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Pleasuring My Lady Friend Online

Posted by: Age: 43 Posted on: 0 comments
2 likes 110 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, Sexting, chat, pussy, cock, cum, tits, fuck, fucking, clit, Mother, Bdsm, Panties, Online

I recently saw someone post a text of an online chat that was't all that sexy but it got me thinking about my online adventures over the last few years and the many times that I have pleasured my online lady friends. I thought that I would post one of them and if it is well received I may post a few more. Aside from changing the names to protect the guilty, and correcting some grammatical errors for readability, this is the exact chat as it occurred, which is a bit lengthy. Please let me know if you want more.


Jess: hi sexy

me: Hi there hot stuff maybe I should call you Sweetlips, Short for sweet pussy lips 


Jess: :D i like that


me: And I love your sweet lips too bad you had to take the pics down


Jess: yeah I know i'm sorry :(


me: Maybe you can send some to me to wank off over and I'll send you something nice to look at


Jess: I'll email them to you since i'm not gonna post them right now


me: Sure what are you doing? A bit wet and horny?


Jess: yes always i am very horny


me: LOL, I love that I love horny women Too bad I am so far away


Jess: I know :( its sad


me: I am surprised that you don't have an army of guys that want to fuck you all the time. Why is that?


Jess: i don't know maybe I do and don't know it i guess. I'm kind of an airhead sometimes :P


me: Airhead? What does that have to do with getting fucked?


Jess: means i might not notice the guys that want to fuck me


me: oh, you mean like any guy with a cock? LOL


Jess: lol i don't think every guy wants to fuck me :P


me: No, not the dead ones :-)


Jess: lmao


me: You don't give yourself enough credit my Sweetlips


me: You are incredibly fuckable if those are really your pics and I believe that they are


Jess: yes they are lol although I don't think i'm that hot only my breasts are nice


me: Aside from the fact that most guys are always horny and willing to fuck anyone, much less someone with a body like yours your breasts are a HUGE asset and nothing wrong with the rest of you I don't know a guy that would turn your pussy down


Jess: awe thank you that's actually really sweet


me: I would fuck you for days if I had the chance

Jess: :D


me: You playing with your pussy for me now?


Jess: yes hell yes


me: All hot wet and naked?


Jess: yes yes and yes


me: Pussy dripping, thinking of sucking my cock?


Jess: omg yes i can barely stand it


me: give me your email and I will send you my cock pic. rub that pussy fuck it with 2 fingers and rub your clit


Jess: yes i am


me: While thinking of me ramming my cock down your throat pushing your head up and down on it


Jess: omg


me: Your tongue running up and down my hard cock


Jess: yes


me: My sweet precum in your mouth


Jess: lol im already cumming :P


me: Your boobs bobbing as your head goes up and down suck bitch suck my cock take it all in


Jess: Yes all of it deep down my throat


me: As I ram it in and out your lips over my knob driving me wild


Jess: i want to feel your head throbbing against the back of my throat


me: My cock starting to throb as I get ready to cum in your mouth white hot spurts of cum shooting from my cock into your mouth onto your tongue you sucking and slurping the head of my cock sucking every last drop out of my cock not wanting to stop or let go as it is so, so good.


Jess: yes that's what i want all of it


me: And I want to give it to you Jess: not one drop wasted me: Keep sucking and licking while I enjoy the sensation of your lips on my cock


Jess: omg i came again i love this so much :D


me: Suck me hard again anything to make you happy Sweetlips hopefully I make you cum better than any other guy 


Jess: your the only one who makes me do it more than once in a conversation


me: Thanks that's because I like to make my girls happy you cumming is more important than me cumming


Jess: awe thanks so much but i want you to be able to cum too i just wish i could be there to swallow it


me: We can work on that but I already had some last night. Just never get enough :-) I want you

Jess: :D


me: And your pussy and your Sweetlips


Jess: i want you too and your cock :)


me: Wish my cock could reach that far Jessica

Jess: lmao me too


me: But I can help you to get some real life cock too as I am baffled why you can't get enough?


me: are you shy in real life?


Jess: yes very


me: That's what I figured. and most guys think that you're the good girl type?


Jess: I don't really know what they think but I suppose you're right Jess: honestly i'm not anything like I am on here. I do the sexual things once i'm with someone but i'm not as open as i am about it on here


me: I know. The internet is a wonderful place to explore your sexuality that may be more difficult in real life We can live our fantasies here


Jess: yeah and i like that


me: With no risk to reputation or catch any dreaded diseases :-)


Jess: so very true


me: So you don't want to live out any of your fantasies?


Jess: I do honestly i want to live out all of them


me: So what's holding you back?


Jess: unsure of myself I guess


me: Self-confidence?


Jess: i mean i do have a gf but she is far away right now maybe


me: so you are bi?


Jess: yes i love cock and pussy both


me: That is so great. I love that you really are very sexual and that's why I can make you multicum


Jess: lol no one at work knows but i cum at least three times while at work


me: from online stuff?


Jess: no just cause i'm horny i cant help myself


me: You play with yourself?


Jess: yes that's why i stopped wearing panties


me: Nice and you don't let anyone get a peak?


Jess: lol no


me: you should :-)


Jess: honestly i don't understand why we women wear them anyways i get why guys do but women shouldn't have panties at all me:


Me too, they just block the view when I try to look up their skirt


Jess: lol i like to do that too


me: What kind of work do you do?


Jess: i work in a warehouse counting stuff doing inventories for different stores


me: With a bunch of burly guys? Seems like to perfect place to have tease some guy into fucking you


Jess: yeah but i work with mostly women most of them old :(


me: That sucks. No young studs?


