(M)y younger assistant(f32) is into older guys and isn’t afraid to show it. Long [mf]

I, (44m) thought I would finally share my story of a wanton tryst that honestly never would have imagined in my wildest dreams. These are long, so bear with me and there a several that I’ll break into parts.

I used to have a job where I traveled all over the us to conduct large scale corporate investigations, compliance audits and training. I worked in a small group and was the most tenured so when new folks came into the department I was tasked with taking them on the road their first couple times and getting them up to speed.

About me, I’m a married 44 year old male, pretty successful and am good at what I do. I’m of average looks and build with blond-brown hair, blue eyes but stay in shape and am told I have a very engaging personality and have a lot of charisma. In these trainings I got my fair share of flirtatious smiles or gestures from females but never pursued or encouraged any of it although it’s flattering to know someone still finds me engaging.

My wife and I have been together for 20 years and married for 17 and while we have good sex, it’s very vanilla. She has an amazing body with big hips, big soft breasts and a sexy, paunchy belly that I love. She never understood that I think she’s perfect regardless of how many pounds she’s packed on after giving birth to our kids years ago. It’s made her even more desirable. She doesn’t explore and when I try to get her too it usually ends in disappointment because I like more things than she does. Add to this that she had a long term hidden affair a couple years before and it simply meant that we were together for the kids and only going through the motions. After the discovery she said she’d do anything I wanted from bringing in another woman for a three way to finding another man to bring into the bedroom. It wasn’t what she wanted – she just wanted to repair the damage she caused (which was a lot) and because it wasn’t something she wanted, it didn’t really interest me.

As a result she does accommodate my voyeuristic interest and wears loose shirts around the house with no bra and lets me take pictures of her whenever I want to for use later as I masterbate. To her credit she has offered her body up to to me if she’s sleeping and I need to get off and has no problem if I crouch over her and grope her soft curves as I jack off. Sometimes she wakes up and helps by stroking me, playing with my balls or running her finger lightly across my sensitive asshole. Other times she stays asleep. Sometimes I put in a butt plug or fuck my ass with a prostate massager while I do it but she would short circuit if she saw it.
She’s also given me a green light on taking advantage of her if we drink too much and she passes out (some hot stories for another time) but that’s about as far as her freakiness goes. Instead, we have mostly vanilla sex and I depend on porn to get my fill on my turn ons; girls with dildos, him and her ass play, threesomes and I like to watch amateur video of real husbands and wives sucking a cock together or the husband licking the wife while a fat dick is inside her and he tastes a little dick himself.

Back to the story – One of the employees I trained was a 32 year old curvy smoke show named Taylor. She was 5’7″ with mid-length chestnut hair, a beautiful face, large Dcup natural breasts, wide hips and narrow waist and ass to die for. It didn’t hurt that she was incredible smart and witty and eager to learn and we really enjoyed each other’s company during her first month in the office before her travel started. She kept telling me she was eager to get on the road and start learning.

During the work at our office I walked each person through the program and thats when I noticed Taylor, who was engaged to her fiancé Scott, really started to pay additional attention to me. It didn’t make sense to me, because Tayler was HAWT, and Scott and her seemed to be pretty in to each other. I chalked it up that I was her superior and ‘had all the knowledge’ so maybe she put me on a pedestal as a mentor. She would linger later than anyone else, lay a hand on my arm when talking and even place a few touches on my knee.

Her body was amazing and she was so genuine that I don’t think she realized how perfect it was. I’d spent time watching her walk down the hall with that round ass swaying or imagine what her naked breasts looked like. On casual days she would wear tighter shirts that really showed the shape of them and often I would see her nipples get hard because of the AC and they would poke through her shirt.

Other days she would come into my office and would bend over the front of my desk as she laid a presentation on it and when I’d look up I’d be greeted with an incredible down blouse shot of her smooth round breasts practically falling out of her gorgeous bras. Some bras were thick and had padding to push them up and some were these thin, flowery translucent material that did nothing but hold them up and accentuate their shape. I would try to stay focused but would steal casual glances as much I could as my cock grew hard in my pants. She always seemed completely oblivious to revealing her tits. Several times she would be crouched down near floor level filing drawers and I would just see the tops of her French cut panties or boy shorts while other days I’d see the top crack of her ass indicating she wasn’t wearing any panties and on the days she wore yoga pants i was almost certain I could see her pubic patch through them as she stretched after a long day. She was a complete pleasure to have in the office for sure.

