This is a direct continuation of part 2. Plus, it spaces out the wild events from first night and the kinky hot events of the second night. However, It’s written that neither are required to enjoy this story.
Katie was texting me throughout the workday from how amazing last night was, mirror selfies from the hotel bathroom with and without clothes, to outright sexting. She was even begging me to ditch work to meet up early at one point. No, not distracting at all. Pffft! Who would be distracted by a hot woman wanting sex, in a hotel, that evening, with me? Why does my inner monologue sound an awful lot like a high-pitched Flynn Ryder, I don’t know! But I got through the day by some miracle without getting fired for permanent trouser tent. I made a pit-stop at my place to shower, pick up an extra change of clothes and grab my bedroom fun bag. The traffic was insane heading back to her Hotel but I trudged along knowing happy times were coming. Katie alerted me that she finished up another day of conference booth duties while I was over half way there. Soon, another pic of her naked body selfie looking sultry and tasty dinged on my phone. I was already annoyed at the slow traffic, hungry from skipping dinner and now horny to boot. No! not distracting at all.
I was starving when I pulled into the parking lot an hour earlier than expected. I downed a burger at a local dive across the street. From the outside table, I got a better view of the Hotel’s privacy windows. They were effective enough that even the fully lit room on the 4th floor only showed a blurry human like blob in muted colors at best. I felt better about the window entertainment from last night wasn’t as voyeuristic as I envisioned. I decided that a repeat window adventure wouldn’t trigger further anxiety in me. I texted her a quick story of what I wanted to do to her body in the window again and she was unquestionably responsive. I wrapped up the mental foreplay and told her that I was heading up with, “Hope you’re lubed up woman!” She winky-faced me in return, followed by a “You wish!” Ehh, playing hard to get wasn’t a problem. I’d get that ass tonight for sure!
I already expected something of a repeat door experience when I knocked but she still managed to surprise me. Katie opened it doing a full body door length pose but now completely in the nude. It took a second for my brain to work but I was quick on the take, I said in a nerdy voice “*Are you the Gatekeeper*?” She faltered as she barked out a laugh. We both loved to play out sexy moments to get the other to laugh. I ended up winning at her attempt to get me to chuckle and she smacked my ass as I entered the room. “*Ohh my god, you’re such a dork*.” She turned towards the beer bucket to grab me one while snorting. I dropped into the chair and started to undress.
She was hovering over her room service tray, picking at the plate while talking about her day. The woman loved to be nude and I was still impressed at her comfort level with me. She found ways to do the most mundane things without a single piece of clothing on. Not a care or ounce of modesty in her bones and that in itself turn me on.
Her day was better than yesterday and blah blah blah, clients this, customers that. I tuned most of it out while I gawked at her perfect full-figured frame. I know I talked about her body before, but as I stated in part 1, she’s not exactly easy to describe. Try to picture the thickness of Chun-li’s thighs, a Kardashian ass (ok, not quite as big), the flawless olive-ish skin tone of a model, decent B cup tits with ghost nipples and the stern face of [Lilith Sternin](https://en.wikipedia.org/wiki/Lilith_Sternin#/media/File:Lilith_Sternin_in_%22Sisterly_Love%22.png) from Cheers (Frasier’s ex-girlfriend). The hair is a bit harder to get right as the look alters depending on the day. A tight bun if coming from work, a high ponytail/tied back on her days off, or loose and disheveled when around me and after sex. Her strict chiseled facial features are definitely an acquired taste but I had grown to appreciate it. She was every bit the Business woman stereotype look, but fuck she was kinky hot in bed.
