Jillian-Summer Conference

Each summer for the few years I have had to go to a conference in the mountains west of Denver. This conference takes place the week before the ski slopes open and lasts for three days, and my wife has always gone with me, except 2 years ago.

A little over two years ago, we also hired this program manager, who is 30, 5'11 and 140 pounds and she is fucking gorgeous. "Jillian" looks a lot like Aidra Fox, right down to those dimples. She also wears the tightest A line skirts at work. While in town we probably talk too much without talking about it, sex.

I generally go up a day early to set up our booth as well as run a class on the first day of the conference. As I noted, my wife did not come with me this past year., as she had a competing conference that her boss made her attend I had brought my own computer and an apple TV so I could stream some movies, as well as some porn.

The first night after i get the booth set up, Jillian asked, "are you hungry and or in need of a drink?"

I said "hell yes, and I need to make a phone call and change, first." We agreed to meet in the hotel bar.

I went to my room, and talked to my wife and told her I was turning in, since I had an early morning. I then got a shower and dressed in some casual jeans and grabbed a jacket.

Jill met me at the bar and she was wearing the tightest pair of jeans I'd seen in some time as well as this sweater than highlighted her amazing set of tits. We drank and ate and chatted. During this conversation, I probably said too much when she told me one of the ole bitties in our office had told her, she was heavy, I responded she was gorgeous. Which she is. She brushed my arm and blushed and thanked me. After the dinner, I told her I was going to jump in the hot tub, and then hit the hay.

I went and changed and went down to the hot tub and was totally relaxed and just about to get out and go rub one out, when Jillian shows up. She is wearing one of the resort robes and slides out of it and into the tub, with just enough time to see how fucking smoking she looks in her little two-piece bikini. Thank god I wasn't standing, as I sprung to life in a split second.

She slid in and as the jets were going, she slid closer to me, so she could hear, as we got into a conversation. She had brought a bottle of pre-made mules and we drank most of it, while talking and me occasionally wanting to dive into her tits.

After nearly an hour, it really was getting late and I said I needed to get to bed. I got out and dried off and grabbed my robe, and so did Jillian. She also said she was ready for bed and we walked to elevator together. We got in and she pushed the same floor I was on, and I said "wow, we're on the same floor?"

"It would seem so."

I exited the elevator and went to my room, and as I went to use the pass key, Jillian stumbled and fell, and as she did, I caught her. I had my hands wrapped around her waist and she had bent forward over them, bending at the waist and her ass was pushed right against my cock. I helped her straighten up, she turned/twisted around and was facing me right in front of my open room. I still had my arms around her waist and without even really thinking, let go with my left arm, and with my right arm still around her waist, went into my room. She followed and as the door closed, she looked at me and dropped her robe. I grabbed her by her waist and pulled her to me and planted a kiss on her lips. And soon, her mouth was open and our tongues were moving against one another. As we engaged in this, I moved us towards the bed and then fell back onto it, with Jillian on top of me.

I was moving my hands all over her awesome body and in so doing had undone the straps to her top. As I rolled her on to her back, exposing her tits, I looked at them in awe, as they were solid/firm and had the tiniest aureola, and they were so smooth feeling. I immediately started licking, sucking and nibbling on her upper torso, working my way to her tits, and in so doing identifying her erogenous zones. I spent a good amount of time familiarizing myself with her awesome tits, which were very sensitive, on the sides. I then started to nibble and suckle my way south towards her pussy.

As I got to the level of her belly button, I undid her bikini bottom. I continued working my way to her crotch, and as I did, saw that she had the littlest tuft of hair, just above her clit, but was bald beyond that. Her labia, unlike Merissa were very small and did not protrude out, but she did have, a very nice swollen clit. I ignored this as she begged me to lick her pussy, I went further south looking for more flash points to further torture her, until I was ready to lick her pussy.

After a few minutes of this, I again worked my way towards her crotch and as I did, I pushed her legs back, exposing her. Starting at her puckered little ass, I started licking/sucking and nibbling away at her. Spending a few minutes on her ass, as she told me she loved anal and anal play, was well worth the time. I finally got to her pussy, which was soaked by this time and with little time or effort, she was soon cuming and moaning my name. I did this for a bit longer, and she came a couple of more times, and as she came, she would have the most intense guttural moan, followed by laughter.

