This past holiday season, I was introduced to Katie through a mutual friend at while attending a birthday dinner at a restaurant. Outgoing, charismatic, a natural at maintaining a conversation. We immediately hit it off and continued our evening at the bar after the dinner had ended. I found out she was single, not looking for romance, doesn’t wants children and especially adamant about staying out of monogamist relationships. Her sales job had her traveling all over the country at a moment’s notice so keeping any semblance of a normal life like a b/f , pets or a social life (not online) was impossible. She openly admitted that she was a Tinder woman thru and thru. My kinda woman seeing we had similar views on dating life.
Describing her body is difficult to do without it coming out wrong. She had a full-bodied frame that was bordering on thicc. It was closer to pin-up model’s body than what anyone would deem overweight. She held an elegant grace to her that can only be accurately described as “old-school Hollywood” confidence. Average chest around a B cup, big expression-filled hazel eyes, dimple on her left cheek when she smiled and a large bubble butt accentuated by her tight stretchy jeans. Katie was both attractive and not attractive at the same time. She had this stern facial expression that is on the verge of resting-bitch-face, when listening intently. During our chat, I even had to ask if she was OK or mad. She smiled, re-assured me that she was fine and often got that reaction from new people she met. We chatted for over two hours at the bar until we eventually took a walk to stretch our legs. I was hoping to take her home and even ask what her evening plans were. Being open about her thoughts about me, she confided that she was “out-of-commission” at the moment, but and I quote; “looking forward to it next time. Plus, my place has thin walls and I’m loud as fuck!” I got hard just thinking about when that night would occur. We kissed deeply, made out while I pinned her up again her car. We eventually called it a night but not before she smacked my ass as I turned to walk away. Definitely promising!
We texted and kept in touch for a week and finally agreed to meet up when we both had a day off. I was rock hard knowing she was looking forward to our encounter just as much as I was. Even going so far to text “Only a few more days!!!” first thing in the morning. The anticipation never had a chance to drop as we kept one-upping each other with the sex talk. The night before our big day, we were sexting what we wanted to do to each other and I got a partial nude pic of her in the bath. I commented how awesome her body was and if she had any more. More nude pics got sent my way all of her in the bath. These were all taken right now. I made a bold move and told her to take a pic of her fingers inside her pussy. Careful to keep my wording respectful but never-the-less interested. I got one even better than what I asked for. A quick 10 second video of her fingering herself just on the surface of the bathwater and then putting those into her mouth and sucking. She audibly popped them out with a satisfied moan. “*Tomorrow baby!*” followed by a kiss as the video concluded.
Fucking HOT as hell! I pounded my meat multiple times that night and let her know that the video was the reason why. She wanted to see my cock so I sent her some of my own pics. She giggled and wanted me to text in detail what I wanted to do to her with my big “meat dog”. I complied and sent wall of text after text in a continuous story. Describing a fictional story of us in a mountain wood cabin where we fucked for hours at a time. Eventually, I stopped seeing replies from her and I thought she passed out from the long day and also jilling off. I put the phone down to charge and passed out myself. 10 minutes later I was woken up to several rapid texts in succession, all with attachments. The first pic downloaded and it was a lower body shot of Katie with a dildo inside her but not the best angle. The second picture was a similar pose, yet the view was not able to show the lady bits. One handed camera selfies on body parts while masturbating was hard, ok?!. The 3rd pic took a while to finish downloading and I assumed it was another of the same. When it finally downloaded, the view caused my eyes to bug out. Katie was face down, ass up with her other hand steadying the dildo in place. Slightly obscured behind her hand was a glass ring-style butt plug firmly inserted. My already sore dick got hard once more and I quickly had to adjust to keep the growth in check. I rapidly texted back, “*tomorrow is going to be fuuuuuuun, back door girls are the best!*”. She replied with a winking emoji and a heart. God dammit! My sore cock was rock hard again.
