Hi,
First of all, let me just tell you English is not my first language, so i’ll probably write a few mistakes.
I’m from a small city, and when I went to university I moved to a big city. Luckily (or not), I moved to the same city as my high school girlfriend.
Because we were very young, we decided not to move in together. Needless to say, one year later we broke up, it was not a dramatic break up, we just had different lives and objectives.
A couple of months later, I was working part-time at a clothe store in a big shopping, and become best friend with a gorgeous girl I’ll call Ana.
Ana was beautiful, 5’3″, blonde with great tits (not huge, but perfect to her body), and a smile to die for. Of course I knew the moment I met her that she was way over my league.
I’m not ugly, I’m just a regular guy, and this is a 10/10 girl.
There was never a sexual tension between us, I’ve never tried anything with her, because I knew i didn’t have a chance, but also i was not “her brother from another mother”, we were just close friends.
After a nightshift, we usually went to grab a couple of beers before heading home
During our chats, we usually talk shit about our boss, or about school, our about some sexual adventures we had, of course mine was always with my ex.
One night, after a couple of beers she asked me:
Ana: “So, how is your sex life since the break up? Any new “friends”?”
Me: “Well, my new “friend” is my hand.”
Ana: “Come on… It’s been 3 months, you have to get out more.”
Me: “I know, but I don’t want any new girlfriend at the moment”
Ana: “Who’s talking about girlfriends? Jesus… are you living in 1980?”
Me: “hahah, not everyone is like you, who snap your fingers and guys come ready to fuck you.”
Ana: “I’ll prove you wrong, give me your phone.”
I was intrigued, so i gave her my phone, thinking she would send a message to Sarah, a co-worker that told Ana she found me handsome, but instead, she installed Tinder.
Me: “Oh… Tinder, you know that it does not work the same with guys right? We don’t get 1000 likes a day.”
Ana: “I know, but you’re not on the small city anymore, here there are always tons of girls just looking to have fun, and we won’t use your real name.”
As told before, we talked about everything, and i had shared before a couple of my kinks, being the bigger one… facials.
So she created a fake profile (with a couple of real pictures of me), and on the description she wrote “I don’t want to take you on dates, I just want to paint your face.” After that she swiped right to everyone until I didn’t have any more swipes.
She handed me the phone, and we laugh like hell, I said that would never work, and she said that if in 2 days I didn’t have someone interested, she would pay the beers, otherwise I would pay.
I agreed, we ordered another beer and we talked about other things, about one hour later we said our goodbyes and went home. I was tired and a little drunk, so i just went straight to bed.
Next day I woke up and when I checked my phone, I noticed i had a couple of Tinder notifications. I had 4 matches and 2 messages, I was surprised, because I had used tinder before, an usually I had a couple of matches a week, and 0 messages.
One of the messages was from Mary saying “Lol”, and the other was from a girl named Jennifer saying “hi”.
I checked Mary profile, just to find it was Ana’s fake profile… I smiled and answered “so… do you want me to paint your face?”
Next i check Jennifer’s profile, she was a little chubby, black hair, but she was so pretty, with one of those “angelical innocent” girls who go to church on sunday, also, she had massive tits.
I instantly got hard, but I was getting late to school, so I went to the bathroom to shower.
During my shower I remembered that i haven’t answered Jennifer, and I also remembered something Ana had told me before – “On Tinder, you have to be different, otherwise you’re just another guy with small talk”.
So, when I got out of the shower, answered Jennifer with “Hi, sorry for the delay, but I was out of ink” – Lame i know.
A couple of minutes later Jennifer answered:
Jen : “Oh ok… I guess i have to look somewhere else then.”
Me: “Not really, I just received fresh ink, and I deliver at home or anywhere within 15min drive distance.”
Jen: “Good to know. So… yesterday someone got my paint job?”
Me: “I don’t disclose customer details.”
Jen: “Fair enough, but i need guarantees that you have ink enough for the job. Do you have any references?”
