Good, to Bad, to Better

She smiled, thanked me and when I moved to the bed, she sat beside me and said, "Sorry, I'm a little nervous - it's not like I do this regularly."

"That's ok...I'm a bit nervous too - after all, I'm the one that's going to be on the receiving end of a strap-on from someone I've never met before."

That got a laugh from her and she noticeably relaxed and said, "I guess this'll work better if we undress" and pulled her shirt over her head. I saw instantly that her tits were indeed large but at her age had very little sag and I was right about her nipples - not only were they already slightly hard but the areola around them was at least 2 inches across.

With a "mmm, very nice!" I stood up and dropped my housecoat which got a "that's very nice too!" from her as my already hard cock came into view.

Obviously comfortable with where things were going, she stood up long enough to take off her pants and I was quite surprised that she wasn't wearing anything under them. She must have noticed me looking because she said, "I love the feel of the seam rubbing on my crotch."

I could tell she was still a bit nervous so I asked if she'd like me to give her some oral attention first to calm her down and she said she'd love it so she moved back on the bed to give me some room. As much as I wanted to go right to her pussy, I wanted to spend some time with her tits and as I cupped one, Karen said, "Those big areola's look kind of weird don't they?"

"Actually, I think they look kinda sexy!" and proceeded to not only kiss and lick her nipples but the whole area around them. When I sucked her nipples, they got hard and almost doubled in size, by now they were likely 3/4" long and really fat but surprisingly the areolae were equally sensitive and she was soon breathing heavier and telling me how good it felt.

When I finally kissed my way down her belly, I found her pussy was bare but she had a neatly trimmed triangle above it and I was just moving forward to taste her when she said, "Jess kinda mentioned that when you were licking her you... ummm... well she felt your tongue on her bum hole a few times."

I smiled and said, "Yes but if you don't want me to I won't."

That brought a quick, "No, I was actually kind of hoping you would."

When she said that I moved so I was lying beside her and said, "Well in that case, why don't you just straddle my face so you can move to where ever you want to feel my tongue" and with a big smile she did just that. Her pussy seemed more 'open' than Jess's had but tasted just as sweet. After a few minutes of licking her slit and sucking on her lips, she tentatively moved a bit further up until my tongue was flicking across the bit of skin between her pussy and ass which got a slight moan followed by "Oh fuck" as she slid a bit further forward and the tip of my tongue went right across the pucker of her ass.

She did exactly what I'd told her she could do - she moved to wherever she wanted to feel my tongue so for a minute or so I'd be licking and tongue fucking her pussy, then licking her clit (which had almost tripled in size and was as firm as the tip of my finger) and then she'd move again so she could feel my tongue on her ass. She'd obviously showered before she came over so I happily ran my tongue around and across her pucker and as she got used to that and then I started pushing the tip of my tongue against it until she relaxed enough for it to start sliding inside her. With her legs on either side of my head, I couldn't hear everything but could certainly make out bits - "Oh yes... fuck that's good...oh.... don't stop" and the next time she moved so my tongue was on her clit, I slowly slid two fingers into her well lubed pussy.

As soon as my fingers were all the way inside her, I curled them so I could put pressure on her g-spot, sucked hard on her clit and she went off like a firecracker. There wasn't any real warning - one second, she was moaning and the next she was thrusting her pussy against my face and I could feel her whole body tremble and shake. It was at least 30 or 45 seconds of shaking before she relaxed and pretty much collapsed beside me and another minute before she seemed able to talk.

"Holy shit...that was intense! I've never really enjoyed anal play but your tongue on and in my ass felt amazing. Speaking of asses...now I'm looking even more forward to playing with yours!"

I could tell she was nervous again but excited at the same time so as I was still laying on my back so I grabbed one of the pillows and put it under my hips to bring them up a bit, grabbed the lube I'd brought and started teasing my ass with a finger and then once I'd relaxed enough that it slid in easily, I added a second one and the whole time she was watching and all she said was, "that's so hot - I've never seen a guy finger his own ass before - can I try?"

I just smiled, nodded and pulled my fingers out and she quickly slid two of her own in. Fingering my own ass always felt good but I'd found that someone else's fingers felt better because I didn't know how deep they were going to go or anything else. After a few minutes of her fingers, I suggested she try the strap-on. She obviously hadn't used the harness before so it was a bit of a struggle for her to get it on and buckled securely. Eventually she had it on, lubed and when she pushed the first inch or so inside me she said, "it's going in, it's going in!" and as she kept pushing more of it went in. Having been expecting to meet with Jess for the same thing, I'd made sure that the few days before the trip I'd used a toy on myself at least once a day so it went in a lot easier than it had the first time with Jess but it was still a snug fit.

