Meeting Caitlyn For Lunch [Part 5] erotic short stories

This is the fifth part of my series “Meeting Caitlyn For Lunch”. You can find the previous parts listed below. It took me a little longer to write this part because I was having a tough time deciding where I want the story to go. Please let me know what you think and any critiques/criticisms you have. If there is continued interest I will be writing a part 6. Thank you!

[Part 1](https://www.reddit.com/r/Erotica/comments/klkdkn/meeting_caitlyn_for_lunch_part_1_wholesome/)

[Part 2](https://www.reddit.com/r/Erotica/comments/kmw6tl/meeting_caitlyn_for_lunch_part_2_wholesome/)

[Part 3](https://www.reddit.com/r/Erotica/comments/korx9n/meeting_caitlyn_for_lunch_part_3_mf_wholesome/)

[Part 4](https://www.reddit.com/r/Erotica/comments/kqsewk/meeting_caitlyn_for_lunch_part_4_mf_wholesome/)

# Meeting Caitlyn For Lunch (Part 5)

I pushed my lips forcefully to hers and moved my hands to either side of her face. There was no hesitation from her, she immediately placed her tongue to my lips, they parted with ease. Our tongues tangled when I let her gain access, it was sloppy and passionate. One of her hands slipped up the front of my shirt, tickling my chest with her fingertips, while the other was still on my thigh.

When she put her hands on me the feeling was unexplainable. It gave me the urge to push her back, pin her down, and give her everything I had. I had to slow this down, as much as I wanted her, and as much as she seemed to want me, the whole situation was only a day old. Moving too fast could be dangerous, I could ruin everything if she wasn’t comfortable. I needed to make sure we were on the same page.

My hands fell from her head to her hips and I started to back away from the kiss. I took her bottom lip between my teeth and bit down, she let out a small yelp, I thought I hurt her.

I kind of went into panic mode, “I’m sorry, are you okay? Did I hurt you?”

“Not at all, it was good, I loved that.”

“Oh thank god, it sounded like you were in pain. I thought I screwed up.”

She looked me in the eye, “Listen to me, if you hear me react to something you do, I like it. I trust that you won’t hurt me, plus if you do then I’ll beat you up, you know I can.”

I laughed, most of my worry started to melt away. I still didn’t want to do something over the line, we needed to figure out the boundaries. I also wanted to figure out exactly what this relationship was before we did something there was no turning back from. I needed to bring the conversation up, it was going to make it easier in the long run.

“Caitlyn, can I ask you a question?”

“Of course, what is it?” I could see a small look of worry on her face.

“What do you want this relationship to be? I know you said you want to be with me but what does that mean?”

She was prepared for the question, answering promptly and with confidence, “I want you to be my boyfriend, and I want to be your girlfriend. I don’t want this to just be some stupid fling, I’m serious about you.”. There was a silence for a second before she spoke again, “What about you? What do you want us to be?”

I felt a smile creep over my face, “You described exactly what I want, and what I don’t want. I don’t want this to be a hookup, you’re my best friend, I want you to be my girlfriend. Don’t get me wrong, I want you so bad, but I don’t want us to make a mistake and take this too far and too fast.”.

She nodded in agreement, “Me too, I just can’t help myself when we start doing stuff. I’ve imagined having you for months, and now you’re finally here, sitting in front of me and kissing me. So, what do you want to do about this? How can we do this without making a mistake?”.

An idea popped into my head, “Okay hear me out, how about we go on a date tonight? It can be right here in the house. Have you already eaten dinner?

She shook her head.

“Then let’s order something, we can have dinner together and then do something after. We could watch a movie, go on a walk, anything you want, it’ll be fun. How does that sound, you want to do it?”

“I never thought I’d be going on a date in my own house but that sounds nice, let’s do it!” You could hear the excitement in her voice, she liked the idea.

I threw my arms around her, wrapping her up in a huge bear hug. I wanted to express my feelings without speaking, in my experience hugging someone is the best way to do it. She got the message, returning the sentiment by embracing me back.

The hug wasn’t meant to be intimate, there were no sexual intentions behind it. That is until I felt her nipples brushing against me. The urge was too great, I squeezed with all my force for a split second before releasing her. Her chest pressed against me and a short moan escaped her lips as I felt her body shiver against me.

Leaning away from the hug she slapped at my chest and spoke while giggling, “Hey, quit it! If we’re gonna take our time you can’t be doing that, I won’t be able to control myself. Plus, it’s not fair that I can’t do anything like that to you.”

“Oops, I didn’t mean to.” I said in my most sarcastic voice while moving my face closer to hers. “Just because we’re going slow doesn’t mean I won’t tease you.”

I gave her a quick peck on the lips, “By the way, you can do the same thing to me, only when we’re standing though.”

She gave me a warning, “If you keep teasing me, I won’t be taking this slow. I know you won’t be able to resist me if I decide to do that.

“Oh yeah, what would you do to me?” I thought she was joking around. What she said next told me that she wasn’t.

