tagLetters & TranscriptsFirst Time Chatlog

First Time Chatlog


by Maddirose

(edited by the impervious DeReve)


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imasweetieXX: Hello there

browncoatXXXX: hi!

imasweetieXX: I'm not really sure what to type here...You're the first person to respond to my profile

browncoatXXXX: haha, haven't done this before?

imasweetieXX: Yea not at all...I'm a little nervous/embarrassed

browncoatXXXX: well I'm sad to say it's not the first time for me, but don't worry, I'll be gentle

imasweetieXX: I hope so! The site says we're matched on pretty much everything, so I have pretty high hopes

browncoatXXXX: yea...I mean, from your profile you seem like one of the coolest girls I've seen on here, but those things can be misleading


browncoatXXXX: well, I went on a date with this one girl I met, only to find out three months in that she 'forgot' to mention her husband

imasweetieXX: Oh no! That really sucks :(

browncoatXXXX: yea, it did a little bit. I'm over it now, no bitterness at all

imasweetieXX: Aaw. Well that doesn't do a lot to ease my nervousness. I wouldn't want to be the second bitch who broke your heart

browncoatXXXX: haha, I highly doubt that you're a bitch. And hey, no need to be nervous! There's a first time for everything, right?

imasweetieXX: Well, I have a confession for why I'm so nervous...

browncoatXXXX: darnit, not another serial killer...

imasweetieXX: drat you caught me lol :) nothing quite that bad. It's just on the site I put "looking for casual sex"...and that's not really true

browncoatXXXX: oh

browncoatXXXX: ...well what are you looking for then?

imasweetieXX: Well... I think I'm looking more for something that would lead to something more serious.

imasweetieXX: I'm really sorry, you probably don't even want to talk to me anymore :(

browncoatXXXX: nah, you still seem pretty cool

browncoatXXXX: I'm just confused why you didn't choose "looking for relationship"

imasweetieXX: I dunno...it seemed like a lie at the time...but over the past few weeks I've been wondering if I can handle it anymore

imasweetieXX: The casual thing, I mean

browncoatXXXX: nothing wrong with that

imasweetieXX: And I'm not saying I want to dive into something and go from zero to super-serious all at once...but I don't think I want to just stay casual

imasweetieXX: I'm sorry, I almost didn't want to tell you, 'cause you have a super interesting profile and you're nice to talk to and you haven't asked for a naked pic yet, so you're firmly at the top of the list for guys I've met on here. I didn't want to lie even if it meant having to part ways so soon

browncoatXXXX: no, I'm glad you brought it up. No sense in starting something if we're on different pages, you know?

imasweetieXX: So...

imasweetieXX: Are you saying you still want to start something?

browncoatXXXX: it's out of character for me...but I actually think I'd maybe be okay with that. I was looking for something more casual...but I'd maybe try a date. With you, I can see that happening

browncoatXXXX: fuck that sounded cheesy as hell

imasweetieXX: I like cheesy

browncoatXXXX: :-)

browncoatXXXX: so tell me a little about yourself

imasweetieXX: Oh jeez put me on the spot. Um...I'm five feet six...long black hair...medium sized boobs...green eyes...

imasweetieXX: Let's see

browncoatXXXX: lol I meant personality...since I assume we're going to meet up at some time, I think I'll see what you look like eventually ;-)

imasweetieXX: ...

imasweetieXX: Oh jeez

browncoatXXXX: lol

imasweetieXX: I'M NEW AT THIS

browncoatXXXX: hahaha, it's okay. It just read like the start of a cybersex session for a second there

imasweetieXX: haha ummm change of subject

browncoatXXXX: not a fan of cybering?

imasweetieXX: Never done it. I feel like I would suck at it

browncoatXXXX: you never know until you've tried ;-) but as you say, change of subject. So would you like to meet up?

imasweetieXX: Sure! When?

browncoatXXXX: well...are you busy now/this evening? Short notice I know but there's a little ice cream place that's local, I have a feeling you'd like it

imasweetieXX: Whoa, on the spot again.

imasweetieXX: Sure!

browncoatXXXX: I'll send you the address on the site and meet you there?

imasweetieXX: Okay :) see you soon!

browncoatXXXX has logged off at [4:26pm]

browncoatXXXX has logged on at [12:17am]

browncoatXXXX: I've informed my roomate that his new name is "Mister Cockblock"

imasweetieXX: hahahaha. Did he get in alright?

