Four nights
Night 1:
My road trip didn’t get off to a great start. In the space of 15 minutes, I got a speeding ticket and two messages from girls I was wanting to play with.
The first girl wanted to wrestle. She was 5’11, only three inches shorter than me. The thought of taking her on was thrilling, because I wouldn’t have an easy win. She also had a pretty face and great tits. But she was also hosting a friend from out of town, and felt guilty being a bad host. Ultimately, she had to say no.
The second girl, was one I found a few weeks earlier, and she was at the time in no shape to be a play partner. She was going through the stages of a break-up and didn’t really notice it when she first started chatting with me. The week before she had been to her first dungeon, and she allowed a Dom to play with her with a shock baton. She really loved it, but she didn’t tell her then-boyfriend about it. I could see the start of a bad pattern, so she got some hard questions from me.
I helped her understand that she had three possible paths – talk to the boyfriend and get him to join her in her kink explorations, break up with the boyfriend, or stop exploring her kinks behind her back.
She chose to break up with him. And for the next week or so, I became her digital shoulder to cry on, as well as a voice of almost-reason. At one point, she became very certain that she wanted to fuck me. Being a fan of her ass, tits and lips, I was not going to turn her down. I picked out how I wanted her hair and make-up. I chose what shirt, skirt, bra and panties I wanted her to wear.
But her pussy had other plans, and her “time” of the month made that off-limits.
Honestly, I don’t have a problem fucking a woman while she’s on her period. I’m not as likely to go down on her, and usually my hand stays on her clit. But I have no problems whatsoever grabbing a condom and a towel. My main concerns are for the woman – is she comfortable? Does she feel sexy? Do I have any chocolate and Midol handy?
In her case, she didn’t feel too comfortable. But she did have a different desire.
“Well, I don’t want to be too forward but how do you feel about anal/ass play?” she wrote.
That made us talk about her anal limits – how often has she had anal, how often she plays with her ass, and what does she use for her ass play. As it turns out, she was into being fingered in her ass, but didn’t have any toys.
I instructed her to buy a plug and insert it for up to 30 minutes for her first day, but to remove it immediately if there was too much pain. Anal play is tricky. If a fucktoy can fit a plug in with no problem, then there’s a good chance she’s going to enjoy and be able to handle getting fucked hard. If not, you need to start with a small plug, and train your asshole over a couple weeks.
She reported back with pride that yes, her asshole was ready and fuckable.
So I added in two more plug sessions for her.
On my drive up, and after one cancellation and a speeding ticket, I got a fairly cryptic message about a small emergency that she needed to take care of, and couldn’t make it. I waited until I got to my hotel an hour later and told her it was OK, these things happen.
Something was making her sad, and I let her know that I was there if she needed someone to talk to. Technically I was offering to chat with her online. She saw an opening and asked if it would be OK to swing by and just talk. I agreed, because hey, why not? I’d been alone in my car all day, some human company would be nice.
I did have to note that there was one thing I needed to take care of before she got there – I hadn’t had a chance to cum in 48 hours, and I felt like I was about to explode. I needed to cum before she got there.
Or…
Or, maybe…
I’m not sure which of us suggested this, but eventually the plan was that she would watch me stroke my cock and cum. Something to cheer her up, take her mind off of things.
40 minutes later, she met me in the lobby of my hotel. I noticed right away that she had done her hair and makeup exactly as I wanted her to. And she was wearing the shirt and skirt I had picked out for her. I wondered if she was wearing the bra and panties I picked, or if I would find out.
I gave her a gentlemanly hug, then took her to my room. I let her know what number the room was, in case she needed to text it to someone. We came inside, and I did my very best to not touch her.
I asked her to go over her limits again, since this was a fairly newly renegotiated scene. She demurred.
“Maybe?”
Maybe is a very interesting limit.
“Are you thinking you want to do more than just watch?” I asked.
“Yes.”
I reminded her of my “Stoplight” system. I went over the earlier limits and safewords, and she nodded. I’m not a fan of renegotiating a scene in the middle of a scene, but I could see her ass filling out her denim skirt, and I wanted her lips on my cock.
