"For the third time, I want to fuck you"
That one sentence was how I found myself parked at this hotel in Central Jersey. Ok, clearly not just that sentence.
It all started with an ad. My first on Lit. Not sure how I got to their personal sections after years of reading stories, but there I was, posting for the first time on Lit. "Married man, 44, looking for someone to roleplay and tease during the day," or something similar. Two lines max. Not my best writing.
My expectations were not too high. After a series of flings and some really strange situations on another online board, I just wanted someone to innocently play with during the day. A little teasing, some roleplaying. Nothing serious. Locals need not apply. Just a fun distraction from the mundane monotony that being a mid-level manager in a small software company brings on in spades. Nice and easy.
I'd love to say the responses to such a deeply and thoughtfully written ad came rolling in like wildfire, but we all know it wasn't true. Aside from the expected spam and folks so far out there they had to be fake, I got a single private message.
"MWF, 43. Sounds fun."
That started a whirlwind of fun and flirtation. The first day was filled with the usual get-to-know-you type stuff. We actually grew up just a few towns away from each other. Potentially knew some of the same people back in the day. Then pictures were exchanged. Physical characteristics shared.
She was tall. Taller than me, although that is easy as I top the ruler at five-foot-seven. That typically ends the conversation right there, but not this time. Short men? No problems for her. After all, this was roleplay. Fantasy.
Over the next few days, texts quickly turned to sexts. Sexts became FaceTime. Toys became involved. We had "Friday Lunch" together. FaceTime playtime when she worked from home. As cliche as it seems in stories of this type, this woman was as horny and worked up as I was daily.
Conversations became nightly. Wants and desires spoken of and fantasized about. Phone sex on the way to work even. Surreptitious pictures of the tent in my jeans after a hot conversation during a conference call. Damn, was that a fun first few weeks.
I don't want you to think everything was sunshine and lollipops. We definitely had some hiccups along the way. Like the disastrous first pic I sent her that she still makes fun of to this day. The sad first attempt at phone sex while she rode a train to Connecticut for work. But something just clicked. We got past those without batting an eye, and the conversations grew hotter. More passionate. Insanely erotic.
When I say it was everything I was looking for when I posted that ad, that is not an exaggeration. We texted daily. We sexted daily. To and from work.
One day, I told her how I would make her come at every traffic light on her long drive to work. The next, she texted how she'd blow me nonstop on my way home. Coaxing as many orgasms out of me as she could.
She made recordings of getting herself off at a friend's pool party and sent it to me. If I had a break in my daily grind on the weekend, I checked my KIK account to send her a note and see if she had time to play. She was already a step ahead with a simple note asking: What are you doing? Inevitably, one or both of us got off by the end of the conversation. Fuck, it was hot.
Then, nearly two months into the fun, fate decided to shine its light on me. I was going to be travelling to see family without my wife in October. Less than 60 miles from my fantasy girl. Now, I have not been a saint in my marriage, and I have had a female friend or two. But those were all online. A fleeting moment. A truly sage NSA encounter. Not sex but definitely close. This was different. Not quite sure how, but definitely different. It was a long shot, still, I had to ask if she could get away that Saturday night.
It was a big moment going from fantasy to reality. Heart (and hard-on) in hand, I waited for the answer which ended up not being the one I anticipated. You see, she had yet to venture outside her vows except for our flirtations and fun. She would love to get together but wasn't sure she'd be ready to take that final step yet. Being the kind and respectful gentleman I was (no... the irony of also being a philander wasn't lost on me), I said I'd love to see her and we didn't need to do anything she didn't want to. In fact, I wasn't going to sleep with her unless she told me three separate times she was ready. That was my brilliant philosophy!
So plans were set with hotel reservations made, and flirting ratcheted up about 300%. Generic teasing and fantasies became crystallized around that weekend. That hotel. That room. Every conversation began with her opening the door and ended with us exploding in mutual orgasm, as all true fantasies should. Roles began to form. She wanted someone to take control. Not my usual style, I was so invested in giving her what she wanted that my fantasies and stories went down that road. Telling her what I wanted. Taking control. Fuck. That got me so turned on. After 25 years of being the nice guy, being somewhat dominant in my fantasies opened my eyes to a new world... but that's all it was. Fantasy.
Until, the first time she said she was ready.
We are about two weeks out. Sexting and Face-Timing nonstop. Everything was about the room. Pushing her up against the door. Kneeling behind her and eating her out until she begged for my cock. Straddling my head as she took me into her mouth, swallowing every inch. Her sitting in the chair as I filled her with every hard thrust. This wasn't making love. This wasn't just sex. This was FUCKING. And quite frankly, I hadn't fucked since college. To say this was intense was an understatement. Then at the end of one of sexting sessions came the message:
"I want to fuck you."
"That's one", I said.
Two more times were needed. And I had meant it. A night of pleasing her orally, manually, and with her ever-present set of toys was more than enough for me. I wasn't going to push. Not for her. Not for the timing and the step she needed to take. But that didn't stop the fantasies from being fuck-filled, for lack of a better term. Through the fantasies, my tendencies grew more dominant. Grabbing her hair to pull myself deeper inside of her. Smacking her ass while I fucked her doggie-style. Sliding a finger into her ass while I fucked her with my other fingers. Things I had never done but still turned me on more than I could ever imagine.
The ideas kept growing, but always in that room. Sometimes, we entered together. Sometimes, I opened the door. Or she did. But it was always hot. Always amazing. Even if it was all virtual.
I don't remember the details of when the second time she told me she wanted to fuck me, but it was at least a week later.
I am not quite sure how the temperature kept getting raised, but it did. I kept playing the nice guy in between sessions. Of course, I was fine if we never got to number three. Whatever made her comfortable. I would never push. And all of it was true. I firmly stood by that.