Breaking Up is Hard To Do

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One last night together. Or is it?
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fearthisss
fearthisss
2,167 Followers

Dana and I had been seeing each other for about 18 months. We had known each other for 10 years or so prior to that as co-workers for two different employers. She was gorgeous! She was a tick taller than me, standing right around 5' 10", with wavy, shoulder length, light brown hair, beautiful green eyes, and a smile that would light up a room. One of the nicest people you'll ever meet. Even though she was in her late 30s she still has a totally rockin' bod! 38DD's that, as Bob Seger would say, stood way up firm and high, a tight little waist, and legs that stretched to the sky. Me? I stand about 5' 9", back then I weighed about 200 lbs and was in really good shape. Dark brown hair starting to show some gray in the temples, hazel eyes, a bright smile surrounded by a goatee, and a hearty laugh that was quick to come.

Our employer decided we needed the latest and greatest estimating software. This six-figure software included off-site training with on-site follow up training. Of course, Dana, our estimator, would be sent to the training. And, being her immediate supervisor, it only made sense that I be sent also. So Dana and I packed our bags and flew from our homes in cold and gloomy Indiana in the middle of winter for 4 nights and 5 days of training in warm and sunny Phoenix, Arizona. By this time Dana and I had been working much closer together than we had at our previous employer and had become quite comfortable around each other. We were actually pretty excited about this trip. Not so much because we were going to be alone together. More because, even though we knew our days were going to be filled with software training, we also knew our evenings were going to be free to explore an area neither one of us had ever been to. Better yet, on the company's dime!

That's how it all started. Two and a half days of mind-numbingly intense software training, each followed by just the two of us having dinner and drinks. This is when she informed me that she wasn't happy in her marriage and - this blew me away - that she had a crush on me at our first employer! She couldn't believe I didn't know. "Why do you think, every time you came back to visit everybody after you left, I found a reason to come into your department, silly?" As you have probably gathered by now, by that last night in Phoenix we were no longer staying in separate rooms. I wound up being in her room. You didn't have to be around Dana very long to realize she was a people pleaser. She was more worried about the people around her being pleased than herself. I always wondered if that carried over to the bedroom. Much to my delight, it did. That's when I found out she loved to fuck...she liked it a lot.

Now fast forward 18 months. Dana and I no longer worked together but were still seeing each other. By this time I was divorced but she was till with her husband. Now that we no longer worked together, we didn't see each other every day. We saw each other a couple times a week and then every other weekend, when I didn't have my son. No more getting a whiff of her sweet smell every day. No more blow jobs under the desk. No more flashing of her tits when I walked past her office. None of that. We had talked about her leaving her husband and moving in with me but she couldn't bring herself to do it.

Dana came over on her usual Tuesday night. We grabbed some dinner and then headed straight to the bedroom, where we fucked like rabbits. I'm not stupid. Get laid before you have "the talk." She sensed something was up, though.

"Dana, we need to talk."

"About?"

"This. Us. I don't even know how to say it, so I'm just gonna say it. This isn't working for me. When I could see you every day, that was one thing. But now? We talked about you leaving Dave, and yet you're still with him. It just kills me knowing that you're laying with someone else every night instead of me."

"But Dave and I haven't had sex in forever! I swear!"

"No, you say that. But it kills me knowing you're in his bed and not mine."

"So what are you saying?"

"I think we've run our course. I think it's time for both of us to move on."

"Don't say that! I don't want to lose you! I can't lose you!"

"You know what to do."

"But...but...I can't leave Dave." Tears were streaming down her face now.

The conversation went on something like this for quite awhile. She finally got dressed and left the building crying, nearly inconsolable. I felt terrible. But I knew it had to be done for both of our sakes.

Wednesday and Thursday went by. Friday afternoon I got a text from Dana. "Can I come over 2nite?" My response was "R you leaving Dave?" "I can't." "Sure, come over. You've got some stuff here."

She showed up at my little one bedroom apartment a little after dinner looking totally smokin' hot. She was dressed in those Daisy Duke shorts and a crop top that I love so much. I got an instant hard on.

"I put your stuff together in the bedroom."

She placed one hand gently on my chest and the other gently on my cheek. "Please, Mark..."

"No, Dana, my mind's made up."

With that she drew me close and planted a hot, passionate kiss on my lips. I could feel her nipples poking through her top on my chest.

