A Lucky Mistext

Story Info
A night of text messaging takes an interesting turn.
4.6k words
4.49
72.4k
52
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When mobile phones came onto the scene I instantly became a big fan and kept up to date with the latest models and the gadgets that came with them, upgrading whenever a new fancy model with some fancy new feature became available. When camera phones were eventually released I naturally snatched one up and as they became common my friends began using them to send photo messages. I was inundated on a weekend with pictures of drunks mooning, close ups of vomit and other questionable substances (some of my friends are animals). Right from the onset of the mobile revolution I had never really been a fan of text messaging but with the addition of photos I started getting into it, sending my own images to friends and family, just not as vulgar as the majority of the ones I was receiving.

My friends were mainly guys, people I had known all my life and had grown up with. I had a few female friends, some of whom I had met at college others from various jobs I had held. It was in one of these jobs I met Karen who became one of my closest friends. I had befriended her on her first day at work, she looked a little lost and out of her depth so I took it upon myself to offer her a hand and show her the ropes. She was in her late teens at the time, a couple of years younger than me. After a few shared coffee and lunch breaks we found that we had a variety of things in common, same sense of humour, interests and hangouts and we quickly became good workmates.

Obviously my initial reasons for helping her on that day were less than chivalrous, Karen was around five nine tall with a great figure, magnificent toned legs and perfect white porcelain skin, long straight blond hair, brilliant blue eyes and a gorgeous smile. She was never without a boyfriend, although they never seemed to stay around long and even though over time we had grown extremely close the question of us getting closer never arose, we had slipped seamlessly into a platonic relationship, what most guys call the dreaded friend zone. I did though vividly dream of being more than friends with her on a regular basis throughout our early years of friendship.

As the years went on I eventually left the job I had met Karen at for a better position somewhere else. As we had gotten to be good really workmates we kept in touch and carried on socialising together. Karen got to know some of my old friends and even slept with one of them on one particularly drunken night out, something I found myself getting quite jealous about when I found out but the feeling quickly passed.

We would frequently chat on the phone or have lengthy text conversations. We would talk about what was going on in our lives, in our jobs, sometimes gossip and we would share our secrets. When we would be on nights out together or having a meal we sometimes would be mistaken for a couple, when this happened I would get a buzz but Karen's swiftness to correct the mistaken perception would bring me back down. It would confuse me at how easy it was to talk to Karen and how well we got on and had in common. Had she been someone I had met on a night out or under any other circumstances she would have been my ideal partner. But as fate had dealt the hand, it seemed we were destined to only ever be just good friends.

As our lives moved on, we both ended up meeting a special someone and were in separate serious relationships. We had both at some point experienced a jealous partner who could not grasp our friendship, most of the time we had taken friendship over the jealousy but there were occasions when the potential love took priority. Eventually the amount of time we spent chatting and texting started to lessen. Karen eventually got a really good job offer and moved away with her guy. We kept in touch, calls, emails and texts and we would arrange to meet for an occasional night out, sometimes just the two of us, sometimes with our partners. However the distance and life took its toll and we eventually drifted apart, the nights out would get cancelled at the last minute, emails and text messages would go unanswered.

We had known each other almost ten years but it would be over three years before I heard from Karen again.

It was the emergence of social media that got us back in touch. Karen sent me a friend invite on Facebook and we caught up with each other and our life stories. I was still living in the same town, in the same house, hitting my early thirties and with a string of bad career decisions and broken relationships behind me. From her page Karen seemed to have fared a lot better, she was clearly in a good job; she had a husband, nice house and was apparently living closer now. She explained in an early message that she had meant to get in touch sooner but had apparently lost my contact details and was not even sure I would still be living in the same place. I was really pleased to hear from her as my life had been crappy for a while.

We started to email and text each other at least once a week, usually just day to day comments; sometimes it would just be to have a bit of banter. Occasionally the banter would be flirty, it was never blatant just an innuendo or double entendre that would get lost in the rest of the conversation. It was kind of like old times but there was something else there, things had changed but I could not quite determine what had.

