I’d known Kate for over 25 years, her full name was Katherine but I was one of the few that could get away with calling her Kate. I used to work with her boyfriend, Mark and they got married a few years later. My girlfriend and I spent a lot of time together with them and another couple Pete and Jean – May 24 camping, New Years, Birthdays, BBQ’s – you name it and we were likely hanging out for it. Kate was shorter with long dark hair, slim, nice ass, not huge in the chest but very proportional to her build and generally what almost any guy would consider ‘beautiful’.
Eventually, I married my girlfriend but unfortunately within 10 years Mark and Kate got divorced. A few years later she met a guy in Dominican and she eventually brought him to Canada and they got married. At first everything with them went great but he started to become more controlling which eventually turned into verbal and psychological abuse so we didn’t see as much of her or them and eventually they split. This time the divorce was nasty, even more so because they had a son who was now 4. A few years after that, my first wife and I ended up divorcing as well.
Over the next 10 or so years we stayed in touch, usually by Facebook. I knew she’d gotten and beaten breast cancer; she knew my second wife needed three stents because of a heart attack but we never really got together on any regular basis.
Oddly enough, within 6 months of each other, my wife passed away from cancer and her current husband Don passed away from a heart attack. He was a fair bit older than she was and she’d mentioned a few times that it was more of an emotional relationship than a physical one because of his health problems and her mental issues from her ex, they still had sex but not on a regular basis. We each had support from family and friends but the old friendship returned and we soon found ourselves hanging out together either to watch a movie, go for a walk or just have a few drinks.
One Friday night we were watching a movie at my place and one of the scenes triggered Kate to break down in tears and without really thinking about it, I put my arm around her, pulled her to me and just held her. When it had passed, she said “thank you…I’ve had way too many nights of crying when there wasn’t anyone there.”
She didn’t really move away so I kept my arm around her and after a while I noticed she’d fallen asleep against me. The movie had been done for about 30 minutes when she started talking and crying in her sleep so I gently woke her to let her know she was ok and when I did, she pulled me to her so hard I thought she might leave a bruise. When she’d calmed down again, she just looked at me and said, “I’m sorry.”
I gave her a quick kiss on the forehead and said, “nothing to be sorry about, we’ve been friends too long for that. Are you ok to drive home?”
She thought about that for a bit and then said, “I am but….”
“But what?”
“I really don’t want to go home to an empty house. If it’s ok with you, could I stay here?”
I just smiled and said that would be fine. I didn’t have anything that would fit Kate for sleepwear so she settled for one of my t-shirts that went almost to her knees and I cleared the spare bed off. After letting the dog out for a pee and changing into a pair of boxers (I usually slept nude I figured I’d best wear something while she was there) I was just heading from the bathroom to my bedroom when I heard her say quietly, “Mike, would you mind just holding me again until I go to sleep?”
I’d had more than one thought over the years of what it would be like to end up in bed with her but none of them had been because she was scared. I lay beside her on the bed and soon I was on my side with her curled up against my chest and one arm around her. My plan was to wait until she fell asleep and then head home back to my bed so I was a bit surprised to realize I must have dozed off when I looked and saw the clock showing 3am. I also realized that I now had one hand over her small but very firm breast.
Not wanting to look like I was taking advantage of her if she woke up, I started to slowly move my hand away but as I did, she brought one of her hands up to hold mine in place. I froze thinking she was awake but then realized that she was still asleep so instead of waking her I figured I might just as well go back to sleep and deal with things in the morning.
When I woke up a few hours later, we’d shifted positions and now I was on my back with her arm plus a leg over me and her head against my shoulder. My one hand was on an almost bare ass cheek and her hand was laying right on top of my cock which was fully hard not only from ‘morning wood’ but also from her hand being right there.
I was just trying to figure out what she’d think if she woke up this way when I felt her shift, move even closer and then suddenly roll away with a ‘Shit!”
She looked around, then at me and I could tell she was almost ready to cry again so I said, “That’s not the reaction I like to get when I wake up with a lady.”
That got a bit of a smile followed by a very flustered, “I just wasn’t sure who’s bed I was in or who was with me.
That made me smile and ask, “So, does this happen often?”
That got me a well-deserved smack on the arm but at least she didn’t look like she was going to cry anymore. “I didn’t mean it that way. It’s just been so long since I’ve slept through the whole night without waking up crying that I was still a bit disoriented.”
I was a bit surprised when she rolled back so she was facing me and looked at me quietly for what felt like forever before saying quietly, “Would it be wrong if I said that it felt really good waking up with you holding me, me touching you and that I’d like to feel even more?
Knowing how much she’d been through with both her ex’s and then losing her husband recently I knew how hard it would be for her to say that so I reached over, touched her face before cupping her cheek in my hand then saying, “I’ve got to admit that I’m feeling pretty much the same way so if it’s wrong then maybe two wrongs can make a right – at least for now”. Before she could say anything, I leaned forward and gave her a very soft kiss on the lips before moving away again.
I wasn’t sure which way things would go so I was pleasantly surprised when she brought her face back to mine and returned the kiss except hers was firmer and longer before she pulled away. “So I take it that’s a yes?”
“Yes, if you want more, I’d love to be the one to give you whatever ‘more’ you need but I’d best let the dog out or there’s a good chance one of us will get poked with a cold nose before long.”
While I was waiting for the dog, I heard Kate get up and use the bathroom and I did the same before re-joining her in bed. We shared a few more kisses before I said, “I want to make sure of a couple of things. ”
With a bit of a puzzled look she said, “What?”
“Well, I don’t know everything you’ve been through but from what I do know, I just want to make sure you’ll let me know if you’re not comfortable with something or change your mind.”
A bit more relaxed, she smiled, gave me a quick kiss and replied, “Thank you, I certainly will. What was the other thing?”
“I hope you don’t have any plans until at least this afternoon.”
“Why?”
Now was my turn to smile, “Maybe I shouldn’t say it but ever since I first met you years ago, I’ve wondered more than once what it would be like to be the one holding, kissing and making love with you and now that it looks like it’s going to happen, I’m not planning on rushing things at all!”
With a soft, “That sounds perfect” she leaned into me and we spent the next few minutes just kissing softly and enjoying holding each other. Initially my hand was just tracing random patterns from her neck to her lower back but bit by bit, my ‘range’ expanded until I was caressing her ass and a breast but both through the nightshirt she was wearing. I knew she didn’t have big nipples but it was exciting to feel the little nubs harden and press against the fabric as I touched her. Her hands weren’t exactly idle either and by the time I was feeling her nipple harden against my hand, my cock was doing the same thing against hers through my boxers.
Eventually she pulled away a little, bit her lip for a second or two while she was obviously considering something. I got my answer when she sat up enough to pull the nightshirt up over her head and off. When I’d woken up with my hand on her ass, I was pretty sure there’d been a pair of panties there and with the way she was sitting I couldn’t be sure, but it certainly looked like there was nothing there now so she must have taken them off when she went to the bathroom.
I could tell by the way she looked at me that she wasn’t sure if I’d like what I was seeing or not so I gently I cupped the other boob in my hand, pulled her down on top of me, whispered, “Beautiful!” and gave her a much longer, more passionate kiss than we’d had so far. At first, I don’t think it was intentional but as we kissed, I could feel Kate pushing her hips down slightly against my crotch. After a minute or so of that, I started pushing back against her and when I heard her first soft moan, my tongue parted her lips for the first time. It wasn’t long before we were kissing passionately and grinding against each other like a couple of teenagers in heat.
Maybe she could have orgasmed just from the kissing and rubbing but I wanted her first cum with me to be a lot more intense so as much as I didn’t want to stop what we were doing, I slowly rolled her over and as we continued kissing, I ran my hand from her cheek, down her neck, along her side, over her hip and down her leg to the knee and then reversed and came back up except when I came back up I ran my hand over her breast and slowed just long enough to rub her nipple with the palm of my hand. That got a very sexy moan and a slight shiver so each time I ran my hand up and down her body, I spent more time touching her breasts and teasing her nipples. I also let my fingers get closer and closer to her crotch until they were regularly running up the inside of her leg and up across her pussy before continuing up the rest of her body.
