Finally Experienced a Pegging

I was nervous as hell but still determined to see where things would go but I guess a bit of background first. I'm Phil, 29 yrs. old, had quite a few girlfriends but never married. I had a pretty good job as a repair technician with the local school board. I love sex but had always had a bit of a kink that I'd only shared with a few girlfriends and none were really interested in taking me up on it.

It had started years ago when I was lying in bed, watching a porn flick on the TV and the woman had been teasing her asshole with a finger for a few minutes. As I watched, my cock got harder and harder and eventually I was stroking myself. I'd never had anal sex with a woman but had also never really wanted to but watching her finger her ass was totally turning me on. By the time she'd added a bit more lube and a second finger, my cock was oozing precum so just for the hell of it, I gathered up as much as I could and spread it over my own pucker. This was the first time I'd ever touched my own ass sexually and I immediately loved the feeling. As she went from two fingers to a vibrator, I went from one to two fingers along with a bit of lube from the nightstand. As I stroked my cock, I fingered my ass and the load of cum I eventually shot was one of the largest I could remember.

From that night on, it wasn't unusual for me to end up fingering my ass while I watched porn and eventually, I found myself looking for porn where the woman was fingering a guy's ass or using a vibrator on it. One day on the way home from work, I got brave enough to stop in at the local adult store and buy a vibrator that was just a little bit smaller than my cock. I'm pretty sure the woman working there figured it was for my girlfriend and I wasn't going to correct her. When I got it home, I immediately stripped, got onto the bed and found some porn to watch. When I first started playing with my ass, the thought went through my mind that maybe I was gay or even bi but seeing a guy's cock in a video did absolutely nothing for me but one of a woman playing with a guy's ass got me totally turned on.

As I watched one, I started spreading some lube around my pucker until I was able to slide one and then two fingers inside. Since I'd started fingering my ass regularly, I'd also found it was easier and easier to get a couple of fingers in and the night before, I'd gotten three in which felt amazing. After a few minutes of that, I switched to a video of a woman sliding a vibrator in and out of the ass of a guy who was supposedly her boyfriend. I turned my new vibrator on and slowly pushed the tip up against my nicely lubed pucker. The head went in fairly easily, followed by the first couple of inches and that's when I realized that the vibrator was going to be going a lot deeper than my fingers had ever gone. It was new territory for me and took a bit more lube and some gentle pushing before I finally felt the head slide past the second muscle ring and all the way into my ass. I could feel the vibration through almost my whole body and it felt great. I damn near came just from the feeling but managed to hold off so I could play a bit more. It didn't take me long to figure out exactly where my prostate was because I could feel a very intense 'tingle' every time the vibrator hit it and after a few minutes of that stimulation I let loose with several huge spurts of cum.

Since that night, I've bought a second vibrator that was a bit bigger than the first and one night after more than a few drinks, I even experimented with a medium cucumber and a few other things I found around the house. I quickly realized I was hooked on anal play but also found that if I mentioned it to any of the women I went out with, they either wondered if I was gay or thought it was too kinky so I was left to my videos and masturbation.

Then one night while looking for some new video's, I found an adult chat site. Video on one screen, cock in hand and watching the chat on the other screen was hitting all the right buttons to take me to a big cum. Once I figured out the site, I found there were more 'rooms' to chat in that had been set up by the users so I checked a few of them out and saw one called 'pegging' - I knew from my video's that pegging was where a woman used a harness and strap-on to fuck a guy and had found those videos were an even bigger turn on so I immediately joined that room and got a quick 'hello' from some of the people there. As I started reading the chat, I could see it was a bit of a poll; how many had tried pegging vs how many were interested in trying it for the first time. Eventually I got brave enough to type that I'd used toys on myself but had never been pegged. When one of the women asked if I'd be interested in actually trying it, I said, "definitely!"

Shortly after that, a private chat window popped up and a different woman said she'd love to know what I'd already done anally. I figured it was pretty anonymous so I told her the story of how I started, what I'd done and that I'd been thinking more and more of having a woman do it to me instead of doing it myself. I hadn't noticed but when I looked quickly at her profile info, she was just under an hour's drive east of me and we spent the almost the next hour chatting about pegging. I told her that I'd been wondering what it would feel like to have a woman fucking my ass with a toy instead of doing it myself and she told me that she could sometimes cum just from the thought of playing with a guy's ass.

