The Business Retreat – Anal

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“Ok baby, have fun tonight. Don’t get too hammered!” my wife, Kate, teased me over the phone.

“I’ll do my best, my love,” I replied, the smile on my face evident through my voice.

I was halfway across the country for my business’s annual retreat. As I hung up the phone, I wondered about how lucky I was to have such a great wife. We’d been together for over a dozen years and our relationship had evolved over time. What began as a hot and heavy relationship mellowed over the years and we had to adapt with that.

Kate was a bit more traditional when it came to sex and our love life was pretty vanilla. I, on the other hand, had much more varied interests which she was well aware of but not interested in. I had generally resigned myself to this as my future because I was and remain very in love with her and her with me.

That’s why I was so surprised last year when we were at a restaurant one night. Over drinks she said, “I know there are things that you like in bed that I don’t do. If you wanted to get those things elsewhere, I would have no problem with it.”

My mouth must have hit the floor because she started laughing. She added, “Listen I’m not telling you to go fuck everyone you meet or start having affairs. I don’t want you in another relationship. But if you have a one night stand or hire a call girl to get those needs fulfilled, go for it!”

My mind whirled at the idea and I asked several clarifying questions to make sure this wasn’t a trap. And it turns out it wasn’t. I asked her about it several months later and the answer was still the same. “If you have the opportunity, don’t hold back because of me,” Kate insisted. She didn’t want to hear about it or even know it happened, but she didn’t begrudge me from taking benefit.

Coming back to the present and with the phone call with my amazing wife over, I went about preparing for the party that evening. Every fall, my business has an in-person retreat where they bring the whole business to headquarters to celebrate the past year. We had all dressed up a bit for a fun awards-style evening where the top performers in the business were recognized for their contributions.

Once the award show was over, I came back to my hotel room to chat with Kate and get ready for the after party at the office a block from my hotel. I changed into a clothes that were a bit more casual. I’m not big on fancy clothes but I didn’t want to look like a bum either.

I walked over to the office without any goal for the evening in mind other than making sure I didn’t get too drunk and embarass myself. Beyond that, I figured I’d let the night take me where it willed.

When I walked in the door of the office, I took it all in. The place was jumping with dancing, drinking and loud music. The alcohol was flowing and there was a ton of food available.

I made the rounds, making sure I said hi to the people and friends that I saw. Eventually, I found a smaller room that could comfortably hold five or six people. There were a couple of guys sitting around a coffee table and a few bottles of scotch available to choose from. I made myself at home and we quickly jumped into conversation. Over the next hour or so people would pop in and sit down, have a drink and stay for a while or make their way back out of the room.

At one point, I noticed a woman who I hadn’t met before as she came in. She sat across from me at the low coffee table I was relaxing at and said, “Hi! I’m Annie from the Sales team. Who are you?”

I gave a quick laugh at the very direct question but replied the same, “Hey Annie, I’m Craig. I’m on the Tech side.”

Annie was about 5’2″, from Georgia and was a very big girl. If she were in porn she would comfortably fall under the “BBW” category. But that was far from her defining characteristic. She had a very pretty face and as we talked more, I loved her to-the-point style. There wasn’t a lot of beating around the bush, she said what she meant and I enjoyed that.

We ended up talking for at least an hour, probably closer to two. There was definitely a bit of a connection which was probably helped by the scotch. Eventually I excused myself to go to the restroom to take a piss. When I came back, I saw she was no longer in the room we had been in. I shrugged and figured maybe I’d see her again, maybe not.

I made my way through the crowds and ran into a couple of guys who work on a team that I helped out. We chatted for a bit and then out of the corner of my eye, I saw Annie approaching.

“Oh hey Annie, I was ju-” I started. I was interrupted when she walked up to me and stood on her tiptoes to kiss me on the mouth quickly, her tongue just barely brushing over my lips. With a pleased laugh she moved on into the crowd, having momentarily paused to kiss me.

The three of us who were still there looked at one another, the surprise evident on our faces. Then we all broke out laughing and shook our heads. Company parties, man!

The evening started winding down around midnight. I had kept an eye half-peeled for Annie but she had disappeared. It looked like I was done for the night but I pulled my phone out and figured I’d take one last shot.