Boosted by the good feelings I was having at being back in touch with Karen I finally plucked up the courage to ask a colleague out on a date. Anne was in her late twenties, a brunette with a good figure and she was a power dresser, something that I always found extremely sexy. She was career minded and had risen to a senior position quickly, being a beautiful young woman this rubbed up a lot of people the wrong way and she had made more than a few enemies. I found her to be a nice person however, once you got past her serious exterior and we had been casually chatting over coffee in the kitchen for a few months.

To my delight Anne accepted my offer of a date and after another two we began seeing each other on a regular basis. Anne was quite controlling and she made it clear that she did not want to be tied down to a serious relationship. We kept it casual, basically we were fuck buddies, and the sex was fantastic which kept us coming back to each other. It was great seeing her during the day in her sexy business suits then fucking her on an evening as she kept part or all of them on. She would tease me with flashes of stockings or exaggerated leg crosses during meetings when only I was looking, often going commando to drive me wild.

We explored each other sexually, pushing our boundaries, experimenting and indulging each other's fetishes. Anne liked her feet being touched, toes sucked and licked. She loved cum, she would let me cum in her mouth almost every time we fucked, I hardly ever got to fill her pussy. She also had an exhibitionist side which I had kind of already discovered early on from her flashes at work but when we on dates sometimes she would bare herself in the most public of places. Anne also had a thing for sexting, dirty emails and she would send me sexy and dirty messages when I least expected them, when she knew I was in meetings, visiting parents or out with friends.

I managed to get to try anal for the first time with her and she entertained my stocking and CFNM fetish. On one occasion we fucked fully clothed at work in an empty meeting room over the table just after all the senior managers had left.

My life had turned around, I had been down a while but work was going well, I was getting regular sex with a hot woman and I was back in touch with my good friend Karen. Everything was good.

After a year of us starting our thing Anne was promoted to a higher position at work which meant she was constantly away on business trips out of the country for weeks at a time. She would make me promise to abstain from sex until she got back so that I was extra horny and had a nice load for her. We would sext, web chat and had developed a taste for phone sex, however neither activity beat actual fucking and I was always bursting to cum by the time she would get back from a trip.

It was during one of Anne's lengthy business trips that an accident started something that flipped my life upside down.

[Text to Anne] Only 4 more days babe. Have a present for you as soon as you come see me. xxx <smiley face>

[Text from Anne] Hmmm. Wonder what that can be. Is it a big present, will I like it?

[Reply to Anne] Yes and yes, you can put it in your mouth. <smiley face>

[Text from Anne] Is it a big box of chocolates?

[Reply to Anne] No.

[Text from Anne] Is it a cake?

[Reply to Anne] LOL No.

[Text from Anne] What is it, tell meeeee!

[Reply to Anne] It's my cock. x

[Text from Anne] LOL mmmmm xxx

[Text from Anne] I'm impatient I want it now. Please, pretty please...

[Reply to Anne] Wish I could babe. It's hard for you right now. x

[Text from Anne] Oooo is it?

[Reply to Anne] Yes. I'm stroking it thinking about fucking you...

[Text from Anne] Show it to me. Send me a pic of your hard cock.

[Reply to Anne] I can't send you a pic of that!

[Text from Anne] Please! Yes you can, pretty please for me xxx

[Reply to Anne] Hmmm OK I'll give you a preview. x

[Text from Anne] Mmmm yeah. Send me a pic. NOW.

[Text from Karen] Hey there, how's it going?

[Image Sent]

...

[Text from Karen] Erm I don't think that was for me lol <confused smiley>

...

I could feel the colour drain from my face; my heart was racing and my head reeling. I had just sent my oldest dearest friend a picture of my erect dick. I was desperately trying to think about what to say in my reply when my phone beeped startling me. Checking it I saw it was a repeat of the same message from Anne asking for her picture. I carefully sent it to her, checking several times that it was going to the correct recipient. Moments after the message was sent from my phone it beeped again.

[Text from Karen] <laughing smiley> Cannot believe you sent me that! I take it was a mistake! <boggle smiley>

After reading the message it calmed me a little, Karen was making light of the incident and the feeling of numb shock I had experienced quickly turned to embarrassment and I texted her a swift reply.

[Reply to Karen] I am so sorry!!!!

