Voyeur to Couple

I was in second year university, going for a masters in computer science. As much as I really wanted to have a place of my own, my parents wouldn't go for that much money so I was in a dorm with three bedrooms and a common living/kitchen area. At least I had a part time job and they had promised me full time hours over the summer so hopefully I could get an apartment or something of my own in the fall. Not good for him but one roomates had dropped out a few weeks ago so right now it was only two of us and Sam had a girlfriend off campus so he spent quite a bit of time there. The only real advantage was that our dorm faced a coed dorm so there were a few times that I was able to see either a couple going at it or a naked woman through my window and theirs.

Normally it would be hard to see much detail but when I was still at home, I'd bought a fairly good telescope for star gazing and found it worked very well for a bit of voyeur action. I spent many a night with the lights in my room off, the curtain partly open scanning back and forth across windows to see what I could see. If I got lucky and there was either a nude woman or couple then I'd often be stroking my cock while I watched or when I was done. I'd found there was one window in particular that I kept an eye on as the woman in that bedroom was often naked and even better, several times I'd been able to catch her on her bed masturbating with fingers or a toy. It was hard to tell her height but I'd have guessed about 5'6", straight red hair, and while her boobs were fairly small (maybe a 'B' cup), even from where I was, I could see that she had large, dark areolae and when they were hard, her nipples looked much longer than most.

Her hair looked naturally red and while her pussy was bare, there was a small red patch of hair just above it. She obviously either worked out, played sports or both because she was slim and looked like she was in great shape. I didn't know her from any of my classes but with a university of a few thousand people, that wasn't surprising. It didn't take long for me to get a pretty good idea of her schedule so I knew what nights or days she would likely be there. As much as I was trying to save money, after a couple of weeks of watching, I decided to spend $50 and get an adapter that would connect my digital camera to the telescope so I could take pictures or video of anything that looked really good. I also got an cable to connect the camera directly to my tv so I could watch on my tv whatever the telescope was pointing at because it was a lot more enjoyable stroking my cock while laying on the bed instead of trying to watch through the telescope.

As the year went on, I built up a fair collection of pictures and videos of various people from the other dorm that were great to watch whenever there were no 'live' views to be had. A few times that I'd been shopping, at the cafeteria, library, hallway or somewhere else, I'd seen someone I'd watched sometime which was also fun because my first thoughts were always of what I'd seen when they were naked. The one woman I often enjoyed watching had taken to masturbating more frequently and had got a couple of bigger toys. One night, I'd even been able to see her fingering her ass at the same time. A week or so after that, I was laying on my bed, slowly stroking my cock while I watched her fucking herself with a vibrator. She'd started slowly but had worked up to fairly fast, deep thrusts when suddenly she stopped and reached for the nightstand. I was thinking maybe she was reaching for a different toy but instead she grabbed some lube. That immediately made me think that this was going to be one of the nights that she was going to finger her ass too and my cock got even harder at the thought.

While I wasn't a virgin by any means, even though I'd tried a few times, I'd never met a woman who would let me fuck her ass so this was as close to it as I'd ever gotten. To my surprise, after getting her pucker nice and slick, instead of using a finger she took the vibrator out of her pussy and pushed the tip up against her pucker. I really wished I had a bit more zoom to see closer but I was still able to see a clear image of the toy as she worked it further and further into her ass. Obviously, I couldn't hear anything but if I shifted to her face, I was pretty sure she was moaning and it definitely looked like she was enjoying it. I panned back down and for the next 10 minutes or so, I watched as she fucked her ass with the vibrator and either stroked her clit or fingered her pussy at the same time. Eventually her movements got really erratic and then she totally relaxed so I figured she'd finally came. After a minute or so, she got up and left the room for a few minutes, likely to go to the bathroom and when she came back, she turned out the light beside her bed so I knew the show was over for the night.

