I was in Chicago for a couple of days of business meetings which usually also means a couple of days of extreme boredom in the meetings and being too tired to do much afterwards. Thankfully my company put me up in a nice hotel just across from the convention hall we were meeting in so after I’d finished for the day I figured I’d stop at the hotel bar for a beer or two before going back to my room. I was just leaving the hall when I heard a woman’s voice call my name. I didn’t recognize the voice and figured she must be calling to someone else when I felt a hand on my arm and the same voice said, “If you’re not Dave I’m going to feel very silly”.
As I turned I took a quick look at her – about my age (40ish), a few inches shorter than my 5’10”, green eyes, reddish blonde hair, a great smile and as my eyes flicked lower I could tell she was quite slim and seemed fairly well built. She had on a nice blouse with an open blazer over it and a skirt that ended just above the knees allowing a more than a glimpse of her very shapely, nylon covered legs. That only took a second or two but it was a good 10 seconds before I could place the face. “Tina? Tina from Edgemont High?”
“Oh thank God you’re who I thought you were. I wasn’t sure you’d remember me but at least I don’t have to explain myself to a stranger!”
She was smiling now and that made her look even prettier. “You look great Tina, it took me a second but sure I remember you. Functions, outside row, second desk back. You had glasses then and your hair wasn’t the same colour.” As I was talking, I was thinking – “she was the hottie that everyone wanted but she’d just tease most of the guys who asked her out and never dated anyone for long.”
“Wow, good memory! Laser eye surgery and a bottle of hair dye does wonders. What are you doing in Chicago?”
“Here for a few days of meetings, the company I work for is rolling out a new line and wants everyone to be updated before it hits the stores. How about you?”
She seemed to hesitate for a couple of seconds before replying, “Just here for a couple of days on business myself. Where are you staying?”
“Right across the road at the Hilton and you?”
“Same place. Hey, want to grab a beer and catch up?”
“Sure, I was already planning on a beer or two. I’m going to go up and get out of this suit, check email and I’ll join you as soon as I can.”
About 30 minutes later I walked into the bar and saw her at a booth near the back. As I got to the booth she surprised me by standing up and giving me a big hug. I instinctively put my arms around her too and as I was wondering what the hell was happening she whispered in my ear, “there’s a guy a few tables over that’s been hitting on me since I got here – I finally told him my boyfriend was meeting me here so I need you to be my boyfriend.”
I catch on pretty quickly so I whispered right back, “Ok” and as we released each other she leaned in and kissed me. I didn’t know if she was married or not and I wasn’t so I figured if she wanted to put on that good a show then I was all for it. I let one hand slide down her back until I could just feel the curve of her ass and brought the other one up to cup her face and drew her back to me for another kiss. At first she was a little surprised but quickly relaxed and I could feel her lips clinging to mine as we kissed. When we pulled back again I could still taste a hint of strawberry from her lipstick.
All of a sudden I had a feeling this could be a very interesting evening. We sat down at the booth side by side, I held her hand and my other arm slid very comfortably around her back. I leant in and nuzzled her neck and at the same time whispered, “which one is he?” and as I pulled back, she turned her head and started kissing and nibbling my neck right from the collar bone all the way up to my ear.
When she got to my ear she whispered back, “dark hair, wire glasses, jeans and a white muscle shirt”.
Thankfully the waiter came up to see if we were ready to order which gave me a good opportunity to look past him at the other patrons. I spotted him pretty easily and was pretty sure he looked away just as I glanced over – a pretty average guy about my age. We ordered a couple more beer, a plate of nachos and continued talking. At least knowing where he was sitting I knew he couldn’t hear us so we were able to talk. While we were waiting for our order I found out she was recently divorced which explained the whiter skin around her ring finger, had no kids and actually lived only 50 miles from where I did.
The food and drinks arrived and we talked some more as we ate. At one point I looked up and Tina had some sour cream from the nachos on each side of her mouth. I have to admit – it was kind of sexy and I had a quick thought of other cream around her mouth before I reached out with one finger, wiped it off and then licked the finger. Just to keep up the show (ya right!) I leant over and licked the other spot off. I wasn’t sure how she’d take it but as I licked she turned her head slightly so my tongue slid across her lips. It quickly went from a light touch of my tongue to our lips pressed firmly together and I know I felt her tongue slide forward to meet mine. I’m not sure how long we kissed for but it seemed neither of us wanted to end it. The bar wasn’t well lit or she’d most likely have noticed that there was now a bulge in my pants that hadn’t been there before the kiss.