[Text from Karen] LOL who was it for?

[Reply to Karen] Just someone I'm seeing. Again so sorry!

[Text from Karen] <laughing smiley> <laughing smiley> <laughing smiley>

My heart beat returned to normal, I could feel the cold sweat on my body as my temp returned to normal from the burning heat of embarrassment. I realised I had a massive throbbing hard-on, not just from the week of abstinence, this stiffy was different; the idea that Karen had seen my cock had awakened something in me and it was raging.

My phone beeped.

[Text from Anne] Mmmm definitely something I can put in my mouth xxx

I read the message from Anne and I felt a little disappointed, I had hoped it was Karen, the idea of discussing with her about seeing my cock excited me in new ways. I tapped out my response to Anne.

[Reply to Anne] I cannot wait babe. x

[Text from Anne] Send me another; I want a pic of you stroking it mmmm

[Reply to Anne] Someone's a horny little thing tonight <laughing smiley>

[Text from Anne] After seeing what I've been missing yes I am x

[Reply to Anne] Well all you're getting is the preview; you have to wait a few days to see it again. xxx

I smiled to myself at how horny Anne was getting when my phone beeped twice in succession.

[Text from Anne] Please. Pretty please send me another pic.

[Text from Karen] She's a lucky girl.

I was surprised at Karen's message; I thought she had just left the conversation after the brief exchange and apology. Endless possibilities began popping into my head, was it a jokey statement, flirting or her way of finalising the incident. I decided to test the water.

[Reply to Karen] Ha! I get no complaints. <laughing smiley>

[Text from Karen] LOL OK...

[Text from Anne] I'll sulk. Send me another pic. <crying smiley>

[Text from Karen] Cannot believe you send naughty pics like that to people. <shocked smiley>

[Reply to Karen] I don't! Tonight was my first time and look how that turned out <embarrassed smiley>

[Text from Karen] Erm, yeah I definitely SAW it! LOL

[Reply to Karen] Again so so sorry about that!

[Text from Karen] You got nothing to be sorry about by looks of it. lol

[Reply to Karen] You teasing doesn't help <sad smiley>

[Text from Karen] Sorry. Am I teasing? I think you'd know if I was teasing. And I'm not the one sending rude pics <laughing smiley>

[Reply to Karen] I did not mean to!

[Text from Anne] Hey. You better not be playing with it! I want another pic of that lovely cock. <devil smiley>

[Text from Karen] Still cannot believe you send naughty pics like that. <shocked smiley>

[Reply to Karen] I don't normally, my girl wanted it and she wants another one. Don't want to now, might send it to the wrong person <sad smiley>

[Text from Karen] Just do it. Don't keep the gal waiting.

[Reply to Karen] Wow. Not the conversation I thought I'd ever have with you!

Throughout the exchange my cock had grown rock solid hard; I had been periodically stroking it due to the thrill of events but not too much. I was almost bursting and every touch was getting me closer to the edge. I reread the last few messages from Karen and checked Anne's. I switched to my camera and took another shot of my dick holding the phone further away to get a down body shot of my hand holding it upright.

[Text from Karen] Have you sent it?

[Reply to Karen] LOL not yet!

I briefly thought of asking Karen why she was eager to know what I had done but I already knew. She must be getting off on this situation just as much as I was. There was no need to state the obvious. Plus the thought of her knowing about what I was doing and messaging me about it was adding to the horniness of the moment and I did not want to ruin that by being blunt or pushy.

I double checked that it was Anne's name in the recipient's box and then I sent the second picture. I was having a crazy night; I was texting two women one my fuck buddy the other an old friend. I was sending one pictures of my cock and sexting while kind of flirting with the other because she had seen one of the pictures by mistake. It was a surreal situation but also a very horny scenario to be in.

...

[Text from Anne] Oooo nice. I hope you are just holding him up for me and not playing, naughty boy. <devil smiley>

[Text from Karen] So did you send another or have you chickened out? LOL

[Reply to Karen] Yeah I sent it. I am not a chicken!