We always kept it professional and I counted myself lucky when I would get the voyeuristic shots which happened at least couple days a week.

It wasn’t long before I had an issue come up that required travel to Hawaii for 5+ days from our Midwest state on the following Monday. Taylor was to tag along with me to train and to learn the ropes and would be her first business trip she’d ever taken. The Friday before we were to leave she came to my office very excited for what she called ‘our adventure’. I told her it would be mostly business but that we would have our evenings free to explore, sight see, whatever she wanted. I’d been to Hawaii many times but she hadn’t and was excited for that to be her first destination.

She threw me for a loop when she asked if I was bringing a swim suit to go swim at night. I told her I always do because it helps relax me after traveling and she said, ‘well good! We can go swimming, have some drinks around the pool and sit in the hot tub. I’ll make sure your relaxed!’ I’m sure I blushed as I pictured her in a bathing suit and again my cock started to stir.

‘I’ll have to shop to get one that is more appropriate for work so I don’t make an ass of myself’ She said.
Before I could stop myself I said, ‘don’t shop on my account, I’m sure you’d look fantastic in anything you decided to wear!’ She smiled a little smile and looked at me for a second as I silently berated myself for it.

As we were walking out she surprised me by giving me a hug and saying, ‘I doubt I’ll get any sleep all weekend – we are going to have a great time!’

At home I found myself getting excited to be spending that much time with this gorgeous young lady (and the prospect of seeing her in her bathing suit) and had to really stay focused to hear what my wife was saying to me. When the wife and I had sex Saturday night I kept picturing Taylor being on the receiving end of my tongue, fingers and cock and the wife wasn’t very receptive. Instead she worked to get me to cum quick by running a finger lightly over my asshole as she rode me rather than taking time and enjoying each other’s bodies. That was the crux of it for me – I see sex as exploring and finding different pleasures and rubbing and sucking and giving in to what turns you and your partner on. With her, although it’s just about checking it off the list and moving on to the next household chore.

Monday morning I showed up to the airport and checked in, grabbed us each a cup of coffee and sat down watching people as they made their way to the terminals. When Taylor arrived I was pleasantly surprised to see she had chosen a nice pair of khaki shorts that pulled tight on her butt and a snug white button-down shirt that accentuated the size and shape of her breasts and she clearly had a darker bra underneath.

‘Hi’, I said, standing to hand her her coffee as she approached. She took her sunglasses off and said, ‘that was so sweet of you!’ and then she started crying. She gave me a big hug where I could feel her large breasts pressed against me and it seemed to linger for a second longer than normal.

‘I’m sorry. I told myself I would keep it together. It’s my fiancé – he’s such an asshole. We went to a concert on Saturday night and he got so drunk that he got lost and I couldn’t find him anywhere. I was getting hit on by drunks, walking alone to his car only to find it gone. He wouldn’t answer his phone so after waiting 2 hours I got a cab home and he was there! He’d left me there and drove home drunk, damaged his car and was completely unapologetic. We fought all weekend and I’m just having a hard time with it.’

She wiped her eyes a smiled a little as she looked at the cup in her hand. ‘He’d never get me coffee or even know how I take it – thank you for being so sweet. Why can’t more guys be like you?’

I told her, ‘no worries. I’m sorry about your guy. If you need to take care of home stuff and feel like you need to stay home it’s no problem – there will be plenty of other trips for sure.’ And hoped that my disappointment of her possibly not going with me didn’t show on my face.

‘No way! I’m not going to let him ruin this trip for me. I have a lot to learn and couldn’t be more excited. Im starting to realize how much he and I aren’t right for each other I’m sorry to walk up crying, you must think I’m an idiot.’

As we sat there I could see her firing off angry texts to her fiancé. With about 30 minutes until boarding time the flight crew paged me and asked me to come to the desk. Taylor followed and when I got to the desk they apologized but the flight had been over sold and they were upgrading me and another traveller to first class because of mine and his frequent traveller miles. When I told them I wasn’t traveling alone the stewardesses face broke into a worried face as if she didn’t have any other option but to separate us.

