Jillian-Summer Conference

I go to my room and apparently someone has been in my room as there is a box on my bed. I open it and find an Aneros anal/prostate massage plug. Just then my phone rings and it is Jillian. She asks if I found my present, and said sure, and she asked if I was adventurous enough. I laughed and said she could find out in 10 minutes. I hung up, grabbed some lube, lubed that bad boy up and inserted it in my ass. I then went to my bathroom, grabbed a viagra and took it. Showered and got to her room, 15 minutes later.

I let myself in and found Jillian, naked on her bed, laid out, with a plug still in her ass, and she was in control of it, as I could tell from her movement and her activity on the phone in her hand. I smiled and started stripping, at which point, I dropped my trousers she lit up, as I was getting harder from watching her.

She asked me to turn around, which I did, then bent over to show her the plug. She scooted to end of the bed and took out this little bullet looking vibrator pushed on my back, exposed my ass and then I felt the vibrator being inserted into the aneros. She motioned for me to take a seat, which I did. She pushed me onto my back, reached down between my legs and turned on the vibrator. My cock, sprung even more to life.

Jillian then mounted the bed again, and then mounted my face, such that she was facing my feet, and said, "it ain't gonna lick itself." I took the hint and grabbed the sides of her fucking awesome hips, and pulled her down on to my tongue and slid it into her wet pussy and went to working it around inside her, and as I did, I took my hands from her hips and slid them up her torso to her tits and played with those as I continued to fuck her pussy with my tongue.

As all this was going on, she would occasionally, stoke my cock, which was being stimulated by the Aneros plug. I could feel pre-cum leaking from my cock, to the point, I felt a drop land on my torso. Shortly after this, I felt her hand in that spot, and she scooped it up, and I am guessing she put it in her mouth.

After getting her to cum a couple of times, she finally got up off my face and asked what I wanted. "I want to fuck that tight little pussy, i just got done licking to orgasm."

She slid down my body until she was straddling my cock, with her pussy and started sliding along the length of it, using some of my pre-cum as lube.

She mentioned how hard my cock felt and attributed it to the vibe in my ass, which had something to do with it, but I told her, I'd popped a viagra, and her smile was priceless.

She said, "you mean I can fuck you LOTS tonight?"

And with that, she slid forward enough, that on the back slide, when I flexed my cock, it found the sweet spot and slid right into her super wet hot pussy. She moaned and worked it in slow, long and deep strokes into and out of her pussy as she leaned over and between deep kissing and playing with and/or sucking on her tits, she came twice and then sat back a bit, bent her legs and started squatting up and down on my cock. This was more than I could tolerate and told her, I was going to cum and cum hard, at which point, she slammed her pussy down on to my cock, the effect of it buried in her pussy, as I started to cum and coat her cunt with my cum. She also came at this time and I could feel her pussy squeezing my cock, with each spasm.

Jillian, slid off my cock, and took it in her hot mouth and sucked and licked it clean, and then said, "I would love for you to lick me clean, if you're up for it?"

I was more than happy to, and had her slide over me and sit her pretty little pussy right onto my face. I licked her clean and took about 10 minutes and two orgasms to do so.

Needless to say she and I were still horny as hell and since I had taken a Viagra, it wouldn't take long for me to be ready again. She was laying there and stroking my cock with this smile and contemplative look on her face. "What are you thinking about," I asked?

"I loved having your cock in my ass last night and would love to have you fuck me in the ass again, tonight." Of course this whole time, we both still had plugs vibrating away in our asses. Mine was working magic again, as I was getting hard, and some pre-cum had accumulated on the tip of my cock.

I noticed it and leaned over to Jillian and told her, "there is a gift for you down there." She proceeded to sit up a bit, then lean over and with her tongue licked the bead of pre-cum off my cock, and then in one fell swoop, took the length into her mouth and once she bottomed out, she licked my balls.

I moved so now we were sitting facing one another and pulled her into me, after placing a leg on either side of me. We held one another like this and made out for quite some time, as well as running our hands over each other. When we finally broke our kiss, I reached between us and grabbed my cock, and told Jillian, "lift yourself up and mount me."