When I felt her start to push her hips up as my fingers touched her pussy, I stopped so I could just admire her nakedness again as she lay there on her back. Her breasts were small but they stayed firm and pert, her belly flat and tight and her pussy beautifully bare. Before leaning back down, I whispered, “You look amazing!” and then kissed her some more.
There was lots more of her I wanted to kiss so I moved to her neck and slowly kissed my way down her chest until I was enjoying the feel of first one, then the other nipple against my lips and tongue. From the way her one hand was holding my head and the other one was touching my back; I was pretty sure she was enjoying it too. As I enjoyed finally seeing and touching her bare breasts, my fingers weren’t exactly idle and I was slowly teasing her smooth, bare pussy at the same time. Finally, I just had to explore the rest of her so I started kissing a trail down her belly until she was feeling my lips on the inside of her thighs. As I continued my kisses, she parted her legs more and finally I was able to enjoy the first taste of her as my tongue drew a slow line from the top of her slit to the bottom and back up. She tasted slightly tangy but very sweet and I could already feel the wetness that had been building up there. The more I licked, sucked and nibbled, the louder and longer her moans got. When I started tracing circles around her clit for the first time, her whole body quivered and I heard a definite, “Oh, ya – feels so good!”
Apparently, it felt even better when I focused more on her clit and slowly slid a couple of fingers inside her pussy because after a minute or so of that she stared making what I’d best describe as little ‘mewing’ noises and followed by a long ‘Ahhhhhh’ as she came. I love making a woman cum from oral so I kept up the licking, sucking and fingering until she came again just a few minutes later. I would happily have kept going but I could feel her gently pushing my head away so I reluctantly pulled away and moved back up beside her.
I was a little surprised to see tears on her cheeks so I quickly asked if everything was ok. With a big smile she said, “I’m very ok, it’s just been a long time since I’ve felt this good, this wanted and this comfortable with anyone.”
After I wiped the tears away with a finger and we shared another long, slow kiss, I asked if she wanted to stop for a bit and she just whispered, “As long as you’re ok with a few tears, I definitely want to keep going and feel you inside me. Just don’t stop if you see me crying” and then with a smile she added, “It’s been a while but I’m pretty sure it’ll work better if you take your boxers off too or maybe you’d like me to do it for you.”
When she mentioned her doing it, the twitch in my crotch was all she really needed to know so as I lifted my hips up a bit, she pulled my boxers down. As soon as she pulled them down far enough, my cock sprung free and was standing hard and long against my belly. I could see her looking at it for a few second before pulling my boxers all the way off.
As much as she said she wanted to keep going, I could tell she was a little nervous about me actually penetrating her so I rolled both of us over, pulling her on top of me and said, “How about I let you go at whatever speed you want and I’ll just lay here and enjoy watching as you do it.”
With another of her sexy smiles she leaned down for another kiss, whispered a quick “Thank you!” and then as she sat back up, I felt the opening of her pussy push against the head of my cock.
She stopped for a second or two before starting to rock slowly back and forth against the head, with a little more sliding inside her each time. As I enjoyed that feeling, I reached up to cup and caress both tits before sliding one hand down so I could cup her ass cheek as she rode me. By now she was taking all of me inside her. I say ‘all of’ which for me that wasn’t huge by some standards, just under 7″ but the way she was sliding up and down on it and how tight she felt, it made it feel like I was a lot bigger than I was.
I would have loved to have been able to suck her nipples while she slid up and down my cock but there was too much of a height difference for that so I had to settle for being able to pull her close for a series of long, passionate kisses and then reaching down to cup both ass cheeks so I could push up a little as she pushed down. That must have changed the angle slightly because it was only a minute or two later that she was moaning that she was going to cum and I loved the feeling of her pussy pulsing on my cock when she did.
She moved to sit back up a bit and I could see more tears rolling down her cheeks but seeing as she’d already told me it was likely to happen, I just wiped them away and said, “Damn you look and feel great. How about you lay back and enjoy for a bit?”
Kate just nodded and rolled onto her back allowing me to shift so I could slide back inside her. Before I did, I just couldn’t resist bending down and giving her pussy a couple of quick licks then moving up, lifting her legs slightly and sliding the tip of my cock into her pussy. If we ever did this again, maybe it would be more of a ‘deep, hard and fast’ kind of fuck but I was pretty sure that this time Kate was looking for more of a ‘long and tender’ kind of thing so I spent a few minutes just teasing her, sliding in until I could feel her starting to open and then backing out again. Without going any deeper, I slowly sped up until I was rapidly sliding in and out with just the first inch or so and when she got used to that, I slowed way down and slid the whole shaft inside her with a single long, slow thrust and then just held it there for a bit before pulling back out and repeating the long, slow thrusts. I kept that up until I felt her starting to thrust up against me and then switched to short thrusts again except this time I stayed as deep as I could and just pulled back a bit before sliding back in again. Just to kick it up a notch, I reached down and started rubbing her clit at the same time. I was hoping to work her back up to another nice orgasm but as soon as I started touching her clit, I realized she was a lot closer than I’d thought because less than a minute later she was moaning, “yes, yes” over and over, then there were a couple of hard thrusts up against me and I could see pretty much her whole body shake just as I felt her pussy clench on my cock, release and clench again as she came.
As soon as I felt her coming, I kept playing with her clit but went back to long, full strokes that took her from that orgasm right into another one. I’d been doing my best to hold off but when I felt her second orgasm start, I couldn’t help but moan out a “Damn, gonna cum soon too!”
I wasn’t sure if she’d be ok with me cumming inside her but the way her legs locked around my waist told me she was, so I quit holding back and was soon making her hot, wet pussy even wetter and more slippery as I came too. When I half fell and half lay to the side, I pulled her with me as best I could. I wasn’t surprised to see more tears on her cheeks but I was a bit surprised that I was crying a bit too. This time it was Kate that brushed my tears away and asked if everything was ok and all I could say was, “Right now, everything feels better than it has in a long time – thank you!”
With a nod of her head, Kate said, “I totally agree” and then more seriously added, “So now what?”
I pretended to think for a bit then pulled her close for a kiss before saying, “it’s up to you but I was thinking of enjoying the feeling of curling up with you for a while, then maybe a shower and then coming back to bed – or wherever else you’d like to make love again. I might even be open to making you some breakfast in there somewhere if you’d like. After all, I did tell you that I hoped you didn’t have any plans for the rest of the morning. Then we’ll have the rest of the day to figure things out but the only thing I really hope is that this isn’t a one-time thing – I’ve enjoyed finally touching you, tasting you and feeling you cum way too much to want it to end today.”
As I talked, I was looking at her to get a feel for whether she liked the idea or not but I saw nothing that made me think she didn’t. When she smiled, kissed me and then rolled over so her back was against my chest and pulled my hand up so it was cupping one breast, that was the only answer I needed. I really didn’t expect us to dose off again so I was surprised that the next time I looked, it was already 11am. I could also tell that the feeling of Kate’s ass against my crotch was getting me nicely hard again but when I pulled slightly back, Kate just rolled over so she was facing me again and whispered, “It’s ok, you felt really good against me but let’s grab that shower you were thinking of.”
I didn’t have a big shower – just your basic tub/shower combo but I was fine with Kate and I touching, rubbing and generally enjoying being close as we showered and at one point, I pulled her soapy body against mine, gently tipped her head back and we kissed for several minutes before finally rinsing off. Once we were out, at first, we were drying ourselves off but it didn’t take long before that changed to us drying each other off and soon the towels were forgotten and we were just touching and teasing each other as we kissed. In between kisses, Kate whispered, “How about that breakfast you’d mentioned, or considering it’s almost noon maybe lunch?”