browncoatXXXX: oh yea, once I brought him a key his drunk ass stumbled to bed just fine.

imasweetieXX: I'm glad you got home safe. Sorry you had to leave so soon, and sorry that your roommate called at such an inopportune time ;)

browncoatXXXX: Yeeea me too. Well, at least we had time to give you a good time :-P

imasweetieXX: heh what an appropriate emoticon

browncoatXXXX: hahaha

imasweetieXX: I feel kind of bad though...I had so much fun, and you were about to have fun and ended up with blue balls :(

browncoatXXXX: hey now, I DID have a ton of fun

browncoatXXXX: and then ended up with blue balls

imasweetieXX: heh

imasweetieXX: Ok can I just say something I've been thinking ever since you left?

browncoatXXXX: go ahead and say something

imasweetieXX: You have the most delightfully long tongue I've ever seen

browncoatXXXX: HAHAHA

imasweetieXX: Like, seriously, I'm not sure how far into my pussy your tongue was, but it felt...wow

imasweetieXX: Certainly far enough, we'll say that :D

browncoatXXXX: wow :-) heh suddenly she's not quite as shy about cybersex

imasweetieXX: What can I say, I feel bad for how frustrated you've got to be right now...

browncoatXXXX: aw that's no reason to start :-(

imasweetieXX: Ok how about we'll say your tongue was so skillful it broadened my horizons

browncoatXXXX: I like that explanation better

imasweetieXX: You tongue-fucked my mind open

browncoatXXXX: bahahaha

imasweetieXX: Seriously, I mean it, let's do this. It's the least I can do after such a mindblowing evening

browncoatXXXX: wow okay, awesome!

imasweetieXX: But um...you'll have to tell me how. 'cause honestly I have no clue how

browncoatXXXX: well I dunno...how about just start with this; what did you enjoy the most of the night?

imasweetieXX: Taking the ice cream to the park

browncoatXXXX: that *was* pretty nice :-)

imasweetieXX: But you probably meant what dirty part did I enjoy the most

browncoatXXXX: but I was thinking more of the later part of the night

browncoatXXXX: yea, lol

imasweetieXX: Well that would probably be when we were against the door :D

browncoatXXXX: okay, there you go, just describe that.

imasweetieXX: But you already know what happened!

browncoatXXXX: not from your point of view :-D plus the hotness of cybering isn't exactly due to the plot twists

imasweetieXX: Heh true. Ok let me think

imasweetieXX: We got back to my apartment, and you kissed me. It was a really nice kiss, you're a good kisser.

imasweetieXX: I invited you in for coffee...and full disclosure, I literally did not connect how that sounded. I really did just want some coffee to go with the ice cream

browncoatXXXX: haha whaaat so did I...I swear *innocent look*

imasweetieXX: Sure you did, that's why you attacked me as soon as we were inside :P

browncoatXXXX: I wouldn't call it "attacking"

imasweetieXX: Oh I would...and it was amazing. I've never had someone kiss me like that before...up against the door, pushing against me? That is the point you officially got into my pants

browncoatXXXX: really? I thought that was later ;-)

imasweetieXX: Figuratively got into my pants, smartass

browncoatXXXX: sooo what happened next?

imasweetieXX: Hmm let me think OH YEA you then started nibbling on my earlobe, going straight for my weakspot

imasweetieXX: I don't know if you felt my legs trembling...but they were

imasweetieXX: And then you got all suave and steamy, whispering amazing dirty things into my ear. I think that's when your hands got into my shirt too, touching my stomach and my sides

imasweetieXX: The whispering instantly made me wet. I mean, I was wet before, but the nibbling and the whispering...yea I could *feel* my underwear getting soaked

browncoatXXXX: hmm, I didn't realize my little dirty nothings were so effective...what did you like most?

imasweetieXX: I'll never tell :P

imasweetieXX: But um yea, overall, very very effective

imasweetieXX: btw...are you jerking off to this?

browncoatXXXX: ...

browncoatXXXX: does that bother you? :-)

imasweetieXX: No not at all! I actually like that you are

imasweetieXX: I like that I can in some way return the favor ;)

imasweetieXX: K so let's see

browncoatXXXX: oh you're certainly doing that!

imasweetieXX: Ok so when I started moaning into your ear I think you could tell I was really getting into it. I liked that you didn't stop nibbling my ear as you unbuttoned my pants.