The topic of conversation changed instantly when she brought up last night’s window venture. “Fuck that was hot… the palms on the window… the hair pulling…” Katie chewed a piece of chicken. “Ya did good stud.” the permanent bachelorette in her often came out when she was comfortable. I replied smoothly, “Well, when you’re this good…” letting the statement hang in a playful tone. She laughed and popped more food in her mouth. I finished undressing and unzipped the toy bag I brought up. “Wanna step it up tonight?” giving her the Groucho Marx eyebrow waggle. She gave me that sultry-interested look and sauntered over to sit on the bed to have a peek. “…maaybe”
She immediately pulled out the wrist cuffs, a staple choice of hers back at my place. The floggers and paddles were tossed aside per usual (still trying to get her into spanking) and she pulled out the nipple suction cups. The medium black butt plug was spotted and she looked up at me with that ‘…really?’ face. “God, I swear you just want my ass and nothing else” I smiled, “I like what I like Babe”. She shoved it aside and grabbed the pink vibrator to finish her toy line up. “Ohh ha ha, quit trying to shove that huge thing up my butt. I’m a good girl.” I joked, “Pfft, please what about last night?! Plus, this one nearly slipped out of you 2 weeks ago. Your ass is almost ready for the large one.” She opened her mouth in mock outrage and gave me a loud guffaw. Moments later she smacked my arm with the vibrator. “Whatever..” she scoffed as she got up to apply the nipple cups on with careful attention. “I’m a good girl” saying in an playful girly tone.
I knew applying the suction cups took focus so I stopped the banter until she was finished. I admired her work knowing how sensitive her nipples were. My previous attempts at doing this task only left her jumpy, in pain or too sore to continue. The second cup now firmly in place, I continue where we left off, “Hah, good girls don’t like to DP as much as you.” Katie gave me that mischievous grin, but chose to ignore my comment “Good girl or no butt stuff tonight” I became mock serious for a moment. “The best good girl I know! Halo like even” She bounced each suctioned cup titty in her hand for both of our amusement. Katie tossed me the wrist cuffs, “That’s right, now put these on this good girl stud!” ending her sentence in an imitation Texas twang.
I got to work securing each strap to her wrists behind her back and attaching them at the link. The metal jingled in place as she tested the resistance. Turning back around, she gave me the innocent pouty face, “I’ma good girl!”. Continuing the Texas drawl. I grinned, “Does this Good girl want it in her ass first? Or does she need to get on her knees.” She scrunched her face in disapproval of her choices but agreed to knees. I helped guide her down to the floor, even stuck a pillow under her for comfort.
Katie looked up at me with hungry eyes and I pulled my boxers down just enough to whip my cock out. She took my length fully into her mouth in one swallow. Katie was a self-proclaimed BJ queen and I wasn’t going to disagree. She was very good, but I braced for the shock of teeth but none came. Jaw opened wider than normal; she tongued the bottom of my cock while fully enclosed creating suction. She took great care to avoid the teeth this time and fuck did it feel good. Gagging as my tip hit the back of her throat, I enjoyed the moment for what it was worth. She was determined to give me a tooth free BJ that often plagued her previous attempts. I grabbed the sides of her head with her hands now secured behind her back. Katie’s eyes locked onto mine and she gulped loudly with exaggerated gasps of air. She was enjoying this as much as I was. “Yes, yes you are a good girl” She beamed a smile with high cheekbones knowing she loved words of encouragement.
I felt the urge coming to the surface and I stopped her mid suck so that I could pull out. She sucked harder on the last few inches before my shaft popped out of her mouth. I quickly helped her up and turned her around to face the bed. I directed her to place her head on the bed, pillow under her upper chest for support. I entered her wet pussy from behind and fucked her bowed form from the hips. Both hands held her up and her hands flexed from the bound position on her back. The suction cups on her tits stretched her nipples but she enjoyed the mixed pain it brought. One of my hands eventually grabbed the chain holding them together and I used it to pull her back into me. Katie moaned with each shove and her breath started to come in gasps and extended waves.
Not wearing a condom this time around, I had to time my orgasm just right. A few more moments of bliss and I busted a nut while pulling out. I covered her round ass, back, hands and wrist cuffs with cum. It was a small amount but I was just getting warmed up.
Katie stayed bound and in that same position while as I went to clean up. I took my time, teasing her knowing she hadn’t cum yet. I eventually came back and toweled her off. I slapped her round ass a few times while I settled in for round 2. I lubed up the vibrator and gave her clit a long teasing. She squirmed in place and moaned loudly for me to shove it in. I held her down and in place as I played with her pussy until she was begging me to fuck her with it.