After her last orgasm, she said "I want to taste your cock." So, I slid up her body, dragging my cock across her pussy and her clit, and up her chest, until is was right in front of her mouth. She took me with her left hand and directed my cock towards her mouth and then stuck out her tongue and grabbed a bit of my pre-cum that had found it's way to my tip. She moaned and asked if I had any condoms, as she wasn't on any birth control.

"No, and I had a vasectomy years ago and have never had a concern about anyone I have fucked getting pregnant." I didn't tell her one of them was my step-daughter and her step sister.

She then said, "you mean I can fuck you raw, and not have to worry about your cock flooding my pussy with cum?"

"Well, I am going to flood your pussy with cum, but no, you don't have to worry about getting pregnant."

Immediately she squeezed my cock and, I had leaked a bit more pre-cum, which she licked up, and then proceeded to lick all around my head. Then she used her tongue to slide down the shaft until she got to my balls, which one at a time, she sucked into her wet mouth, with the utmost of gentle care and caressed them with her tongue. While doing this her hand was stroking my cock, and running her fingers around the head of it, at the same time. Then, again using her tongue, went up my cock to the head and then engulfed the whole thing and went balls deep in a very slow motion. Once there, she then surprised me, by opening her mouth, pushing a bit further down and took both of my balls into her mouth. Once there, I could feel her tongue swirling around the base of my cock, and she started pushing on my taint/sweet spot, which had my cock throbbing and pushing more pre-cum into her mouth.

Jillian then pulled back in the same slow, deliberative manner until my cock popped out of her mouth and she said, "I want this cock in my pussy, Jack."

"What position do you like best?"

"I love it from behind, and I don't mind it a little rough and some hair pulling."

Not gonna lie, I almost nutted right then. She flipped over, and in a very erotic move, popped her lovely ass into the air. She then had one of her hands underneath her and on her pussy, with her god awesome French manicured nails, rubbing her pussy. I spread her legs a bit as I moved in behind her and I placed the head of my cock, on her hand, and she took it and directed it into her pussy, which was soaked and hot.

Her pussy was so wet and so fucking hot and so tight, it was incredible. I let my cock sit right inside the entrance to her and felt her hand wrap around my cock, then she pushed back on to my cock, and as I bottomed out, she moaned, "please fuck me hard." I grabbed hold of her ample, but not fat hips and started rocking her as hard and as fast as I could. After a few seconds of this, I reached up and grabbed a handful of her auburn hair and pulled it back towards me. She arched her back and slid back with me pulling her hair until our torsos, were in contact, and I grabbed her face, and twisted it towards me and we full on locked lips and tongues were going everywhere. I could feel her moaning and occasionally she would break free and say my name and tell me to fuck her harder.

After a few minutes of this, as well as groping her awesome tits, I pulled away and told her "I am going to flood your pussy with my come now, Jillian." I pushed her by her back, so she was again, face down, I moved in such a way as to be squatting behind her, and driving my cock down into her pussy. Then, as I felt my load building, I slammed my cock into her as far and as deep as it would go, and at the same time pushed my thumb into her spasming ass and held them both there as I came into her great little pussy.

I held my cock in her sloppy pussy until Jillian said she wanted to clean our combined cum off my cock. So, I slid up along side her and she went about licking, and sucking my cock and cleaning it. When she was done, I was a little hard still and she said, "I could use some more of your cock, if you are up for it."

"I am up for it if you are."

She pushed me over, mounted my torso, facing me and slid her pussy up my torso, until it was right in my face, "clean out my pussy," she said as she grabbed my head and pushed it into her cunt. I started licking and massaging her hips/ass as I did so, and occasionally reached up and started rubbing her tits as well. She reached back and kept my cock engaged by stroking it every now and then. I got her to cum again, twice and finally pushed her off me.

As I did so, I said, "put that white hot pussy on my cock!"