I was getting hungry too so it didn’t take too long before we were enjoying some French Toast, juice and some scrambled eggs. After we’d eaten, we were putting things away when I felt her press up against my back, reach around to hug me and then she slid one hand down to stroke my cock a few times which got a series of quick twitches as I hardened again. I turned so I could hug her back and when I reached down to grab her ass and pull her close, she put her arms around my neck, her legs around my waist and said simply, “bedroom”
My bedroom was just down the hall so it was an easy carry. When we lay back down on the bed, I started to say something when ‘shushed’ me and said, “I just want you to know it feels so good to be with someone you’re not scared might hurt you and can get hard just by looking at and touching you. Both of those things mean more to me than almost anything I can think of right now because it makes me feel both safe and desired.”
I was going to say something but it’s hard to talk when someone’s kissing you and teasing your tongue with theirs so I went with the kissing until we mutually pulled apart, smiled, took a couple of deep breaths and went back for another round of kissing.
Finally, Kate pushed me ever so gently onto my back and began stroking my cock. I was expecting her to climb on top and start riding me again but instead she looked at me, down at my cock and back at me again. Apparently, she made whatever decision she was trying to make because she said, “I know I’ve told you I don’t like sucking a guy and that was mainly because the few times I did it with my ex he’d either thrust so hard or pull my head forward that I’d gag and unfortunately even though I tried a few times with Don, he often had trouble getting hard so it didn’t work which made me feel like I wasn’t sexy enough. You’ve made me feel so good that I’d like to try it with you as long as you don’t mind if I’m not very good or don’t do it for very long.”
After assuring her that whatever speed, duration or skill she had was fine by me, she took her first tentative licks of my shaft. I couldn’t help but moan a little and that seemed to be all she needed to move to sucking and licking just the head. Bit by bit she took more into her mouth and as she did, I started gently touching and teasing her from nipple to pussy which seemed to encourage her to suck harder and more. Initially I was figuring it would be a few licks, a few sucks and then done but the more she sucked, the better it felt until I knew I’d be coming soon. With everything she’d said, I wanted to make sure I didn’t surprise her so I reached down and stopped her for a second. When she pulled back and looked up, she must have thought she’d done something wrong because she said, “doesn’t it feel good?”
Now it was my turn to smile at her before saying, “No, just the opposite – what you’re doing was feeling so good that I was getting close to cumming but I didn’t want to just cum without you knowing.”
I was pretty sure that knowing I was going to cum that she would stop so I was quite happily surprised when she took me back into her mouth and started sucking again. The urge had dropped slightly when I’d stopped her but as she started sucking again it quickly came back and soon, I was shooting into her mouth. It had only been an hour or so since my last cum so it wasn’t a big load but it certainly felt like it.
Considering the experiences that she’d had giving head other times, I wanted to make sure she knew how much I appreciated that not only had she gone down on me but let me cum in her mouth as well. I was pretty sure from the look on her face that she still had my cum in her mouth so I did something I hadn’t done for years, I reached down with both hands and guided her face up to mine so I could kiss her. At first, I don’t think she realized I knew she still had come in her mouth because she pulled back a little but when she felt my hand cup the side of her face pulling her back and my tongue parting her lips, she went with it and soon we were sharing the cum that I’d spurted there just moments before.
When we finally separated, Kate looked at me and said, “Wow, I haven’t sucked a guy for a long time and I don’t think it’ll ever make the top three of fun sex things to do, but having you kiss me when I still had a mouthful of cum made it a lot more exciting! Did you enjoy it?”
“Well, it’s not at the top of my list either but every so often I enjoy something a little bit different. Partly because I always figured if my cum’s ok for a woman’s mouth, it should be ok for mine plus you went past your comfort zone in going until I came so the least that I could do was go outside my comfort zone and let you share it with me. ”
“It sure was different, kinda fun and it actually turned me on more than I thought.”
“Then I guess I’d better do something to look after that horniness of your until I’m hard enough to slide inside you again. Come on up here sexy lady!” and with that I put my hands on her hips to pull her up so she was basically straddling my face.
At first, she just stayed in one place while my tongue worked its way up/down/across her pussy lips and occasionally giving her clit a flick with my tongue. As her excitement built, she started moving back and forth a little and before long I was pretty much laying still while she moved forward and back so she could feel my tongue wherever she wanted to.
It wasn’t long before I could feel how much wetter she was getting and even her taste seemed to change. The nice thing with her being shorter was that I could easily reach up and caress, rub and generally play with her tits and nipples while my tongue danced with her pussy. Her first orgasm took about 5 minutes but the next two came very quickly after that and I quickly learned that when she her moans got faster and shorter, she was close and just before she came her whole body would tense and then quiver as she came. After the third one she pretty much fell to the side and at first all I could make out was “too… much” but as she calmed down a bit she said, “oh god, that was so intense. I can’t remember the last time I came three times that hard or that close together.”
I just smiled, kissed her and said “well, I guess that means you’re don’t want to feel me inside you again?”
“What, you’re hard alre….” and with a quick look down she said, “I guess you are! I don’t think I’ve got the energy to ride you but I’d love to just lay back and enjoy.”
That was fine with me so I stood up, pulled her close enough to the edge of the bed that I could stand and enter her that way. Soon we were both enjoying the feeling of me sliding in and out of her again. When I started going as deep as I could and a little harder, she moaned “Damn that feels good, just keep going like that or even harder if you want!”
That sounded even better so I reached down and grabbed an ass cheek in each hand and started pulling her up as I drove into her. Having cum twice in the last few hours I knew I’d be good for a while so I focused on hitting the spots that I could tell she enjoyed the most and after a about 10 minutes of deep, hard thrusts she suddenly yelled, “Fuck yes!” and had the strongest orgasm I’d felt yet.
As much as I’d have loved to keep pounding her, I was pretty sure she’d be too sensitive so I slowed down so I was going almost as deep but much slower. I was hoping she’d cum again so I started teasing her nipples with one hand and her clit with the other. That did the trick and she was soon cumming again. As that one tapered off, I asked her if she liked it from behind and she said “Yes, as long as you stay slow and gentle, I just know I’m going to be tender tomorrow but it’ll be totally worth it.”
When I got behind her on the bed, I realized I really hadn’t had a chance to appreciate her ass until now. It was a little bigger than it had been years ago but it was still firm, round and silky smooth and I couldn’t help but wonder if she enjoyed any anal play. After placing a few random kisses on each cheek, I shifted so I could line myself up and slide back into her. As she’d asked, I did it slowly and gently. I’d always found that doggie style put a different pressure on my cock that seemed to make me cum quicker and it was no different with Kate. About 15 minutes later, I could feel another orgasm building so I whispered, “I’m close, why not play with yourself and see if we can cum at the same time?”
I wasn’t sure if she would or not until I felt her fingers brush my shaft as I slid in and out. Soon both of us were moaning and just when I thought I’d be cumming before her, I felt the tell-tale tensing so I quit trying to hold back and just as she came, so did I. The feeling of her pussy clenching on my cock at the same time I was cumming was amazing and later she said the same thing about the feel of me shooting into her as she clenched on me. After we’d both came, she lay forward on the bed and when I lay beside her, she rolled enough to her side that she could put one leg over me and curl up with her head in the hollow of my shoulder. We lay there with my arms around her just enjoying holding and being held. A few minutes later I went to say something and realized that she was sound asleep so I carefully pulled the sheet up over us and soon I was asleep too. We didn’t sleep long, maybe an hour but I know I woke up feeling better than I had in a long time and when I looked over a bit, I saw that Kate’s eyes were open and with a sleepy smile, she brought her head up enough that we could share random kisses as we both fully woke up.
Eventually I looked at her and said, “I don’t know about you but I’m really hungry. I assume you still like Chinese so how about I order us some supper and have it delivered?
A few more kisses confirmed that she liked the idea and about 2 hours later we were full and trying to decide what to do for the rest of the evening. While I know that making love again was likely on her mind and it was certainly on mine, we decided to just relax and watch a movie before going to bed.
I finally found something on Netflix we both thought we’d like. Initially, we just sat close with my arm around her and her hand on my leg, then she moved so she could lay on the couch with her head in my lap. For the last half of the movie, we were both laying on the couch with her in front of me and my arms around her. I was in my boxers and she was in the t-shirt she’d slept in the night before so movie or not, it wasn’t long before I was getting hard against her ass.
