Building a Life in Chicago

I finally matched with a female on Tinder. After a weekend of fucking Chad and Owen, I had had my fill of guys for a while, especially after getting a picture of Jessica fucking Danny and realizing how much I missed them. So, for the next week, I kept my Tinder on exclusively girls, finally matching with one towards the end of the week.

Her name was Rachel, and she was a dance instructor, theater actor, and singer. She was absolutely gorgeous. After talking for just over an hour, we exchanged phone numbers and agreed to meet the next day for a coffee date.

I was super nervous the next day as I got ready. Was I really going on a date with a female? Would she see right through me? Is this what I really wanted? Was I actually attracted to all females or just one? I pulled my black hair back into a ponytail, put on a white, loose-fitting blouse, black and blue leggings, and drove over to the coffee shop.

Rachel met me outside the little coffee shop, greeting me with a handshake and a quick, awkward hug. Standing five feet, six inches tall, she had brown, curly hair that went just past her shoulders. She wore it loose today, with her bangs parted to each side. With a hint of make-up on her face, she wore a blue tank top, the cleavage of her C-cup-sized breasts just barely visible, and a red, floral printed skirt that went down to her ankles. Pink fingernails and a white scrunchie on her wrist completed her outfit.

We went into the little shop, made small talk, ordered a coffee and a sandwich, and found a table to sit down at.

"So," Rachel said with her mid-western accent, "I noticed on your profile that you said you're from Utah. What brings you to Chicago?"

"Dental school," I told her. "And just wanting to get out of Utah."

"I've never been, but I hear it's beautiful, just with some weird people. I'm guessing you're not Mormon." Rachel asked me as she sipped her coffee.

"I was. I grew up Mormon but fell away pretty quickly. Utah really is beautiful, but I needed a change," I told her.

"I get it. I'm from Indiana, went to college in New York, moved to Chicago, and travel as much as possible," she told me. "Your profile also said something about being divorced? Does that have to do with the change of scenery?"

"Definitely. It's a long story, but it was messy, and I needed to get away," I said, almost hoping she didn't want more details.

Rachel took a bit of her sandwich and said, "I like long stories."

"Including ones that involve lots of drama? I don't know; it might make you run away," I said.

"I'm a theater nerd; of course I love drama filled stories. And you're too cute to just run away from," she told me, continuing to eat and drink.

"Alright, but I warned you. A few years ago, my entire family went to Las Vegas to watch my youngest sister get married. I'm the second-oldest of four, by the way. The last night there, I caught my oldest sister's husband having sex with my brother's wife in the hot tub," I started the long story.

"At the time, I was married and had a bit of an open relationship with my husband. He couldn't take care of my needs and let me sleep around, so long as I was the primary source of income. Dumb arrangement, I know. Anyway, I had always had a crush on my brother-in-law, so I told him that I knew he was cheating on my sister and wanted some of the action," I said, with Rachel intently watching me.

"We foolishly kept it up for the next few months," I continued, but Rachel interrupted me.

"Just you and him? Or did he keep sleeping with your sister-in-law? How long had they been cheating with each other?" She asked all at once.

"No, he was sleeping with both of us. And that was the first time," I said.

"What's their name?" It'll make the story easier to follow," Rachel said.

"Danny and Jessica," I said.

"Sorry, one more question. Did you guys have a threesome together?" Rachel asked.

"Kind of? "We were all in the same room, naked, having sex, but outside of me doing one thing with Jessica's breasts, we didn't touch or kiss," I explained to her.

"Fair enough," she said.

"A few months into the affair, Jessica left my brother and divorced him. She got her own apartment and kept sleeping with Danny. Around that time, I was looking at dental schools and getting an interview here. I invited Danny to fly out here with me; we spent a lot of time in the hotel room and flew home the next day. When I got home, my husband confronted me. I admitted I was sleeping with Danny, and he left me. I got super drunk that night, called my sister that Danny was married to, and confessed everything to her," I said, watching for Rachel's reaction.

"Oh my God!" She exclaimed.

"I know. It was wrong of me on every level. You can leave if you want to," I said, hoping she wouldn't.

"Nope, I'm too invested now. What happened next?" She asked.