That’s when Taylor wrapped her arm through mine, squeezing her breast firmly against my arm and said, ‘honey what are we going to do? I don’t want to fly all the way there alone – this trip is supposed to be our romantic getaway!’ The stewardess mistook my mouth hanging open in speechless shock as me getting ready to get angry and quickly said, ‘it’s no problem – I’ll upgrade all three – we have plenty of room on First class honestly so you will have as much privacy as you want. We are all good – you two enjoy your trip’.

I was taken aback and when we were done I said, ‘what was that about?’ She replied, ‘I figured it was the only way to not miss being up there with you and Ive never flown first class. It worked though, now we just have to continue the act’ as a big, gorgeous smile spread across her face.

Regardless of how uncomfortable it was to have this interaction with my employee I decided there was no harm in it and figured I’d call her honey a couple times and be done with it.

As we were called to board I motioned for her to step in front of me as we moved through the line. When we got close to handing our tickets over she reached back and grabbed my arm pulling me right up against her and wrapping my arm around her body under those magnificent breasts laying her hand on top of mine where it rested just at her belt line. As we stood there waiting, her ass pressed against my crotch, my arm under her heavy breasts and my hand on her soft stomach and bikini line my dick immediately started to throb and grow hard pointing sideways. And did I say throb? It felt like there was pneumatic pump attached as it pulsed and grew. I attempted to pull back a little to avoid being further embarrassed and she actually pulled me tighter, maybe even arching her back a little to press harder against my growing member, there was absolutely no hiding it. I’m not terribly long, 6.5″ or so, but I’m very thick.

She could feel just how hard I was now that it was pressing fully along the warm, soft cheek of her ass. I reached between us to try to move it to make it less obvious but all I did was point it straight up where it now nestled nice and snug in the crack of her ass.

While I turned 3 shades of red, she turned her head to look at me and I saw a glint in her eye I’d not seen before; almost mischievous and curious. As we handed our tickets over the stewardess noticed my crimson face and said, ‘you all are such a cute couple – you all enjoy your trip!’ Continuing her charade Taylor pulled my hand up between her big breasts and pulled me closer driving my cock tighter between her ass cheeks and said, ‘oh we will….’

Needless to say I was more than a little flustered and wanted to crawl in a hole. Within a half hour of showing up for travel with my newest employee I’m in a situation where she has me groping her breasts and my very noticeable hard dick is sandwiched between us and nestled in her butt.

We broke free as we made our way down the gangway to the aircraft she turned to me and said, ‘see?! That wasn’t too hard was it?’
With that I blushed even redder while she laughed as she realized what she’s just said and replied, ‘whoops! Don’t be embarrassed ~ honestly from what I could tell you have absolutely nothing to be embarrassed about. I think I may have to go clean myself up after that as well’ and with that her eyes flicked down to my crotch and lingered for a second where my raging hardon might as well as had a big lighted arrow pointing at it. A quick look at her revealed that her face was a little flushed as well.

I told myself i imagined that part and that she was now thinking of me as a perverted older guy that likes to grind against their employees.

As we got closer i realized we were on a huge 747-400 and was just hoping to get seated quick so I could do damage control and hide my raging hard on that was noticeable to anyone that looked at it. When we got to our seats it was actually business class with large roomy seats, and a curtain you could pull for privacy and sleeping.

Taylors eyes lit up and said, ‘this is awesome! I’m sorry about back there I didn’t mean to embarrass you but this was well worth it don’t you think?’

I had to agree as I grabbed our bags and stowed them, and then offered her the window seat. As we sat there waiting for everyone else to board she said she was freezing from the AC vent and said, ‘I’m sure everyone boarding can see my headlights shining’. Sure enough her hard nipples were standing at full attention. ‘Not to be crude but there isn’t a bra on earth that can cover these when I’m cold. I’m sure you and everyone in the office have noticed.’

When I lied and said with a laugh that I hadn’t noticed I almost thought I saw a momentary look of disappointment on her face. But, being raised in the south, being married and a professional I simply didn’t make it a practice to flirt or have sexual innuendo with anyone other than my wife. I’d seen too many guys get their lives turned upside down by sexual harassment claims to do that.

