‘Sure, whatever you want.’ Lindsay said.
With that, she turned over and lay prone on the bed, looking over her shoulder at me. I quickly moved over to her and straddled her ass, allowing my heavy balls to flop onto her and the base of my cock touch her ass.
I leant forward, making the whole shaft of my cock line up along her ass crack. I rubbed myself on her, enjoying the sensations. Our lips met in an awkward kiss, Lindsay having to twist her neck to reach me. I sped up my thrusting, feeling pleasure from the friction between us. I wasn’t far away.
I adjusted my hips so that my cock head was now between her cheeks, each thrust forward making it press onto Lindsay’s anal opening. Lindsay was making small sounds of pleasure every time my cock pressed onto her anal ring. I wasn’t trying to fuck her anally, it was just where my cock ended up as I humped her ass.
It quickly became too much, I was too turned on and the next time that I thrust forward, my cock exploded, shooting cum out against Lindsay’s asshole. Rope after rope of cum squirted out, completely filling her ass crack. I moved off her as my cum stopped and looked at the mess I had made!
Lindsay opened her legs and wriggled her ass about, enjoying the feeling of my cum on her skin. I was turned on watching my cum dribble down her ass, over her pussy and onto the bed sheets. Lindsay was a mess, but what a sexy mess.
‘I think I need another shower now!’ Lindsay said.
She got up and went into the bathroom and into the shower. I followed her but did not get in the shower.
‘Thanks Lindsay that was another of my fantasies!’ I said.
‘I loved it, I especially liked feeling your cum on me. You know I think I like anal play, what with you having stuck your fingers in my ass for the first time today!’ Lindsay replied.
Lindsay then got out of the shower and walked over to me. She bent down and swiftly took my cock in her mouth, swirling her tongue around it.
‘You had a little dribble of cum on the end, shame to waste it!’ Lindsay said as she stood up again.
‘Hey, thanks, you won’t find me complaining!’ I said.
‘I don’t think I can take anymore orgasms tonight.’ Lindsay said, before continuing, ‘so how do you want to do sleeping? I’m not sure how I would feel about actually sleeping in the same bed together.’
‘You know, neither do I! It’s weird isn’t it? Here we are having done so much sexually just now worried about sleeping in the same bed! How about we say this, let’s go back to our own rooms tonight and see how we feel about it all tomorrow. We have another night after all!’ I said.
‘OK, I think you are right.’ Lindsay said.
With that, I got dressed and left Lindsay with a passionate kiss, having arranged to have breakfast together at 7am the following day.
The next day I met Lindsay for breakfast. I had to ask her a question that had been nagging me,
‘So Lindsay, any regrets about last night?’ I asked.
‘None whatsoever! It was amazing and I can’t wait until we can do it again. That is if you still want to?’ she said.
‘Phew, I was hoping you would say that. I’m still keen. Having slept on it, it feels so right. I responded.
‘Great! I agree, it does, doesn’t it?’ Lindsay said.
We had a good breakfast and enjoyed chatting over a leisurely coffee at the end. We talked for so long that we realised that we would be pushed for time to get a taxi and get to the office on time. Not that it really mattered as we kept our own schedules but it looked good if company management were there for opening time!
We managed to arrive with minutes to spare and went on in and got caught up in the minutiae of managing an outpost office. One thing that was good was that they had set aside their meeting room for us both to use as out temporary office when we were there. It was one of those cool glass walled on two sided rooms that had that special glass that would become totally opaque at the touch of a button on the central control.
About half an hour before lunch, we both found ourselves back in the office, alone. Lindsay looked over to me.
‘You know what I’d like to do right now?’ she asked
‘No?’ I replied, looking up at her.
‘I’d like to crawl under this desk, take your cock out and suck you off until you came in my mouth!’ Lindsay stated.
‘Ummh, Lindsay, I’d love that. Fancy trying it?’ I asked.
Lindsay was already reaching for the control unit to frost the glass when there was a knock on the door. Lindsay looked at me and raised her eyebrows as someone walked in and the moment was lost.
At lunchtime, we went to a local mall to eat as it was the closest place with a decent restaurant in it. We had a light lunch and then wandered round the mall aimlessly for a while before chancing on a disable toilet that had no one nearby. I grabbed Lindsay and dragged her inside.