**The Night begins:**
5pm could not arrive fast enough. I had to rub one out just to keep my libido in check due to the anticipation. I forced myself to keep from texting her throughout the day. I later found out; she was refraining from doing the same thing. Finally, it was 5 pm and Katie was a no show. A full half hour goes by and then an hour. I keep my anxiety in check by watching some Netflix but I was bummed to be sure. I texted her at 6:15 or so asking for an ETA, and nothing. 6:45 rolls around and I get a phone-call from Katie. She was clearly driving and apologized profusely for being late. She was 15 minutes away and my depressed mood perked right back up. We chatted for a bit as she seemed like in a talkative mood so I stayed on. When I asked her why she was so late, she claimed she lost track of time. I don’t know why but I immediately didn’t believe her. Something that is characteristically not like me. I take people at their word but the way she said it, caused me to question her. In a bold move, I made a statement of, “*Ok… so what were you really doing?*” silence on the other end of the phone. “*Were you using the toys from last night?*” Long silence again, then she meekly said, “*Yes*…” We both barked a laugh and she followed up with a series of embarrassed sounds. “*I’m impressed… not going to lie. Hope you didn’t over exert yourself*?” Katie just laughed self-consciously, “*No, I’m good*” I teasingly remark, “*You know, If the front is too sore, I’ll just have to take the back.”* She laughed wholeheartedly… “*Ohh yeah*?” she paused over my laughter “*maybe*….” In a sing-song voice. Well shit, now I was rock hard again!
She pulls up and I greet her with a kiss by her car. She looks gorgeous, clearly dolled up for my expense in a nice silky loose top showing off a bit of cleavage accented with a casual business skirt that highlighted her curves. I walk her inside to the smells of dinner, scented candles and her favorite opened bottle of wine. We have a lite but flavorful dinner and talked until the conversation came to a lull. She took that opportunity to lead to the night’s activities with, “*Dinner was goooooood, I need some Dessert.*” I casually agree with a smile, not trying to sound too eager.
Katie is peeling off layers of clothing as we make our way to the bedroom. Her outgoing, take life by the horns was sexy as hell and I couldn’t get enough of it. The silky top hits the floor and she’s flipping the heals off as they bounced off the walls and furniture. Only in her lacy black bra and skirt by the time she reached my bed, I couldn’t help by stop at the door and admire her silky-smooth skin. No freckles or scars, no blemishes or imperfections anywhere to be seen. Like a olive skinned porcelain doll. Only a few small moles scattered across her otherwise flawless body. She noticed me watching her undress and tells me to get my butt over there and help her take off the rest. I oblige her and the bra comes off while her back is to me. Looking over her shoulder, she has medium ghost areolas that look perfect on her B cup breasts. I cup them from behind and gently massage and squeeze each with care. Katie had told me several times that her nipples are ultra-sensitive so to go easy on them when I play. Her gasps and soft moans were a sign I was doing it right. My hands traveled up and down her front, caressing her soft skin until they got to her skirt. I unhooked the front and carefully slid both the fabric and the panties down her ample hips. Guiding the clothing down to the floor, I kissed her bare ass on the way back up. She moaned in approval.
Completely naked before me, she turned around and gave me those “fuck-me” eyes. Her hand shot out and firmly grabbed my cock through my pants. It surprised me but it didn’t hurt. “*Mine*!” she said in an authoritative tone. I grunted in approval only to mirror her actions with my own as I cupped her bald pussy in a forceful grip of my own. “*Mine*!” I mimicked. Her mischievous smile was all the response I got.
I was eager to give her oral but she had other plans. Katie got up on the bed and laid back with legs spread far and wide. She was clearly ready to go straight to the good stuff, commenting that she wanted to apologize for being late. I was hoping for a Blowjob but I wasn’t exactly complaining. I wasted no time in unrolling a condom and getting up on the bed. She was rubbing her clit slowly, clearly spreading her juices over her wet pussy. I guided my cock to her entrance, getting it nice and wet before going in. I entered and she moaned all the air out of her lungs to the point that she had to gasp to get air back in. I’m on the thicker side so going her tight pussy left her speechless. She propped herself up by her elbows to get a deep kiss, spread her legs wider so that I could go deeper. She was definitely on the flexible side with her body moving to accommodate my mounting.
