This Job Finally Pays Off

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A business trip with an odd benefit.
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I was stuck at my job for another year until I could save enough to buy part of my uncle's auto repair business and be my own boss, or at least half until my uncle retired and I could buy him out. But as crummy as my current office job was it started paying off in fringe benefits big time.

Somehow I got chosen to attend a conference in Dallas. I discovered no one considered it a plum assignment because the other attendee was a division manager who not too many people liked.

I had met Alyssa a couple of times in big meetings and had no problem with her but her reputation was that of a ball buster and four star bitch.

Just by appearance Alyssa was somewhat intimidating, an attractive black woman of 35 she stands 5-9 tall and weighs in at 220 pounds. With thick wavy black hair Alyssa has a body that is wide, thick and almost the same width from top to bottom with big tits. The talk was that she was a lesbian, which didn't much matter to me. I was getting five days in Dallas.

Maybe whoever picked me figured that at 28 years old, standing 6-1 and weighing 235 pounds I wouldn't be physically intimidated by Alyssa, who knows but I spoke to her a few times setting up the travel itinerary and seminars and it all seemed good.

We arrived in Big D Monday afternoon with only a dinner on the schedule that evening. The surprise came when we discovered that our more than cheap company had booked us one double room, and not even a suite at that. We were both a little upset but with no recourse, Alyssa shook it off so I figured we would make do with what we had.

So after our dinner we decided to head down to the pool. I've got to say stretching her black and yellow one piece to the max Alyssa is one awesome full figured woman. I went with the long baggy shorts.

We spent time in and out of the water socializing Alyssa referred to me as her 'roomie' and after a couple of hours we headed back to the room. Alyssa opened the door and motioned graciously for me go in first, which I did. Before the door even closed I felt one arm go around my waist, a hand rubbing my stomach and another hand reach into my shorts rubbing my ass.

"Oh, Kevin how would you feel about getting down for some serious making out?" asked Alyssa.

I thought about the lesbian talk and wondered if it was just talk but more than that I was thinking about peeling that swimsuit off and getting at Alyssa's sweet thick body. So I replied, "I believe that sounds like an excellent way to kick off the night's activities."

Alyssa still had her hands rubbing my stomach and ass and said, "You got that right but so you know the score, no pussy for you." Then reaching into my shorts took my stiffening cock in her hand she continued, "I reserve my pussy for women but I'll enjoy every bit of this sweet piece of meat and you can play with all of this body you can handle. Understood?"

I was processing this two part shocker quickly and figured half a loaf was better than nothing and why bother trying to figure it out. I decided to just go for what you can get replying, "Unusual but I'm game for those rules."

As I turned around Alyssa slid my shorts down to my ankles saying, "Oh hot damn, good and hard is how I like it" as I stepped out of my shorts.

I then proceeded to assist Alyssa out of her swimsuit which took some doing. She had a lot of woman squeezed into that slippery fabric but we managed and it was my turn to say, "Damn now you know why I'm stiff, impressive all around."

"Thank you now let's cut the talk and get to it." Alyssa then took my cock in her hand and led me to the closest bed. If she's anything Alyssa is assertive, she pushed me down so I was sitting on the edge of the bed then dropped to her knees.

Holding my stiff dick in her right hand Alyssa looked up at me and said, "No grabbing my ears, you'll get enough, just enjoy."

That thought hadn't actually crossed my mind but one thing I wasn't going to risk was crossing this bitch. That's when Alyssa took the head of my cock in her mouth and went at it.

For a lesbian Alyssa sure seemed to enjoy sucking dick and damn if she wasn't skilled at it. It was a pleasure to watch her head bob up and down as Alyssa took more of my cock down her throat as she sucked me off but not as much pleasure as the blowjob she was giving me. Damn she deep throated my 8 inches and massaged my balls as she did it.

With her 'ear' warning in mind I reached forward and massaged Alyssa's shoulders which I took from the humming she started was to her liking. Finally I was feeling it and quietly said, "I'm going to cum."

Alyssa responded by rubbing my thighs and pulling back to leave only the head of my cock in her mouth. As Alyssa worked the shaft with one hand I came and she sucked on my dick like she had a straw buried in a thick milkshake taking everything I had.

Pushing up with her arms on my thighs Alyssa looked down at me and said, "Oh Kevin you are a sweet delight."

I just smiled and stood up then taking Alyssa by the hand lay face down on the bed to give her a massage. Straddling her thick body I worked my way down her broad back, gave her big butt the attention it deserved and worked her powerful legs. I moved up and sat on Alyssa's big butt, bigger than mine in fact, and rubbed her shoulders for a bit then leaned forward to kiss the back of her neck.

Alyssa moaned and said, "OK let me flip over got to give the front some attention." So I raised up off of Alyssa's meaty ass and she rolled onto her back, still under me, and I sat gently down on her stomach.

On her back with those big fat jugs staring up at me like two gigantic Hershey's kisses Alyssa moaned and said, "Double my pleasure big boy."