Eventually I had to sign off because of work the next day but she'd told me her name was Denise and she hoped we could chat again sometime. A few nights later I was back on and she pinged in with a chat request. After chatting for a few minutes, she told me that after our first chat, she'd gone to bed and masturbated to a really long orgasm and I told her that I'd done the same. When she asked if I'd played with my ass and when I admitted that I had her next question was, "What with?"

Even though I had no idea who she was, I was still a bit hesitant to say but after a bit of prompting, I told her I'd started with the vibrator but decided I wanted to try something a little bigger so I'd grabbed a long-necked beer bottle to see how much I could take. Her reply of "Holy fuck that would be so hot to watch" took me by surprise but the thought of having someone watch what I was doing got me turned on even more.

I'd noticed there was an option for video chat and I wasn't really sure I wanted to but horniness finally won so eventually typed back, "Do you want to see right now?"

"Really? For sure!"

"Hang on, I'll be right back!"

It took me a couple of minutes to get the webcam hooked up and running on my computer, grab the lube, the bottle and get undressed. When she saw my hard cock she typed, "Looks like you're turned on... I am too!" and the next thing I knew, I was seeing an image on my screen of her bare pussy and even over video, I could tell she was a bit wet.

I grabbed the lube, adjusted the camera and was soon happily fingering my ass. By the time I had a couple fingers in my ass, she was fingering her pussy and when I switched to one of my toys, she started using one of her own vibrators. We'd occasionally stop playing to either tell each other how good it was feeling or tell the other how hot they looked. When I typed, "Bottle time?" her immediate response was "fuck yes!" so I replaced the vibrator with the neck of the bottle and after a few minutes I had the whole neck in but the main part of the bottle was just too wide to fit.

When she asked me to stroke my cock at the same time, I happily did that and it wasn't long before she was seeing spurt after spurt of cum shooting up and onto my belly. From that night on, we'd regularly meet online so she could watch me play with my ass. A few times she'd 'direct' what was I doing by telling me to go slower, faster, shallow or deeper and that made it feel even more like she was there doing it. One night as we were chatting, playing and getting close to cumming, she said something about it would be even hotter to watch in person and when I replied, "I'd love you to watch or better yet do it for me."

That set both of us off in a huge orgasm and just as we were getting close to signing off, she typed, "I've seen you're not that far away, I used to live in London years ago. Would you like to meet sometime at a Timmies or something and if we're both comfortable, I'd love to take you up on your offer of letting me do it to you."

I hadn't really thought of it as an 'offer' but the idea definitely turned me on so I agreed and we decided to meet about halfway in between our places in Woodstock, at a Timmies just off the highway. Neither of us had shown our faces on cam and decided to leave it that way until we met. I told her what I looked like and what I'd be wearing and she did the same. She made it clear that she wanted to meet just to watch me and maybe play with my ass herself but wasn't planning on having sex, at least not the first time we met. I told her that was fine and we finalized the details.

Now here we are back at the start; I was nervous as hell but still determined to see where things would go. I was early so I'd been sitting in my car at the Timmies trying to get up the nerve to go in and finally decided that if I didn't, I'd always be wondering what could have happened. When I went in and looked around, I couldn't see anyone matching the description she'd given so I went to the bathroom then grabbed a hot chocolate and a table away from everyone else. I almost missed her because I was watching the entrance but out of the corner of my eye, I saw a woman coming from the bathroom area who looked like she fit the description that Denise had given me and was wearing the floppy beach hat she said she'd be wearing. She must have come in when I was in the bathroom and gone to the bathroom herself. She grabbed something to drink and when she turned around, I waved and as she came over, I was suddenly thinking that maybe this wasn't the best idea after all. She was wearing a skirt that came a bit more than halfway to her knees and what looked like a tube top with a loose shirt over it.