As Taylor was getting situated I got up and walked to the bulkhead to get Taylor a blanket and when I got back and handed it to her she got this look on her face and said, ‘I honestly don’t know that I’ve ever met a nicer guy Rich and I believe it’s just who you are. It’s the little things you do and I wanted to tell you thank you. Thank you for all the training, the extra time, taking me on this trip and being my mentor.’

I nodded and said, ‘thanks, it’s no problem Taylor I promise. It’s not often that you get upgraded to first class. How about we enjoy it a little and have a couple drinks to relax and talk. By time we get to Hawaii we’ll be ready for a light night and then to get to work in the morning.’

The stewardess asked if we wanted something to drink and I ordered a screwdriver and Taylor ordered wine. We continued our small talk until the flight took off and settled in. We talked business for the first two or do hours and we had a couple more drinks. As it usually does, as the alcohol flowed our conversation became less inhibited.

She told me about her fiancé and that she needed to find a nicer guy. ‘He used To be a good guy but now he’s just self centered and selfish. He only thinks about himself and he’s selfish with his time. I mean who forgets their fiancé? What’s wrong with me? He’s selfish in bed too and leaves me to take care of myself all the time.’ As my mind went to a happy place imagining her getting herself off she got quite for a second as she ran her finger over her wine glass.

I said, ‘Taylor, you need to not beat yourself up – people change. You are a young, smart and stunningly gorgeous woman that any man would be happy to be with.’

Her eyes lit up as she looked at me with a smile. ‘You think I’m stunningly gorgeous?’ I replied with, ‘actually I do – I apologize if that seems forward but you’ve got to see it, right? That men fall all over themselves around you?’

She said, ‘I see some guys do it but they do that for all the girls. My fiancé said I’ve packed on weight and that i need to tighten it up. He used to be at least a little adventurous in bed and now it’s just vanilla and he blames my weight.’ With that she lifts up her shirt a little to show her stomach right above her belt. Even sitting down it was nice a smooth and although it wasn’t rock hard it was hardly fat – in fact it was beautiful. She said, ‘am I fat?’

I said ‘he’s and idiot for saying that to you honestly. Your stomach is incredibly sexy from what see.’ With that she put her shirt back down and is when I noticed her middle shirt button had come undone and I was able to see the side of her right breast and the hint of a pink areola peaking out of a navy blue lacy bra barely containing her boob.

The stewardess chose this time to come take another drink order and this time I ordered a double vodka and tonic and Taylor said, ‘I’ll have a vodka tonic as well’.

We continued our conversation as the drinks arrived and I enjoyed my view of her breast. When she moved I had this perfect view of her entire right breast and could see why her nipples showed through – they were as big as pencil erasers on top of quarter sized areolas and were gorgeous.

Continuing her discussion about her fiancé she said, ‘I don’t know why am talking to you about this, but Scott and I used to have so much fun in bed and then something changed in him. Now it’s a chore.’

The alcohol was catching up to me now. I said ‘you know, that happens to a lot of people. I’m stuck in a vanilla bedroom, although my wife was never really adventurous. Ive had to back off to keep from shocking her,’ as I laughed. ‘But I manage. I wish it was different sometimes but what do you do? I suggest you find who you are sexually and THEN find someone so you are satisfied with in the bedroom, or wherever your proclivities take you, so you don’t live a sexually frustrated life.’

She was instantly interested. ‘Really, you hide your turn-ons from her?’

‘Well, the more shocking ones I guess.’ I replied.

‘You seem so squared away and straight laced. Your wife isn’t in to exploring with you?’

‘Ha, not at all. At least not with me. She had a long term affair a couple years ago that initially broke my heart but I owe it to my kids to keep them secure until they at least get through high school. Even still, she never has to ‘take care of herself’ as you say because I enjoy doing it. Hell, i have a really high sex drive so I think about it morning, noon and night. She ends up pushing me off just as I’m getting warmed up. Add alcohol and some drunk sex and I’m in heaven because it lowers your inhibitions and is the only reason I’ve been able to get her to loosen up and play in the past.’