I broke the kiss. ""Dana..."

"I know, I know, you've made up your mind," she said with a trembling voice. She looked into my eyes. "How about one more time? Just one more time?" I felt her hand on my already hard cock.

"One more time, huh?"

"Please. One more time."

My mind raced. I had a thought. Several actually. I could feel the crooked smile crossing my face. "How about one more night?" I said, emphasizing "night".

"Night?" Her mood brightened.

"Night. You'll do exactly what I say. We do what I want for as long as I want. That's the deal."

"Anything you say?"

"That's the deal."

She planted another long, passionate kiss on my lips while her hand rubbed my crotch. My hand found it's way up her top and started pinching her nipples.

"Yes. Yes! Whatever you want, as long as you want, all night."

"Good. Come with me." I grabbed her hand and led her to the living room. I turned her back to my patio on the first floor. "Now suck my cock." Without the slightest hesitation she had my pants unzipped and was gobbling my cock like a starving woman at Thanksgiving. As hard as I was, and as horny as I was, I knew this wouldn't take too long.

Dana loved giving head. And she was good at it. One of her hands would always find it's way to her pussy. This time was no different. She had her hand stuffed down her shorts, moaning from the touch of her own hand on her clit. I pulled her top off over her head, freeing those incredible tits. My hands were on the back of her head, helping her with the rhythm. Her other hand was holding the shaft of my cock, tugging at the base.

We were both lost in the moment. Then I felt a presence. I knew the drapes to the patio were open. I looked out and could see one of my neighbors, Steve, in the darkness, just beyond the light my kitchen light was casting. He was absolutely entranced at the sight of her head bobbing up and down on my cock. What could I do at this point? I don't know how long he'd been there or just how well he could see inside. I gave a devilish grin and simply gave him the thumbs up. He smiled and gave me the thumbs up back. Apparently he could see inside fairly well. At that point I held my hand up to my lips to say "shhhhhhhh". He nodded in reply.

My breathing became heavier and her pace quickened. My grip on the back of her head tightened. "I'm...gonna...cum..." Her lips moved away and she started to furiously stroke the beast with both hands. In no time I shot a huge load all over her face and tits. Her tongue rolled around the edge of her lips, licking what she could. With one hand still on the shaft, her other hand scooped a little cum from her tits and lifted it to her mouth, sucking it dry. Then she started to rub what was left around on her tits.

"Mmmmmm, that was yummy, " she purred. "How was that?"

"That was awesome...for starters."

"Starters?!" She almost squealed.

"Remember? Whatever I say, for as long as I say."

"I remember," she said with a sly grin and a twinkle in her eye.

"Go take a quick shower, get cleaned up. We've only just begun." She sprang up and practically ran to the bathroom. "Go to the bedroom when you're done."

While Dana went to the shower I went to the patio door and flipped the patio light on. Steve was still standing there.

"Like the show?" I asked.

"Dude, that was awesome!"

Steve was a good guy, nice looking I guess. I'm guessing late 20s-early 30s built similar to me but 10-15 years younger.

"If you liked that, stick around." He got a confused look on his face. "Do you know how to record video on this?" I showing him my cell phone.

"Duh. Who doesn't?"

"Perfect. Give me 15-20 minutes. When I come around that corner start recording. And keep your mouth shut!"

"Got it," and he grabbed my phone, looking it over. I left the patio light on and went back to the bedroom.

I went to my closet and pulled out an old, long sleeved, button up denim shirt of mine and threw it on the bed. Then I went over to my night stand and pulled out a pair handcuffs and a sleep mask I had for just such occasions as tonight and threw them next to the shirt.

A few minutes later she came bouncing out the shower with a towel wrapped around her that barely covered her. She looked like a cat that had just gotten the canary. I have no doubt she fingered herself to orgasm while she was in there. She walked straight over to me and planted another long, hot kiss on my lips while rubbing my cock through the shorts I had put on.

"Now what?" she whispered in my ear. I reached over and grabbed the cuffs and mask off the bed. She practically squealed and gave a childlike clap of her hands.

I pointed at the shirt laying on the bed. "Put that on first." The towel dropped to the floor, revealing that incredible, tan body. She threw the shirt on and buttoned it up. I shook my head. "Uh huh," and unbuttoned it down far enough to reveal the cleavage those 38DD's created. The tips of the shirt reached just far enough to cover her goodies down south.