She must have felt it too because when the movie ended, she turned her head and said, “As much as I’d love to go again, you’ve made me cum more in the last 24 hours than I had in the last 24 days and I’m not sure I could handle more tonight…but tomorrow morning is a whole new day!”
I gave her a quick kiss and said, “You’ve got a deal, are you ready for bed?”
With a quick nod she got up, I got up and after we’d done what we needed in the bathroom, we were soon curled up together in bed. I woke up once or twice in the night because Kate was moaning a bit but as soon as I put an arm around her and talked to her, she calmed down and was quiet again. I woke up before she did in the morning and she must have gotten too hot because when I looked over, she was sprawled on her back with the covers almost kicked off.
I wasn’t sure if I should or not but she looked so good laying there naked that I moved as quietly as I could so I could gently kiss and lick her pussy. At first there was no reaction, then she started moaning and flexing her hips up a little. By now I could feel the start of her pussy getting wet. I stayed nice and slow, with gentle swipes of my tongue and after a few more minutes of licking I heard a slightly sleepy, “Mmmm, feels good!”
Now that I knew she was awake, I sped up as well as including her clit in my clicking until she came a few minutes later. “You can certainly do that again another time…what a nice way to wake up!”
I kissed my way back up her body until my mouth was on hers and we were kissing passionately. I was just about to start easing my cock into her when she said, “hold me like you were last night on the couch.”
I figured maybe she didn’t want to have sex right away so we both rolled onto our sides and I moved up tight behind her. As I did though, she reached back and guided my cock in between her legs and after a little bit of shifting and rocking, I was able to slide into her from that position.
“Mmmm, ya just like that for now. I was thinking about trying it this way when we were laying on the couch last night but I didn’t have the energy to try. ”
I wasn’t able to go as deep or as fast this way but there was something more intimate about it. As a bonus, I was able to not only cup and tease her tits, I was also able to kiss her neck which I’d found she really liked. I asked her a couple of times if she was ok like this and both times, she said she was really enjoying it and I thought she had a couple of small cums. Eventually I pulled out and rolled her onto her back but moved so I was still on my side, lifted her closest leg slightly and slid right back in. This way I could go a little deeper but was also able to tease her clit, lips and the inside of her legs which quickly put her over the edge and she came twice within a minute or so. As she came the second time, I came too and enjoyed the feeling of shooting my cum into her pussy as it pulsed on my cock.
When I finally shifted away, I enjoyed the site of her freshly fucked pussy – lips red, puffy and shiny with our juices. Just as I reached down to stroke her slit, there was a bit ooze of my cum so I used it as lube so I could finger her and rub her clit until she came again except this time as she came, my mouth was covering hers and our tongues were already teasing each other’s. I could feel her moan into my mouth and her hips arched up off the bed before collapsing back down.
We lay there for a while just enjoying the feeling before Kate said, “Damn, I wish I could spend the rest of today here too but I promised Curtis that I’d meet him near the college for lunch.
She could see my disappointment so she gave me a big kiss and said, “It’s just for lunch – I could easily come back later!”
“I’d love that but I’ve got a bunch of running around and a meeting tonight. Can I take a raincheck for one night this week?”
A few more minutes of kissing followed by, “You might even be able to convince me to make it more than one night.” but before I could grab her and see if I could convince her to stay for a bit longer, Kate rolled over, off the bed and with a sexy smile said, “But you could join me in the shower if you’d like.”
I certainly ‘liked’ and even though we didn’t do much more than touch, hug and kiss, it was still an awesome way to start a Sunday.
True to her word, I was able to convince her to get together more than one night that week – several in fact and by the time summer ended, we were spending the night together almost half the time either at my place or hers and even if we didn’t spend the night together, we found ourselves getting together more and more for movies, dinner, drinks, walks or anything else where we could enjoy spending some time together.
The weather had just gone from ‘cool’ to ‘cold’ and we were laying on an air mattress in front of the gas fireplace. We’d had a great supper, had watched a movie, had just finished making love and were laying there relaxing. After a bit, I looked at Kate and asked, “How much notice would they need for you to take a week off work?”
“Why, what are you thinking?”
“Well, I’ve been thinking of this for a while now but didn’t want to rush things with you. I really need to get away somewhere warm and I’d love to have you go with me.”
“Oh sure, you just want to make sure you can have lots of sex while you’re away!” I could see her smiling so I knew she wasn’t too serious.
“Well, if sex was all I wanted, if I put an ad online, I’m sure there’d be lots of ladies willing to trade sex for a vacation but I really want to go with someone I’ll also enjoy sharing it with and not only is that a short list – right now you’re the only one on it.” I stopped for a few seconds to see what her reaction was and from the look on her face I was pretty sure she was going to say yes so I continued with, “When Laura passed away, I was pretty sure I’d never be happy again but the last few months of being with you have shown me that not only can I be happy but I can make someone else happy too. We’ve both got our jobs, our families and other commitments here so I was thinking it would fun for us to get away, spend a week somewhere with a beach, do some snorkeling, a few bars/restaurants and yes some sex too. At the very least we’ll both enjoy some time away and,” I paused for a couple of seconds before finishing, “I’m really hoping that we both enjoy being with each other enough that when we get back, we’re both interested in being a full couple, not just friends and lovers.”
I’d seen a lot of smiles from Kate lately but the one on her face when I finished was the biggest one that I’d seen. “That should be pretty easy, they’ve been after me for a while to take a vacation but I just couldn’t face time off work with nothing to do but sit at home and be miserable. I’d love to go with you. Yes, I’d certainly like to see how we feel when we get back. The sex has been awesome but I know I’ve started feeling like there could be more too!”
Monday
The next week or so was a bit of a flurry of planning. Her boss had no problem with her taking time off and I didn’t have any problems either seeing as I ran my own business. Next was to figure out where to go and we finally decided on Roatan because I’d been there several times so knew where to stay, where to snorkel, etc. Surprisingly, there were flights available so I got those booked on points and 2 weeks later we were landing in Roatan, Monday just after supper.
The resort supplied transportation so all we had to do was get our bags and get them to the van. Knowing we had a small kitchen in the room, I had the driver stop so we could get enough groceries for a few days including alcohol and mix before heading to the resort.
It was a small, family run resort that I’d stayed at several times before and I knew they’d remember me so I’d messaged the owner with what had happened so he knew and asked him to fill in the staff who’d know me to reduce any emotional/embarrassing questions. When we got there, both of us were greeted with hugs from the owner and taken to the bar for a drink while the staff took our bags to the room for us.
We were somewhat tired from our flight so after a couple of drinks we headed to the room. I’d told Kate that the rooms were ‘rustic’ – it was an older resort that sometimes-needed repairs but that the staff would look after everything. I don’t think I’d ever been there and not had to get the staff to find some cutlery or a fuel tank, or pots and pans so I was mildly surprised that not only was everything there that should be, there were fresh flowers on the table along with a bottle of wine, a bottle of rum and a ‘welcome back’ card. I’d certainly have to thank the owner the next time I saw him but for now we just wanted to get everything away and relax.
After unpacking, I asked Kate if she’d like to go for a walk up the beach so we both changed into our bathing suits and took a walk. As we walked, I showed her where some of the different restaurants/bars were, said hi to a few of the people that I remembered from other years, grabbed a drink from a beach bar and just before sunset we made it to the far end of the beach, just in time for a quick swim before the sun started setting. We went back to the beach and walked back a little to a spot without a lot of lights from the resorts and watched it together with Kate sitting in front of me leaning back against my chest with my arms wrapped around her. Of course, I made sure that not only did I get one hand on her breast, there was no one around so I was also able to slip a couple of fingers under her top and tease her nipple at the same time as I kissed her neck. When she started to respond to that, I used the fingers of my other hand to trace random lines up her leg, over her pussy, across her belly and then back down again.
I was pretty sure she could feel my cock growing against her ass and she confirmed it when she whispered with a giggle, “If you keep that you’ll have trouble walking back to the room.”