About the same time, I realized that I'd been so focused on watching her that I'd stopped stroking my cock but I was still hard as hell. As I went back to stroking myself, I went to the recording so I could watch again from the beginning. I really enjoyed the part where she lubed her ass and then slid the vibrator in. After watching it a few times, the precum was literally dripping off the tip of my cock and just on a whim, I did something I'd never done before. I gathered a bit of it up and as I watched her lube her pucker, I slid my slick finger across mine. To my surprise, my cock immediately twitched and I felt a bit of a tingle from my ass to my cock. I did the same thing a few more times and then tentatively slid the tip of a finger in through my slippery rosebud. The more finger that slid inside, the better it felt but it wasn't easy to get in so I grabbed a bit of lube from the dresser and after adding a bit of that to my finger, I was able to slide it in much easier. Between watching her fucking her ass with a vibrator, my finger up my own ass and my other hand stroking my cock, when I came, it was huge! The first couple of spurts hit the pillow beside my head, the next couple hit my chest and the rest pooled on my lower belly. I'd had a lot of good orgasms but it had been a long time since I'd cum that hard or that much.

From that night on, any time I was able to catch her and she was fingering or toying her ass, I'd finger my ass while I watched her on the tv and almost every time, when I finally came, it was a huge one. One night I'd been out with the guys for a few drinks after classes and then had a few more when I got back to the dorm so I was more than just slightly drunk. Of course, drunk and horny often went together so it wasn't long before I was scanning windows of the other dorm and to my delight, my favourite subject was laying on her bed, playing with her pussy. I wasted no time in stripping naked, firing up the tv and video record as well as grabbing some lube. Sure enough, it wasn't long before she was playing with both her pussy and her ass and after a little while, she rolled to her nightstand and came back with the toy she usually slid into her ass. A few weeks before, I'd tried two fingers in my ass and really enjoyed it so as I settled onto the bed, I had the thought that it might be fun to try something a bit bigger but at first I couldn't think of anything that would work and then I remembered that an ex girlfriend had left a dildo behind. It was only an inch or so across and about 6" long but I figured for the first time, that would be plenty big enough.

I eased the tip against my pucker and the feeling of my rosebud stretching as it slid in felt great but it only went in an inch or so before it stopped at what I realized was a second ring of muscle. It took a bit more time and a bit more lube than I thought but eventually I felt my inner muscle stretch enough to let it in and even the slight bit of pain that it caused quickly turned to pleasure. Now I was able to actually slide something in and out of my ass at the same speed she was doing it and when I came, it was another really huge one. That got me hooked and after using that for the next week or so, I decided to go to the local sex shop to find something that was a bit bigger and would vibrate. When I got there, the guy seemed pretty bored as he said, "Can I help you?"

Just the way he said it sounded like what he really meant was 'If I have to, I'll help you but I'd just as soon stand here and do nothing until you're ready to pay.' When I told him I was looking for a somewhat life-like vibrator for my girlfriend, he pointed in the general direction of the back corner and said, "Should find something back there."

Wow, so apparently customer service wasn't high on their list but after a few minutes of looking, I'd eliminated the ones that were too small, too big, looked too hard or were stupid expensive and settled on a kit with two of them in it, one a bit bigger than the other.

That night, other than a quick flash as she came from the shower to her room, there wasn't anything to be seen in the room of my favourite view so I fell back on some of what I'd recorded and tried the smaller of the two vibrators. It was just a bit bigger than the one I'd been using but when I hit the button and it started to vibrate, it was an entirely new and very pleasureable feeling.

Over the next month, I enjoyed watching a few others in the opposite dorm but always hoped that I'd see my favourite lady and any time I did, I'd enjoy an awesome orgasm as I played with myself at the same time. I'd even moved from the smaller toy to the bigger one. It was about an inch and a half across and the first couple of times I used it, I could feel a definite stretching as it slid in and there was a slight pain but at the same time there was a feeling of intense pleasure. Of course, I'd grown up hearing all the "any guy that likes something in his ass must be gay" kind of things but I had no urge to see, touch or do anything with another guy or his cock but enjoyed the feeling of a vibrator in my ass at least a couple of times each week.

One Friday after classes in early spring, there was a karaoke event at the campus bar. I wasn't much on karaoke, but I did enjoy the cheaper drinks they offered to anyone who bought event tickets and of course there was always the possibility of meeting a lady I'd like to date or at least take back to the dorm for the evening. Unfortunately, other than the cheap drinks, the 'lady' part didn't seem to be working out so just as I was considering heading back, I saw a familiar face and when I took a better look, I was totally surprised to realize that it was the woman that I often watched in the other dorm and she was sitting with three of her friends, two blondes and a brunette. That changed my decision to leave so I grabbed a couple more drinks and was able to move to a seat nearer their table. Either in between songs or if the music wasn't too loud, I was able to hear some of their conversation and over the next while, I learned her name was Claire, it sounded like she was a second-year student and was taking some sort of an arts program.