When I first saw her, she looked familiar but as she got closer, I knew exactly who she was, Denise McDonald, the vice principle at the school that I'd been to for computer problems quite a few times before she transferred to take the principal's position where she was now. I remembered her fairly well, brunette, about 34b cup, nice legs, great smile and always looked sexy without flaunting anything. She obviously recognized me too because she suddenly stopped and at first, I thought she was going to leave but after a couple of seconds she kept moving toward the table but I could tell she wasn't sure that she was doing the right thing either.

After she sat down, neither of us said anything for a bit until eventually I stammered out, "Well, I guess we don't need as much of an introduction."

That got a bit of a smile from her before it quickly faded a she said, "Please promise that you won't tell anyone about what we've talked about online."

"Don't worry, I really can't see me saying to anyone I know, 'So, the weirdest thing happened, I'd been chatting with a random woman on a website about fucking my ass with a dildo and it turned out to be someone I knew."

She'd just been taking a nervous sip of her tea when I answered and she promptly blew some of it across the table. That made both of us laugh which made both of us a lot more relaxed. I already knew she'd been divorced when she'd been Vice Principal but she hadn't given me any details until now. Bit by bit, I learned that her and Nate had met in college, fell in love and got married right after graduation. Over the next 5 or so years, they slowly drifted apart, partly because she wanted to get a good career and he was happy moving from job to job regularly. Even though they both enjoyed sex, he pretty much wanted to go missionary every time until they were done and wasn't into trying anything at all kinky where she wanted to experiment a bit and see what she did or didn't enjoy. Apparently, one of the things she'd always wanted to try was playing with a guy's ass but that was a hard and fast 'no' from him.

By the time we'd chatted for almost an hour, almost all the nervousness was gone and we'd spent the last 15 minutes or so finally chatting about our joint interest in playing with my ass. I know I was hard, likely oozing some precum and from the way she was shifting and how hard her nipples looked through her top, I was pretty sure she was getting turned on too. Eventually I looked at her and said, "I really wasn't sure where things were going to go today but just in case, I threw a few toys and some lube into the car. Either I'm going to go home and use them, maybe on cam with you or if you'd like, I'd love to grab a room at a hotel and you can actually watch me play or if you're comfortable maybe even take over."

I could tell she was thinking about it which was definitely better than a "no" so I waited and after a bit more thinking she said, "What the hell... I've always wanted to do this so if I say no now, I may never get a chance. Which one?"

There weren't a lot of hotels in town but there was one right down from the Timmies so we headed there and after booking a room, we headed up. Now that it was at the 'gonna happen' stage, I was a bit nervous again so I headed for the bathroom to calm down and make sure I was nice and clean for whatever was going to happen.

When I came out Denise was sitting on the bed and I was nude except for my boxers but I'd gone totally soft. Here I was, planning on doing one of the things I'd fantasized about yet suddenly, I wasn't sure I was ready to go through with it. She must have sensed it because she said, "You look nervous, maybe this will help!" and with that she undid the shirt, shrugged it off her shoulders and then peeled the tube top up over her head.

I'd never been a huge tit guy, sure I loved seeing a nice set of boobs but what I really enjoyed were nipples; the longer and harder the better and hers definitely fit the bill. Her tits weren't small but her nipples were over 1/2" long with fantastic dark areolae. I'd seen all that over the webcam before but seeing them certainly did the trick and my cock quickly started to harden again. Seeing my reaction, she grinned and said, "Nice, now just to see you stroke it while you're playing with your ass."

Hearing her say that got me past my hesitation so I took off my boxers, grabbed the lube and with her watching closely, I spread some around my pucker and then started easing a fingertip in and out. It went in easily but I wanted to go slow, partly to give her the best show I could and partly to give me time to get over the last bit of nerves. Soon I was able to focus on the feeling of a couple of fingers in my ass and had almost forgotten she was watching until I added a third finger and heard her moan, "Fuck that's hot!"

When I looked up, she was rubbing a nipple with the fingers of one hand and the other was under her skirt but I was pretty sure what she was doing. Feeling a lot braver, I looked at her and asked, "Do you want to try?"