As we continued eating, she leant over to get some more nachos and put one hand on my upper thigh, at first I thought it was perfectly innocent but not only did it stay there when she leant back, I could feel her hand moving up and down slightly and her fingers exploring the inside of my leg. As luck would have it, the side she was exploring was the side that my now hard cock was trapped against and when she first brushed it she stopped quickly and I fully expected her to pull away but when I looked over at her she had a very sexy smile on her face and her hand continued higher until she was stroking the length of my shaft through the clothing.
Ok fair’s fair I thought so I brought my arm back and ‘accidently’ knocked my knife onto the floor. As I bent down to get it I put my hand on her leg for balance and immediately noticed that my hand was on bare skin not nylons. Thinking I’d surprise her, I ran my hand up her leg under her skirt and the surprise became mine when not only didn’t she stop me, her legs opened a bit more and my hand was soon right against her panty covered mound. As much as I’d like to have stayed there, it was a fairly cramped position so I sat back up but not before running my fingers up and down the bulge of her noticeably damp pussy a few times.
Once I was back beside her, we continued teasing each other until the meal was done. Just as we were finishing, Tina said, “Oh good – he’s getting up and leaving.” When I looked over, I saw him heading out but instead of leaving out the front, he went out the side door which led into the hotel lobby. She saw it too and groaned, “Oh shit, I’ll bet he’s staying at the hotel too!”
We had another drink before deciding to call it a night. I was pleasantly surprised that after the guy left Tina made no effort to move away from me but I wasn’t sure if the game was still on or not. She must have felt my uncertainty because she looked right at me and said, “I was really enjoying myself and I think you noticed when your hand went up my leg – just because he’s gone doesn’t mean we can’t keep going” and as she finished she leant in and gave me an even longer, hotter kiss than we’d had so far. As we kissed I slid my hand back up her bare leg and excited she was – her pussy felt damp before but was definitely borderline wet now.
“Seeing as you’re my boyfriend it only makes sense that we go back to our room together don’t you think?” she asked.
“I’d love to…which ‘our’ room are we going to go to?”
“Seeing as my reservation got messed up and they ended up giving me a penthouse suite why don’t we go there?”
Nothing else really needed to be said as we paid the bill, got up and headed out hand in hand. The elevator door hadn’t even shut when we were kissing again except this time our bodies were pressed as tight together as our lips and just knowing that it wouldn’t be long before we were skin to skin got me even harder than I already was. We made it from the elevator to ‘our’ room in record time and as soon as we were inside we were kissing and touching each other like a couple of horny teenagers. Taking a quick look around I noticed it was closer to an apartment than a hotel room. There was a kitchen, dining area, living area and when we finally got to the bedroom it was huge. There was a king size bed, ensuite bath as well as closets, dressers and a huge TV.
We’d started undressing on the way to the bedroom but now that we were there we quickly got out of what clothes were left off of each other. She undressed me first, running her hands over my shoulders, down my chest and then down my legs as the pants came off. I heard a quite but approving “mmmmm” as my hardon sprung into sight when she pulled down my jockeys. Once I was naked it was her turn and I made sure my hands, lips and tongue tasted and teased a quick path from her shoulders to her bra and as that came off I saw her breasts for the first time. Firm, smooth with very perky nipples that stood out proudly from her chest. From there I worked my way down her belly until I could undo her skirt which fell to the floor revealing that wonderfully wet mound that I had only touched so far, nicely covered by the sheer material of her panties. Those quickly came off as well and as it did I told her to sit on the bed.
As she sat down, I knelt down in front of her and soon my face was at the same level as her pussy. I wanted to dive right in but forced myself to feel and kiss my way up her legs – the closer I got to her crotch the wider she spread her legs. It was a beautiful sight – smooth as her legs and glistening with her juices. Just to tease her I planted a small, quick kiss right on her slit and she moaned and I swear I saw a few more drops of fluid ooze out. If I hadn’t been as horny as I was, I would have teased her longer but I couldn’t hold back so started at the very bottom of her slit and with as light a touch as I could, I ran my tongue slowly right up the slit to the hardness of her clit. When I touched her clit she screamed and came – not a few drops this time but a small squirt of fluid that I felt hit my face. That just turned me on more so I kept going, alternating between long slow licks, fast tonguing in and out of her hole and sucking on her erect clit. I’m not sure how many times she came some were so close together that it was hard to tell whether it was one or more but it was easy to tell when the biggest one hit. She grabbed the back of my head and pulled me against her pussy, screamed, moaned and I felt not one but three distinct gushes of fluid spray my face. I could feel her legs trembling against my head and shoulders and she pretty much collapsed backwards onto the bed.