Opening Slack, I found her profile and opened it. She had a cute profile picture and I typed out a quick message to her.

“Where did you go?” I asked.

Within seconds she replied, “The Delta hotel”.

That wasn’t my hotel but regardless, I responded, “Funny, I’m heading that way.”

Almost immediately, the reply I got back said, “I’m in room 419.”

I felt a little surge of adrenaline in my chest and grabbed my coat. The Delta was a short walk away, five minutes at most. As I walked, I thought about how I might approach this but in the end I just figured I’d knock on her door and see what happened.

Once inside the hotel it was a short elevator ride to the fourth floor. I wound around the hotel hallways until I came across room 419. It was close to 1am at this point so I knocked softly, not wanting to disturb other guests, particularly if they happened to be my coworkers.

The door opened right away and Annie stood in front of me. She was wearing a long button-up pajama shirt, the bottom of which ended about mid-thigh. “Come in,” she said with a small smile.

I walked in and she closed the door behind me. “You disappeared from the party, didn’t think I’d see you,” I said.

She laughed and shook her head, saying, “My team abandoned me, can you believe it? So I just took off figuring I’d call it a night. ” She looked more pointedly at me, “Until you messaged me, that is.”

“I figured I should at least do that given that you kissed me in the middle of the office,” I said with a laugh.

As if goaded, she walked up to me and kissed me again, this time grabbing my ass with one hand to pull me closer. “Like this?” she asked in a half whisper once she broke the kiss.

“Just like that,” I said as a I reached out and started unbuttoning the top button of her pajamas. After the second button was undone, I slipped my hands under the fabric on her shoulders. Spreading it apart, the clothing fell off of her shoulders and quickly pooled around her feet. The pajamas were all she had been wearing and my eyes followed the length of her naked body.

I had never seen a woman naked before that was as thick as Annie. She had curves everywhere although her breasts were smaller than I would have expected of a woman her size. I guess I just always attributed heavier women with larger breasts. She stood in front of me with no discomfort, more than happy to be checked out by my wandering eyes.

My gaze came back to her cute face and she smiled. “I can not be the only one undressed,” she said as she lowered to her knees.

I watched with great focus as she took hold of my belt and unfastened it. When her fingers moved to the button on my pants, her tongue stuck a little ways out of the corner of her mouth, as if there was great concentration happening. When my zipper was down, she reached into my boxer briefs and grabbed hold of my very hard cock. I’ve got a nice sized member, roughly eight inches and thick. It’s not a monster but I get no complaints.

As her chubby fingers wrapped around my shaft, she smiled as if a question in her mind was being answered positively. She pulled my dick out with one hand and pulled my pants down around my ankles with the other. As I stepped out of my shoes and pants, she opened her mouth and wrapped her lips around the head of my cock. Swirling her long tongue around the underside, I found that unbuttoning and removing my shirt was taking more effort than usually necessary. I disrobed completely and stood still as she started moving forward and back on my cock, quickly getting it wet. Each time I disappeared between her lips, she took me in a little farther. Unconsciously, my hands went to her head, slowly guiding her as she blew me.

Soon, the head of my cock was getting close to the back of her throat. Without thinking, my fingers closed in her hair and started pulling her deeper. She gagged as the head of my dick hit her throat solidly.

“Oh fuck, I’m sorry about that,” I sputtered, releasing her hair instantly. She didn’t break stride and kept blowing me and made a sound around my shaft as if to say, “Don’t apologize, do it again.” She winked at me as she stared up into my eyes with my cock going in and out of her mouth.

I tentatively grabbed her hair again and started thrusting gently into her mouth. I banged against her throat a couple more times, each making her gag, the reflex accompanied by guttural sounds from her throat.

She leaned back, my cock coming free from her mouth. There was a string of drool that connected from the tip to her chin. She looked up at me and said, “I don’t think there’s any way I’m getting this thing down my throat.” Then she smiled wickedly adding, “Not at this angle at least.” She stood up and took my hand, leading me to the hotel bed. This was the first time I’d gotten a chance to check out her ass and there was plenty to look at. I love a big ass and this was the biggest I’d seen.