I handed her the blindfold which she eagerly threw on. She held out her arms for the handcuffs, but I only used one cuff on the left arm. I grabbed her hand and proceeded to lead her out of the bedroom.

"Where we goin'?"

"You'll see."

When I rounded the corner into the living room, leading Dana by the hand, I saw Steve, just beyond the patio, raise the phone. Now I just hoped he was actually recording! I held my finger to my mouth reminding him to shush.

I lead her to the patio entrance and stopped. I opened the patio doors and cuffed her left arm to the patio door handle.

"Isn't this the patio door?"

"Yep," I said as I placed myself between her and the door, pushing her to her knees, and pulling out my semi-hard cock.

"What are we going to do?"

"Well, first you're going to suck my cock."

"Oh, you think so, huh?" she said almost giggling.

"I'd be willing to bet on it," I said as I pulled her face to my crotch. That was all it took for her grab the shaft with her right hand and swallow my cock whole.

She removed it from her mouth long enough to ask "What if somebody sees us?"

"What? Because nobody's seen you give me a blow job before? Hell, there's a video of it on the web that has over 10,000 views of it."

"This is true," she said, just before licking the under side of the shaft.

"I'd be willing to bet somebody's watching right now," I said as I winked in Steve's direction. "Admit it, that makes you hot," as I reached down to pinch a nipple. She nodded her head in agreement.

I could feel my cock hardening with each bob of her head. "What they haven't seen, as far as I know, is you taking a cock in the ass."

She stopped for a second, then looked up at me even though she couldn't see me with the blindfold. "I love getting fucked in the ass," she purred.

"What was that? I didn't hear what you said." I just wanted to make sure the recording Steve was making heard it loud and clear.

She spoke up. "I love...having your big, fat cock...in my ass."

"Good girl, I know you do. And, as soon as you get me good and hard, that's exactly what you're gonna get." She gave a muffled squeal.

The longer her head bobbed the harder I got. Her hand had left the shaft and found her naked pussy. Her breathing was getting harder and deeper. And I could see a bulge in Steve's pants.

I pulled my hands away from her tits and stopped her bobbing head. I reached under her arms and pulled her up to a standing position. "Is your ass ready for this." She nodded her head aggressively in approval, a sly smile crossing her face.

Once upright, because of how she was cuffed to the patio door, she could only spin to face Steve and the recording full frontal. She put her left hand on the edge of the patio door and her right hand on the door jam, bracing for what she thought was about to come. She even started to bend over, thrusting her ass in my direction.

"Oh no no, not just yet," I told her, grabbing her waist and pulling her back up to me.

"But I thought..."

"Soon enough," I said as I snuggled in on her neck, pulling her tight to me. I reached around and started to unbutton the front of the shirt.

"No no," she said, grabbing my hand.

I unbuttoned one more button. That left the bottom three left. I reached in with my left hand and started playing with her breasts, while my right hand went down to her pussy and her throbbing clit. Her pussy was absolutely soaked. Her hand went for my hand inside the shirt.

"What? Why not?" I asked.

"People will see. People will see you fingering me." She let out a small groan.

"Seriously? You're okay with people seeing you with a cock in your mouth, you can't wait to get fucked in the ass where they can see, but you draw the line at my fingers in your pussy?"

"I'm so close to cumming. I want to cum with your cock in my ass."

I pulled my hand out from under her shirt and my fingers out of her pussy. Then I finished unbuttoning the shirt and pulled it open for all to see, especially Steve and his video. A gasp escaped from between her lips. I grabbed her tits with both hands. "Okay, if you insist. Bend over."

Once again she braced herself for what was coming.

I rubbed the head of my cock on her pussy lips, brought it up, and barely inserted the very tip in her ass. No lube would be required tonight, her juices had flooded the area. The moment my cock touched her ass she let out a sexy moan.

"Tell me what you want," I asked.

"Fuck me."

"What's that?"

"Fuck me. Fuck my ass!"

I grabbed her hips and, unlike previous times, drove it into her ass balls deep in one thrust. She let out a guttural groan like I'd never heard out of her before. Her back arched. Her head flew back. As I pulled back she relaxed a bit and gathered her breath. I drove it balls deep again and got almost the same physical reaction.