I pushed her up against the wall and kissed her hard, glad to feel her kiss me back, she pulled my head onto hers and returned my kiss with interest.
My hands moved up to her breasts. They looked fantastic today, straining against the white blouse she was wearing.
‘Lindsay, I’ve been staring at your breasts since this morning, they look fantastic.’ I said lustily.
‘Play away, they’re all your whilst we are away, my whole body is!’ Lindsay replied.
We resumes kissing while my hands roamed all over her blouse and bra encased tits. Lindsay’s hand had reached down and was fondling my by now hard cock through my pants when a knock came on the door. We pulled apart and looked at each other and laughed. We straightened ourselves out and opened the door to a startled little old lady and walked away happily back to work.
The afternoon was hard as I just wanted to ‘play’ with Lindsay but had to do something. Lindsay felt the same way as she suggestively undid a button on her blouse when we were alone and leant forward for me to enjoy a view of her cleavage. The button was quickly done up again as the door was again opened. It seemed we couldn’t catch a break.
 At the end of the day we bid our farewells to the team in the office and left for the day. We had one more night here and then would catch a flight out early the next morning.
Back at the hotel, we managed to keep our hands off each other until we got to Lindsay’s room. Once the door was closed we were all over each other. We were like horny young kids, not 30 somethings! We were kissing and trying to undress each other, getting in each other’s way in the rush to disrobe!
Eventually all our clothes were off and that seemed to calm us down. We stood there in the middle of the room kissing, my hard cock squashed between our bodies. My hands were roaming all over Lindsay’s ass, cupping her cheeks and having the best grope and fondle ever!
I broke the kiss and led Lindsay over to the bed.
‘Wanna sit on my face?’ I asked.
‘Oooh yes please!’ Lindsay replied enthusiastically.
I lay down on the bed and Lindsay climbed on and straddled my face.
‘I want you to dive straight in, no teasing, eat me straight away.’ Lindsay ordered.
I was happy to oblige and when she lowered her pussy down onto my mouth I went for it and thrust my tongue right into her pussy. This made Lindsay gasp and grind herself down harder. I held onto her ass with my hands and used them to help guide her where I wanted her to be. My tongue was lapping happily at her slit, enjoying the increasing juices, staying away from her clit for the moment. I gave her long licks, making sure I got a good tongue onto her asshole before moving up and licking the length of her slit, ending up just short of her clit.
I continued this for a while before making sure that I then included her clit in my licks. Lindsay exploded and thrust with her hips, grinding her pussy onto my mouth, trapping my tongue on her clit. I let her have it full force, sucking and licking it hard.
‘Yeah, yes, yes, yes! Like that, just like that, keep going! Uh, uh, uh, uh!’ Lindsay moaned.
I upped my intensity and this drove Lindsay wild, she was bucking her hips, desperate to keep her clit in contact with my mouth. Lindsay soon exploded into orgasm and her thrusts calmed down accompanied by a soft mewling sound as she rode out her orgasm on my face.
When her breathing had returned to normal, Lindsay climbed off and straddled my stomach and leant down and kissed me passionately. As her juices were coating my face, we soon became a wet mess as we shared a post orgasmic kiss. In this position, I could feel the very tip of my cock pressed against her wet pussy. It felt amazing, her hot, slick pussy radiating heat against my pulsating cock, desperate to enter her. Even in my clouded lust I knew better. Lindsay broke off our kiss, obviously feeling the same sensations.
‘Oh my, your cock feels so good nestled against my pussy like that. I know we can’t fuck but do you mind if I stay in this position for a while? The feelings shooting through me after that amazing orgasm are incredible.’ Lindsay said.
I didn’t bother to respond, I just pulled her head down and resumed our tongue lashing in each other’s mouths.
My cock was at the gates of heaven and it could feel nirvana ahead of it. It had a mind of its own at this point and I could feel myself lift my hips ever so slightly to increase the friction on my cock head with Lindsay’s pussy.
‘Ummh, it feels soooo good there.’ Moaned Lindsay into my mouth.
‘Lindsay, we can’t.’ I said, coming back to my senses.
‘You’re right.’ Replied Lindsay climbing off me and laying down at 90 degrees to me, her head resting over my navel.
