Anal Fantasy to Reality

"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!"