Now it was her turn to look a bit nervous but after a few seconds she nodded and moved closer. I could tell she wasn't quite sure what to do next so I took her hand, got a few fingers nice and slick and as I slid my fingers out, I guided hers against my slick pucker. That was all the encouragement she needed and it wasn't long before I had someone else's fingers up my ass for the first time in my life and it felt even better than I'd imagined it would and I let out a slight moan of pleasure. After sliding her fingers in and out for a minute or so, she tentatively started stroking my cock. When I moaned a bit louder, she smiled and as she stroked my cock, she added a fourth finger. Her hands were considerably smaller than mine so I was able to take her four fingers almost as easily as I could take three of mine.

When I was ready for more, I reached over to grab a vibrator from the bag and handed it to her. It was just a little narrower than her fingers had been so after lubing it up nicely, she slid the head easily into my ass. I was pretty sure it would feel different with someone else doing it and I was right, there was a whole new level of excitement not knowing how fast or how deep it would be going. She took it slow, learning as she went but pretty soon, she was sliding the whole length in and out of my ass as she stroked my cock and it felt incredible. I hadn't been sure exactly what if anything would happen after we met but I'd thrown a few other things into the bag and once both of us were comfortable with what was happening, I reached back into the bag and pulled out a slightly larger toy except this one was a vibrating strap-on with a piece on it to fit into a woman's pussy. I'd bought it almost a year earlier when I was going out with a woman who said she'd be interested but we broke up before we had a chance to try it.

When Denise saw it, I could tell by the look on her face she liked the idea and quickly figured out how to put it on. When I reached down and hit the 'on' button, her gasp told me that she could feel the vibrations in her pussy and even better I knew I'd soon be feeling them in my ass.

Her simple, "What position?" was answered by me moving to the center of the bed and sliding a pillow under my ass to raise it up a bit.

A quick nod from her told me she was good with it and a few seconds later I was feeling the buzzing end of it pressing against my pucker. There were a few slips and missed before she got the head inside and then a few more slips when she pulled out a little too far but it wasn't long before she'd gotten the feel for it and I was enjoying having a woman fuck my ass for the first time in real life. I was moaning, she was moaning and when I reached down to start stroking my cock, she stopped my hand and used hers instead.

By now the precum was dripping off my head and a couple of times, she scooped up a finger-full and licked it off which I loved watching. The next time she did it, she surprised me by bringing it to my mouth instead of hers. I'd tasted my own precum and cum a few times and it hadn't really done anything for me but licking the precum off her fingers as she fucked my ass was a whole different thing and I found it really turned me on. I'd been trying to hold back but it wasn't long before that wasn't an option and soon sprayed the first of several huge spurts up cum up and across my belly. After the spurts had reduced to dribbles and then finally stopped, Denise used a couple of fingers to scoop up some of the cum and then as I watched, she brought them up to her mouth and licked them off. She did the same thing a couple more times and then the next time she did it, she paused, looked at me and then slowly brought her fingers to my mouth. I guess when you've just been fucked in the ass by a woman you already knew but just sexually met, it's a lot easier to do something you normally wouldn't so I used my tongue to lick most of it off and then as she slid her fingers into my mouth, I sucked them clean.

"Thanks! That's something else I always wanted to try but Nate would never go for and it was just as hot to see as I thought it would be."

After saying that, she stopped for a few seconds before saying, "Can I try something else?"

"What the hell, why not? Go for it."

With a big grin, she leaned forward to lick up a lot of the remaining cum from my chest and then moved up a bit further and leaned toward my face. I figured out pretty quickly what she was thinking and surprised myself by reaching up so I could pull her down for a kiss. I caught a quick view of surprise before our mouths met for my first cum-swap kiss. When the last of the cum had been swallowed by both of us, she pulled back and whispered, "Damn, that's three things in one night that I'd always wanted to try but never did in 8yrs of marriage."

"Well, I'd never done any of them before either and I really hadn't considered swapping cum before."

"And?"

With a bit of a grin, I said, "And I thought it was pretty damn hot too!"

That led to another series of kisses except these were without any cum. When we stopped, we looked at each other for a bit before she finally said, "Do you need to get home in the next few hours?"

"No, why?"

Denise hesitated a bit before saying, "Well, I came once from the vibrations from the strap-on but I'd really like to cum a few more times if you wanted to play some more."

"I'd love to but as much as I enjoyed it, I'm not sure my ass would take any more fucking."