She reached forward to stroke my cock which was, no surprise, hard then moved to squeeze her fat jugs together and said, "Timeout on the massage since this fat fucker is activated. It's tit fuck time, move yourself up and slide that meat in the brown mountain valley."

True enough Alyssa has a pair of mountains made for the tit fuck. I would never take this position on your average woman but Alyssa is not only above average she had no problem with my weight on top of her and was really into the action.

The big girl was sweating as much as I was so her cleavage was slick and my dick slid between her tits easily, even as she squeezed those fat jugs around it. Alyssa was moaning and smiling so she was enjoying herself and oh it was quite the feeling on my side too. Damn those fat jugs were making my cock throb.

Alyssa leaned her head forward to kiss the head of my cock as it poked out from between her tits and said, "Oh baby it's like the cream filling coming out of a chocolate Twinkie, and oh so sweet too. Kevin you devil."

Well I laughed and couldn't hold back any longer shooting my load which hit Alyssa on the chin at first until she bent her head to get the last of it between her lips. It was her turn to laugh as she said, "Well it's good for the complexion I guess."

I sat back softly on Alyssa's stomach then bent forward to kiss her on the forehead and said, "Feel free to enjoy it any way you like, you earned it."

So Alyssa says, "Now I'm sure you could use break so why don't you relax and give me a little assistance."

I wasn't sure what Alyssa had in mind but it was going just fine so far so why question it. Then she directed me to sit back against the headboard, which I did after positioning the pillows. Alyssa sat down between my legs and taking both of my hands placed them squarely on her breasts. "Now you show me you know how to hand those puppies and I'll take care of myself."

So I got started playing with Alyssa's full fat tits and kissing the back of her neck while she began fingering her pussy.

At that point I saw that Alyssa had a vibrator I had not noticed in her hand and she proceeded to insert it into her well worked pussy. As it buzzed the party really got going. Alyssa was grinding back against my body her big butt bumping my stiffening dick as I continued to squeeze her tits with one hand and massage her heaving belly with the other.

She got off big time and I could only wonder how she did with another woman working on her. But she kept it up and I did all I could from behind her.

That's when the big shocker came, Alyssa asking, "So I can feel that stiff dick back there, do you like to give a woman a good ass banging Kevin?"

OK I'm here I am with the lesbian who I'm not getting any pussy from, she gives great head, tit fucks and gets herself off while I feel up her fat tits and awesome body and now she wants me to give it to her up her big butt. Well it's quite a way to cap off the strangest night of my life so I responded, "Of course, when there's such a fine full ass looking for action is there even a question?"

Alyssa quickly rolled out from between my legs and pulled a tube of lubricant and some condoms from her bag and said, "Now Kevin, pick one that works for you and grease the target, you've got a job to do."

She then jumped up on the bed and positioned herself on all fours. I set a condom down on Alyssa's back and kneeling behind her I opened the tube of lubricant. As I worked one then two fingers up Alyssa's tight hole I couldn't help but realize this was THE biggest ass I've ever taken on and damn it looked like a challenge.

As I worked to open her up Alyssa was rocking back and forth and after I had three fingers probing her as she turned her head back at me and in a low growl said, "OK that's enough priming that hole now line that bad boy up and bang that booty."

Well it was now or never so I slapped one cheek of that big black ass and said, "Get ready to rumble, I'm hard and ready to put it to work."

I rolled that condom on and pushed the head of my stiff dick into Alyssa's meaty ass. Alyssa gave out a low grunt as I pushed the head of my dick in then sighed as I began pumping in the first few inches. I had a firm grip on her wide hips as I slowly pushed deeper.

I was just about putting the full eight inches in her ass when Alyssa turned her head back to me and said, "Oh Honey I'm feeling it, you have got the goods now bang that ass like I know you can."

So taking a good hold of her hips I sped up my pace and was slamming my body into Alyssa's meaty ass and giving her all eight inches. It was amazing but also quite the job, Alyssa is a lot of woman to hang onto and she was moving with my actions not to mention hitting her solid ass on every stroke was a collision.

Finally I couldn't hold back so I put my hands on Alyssa's shoulders and with my cock buried in her ass shot my load. Alyssa was winded as well and pitched forward on her stomach. Kneeling behind her I slapped her on the ass and said, "That was fantastic."

Alyssa sighed and said, "That was awesome Kevin, you know how to stuff a woman's ass and make it happen." Before drifting off to sleep.

So I was satisfied we both enjoyed ourselves. I stumbled over to the other bed to get a couple of hours of rest before the next day's work.

We did repeat performances the next 3 nights and left for home Friday about noon. On the plane home Alyssa said, "Kevin you had such a good week I am going to talk to a girlfriend of mine, she's bi and we'll see how you perform in a threeway." Then squeezing my thigh added, "If you can do pussy like you did me, that bitch will owe me big time."

A bit surprised but more than interested I said, "Well Alyssa if there's any way we can work together I'm in."

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