Jillian-Summer Conference

During the day I could not help but stare at Jillian, and think of her bare pussy, just under her dress and those god damn hot stockings and her hair up, as it was. She was smoking, and more than once, she caught me staring, and each time, she would lick her lips in a very seductive manner. Most of the day I spent in a chunky mode, not quite hard, but certainly not soft, due to her and the way she looked. At 145 I grabbed my bag, and walked past Jillian and whispered in her ear, "come to that address exactly as you are right now, and bring a change of clothes."

I also slipped a Viagra into her hand and told her to take it about 30 minutes before she left to meet me. I did this, as she had mentioned how it may effect women, making the blood flow and back up in their clit, as the tissues are, basically the same. And with that I turned and walked away, before she could ask me anything, which I knew she wanted to.

I arrived at Chris' cabin and made sure the hot tub and sauna were in good order then went to the play room to get some toys and to make sure the swing was in place as well.

The play room is basically half of Chris' basement and it is finished to be convertible to a bedroom, should the need arise. It has a twin bed in it as well as a restraint wall, and a ton of toys. I went with the feathers, and soft restraints, and some nipple clamps and of course, who can not grab a nice red ball gag?

At 345 I popped a Viagra and 15 minutes later texted another co-worker to see if Jillian was still there. He told me she had went to her room about five ago and then he saw her walking towards the desk.

About 20 minutes later Jillian pulled up and exited her SUV, and was still dressed to the nines and looked hotter by the second. When she got inside we grabbed one another in a hot embrace, and I tried hiking her skirt up, to see about the stockings, which had been on my mind, all day, but she pushed my hand away and said, "all in due time, lover. So, what have we here that we wouldn't have at the hotel," she asked?

I walked her outside and showed her the expansive deck, as well as the huge hot tub, then upstairs to show her around the living space up there. When we got back to the main floor, Jillian said, "that can't be all of it?"

"Nope it isn't, and what I am about to show you, you have complete and utter control over where this goes tonight."

"Do I need a 'safe word,'" she asked? "I will let you decide," as I escorted her to the basement.

Once we were there, I turned on the lights, which I had intentionally dimmed, to set the correct mood, and she looked around the room and then turned to me, and I got dimples and a smile. "How could you possible know about this little quirk?"

"Well the desire to be choked was a little hint, and I thought I'd take a chance. Again, I want you to know, I would never harm you and wherever this goes to tonight, you are the one who has the final say." She came in close and hugged me, and grabbed my head and we kissed for a few minutes, I again trying to see the stocking, and again getting shut down.

When we broke our kiss, Jillian looked at me with an odd look and asked, "my god is this what Viagra does for you?"

I looked at her and asked, "depends, what is it doing for/to you?"

"My clit feels like it is huge, and my pussy feels like it is ten degrees hotter than I am, which is odd, since my face feels flushed."

"Yes, I am flushed as well, and it works by flooding the muscles and vasculature in both our organs with blood, which it sounds like it makes yours more sensitive?"

"God, yes, just rubbing against your torso while kissing nearly made me cum. when can we get naked?"

I took her hand and walked her over to the bed, that I had already placed the soft restraints on, and while holding her by her hips, "tell me, what is your safe word?"

"Rainbow."

"Great and do you trust me?"

"Explicitly."

"Great to hear, now please take that top off."

Jillian proceeded to unbutton her blouse, and then one arm at a time, took it off, revealing her great tits covered with a nice little white bralette which her hard little nipples were straining against. I stepped close to her, and reached around her back, and unzipped her skirt, which shortly fell to the floor. My god she was gorgeous. The stocking question was resolved. They were thigh highs and not with garter. Jillian was indeed commando.

I had her sit back on the bed, and when she did, she finally noticed the toys that had been laid out on the nightstand, Ball gag, feather, pinwheel, nipple clamps, flogger. She then laid back and the look of pure sex and desire on her face was unmistakable. She was more than ready. I however, was going to take my time and by the time, I was ready, she'd be a mess.