About 20 minutes later, two of her friends had left and by now Claire and her remaining friend seemed a bit tipsy and were getting a bit louder so it was a lot easier to hear them. Just after their next round of drinks got served, I missed what Claire said but her friends reply of, "Seriously, you think you're going to find a guy who likes things up his ass as much as you do who's not gay? I can't even find a guy knows how to get me off with his tongue!"

I lost the next few bits of the conversation and then heard Claire say, "It shouldn't be that big a deal, I mean an ass is an ass so I'm pretty sure it would feel as good to a guy as it does with me. I've watched enough videos; I just think it would be cool to at least see a guy playing with his ass in real life and maybe even use a toy on each other."

There was a bit of a break on stage so I clearly heard Claire's reply of, "Ya, you're likely right but at least I can think about it while I'm masturbating occasionally. Anyway, I gotta go for now, all this talk has made me a little 'damp' so I think I'll go back to my room and take care of things if you know what I mean."

"Oh great, you're leaving me with that bit of information so now I'll have those thoughts running through my mind the next time I'm playing with myself."

Claire just laughed and said, "Well maybe you should try it sometime! I didn't always like something in my bum but once I tried it, I came really hard whenever I did it."

"Nope, not interested. I get plenty of pleasure getting my pussy filled and speaking of that, if you're leaving maybe I'll just find a guy who'd be interested in a quickie tonight."

That got a laugh and "What about your boyfriend?" from Claire.

Deb's response was, "He's not here and I'm horny plus I'm pretty sure we're done because he hasn't called or returned my calls all week."

When they got up for a quick hug goodbye, I could see that Deb was short, likely just over 5' tall but her chest was at least a DD and even though I was pretty sure she wasn't wearing a bra, there wasn't much sag at all. She obviously wasn't a fitness nut because she had a few extra pounds but they were all in the right places to make her look very good and her jeans totally emphasized a nicely packed ass. After Claire left, I knew that if I headed to the dorm then I could get to my room before she got to hers and I would likely get one hell of a show but at the same time, I'd just heard her friend say she was going to see if she could find someone for a quickie. 'Quickie' immediately won over 'show' and on the way up to grab a fresh drink, I 'accidently' bumped into Deb. After apologizing, I introduced myself as Paul and asked her if she'd like me to buy her a drink. Without being too obvious, she looked me over and apparently just under 6', curly dark hair, clean shaven and in good physical shape was enough to get a "Sure." from her.

A few drinks later, she talked me into going up with her to do an old Kenny Rogers/Dolly Parton song. At first, I said no but after she promised me a kiss afterwards if I did, we were soon up on the stage. Neither of us could sing well but it was fun doing it and when we got back to the table, I said, "That was fun but I'm really looking forward to that kiss you promised me."

With a bit of a smile she said, "And I thought you'd forgotten!"

"Forgot about getting a kiss from a sexy brunette, I haven't had anywhere close to enough to drink to forget that!"

That got an even bigger smile followed by a very hot kiss. "So, how sexy do you think I am?"

I figured it was a pretty good time to get a definite 'yes' or 'no' for any fun so I said, "Hmm, let's see... I love tasting a woman so how about 'straddle my face so I can lick you until you cum' kind of sexy?"

If she said 'yes', then that would pretty much be a guarantee of sex and if she said 'no' then I could likely still get home to watch Claire for a bit before she was done.

I could tell that she was slightly shocked by my answer but after a couple of seconds, she gave me another big kiss and said, "I like a guy that's pretty straight forward and I LOVE the way you think. I'm pretty sure my roommate, Sandy is already gone for the weekend, I'd love to take you up on that offer if you want to come over."

That was exactly what I wanted to do and within a couple of minutes, other people were taking our seats because we were already heading outside. I found out she shared a basement apartment not too far away and when we got there, we were both happy to find that her roommate wasn't there. We kissed some more once we were inside and then again when she led me to her bedroom. From there it was a flurry of kissing, undressing and touching before we were both naked and making out on the bed. After a few minutes, she looked at me and said, "How about that licking you promised me?"