I started to slow fuck her and Katie stared daggers into my eyes with her stern expression. Concentrating on my girth as I pumped her unhurriedly, I had to focus on something else given her scary look. Her pussy was tight, not something I was used too with women my age. Either exercise, Kegels, naturally small pussy, I wasn’t sure what kept her so tight but I was loving how she felt around my dick. Just as I was increasing in pace, she took charge and rolled me over so that she could ride me on top. I was impressed she could do this while I was still inside and I happily let her control the motions for a bit. The angle was a bit off for cowgirl position but she made the best of it.
We tried several more non-traditional positions before she gave up and got onto her hands and knees. This was the first time seeing her bubble butt ass from this vantage point and I took a few moments to admire the view before continuing. Her silky-smooth ass matched the rest of her perfect skin and I absolutely loved it. She noticed the delay and twerked a few times to break my hypnotized gaze. “*Gawd damn woman, you have no idea how fine an ass you truly have.*” I didn’t care how I sounded, it was the truth. Katie only cooed in a sultry voice, “*All yours baby*”. I guided my cock back home and proceeded to truly fuck her now. I was careful not to hurt her but I wasn’t gentle at all in my thrusts. I felt my orgasm coming while she started moaning in deep gasps, completely out of rhythm from my pumping. She wasn’t loud like she said she was, but keeping her orgasm silent for some reason. My cock exploded into the rubber and I felt her breathing come further apart and deeper in motions. She was holding her breath to extend the sensations.
**Round Two:**
We collapsed into the bed, my cock still spasming uncontrollable inside her prone body. Katie cooed and moaned playfully while gently squirming underneath me. “*Were… were you holding your… breath at the end?*” I gasped softly. “*Hmmmmm, yeah, helps me get off better. I love to be choked*”. Good details to know I thought to myself. I cleaned up in the bathroom and returned to bed. We recovered by talking gently, reliving our texting the past week and taking sips of water and wine. I couldn’t tell you how long it took but it seemed shorter than normal. She tried sucking my cock a bit but she wasn’t exactly the best. We tried 69 but she wasn’t into receiving oral. Not her thing. For 20 minutes we tried various fun and new positions for oral, sex, fingering her pussy and the like. She even to try fingering me while giving a blow job but I had to stop her from lack of experience. Damn she was rough and not exactly my thing.
Running out of ideas as the hour got late, I suggested she let me toy her for a bit knowing she brought a small treasure trove of personal effects. She agreed and allow me to fetch her bag from the other room. As I opened its contents, I was surprised she brought monster cock from the video the previous night. I pulled it out and wobbled its gelatinous figure with a shit-eating grin in her direction. She covered her face in embarrassment and rolled over to hide her expression further. “*Sooo, big daddy huh?*” she grabbed the pillow and comically shoved it over her head with both hands. “*Want it in the front? Or the back?*” She shot up from her prone position and stared at me with wide eyed surprise before launching the pillow at me. It missed by a mile but that didn’t stop her from running over to me and attempt to grab the dildo from it’s still wobbling spot. We playfully wrestled and she allowed me to overpower her back to the bed. I pinned her arms with my own and followed her flailing legs down with my own. I teased her more and she halfheartedly attempted to break free. When she calmed down enough to look at me, I half seriously stated, “*wanna try DP*?”. Katie’s entire demeanor shifted and she froze in what I would call a lust-filled shock. She didn’t answer, didn’t even make a noise, just stared at me with this wanting look with lips slightly apart. I smiled and softly let her know through my actions that I would go slow and gentle as she needed. Katie kept that same expression of lustful shock on her face and nodded in approval.