Once Jillian was on her back, I applied the arm restraints, and then the legs, the latter had more laxity in the restraint to allow her legs to move a bit. Seeing her laying there, naked splayed out, really got the blood flowing. I leaned over the bed, and locked lips with Jillian and as I did her tongue and mine danced in each others mouths, and I had grabbed the ball gag, as I did bend over, and after a minute, or so of kissing her, I pulled back and placed the gag in her mouth. When I did Jillian's eyes said she was enjoying it so far.

I then stepped back and stripped and had a raging hard on. I grabbed the feather and then walked around to the other side of the bed and starting at her left foot, used the feather to work my way Jillian was moaning and writhing about on the bed and against the restraints. When I reached her head, I reached over with my free hand and used the feather on the base of her skull, which I know is a tender spot for her, and in addition to being my favorite look, was the other reason I mentioned the "bun" look. Her nipples were hard enough to cut glass and her entire torso was flushed, as she thrashed about on the bed. I then repeated the same thing on her other side.

When I was done with the feather, there was clearly a damp spot on the sheet directly below her pussy, and her pussy had a visible sheen to it, and it was then that I noted, in fact her clit did look a bit larger.

Lastly, I took the feather and starting at her chin, worked my way down Jillian's chest and abdomen, and finally on her clit, and I told her to push her pelvis forward so I could watch her response to the feather on her clit. Moving it around and teasing her was great, as I could see her contracting her pelvic floor muscles, which in turn would have the effect of both her pussy and ass clenching and relaxing. The whole time, she is writhing on the mattress and I note that a fair amount of drool is accumulating around the ball gag.

Being done with the feather, I I grabbed the nipple clamps and the pinwheel, placing the latter on the bed near her feet. I then reach up, and remove the ball gag, only to replace it with my cock. I did so, by dragging up her cheek and accumulating some of her drool, before placing it in her mouth. Jillians suckled on it, and used her tongue all around the shaft, as I fucked her mouth with it for about 10 strokes.

Not wanting to cum, just yet, I pulled my cock out and placed the ball gag back in its place. Then I grabbed her left nipple and gently applied the clamp to it, and then repeated the process on the right nipple. After which I asked Jillian if she was still "OK" with this, she showed me some dimples and nodded her head yes. So I grabbed the pinwheel.

I started on her arms, and worked very slowly towards her torso, then repeated the same thing on her side all the way down to her feet. I ran it up the sole of her left foot towards her pussy, and got within a couple of inches of it, and stopped. I then repeated the process on the right side, only this time, I took even longer to play on that side and eventually, I actually did get to her clit, and when I did, there was clearly fluid leaking from her pussy on to the bed.

By now, my cock was leaking lots of pre-cum and was achingly hard. I went back to her mouth and pulled the ball gag out, and as my cock got close, Jillian stuck her tongue out and licked, it, I slowly slid my cock into her mouth, and fucked her mouth for a minute or so, and then stopped. I then asked Jillian, "are you ok with the flog?"

"Yes, of course, but not too hard, please." I had no intention of using it harshly, more as a brush against her soft skin, and knowing there was potential.

Grabbing the flog, I immediately started on her tits, and worked my way to her pussy, and ever so gently flogged her alternating between the two for a good three to five minutes. It was during this that with the gag out of her mouth she was literally begging for me to fuck her.

Myself, I could feel and see more pre-cum forming at my head and stuck my finger in it, and brought it to her lips, and drug it across the bottom one, which Jillian then licked off. At this point I had to have her, or I was going to bust. So, I untied her legs.

With her legs untied, I knelt down at foot of bed, and starting with her left foot, started licking, nibbling, sucking and biting my way towards her pussy. I stopped on her inner thigh, when the tip of my nose contacted the bottom of her wet pussy. Which made her buck, in an attempt to get something to touch her engorged clit. I then went back down and repeated the process on the other leg, only this time, when I got that close, I inched back a bit, grabbed her thighs and pushed them towards her chest. This exposed both her ass and her pussy, and starting on the backside of her ass, I started licking, sucking and biting around it, then her taint and finally, I stuck my tongue into her hot little pussy. When I did this I made a point of not touching her clit with my nose or anything else. I had my tongue inside her pussy for a good thirty seconds or so, and she was writhing hard and trying to get me to pay attention to her clit.