This gave her the perfect position to reach her tongue out and flick the end of my cock. It felt great and Lindsay continued with this teasing for a while. I let my hands roam up and down her smooth back, down over her ass and back up again. Lindsay moved her head forward and sucked the end of my cock into her mouth. She continued her teasing with just my cock head in her mouth, lashing her tongue all over and round it, building me up into a frenzy of lust.
Lindsay then moved her head down and took more of my cock into her mouth. I reached down and put my middle finger onto her asshole and pushed it in, causing Lindsay to moan loudly, the vibrations in her mouth adding to the sensation on my cock in her mouth. I put my other hand on the back of Lindsay’s head and pushed gently, causing her to take more of my cock in before releasing her and repeating the process. Lindsay moved her head in unison with my urges and she was soon building up a fantastic rhythm and giving me an excellent blowjob.
I increased the speed of my finger going in and out of her ass, making Lindsay moan continually on my cock. She had one hand on the base of my cock and was furiously wanking me as she sucked me off. I felt myself preparing to cum.
‘Lindsay, I’m going to cum! I want to spray it on your face.’ I said.
Lindsay moved her head back slightly so she was just licking the end of my cock, her hand moving in a blur as she wanked my shaft.
‘Lindsay, I’m cumming, I’m cumming.’ I blurted out as the first ropes of cum boiled up out of my balls.
Lindsay stopped licking my cock head and just wanked me off close to her face. I felt myself erupt and Lindsay continued with her wanking, not stopping until every drop was out of my balls and on her face. She then licked my cock again, obviously hunting for any stray bits of cum that weren’t on her face.
‘Wanna see the mess you’ve made?’ Lindsay asked me.
With that she sat up and turned her face to me. Her face was plastered in my cum. Both eyes were nearly glued shut, her cheeks and lips were covered and there was even some on her forehead and in her hair.
‘Wow! Lindsay, that was amazing, thank you. I hope that was alright?’ I asked
‘It was awesome! I loved it. But next time, I wanna be looking in your eyes as you cum on my face.’ Lindsay replied.
She then licked her lips and used her fingers to brush the cum off her face and into her mouth. It was such an erotic sight, her eating my cum off her face.
We were both pretty wiped after those immense orgasms, Lindsay again commenting that it was one of the best of her life! Her husband must really neglect her I remember thinking!
We went to clean up before dinner. I went back to my room to get clothes and we met again in half an hour outside Lindsay’s room and walked down together.
We went to the bar and had a couple of drink before having a great dinner in one of the hotel restaurants. We had discussed going out somewhere but wanted to get back to the room to have more time to play!
Over dinner Lindsay quizzed me about my lingerie fetish, getting a better idea about what turned me on. She said that she would make sure that she had everything that I liked with her next time. We also took the time to lay some ground rules for when we were away. We agreed that it would not be a good idea to call or whatsapp each other when we were apart with our families. Any communication should be done through the work email to ensure we did not get caught out by our partners. We also decided that Lindsay would avoid coming to my home city (I live there primarily for my wife’s work, not having too much to do in our office there as I tended to work out of Headquarters. Lindsay agreed to palm this off on someone else so we were not tempted by anything close to home! The same went for when I visited HQ as that would also not be safe for her as she lived in that city.
The subject moved onto sex and what we were doing. Lindsay told me that she just loved what I was doing to her pussy and how it made her feel. Lindsay even said how much she was getting out of our anal play, something she had never experienced before! I assured her that I loved my cock in her mouth and exploring her body with my tongue and hands. We looked at each other and agreed that this could be the perfect relationship, each of us getting something we wanted that our partners could not or would not provide for us. I wondered if she would consider letting me fuck her ass but felt it was a bit early in our new relationship to ask that, even with a few drinks over dinner!
After dinner we went back to Lindsay’s room for more ‘playing’, as she put it! Once through the door, she turned round and invited me to unzip her dress. I gently grasped her shoulders and rubbed her up and down, before taking the zip and slowly running it down the zipper. Leaving the dress on but still on her shoulders, I leant forward and gently kissed and licked my way down her spine, from her neck to the zip bottom, just above her panties. Once at the bottom, I reached inside her dress and fondled her breasts that were encased in her bra.