imasweetieXX: Then you pulled them down really slowly (too slowly!) while kneeling down and kissing my body on the way down, including kissing my bare stomach

imasweetieXX: And you spent an amazing yet frustrating time kissing my bare legs, and the hemlines of my underwear

browncoatXXXX: I liked how wet you'd gotten :-)

imasweetieXX: I liked you down there...it felt amazing, even when you weren't kissing I could feel your warm breath on my legs and on my puss

imasweetieXX: So amazing <3

imasweetieXX: ahem, pussy*

imasweetieXX: Okay so anyways, after way WAY too long, you slowly pulled my underwear down, just an inch at a time, kissing my mound the whole time

imasweetieXX: Again, way too slowly

browncoatXXXX: :-) I was giving you a chance to say 'no' if you wanted to

imasweetieXX: Are you kidding? I almost grabbed your head and pushed it between my legs!

imasweetieXX: Hell I wanted you back in the park, by the time I was against the door you had me whenever you wanted me

browncoatXXXX: hmm...note to self, next time do dirty things to her in the park

imasweetieXX: "next time"? :) :) :)

imasweetieXX: Sooo yea. My underwear were around my knees, my back pressed against the door, my fingers running through your hair, and you continued teasing me, just kissing my mound and brushing your fingers through my pubic hair

imasweetieXX: And the whole time I was mentally begging you to stick your fingers inside of me already

browncoatXXXX: idk I liked the effect I was having teasing

imasweetieXX: Well then you finally finally stopped teasing, and you flicked your tongue against my clit. I'm pretty sure that's when I started moaning

browncoatXXXX: and breathing heavy

imasweetieXX: Yes and breathing heavy ;) and you kept on going, just flicking it back and forth really fast but really light. I didn't have time to recover from each flick before you flicked it again

imasweetieXX: It felt so good...it was so fast it was like little shoots of fire in my cunt that wouldn't stop and kept on feeling better and better

imasweetieXX: Then you changed it up and just slid your whole tongue inside of me

imasweetieXX: And *that* is when I realized how freaking long and skilled your tongue is

imasweetieXX: Seriously you should've put that on your profile, "a God with his tongue", you'd have girls all over you

browncoatXXXX: haha yea I'm sure that's how that works

imasweetieXX: It worked for me. God it worked for me. I literally could not think of anything but how fucking good it felt to have your tongue in my pussy. I almost fell over on top of you haha.

imasweetieXX: And you kept switching between sliding it in me, licking my clit, and every once in a while just stopping, which was infuriating but then felt so so good once you started again

browncoatXXXX: and then?

imasweetieXX: I came. Hard. Harder than I can remember cumming in a long, long time. It was amazing, my legs were trembling and my whole body was quivering against the door, and I'm pretty sure I screamed :)

browncoatXXXX: you did :-) you might want to apologize to your neighbors

imasweetieXX: Oh jeez...I didn't even think of that

imasweetieXX: That's embarrassing

imasweetieXX: Oh well, worth it

imasweetieXX: I kind of couldn't stand anymore after that, so I slipped down next to you on the floor

imasweetieXX: And I started kissing you all over your face

imasweetieXX: Grabbing you with both hands

imasweetieXX: It had been a while since I came at all, I just really wanted to make you feel as good as you made me feel :)

imasweetieXX: And THEN your goddamned fucking roommate "Mister Cockblock" called and interrupted and you had to go to let him in to your stupid apartment :(

browncoatXXXX: yeeea I am not very happy with him

imasweetieXX: Oh really I didn't get that from the swearing :D

browncoatXXXX: soo what would've happened if he hadn't called?

imasweetieXX: Hmm...I was pretty grateful at that point...you probably would've gotten a lot ;)

browncoatXXXX: yea?

imasweetieXX: Oh hehe was that a cybering 'prompt'? Heh fair enough let's see

browncoatXXXX: maaaaybe

imasweetieXX: Well we were conveniently on the floor...I think I probably would've taken advantage of that

imasweetieXX: I would've kept on kissing you, I know that. Moved to your mouth and kissed you a lot more deeply. A kinky little part of me feels like I wouldn't have minded tasting myself on your tongue...

