Over the next few days, I couldn't help but fantasise about packing up my whole life and just going for it. As scary as it seemed, I knew I could get work doing what I do anywhere in the country. It may not have been a great-paying job, but it was a growth industry that was in high demand. Being that I owned my own home, which was a part of the divorce settlement, as well as it being in a prime tourism area, I knew that I could rent it out and use that money to supplement my income. Or I could sell it and use the money to make a fresh new start.
Moving away from my ex was definitely a selling point for me, but that was also the problem. Until the kids were self-sufficient adults, there was no easy way to move without abandoning them. I knew they wouldn't want to move away; it was too far to move away from their mother and their friends. I knew that I still had at least two years of them being here before I could move away. It was a tether to their mother, my ex-wife, that I both hated and understood. I would have loved to have just packed up and left, but I also knew it wasn't going to happen. Not yet, anyway.
None of this meant that I couldn't take some time off work and travel, though. I had spent every evening this past week talking to Anne. Mostly just talking on the phone, but we had figured out how to video call, and after some initial shyness, things had progressed to the point where we were as close to making love as possible with several thousand kilometres between us.
The initial reservations we had about our family, our history, and that nervousness that comes with the firsts of any new relationship soon evaporated as we thrilled each other with the fantasies of what we wanted to do to, for, and with each other. We spent many hours just talking about the day-to-day of our lives, and we were really getting to know each other on a deep level.
We returned to the initial flirtation one evening when Anne asked me to consider one of the questions she first posed to me as AK-47.
“Charlie, I want to ask you something.”
“Sure, what's up?”
“Do you remember when we first started talking, and I asked what you would have me do?”
I smiled at the memory and instantly felt that all-too-familiar stirring as my cock began to twitch and swell.
“Mmm, I sure do.”
“Well, I want you to think of some of the things you would challenge me to do. I want to take some risks. I want you to make me feel excited and alive. Would you like to do that?”
Fuck, yes, I would.
“I would love to do that. I'm not sure how deep to go in straight up, though.”
I could hear the smile in her voice as she responded.
“Obviously, I don't want to get arrested or lose my job, but I am keen to expand my horizons.”
“Okay. Well, how about you spend the rest of today naked?”
Her laugh was throaty and warm.
“Well, that's not much of a challenge. I'm home now; I have already stripped off and don't have to go anywhere for the rest of the day. Truth be told, I was going to do that, anyway.”
“Mmm, I wish I could be there to watch you.”
“Hmm, me too, but I would want you to do more than just watch me.”
“I really wish I could be there, but I guess I'll just have to make the most of what we have. What about tomorrow? What are you doing tomorrow?”
“I have to work tomorrow, so I'm afraid I can't be naked at work.”
“No, you can't do that, obviously, but I wonder if you would be game to go the entire day without any underwear on?”
“Hmm. That does sound interesting. Does that mean no bra as well or just no panties?”
“No bra or panties.”
“Well. That could be quite a challenge. I have to meet with some clients tomorrow. My work skirts come down to my knees, so that shouldn't be a problem, but I suspect having my hard nipples showing through my blouse would most likely be noticed. I might have to wear a jacket for some of the time. I hope it doesn't get too hot.”
“Does that mean you accept my challenge?”
“Hmm. It could be a bit risky, but that's kind of the point, isn't it? God, I'm getting wet again just thinking about it. Yes, I'll do it.”
“God, you are so fucking hot. Will you talk to me tomorrow night and let me know how it went?”
“Oh, I suspect I'll be so horny by the time I get home that I will need some time alone with you.”
“I want you so badly, Anne.”
“I know. I want you too. We just have to wait for now.”
My exasperation and desire leaked out of my voice as I sighed.
“Yeah.”
“It's going to happen, Charlie. I can feel it. I want it as much as you do. One day, we will be alone together, and there will be nothing stopping me from doing all of the things I want to do to you.”
“Mmm, I desperately want that. I'm curious, though; will you tell me what you want to do to me, Anne?”
I put her on speakerphone and began to get undressed as her throaty voice poured out of the phone.
“Ooohh. Well, let's see. A lot of the things you said you wanted to do to me the other day are the same things that I want to do to you. I want to pay a lot of attention to your body. Mostly, though, at the moment, I want to taste you. I want to feel the delicate, soft skin of your hard cock against my lips. I want to tease that sensitive spot on the underside of your cock with the tip of my tongue.