Once she was all the way in, it took a few 'oops' before she found a nice rhythm where she wasn't falling out or going too deep. Now we were both enjoying it and she said, "I knew I'd like this but between the pressure on my clit and seeing the strap-on go in and out of your ass it's even better than I thought."

"Trust me, it feels great for me too!" and that was confirmed by drop after drop of precum dripping from my cock to my belly. "Try a few short strokes where the head almost comes out but then only go back in a couple an inch or so."

She did and found that when she hit just the right spot, my cock would jump a little which made her smile so she did that a few more times and then went back to long strokes for bit before giving me a bunch of shorter strokes. As good as it felt, eventually I asked her to stop because I was getting a bit tender from the toy and as it finally slipped out she looked at me and said, "I was planning on doing what Jess did and suck you until you cum but after you making me cum so hard with your tongue, I'm still horny enough that I'd like to ride you until we both cum."

A simple, "I'd love that!" was all it took and before long I felt her slick pussy surrounding my cock as she slid down on it. I knew I wasn't going to last long and thankfully she was turned on enough that she didn't last long either and after only about 10 minutes of fucking she came again and it was just like the first one - no warning then her whole body shaking as she moaned "Fuck yes, I'm cumming!"

If I hadn't been so close, I might have been able to hold off a bit longer but as soon as I felt her pussy clenching on my cock, I started cumming and it felt like it had been weeks. After both of us finally stopped cumming she ended up laying on me as I softened inside her.

As she got her breathing back to normal, she looked at me and said, "I don't think Jess would agree but I'm really glad Jade was sick tonight!"

That made both of us smile and then she got a more serious look on her face and said, "there's one more thing I've always wanted to try but no one's ever been willing."

"What's that?"

"Well, I loved the feeling of you licking my pussy earlier but I've always wondered what getting licked would feel like....well...um....after a guy came in me" and as she finished she looked at me, likely wondering how I was going to react.

"It's been a long time but won't be the first time" and with that I put my hands on her hips and pulled upwards.

She quickly got the idea and shifted so she could move up and straddle my face again except this time I could see some of my cum drip from her pussy onto my chest on the way up. Another drip started just as her pussy came over my face but I caught it with my tongue just as her pussy got close enough to lick - and lick I did! I'd always figured if it was ok for a woman to take my cum in her mouth then it should be ok for me too and the kinkiness of it turned me on.

The more I licked and sucked on her pussy, the more she moaned and more cum oozed out into my mouth but now that it was mixed with her juices, it had a totally different flavour. As I ate her, she told me how good my tongue felt and how she could feel the cum oozing out before I licked it up. At one point she said, "Fuck it's hot knowing that you're eating your own cum from me - it feels even better than it did before you fucked me."

Even though she'd just came I could feel her starting to thrust her pussy against my face more and more and moved up a few times so I could tease her ass with my tongue again too. As I ate her, I managed to get a finger in between my mouth and her pussy just long enough to get it nice and slick with the mix of our cum and then pressed the tip against her ass. Initially I felt her pucker tighten but then she started to relax and I slowly slid it up her ass. I thought I had almost all the cum but as soon as she felt my finger slide inside her she clenched even harder and some more was forced out into my mouth.

As I kept fingering her ass in sync with my tongue licking her slit she really started moaning and then came again and it was bigger than the first two. With each contraction I felt what I thought was a bit more cum getting forced out but then I realized that it was a lot thinner and had a different flavour than my cum mixed with her juices had then I realized it wasn't my cum - it was just hers and she was squirting. That turned me on even more so I found her clit with my lips and sucked long and hard on it and got rewarded with several even stronger squirts and I could feel her body shaking against my face and hands. A few seconds later she pretty much fell to the side and said, "oh my god, that was intense...what just happened?"

"Well, not 100% sure but I'd say you just squirted, have you ever done that before?"

"Never....I've seen it in porn videos but always thought it was faked somehow. Damn, I'm still shaking a bit. It felt like I was peeing but I couldn't stop it and it felt so good I didn't want to - holy shit your face is soaked!"

I just smiled at her and said, "yes - but it was totally worth it!"

Karen just smiled, leaned over and kissed me which started a few minutes of kissing and touching before she said, "As much as I don't want to - I work tomorrow so really should get home and get some sleep. I'm not sure what you and Jess have going so I don't want to mess that up but I'd love to do all this again sometime."

"Jess and I don't really have anything 'going' - we met once and were supposed to meet tonight but you know how that worked out. I'll definitely keep in touch and would love to get together again" and in my mind I was thinking how much fun it could be to play with both of them at the same time.

As I was going to sleep later, my last thought was how I could get more business in the area.