I took the dress off her shoulders and let it fall, leaving Lindsay stood there in just her bra and panties. I knelt down behind her and eased her panties down to the floor. I then buried my face in her ass as she stood there, flicking my tongue out to find her bum hole.
‘Lindsay, kneel on the bed for me.’ I commanded her.
Lindsay went and assumed the position, taking her bra off as she went over there. I crouched down behind her, savouring the view of her pussy and asshole exposed to me in this position.
I started with her asshole, pushing my tongue onto her little starfish and licking all around it before pushing my tongue into her yielding anal ring, enjoying the spicy aroma of her ass as I penetrated her with my tongue. I had a thumb on her clit and was gently rubbing. Lindsay was gasping again as she was pleasured. Her foot started rubbing my crotch through my pants.
‘Take your clothes off, then please continue with what you were doing?’ Lindsay said.
I did so and then resumed my reaming of her ass as her foot found my naked cock and rubbed me to full stiffness. I allowed two fingers to enter her pussy as my thumb continued its steady rubbing of her clit. With her pussy and ass being stimulated, Lindsay was now moaning loudly, begging me to keep going as her pleasure levels increased.
‘Oh yes, yes, yesss! Keep doing that, keep doiiiiing…….. uuugh, uuugh, yes, yes!’ Lindsay panted out.
I was now alternating my tongue between her asshole and her pussy. When my tongue was in her pussy, my nose was rubbing her asshole, keeping the stimulation there. Lindsay had a massive amount of pussy juice leaking out of her cunt and I was trying to lap it all up. Lindsay had an orgasm hit with me stimulating her ass, pussy and clit, she pushed her ass back at me, making me increase the pressure I was putting on all three areas. Lindsay dropped her head to the bed sheets and let out muffled cries as her body shook and she orgasmed for what seemed like ages.
‘Oh that’s amazing again. Now I want you to rub your cock all round my pussy. I need to feel your hot cock touching my pussy.’ Lindsay begged.
I knelt in between her legs and rubbed the head of my cock all round her pussy. Lindsay was so wet that my cock was quickly covered and the sensations on my sensitive cock head were incredible. Feeling Lindsay’s hot pussy on my cock felt out of this world. I was desperate to just thrust forward and fuck her but I somehow managed to hold off doing it. I continued to move my cock around, now making sure that it moved over her puckered anus as well as her pussy.
Lindsay was loving it as much as I was, she was breathlessly saying,
‘Oh yes, your hot cock on my pussy feels so amazing. I love it, oh yes, oh yes! Rub it on me, make me feel your cock, rub your cock head through my pussy lips.’ Lindsay moaned.
I targeted her pussy lips and allowed my cock head to just nestle in between her inner lips and rub in very small movements. The feeling was electric as her slick wetness seemed to engulf my cock, making me grunt loudly.
All it would take was one small thrust forward and I would have slipped straight up her pussy. I didn’t want to risk it though as we had an agreement. Her asshole though? Well we hadn’t mentioned that!
I removed my cock from the outside of her pussy and rubbed it round her tight asshole, smearing her pussy juice and my pre-cum all around her anal opening.
‘Uummh, that feels good as well!’ Lindsay moaned back at me.
I took that as permission to continue and increased the pressure on her tight asshole. Lindsay stiffened and pulled away.
‘I’m scared it will hurt. I want to let you fuck my ass, I really do but I’m scared of the pain.’ Lindsay said.
‘Lindsay, we don’t have to do anything you’re not comfortable with. How about I stop that now and we work on loosening your bum hole together so that we can do it sometime in the future?’ I said.
‘Do you mean you’ll buy me a butt plug? I’ve heard about them and as horny as I am now, it sounds quite appealing!’ Lindsay said.
‘Sure, let’s get you one of those and then we’ll fuck another time!’ I said, relieved that she had not said no to anal sex.
I stood back off the bed and Lindsay turned round and sat on the edge of the bed. She hungrily took my cock straight into her mouth, going down as far as she could on it before releasing me and then repeating the process. I took a hold of her hair either side of her head and used it to work her mouth around my cock, pushing her deep onto it and then pulling her off of it.
I wasn’t far from cumming at this rate and wanted to look her in the eyes as I came in her mouth.
‘Lindsay, I’m going to cum into your mouth and I want to look into your eyes as I do so.’ I said.