We got into a new position where she was on her back with her ass hanging slightly over the edge. A pillow under her for support, she grabbed her ankles in Happy Baby yoga pose. We swapped out the comically large “Big-Daddy” dildo for a smaller vibrating one. I used it on her pussy and Katie moaned in satisfaction. I pumped her pussy until she was on the verge of cumming, which took a lot longer than I was expecting. I stroked my cock back up to rock hard as Katie took over dildo-duties. Her eyes were wide with excitement knowing she was about to be DP’ed.
I applied lots of lube to her ass and my fingers as I slowly worked her rear. I made sure to go as slow as possible and even then, it took an obscene amount of time to get her loose enough for me to go from one finger to two. At some point, her winces turned to moans and she was becoming ready to try my girthy cock. I stroked myself hard, wrapped it up once again and dumped more lube on it. I stood in place just at the entrance of her ass and slowly pushed in while she vibrated her clit. It slid passed the point of no return and her anus popped. She jumped in pain and I wanted to pull out. She stopped me and told me to don’t move. I watched her stroke her clit, fingering herself to focus on anything else but the massive cock at the entrance of her tight ass.
I watched her pained expression lessen while slowly turning to a wide gasp of satisfied shock. I took my cue and slowly started to push further in. There was no more pain what-so-ever. Katie helped guide me in with visual aids of how fast/slow to go. Within minutes, the snail’s pace was now a steady average paced butt fucking and she could now focus on getting the dildo inserted. I helped guide it in due to the angle and eventually it nestled smoothly in place. Katie’s moans were louder now and more enthusiastic than before. All pretense was gone as both of our paces increased. I honestly don’t know how long we were going at it in that position but it was long enough that she started to cramp up in her legs. She tossed the dildo aside, rubbed her clit harder and started telling me to fuck her hard.
I couldn’t keep up the pace in this position as the angle was tiring on me. I pulled out, flipped her onto her front with legs hanging over the bed and onto the floor. She was bent over completely with the pillow now propping up her stomach. Wasting no time, I slid back into her ass and was met with zero effort. Her ass was still tight, but there was no resistance now. I grabbed her hips and trusted myself balls deep. Katie screamed in pleasure, “*oohmygod!!! Jeeesussfuck me*!” My pull out game was fast but my penetrating thrusts were as hard and deep as I could go. The solid metal bedframe even began to squeal and even move at some point but I didn’t stop. I shoved my cock deep into Katie’s ass and she gasped for air. I noticed she was holding her breath again and I took it upon myself to pull back her hair so she was arched up. I used this new position to grab her throat while the other pulled her hair back. She was visibly straining to keep from being entirely held up by my hands but her desire to be fucked this way was clear. Katie even attempted to get me to choke her harder by forcing her head down even though her hair was being pulled back. My cock was pile driving into her ass at this point and I was near an epic worthy orgasm. Our body slapping combined with her breathless chokes made her screams of pleasure that much hotter. My hand was now only gripping her throat, she was doing all the choking herself.
I didn’t so much sense her orgasm as I felt her entire body shutter in convulsions. She tensed her upper body while a wheeze of air escaped her open mouth. A gush of juiced squirted from her pussy and hit my balls and leg. Katie gulped in air as her body collapsed to the bed below her. My own orgasm a mere shadow of what she went though. Seconds later, she was wincing in pain, “*Ow, ow, pull out slowly…* “ I eased myself out and she flinched when I popped out. Panting, she slurred out her words, “*hooolyshiet…ooomygod, fuck*” My own breathing matching hers, not even sure how I was still standing on two feet. “*Soo, how was that?”* I wheezed through a head rush. Her hand rose with great effort to imitate gripping a cup like object, “*you… get… the award.*” Her arm plopped back down from the effort. I laughed, “*pretty sure I already got my award*” She just smiled through closed eyes.
End of Part 1
More of Katie soon
Source: reddit.com/r/gonewildstories/comments/bmjykt/mf_when_a_business_professional_holds_her_breath
Nice man! Very descriptive
Duuuuddeee this story was awesome. Loved the descriptions and she seems like so much fun.