When I finally did touch her clit, she bucked her hips up so hard I thought I might be concussed. Instead I stuck to it and licked her clit, which honestly seemed about 25% larger, to at least three orgasms. The last one was extended a bit, as she was on the descent, I pulled on her nipple clamps, which I had almost forgot about, this escalated her into another orgasm, at which point, she was literally begging me, to fuck her.

I slid back a bit, and was now kneeling between her legs, which where now draped over mine. I took hold of them and again, pushed them back towards her chest. Then I slowly slid forward, and grabbing my cock, ran it from the bottom of her pussy, to the top, slapping her clit with it, and then repeated it a few more times,

Jillian was desperate to have me penetrate her, as she was bucking and writhing all over the bed and stating, "I want your cock, I need your cock, please fuck me already."

Finally, I slid the head of my cock into her and just held it there, as she writhed and bucked around trying to get me deeper into her. I timed one of these such that when she bucked her hips up, I pushed forward, so that when she came down, I slid all the way into her sloppy wet pussy. I held myself there, and started rubbing her clit, and she kept trying to buck to try and get me to fuck her, but I held her pubis down while I rubbed her clit. She was clearly getting ready to cum, with my cock buried in her, so I worked her clit just a bit more, and as she started to cum, I grabbed the nipple clamp chain again and pulled it, while at the same time, started working my cock in and out of her. She was all over the bed, as much as her restrained arms would allow and the amount of juices flowing from her pussy was impressive.

I kept pulling on the chain attached to her tiny, but hard nipples, as she came on my cock, and then since I wanted to release for the first time, I let go of the chain and took her left leg and moved it under my right leg, into a scissor like position and really started grinding my cock against her clit, each time I would drive my cock into her. After a few minutes of this, I had to cum, and I pulled my cock back to point the swollen head was just inside her, and I shot two ropes into her. I love the feeling of my cock then sliding through that as I push into her pussy even deeper to deposit the rest of my cum into Jillian.

Once my cock deflated I took it out of Jillian and laid on top of her and asked her what she would like, at this point.

"I want my hands undone so, I can properly embrace you for the next few minutes for a totally great experience, to start the night." I undid her soft restraints from her arms, and as soon as I did, she pushed me over onto my back and laid on top of me as we made out for a good 5 minutes or so. Jillian then, stopped, pushed off of my chest and said, "I want to restrain you and allow you to feel the great pleasure you brought to me."

"ok."

And with that she restrained my hands, while still sitting on my torso. Once they were restrained, Jillian sat up straight and said, "I really want you to clean out my pussy, and pleasure me a few more minutes," and she then slid up my torso and planted her pussy squarely on my face.

I immediately went to work on sticking my tongue into her hot little box, as she ground her pussy and clit onto my upper lip, and occasionally on my nose. I licked her clean and she came at least three times, the last one, she grabbed the back of my head and was screaming "lick and suck my clit, harder!" When she was done, she slid back onto my torso and said, "you really know how and clearly love to eat pussy."

"I learned after I ate a girl out in HS, that she loved it. I also learned that girls talk about sex as much, if not more than men, and that at the time, most of my peers were not eating pussy. Being that they had little else to compare to, and because they talk, I ate a lot of pussy, my senior year of high school."

After telling Jillian this, she leaned over and again engaged in a very deep kissing session.

"I am so glad you took that bold step as a young man. I am even happier that you and I are here now." Before I could say anything she again leaned over and kissed me, and then disengaged and before I could say anything, she had the ball gag in my mouth.

Jillian then reached into her bag, and brought out an anal plug, and a bottle of lube. She then sat with her ass on one of my legs, and lifted the other, squirted some lube on my ass, and on the plug, and then slid it into my ass. She then produced a remote, and when she pushed the button, the plug came to life. Jillian then moved through the different settings and then when back to start told me to nod when I had the one I wanted. She again started changing the mode, and hit on one that felt awesome. It would start slow, build up and then hit with three hard vibes, then start over.

Once she had this set, she grabbed the flog first and used it to hit my feet, then moved her way up to my cock, which she kept stroking with it for a few minutes, each time she'd hit me with it, my cock would throb, and combined with the vibe working on my prostate, I soon had a drop of pre-cum on my cock. Jillian saw it, and bent over, stuck her tongue out, and barely touching my cock, licked that drop up.