Lindsay immediately looked up and I pistoned my cock faster into her mouth, feeling her incredible suction, enjoying the sight of her hollowed out cheeks as she sucked me off.
Pretty soon I was ready and I looked her in the eye as I held her head mid way on my cock and spurted rope after rope of cum straight into her waiting mouth. I moved her head up and down short distances to help milk the cum out of my cock. Lindsay didn’t even blink at me as she looked at me as she swallowed every drop.
It was a fantastic experience, looking a beautiful woman in the eye as she swallowed your cum with your cock in her mouth. One I recommend for every man! Lindsay eventually released my deflating cock out of her mouth and we both collapsed back onto the bed.
‘Lindsay, that was amazing, thanks!’ I said.
‘Hey, I love it! And I love what you do to my pussy too!’ Lindsay replied.
We snuggled for a bit then went and cleaned up in the shower. We enjoyed a very sensual shower together, both spent from our earlier activities. It was very nice to relax with a beautiful, naked woman.
I went back to my room for the night and had no trouble getting to sleep after all the fun we’d had!
The next morning we were up early and after a quick breakfast, off to the airport to catch a flight back to HQ.
Everything went smoothly until we were sat in the airline lounge (thankfully we travelled Business class!) and the airline announced that there was an unexpected delay for an unspecified time. Luckily we were both able to make calls and use the wifi for emails and quick FaceTime calls. Technology really makes life easier sometimes!
We worked away for a couple of hours, and I felt my horniness levels rising again. I moved closer to Lindsay and said,
‘Lindsay I really need to cum one last time before we get back. How about it?’ I suggested
‘Ummh, me too. I’m so horny right now. Shall we risk going off to the restroom together?’ Lindsay suggested.
I was about to take her up on it, in fact, I was already rising out of my seat to go, when they called our flight! Typical, a delay and then just when it was about to get interesting the delay doesn’t even work in your favour!
‘To be continued!’ I said, putting my tablet and other items away.
Lindsay just winked at me and we made our way to the gate. Thank god for priority boarding for business travellers! We were soon seated in our seats enjoying a cold drink whilst the rest of the plane boarded. We were sat together, Lindsay next to the window and me in the aisle seat to her right.
Lindsay leant over and whispered in my ear, ‘I’ve never done it on a plane before, how about we sneak into the toilet and see what we can manage?’
‘Yes, we will. Now, Lindsay, take off your panties and give them to me. Do it now!’ I told her.
Lindsay looked at me and smiled, ‘OK kinky one, I’ll try!’ she replied.
With that she opened her blanket and spread it over her lap. I could see her hands working her skirt up over her hips and then see her legs moving as she eased her panties down. Eventually she bent over and picked them up off the floor and pressed them into my hand. I covered them with my hand and brought them to my nose to sniff her aromas. I then put them in my shirt pocket.
‘Oh my god! That was such a turn on! And to see you sniff my panties after I gave them to you! I’m so horny right now!’ Lindsay whispered to me.
I reached my hand over and let it slide under her blanket. I slipped it under her skirt and brought my fingers up to find a very wet pussy indeed. I gently rubbed her for a moment, eliciting a groan from Lindsay before withdrawing and leaving her frustrated and even more horny.
We soon took off and settled in to the flight. There were a few others in business class but it was nowhere near full. When it was all quiet, I got up and raised my eyebrows to Lindsay and walked off to the toilet. I went inside and didn’t bother to lock the door. Sure enough, less than a minute later the door opened and Lindsay squeezed herself in with me and locked the door behind her. There wasn’t much room to manoeuver in and Lindsay was facing the door, having just locked it. I didn’t even let her turn round, I launched straight in and grabbed her boobs through her blouse and bra.
Lindsay leant her head back and we kissed awkwardly as I fondled her breasts. I pulled her blouse out of her skirt, pushed my hands up inside and lifted her bra over her tits, letting my fingers tweak her nipples. My rock hard cock was pressing into her ass and Lindsay reached behind her and stroked my through my pants.
With one hand working her nipples, I let me other trail down and pull her skirt up, Lindsay helping me to bunch it up round her waist. This gave me access to her pussy and I dived straight in with my fingers, working them over her clit and in and out of her hole.
