropes before. It always seemed like it’d hurt. “I’ve never done anything like this before. But it is *only* a sleep mask. Let’s try it! If I’m not into it, I’ll let you know.”
“Sounds good,” Olivia said as she slipped the mask over my eyes.
Unable to see, even when I opened my eyes, I lost my bearing. Everything intensified. Olivia’s room smelled of lavender and patchouli. I felt her soft lips kiss my stomach. Her hands gripping on my thighs. Her tongue as she took me. Then the warm, moist feeling that took me over the edge.
“I’m going to come soon.”
She took a break and said, “That’s fine. Come in my mouth.”
I did, and it was pure bliss. She took it all. I felt her make her way up toward me. Then, my come lingering, she stuck her tongue in my mouth.
“Your turn,” I said, pulling off the mask, rolling us over, and putting it on her.
I kissed her from her neck to her pussy, pausing at her breasts on the way down. I kissed all around her vulva, then her clit. “Ahhh,” she said. “That’s it.”
I pushed my tongue firmly against it, lapping it up. She reached for me, finally finding my hair. She ran her fingers through it. We were both breathing heavily. Her wetness covered my entire face as I used my mouth the best I could. She pushed my head against her and said, “I-I-I’m going to orgasm.”
Her hips and upper thighs shook uncontrollably while I continued to eat her out. When her orgasm finished, I slowed down and then kissed my way back up to her mouth. I lifted the mask from her eyes.
“How was that?” I asked.
“Fucking amazing,” Olivia said. “What’d you think of the mask when you were wearing it?”
“Super fun, really sexy.”
We kissed. We snuggled.
After a few minutes, she rolled over to her bedside table drawer and grabbed a few more things. At the time, I didn’t even know what they were. A cock ring, a butt plug, and a small vibrator shaped like an egg. “That was a fun start,” she said grinning. “How about we try these next?”
—
_This story is a lightly fictionalized tale from a date I went on about nine years ago. Thanks for reading!_
Source: reddit.com/r/eroticliterature/comments/ocb5um/trying_new_things_mf