"Well, my sister kicked Danny out, and they ended up divorced. Me and my husband went to therapy once, figured out it wasn't going to work, and got divorced. But, before that even happened, I convinced Danny to sleep with my youngest sister; that made Jessica mad, and her and Danny had a falling out, and she moved to Idaho," I said.

"Jesus," Rachel said.

"Right? Anyway, after about a month, I missed Danny so much that I went to his apartment, and we started our affair back up. He and Jessica started talking again as well. After a few trips back and forth, they confessed their love for each other, Jessica moved back to Utah, and they got an apartment together," I said.

"And that all led to your moving to Chicago? Are you still friends with Danny and Jessica?" Rachel asked me.

"Yes. I actually ended up living with them for the last three months I was in Utah and texting them both pretty much every day," I told her to finish the story.

"I feel like you could turn that story into a play," Rachel said with a laugh, making me laugh too. "So, I guess my final question would be, have you ever actually been with a woman? Or is it just a thought you've had?"

"Nope, I've never been with a woman. But I have seen plenty of videos of Danny and Jessica together, and I find myself watching Jessica way more," I said. "So, I'm really curious what it's like. And, after the luck I've had with guys in Chicago, I wanted to try something different."

"I hear you. I always had a feeling I was different when I was growing up, but I still liked guys too. It wasn't until I went to college that I figured out that I like girls too," she told me.

"Would it be rude if I asked how many you've slept with?" I sheepishly asked as I finished off my sandwich.

"Boys or girls? I'll only tell if you do," she replied back.

"Both?" I asked.

"Probably something like nine boys and seven girls. What about you?" She said, finishing her sandwich.

"Way too many to count boys and no girls," I told her.

She laughed as we finished our coffees. We changed subjects, talking about our current jobs, career plans, and other future plans. Rachel eventually asked if I wanted to go for a walk around the park next to the coffee spot, and I said yes. For the next hour, we walked and talked, getting to know each other. Eventually, she had to leave to go teach a dance class, and we left each other with a longer hug than when we first met and a promise to call later that night.

I went home that night, feeling happy to have met her and that the date went well. As I relaxed in bed, thoughts of Rachel and a potential hookup filled my mind. She had told me that she had a decent following on Instagram, and I decided to find her page. It wasn't too hard, as it popped up first when I typed in her name. I gasped when I saw that she had almost 70,000 followers. She had told me that her TikTok was even bigger, but I would have to download it to see.

I pressed the 'follow' button and started to scroll through her page. She posted a ton! Her dance classes, places she visited, friends, family, the beach, plays, her singing, and on and on. In a lot of her pictures, she was either showing off her cleavage or dressed up fancy to go to a play.

I could feel myself starting to get turned on as I looked at her pictures, and I reached my hand down in between my legs and started to rub my groin. As I got wetter, I lifted my butt off the bed and pulled my leggings down, quickly followed by the black thong I had on. I rubbed my fingers on my bare pussy and spread my legs to give myself lots of access.

I found a video of her dancing to a Broadway song, wearing a tight purple top and black spandex shorts. As she moved around, her breasts bounced and jiggled, and I slid my finger inside myself, memorized by them. As she dipped and dived, she kept giving views down her top, and I wanted to know what her breasts felt like.

As I kept playing with myself, I scrolled some more, finding pictures of her in evening gowns, mini-skirts, and tight tops. I put the phone down for a second, reached over to my nightstand, and pulled out my vibrator. I replaced my fingers with the vibrator, running it up and down my vagina, leaving it for a few seconds on my clit, and repeating the process.

I scrolled back far enough on Rachel's Instagram that I was in the previous summer, and I found a series of pictures of her at the beach with somebody that must have been her sister, because they looked just alike. But my eyes were drawn to Rachel. Her breasts looked magnificent in her multi-colored bikini top, and it looked like she had a bush in the white bikini bottoms she was wearing.

I stared at her amazing body as I felt an orgasm building up inside me. I left my vibrator on my clit until I started to cum. My back lifted off the bed, my mouth opened as I moaned, and my eyes closed as I felt the wonderful feeling of an orgasm. "Oh my God," I heard myself say as it kept going, spurred on by the stimulation on my clit.

When I was finally able to pull it away from my clit, I turned the vibrator off and sat it down. I smiled at the picture I just came to, hoping to see more of her soon.