My grin told her pretty much what I was thinking when I whispered back, “Hmmm, you could be right…any suggestions?”
“I don’t think I’m quite ready for sex on a public beach – at least not tonight, but I should be able to give you a hand.” She looked behind us then stood up, took my hand and said “Over there.”
When I looked over there was an old section of stone wall that had broken down over the years but was still big enough so anyone walking up the beach couldn’t easily see behind it.
We moved behind the wall and as we kissed, I felt Kate easing my bathing suit down. From what she’d said, I figured I was in for a quick hand-job so I was totally surprised when she knelt down and started by sucking on the head and then bit by bit took more of the shaft into her mouth. It was only the second time she’d given me head and it felt even better than the last time. I’d already been worked up from playing with her on the beach and even though she was pretty well hidden the thrill of doing it in public made it even hotter. I’d have liked to be able to hold off longer but after only a few minutes of her mouth, tongue and hand I mumbled a quick, ‘cumming’ just to give her the option of finishing me with her hand but instead she went even faster with her mouth and it didn’t take much longer before I was cumming. With a long groan, I could feel my cum pulsing into her mouth and at the same time I was pretty sure I could feel her swallowing. As she let me slide out of her mouth and stood up, I whispered, “Thank you” and pulled her in for a kiss. Even though she’d swallowed most of my cum, when our tongues started dancing together, I found that there was still some left that were soon sharing. After a few more minutes we heard a group of people coming down the beach so rather than take any chances, I pulled up my bathing suit and we made our way back to the room.
When we got back, we stripped off our wet suits and I surprised Kate by falling back on the bed and pulling her with me for a few minutes of kissing and took the opportunity to grab and caress her ass at the same time. “I think it’s your turn to enjoy” and with that I put my hands on her hips, pulling them gently toward my face saying, “how about you just move to wherever you’d like to feel my tongue?”
Both her smile and her ‘Mmmmm’ told me she that she liked the idea so as her pussy settled over my face, I licked and kissed whatever bits were available. At first, she just moved so I could lick the length of her slit, then she moved further so I could also tease her clit with my tongue. I’d already found that when she’d had a few drinks she seemed to cum a lot easier and tonight was no exception. The more I licked, the more she moaned and moved back and forth on my face. In less than 5 minutes she was already cumming and when she did, she suddenly moved up even further which led to my tongue running right across her pucker. I’m not sure if she didn’t want to move or couldn’t but she pretty much froze right there as she came. It wasn’t something I’d ever done before but I was always open to something new so instead of backing off, I started licking around and across her backdoor as she came. It seemed like we were in a loop for a bit – the more I used my tongue on her ass, the harder she came and the harder she came, the more I used my tongue on her ass.
When she finally collapsed beside me, the first thing she said was, “I’m sorry, I didn’t plan on moving so you could lick me there but when you did, I felt like I was frozen and just kept cumming.”
“That’s ok, I wasn’t sure if you meant to or not but when I realized you were cumming that much harder because my tongue was teasing your ass, I figured I’d just go with it. I’ve never done it before but it seemed to really get you off and it actually turned me on too. I’m guessing you enjoyed it?”
“I’ve never really enjoyed anything anal before – I’ve been fingered there before but it didn’t do much for me and I’ve only tried anal sex twice and both times it hurt too much so I think I was more shocked at how good it felt and how hard it made me cum.”
“So, is it something you’d want to do again?”
With a bit of a blush she quietly said, “Maybe…but only if you want to.”
I gave Kate a quick kiss and said, “If you haven’t figured it out yet, I’m open to pretty much anything you enjoy and seeing as I enjoyed it too…yes, I’d certainly try it again.”
I’m pretty sure both of us had thoughts of curling up together and then having sex in a bit but apparently, we were both more tired than we thought because the next time I woke up, the sun was already up.
Tuesday
We took our time getting started but it was a great day. Most of it was spent snorkeling with a good bit of relaxing in the hammock and a few drinks. Late in the afternoon I looked up at the sky and told Kate, “Let’s pack things up, I think it’s going to rain soon.”
Sure enough, by the time we’d packed up our stuff and gotten to the room it was raining and shortly after that the wind picked up and the rain was coming down in sheets. Maybe it wasn’t funny to them but we had a bit of a laugh watching the other people on the beach getting drenched while they packed their stuff up and either ran to rooms or tried to stay dry under a tree.
We’d hoped that by the time we’d had supper, it would clear but if anything, it was worse so we decided to cuddle up in the hammock on the deck and just enjoy the smell of the rain and watching it running off the trees. I was quite enjoying teasing Kate as we lay in the hammock with touches and kisses. I wasn’t sure about her but I knew I was getting worked up and it wasn’t long before we’d shifted so we were sitting in the hammock facing each other and the teasing touches were now much more deliberate. The drawstring on my trunks was already undone so Kate could reach in to feel me more easily and I had one breast exposed and her bottoms pulled to the side so I could slowly finger her. After a bit Kate said, “I’ll be right back, I’ve just got to go pee.”
She wasn’t long but I noticed that when she came back she’d changed from her suit into a short skirt and loose top and sat back down facing me. She must have seen the puzzled look on my face so she kissed me and said, “remember last night when I said I wasn’t ready to have sex on a public beach?”
“Yup”
“Well, (kiss) we’re not on a beach right now (kiss), it’d be pretty hard to see us up here (kiss) and with the rain I doubt anyone will be out anyway. (several kisses)” With that said she pulled my trunks open far enough so that my cock was fully out then flipped her skirt back and pretty much slid down and forward onto my cock. It wasn’t the most comfortable position I’d ever had sex in and it wasn’t that easy to move either but we eventually found that rocking the hammock a little caused me to move inside her as well. As we rocked, we kissed and I enjoyed the feel of cupping her breasts under the shirt and feeling her hard nipples against my fingers. We eventually found a rhythm that worked and while there was no way to get long thrusts, it was very easy to stay fully inside her and get quick, short thrusts that seemed to put just the right pressure on her clit. She’d already came a few times before I reached the boiling point and exploded inside her. Neither of us moved until I softened enough to slip out and then we both laughed a little at the sound of our combined juices dribbling onto the wood below. At least with a hammock there wasn’t any ‘wet spot’ but it was cooling off so I went inside, grabbed a blanket, wrapped it around us in the hammock and we spent the next hour or so curled up and talking about what we wanted to do the next day. We finally decided to do the 45-minute walk up the beach to the next little town to look around and do some souvenir shopping.
Wednesday
We slept really well and got up a bit later than usual but felt totally relaxed. As much as we both wanted to stay in bed and play, we also wanted to get out before the heat kicked in so we grabbed a quick breakfast and headed out. We held hands as we walked and by now it felt totally natural and so did our stops for a quick kiss or two along the way. Once we got there, we spent about 2 hours just looking through the shops and talking to some of the vendors. Kate really liked a stone and shell necklace that one of the vendors had so after a few minutes of haggling over the price it was around Kate’s neck and her arms were around mine. We grabbed a really good chicken lunch from a street vendor, spent a bit of time at the beach, did some more shopping and finally grabbed a water taxi back to our resort.
Neither one of us felt like cooking so Kate changed into a dress while I grabbed a shirt and shorts then we walked down the beach, had supper at one of the bars and when we found they had a live band in that night we stayed for that. About an hour before closing time, it was totally packed so we grabbed fresh drinks and looked to see if we could find a couple of chairs on the beach just outside the bar. The only thing we could grab was a single ‘Adirondack’ style chair but it was big enough for Kate to sit in my lap quite comfortably. Having Kate right in my lap gave me perfect access to not only kiss her neck which I’d quickly found got her turned on, but the lighting wasn’t good so I was occasionally able to sneak in a quick grope.
It wasn’t long before she had to go to the bathroom so when she got up I pulled her in for a kiss, pointed to a darker area and said, “How about I move the chair over there and when you come back, have your panties in your purse?”
At least her reply of, “No promises that I’ll be comfortable enough to do anything but I guess there’s nothing wrong with leaving them off” was a lot better than the ‘no’ that I was kind of expecting.