I moved up beside her and she rolled to me, kissing and licking her juices off my face and eventually just laying there being held. It took a few minutes for her to get her strength back and she said, “That was the best orgasm I’ve ever had – I just hope I can do the same for you” and slid off the bed to her knees on the floor. I got the idea pretty quickly and sat up in front of her. At first she just stroked me gently with her hand but then she started kissing my legs and stomach. Just as she moved to take my head into her mouth I heard a clunk, the closet door opened and out came the guy from the bar except now he was naked.
Instinctively I moved to protect Tina and deck him until I heard her scream “No, he’s my husband”
Ok, now that was a fuck of a mood killer, even more when I heard him say, “I can’t go through with it – I don’t want to see you fuck him after all”
For the next couple of minutes it was like I wasn’t even there as she yelled at him.
“What the fuck do you mean you can’t go through with it? You’ve been telling me for the last year that you wanted to see me fuck someone else & I’ve always said no because I love you and don’t want to have sex with anyone else but you kept bugging me about it. You bring home porn flicks of wives getting fucked by other guys, you tell me how much it would turn you on to see me fucking someone else and finally I gave up and said yes just to get it over with as long as I could choose who I had sex with ’cause your friends are way too creepy. We got this nice room so you could hide in a closet and watch and when I saw Dave I figured at least I’d known him in high school and would be more comfortable with him. We had a great dinner – touching, kissing and teasing and he got me wetter than you have in a long time. Now he’s given me a mind blowing orgasm with his tongue which you won’t even do and as soon as I start to go down on him you decide you can’t go through with it. Well FUCK YOU! I’m hot, I’m horny, he turns me on and if he’s willing I’m going to go through with it. You’ve got two choices – leave and you can consider the marriage over or sit the fuck down and watch like you were going to and maybe there’s a chance of saving whatever it is that we’ve got.
The look on her husbands face was a combination of total shock and surprise. Then Tina looked at me and said, “I’m really sorry about this, you weren’t ever supposed to know he was there, I was supposed to take you to bed and make sure that shithead there could watch everything. I won’t blame you if you walk out of here but I wasn’t lying to him – you’ve gotten me hotter and wetter than he has in years and I’d really like to have sex with you except that now it’ll be for you and me, not for him. Are you up to it?”
I was going to make a joke about not being up at all anymore but when I looked down, I realized that obviously my cock hadn’t heard much of the conversation and was still ready and willing to go. “So you really weren’t interested in me, I was just being used so your husband could have his fantasy come true and now he doesn’t want it? Well you’re a damn good looking woman and if he’s stupid enough to want you to fuck someone else then I’m ok with it on one condition – I don’t want to have to keep one eye on him in case he does something stupid – do you have anything like pantyhose to tie him up with.”
She gave me a huge smile and rummaged through her stuff coming up with a couple of pairs of nylons. I could tell he didn’t like the idea but soon his arms, legs and chest were securely tied to the chair that he’d pulled out from the corner. She looked at him and said, “enjoy what you’re going to see – if you make any noise I’ll gag you with something” With that she turned back to me and said, “where were we – oh ya, I was going to suck on your long hard cock until you cum in my mouth”
I’m sure the description was more for his benefit but my cock certainly twitched when I heard it. Without hesitation she took me into her mouth and was soon licking, sucking and stroking me towards one hell of an orgasm. I was doing my best to hold back and I think she could tell because she paused for a second as she stroked me and whispered, “go ahead – cum in my mouth!”. Not wanting to disappoint her it wasn’t any more than another minute and I did just that. Pulse after pulse of cum shot down my shaft and into her mouth and while a little bit oozed out the corners of her mouth I really couldn’t tell if she’d swallowed it or not. The answer became pretty clear when she stood up, walked over to her husband, grabbed him by the hair, tipped his head back and kissed him. I could tell by his reaction he wasn’t enjoying it and when she finally pulled away from him and he started spitting my cum out of his mouth I could tell why!
“There you go, you wanted to see someone cum in my mouth or on my face – I’ve done one better, I’ve shared it with you!” and with a great big smile she came back to the bed. If the sex is good enough I’m usually good to stay hard for a while and her blowjob had gone way past just ‘good’. Up until now, hubby had stayed quiet but when she lay on her back, spread her legs and told me she was ready to get fucked he blurted out, “No, don’t! I get your point.”
“No, I don’t think you do,” she replied, “originally this was all about you – you getting off watching me get fucked, you living out one of your fantasies, you having your way even though I said I didn’t want to – now it’s about me. I’m hot, I’m horny and I want to know if his cock feels as good in my pussy as his tongue did. I want to get fucked, I want to cum and I want to keep doing it until neither of us can keep going. Last warning – one more word out of you and you’re going to get gagged!”