[Text from Anne] I'm looking at both pictures now....while playing mmmmm

[Text from Karen] LOL

[Reply to Karen] You better not be playing with yourself, if I'm not allowed you shouldn't be <devil smiley>

I cursed myself, I sent another mistext again, I cursed Android phones for the way the interface worked and I then I cursed myself again for being so stupid. This message was bad I thought to myself, although Karen took a picture of my cock in her stride something as forward as this might be crossing the line. The uneasy feeling was creeping back just as I got a message.

[Text from Karen]!!!!!!

I quickly tried to recover by doing what Karen had initially to diffuse the situation, I tried humour.

[Reply to Karen] Another mis-text LOL I am so sorry again, at least it wasn't another naughty pic!

[Text from Karen] I'm starting to feel left out, she's getting all the pictures and you are both being naughty! <sad smiley>

I was astonished, this was getting very hot very quickly and I was dying to wank myself stupid at the fantasies that were going through my mind involving my good friend playing with herself over pictures of my cock. But then I quickly thought, wasn't she married, hadn't she been with her guy for a long time? I decided to try something in my reply.

[Reply to Karen] Why do you need a pic of mine, just get your bloke to take a pic of his <laughing smiley>

...

The wait for another message from either of them felt like it was taking longer than usual. Thoughts ran through my mind, had I ruined it, had my mention of her partner snapped her out of whatever she was feeling. Had I sent it to Anne! I checked and to my relief I had not sent anymore mistexts. The familiar noise of my message beep interrupted my slight moment of worry. It was from Anne.

[Text from Anne] I don't want you to feel left out babe. <happy smiley>

[Image Received]

After opening the message I was greeted to a view of Anne posing sexily and completely naked on a hotel bed. Ever the careful one she kept her face out of the shot, but I had done so many dirty and horny things to that body I knew it was hers, the tiny butterfly tattoo on her inner thigh also gave it away. Receiving the image was a horny moment and my cock lurched of its own accord and some pre-cum escaped. I needed release, waiting for Anne's return was going to be torture.

[Reply to Anne] WOW <boggle smiley> <boggle smiley> <boggle smiley> xxx

[Text from Anne] giggle xxx

[Image Received] [Image Received] [Image Received]

Anne bombarded me with different images of herself, close ups of her breasts or of her immaculate pussy, full body shots in the mirror of her posing. Seeing the pictures had me stroking furiously and I resorted to using a rhythm method in order to stop myself from shooting my load. I had already brought myself close a few times and should have stopped, I was supposed to be saving it for her return but the combination of her photos and the messages with Karen had me completely worked up.

Karen I thought! I had not thought about her after being distracted by all the nudity from Anne. Had my message upset her? As if on cue my phone beeped.

[Text from Karen] We separated. We have been for a while now. It was a mutual thing both our jobs took up a lot of our time and we grew apart. He has someone else now. A girl from his office, not sure if he was with her before we decided to split. Do not care to be honest it had been over a while even before we separated. I have not even considered seeing anyone else until tonight LOL your little accident was kind of like a switch turning me on to what I have been missing. So thanks actually. Am I being weird LOL Bottle of wine I have had tonight doesn't help. Hic LOL

I was relieved after reading her message; she had not been scared off and now I was piecing things together. Karen was single, had been for a while and the first cock she had saw in a long time had been mine and now she was feeling things she had not felt in a while. Fantasies and scenarios raced around my dirty mind, again, for the umpteenth time tonight.

[Text from Anne] Bet you want to cum now don't you. <devil smiley>

[Reply to Anne] You have no idea <angry smiley>

[Text from Anne] Mmmm I have twice. LOL

[Reply to Anne] Not fair! <angry smiley>

[Text from Karen] You still awake. Sorry for the vent.

[Reply to Karen] Yeah. And you don't need to apologise. I'm texting you and Anne at the same time it's getting confusing LOL as you already know. Sorry to hear about shit going on. Here for you x

[Text from Karen] Who's Anne? Is she your girlfriend? Don't want to interrupt your sexting LOL I'll catch up with you later. Make sure you don't send me anymore pics LOL x

[Reply to Karen] Hey, I'm getting the hang of it, and I won't send you anymore rude pictures. Yeah, Anne's sort of my girlfriend.

12