I remembered that i had a video on my old phone, that i had sent to my ex a year before, when she was on vacation, of me unloading a huge load (no face was on the video). But i wanted to be sure that Jennifer knew what she was asking for.
Me: “I’ve a sample video on my old phone… but just to be clear, you know what type of ink I’m talking about right?”
Jen: “If I’m not dumb, i think we’re talking about cum.”
Me: “Exactly, I just wanted to be sure, I’ll share some references with you later.”
Jen: “I’ll be waiting.”
After school I went to work, and on a break i checked my phone and had a message from Jen.
Jen: “Still waiting…”
Me: “Sorry, I’m at work at the moment.”
Jen: “Are you Painting someone else??? :) ”
Me: “Haha, I wish i was payed to do that.”
Jen: “Some pleople are ;)”
Me: “haha you’re funny, and migh I say, you’re beautiful. Well going back to work.”
Jen: “Thanks. I like you’re marketing skills.”
After work I went straight home, plugged my old phone, and found the video. It was not a great video I have to say, it was just me laying in my bed, stroking my dick until i cum… a lot.
Cumshots have always been a fetish of mine, I don’t have a huge dick, just normal I guess, but I do cum a lot, especially if I build up for a couple of days.
I created an account on a porn tube site, and upload the video, i double checked that there were no possible way I could be identified.
After that I send a message to Jen:
Me: “Go to “porn site” and search for “Paintjob reference 1” “.
An hour later, Jen haven’t replied, and i though that maybe the fun was over. It was fine, I had fun for a day, and maybe some other girl would come up. I started watching a movie and quickly fell asleep.
Once I woke up, I had a message from Jennifer.
Jen: “WTF?! that isn’t you.”
Me: “I agree i need to invest on video editing, but yes… it is me.”
Jen: “Damm… that is some pornstart quality cumshot!”
Me: “haha, thank you I guess.. so are my refences good?”
Jen: “If that is you, yes!”
Me: “So… when can we arrange your “job”?”
Jen: “When was the last time you cum?”
Me: “A couple days ago I think.”
Jen: “I need you to build some more paint for me.. so Friday night?” (It was Wednesday)
Me: “Deal!”
Jen: “But you’re not allowed to cum until Friday night!!”
Me: “Will you let me cum on your face right?”
Jen: “Of course.”
Me: “Then I can do that!”
After that we had some small talk for about an hour, and then I went to sleep.
Next day I went to school, and later to work, this time Ana was also working, and during a break she asked me who would pay the beers later, I smirked and said… you.
As usual, after the shift was over, we went straight to our pub.
We talked shit about our boss, school, and when i was going to the bathroom, Ana said:
Ana: “Leave your phone, I have to check who is paying this.”
Me: “Hahah, sure.”
I left my phone and went to take a piss, as I knew i would have to pay the beers.
Once I got back, Ana was smiling and had two more beers ready.
Ana: “So… Tomorrow night with Jennifer!!” and started to do a silly dance
Me: “Haha, looks like it! I have to thank you for that, you were right, and I’m having a lot of fun!”
Ana: “You can thank me when you bang her!”
She drink a little bit of the beer and then she said.
Ana: “So… what about this video?”
Shit.. I’ve forgotten about the video, It was not a big deal, Ana knew my fetish will cumshots, but I didn’t want her to see the video.
Me: “Did you watch it??”
Ana: “No, i haven’t, but maybe i will!”
Me: “Fuck you, i will take it out!”
Ana: “haha ok.”
After a few more beers I went home, and because i didn’t have work or school the next day, I was a bit drunk.
I texted Jennifer.
Me: “I’m a bit drunk… Are you sure you aren’t free today?”
Jen: “NO, Tomorrow, go to sleep!”
Me: “Gggrrr, It is getting really hard not to masturbate thinking on you.”
Jen: “Don’t you dare to cum!!!”
Me: “Fine… but tomorrow I’m going to fuck your face until i blow all over you!”