"I know I told you I was only interested in seeing what it would be like to play with your ass but as long as you're ok with me changing my mind, I was actually thinking that I'd like to cum from your cock in my pussy."

I didn't have to think too long about that at all and got one hell of a kiss when I said, "I'd love to!"

While there wasn't much need for foreplay, if we were going to fuck, I'd have to get hard again so Denise stood up and did a sexy striptease with her skirt and thong before laying back on the bed and slowly stroking herself. Her pussy was bare, her lips small and I could already see the tip of her clit showing between them. From the slight stiffening of my cock, we could both tell what she was doing was working and after a few minutes of watching, I ran my hand up the inside of her leg to see what her reaction would be.

With a sexy smile, she moved her hand out of the way when mine got to her pussy and the next few minutes were spent with me touching, teasing and eventually slowly fingering her pussy. Right from the first touch I could tell she was wet and the more I touched, the hotter and slicker her pussy felt.

"That feels great but if you're hard enough, I'm pretty sure your cock would feel even better!"

I was definitely hard enough but instead of taking her suggestion, I asked, "Is this going to be a one-time thing or ongoing?"

"Why?"

"Well, if it's just going to be a one-time thing then I really want to taste you before we go any further."

"Mmmm, go right ahead. I don't think I ever have or ever will say 'no' to having a guy give me a good licking!"

So, a 'good licking' is exactly what I gave her and she tasted amazing, especially when she came and I got a small trickle of her juices as a reward. It didn't take me long to find that while her pussy was sensitive, her clit was even more sensitive so I'd tongue her pussy for a bit, give her clit a few licks, tongue her pussy a bit more, suck on her clit and then repeat. After three good orgasms I felt her gently pushing my head away and as she did, I heard a quiet, "I need a minute or two."

I moved to lay beside her and she apparently didn't mind the taste of her own pussy because she gave me a passionate kiss followed by, "Holy shit that was amazing! I don't think I've ever cum more than once from oral and often not even once."

Pretty sure what her answer would be, I asked with a grin, "So you said you wanted to cum a few more times and you have, does that mean we're done for the day?"

With an equal grin she said, "Don't even think about going anywhere. All I need is a couple of minutes to recover and I'm going to climb on and ride your cock until I feel you cum and will likely cum a couple more times myself."

True to her word, a few minutes later, I was feeling her hot, wet pussy surrounding my cock as she lowered herself onto me. Not too tight, not too loose; a pretty much perfect fit. I didn't think I'd last long so after she found the rhythm that worked for her, I started playing with her nipples and when that got a moan of pleasure, I let one hand drift down until I was able to gently stroke her clit. Each time I touched it, she moaned and tried pushing harder against my finger but whenever she did, I'd back off for a few seconds.

Even with the pauses, she came with a long, low moan a couple of minutes later so I waited until that orgasm was just about over and then started rubbing her clit again but this time I went faster, harder and didn't stop. It wasn't long before she was moaning even more and then after a few seconds of just her mouth opening and closing with no sound, she let out a loud, "OH FUCK!" and it felt like her pussy was spasming on my cock. That was all it took for me to cum and I exploded inside her.

When both of us had come down from our sexual high we pretty much lay there for a bit before I rolled over far enough to give her a kiss and say, "Even though you came more than three times, I really hope this isn't a one-of because I really want to feel you play with my ass again and hopefully have some more sex afterwards because that felt amazing!"

"Mmmm, I'm glad you think so because I do too and yes, I definitely want to get together again!"

We got together online occasionally but more often Denise would come to my place or I would go to hers, sometimes just for an afternoon or evening but occasionally overnight or even for the whole weekend. Over the next month or so, we learned more about each other including and a few of our conversations were around what we did or didn't like plus what we would or wouldn't like to try. When we first met, she'd said that she was interested in trying different things and had already tried some of them. She'd had a boyfriend who was willing to spank her but even though he'd enjoyed it, she hadn't gotten anything sexual from it at all. I'd never spanked or been spanked but even though I'd watched a bit of spanking porn, the thought of spanking or getting spanked didn't do much for me either. When I told her I'd had one girlfriend who enjoyed both tying me up and getting tied up, she said she'd tried being tied up and didn't really like it but would kind of like to try tying up a guy for sex. There were a few other things we talked about but nothing that really caught both of us as a "Let's try it."