Behind the fog of 4 or so heavy vodka drinks I could hear my upper brain saying, ‘stop you fool!’ As my lower brain won out by saying, ‘keep on you sly dog!’

The alcohol must have slowed slowed my reflexes and I wasn’t as sly as I thought because as I was finishing my sentence I was staring at her gorgeous breast through the gap in her shirt. She saw me looking and looked down and said, ‘good god I can’t keep these things contained some times, I’m sorry’ but didn’t fix her shirt.

‘Ummm, don’t apologize – I have thoroughly enjoyed the view and I should be saying thank you, I’m a breast man myself!’ As I smiled like a Cheshire Cat.

She got this look in her eye again and I figured I had just over stepped my bounds. She said placed her drink down and said ‘if you’ll excuse me, I have to use the restroom and fix this and grabbed her small sweater to take with her.

I silently groaned and berated myself for crossing the line. Alcohol has a way of doing that to me and is usually why I never talked sex at work or drank with colleagues. I told myself to straighten up and to clean up the conversation. I ordered some snacks from the stewardess in order to get some food in my stomach.

When Taylor returned she was wearing her little sweater. Bummer, I told myself – at least it was good while it lasted. She was quiet as she got settled. I sipped the remains of my drink and thought it was time to switch to water to keep from embarrassing myself any further.

As she got her things straightened out she took her sweater off and I immediately noticed two things; first – she hadn’t fixed the button that was open, in fact now the one above it was open as well leaving a large portion her chest exposed. And second – she had completely removed her bra and I now had an unobstructed view of her amazing tits through her gaping shirt. She bent down and stuffed her navy blue bra and something else into her bag.

She raised her arm to call the stewardess over which caused her shirt to open even further and I could see just how big her breasts were. She watched me stare openly with a wry smile on her face. they looked heavy and smooth. My mouth went dry and my dick started to grow once more as she said to the attendant – ‘We’ll each have another drink please.’

Her eyes were glossy and she looked me in the eye and said, ‘alcohol does the same thing to me – I love it.’

This beautiful woman was showing off to me. Not to look a gift horse in the mouth I said, ‘well, it looks like you fixed your problem.’

She replied, ‘it’s way more comfortable this way and I like that someone appreciates them, i have to admit their are quite nice, so why make it hard on you?’

Her gaze lowered and again she locked her eyes on the outline of my growing cock in my shorts. I looked down to see my bulge outlined very clearly, from the swollen head, to the thick shaft and went to place my hand over it to hide it when she said, ‘you really don’t have to be embarrassed, I like it. It looks nice.’

I moved my hand and then adjusted my aching cock to relive some pressure. Her eyes were locked on it still. As the attendant brought our drinks she turned a little sideways in her seat to face me, her cleavage was on display. I could see the swell of both breasts clearly and her large nipples poked out at me and I was in visual heaven. The only thing better would be her totally naked with those big tits on display.

I started to come to my senses for a second and said, ‘Taylor, you are very sexy and I appreciate the interest but we need to stop this. I shouldn’t have been so forward. This is wrong.’

She replied, ‘stop what? Some harmless discussions? I’m a big girl and I honestly I like the attention. If you don’t mind looking i don’t mind showing it…it’s a turn on and my fiancé could care less about me or this.’ Gesturing to her glorious curvy body.

We continued our banter back and forth as we sipped our drinks. Even when it was quite it wasn’t uncomfortable. I’d stare openly at her breasts and that gorgeous face and she’d lean forward feigning getting something out of her bag giving me an incredible view of her natural tits swaying. She would laugh playfully looking at my expressions and would touch my leg or my thigh or my arm. My dick was so hard it could it have cut diamonds and I would occasionally place my fingers around it and stroke it once or twice. She would lock her stare at my cock while I stroked it.

I asked her if she’s ok – I didn’t want to be the forward one and then her back off.