Jen: “We’ll see… go to sleep!”
I woke up Friday morning still half-drunk and with a huge boner, I was hard but I did not jerk off (as I usual would do), I check my phone and had no new messages from Jennifer, so I sleep a little more.
It was around 1pm when i woke up again, and still no messages from Jennifer, i though that maybe she got mad about our talk the night before so i send her a message
Me: “Good morning, sorry about yesterday, I was drunk and really exicted to see you.”
Jen: “It’s ok, I just don’t like to chat with drunks, usually nothing good comes from that.”
Me: “You’re right, sorry again. are we still up for tonight?”
Jennifer didn’t answer, so i got out of bed and went to take a shower and shave (i wanted to look good).
It was about 5pm when i got a message from Jennifer
Jen: “Hey, sorry, but I have to cancel tonight.. It is not you, but I’m just not in the mood today.”
I was disappointed, I was looking for that night for almost a week, but i knew it was my fault, so i just answered
Me: “Ok, I apologize again for my behaviour last night”
Jen: “No need to apologize, it’s not you… I’ll explain another day.”
Me: “No problem. Have a nice day!”
And with that my plans were over.. I’ll admit i was angry with the “It’s not you” excuse (later I would find it really was not my fault.).
I was so disappointed that i didn’t even masturbate after almost a week “clean”.
Later I ordered some pizza and was ready for a night of netflix with no chill.
It was about 8pm when i received a message from Ana:
Ana: “Good luck tonight! Make me proud!”
Me: “Jennifer cancel, no fun tonight.”
Ana: “Shit :\ do you want to go out or something?”
Me: “Not really, I’m still a bit hangover, I’ll just stay at home.”
Ana: “I’ll be at XPTO Bar with a couple of friends, if you change your mind join us!
Me: “Sure, have fun.”
I put my phone away and resume watching my movie and eating pizza.
A couple of hours later my phone beeped again
Ana: “Hey, awake?”
Me: “Yep, whats up?”
Ana: “Can i crash on your sofa?”
Me: “Sure”
Now, this was not unusual, I live close to the pubs we usually drink at, and Ana lived about 30min away, so usually she slept in my sofa whenever she was a bit drunk.
About 30min later she was ringing my door.
I opened the door and Ana had bought a bottle of cheap red wine, and i could see she was already drunk. She was wearing a summer dress, showing a lot of cleavage and that put a smile on my face.
We opened the bottle, and went into the leaving room, Ana layed on the sofa, and i sit on the floor with a couple of pillows.
We chatted about her night, and then she asked what had happened with Jennifer, I explained, and she said:
Ana: “well, you know that these kind of internet “dates” are a bit more difficult for girls, maybe she got cold feet, but give her time.”
Me: “Yeah I guess, It’s not a big issue, i was just excited, have been a while. lol”
Aa: “haha, there are plenty of fish in the sea, don’t sweat!”
Me: “Yeah, the worst thing is that she made me not masturbate for a week!”
We laughted a lot and started talking about the movie we were watching and having more wine.
About an hour later we were no longer drinking, and we had calmed down, the movie ended, and I stood up and told Ana I was going to bed.
A few minutes later, I was already in bed, scrolling reddit when I got a message from Ana
Ana: “May I ask you a question?”
Me: “Sure”
Ana: “Was that really you on that video?” -> Only at this point I remembered didn’t took the video down.
Me: “You promised you were not going to watch it!! but yes.. it was me”
Ana: “Shit… you really do cum a lot! hahah”
Me: “Now that you talk about that… i need to get my computer from the living room :P”
Ana: “ahahahaha, are you going to jerk off??”
Me: “A gentleman never tells!”
Ana: “Picture.jpg”
Ana send me a picture of her laying on my sofa, with just panties, and one arm covering her tits.
Ana: “I’m sorry about Jennifer.. I hope it helps!”
Me: “That is hot… now i really have to jerk.”