The more we got together, the more I looked forward to seeing her again even though we'd already agreed that we didn't want to rush anything and neither of us were looking for a full relationship right then. Whenever we got together, I enjoyed her using her fingers in my ass, a variety of toys (we bought a few more), a couple of different sized butt-plugs that I'd sometimes put in a few hours before we got together. We tried lots of different positions too, me on my back, kneeling, bent over the bed and bent over the couch. It wasn't always about the sex, we found we both enjoyed being together and trying new things. One of them was going to a local nude beach and one day that we were there I was laying on my side with her on her side behind me. She surprised me by sliding a couple of lubed fingers into my ass for a minute or so and then replacing them with one of our toys that she'd brought along without telling me. There were a few other people around so I had to make sure I didn't moan too loud and when she realized no one was watching, she reached around and stroked my cock in time with the thrusts into my ass until I shot a huge load into the sand. When we talked afterwards, we both agreed that the thrill of doing it in public just added to the overall sexual pleasure.

One afternoon after a few drinks and a toke or two at her place she told me she'd remembered me telling her about using a cucumber and wanted to know if I'd be ok with her trying that. When I agreed, she grabbed one from the kitchen and it was bigger than the one I'd used, in fact it was bigger than anything I'd had in my ass before but with me laying on my back with my legs up a bit, lots of lube, patience and gentle pressure, my ass finally accepted it and even though it hurt a bit at first, the feeling was amazing. When she was able to slide it in and out fairly easily, she started stroking my cock. After a few minutes, to my surprise, did something she hadn't done before and replaced her hand with her mouth. She'd told me early on that she really never enjoyed giving head so not to expect it and I told her that while I certainly enjoyed it, I could easily live without it.

As she sucked me, I quickly realized that while she'd said she didn't enjoy it, she was really good at it. I encouraged her with, "Damn that feels great!" as she continued to suck, lick and kiss my cock and at the same time she stroked the cucumber in and out of my ass.

Seeing as it was the first time that she'd ever done it and by now I was hoping she'd do it again another time, when I got close to cumming, I let her know. I was kind of expecting her to stop and finish me with her hand but instead she took as much of my cock into her mouth as she could, wrapped her fingers around the base and started quickly stroking my shaft. That was more than enough to make me cum and I'd found that any time anal play was involved, I came harder than usual and today wasn't any exception. I felt pulse after pulse of cum shoot down my shaft and into her mouth but she didn't move away and took it all. With as much of a grin as she could manage with a mouthful of cum, she grinned and then swallowed all of it. She'd 'fed' me cum off my finger and shared a bit that she'd licked off my chest before so I was fine when she gave me a kiss that still had a trace of cum with it.

As we lay on the bed recovering, Denise looked at me and said, "Pizza?"

"What?"

"Pizza... I'm hungry and I think I'd like pizza!"

That got both of us laughing and soon I was on the phone ordering our supper. After we ate, we had another drink or two and when I suggested going back to bed, her response was, "I'd love to, how about a nice soak first?"

Denise had a hot tub that we'd used a few times and were soon enjoying the heat, the jets, a couple more joints and of course making out at the same time. By the time we went back inside, I was totally hard and we were both ready to go. I certainly wasn't going to say no when Denise suggested giving my cock a little 'oral warmup' as she called it. I was totally enjoying the feeling of her licking and sucking my cock when suddenly I felt one of her fingers drift across my pucker. After the cucumber earlier, I wasn't thinking of any anal action and when she pushed against my entrance I said, "I'm a little tender back there."

After lifting her mouth off my cock, she said, "Hmmm, then let me see if I can make it feel a little better."

At first, I wasn't sure what she meant but then instead of going back down on my cock, I felt her tongue flick over my entrance just like her finger had done a minute or so ago. After a few tentative swipes, I felt it push harder as it circled my pucker which felt great and then it got even better when I felt her push the tip of her tongue against my entrance. My moans of pleasure seemed to encourage her and she was soon rimming and tonguing my ass as she stroked my cock at the same time. I'd have been quite happy for her to continue until I came again but apparently, she had other plans as she suddenly stopped, turned a bit and straddled my cock. We'd had sex in pretty much every position we could think of but she really liked riding me and I was totally fine to lay back and enjoy not only the feeling but the look on her face, the way her nipples got long and hard (especially when I played with them) and the way she came when I played with her clit at the same time.