Dragging me onto the bed, she pushed me until I was laying on my back. She crawled between my legs and went back to work, her head moving up and down, one hand wrapped around my cock, milking it in unison with the pace of her mouth. The feeling was incredible.

This time, she didn’t wait for my hands in her hair. After a minute or two, she was banging the tip of my dick against the back of her throat again, trying to get it past the barrier. After several attempts and the accompanying gagging sounds that were turning me on even more, she sat up.

“Nope, this big dick of yours is apparently just too much for my little throat,” She said with a smile. “That’s ok, we can try other things. Roll over for me.” There must have been a confused look on my face because she tilted her head to indicate where I was supposed to go. Following direction, I rolled over onto my stomach.

I felt Annie’s weight shift on the bed as she stepped over one of my outstretched legs so that she was between mine. I’d never had a blowjob immediately followed by a massage but who I was I to complain. That thought probably contributed to why my body jerked slightly when Annie leaned forward and grabbed each of my ass cheeks. She pulled them apart gently and I suddenly felt her tongue sliding across my asshole. I could feel her breath against my ass as she chuckled, her tongue gliding around my puckered hole.

She paused for a moment and asked, “What’s the matter, never had a girl’s tongue in your ass before?” I had, but never by surprise. Before I could respond, she had stiffened her long tongue and slipped it past my sphincter, tonguefucking my asshole with a steady pace.

“Fuuuuuck,” I moaned at the intense feeling. My hips involuntarily rose a bit from the bed to give her what felt like a better angle. Seeing an opening, she released one of my ass cheeks and took hold of my cock where it had been resting beneath my body. She pulled it back so that it ran parallel with my legs, the underside exposed to her.

Annie ran her tongue from my asshole down across my taint. She made small circles with her tongue there for a moment and then moved down to my balls, licking at them and then sucking each one into her mouth. I could feel her humming quietly before letting them fall from her lips. She continued to lick the length of my shaft downwards and settled into licking the underside of the head of my cock. Then with one continuous stroke, she dragged her tongue from the tip of my cock back into my ass.

“FUUUUUUUUCK,” I said breathlessly.

“I like making you squirm!” she exclaimed wickedly. “But enough of this fun, I need this fat cock inside of me.” She pulled back off of me and rolled over onto her back, crooking a finger towards me to tell me to join her.

I didn’t need a second to think and got off of my stomach. She laid out on the bed and spread her thick legs. Her stomach spread across her body, every move I made as I climbed atop her sending ripples across her curvy flesh.

“Stop watching the motion of the ocean,” she giggled. “Fill me up!”

Without another thought, I lined my cock up with the lips of her pussy. I wondered if I would need to use some saliva to get things started but I felt her heels on my ass as she pulled me into her. She was very wet but also very tight. I slid all of the way in until our pubic bones met. That initial thrust caused her to to gasp and her eyes widened a bit. “Yessss,” she whispered, “stretch my cunt out.”

I flicked my tongue across each of her nipples making them stand at attention. I nipped at one making her yelp. She was about to say something when I used that distraction to pull out and slam back into her. Whatever she was going to say died in her throat as she groaned. I slowly started to fuck her rhythmically, her hands grasping at my back to pull me closer.

I picked the pace up a bit and started thrusting into her with a little more force. Her nails dug into my back as she moaned more loudly. Between the sounds she was making and the sensation of her tight walls around my cock, I could feel myself starting to get close. Not wanting to end the evening so quickly, I suddenly pulled back and my cock popped out of her juicy vagina.

“Oh you fucker! I was starting to get close!” She said. I smiled wickedly at her and replied, “You’re in a rush?”

She pouted but that quickly dissipated as I slid down the bed and spread her pussy lips apart. I ran my tongue up and down her slit, tasting her juices. With two fingers I pulled the hood of her clit back and started flicking my tongue around with purpose. She groaned loudly and grabbed my head, grinding her pelvis against my open mouth.

I slid my tongue down again and pistoned it in and out of the entrance to her vagina. Her juices were really starting to flow and I was lapping them up. Hooking my hands under her knees, I lifted them up, exposing her asshole to me. I slid my tongue down and repaid the favor, licking in and around her asshole.