‘Im perfectly fine. I have some turn ons that I haven’t shared because I didn’t want to be judged. I love openness and fun and at least the though of uninhibited love making. And I love the look and feel of a cock….the soft feel of the spongy head in my mouth. The hard yet silkiness of the smooth skin of the shaft. I love to see a guy touch himself and stroke himself…’

As she finished her sentence her knee fell to the side and the leg of her shorts opened revealing a clear shot of her naked pussy. Apparently when she went to the lav this little minx doubled down and removed her panties as well. I could just see her lips and a triangle patch of dark hair above it in the shadow of the opening. She looked down at her barely covered nakedness as if she was making sure i could see it all. She picked up her drink and said, ‘so tell me what some of these things that scare your wife’ as she grinned and opened her legs even further.

Picture this; is two, in a fairly secluded business class cabin of a ridiculously large aircraft. A gorgeous curvy goddes sitting before you with her legs spread wide, her pussy barely on display and her large tits on the verge of spilling out asking you about your darkest sexual interests.

At this point I figured she’s a freak like me and whether it was the booze talking, the years of stifling my proclivities , or the fact that in the last 2 hours I had stared openly at her breasts and now straight at her pussy and opened the flood gates. I said, ‘she’s never masturbated for me – even though that’s my biggest turn on.’ I wrapped my fingers around my cock in my shorts and noticed a large growing wet spot as precum leaked out.

With her legs spread wide she slid down in her seat which pushed her pussy right up against her shorts. She looked amazed at how wet i was. I said, ‘I have a lot of precum when I get turned on like this.’

Her hand moved slowly down her stomach to her open short leg and she slid her finger along her slit and parted her lips to reveal just how wet she had become. She had a beautiful pussy with swollen, peach-like lips. Her clit was on the smallish side but was very prominent within its hood. She moved her finger up and down her lips and circled her clit several times ‘she won’t touch herself like this?’ She asked as her eyes closed slightly as she stroked herself.

She said, ‘this makes me so hot. Ive seen you watching me at work and for the last 3 weeks I’ve been showing you all I can, sometime you notice sometimes you don’t. The biggest turn on was that you never made it an issue. I was staring to wonder if you simply didn’t like what you saw – your wife is very beautiful.’

I told her the sneaked glimpses and the voyeurism was a huge turn on and she was simply a goddess.

Reaching for my cock I discovered the head was now just peaking out of my shorts. We both looked down to see a big glob of precum on the tip dripping off front of the head. I drug my finger across it and scooped it up to taste it. I love the taste of my precum and whenever I have a good stroke session I lap it up. Her eyes opened wider and she smiled as she placed two fingers in her wet pussy. ‘That’s so fucking hot Ritch do it again for me’.

I reached up and pulled the sleep curtain closed and quietly undid my top button and zipper releasing my cock. Her eyes flickered with delight as she saw it. It was a proud moment; exactly what you want when showing your dick to someone for the first time. It was engorged and swollen, veiny and standing at full attention. I grabbed it from the bottom squeezing more precum out and scooped it up and placed it in my mouth again.

‘I love how dirty you are – Scott couldn’t be more reserved and it sucks’ she said.

She opened her shirt a little more and slid her hand in and lifted the weight of her breast and said, ‘tell me all of it and stroke your cock while you do it. This is so hot you’re going to make me come if we keep this up.’

Here I was at 30,000 feet with my employee having a discreet, inebriated mutual masturbation session (which id never done with my wife) and I didn’t care.
As I stroked my cock slowly watching her feel herself, I said, ‘I want to watch you fuck yourself with a dildo.’ She now placed 2 fingers inside her. ‘I want to fuck your ass while you fuck your pussy with a big thick dildo’. She moved her shorts further to the side revealing her perfect little asshole as she circled it with a wet finger clearly enjoying the sensation, her juices were literally glistening down the crack of her ass.

I stroked some more. ‘I want to eat your ass while I fuck your pussy with a dildo’. She moved her hand faster – ‘mmmm, that sounds nice – I’d love that.’
‘go on’ she pleads.
‘I’d lick that beautiful pussy while i fucked you with a fat dildo.’ She looked at me and said, ‘would you lick the dildo too?’
‘From top To bottom’ I said and her eyes lit up, ‘mmm, I’d love to watch a man with a big cock in his mouth.’

Who was this woman and had she somehow entered my mind or could it be she was just as perverted as I?