When she came back, the chair was in the darkest area I could find and she sat back down in my lap. After a few minutes I slowly slid my fingers up the outside of her leg and then around to the front and quite happily found that she’d actually left her panties off. I teased and fingered her through the next couple of songs and when I slid one hand up her chest, she must have taken her bra off as well because there was nothing but a thin layer of fabric between my hand and her nipple.
At the end of the song, everyone stood up to applaud so I took the opportunity to unzip and pull my totally hard cock out. When we sat back down, I made sure I held the back of her dress and the lineup was perfect. She sat down perfectly for my cock to slide right inside her pussy. Thankfully the music was loud enough that no one heard her “Oh fuck!”
It didn’t take her long to figure out that if she gripped the arms of the chair, she could alternate between moving up and down or just holding herself up a bit so I could thrust up into her. At one point, I looked around to make sure no one could see us and saw a couple who’d been busy groping and kissing each other since we moved to the sand. The way they were standing and moving back and forth I thought maybe they were fucking too and it was pretty much confirmed when he looked over at me, grinned and gave me a ‘thumbs up’ at the same time he shifted her skirt so even though it was dark, I got a quick flash of her ass.
I figured I’d wait to tell Kate just in case she decided to stop but knowing the other couple was fucking less than 15 feet away was a big turn on and it wasn’t long before I was cumming at the same time Kate did and while I don’t think he could see us, from the look on his face, I’m pretty sure he heard us.
After she came, Kate just dropped back onto my lap and I wrapped my arms around her and held her. Our timing had been pretty much perfect because the band was just finishing its encore song and soon everyone was leaving. We stayed where we were until the majority of people were gone. It was easy for Kate to just let her skirt drop when she stood up but I had a little more trouble tucking myself in and zipping up but thankfully no one noticed.
We were about half way back to our room when Kate stopped and pulled me to her for a kiss before saying, “That was likely the most daring and hottest thing I’ve ever done sex wise but it’s a weird feeling walking with your cum trickling down my leg. If we ever do it again, I’ll have to remember to go to the bathroom before heading back!”
Her smile told me it wasn’t bothering her that much so I chuckled, kissed her some more before we started again. Once we were in the room and turned the lights on I chuckled again because there was a very noticeable wet spot on the back of her dress so she decided that she’d better shower and give it a rinse at the same time. I joined her and after a nice shower we dried off, slid into bed and cuddled until we both fell asleep.
Thurs
We woke up to more rain which was ok by me because that gave us the perfect excuse to grab a quick breakfast and then head back to bed. Knowing there wasn’t much to do outside, we took our time – kissing and touching each other until I finally rolled Kate onto her back and slide my cock inside. I still wasn’t in a hurry so I kept it to nice long, slow thrusts and whenever I felt like I was getting close to cumming I’d either stop so we could lay there and kiss some more or I’d slide down so I could use my tongue on her. My goal for the morning was to have her cum as many times as possible before I did. I really couldn’t count because sometimes it was hard to tell if it was three little orgasms or one long one.
After a while, Kate said, “You don’t have to hold back, I want to feel you cum!”
That was all I needed to hear so I shifted a bit so I could hold her legs and go a little deeper with a different angle and started going faster and harder. As soon as I knew I was going to cum, I reached down and started rubbing her clit and held on just long enough for her to cum one last time as I shot spurt after spurt of cum inside her.
When I looked at the clock, I realized we’d been making love for almost 2 hours so we decided to shower, do some snorkeling, grab lunch somewhere on the beach and then maybe just relax on the beach for the rest of the afternoon. We got some great pictures of fish and coral so while we were having lunch, I asked Kate if she’d like to try night snorkeling. She laughed and said we wouldn’t see much but I told her I’d been talking with the dive shop I used to go to and they said they’d rent me a couple of lights if I wanted. It took some doing but I finally convinced her. The rest of the afternoon was spent alternating between swimming, relaxing on the beach and more than a little playing around in the water before grabbing some supper. As we were paying our bill, the waiter who looked after us said, “I want you to know I’m not just trying for a bigger tip but the two of you look like a great couple.”
We just smiled, thanked him and then headed back to catch the sunset before going back to the room. While we were watching the sky start glowing from the setting sun, I wrapped my arms around Kate from behind and said, “You know, I think the guy was right.”
“What guy and what was he right about?”
“Our waiter on the beach – the one that said we looked like a great couple. I’ve loved every day we’ve spent with each other here. We’ve known each other so long but I feel like I know you so much better. Before we left, we agreed that we were both open to becoming a couple when we got back but I don’t think I want to wait that long. It sounds a bit funny at our age but would you like to be my girlfriend?”
Kate laughed for a few seconds, “It does sound funny and I didn’t know if I’d ever want to be serious about anyone again but I feel the same way you do so yes, I’d love to be your girlfriend!”
We reached for each other at the same time and spent the next few minutes holding each other and kissing passionately. When we finally pulled away, I realized that both of us had tears on our faces and that we’d actually missed the best part of the sunset. When I mentioned that to Kate she just smiled, wiped the tears off my cheeks and said, “It’s ok, I’m happy to miss one knowing there’ll be more to watch together other evenings.”
We kissed for a few more minutes before I said, “Speaking of evenings, are you still good to try night snorkeling with me?”
“I think so. I know I’ll be nervous so promise you’ll stay close?”
“Don’t worry – I’m not going to let you get too far from me at all…in or out of the water.”
We went back to the room, changed, grabbed our snorkeling gear, cameras and lights and headed down the beach. By the time we got to the end, it was just nicely dark. Rather than go too far/too fast, I spent the first 5 or 10 minutes with Kate near the shore in fairly shallow water until she felt secure and then we spent the next hour or so checking out the reef. It was a perfect night, warm with almost a full moon and very calm so there was lots to see. Once she got totally comfortable, I loved her excitement whenever I pointed out something with my light. The highlight of the night was seeing three octopus and a small stingray but beyond those there was lots of fish, lobster, shrimp, a couple of eels and lots of little reef critters to look at. Eventually we started getting chilled so we headed back to the beach and were just coming out of the water as another couple were getting ready to go in, except they were obviously planning on skinny dipping as they were both nude. Neither of them must have seen us because they both jumped and she let out a little scream that I hoped for their sake didn’t make one of the security people curious. I certainly checked her out and I’m pretty sure Kate checked him out. As we passed them, I simply said, “Enjoy!” and with a grin and a quick look at his lady friend he said, “We plan to!”
I wrapped a towel around both of us to warm Kate up for a bit and was a bit surprised when she said, “maybe we should try skinny dipping sometime while we’re here.”
After quickly agreeing, we were soon headed back up the beach and enjoyed a nice, hot shower when we got to our room before climbing into bed. We were both pretty tired from the day so we curled up together, watched a movie and then went to sleep.
Friday
When I woke up Friday morning, Kate was still sound asleep but must have gotten hot during the night as she’d thrown most of the covers back, giving me a great view of her naked body with the sun lighting her up. I was torn between curling back up with her until she woke up, getting some breakfast ready hoping she’d wake up or waking her up with my tongue and fingers.
It didn’t take much to decide that option 3 would be the most fun and thankfully she was laying on her back with one leg kind of drawn up so I had easy access. Slowly, so I didn’t wake her up yet, I moved onto the bed and as gently as possible started tracing patterns across and around her pussy lips. It took a few minutes but eventually I heard a few small moans that told me at least part of her was responding to what I was doing. This was different because usually by the time I started tonguing her, she was already wet but now I could actually feel her getting wetter as I licked her. Bit by bit I sped up and soon not only was she nice and wet but she was moaning with each lick.
It wasn’t until I slid a couple of fingers into her pussy, curled them against her g-spot and ran my tongue across her clit that she woke up. She seemed to go from asleep to awake almost instantly and it was only about 30 seconds later that she moaned, “Oh shit, I’m cumming!”.
It wasn’t the most intense orgasm she’d had since we got together but it seemed to last a lot longer than usual. When it finally ended, she gasped out, “At first, I thought I was dreaming and when I woke up, I realized it wasn’t a dream and wow…. you can wake me up that way any time you want!”