Ana: “Picture2.jpg”
This time Ana sent me a picture of her face, with eyes closed and her tongue out
Ana: “I forgot you were a face painter :P”
Me: “You are really beautiful.”
She didn’t answer, and I just started jerking really slow watching the photos she had sent me, because i knew i wouldn’t take long to cum, and i wanted to enjoy.
About 5min later i received a Tinder notification, it was a message from Mary (Ana’s fake profile), it just said… “yes”.
I could not believe what was on my phone:
Mary: “Lol”
Me: “so… do you want me to paint your face?”
Mary: “yes”
I though about what to do for a couple of minutes, and decided i need to take this chance. I stood up and walked to the living room, I was hard as a rock, and only wearing boxers.
As soon as I was at the door, i could see Ana laying on the sofa, with just her panties, and one arm still covering part of her tits.
Me: “Are you kidding me?”
Ana: “No, I’m drunk, i watched your video, and thinking you might be jerking off in the next room made me horny.”
Me: “So… you still want me to paint your face?”
Ana: “I don’t want to fuck you… I just want you to cum for me…”
Me: “Ok”
I slowly walked to her, and she pulled my boxers down without touching me, during this, i finally saw those beautiful tits, she had big puffy nipples, I have never seen nipples like that.
I was standing next to her, naked and rock hard, because she was laying on the sofa, my cock was just a few inches above her tits
Me: “You have amazing nipples”
She grab them and said “Do you like them?”
Me: “Yes!! can I touch them?”
Ana: “ok.. but you can only touch my tits!”
I grabed both her tits an played with her puffy nipples. they were amazing, for a moment i tough i was going to cum without touching my dick. She saw my dick pulsating and asked me
Ana: “aren’t you going to jerk?”
Me: “Yes!”
I resumed jerking off, but really slow, I knew I wasn’t going to last long. A lot of precum started to drool, and a little bit fell on her right tit. She noticed it, and started to massage her tit with my pre-cum
Me: “You’re so sexy!”
Ana: “I know… and so are you. You have a beautiful dick!”
A lot of precum was again starting to drool, and this time Ana catched the drop of precum with one finger, and put the finger in her mouth
Ana: “hhhmm You taste so good!”
This send me over the edge, I knew i was going to cum, and i warned her.
Me: “Shit, I’m going to cum”
Ana: “Yes? do you want to cum on my face?”
Me: “Yes!! Yes!!”
Ana: “Come on my face… paint my face!!”
That was it.. I pointed my dick to her face and started to cum.
The first two ropes passed by her and landed on the wall, she quickly adjust her position and the next ropes landed right on her face, and her hair, and the last ones on her tits.
This was one of my best orgasms I’ve ever had, and for a moment I couldn’t open my eyes.
When my vision adjusted, the vision I had in front of me was beautiful.
Ana.. my beautiful friend that was out of my league was drenched in my cum. She had her eyes closed, because they had a poll of cum over them, her hair had 4 huge and thick ropes of cum, and she couldn’t open her mouth without ropes of cum being in between her lips.
For a moment… I was in love.
After a few seconds of rest, i noticed she was makig signs with her hand… like “help me!!”
I started laughing like crazy, and so did she, and I quickly grabed a towel.
After a minute or so… she said:
Ana: “How can you cum so much? I wasn’t prepared for that!”
Me: “I don’t know… it is my super power.”
We laughed a lot, and then she said something that would haunt me for a long time
Ana: “Go to bed… I need to sleep and I think i might need to rethink this friendship!” and smiled… that beautiful smile.
I was empty, tired, and happy. I kissed her forehead (i don’t know why) and went into my room.
As I lay down I noticed a notification on my phone, it was Jennifer with a message:
Jen: “I’m sorry for today, I think I’m free tomorrow”.
Source: reddit.com/r/gonewildstories/comments/bn2brw/paint_my_face
Great story!!! Very well written and erotic
Follow up
Following ??
This shit is so fuckin fake
Very well written and hot story! Would love to know what comes after