She stared into my eyes, “I could hug you while we’re standing and push my waist into yours like you pushed into my chest. I could make you twitch a little, but that wouldn’t be enough for me, I’d want you completely at my mercy. Instead, imagine if I got up and sat back down in your lap right now, my entire weight on top of you. I’d wiggle my hips until you settled, pushing up against me. Then I’d start rocking forwards and backward, it’ll make you pulse, and I’ll be able to feel every part of it. You’ll be able to feel the heat radiating from between my legs, I’ll be enjoying it as much as you. I know that you wouldn’t last, within minutes I’d have you moaning my name, begging me to stop, while you secretly want me to keep going. You’d be mine.” She leaned forward and kissed me deeply, tickling my lips with her tongue before pulling away.

She was right, even the thought of it made my body weak and caused me to throb. “We’re going to have to reconsider this whole taking our time thing then because I’m not going to stop teasing you.” I wanted what she said, and I needed to push her towards doing it.

We were staring intently at each other, both of us waiting for the other to make a move. I knew if one of us did, we wouldn’t be able to stop, all bets would be off, and so would our clothes.

Caitlyn broke the silence and somehow acted as if nothing had happened. “Come on, we’ve got a date to be on, let’s go get some dinner. If you’re good, I’ll let you have a little dessert after.” She winked at me and gave me a peck on the cheek before getting up off the bed.

The food arrived at the house; Caitlyn had ordered Chinese food from a local place. We were in the kitchen getting everything ready and there was music coming from her Bluetooth speaker. I wasn’t paying attention to what was playing, it was nice background noise. She was at the counter putting everything on plates and I was about to get drinks for the both of us.

“Hey where are your cups and what do you want to drink?” I asked.

“On the bottom shelf of this cabinet above me, and I’ll take a water please.”

I walked behind her, about to reach over and open the cabinet. Instead, I wrapped one arm around her waist. My other hand brushed her hair aside, I laid a kiss on the side of her head, directly on the temple. She turned to look at me and smiled, it was so intoxicating.

“What was that for?” She asked.

“I wanted to let you know how great you are.”

“Aww, but that’s all you.” She leaned back into my arms, allowing me to hold her.

A new song came over the speaker and I recognized it right away. The song was “Stuck Like Glue” by Sugarland. That song is my ultimate Feel-Good song, it never fails to put me in a better mood, even if I’m as happy as could be.

Caitlyn began to hum along with the song, I joined in with her by quietly singing.

She laughed at me, “Are you singing?”

I know I’m a horrible singer, but I had no shame around her, “You know it.”

I took her hands, spun her around, and began to sing louder. We started to dance to the music and sure enough, I got her singing along with me. Now, I’m no dancer either, it’s worse than my singing which is saying something. But with her, there were no worries about how I looked or sounded.

Soon enough we were fully dancing in the kitchen, doing clumsy spins and dips. I’m sure it looked ridiculous. When the song ended, it moved onto something slower and I stopped paying attention to it. My focus was on her.

I pulled her in close to my body as she was gathering herself back up, both of us had the biggest smiles on our faces. We started swaying, it was our terrible rendition of a slow dance, but we were close, and that’s all that mattered. She rested her head on my chest as we kept dancing, her arms wrapped around my body and held me tight. We separated a few minutes later as the song ended, and she kissed me.

“That was stupid, but it was the most fun I’ve had in a long time. I hope you know that you’re not a very good singer though.” She teased.

“I’m well aware, neither are you though.”

“Oh shut up, now let’s eat before our food gets cold.”

We went to the living room to eat; we could have something on the TV, and it was super casual. There was a couch in the living room, Caitlyn sat down next to me, brushing up against my side. She turned the TV on and started playing *Enola Holmes.* I had mentioned a few weeks earlier that I’ve been wanting to watch it.

“You haven’t watched this yet, right?” She asked.

“No, I haven’t. But how did you even remember that I wanted to see this, I mentioned it for like two seconds.”

Her eyes rolled at me, “Because I remember everything, obviously.”

We finished eating and as we found out, putting on the movie was pointless, we ended up talking over it. I can’t even remember what we talked about, time was flying, every minute I spent with her felt like it was a second.

Eventually, though, the conversation turned to the dirty side, it was inevitable.

Caitlyn turned and faced me, hesitantly asking something. “So this might be a weird question, but what do you like to see someone wear? Like, what would your favorite outfit be on me?”

“I guess it would depend, I would have different answers if this outfit has to be appropriate for public or not.” I was curious about what she was getting at.

She let out a short laugh, “Hmmm, give me appropriate first.”

“For appropriate, I think it would be those leggings you’re wearing and some sort of lower cut top.”

“Really? You like leggings more than anything else? They’re so simple.”

“That’s part of the reason I like them, the simpler the better. Not to mention they don’t leave much to the imagination, especially when they’re kind of see-through like those.” I said as I pointed to her legs.