"Oh my GOD!" she screamed. "Holy shit! Oh my god, yes!" She was in pure ecstacy.

After a few more of those ass pounders I slowed to a more normal pace. I took one hand off her hip and reached around. Her pussy was absolutely drenched, juices running down her leg. She quivered as I touched her hardened clit.

"You like that?" I asked, knowing the answer.

"Oh fuck yes! Don't you fucking stop!"

I almost forgot Steve was there. There he stood. He'd pulled his cock out, stroking it with one hand, holding the phone in the other. He was a little smaller than I was and definitely not as thick. I again held up my hand to my lips telling him to shush. Then I wagged my finger at him to come closer.

"Hey man, why don't you take your dick out of your hand and come over here and grab her tits." Dana's ass literally puckered, she gasped, and Steve's jaw dropped. Again I gave the shush sign. "She loves to have her tits played with when she's getting pounded in the ass, but I can't reach 'em. If you're lucky she'll even suck your dick."

"Who's there?! How long have they been there?!"

"Long enough to have a raging hard on," I told her.

Steve came close enough for me to grab the phone from him, and I turned it around, switching back and forth from him and the back of her head to my cock pounding her ass. He wasted no time reaching down to grab her amazing tits with both hands, his stiff cock practically slapping her in the face.

Without missing a beat she lifted her head and swallowed his pole like a champ. Steve let out a massive groan and "Ohhhhh fuuuuuuck." Again I reminded him to shush.

This went on for several minutes. Dana had already cum once, shortly after swallowing Steve's sword. I could tell Steve wasn't going to last much longer. There wasn't going to be any shushing him this time.

He had both hands on the back of her head, fucking her face. "Fuck...fuck...fuck...I'm gonna...cum...I'm gonna..." He let out a moan and dumped what must have been a massive load into her mouth. I could see droplets of cum escaping her mouth onto the patio cement. He finished pumping and pulled his already softening dick from her mouth.

I quickly handed the phone to Steve. Hopefully he could hold it steady enough to get some decent footage.

Dana followed suit almost immediately. "Oh my god! Cumming! Cumming! I'm cumming!" Her body quivered like never before. She was having a massive orgasm! Her ass puckered up so much around my cock I could barely continue the ass pounding.

Dana had no sooner finished when I pulled out of her ass and spun her half way around. I proceeded to shoot a load, missing her open mouth and hitting her chin and neck, cum flowing down onto her tits. What a beautiful sight!

I grabbed the phone from Steve. We gave each other the thumbs up and he disappeared into the night. I helped her up from her knees. I knew what was coming next.

She wiped some of the cum from her chin with her finger and licked it clean. I pulled the blindfold off and unlocked the cuff.

"Who was the other dick?"

"How'd you like that? Did you enjoy it?'

"OMG, yes! I've never done that before, taken two at one time." She paused. "So who was the other dick?"

"Does it matter?"

"No, I guess not. I'd just like to know. So who was it? Somebody you know? A friend of yours? Did you set that whole thing up in advance?"

"Honestly, I have no idea who that was." A look of shock raced across her face. "Somebody was passing by and stopped to watch the show. He had such a raging hard on, I felt bad for him." Her eyes widened and jaw dropped..

"Are you fucking kidding me?!"

"Nope, serious as a heart attack," I replied with a sly grin and a twinkle in my eye. "Go get cleaned up, we're not done yet."

"Really?! What else do you have planned?" She hadn't recovered from the information she was just fed.

"Just go get cleaned up."

She sauntered back into the bathroom for her second shower of the night. I have no doubt her mind was racing after that little episode, wondering what could possibly be in store next. I quickly checked some of the video on my phone. Awesome. That should get a few hits after I post it.

While she was in the shower I went through her clothes I had laid out on the bed, thinking she'd be taking them home shortly after she arrived. I knew exactly what I was looking for. Ahhh, there it is.

She came out of the shower, this time not even bothering with the towel.

"Now what?" she asked.

"Put this on." I handed her one of my favorite outfits she owned. A little summer dress, yellow with white flowers, that didn't leave much to the imagination. Not even mid thigh, more like one-quarter thigh, with thin little spaghetti straps, reaching down to a top that just barely contained those 38DDs, and a nice, little slit right in the middle of the top, showing off some nice cleavage. Easy access to everything. I loved this dress!

fearthisss
fearthisss
2,167 Followers