Good to Bad to Better

My wife and I teach industrial health and safety as well as certifying others how to teach. Occasionally if someone's coming in from out of town for a course and we either know them or are comfortable with them, instead of them having to grab a hotel, we'll let them use one of our spare bedrooms and that's how we met Jess. She was 24yrs old and had a 16-month-old named Jade and she wanted to get into training so she could kind of set her own hours to make daycare easier. Everything went fine, I was sure she'd be a good instructor and we stayed in touch after the course was done for any questions or problems she had.

A few months later I mentioned via Facebook that I'd be coming to her city of Hamilton to teach for a couple of days and she offered to let me use a bedroom at their house but knowing they had the baby I thanked her but said it would likely be easier/quieter if I just grabbed a hotel. Jess agreed but said she'd enjoy getting out for a little bit and did I want to grab supper or a drink with her while I was there. That sounded good to me and we decided to meet at the hotel at about 6pm the first night I was there and she'd drive from there because she knew the area.

I'd just gotten back to the hotel at 5 and figured I'd grab a quick shower when she messaged me to say she would be a bit early. Rather than have her wait in the car, I gave her the room number and told her I'd leave the door ajar because I was just going to grab a quick shower She said that was fine and I was just getting out of the shower when I heard the door open so I hurried a bit to dry and get dressed.

Even when she'd stayed with us, I'd noticed that while she wasn't beautiful she was certainly sexy - about 5'10, maybe a 32B cup and a thin waist with a small but firm ass. Ok, so maybe a married 57 year old guy isn't supposed to notice those things but I was only older - not dead.

When I came out of the bathroom, she was sitting on the bed and after a few minutes of chatting she said, "I've been wondering something since I stayed at your place but I'm not sure how to ask."

"I'm generally pretty open to questions so how about just going for it?"

After a deep breath she said, "Well, I'm sure you didn't see me but you were up working on the computer when I had to go pee later that evening."

"Ok, but there's got to be more than that."

"Well, I couldn't help but see what you were watching."

Now that had me going - I remembered working on the computer but I didn't recall watching anything and then I remembered I'd searched for a bit of porn before going to bed. Shit - what had I been watching when she came out? Damn, this could get embarrassing but I figured there was only one way to find out so I said, "Well, about the only thing I remember 'watching' that night was a bit of porn before going to bed - what did you see?"

Jess paused for a few seconds again before whispering, "a woman fucking a guy with a strap-on."

Now totally embarrassed, I stammered "Ya, I enjoy watching a few different things sometimes and that's one of them. Sorry if it upset you."

"I was a bit shocked but I actually watched it for a few minutes before going back to bed. It's kind of personal but can I ask if you and your wife ever do...well...that?"

Knowing she wasn't upset, I smiled a bit and said, "No, we tried it a couple of times but she thought it was really weird and didn't enjoy it."

Another pause and then, "did you enjoy it?"

Now I was starting to wonder where things were going. "Actually yes, I it felt really good. Is it something you and your husband have tried?"

"Well, no - in fact I'd never even thought of it until I saw what you were watching that night but when I went back to bed I was really turned on and had to...well 'take care of things' before I could go to sleep. I thought about it for a few days after I got home and found a few videos online and they really got me going.

For a surprise, I bought a harness and strap-on but when I showed it to him he laughed, said there was no way I was going to use it on him so I might just as well throw the harness away and keep the toy to use on myself. I didn't say anything more but I keep thinking about it and watching it in videos always gets me going. I was kind of wondering if you could help."

"I'd suggest not to push it but maybe some time when you're giving him head just try teasing his ass a bit with a finger and see if you can get him interested that way."

Now I could see that she was the one getting embarrassed. "That wasn't quite what I was thinking by 'help'. I was kind of thinking that you...well your wife doesn't like it...and I'd like to try it....oh fuck - would you let me try it with you?"

Now that certainly wasn't what I was expecting and I think she took my silence for a no because she turned totally red and lowered her head saying, "that's ok...I knew I shouldn't have asked. Can we just forget this whole conversation?"