I just smiled and said, “There’s a good chance I’ll take you up on that – and more than once too!”
As she looked down at my crotch, Kate smiled and said, “And it looks like I’m not the only one that enjoyed it!”
Considering I was naked and totally hard there wasn’t much sense in denying it, especially when she was already reaching out so she could stroke me. Her hand felt great but I really wanted to slide into her pussy so I shifted so I was over her and we kissed as she guided me into her pussy. Once I was all the way in, we spent the next half hour or so making love. We started with me on top, then went to doggie, then she moved to the edge of the bed so I could give her some long, hard strokes. It wasn’t long before I knew I was getting close so I lay on my back and she climbed on and started riding me.
By now she’d already came a few times so I wasn’t too worried about holding back and thrust up against her as I came. After she felt me stop spurting, she moved to lay beside me but when I felt her moving, I reached down and gently grabbed her hips to keep her in place. When I saw the puzzled look on her face I said, “Would you like to cum again?”
“For sure, but you’ll likely need a bit to get hard again.”
“My cock may not be ready but my tongue is… how about you move up so I can lick you to one more?”
“Are you sure? It felt like you came a lot.”
“Yes, I’m sure. I’ve thought about it a few times. I’ve already tasted my cum from your mouth after I came there and that turned me on and I know I enjoy tasting your pussy so why not taste both of us together.”
Kate looked at me and finally said, “As long as you’re sure, I’m fine with it!” and with that she lifted off of me and moved up so her pussy was right over my face.
When I saw the first bit of cum ooze from her pussy and start to drip, I wasn’t as sure I’d like it but definitely wanted to find out. When it landed on my lips, I licked it off and was a bit surprised that it tasted different but actually better mixed with her juices. By now her pussy was right against my lips and I spent the next 5- or 10-minutes licking and sucking her pussy. She had a few more small orgasms and each time there was a new trickle of my cum mixed with hers.
My hands were still on her hips but after the third orgasm, she reached down and grabbed my right hand with hers. Initially, I wasn’t sure what she wanted but when she pulled it over and pushed one of my fingers against her pucker I quickly got the idea. I reached forward a little more to get a finger nice and slick with our juices from her pussy and then rubbed them around her pucker. As she relaxed, I was able to slide the tip of my finger inside and was rewarded with a nice moan. It was a really tight fit so I re-lubed my finger and then slid the tip back in again. This time it went in much easier and soon I was up to the second knuckle. I went very slowly and gently so it took a few minutes but eventually I was sliding the whole length of my finger in and out of her ass at the same time I was licking and sucking her pussy.
The more I pleased both her holes, the louder she got. Eventually I felt her start to shake and heard her moaning, ‘Oh fuck!’ over and over again which surprised me because Kate rarely swore.
The first orgasm she’d had when I woke her up with my tongue hadn’t been a huge one but this one was. Her whole body seemed to tense up, she let out a long, loud, “Fuuuccckkk!” and I was totally surprised when I actually felt a splash of her juices against my face. I kept on licking until finally she rolled to the side mumbling, “enough…too sensitive”
When I shifted so I could face her, I could see she was crying. When I asked if everything was ok, she put her arms around me, melted to me and whispered through the tears, “It’s so ok that I feel totally overwhelmed but in a great way.”
We just lay there holding each other until she’d calmed down and felt like saying more. “When Mark and I were together, the sex was good but not great and a couple of times he talked me into letting him finger my bum or try sex that way. Maybe we weren’t experienced enough or something but it either hurt or just didn’t do anything for me. When Jorge and I got together the sex was great at first but then I found that sex was more for his pleasure than mine and the one time he tried putting his cock in my ass he was rough and didn’t use any lube. Even when I told him it hurt, he didn’t quit trying until I told him he’d lose his nuts if he didn’t stop. Don was very gentle and I might have let him try except he wasn’t interested in anything other than ‘normal’ sex. No one ever kissed me after cumming in my mouth, getting my pussy licked was rare and there’s no way they would have done it after cumming in me. Now here we are and you’ve shown me that not only are all those things ok, they can actually feel amazing and are a definite turn on. I’d pretty decided years ago that no one would ever put anything up my bum again but when I felt you licking and sucking on my pussy right after you came in me, I thought that if you’d do something like that then the least that I could do is see if your finger felt as good as your tongue had the other night. I can’t remember the last time I came that hard and I think I might have squirted a bit.”
I smiled, wiped my beard with my hand and said, “yup, I’m pretty sure you squirted a bit too and I loved it!”
I could feel her arms tighten even more around me as she brought her mouth to mine. We kissed for a bit and then she said, “You’ve made me feel so good, not only about myself but about the future.”
After giving her a quick kiss back I said, “I feel exactly the same way. I want to go other places with you, see and do other things and basically just make sure we enjoy as much together as we can!”
As we lay there just enjoying being with each other, Kate looked at me and quietly asked, “Have you ever done that before?”
I was pretty sure I knew what she meant but figured I’d have a bit of fun with her so I replied, “Done what, fingered someone’s bum?”
“No, not that…. I meant what you did after you came…. with your tongue.” Even as she was finishing, she realized I’d been playing with her which got me a quick smack on my butt and a “you’re terrible, you just wanted to hear me say it.”
“Guilty! But no, I haven’t done it with anyone else and before you ask, I enjoyed it more than I thought and as long as you enjoyed it too, I’d definitely do it again. You seemed to enjoy the combination of my tongue and my finger – is that on your ‘do again’ list?”
“Well, I’m still not sure I’d want to try anal sex again but a finger” and then a little more quietly, “or maybe a tongue would be fine.”
“Sounds good to me. I’ll never push you to do more than that but if you ever decide to try just let me know and I’ll do my best to make sure you enjoy it.”
Knowing that we had to fly back the next day, we spent the whole day either laying on the beach, swimming or snorkeling. I’d made reservations at one of the restaurants so we could have a nice, romantic dinner on our last night. As we were finishing, I looked at Kate and said, “I remember you saying something about going skinny dipping while we were here – tonight’s our last night.”
She only thought about it for a second or two before saying, “Let’s do it! Even if someone does see us odds are really good that we’ll never see them again anyway.”
After we had dessert and settled the bill, we popped back to our room to change and grab a couple of towels and thinking ahead I grabbed a blanket without Kate seeing and put it in the carry bag as well. We walked to the end of the beach where we’d seen the naked couple going in the other night. I put our bag down and took off my bathing suit. When I looked over at Kate, she had her top off but seemed to be hesitating about taking the bottoms off too so I gently pulled her to me for a kiss before whispering, “No one will likely see us and if they do, that’s ok by me because you look amazing!”
That seemed to give her the confidence to take the rest of her suit off and we held hands as we went into the water. I’d gotten a little hard watching Kate undress but the cool water quickly took care of that which got a giggle from Kate. We splashed, swam and spent a fair bit of time touching and kissing as well before heading back to the beach. When we got there, I spread out the blanket, gave Kate a long passionate kiss and said, “If you don’t want to that’s fine but I thought seeing as it’s our last night here maybe we could make love right here on the beach.”
I could tell she wasn’t sure but happily surprised when she said, “I’ve never done anything like that in public but if I’m going to do it, this is likely the best place so yes.”
Hearing that, I didn’t want to give her a chance to change her mind so after kissing for a minute or so, I leaded down to kiss and suck her nipples before whispering, “Why don’t you lay down so I can kiss more of you?”
With a smile I could even see in the dark, Kate lay down and I went back to kissing her mouth before slowly working my way down to her nipples again and then all the way down her belly to her pussy. I could taste the salt water on her but as I started licking her pussy the taste quickly changed as she got wetter from my tongue. As hot as it was giving her pleasure with my tongue, being right there on the beach made it even hotter and from the way she was moaning, I was pretty sure she was finding it more exciting as well because it only took a minute or so for her first cum. When I felt the little tremors of her orgasm stop, I sucked her clit in between my lips and while I held the suction, I rapidly flicked the tip of it with my tongue which put her right into her second orgasm. I’d have happily licked her to several more but because there was a chance of getting caught, I decided to shift up and slide my hard-on into her. Over the next 10 minutes or so, she came at least twice more and I was just getting close to cumming when we saw a flashlight come on about 60 feet up the beach and it looked like it was heading our way.