She then kept moving up and was soon flogging my torso and alternating with my crotch. After a few minutes of this, she stopped and placed the flog on the night stand and picked up the pinwheel. She repeated the manner in which I had done to her, starting with my feet, and moving around, not near my cock initially, but on second sweep she did grab my cock and ran the pinwheel up and down it several times, and again I had produced some pre-cum, which this time, Jillian just held my cock straight up, and engulfed it with her mouth. She took me balls deep, and just held me there for a few seconds while she actively swallowed, which since my cock was at the top of her throat I could feel each time she did so. The feeling of her doing so is hard to describe, it was so awesome.

Jillian took me out of her mouth and now grabbed the feather, which I will be honest about, turns me on immensely to be teased with it. She started on my arms and then moved to my legs and torso, and finished again at my cock, since the feather is a huge turn on, I had produced a good amount of pre-cum, which just stayed where it was, and then Jillian once again straddled me, at just below my cock, high on my thighs. She raised up, and with her right hand grabbed my cock, and directed it towards my feet, and as she did, her thumb took that precum and spread it around me cock head. She then pushed her pelvis forward and directed my cock right into her super hot and wet pussy.

Her pussy was so hot as it engulfed my cock, and slick as Jillian was clearly getting turned on as she teased me. She sat down on me and just sat there. She leaned forward and whispered in my ear, "I am going to remove the gag, but only as long as you have one of my tits in your mouth as I lay here and fuck you."

This is exactly what she did, she moved her hips and I sucked on her tits until she just stopped, and leaned far back and moaned very loudly, "I am going to cum so hard!" By cumming hard, she was squeezing my cock, and it was hitting her inner vaginal wall, I suspect her g-spot, and while she did not squirt, her pussy was so wet it was difficult to stay in her, which is about the time I was ready to cum, and slipped out, and shot on load across my stomach, and then Jillian engulfed it with her mouth and swallowed the remainder of them.

When she was done, she looked up and smiled and said "now that we have done that to one another can we get something to eat and sit in the hot tub, before we try out that swing?"

Jillian first pulled the plug from my ass and then undid me. Once she did I returned the favor of rolling her over and making out with her, and even went down on her again, as I have said, I love eating pussy.

When I had made her cum twice, we jumped from the bed and now that is was dark out, neither one of us wore any clothes as we went up the the kitchen, and I pulled out some wine and the prepared Charcuterie board I had made earlier, and we went to the tub, on the back deck.

Once it was open we both jumped in and I filled our glasses and brought the board to the tub side counter. We sat in the tub for about an hour, eating, drinking and chatting. One of the things I wanted to know was why did Jillian decide to start this with me. Her response was she found my bald head and gray goatee attractive but more so, the amount of times I had stood up for her in the workplace, just made her hot and she was surprised at how old I was, when she found out, because she only thought I was forty, not fifty-five.

She asked me the same, and my response was "because you are frigging HAWT!. You are tall, your curves are just ridiculous and your ass is beyond words, your stomach, which is as flat as I could ever have imaged, your smile is infectious, and the clothes you wear to work only accentuate all of this. You always look professional but at same time, I have wanted to pull you in my office, hike your skirt up and just eat you!"

Jillian was clearly blushing and smiling very shyly. I leaned into her and took her head in my hand, pulled her the rest of the way, and started kissing her, and her kissing me passionately. She broke away and said, "I have to tell you, I have applied for a job at a different facility, and I am going to take it, and I would have allowed you to have your way with me, if you'd done that, since the first day I started here. And, since that job is still in this industry, if we ever find ourselves in a similar situation, I am going to jump your bones. Just know that."

Again we started making out, and at some point, she sat on my lap, and wrapped her long legs around my torso. Shortly after, she starts grinding on my cock, which was already somewhat hard. After a minute or two of this, she reaches down between us, grabs my cock, and lifts herself, up, then sits down on my cock. She just sat there and squeezed her pelvic muscles while we made out. She kept me hard and totally engaged with making out with her, while I was in her pussy. We sat and made out like that for a good ten minutes, the whole time, her occasionally flexing her pelvis and squeezing my cock. Then I said, "let's got try out that swing, you wanted to use."