I'd found long ago that a joint or two really seemed to make me a lot hornier but able to hold off cumming easier which worked out well for both of us. Every so often we'd switch to a different position but when I could feel I was close to cumming, I let her know and asked if she'd like to finish on top. She just grinned, nodded and after a few more minutes of her thrusting up and down on my cock, I groaned and let go with a huge load into her pussy. As I did, I pulled her close enough to whisper, "You've done things with your mouth and tongue tonight that you've never done before with me and they felt great. I'd like to do the same for you" and with that, I put my hands on her hips and pulled upwards gently. As she moved up toward my face, she must have realized what I was thinking because I heard a whispered, "Oh yessss!"

Sure, I'd watched porn of a guy eating his cum from a woman but it wasn't something I'd really thought of trying but right then, it was something I really wanted to do. When her pussy was right over my mouth, I gave it a couple of tentative licks and was surprised that other than a slightly different taste, there was nothing to really make me think that she was full of my cum. That quickly changed as gravity took over and soon, I was tasting her juices mixed with mine. When she came the first time, there was even more cum pushed out into my mouth but if anything, that just made me want to lick and suck on her pussy even more. After at least 10 minutes and a couple more orgasms, I was back to tasting just her juices so I figured that there wasn't any more of my cum left inside her. When she finally lifted off my face and moved so she was lying beside me, I could see traces of tears on her cheeks.

When I asked what was wrong, she smiled a little and said, "Nothing's wrong, in fact everything's very 'right' right now!"

Seeing the puzzled look on my face, she explained, "Remember when we talked about the things we did or didn't want to try? Well, I wasn't totally honest and left out what you just did. I've asked several guys I was dating and not only did they all say no, they usually broke up with me shortly afterwards. I'd even asked some of my girlfriends if their boyfriend/husband ever went down on them after sex and while some of them said it sounded hot, none had ever been with a guy who'd do it. I've really enjoyed everything that we've done and was afraid if I told you I wanted to try it, you'd say no and not want to get together again."

The whole time she talked, she watched for any sign that I was upset by what she was saying and when she finished, she simply said, "Well?"

Instead of answering, I just pulled her closer so I could give her a long, hot kiss followed by, "I'd never done that before and honestly never really even thought about doing it but now that I've done it, I'm definitely ok to do it again another time."

Hearing that, her look of concern was replaced by a big grin, followed by an even bigger kiss. When we finally pulled away, I said, "I don't think it'd be an 'every time' kind of thing but I liked it way more than I thought I would" then as a bit of an afterthought, I added, "maybe next time we can kick it up a notch?"

"I'm not sure what could kick that up a notch, what are you thinking?"

"Well, maybe next time instead of swallowing it, I'll hold as much of our juices in my mouth as I can and we can kiss and share them after you cum."

"Hmmm, you're right - that would be kicking it up a notch. I'm usually not a huge fan of cum in my mouth but just thinking about what you're suggesting made my pussy tingle so I'm good to try it. Does that mean you'd be ok swapping cum if I sucked you until you came in my mouth?"

Before my brain could really process what she was asking, my mouth went ahead and said, "Sure, why not?"

"Mmmm, you're the first guy I've ever met who's ok with the taste of his own cum. No guarantees but that might just mean there'll be a few blowjobs in your future!"

I just laughed and said, "Seeing as I'm also the first guy you've ever met who enjoys having his girlfriend fuck his ass with a strap-on, that shouldn't be too surprising."

As soon as I realized I'd said 'girlfriend', I looked to see if she'd caught it and it was quickly apparent that she had. Oh boy, call it a Freudian slip if you want but now that it was out there, I wasn't sure which way things were going to go. Any fears were quickly dispelled when she leaned in, gave me a long, soft kiss and whispered, "Girlfriend eh? I think I like the sound of that!"