She used my shoulders to lift a bit, and I directed the head of my cock to her hot wet spot, and when she felt it was in the right spot, she slid down onto me. I grabbed her hips and pulled her torso even closer, such that our pubic bones were touching and then told her to do her Kagels.

She started flexing her pelvic floor, as well as I was and we started making out again, while we carried on like this for more than a few minutes, during which I continually held her hips and pulled her into me. I broke the kiss and with one of my hands pushed her torso back, arching her back, further pushing her into me, as well as looking sexy as hell, I then started licking, suckling and nibbling her tits.

I kept this up for a bit, and again at one point my right hand was on Jillian's upper chest, when she grabbed it and placed it on her throat, and begged "please choke me, and do it harder than last night, please."

I continued with my oral play on her tits, and started applying pressure to her throat, she was clearly getting turned on, as her nipples were like diamonds they were so hard. She was also beyond just Kageling my cock, as she was now rocking hard on it. She suddenly opened her eyes wide and demanded, "CHOKE ME HARDER!" I squeezed even harder and felt her pussy spasm, and seemingly continue to do so and I thought she was going to pass out, and instead, she slapped my hand away, pushed off the mattress with her legs, pushing me onto my back, and fell onto me, engaged with my mouth as she continued to orgasm on my cock.

When she was done, she sat straight up and looked me in the eyes and said, "I loved how hard you were choking me, and I have't cum like that for a long time, since I haven't found anyone willing to take me to the edge."

She slid off of me and then pulled my legs back and extricated the plug from my ass, and as she did, she inserted two fingers and started messaging my prostate. "That feels fucking amazing and would only be better with my cock in your mouth, Jillian."

She took the hint and while continuing to message my prostate, sucked and licked my cock until I was ready to burst.

She must have felt that, as she stopped suddenly, and lifted her leg, and pulled her own plug out of her ass, leaving a tiny gape for a split second. She then asked "what position would you like to fuck my ass in?"

She had a suite, so she had some living room furniture, that included an ottoman, and I told her, "why not place yourself on the ottoman, on your back with those long gorgeous legs of yours pulled back a bit."

Jillian grabbed the lube as she stepped off the bed and went to the living area with the ottoman, and laid down on it, with her legs dangling over the edge. I walked over and leaned over her, and planted a hot kiss on her gorgeous lips, while I grabbed, first a handful of tit, and then her throat, as I began to use my tongue on hers, and choke her a bit. This lasted a minute or so, and I again almost choked her out, which brought a huge dimple filled smile to her face.

I stood and walked a pace to the left, which put my cock right above her face and I squatted down, until my cock dropped into her now open mouth. "Just keep your mouth open, while I fuck it, beautiful," I told her. I then proceeded to do just that, making her gag on about every other probe of her mouth with my cock, and on about every 5th one I would just hold in her her, as far as she could take it, and watch her get teary eyed, and at same time give me a dimple filled smile, around my cock. I was close to cuming and told her so and to take care of it for me, which she did by pulling my cock out and slapping the head really hard.

My cock still covered in her slobber, I moved her feet and starting on the left one and then repeating on the right, I splayed them apart a bit, and then licked, nibbled, suckled and bit my way to her slit, which by the time I got to it was on fire and wet as hell. I pushed her thighs back a bit, and in so doing her little puckered hole, came up off the ottoman and starting there, I licked and stuck my tongue in her multiple times, and then nibbled on her taint, which is one of her erogenous areas.

Finally I arrived at her pussy and worked my way from bottom to top, purposefully ignoring her clit, as I did so. Once I placed my tongue on her clit, Jillian had an orgasm, and I could visibly notice her pussy get wetter. I had my tongue as far up her pussy, lapping up her juices, while rubbing my nose on her now sensitive clit, which brought her to another orgasm.

As she was coming down from that, I grabbed the lube and ran some around her asshole, as well as my cock. I once again grabbed her thighs, and since I had to squat a bit, pushed them back to nearly touch her chest. Jillian in the mean time was rubbing her pussy and alternatively shoving fingers into her drenched pussy, which by way of being as wet as it was, each time she extracted them from her pussy, her juices would flow down to her little puckered ass.