She stood and lowered herself onto me and then ever so slowly, slid down until I was buried in her pussy, and I was still playing with her tits and we were heavily kissing. She started to twerk on my cock, which was driving me a little crazy, but since I had cum earlier, that wasn't going to happen for a bit. I finally got one of my hands on her backside and put two fingers in her ass, which got a reaction from her. She pulled back from our kiss and said, "you wanna fuck me in the ass, don't you."

"You are god damn right I do!"

She got off of me, moved to the head of the bed and then showed me her flexibility, apparently from Yoga. She pulled her lusciously long legs back over her head and locked them. Her left hand was on her ass and pulling her cheeks apart and she said as she spit on her hand and moved it to her little asshole, and rubbed it around and said, "put your cock right here, please."

She then put two of her fingers in her pussy and squeezed at same time, bringing a nice little gob of cum out, she rubbed it on her little asshole and that is when I placed the head of my cock in the same spot. I put some pressure behind it, and when Jillian felt that, she pushed out a bit on her ass, and as it relaxed, my cock slid into her hot little ass. I slowly pushed further into her ass as she repeated the process twice more. Finally, I was balls deep in her ass, which was hot and tight as any I have had the pleasure to penetrate. She loved it and moaned really loud, "fuck my ass hard, and I mean it." I was ploughing into her in the longest, hardest strokes I could muster, and at one time my hand was kneading her gorgeous tits and my right hand ended up on the top of her chest.

While I was fucking her hot little ass, she took my hand, and moved it up to the base of her throat and once there, she was ever so softly stroking my arm. She then wrapped both hands around it, and whispered in a soft voice, "choke, fuck me, Jack" I had experienced this a bit with Merissa and it made the sex amazing.

I establish a pattern/rhythm, wherein, I would pull nearly out, hold it still, while making the head of my cock pulse with a little kagel. Then take my time bottoming out in her ass, where I do the same thing. I am also at this time alternating the squeezing on her throat. She was on the other side of this, playing with her clit with one hand and begging me to fuck her harder and faster. So, I picked up the pace a bit and really ploughed her hot little ass.

After a few minutes of this, "I want to fuck you from behind with you face down and this hot ass sticking in the air." So, I pulled out, and flipped her over and then grabbed her hips and popped them up and grabbed one of the pillows and placed it under her hips.

I then leaned forward and starting with her pussy, licked my way to top of her little ass, and spit in it. I leaned back and again put the head of my cock on Jillian's little pucker, and once there, she began pushing back, until the head of my cock popped into her ass. I grabbed her torso and while still in her ass, pulled far enough back, her back was touching my chest and I engaged her in some deep kissing for a few seconds, and then with my left hand I wrapped it around her throat and started to squeeze, as well as play with her tits. After I few minutes of this and nearly choking her out, I relaxed my grip.

In short order I was ready to cum again, and as I approached the orgasm, I started to squeeze her throat again as I started to cum in her hot little ass, I kept squeezing, and felt her ass spasm as my last load emptied into her.

We laid there a bit and kissed some more and then she said we should shower, which we did and I got to run my hands all over her hot body some more before we fell asleep.

Day 2

I woke up early the next morning so I could workout, and Jillian was still in the bed, and still naked and still gorgeous. I got my gym clothes on and ran to the gym for some weights and bike riding, prior to having to actually, work.

About halfway through my workout, I saw some movement at the door, and in comes Jillian. She is wearing sweatpants and a sport bra and her hair is a mess and she looks fucking hot. I lost track of what I was doing and got behind, so I had to leave, and she was clearly engaged in her treadmill.

Once I was cleaned up, I went down to conference and set up the booth for the day, and then went to grab some food. While I was there, Jillian came in wearing one of her A-line skirts and a blouse that accentuated her awesome tits. The skirt, allowed her to show off her awesome ass, and long legs. She had these great looking, but not slutty high heels, on, which made her taller than me. We ate breakfast together and didn't mention the night before, but clearly it was on both of our minds, as more than once, I caught her blushing and looking at me. She also had this sly smile, like she had some secret to tell, but didn't want to.