“Ohhhhh gawwwwwwd,” she moaned loudly. I wondered how thick the walls of the hotel were. Just as I pulled my tongue out of her butthole and slid it back up to her cunt, she froze, her moans silenced as her body started to vibrate. As she groaned loudly, I felt a warm rush of sweet juices flood my mouth and run down her ass crack.

I smiled and licked my lips. As her orgasm subsided, I looked up at her over her belly and said, “I’ve never had a squirter before.”

She smiled broadly and replied, “I don’t usually do that unless I come like crazy. You know what you’re doing.”

I laughed at the compliment and rose back up over her to kiss her. Her long tongue speared between my lips and began to lick around the inside of her mouth. Soon, she was licking the sides of my face, exclaiming, “God I love tasting myself on a man.”

When she finished, she had a gleam in her eye and said, “you’re not finished and I still need that cock in me.” She pushed me to the side and rolled over, pulling up to all fours. She wiggled her large ass at me and said, “Come on big boy, fill my cunt back up with that meat.”

With a grin I climbed between her legs and my cock slid effortlessly into her sopping wet pussy. Without waiting for me, she started thrusting back and forth, spearing herself on my dick repeatedly. I gripped her ample ass and started meeting her thrusts with my own. There was a loud, wet slapping of flesh every time her ass hit my hips and I marveled at the shockwaves as they rippled across her ass cheeks. I could tell her pussy was just as tight as it had been when I was inside of her previously but she was just so damn wet it felt like my dick was swimming inside of her.

With every thrust she moaned louder. “Harder… give me that fucking cock harder!” I leaned forward, putting more weight against her ass and lightly bit her on the shoulder as I kept fucking her with long, deep strokes. Balancing on one hand, she wrapped an arm around my head and whispered into my ear, “You can come inside me…” That turned me on big time and I picked up the pace but my cock was still doing the freestyle stroke in her flooded cunt.

“You’re so fucking wet, I don’t know that I actually can,” I replied back. She burst out laughing and collapsed on the bed. “Damn, that’s one I haven’t heard before!” I pulled back and as my cock slipped out of her pussy, it was followed by a stream of her juices that were quickly soaking the sheets. Looking down she cackled and asked, “Do we need lifejackets?” We burst into laughs at the ridiculous situation.

As we quieted down, she looked between my legs at my still rigid member and tsked. “Well after you made me come like a firehose, I can not send out into the night without taking care of you.”

I smiled and asked, “What did you have in my mind?”

She pulled back up onto all fours and reached back, pulling one of her large ass cheeks apart. “How about you slide that snake into my asshole?” The adrenaline in me surged again. I was a big lover of anal but hadn’t had the chance to partake once Kate and I had gotten together yeas ago.

I probably looked a little eager because as I got into position behind her, she let go of her ass and pressed her hand against my hip. “Go slow. This is my first time taking it in the butt.” Surprised, I replied, “Seriously? Your invitation sounded like this is something you had experience with.”

Her expression became a bit bashful as she held her hand against my hip to make her point. “I mean, I’ve had dildos up there. I loved that feeling so I’ve wanted to try the real thing.” She paused before continuing, “But you are way thicker than any dildo I own, so… Take. It. Slow.”

I nodded and said, “Don’t worry, I’ve got you.” Annie let her hand drop from my hip and got back onto all fours. “I don’t have any lube here so we’ll have to use what we’ve got,” she said.

Looking down at her exposed asshole which was drenched from her squirting earlier, I said, “I don’t think that’s gonna be a issue.”

I settled back behind her and thrust my cock back into her dripping pussy, making her jump. “Hey! You’re in the wrong hole!” I laughed and smacked her ass replying, “Relax, I’m making do with what we’ve got.”

Pulling back out, I laid my cock between her large ass cheeks, the tip resting just outside of her asshole. Gripping her ass from both sides, I spread her to expose her sphincter more clearly. “Here we go,” I said, pressing the tip against her ass.

“Mmmm,” she hummed, “feeling that pressure.”

I leaned more forward, gently putting a little more force against the resistance. I could feel her sphincter instinctively clenching and releasing against the tip. “Relax a bit,” I said quietly. She took a deep breath and I felt her hole relax considerably, allowing the head of my cock to slip in.

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