As I was squatting, I pulled Jillian closer to and actually a bit over the edge of the ottoman, not that I think she noticed, because as I did this, I placed my cockhead right at her little sphincter and as I pulled Jillian towards me, I slid right in to her hot little shitter, which brought her out of her cum/cock drunk state with a little gasp. I wasn't quite pile-driving her but that was just a matter of elevation of her torso. I slid in and out of her a few times and then suggested she place a couple of fingers in her pussy, towards the back a little.

As she placed them in her pussy, I made sure I was buried in her ass. "hold them right there," I told her, as I could feel her fingers on the other side of that membrane that separates the vaginal canal and anal canal. I then told her to concentrate on the things she was feeling as I backed out of her ass.

As the head of my cock slid past her fingers, she could definitely feel it, and asked, "is that your cock, I feel?"

"Yes it is, now keep using your fingers on your pussy as you feel me slide in and out of your hot little ass." I put some more lube on my cock, as I nearly came all the way out of her ass, and then proceeded to fuck her in long, slow strokes.

I was close to cuming and told her so, and with that she took her hand and surrounded my cock with her manicured fingers, as it slid in and out of her ass. "I want to feel your cock dump it's load in my ass," she said. And on that note, I pulled nearly out again. To point I could see the back side on the head of my cock. I then felt my cum boiling its way to my head, which was swelling with anticipation, and Jillian said, "I can feel your cock swelling," as I shot a load just inside her sphincter, and then I rammed my cock back into the hilt, as I shot two more loads into her. Jillian at this point started to cum as well, as I could feel her ass clenching my cock in its spasms, which only served to squeeze every bit of cum from my cock.

I left my cock buried in her as we made out, and finally, deflated my cock slid from her ass, as did a glob of cum. Which she felt slide down and grabbed it with her right hand and brought it to her mouth and licked it from her fingers. If, I'd had anything left in the tank, I'd have had to fuck her again. As it was, we ended up chatting a bit.

One of the things that Jillian admitted was she had thought of being tied up, as well as she'd always thought about wanting to try out a sex swing. I have a friend, who actually lives outside of town and knowing him as I do, as well as having visited his cabin with Merissa, I knew he had a swing. I just needed to see if he was home this week or not.

Jillian must have seen my mind working, because she asked, "what is going on in that head of yours."

I hinted at it by telling her I wanted to work on her swing thing. She then surprised me by saying, I was clearly the oldest man she had been with, and thus far, she was pleasantly surprised and would have to consider more of the same in the future. The age difference is like 23 years, as she is 30 something, and I am 58. After this and a shower, we both fell asleep.

Day 3.

Again, I got up before Jillian and went to the gym. I had been down there for about half an hour when Jillian comes in wearing her sports bra and these very tight shorts. I was working chest this day and asked her if she would spot me on my last two sets. On set one, I got a little distracted as all I could see was her fat pussy in her tight shorts. At the end of the second set, after I placed the bar in the rack, and before I could get up, she literally squatted over my face, but not on top of it, and said, "My pussy is hungry for some cock today, Jack." Thankfully, there was no one else in the gym.

I say thankfully, as the next set was chest fly's, and instead of spotting me, Jillian just sat on my lap, after I laid down and was grinding on my pelvis. This got me hard and being that is was only 4 am, and no one else was around, I sat up, grabbed her hand and pulled her with me into the mens locker room.

Once there, we scanned the room to make sure no one was there and then, I had Jillian sit on the bench and as she laid back, I pulled her shorts down and past her shoes, and then pulled mine off as well. With her lying on her back, I then went around to her head, and leaned over and started licking on her beautiful pussy, while she took me in her mouth. I licked her to an orgasm, and almost a second one, when I stopped, mostly because I was getting close to coming.

I went to where her feet were and had her scoot to end of bench, and then, placing her legs on my shoulders, I had her direct my cock into her waiting, wet and hot pussy. She was super wet, what with her own juices, as well as those I contributed, and thus I slid right into her. I held it in there for a bit, and had all intent of pulling back, but before I could, Jillian started using her leg muscles to move her torso such that she was fucking me, while I just stood there.

