This is part 6 of my series. I’m sorry for taking so long with this next part but I hit a bit of writer’s block. I wasn’t happy with how I was continuing the story so I had to restart multiple times lol. I’m not sure how many more parts I’m going to write, but I’ll try to post them in a timely manner. As always, critique is always encouraged! 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/)
[Part 5](https://www.reddit.com/r/Erotica/comments/kwcjzv/meeting_caitlyn_for_lunch_part_5/)
# Meeting Caitlyn For Lunch (Part 6)
My heart and mind started racing. I thought Caitlyn was this sweet, innocent girl. Forget about innocent though, she wanted me to take her panties off.
I tried to speak but my mouth had gone dry. “You’d want me to do that?” I managed to croak out.
She was gazing into my eyes. “Yes, well I would if you wanted to go that far. But I like the answer you gave, I’m okay with taking this part slower. It could be more fun anyway.” She ended her sentence with a smile.
Oh? I’d like to know how she thought so.
“Now, we have a game to play, but first we need to get the rules straight.”
I scoffed. “Isn’t it truth or dare? How complicated can it be?”
She rolled her eyes at me. “Yes, it is truth or dare but I want to make sure we’re on the same page. If either of us picks truth, we have to answer honestly and there’s no getting out of a question. Oh, and you can’t copy what the other person just asked. For dares, if one of us is uncomfortable with anything we can say no with no questions asked. Are you okay with the rules?”
I nod in agreement with her.
“Okay. I said I’ll go first, so I pick truth.”
My question came quickly. “I know you said you’ve had feelings for me for a couple of months now. Were they always these types of feelings, about wanting to do all this with me?”
She thought for a moment “No, it wasn’t like this at first. This is all somewhat recent; I’d say it started within the past few weeks. Truth or Dare.”
I hoped she’d give up more than that, it’s my fault though, I didn’t ask a very specific question.
“Truth”
She smiled at me warmly. “I’ll go easy for this first one. Did you ever have a crush on me in high school?”
My face flushed. “Yeah, in my junior or senior year. I liked you a lot, I didn’t think you felt the same way though.”
“I did, just not then. I had a small one when I first met you, but it was the same deal, I didn’t think you liked me back.”
“Truth or dare?”
She spoke with confidence. “Dare.”
I still didn’t want to rush things. “I’ll give you an easy one too. I dare you to kiss me… anywhere but the lips.”
Her face turned into a fake pout. “That’s not easy, that’s where I really want to kiss you. But if you insist.”
She moved a hand to the side of my neck and moved closer to me. I felt her lips below my ear, lightly pecking, then without warning, sucking. I tilted my head giving her easier access as a quiet groan escaped me.
I felt teeth press into my skin before she released her lips. “How was that?” She whispered.
Every hair on me stood up, her soft breath sending shivers through my body. I had to clear my throat before speaking again. “That was incredible, you should remember that biting thing though, it was a good one.”
She grinned at me. “Truth or dare?”
“I know you’d have me kiss you on the lips, so truth.”
She pouted again. “Fine, but I’m not going to make this easy now.”
“I don’t want it to be” A sly smile formed on my face.
“If you could touch me anywhere you wanted, where would it be?”
“Your butt? I think?” I spoke timidly, waiting for her reaction.
She stood. Oh no, did I make her mad? Was she about to storm out on me?
No, when she got up, she faced away from me, just standing there. “So do it, if you want to, you can. Touch it however you want.”
She was serious about this, she wanted me to touch her ass. I reached out and my hand met the soft fabric of her leggings, I had it laid flat against her ass. She let out a small hum as I touched her.
“You said however I want?”
“Yes,” Her voice shook.
I squeezed, grabbing a handful, it was firm but plump at the same time. Her head tilted back, and she made a soft moan, she liked what I was doing. Then I had an idea, she would either love or hate what I was about to do.
I drew my hand back and smacked her ass with an open palm. It wasn’t too hard, enough to make a quiet slapping sound. She yelped as I made contact, more out of surprise than anything else.
I pulled her around to face me. “Was that okay?” I was afraid I screwed up.
“Mmhmm, especially that last part.” Her face was beet red when our eyes met. “Can you do it again?
“Really?”
She nodded in response.
My eyes lit up, she enjoyed it. “Turn around again, I’ll do it two more times.”
She eagerly spun back around and barely bent over, sticking her butt out a little bit.
My hand made contact right as she turned her back to me, she let out another yelp as it caught her off guard. It was the same strength as before, hard enough to make a light smacking sound.
“Can you try the next one harder?”
I couldn’t believe what I was hearing. I wanted to but was worried about hurting her.
“Are you sure? I don’t want to do it too hard.”
“You won’t, I trust you. Please, I want it.” She whimpered with a shaky voice; you could hear the desperation in it. I wanted to give her what she wanted; I wasn’t going to say no to something she was telling me to do.
A crack filled the quiet room as I smacked her ass, it was twice as hard as before. Her back arched and she rose to the balls of her feet as she let out a loud, low, moan.
“Was that too much?” I asked. Once again, I pulled her around to face me, holding her hands in mine.
She pushed forward into my body and started kissing me, it was deep and passionate. Her tongue pushed inside of my mouth as she slipped her hands around my lower back and pulled our hips together. I felt myself barely push against her and couldn’t help but to let a quiet groan escape into her mouth. She pulled with more force and I pressed fully against her, I felt myself throb from the pressure as my knees weakened and I let out another groan, louder this time.
She pulled away from the kiss, arms still wrapped around me and hips pushed against mine, with a mischievous grin on her face. “No, it wasn’t too much. That was exactly what I wanted.”