‘I want you to finger my ass while giving me a blow job.’ I said pulling my underwear down to pull my heavy balls out too. Now her middle finger disappeared into her ass up to the second knuckle and her eyes glazed over in ecstasy.

As for me I was near the blowing point. She locked her gaze on my dick as i snaked a finger down and probed my own asshole. When she saw that she started scooting forward – pushing her pussy tightly against her shorts as she drove two fingers in and out and still fingered her own asshole. Her clit had swollen to nearly double its size and I decided I had lick it – I leaned forward aching for a taste of it and she spread her legs obscenely wide pulling her shorts to the side to give me better access as she started humping the air with her hips and pushing her crotch closer to my face knowing what I wanted and clearly wanting it too. She was beside herself lost in ecstasy.

Up to now there had been no touching. It was as if, in my mind, I was watching an incredibly lifelike porn video, but I couldn’t take it any more. This woman has the same turn ons as me and it was too good an offer to pass up. As I got closer I could smell her musky scent and I lowered my mouth to her pussy reaching my tongue out, to the first new pussy I had touched or tasted in 20 years and there was an electricity that sparked from my tongue as I encountered her soft folds and her tangy flavor.

She reached out and grabbed the back of my head and forced it fully on to her mound as I pushed my tongue deep inside her. She moaned from deep within her chest and I latched onto her clit, sucking on it and circling my tongue around it. I pushed two fingers into her pussy getting them nice and wet and sawing in and out as she writhed her hips enjoying the sensation. After ten or so strokes I pulled them out and then pushed both fingers straight into her tight asshole up to the first knuckle where she immediately bore down onto them with all her weight, driving them deep inside her ass.

‘I’m gonna cummmmm’, she groaned as her body started to tremble and I felt her pussy contract and start flowing juices that I lapped up as fast I could. Her asshole spasmed around my fingers as wave after wave of her orgasm hit her. The pressure on the back of my head increased as she mercilessly ground her swollen, dripping pussy on my face and I loved every minute of it. I looked up and she was staring down at me with intense concentration, her face flushed and a large breast half out of her shirt, knees spread wide and her pelvis thrusting upward and then forcing her ass back down on my fingers with pure lust like she was ass fucking a cock.

Somewhere outside my lust filled haze I began to come back to reality as I felt turbulence that wasn’t caused by our groping and wanton grinding. I looked up with my fingers still in her ass and said, ‘are you good?’ She nodded her head with a content smile on her face and said, ‘I’m very good but holy fuck your great!’ With that I put my face back down and placed a long French kiss in and around her wet, swollen lips, licking up her juices and swirled my tongue around her asshole where it clenched my fingers. At the touch of my tongue at her back door she bore down again trying to drive them deeper inside of her as I slowly pumped them in and out. I buried my thumb in her pussy and stared rubbing the thin wall seperating her pussy and ass between my finger and thumb when she let out a little squeal and came again, contracting and spasming all over. She began trying to push my face away at the same fucking my fingers with her ass. She seemed to really enjoy ass play. It was all so incredible hot and carnal.

My cock was forgotten in all the excitement as I slowly sat up from my hunched over position and withdrew my fingers from her holes. She all but collapsed still in disarray; legs spread wide with her glazed pussy and ass peaking out of her shorts and both magnificent breasts splayed out where her shirt had opened. I peaked my head out of the curtain to check if we had an audience and to see if I had time to straddle her face and force my cock down her throat or even to drive it into her warm wet pussy when I noticed the cabin attendant was making her way up through the cabin asking folks to put on seat belts as the turbulence continued.

I stood and turned towards her, my cock at full mast, thick and veiny and about to burst with my heavy balls hanging low. A thin rope of precum hung from the tip and made my shaft glisten. Her eyes locked on it in all its glory and as she straightened up in her chair it was now even with her mouth. When she went to grab for it I quickly pulled my waistband up and put It away. In answer to her look of disappointment and confusion I said, ‘we are about to have company – don’t worry about me, I can still taste you and smell you I’ll be ok.’

She looked at me and said, ‘I want to suck your cock. Just a taste, we have time before she gets here. I want it!’ She said pleadingly.