Jess: no not really


me: I sent you something you still there naked smelling of dry pussy juices? :-)


Jess: oh its so nice and thick i love it :)


me: and hard for you


me: you on a mobile phone?


Jess: no i'm on my computer


me: OK, you fade in and out


Jess: just cant multi task well lol hard to finger cum and talk at same time :P


me: Still playing with your self? LOL


Jess: yeah


me: We can just make you cum some more

Jess: :D really


me: Since by now you've sucked me hard again your lips working my cock


Jess: mmmmm yeah


me: Up and down. tongue circling the head of my cock giving new life to it rising to life under your prodding your fingers playing with my balls as you suck


Jess: yes yes


me: Feels so good


Jess: and your cocks so yummy


me: I can feel my cock getting harder you're so good at cock sucking alternating between sucking and licking my cock rising to the occasion, almost fully hard again for you I push you back down on the bed and admire your amazing body


Jess: oh i came again


me: Nice

Jess: omg its happening even faster i love it


me: I get out the ropes and tie your hands to the bedpost and tie your ankles to the other end Jess: :D


me: Having you spreadeagled in front of me


Jess: my pussy is quivering with anticipation


me: Your luscious pussy gaping your boobs so enticing I am amazed at your body as I admire it


Jess: oh god yes


me: I stick my fingers in your wet pussy your pussy juices flowing and rub it onto my cock


Jess: mmmmmmmmm


me: I then move up and stick my wet cock between your tits squeezing them around it tightly and begin to fuck your enormous boobs the sensation on my cock is incredible the best tits that I have ever fucked back and forth I go you loving it, moaning in delight


Jess: ive never cum so much before please more. I want to cum more


me: While I slowly, rhythmically titty fuck you


Jess: oh god


me: While I slowly, rhythmically titty fuck you the sensation of your warm, smooth tits on my cock is incredible your body starting to writhe in pleasure you begging me loudly to fuck you "Fuck me, Fuck me" you keep saying. "Fuck me like a whore." I ignore your pleas driving you wilder


Jess: yes fuck me like the slutty whore i am please


me: Finally, giving in... I let go of those luscious tits I position my cock over your pussy as you push your hips up at me, wanting my cock in you I slowly tease your pussy, rubbing my cock on your slit and up to your clit back and forth as you moan and beg louder to be fucked like a whore


Jess: oh mmmmmm yes

me: Finally, surprising you. I ram it into your pussy plunging my cock all the way in

Jess: fuck me do everything and anything you want to me oh yes me: And begin to pound your hot, drippin' wet pussy you moan louder and faster, cummin' almost immediately after I enter you, from so much excitement and anticipation

Jess: omg me: I keep fucking you, harder and faster hot flesh against hot flesh pubis to pubis you grinding your pussy into my cock not wanting to stop your orgasmic screams make me pound into your pussy even harder and faster Jess: please don't stop i've never cum this many times before i'm begging don't stop

me: I have never had pussy this good your pussy clenching around my cock as I pound away at your pussy your hips bucking like a wild horse as you enjoy my cock while I'm yelling at you,."Take that you whore." "I'm going to fuck you 'til you beg me to stop"

Jess: yes i'm a whore please more more

me: Which, since I just came before I can do as my cock is still partly desensitized from before. "You fucking whore bitch" Your moaning gets louder your hips grinding wildly as I fuck you


me: I have to hold on to not get thrown off cock going in and out loving the sensation of your pussy lips as it tugs on my cock head as I enter your pussy on each stroke as I fuck you deep and hard your moans even louder now "Fuck me, fuck me" you keep yelling


me: Not wanting it to end

Jess: fuck my ass, fuck every hole I have just fuck me :)

me: I stop to untie you and have you get in a doggy position and enter your pussy from behind fucking you hard your tits bouncing wildly under you the sensation of your pussy on my cock being very different I can feel your pussy juices flowing freely, bathing my cock and balls I reach around, grabbing your tits as I fuck you like a dog in and out rhythmically pushing forward as you ram your ass against me the feeling of your boobs in my hands Incredible skin so soft

Jess: oh wow

me: never felt boobs like yours I grab onto them while I keep fucking you from behind

Jess: hun i can't thats six times and my fingers are cramping now lol

me: Your pussy feels so good on my cock LOL

Jess: i have never been pleased that much just from text

me: Finally, your pussy getting the better of me I shoot a white hot load of cum deep into your pussy as we collapse in delight...totally exhausted holding you closely, squeezing those enormous tits against my chest. finally satisfied :-) glad I could pleasure you that much my Sweetlips :-) really wish that I could enjoy you like that for real :-)

Jess: me too hun

me: Came 6 times?

Jess: yeah 2 earlier and 4 on this story me: :-) I am speechless which doesn't happen often and you do know that I am so sexy that if we keep talking that you're going to keep getting horny again and again? :-)

Jess: lol yes which is why i must get my rest before you give me carpel tunnel syndrome. Lol going to wear my wrist out :P

me: I know, don't want you to hurt yourself cumming :-)

Jess: lol me either but it sure is worth it me: But I just love to pleasure you you are so hot and sexual Jess: :) lol ok goodnight i can feel that tingle down below :P

me: Hopefully this is just the start of a long and pleasurable relationship

Jess: it is night

me: You in California? Bedtime now? Where are you?

Jess: lol i work the night shift silly this is my schedule :P

me: Ah, I see some nookie before bedtime OK, next time I want to hear how you pleasure yourself at work.

Jess: normally no but today was a nice break from that routine ok




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