Her eyes went wide, “These are see-through? You’re joking, right? Please tell me you’re joking.”

“Don’t worry, they aren’t in any of the best parts.” I chuckled as I said it.

She punched me on the arm, laughing with me, “HEY! I’m serious, are they really that thin?”

“Okay, okay. Yes, they are, but only at some parts like further down your legs.”

She clutched her chest, “Oh thank god, I’ve worn these everywhere, I would’ve been so embarrassed if people could see through them. Alright, get back on track here, what about something not appropriate?”

“I think it depends again, are we talking about ‘actual clothes’ or something you’d wear underneath.”

“Actual clothes I guess, we’ll work our way through the layers.”

“For a top, I’d say like a super-thin, tight, crop top. Not something you can necessarily see-through, but thin enough that you can get an idea of what’s underneath.” She nodded her head, making a mental note of what I was saying.

“Okay, what about underneath, what kind of bras do you like?”

“My favorite type of bra I think would be a bralette or whatever they’re called. Something strappy and lacy. Preferably it would be very low cut in the front, and I’d be able to see through it except for where the lace covers.”

“Ooh good choice, I love wearing those. What about pants?”

“High waisted, tight, short shorts, hands down, there’s not even a competition for those.”

“How short?” She asked.

Instead of telling, I showed her. I put my fingers on the top of her thigh, a few inches off her body. “About that short.”

She giggled, “Okay, so pretty short. Last up is panties.”

“This is like the shorts, there’s no competition. My favorites are low rise boyshorts, as low cut in the front as possible and the same in the back, I want them to be cheeky. I like a lace material, similar to the bra.”

Her face darkened, “I think that’s the exact thing I’m wearing right now, but I’m not sure.

“Let me see then, I’ll tell you.” I was joking when I said it. Either she didn’t realize or didn’t care.

Do you want to see them? I kind of want to know if they’re the right ones.”

My heart and mind started to race. Was I about to see her in panties? “Sure.” Was all I could muster up; I could hear the nervousness in my voice.

Caitlyn leaned to the side, giving me a better view, and moved a hand to her hip. Her fingers hooked into the leggings and she started pulling down. Her underwear started to come into view, she kept going until her entire hip was exposed. They were hot pink, lacy, and her skin showed through the thin parts, exactly what I described.

“So, do you like them?” Her breathing quickened waiting for an answer.

I tried to push her a little more, “Yes, definitely yes. I think I might like them, even more, depending on what the rest look like though.”

“Ha-Ha, nice try, but you’re not getting me to take off my pants that easy. You’ll have to earn that.” She said while going back to her regular sitting position and pulling her pants back up.

“Oh yeah? How would I do that?” Again, I said it jokingly, I didn’t expect her to have a real answer.

Her voice was now serious, “All you have to do is answer one question.”

I was wary but curious, this seemed too easy. “One question, and then I’ll get to see the rest of what you just showed me?”

“Yes, one question, and depending on your answer you’ll get to see the rest. There is one rule though, if I ask the question, you have to answer it, you can’t chicken out and not tell me your decision. Keep in mind, I’ll have zero issues with you saying no to hearing the question, it won’t upset me. With all that known, do you want me to ask?”

“Yes.” I had to know; I wouldn’t forgive myself I didn’t say yes.

“Okay, here we go. Do you actually want to take this whole thing slow? Because right now, all I want is to find out what I like, and I want you to be the one who helps me.”

That was the most difficult question she could’ve asked, “Oh come on, you can’t expect me to answer that.”

She held up a finger, telling me to stop talking, “Oh yes I can, you agreed to answer it. And I don’t think you’ll like what happens if you don’t.”

“What happens if I don’t answer it?”

“I guess if you really want to know, you can find out.”

I wasn’t going to test her, I agreed to answering the question. “Alright, Alright, I’ll answer. Yes, I want to take it slow, also no, I don’t want to. I don’t want to screw this up, but at the same time, all I can imagine is your hands on me, and mine on you. I want nothing more than to help you. If you have a solution for not wanting to screw this up, I’m all ears.”

She looked puzzled, like she was thinking very hard. “How about this, we take it slow, but not in the way we talked about before. My friend told me about something she did with her boyfriend when they first started dating. It sounds stupid, but they played truth or dare. She said it helped with figuring out what they both wanted. It’ll let us find out things we like and also give us a chance to do them. If there’s something either of us wants to do, or ask, this gives us the chance to. If one of us is uncomfortable with anything, we can say no, with zero questions asked. What do you think?”

This was going to get interesting; I didn’t want to deny this opportunity. “I like it, let’s do it. But before we start, was that answer good enough for me to get my reward?”

“Oh no, I needed a firm yes, I’ll tell you what would’ve happened if you did say yes though. ” She put both hands on my legs and moved her face close to mine. “By now I’d have slipped my pants off, giving you a good show. Then I would’ve told you to put your hands on my hips. I’d let you peel my panties off, leaving myself exposed. You would’ve been able to do whatever you want to me.”

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