I want to taste and smell the clean skin of you as I taste the pre-cum that's leaking from your cock. I want my hands squeezing your ass as your cock thrusts slowly into my mouth. I want to feel your legs shaking as the sensations that I am giving you start to build up inside of you. I want your hands to wrap in my hair and hold me, making my scalp tingle as you fuck my face.
I want to show you that I won't let up or quit to get my own pleasure; I get plenty of that from making you feel good. I want to look up and see the pleasure in your face as you begin to lose control. You might warn me that you are about to cum, but that just increases my desire for you. I want you to cum. I want to taste your desire; I want to feel you lose yourself in this moment. I want your eyes to stare into mine as you realise what I am offering you, and I want to enjoy the moment as you relax and release into me. I want to feel your cock swell as you orgasm, and I want to feel your cum burst forth from you and fill my mouth with your hot, slippery cum. I will swirl it around your cock with my tongue before swallowing it all down. I want to suck on you until every last drop that your body can offer slips down my throat. I want to feel my belly full of your hot cum.”
“Oh, fuck, Anne.”
It was all I could manage to say as pulse after pulse of my cum landed on my stomach. I was panting like I had just run around the block, and my balls were almost aching with post-orgasmic relief.
In a soft voice filled with a mixture of awe and desire, she whispered to me.
“Did I just make you cum, Charlie?”
“Oh, yes, you did, Anne.”
She giggled quietly.
“I love making you cum with my words, Charlie. I love that you can make me cum with yours. It's a wonderful feeling to make you cum with my mouth, but I do wish I were making you cum in my mouth instead of just with words, Charlie.”
All I could do was groan with desire as my spent cock twitched feebly.
“I have to admit, I want that too. Almost as much as I want to make you cum in my mouth.”
“God, Charlie, if we don't make this happen one day, I swear I will explode.”
“I feel the same way.”
We spent the next hour or so just chatting about our day, but before we each said good night, I asked Anne if we could talk again tomorrow after she got home from spending the day with no underwear.
“Of course. Telling you about it is the second most exciting part of doing this.”
The whole next day was filled with nervous excitement. I was desperate to hear how it was going, but I had to be patient. It didn't help that she sent me a couple of photos first thing in the morning. One shows her standing in front of a mirror in her work uniform. Her jacket was unbuttoned and open wide as she stood there with her hands on her hips, holding the jacket back. Her nipples were pushing out the material of her blouse, and the darker skin of her areola was visible through the thin material. She was trying to look serious, but I could see a grin beginning on her face. She looked so fucking sexy that I was instantly hard. The next photo showed her from behind, but she was looking back over her shoulder. She had an exaggerated look of surprise on her face with one hand covering her mouth, and her eyes were wide as though she was shocked by her own behaviour. Her skirt was being blown up by a fan on the floor, and I could see her naked ass on full display.
I just couldn't get over how sexy she was. I had a moment where I remembered the friendship we had as kids and the early years of our teens. I would never have guessed back then that she would turn into the absolute vixen that she is now. Maybe I just wasn't paying attention, or maybe she was just as surprised as I am that things turned out the way they had. Regardless, I couldn't believe my luck at finding such an incredibly sexy woman who seemed to want me as much as I wanted her.
She inspired me, and on my lunch break, I began writing a new story about a woman who appeared to be shy but, with just a little bit of encouragement, discovered her hidden desires. At the end of the day, I sent her what I had written, despite it being a very rough draft with no editing or ending. About an hour after I got home, I received a message with a photo of her standing back in front of the mirror again. This time, she had a look on her face that was just full of raw desire. She no longer had the jacket on, and her nipples were very noticeable as they protruded.
The next photo showed her skirt pulled up around her waist, and her pussy was on full display. She appeared to be very wet, and there was a string of cum stretching from her pussy to her damp, shiny thighs. It was the most outrageously sexy thing anyone had ever sent to me, and I was in awe.
The next photo had her shirt open and her breasts bared. One hand was squeezing her breast as her fingers pinched her nipple. Her eyes appeared to have rolled back in uncontrolled desire. Her other hand was on her stomach, fingers spread wide apart, and her knees were bent.