“So you liked it?” I asked hesitantly, I was still worried about crossing some sort of line.
She rolled her eyes at me. “Yes, I liked it you big dummy, way more than I thought I would. You can touch me there anytime you want.”
“I could touch you there right now then?”
She leaned close to my ear and whispered. “I’ll say this one time and one time only. You can touch, grab, or slap my ass whenever you want. I like it and it’s obvious that you do too.” She gently pulled my waist harder against her again, letting me know that she was able to feel me.
My knees weakened again after hearing that, if she kept doing this I wouldn’t be able to stand, but I was still concerned about doing something wrong. I needed to make sure that her boundaries were clear. “Did it hurt when I smacked it? I don’t want to hurt you by doing it any harder.”
The question made her think for a moment. “Yes, it did kind of hurt, but it was in a good way, like what you said about me scratching you. I might ask you to do it harder, but if I don’t, then do it like you just did. Okay?”
“Of course.” I threw my arms around her and gave her a huge hug. We were both in a vulnerable spot and I wanted to make sure she was comfortable.
She pulled away from the hug and glanced at the clock. “Oh my god, it’s already one in the morning. It’s way past when I usually go to sleep, do you want to go back to my room?”
It was true, her usual bedtime is around 10 PM. It was very rare for her to stay up past then, and this late was unheard of. “Yeah, let’s go.”
“Come on then.” She took my hand and led us back to her room.
Back in her bedroom, I flopped down on the bed and she immediately walked towards the closet. I scrolled through my phone without purpose while she dug through her clothes.
“Okay, I’m going to go change. I’ll be right back.” She said after a few minutes while walking out of the room.
She came back after no more than a minute, and what I saw left me speechless. She was wearing a beige sweater that had to be at least two sizes too big for her. The arms fell to her fingertips and the base fell to the middle of her thighs, which appeared to be completely bare.
I guess she saw my eyes come to rest on her legs. “Don’t get too excited, I am actually wearing something under this.” Whatever it was had to be revealing.
“How can I be sure?” I said in a mischievous voice.
“Do you want me to come over there and show you?” She was already inching towards me.
I nodded and sat up, scooting to the edge of the bed. Her hips swung with every step she took, only stopping when she was a few inches in front of me. My heart was racing.
“Stand up.”
I complied quickly. We were so close our faces brushed together when I stood.
“Front or back?”
I guessed she was asking what I wanted to see first, the answer was obvious. “Back.”
She spun around, putting her back was to me. “Before I show you, I want to try something. Try to guess what I’m wearing by touching me, you can lift my sweater to feel but no peeking. You want to try?”
“You think I’m going to say no to that?”
“Nope.” She said while giggling. “Now hurry up and start.”
My hands started on her hips and slid down her body until they reached the bottom of her sweater. I slipped them under and started moving back up. There was a thicker cotton material that started at her upper thighs, and it went all the way up past her waist.
“Is it high waisted shorts?” She could have recalled what I had told her earlier, about liking shorts like that.
“Close but not exactly. I’ll give you one more guess.”
My hands came around to her ass, palms spread and flat against her. They were the same cotton material all the way up and around, but I couldn’t tell anything else about them. I wondered if she was wearing anything underneath, or if this was it.
I moved my palms back up until my fingers rested on the waistband. I slipped the tips under and her breath quickened in response.
“Do you want me to keep going?”
“Yes.” She squeaked out.
My hands moved under whatever she was wearing, there was nothing there. I started grabbing at whatever my hands could find, her skin was silky smooth, and soft wherever I touched. She was taking sharp breaths every time I changed how I was touching her.
“I was going to give you a hint that it was some type of underwear, but you’ve found that out for yourself.” I could hear the smile in her voice. “Do you have your next guess?”
“High waisted underwear, you said I was close before with the shorts.”
“That’s close enough.” Her voice was shaking.
“Are you going to show me then?”
“Yeah, if you take your hands off my ass.” She said, teasing me.
“Fine.” I said with a fake annoyance before slipping my hands out of her underwear.
She took a step forward and put her hands on the edge of her sweater, pulling it up with ease. My jaw dropped as she exposed what she was wearing. It was the hottest thing I had ever seen, and not only because she was standing in front of me in underwear. It was because it was MY underwear, she must have taken a pair of boxers that I brought. She had them pulled up her waist, her entire ass was covered but it gave a cheeky look. I had to resist the urge to reach out and grab it again.
“Wow.” Was all I could get out.
She spun around to face me again and moved her face to mine. Brushing our lips together, she gave me a light kiss and spoke into my mouth. “I take it you like them?”
I kissed her back and hummed an approving sound before pulling away. “You have no clue how hot it is to see you in those.”
She pressed her waist into mine with force. “I have a pretty good idea.” She said with a smirk before pulling away.
“Oh, and by the way, I only picked this sweater to hide the underwear from you so I’m going to put something else on. You have any preferences?”
“Anything that lets me see more of that.” I pointed down at her underwear.
She thought for a moment before her eyes lit up. She laid her hand on my chest and grabbed at my shirt. “I want to wear this.”
“You want to wear my shirt?” I got caught off guard.
She nodded in response.
I wasn’t going to say no, the thought of her wearing more of my clothes was attractive. “Okay, let me get another my other one and I’ll go change.”
She moved her hands to the bottom of my shirt and tugged at it while biting her bottom lip. “Or you could let me take it off for you.”
Source: reddit.com/r/Erotica/comments/lfu2bp/meeting_caitlyn_for_lunch_part_6_m19_f18
Finally part 6 at last!