I sat down, reached over to her still open shirt and felt the full weight of that succulent breast and said, ‘it’s ok, I promise. We have a 5 full days to enjoy’ as i gently closed her shirt in time for the attendant to appear and tell us we need to put our seat belts on because we were entering turbulence that lasted another two hours.

Taylor was beside herself horny. She kept whispering seductively in my ear that she wanted to pull my cock from my pants and swallow it whole. She would lick my neck and drive her tongue into my ear saying she wanted to taste my cum and play with my ass.
‘Don’t you want to feel me suck that thick cock and play with your ass like you did to mine?’ Did you enjoy licking my wet pussy and sliding your fingers into my tight ass? I want to slide that dick into me. Anywhere into me.’

She would grip my cock through my shorts and comment on how thick it was.

When the attendant vacated our area I looked Taylor in the eyes as I unzipped my shorts and pulled out my dick.

She opened her shirt and placed my hand on her breast as she got up on her knees in the seat. She reached down and undid her own shorts as she bent over and took my cock into her warm mouth and I almost blacked out. She wasn’t kidding – she could suck cock.

She took me all the way in, gagging as she did and at the bottom she shot her tongue out licking as far down as she could. Her mouth worked wonders as she worked my cock up and down over and over. I didn’t understand why she undid her shorts until she came up for air and took my hand putting my fingers in her mouth and covering them with spit and the slid them down the back of her pants, between her soft ass cheeks and placed them firmly on her asshole leaving no doubt what she wanted as she pressed my index finger into her anus.
‘Finger fuck me Rich’ she said as she tried to push her ass further onto my fingers as I teased her by pulling them back. Watching her swivel her hips to try to get penetration was insanely hot.

Lost in the sensation of what her mouth was doing to my rod, I slowly explored her silky soft, wrinkled, tight asshole teasingly. As I would put tension on her sphincter she would desperately push down wanting me to penetrate her again.

She looked up and said, ‘push them in! Please!’ While squatting as low as she could. She was crazed at the moment. I reached down and pulled her face to mine snaking my tongue into her mouth to kiss her deeply.

I reached further down sliding my fingers along her sopping wet pussy and rubbed her clit, my wrist now resting against her asshole. Again she squatted hard wanting to fill her ass with something.

She then changed the game. She took her now slobbery wet hand and shoved it into my shorts and quickly shoved one finger up my ass as far as it would go. I responded by pushing two soaking wet fingers into her ass as she moaned around my cock. She snaked another wet finger into me as she curled them towards my prostate. We were both now grinding our asses on each other’s fingers with no cares at all – we were simply chasing the pleasure. Her shorts had fallen past her hips and as I looked over I could see her large, white ass cheeks and when I noticed the reflection in the window of my fingers buried to the hilt in her ass, her gorgeous pussy sandwiched between her tightly grasped legs and the fact she had her fingers planted firmly in my ass I’d had enough.

I grabbed her head and shoved her down on my cock and ground my asshole down on her hand as I started to come. She continued to fuck my ass and suck me and wiggle her ass as i shot glob after glob of cum down her throat which swallowed without hesitation.

She continued to suck until every last drop was gone as her fingers slowly fingered my ass. I continued to fuck her ass steadily as she laid her head on my lap and pointed her ass up in the air for more. She looked up and planted a kiss on me and I could taste my cum for the first time. Precum while stroking was one thing but after coming and the horniness fades I thought I’d never go through with it.
Now she licked all over my mouth and I could taste it and it tasted good.

She reached back with her other hand and started working her clit furiously. As I grabbed her hanging breast and squeezed her prominent nipple she came for the third time.

With that we started to gather ourselves. She straightened her clothes and said, ‘you have such a thick cock. Will you fuck me this week? We can do our work thing but I want to spend time working that fat cock….’
she paused as I simply stared at her – in shock that this nubile goddess was saying that to me. And she added, ‘if that’s ok with you boss. You can do whatever you want with me…I need it.’

I though to myself, ‘it’s going to be a good week’.

Source: reddit.com/r/gonewildstories/comments/8kw0ws/my_younger_assistantf32_is_into_older_guys_and

9 comments

  1. Great story, but there’s no planes that fly from the mainland to Hawaii with curtains…

  2. Now you have to tell us about the awesome 5 days you must have had

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