The final image showed her mouth dropped open in a classic “O” shape as the hand that had been on her stomach was now between her thighs. The two middle fingers of her left hand had disappeared into her pussy.
I lay down on my bed and pulled my aching cock from my pants and gave it a gentle squeeze, careful not to overdo it so I didn't just cum immediately. I couldn't get over just how sexy Anne was, and to see her like this, as well as the trust she had in me to send me these, was just so intensely erotic.
I was looking at her cum-smeared thighs and her hand that was half in her pussy when the phone rang, startling me.
I didn't even get the chance to say hello. The moment the call connected, she was moaning huskily.
“I need your cock inside me, Charlie. I need you to come here and fuck me right now. I need to feel your cum inside my body.”
She was panting as her breath got heavier and an orgasm overtook her body. She was making all kinds of erotic sounds as she grunted and cried out and even squealed as she came hard. I gave her a few moments to wind down, and I was just about to say something when she started talking again.
“Oh, God. I can't stop cumming, Charlie. That's the third orgasm I have had since I walked in the front door. I didn't even make it to the bedroom before I had my first; I barely had the front door shut. I would have just left it open and cum right there if I wasn't expecting the kids home soon. Fuck, I'm so horny, Charlie. I want you to fuck me in every possible way you can. Fucking fill me up with your cock, your fingers, and your tongue.”
Her breath was speeding up again, and I could tell she was building towards yet another orgasm.
“I wish I could just get in the car and go to you right now, Anne. I want you so much.”
“Yes, Charlie. Drive here now and fuck me senseless. Fuck me until my legs don't work anymore. Fill my holes, Charlie, fill them with your cum. I want to feel it leaking out of me.”
I could hear the distinct sounds of her very wet pussy getting pounded by what I assumed was her hand, and she clarified my thought moments later as though she could read my mind.
“I've got three fingers deep inside my pussy, Charlie, but it's still not enough; I need your cock.”
The last few words turned into a whining moan as once again she was overtaken by another orgasm.
I could hear her grunting and shaking as it completely took her over, and when she called my name out loudly, my cries joined hers as I too came.
Once everything had calmed down and we got back to talking, it was almost like the pillow talk of two lovers who had been together forever. We talked about our day and what we had planned for the next few days.
I heard a lot of noise in the background with people talking and Anne responding. Then Anne, sounding curiously relieved and annoyed at the same time, spoke to me.
“I'm sorry, Charlie, but I have to go. The kids have just got home.”
Then, in a whisper, she added, “I need to go wash all this cum off me before I go and greet them. I probably should have more on than just my dressing gown. True or not, I don't want my kids thinking I was just lying around coming all over myself.”
I couldn't help but laugh.
“No, that probably wouldn't be ideal. I have to say, though, I would be happy to lick all that cum off your body and clean you up.”
“Mmm, fuck, Charlie. I wish you could, too.”
“I better let you go before we get started again.”
“I don't want to stop, but I really should. I'll talk to you soon. Sweet dreams, Charlie.”
“Oh, they will be because they will be of you.”
We hung up the calls, and I went to have a shower. After I was clean again, I reluctantly got dressed and made myself something for dinner. I wrote a bit more of the new story I was working on while I was eating, and later, I called my kids.
That night, I had just hopped into bed when I heard the messenger app ping on my phone.
“I am having so much fun, Charlie. I hope this never ends. I'm lying in bed thinking about you and the dare you had me do today. I was so worked up when we were talking that I didn't get to tell you just how exciting it was walking around houses, dealing with clients while my nipples tried to tear their way through my blouse. I had to keep my jacket on while people were around me, but every chance I got, I opened it up or took it off. Every step I took, I could feel my breasts bouncing inside my blouse, my nipples rubbing against the material all day. My pussy was so wet that I was genuinely concerned that one of my clients would smell my cum, or it would run down my thigh and someone would see it.
Is it weird that I was scared of that happening, and at the same time, I wanted it too?
Anyway, what I wanted to say was, 'Thank you for making me feel this way and for helping me indulge in these fantasies.' I am loving life at the moment, thanks to you. I hope I am making you as happy as you are making me.
I am going to go to sleep now. I am exhausted, happily exhausted. But... I would love it if you could give me another dare. It might not be as easy to complete any over the next two weeks until Charlotte and Philip go back to their dad's house, but we will see how we go.”
“I am so glad that you are having as much fun...
