Estate Sale Adventures: Early Entry

Estate Sale adventures: Early Entry

Maddie was in a weird mood. She had been working her ass off on a new piece for a Bank lobby. Yeah, I know, it sounds fascist, but all major artists try to get there stuff in a big ass lobby no matter how Polly Progressive they are, so get over it. Oh, and they were paying her $50,000. That's a years rent for Maddie. So it wasn't just a big deal for her, it was The biggest deal EVER, for her. And despite all this, she still seemed to be acting weird. I mean she was a pretty straightforward person, the kind of bullshit-caller I always wanted to be be. And went it came to her work, once she got an idea nothing would stop her from getting it done. She was a beast! And woe betide the poor MF who got between her and her art. She never had any problem telling anybody anything, she was fearless. So when she wouldn't say why she wasn't wearing a bra under her favorite sexy retro WW II top, the red silk one that that was tied at the bottom in a little knot, I was concerned. Why would she dress like that just for an Estate Sale?

Finally, on the way, she told me.

"Ok look Carson, first of all I have to get in this sale as soon as possible, there's a huge set of costume jewelry and sewing notions that I HAVE to have for the Lobby Piece." She put her hand on my leg and squeezed. "Carson, I HAVE to get in that sale early."

She had my attention.

"Alright..." was all I could manage.

"So that means I'm gonna have to... Estate Sale Groupie this guy to get in."

The coin began to drop.

I spoke slowly, "Oh. Groupie? As in a Rock Star backstage Groupie."

"Yup."

The coin clunked on the bottom.

I paused, and thought carefully.

"Sex or..."

"A blowjob to completion for at least 10 minutes." She said quickly and without feeling, like it was an order at a drive through window."

"... Do I have to do anything?"

"I need you to monitor the event."

"I have to watch?"

"Not necessarily."

"Ah. Gimmie a second."

All of a sudden, I had to figure out what kind of man I was. Or at least, what kind of man I was going to be with Maddie. We were a couple who had sex, and were dating exclusively but now....

"Does this event change our monogamy?" I asked.

She seemed startled. "Oh. Ah. Well, I want to say no. But that doesn't seem fair, does it. Damn...."

"Hold on Maddie, this is new territory for me, let me think it out a bit."

I pictured Maddie going down on a guy. It bugged me. But did it bug me because I thought it should bug me, or because I truly found it disgusting? My dick was getting hard thinking about it, so does that mean I'm actually OK with it? Nope, my dick gets hard when I ride the bus on a bumpy road, so you can't trust that lying prick. I had never had a threesome, though I had thought about it. But this was just Maddie blowing a guy, and she wasn't my wife...

"... and no matter what I say, you are going to have to blow this guy anyway, so you can get in and get the stuff you need."

"Yup. The Guy's strict about that. No bribes. Just blowjobs, and good ones. He's a very nice person, and it's actually a compliment to be allowed the early entry privilege."

"A compliment to what?!"

"A compliment to my blowjob skills, you schmuck."

"Well, that is deserved. You are wonderful at it."

"Thank you."

"So you've...gone down on this guy before?"

"Yes. But not since we've started seeing each other."

"Are there any other Estate sale companies that grant, what was it, early entry privileges?"

She laughed. "No, but to be honest there's a couple who I wish would."

"Really? So you like it, you like going down on a guy just to get in early?"

"Jeeze, not every day. You know how much I like sucking cock, Carson. I don't sell my skills cheaply, or often, buy yeah, I like doing it, and don't mind it, especially when the guy appreciates it like you do, and like Harry does."

"Hm. That sort of makes it okay ... as much as it is for me to approve, I guess. Alright I'll monitor."

"Thanks. It makes it easier. His cousin, Aretha used to monitor for us, but she moved to Pittsburgh."

"And thereby giving me a new experience in life."

She smiled, and so did I. But I was still a little nervous.

The Estate sale was at a sprawling ranch home in a leafy green suburb. We parked in the street and made our way to the front door, where Maddie asked for Harry, and we were directed to go around to the back. We made our way to the backyard where a middle aged guy was doing some final pricing on a table full of garden implements. Maddie greeted him as Harry, and they hugged. He was about 45 with salt and pepper grey hair, about 5'10 with a medium build. Nice shoulders and arms, I thought to myself a little jealously. She introduced me as a good friend, and we shook hands. Yup, he seemed nice. Rats.

Harry led us inside to the house, and down the hall to a back bedroom. He locked the door and moved over to a corner of the room. Maddie looked at me hard. "OK, you ready for this?", she asked in a serious voice. "Yeah, I'm cool. You do your thing." I sounded cool about it as well, because I was. "Allright then. Hold my purse." She gave me her purse, Harry undid his pants and Maddie moved over to kneel in front of him.

Maddie's shoulder length brunette hair began to bob back and forth slowly. Her back was to me, so that's all I could see. Her hands were on Harry's waist, and as the seconds passed, I could see from Harry's face she was getting his cock good and hard. She leaned back a bit to jack it off in her hands. Then I could see it was about as big as mine, but thicker. I was mesmerized with the sight of her smiling face poised near this strange cock, her strong hands working his shaft with care. Harry was staring straight downwards, towards her tits, as he should. Her 38 C's were fucking great! Just big enough to be big, you know? She wasn't fond of tit play, but she liked to show 'em off! Harry's hands sneaked down towards Maddie's chest, and she swatted him away, making him laugh.