"No, wait - I'm not saying no, you just surprised me. Just to make sure - you'd like to try pegging me to see if you really enjoy it?"

Bringing her head back up she said, "Ya, that's pretty much what I was wondering."

"I'm definitely interested - I've used a toy on myself but it's been years since my wife used on one me. Can I assume you brought some sort of toy with you?"

"Yes, I kept the harness just in case I ever got a chance to use it."

"If I say yes, I'd want you to be naked too....you look great dressed but I'd enjoy it a lot more if I wasn't the only one naked."

"That's fair - but just naked - you don't get to fuck me but if you'd like I'll suck you off when you get close - I love the taste and feel of cum in my mouth."

I was going to say yes anyway but that just sealed the deal and soon we were both undressing. When her top and bra came off, I could see that she definitely wasn't huge in the tit department but they were firm and she had small but very suck-able looking nipples. When I finally pulled my pants and boxers down, my cock sprung free and was hard enough to be pointing up all on it's own.

"Mmmm, I'm going to enjoy sucking that - you're not as thick as my hubby but you're longer so it'll be fun to see how much I can get in my throat! But before that happens, I want to find out what it's like to use this on a guy" and with that she pulled out a harness and a strap-on. As she took her pants and thong off, I was treated to the sight of her smooth pussy with her lips open just enough to hint at what was inside.

The strap-on was fairly big but one of the toys I used on myself was about the same size so I knew I'd be able to take it in my ass but it wouldn't be an easy fit. "How do you want me - on my back or on my knees?" I asked.

"Well" she smiled, "I kind of want to try it both ways but I really want to see the look on your face as I slide it in the first time so how about starting on your back?"

With a smile I said, "Certainly" and rolled onto my back as she pulled the harness on. She must have practiced a few times because she was quite familiar with the straps and buckles and she quickly got it on and was standing there with the toy jutting forward. My cock was already hard and oozing some precum just from thinking about what was going to happen so Jess took that opportunity to stroke me a few times to gather as much as she could and then apply it to my asshole which let the tip of her finger slide in but that was as far as it went easily. To make things a bit slipperier, she reached back into her bag and pulled out a bottle of Astroglide and applied a liberal coat to her fingers and my ass. As one, then two and finally three fingers found there way deep into my ass, she watched every bit of it and every time I moaned, she smiled and went either a bit deeper or a bit faster. "Damn even fingering your ass looks hot - how's it feel?"

"Hard to explain, it feels really good, it hurt a little each time you added another finger but not for long and then it started feeling really good again."

When she was satisfied that I was nice and lubed she asked, "Are you ready?" and when I nodded, she used some more of the lube on the strap-on before pushing the head against my hole. "Wow, that looks awesome! I get excited just watching the videos but actually seeing it open you up and slide into your ass is a huge turn-on."

Having just had three fingers inside me, the first inch or so went in very easily but if you've ever taken anything in your ass, you'll know but there's a second 'ring' of muscle a couple of inches in. Her fingers hadn't opened that up any and both of us felt when the strap-on didn't want to go any further. I was a bit worried that she'd just keep pushing but apparently, she'd paid attention to the vids she'd watched and backed off with the pressure and started making short/slow thrusts, each one going a bit further in. I kept giving her feedback - "slow down, ok a bit more...it's starting to go in...no, a bit slower" until finally "Ohhh, fuck...yes it's in!" as her hips finally touched the backs of my legs. "Ok, that feels great. Now nice, long, slow strokes at first."

She did exactly that and pulled back until I could just feel my ass closing around the tip of the strap-on before she started sliding back in and as she did she must have pressed a button or something because the whole thing started vibrating and holy fuck did that feel good! The more of the strap-on she got in, the more I could feel the vibrations and the better it felt. There was still some resistance but it went in much easier than the first time and each stroke after that went easier and easier as the toy opened me up. The more I relaxed the better it felt and soon my cock was literally dripping with precum and I was moaning with each of her strokes.