We both walked back to the convention center to "man" the booth, with a couple of our co-workers, who were none the wiser about our little encounter last night. We made some small talk and at least once I am sure Jillian made some sexual innuendo. Which made me do a double take and blush myself, which brought a little smile to her face and busted out those dimples of hers.

As more people came in for the lectures, we got busy handing out swag and yapping with people, and checking them in. So much so that I hadn't checked on my phone in a long time. At one point, I looked over at Jillian, bent over the table, answering someones question and she looked my way and winked. She then held up her phone and gestured for me to check mine.

I again got kind of busy and then when there was a lull in the masses, I went in to listen to a lecture, I wanted to hear. I excused myself and walked in. I sat there for a second and then, I recalled Jillian had wanted me to check my phone. I pulled it from my breast pocket and it opened, and there was an iMessage from her. I opened the phone, and there was an app icon for "b-vibe" and below that the information to activate it. So, I did.

After the presentation, I went back to the booth and told Jillian and our coworkers I was going to get some lunch and asked if they wanted anything. Jillian asked if she could go with me, and off we went. About half way to the exit, she pulled me by my hand and pulled me into a small conference room, that was vacant. She then, bent over and lifted her skirt, showing me she was commando and had a plug in her ass. She stood up straight, straightened her skirt, grabbed me by my collar, pulled me in for a long deep kiss and opened the door and left me standing there, getting hard and flummoxed.

I went and got my lunch from my room and came back to booth and was told Jillian had gone into a lecture. I asked if they noticed which side of room she went in, and then went in the other side. After taking a seat at back of room, I scanned and finally found her, about half way up, and sitting on the aisle. I took out my phone, activated the app, and started the vibe on the lowest setting with a wave like pattern and watched. When the connection was made, it was clear, as Jillian, didn't quite jump, but did twitch a bit in her seat. She looked around and started to stand, when I hit max intensity, which she handled well, but still kinda fell into her chair. I then texted her and told her to stay put, or I'd hit it again. Her text back was a devil face, with a peach and an eggplant. I responded with the eggplant with the three raindrops or whatever they are that look like a cumshot. I saw her get it, and quickly put her phone away.

After a few minutes, I clicked up the intensity a bit, which again got her attention. Then just as quick, turned it off. After noticing it was off and nothing happened, I saw her slowly rise from her chair and seeing/feeling nothing happen, she quickly made way to exit. I finished the lecture, then came out, and she was working the booth and saw me, and smiled then winked at me. I came over and made some small talk with another co-worker, then made my way to her. I leaned in and asked "how far do are you willing to take this, sweetheart?"

She smiled and said, "you take it as far as you think I can take it, big boy."

I walked away and waited for over half an hour, then opened app again, and set it for previous settings, and then turned it on, as she was talking to some conference goer. I could see how it effected her, in that her knees locked, and due to that her hips, swung into the counter she was leaning over. She adapted, gave me a sly look and winked, so I turned up the intensity a LOT to see how she'd do, and damn if she didn't do pretty well. Her tell, was again, her knees locked and she swung her hips into the counter. But then, ever so subtly, I noticed her legs moving back and forth, as though she had to go to the bathroom really bad. I left the intensity where it was and then started messing with the pattern to mess with her. She handled it all very well and after a few minutes on the highest intensity, I dropped it to the lowest and left it there for close to 15 minutes then turned it off. At some point in the afternoon, I lost track of Jillian, and someone had said she went to town for something and would be back in an hour.

As the day was winding down, we all sat down and some one started talking about the amount of shit people, specifically men carry in their wallet, as opposed to women and purses. Me and the other guys all take out our wallets and mine isn't even a wallet, but a card holder. I guess I won. Anyhow, not paying attention, i get my wallet back and put it back in my pocket and by then the day is over and we are packing up. Small talk ensues and I act like I could give a fuck. At which point my phone buzzes and it is from Jillian. She says I need to check my wallet.

Casually, I pull it out and everything looks legit, and then I notice, I have an extra card/hotel pass key. It has a room number written on it, clearly in female hand writing. I look up and get winked at, again and then my phone buzzes again, telling me the time, which is half hour from now.