That seemed to shut him up and when I felt her hand on my erection pulling me closer I happily obliged. She wasn’t a virgin but she was still incredibly tight, even with all her natural lube my 7″ rod was still a very snug fit. Seeing as I’d just cum I didn’t have to worry about cumming again too soon and she had said she wanted to get fucked so once I was in all the way I pulled back and then drove in again. Her gasp was a mix of surprise and pleasure and seeing as she kept moaning and gasping with each thrust I figured the surprise part was over so the majority of it had to be pleasure. It was only a few minutes of hard pounding before she came for the first time since I’d entered her and it was a big one. Her whole body tensed up, she arched against me and then relaxed, as I felt her relax I also felt a gush of warmth against my crotch and realized she’d squirted again. Now I slowed down and varied both the speed and the depth until she was building up to another orgasm. I teased her for a while – stopping just when I felt she was ready to cum and then starting again when she relaxed a bit.
Finally she said, “no more teasing, I need to cum again.” Instead of keeping going, I pulled right out and guided her onto her side facing her husband. Once she was over, I pushed her top leg up toward her belly which gave me perfect access to her pussy and then I thrust back inside her. She quickly found that in this position both the depth and the angle changed and I was now hitting areas that I hadn’t a few minutes ago. As I built up both depth and speed she was telling me not to stop but I had no intention of stopping again until she’d had another orgasm and I told her so. I wasn’t disappointed either – this one was even bigger than the first one. It started with a few small moans and light pulsations of the walls of her pussy with both the moans and the pulsations increasing in volume and intensity until I was actually having problems getting my cock back into her. Rather than take a chance on getting pushed out I pushed back in as deep as I could and held it there. That seemed to put her over the edge and with a scream she almost convulsed as she came, and then went pretty much limp but the contractions continued.
Even after the big contractions were over I could feel little ‘aftershocks’ and with each one she shivered a little bit. I hadn’t cum yet but I was close so before she could totally relax I pulled her back over and pulled her up to her hands and knees and thrust back into her doggy style. It wasn’t my favourite position but it did give me the best thrusting and thrust I did. I started slow but within a dozen or so strokes I was going full depth and almost as quick as I could go. This one wasn’t for her it was for me and by the way she started thrusting back against me I could tell she knew it. I doubt I made another thirty strokes before the orgasm that I knew was close erupted. I could feel the surge and even though it was my second orgasm I pumped at least 6 strong spurts of cum deep into her pussy.
This time it was me who pretty much collapsed after I was done cumming. It had been some of the most intense sex I’d had in a long time and as much as I hoped it wasn’t over, I also knew it could be a bit before I’d be hard enough to go again. We were pretty much laying together on the bed and Tina very naturally moved up against me and I held her close. As we relaxed and enjoyed what we had just shared she moved her head even closer and whispered so that her husband couldn’t hear, “If I get you hard again would you like to do my ass?”
Well shit that was like asking an alcoholic if he’d like a drink but I still wasn’t sure if the body was as willing as the mind and pretty much told her that.
“I’ve got faith in both our abilities!” and with that she guided me onto my back and started kissing her way down my chest. By the time she’d gotten to my belly my cock was already twitching and when her tongue gently licked the traces of both our cums off my shaft it started to swell. It did take a few minutes of very skillful sucking but eventually I was hard enough to go again and the thought of where she wanted it kept me hard as her lips pulled away. Now it was my turn to guide her back over onto her knees and slid my newly hardened cock back into her hot, wet pussy. At the same time she reached up under the pillow and brought out a tube of lube.
As I slowly stroked in and out of her pussy I took the lube and trickled some down the crack of her ass. I could see her rosebud almost pulse as the cool liquid hit it and could actually feel it pulse as my finger pressed against her anus. It was so tight that it took a few minutes just to work the tip of my finger in but bit by bit she relaxed and more and more of my finger found its way into her ass. Soon I had a nice easy rhythm going – in and out of her ass and pussy at the same time. When she was lubed and loose enough for one finger to easily slide in and out I added a second finger and worked those two in just as slowly. By the time she could accept two fingers easily I’d already felt a couple of small contractions from her pussy that told me she was building up to another orgasm. I wasn’t sure that she was totally ready for a cock in her ass but she obviously knew she was ready because she looked back over her shoulder and said, “Do it!”
Ok I thought, I know I’m ready so I pulled both my cock and fingers out of their respective holes and lined my cock up with her ass. I’d have thought that her husband had already figured out where things were going but apparently not because it wasn’t until the head of my cock started opening her butt hole up that he shouted out, “No, not her ass -she won’t even let me fuck her there!”