Once I was able to take it all with no resistance, she started teasing me - going from stopping just as the head slid inside then pulling back out, to long, deep, slow thrusts and then to only pulling back a little before bottoming out again.

I couldn't resist reaching up and cupping her tits so I could play with her nipples. "I know, there's not a lot there to play with."

That's ok, I'm more of a nipple guy than a tit guy and I love how nice and hard your nipples already are. As I played with them she started moaning a bit so I realized they were also really sensitive.

At one point as she was giving me nice long, slow strokes she asked, "How's that feel for you?"

"It feels awesome, every time you slide back in, it touches my prostate and I can feel a tingle all the way through my cock and even more when you're just sliding in and out with short strokes. How's it feel for you?"

"Physically it's really good - there's a bit of the strap-on inside my pussy and a nub that presses against my clit every time I push in but mentally it's amazing! I love the feeling of being in charge, being the one that's penetrating you and then you add the kink of a guy taking it up the ass. The combination of the two is a huge WOW! Are you ok to let me try doing you doggy?"

When I nodded, she pulled out and I moved over so I was braced on my arms and knees. As Jess moved behind me and I felt her start pegging me again she said, "This is different, I can't see your face but I can see why guys like doing it this way - it feels really dominant! How about you?"

"Oh it feels good.. maybe even better because you're hitting my prostate on every stroke."

"Well let me know if you get close to cumming - don't want to waste it all over the bed" and with that she really started fucking me harder - it hurt slightly but it was a good hurt so other than moaning I didn't say anything and just let her fuck me how she wanted. Usually when I use a toy on my ass, I have to masturbate to actually cum but the kinkiness of what we were doing and the way she was hitting my prostate had me getting closer and closer until I finally told her I was going to cum soon.

With that she pulled out and told me to roll over again. As I did, I could see her pulling the harness off before moving so she could take me into her mouth. Just like when she was fucking my ass, she was going back and forth between taking as much of it in as she could (and eventually took all of me down her throat) and then she'd either take just little sucks on the head or stop and lick and kiss my shaft before starting to suck me again. At one point she stopped and shifted - I thought maybe she wanted to get more comfortable but then just as she took me back into her mouth, I felt the head of the strap-on being pushed up against my asshole. Holy fuck what a sensation - a vibrating strap-on being slid up my ass at the same time as she was sucking my cock - that was a first! I wanted to last as long as I could but when she started speeding up with both the sucking and the strap-on in my ass, I knew that cumming would be inevitable and less than a minute later I was shooting into her mouth.

When she felt the first spurt, she took me all the way into her throat again so I was actually shooting my cum straight down her throat and she held me there until I was done cumming and started to soften. When she finally let my softening cock slide out of her mouth I asked, "Did you cum while you were fucking me?"

"No, I got close a few times but didn't actually cum - I know I'll be taking care of that when I get home."

"Well, I'd be more than happy to take care of it for you right now if you'd like."

"I 'd like that but I told you when we started that I couldn't let you fuck me."

"I know...but if I gave the toy a good wash, I'd love to use it and my tongue on you at the same time until you came."

She considered that for a few second then said, "Mmmm, I love getting eaten and a toy at the same time does sound great...what the hell, but nothing more than your tongue or maybe a finger or two" and with that handed me the toy, rolled onto her back and said, "I'll be right here."

She was certainly there when I got back. She was slowly stroking her pussy and clit and she looked awesome. Being aroused had made her pussy lips puffier and more open and I could see the moisture between them. I love giving oral to a woman so before I used the toy I spent a few minutes licking and teasing her pussy. Jess tasted sweet and the more I tongued her, the wetter she got. When she started moaning and thrusting up against my face,

I took the opportunity to tease her asshole with my tongue a few times which got a few much louder moans (have to file that away just in case we ever played again) before sliding the toy into her pussy. It went in much easier than it had earlier into my ass but the reaction when I turned it on was much the same -"Oh fuck that feels good!" and she moaned even louder when my tongue started flicking her clit at the same time.