With as straight a face as I could manage, I said, "And I thought you'd forgotten!"

Apparently, she found that hilarious and was still laughing as she straddled my face and I gave her pussy the first couple of licks. I'd had a number of girlfriends and they'd all said they enjoyed both the quantity and quality of oral that I gave them so I grabbed Deb's hips and spent the next 10 minutes licking, tonguing, kissing and nibbling her pussy and clit. Every few minutes she came and by the time she rolled to my side, I know she'd cum at least 6 times and likely more.

"Holy shit! You weren't kidding when you said you loved tasting a woman, you definitely meant it and damn, I gotta say you're good!"

After thanking her with a kiss, I said "I'd love to put more than my tongue in you if you'd like."

"Mmmm, I'd really like that too!" and to prove it, she rolled over and pulled her legs up a bit to give me perfect access.

It only took a few strokes before my 7" was in as far as it could go and while it definitely wasn't the first fuck she'd had; she was very snug so I had to wonder just how big her 'boyfriend' was. She kind of confirmed my thoughts when she said, "Go easy for a bit, you're bigger than I'm used to but once I get used to it, fuck me nice and hard."

Those were pretty easy directions and I took them well. Just as she'd said, within a few minutes, I was sliding in and out much easier so I started going harder and faster until she came a couple more times. When I pulled out, she said, "Did you cum and I didn't notice?"

I just gave her a grin and a long kiss followed by, "I'm not there yet, I just thought you might like it from behind."

With a quick, "I do!" she rolled over and I slid right back into her in one thrust. I took a bit of time for her to get used to the new angle and then sped back up again. Soon my thighs were making 'smacking' noises against hers as I bottomed out with every stroke. I not only had a perfect view of my cock going in and out of her pussy, but right above that I could see her pucker and with every thrust in, it opened slightly before closing as I pulled back.

I had no idea if she liked anal or not but figured I didn't have much to lose so after caressing and rubbing her ass cheeks for a bit, I got one finger nice and slick with some spit and gently teased her pucker. At first, she pulled back but then looked over her shoulder and said, "I don't mind a finger but that's it - ok?"

Of course, I'd really been hoping that she'd tell me she wanted to feel my cock up her ass but a finger was better than nothing so I grinned, nodded and over the next few minutes I teased her pucker with just the tip of a finger before I started sliding more of it in. With a bit more saliva, I was eventually able to work the whole length in and by the way her moaning increased, I was pretty sure she was enjoying it. I reached around with my other hand to play with her clit and it wasn't long before she came again. By now I was a whole lot closer to cumming than I'd been before and when Deb looked back and whispered, "I want to feel you cum in my pussy" that was all it took and a couple of strokes later I erupted inside her.

Now it was my turn to roll to the side and after a few seconds Deb said, "Damn, that was exactly what I needed and it felt like it was what you needed too. Just to make sure we're on the same page, I think I just got dumped by my boyfriend so not looking for another one but from the way you ate my pussy, I'm certainly open to an occasional 'rematch' if you'd like."

"That sounds perfect to me and if I happen to see you with another guy, I'll be sure not to say 'hi'!"

I was pretty sure I wasn't going to get an invite to stay for the night but she didn't seem like she was in a hurry for me to leave either, so as I lay there, I gently rubbed from her neck, across her nipples, down to her pussy and back up again. When she started stroking my cock, I thought maybe we'd have a second round before I left. Then when she shifted so instead of her hand on my cock, I was feeling her mouth, then I was pretty sure we'd be having some more fun. She either didn't care that my cock tasted like her pussy or she didn't notice but it wasn't long before I was fully hard again and she was taking almost all of me into her mouth. She couldn't seem to get the last inch or so but what she was doing with the rest of my shaft more than made up for it. I was just getting into the feeling of her lips and tongue, she stopped, looked up at me and that's when I felt her finger gently pushing against my pucker. I could tell she was watching to see what reaction she'd get and she seemed surprised when I just grinned, nodded and even pushed against her finger slightly. For the next 10 minutes or so, she gave my cock one hell of a sucking and at the same time, gave my ass its first fingering by someone other than me. She was gentle, took her time and it felt even better than when I'd done it myself. Without stopping with her finger, she looked up and said, "I'm not usually into swallowing but I came so many times from your tongue that I thought I'd return the pleasure" and went back to sucking.