I released her tits with my other hand and brought it behind her and gently worked her asshole, rubbing my middle finger round her puckered anus whilst fingering her pussy with my other hand. Lindsay was writhing against me and she went wild when I pushed a finger into her asshole as I rubbed her clit.
‘I want you to fuck my ass now!’ Lindsay gasped out.
I didn’t need a second invitation! I took my hand out of her pussy and undid my pants and pushed them and my boxers down to my ankles. My cock was a hard as iron at the thought of finally invading Lindsay’s bowels with it!
I moved my hand back to her pussy and assaulted both of her holes, adding a second finger into her ass to loosen her anal ring a bit. I had noticed some hand cream in the toilet and I squirted some out and rubbed it into Lindsay’s ass and repeated it onto my cock.
I bent my knees a bit and Lindsay stood on tip toes and I brought my cock to rest against her asshole. I pushed forward gently, feeling her incredibly tight anal ring, before my cock head pushed through and I was part way into her ass. Lindsay let out a very loud moan, somewhere between pain and pleasure. Before continuing, I took her panties out of my top pocket and reached forward and stuffed them into her mouth to try and keep her quiet!
I then pushed forward again, inching a bit more of my cock into her asshole before withdrawing a little and pushing in again. I kept playing with Lindsay’s clit whilst I was starting to fuck her ass, to ensure she got maximum pleasure before I plundered her asshole to hard!
Lindsay was moaning and writhing and even starting to push her ass back against my very gentle thrusts forward. I took this as a sign to speed up and I duly did so, driving more of my shaft into her asshole, feeling her anal ring clenching tightly onto my cock, gripping me like a vice.
Lindsay was now meeting my thrusts and was obviously accustomed to my prick in her bowels. I left her clit alone and grabbed her hips and began pistoning my cock in and out of her ass, making my cock almost leave the grip of her anal ring before plunging back in, her asshole eating up more and more of my cock before I was finally fully inside her. I stopped thrusting and savoured the feeling of my cock buried deep in her ass. I could feel that Lindsay had brought one of her hands down to her pussy and she was frantically rubbing her clit, moaning out into the panties in her mouth, which were doing a good job off muffling her cries!
I was now plunging my cock hard and fast into her asshole, enjoying fucking a virgin ass for the first time. Lindsay’s anal ring was gripping my tightly and the sensations running through my cock felt incredible. I could feel Lindsay trembling through one orgasm and I knew I wouldn’t be too far behind her. I took long, deep strokes into her ass, feeling the familiar build up in my balls.
I took several hard, quick thrusts before burying myself deep in her asshole and my cock erupted my hot cum deep into Lindsay’s bowels as I moved my cock in small motions, allowing her ass to milk all of my creamy jizz out and into her well fucked asshole.
I could hear Lindsay panting as I came into her bowels and she gave a low moan as each spurt hit her hot insides, painting her bowels with my cum, filling her up with my seed.
Eventually I was spent and I let my by now flaccid cock slip out of her asshole. Lindsay turned round, took the panties out of her mouth and we kissed passionately.
‘That was the most incredible sex of my life!’ Lindsay said. ‘I want to do that again and again. When you came and I felt your cum hit me was just amazing!’ Lindsay went on.
‘I agree, that was simply amazing! I can’t wait to repeat it!’ I replied.
‘There is so much cum leaking out of my ass right now! Pass me some tissues.’ Lindsay said.
I reached over and took a handful of the paper and Lindsay reached behind her and mopped up my leaking cum as best she could.
‘You know Lindsay, I love watching my cum run out of a pussy or asshole, perhaps I can watch it next time?’ I asked
‘You sure can! I’d love you to fill me up again but maybe wear a condom if we do it in a public place again as you cum is everywhere! I’m going to be stinking of cum when we get off!’ Lindsay laughingly said!
‘Don’t worry, remember there is a business lounge with a shower you can use to change at the other end!’ I reminded her.
We cleaned up as best we could and made our way back to our seats and enjoyed the rest of the flight making plans for our next trip away together.
Arriving at our destination, Lindsay went ahead to clean up properly and I waited for her.
‘Can’t go home smelling of your cum!’ she said as she rejoined me.
We said our goodbyes there as, due to the flight delay, I was going to catch my next one home.
I couldn’t wait for the week after next when we would travel together again!!

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