Obviously pissed, Tina pulled away from me and looked at him. “You were told, you were warned and you still won’t keep quiet” and with that she picked up her panties, wiped our combined cum from her dripping pussy with them and shoved them in his mouth, tying them there with another piece of her nylons. Now that he was gagged she kept going, “You know why I won’t let you fuck my ass? We’ve tried a few times and you always rush, never make sure I’m lubed or relaxed enough and it hurt too much every time. Right now my ass is slick, relaxed and you’re going to see what you’ve been missing because you never cared enough to make sure I was ready.”
With that she started to get back onto her hands and knees but I had a better idea. I got her to lay on her back and I put her legs up over my shoulders giving me perfect access to her ass as well as being able to see her face and touch her nipples and pussy. My cock was larger than the two fingers had been and she’d tightened up a bit from getting pissed at her husband but I took it slow, rubbed her pussy and clit and soon the head of my cock popped into her ass. I could tell by the look on her face it hurt a little so I stopped and waited. Sure enough in 10 or 15 seconds she started to push against my hardon letting me know she was ready for more. It went on like this for a few minutes – a little bit further in, she’d tense up, I’d stop and when she was ready she’d push against me. Finally I was all the way in and more to piss him off than anything I said, “There, you’ve got all 7″ of my cock in your ass – do you like it?”
“Oh ya, the feeling is wild! Be gentle but fuck my virgin ass.”
It wasn’t the first time I’d gone in the back way and I knew that this wasn’t the time or place to be pounding heavily so I stayed nice and slow, easing my shaft in and out of her ass, occasionally coming out just far enough that her hole started to close before I slid it back in again. As things loosened up I went a bit faster but no where close to the speed I’d been pounding her pussy earlier. “Reach down and play with yourself.” I told her.
She’d already started moaning but I could tell as soon as she started to finger her slit because her pucker tightened up around my shaft and I felt a couple of small spasms. The more she played with herself the more spasms I could feel around my shaft and I’d get an especially loud moan every time I either bottomed out in her ass or pulled almost all the way out before going back in. Other than the occasional grunt from her husband we’d both pretty much forgotten he was even there as we both built to yet another orgasm.
It had been a long time since I’d cum three times in as many hours (not counting my own hand) but I could tell that this was going to be one of those times. I knew she was building to a big orgasm so I was doing everything I could to not cum but it wasn’t helping a whole lot so I started telling her how tight her ass was, how hot and slick it felt and how good it was going to feel to fill her ass with every last bit of cum I had left. I don’t know if it was her fingers or the talking but all of a sudden my cock felt like it was in a vice and she let out a yell that was likely heard in the next room. The feeling of her ass clenching that hard on my cock was all it took and I started cumming too. Neither of us seemed to have the ability to move so we just braced against each other until our orgasms finished. Now I knew I was done for a while and just to confirm it my softening cock was released from her ass with a slight ‘pop’ and I could actually see her pucker slowly contracting back to the fully closed position. She fell forward, I fell partly beside & partly on top of her and we just lay there for a few minutes until I was able to roll over and Tina rolled somewhat on me. Without even thinking, I put my arms around her and pulled her close for a kiss – which turned into several before we finally pulled apart.
Looking over at her husband, Tina said, “Hey, he must have enjoyed himself after all.” and pointed out several splashes of cum on his belly and legs.
I wasn’t really sure where to go next, I’d never been in a situation like that and obviously neither had she because there was an awkward silence for a bit until I said, “Well, I
guess I’d better get back to my room.”
“Ya, I guess so…thanks Dave, thanks for everything.”
After I’d dressed, Tina walked with me to door and as we got there I pulled her close for several more kisses which she fully responded to then asked, “is it going to be ok – I mean is he going to get nasty when you untie him?”
“No, I don’t think so. I think he knows pretty much what will happen if he does.”
“Ok, but just in case, here’s my card. We don’t live that far apart and I’ve almost always got my cell phone with me if you need to call.” I made the offer not because I felt I had to but because I sincerely meant it even though in my heart I knew I’d likely never hear from her again. She gave me one last kiss before the door closed – “you never know, I might just take you up on the offer.”
A few months went by, work and life continued but unfortunately I’d yet to find anyone else who could compare to the feelings and the memories of my evening with Tina. It was a shitty, rainy, cold March night and I’d just gotten home, changed and was getting supper when my phone rang. I recognized Tina’s voice immediately and could tell she was upset. “Did you really mean it when you said I could call if I needed anything?”
“Yes, I meant it then and I still do – what can I do?
“Well, for starters you can come open your door and let me in, it’s cold and wet out here.”