"Unh Unh Unh, no titties for you Harry, that's not part of the deal!" Maddie said, also while laughing.

"Dang, Maddie, that's almost mean of you, showing them off like that and then not letting a brother have a feel?" You could tell that Harry wasn't making a serious demand, in fact the tone sounded like a joke often told between two friends.

"Well, let me make it up to you." Her head lunged downwards as Harry's eyes rolled back into his head.

"Ohhhhhh Dammmmnnn! Oh that's so damn good!" Harry moaned out. I heard Maddie give a throaty little chuckle, made very faint by the cock in her mouth. I couldn't help but smile. A smile that Harry apparently saw.

"Hey, Carson, you have to see this, really. Get over here."

"Uh, are you... sure? I..."

"Yeah, Aretha used to watch all the time. Sometimes she'd even masturbate while watching. But she was a little weird."

Maddie popped the dick out of her mouth to say, "She sure as hell did it while watching me, I consider it a compliment." She went back to his dick, and I hustled over to the bed, and laid back on it so that I had a good side view of Maddie as she knelt in front of Harry. Her red shirt was unbuttoned, and her round but tiny nippled tits were out in full view. Damn I loved looking at her sweet tits! And I never before had a chance to see them from this angle. Her thick red lips were wrapped around Harry's dick, sliding over the engorged head as her two hands twisted back and forth at the base of his shaft. She was doing that all business blowjob, the one that gets you to come fast; I recognized it from experience. Maddie then noticed out of the side of her eyes that I had moved closer to watch, and she pulled his cock out of her mouth, turned to me and smiled a wicked, wide smile with lips slick from her efforts. Damn! Then she reached down and took her one of her tits in her hand and began to caress and squeeze it while starting a luscious licking and teasing of Harry's dick with her tongue and lips, all while keeping her eyes right on me. Her tongue swirled around the tip of his cock and then her mouth would engulf the head for a second or two, and then back to her pink tongue.

"Oh my fucking God, Maddie! What the...ungh. Carson, please stay right there, you are....ungh...obviously a good...ohohohohoh.... inspiration!", Harry managed to squeak out while Maddie kept teasing and tantalizing his thick dick. Her other hand moved to his balls and she began to caress and gently squeeze them. She then suddenly took the root of his cock and grabbed it fiercely, and then flicked the tip of her tongue on the very tip of his dick, like a snake. Her clenched fist at the root acted as a cock ring, and Harry's dick was getting redder, and thicker as her tongue danced over the glans like a living thing. Maddie's huge Green eyes now bored into Harry's face as she brought his cock to an even fuller state! I was wide eyed at the spectacle, and also hard dicked.

"Shit, can I jack off to this, please?!" I spat out without thinking.

Maddie leaned back, turned her face, wiped her chin and said, "Yeah. 'bout time." And then leaned back into Harry, this time swallowing his cock about halfway, her lips barely able to take it's width. My own dick was now in my hand and I was pumping it furiously, my mouth hanging open while I watched my hot big titted girlfriend blow this middle aged guy.

Now Maddie started to loose herself in it act. She started to truly fill her mouth with Harry's cock. Her cheeks bulged with his dick and her hands danced up and down the man's shaft. Finally, she found a rhythm she liked and began to bob up and down, about three quarters all the way down and back. Her eyes were closed, and she was in Oral fixation heaven and she blissfully sucked, and sucked, and sucked, and bobbed up and down relentlessly on Harry's dick. His face was a mix of pain and pleasure, as she kept going like she would never stop! Up and down, up and down! I could not believe that Harry hadn't cum yet, this old guy was impressing the shit out of me. Maddie was squeezing her tits and softly pressing the palms of her hands against her nipples, a thing she likes to do when she masturbates.

Maddie finally took a second to say, "Okay, time to get to the sale. Are you ready?" She said to Harry. He nodded. Then she looked at me. "Are you ready?" She asked. I nodded. "Well then." She took Harry's cock back in her mouth, and this time slowly swallowed the man's entire dick. She held him trapped in her throat for what seemed like an eternity, and then as she came back up for air, she took a breath and then started sucking his cock and pumping the shaft with both hands. I could also see by the odd bulges in her cheeks she was doing this thing with her tongue....I can't describe it, but it sort of presses the underside of the head of your dick every time she goes down in it, and it feels....

"Oh shit that feels... amazing!" Harry yelled. "Oh God, I'm gonna cum!" He tensed up hard and Maddie started sucking him off even faster. Harry then clenched up, and shook all over for a couple seconds, barely able to keep standing. Maddie had clenched down on his cock and drained every drop and as she pulled his softening dick out of her lips, she turned to me and said, "Here, come on my tits. But don't touch them."

She scooted closer to me, and held out her large tits with both her hands, pressing them together and looking at me with eyes flaming with lust. My hand was flying over my cock. I had never cum on her tits before. Her hands kept playing with them just like a pornstar would, and she leaned forward just a little bit and wiggled her entire body. That was it! I groaned and came hard, showering her tits with cum, as she leaned back to catch it it all, laughing with delight at the power she had over us both.

We all cleaned up, and got to the sale. Maddie spent two hundred dollars on the things she needed, things that would have been a thousand dollars at retail prices. And the finished work pleased the Fascist bankers. Maddie and I also had a long talk, and we decided to take our relationship to the next level. What that level is, will be in the next chapter.