We quickly decided that we’d better play it safe and it was a good thing we did because at least by the time the security guard made it down to us, we had our bathing suits on and were just talking. He didn’t say anything to us but from the grin on his face I’m pretty sure he knew what we’d been doing. Rather than risk another interruption, we gathered everything up and headed back to our room.
Pretty much as soon as we were inside, the suits came back off and we were naked on the bed. I was planning on picking up where we left off but apparently Kate had other ideas because she told me to lay back on the bed and then moved so she could take my cock into her mouth. I knew something was up when she stopped long enough to say, “can I try something?”
Now with most people, I’d have asked ‘what’ first but I was pretty sure that whatever Kate was thinking was something I’d enjoy so instead I said, “Sure.”
She just smiled, got off the bed to rummage through her suitcase before coming back and taking my cock back into her mouth. I was just going to ask what she wanted to try when I felt her run a very slippery finger over and around my asshole. Now I’d played with my ass a few times but never had anyone else do it so I was a little surprised but it felt good so far so when Kate looked up, I just smiled and nodded.
Knowing I was ok with what she was doing, she continued her exploration and before long had a finger fully in my ass and then started slowly sliding it out and back in again. As she did that, she resumed licking and sucking my cock and I was quickly finding the combination of the two felt really good. Her fingers were fairly small so there was no problem when she added a second finger and as it slid in, she looked up and said, “How’s that feel?”
“Feels really good, give it a bit and maybe try three.”
After a couple more minutes, she tried a third finger and while it took a bit more time and a bit more lube, I soon had three fingers in my ass for the first time ever. I’d been close to cumming on the beach but the guard’s arrival and the walk up the beach had killed that temporarily but the combination of her mouth and fingers had me right back to the boiling point. When I whispered that I was close to cumming she just started sucking harder as she fingered my ass. I’d cum hard before but it had been a long time before I’d cum that hard or for that long. After the last spurts had finished and I was going soft, Kate moved up beside me for a quick kiss before lying beside me and whispering, “Did you like it?”
“I was a bit surprised but I loved it, what made you decide to try it?”
“Well, I think one of the reasons I’ve never wanted to let a guy do anything with my bum again was because any time I even suggested that I play with theirs they’d freak out and say no. I’ve been thinking about trying it with you since your tongue ended up teasing my bum but didn’t have the nerve to ask or try it but now, I’m glad I did.”
“So am I, the most I’d ever done was try one finger on myself and it felt good but nowhere near as good as feeling you do it.”
I could see how relieved she was as she said, “So…one more thing on our ‘do again’ list?”
“For sure!”
After a “thank you!” and a few more minutes of kissing, we were soon asleep in each other’s arms.
Saturday
My first thought waking up was that we had to go home that afternoon but my second was how much I’d enjoyed the week with the sexy lady lying beside me. It wasn’t long before she woke up – ok, maybe me lightly teasing her nipple had something to do with it. I was hoping for a morning quickie but Kate told me she wanted breakfast and a quick shower first. While she was in the shower, I got the tea ready and threw together some eggs and bacon. After we were done breakfast, she suggested I take a shower and then we could figure out what we wanted to do before we left. I already knew what I wanted to do but went for the shower anyway. When I got out, I looked over at the bed and just about tripped over my own feet.
Kate was naked, on the bed, on her elbows and knees with her bum in the air. I also quickly noticed a tube of lubricant lying beside her. She was kind of looking over her shoulder at me and obviously enjoyed the combination of shock and arousal on my face because she just smiled as she explained, “I wanted to do something special on our last morning and decided that before I lost my nerve, I’d see if you wanted to have any anal fun this morning. No promise that I’ll let you put your cock there but we’ll see.”
I just smiled, nodded and moved so I was able to place a few random kisses on the cheeks of her bum before running my tongue the full length of her slit and then right across the pucker of her ass. I spent the next few minutes, kissing, licking and tonguing her ass while I fingered her pussy until she was moaning and pushing back against my tongue.
When she started doing that, I knew she was ready for a little more so I kept fingering her pussy but grabbed the lube and with a bit of lube, eased a finger into her ass, knuckle by knuckle until it was all the way in. “How’s that so far?”
“Mmmm, it’s good – try another finger.”
I did just that and while it took longer than the first with a few stops along the way, eventually I had two fingers sliding full length in and out of her ass in time with the fingers in her pussy. When it felt like she was going to cum, I slowed down with my fingers until they were just barely moving, leaned forward and whispered, “do you want to cum like this or do you want to try my cock instead of just fingers?”
“I want to cum, but I want to feel your cock in my bum too, just go really gently.”
I leaned forward and kissed her neck, “I will and if you want me to slow down or stop all together you just say so. I want you to enjoy not be hurt. How about you lay on your back so I can touch you and kiss you at the same time?”
Kate nodded and rolled over, and at the same time I took a few seconds to make sure my cock was well lubed as well. Once I was sure we were as ready as we were going to be, I slowly eased my fingers out and just as they were almost out, I eased the head of my cock against the opening before it could fully close. As I pushed gently, her bum opened back up enough to almost let the head in and Kate moaned slightly and whispered, “You feel huge but it feels ok so far.”
Knowing that she was ok with things so far, I eased almost all the way back out and then back in again. I kept that up, each time going a little deeper than the previous time. I kept watching her face for any sign she wanted me to stop but every time our eyes met, she smiled and either nodded slightly or mouthed, “it’s ok”.
After several minutes I was about halfway in then on the next gentle thrust it was like everything relaxed and I slid full length into her ass. Kate had been moaning as she felt more and more of me enter her bum and when it went all the way in, she let out a long moan so I stopped and waited.
After a few seconds she said softly, “It’s ok, keep going – nice and slow.”
I did just that plus I reached down so I could tease her pussy and clit at the same time. That seemed to make the difference because it wasn’t long before she said, “Damn, yes, keep going. You can even go a bit faster if you want.”
Oh, I wanted so I trickled a little more lube on my shaft and then not only sped up but started thrusting a little harder until I heard, “Perfect, just like that!”
I stayed as close as I could to the speed and force and as I kept fucking her ass, she started moaning that she was close to cumming. I wasn’t sure just how close until she let out a loud, “Yessss!” and I felt a couple of squirts of her juices hit my hand. As she came, I could feel her ass clench against my cock and that was all it took for me to start shooting my cum into her ass. I stayed in place until I could feel my cock soften and after I slid out, I grabbed a warm, wet washcloth to give both of us a bit of a wipe but other than lube and cum there wasn’t really anything that needed wiping.
When I lay back down and we hugged each other, I could see traces of tears on her face. Worried, I asked if I’d hurt her at all and with a bit of a smile she replied, “it hurt a little at first but it was a good hurt and once that passed, it actually felt really good. I was just thinking that it was a shame I had so many years of bad relationships and bad sex until we finally got together and this week has been so wonderful, I almost don’t want to go back to how it was before.”
I hugged her tight for a minute then said, “Don’t think of it as going back to how it was before, think of it as going back to something that you didn’t have when you left.”
“I know but it’s still going to be hard not going to sleep every night with you holding me and waking up beside you in the morning.”
“I feel the same way and I’ve been thinking about it. I wasn’t going to say anything until we got back but your place is really close to the University so it wouldn’t be hard to rent out and mine’s a bit bigger so there’d be lots of room for all your stuff. If you’d want to move in with me that is.”
The look on her face said everything and the kiss I got made sure I understood that she was saying yes. With that to look forward to, any sadness of leaving seemed to disappear and after a last swim, we showered, packed and by noon were at the airport. We’d just gotten altitude when Kate looked at me and said, “so do you think we should buy a new bed or keep one of the ones we’ve got?”
I just smiled, kissed her and said, “Why don’t we leave that until we see how everything fits once we get you moved in?”
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