Watching her fuck me like that was so hot, I could only take so much and needed/wanted to extend this session a bit, so, I leaned over her, and had her legs slide down to my waist, as I then grabbed her around her torso, I stood up. Which is no easy feat, as Jillian is 5'8" and a good 140#, all solid and hot, but I digress.

Having stood up, she slid down on to my cock, and due to gravity, there was a lot of pressure, with each down stroke on her clit, which for the short time we stood clearly had a positive effect on her. I turned and then sat down on end of bench, and Jillian said, "let me turn around and really ride your cock!"

She then stood and turned around, and reaching between her long gorgeous legs, grabbed my cock, and directed it back into her wet pussy, as she sat down on me. She then leaned forward, touching the bench right next to ours and used it to balance herself as her tight little pussy bounded up and down on my cock, in long not fast strokes.

As I was once again close to cuming, I reached up and pushed her off, which got me a disappointed look from Jillian. I told her to turn around again, and come in between my legs, which I was now holding open and wide (YEA YOGA), As she came in she squatted right into my crotch and grabbed my cock, and started riding me, amazon style.

The great part about this position is, it really rocks the clit and the g-spot, as it maintains a LOT of pressure on the front wall of the vagina and the woman gets to control it, and I got to grab and play with her awesome tits. Jillian was really working this position and I was not going to last long and told her so, which brought her off, of my cock after a few more bounces, Jillian dismounted me and before she could get her mouth on my cock, I shot one load right into the air, and the rest landed in the back of her hot throat.

Jillian got up, as did I and we found our clothes and put them on. No sooner than we did, someone an older gentleman, thankfully no on either one of us knew, walked into the locker room, and clearly looked like he knew what had happened as Jillian's hair looked a little disheveled. He winked as he walked by and we left the locker room, and went to the elevators. As my room had all the rest of my clothes, I went there to get cleaned up and dressed prior to the start of the day, and as I was about to enter my room, Jillian pushed me past the door, pushed me against the wall and kissed me hard with open mouth and lots of tongue and then said, "I can't wait to see how tonight goes. I hope you're ready for the day that lies ahead." And then she left.

I showered and got all dressed and still had time for some much needed coffee and breakfast so I headed to the only place that had both and did't try to scalp you for holding a conference at a resort, in the off season.

I had just sat down and was drinking my coffee, when in waltzes Jillian. Again in an "A" line skirt and great heals, but not slutty. She clearly is wearing stockings, as they have some heart shaped things on the back, from her heel to wherever the hell the ended, which I really wanted to find out. To top her look off, I had informed her in our discussion two nights ago, I have a thing for two hair looks. First and highest on the list is when the hair is braided and then a bun at the base of the skull. The other is two buns, one on either side of the head. Jillian was sporting the former and my god was she hot!

She got her food and coffee and came and sat down across from me in the booth, and asked, "how do you like my outfit today?"

My reply was, "please tell me those stockings are not panty hose hose and are at least held up by a garter or just the thigh highs."

"Sorry, cowboy, I will only say they are NOT panty hose. As for what they are, you'll have to wait and wonder until tonight. Until then know this, I am commando."

After breakfast I called my buddy and asked if anyone was going to be using his cabin tonight, and thankfully he said no and gave me the code to the door lock box. All he asked was that if we used the hot tub or the sauna to drop some chemicals in the former and wipe down the latter, and to toss any bed linen or towels into the washer when we left. I asked him if his "play room" was still functional or if he'd had kids yet and transformed it into a baby room. I was assured all his toys were intact and still functional.

As an aside, Chris is into some nice BDSM and in addition to the swing has a wide variety of toys and restraints and wax and, well you get the idea.

I went into the conference center and talked to my boss and asked if I could skate out around 2 instead of 4 and asked if he could keep Jillian busy until at least 4. He assured me she could and then started to ask me something, but probably thought better of it. Next I went to my iPhone, and got Chris' address and sent Jillian in invite for 6 pm at the address, which is about 15 minutes from the conference.