I was hoping that Rachel would really call me later that night, but I had to settle for a text. It read, "Hey, I really did have a great time with you today. I guess I should have made two things clear to you. First, I'm not looking for a hookup, at least not with another female. So, if that's what you want, I'm not for you. Dating, yes, definitely. Hopefully that's not a deal breaker for you, since I know you're just kind of exploring this whole lesbian/bi thing. Second, I'm applying for a theater camp in London this summer, and I would be gone for a couple of months. Again, I really did have a good time, and I hope we can do it again!"

I smiled as I read her text and then thought about what she said. Was I just looking for a hookup? I don't think so. I texted her back, "Hey! I had an amazing time, too. I honestly hadn't thought about what I was looking for. But I found you! Oh God, that was cheesey. Going to London would be super cool and sounds like a good experience for you. Hopefully I can get to know you better and more often before you go!"

"Oh man, that makes me so happy to hear! I was really hoping those wouldn't turn you away because it wouldn't be the first time. I guess we just need to find a time to go out again," she replied back.

"How about Monday?" I asked her.

"I'm free Monday night. Dinner?" She answered.

"Yes, please," I told her, and we spent the next little bit talking about places to go before we finally settled on one.

Dinner that Monday with Rachel was just as good as the coffee date a few days before. She told me more about her life, the plays she had been in, the dances she had choreographed, the venues she had sung in, and what she ultimately wanted out of her career. I felt like I had spent so much time talking about myself on the first day that I just let her talk and talk.

As we walked out of the restaurant and back to our cars, she asked me, "Hey, so, what are you doing this Friday?" I told her I didn't have any plans, and she said, "There's a little underground lounge that me and some friends will be signing at that night. You should come, if you want. And maybe we can spend some time together afterwards."

I told her that sounded great, and she said that she would text me all the details. Before we left each other, she gave me a hug and a kiss on the cheek that made me blush.

That Friday, Rachel had told me that I should dress like I was going to a Broadway play, so something pretty nice. I panicked for hours trying to figure out what to wear, almost went to a store to try to find something, thought about canceling but didn't want to miss listening to her sing, had a phone conversation with Danny, who reminded me to just be myself, and finally settled on a dress that I already had in my closet.

It was a black, spaghetti string, floral print dress that ended just below my knees. I didn't put a bra on, which I hoped would be an advantage later in the night. I finished it off with a black thong, put a little hint of make-up on my face, and left my black hair loose and slicked behind my head.

When I arrived at the lounge, I gave my name to the hostess, as Rachel told me to do, who showed me to a little table just off the front of the stage, and I ordered a glass of wine from her.

When Rachel came onto the stage a few minutes later, my jaw dropped. She had her brown, curly hair mostly loose, but a little ponytail on top of her head. Stage makeup on her face with bright red lipstick. Her breasts were on full display in the purple dress she had on. The dress was tight around her midsection and waist and ended just below her groin. A tiny pearl necklace finished off her outfit. She saw me, smiled, and waved just as she and her friends started to sing.

Listening to them sing, I finished my glass of wine, switched over to water, and ordered some food as well. For the next two hours, I listened to Rachel and her friends singing a variety of Broadway songs, some of which I knew and some of which I didn't. I was glad I was sitting alone, being able to focus only on Rachel as she moved around, doing cute little dances, even blowing a kiss to me once, and laughing as I pretended to catch it.

When the show was done, Rachel and her friends received a standing ovation. I paid my tab, and I tried not to look too awkward as I stood around waiting for Rachel. When she eventually came out, she was saying hi to everybody else she knew there as she made her way to me. She greeted me with a hug, and I said, "You're so beautiful! That was amazing!"

"Oh, thanks! It was so much fun. And talk about beauty. Look at you!" She replied back, taking my hands in hers and pushing away a bit to look up and down my body. She introduced me to some of her friends, holding my hand the entire time, which drew more than a few curious looks.

After saying hi to everybody, Rachel turned to me and asked, "Did you drive here?" I told her yes, and she said, "I took an Uber to get here. Would you be OK to give me a ride home?" I told her, of course, as she sat down with a plate of food that she had ordered.