I inserted it slowly and applied pressure to her G-spot knowing she was on the verge. She came within seconds. Minutes later and I forced another 2 small orgasms out of her. She was helpless in my control as I used the thumb on the hand holding her down to rub her asshole. She clenched her cheeks in involuntary protest. “Seriously? Already after my ass?” I let me thumbs do the talking and applied pressure at her back entrance. She sighed and just went with the flow. It took a long time to coax her ass into letting my lubed thumb in but eventually it sucked me in with little resistance.
I fingered her ass and fucked her pussy with the vibrator for as long as it took her for her moans to become deeper and on reflex. I slowed down and pulled both out to give her body a moments break. “How about a repeat of the window?” She smiled greedily knowing full well she wanted that more than anything. “… only I’m in your ass this time” The smile only faltered for a moment and giggled, “I’m a good girl!”. I answered her happily, “Yup! A good girl taking it in the ass tonight”. She rolled her eyes and smile while jiggling her hands for the cuffs to be removed.
Minutes later, her palms were up against the window in a repeat posture of last night. I applied another generous helping of lube and Katie sucked in a breath at the insertion of my fingers. She was more relaxed than our first time and sliding in and out of her ass with the lube gave me a rock-hard boner. I pressed my wrapped cock up to her back entrance and pressed gently. She grimaced in minor pain but exhaled slowly like she’d been taught. Her asshole relaxed and my cock glided in slow and steady with no resistance. Her cry of “oohhhh, easy!” caused me to halt. I let her adjust to my girth for however long it took. A moment later, she was slowly pumping her ass back.
I looked out over the nighttime cityscape feeling the deep satisfaction of fucking one of the hottest women in the ass at that very moment. I grabbed handfuls of her cheeks and pumped slow and deep looking out at all the lights and traffic below. Katie used her leverage to push back into me while allowing my thrusts in to push her slightly forward. I could see from the reflection that she was looking out the window as well, giving whoever could see an awesome show. I picked up the pace and dove in faster and with pleasure. Her ass was tight and all but it was her secret enjoyment that got me harder that diamonds. Where last night she was fairly reserved in her vocals, tonight she was deep in the throws of moans and frenzied cries.
The neighbors had to be hearing her screams and they were loud enough to make me worried that security would be called. I had been butt fucking her for close to five minutes now and she had cum once so far with another about to materialize. I gentled pulled back on her hair to encourage her to keep it to a dull roar. But after her 3rd body shaking orgasm, I gave up that security was sure to be on their way. I lost track of time trying to extend this moment as long as I could. I figured ten minutes had passed since we started at the window but I wasn’t exactly keeping count. I was close to orgasm myself but Katie was coming up on another big one, I lost count there too considering she was shaking every few moments at this point.
The urge to blow was coming to a boiling point and I grunted, “I’m cumming,” unable to say anything else. I shoved my cock as hard as I could in her ass and I nearly pancaked her up against the window. The nipple cups popped off painfully and we adjusted our position. Her lower half was still attempting to stay in position but Katie’s arms now against the glass. Her face was pressed sideways as I shifted from hair pulling to head pushing. “Fffuucccckk meee!” was all she could utter as my dick gave her the rectal reaming of a lifetime. Slamming hard one more time, my cock exploded and Katie squirted with a long continuous grunt onto the carpet. Crying out for air with spittle landing on the window, she rode out her ecstasy for longer than I could imagine. My fucking eased to a slow crawl and she moaned in place without moving. I almost passed out it was so good. I had to wobble to the bed while collapsing face up. Katie stayed plastered against the window, occasionally shaking to an aftershock-gasm.
“Good girl…” I gulped in air, “Good, good girl” She smiled. “…told ya”
Security never came. It was a good night.
**TL:DR** Had kinky sex with a FWB while in her Hotel room for the second night in a row. First a wrist-cuffed blow job, followed by multiple forced orgasms with toys. Finished the night with her pressed up against the window while I butt-fucked her in front of an unseen city-wide audience.
Source: reddit.com/r/gonewildstories/comments/bnguuv/mf_the_business_professionals_view_in_the_end
Hot! Why add the TLDR at the end?