browncoatXXXX: oh god

imasweetieXX: Yea I thought you'd appreciate that >:) I'll have to remember you like that for next time

imasweetieXX: Anyways, I would've kissed you. I think I would've kept on kissing you for the entire rest of the night really. And then pushed you backwards onto the floor, and straddled you

imasweetieXX: I'd've had to pull my pants and underwear off of one leg first. I really wanted you; I don't think I would bother to take them all the way off

imasweetieXX: I'd pull your shirt up and admire your sexy abs

browncoatXXXX: what if I don't have abs :-P

imasweetieXX: Oh you do. I copped a feel when you were kissing my neck against the door ;)

browncoatXXXX: hahahaha

imasweetieXX: Stop interrupting :) So I'd maybe slip my shirt off, and you would've seen that I wasn't wearing a bra. Then leaving you with that view, I'd reach backward and undo your jeans

browncoatXXXX: oh jeez no bra?!

browncoatXXXX: seriously hating my roommate right now

imasweetieXX: Yep just for you :D

imasweetieXX: ANYWAYS so I would slip your cock out of your pants and slide my hand up and down it for a little while, grinding my pussy against your lower abs while I did so.

imasweetieXX: And then, I'd scoot back and lift my ass, and slowly slide you all the way inside of me

browncoatXXXX: what no protection? I'm shocked and appalled

imasweetieXX: pill ;)

browncoatXXXX: oh ok carry on then

imasweetieXX: So anyways, at that point I'm 100% sure you'd hear me moaning again

browncoatXXXX: wow you are really good at this

imasweetieXX: Thanks :) Secret time; I'm typing this with one hand now because I'm getting so turned on describing this that I have to take care of myself. Again

browncoatXXXX: fuuuuuck

imasweetieXX: I'm not gonna lie and tell you I'd tease or take it slow, in this hypothetical scenario. The first orgasm was amazing, but I'm already craving another one and we're not even together. I would be riding you pretty much as soon as you were inside me

imasweetieXX: Lifting up until just your tip was nestled inside me, then slamming myself down again, enjoying every single inch inside my body. Oh I'd try to be restrained about it, I'd try to slow myself down, but I have the feeling that each time I lifted up I would want you back inside me so much that I couldn't push back down fast enough

browncoatXXXX: fuk

imasweetieXX: Oh and I should tell you...I just stopped fingering myself

imasweetieXX: So that I could lick the pussy juices off my fingers

imasweetieXX: You still there?

browncoatXXXX: sorry, I was NOT expecting that and kind of came all over my hand and pants...had to change real quick

imasweetieXX: hehehehehe! Wow I'll take that as a good recommendation of my skills then :D

browncoatXXXX: fuck yes I'll say you can take that as a recommendation

browncoatXXXX: hell after that I'll say whatever you want me to, haha

imasweetieXX: Now you know how I felt after experiencing your tongue ;)

browncoatXXXX: :-)

imasweetieXX: Sooo...you mentioned there would be a 'next time'?

browncoatXXXX: yea, I certainly hope so...I mean, I had a lot of fun tonight

browncoatXXXX: not just the sex stuff either. I'm not big into dating or things like that, but I thought this whole evening was really nice

imasweetieXX: And what I said before...about possibly this sometime becoming something more than a casual thing?

imasweetieXX: Just to be clear, *not* asking you to be my boyfriend or trying to be clingy or anything...

imasweetieXX: Just hoping you'd be open to maybe something like that happening, someday

browncoatXXXX: yes

imasweetieXX: Oh

imasweetieXX: Yes?

browncoatXXXX: yea. I think I want to see where this goes beyond just a casual thing

browncoatXXXX: are you busy this Friday? We could do the whole cheesy-cute 'dinner and a movie' bullcrap :-)

imasweetieXX: :) :) :) :) <3

browncoatXXXX: hahaha I'm gonna take that as a 'yes'

imasweetieXX: :) yea you can take that as a "yes"

imasweetieXX: Bring that tongue of yours ;)

browncoatXXXX: uuuum

imasweetieXX: ...

imasweetieXX: Okay that was meant to come out flirty and cute, not weird and creepy hehe

browncoatXXXX: haha we'll call it 'flirty and cute and also a little weird and creepy'

imasweetieXX: :) okay

imasweetieXX: Oh crap it is 2 in the morning!

browncoatXXXX: holy shit :-( I've got to wake up in two hours

imasweetieXX: :( sorry!

browncoatXXXX: nah this night has been definitely, definitely worth it

imasweetieXX: I'm really glad you think so

browncoatXXXX: I'm gonna turn in now, but I'll talk to you tomorrow!

imasweetieXX: Okay, talk to you tomorrow!

browncoatXXXX has logged off at [1:57pm]

imasweetieXX: squee!

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