We left about an hour later, Rachel having finished her food and grabbing a duffle bag from behind the stage. Rachel put her bag in the back seat of my car before climbing into the passenger seat as I started it. "Wait," Rachel said, placing her hand on my hand that was on the gear shift and preventing me from changing it.

I looked over at her and was going to ask what, but Rachel surprised me by leaning over the center console to me and planting a soft, sweet kiss on my lips. I leaned forward to return the kiss, but Rachel pulled back and said, "You don't have any roommates, right?" I told her no, and she smiled as she said, "Maybe we should go back to your place. If you want to."

Rachel put her hand on my leg, close to my groin, and I glanced down at it, and said, "I do want to."

By the time we arrived at my apartment, my thong was soaked in anticipation of what could be happening. I let Rachel into my apartment, shutting the door behind her, and giving her a quick tour of the small, one-bedroom apartment.

"It reminds me a lot of my first apartment here in Chicago," she said.

"It's not bad. I at least feel safe here," I told her.

I followed Rachel back into my bedroom and watched as she sat down on my bed, closing her legs and putting her hands in her lap. She looked up at me and asked, "Would you like to join me?"

I gladly sat down next to her. We looked into each other's eyes, and I watched as Rachel brought her hand up to my face, caressed my cheek, put her hand on the back of my head, and pulled me towards her. Her lips met mine, and this time, I returned the kiss. I brought one of my hands over to her body and tried to move it to her breasts, but she grabbed it with her free hand and lowered it down. We continued to kiss, our eyes closed, our heads moving in sync, and I truly felt another woman's lips for the first time.

When we ended the kiss, I said, "Wow," as we both opened our eyes.

"Kourtney, I really do like you. When I saw you tonight, I got so happy. I'm really glad to have met you," Rachel told me.

"I feel the same," I told her.

"I don't want to rush things too much between us. I want to take it slow, if that's OK with you?" She said this, holding both of my hands.

"Of course. I totally get it," I told her, releasing a deep breath that I didn't realize I had been holding in.

"Are you OK?" She asked me.

"Of course. Why do you ask?" I replied back.

"Just making sure. Were you hoping for something more to happen tonight besides a kiss?" She asked me.

"I don't know. Maybe? I guess I'm just used to bringing guys home and knowing exactly what they want," I told her, trying to hide my disappointment, looking down and away from her.

Rachel laughed and said, "Kourtney, girls aren't that much different."

My disappointed expression quickly turned to surprise as Rachel started to kiss me. But this kiss was different from the first kiss. More forceful and passionate. As we kissed, Rachel forced me to lay down, partially laying on top of me. She brought her hand up and grabbed my breasts through my dress, rubbing my nipples at the same time.

She stopped kissing my lips, instead kissing my cheeks, my neck, my chest, and the upper part of my breasts. She used her hand to pull my dress down over my nipples, exposing my B-cup-sized breasts to her. She smiled as she heard me moan when her tongue flicked around the nipple of my right breast. I watched as she took her fingers and rubbed my left nipple with them. Her lips wrapped around my nipple and sucked it into her mouth. She then switched her mouth to my left nipple, giving it the same treatment as her tongue and mouth.

Looking up at me, she asked, "Is that better? More, what were you expecting?" I nodded my head yes as Rachel smiled and said, "Good. I'll keep going."

I instantly got butterflies in my stomach and felt my vagina getting wetter as I watched Rachel, still in her purple dress with her make-up and hair all done up, move down my body. I spread my legs and started to pull up my dress when she reached my groin, and she helped to hike my dress up. She smiled when she saw my thong and asked, "Did you wear this for me?"

I nodded my head, and she said, "It's hot, but it's got to go." She hooked her fingers into the thong and started to pull it down as I lifted my butt off the bed. Seeing my shaved pussy, Rachel smiled, leaned down, and started to lick and kiss around my vagina. I moaned as her lips and tongue briefly touched my pussy lips and closed my eyes when she finally licked up and down my slit.

She brought her hand up and used her fingers to pull apart my wet pussy, inserting her tongue into it, and started to dart it in and out. I moaned loudly as she tongue fucked me and Rachel expertly worked her tongue all around my pussy, both inside and outside, using her lips to suck my pussy lips into her mouth, flicking my clit with her tongue, and humming as she did so, sending vibrations deep into me.