It took me a second or so to realize what she was saying before we ended up in a tangle of arms and legs as we hugged and kissed at the same time, we were gently touching each other. The realization that we were taking what we had to a whole new level seemed to also give us a new level of energy and we spent the next couple of hours touching, kissing and making love.

A week or so later, we decided to go back to the nude beach for the afternoon. Once we got our things laid out and got undressed, Denise pulled out some lube and a butt plug. She really didn't need to say anything and soon I was enjoying the feeling of her sliding it inside me. I wasn't totally sure which one she'd grabbed until a few minutes later when I suddenly felt it vibrating. When I looked over at her, she just grinned and held up the Bluetooth remote. As the afternoon went on, this time it was me curled up behind her. We'd been kissing and touching and I knew she was pretty wet so when I grabbed her hips and slid into her pussy, I went in easily on the first stroke. If anyone looked closely, they'd have known what we were doing but from a distance we were just another nude couple curled up together on a blanket.

With the limited movement, it took a bit longer for either of us to cum but she'd came twice before I finally exploded and I could feel my ass clenching on the plug as I came. I was a bit surprised when Denise got up and sat on the big log by us with her back to the beach. When she said, "I'd love to feel your tongue for a bit" I quickly caught on and moved in front of her. The combination of her and the log pretty much blocked anyone's view of what I was doing and soon I was licking and kissing her freshly fucked pussy and was quickly treated to the combination of both our juices. Even though she'd already cum twice, neither had been a 'big' one so I gave it everything I could to bring her to a nice big orgasm and it wasn't long before she did. Not only did the clenching of her orgasm force the last few bits of my cum out. As she came, I could easily hear her, "Oh fuck yes, I'm going to... FUCK!" and that's when she squirted for the first time since we'd been together.

The first squirt caught me by surprise but I'd dated a squirter a year or so ago so once I realized what was happening, I dove back in and licked her through several more squirts. Each time she squirted, I could hear her moaning loudly, "Oh damn... again!" with lots of loud moaning in between each squirt.

When she finally stopped squirting, she pretty much melted to the blanket I was kneeling on and before she realized what I was doing, I shifted to give her a long, hot kiss while I shared my mouthful of our cummy mixture with her. At first, I think she was a bit surprised but quickly got into it and soon we were kissing on the blanket like a couple of teenagers making out. Eventually we mutually rolled onto our backs to catch our breath and then after a few minutes decided to go for a quick swim and rinse off. As we came back out of the water, there was a woman walking along the shore that had been sitting with her husband about 30 feet from us. As we passed, she looked at Denise and said, "I'm not sure what was happening but from the sounds you were making a little while ago, I wish it had been me!" and then kept walking.

Denise blushed, I laughed and we headed back to the blanket to enjoy the rest of the afternoon before we had to leave. Unfortunately Denise couldn't stay the night but once we got back to my place, both of us were able to enjoy the feeling of her sliding the vibrating strapon into my ass and fucking me with it until we'd both cum again.

Other than our new commitment to each other, we kept everything else pretty much the way it was. We talked about options of one of us moving in with the other but seeing as we both had good paying jobs with good benefits, neither of us was really in a position to move but we certainly enjoyed every minute we could spend together. All that changed a month or so later when I got a text from her that simply said, "Check your email!"

When I did, I could see that she'd forwarded me an internal memo indicating that the board would be looking for a new manager of the IT maintenance department along with the direct contact info of the HR person and that I was welcome to use her as a reference. One telephone interview, one Zoom interview and one in-person interview later, I got a call letting me know that I'd been selected and as of the first of the month would be the new head of the IT maintenance department.

I immediately called Denise and when she answered, I said, "I've got good news and bad news."

"What's up... what's the good news?"

"I got the job as IT manager!"

"That's awesome! What's the bad news?"

"Well, I'll need to move so I was hoping you might know somewhere I could stay temporarily until I can find a place there?"

It took Denise a few seconds to realize I was kidding before she said, "Oh, I'm pretty sure I can find somewhere for you to stay but the rent would be high enough to feel it all the way to your ass!"

"Exactly what I was hoping for! I'll let you know once I work out all the details."

Of course, when I submitted my resignation with my current board, they came back asking how much of a raise it would take for me to stay but I simply told them, "You might be able to match the money, but you won't be able to match the benefits!"