She must have been really close to cumming earlier because it was only a minute or so of toy and clit play before I heard a loud, "Fuuuuck!", her whole body tensed and then relaxed and I could actually feel the contractions of her pussy against my tongue. Not one to leave a lady wanting, I kept licking, nibbling, sucking and using the toy on her until she'd cum twice more and finally pushed my head away mumbling, "no more...too sensitive."

I moved up beside her and after laying there smiling for a few minutes, Jess looked at me and said, "wow...I thought just pegging you and sucking your until you came was good but damn...those were some of the best orgasms I've had in a while! When I came here tonight I was planning on it being a onetime thing just to know how it felt to fuck a guy but if you're interested and we're in the same area - I'd definitely be interested in doing it again. One question though - when you were licking me your tongue hit my butt hole a few times - was that just an accident?"

I smiled and said, "no...I wanted to see how you'd react."

"Well, it kinda surprised me at first - no one's ever done that before but it felt good. If it wasn't an accident does that mean you'd do it again next time?"

"I certainly would...and everything else we did too!" and with we hugged, she got dressed and soon I was by myself again but wondering how long it would be before I could get back down her way.

Fate was on my side and it was only a couple of months later that the same company had me back down to monitor a class and make sure the new instructors were doing it right. I sent her a message on Facebook letting her know I'd be coming down again and asked if she wanted to go for a drink or maybe something to eat. I didn't get a reply for a few days so was thinking she'd decided not to but then I got "Sorry for not getting right back to you, hubby's working that night so I had to make sure I could get a babysitter. It'd be great to get out for a bit."

I'd just gotten back to the hotel from the course when I got a FB message from Jess but all it said was "can I call you?"

I replied "sure" and sent her my cell number. A few minutes later she called and I could tell something was up. "I'm really sorry but tonight's not going to work. Jade's been sick all day and she's running a fever so I really don't want to go out and leave her with a sitter."

Damn - there goes my plans of fun but I just said, "No prob, I can understand that. I hope she's feeling better soon and there'll be another time."

"I know but I'm pretty sure you were looking forward to it as much as I was so..." and she kind of tapered off.

"Ok, what are you thinking?"

"Well, I hope you're not mad but my neighbour's the one who always babysits. We've been friends for years and are pretty open with each other. We were chatting last week and she told me she broke up with her boyfriend last month. When I asked why, she said she'd tried fingering his ass while she blew him and he got really upset. She was hoping he'd enjoy it and maybe want to do more because she'd always wondered what it would be like to fuck a guy's ass. It just slipped out, but I said it felt great. Anyway, she picked up on it and I made her swear she wouldn't tell anyone else but I told her what you and I had done and she said she wished it had been her doing it."

I had an idea where this might be going but needed to know for sure so I asked, "So, does that mean she wants to take your place?"

"No, well maybe. I haven't asked her but thought if you wanted to then I'd see if she wanted to and maybe you could still have some fun tonight."

I thought for a few seconds and said, "Well, not what I was thinking would happen but sounds interesting. Do you think she'd be open to giving/getting some oral as well?"

"Oh, I'm pretty sure - she's said that the only thing she really misses other than the sex itself is getting eaten. Is it ok if I ask her and if she's interested give her your number?"

"Ya, it's sounding more and more interesting - let's see what she says."

It was only about 20 min later I got a text from a new number that read, "Hi, it's Karen, Jess's neighbour. From what Jess told me I'm definitely interested in having the same fun that Jess had with you. "

After sending her directions and the room number, I grabbed a quick shower before she got there. Rather than getting fully dressed, I just pulled on a robe and waited. I realized I'd forgotten to ask Jess what she looked like but when she got there I was very pleasantly surprised. She looked about the same age as Jess but that's where it stopped - where Jess had short, blonde hair, Karen had long dark hair and instead of the small breasts that Jess had, judging by the way her shirt was pushed out, Karen was at least a 40DD with her nipples were already clearly showing through the fabric so I was pretty sure there was no bra. Her hips and ass were also bigger than Jess was but her tight pants made every curve look totally sexy and I told her so.