Anal Fantasy to Reality

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."