I took it slow with her – caressing touches on her legs, kisses, pushing up her shirt to see that she did indeed put on the bra I demanded. She had been planning this. That was a brat move, and I knew how to deal with brats.
Caught, she grinned. I bent her over my lap and pushed up her skirt. There, barely covering her ass cheeks, was the panties I had picked out. I wouldn’t need to pull them down to spank her. Instead, I went about covering her with red hand-marks, occasionally pulling her hair or squeezing her neck to remind her that she’s a naughty little slut.
I licked my middle finger, then slid it under her panties and between her asscheeks. Circling her asshole, teasing it, she started to whimper in anticipation. Pushing the finger inside of her, I was pretty sure that I was going to be able to fit in her ass. It was tight, but there was enough give.
I had to unzip her shoes and pull down her panties. Grabbing some lube, I started to work her asshole. The ass itself was spectacular – firm, round, mostly unmarked except for some rude red hand marks. The cleavage between her buttocks was a solid two inches deep. Honestly, if I couldn’t fit inside of her asshole, just lubing up and fucking that valley would have been fun.
But eventually I started fingering her asshole with two fingers. She was moaning like the good little slut she was. I spread the fingers just slightly (my cock is roughly as thick at two and a half of my fingers. I know that a pussy is fuckable for me if I can slide two fingers in, but an asshole needs just a little more stretching).
Next, it was time to get my cock ready. I pulled my pants off, then pulled her by the hair until she was off the bed. Because I’m a nice guy, I put a pillow on the floor and demanded she get on her knees there. It took longer than I wanted, so I grabbed her by the hair and dragged her until she was in place. Then I yanked her head back and pushed my cock in her mouth.
At this point, I was already throbbing hard and ready for her ass. I’m not sure she was fully ready for it, though. And feeling my girth in her mouth probably wasn’t calming her, knowing that I was about to be very, very rough with her. So I let her be a mindless little cocksucker for a while longer. I wasn’t going to let her drain my cum into her mouth, though. I wanted that ass.
When I felt she was ready, I pulled her up by her neck, then pushed her over. I went back to fingering her asshole – it was still ready for my dick.
I pushed and guided my cock. She started to struggle and tighten up against me. I had to tread the fine line between being rough and being a Dom, and being gentle enough to not break her ass.
I gave her a moment, switching back to my fingers. She started to wriggle away, across the mattress. So I yanked her ankles and dragged her back. I placed a hand firmly on the back her head, pushing her into a mattress. She started whimpering, repeating, “No no no no no.”
I stroked my cock along her ass crack. I could feel her hole as the tip of my cock rubbed it.
“Stoplight,” I said.
She stopped her “no’s” for a second, but said nothing.
I pulled her head back by her hair and pulled her ear to my mouth.
“Stoplight,” I said, with more force.
“Green,” she said, with a little grin.
“Take a deep breath,” I said.
I pushed hard, forcefully. She had slightly more care than some of my previous painal victims, but not that much. I have had that sensation described to me – that searing pain, that complete lack of control and total submission to the weight of my body, the size of my cock, and the desire of her body. The pain doesn’t leave, but it does ebb away, as the sensation of my cock pumping her asshole, rubbing against the nerve-endings shared by her pussy, plucks a deep, submissive pleasure out of her soul.
I started to pump her harder and harder. I could feel her completely surrender to it. The control rushed to my head, and I soaked it in. That power, breaking her, feeling her perfect ass rub against the bottom of my cock’s shaft, and her tight hole squeezing the top two thirds of my cock – I let it intoxicate me. I gave in to my desire to cum.
We had some oral play after that. She was able to cum from me sucking on her tits and rubbing her clit. I let her suck my cock for a bit, but after a 10-hour drive and that particularly intense orgasm, I was having a rare one-and-done night. Plus it was 2 a.m., and I had a busy day ahead of me. I helped her find her scattered clothes, gave her a hug goodbye and passed out.
Source: reddit.com/r/gonewildstories/comments/d2fv2a/the_business_trip_night_one_mf